Fatty Alcohols Petition
Fatty Alcohols Petition
Fatty Alcohols Petition
Fatty Alcohols
Petitioner:
Subi:nitter/consultant:
Cover Letter 1- 4
Item B 1
1. Product's Common Name
Substances Common Name
IUPAC Name
Other Names
2. Manufacturer's Name, Address and Telephone Number
3. Intended Use 2
4. List of Activities for which the substances will be used
5. Source of the substance and description of 3
manufacturing procedure
6. Previous reviews
0 7. Information regarding EPA, FDA and State
Regulatory Authority registrations, including
4
registration numbers
8. Chemical Abstract Service (CAS) number or
other Product Numbers
9. Substances physical properties and chemical 5-33
mode of action
10. Safety information including MSDS form 34-35
TABl
List of Activities for Which the Substances will be Used 1
TAB2
Previous Reviews by State, Federal and International Agencies
(Industry Experts, OMRI Reviews and Industry Certifications)
• ICOF America Communication 1- 3
• Communications with Organic Materials Review Institute (OMRI) 1- 8
• University of Wisconsin Department of Food Science Letter 1- 2
• University of California, San Diego Letter 1
0
1
ISO, GMP, RSPO and Other Certifications
• GMO Free Statement Letter 1 0
• Certificate - RSPO SCCS 1- 2
• Kosher Certificate 1
• SGS Certification 1
• Certificate of Accreditation KAN 1
• SGS Certification - ISO 14001 : 2004 1- 2
• SGS Certification - ISO 18001: 2007 1- 2
• SGS Certification- ISO 9001 : 2008 1
TAB3
EPA, FDA, EAFUS and State Authorities, Spec. Sheets Labels & MSDS Forms
• Memorandum
Aliphatic Alcohols: Human Health Chapter of the Registration 1 - 13
Eligibility Decision (RED) Document. Reregistration Case Number 4004
• Monograph
0
Literature Review on Fatty Alcohol Compounds 1 - 60
TAB4
MASCOL 80 Fatty Alcohol
TABS
Manufacturing and Production Process Fatty Alcohols
0
4
• Petition Justification and Other Relevant Support Documents
Green Chemistry Support Documents
• Up Close and Green
TAB7
1
1- 4
• Clean and Green 1- 2
• The Greening Game 1- 6
• The Highs and Lows of Green Certification 1- 2
• Make Your Green Claims Mean Something 1- 3
TABS
NOP Communications, TAP Review NOSB Committee Actions & Vote
TAB9
Pending Petition Information (Correspondence) pertaining
To other proposed uses:
Pending Cotton 1 - 33
0 Pending Vegetable Rootstock 1 - 17
0
5
0 Lehigh Valley Organic Growers, Inc.
125 West Seventh Street A Company of L VOG Inc. Telephone: 610 863-6700
Wind Gap, Pennsylvania 18091 USA Facsimile: 610 863-4622
Email: [email protected]
The purpose of this correspondence is to respond to your September 25, 2015 letter that
addresses your comments pertaining to the petition filed on June 24, 2015 which requested the
inclusion of natural fatty alcohols in Section 205.601 of the National Organic Program's (NOP)
National List of Allowed and Prohibited Substances (National List).
We are modifying the previous petition and resubmitting petition which includes the following
actions I modifications:
We agree that since the fatty alcohol blend (natural fatty alcohol - Mascol 80)
is registered by EPA as a growth regulator and that it will be considered by the National Organic
Standards Board under section 205.601 (k)(2) rather than 205.601 (a).
With respect to your point "The petition should also clearly indicated why a single petition is
needed for the fatty alcohols mixture (ie blend of octanol and decanol) instead of separate
petitions for octanol and decanol as individual active ingredients," the blend of CsC 10 fatty
alcohol is the product that is specifically manufactured for use in the end products, (eg N-TAC,
0-TAC PLANT CONTACT AGENT). The only other registered uses for individual fatty
alcohols is for C 10 (decanol)- EPA Reg. No. 63896-2 and is not included in this petition. There
is no EPA registered use for Cs (octanol) fatty alcohol. The raw material for this alcohol is
derived primarily from Palm Kernel Oil and Palm Oil, not synthetic alcohol.
0
1
Item B - 6 Previous Reviews: .
We have added the following summary of the information provided in Tab 2 of the petitio$.:
!
0
The information provided in Tab 2 (Industry Experts OMRI Reviews & Industry Certifica~ions)
concerns the debate on whether the naturally derived fatty alcohol (Mascol 80) from the natural
sources of palm oil, coconut oil, etc. are considered natural alcohols. Apparently OMRI' s •
classification would depend on the review the specific ingredients and manufacturing processes
to be sure about the classification as a synthetic or natural alcohol. We believe that an alcohol
derived from natural plant sources should be classified as a natural alcohol as does Franco X.
Milani, Assistant Professor, Extension Food Manufacturing Specialist, University of Wisconsin
and Dr. James K. Whitesell, Professor of Organic and Materials Chemistry, University of
California, San Diego.
• Various certifications
a. Certified Kosher
b. Compliance with RSPO (Roundtable on Sustainable Palm Oil) Supply Chain
Certification Systems
c. Certified as to meeting the requirements of GMP Codex Alimentarius -
Recommended International Code of Practice General Principles of Food Hygiene 0
d. Certification of the Mascol 80 supplier, P.T. Musim Mas has met the requiremehts of · ·
ISO 14001: 2004, ISO 9001: 2008 and OHSAS 189001: 2007 for the manufacture of
Oleochemicals.
You are correct in noting that the products 0-TAC PLANT CONTACT AGENT and N-T~C are
labeled only for use on tobacco. Petitions for the other uses are pending with EPA and are hot
currently permitted by EPA; therefore, we have amended the petition to remove the followihg
uses
• Sucker control on tomatoes
• Meristematic regrowth on vegetable grafts
• Desiccant/defoliant on cotton
Therefore, we are resubmitting our petition that has been revised per the following- note tht')
changes are in blue:
0
2
1. Page 1 Item A
0 NOP Reference changed to 205.601 (k)(2) and Requested annotation changed to "For use
as a sucker control on organic crops."
3. Page2 ItemB-3
Intended Use: As a sucker control on organic crops (the other proposed uses have been
deleted)
4. Page 2 Item B - 4
List of Activities for which the substance will be used:
4 A - delete on tobacco and tomatoes: Change to: Sucker Control on organic crops:
4 B and 4 C have been deleted.
5. Page 3 Item B - 6
Previous reviews
0 The information provided in Tab 2 (Industry Experts OMRI Reviews & Industry
Certifications) concerns the debate on whether the naturally derived fatty alcohol (Mascol
80) from the natural sources of palm oil, coconut oil, etc. are considered natural alcohols.
Apparently OMRI's classification would depend on the review the specific ingredients
and manufacturing processes to be sure about the classification as a synthetic or natural
alcohol. We believe that an alcohol derived from natural plant sources should be
classified as a natural alcohol as does Franco X. Milani, Assistant Professor, Extension
Food Manufacturing Specialist, University of Wisconsin and Dr. James K. Whitesell,
Professor of Organic and Materials Chemistry, University of California, San Diego.
• Various certifications
a. Certified Kosher
b. Compliance with RSPO (Roundtable on Sustainable Palm Oil) Supply Chain
Certification Systems
c. Certified as to meeting the requirements of GMP Codex Alimentarius -
Recommended International Code of Practice General Principles of Food Hygiene
d. Certification of the Mascol 80 supplier, P.T. Musim Mas has met the requirements of
ISO 14001: 2004, ISO 9001: 2008 and OHSAS 189001: 2007 for the manufacture of
0 Oleochemicals.
3
6. Page 4 Item B - 7
Information regarding EPA, FDA and State regulatory Authority Registrations: We have
0
added the following :
Active substance EPA Reg. No.
C8C 10 fatty alcohol blend 63896-1
7. Tab 1
List of Activities for which the substance will be used:
1 A - delete on tobacco and tomatoes: Change to: Sucker Control on organic; crops:
1 B and 1 C have been deleted.
8. Tab 3
Removed all the information on rootstock and cotton after the NC Department of
Agriculture registration of product and license renewal. Move to TAB 9.
9. Tab 7
Under Petition Justification Statement:
We have deleted; "Crop sucker control and Plant Desiccant/Defoliant Use" and replaced
it with Sucker Control on organic crops".
In the last paragraph on this page we have replaced the words "various production crops"
to organic crops. On the second page "Meristematic Regrowth Control Use:" has peen
deleted. ·
10. Tab 9
Information (EPA Communications) pertaining to pending petitions I actions for uses
0
other than tobacco
We trust that the information provided here answers the questions that you raised and that the
updated; revised petition will progress smoothly towards approval.
Sincerely,
0
4
"ti
m
-I
-I
0
z
·. National Organic Program (NOP)
National Organic Standards Board (NOSB)
Fatty Alcohols
Petitioner:
Submitter/consultant:
Consultant: LVOG,lnc. ·
Lehigh Valley Organic Growers, Inc.
125 West 7th. Street
Wind Gap, PA. 18091
Thomas B. Harding, Jr.
[email protected]
610-863-6700
NOP Reference: 205.601 (k) (2) - Synthetic Substance Allowed for use in Organic Crop
Production.
ITEMB
1. Product's common Name: Cs-C 10 Fatty Alcohol (MASCOL 80)
Rather than filing separate petitions for octanol (Cs) and decanol (C 10) this single petition focuses
on the blend of C8C10 fatty alcohol (EPA Reg. No. 63896-1) since it is the product that is
specifically manufactured for use in the end products N-TAC and 0-TAC PLANT CONTACT
AGENT. The raw material for this alcohol is derived primarily from Palm Kernel Oil and Palm
Oil, not synthetic alcohol. The only other registered uses for individual fatty alcohols is the C 10
(decanol) - EPA Reg. No. 63896-2 and it is not included in this petition. There is no EPA
registered use for Cs (octanol) fatty alcohol.
1
3. Intended use: (
\
Sucker control on organic crops
a. Sucker control on organic crops: 4-6% solution of the formulated product applied
directed broadcast over the top of tobacco plants in the early button to early flower
stage of growth when suckers, axillary buds are succulent tender, utilizing 50 gallons
of spray solution per acre.
Mode of Action:
Upon contacting the axillary buds/suckers at the leaf axils, the solution containing the
active substance quickly dissolves the thin undeveloped cuticle or waxy area and
results in desiccation of the axillary bud/ sucker by rupturing cell walls and rapidly
evaporating liquids.
Chemical Structure:
HHHHHHHH
H C-C-C-C-C-C-C-C-OH (1-octanol)
HHHHHHHH
HHHHHHHHHH
H-C-C-C-C-C-C-C-C-C-C-OH ( 1-decanol)
HHHHHHHHHH
(.
~--
2
5. Source of the substance and description of manufacturing procedure:
The alcohols derived from natural sources are generally isolated from any of a variety of
natural occurring fats, oils and waxes of either animal or vegetable origin. The most
commonly used sources are coconut oil, palm kernel oil, palm oil, lard and tallow. The
alcohols are prepared by a transesterification of the fatty acids in the triglycerides found
in natural oils and fats followed by a catalytic hydrogenolysis of the resulting esters.
Purification and fraction of the resulting alcohols is similar to the synthetically produced
materials.
6. Previous reviews:
The information provided in Tab 2 (Industry Experts OMRI Reviews & Industry
Certifications) concerns the debate on whether the naturally derived fatty alcohol (Mascol
80) from the natural sources of palm oil, coconut oil, etc. are considered natural alcohols.
Apparently OMRI's classification would depend on the review the specific ingredients
and manufacturing processes to be sure about the classification as a synthetic or natural
alcohol. We believe that an alcohol derived from natural plant sources should be
classified as a natural alcohol as does Franco X. Milani, Assistant Professor, Extension
Food Manufacturing Specialist, University of Wisconsin and Dr. James K. Whitesell,
Professor of Organic and Materials Chemistry, University of California, San Diego.
• Various certifications
a. Certified Kosher
b. Compliance with RSPO (Roundtable on Sustainable Palm Oil) Supply Chain
Certification Systems
c. Certified as to meeting the requirements of GMP Codex Alimentarius -
Recommended International Code of Practice General Principles of Food Hygiene
d. Certification of the Mascol 80 supplier, P.T. Musim Mas has met the requirements of
ISO 14001: 2004, ISO 9001: 2008 and OHSAS 189001: 2007 for the manufacture of
Oleochemicals.
3
7. Information regarding EPA, FDA and State regulatory Authority registrations,
including registration numbers:
FDA Information:
Documentation that the Active Substance (fatty alcohol blend) and inert ingredients
(polysorbate 80) used in the formulated products, Fair 85, N-TAC and 0-TAC PLANT
CONTACT AGENT, are approved as food additives by the U.S. Food and Drug
Administration.
4
Product Labels:
See Attached
0-TAC PLANT CONTACT AGENT
N-TAC (Use as Plant Contact Agent)
5
PHYSICAL AND CHEMICAL PROPERTIES OF THE ACTIVE SUBSTANCE (FATTY
ALCOHOL BLEND)
54.5% decanol \
II A 2.5.1 830.7050 Alfol 810 The product in y MRID 47589901
UV Spectra basic methanol
Lot 1169975
shows an
absorbance
maximum at
204nm
6
PHYSICAL AND CHEMICAL PROPERTIES OF THE ACTIVE SUBSTANCE (FATTY
ALCOHOL BLEND)
7
PHYSICAL AND CHEMICAL PROPERTIES OF THE ACTIVE SUBSTANCE (FATTY
ALCOHOL BLEND)
(--
\
8
PHYSICAL AND CHEMICAL PROPERTIES OF THE ACTIVE SUBSTANCE
\
9
REFERENCES
IDENTITY OF THE ACTIVE SUBSTANCE:
10
a. Chemical interactions with other substances, especially substances usual in
\ organic production:
None known
There are no available studies on the environmental fate of the fatty alcohol blend/ aliphatic
alcohols. It is important to remember that active substance, fatty alcohol blend, is classified and
approved as food additives by the US food and Drug Administration. The following has been
reproduced from EPA's document "Registrations Eligibility Decision for Aliphatic Alcohols,
Case No. 4-004, March 2007, EPA 738-R-07-004.
Because environmental fate data are not available, physical and chemical properties for
the aliphatic alcohols were estimated by Quantitative Structure-Activity Relationships (QSAR)
using EPISuite v 3.21 (Estimation Programs Interface for Windows (EPIWIN)). The estimated
properties of 1-octanol, 1-decanol and 1-dodecanol differ somewhat, due to the different lengths
(i.e. number of carbons) in their straight, saturated carbon chains. As suggested by their
common names, 1-octanol has 8 carbons in its chain, 1-decanol has 10 carbons, and
1 -dodecanol has 12 carbons.
In spite of these small differences, the expected behavior of these aliphatic alcohols in the
environment is generally similar. The major route of dissipation in the field for these chemicals
is likely to be volatilization. The volatility half-lives for 1-octanol and 1-decanol were estimated
using the Dow Method described in the Handbook of Chemical Property Estimation Methods by
Lyman, Reehl and Rosenblatt. The half-lives for volatility from soil for 1-octanol and 1-decanol
were estimated to be 3.5 minutes and 1 minute, respectively. 1-dodecanol would likely volatilize
even more quickly, but the half-life was not estimated, since volatility from pheromone traps is
the known route of dissipation.
There is some uncertainty about the rate of volatility of 1-octanol and 1-decanol from
plant surfaces, since aliphatic alcohols are hydrophobic and, therefore, have affinity for the waxy
surfaces of plants. However, these volatility half-lives suggest that the aliphatic alcohols will not
be available long to expose non-target terrestrial animals, nor to be transported to surface water
bodies in runoff. Residues of 1-dodecanol are not expected on plants or in soil, since they are
dispersed in the air from pheromone traps, and then degraded by photolysis. The ecological risk
assessment concluded that except for terrestrial insects, which are the target for the pheromone
use of 1-dodecanol, "environmental exposures resulting from this use are likely negligible." The
risk assessment for this use was therefore qualitative.
11
Additional estimation of environmental fate parameters obtained from EPISuite provides
a basic set of data to perfonn a screening-level environmental risk assessment. The model
indicates that aliphatic alcohols have a moderate tendency to bind to soils. The portion of
applied chemical that binds to the soil, rather than volatilizing, will be subject to biodegradation,
with estimated half-lives forl-octanol and 1-decanol of 2.3 days. The portion of applied chemical
that does volatilize is estimated to degrade in the air by reaction with hydroxyl radicals with half-
lives of about 10 hours.
As mentioned above, dissipation via volatilization will greatly reduce the amount of
aliphatic alcohols reaching surface-water bodies, and aliphatic alcohols will volatilize from water
as well as soil. However, the fraction that does reach surface water will not be degraded by
hydrolysis. These alcohols have the potential to bioaccumulate in fish, but the rates of uptake,
metabolism, and depuration, as well as the nature of metabolites, are not known. However, the
magnitude of the bioconcentration factors (BCF) suggests a low potential to bioconcentrate.
EPISuite does not provide infonnation on the rates of formation/decline of product, the
nature and relative amounts of transfonnation products, and their distribution in soil/sediment-
water- air. Therefore, the specific nature and persistence of potential biotransfonnation products
(primary biodegradation) are not known. However, the ultimate biotransfonnation products of
the aliphatic alcohols are water and carbon dioxide.
The Agency uses a pesticide's use profile, exposure data, and toxicity information to ( .
determine risk estimates to non-target terrestrial and aquatic organisms. Estimated
environmental concentrations (BECs) are used to calculate risk quotients (RQs). EECs are based
on the maximum application rate(s) which would potentially yield the greatest exposure. An RQ
is derived by dividing the EEC by a single estimate of toxicity. The Agency then compares an
RQ to its Level of Concern (LOC) to determine if exposure to the aliphatic alcohols could
potentially pose a risk to non-target organisms (RQs that exceed the LOC indicate potential
risk). Table 5 outlines LOCs, and the Agency's corresponding risk presumptions.
Risk Presumption LOC Terrestrial Animals LOC AQuatic Animals LOC Plants
Acute Risk - there is a 0.5 0.5 1
potential for acute risk
Acute Endangered 0.1 0.05 1
Species - endangered
species may be adversely
affected
Chronic Risk - there is 1 1 NIA
potential for chronic risk.
c:
12
a. Exposure to Aquatic Organisms
Although GENEEC is not designed to consider volatility from soil directly, the Agency
used an indirect method to consider volatility with the GENEEC model and to refine the aquatic
exposure assessment. As described above, the volatility half-lives for the aliphatic alcohols were
estimated using the Dow Method described in the Handbook of Chemical Property Estimation
Methods (Lyman, et al., 1982). The half-lives for volatility from soil for 1-octanol and 1-decanol
were estimated to be 3.5 minutes and 1 minute, respectively. Such short volatility half-lives
mean that little pesticide will remain by the time a runoff event occurred, unless rainfall began
immediately after application.
To simulate this scenario using GENEEC, the Agency determined the amount of 1-octanol
or 1-decanol that would remain in the field 3 to 4 minutes after application at the maximum rates
allowed on the label. GENEEC was then run in the standard fashion, but with this "effective
/ application rate." Even though this was done using estimated volatility half-lives on the order of
\
a couple of minutes, the resulting EECs are still considered upper-bound.
GENEEC does not simulate a rainfall event until two days after application; if rainfall does not
occur until two days after actual application of 1-octanol or 1-decanol, there could be very little
product remaining to be subject to transport in runoff. For this reason, the simulations considered
only a single application, although aliphatic alcohols can be used more than once within a single
growing season.
Registrant-submitted data and open literature studies suggest that the aliphatic alcohols
are "slightly" to "moderately" toxic to freshwater fish. Although the data base is not complete
for all compounds in the aliphatic alcohol registration case, there are adequate data to assess the
acute risk to freshwater fish. Although there are no registrant-submitted acute toxicity data
available for estuarine/marine fish, data from the open literature provided the information to
assess the acute risks of aliphatic alcohols to these organisms. The relevant study from the open
literature indicates that 1-octanol is "slightly" toxic and 1 -decanol is "moderately" toxic to
estuarine/marine fish.
13
No chronic toxicity guideline studies exist for any of the aliphatic alcohols. However,
chronic data for freshwater fish from the open literature on 1-octanol provide an endpoint which
the Agency used to calculate RQs. Chronic toxicity data for aquatic invertebrates on the
aliphatic alcohols were also drawn from the open literature. The Agency used a chronic no
observed adverse effect concentration (NOAEC) ofl mg/L for reproductive effects for 1-octanol.
The Agency notes that chronic toxicity data on 1-decanol for aquatic invertebrates would reduce
the uncertainty posed by the lack of these data. A summary of all toxicity endpoints is presented
below in Table 6.
Table 6 - Toxicity Reference Values Used to Calculate RQs for Aliphatic Alcohols
Taxonomic Assessment 1-0ctanol 1-Decanol
Group Endpoint
Species/ Toxicity Species/Toxicity
Endpoint Endpoint
Survival Fathead Minnow Fathead minnow
Acute LC 50=12.2 mg/L Acute LC 50=2.3 mg/L
Freshwater Fish Reproduction, Growth Fathead minnow No data available
NOAEC=0.75 mg/L
Survival Water flea Water flea
Acute LC 50=4.16 mg/L Acute LC 50=6.5 mg/L
Freshwater Invertebrates Reproduction, Growth Water flea No data available
Chronic NOAEC=l mg/L
Survival Bleak Bleak
Acute LC 50= 15 mg/L Acute LC 50=7.2 mg/L
Estuarine/marine fish Reproduction, Growth No data available No data available
Survival Harpacticoid copepod Harpacticoid copepod
LCso=58 mg/L LC 50=4 mg/L
Estuarine/marine
Invertebrates Reproduction, Growth No data available No data available
Based on the refined surface water EECs and the available ecotoxicity data for 1-octanol
and 1 -decanol, RQs for aquatic animals do not exceed acute LOCs. In addition, although chronic
toxicity data are available for 1-octanol, but not 1-decanol, aliphatic alcohols do not appear to
pose a chronic risk to freshwater aquatic animals. No chronic toxicity data are available for
estuarine/marine fish and invertebrates. In spite of these data gaps, the Agency does not
anticipate chronic risk to estuarine marine fish and invertebrates. As described above, little
1-octanol or 1 -decanol would likely be available for transport in runoff if a significant rain event
did not occur within a few hours of application. Estimated RQs for 1-decanol and 1-octanol are
summarized in Tables 7 - 10 below. (. \
14
Table 7- Acute and Chronic RQs for Freshwater Fish
15
Aquatic plant toxicity data from open literature were only available for 1-octanol. Based
on these data, the acute RQs for aquatic plants do not exceed the Agency's acute and endangered
given that the NOAEC for 1-octanol is unknown, and no aquatic phytotoxicity data are available
for 1-decanol. The NOAEC is used to calculate an RQ to evaluate potential risk to endangered
species. Because the NOAEC was not established, the EC 10 for 1-octanol was used. Since the
LOC for endangered aquatic plants is 1.0, and the RQ derived using the EC10 is 0.05, the
NOAEC would have to be at least 20 times lower than the EC10 for the Agency to have an
endangered species concern for aquatic plants.
Based on the analysis of the volatility of the aliphatic alcohols, aquatic exposures
resulting from the labeled use of 1-decanol and 1-octanol are unlikely to reach concentrations
that exceed the Agency's LOC. As a result, the value of additional aquatic plant studies for the
aliphatic alcohols is low.
Birds
Available toxicity data indicate that the aliphatic alcohols are categorized as "practically
non-toxic" to birds on acute oral and dietary bases. Acute risks to birds were not quantified,
because no discreet median lethal doses or concentrations were established in the acute oral and
dietary studies. An acute dietary study from the open literature reported a dietary LC 50 for
bantam chickens of 201,000 ppm (I 00% 1-decanol). This level is more than 20 times greater
than the highest predicted dietary exposure level(~ 10,000 ppm). Therefore, the Agency
concludes that the aliphatic alcohols do not pose an acute risk to birds. No avian chronic toxicity
studies were available for any of the aliphatic alcohols and, therefore, the Agency cannot directly
assess the potential chronic risk to avian species. However, since 1) the aliphatic alcohols are not
acutely toxic to birds at doses many times higher than
expected exposure, 2) the volatility of the aliphatic alcohols makes chronic exposure unlikely,
with EECs dropping more than an order of magnitude within 30 minutes, 3) the aliphatic
alcohols assessed are listed as food additives and are "Generally Recognized as Safe" (GRAS)
by the U.S. Food and Drug Administration 1, and 4) a mammalian chronic toxicity study indicates
the aliphatic alcohols are not chronically toxic to mammals, the Agency does not expect a
chronic risk to birds, and will not require chronic avian toxicity studies at this time.
(
\_
16
Mammals
Acute oral mammalian toxicity data indicate that the aliphatic alcohols are "practically
non-toxic" to mammals on an acute oral basis. Four studies performed with laboratory rats did
not result in LC 5o endpoints with which RQs could be calculated. The Agency concludes that
aliphatic alcohols do not pose an acute dietary risk to mammals.
In the single chronic mammalian developmental toxicity study, which used a 1- decanol I
1-octanol blend, no chronic effects were observed in laboratory rats, even at the maximum tested
dose of 957 mg/kg bw/day. It is unknown ifthe predicted exposures approach
the level at which effects may occur since no LOAEC was identified in the chronic study.
However, the Agency does not anticipate chronic risk to mammals, considering the volatility of
the aliphatic alcohols, and the acceptance of these chemicals as food additives, as described
above.
Terrestrial Insects
Available toxicity data indicate that aliphatic alcohols are "practically non-toxic" to
honeybees (acute contact LD 50 > 25 µg/bee). However, given that aliphatic alcohols can be
used as Lepidopteran sex inhibitors, there is a potential for sublethal (e.g., reproductive) effects
on non-target Lepidopterans, such as butterflies. This potential effect cannot be quantified at this
time.
1
http://vm.cfsan.fda.gov/- dms/eafus.html
/
Terrestrial Plants
Tier-I terrestrial plant seedling emergence study data suggest a fatty alcohol blend (1-decanol
and 1-octanol) is not toxic to most plants at the maximum rate tested (18.03 lbs ai/A).
An EC 25 could not be established for tested species, although lesser effects were observed in
cucumbers, carrots and tomatoes. Therefore, the Agency did not calculate RQs based on
seedling emergence effects.
EC25 values and related no-effect levels were established for two (com and cucumber) of
10 crop plants tested in a submitted vegetative vigor study. The Agency used these endpoints in
the TerrPlant model to calculate RQs (Table 12). All were below the Agency's LOC of 1.
17
f. Endangered Species
Based upon the screening-level assessment conducted on aliphatic alcohols, the Agency
has not definitively identified exceedences of endangered species LOCs for direct effects to non-
target animals or plants. Acute RQs did not exceed endangered species LOCs for birds,
mammals, terrestrial plants, freshwater fish and invertebrates, or estuarine/marine fish and
invertebrates. Chronic data were not available for birds and estuarine/marine fish and
invertebrates. As described above, the Agency believes that the volatility and low toxicity in
available acute and chronic toxicity studies for mammals and freshwater animals suggest that
chronic risk to birds and estuarine/marine animals is unlikely. However, because the toxicity
data are not available, the Agency cannot completely preclude risk to listed birds and
estuarine/marine animals at this time. Similarly, since a no-effect level was not determined for
aquatic plants, the Agency cannot preclude direct effects on these organisms, although exposure
is expected to be negligible.
The Agency considers a potential for not only direct effects, but also adverse indirect
effects to listed species that rely on other affected organisms. Because direct effects to aquatic
plants cannot be precluded, indirect effects to listed aquatic species which rely on aquatic plants
can also not be dismissed. Similarly, indirect effects to terrestrial plants and animals cannot be
precluded because of potential reproductive effects of aliphatic alcohols to some terrestrial
insects.
Table 13 - Potential Listed Species Risks Associated with Direct or Indirect Effects Due to
Applications of Aliphatic Alcohols as Shoot inhibitors on Tobacco. (
\
Direct Effects
Listed Taxon Acute Chronic Indirect Effects to Endan2ered Species
Terrestrial and semi-aquatic plants- No NIA Possible
monocots
Terrestrial and semi-aquatic plants- No NIA Possible
dicots
Birds No NIA Possible
Terrestrial-phase amphibians No No Data Possible
Reptiles No No Data Possible
Mammals No No Data Possible
Aquatic non=vascular plants* Insufficient NIA NIA
data
Aquatic vascular plants Insufficient NIA NIA
data
Freshwater fish No No Possible
Aquatic-phase amphibians No No Possible
Freshwater crustaceans No No Possible
Mollusks No NIA Possible
Marine/ estuarine fish No No Data Possible
Marine/estuarine crustaceans No No Data Possible
•At the present time, no aquatic non-vascular plants are included In Federal listings of threatened and endangered species. The
taxonomic group is included here for the purposes of evaluating potential contributions to indirect effects to other taxa and as a
record of exceedances should future listings of non-vascular aquatic plants wanant additional evaluation of Federal actions.
18
Further analysis regarding the overlap of individual species with each use site is required
prior to determining the likelihood of potential impact to listed species. At the screening level,
this analysis is accomplished using the Location of Crops and Threatened and Endangered
Species (LOCATES) data base, which uses location information for listed species at the county
level and compares it to agricultural census data for crop production at the same county level of
resolution. The ecological risk assessment includes a complete listing of aquatic plants, birds,
reptiles, terrestrial-phase amphibians, mammals, and terrestrial invertebrates associated with the
States where the aliphatic alcohols are use as a plant growth regulator on tobacco.
SUPPLEMENTAL INFORMATION:
19
The conclusions reached as a result of this study/ literature review were as follows:
OPP Guideline Number 160-5, OPPTS (form 8570-4), OECD data point (II A 1.10), Chemical
Identity: Normal fatty alcohols are considered chemically "inert" and are precursors to fatty
acids. Their production and manufacture yields a relatively pure product mixture, depending
upon the "cut" desired. The C6-C 12 alcohols used in tobacco sucker control agents would be
expected to contain no unusual or high levels of impurities.
OPP Guideline Number 161-1, OPPTS (835.2120), OECD data point (II A 7 .5) Hydrolysis:
Hydrolysis is not a major pathway of degradation for C6-C 12 alcohols.
OPP Guideline Number 161-2, OPPTS (835.2240), OECD data point (II A 7.6)
Photodegradation in Water: Photolysis of C6-C 12 n-alcohols in water would not be expected to
occur.
OPP Guideline Number 161-3, OPPTS (835.2410), OECD data point (II A 7.1.3)
Photodegradation in Soil: Photolysis of C 6-C 12 n-alcohols in soil would not be expected to
occur.
OPP Guideline Number 162-1, OPPTS (835.4100), OECD data point (II A 7.1.1) Aerobic Soil
Metabolism: Aerobic soil metabolism is the major degradation pathway for C6-C 12 n-alcohols.
Breakdown or assimilation by microbial organisms is rapid and complete. Half-lives may be as
short as a matter of hours, and would not be expected to exceed 3 to 5 days.
OPP Guideline Number 162-3, OPPTS (835.4400), OECD data point (II A 7.8.2)Anaerobic
Aquatic Metabolism: Anaerobic aquatic metabolism is similar to other microbial metabolism
pathways for C6-C12 n-alcohols. End products may differ due to individual organism output, but
products will be natural components of the aquatic system. Breakdown or assimilation by
microbial organisms is rapid and complete. Half-lives may be as short as a matter of hours and
would not be expected to exceed on day.
OPP Guideline number 163-1, OPPTS (835.1230, 835.1240); OECD data point (II A7.4.1, II A
7.4.3) Leaching/adsorption/desorption: C6-C 12 fatty alcohols strongly adsorb to soil and would
not be expected to move through the soil column. Desorption is expected to be minimal.
OPP Guideline Number 164-1, OPPTS (835.6100), OECD data point(II A 7.3.1) Terrestrial
Field Dissipation: Dissipation of C6-C 12 fatty alcohols under field rates and conditions is rapid
and complete. Half-lives as short as a matter of hours could be possible. Half-lives would not be
expected to exceed 3 to 5 days.
OPP Guideline number 165-4, OPPTS (835.1730), OECD data point (II A 8.2.6.1)
Bioaccumulation in Fish: C6-C12 fatty alcohols will not bioaccumulate in fish.
20
REFERENCES
FATE AND BEHAVIOR IN THE ENVIRONMENT:
summary of Conclusions
The report is dated September 17, 1975. Test materi-
al was received on August 14, 1975. Specific dates of
testing are n__ot reported. The results of the acute
oral toxicity study conducted with Alfol 810 in mallard
ducks showed the LD~ to be in excess of 4640 mg Alfol
810 per kg body weignt.
21
Avain dietary Toxicity in Quail or Mallard Duck
Sullllllary of Conclusions
The test material was received on August 14, 1975. The
report is date~ September 17, 1975. The exact dates of
testing are not reported. The acute Le50 of Alfol 10
was determined to be in excess of 10,000 ppm in bob-
white quail.
~ummary of conclusions
The test material was received on August 14, 1975. The
report is dated_ September 17, 1975. The exact dates of
testing are not reported. The acute Le50 of Alfol 810
was determined to be in excess of 10,000 ppm in mallard
ducks.
Fish Toxicity
summary of conclusions (
The report is dated September, 1975. Specific dates of
testin~ are not reported. Acute 96 hour Lc50 values
are reported in parts per million for two species (with
95% confidence intervals) as follows:
22
Acute Toxicity to Aquatic invertebrates:
I
\
Table l Acute toxicity of Alfol 810 Alcohol· and Alfol 10 Alcohol to.
the water flea 8 (Daphnia maqna). These date are baed on
the results of bioassays conducted-at the Aquatic Toxicology
Labor.atory of E G & G, Bionomics, Wareham, Massachusetts.
,.!
No discernible
r...; effect level
LCSO (milligrams active ingredient/liter) at 48 hoUrs
compound 24-hour 48-hour (mq/l)
/
a fi H••rnHilY conducted at 22 :!:_ 1. o0 c, Daphnia < 24 hour old at initiation
b
95 i c•:>11fidence interval.
Effects on Bees:
1. Active Substance:
CONCLUSION
The honey bee 48 hour contact LOSO value for Fatty Alcohol Blend; Lot
#CSI-91FA01-27 was determined to be greater than 25 pg/bee, the highest-,
dose tested. Based upon the LOSO value, Fatty Alcohol Blend; lot fCSI-
91FA01-27 was classified as relatively non-toxfc according to the tox1c1ty
categories of Atkin (6). The no observed effect dose was 6.3 pg/bee,
based on possible treatment related 11ortality and signs of toxicity at
doses ~ 12.S pg/bee.
23
REFERENCES
ECOTOXICOLOGICAL STUDIES:
Author(s) EPA Year Title Data Owner MRID#
Guideline Protection
Number Claimed
McGaughey, 850.2100 1990 Fatty Alcohol Task Force y Fatty 94313004
B. Phase 3 Summary of MRID Alcohol Task
00046991. Acute Oral LD50 - Force
Mallard Duck: Alfol 810
Alcohol: VISDUCK.2:
Prepared by Truslow Farms,
Inc. 11 p.
McGaughey, 850.2200 1990 Fatty Alcohol Task Force y Fatty 94313006
B. Phase 3 Summary of MRID Alcohol Task
00058024 Eight Day Dietary Force
LC 50 Bobwhite Quail: Alfol
810 Alcohol: VISQUL2:
Prepared by Truslow Farms,
Inc. 10 p.
McGaughey, 850.2200 1990 Fatty Alcohol Task Force y Fatty 94313010
B. Phase 3 Summary of MRID Alcohol Task
00058025. Eight Day Dietary Force
LCso - Mallard Duck: Alfol
810 Alcohol: VISLCDK2:
Prepared by
Truslow Farms, Inc. 10 p.
McGaughey, 850.1075 1990 Fatty Alcohol Task Force y Fatty 94313012
B. Phase 3 Summary of MRID Alcohol Task
00122381. Acute Toxicity of Force
Two Conoco Compounds to
Bluegill and Rainbow Trout:
VISFISH. Prepared by
Bionomics, Inc. 15 p.
LeBlanc G. 850.1010 1976 Study of the Effects of Fatty y Fatty 42847201
A. Alcohols on Acute LC50 Alcohol Task
Freshwater Invertebrates Force
(Daphnia); Report Number:
CSI-FATF-TX-9301; EG &
Bionomics Aquatic Toxicity
Laboratory 13 p.
Hoxter, J. A. 850.3020 1992 Fatty Alcohol Blend; Lot # y Fatty 42495102
and Jaber, M. CSI-91FA01-27: An Acute Alcohol Task
Contact Toxicity Study with Force
the Honey Bee; Project
Number. 346-10 IA: Wildlife
International Ltd. 44 p.
24
d. Effects on human health
\
1. Active Substance:
25
Summary of Mammalian Toxicity (CONT):
26
REFERENCES
(
\
TOXICOLOGICAL AND METABOLISM STUDIES
27
TOXICOLOGICAL AND METABOLISM STUDIES
28
TOXICOLOGICAL AND METABOLISM STUDIES
29
TOXICOLOGICAL AND METABOLISM STUDIES
N-TAC:
30
References:
I
\
Author EPA YEAR TITLE OWNER MRID#
GUIDELINE
NUMBER
Lowe, Carolyn 870.1100 2013 Acute Oral Fair Products, Inc. 49218303
Lowe, Carolyn 870.1200 2013 Acute Dermal Fair Products, Inc. 49218304
Lowe, Carolyn 8870.1300 2013 Acute inhalation Fair Products, Inc. 49218305
Lowe, Carolyn 870.2400 2013 Primary Eye Fair Products, Inc. 49218306
Irritation
Lowe, Carolyn 870.2500 2013 Primary skin Fair Products, Inc. 49218307
Irritation
Lowe, Carolyn 870.2600 2013 Dermal Sensitization Fair Products, Inc. 49218308
1. N-TAC: Acute Oral Toxicity Up and Down Procedure in Rats - Limit Test; Product
Safety Labs, Laboratory Study Number 36692; August 20, 2013; 14 pp.
2. N-TAC: Acute Dermal Toxicity Study in Rats- Limit Test; Product Safety Labs;
Laboratory Study Number 36693, August 20, 2013; 14pp.
3. N-TAC: Acute Inhalation Toxicity Study in Rats- Limit Test; Product Safety Labs;
Laboratory Study Number 36694; August 20, 2013; 21pp.
4. N-TAC: Primary Eye Irritation Study in Rabbit; Product Safety Labs; Laboratory Study
Number 36695, August 20, 2013; 17pp.
5. N-TAC: Primary Skin Irritation Study in Rabbit; Product Safety Labs; Laboratory Study
Number 36696; August 21, 2013; 14 pp.
6. N-TAC: Local Lymph Node Assay (LLNA) in Mice; Product Safety Labs; Laboratory
Study number 36697; August 20, 2013; 24pp.
'
'
31
e. Effects on soil organisms, crops, or livestock:
Effects on Terrestrial Vascular Plants (corn, onion, sorghum, wheat, carrot, cucumber, lettuce,
radish, soybean and tomato).
There were no phytotoxic abnormalties observed in any of the species from any of the
treatments. Overall, emergence was excellent, however, onions and carrots were much slower
emerging than the other species (non-treated controls included) . This resulted in no emergence
data collected at 7 days after
treatment for these species . This effect was not treatment related. There was no detrimental
effects from the fatty alcohol on seedling emergence or total fresh weight. Height of tomatoes
and radishes, at 21 DAT, was reduced in the fatty alcohol treatment by 11 and 15%,
respectively.
CONCLUSIONS
These data indicate that the fatty alcohol blend rate necessary to cause economically adverse
effects on these species is greater than the maximum labeled use rate. These data coupled with
the fact that the fatty alcohol blend is commercially applied to tobacco in a manner
which significantly reduces the likelihood of off- target movement indicates that this product
poses little threat (to non-target plant species. These data indicate that a more elaborate multiple
rate study (Tier 2) is not necessary to assess the potential impact of continued use of fatty alcohol
blends in commercial tobacco production.
32
\ References
33
10. Safety information including MDSD Form: (
\ .·
MASCOL80
Reference Tab 3
• Explain why the synthetic substance is necessary for the production of an organic
product?
The Fatty Alcohols being petitioned for use in organic crop productions, have beeen used
on farms for several decades with a positive and effective use history, has an excellent
record in the field, the environment, and human safety; with cultural benefits.
Proper crop use of these Fatty Alcohols reduces overall insect/pest pressures and
chemical use, farm labor exposure, farm labor cost and energy. Through carefully timed
;applications as required, it reduces crop hand topping and suckering, this activity benefits
the overall farm resources management, during the pre-and- post harvest peiords.
When used in conjuinction with traditional cultural practices, Fatty Alcohols, increases
crop yield, quality and marketability and has been shown to increase gross yield by
several hundreds pounds per acre, with a substandial income increase in crop value for
the farmer!
34
/ Additionally, clean sucker and foliage control enables machine harvesting, once again
increasing crop yield and quality, and providing major energy and labor savings.
Following are a few benefits realized by the farmer when using Fatty Alcohols:
• Increase crop quality and yields and gross income margins to the farmer .
In summary, the proper use of Fatty Alcohols on crops, increases crop quality, yield, and
value-added components, at substantial labor and energy reductions, which contribures
significantly to the farm gross/net income of the family farm unit!
Reference Tab 7
We are not declaring any Confidental Business Information (CBI), at this time!
REFERENCES:
Please Utilize the Reference List and References as indicated throughout this petition.
(
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35
1. List of Activities for which the substance will be Used:
a. Sucker control on organic crops: 4-6% solution of the formulated product applied
directed broadcast over the top of tobacco plants in the early button to early flower
stage of growth when suckers, axillary buds are succulent tender, utilizing 50 gallons
of spray solution per acre.
Mode of Action:
Upon contacting the axillary buds/suckers at the leaf axils, the solution containing the
active substance quickly dissolves the thin undeveloped cuticle or waxy area and
results in desiccation of the axillary bud/ sucker by rupturing cell walls and rapidly
evaporating liquids.
(
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Chemical Structure:
HHHHHHHH
H C-C-C-C-C-C-C-C-OH (1-octanol)
HHHHHHHH
HHHHHHHHHH
H-C-C-C-C-C-C-C-C-C-C-OH ( 1-decanol)
HHHHHHHHHH
Industry Experts
/
····--··········-----------------'---------
May 8, 2014
We consider the MASCOL 80, produced from sustainable PKO, to be from a Natural Process,
utilizing the D1;1vy Methodology; and therefore is not considered a synthetic alcohol, in our
industryI
Sincerely yours,
·z~lU~
. John Schnieder. . ...
_,_
Renee Allen r·
---------------------------ii-----------------------------------------
'=rom: [email protected] "·
Sent: Thursday, March 14, 2013 3:59 PM
To: Renee Allen
Subject: · RE: Request from Frank
Attachments: RE: {Contact OMRI] Classification of fatty alcohol (2.98 KB); RE: [Contact OMRIJ
Classification of fatty alcohol (4.28 KB)
Renee,
Yes this is funny and this was the same reply I got when I queried the US Agency for the classification
of our alcohol as not natural. If this is the case then only the wax ester route of Lurgi will be
classified as 'natural'. The Lurgi methyl ester route also employs methanol in the
transesterification. The short chain alcohol is never produced from wax ester route so this means
there are no natural short chain alcohols in the whole industry.
Please see the emails received on the definition of synthetic alcohol. By this definition, there will be no
natural alcohols at all unless the Lurgi wax ester route is modified so that the hydrogenation plant can
be run on short chain alcohol. We have tried this in Ecogreen but the He content will be too high to
meet the market requirement and it will be too costly to fractionate the C6-Cl0 alconoJ. More so, the ( .·
•ax ester route does not allow change in feedstock as too much downtime will be employed to flush the · · .·
-- -- - s·ystetri ·c,f-fhe-prevfous -materfuCtn-sliorf no. company-wili produce-short chain
alcot1~1 ·usingthe wax -. ----
ester route. Therefore, where will they source natural short chian alcohol.
Thanks,
John Schnieder
Office: 513-245-7061
Cell: 513-746-7663
Fax: 513-791-2767
Note: Purchase orders should be sent to the ICOF America customer service group at [email protected].
From: Renee Allen [mailto:[email protected]]
Sent: Wednesday, March 13, 2013 3: 16 PM
To: [email protected]
Subject: Request from Frank
Importance: High
Hey John,
Frank asked me to tell you that we need an absolute argument from your chemists indicating that the alcohol ls a non-
synthetic alcohol.
Thank you,
Renee' Allen
FAIR PRODUCTS, INC
www.fairproductsinc.com
(919) 467-1599
- ~-
Renee Allen
Hello,
Fatty acid alcohols are usually derived from vegetable oil via some sort of hydrolysis. Depending on the type of
hydrolysis (i.e. chemical vs steam/pressure) we would consider it synthetic. Further, the fatty acid alcohols are usually
fractionated in some way; we would want to see that process to make sure there were no synthetic reactions occurring
there as well.
In short, not all fatty acid alcohols would be considered synthetic, but some would. OMRI would have to review the
sp~cific ingredients and manufacturing processes to be sure.
Regards,
Lindsay Fernandez-Salvador
Program Director
Organic Materials Review Institute
P.O. Box 11558
Eugene OR 97440-3758
\ 1ffice {541)343-7600 x117
.'~ ·- · - ·t=ax (541)343J8911 · ·- · · ·
www.omri.org
CONFIDENTIALITY NOTICE
This email, including any attachment, may contain information that Is confidential for the use of the Intended recipient
only. Any review, reliance or distribution by others or forwarding without express permission is strictly prohibited. If you
are not the intended recipient, please contact the sender"and delete all copies. Information submitted to OMRI is
considered confidential in accordance with the OMRI _Policy and Standards Manual Section 1.6.
-Original Message-
From: Jean Schauerman
Sent: Monday, October 29, 2012 7:38 AM
To: Lindsay Fernandez-Salvador
Subject: FW: {Contact OMRI] Classification offatty alcohol
Jean Schauerman
Administrative Specialist
Organic Materials Review Institute
P.0. Box 11558
ugene OR 97440-3758
Office (541)343-7600 ext.100
Fax (541)343-8971
.. 1 ...
www.omri.org
CONFIDENTIALITY NOTICE
This email, including any attachment, may contain information that is cor:ifidentlal for the use of the intended recipie
only. Any review, reliance or distribution by others or forwarding without express permission is strictly prohibited. If yo ..
are not the intended recipient, please contact the sender and delete all copies. Information submitted to OMRI is
considered confidential in accordance with the OMRI Policy Manual and Standards Manual Section 1.6. .
--Original Message-
From: [email protected] [mailto:[email protected]] On Behalf Of
Sent: Monday, October 29, 2012 2:14 AM
To: [email protected]
Subject: [Contact OMRI] Classification of fatty alcohol
Please clarify why fatty alcohols derived fro,m vegetable oils are classified as synthetic.
(
'·
... 2 -
Renee Allen
Hello,
The vegetable oil that is hydrolyzed by steam would be nonsnythetic. However, the esterification step to produce
methyl esters would then render your particular substance as synthetic. This is because it is a synthetic reaction to
produce a third, unique chemical. Your product would need to be reviewed by the NOSB for addition to the National
List.
Regards,
Lindsay Fernandez-Salvador
Program Director
Organic Materials Review Institute
P.O. Box 11558
Eugene OR 97440-3758
Office (541)343-7600 x117
Fax (541)343-8971
www.omri.org
':ONFIDENTIAUTY NOTICE
This email, including any attachment, may contain information that Is confidential for the use of the intended recipient
only. Any review, reliance or distribution· by others or forwarding Without express permission is strictly prohibited. Jf you
are not the intended recipient, please contact the sender and delete all copies. Information submitted to OMRI is
considered confidential in accordance with the OMRI Policy and Standards Manual Section 1.6.
-Original Message-
From: [email protected] [mailto:[email protected]]
Sent: Tuesday, October 30, 2012 3:52 PM
To: Lindsay Fernandez-Salvador
Subject: Re: [Contact OMRI] Classification of fatty alcohol
our fatty alcohols are produced from methyl esters. The methyl esters are produced by esterification of fatty acids. The
fatty acids are produced by splitting the oil with steam. Are c:>urfatty alcohols classified synthetic?
Hello,
(
'.atty acid alcohols are usually derived from vegetable oil via some sort of hydrolysis. Depending on the type of
hydrolysis (i.e. chemical vs steam/pressure) we would consider it synthetic. Further, the fatty acid alcohols are usually
- ;3-
fractionated in some way; we would want to see that process to make sure there were no synthetic reactions occurring
there as well.
In short, not all fatty acid alcohols would be considered synthetic, but some would. OMRI would have to review the
specific ingredients and manufacturing processes to be sure.
Regards,
Lindsay Fernandez-Salvador
Program Director
Organic Materials Review Institute
P.O. Box 11558
Eugene OR 97440-3758
Office-(541)343-7600 x117
Fax (541)343-8971
www.omri.org
CONFIDENTIALITY NOTICE
This email, including any attachment, may contain information that is confidential for the use of the intended recipient
only. Any review, reliance or distribution by others or forwarding without express permission is strictly prohibited. Jfyou
are not the intended recipient, please contact the sender and delete all copies. Information submitted to OMRI is
considered confidential in accorda11ce with the OMRI Policy and Standards Manual Section 1.6.
-Original Message-
From: Jean Schauerman
Sent: Monday, October 29, 2012 7:38 AM
To: Lindsay Fernandez-Salvador
Subject: FW: [Contact OMRI] Glassification of fatty aleohol
Jean Schauerman
Administrative Specialist
Organic Materials Review Institute
P.O. Box 11558 .
Eugene OR 97440-3758
Office (541)343-7600 ext. 100
Fax (541)343-8971
www.omri.org
CONFIDENTIALITY NOTICE
This email, including any attachment, may contain information that is confidential for the use of the intended recipient
only. Any review, reliance or distribution by others or forwarding without express permission is strictly prohibited. If you
are not the intended recipient, please contact the sender and delete all copies. Information submitted to OMRI is
considered confidential in accordance with the OMRI Policy Manual and Standards Manual Section 1.6.
--Original Message--
From: [email protected] [mailto:[email protected]] On Behalf Of (
Sent: Monday, October 29, 2012 2:14 AM \_ . . ··
To: [email protected]
Subject: [Contact OMRI] Classification offatty alcohol
- If-
Leng Gador sent a message using the contact form at http:Uwww.omri.org/contact.
\
Please clarify why fatty alcohols derived fro,m vegetable oils are classified as synthetic.
/
I
\
(
I
AgriSystems lnternationa/Tll\ \_
Please find herein· and herewith attached our Rebuttal To The OMRI Decision for the Natural Alcohol used in
· 0-TAC Plant Contact Agent, being submitted on behalf of my clients Santa Fe N:atn.ral '.fobacco Company
(SFNTC) and Fair Products, IncJSouth Atlantic Services , Inc. , located in North Carolina.
AgriSystems International, are the Organic Program Consultants for these companies and the primary contact
for this OMRI Application for 0-TAC.
We are submitting our Rebuttal per your email letter dated August 3, 2012, whereas the OMRI Decision stated that
the Natural Alcohol used in the 0-TAC Product was· a proht'bited synthetic material and tberefore·the 0-TAC
Product.is not approved for or.genie crop productipn, cenifie..d un~the }{OJ>_?___ ... _ _ _ _ _ ______ .. _
Please find her~with (FedEx) our check for $250.00 to cover the O:MRI Rebuttal Fee, any questions, contact me.
• We are rebutting this decision based upon the information contained in the Independent Third Party Review
and other relevant documents, herewith attached; whereas, the (hydrogenation step) is actually il ReductJve
Environmental Process Step found in nature and therefore is a natural process step end not a synthetic
hydrogenation step!
. It is our desire to have the OMRI Decision ·reversed and therefore recognize and permit the Natural Fatty
Alcohol as naturally derived and not synthetic; and therefore approve the 0-TAC Product for use on NOP
organic crop production!
. Our formulation has not changed since our original product review submission to OMRI!
It hes been our goal ove.r the last forty (40) years to incorporate into our work and recognize - that one of the main
tenants of organic agriculture , the community and industiy is attempt to avoic:l wherever possible the use of
synthetic compounds not found in nature and utilize ali elements of a sustainable system.
However, a balance of using modem lmowledge and compounds found in nature is needed to prevent ex®ssive crop ·
loss and maintain a quality crop harvest. lt is recogniZed in the strictest sense, all agricuJtme disturbs the natural
ecosystem, our goal in organic farm production is to maintain reasonable yield$, ~emonstrate exceJJentr~ource
stewardship that truly builds a sustainable system . Therefore production tools, p.x:oduc~ using natural coippounds are
essential for the organic fllfI!ler today! ·
We therefore request your further review of all documents submitted to OMRI and thatyou recognize the 0-TAC
Product meets the Requirements of the National Organic Program (NOP).
Thank you very much for your consideration of our Rebuttal and I look forward to hearing from you soon.
Sincerely yours,
AgriSystems International
~~~~
Thomas B. Harding, Jr.
President
Organic Program Consultants SFNTC
Build~g Sustainable Partnerships With Nature Through Organic Food and ~~iculture
.
:' _,,
......
.. .. _...... ....
..- /
... . . 4'. . . . . . . . - - -
·'
..
Thomas Harding, Jr.
· Fair Products, Inc.
125 W. Seventh Street
Wind Gap. PA 18091
Subject: 01\.ffi.I Status Notification for 0-TAC Plant Contact Agent® (fai-3376)
Dear Thomas,
The OMRI Review Panel has reviewed 0-TAC Plant Contact Agent® (fai-3376) and deteimined that it is·
Prohibited for use in organic production because it does not comply with the OMRI Policy and Standards
Manual which is based on the requirements of the USDA~ational Organic.Program (NOP) Rule (7.CFRPart ·
205). . . . . . . . . .
Specifically, the Review Panel detennined that 0-TAC Plant Contact Agent® is prohibited because the
active-ingredient is a ,Synthetic ~ateriaJ which does not appear-on the National List a~ §2PS.601. As such it is not
allowed for use in organic production. · ·
.You can petition the NOP to have the prohibited substance considered for use in organic production. Fo~ (
information on the petition procedure, see the N9P website. You ·may also choose to refo~ulate your product ·
to remove·any:prohibited· substances,·and submit a new product application and-fee-to ~MRI for review at any .-
thn~.
Please he advised tl).at the OMRI Listed® seal and wording can not be used for this product Any · ·
unauthorized use of the OMRI Listed seal and name may result in legal action against tlie company that'violates
the OMRI ~eiil Use Policy. A list of prohibited products is periodically circulated ~o subscritiing certifiers.
'This letter serves as OMR.I's final re8ponse regarding the status ofthis product. Ifyou wish to rebut this
· decisio~. please refer to §5.2 of the OMRJ Policy and Standar~. Manual, and ensure that the rebutta1 is received
within 30 days of the date of this notice. Please be advised that, in accordance with our policies, a notice of.
reforniulation does not constitute a rebuttal. · ·
PI~e contact me with any questions.
Sincerely,
Andria Schulze .
Product Review Coordinator . .. . " · ··
(541)343-7600 xf12. . · · · .., · ·~· · · · ·· ·
[email protected] · · : :. : · .
·.
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: .•::;,.·:.;.. : •.&A•,•,,.,,/ ,·•.\,_4•;:"".?;•' ··,:.• ~·- ;: : i;-t.,.. "•'•• ,~, 0 1•,,:. ~ ~ :•,/.,, :, •: ..... ,\ i
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0
0
•.,
WISCONSIN
MADISON
Re: Independent third-party review of 0-TAC agent (AKA Mascol 80, fatty alcohol methyl esters)
This document outlines the production fatty alcohol methyl esters and the similarities with
natural processing found in microbiological fermentation. The rationale is to show the chemical
modifications, as outlined in the fatty alcc:>hol methyl esters process, prod~~e the same .
compoun·ds as found in fermentation processes. Fermentation Is considered by many agencies.
to be a natural process. Benefits of the fatty alcohol methyl esters process provide for more ·
specific chemical- specie, better yields, and with substantially less collateral waste as compared
to fermentation. · ·
_l_J)_tl]e_ s~rJ9:~g s_~n~e, ~!"IY.f~.en}_tc~J. ".!IC?dJf!c'!~~o_!l_~QUI~ ~e- c~ry~i_(j_er_e~ ~nthetlc. -Even something
as simple as leaving naturally occurring and extracted compounds exi:>osecf tci"air "co.ul~f° produ~e
oxides that would potentially change the function of the.material. However, in this case; the
- reductjve environment is more similar.to processes found In nature than true·s'Jnthetlc a
hydrogenatio!l. One example Is the instan·ce of natural acidification through fermentation, for
example, the production of an organic acid when another organic substrate Is metabolized.
These are chemical changes, yet, it Is widely accepted t~at it is also a natural process. This
results in one of the most simplest chemical modification reactions: the addition of ionic
hydrogen (H+) to the organic acid (COO-) to produce the protonated form of the acid (COOH).
Also, once these acids are produced, they are free to react with alcohols to form est~rs, thus .
producing many of the "fruity" favors we see with fermentation (wine, cheese, beer, etc).
Another.well-known product of fermentation is ethyl alcohol, as well as many other alcohols.
Levels of ethanol produced by yeast can g~t as high as 20% as _seen in some biofuel applications.
Alcohol production in fermentation syste_ms is used to shuttle and store electrons to extend as
much as possible the oxidation requirements of the organism's metabolism.
The fatty alcohol methyl esters process outlined prodyce compounds that are found in nature
and are also produced in large amounts within a fermentation process. However, fermentation
may have low yields and thus the fatty alcohol methyl esters process employed uses modern
chemistry to produce something that could be created by natural processes, but in a way that Is
more economical and potentially less impactful to tbe environment. It Is also interesting to note
in fermentation systems the lack of report relative to reduction of unsaturated double bonds on
/
I the fatty acids, which Is in contrast to·well known and well accepted synthetic position In the
\
hydrogenation proc~ss used with margarine manufacture.
'
\
THE. UNIVERSITY
N_SIN-
WISCO___
MADISON
There can be co·mparison of a fermentation process versus the fatty alcohol methyt·esters
process. Fermentation could be set up to produce free fatty acids from the plant-sourced
triglycerides. Also, fermentation could also lower the oxygen content su~h to produce a very low
oxidation-reduction potential, that is, favoring the reduction of oxygen containing compounds.
This would promote the reduction of acid to th~ alcohol. Also, fermentation could produce
methanol. The .production of esters from acids ·and alc;ohols Is very common in fermentation as
well. The outlined fatty alcohol methyl esters process does not use fermentation, so the use of
hydrogen provides for a reduced· oxygen-limited environment. In blogas reactors (a specific type
of ferm~ntatlon), hydrogen Is produced as weil. ·
Fermentation systems have the benefit of bacterlafenzymes that catalyze reactions·. The benefit
or° using enzymes is that specific chemkal motlifications can be done at biological appropriate ·
temperatures. The used of a catalyst in the fatty alcohol methyl esters process promotes the
reduction of the acids, but does not get added or consumed into the chemical reaction. Just like
fermentation uses moderate tern peratures, the use of the catalyst In the fatty alcohol methyl
est~rs process also allows lower temperatures to control better compounds produced. There Is
~lso on!y about 1 atmosphere of pressure used, just enollgh to help the efficiency, so again, mild
corydltions are employed when compared to other lndust~ies.
-- -···--- . -"·------- -·---.--·--- ------·.··· ------·
In conclusion, it is my opinion after reviewing the Masco! BO/fatty alcohol methyl esterification
and reduction process flow, that this Is more similar to a natural alcohol {green.chemistry)
process than ·a truly synthetic process.
Franco X. Milani
Assistant Professor, Extension Food Manufacturing Specialist
. !
c
Department of Pood Science
Babeock Hall University of Wisconsin-Madison 1605 Linden Drive Madison, Wisconsin 5370&-:1519
608/262-3046 Fax: 608/262-6872 http://www.wisc.edu/foodsci/
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Certifications
PT. MUSIM MAS
Head Office: JI. K..L. Yos Sudatso Km. 7,8 Faclory: JL Oieo, ICnwwn Jndustri Medan II
~njung Muliil -Mcda'll 20241 Sacntis - Pcrc\ll Sei 1\w:I, Ot:li SCidang
Sumatera Utara - Indonesia Medan 2037 J -Indoncaia
Tel: (62-61) 6615511 - 6619866 Tel; (62-6116871123
Fax: (62-6Ji 6613060. {;617386 Fax: (62-61} 6871152-'871153
Email: oleo@mµsirnmas.eom
Based on our knowledge of the production methods and product formulation, fatty alcohol
manufactured by PT. Musim Mas is free from GMO.
(
RSPO member number: 201411000000
. .
* Contact details of management representative responsible for overseeing the certification process
Signature of certifier:
On behalf of the Managing Director.
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Control Union Cenificatlons
"°*"'"OfttMl'OI UnlonWDltd Cilllup
Page 1of2
.RSPO
Roundlable on Sustainable Palm OJI
I,
Annex 1 to Certificate - RSPO SCCS
Certificate infonnation
Pwr;hase of certined Crude Palm OJ/ and Crude Palm Kernel Oii, Renne, Process, Fractionate and
Sales of RSPO Certified palm o/I (CPO) and Palm ~eme/ o/I (CPKO) through Identity Preserved, ·!
Segregation and Mass Balance supply chain model and processing into certified CPOL, CPST, \_
CPKOL, CPKST, .8.BDPO, RBDOL, Double Fractionate Oleln, .Palm Mid_ Fractionate, RBDSI, Palm Mid
Stearln, Double Fractionate Stearln, PFAD, RBDPKO and PKFAD, RBDPKOL, RBDPKST, Glycerlne
and Fatty Acids, Soap noodles, Finished Soap Bars, Amides, Esters, Fatty Alcohols and Methyl
Esters.
This certificate Including the annex remains the prop~rty of Control Union Certifications and can be
withdrawn In case of terminations as. mentioned In the licensee c:Ontract, or In case changes or
deviations of the above mentioned data ocrur. The licensee is obliged to Inform CUC Immediately of
any changes In the above mentioned data. Only an original and signed certificate Is valid.
Authenticated by:
Date: 04/12/2012
Certificate no: cs1sss1cu-RSPO sccs-01.2012
Signature of certifier:
On behalf of the Managing Director.
//
Central Union Certifications
M«dltl ofCtMl'JI Ul'doftWutd GNIUP
Page 2 of2
RSPO
Rcuncllable on sustainable Pam OR
~ ~OSHER CERTIFIOATif KCI 3281991 - l
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®KOSHER
f£~!~,~JJQN P.T. MUSIM MAS (OLEOCHEMICAL DNISION)
28 Adar I, 5n4
February 28, 2014
391 li Avenue, Brooklyn, New York 11213 U.S.A.• Tel: 718 756-7500 Fax: n&-756·7503 • E-Mail: [email protected]
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Jalan- or~;~~$'.fl'idUstrfM~il~n IJ
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CERTIFICATE OF ACCREDITATION
LP-668-IDN
Date cl issue : 23 November 2012 Date of expiry : 22 November 2016
Granted to
ANALYTICAL LABORATORY OF OLEOCHEMICALS AND SPECIALTY FATS
- PT. MUSIM MAS
. 'cit- -. -- - - ~ - - - - - - - - - - - -.
JI. Oleo Kawasan Industri Medan II Saentls, Percut, Sei Tuan Deli Serdang, Medan 20371
Which has shown Its competence as
TEmNG LABORATORY
by Implementing consistently
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CHAIRMAN
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PTMUSIM MAS
KIM I: JL. Pulau Palu, Kawasan lndustrj Medan 1
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: :... .•·:.: has been assessed and ce1111ied as meeting Ille requlremen1$ of
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This certificate is valid from 28 May 2012 until 27 May 2015 and remains
varJd subject to satisfactoty su1Ve1llance auarts.
Re certification audit due before 15 March 2015
Jss'ue 1. certified since 28 May 2012
. . . _ . This is a mufti.,site certification.
Addftlonal Site details are listed on the subsequent M)e.
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UICAS
MANAGEMENT
SYSTEMS
SGS Unled K11¥1doll! ltd Systems & SeNices C8ltiliCaliOn
ROSSlllGlll Business Palk Elesmere Port Chashia CH65 3eN U)( 005
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ISO 14001:2004.
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KIM II: JL OJeo. Kawa.san-lndostrl Medan J~ SE!entis- -.. - - - -· - - - - - - - - - - - - - - - - . ~
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INDONESIA
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... ,, Certificate MY12/00932
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PT MUSIM MAS
KIM 1: JL. Pulau Palu, Kawasan Jnclustri Medan 1
Mabar, Medan 20252, Sumatera Utara
INDONESIA
has been assessed and cenllled as meeting the l'Bqlliiemenls of
~,,f ·.~!;· thir~!·!~l··t·{ This certificate is valid from 28 May2012 unb127 May 2015 and remains
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1 ·;:,'ji'·'~·,H~·.w Re certiffcation audit due be1bre 15 Maid12015
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This Is a muJtl..site ceJ6fication
Addl1iOnal $ite details are iisted on the $\lbsequent page
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Certificate MY12/00932, continued
PT MUSIM MAS
OHSAS 18001:2007
IS$Ue 1
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UNITED STATES ENVIRONMENTAL PROTECTION AGENCY
WASHINGTON, D.C. 20460
OFFICE OF
PREVENTION, PESTICIDES, AND
TOXIC SUBSTANCES
MEMORANPUM
DP Barcode: 325712
PC Codes: 079029, 079038, 079059
AND
AND
Page 1of13
1. Executive Summary
This document represents the human health risk assessment chapter of the Reregistration
Eligibility Decision (RED) document for the aliphatic alcohols, which include N-decanol,
Cx-Cxx alcohols, and fatty alcohols. Aliphatic alcohols are contact sucker control agents
used primarily on tobacco. There are no tolerances or tolerance exemptions established
for residues of aliphatic alcohols on food.
It should also be noted that the one active product (EPA Reg. No. 53263-29) for the fatty
alcohols has recently been voluntarily canceled (Anastasiou Memo, 6/7/06). Therefore,
there are no supported products for the active ingredient use of the fatty alcohols. Based
on the supported tobacco use, there are no residential uses for the aliphatic alcohols. In
addition, the pesticidal uses of the aliphatic alcohols do not involve use on food and,
therefore, are not subject to the Food Quality Protection Act (1996).
The available acute toxicity studies indicate the aliphatic alcohols are of low oral and
dermal toxicity. Acute inhalation studies with the rat resulted in LDso estimates above
the limit concentration of 2 mg/L. Eye irritation studies, however, resulted in severe and
sometimes non-reversible eye irritation. Dermal irritation studies revealed slight to
moderate irritation in rabbits. The aliphatic alcohols generally did not produce
sensitization in tests with guinea pigs.
A 90-day dermal rat study (fatty alcohol blend) resulted in irritation at lower
concentrations and before the development of any marginal systemic effects. Slight
changes in hematology, clinical chemistry, and organ weights were noted at the limit
dose of I 000 mg/kg/day. Severe irritation including fissuring of the skin occurred in
40% of the animals at 100 mg/kg/day and in 80% of the animals at the limit dose.
Available developmental toxicity studies (rat) via the inhalation ( 1-decanol) and oral
(fatty alcohol blend) routes of exposure resulted in no adverse effects when examined at
the maximum attainable vapor concentration ( 100 mg/m3) and oral limit dose ( 1000
mg/kg/day) based on fetal and maternal parameters. Genotoxicity and mutagenicity
studies available were negative and long-term rodent studies to infonn the carcinogenic
potential of the aliphatic alcohols are not available. However, as a class, the straight
chain aliphatic alcohols are generally not carcinogenic. Neurotoxicity information is
currently not available, however, there were no clinical signs in any of the acute,
subchronic, or developmental toxicity studies to suggest the aliphatic alcohols elicit a
neurotoxic effect CUrrently there is insufficient hazard concern to warrant a dose-
response evaluation or endpoint selection for quantitative risk estimates. Therefore, no
acute or chronic endpoints have been identified.
An exposure assessment considers the different pathways (food, water, occupational, and
residential) through which exposure to the aliphatic alcohols may occur. Oral exposure
through food is not expected since the aliphatic alcohols have no food uses and there are
no residential uses. Drinking water is not of concern due to: a) the high vapor pressure
and likely volatilization in air; b) atmospheric degradation by reaction with
photochemically produced hydroxyl radicals; c) lack of hazard for the oral route of
Page 2of13
/
I
\
exposure; and d) lack of systemic endpoints based on the available studies. Acute and
chronic dietary endpoints have not been selected. Therefore, based on the low hazard
concern, lack of food uses, along with no quantitative toxicological endpoints, a dietary
(food and water) risk assessment is not required.
Since a quantitative dermal endpoint was not identified, no quantitative post application
dermal risk was assessed. For uses within the scope of the Worker Protection Standard
for Agricultural Pesticides (40 CFR 170), a restricted entry interval (REI) must be
established. The REI should be based on the category assigned to the acute dermal
toxicity, skin irritation potential, and eye irritation potential of the active ingredient. The
appropriate REI is 48 hours if any of the three categories are classified as toxicity
category one.
Based on the lack of food and residential uses and low hazard via the oral, dermal, and
inhalation routes of exposure, quantitative dietary (food and water) and
occupational/residential exposure assessments have not been conducted.
( Additionally, the aliphatic alcohols are 'non-food use' chemicals and are not subject to
'.
the amendments to the Federal Food, Drug, and Cosmetic Act (FFDCA) promulgated
:under the Food Quality Protection Act (FQPA) of 1996, and an aggregate risk
assessment is not required.
2. Introduction
This risk assessment evaluates the aliphatic alcohols that are comprised of decanol,
alcohols Cx-Cxx, and fatty alcohols. Because of the low hazard concern of the aliphatic
alcohols, no toxicological endpoints have been selected for dietary or exposure risk
assessment purposes.
b. Ingredient Profile
The review of the product chemistry for the aliphatic alcohols was .not based on a single
chemical or pc code but rather based on the collective nature of tlie aliphatic alcohols.
Page 3of13
i. Structure and Nomenclature
Chemical structure
n-Decyl Alcohol
~'11
Common name Simple Aliphatic Alcohol: Ethanol 1-Decanol
Molecular formula WHsOH CH3(CH2)~H
Molecular weight 46.068 glmol 15829g/mol
IUPAC name (denotation) lnChl=1/C2H60/c1-2-3/h3H,2H2, 1H3 Not Reported
CASname Ethyl Alcohol n-Oecyl Alcohol
CASnumber 64-17-5 112-30-1
PCCode 001501 079038
1.59 4.5
"-- - -
Vapor Density at 20 degrees Celsius
ChemFlnder . MSDS
Fully miscible; >=10g/100 ml at23 °c 37 mg/L ; Insoluble; poor
Water solubility
Riddick, JA et al. (1996); ChemFlnder Barton, AFM (1984)
Organic solids of low molecular weight are
usually soluble In ethanol. -Among g
compounds, many mono-valent salts are
at least somewhat soluble In ethanol, with
sans of large, po!arizable Ions being more
soluble than salts of smaller ions. -
Solvent solubility at Most salts of polyvalent Ions are
practically insoluble In ethanol. Not reported
20 degrees Celsius
1) Va!fa, et al., Appl. Biochem.
Biotechno/., 1, 51, 1982. 2) J. M. Lee and
J. Woodward, Biotech. Bloeng., 25, 2441,
1983. 3) Encyclope<fia
40mmHg at 19°C
44 mmHg at 20°c 0.00851 mmHg at 25°C
Vapor pressure 59.3 mmHg at 25°C
Daubert, TE & Danner, RP (1985);
MSDS Daubert, TE & Danner, RP (1989)
15.9 (H• from OH group} Not reported
Page 4of13
Table 2. Physicochemical Properties Aliphatic Alcohols
Simple Aliphatic Alcohol Aliphatic Alcohol : 1-0econol
Parameter
Value/Reference Value/Reference
Dissociation constant, pK. Hansch, c et al. (1995)
Log Ko.. Log P = -0.14 Log Kort Log p = 3.79
Octanollwater partition coefficient
Hansch, c et al. (1995) Hansch, c et al. {1995)
UV/visible absorption spectrum Data Gap DataGap
Refer to htn>:llwww.epa.gov/athens/research/regsupport!pmperties.html for further details relating to
physical and chemical chemistry
All three chemicals that comprise the reregistration case for the aliphatic alcohols serve
as plant regulators. N-Decanol, alcohols (Cx-Cxx), and fatty alcohols are formulated as
liquids and are applied via the following methods: groundboom sprayer, backpack
sprayer, handgun sprayer, high pressure handwands and low pressure bandwands.
d. Tolerances
As the aliphatic alcohols are not registered for use on food crops, there are no tolerances
established for residues on food. Similarly, there are currently no tolerance exemptions
for the aliphatic alcohols.
The available toxicity database for the aliphatic alcohols consists of acute toxicity,
irritation, and sensitization studies. In addition, there are developmental rat (oral and
inhalation) toxicity studies and a 90-day rat (dermal) study. Mutagenicity studies
available include the Ames, micronucleus, and gene mutation assays. Sources from the
published literature are also included in this hazard assessment. The combination of the
published literature and submitted toxicity studies are sufficient to assess the pesticidal
nonfood uses of the aliphatic alcohols. Based on the low hazard concern via the oral,
dermal, and inhalation routes of exposure, a qualitative hazard assessment is appropriate
for the aliphatic alcohols.
1-Decanol has been found as a natural component in apples and oranges and has been
reported in essential oils of ambrette seeds, almond flowers, citrus oils and fermented
beverages (as cited in HSDB, 2005). 1-Decanol is also a permitted food additive for
direct addition to food for human consumption as a synthetic flavoring substance and
adjuvant in accordance with the following FDA conditions: 1) the quantity added to food
does not exceed the amount reasonably required to accomplish its intended physical,
nutritive, or other technical effect in food, and 2) when intended for use in or on food it is
of appropriate food grade and is prepared and handled as a food ingredient (21 CFR
(
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Page 5of13
172.515). There is currently no known mode of action for the aliphatic alcohols. There
are currently no guideline metabolism studies in rats available for the aliphatic alcohols.
The acute toxicity studies available for all three of the aliphatic alcohols (PC Codes
079038, 079029, 079059) are listed in Table Al. The available acute toxicity studies
indicate the aliphatic alcohols are oflow oral and dermal toxicity (Toxicity Categories ill
and IV). Acute inhalation studies with the rat resulted in LDso estimates above the limit
concentration of 2 mg/L. However, eye irritation studies resulted in severe and
sometimes non-reversible eye irritation (Toxicity Category I, II, and III). Dermal
irritation studies revealed slight to moderate irritation in rabbits (Toxicity Category III
and IV). The aliphatic alcohols generally did not produce sensitization in tests with
guinea pigs.
Oral subchronic toxicity studies are not available for the aliphatic alcohols. However, a
90-day dermal toxicity study in the rat is available (MRID 43701201). Results of the
dermal exposure to a fatty alcohol blend (56. 7% decanol, 42.7% octanol) at 0, 100, 300,
or 1000 mg/kg for 5 days/week for 13 weeks included erythema, edema, desquamation,
eschar formation and exfoliation of all treated animals. The irritation occurred early
(within two weeks of the application process) with irritation apparent in a dose-response
fashion. Fissuring of the skin occurred in 40% of animals at 100 mg/kg/day while in
80% of animals at the limit dose of I 000 mg/kg/day'. Decreased body weight was also
observed at the limit dose (-19% M, -13% F). Slight changes in hematological
parameters, clinical chemistry, and organ weight changes were apparent at the limit dose.
No other gross or histopathological organ pathology was associated with the skin
application of the fatty alcohol blend. The dermal irritation NOAEL was not established
with an irritation WAEL of 100 mg/kg based on severe initation. The systemic NOAEL
was 300 mg/kg/day with systemic WAEL of 1000 mg/kg/day, based on hematological,
clinical chemistry, and organ weight changes.
Developmental toxicity studies via the inhalation (1-decanol) and oral (fatty alcohol
blend) routes of exposure resulted in no adverse effects based on fetal and maternal
parameters. A developmental inhalation study exposed Sprague-Dawley rats (15) to 15
3
ppm (100 mg/m ) 1-decanol for 7 hours per day on GD 1-19 (Nelson et al., l 990a;
Nelson et al., 1990b). The concentration of 1-decanol selected was based on the highest
concentration that could be generated as a vapor at an average daily chamber temperature
of70-80°F. No treatment-related effects were observed in pregnant females or fetuses
including frequency of resorptions, fetal weights, or skeletal/visceral malformations. An
oral developmental study exposed 25 female Sprague-Dawley rats/dose at 0, 125, 375, or
1000 mg/kg/day to a fatty alcohol blend (55% decanol; 40.7% octanol) on GD 6-16
(MRID 42609301). The maternal NOAEL was 375 mg/kg/day and LOAEL was 1000
mg/kg/day (limit dose), based on increased incidence of salivation (67%). No adverse
effects were observed in the offspring. The developmental NOAEL was 1000 mg/kg/day
(HDT) with no WAEL being established.
Genotoxicity and mutagenicity studies available were negative for reverse gene mutations
in Salmonella typhimurium, not mutagenic in 2 independent assays with/without
Page 6of13
/
activation at levels ranging from 9.4 µg/ml to 37.5 µg/ml, and negative for micronucleus
induction in bone marrow cells of male and female CD-1 mice harvested 24 or 48 hrs
post-administration of3 daily doses of 500, 1000, or 2000 mg/kg/day. There is currently
no long-term rodent information regarding the carcinogenic potential for the aliphatic
alcohols.
4. Endpoint Selection
Based on the available data, there is no evidence to suggest that the aliphatic alcohols
cause increased susceptibility in infants and children. Furthermore, based on the low
hazard concern from the available studies, no endpoints of toxicological concern have
been identified for risk assessment purposes.
5. Incident Report
Although a summary of the incident data for the aliphatic alcohols is currently not
available for inclusion in this assessment, it should be noted that the aliphatic alcohols are
scheduled to be reviewed. The Agency will consider the results of the incident review
( once the evaluation is available.
\
6. Exposure Assessment
An exposure assessment considers the different pathways (food, water, occupational, and
residential) through which exposure to the aliphatic alcohols may occur. Drinking water
is not of concern due to: a) the high vapor pressure and likely volatilization in air; b)
atmospheric degradation by reaction with photochemically produced hydroxyl radicals
(HSDB, 2005); c) lack ofhazard for the oral route of exposure; and d) lack of systemic
endpoints based on the available studies. Acute and chronic dietary endpoints have not
been selected. Therefore, based on the lack of food uses and the low hazard concern of
the aliphatic alcohols along with no acute or chronic dietary endpoints being identified, a
dietary (food and water) risk assessment is not appropriate.
Aliphatic alcohols are contact sucker control agents used primarily on tobacco [N-
decanol, alcohols (Cx-Cxx), fatty alcohols]. Currently there are no residential uses for
the aliphatic alcohols. There is potential for exposure of occupational mixers, loaders,
applicators, and post-application workers to aliphatic alcohol formulations. However,
due to the low hazard concern of the aliphatic alcohols, no dennal, oral, or inhalation
(
\
Page 7of13
endpoints of toxicological concern have been identified for the aliphatic alcohols.
Therefore, an occupational/residential exposure assessment is not required.
N-Decanol; alcohols (Cx-Cxx), and fatty alcohols are formulated as liquids and are
applied via the following methods: groundboom sprayer, backpack sprayer, handgun
sprayer, high pressure bandwands and low pressure handwands.
Available dennal studies indicate that aliphatic alcohols are acutely irritating with any
possible stress related changes systemically occurring at higher concentrations and over
repeated dennal exposure. Mammals are, therefore, more sensitive to irritation than to
any systemic effects and so dermal exposure should be avoided. Available inhalation
toxicity studies indicate that aliphatic alcohols are oflow toxicity via the inhalation route.
Due to the low hazard profile and lack of endpoint selection for the dermal route of
exposure, no postapplication dermal risk was assessed. For uses within the scope of the
Worker Protection Standard for Agricultural Pesticides (40 CFR 170), a restricted entry
interval (REI) must be established. The REI should be based on the category assigned to
the acute dermal toxicity, skin irritation potential, and eye irritation potential of the active
ingredient. The appropriate REI is 48 hours if any of the three categories are classified as
toxicity category one.
7. Cumulative Exposure
As the aliphatic alcohols are not registered for use on food crops, the requirements of
FQPA are not applicable and a cumulative risk assessment is not appropriate.
(
Page 8of13
8. Summary
1-Decanol has been found as a natural component in apples and oranges and has been
reported in essential oils of ambrette seeds, almond flowers, citrus oils and fennented
beverages. 1-Decanol is also a pennitted food additive for direct addition to food for
human consumption as a synthetic flavoring substance and adjuvant in accordance with
the FDA . Aliphatic alcohols are contact sucker control agents used primarily on tobacco
[N-decanol, alcohols (Cx-Cxx), fatty alcohols]. Currently there are no residential uses
for the aliphatic alcohols.
Based on the hazard profile for dermal exposure to aliphatic alcohols, no post-application
dennal risk was assessed. For uses within the scope of the Worker Protection Standard
for Agricultural Pesticides (40 CFR 170), a restricted entry inteival (REI) must be
established. The REI should be based on the category assigned to the acute dennal
toxicity, skin irritation potential, and eye irritation potential of the active ingredient. The
appropriate REI is 48 hours if any of the three categories are classified as toxicity
category one.
( For occupational uses of aliphatic alcohol~ontaining products, dennal, eye and
respiratory irritation effects are addressed through precautionary labeling requirements
for use of PPE. Most of the current labels for N-decanol, alcohols (Cx-Cxx), and fatty
alcohols require long pants, chemical resistant gloves, shoes plus socks, and protective
eyewear.
Due to the toxicity profile of the aliphatic alcohols, toxicological endpoints of concern
were not warranted for risk assessment purposes. Quantitative dietary (food and
water) and occupational/residential exposure assessments, therefore, have not been
conducted. Additionally, as the aliphatic alcohols are 'nonfood use' chemicals and are
not subject to FQPA, an aggregate risk assessment is not required.
Page 9of13
Table Al: Acute Toxicity Data for the Aliphatic Alcohols
79.2% decanol
870.1100 Acute oral [rat) 079038
44460401 No deaths at 2000 mg/kg III
81-1 1-Decanol LD50>2000mg/kg
Acute oral [rat] 79%decanol
870.1100 079038
46004601 No deaths at 2000 mg/kg Ill
81-1 1-Decanol LD50>2000 mg/kg
37.98% decanol
870.1100 Acute oral [rat] 079038
45507901 No deaths Ill
81-1 1-Decanol LD50>3000 mg/kg
Acute oral [rat] 079038 0060309 78.4% decanol, LD50 = 5000
870.1100
mg/kg IV
81-1 1-Decanol 0064859
Acute dennal [rat] 79.2% decanol
870.1200
81-2 No systemic clinical signs, no
079038
44460402 deaths, very slight erythema at III
1-Decanol 2000 and 4000 mg/kg
LD50>4000 mg/kg
870.1200 Acute dermal [rat] 79%decano1
81-2 079038 No deaths, no systemic clinical
46004602 signs, III
1-Decanol
LD50> 2000 mg/kg
Acute dermal [rat] 37.98% decanol
870.1200 079038
81-2 45507902 No deaths, no clinical signs III
1-Decanol LD50>4000 mg/kg
870.1200 Acute dennal [rabbit] 079038 0046993 78.4% decanol, LD50 = 5000
81-2 mg/kg IV
1-Decanol 0046994
870.1300 Acute inhalation [rat] 79.2% decanol (4 hr nose only)
81-3 1 male died Day 2 post-
079038
44460403 exposure, survivors recovered JV
1-Decano) from 7 to 10 post-exposure
LCS0>5.07 mg/L.
870.1300 Acute inhalation [rat] 79% decano1
079038
81-3 . 46004603 No deaths. IV
1-Decanol LC50>3.35 mg/I..
870.1300 Acute inhalation [rat] 37.98% decanol (4 hr nose only)
81-3 079038 No deaths
45517901 LC50>7.08 mg/L IV
1-Decanol
Page IO of 13
Table Al: Acute Toxicity Data for the Aliphatic Alcohols
870.2400 Acute eye initation 79%decanol
81-4 [rabbit] Corneal opacity, initation
079038 cleared by 6 days. Conjunctive
46004604 irritation, redness, chemosis III
1-Decanol
cleared by 6 days. Moderately
irritating.
Acute eye irritation 37.98% decanol
870.2400 079038
81-4 [rabbit] 45517902 Corneal involvement or irritation III
J-Decanol clearing in 7 days or less
''
Page 11of13
Table Al: Acute Toxicity Data for the Aliphatic Alcohols
870.2600 Skin sensitization 79%decanol
079038
81-6 [guinea pig] 46004606 Not a dennal sensitizer NA
1-Decanol
Table Al: Subcbronlc, Chronic, Developmental, Reproductive and Other Toxicity Prome on the Fatty
Alcohols
Guideline#/ Study MRID# (year)/ Clauification
Type /Doses Results
870.3250 43701201 (1995) Fatty alcohol blend (56.7% decanol, 42.7% octanol)
82-3 Primary adverse clinical signs included ecythema, edema,
Acceptable/Guideline
90-Day dennal desquamation, eschar fonnation and exfoliation of all
toxicity 10 Sprague-Dawley rats/sex/dose treated animals. Irritation apparent within 2 weeks after
of 0, 100, 300, or I000 mg/kg for 5 dermaJ application. Fissuring of skin observed in 40% of
days/week for 13 weeks animals in low dose while 80% of animals in high dose.
High doses animals exhibited vocalization and
hypersensitivity to touch. Body weight was reduced in
high dose (-191'/a M, -13% F) animals. Marginally
increased adrenal glands in high-dose animals, slightly
reduced RBC counts, hematocrit, and increased WBC and
platelet counts in high-dose animals. No gross or
histological alterations other than severe irritation.
Dermal Irritation NOAEL not established, LOAEL
100 mg/kg based on severe initation.
Systemic NOAEL 300 mg/kg/day, LOAEL 1000
mg/kg/day (LID), based on slight changes in
hematological and clinical chemistry parameters, and
decreased bodyweight
Developmental 42634201 (1991) Fatty Alcohol Blend: 96.6%.
Range Finding Rats Dose levels tested: 125, 375, 750, and 1000 mg/kg/day.
No treatment-related effects were seen in the dams or in
the fetuses of dams given the highest dose. Based on this
study, does level selected for the main study were: 0, 125,
375 or 1000 mg/kg/day.
42609301 (1992) Fatty alcohol blend (55% decanol; 40.7% octanol)
870.3700a
83-3a Acceptable/Guideline Maternal NOAEL 375 mg/kg/day
Developmental 25 F Sprague-Dawley /dose at 0, Maternal LOAEL 1000 mg/kg/day, based on increased
Toxicity (rat) 125, 375, 1000 mg/kg/day on GD incidence of salivation (67%).
6-16 Developmental NOAEL 1000 mg/kg/day
Developmental LOAEL not established
Page 12of13
/
Table Al: Subcbronlc, Chronic, Developmental, Reproductive and Other Toxicity Prome on the Fatty
Alcohols
Guideline#/ Study MRID# (yearV Classification
Type /Doses Results
Nelson et al., l 990a, I 990b Dams weighed daily for first week and weekly thereafter.
Developmental
Toxicity (rat) I 00 mg/m3 (max vapor achievable) Rats sacrificed on GD 20.
15 F Sprague-Dawley/ 7 hrs/day on No treatment related effects observed in pregnant
GD 1-19 females, frequency of reso1ptions, fetal weights, or
skeletal/visceral malformations.
42372002 (1992)
Gene Mutation Negative for reverse gene mutations in Salmonella
84-2 Acceptable/Guideline typhimurium TA 1535, TA 1537, TA 1538, TA98, and
870.5100 (553% decanol, 40.7% octanol) TA I 00 in presence or absence of S9 activation to 6 doses
(Salmonella from 1.5 µg/plate to 500 µg/plate (2 independent trials).
typhimurium) Cytotoxicity was apparent for all strains at 500 µgi'plate
+/-89.
42372003 (I 992) Not mutagenic in 2 independent assays with/without
Gene Mutation
870.5300 Acceptable/Guideline activation. Initial assay non-activated & S9 levels ranged
84-2 (553% decanol, 40.7% octanol) from 9.4 µg/ml to 37.5 µg/ml; doses of75 µg/ml severely
(mouse lymphoma cytotoxic. Confinnatory assay with 10-50 µg/ml -S9 and
cells) 30-70 µg/ml +89 were evaluated with severe cytotoxicity
observed at non-activated levels (60 µglml and at 89
activation 80 µglml).
42372001 (I 992) Negative for micronucleus induction in bone manow
Micronucleus
870.5395 Acceptable/Guideline cells of Male and Female CD-1 mice harvested 24 or 48
84-2 (55.3% decanol, 40.7% octanol) hrs post-administration of 3 daily doses of 500, 1000, or
(mouse) 2000 mg/kg/day. No overt toxicity in any treated animal
or target organ in any treatment group.
References:
Nelson BK, Brightwell WS, Khan A, Krieg EF Jr, and Hoberman AM (1990b).
Developmental toxicology assessment of 1-octanol, 1-nonanol, and 1-decanol
administered by inhalation to rats. Journal of the American College of Toxicology. Vol
9(1): 93-97.
HSDB, 2005. Hazardous Substances Data Banlc. National Library of Medicine. Search
Term: 1-Decanol. http://toxnet.nlm.nih.gov/cgi-bin/sis/search/f?./temp/-fK9cOq: 1
Page 13of13
(
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March 2007
United States Prevention, Pesticides EPA 738-R-07-004 (--,
OEPA. Environmental Protection
Agency
and Toxic Substances
(7508PJ
Reregistration
Eligibility Decision
for Aliphatic Alcohols
(
~,__ ,
( ·.
\ .
/
i
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List D
Approved by: _ _ _ _ _ _ _ __
Date: - - - - - - - -
Abstract v
I. Introduction 1
II. Chemical Overview 1
A. Regulatory History I
B. Chemical Identification 2
III. Summary of Aliphatic Alcohols Risk Assessments 4
A. Human Health Risk Assessment 4
B. Environmental Risk Assessment 6
1. Environmental Fate and Transport 7
2. Ecological Risk Assessment 8
IV. Risk Management, Reregistration, and Tolerance Reassessment Decision 14
A. Determination of Reregistration Eligibility 14
B. Public Comment Period 15
C. Regulatory Position 15
1. Regulatory Rationale 15
2. Endocrine Disruptor Effects 16
3. Endangered Species 16
D. Labeling Requirements 17
V. What Registrants Need to Do 17
A. Manufacturing Use Products 18
1. Additional Generic Data Requirements 18
2. Labeling for Manufacturing-Use Products 18
B. End-Use Products 18
1. Additional Product-Specific Data Requirements 18
2. Labeling for End-Use Products 18
C. Labeling Changes Summary Table 19
II
Glossary of Terms and Abbreviations
ai Active Ingredient
CFR Code of Federal Regulations
CSF Confidential Statement of Formula
DCI Data Call-In
EDWC Estimated Drinking Water Concentration
EEC Estimated Environmental Concentration
EPA Environmental Protection Agency
FDA Food and Drug Administration
FIFRA Federal Insecticide, Fungicide, and Rodenticide Act
FFDCA Federal Food, Drug, and Cosmetic Act
FQPA Food Quality Protection Act
GENEEC Tier I Surface Water Computer Model (Estimated Aquatic Environmental Concentrations)
LC so Median Lethal Concentration. A statistically derived concentration of a substance that can be expected
to cause death in 50% oftest animals. It is usually expressed as the weight of substance per weight or
volume of water, air or feed, e.g., mg/I, mg/kg or ppm.
LDso Median Lethal Dose. A statistically derived single dose that can be expected to cause death in 50% of
the test animals when administered by the route indicated (oral, dermal, inhalation). It is expressed as
a weight of substance per unit weight of animal, e.g., mg/kg.
LOC Level of Concern
LOAEL Lowest Observed Adverse Effect Level
mg/kg/day Milligram Per Kilogram Per Day
mg/L Milligrams Per Liter
MRID Master Record Identification (number). EPA's system ofrecording and tracking studies submitted.
( MUP Manufacturing-Use Product
< NIA
NOAEL
Not Applicable
No Observed Adverse Effect Level
OPP EPA Office of Pesticide Programs
ppb Parts Per Billion
PPE Personal Protective Equipment
ppm Parts per Million
RED Reregistration Eligibility Decision
REI Restricted Entry Interval
RQ Risk Quotient
TGAI Technical Grade Active Ingredient
UV Ultraviolet
WPS Worker Protection Standard
iii
ALIPHATIC ALCOHOLS TEAM
Registration Division
Tony Kish
Risk Management
Kevin Costello
Tom Moriarty
c
Kimberly Nesci
(
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IV
Abstract
The Environmental Protection Agency (EPA or the Agency) has completed the human
health and environmental risk assessments for the Aliphatic Alcohols case 4004 and is issuing its
risk management decision. Currently, case 4004 consists of four active ingredients. Three of
these active ingredients, 1-octanol, 1-decanol and a mixture of aliphatic alcohols described as
"fatty alcohols," are used as plant growth regulators on tobacco. The fourth, 1-dodecanol (also
known as lauryl alcohol), is registered as a Lepidopteran pheromone/sex attractant in pear and
apple orchards.
The potential for ecological risk from the pheromone use and from the growth-regulator
uses is considered in this document. The ecological risk assessment identifies no ecological risks
of concern from the use of aliphatic alcohols.
The risk assessments, which are summarized below, are based on the review of the
required target database supporting the use patterns of currently registered products. After
( considering the potential risks identified, EPA has determined that aliphatic alcohol-containing
\
products are eligible for reregistration. That decision is discussed fully in this document.
/
<
v
I. Introduction
The Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA) was amended in 1988
to accelerate the reregistration of products with active ingredients registered prior to November 1,
1984. The amended Act calls for the development and submission of data to support the
reregistration of an active ingredient, as well as a review of all submitted data by the U.S.
Environmental Protection Agency (referred to as EPA or "the Agency"). Reregistration involves
a thorough review of the scientific database underlying a pesticide's registration. The purpose of
the Agency's review is to reassess the potential risks arising from the currently registered uses of
the pesticide, to determine the need for additional data on health and environmental effects, and
to determine whether or not the pesticide meets the "no unreasonable adverse effects" criterion
ofFIFRA.
This document summarizes EPA's human health and ecological risk assessments and
reregistration eligibility decision (RED) for aliphatic alcohols. The document consists of six
sections. Section I contains the regulatory framework for reregistration; Section II provides an
overview of the chemical and a profile of its use and usage; Section III gives an overview of the
human health and environmental effects risk assessments; Section IV presents the Agency's
decision on reregistration eligibility and risk management; and Section V summarizes the label
changes necessary to implement the risk mitigation measures outlined in Section IV. Finally, the
Appendices list related information, supporting documents, and studies evaluated for the
reregistration decision. The risk assessments for aliphatic alcohols and all other supporting
documents are available in the Office of Pesticide Programs (OPP) public docket
(http://www.regulations.gov) under docket number EPA-HQ-OPP-2007-0134. (
A. Regulatory History
Reregistration case number 4004 consists of straight chain aliphatic alcohols with 6 to 16
carbon atoms in the chain, which has been abbreviated in previous documents as aliphatic
alcohols (Cx-Cxx) or (C6-Cl6). Currently, case 4004 consists of four active ingredients. Three
of these active ingredients are used as plant growth regulators on tobacco. These are described
as fatty alcohol blend (PC code 079029), 1-octanol (079037) and 1-decanol (079038). The fatty
alcohol blend under PC code 079029 is predominantly a mixture of 1-octanol and 1-decanol,
although some labels list 0.5% 1-hexanol (C6) and 1.5 % dodecanol (Cl2) among the active
ingredients. The single product listed under PC code 079037, although listed as 1-octanol, is
also in fact a mixture of 1-octanol and 1-decanol. The earliest registered label for use of
aliphatic alcohols for tobacco sucker control included in the Agency's Pesticide Product Label
System (PPLS) was issued to Uniroyal in 1964.
The fourth active ingredient in case 4004, 1-dodecanol (PC code 001509), was first
registered for use as a Lepidopteran pheromone/sex attractant in 1993. The potential human
health risks from 1-dodecanol were reassessed in 2002 by the Agency's Biopesticides and
Pollution Prevention Division (BPPD), as described in the document, Tolerance Reassessment
Decision Regarding Tolerance Exemption for the Biochemical Lepidopteran Pheromones. July
c·
26, 2002. This RED document describes the potential ecological effects of the use of 1-
dodecanol.
Other aliphatic alcohols are not assessed in this document. The fatty alcohol product
included under PC code 079059 is not being supported, and will be voluntarily cancelled. In
April 1995, the Agency completed a Reregistration Eligibility Decision (RED) for case number
4003 (C 1 - C5), which consists of aliphatic alcohols with only one to five carbons. The active
ingredients addressed in that assessment included ethanol (PC code 001501), and isopropanol
(PC code 047501).
B. Chemical Identification
The aliphatic alcohols are considered primary alcohols (i.e., the -OH group in the C-1
position). The aliphatic alcohols 1-octanol (PC code 079037) and 1-decanol (PC code 079038)
are also known by many other common names, and the fatty alcohol blend (PC code 079029) is a
generic term meaning that the compound is obtained by the hydrolysis of fatty acid esters. The
registrations under the name fatty alcohol blend (PC code 079029) are considered a mixture of
the linear, straight chain chemicals 1-octanol and 1-decanol. Tables 1 - 3 provide the chemical
identification for 1-octanol, 1-decanol, and 1-dodecanol, respectively.
Chemical Structure OH
f
I
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2
T e oflnformation Information for this Chemical
Chemical Structure
Chemical Structure
The aliphatic alcohols 1-octanol and 1-decanol are applied as water-based sprays to
burley, flue cured and dark tobacco by hand using a back pack sprayer, or to tobacco plants by a
boom. The aliphatic alcohols are applied to tobacco at the button or early flower stage and act as
chemical pinching agents to control sucker shoots. The aliphatic alcohols dissolve the layer of
waxy cuticle on the plant, causing dehydration of the young sucker. Because these aliphatic
alcohols are applied solely on tobacco, its use is limited to the tobacco growing states, mainly on
the east coast (Connecticut, Pennsylvania, Virginia, North Carolina, South Carolina, Georgia,
and Florida), but also in Kentucky and Tennessee. Between 1.5 and 2 million pounds of
aliphatic alcohols are applied annually.
The volatility of 1-dodecanol is essential to its use as a pheromone in apple and pear
orchards. The pheromone is applied from polyethylene dispenser tubes hung throughout the
orchard. The active ingredient, 1-dodecanol (lauryl alcohols; PC code 001509), disperses
passively from the tube into the atmosphere over 3-4 months. Once dispersed from its dispensers,
1-dodecanol degrades quickly by photolysis in the air.
The aliphatic alcohols are used in, or can be naturally found in various food items. The
Food and Drug Administration permits the use of aliphatic alcohols as a food additive, under
certain conditions. The aliphatic alcohols have been found to be natural components of apples
and oranges, and have been reported as a component of edible seeds, oils and fermented
beverages.
3
I
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III. Summary of Aliphatic Alcohols Risk Assessments
The purpose of this summary is to assist the reader by identifying the key features and
findings of these risk assessments, and to help the reader better understand the conclusions
reached in the assessments. The human health and ecological risk assessment documents, and
supporting information listed in Appendix C were used to formulate the safety finding and
regulatory decision for aliphatic alcohols.
While the following risk assessments and related addenda are not included in this
document, they are available from the OPP Public Docket, docket number EPA-HQ-OPP-2007-
0134, and may also be accessed through the website http://www.regulations.gov/. Hard copies of
these documents may be found in the OPP public docket under this same docket number.
The Agency has conducted a risk assessment of the tobacco plant growth inhibitor use of
the aliphatic alcohols. The Agency's screening level assessment was conducted using data
submitted by the registrants and published in the open literature. A summary of the Agency's
human health risk assessment is presented below. More detailed information associated with the
risks posed by the tobacco plant growth inhibitor use of the aliphatic alcohols can be found in the
human health risk assessment, Aliphatic Alcohols: Human Health Chapter of the Reregistration
Eligibility Decision (RED) Document. Reregistration Case Number 4004, which is available in
the public docket.
The potential human health risks from 1-dodecanol were assessed in 2002 by the
Agency's Biopesticides and Pollution Prevention Division (BPPD), as described in the document,
Tolerance Reassessment Decision Regarding Tolerance Exemption for the Biochemical
4
Lepidopteran Pheromones. July 26, 2002. The tolerance exemption for Lepidopteran
pheromones, including 1-dodecanol, was determined to be in compliance with FQPA.
The data base of submitted toxicity studies and published literature is sufficient to assess
the uses of the aliphatic alcohols. The available toxicity data base for the aliphatic alcohols
consists of acute toxicity, irritation, and sensitization studies. In addition, there are
developmental rat (oral and inhalation) toxicity studies and a 90-day rat (dermal) study. The
available mutagenicity studies include the Ames, micronucleus, and gene mutation assays.
Currently, there is no known mode of toxicological action for the aliphatic alcohols.
Based on the low hazard concern via the oral, dermal, and inhalation routes of exposure, a
quantitative risk assessment for the aliphatic alcohols is not appropriate. Therefore, the Agency
conducted a qualitative assessment.
Toxicity Profile
Available acute toxicity studies indicate the aliphatic alcohols are of low oral and dermal
toxicity. Acute inhalation studies with the rat resulted in estimates of the median lethal dose
(LDso) above the limit concentration of 2 mg/L. However, eye irritation studies resulted in
severe and sometimes non-reversible eye irritation. Dermal irritation studies revealed slight to
moderate irritation in rabbits, and the aliphatic alcohols generally did not produce sensitization in
tests with guinea pigs.
There are few subchronic or chronic toxicity data available for the aliphatic alcohols;
however, the available developmental toxicity studies revealed no adverse effects in fetal and
maternal parameters. The available genotoxicity and mutagenicity studies were negative. There
is currently no long-term rodent toxicity information regarding the carcinogenic potential for the
aliphatic alcohols. While neurotoxicity information is currently not available, there were no
clinical signs in any of the acute, subchronic, or developmental toxicity studies to suggest the
aliphatic alcohols elicit a neurotoxic effect. Based on the available data, there is no evidence that
warrants determining any dietary, oral, dermal, or inhalation endpoints to quantify sub-chronic or
chronic toxicity.
Finally, there is no evidence to suggest that the aliphatic alcohols cause increased
susceptibility in infants and children. Therefore, based on the results of the available studies, no
endpoints of toxicological concern have been identified for human health risk assessment
purposes. Table 4 summarizes the available toxicity data for the aliphatic alcohols.
870.1200 Acute dermal [rat] 079038 44460402 LD 50 reported as > 2000 mg/kg;
III
(other studies reported LD 5o>
81-2 1-Decanol 46004602 4000 mg/kg and one study
45507902 showed LD 50 = 5000 mg/kg
870.2500 Acute dermal 079038 44407601 In one study, erythema, eschar III-IV
irritation [rabbit] 1-Decanol formation and edema was
81-5 44460405
evident at 72 hrs.
46004605
Test substance reported as mild
45517903 irritant.
The Agency has conducted a screening-level risk assessment of the tobacco plant growth
inhibitor and pheromone uses of the aliphatic alcohols. The Agency's screening level
assessment was conducted using data submitted by the registrants in conjunction with acceptable
,/·
6
ecotoxicity data from the open literature. Anticipated exposure pathways to non-target species
include oral exposure, and inhalation of aliphatic alcohol products.
Because environmental fate data are not available, physical and chemical properties for
the aliphatic alcohols were estimated by Quantitative Structure-Activity Relationships (QSAR)
using EPISuite v3.21 (Estimation Programs Interface for Windows (EPIWIN)). The estimated
properties of 1-octanol, 1-decanol and 1-dodecanol differ somewhat, due to the different lengths
(i.e. number of carbons) in their straight, saturated carbon chains. As suggested by their
common names, 1-octanol has 8 carbons in its chain, 1-decanol has 10 carbons, and 1-dodecanol
has 12 carbons.
In spite of these small differences, the expected behavior of these aliphatic alcohols in the
environment is generally similar. The major route of dissipation in the field for these chemicals
is likely to be volatilization. The volatility half-lives for 1-octanol and 1-decanol were estimated
using the Dow Method described in the Handbook of Chemical Property Estimation Methods by
Lyman, Reehl and Rosenblatt. The half-lives for volatility from soil for 1-octanol and 1-decanol
were estimated to be 3.5 minutes and 1 minute, respectively. 1-dodecanol would likely volatilize
even more quickly, but the half-life was not estimated, since volatility from pheromone traps is
the known route of dissipation.
There is some uncertainty about the rate of volatility of 1-octanol and 1-decanol from
plant surfaces, since aliphatic alcohols are hydrophobic and, therefore, have affinity for the waxy
surfaces of plants. However, these volatility half-lives suggest that the aliphatic alcohols will not
be available long to expose non-target terrestrial animals, nor to be transported to surface water
bodies in runoff. Residues of 1-dodecanol are not expected on plants or in soil, since they are
dispersed in the air from pheromone traps, and then degraded by photolysis. The ecological risk
assessment concluded that except for terrestrial insects, which are the target for the pheromone
use of 1-dodecanol, "environmental exposures resulting from this use are likely negligible." The
risk assessment for this use was therefore qualitative.
7
As mentioned above, dissipation via volatilization will greatly reduce the amount of
\.
aliphatic alcohols reaching surface-water bodies, and aliphatic alcohols will volatilize from water
as well as soil. However, the fraction that does reach surface water will not be degraded by
hydrolysis. These alcohols have the potential to bioaccumulate in fish, but the rates of uptake,
metabolism, and depuration, as well as the nature of metabolites, are not known. However, the
magnitude of the bioconcentration factors (BCF) suggests a low potential to bioconcentrate.
EPISuite does not provide information on the rates of formation/decline of product, the
nature and relative amounts of transformation products, and their distribution in soil/sediment-
water-air. Therefore, the specific nature and persistence of potential biotransformation products
(primary biodegradation) are not known. However, the ultimate biotransformation products of
the aliphatic alcohols are water and carbon dioxide.
The Agency uses a pesticide's use profile, exposure data, and toxicity information to
determine risk estimates to non-target terrestrial and aquatic organisms. Estimated
environmental concentrations (EECs) are used to calculate risk quotients (RQs). EECs are based
on the maximum application rate(s) which would potentially yield the greatest exposure. An RQ
is derived by dividing the EEC by a single estimate of toxicity. The Agency then compares an
RQ to its Level of Concern (LOC) to determine if exposure to the aliphatic alcohols could
potentially pose a risk to non-target organisms (RQs that exceed the LOC indicate potential risk).
Table 5 outlines LOCs, and the Agency's corresponding risk presumptions.
(
' T a ble 5. A.2ency L eve I ofC oncerns an dR"IS kP res um p f IODS
LOC Terrestrial LOCAquatic
Risk Presumption LOC Plants
Animals Animals
Acute Risk - there is a potential for
0.5 0.5 1
acute risk
Acute Endangered Species -
endangered species may be adversely 0.1 0.05 1
affected
Chronic Risk - there is potential for
1 1 NIA
chronic risk
Although GENEEC is not designed to consider volatility from soil directly, the Agency
used an indirect method to consider volatility with the GENEEC model and to refine the aquatic
/ exposure assessment. As described above, the volatility half-lives for the aliphatic alcohols were
8
estimated using the Dow Method described in the Handbook of Chemical Property Estimation
Methods (Lyman, et al., 1982). The half-lives for volatility from soil for 1-octanol and 1-decanol
were estimated to be 3.5 minutes and 1 minute, respectively. Such short volatility half-lives
mean that little pesticide will remain by the time a runoff event occurred, unless rainfall began
immediately after application.
To simulate this scenario using GENEEC, the Agency determined the amount of 1-octanol
or 1-decanol that would remain in the field 3 to 4 minutes after application at the maximum rates
allowed on the label. GENEEC was then run in the standard fashion, but with this "effective
application rate." Even though this was done using estimated volatility half-lives on the order of
a couple of minutes, the resulting EECs are still considered upper-bound. GENEEC does not
simulate a rainfall event until two days after application; if rainfall does not occur until two days
after actual application of 1-octanol or 1-decanol, there could be very little product remaining to
be subject to transport in runoff. For this reason, the simulations considered only a single
application, although aliphatic alcohols can be used more than once within a single growing
season.
Registrant-submitted data and open literature studies suggest that the aliphatic alcohols
are "slightly" to "moderately" toxic to freshwater fish. Although the data base is not complete
for all compounds in the aliphatic alcohol registration case, there are adequate data to assess the
acute risk to freshwater fish. Although there are no registrant-submitted acute toxicity data
available for estuarine/marine fish, data from the open literature provided the information to
assess the acute risks of aliphatic alcohols to these organisms. The relevant study from the open
literature indicates that 1-octanol is "slightly" toxic, and 1-decanol is "moderately" toxic to
estuarine/marine fish.
No chronic toxicity guideline studies exist for any of the aliphatic alcohols. However,
chronic data for freshwater fish from the open literature on 1-octanol provide an endpoint which
the Agency used to calculate RQs. Chronic toxicity data for aquatic invertebrates on the
aliphatic alcohols were also drawn from the open literature. The Agency used a chronic no
observed adverse effect concentration (NOAEC) of 1 mg/L for reproductive effects for 1-octanol.
The Agency notes that chronic toxicity data on 1-decanol for aquatic invertebrates would reduce
the uncertainty posed by the lack of these data. A summary of all toxicity endpoints is presented
below in Table 6.
Table 6. Toxicity Reference Values Used to Calculate RQs for Aliphatic Alcohols
1-0ctanol 1-Decanol
Taxonomic Assessment
Group Endpoint Species/ Species/
Toxicity Endpoint Toxicity Endpoint
9
1-0ctanol 1-Decanol
Taxonomic Assessment
Group Endpoint Species/ Species/
Toxicity Endpoint Toxicity Endpoint
10
Table 8. Acute and Chronic RQs for Estuarine/Marine Fish
60-Max
Peak
Effective Application Toxicity Value Acute Average
Chemical EEC Chronic RQ
Rate (lbs a.i./acre) (µg/L) RQ EEC
(µg/L)
(ue:/L)
LC 50 = 7200
1-Decanol 1.95, 1 application 57 <0.01 13 nd
NOAEC-nd
LCso= 15000
1-0ctanol 4.4, 1 application 140 <0.01 29 nd
NOAEC-nd
Aquatic plant toxicity data from open literature were only available for 1-octanol. Based
on these data, the acute RQs for aquatic plants do not exceed the Agency's acute and endangered
species LOCs (both 1.0) (Table 11 ). However, there is some uncertainty in this risk conclusion,
given that the NOAEC for 1-octanol is unknown, and no aquatic phytotoxicity data are available
for 1-decanol. The NOAEC is used to calculate an RQ to evaluate potential risk to endangered
species. Because the NOAEC was not established, the EC1o for 1-octanol was used. Since the
LOC for endangered aquatic plants is 1.0, and the RQ derived using the EC 10 is 0.05, the
NOAEC would have to be at least 20 times lower than the EC1o for the Agency to have an
endangered species concern for aquatic plants.
Based on the analysis of the volatility of the aliphatic alcohols, aquatic exposures
resulting from the labeled use of 1-decanol and 1-octanol are unlikely to reach concentrations
that exceed the Agency's LOC. As a result, the value of additional aquatic plant studies for the
aliphatic alcohols is low.
.
T a ble 11 R"IS kt0 A,quaf IC Plans
t
Peak EEC
Chemical Rate (lbs a.i./acre) Toxicity Value (µg/L) AcuteRQ
(u!!/L)
ECso = 6500 0.02
1-0ctanol 4.4, I application 140
EC 10 =2800 0.05
1-Decanol 1.95, 1 application 57 No data --
( /
11
/
Birds
Available toxicity data indicate that the aliphatic alcohols are categorized as "practically
non-toxic" to birds on acute oral and dietary bases. Acute risks to birds were not quantified,
because no discreet median lethal doses or concentrations were established in the acute oral and
dietary studies. An acute dietary study from the open literature reported a dietary LC 50 for
bantam chickens of 201,000 ppm (100% 1-decanol). This level is more than 20 times greater
than the highest predicted dietary exposure level (~10,000 ppm). Therefore, the Agency
concludes that the aliphatic alcohols do not pose an acute risk to birds.
No avian chronic toxicity studies were available for any of the aliphatic alcohols and,
therefore, the Agency cannot directly assess the potential chronic risk to avian species. However,
since 1) the aliphatic alcohols are not acutely toxic to birds at doses many times higher than
expected exposure, 2) the volatility of the aliphatic alcohols makes chronic exposure unlikely,
with EECs dropping more than an order of magnitude within 30 minutes, 3) the aliphatic
alcohols assessed are listed as food additives and are "Generally Recognized as Safe" (GRAS)
by the U.S. Food and Drug Administration 1 , and 4) a mammalian chronic toxicity study indicates
the aliphatic alcohols are not chronically toxic to mammals, the Agency does not expect a
chronic risk to birds, and will not require chronic avian toxicity studies at this time.
/
I
\
Mammals
Acute oral mammalian toxicity data indicate that the aliphatic alcohols are "practically
non-toxic" to mammals on an acute oral basis. Four studies performed with laboratory rats did
not result in LC 50 endpoints with which RQs could be calculated. The Agency concludes that
aliphatic alcohols do not pose an acute dietary risk to mammals.
Terrestrial Insects
Available toxicity data indicate that aliphatic alcohols are "practically non-toxic" to
honey bees (acute contact LD50 > 25 µg/bee). However, given that aliphatic alcohols can be
used as Lepidopteran sex inhibitors, there is a potential for sub lethal (e.g., reproductive) effects
on non-target Lepidopterans, such as butterflies. This potential effect cannot be quantified at this
time.
1
http://vm.cfsan.fda.gov/~dms/eafus.html
12
Terrestrial Plants
Tier-I terrestrial plant seedling emergence study data suggest a fatty alcohol blend (1-
decanol and 1-octanol) is not toxic to most plants at the maximum rate tested (18.03 lbs ai/A).
An EC 25 could not be established for tested species, although lesser effects were observed in
cucumbers, carrots and tomatoes. Therefore, the Agency did not calculate RQs based on
seedling emergence effects.
EC 25 values and related no-effect levels were established for two (com and cucumber) of
10 crop plants tested in a submitted vegetative vigor study. The Agency used these endpoints in
the TerrPlant model to calculate RQs (Table 12). All were below the Agency's LOC of 1.
There are currently no adverse ecological incidents listed in the Ecological Incident
Information System (EIIS) that are associated with the aliphatic alcohols.
f. Endangered Species
Based upon the screening-level assessment conducted on aliphatic alcohols, the Agency
has not definitively identified exceedences of endangered species LOCs for direct effects to non-
target animals or plants. Acute RQs did not exceed endangered species LOCs for birds,
mammals, terrestrial plants, freshwater fish and invertebrates, or estuarine/marine fish and
invertebrates. Chronic data were not available for birds and estuarine/marine fish and
invertebrates. As described above, the Agency believes that the volatility and low toxicity in
available acute and chronic toxicity studies for mammals and freshwater animals suggest that
chronic risk to birds and estuarine/marine animals is unlikely. However, because the toxicity
data are not available, the Agency cannot completely preclude risk to listed birds and
estuarine/marine animals at this time. Similarly, since a no-effect level was not determined for
aquatic plants, the Agency cannot preclude direct effects on these organisms, although exposure
is expected to be negligible.
The Agency considers a potential for not only direct effects, but also adverse indirect
effects to listed species that rely on other affected organisms. Because direct effects to aquatic
plants cannot be precluded, indirect effects to listed aquatic species which rely on aquatic plants
can also not be dismissed. Similarly, indirect effects to terrestrial plants and animals cannot be
precluded because of potential reproductive effects of aliphatic alcohols to some terrestrial
insects.
13
Table 13. Potential Listed Species Risks Associated with Direct or Indirect Effects Due to
A,pp r1cafions 0 f ArIP h a f IC Alcoh oIs as Sh00ti n h•b•t
I 1 ors on T 0 b acco.
Direct Effects Indirect Effects to Endangered
Listed Taxon
Acute Chronic Species
Terrestrial and semi-aquatic plants - No NIA Possible
monocots
Terrestrial and semi-aquatic plants - No NIA Possible
di cots
Birds No No data Possible
Terrestrial-phase amphibians No No data Possible
Reptiles No No data Possible
Mammals No No Possible
Aquatic non-vascular plants* Insufficient data NIA NIA
Aquatic vascular plants Insufficient data NIA NIA
Freshwater fish No No Possible
Aquatic-phase amphibians No No Possible
Freshwater crustaceans No No Possible
Mollusks No NIA Possible
Marine/estuarine fish No No data Possible
Marine/estuarine crustaceans No No data Possible
.. of threatened and endangered species.
* At the present time, no aquatic non-vascular plants are mcluded m Federal hstmgs The
taxonomic group is included here for the purposes of evaluating potential contributions to indirect effects to other taxa and as a
record of exceedences should future listings of non-vascular aquatic plants warrant additional evaluation of Federal actions.
Further analysis regarding the overlap of individual species with each use site is required
prior to determining the likelihood of potential impact to listed species. At the screening level,
this analysis is accomplished using the Location of Crops and Threatened and Endangered
Species (LOCATES) data base, which uses location information for listed species at the county
level and compares it to agricultural census data for crop production at the same county level of
resolution. The ecological risk assessment includes a complete listing of aquatic plants, birds,
reptiles, terrestrial-phase amphibians, mammals, and terrestrial invertebrates associated with the
States where the aliphatic alcohols are use as a plant growth regulator on tobacco.
Section 4(g)(2)(A) of FIFRA calls for the Agency to determine, after submission of
relevant data concerning an active ingredient, whether or not products containing the active
ingredient are eligible for reregistration. The Agency has previously identified and required the
submission of the generic (i.e., active ingredient-specific) data required to support reregistration
of products containing aliphatic alcohols as an active ingredient. The Agency has completed its
review of these generic data, and has determined that the data are sufficient to support
reregistration of all products containing aliphatic alcohols (C6 - C 16).
The Agency has completed its assessment of the human health and ecological risks
associated with the use of pesticide products containing aliphatic alcohols (C6-C16). The
Agency has determined that aliphatic alcohol-containing products are eligible for reregistration
provided that label amendments are made as outlined in Chapter V. Appendix A summarizes the
14
uses of aliphatic alcohols (C6- Cl6) that are eligible for reregistration. Appendix B identifies
the generic data requirements that the Agency reviewed as part of its determination of
reregistration eligibility of aliphatic alcohols (C6 - C 16), and lists the submitted studies that the
Agency found acceptable.
The Agency has identified eye-irritation concerns that warrant specific label language
concerning personal protective equipment (PPE) and the length of restricted-entry intervals after
application for tobacco uses of the aliphatic alcohols (C6 - C 16). If all changes outlined in this
document are incorporated into the product labels, the eye-irritation concerns will have been
mitigated. Should a registrant fail to implement any of the reregistration requirements identified
in this document, the Agency may take regulatory action to address these concerns.
Because the risks associated with the use of aliphatic alcohols were low and did not
warrant mitigation measures, a Phase 3 public comment period on the aliphatic alcohols risk
assessments was not conducted. However, a 60-day public comment period will be conducted
after the RED is issued, and will be announced in the Federal Register. Comments may be
submitted under Docket number EPA-HQ-OPP-2007-0134 at http://www.regulations.gov/. The
RED document and technical supporting documents for aliphatic alcohols are also available to
the public under docket identification (ID) number EPA-HQ-OPP-2007-0134. In addition, the
aliphatic alcohols RED document may be downloaded or viewed through the Agency's website
at http://www.epa.gov/pesticides/reregistration/status.htm.
C. Regulatory Position
1. Regulatory Rationale
The Agency has determined that aliphatic alcohols-containing products are eligible for
reregistration provided that specified label amendments are made. The following is a summary
of the rationale for managing risks associated with the use of aliphatic alcohols.
There are no human health risk concerns for the aliphatic alcohols with the exception of
eye irritation for 1-decanol. 1-decanol, which is a component of all active tobacco use
formulations of the aliphatic alcohols (C6 - C 16), is an acute toxicity category I eye irritant and,
therefore, pursuant to the Worker Protection Standards (WPS), products with agricultural uses
must require a 48 hour REI and the following PPE for early entry: coveralls, chemical-resistant
gloves made of any water proof material, shoes plus socks, and protective eyewear.
The risk assessment identified no exposure scenarios with aliphatic alcohols that pose
ecological risks of concern to the Agency, including direct effects on endangered species. Thus,
15
\ no mitigation measures to address ecological risks are necessary for the reregistration of aliphatic
alcohols.
Moreover, because of the low risks associated with the use of aliphatic alcohols, as
summarized in this document, the Agency concludes that spray drift mitigation is not needed as
part of the reregistration eligibility determination.
When the appropriate screening and/or testing protocols being considered under the
EDSP have been developed, individual pesticides may be subject to additional screening and/or
testing. However, in the available toxicity studies for the aliphatic alcohols, there was no
evidence of endocrine disruption.
3. Endangered Species
The Endangered Species Act required federal agencies to ensure that their actions are not
likely to jeopardize listed species or adversely modify designated critical habitat. The Agency
has developed the Endangered Species Protection Program to identify pesticides whose use may
cause adverse impacts on federally listed endangered and threatened species, and to implement
mitigation measures that address these impacts. To assess the potential of registered pesticide
uses that may affect any particular species, EPA puts basic toxicity and exposure data developed
for the REDs into context for individual listed species and considers ecological parameters,
pesticide use information, the geographic relationship between specific pesticide uses and
species locations and biological requirements and behavioral aspects of the particular species.
When conducted, these analyses take into consideration any regulatory changes recommended in
this RED being implemented at that time. A determination that there is a likelihood of potential
effects to a listed species may result in limitations on the use of the pesticide, other measures to
mitigate any potential effects, and/or consultations with the Fish and Wildlife Service or National
Marine Fisheries Service, as necessary. If the Agency determines use of aliphatic alcohols "may
affect" listed species or their designated critical habitat, EPA will employ the provisions in the
Services regulations (50 CFR Part 402).
The ecological assessment that EPA conducted for this RED does not, in itself, constitute
a determination as to whether specific species or critical habitat may be harmed by the pesticide.
Rather, this assessment serves as a screen to determine the need for any species specific
16
assessment that will evaluate whether exposure may be at levels that could cause harm to (
specific listed species and their critical habitat. That assessment refines the screening-level
assessment to take into account the geographic area of pesticide use in relation to the listed
species, the habits and habitat requirements of the listed species, etc. If the Agency's specific
assessments for aliphatic alcohols result in the need to modify use of the pesticide, any
geographically specific changes to the pesticide's registration will be implemented through the
process described in the Agency's Federal Register Notice (54 FR 27984) regarding
implementation of the Endangered Species Protection Program.
The Agency has reviewed data and other information for the aliphatic alcohols (C6 -
C 16) and concludes that this plant growth regulator does not pose a risk of direct acute effects to
most species listed under the Endangered Species Act, because EPA's screening-level
assessment shows 'no effect' on listed species or their critical habitat (RQ values were below the
level of concern for endangered species). There is some uncertainty regarding acute risk to
aquatic plants, however. Although the volatility of 1-octanol and 1-decanol suggests that
exposure to aquatic plants would be negligible, a no-observed-adverse-effect-level could not be
established and, therefore, indirect effects to listed aquatic animals which depend on aquatic
plants could not be precluded. Similarly, the Agency believes that the volatility and low toxicity
in available acute and chronic toxicity studies for mammals and freshwater animals suggest that
chronic risk to birds and estuarine/marine animals is unlikely. However, because the toxicity
data are not available, the Agency cannot completely preclude risk to listed birds and
estuarine/marine animals at this time.
D. Labeling Requirements
In order to be eligible for reregistration, various use and safety information will be
included in the labeling of all end-use products containing aliphatic alcohols. For the specific
labeling statements, refer to Section V of this RED document.
The Agency has determined that aliphatic alcohols (C6-C16)-containing products are
eligible for reregistration provided that the required label amendments are made. The Agency
intends to issue Data Call-In (DCis) Notices requiring product-specific data. Generally,
registrants will have 90 days from receipt of a DCI to complete and submit response forms or
request time extension and/or waiver requests with a full written justification. For product-
specific data, the registrant will have eight months to submit data. Below are the label
amendments that the Agency intends to require for aliphatic alcohols to be eligible for
reregistration.
17
A. Manufacturing Use Products
The generic data base supporting the reregistration of aliphatic alcohols for currently
registered uses has been reviewed and determined to be substantially complete. However, a few
data gaps remain, and these are listed below.
Product Chemistry
B. End-Use Products
18
C. Labeling Changes Summary Table
c
In order to be eligible for reregistration, amend all product labels to comply with the
following table. Table 14 describes how language on the labels should be amended.
(
19
/~ -~. _,.,..-~,
Manufacturing-Use Products
Required on all "Only for formulation into a growth regulator for tobacco sucker control." Directions for Use
MUPs
One of these "This product may be used to formulate products for specific use(s) not listed on the MP label ifthe Directions for Use
statements may formulator, user group, or grower has complied with U.S. EPA submission requirements regarding
be added to a support of such use(s )."
label to allow
reformulation of "This product may be used to formulate products for any additional use(s) not listed on the MP label
the product for a ifthe formulator, user group, or grower has complied with U.S. EPA submission requirements
specific use or all regarding support of such use(s)."
additional uses
supported by a
formulator or
user i;!;roup.
Environmental "Do not discharge effluent containing this product into lakes, streams, ponds, estuaries, oceans, or Directions for Use
Hazards other waters unless in accordance with the requirements of a National Pollution Discharge
Statements Elimination System (NPDES) permit and the permitting authority has been notified in writing prior
Required by the to discharge. Do not discharge effluent containing this product to sewer systems without previously
RED and Agency notifying the local sewage treatment plant authority. For guidance contact your State Water Board
Label Policies or Regional Office of the EPA."
20
End-Use Products Intended for Occupational Use (WPS and non-WPS)
HandlerPPE "Personal Protective Equipment (PPE) Precautionary
Requirements 1 for (insert Statements:
type of formulation) Mixers, loaders, applicators, and other handlers must wear: Hazards to
> Long-sleeved shirt and long pants and, Humans and
Note: Separate sections > Shoes plus socks" Domestic
should be used for each Animals
formulation type (i.e.
liquids, powders,
granulars, etc ... ) unless
the required handler PPE
is identical for all
formulation types.
User Safety Requirements "Follow manufacturer's instructions for cleaning/maintaining PPE. Ifno such instructions for Precautionary
washables exist, use detergent and hot water. Keep and wash PPE separately from other laundry." Statements:
Hazards to
"Discard clothing and other absorbent material that have been drenched or heavily contaminated Humans and
with the product's concentrate. Do not reuse them." Domestic
Animals
immediately
following the
PPE
requirements
User Safety "USER SAFETY RECOMMENDATIONS" Precautionary
Recommendations Statements
"Users should wash hands before eating, drinking, chewing gum, using tobacco, or using the toilet." under:
Hazards to
"Users should remove clothing/PPE immediately if pesticide gets inside. Then wash thoroughly Humans and
and put on clean clothing." Domestic
Animals
"Users should remove PPE immediately after handling this product. Wash the outside of gloves immediately
before removing. As soon as possible, wash thoroughly and change into clean clothing." following
Engineering
Controls
(Must be
placed in a
21
,,.- - ....""
,f '
,.,,.-----~.,
.,..--......_
box.)
Environmental "ENVIRONMENTAL HAZARDS" Precautionary
Hazards Statement Statements
Do not apply directly to water, or to areas where surface water is present or to intertidal areas under
below the mean high water mark. Do not contaminate water by cleaning of equipment or disposal Environmental
of wastes." Hazards
Restricted-Entry Interval "Do not enter or allow worker entry into treated areas during the restricted entry interval (REI) of Directions for
for products with WPS 48 hours." Use,
uses Agricultural
Use
Requirements
Box
Early Entry Personal "PPE required for early entry to treated areas that is permitted under the Worker Protection Directions for
Protective Equipment for Standard and that involves contact with anything that has been treated, such as soil or water, is: Use,
products with WPS uses Agricultural
> coveralls, Use
> shoes plus socks, Requirements
> chemical-resistant gloves made of any waterproof material, Box
> protective eyewear."
General Application "Do not apply this product in a way that will contact workers or other persons, either directly or Place in the
Restrictions for products through drift." Direction for
with WPS or non-WPS - Use.
uses on the label "Only protected handlers may be in the area during application."
PPE that is established on the basis of Acute Toxicity of the end-use product must be compared to the active ingredient PPE in this document. In the case of multiple
active ingredients, the more protective PPE must be placed on the product labeling. For guidance on which PPE is considered more protective, see PR Notice 93-7.
22
\
Stephen M Mudge
November, 2005
c
© 2005 The Soap and Detergent Association. All Rights Reserved.
Table of Contents
Chapter 4.....................................................................................-._··························45
Metabolism ofFatty Alcohols ..................................................................................... 45
Natural degradation ...................................................................................................... 48
Short chain moieties ..................................................................................................... 49
Long chain moieties ..................................................................................................... 53
Degradation Rate Constants ......................................................................................... 55
Phytol degradation ....................................................................................................... 57
Effect of chemical associations on transformation rates .............................................. 57
''Natural" fatty alcohols in STPs .................................................................................. 57
Anthropogenic fatty alcohols in STPs ......................................................................... 59
<G 2005 The Soap and Detergent Association. All Rights Reserved. 1
i
I
The published and grey literature on the environmental occurrence, fate and behaviour
of fatty alcohols has been reviewed. The principal focus has been on the natural
production, which occurs in all living organisms from bacteria to man, and the
profiles and co1;1centrations of these compounds in water, soils and sediments. Their
relatively non-polar nature means they are principally associated with solid phases
(e.g. sediments) rather than dissolved in water. The major production mechanism is
from the reduction of fatty acids, through aldehyde intermediates, to fatty alcohols
and in many organisms to esters with fatty acids to form waxes. These waxes are used
for a variety of purposed from the prevention of desiccation in the terrestrial
environment to energy reserves in the ma.rine envLron.rnent. They are ubiquitous and
occur in most environments around the world including the deep ocean and in
sediment cores.
Due to the nature of the synthetic pathway using acetyl-CoA, most fatty alcohols are
of an even chain length. Terrestrial plants utilise fatty alcohols as waxy coating and
·lliese· coinj>OWic1S areaoriiliiiifod-oy-1ong cliain moieties with cham leiiglhS from C22 to ·
C32; in contrast marine organisms synthesise smaller compounds with peak chain
lengths of C1 4 to C16· Bacteria also produce fatty alcohols but these can als_o be odd
chain lengths and contain branches. Titls aspect of their occurrence enables them to be
used as biomarkers for organic matter sources.
As well as their natural production and occurrence, fatty alcohols are also utilised in
detergent formulations principally as polyethoxylates. The analytical method used to
measure the concentration of the ethoxylates involves direct derivatisation with a
pyridinium complex and quantification via LC-MS. This technique will detect free
fatty alcohols as well as the ethoxylates but will not detect any of the bound alcohols
such as the waxes. To detect this group, a saponification step is required. This second
method in combination with the LC method will detect all of the ethoxylates and may
be considered a good measure of the total fatty alcohols present in the system.
The concentration ofindividual fatty alcohols in the environment ranges from low
values in old deep cores and the open ocean floor {undetectable to 12 ng.g"1 DW for
C16) to high values near natural sources and especially in suspended particulate matter
The different compound profiles for each source has made them suitable as
biomarkers and the use of multivariate statistical methods can clearly distinguish
compounds from each potential source as well as sites. Principal Component Analysis
(PCA) is particularly useful in this regard. Signature analysis using Partial Least
Squares (PLS) analysis is successful when the marine I terrestrial sources are used to
discriminate samples, however, due to the commonality of commons present in
detergent formulations and the natural environmental alcohols. source partitioning on
the basis of compounds alone is not as successful. When ascribing proportions to such
sources, a different approach such as stable isotopes may be more appropriate. .
Key issues and directions for further study which have arisen from this review include
(
-·-·--···· ~----~~}a.~-~~-~l?~~i?!'o~~~~np~es~~~wJi~-~~P~~~~~~~h_o~~~9~ti~~;- ________ _
no corresponding measure of total (including wax bound) alcohols is made and this
may serve as a useful indicator of the relative importance of each source. Further
information is· needed on the rates at which free alcohols may be derived from bound
sources or fatty acid precursors both in sewage treatment plants and in the
environment as a whole. These aspects will .have repercussions on the toxicity and
ecotoxicity of alcohols in the environment, an aspect that was not included in this
review.
(
i,
compounds, how they are referred to, the likelys_tructures that will befoimd and their
chemistry.from an environmental point ofview).
The generic structure of fatty alcohols or n-alkanols can be seen in Figure 1.1 and
specific examples in Figure 1.2. The value of then component is variable and is
discussed below.
Figure 1.1 Generic structure of a: fatty alcohol -the total number of carbons needs to
be greater than 8 - 10 to be a "fatty" alcohol; shorter chain compounds have an
appreciable water solubility.
The range of chain lengths for these n-alcohols can be from 8 to values in excess of
32 carbons. With such a wide range of chain lengths, the chemical properties and,
consequently, environmental behaviour vary considerably. As well as these straight
chain moieties, a range of branched chain compounds are also naturally produced by
micro-organisms in the environment. The major positions for the methyl branches are
on the carbons at the opposite end of the molecule to the terminal -OH. If the methyl
branch is one in from the end of the molecule (co-I) it is termed an iso fatty alcohol; if
it is two in from the end (co-2) it is called an anteiso fatty alcohol. Examples of these
branches can be seen in Figure 1.2.
Figure 1.2 Example fatty alcohol structures. The majority found in nature are of the
straight chain type with smaller amounts of the branched chain compounds also being
present.
Most fatty alcohols are saturated in that they have no double bonds present in their
structure. However, there are a limited number of mono-unsaturated compounds that
can be found in nature. The two most C01JllD.On compounds are phytol (3,7,11,15 -
tetramethyl-2-hexadecen-1-ol), an isoprene (Chikaraishi et al.• 2005) derived from the
(
\
.. s~d~ ~h~ of C?bJ~!OP~YP. ~i-~ 1.~)_an_d ~ s_~~8!i! ~~~~-~Q .~~o!i~I_\!i~ _!1 E~'!.We __________ .__ _
bond in the ro9 position counted from the tenninal carbon (eicos-11-en-1-ol, Figure
1.4, (Kattner et aL, 2003).
OH
phytol
Figure 1.3 The chlorophyll a molecule with the phytyl side chain labelled~ Cleavage
( of this chain at the COO- group produces free phytol in the environment.
\.
Figure 1.4 Eicos-11-en-1-ol or 20:1 fatty alcohol, one of the most frequently
measured straight chain mono-unsaturated alcohol in the environment
There have been occasional reports of polyunsaturated fatty alcohols but these are
relatively rare (e.g. Ju and Harvey, 2004) and are confined to di-unsaturates such as
18:2. There is a group ofisoprenoid lipids which may be found in bacteria which are
essentially repeating isoprene subunits strung together and tenninated by a hydroxyl
group (Perry et al., 2002). These compounds are also uncommon in environmental
analyses and are not reported to any great extent.
Fatty alcohols together with many other groups of compounds have both systematic
and trivial or common names. This trivial name is based on the length of the alkyl
chain and the root is common between aliphatic hydrocarbons and fatty acids. These
names together with the systematic name and carbon JJ.umber are shown in Table 1.1.
Physii:o-Chemical Properties·
One of the key factors in detennining the environmental behaviour of any compound
is its water solubility; this will detennine the partitioning between solid and solution
phases. Compounds with low water solubility will be preferentially adsorbed to
particulate matter, either settled or suspended in water. These compounds will also
partition into the lipid phase of organisms and have higher bioconcentration factors.
The available physico-chemical properties for the fatty alcohol series from Ci to C30
are summarised in Table 1.1. These data are drawn from many sources but principally
from the Beilstein Chemical Database {Elsevier :MDL). The density and melting
points in the summary data (Table 1.1) have a degree of uncertainty about them as
some compounds, especially the longer chain and odd carbon number moieties, are
less well studied. The density data are not available for all compounds.
MQNQGRAPH
REPQRTDATE
November 15, 1991
PROJECT NUMBER
PATF-9101
REPORT AUTIIOR
Bemalyn D. McGaughey, Compliance Services International
DATA REQUIREMENTS
.\ Pesticide Assessment Guidelines, Subdivision N, Sections
160-S, 161-1, 161-2, f61-3, 162-1;'1'62-3, l&:r-:1, 164-f: I6S-4
SPQNSOB.
Fatty Alcohol Task Force
c/o Cochran Corporation, 2227 Deadrick Road, Memphis; Tennessee 3811~3
901-452-2107 .
· PERFQRMJNG LABQRATORY
Compliance Services International
700 Seafirst Center, 950 Pacific Avenue, Tacoma, Washington 98402
206-272-6345 .
STUDY DIRECTOR
Beroalyn D. McGaughey
Page 1 of~
.(.
\...
(
\
Compliance Services lpternational Report Number FATF-9101
Patty Alcohol Compounds Page S
I. ABS'11RACT • . . • • . • • • . • • . . • . • . • • • • . • • • . . • • • . • • • • • • • . . . • • • • • • • • • • • •
n. 1NmooucnoN ............................................ _... .
m. GENERAL INFORMATION •••••••••.••.••••.: •..•••••••••.........•
.'XV'II... FIGURES . . . . . ~ . . . . . . . . . . . . .. . . . . . . . . . ~ . . . . . . . . . . . . . . . . . . . . . ·
....·
Compliance Seivices International Report Number FATF-9101
Fatty Alcohol Compounds Page 6
\
f
I.ABSTRACT
The scientific da41 bases available by on-line access to the Dialog Information Services
were searched for information on fatty alcohols and their behavior in the environment.
The data reviewed and presented here support many of the basic assumptions of fatty
acid metabolism and straight-chain carbon compound breakdown. Fatty alcohols have
been investigated as }?iomarkers, because they are associated with virtually every life
form. Different species have different ranges of chain-length alcohols, and are variously
able to transform these products into shorter or longer<hain fatty acids, ketone, glycols
. or other compounds which are natural components of living organisms.
The fate and metabolism of straight-chain fatty alcohols is explained by basic biochemi-
cal principals. The compounds of interest in tobacco sucker control are short chain fatty
alcohols, primarily C1 and C10 norm.al alcohols, with small amounts of C8 and 0 111 normal
alcohols. Many of the articles reviewed dealt with chain lengths above and below this
number, or with iso- or antesio-chains; some investigations on fatty alcohol detergents
}.lave valuable information, but dealt with fatty alcohol ethoxylates.
) While no reviewed information addresses the classical requirements of the EPA guide-
lines Jor environmental fate testing, there does appear to be some inforn-uLtion available
which -allows the prediction of the behavior of n-fatty alcohols of 0 6 to C12 chain length.
Basic breakdown in alt" systems is by 2-carbon oxidation, followed by mineralization or
use of the components in fatty acid synthesis pathways.
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· Fatty Alcohol Compounds Page 7
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IL INTRODUCTION
As requested by the EPA in Dr. Allan S. Abramson's letter to Harley D. Hathaway of
Cochran Corporation (August 21, 1991), a literature search was conducted to address the
environmental fate aspects of the FIFRA Section N Guidelines for Pesticide Registration.
A search of on-line data through Dialog Information Services was conducted on Septem-
ber 8, 1991. The ..science end technical files" of Dialog were searched (120 files). No
effort was made to limit this search by alcohol chain length or nature. There were
11,456 citations availa'ble on fatty alcohol compowids. In order to develop a reasonable
list of citations, terms related to environmental fate were used to nBITow down the num-
ber of "hits" on the data system. A print-out of 677 citations was the result of this
search process; many of the citations had abstracts included. Particularly relevant arti-
cles, which were available in the English language, were obtained for review.
Where abstracts presente·d relevant information, b~t the article was _either not directly
related to our investigation or was published in a language other than English. appropri-
·ate excerpts of the abstract were noted in a bibliography. Full copies of articles were
·,reviewed and built into the bibliography on fatty alcohols. Lastly, articles which were
•.
; described or cited by authors whose publ~cations are reviewed here (secondary references)
) .were included in the bibliography as possible further source documents. Time did not
· ·allow the procurement of secondary references. It is important to includ!;! these publica-
tions in our list, since much of the research on fatty alcohols was elementary in that the
predictability of the behavior of the compound is based on early biochemical discoveries
related to the metabolism and global recycling of organic carbon compounds. · All refer-
ences found to be relevant (abstracts, reviewed articles and secondary references) are
included in the appendix of this document.
The body of this document is arranged by guideline number, in accordance with the data
requirements this monograph was intended to address. AB might be expected, no publica-
tions approached fatty alcohol fate in a typical FIFRA-guidellne testing ~fi!r. The
findings of various authors do corroborate one another and can lead to a buic under..
standing of the behavior of normal (or straight chain saturated) fatty alcoh~Is•
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Fatty Alcohol Comoounds Page 8
Fatty alcohols for use in tobacco suclter control are from natural and synthetic sources.
The process of manufacture or isolation of the chain lengths of interest is by one of two
·· means: hydrogenation of natural raw materials, such as coconut oils or palm kernel oils
or the Zigler alcohol process which uses petrochemical feedstocks. The fatty alcohols
·synthesized by the Zigler processes are structurally similar to natur~ fatty alcohols
(Noweck, 1987). These processes are the. most appropriate for providing the basic ingredi·
ents of sucker control agents due to their production of materials which are high in
· purity and due to the range of chain-lengths obtained.
In the following discus&ions, several synonyms for primary alcohols will be u.Sed inter-
changeably, These are: n-fatty alcohols, l·xxxxol (where xxxx is the description of the
chain length), straight-chain alcohols, [normal] aliphatic alcohols and saturated alcohols.
For ease in identification of the nomenclature which relates to various chain·Iengths, see
Table 1.
; Son._e very valuabie information comes from BW.dies conducted on biodegrtidable deter-
gents which are based on fatty alcohol. These studies followed the fate of the ring com-
pounds a8 well as the fate of the straight-chain alcohols and used radiolabeled tracers to
identify those components. The findings confirm the assumptions that .basic ~arbon
oxidation and fatty al~hol assi,milation or ~alization is rapld m;u~ c~inplete, without
the formation of exf:>tic metabolites. ·
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Fatty Alsahol Compounds Page 9
Fatty alcohols are aliphatic alcohols with chain lengths between CG and Cu; alcohols
with a chain length above C 12 are refen-ed to as "wax alcohols". Coconut ("natural")
alcohols produce very few impurity peaks and contain less than 0.1% n-tridecanol and
varying amounts ofn-alkanes. Zigler alcohols are primary, straight chain alcohols with
an even carbon number. Gas chromatography shows up to 1.0% impurities, consisting of
numerous even-numbered, isomeric fatty alcohols (Noweck, 1987).
The compounds used in tobacco sucker control predominantly contain C1 (1-octanol) and
· 010 (1-decanol),which are considered the effective ingredients in sucker control. The
presence of C41 and Cu1 are. partly due to artifact and partly due to their contribution to
the desiccation properties of the product. Saturated fatty alcohols up to 1-dodecanol (C1J
are clear, colorless liquidS with a lower specific gravity than water. The lower members
of the series have a characteristic odor. Boiling points and melting points increase uni~
formly with chain length. There ere no gaseous alcohols. Sinniah (1983) reports a melt-
ing point value for 1-decanol which is significantly different from that reported by No~
week (-26.6° vs. 7°0, respectively). The influence of the polarizing hydro"Yl group dimin-
..
ishes with chain length; thus hexanol and even octanol show some water solubility, but
l
decanol is immiscible with water. Fatty alcohols are soluble iii common organic solvents
such as petroleum ether, lower alcohols, and diethyl ether (Noweck, 1987).
Available details on the production, properties and nomenclatme of fatty alcohols are
given in Tables 1, 2, 3 and 4 and in Figure L Approximately 60% of the fatty alcohols
produced are based on petrochemicals. Price fluctuation in raw materials (natural versus
petrochemical) could affect the future distribution of the use of these two raw materials.
Fatty alcohols and their derivatives are used in synthetics, surfactants, oil additives and
C:osmetics (Noweck, 1987), as well as in the uses being supported by this review.
In Chemistry for Agrlcylture and Ecology. the author makes the followins }Jl"esentation
regarding general ~c: di~
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Fatty Alcohol Compounds Pai:e 10
Hay notes further that the length of the chain has a small effect on the chemical proper-
ties of the eompo~d, but can have a large effect on the physical properties of_ the com-
pound, such a6 melting poin~, boiling point and solubility (as we see in the information
from Noweck, 1987). The high temperatures for changes of state and the high water
solubilities of C1-C1 alcohols are due to the formation of strong hydrogen bonds between
hydroxyl groups of the molecules and water molecules. However, as the hydrocarbon
chain becomes longer, its hydrophobic properties dominate. This dominance is generally
reported to occur at a chain length of 10 carbons.
Alcohols are very weak acids. For their ionization, K. values vary from 10-13 to 10-18,
depending upon the length of the carbon chain. Primary alcohols are oxidized by strong
oxidizing agents, such as potassium dichromate or potassium permanganate, and yield
first aldehydes and. subsequently carboxylic acids. Alcohols react with carboxylic acids to
· give·esters; for example, ethanol reacts with acetic acid to give ethyl acetate. Alcohols
may also be "condensed to form carbohydrates or other more complex molecules. Prima-
ry alcohols are very basic building blocks of organic molecules, and without biological
processes or extreme conditions not foun~ in the environment, n-fatty alcohols would be
expected to be generally inert.
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Hydrolysis studies reported in the literature ere based on studies which utilize more
complex compounds than normal saturated fatty alcohols. Lindstedt (1990) reported that
fatty alcohol esters hydrolyze and produce normal human metabolites. The fate or action
of hydrolysis on the chain itself was not discussed in the abstract which was reviewed;
contents of the abstract suggested that the information was not ·directly relevant to the
range and charac;ter of alcohols in which we have an interest.
In studies by Hosotani, Ohkochi and Inui (1988), there WaS no apparent interference from
hydrolysis when the photoassimilation of fatty alcohols was studied in Euglena .gracilis Z.
Experiments were run in both light and dark conditions; in studies using sucrose as the
nutrient source, hydroiysis of sucrose was reported to have interfered. No such mention
was made for the studies conducted with fatty alcohols as a carbon source. Euglena
cultures were maintained for up to 14 day~.
The properties of fatty aicohol as displayed by the available literature suggest that
hydrolysis is not a major degradation pathway for n-aliphatic alcohols. The behavior of
lower chain (C2 to CJ alcohols in water-based formulations and their use as solvents in so
many arenas suggest that decomposition by hydrolytic means is not a factor. The influ-
ence of the polarizing hydroxyl group, which in turn influences miscibility, diminishes
:with chain length (Noweck, 1987). The Use of octanol in the FIFRA. guideline study
which determines an "octanoVwater. parlition coefficient" is also a statement toward the
stability of octanol under sterile solution conditions.
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· Peltzer and Gagosian (undated) compared concentrations of fatty alcohols in air and rain-
water samples in order to test the efficiency of their sampling and analytical methods.
Their interest was in the analysis of fatty alcohols and their use as biomarkers. No
report of interference due to breakdown in water was given in the abstract reviewed
here.
The single study found that specifically dealt with hydrolysis assessed breakdown by
titration, with the experimentation being conducted on fatty alcohol esters (Brown, 1983).
Since specific break.down products were not identified, and the parameters of the test
were·far from those of "natural" conditions, the study provided no additional data specific
to n-fatty alcohols.
The fact that marine and riverine surface sediments and oceanic surface samples contain
/ fatty alcohols and acids which reflect the nature of life or organic carbon soui:ces they
contain (Sargent, et. al., 1983; Romankevich et. al., 1982; Garrett, 1964) also supports the
thesis that these compo\lllds do not degrade readily by photolysis.
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VII. SECTION N GUIDELINES, 161-3: PHOTODEGRADATION - SOIL
AB with the literature citations on photolysis in water, no_ studies were found .which
specifically dealt with this aspect of fatty alcohol behavior. 'Many researchers have
· undertaken to utilize fatty alcohols as biomarkers in identifying the origin of 8ncient
sediments and in identifying the airborne sources of carbon compounds (Sargent et. al.
· (1983)i Simoneit (1989); Simoneit and Mazurek (1982)j Currie and Johns (1989); Venka·
tesan and Kaplan (undated); Sever and Parker (1969)). These researchers have found
that the distribution of fatty alcohols and fatty acids in th~ samples collected are in
many cases representative of the distribution of life forms which created the sediment or
particulate matter dispersed tlµ-oughout the associated environment. These similar
"fmgerprints" suggest that these compounds are relatively stable when not being cycled
through a living organism. The presence of-fatty alcohols in sedimentary rocks and in
uncontaminated soils (Roering (1969); Ambles (1991)) further supports this thesis.
(
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Several investigators have worked with isolated soil organisms to determine the ability
of such organis~ to degrade fatty alcohol or to use it ~ a food source. In experiments
by Buning-Pfaue and Rehm (1972), Pseudomonas aeruginosa was able to produce fermen-
tation products based on. the use of decanol as a sole source of nutrients. His fmdings
suggested that soil microorganisms of this type readily incorporate fatty alcohols into
their nutrient assimilation cycles.
Ambles, et. al, 1991, noted that soil lipids include a great number of neutral or acid
components (including fatty alcohols). These h~ classed es •simple lipids";. the ~own,
barely soluble fraction was reported as complex·lipids or the "po.Jar fraction" of the soil
lipid components. Ambles observed that the experimental work of others (and his work)
."suggested that the soil polar fraction may correspond to a polar matrix (a biopolymer)
which can 'react' with: simple lipids, [with] the process of incorporation of simple lipids
b~g reversible in biologically active soils."
In his work, Ambles compared. the simple lipids. in the soil to breakdow:n products of the
'"polar fraction". Even .carbon number, straight Chain fatty alco~ols.~re found in soils
from the two locations he tested. His work 84owed that the distributj.on of simple lipids
was fairly similar to the produc~ derived from the bre.akdown o( the .polar fraction and
that his initial pre~ may be valid. This work provides evidence that microbielly
active soil has an existing metabolic pathway for .the immediate incorporation of short.
chain fatty alcohols such as th~e used in to~acco sucker control. Since componepts Qf
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Fatty Alcohol Comoounds Page JS
the formulation are already naturally present in the soil, microbial metabolism may be
expected to proceed rapidly, with the use of 0 8 and 0 10 normal alcohols as a food source.
Fatty alcohol based detergents and surfactants have been shown to degrade thoroughly
and completely in the environment (Steber, et. al, 1988; Richterich et. al, 1985). Steber
reported generally that this group of detergents showed a very rapid and complete
biodegradation under both aerobic and anaerobic conditions with respect to j>rimary
breakdown and ultimate degradability (mineralization and assimilation). Richterich
reported a biodegradability (the German BiAs reduction test) of 93% to· 98% for a 0 1./018
· based fatty alcohol deter~ent.
The straight chain fatty alcohol sulfates (detergents), whether derived from natural
alcohols, natural fats or oils, or from ethylene by Zigler-type processes, are generally
considered to be completely biodegradable (Speel, 1963).
'fhe relationship of the above articles to the degradation of fatty alcohol will be discussed
further in Section IX (Anaerobic: Aquatic Metabolism); investigations with [1·14CJ.stearyl
alcohol ethoxylate and EO-labeled compound further identify the specific behavior of the
alkyl portion of that compound. Two Italian language articles were not translated which
.could support further the microbial breakdown of aliphatic alcohols (Sabastiani et. al,
1971). Work by Langley (1970), which investigated the properties of monolayer films in
connection with their proposed use as evaporation control agents, is also reported in the
1'.ext section. The work reported in that section reinforces the 8.ssumpti,on that metabo-
.\ lism of fatty alcohols in soil is rapid and complete and without the formation of exotic
} metabolites.
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IX. SECTION N GUIDELINES, 162-3: ANAEROBIC AQUATIC METABOLISM
The ~bic and anaerobic degradation of fatty alcohol-derived detergents has been well
reported in publlshed literature. Since some of these studies follow the fate of the fatty
alcohol moiety, they are valuable to our understanding of the aquatic metabolism of
these eompounds. Fatty alcohols are generally accepted as biodegradable under both
aerobic and anaerobic conditions (Steber, et. al, 1988) and will be used as a carbon source
by the microorganisms which occupy those respective environments. The pathway of
incorporation and the assimilated products may vary based on many environmental
factors, but all assimilated products will be typical compounds found in the fatty acid
synthesis process which is basically "common" to all life forms.
The articles reviewed below give credence to the statement made above. They also
provide some evidence of the possible end points which would be typical in a classical
FIFRA guideline study on aerobic or anaerobic aquatic metabolism.
E. gracilis growth varied depending upon the chain length of the alcohols included in the
culture medium. 1-dodecanol (C1J, 1-tridecanol (018), and l-tetradecanol .(014) supported
considerable growth Under illuinination. Assimilation of dodecanol and tetradecanol for
growth strictly depended upon lighl The fatty alcohols C11-Cu inhibited growth, while
methanol and the alcohols 0 15-020 did not support growth. The growth pattern of E.
gracilis on fatty alcohol is shown in Figure 2.
.The reason for variance in growth rates from one compound to another was not clear.
·The alcohols with chain lengths of 5 to 11 carbon& inhibited photoautotrophic growth
completely, and killed the cells. 0th~ varieties .of Euglena gracilis have been reporte~ to
grow o~ these middle. carbon-chain-length alcohols.
The results of the photoassimilation experiments sliow that photosynthetic energy is not
·completely necessary for the photoassimllatio~.ofthe.alcohol. Shading ()f Euglena grow-
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ing on myristyl alcohol may have caused the accumulatiOn of paramylon and lowered
synthesis of amino acids and protein which ~e essential for the cell growth. The
bleached mutant has been shown to adapt. to my-ristyl alcohol medium after several
transfers and an increase in (NHJ2SO, concentration. The mutant may induce an ability
to synthesize amino acids from myristyl alcohols by this adaptation.
Steber and Wierich, in two publications (1983 and 1986), discuss the biodegradation of
fatty alcohol ethoxylates. their work is particularly relevant to our interests here due to
the labeling of both the alkyl chain and the ethoxylate in separate but parallel experi-
ments. The [1-14CJ stearyl alcohol • 7 EO had a specific activity of 19.2 mCi/g; the
radiochemical purity was 98%. Only the results of the experimentation conducted on the
labeled alkyl compound is discUssed here.
In the first publication (1983), the simulation tests used a model plant which was a
miniature continuous flow activated sludge unit constructed according to Swisher. The
die-away tests were discontinuous tests analogous t.o the OECD Screening Test and were
perfonned in shake flasks modified t.o a closed system. In the simulated plant study,
after a working-in period of approximately two weeks the plant was fed for about one
week with synthetic sewage containing one of the radiolabeled surfactants. AB expected,
the carbon in the I-position of the elkyl·labeled compound was mineralized to HCQ2 to a
greater extent than the EO-moiety·of the analog9us icc.EO surfactant. Mineralization
rates were 50 to 60% after 2 to 3 days of 14C-feeding, with a slightly increasing tendency.
'.fhe radioactivity of the efiluent from the· alkyl-labeled surfactant only amounted t.o
'1 about 6% (undegraded). When results were adjusted for recovery (93.8%), it was reported
J that 99% of the fatty .alcohol ethoxylates present in the influent incurred microbial
attack within 3 hours retention time in the model plant. ·
The lipid fraction of the ·sludge from the [1-1'C] alkyl ethoxylate experiment had a consid-
erably higher radioactivity than sludge from the ring labeled experiment. This was· ·
explained as a consequence of microbial degradation of the alkyl-chain via ti-oxidation
according to general biochemical pathways, resulting in the production of acetyl units,
which represent the elementary precursors for fatty acid biosynthesis.
The relatively high surfactant content in the sludge may result from the comparatively
low water solubility of stearyl alcohol + 7 EO. Additionally, the hydrophilic ECkhain of
alcohol etho.xyJates exhibits a slower bJodegradation rate than the hydrapho&Jc part of
the surfactant molecule. The faster biodegradation of the alkyl chain is clearly shown by
the fact that the intermediates of the [1-140] _stearyl alcohol ethoxylate biodegradation
found in the effiuent consisted largely of higher EO-numbered acidic polyethylene glycols
which obviously must contain a small uc labeled moiety. In addition, it is evident that
these polyethylene glycol earboxylates can only arise if degradation -of the alkyl chain
.starts at the terminal methyl group. This is in accordance with conclusion,s drawn by
other authors.
.The alkyl ch~ of the fatty alcohol ethoxyh~te exhibited an ultimate biod.egradation of
about 76%. The actual extent of degrad,ation may exceed this value for two reasons: q)
µie steady state. mineral~on rate was higher than the balanced. value of total 1'001-
evolutiQn an~
. (2). an :undervaluation
. .re.suits
. from ~ ~4 C·labeling position
- . in connection
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with the degradation mechanism. The biodegradatlon begins at the terminal. methyl of
the alkyl chain, so that in this case, the alkyl carbon in position 1 represents the last
carbon being transformed.
From these studies it was concluded that the biodegradation of stearyl alcohol + 7 EO
formed no recalcitrant metabolites and would be expected to completely ·biodegrade under
primary sewage treatment, as well as by self-purification processes in surface waters.
These ~dings relate. to both aerobic and anaerobic metabolic pathwgys.
A second study by these authors was published in 1985. Here, Steber and Wierich report
that there are two distinct primary degradation mechanisms acting simultaneously in
the microbial biocenoses of fatty alcohol ethoxylates: intramolecular scission of the
surfactant as well as tat- and ti-oxidation of the alkyl chain. In this report, a picture of the
microbial pathways that bring about ultimate biodegradation of fatty alcohol ethoxylates
in the environment were made. Studies were again conducted in a model continuous
flow activated sludge pl~t simi.lar to that described by the OECD Conf1.rma~ry Test.
A fast degradation of the fatty alcohol moiety of the surfactant occurs, beginning with
terminal methyl group and slowing down before the radiolabeled C-1 is reached. The
terminal oxidation of the alkyl chain. (c.>·oxidation) and subsequent stepwise removal of C1
Units by 13-oxidation is presented as the fatty alcohol chain metaboljc process. The result-
ing products represent the elementary precursors of fatty acid biosynthesis.
. .
.. In addition to the above work, Speel reports that sodium lauryl sulfate (Cu} disappears
) from water in less than 3 days. The studies with fatty alcohol detergents have generally
demonstrated "complete biodegradeability" in three days or less.
Work by other authors has shown that straight-chain alcohols may be a preferred carbon
source, or at minimum microorganisms require little conditioning to utilize norm.al fatty
alcohols as a carbon source. Langley (1970) conducted experiments on hexadecanol (C 1J
and octadecanol (C1J in conjunction with research on the control of water loss from soil in
the arid southwest. In conjunction with these efforts, this project was de8igned to meet
two goals: (1) to investigate the behavior of hmdecanol and octadecanol ·in ~icrobial
systems, including the detection, identification and behavior of any intermediate or end
products formed as a result of biological transformation; and (2) to correlate the behavior
of long.i:hain fatty alcohoJs with studies of lower ·moJecuJar weight alcohols.
Three ,primary analytical techniques were employed to obtain ·Qirect and specific mea-
surements of the rate and extent of degradation of hexadecanol and octadecanol by adapt;.
ed mi~ganisms: gas chromatography,. total oi.-ganic carbon analysis and recorded
. oxygen uptake. A se~ed sewage supernatant was .used· as the so~ce .of mici'.obial organ-
: isms which were adapted to the alcohol. substrate. Low
chain lenith 8.Jcohols (3 and 5
carbon) were used to condition the S,Y$tem and demonstrate its capability to adapt to
&oluble alcohols as a carbon source. The higher chain alcohols were insoluble in water
but formed a film on ~e water S,W'face. Due wthis filming tendency, l·h!!xadecanol·and.
1-octadecanol were ~s_ted in a sta£ic env~~nt to avoid loss of the compound on ~k
walls. . · . . · : . . .
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1-butanol and l·pentanol were removed from the solutions within 4 to 6 houra. of their
introduction. When isopentanol was also present, there appeared to be a selectivity or
response which favored the straight chain alcohols. The total organic carbon removal
during this phase of experimentation approached first order microbial response with half-
lives as short as 2 hours. Shiillar responses were evoked when cultures were exposed to
isobutanol, 1-butanol and 1-pentanol; response to straight chain alcohols was virtually
non-selective and the removal or isobutanol was esse~tially stopped until the straight
chain alcohols were removed or converted.
~e complications of studying these compolinds in both the field and !~oratory were
discussed. The fact that solvents such as hexane or isopropanol must be used to disperse
the compounds in an aquatic system and the :ubiquitous presence of carbon make qualifi-
cation and identification of breakdown products extremely difficult.
In work with fatty alcohols as biomarkers, Simoneit and Mazurek (1982) reported that
absolute concentration of the homologs of <Cao in aerosol samples were not accurate
although quantitative comparisons could be made. They speculated that the presence of
shorter chain fatty alcohols were equal to or greater than the concentration of fatty alco-
hols which are > C.,. The quantitative comparisons made by Simoniet and Mazurek
whic.h include data on chain lengths of 10-35 carbons which are shown in Figure 3.
These authors propose that the concentration or <Cm fatty alcohols is relatively high in
· dispersed aerosols, end that the origin of these products is microbial activity resulting
primarily from the breakdown of plant waxes. ·
In a living aquatic system, be it aerobic· or anaerobic, fatty alcohol breakdown is rapid
and complete. Papers reviewed here suggest th.at the aquatic half-life· of shorter-chain
fatty alcohols may be a matter of hours, and is likely. to be less than 3 to 7 days. Be-
cause these types of compounds are a prefened· carbon source, they will be rapidly bioas-
.sim.ilated or mineralized to C02• ·
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Some of the papers reviewed and the chemical and physical properties of n-alipatic alco-
hols suggest that these compounds are not mobile in soils. One publication was found
which provides data on the movement of n-fatty alcohols in soil. Unfortunately a full
copy of this article was not available within the time period for this report's preparation.
However, the abstract does provide the following summary informatiol\: hydrogen
bonding was the primary attraction between the fatty alcohol compound and Wyoming
bentonite clay. Binding was rapid and strong, with virtually no lateral or vertical move-
ment detected. Fatty alcohols tendency to bind to soil and stay in place, and the ftlm-
forming properties of fatty alcohoJs of chain length C16 and above, are the specific proper·
ties which lead to the investigation of these compounds as evaporation inhibitors in soils
where water Use is critical.
The discovery of fatty alcohols in sedimentary rocks Uioering, 1969) suggests that move-
ment is limited once the substrate involved is no longer bioactive. Microbial biosynthesis
or mineralization may result in the formation of fatty acids or other natural products as
well as carbon dioxide. The movement of these compounds may vary; however, they are
natural constituents of the soil and are likely to be thoroughly involved in the carbon
cycling process.
Again. no FIFRA-guideline type studies are available for the leaching, adsorptive and
desorptive properties of 0 1 to 0 12 alcohols, but the information presented above, and the .
general properties of these compounds as described by Hay (1981) suggest that this range
of fatty alco\lol compounds will not be mobile in the soil.
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In a later publication, Brengle (1969) conducted field tests of the ability of hexadecanol
and octadecanol to inhibit soil moisture loss. Octadecanol was broadcast at O, 300, 600 or
900 pounds per acre each May for three years. Fatty alcohol, at the rates used in this
study, did not retard soil wa~ loss enough to warrant use in a fallow 'system. The
treated area did maintain a protective vegetation cover. Apparently, even.these extreme-
ly high rates did not affect the productivity of the soil over the three year test period.
The dissipation of fatty alcohols from soils would be expected to follow first order kinet-
ics, with half-lives varying based on the level of microbial activity in the soil. Since most
agricultural soils are quite bioactive, and. receive fatty alcohols in the form of plant
waxes on a regular basis, the dissipation of C8 through C12 n-alcohols can be predicted to
be quite rapid. Use rates for tobacco &Ucker control are several orders of magnitude
} below those used by Brengle. Brengle used longer chain compounds; however, since
oxidation occurs carbon-by-carbon, the shorter chain compounds would be·degraded more
rapidly, if they are not simply assimilated for use in the fatty acid synthesis pathway.
Several studies in plants dealing with the synthetic pathways used in the production of
plant waxes and wax esters give some information on the level of low-chain .length fatty
alcohols which may be deposited in agricultural soils. That data is not included in the
Jection but is reviewed in the attached bibliography (see: Moreau and Huang, 1979;
Wilkinson, 1973; and Wilkinson, 1974). These studies also suggest that the variability of
background fatty alcohols in soil will be great, depending upon the specific environmen·
tal factors relating to plant ~wth, nutrition and soil metabolism.
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Fatty alcohols and wax esters are abundant in nature. The fact that one source of the
fatty alcohols us~d in tobacco sucker control agents is plant material is the strongest
evidence of their occurrence. Bioaccumulation would not be expected since these com-
pounds are constantly cycled through the carbon pool. Several articles reviewed support
this hypothesis.
Wax esters are an abundant source of energy in the marine envirOnment (Place and
Roby, 1986). Hydrolysis of wax esters produces fatty alcohols which then are oxidized to
or assimilated into fatty acids. Cycling of fatty alcohols begins at the "base" of the food
chain. Annelids, crustacea end single celled organisms all assimilate fatty alcohols and
acids end are important in affecting the flux of lipids through food chains (Bradshaw, et.
al, 1990 end 1990a; Hosotani, et al, 1988). •· -
Obst (1986) reported that the feces of wu-fed birds (Wilson's storm petrel) contain fatty
alcohol and fatty acid, again the products of. wax hydrolysis. Fish feeding on zooplankton
readily digest fatty acids of 0 18 to 0 20 chain length; higher chain lengths are excreted in
the feces. The same pattern would be expected for fatty alcohols, except that they ere
likely to be converted to fatty acids or synthesized into more complex molecules.
In further studies on fish, Cowey and Sargent (1977) followed the distribution and fate of
fatty alcohols which resulted from wax ester hydrolysis. These authors reported that
fatty alcohols were oxidized to the corresponding acid and thereafter follow pathways of
fatty acid metabolism. Some species were reported to have the ability to convert short
chain acids into longer chain polyunsaturated acids that have full essen~ial fatty acid
activity. 'lhis fin~g would suggest that pathways exist for the rapid assimilation of
fatty alcohols.
Similar .findings are reported in other types of organisms. Konµlick and Baue.rfeind
(1991) reported that dragonfiy larvae hydrolyze wax
esters and absorb &0th the fatty aeid
and fatty alcohol moieties. These moieties are then used in the synthesis of triglycerides
and wax esters. No accumulation of lipid droplets occurred after ingestion of free fatty
~cohol alone. Again supporting the rapid assimilation of this class of compounds.
Straight-cha.in fatty alcohols are considered "building blocks" in fatty acid synthesis and
i other carbon cycling pathways (Hay, 1981). The existence of these pathways provides for
mechi;misms which prevent bioaccumulation .from occurrhig. Hence, bioaccumulation in
fish, a result of the use of fatty alcohols in tobacco sucker control, dermitely w0uld not be
expected to occur. • '
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XIII. CONCLUSIONS
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Guideline Number 160-~ Chemical Identity: Normal fatty alcohols are considered chemi·
cally "inert" and are precursors to fatty acids. Their production and manufacture yields
a relatively pure product mixture, depending upon the "cut" desired. The C,·Cu alcohols
used in tobacco sucker control ·agents would be expected to contain no WlUSUal or high
levels of impurities.
Guideline Number 162-1, Aerobic Soil Metabolism= Aerobic soil metabolism is the major
degradation pathway for C8-C12 n-alcohols. Breakdown or assimilation by microbial
organisms is rapid and complete. Half-lives may be as short as a matter of hours, and
would not be expected to exceed 3 to 5 days.
Gu~line Number 164-1, Terrestrial Field Dissipatio,n: Dissipation of C.-Cu fatty alco·
hols \inder field rates and conditions is rapid and .complete. Half-lives as short as a
~atter of ho~ could be porsible. HalFlives woul~ not be upeeted ta exeeed. 3 t.a 5 dJJys.
· Guideline Number 166-4, Bioaccumulation in Fish: C8-C11 fatty' alcohols will not bioac·
cumulate in fish.
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,.
The final copy of this report will be archived in the Quality Assurance files of Compli-
ance Services International. The references collected will be retained or returned to the
sponsor and will be made available for further review if that is the desire of the sponsor
or regulatory agencies.
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XV. CERTIFICATION
The data presented in this report are true and accurate to the best of my knowledge end
were taken from peer-reviewed, published articles. Hypotheses presented on the behav-
ior of specific compounds are logical extensions of the information reviewed to date•
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.. _ __ Date: _ _ __
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XVI. TABLES
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Table 1. PHYSICAL PROPERTIES OF FA'ITY ALCOHOL
CAS Molecular Mi Hydroxyl mp. hp, ·c Density, Refractive
lUPACName Common Name registry No. formula Number ·c. (p.kPa) g/cm3 index
(t, ·c) (t, .C)
1-Hexanol caproic alcohol 111-27-3 C6 H 1 ~0 102.2 548 -52 157. 0.819(20) 1.4181(20)
1-Heptanol cminthic alcohol 111-70-6 C,H 160 116.2 482 -30 176 0.822(20) 1.4242(20)
1-0ctanol caprylic alcohol 111-87-5 C1H1e0 130.2 430 -16 195 0.825(20) 1.4296(20)
1-Nonanol pelargonic alcohol 143·08-8 C,Hzo{) 144.3 388 -4 213 0.828(20) 1.4338(20)
1-Decanol capric alcohol 112-30-1 C10H210 158.3 354 7 230 0.829(20) 1.4371(20)
1-Undecanol .... 112-42-5 CuH2,0 172.3 326 16 245 0.830(20) 1.4402(20)
~ 1-Dodecanol lauryl alcohol 112-53-8 C12H200 186.3 300 23 260 0.822(40) 1.4428(20)
u
·~ 1-Trldecanol 112-70-9 C13H210 200.4 280 30 276
Cl.I
}a~
1-Tetradecabol myrislyl alcohol 112-72-1 C 1 ~H,o0 214.4 261 38 172(2.67) 0.823(40) 1.4358(50)
1-Pentadecanol ··629-76-5 CuHnO 228.4 245 44 1.4408(50)
6
8 1-Hexadecanol cetyl alcohol 36653-82-4 C10H340 242.5 230 49 194(2.67) .0.812(60) 1.4392(60)
1-Heptadecanol margaryl alcohol 1454-85~9 C11H,,O 256.5 218 54
1-0ctadecanol stearyl alcohol 112-92-5 C18H310 207.5 207 58 214(2.67) 0.815(60) 1.4388(60)
1-Nonadecanol 1454-84-8 C1,H4o0 284.5 196 62 1.4328(70)
1-Eicosanol arachidyl alcohol 629-96·9 CioR.20 298.6 187 64 215(1.33) 0.806(70)
1-Heneicosanol 15594-90-8 C21 H~O 312.6 179 68
1-Docosanol behenyl alcohol 661-19"8 CnH4oO 326.6 171 71 2411.33 0.807(80)
",, ..
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XVII. FIGURES
.,
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.1101. A 10 Fatty Alcohols 291
.·
I fo0
L:100 h100 !:100 L:90
1· 30
. 20
j
~ 10
~ . 0 ..._,.,_,.,_,_ _,,.,..~,_.
6 8 10 12 14 1618 2 4 6 8 1012141618 202224 ~ 8 10 12 lC. 1618 20 10 12 14 16
Hydrogenation ·Ziegter- Modified Hydrag~na tion
of fatty acid Alfol . ~· Ziegler of fatty acids
methyl ester process process from paraffin
from coconut lEpall oxidation
oil
'i 20
§0 10
E
< 0 ~-..ud"!.Al,.f.lr.LI.-
•
10 12 14 10 12 14 10 12 14 10 12 14 16 18 20
Oxo alcohol Oxo alcohol Oxo alcohol Unsaturated
from by phosphine from ;lcohol from
.br~nche' · catalysis •.. statistical tallow
olefins n-olefins
-
.
- 15 ...
E ~
;!
tJ
-
u
.._
0
0
. 10 -
zx ..
.... ' .
0 .
5 - - ..
'
. ,.. -
~: . -.
-
0
-
2 J
...
4
- - -
t •V
~-......,..-
- I
:... ... ......
5 6 7 8 9 IU II 12 13. 14 15 16 17 18 19 20
- -. - -
Carbon-chain kngth of fatly alcohols
Photoautotropbically grown cells are transferred to culture media containing individual fatty
alcohol and cultivated for 14d with or without illumination. Initial cell number was 0.9· x 10"1•
Open and closed bars represent growth of Euglina with and Without illumination respectively.
A carbon chain length of 0 indicates photoautotrophic growth.
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a,4 b74
c• 111 26
26 18 t6 ie
18
24
'\., ... ,_ .
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32
~lv.i.3
37
16
nq/rn3
9
20
54
26 2S
I-·. - . 2?
tfti/tr:l • 2~
ZS
16
( :e
\
20 30
·- c-
21 ?O
I
to 30 4Q 10 zo 30 co '' ao ~ -. :c zc :!(
c- c- c - c--
Fig. 3 • Distnoutioa. diagrams for then-fatty alcohols: (a) Battle Creek M~ow Ranch (s:implc 6): lb} Suprpiae
Point State P:irk, night. summer (sample I); (c) S"Lem. Ski Ranch (s:implt S); (d) "Suprpinc Point State Park. winter
(sample 3): (c) D and D R.:mc:h. summer (s:i.mplc S); (I) Corvallis. forest {s:unplt 14): lt) C:mog-J Park. Santa Ana
conditions (sample 16); (h) Pasadena (sample 17); (ij Composited grass. ~-ax (sample :?O\: (jl Compositcdconifc.'"1. wax
·sample 21): (k) ~nan aerosol. Jos. Nigeria (Cox er al.• 1982): ll) Adantic Oc=n. ~ 4 {Simonet. 1977a.).
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XVIll. ANNOTATED BIBLIOGRAPHY
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\. \ .~bstracts only (-)
Article reviewed (,/*)
Referenced by author
and referenced information
is
presented . (*)
J"'Ambles, A., J.C. Jacquesy, P. Jambu, et al. 1991. Polar lipid fraction in soil- a kerogen-like matter. Organic Geochem-
istry 17(3):341-349.
.
. .
•soil lipids include a great number of neutral or acid components (hydrocarbons, esters, ketones, fatty alcohols and
acids) which can be easily studied ("simple Jipidsj and an unknown, barely soluble, fraction called •potar fraction• or
•complex lipids": •,
In reviewing the work of others, conducted to identify the relationship of simple lipids to complex lipids in soils, Ambles
observed that the exper~ental results •suggested that the soil polar fraction may correspond to a polar matrix (a
biopolymer) wbi~ can "react• with simple lipids, the process of incorporation of simple lipids being reversible in
biologically-active soils."
Ambles selected two hydromorpbic soils from the western part of France for his studies. He compared the s~ple lipids
in the soil to the breakdown products of the "polar fraction•. The n-alkabes displayed a relatively regular distribution
ranging from C16 to C,.. In further extraction processes, primarily even-carbon number, straight chain alkaJ}ols (maxi-
mum chain length Crz) were found in both soils. His work also showed that the distnoution of simple lipids was similar
to the products derived from the breakdown of the polar fraction of the soil, suggesting that his initial premise may be
valid, and that the polar fraction of the soil is a •smt• for the fatty alcohols and lipids introduced into the soil from plant
fractions and microbial activity. ·
*Aubertin, G.M., G. W. Gorsline. 1964. Effect of fatty alcohol on evaporation and transpiration. Agron. 156:50-52.
*Barras, D. R., & B. A. Stone. 1969. Carbohydrate composition and metabolism in Euglena. In 1be Biology of Euglena,
Vol. 2, pp. 149-191. Edited by D. E. Buetow. NY:Academi' Press.
Bradshaw, S. A., S. C. M. O~ E. D.S. Comer, et al. 1990•. Changes In lipids during simulated herbivorous feeding by
the marine crustacean Neomysil integer. Journal of the Marino Biological Association of the United Kingdom. 70(1):225-244.
The results of these investigations indicate that crustaceans such as that tested here would have a profound effect on fatty
acid and alcohol fractions in material that passes though the pelagic food chain; feeding activity of these organisms may
determine certain aspects of the sedimeDtary lipid distributions. ·
Bradshaw, S. A., S. C. M. O'Hara, B. D.S. Comer. 1990. Dietary lipid changes during herbivory and coprophagy by the
marine invertebrateNereisdiversicolor. Journal of the Marine BiologicaJ Association of the United Kingdom. 70(4):771·788.
Herbivorous and particularly coprophagous feeding by the annelid worm, Nereis diversicolor leads to relatively high
abundances of •bacterial• odd carbon-number normal and branched chain fatty acids and these organisms are important
, in affecting the flux of lipids through marine food cJudns.
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( ~rengt8, K. G. 1965. The behavior of fatty alcohol applied to soils. Dissertation, Michigan State University (reponed in
· ·1 .1.....sertation Abstracts International, 26(2):615.
Fatty alcohol absorption by Wyoming ventonite was studied by x-ray diffraction, differential thermal analysis, infra-red
absorption and angle of wetting. Hydrogen bonding was wumed to be the primary attraction between fatty alcohol and
ventonite. Fatty alcohols were found to be active in reducing water movement in soil at extremely high rates (see
Brengle, 1969). This research was conducted with a special interest in fatty alcohols as evaporation control agents.
Vertical and lateral movement of fatty alcohol in the soil was practically non-existent. the Jack of lateral movement
sugges? that compressed monofilms are not formed at the air-water interface· in the soil.
*Brengle, K. G., H. 0. Mann. 1969. Effect of fatty alcohol on change iii soil water during the summer fallow period.
Journal of Soil and Water Conservation. 24(1):25-26. ·
Hexadecanol and octadecanol were used ~ an experiment assessing the capability of th~ compounds to inhibit soil
moisture loss. Octadecanol was broadcast at 0, 300, 600 or '900 pounds per acre each May for three years. ·Fatty
alcohol, at the rates used in this study, did DOt retard soil water loss enough to warrant use in a fallow system. The
tteated area did maintain a protective vegetation· cover.
*Bro(ldin, G. W. Cautreels & D. van Cauwenberghe. 1980. On the aliphatic and polyaromatic hydrocarbon levels in urban
and background aerosols from Belgiwn and the Netherlands. Annospheric Environment 14:895-910.
~rown, H. 1983. The stability of esters to hydrolysis. Cosmetics and Toiletries. .98(12):56-58.
Six fatty alcohol esters were selected for hydrolysis studies: C1~u alcobOls beµzoate, isopropyl myristate, isopropyl
palmitate, lauryl lactate, dioctyl adipate and isononyl isononate. Lauryl lactate was included since it hydroly;es readily
and would be a good comparison standard reference. The hydrolysis methodology utilized 959'0 ethanol solutions and
pH levels of 2, 3, and 12. Ten percent ester solutions were prepared and subjected to 3 hour reflux and oven storage
(47° C for 30 days). Hydrolysis was measured by titration. The method utilized for alkaline hydrolysis was Inadequate
and no results were obtained. Under acid conditions, laurel lactate had the greatest degree of hydrolysis at.both 3 hour
reflux and 30 day storage intervals. While the behavior of the ester is determined in these studies, DO specific data is
provided on the alcohols or their stability in this system.
Buning-Pfaue, H., H. J. Re1un. 1972. Production of aldehyde from •batch• fermentation by Pseut1omoruu aeruglnosa
growing OD decanol. Arch. Mikrobiol. 86(3):231-40. .
APltlldomonas species was able to produce fermentation products based on the use of 4ecanol as a sole source of
nutrients. This suggests that soil microorganism readily incorporate fatty alcohols into their nutrient assimilation cycles.
*Cook, K. A. 1979. Degradation of non-ionic surfactant Dobanol 45-7 by activated sludge. Water Res. 13:259-266.
Cowey, C. B.• J. R. Sargent. tm. Lipid nutrition in fish. Comparative Biochemistry and Physiology B: Comparative
Biochemistry. 57(4):269-274.
Currie, B. R., R. B. Johns. 1989. An organic geochemical analysis ofteaestrial biomarkers in a transect oftbe Great Barrier
Reef Lagoon. Queemlaod, Australia. Australian Journal of Marine and Freshwater Research. 40(3):275-284.
Fatty alcohols, as well as certain other compounds are being used as •biomarJcers• to determble the deposition and
source of marine sediments. Fatty alcohols are deposited not only from terrestrial .sources but also from planktonic
sources and thus are not well correlated with distance-from·land.
I
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Fatty alcohols resulting from wax ester hydrolysis are oxidized to the corresponding add and thereafter follow pathways
of fatty acid metabolism. Some species have the ability to convert short chain acids into longer chain polyunsaturated
acids that have full essential fatty acid activity.
*Finnerty. W. R. &.. M. E. Singer. 1984. A microbial biosurfactant- physiology, biochemistcy and applications. Dev. Ind.
Mierobiol 25:3140. :
Garrett. Vf. D. 1964. The organic chemical composition of the ocean surface. Naval Research ~aboratory (Washington)
R.eport ~o. NRU;20l. N11S No. AD-610 396.
The major water-Insoluble organic constituents of the sea are.fatty esters, free fatty acids, fatty alcohols and hydrocar-
bons. The distn'bution of the various fatty acids and alcohols varies according to the meteorological and oceanographic
conditions prevalent at a particular location. The high molecular -weight and less-water soluble fatty alcohols are the
most surface active (likely to be found absorbed to the surface) while the more water soluble (less surface active)
compounds are excluded from the surface by competition with th~ compounds.
*Gentner, W. A. 1966. The influence of EPTC on-external foliage wax deposition. Weeds 14:27-31.
Gerllold, R. M. & G. W. Malaney. 1966. Structural Determinants in the Oxidation of Aliphatic Compounds by Activated
Sludge. Journal Water Pollution Cont Fed. 38(4):562-79.
JIHosotani, K., T. Ohkocbi, H. lnui, et al. 1988. Photoassimilation of fatty acids, fatty alcohols and sugars by Eugle1U
gracill.r Z. Journal of General Microbiology. 134(1):61-66•
.
The assimilation of fatty alcohols and other carbon sources by Euglena gracilis Z. was. inve.uigated by studying th1
growth of the organism and its photoassimilation of these compounds. This investigation demonstrates the effect of lip
on the growth of Euglena and compatt.\I the mechanisms of their photoassimilation.
E. gracills Z and its streptomycin-bleached mutant from established stock cultures were. exposed to growth medi:
containing 0.25 fatty alcohols (carbon chain lengths of 1 to 20). Cell numbers were :determined by hepw:ytomete:
counts. Where inve$tlgation included the use of 1-tetradecanol (myristyl alcohol), extraction was by chloroform, wid
· determination by gas-liquid chromatography.
. .
E. gracllU growth varied depending upon the chain length of the alcohols included in theculture medium. Ethanol wa
the best cubon source in both light and dart. Propanol, butanol, 1-dodecanol, l~ecanol, and 1-tertadecanol aJs.
supported considerable growth under ·illumination. Assimilation ~f butanol, dodecanol and tetradecanol for growr:
strictly depended upon light The fatty alcobols.CrC 11 inhibited growth, while methanof and the alcohols Cu-Ca did DC
support growth. .
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Fany_ Alcohol Comp~unds Page 39
20 .....
.
- 15 -
E ~
er.
CJ
-
:.J
c.....
0
. 10
o.
~ ..
;;z: '
....x
. .
0
,
.•
.
5 ...
.
~~
2
.. -5
3 4
- -
7
~
~
8
-
·v
~-
9 IO 11 12 13. 14
I- .. .. - .....
15 16 l 7 18
.._ ....
0 6 , 19 20
Carbon-chain length of fatly alcohols
..
... -:; ·
./
\,
Photoautotrophically grown cells are transferred. to culture media containing individual fatty
alcohol and cultivated for 14d with or without illumination. Initial cell number was 0.9· x 10-1•
Open and closed bars represent growth of Euglina with and without illumination respectively.
A carbon chain _le!i~th of 0 indicates photoautotrophic growth•
..
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Compliance Services International Report Number FATF-9101
Fatty Alcohol Compounds Page 40
( . .
The results of the photoassinulation experiments show that photosynthetic energy is not completely necessary for the
pbotoassimilation of the alcohol. The blue light receptor may take part in the pbotoassimilation of myristyl alcohol;
photosynthesis also appears to have some relation to photoassimilation since the occurrence of photosynthesis during the
soldering caused a higher cell yield •
..-Roering, T. C. 1969. Fatty alcohols in sedimentary rocks. Yearbook of the Carnegie Imtitute. of Washington. 67:202-
~. - . -
". • • Mild thermal treatment of unextracted recent sediment produced a good yield of the normal alkanes 11-CJJ.i& and
lJ-CuH,, and that under the same conditions recent sediment will reduce fatty alcohol to an alkane. These considerations
suggest that fatty alcohols in the form of wax esters may be p~esent in sedimentary rocks. Plant waxes are esters of fatty
acids and fatty alcohols •.• where [carbon chain lengths] typicalfy run from 12 to 30." [plus two for the initial and
.terminal carl>ons] • • • Fatty alcohols, presumably present in the fonn of wax esters, make a small but significant
contnlrution to the inventory of normal alkyl groups found in s~imentary rocks.•
*Ichikawa, Y., Y. Kitamoto & N. Hosoi. 1978•. Iregradation of polyethylene glycol ethers by a Pseudomonad isolated from
activated sludge. J. Ferm. Techanol. 56:403409:
*Joneda, T. 1984. Lips of Actinomycetes: Their structure and biosynthesis In Biological, Biochemical and Biomedical
Aspects of Actinomycetes. Ed. by L. Ortiz-Ortiz, L. F. Bojalil and Y. Yakoleff. Acad. Press. NY pp. 239-49.
*Jambu, P., G. Coulibaly, P. Bilong et al. 1983. Influence of lipids on physical properties of soil. Studies About Humus
Humas &. Planta. VIlI 1:46-50.
'· *Kolattukudy, P.E. 1968. Tests whether a head to head condensation mechanism occurs in the biosynthesis of n-hentriaconta-
ine, the paraffin of spinach and pea leaves. Plant Physiol. 43:1466-1470.
*Kolattukudy, P.B. & T. J. Liu. 1970. Direct evidence for biosynthetic relationships among hydrocarbons, secondmy
alcohols and kitones in Branica oleracea. Biochem. Biophys. Res. Commun. 41:1369-1374.
Komnick. B., R. Bauerfeind. 1991. Intestinal absoq>tion of defined lipids by the larval dragonfly Auhna cyanea ~
Odonata)- wax esters and fatty alcohols. Journal of Insect Physiology. 37(3):179/.
Dragonfly larvae hydrolyse wax esters and absorb both the fatty acid and fatty alcohol moieties. These components are
then used in the synthesis of triglycerides and wax ester. No accumulation of lipid droplets occurs after ingestion of free
fatty alcohol alone. Wax ester is a natural constituem of the larval cuticle of this species.
~ey. W. D. Intermediate products in the bacterial decomposition ofhexadecanol and octadecanol. Tecbnical Report I
TR-29; W70-09829; OWRR-A-012-TEX(l). Texas A&M University Water Resources Institute. NTIS Accession fPB.194-
237.
In the arid climate of the southwest, control of water loss by the use of monolayer films was. investigated. In conjunc-
tion with these efforts, this project was designed to meet two goals: (1) to investigate the behavior of bexadecanol and
octadecanol in microbial systems, including the detection, identification and behavior of any intermediate or end produces
formed as a result of biological transformation;' and (2) to correlate the behavior of long-chain fatty alcohols with studies
of lower molecular weight alcohols.
Three primary analytical techniques were employed to obtain direct and specific measure of the rate and extent of
degradation of hexadecanol and octadecanol by adapted microorganisms: gas chromatography, total organic carbon
( analysis and recorded oxygen uptake. A settled sewage supernatant was used as the source of microbial organisms
Compliance Services International Report Number FATF-9101
Fatty Al£.Q.hol Compounds Page 41
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\. which were adapted to the alcohol substrate. Low chain length alcohols (3 and S carbon) were used to condition the
system and demomtrate its capaJ>ility to adapt to soluble alcohols as a carbon source. The higher chain alcohols were
insoluble in water but formed a film on the water surface. Due to this filming tendency, 1-hexadecanol and 1-octadec·
anol were tested in a static eovironmeot to avoid Joss of the compound on flask walls. ·
1-butanol and 1-peotanol were removed from the solutions within 4 to 6 hours of their introduttion. When isopentanol
was also present, there appeared to· be a selectivity of response which favored the straight chain alcohols. The total
organic tarbon removal during this plme of experimentation approached fust order microbial re,,ponse with half-lives as
sbort as 2 hours. Similar re,,pomes were evoked when cultures were exposed to isobutanol, 1-butanol and 1-pentanol;
respense to straight chain alcohols was virtually oon-selective and the removal of isobutanol was essentially stopped until
the straight chain alcohols were removed or converted.
Considerable operational difficulty was experienced in attempts ~'conduct growth and utilization trials on the higher
chain alcohols. Given sufficient time In contact with the adapted microbial species, complete disappearance of 1-
hexadecanol and 1-octadecanol as an identifiable molecular speties will occur. Experimental difficulties precluded the
establishment of an exact half-life; but degradation appeared to be fairly complete within 7 to 10 days. Where these
substrates were added in granular, slow rel~ forms, so that disappearance was also slowed, no significant soluble
organic accumulation occurred. Where substrate was added in dissolved form (a hexane solution), microbial growth was
rapid and there was evidence of soluble organic accumulation above the level of controls. Efforts to extract and identify
the organs were unsuccessful, partly due to the presence of hexane as a complicating factor (some adaptation to hexane
may have oCClllted). ,_
The complications of studying these compounds in both the field and laboratory were discussed. The fact that solvents
such as hexane or isopropanol must be used to disperse the compounds in a aquatic system and the ubiquitous presence
:.i of carbon make qualification and identification of breakdown products extremely difficult
*Larson, R.J. & L.M. Games. 1981. Biodegradadon oflinear alcohol ethoxylates in natural TRANSLATED BY The British
Library DOcument Supply CeQter. Boston Spa, Wetherby, West Yorkshire LS23 7BQ, United Kingdom. BLDSC 5828.4 (M·
52051).
._ ..
Lindstedt, M., S. Allemnark, R. A. Thompson and L. Edebo. 1990. Antimicrobial activity of betaine aters quaternary
ammonium amphiphiles which spontaneously hydrolyze into non-toxic components. Antimicrobial Agents and Chemotherapy.
34(10): 194!).19S4.
*Lorenzen, G.A.· and W. W. Meinke. 1968. A feasibility study on the utilization of monomolecular _films for mosquito
abatement. Mosquito News 28:230-232.
*Mann, H. Biological effects of fatty alcohols on freshwater animals. Internationale Revue der Gesamten Hydrobiologie.
56:599-601. TRANSLATED BY The British Ll"brary Document Supply Center. Boston Spa, Wetherby, West Yorkshire
LS23 7BQ, United Kingdom. BLDSC S828.4 (M-S20Sl).
*Miller, S. and Q.D. Maddock. 1970. Ovicidal effect of selected compounds on.the eggs of Anopheles albimanus. Journal
of Economic Entomology. fi3:11S1-1154.
Moreau, R. A., A. H. C. Huang. 1979. Oxidation of fatty alcohol in the eotyledOJIS of jojoba seedlings. Archives of
Riocbemistry and Biophysics. 194(2):422-430.
During the germination of jojoba (Sbnmondsia chlnensis) seeds, fatty alcohols are formed from the hydrolysis of stored
wax esters. The cotyledon ex~ has the ability to convert fatty alcohols to fatty aJdehydes in the presence of molecular
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Fatty Alcohol Compounds Page 42
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Oi and subsequently to fatty acids when NAD+ is added. 'The whole fatty alcohol oxidation system is capable of
·,. .oxidizing monosaturated fatty alcohols which are the physiological substrates in jojoba cotyledons.
.,
.i-Noweck, K., H. Ridder. 1987. Fatty alcohols. Jn Ullman's Encyclopedia of Industrial Chemistry, 5th ed. Al0(4): 277-
296. VCH Publishers Inc., New York.
Fatty alcohols are aliphatic alcohols with chain lengths between C. and Cu· They· are predominantly stralght-dlain and
monobydric, and can be saturated or ~e one or more double bonds. Alcohols with a chain length above C:,z are
referred to as wax alcohols. The character of fatty alcohols is determined by the manufacturing process and the raw
materials used. Natural productS, such as fats, oils and waxes, and the Ziegler alcohol process give straight-chain,
primary, even-numbered alcohols. Other types of dimerization and oxidation processes give branched chain or second-
ary alcohols of various characteristics. •.
..
•Natural fatty alcohols• are derived from renewable reso~ such as fats, oils and waxes of plant or animal origin.
•synthetic fatty alcohols• are produced from petrochemicals such as olefins and paraffins. Up blltil 1930, the manufac-
ture of fatty alcohols was based almost exclusi-~e1y on the splitting of sperm on. The invention of high-pressure hydro-
genation was cleveloped at that time and allo~ed the use of new ra\v materials. In 1985, the world nameplate production
capacity of fatty alcohols was estimated. af 1.3 ·x 106 t/a, of which about 60% was based on petrochemicals. Fatty
alcohols and their derivatives are used in synthetics, surfactants, oil additives and cosmetics and have many ~
uses, such as sucker control agents in tobacco.
Pltysical Properties: Saturated fatty alcohols up to dodecanol (12 carbons) are clear, colorless liquids with a lower
specific density than water. The lower members of the series have a characteristic odor. The physical properties of
straigbt-diain, primary alcohols are summarized in the table b~ow. ·
/ \
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.f (
) tol. A 10 Fatty Alcohols 291
.·
"'
i 20
~ 10
i 0 .....,.,,..,..._..,,.,_,"""""..,.,..,,,.,--
6 8 10 12 14 1618 2 l. 6 810121f.1618202224. 6 8101214161820 10 12 14 16 , .
Hydrogenation
of fatty acid
·Ziegltr-
Al fol
- .•
Modified
Ziegler
Hydrogenation
of fatty acids
methyl ester process process from paraffin
from coconut IEpalJ oxidation
oa
I-
r.o L<tS t:BO L ;:l.O L:lOO
~
130 . 1··
\ ..
.
0
"'i 20
-
.- . 'I._ 'I.
., I
10 12 14 10 12 11. 10 12 14 10 12 14. 16 18 20
Oxo alcohol Oxo alcohol Oxo alcohol Unsaturated
from by phosphine from alcohol from
br~nched· catalysis statistical tallow
otefins n-olefins
c
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Fattx Alcohol Compounds Page 44
( Boiling points and melting points increase unifonnly with chain length. The influence of the polarizing hydroxyl group
.! diminishes with increasing chain length; thus hexanol and even octanol show some water solubility, but decanol and the
higher fatty alcohols can be considered as .immisci"ble with water. Common organic solvents such as petroleum ether,
lower alcohols and diethyl ether are suitable for fatty alcohols.
Under normal conditions, fatty alcohotS am resistant to oxidation. However, they can be converted into aldebydes or
or
carboxylic acids using strong oxidaiits or by catalytic oxidation with air oxygen.
Production Processes: Several ~ are available for the production of fatty alcohols. The base material and the
technique used detennine the type and length of the carbon chain in the final product. The type of process, base
material and the end products produces are outlined below:
.
:. . -..;.
'
-·
(
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Fatty Alcohol Compountfs Page 4S
~ 1-Dodecanol lauryl alcohol 112-53-8 C12HuO 186.3 300 23 260 0.822(40) i.4428(20)
~ 1-Tridecanol 112-70·9 C 13 H210 . 200.4 280 30 276
~ 1-Tetradecabol myrlstyl alcohol 112-72-1 C14H300 214.4 261 38" 172(2.67) 0.823(40) 1.4358(50)
.
~
1-Pentadecanol 629-76-5 CuH,20 228.4 245 44 1.4408(50)
1-Hexadecanol cetyl alcohol 36653-82-4 C111H340 242.5 230 49. 194(2.67) 0.812(60) . 1.4392(60)
~
~
1-0cladecanol stearyl alcohol 112-9.2-5 C 11H510 207.• S 207 58 214("2.67) 0.815(60) 1.4388(60)
1-Nonadccanol 1454-84-8 C"H..00 284.5 196 62 1.4328(70)
~ 1-.Eicosanol arachidyl alcohol 629-96-9 CzoH420 298.6 187 64 215(1.33) 0.806(70)
~
1-Heneicosanol 15594-90-8 Cz1H440 312.6 179 68
§ 1-Docosanol behenyl alcohol 661-19-8 Czzlti,O 326.6 171 71 2411.33 0.807(80)
~
~
....
II)
:g
E-i
.'-'
....-.....
.j
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Fatty Alcohol Compounds Page 41
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Uses: Fatty alcohols are mainly used as intermediates. Surfactants account for 70-753 of fatty alcohol production. The
most important groups of surfactants are alkyl polyglycol ethers, alkyl sulfates and alkyl polyglycol ether sulfates. On
a much smaller volume, fatty al~hols are used In cosmetic creams, lotions and industrial emulsions.
Analytical Methods: Analytical methods for quality control purposes are defined by DIN [101), ASTM (102] and the
Deutsche Gesellschaft fttr Fettwisseoschaft (DGF) [103). the parameters measured typically include (where appropriate
of the· compound under production): composition (by gas chromatography), hydrocarbon content, color, refractive
index, density, viscosity, solidification point, boiling range, flash point, ignition temperature, hydroxyl number, carbonyl
number, peroxide number, iodine number, acid number, saponification number and water content. The sources of &tty
alcohols used for tobacco desuckering include those produced from coconut and other natural oils and those produced
from petrolewm compounds by the Ziegler Process. Coconut alcolJols produce very few impurity peab and contain Jess
that 0.1 ~ IHridecanol and varying amounts of n-alkanes. Ziegler, alcohols are primary, straight chain alcohols with an
·even carbon number. Gas chromatography shows up to 1.9% impurities, consisting of numerous even-numbered,
isomeric fatty alcohols.
*Neufahrt, A-, K. l..Otzsch & D. Gantz. 1982. Biod~ability of 14C-Jabeled ethoxylated fatty &tcohols. Teoside Detergents
19:264-268. •
*Nooi, J.R., M.C. Testa & S. W"J1lemse. 1970. Biodegradation mechanisms of fatty ~~hoi ·non-ionics.· Tenside Detergents.
7:61-65. . .. . .
*Olsen, S.R•• F. S. Watanabe, F. E. Clark Et al. 1964. Effect of hexadecanol on evaporation of water from soil. Soil Sci.
97:13-18.
Obst, B. S. 1986. 1986. Wax dipstion in Wilson's storm petrel Oce{llJites oceanicus. Wilson Bulletin. 98(2):189-19S.
Wax esters are an abundant source of energy in the marine environment.· Hydrolysis of the wax ester produces fatty
·alcohols which 8re then oxidized to or assimilated into fatty acids. ·
*Patterson, SJ., C.C. Scott & K.R.E. Tucker. 1970. Nonionic detergent degradation. m. lnitiaJ mechanism of the
degradation. J. Am. Oil Chem. Soc. 47:37-41.
Peltzer, E.. T., R. B. Gagosian. Sampling and quantitation of lipids in aerosols from the remote marine atmosphere. Anal.
Clim. Acta. 198:125-144.
Air and ram samples were collected to demonstrate the efficiency of an analytical method for five classes of naturally
occuning Up~ one of which was fatty alcohols of C13 to C36 chain length.
Place, A. R., D. D. Roby. 1986. Assimilation and deposition of dietary fatty alcohols in Leach's storm petrel Oceanodroma
leucorhoa. Journal of Experimental Zoology. 240(2):149-162.
Shading of Euglena growing on yield alcohol may have caused the accumulation of paramylon and lowered synthesis of
amino acids and protein which are essential for the cell growth. The bleached mutant has been shown to adapt to
myristyl alcohol medium after several tramt'ers and an increase in (NBJ~ concentration. The mutant may induce
an ability to synthesize amino acids from myristyl alcohols by this adaptation.
-
Prahl, F. G., G. Eglinton, E. D.S. Comer, et al. 1985. Fecal lipids released by fish feeding on zooplankton. Journal of the
Marine Biological Association of the United Kingdom. 65(2):547-S60.
Compiiance Services International Report Number FATF-9101
Fatty Alcohol Compoupds Page 48
Fatty acid (and therefore fatty alcohol?) moieties of Cl8-C20 virtually eliminated in digestion; higher chain lengths were
( enriched in the feces.
The feces of wax-fed (hexadecyl oleate) birds contain fatty alcohol and fatty acid, the products of wax hydrolysis.
*Ristau, E. & F. Wagner. 1983. Formation of novel anionic trehalose tetraesters from Rhodococcus erythropoJis under
growth limiting conditions. Biotecbnol. Lett S:9S-100.
Romankevich, Ye. A., M. G. Bystrova, l. A. Nemirovskaya, et al. 1982. Composition ofJipids ofbenl:hicsediments. Vinltl.
No volume number givm. Pages 100-107. ·
A study was made of the upper layer (0-S cm) of benthic sediments from a river system shelf. The lipids in the organic
matter of the sediments fluctuated from 1.S to 10.7%, averaging 3.5%, with fatty alcohols being one of the 7 lipid
components. This article is in Russian and has ~t been translated.. ·
. ..
Richterich, K., P. Gode, W. Guhl. 1985. Ecological evaluation of a bew non-ionic anti-foaming agent. Fette Seifen Anstric·
hmittel. 87(10) 421-424.
..
The product discussed is a mixture of C12/C18 fatty alcohol with 10 EO butyl ether. In Germany, specific tests are
required for biodegradability \BiAs• reduction). For this product, the BiAs reduction was between 93 and 989'; a
better degree than the minimum regulatory requirement of 80%. Closed bottle tests and a simulation of sewer
plant/riverine environments demonstrated rapid biodegradation (time values are not given In abstract. The article is in
German and bas not been tramlated.) ·
Sabastiani, A., Simonetti, A. D., Borgioli, A., et. al. 1971. Behavior of synthetic detergents In soil. m.. Soft detergents,
microorganisms and soil. Nuovi Ann lg Microbiol. 22(4):229-242•
.)
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This article is in Italian. with no abstract. Lack of other information may require this to be ordered and translated.
Sargent, J .. R.'. ·C: C. E. Hopkins> J. V. Seiring, et al. 1983. Partial characterization of organic material in surface sediments
from Balstjord~ Northern Norway. in relation to its origin and nutritional value for sediment Ingesting anima,ls. Marine
Biology (Berlin). 76(1):87-94.
Basin surface sediments were characterized to assess the nature and origin of the organic material present and its
potential nutritive value for sediment ingesting animals. Fatty alcol)ols accounted for 30% of the non-saponifiable lipids
and pbytol alcohols accounted for 40% of the fatty alcohols. Small amounts of very long-chain fatty alcohols character·
istic of terrestrial plants were present, but long-chain monounsaturated fatty alcohols characteristic of marine 7.00plankton ·
were essentially absent. · ·
No fatty alcohols n-chain-lengths of.Jess than 13 carbons were detected in this experiment. k is possible that the
extraction process volatilized the n-fatty alcohols with lower chain lengths (the shortest chain alcohol detec:ted had a
melting Point near the temperature used in the extraction process and lower .chain length compounds would be expected
·to be more volatile than longer straight-chain alcohols). The percentages of n-fatty alcohols recovered are presented
below:
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.!
Fatty alcohol contents exJu'bited differences in respome among leaves grown under differing photoperiods and tempera.
tures. Since epicuticular fatty acid and fatty alcohol class tot.als were altered by the effects of tho environment on
,euetically uniform leaves, the possibility arose of a random synthesis within a single subclass as opposed to the synthe-
sis of a single product as a major unit within each subclass.
Tobacco epicuticular alkane quality is influenced by photoperiod, temperature and leaf age. Fatty acids aro precursors
to aJkanes in peas and spinach and to primacy alcohols in broccoli. Also, alkanes can be converted to secomlary alcohols
and ketones in broccoli. lbe quantity of each of these constituents in leaf epicudcular wax appears to depend upon the
plaut species and the environment during leaf development. In this experiment, generally, loug photoperiod and cool
temperature were associated with highest Jong-aliphatic carbon chain production on a leaf area basis. Quantity of the
individual alkane, fatty acid and fatty alcohol elasses present under the different growth conditions varied in relation to
the Jeaf metabolic status and not leaf size•
.;hOberl, P., E. KUDkel & K. Espeter. 1981. (No title provided; cited by Steber (1983)). Tenside Detergents. 18:64.
\_
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*ScMbed, ·P. 1982. Mikrobieller Abbau eines Kokosfettalkohol-etboxylates durch Adnetobacter lwoffi, Stamm ML. Tenside
Detergents 19:329-3339.
*Scbnitzer, M., C.A. Hindle, M. Meglic. 1986. Supercritical gas extraction of alkanes and alkanoic acids from soils and
humic materiaJs. Soil Science Soc. Am. 150:913-919.
J"Sever, J., P. L. Parke.r. 1969. Fatty alcohols normal and isoprenoid in sediments. Science (Washington). 164(388-
3):1052-1054.
Normal long-chain fatty alcohols were identified in marine sediments and evaluated as indicators of s~imeut age. Both
normal and isoprenoid alcohols were found in recent and ancient ~~iments. Sediments from three different recent and
three different ancient sediments were aoalyzed by gas chromatography. Ancient sediments were: Miocene age, ftom an
outcrop in the Philippine Islands; Eoeene, from Green River (c'olorado) Shale; and Upper Cretaceous, from an outcrop
near Austin, Texas. Recent sediments were: Baffin Bay, a hypersaline arm of Laguna Madre off Corpus Christi,
.
Texas; Gulf of Mexico, off Port ArBD.W, Texas; and San Nicholas Basin, off the coast of Southern California.
ReCent sediments, even where terrestrial run-off is minimal, contain normal saturated alcohols with 12 to 26 carbons.
AICohols with both even and odd numbers of carbon atoms were present. In addition, normal, monomethyl and isopren-
oid long-ebain hydrocarbons, alcohols and fatty acids were present. The amounts of alcohols found in ~sediments
were from one order of magnitude less to the same order of magnitude as the concentrations of fatty acids.
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SEVER TABLE: Concentration
(Parts Of alcohol per million parts of dry sediment)
of the Normal Alcohols in Sediments
SAN
GULF OF NICHOLAS MIOCENE EOCENE UPPER
ALCOHOL BAFFIN BAY MBXICO BASIN AGE AGE CRln"ACEOUS
n-dodecanol 1.00 - - - - .. .
n-tetndocanot 1.40 0.36 3.00 1.7S 3.20 •.· -· 1.30
Analytical confirmation was conducted to assure that the extraction ~ure did not create any artifacts.
Fatty alcohols in ~ts probably have their origin in the marine life of the areas studied. Baffin Bay,
where C12 alcohol was detected, normally receives very little fresh water and is often twice as saline as nonnal
sea water. Such restricted run-off would probably not transport enough terrestrial organic matter to account
for the unifonn concentrations of alcohols observed in the Bay sediments. The author did not sPecuJate as to
which marine organisms were involved in the formation of organic compounds studied here, although he
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proposed that bacteria may be involved. Isoprenoid alcohols which were detected suggested that these prod-
ucts were side chains of chlorophyll and possibly were partially decayed deposits of plant material.
*Shadiakhy, A., H. Stage. 1981. Influence of double bonds and branchings on vapor pressure as well as the
volatility relations of fatty acids, fatty acid esters, fatty alcohol D:Uxtures or mixtures of the corresponding carbohy-
drates. Fette Seifen Anstrichmittd. 83(11):431. ' ·
This article is in German and is apparently presented only as a meeting abstract. There are no references. It
may be interesting to pursue if no other information on vol~tility is discovered•
.,
Jl'Singer, M. E. V., W.R. Finnerty. 1990. Physiology of biosurfactant synthesis by Rhodococcus species H13-A.
Canadian Journal of Microbiology. 36(11):741-745.
_,
The commercial production of biosurfactants from microbial activity is of interest Biosurfactants are· surface-
active agents produced by bacteria, yeasts, and fungi and include such products as fatty acids, glycerides,
phospholipids, lipopeptides and antibiotics. Biosurfactants produced by microorganisms are generally consid-
ered to repieSent a mechanism for the solubilization or emulsification of water-insoluble substrates to facilitate
transport by the cells.
This investigation descnl>es the identification of a biosurfactant-producing bacterium and the general physiolo-
gy of biosurfactant synthesis in Rhodococcus species H13-A. Rhodococc:us species H13-A was isolated from (
soil after several passages on hexadecane enrichment medium. Extracellular glycolipid synthesis by Rhodoco-
ccus species H13-A occurred following growth on decane through octadecane as sole sources of carbon and
energy. The highest levels of glycolipid results from growth on dodecane, tridecane and teb:adecane.. No
evidence was obtained of cell lysis. The synthesis and release of glycolipid into the growth medium are linked
to nitrogen limitation.
Other studies were referenced which have investigated this process in other organisms. Other sorface-active
.glycolipids are synthesized by actinomycetes during growth on alkanes, including trebalose mycolates by
Arthrobacter parq/fineus. ·
........
Jl'Sinniah, B. 1983. Insecticidal effect of aliphatic alcohols against aquatic stages of Aedes mosquitoes. Tmnsac-
tions of the Royal Society of Tropical Medicine and Hygiene. 77(1):35-38.
Long chain fatty alcohols (Cn-c;J can be applied to water so that a monomolecular layer is formed on ~
surface. Earlier research showed that a surface layer of lauryl alcohol (C12 alcohol) kills all larval stages of
Culex quinquefascialU3. The aim of the cuaent study was to investigate the effectiveness of some aliphatic
alcohols as insecticides against the aquatic stages of Aedes Qlgypti (L.) and Aedes scutellaris (Walker) •
.
The article also presents some information on the properties of the compounds investigated. Compounds of
interest and their properties giv~ ~ ~ted below:
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The alcohols tested :nnged flom chain lengths ofc;-c11• but there were no straight chain alcohols tested below tho chain lenglh
of decanol. Compounds were tested at c:oncentrations equivalent to 1, 2, 4, 8, 10, 20. 40, 80, 100 and 200 liters/hectare, at test
temperatures of 2S to 27 degrees C. Larvae, pupae and eggs were tested. Results are shown below:
24-hour I.DJD and LO,. (") for various alcohols tested against eggs, :firSt. third and fourth iostar larvae and pupae ofk. aegypti
and Ae. scukllaril
1-tetndecanol Egg 20 4 21 42
L1 285 312 280 315
L3-L4 285 3S2 309 335
pupae 59 • 86 62 92
1-he.xadecanol Egg 37 S4 40 59
L1 312 396 296 385
L3-L4 3S6 436 321 409
pupae 86 132 91 140
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In control trials, the solvent (hexane) showed no harmful effect on the larvae. Trials with more than 10%
mortality in the control were not used in the determination of an ~ This author reports work by Miller
and Maddock (1970) which tested. a number of alcohols and found only one that was effective (cinnamyl
alcohol). Most of the alcohols tested were of lower carbon chain length, and they tend to evaporate before
they have a chance to cause damage to the tissues of mosquitoes. Very long chains were ineffective except
at- very high dosages. In separate studies also reported here, Lorenzen and Meinke (1968) found that
larvae fed 1-hexadecanol did not die. It was speculated that mortality was induced by the breakdown of
ciiiicwar: lipids. thus as with most oils, the surface-active properties may be .respOnsible for the ovicidal
activities of these compounds.
.
Simoneit, B.R.T. 19TI_. Organic matter in eolian dusts over the Atlantic Ocean. Mar. Chem. 5:443-464.
,
Simoneit, B. R. 1989. Organic matter of the troposphere V: Application of molecul3r marker analysis to
biogenic emissions into the troposphere for ·source reconciliations. Journal of Atmospheric Chemistry.
8(3):251. -
Aerosols from rural and remote areas in the Western US, South America, Nigeria, and Australia were
· analp.ed for •atmospheric detritus• contenl All samples contained predominantly plant waxes. The
loadings of hydrocarbons included fatty alcohols at 10 to 1650 ng/nr. Higher molecular weight lipids
contn"buted a major portion of the organic carbon in samples from remote and rural areas. They are
therefore important indicators for regional biogenic sources in the global cycling of organic carbon.
.l*Simoneit, B.R.T. 1979. Biogeoic lipids in eolian particulates collected over the ocean. In Proceedlnp:
Carbonaceous Particles In the Atmosphere. (Ed. by T. Novakov), pp. 233-244. NSF-LBL
c
*Simoneit, B. R. T., M.A. Mazurek. 1982. Organic matter of the troposphere. II. Natural Background of
biogenic lipid matter in aerosols over the rural western United States. Atmos. Environ. (F.ngJand). 16(9):2-
139-2159.
This study of aerosols from the Western United States was initiated for the threefold purpose of: (1)
. comparison of the area extremes; (2) characterization of the solvent soluble fractions; and (3) evaluation of
relative organic aerosol contn"butions from natural biogenic emimons and anthropogenic sources. Aetosol
samples were acquired from the rural and urban sites by filtration of the ambient air using a standard high
volume air sampler fitted with a quartz fiber filter. Representative samples of vegetation were taken in
various areas to provide a composite for i1' situ wax analysis. Analysis was by gas chromatography and
GC/MS.
The concentration ~ge for the total lipids (hydrocarbons, fatty acids, fatty alcohols, trace im~ts of
ketones, etc) was discovered to be from 90 to 3600 ng nr' with the fatty alcohols and other polar lipids at
a ~tration of 200 to 2000 ng m·'. The yield of lipid material for these samples represented up to
10% of the total organic:; carbon. 'The total fatty alcohol composition was indicative of derivation from
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vascular plant waxes, especially forest and grassland types of plants. The saw-:toothed distnbution of the
chain lengths (odd> even) compared direcUy with the n-a1kane distributions in specific plant communities.
The total fatty alcohol fractions included chain lengths of C10 to ~' with the middle of this :range predom-
inating.
In this particular investigation, the C. to Cio bomologs were largely lost due to evaporation (according to
their boiling points) in the environment and/or in the· experimental. procedure, or were separated by
distillation in the refining process. Absolute concentrations of the bomologs < Cio in these aerosol samples
are not accmate, but qualitative comparisons can be made.
.
From the infonnation above, the au~ors have concluded ·that the concentration of shorter chain fatty
alcohols is equal to or greater thm·.~e-concentration of fatty alcohols which are > eio. Typical distribu-
tion of fatty alcohols which were quantifiable are shown below, and include data on chain lengths of 10 to
3S carbons. .•
The author speculates that the homologs < Cio may be derived from microbial sources since they are not
prevalent in fresh vascular plant waxes. The predominant alcohols in all samples were normal fatty
alcohols with minor amounts of secondary ~hols and varying amounts of phytosterols. The dominance
of ~ and c;. chain lengths in the aerosol samples compares in general with the distributions for grass
· wax. These data indicate that fatty alcohols from plant waxes preserve their characteristic fingerprint in
aerosols and are a major fraction of the lipid material.
Procedural blanks were analyzed to assess the accuracy of the extraction and analytical procedures. Some
contaminants were discovered and included minor amounts of n-fatty acids and residual phthalate cstersj
but no fatty alcohols•
./*Solberg, Y. 1989. A literature review of the lipid constituents of higher fungi. New investigations of
Agaricales species. International Journal of Mycology and Lichenology. 4(1/2):137-154.
The chemical contents of several higher fungi were studied. Extraction and concentration lead to isolation
of fractions containing aliphatic and aromatic hydrocarbons, fatty alcohols and fatty acids. Fatty acids
(and &tty alcohols?) were predominantly of C1, to C.1 chain length. The details of findings by species
tested are provided, with the discussion centering on fatty acids. ·
.l*Speel, H. C. 1963. Foam, pollution and biodegradability. Journal of the American Oil Chemist's
Society. 40(7):4,12,13,15 •.
This article presents general infonnation but no original research. The biodegradability of detergents is the
topic matter, but their origin (alkyl benzene sulfonates vs. alkyl sulfates) determines their behavior. The
straight chain fatty alcohol sulfates, whether derived from natural alcohols, natural fats or oils, or from
ethylene by Ziegler-type processes, are gCnerally considered to be completely biodegradable. Sodium
lauryl sulfate {C1J, for example, disappears in less than 3 days (m water). The overall process was
oxidative. In general, the lower molecular weight species of each detergent type produces more foam on
agitation, but degrades more rapidly than the higher molecular weight species.
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J'*Steber, J., P. Wierich. 1983. The environmental fate of detergent range fatty alcohol ethoxylates.
Biodegradation studies with a 14C labelle.d model surfactant. Tenside Detergents. 20(4):183-187.
In order to solve several outstanding problems in the biodegradation of a model fatty alcohol ethoxylate
(labelled separately in the alkyl as well as the EO chain) was elucidated in a continuous activated sludge
system using simulation tests and die-away tests. Because the alkyl chain was labeled, some conclusions
can be drawn about the fate of the. stearyl alcohol side chain. The (1: 14c] stearyl alcohol = 7 EO had a
specific activity of 19.2 mCi/g; the radiochemical purity was 98%. Only the results of the experimentation
conducted on the labeled alkyl compound is discussed here.
. .
The ·simulation tests used a model plant which was a mii1iature continuous flow activated sludge unit
constructed acc0rding to Swisher. The die-away tests wpe discontinuous tests analogous to the OECD
Screening Test and were perfonned in shake flasks modified to a closed system. In the simulated plant
study, after a working-in period of approximately two we.eks the plant was Jed for about one week with
synthetic sewage containing one of the radiolabeled suifactmts. As expected, the carbon in the !-position
of the alkyl-labeled compound was minerali7.ed to 14CC>z to a greater extent than the BO-moiety of the
analogous 14C-EO sulfactmt. Mineralizati~ rates were 50 to 60% after 2 to 3 days of 14C-feeding; with
a slightly increasing tendency. The radioactivity of the effluent froQl the alkyl-labeled surfactant only
amounted to about 6% (undegraded). When results were adjusted for recovery (93.8%), it was reported
that 99% of the fatty alcohol ehtoxylates present in the influent incurred microbial attack withiil 3 hours'
retention time in the model plant.
Degradation of the [l-14e] stearyl alcohol ethoxylate led to predominantly (90%) acidic metabolites. This
fraction of degradation products was mainly composed of carboxylated polyethylene glycols. 1be neutnl
c
· metabolites as well as the acidic biodegradation intermediates were reported as highly biodegradable. 25-
30% of the sludge radioactivity accounted for undegraded residual surfactants. The main portion of sludge
radioactivity (70%) corresponded to about 27% of the initial radioactivity and consisted of bacterial
biomass. The lipid fraction of the sludge from the [l-14C] alkyl ethoxylate experiment had a considembly
higher radioactivity than sludge from the ring labeled experimenL This was explained as a consequence of
microbial degradation of the alkyl-chain via P-oxidation according to general biochemical pathways,
resulting· in the production of acetyl units, which represent the elementary precursors for fatty acid biosyn-
tbesis.
The relatively high surfactant content in the sludge may result from the comparatively low water solubility
of stearyl alcohol + 7 EO. Additionally, the hydrophilic BO-chain of alcohol ethoxylates exlu'bitS a
slower biOdegradation rate than the hydrophobic part of the surfactant molecule. The faster biodegradation
of the alkyl chain is clearly shown by the fact that the intermediates of the [l -14C] stearyl alcohol ethoxy-
late biodegradation found in the effluent consisted largely of higher BO-numbered acidic polyethylene
glycols which obviously must contain a small 14C Jabeled moiety. In addition, it is evident that these
polyethylene glycol carboxylates can only arise if degradation of the alkyl chain starts at the terminal
methyl group. This is in accoidance with eonclusions drawn by other authors.
The alkyl chain of the fatty alcohol ethoxylate exhibited an ultimate biodegradation of aboot 1S %• The
actual extent of degradation may exceed this value for two reasons: (1) the steady state mineralization rate
was higher than the balanced value of total 14CC>z-evolution and (2) an undervaluation results from the 1'C- /
I ,
labeling position in connection with the degradation mechanism. The biodegradation begins at the terminal \ .·
Compliance Services International Report Number FATF-9101
Fatty AJcoh~t Compounds Page S6
(
)
methyl of the alkyl chain, so that in this case, the alkyl carbon in position 1 represents the last carbon
being transformed.
From these studies it was concluded that the biodegradation of stearyl alcohol + 7 EO formed no recalci-
trant metabolites and would be expected to completely biodegrade under primary sewage treatment, as well
as by self-purification processes in surface waters. ·
Steber, J., P. Gode, W. Guhl. 1988. Fatty alcohol sulfates: the ecological evaluation of a group of impor-
tant detergent surfactants. Fett Wissenschaft Technologie. 90(1):32-38.
This group of alcohol detergents. showed a very rapiii.and complete biodegradation with respect to
primary breakdown and ultimate degradability (11\ineralization and assimilation). This was true
under both aerobic an~ anaerobic conditions. The similarity of these processes to those for
straight-chain fatty alcohol is not ewlained in the abstract for the article (the article is in German
and bas not been translated).
,/*Steber, J., P. Wiericb. 1985. Metabolites and biodegradation pathways of fatty alcohol ethoxylates in
microbial biocenoses of.sewage plants. Applied and Environmental Microbiology. 49(3):530-537. .
'The results_ of Steber (1983) and subse.quent experimentation are discussed and indicate that there is a
faster degradation of the alkyl than the polyethylene glycol moiety and that there are two distinct primaxy
degradation mechanisms acting simultaneously in the microbial biocenoses: intramolecutar scission of the
( surfactant as well as er>- and P-oxidation of the alkyl chain. In this report, a picture of the microbial
pathways that bring about ultimate biodegradation of fatty alcohol ethoxylates in the environment were
made. Studies were conducted in a model continuous flow activated sludge plant similar to that described
by the OECD Confirmatory Test.
Stearyl alcohol ethoxylate was labeled on the alcohol or EO portion of the molecule. The information
·presented here concentrates on the results obtained with the steady-labeled compound. [l-14€) stearyl
alcohol-7 BO of 19.2 mCi/g specific activity and radiochemical purity of 98$ was used. 'The OECD
model sewage treatment plant bad a 3 hour mean retention time. Radioactivity of the effluent from the
alkyl-labeled model surfactant amounted to 9% of the initial activity. Only small amounts {l" of the
initial level) of each compound could be a~'butecfto·intact parent surfactants. After degradation of the
chain-labeled compound, largely acidic compounds were abstained.
A fast degradation of the fatty alcohol moiety of the surfactant, beginning wilh terminal methyl group and
slowing down before the radiolabeled C-1 is reached. The terminal oxidation of the alkyl chain (c.HJXida-
tion) and subsequent stepwise removal of Ci units at a time by {J-oxidation is presented as the fatty alcohol
chain metabolic process. The resulting products represent the elementaxy precursors of fatty acid biosyn-
thesis.
"Steffens, G. L., T.C. Tso & D.W. Spaulding. 1967. Fatty alcohol inhibition of tobacco axillary&. tenni-
Jal bud growth. 1. Agr. Food Chem. 15:972-975.
*Stephens, U. 1958. Research and Experiments in Evaporation Reduction. Journal of American Water
Works Association. 50:846-854.
Compliance Services International Report Number FATF-9101
Fatty Alcohol Compounds Page S1
(
'
·' *Stevenson, F.J. 1982. Humus Chemistry, Genesis, Composition Reactions. Wtley, New York.
*Still, G. G., D. G. Davis & G. L. Zander. 1970. Plant epicuticular lipids: alternation by herbicidal
carbamates. Plant Pbysiol. 46:307-314.
*Suzuki, T., K. Tanaka, L Matsuhara et al. 1969. Trehalose lipid and a-bI3Jlched hydroxy fatty aci~
formed by bacteria grown Qll n-albnes. Agric. Biol. Chem. 33:1619-1627.
Scharer, D.H., L. Kravetz & J.B. Carr. 1979. Biodegradation of non-ionic surfactants, p. 61-66. Proc. of
the TAPPI Env. Conf. TAPPI, Atlanta.
Simoneit, D.R.T. 1978. 'The organic chenrlstry of Marine S~fuients. In Chemical Oceanography, 2nd ed.
·· (edited by J. P. Riley & ~ Chester) Vol 7:233-311. Academic Press, New York. ·
*Tobin, R.S., F.I. Onuska, B.G. Brownlee et ii: 1976. The application of an ether cleavage technique to a
study of the biode~on of a linear alcohol ethoxylate noniom?-c surfactant. Water Res. 10:S29-53S.
*Vashon, R.D. & B.S. Schwab. 1982. Mineralization of linear alcohol ethoxylates & linear ethoxy sulfates
at trace c0ncentrations in estuarine water. Environ. Sci. Technol. 16:433-436.
Venbtesan, M. L, I. R. Kaplan. The lipid geochemistry of Antartic marine sediments: Bransfield Straight. ·
Marine Chemistry. 21(4);~7-376.
In sections of sediment cores from the area titled; the resolvable lipid compound classes generally occur in
the following order of abundance: n-fatty acids > n-alkanes > n-alcohols > sterols > P411.. 1be
distribution of various lipid components indicate that they are priJicipally from marine autoCbtbonous
sources, Jargely from diatoms and bacteria and to a lesser extent from dinoflagellates. ·
*Willcinson, R.E._ &. MJ. Kasperbauer. 1972._ (No title provided; cited by Wilkinson & ~uer.(19-
80)). Phytochemistry. 11:2439.
/'*Wilkinson, R.B. &. W.S. Haidcastle. 1970. EPTC. effects on total leaflet fatty acids and hydrocarbo~
Weed Sci. 18:125-128.
*Wilkinson, R.E. 1970. Sicklepod fatty acid response to photo period. Plant Physiol 46:463-465. -·
*Wang, T.S.C. 1969. Soil organic matter as cause of increased soil productivity or otherwise phytotoxk;ity.
Int Rice Com. Newsletter 18(2):23-26.
Willcinson, R. E., M. J. Kasperbauer. 1980. Effect of light and temperature on epicuticular fatty acid and
fatty alcohol of tobacco Mcotiana tabacum Cdltivar Burley-21. Phytochemistry (Oxford). 19(7):1379-1383.
· Total fatty alcohol content of sicklepod leaflet epicuticular waxes was significantly increased over the
untreated control by 0.28 kg/ha diaDate and significantly decreased by 1.12 kg/ha diallate. Between these
two Cxtremes~ the intermediate application rat.es of diallate were not significantly different from the un-
treated control This general pattern was repeated in all structural classes of fatty alcohols present in the
epicullicular waxes of sicklepod leaflets with the exception of. the antesio-fatty alcohols which were signifi-
cantly decreased by all application rates of diallate. .,
. .... .
Synthesis of fatty acids was. shown to be greatly inlu"bite(fby qiallate·with the exception of four constituents
(C14:b C1 ~h ~ 1 and C122l. Conversely, 1he synthesis of all fatty alcohols was stimulated by 0.14 and
0.28 kg/ha diailate with the excep.tion of CA17 and C122• These results suggest that the biochemical rela-
tionships between the .various lipid classes is not completely elucidated. In addition, epicuticular fatty
alcohof content was responsive to photoperiod in a different pattern from that of the fatty acids. The two
patterns were not reciprocal. The influence of diallate on individual n·fatty alcohols which are in our
I311ge of interest is shown below.
Each value is the average of 20 determinations; five from each of 10-, 12-, 14-, 16-hr photoperiods.
Fatty alcohol conttmt of the external wax of sickelpod leaflets demonstrated a different photoperiod re-
sponse from that of the fatty acids. The total surface fatty alcohol content was minimal under 12-hour
photoperlods and maximal under 16 hour photoperiods. Earlier experiments with thiocarbamate herbicides
noted ~ reduction of cuticular waxes upon herbicide exposure. Sublethal application ntes of EPTC were
reportt.d to stimulate total fatty acid synthesis and reduce alkane synthesis in the sicklepod. Fatty acids
were converted to alkanes in pea or spinach and to alcohols in broccoµ. The presumption that fatty acyl
moieties produced by fatty acid synthetase serve as general intermediates to the various lipid classes found
in plant cuticular waxes has gained credence. Plant cuticular waxes have been proposed as the end product ·
of metabolism in the epidennis. ·
Wlllcinson, R. E. 1973. Diallate and photoperiod influence:on epicuticular fatty acid and fatty alcohol
contenl Abstracts, 1973 Meeting of the Weed Science Society of America (uMumbered).
In experiments with sicklepod, a common· weed species, it was found that herbicide application and
varying photoperiods could result in variations in plant fatty alcohol content. Fatty alcohol contents were
highest under 10 hour photoperiods. Previous experiments showed that age and temperature could also
induce· variations.
J*Wheeler, J. J., H. Selbnan, A. G._ Motten. 1991. The mode of action of fatty alcohols on leaf tissue.
Journal of Plant Growth Regulation. 10(3):129-137.
Mixtures of C. and C10 fatty alcohols, which usually include small amounts of the C. and C12 alcohols,
formulated with polyoxyethylene (20) smbitan mono-oleate (SMO), are among the agents used in the
control of axillary buds (•suckers•) in the culture of tobacco. Fatty alcohols as emulsions are contact
herbicides; they are not translocated, but instead destroy tissue at the point of contact. In these stluijes, the
fatty alcohol emulsion was applied at label rates and it was found to pass through the cuticle without
disrupting iL The plasma membranes of subtending cells were altered so that, in time, bud tissues were
desiccated and growth of the sucker was controlled•. fight plant species/varieties were used in this investi-
gation: Nicodana tabacum L. and Nicotiana tabacum L. cv Xanthi (tobacco); Nicodana glauca L.; Ficus
elasticaRom. ex Homam.; Taraxacum o.fficinale L.; Lami10n amplexicaule L.; Rosa sp.; and Elodea sp••
The mode of action in each plant type was identical; the induction of desiccation apparently was dependent
upon the time it took fatty alcohol to cross the leaf cilticle (thus the selective desiccation of axillary buds
with incompletely developed cuticular surfaces).
Wertz, P. W., D. T. Downing. 1989. Integlal lipids of human hair. Comparative Biochemistry and
Physiology B:· Comparative Biochemistry. 92(4):759-762.
A series of quaternary ammoniwn compounds that are esters of betaine and fatty alcohols with hydrocar-
bon chain lengths of 10 to 18 carbon atoms were tested with respect·to antimicrobial activities and rates of
hydrolysis. The hydrolysis products were normal human metabolites.
It has been demonstrated that hair contains lipids ••• includingJatty alcohols at levels of trace to 0.2
mgfg.
The mechanism of photoassimilation of C14-alcohol (myristyl alcohol) was strictly light dependent; howev-
er, DCMU, an inlul>itor of photosynthetic electron transfer,. did not inhibit growth completely. With the
bleached mutant Euglena, a long lag-phase extending more than 10 days occurred before growth started
under illumination, and the final cell }'ield was about halfthat observed with wild-type cells. Growth on
myristyl al~ol was almost saturated at light intensities of 600-1000 Ix in comparison to autotropbic ·
growth which increased with light inten~ties to at least 2000 Ix. :_
.·
Biosynthetic bypath~ suggest that short chain fatty-acid synthesis occurs with elongation of the aliphatic
chain to long-ca:d>on chains. Unsaturate, even-carbon numbered saturates, odd-carbon numbered saturates,
and branched Chain aliphatic units.are derived from deaminated Valine and isoleucine. Then, fatty acids
are converted to alcohols and alkanes. Thus, the total variability of epicuticular wax quality and quantity
reflects the activity of the individual enzymatic processes as they are affected by each environmental
condition. These processes include but are not limited to: aliphatic carbon chain synthesis, desaturation,
( reduction and other modification, amino acid metabolism, and the multiplicity of factors influencing leaf
\,
growth.
/
\
S E R v· 1 C E S INTERNATIONAL
·' .
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November 41, 1991
·: :: ...
-
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Ronald B. Ames .-
Uniroyal Chemical company Inc •. · .-· :·
World Headquarters
Benson Road·- ·. · · ··....
Middlebury;
... CT . ,.067.49
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·.
Dear Mr • .AJD.es: ·. . {.
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Monograph report are enclosed (list is also attached). Bernal~
.also requested that I include a copy of the· report. ·: ....
Sincerely,
~-~~
d~~~~e Perry 0
Administrative Assistant
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Abo" encfosed is a printout from the teratology work we ·completed· ~lier in the project.· .·
Let m~ know if there is any further information you may need. · · . · . :ri:: .· ·
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Support Documents
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\
U. S. Food and Drug Administration
Center for Food Safety and Applied Nutrition
Office of Premarket Approval
This list of substances contains ingredients added directly to food that FDA has either approved as food additives or
listed or affirmed as GRAS. Nevertheless. it contains only a partial list of all food ingredients that may in fact be
lawfully added to food, because under federal law some ingredients may be added to food under a GRAS
determination made independently from the FDA. The list contains many. but not all, of the substances subject to
independent GRAS detenninations.
The list below is an alphabetical inventory representing only five of 196 fields in FDA/CFSAN's PAFA database. To
obtain the entire database, including abstractions·or over 7,000 toxicology studies performed on substances added to
food as well as a search engine to locate desired informatio~ order Food Additives: Toxicology, hgulation, and.
Properties, available in CD-ROM format from CRC Press.
Defmitions of the labels that are found in the inventory are:
DOCTYPE
ASP
EAF
There is reported use ofthe chemical, it has. not yet been assigned for toxicology literature ~arch.
NEW
There is reported use of the chemical; the toxicology literature search is in progress.
NIL
Although listed as a food additive, there is no current reported use of the chemical, and, therefore, although
toxicology information may be available in PAFA, it is not being updated;
NUL
There is no reported use of the chemical an,d there is no toxicology infonnation available in PAFA;
BAN
The chemical was formerly approved as a food additive but is now banned; there may be some toxicology data
available.
DOCNUM
pAFA database number of the Food Additive Safety Profile volume containing the printed source information
concerning the chemical.
- I,,.
(
MAINTERM
Naine ofthe chemical as recognized by CFSAN.
Chemical Abstract Service (CAS) Registry Number for the chemical or a numerical code assigned by CFSAN
to those substances that do not have a CAS Registry Number (888nnnnnn or 977nnnnnn-series).
REGNUM
Regulation numbers in Title 21 of the U.S. Code of federal Regulations where the chemical appears.
To access the specific regulations listed below, type in the title number, 21, and then the section and part numbers,
e.g. 184 and 1330 at the Government Priutine Office web site.
To search this list, use your browser's "find" feature. In most web browsers look under the Edit menu at the top of
your browser window and click on Find (or use CTRL-F) to bring up the browser's "find• window. Type in the
phrase you wish to search on, and your browser window should move to the next occurrence of that phrase on this
w.ebpage.
22JAN98
- .5 - 146.3
ASP 2455 NUTMEG {MYRISTICA FRAGRANS HOUTT.) 977051-44-7 182.10
1.01.22
\
U.S. Food & Drug Administration
Nutrition's Librar1, Food and Drug Administration, 5100 Paint Branch Pk~~·., College Park,
MD 20740, or at the National Archives and Records Administration (NARA). For information on
the availability of this material at NARA, call 202-741-6030, or go
tohttp://ll'ww.archives.gov/federal_register/code_of_federal_regulationslibr_locations .html .
(b) The hydrocarbon solvent used in the process described in paragraph (a) (1) of this
section is a mixture of liquid hydrocarbons essentially paraffinic in nature, derived from
petroleum and refined to meet the specifications described in paragraph (b) (1) of this
section when subjected to the procedures described in paragraph (b) (2) and (3) of this
section.
(1) The hydrocarbon solvent meets the following specifications:
(i) Boiling-point range: 17S deg. C-27S deg. C.
(ii) Ultraviolet absorbance limits as follows:
Wave1ength (mi11icrons) Maximum absorbance per centimeter optica1 path 1ength
280-289 O.lS
290-299 .12
300-359 .OS
360-400 .02
(2) Use ASTM method D86-82, "Standard Hethod for Distillation of Petroleum Products," which
is incorporated by reference, to determine boiling point range. Copies of the material
incorporated by reference may be obtained from the American Society for Testing Materials,
100 Barr Harbor Dr., west Conshohocken, Philadelphia, PA 19428-29S9, or may be examined at
the National Archives and Records Administration (NARA) . For information on the
availability of this material at NARA, call 202-741-6030, or go
to:http://Wl"IW.archives.gov/federal_register/code_of_federal_regulations/ibr_locations.html.
(3) The analytical method for determining ultraviolet absorbance limits is as follows:
General Instructions
All glassware should be scrupulously cleaned to remove all organic matter such as oil,
grease, detergent residues, etc. Examine all glassware, including stoppers and stopcocks,
under ultraviolet light to detect any residual fluorescent contamination. As a
precautionary measure, it is reconunended practice to rinse all glassware with purified
isooctane inunediately before use. No grease is to be used on stopcocks or joints. Great
care to avoid contamination of hydrocarbon solvent samples in handling and to assure
absence of any extraneous material arising from inadequate packaging is essential. Because
some of the polynuclear hydrocarbons sought in this test are very susceptible to photo-
oxidation, the entire procedure is to be carried out under subdued light.
Apparatus
Chromatographic tube. 450 millimeters in length (packing section), inside diameter 19
millimeters +/-1 millimeter, equipped with a wad of clean Pyrex brand filtering wool
(Corning Glass Works Catalog No. 39SO or equivalent). The tube shall contain a 2SO-
milliliter reservoir and a 2-millimeter tetrafluoroethylene polymer stopcock at the
opposite end. Overall length of the tube is 670 millimeters.
Stainless steel rod. 2 feet in length, 2 to 4 millimeters in diameter.
Vacuum oven. Similar to Labline No. 3610 but modified as follows: A copper tube one-fourth
inch in diameter and 13 inches in length is bent to a right angle at the 4-inch point and
plugged at the opposite end; eight copper tubes one-eighth inch in diameter and S inches in
length are silver soldered in drilled holes (one-eighth inch in diameter) to the one-
fourth-inch tube, one on each side at the 5-, 7.S-, 10- and 12.S-inch points; the one-
eighth-inch copper tubes are bent to conform with the inner periphery of the oven.
Beakers. 2SO-milliliter and SOO-milliliter capacity.
Graduated cylinders. 2S-milliliter, SO-milliliter, and lSO-milliliter capacity.
Tuberculin syringe. 1-milliliter capacity, with 3-inch, 22-gauge needle.
Volumetric flask. 5-milliliter capacity.
Spectrophotometric cells. Fused quartz ground glass stoppered cells, optical path length in
the range of 1.000 centimeter +/-0.00S centimeter. With distilled water in the cells,
determine any absorbance difference.
Spectrophotometer. Spectral range 2SO millimicrons--400 millirnicrons with spectral slit
width of 2 millirnicrons or less: under instrument operating conditions for these absorbance /--
measurements, the spectrophotometer shall also meet the following performance requirements: \_
Procedure
Determination of ultraviolet absorbance. Before proceeding with the analysis of a sample
determine the absorbance in a 1-centimeter path cell for the reagent blank by carrying out
the procedure without a sample. Record the absorbance in the wavelength range of 280 to 400
millimicrons. Typical reagent blank absorbance in this range should not exceed 0.04 in the
280 to 299 millimicron range, 0.02 in the 300 to 359 rnillimicron range, and 0.01 in the 360
to 400 millimicron range. If the characteristic benzene peaks in the 250 to 260 millimicron
/
I region are present, remo~e the benzene by the procedure described above under "Reagents and
Materials,• "Organic Solvents," and record absorbance again.
Transfer 50 grams of silica gel to the chromatographic tube for sample analysis. Raise and (-
drop the column on a semisoft, clean surface for about 1 minute to settle the gel. Pour 100
milliliters of hexane into the column with the stopcock open and allow to drain to about
one-half inch above the gel. Turn off the stopcock and allow the column to cool for 30
minutes. After cooling, vibrate the column to eliminate air and stir the top 1 to 2 inches
with a small diameter stainless steel rod. Take care not to get the gel above the liquid
and onto the sides of the column.
Weigh out 40 grams +/-0.1 gram of the hydrocarbon solvent sample into a 250-milliliter
beaker, add 50 milliliters of hexane, and pour the solution into the column. Rinse the
beaker with 50 milliliters of hexane and add this to the column. Allow the hexane sample
solution to elute into a 500-milliliter beaker until the solution is about one-half inch
above the gel. Rinse the column three times with SO-milliliter portions of hexane. Allow
each hexane rinse to separately elute to about one-half inch above the gel. Replace the
eluate beaker (discard the hexane eluate) with a 250-milliliter beaker. Add two separate
25-milliliter portions of 10 percent 1,2-dichloroethane and allow each to separately elute
as before. Finally, add 150 milliliters of 10 percent 1,2-dichloroethane for a total of 200
milliliters. When the final 10 percent 1,2-dichloroethane fraction is about one-half inch
above the top of the gel bed, replace the receiving beaker (discard the 1,2-dichloroethane
eluate) with a 250-milliliter beaker containing 1 milliliter of hexadecane. Adjust the
elution rate to 2 to 3 milliliters per minute, add two 25-milliliter portions of 40 percent
benzene and allow each to separately elute as before to within about one-half inch of the
gel bed. Finally, add 150 milliliters of 40 percent benzene for a total of 200 milliliters.
Evaporate the benzene in the oven with vacuum and sufficient nitrogen flow to just ripple
the top of the benzene solution. When the benzene is removed (as determined by a constant
volume of hexadecane) add 5 milliliters of isooctane and evaporate. Repeat once to insure
complete removal of benzene. Remove the beaker and cover with aluminum foil (previously
rinsed with hexane) until cool.
Quantitatively transfer the hexadecane residue to a 5-milliliter volumetric flask and
dilute to volume with isooctane. Determine the absorbance of the solution in 1-centimeter
path length cells between 280 and 400 millimicrons using isooctane as a reference. Correct
the absorbance values for any absorbance derived from reagents as determined by carrying
out the procedure without a sample. If the corrected absorbance does not exceed the limits
prescribed in paragraph (b) (1) (ii) of this section, the sample meets the ultraviolet
absorbance specifications for hydrocarbon solvent.
(c) Synthetic fatty alcohols may be used as follows:
(1) As substitutes for the corresponding naturally derived fatty alcohols permitted in food
by existing regulations in this part or part 173 of this chapter provided that the use is
in compliance with any prescribed limitations.
(2) As substitutes for the corresponding naturally derived fatty alcohols used as
intermediates in the synthesis of food additives and other substances permitted in food.
1As determined by using potassium chromate for reference standard and described in National
Bureau of Standards Circular 484, Spectrophotometry, U.S. Department of Commerce, (1949).
The accuracy is to be determined by comparison with the standard values at 290, 345, and
400 millimicrons. Circular 484 is incorporated by reference. Copies are available from the
Center for Food Safety and Applied Nutrition (HFS-200), Food and Drug Administration, 5100
Paint Branch Pkwy., College Park, MD 20740, or available for inspection at the National
Archives and Records Administration (NARA). For information on the availability of this
material at NARA, call 202-741-6030, or go
to:http://www.archives.gov/federal_register/code_of_federal_regulations/ibr_locations.html.
(42 FR 14491, Mar. 15, 1977, as amended at 47 FR 11837, Mar. 19, 1982; 49 FR 10105, Mar.
19, 1984; 54 FR 24897, June 12, 1989; 70 FR 72908, Dec. 8, 2005]
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• Industry
• Health Professionals
4 U.S Oepa1rrent of Hoalth & Human :Sarvkas:
products.
(14) As a surfactant and wetting agent for natural and artificial colors
for use in barbecue sauce where the level of the additive does not
exceed 0.005 percent by weight of the barbecue sauce.
(d) To assure safe use of the additive, in addition to the other
information required by the Act:
(1) The label of the additive and any intermediate premixes shall bear:
(i) The name of the additive.
(ii) A statement of the concentration or strength of the additive in any
intermediate premixes.
(2) The label or labeling shall bear adequate directions to provide a
final product that complies with the limitations prescribed in paragraph
(c) of this section.
[42 FR 14491, Mar. 15, 1977, as amended at 43 FR 2871, Jan. 20, 1978; 45
FR 58835, Sept. 5, 1980; 46 FR 8466, Jan. 27, 1981]
\
8. . ./cfRL/rl.cfm
9. . ./cfMAUDE/TextSearch.cfm
10. ../cfRES/rcs.cfm
11. ../cfPMA/pma.cfm
1:?. . ./ cfPCD/ classification. cfm
13. . ./cfStandards/search.dm
14. . ./cfCFR/CFRSearch.cfm
15. ../cfPCD_RH/classification.cfm
16. . ./cfAsscm/asscmblcr.cfm
] 7. ../Medsun/scarchRcportTcxt.cfm
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19. . ./cfTPLC/tplc.cfm
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21. http://www.fda.gov/MedicalDevices/DeviceRegulationandGuidance/Databases/ucm135680.htm
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Fatty Alcohols
~
.-..~ MUSIMMAS
MASCOL 80 For: P & G
Octyl Decyl Alcohol
Chemical Property
Acid Value, mg KOH/g 0.10max AOCS Te-2a-64; DIN 53 402
Saponification Value, mg KOH/g O.Smax AOCS 11-1a-64; DIN 53 401
Iodine Value, g/100g 0.1 max AOCS Cd lb-87; DGF C-V 1 tb
Hydroxyl Value, mg KOH/g 380. 393 Derived from chain distnbution
Hydrocarbon, wt% 0.50max GC
\
Moisture, wt% 0.10max Karl Fisher; DIN 51 777 /Tl
Carbonyl of Value, ppm CO 50max MM 1N-AM-ALF06
Physical Property
Color (APHA) tOmax AOCS Ea 9-65; DIN ISO 6271
Appeamnce Oear, no extraneous matter
Bland and &cc from
uncharacteristic odors;
Odor
Typical of previous acccptabl
receipts
CASNo. 68603-15-6
EINECSNo. 271-642-9
The infocmalioa obout the producu produced by us (the "Rcla'IDt Pruducl") coatain<d in dris data lhcd (the •.spea Shtttj: (o) is meant for,......, iafoauatioft
pwJ101CS onlJ ud hu llCt ba:n P"'l'"ml with lll'J pa<ticulu qud ID yom putiaalat i:ittam,.._ or me; (b) doa""' constitute and s1Hlald l10t be co-..d u
coatilutinillllf .~. rcpramtatioa, ........,.., or guaantcc u to the qualiti,p~ coaclilion or othawilc of the Rda'IDt Pmdact ;and (c) Im ba:n ~
hom the soom:a which. ID die best of our ltftowlcdge, is accurate. Ir is yom tt..,._;biliry ID cmun: that the:'* of tbe Rclcvut Produc~ 0t d1< me of the: i116irmatioa
i1I the Spocs Sheet duca""' cunttn...,. any laws of any authurilics, whcthet p"CrMICntal or othawisc,.,.. the rights of any party. in ymr jwisdiclion. .\ceu<diogfy, we
discbim oil liabiity for 1-, iajuty or d2Dil£C which may l:tlUk from the me of the Relevant Pmdm:t, or the use of tbt inrotmatioa in the Spca Sheet to die fullcsr CllCnl
pamih<d by the law.
~PT. MUSIM MAS
, AT..A.~Fatty Alcohol, Methyl Esters and Derivatives
\
~ SAFETY DATA SHEET
1. IDENTIFICATION OF THE SUBSTANCE AND THE COMPANY
Product Identification
Product Name : Octyl Decyl Alcohol
Trade Name : MASCOL80
other Identifier : Alcohols C6-C12, 1-0ctanol+1-Decanol.
Recommended Use : Cosmetic base product for Industrial purpose. General chemicals,
as they are used in many ways in the chemicals Industry.
Company Identification
2. HAZARD IDENTIFICATION
GHS Classification
Physical Hazard : Not classified as hazardous substance
Health Hazard : Serious eye damage I eye Irritation, Category 2
Environmental Hazard : Not classified as hazardous substance
GHS Label Element
Hazard Symbol
/
3. COMPOSITION/ INFORMATION ON INGREDIENTS
Sub&tance
Chemical Name : Alcohols,C6-C12
Synonym : Octyl Decyl alcohol.
CASNo : 68603-15-6
EINECS No : 271-642-9
Ingredients or Impurities that : This product doesn't have impurities that contribute to the hazard
contribute to hazard classification.
Eye Contact : Rinse cautiously with water for several minutes, Remove contact
lenses, if present and easy to do. Continue rinsing.
If eye Irritation persists, get medical advice/attention.
Skin Contact : Gently wash with plenty of soap and water.
Ingestion : Cail a POISON CENTER or doctor/physician if you feel unwell.
Inhalation : Remove victim to fresh air and keep at rest in a position comfortable
for breathing.
Most important symptomps/effects,accute and delayed
: No Information available
Indication of Immediate medical attention and special treatment needed
: No Information available
5. FIRE-FIGHTING MEASURES
Appropriate Engineering : Facilities storing or utlllzing this materials should be equipped with
Controls an eyewash facilities and safety shower
Individual Protection Measures, such as personal protective equipment
Eye/Face Protection : Tightly seal safety glasses.
Skin Protection : Wear suitable protective clothing and glove (butyl rubber, nitrile rubber).
Respiratory Protection : If technical suction or ventilation measures are not possible or are
insufficient, protective breathing apparatus must be wom.
Thermal Hazards : Not applicable
Environmental Exposure : Do not empty into drains.
Controls
/
\
,•T.
~PT.
~
MUSIM MAS
~Fatty Alcohol, Methyl Esters and Derivatives
Ecotoxiclty : LC50
Species : Pimephales promelas
Dose : 2.3 mg/L
Exposure time : 96 h
EC50
Species : N. Spinipes
Dose : 3.1 mg/L
Exposure time : 96 h
Persistence and DegradabllHy : Readily biodegradable
Bioaccumulative potential : Octanol-water partition coefficient: log Pow: 3.15-4.57
Mobility in soil : No information available
Result of the PBT and : No information available
vPvB assessment
Other adverse effects : Additional ecological information : Do not allow to run into surface
waters, wastewater or soil.
\.
~PT. MUSIM MAS
, ATA. ,,Fatty Alcohol, Methyl Esters and Derivatives
Disclaimer
The release of this data sheet to you Is subject to the disclaimers herein. The lnfonnatlon contained Is based on the present
state of our knowledge and this Data Sheet Is for general lnfonnatlon purposes only. No representation, warranty or
111111111ntee ii!' ghMn AA tn ttltt 1.1~.r,,1111cy r)f 11ny stlltelnllnt or lnfomiatlon In the Dl!lta Sheet. We dlscl11lm all llablllty for any lose,
injury or damage which may result from any 1188 by you of the relevant data sheet to the fuDest extent pennltted by the law.
(
\
~PT.
'A~ T.
.. .
MUSIM MAS
,j._ ~Fatty Alcohol, Methyl Esters and Derivatives
SAFETY DATA SHEET
1. IDENTIFICATION OF THE SUBSTANCE AND THE COMPANY
eroduct Identification
Product Name : Octyl Decyf Alcohol
TradeName : MASCOLBO
Other Identifier : Alcohols C8+C10, 1-0ctano1+1-Decanol.
Recommended Use : Cosmetic base product for industrial purpose. General chemicals,
as they are used in many ways in the chemicals industry.
Company Identification
2. HAZARD IDENTIFICATION
GHS Classification
Physical Hazard : Not classified as hazardous substance
Health Hazard : Serious eye damage I eye Irritation, Category 2
Environmental Hazard : Not classified as hazardous substance
GHS Label Bement
'<!>
Hazard Symbol
I
""4,Fatty Alcohol, Methyl Este" and Derivative!
I SAFETY DATA SHEET
3. COMPOSITION/ INFORMATION ON INGREDIENTS
Ingredients or impurities that : This product doesn't have impurities that contribute to the hazard
contribute to hazard classification.
Eye Contact : Rinse cautiously with water for several minutes, Remove contact
lenses, if present and easy to do. Continue rinsing.
If eye Irritation persists, get medical advice/attention.
Skin Contact : Gently wash with plenty of soap and water.
Ingestion : Call a POISON CENTER or doctor/physician If you feel unwell.
Inhalation : Remove victim to fresh air and keep at rest In a position comfortable
for breathing.
Most important symptomps/effects,accute and delayed
: No information available
Indication of immediate medical attention and special treatment needed
: No information available
6. FIRE-FIGHTING MEASURES
Appropriate Engineering : Facllltles storing or utilizing this materials should be equipped with
Controls an eyewash facilities and safety shower
lndMdual Protection Measures, such as personal protective equipment
Eye/Face Protection : Tightly seal safety glasses.
Skin Protection : Wear suitable protective clothing and glove (butyl rubber, nltrlle rubber).
Respiratory Protection : If technical suction or ventilation measures are not possible or are
insufficient, protective breathing apparatus must be wom.
Thermal Hazards : Not applicable
Environmental Exposure : Do not empty into drains.
Controls
\.
14. TRANSPORT INFORMATION
Land Transport (US-DOT) : Not classified
Land Transport (ADRIRID) : Not classified
Sea Transport (IMDG Code) : Not classified
Air Transport (IATA) : Not classified
Inland wate1Ways Transport (AON) : Not classified
Transport In Bulk (Annex II of MARPOL 73nB and the IBC code)
Product Name : Alcohols(C8-C11), primary, linear and essential linear.
Ship Type :2
Pollution. category : Y
c
PICCS (Philippines) : Listed
TSCA(USA) : Listed
Chemical Safety assessment : No information available.
Disclaimer
The release of this data sheet to you Is subject to the disclaimers herein. The lnfonnatlon contained Is baaed on the preaent
state of our knowledge and th!s Data Sheet la for general infonnstlon purpoaes only. No repreaantatlon, wananty or
guarantee Is given as to the accuracy of any statement or lnfonnstlon in the Data SheeL We dlsclalm all llabillty for any 1088,
Injury or damage which may result from any use by you of the relevant data sheet to the fullest extent pennittad by the law.
/
I
\ __
Fatty Alcohols
i lNITED STATES E:'li\'IRONME~TAL PROTECTION AGENCY
\ WASHINGTON. D.C. 20460
Dear Registrant:
The amendment referred to above, submitted in connection with registration under the Federal
Insecticide, Fungicide and Rodenticide Act as amended is acceptable under 3(c) (5).
The new product chemistry and acute toxicology studies submitted are acceptable and will be
placed on file. The revised label reflects the new acute toxicology studies and is acceptable
If you have questions concerning this letter, please contact Banza Djapao at 703-305-7269, or via
email at djapao.banzara:epagov, or myself at 703-308-9443.
Tony Kish
Product Manager, Team 22
Fungicide Branch
Registration Division (7504P)
\
FIRST AID DIRECTIONS FOR USE
lflnEyes Hold eye open and rinse slowly and gently with water for 15-20 minutes. It is a lliolatioo of federal Law to use this prOOuct in a manner inconsistent with its labeling. Do not apply
Removecontactlenses,ifpresent,afterthefirstSminutes,thencontinue this p-OOuct in a YMJ that will contact wcxkersor persons, either directly or indirectly through drih. <Ally
0-TAC
rinsing eye poteaed h.Yidlers may be in the area during application.For any requirements specilic to your State or
Callapoisoncontrolcenterordoctorfortreatmentadvice. Tribe,con'llllt rhe agency responsible for pesticide regulation.
If On Skin Takeoffcont.aminateddothing. 0-TAC PLANT CONTACT AGENT is a c.arefu!!y balanced combin..-ition of active ingredients and wetting
or Clothing Rinse skin immediately with plenty of water for 15·20 minutes.
agents to be used for the conlml of sud:ergrowth on Burley, Flue-Cured, Dark F1red,Maryland and
'311 a poison control center or doctor for treatment advice.
Cigar tobacco. The concentrated product is diluted with water to form a creamy emulsion, which is
'311 a poison control center or doctor for treatment advice. applied as a coarse spray. The emulsion is effective only when it comes Indirect contact with suders;
ff Swallowed
Have person sip a g!ass of water if able to swallow. therefore, the material is applied so thlltmaximum contact is made with the suckers
Do not induce vomiting unless told to do so by the poison control
center or doctor. WHEN TO APPLY:
Do not give anything by mouth to an unconscious person. 0-TAC PLANT CONTACT AGENT can be applied before or after topping. Best results are usually ob-
If Inhaled Movepersontofreshair.
lfpersonisnotbre.;ithing.call911 oranambulance,lherigiveartificial
respiration, preferably by mouth-to-mouth, if possible.
C<!U a poison control center or doctor for treatment adllice.
PLANT CONTACT tained by spraying the tobacco with 0-TAC PLANT CONTACT AGENT before topping in th:- early to late
button stage and then topping the toOOcco immediately full owed by additional applications of().TAC
Pl.ANT CONTACT AGENT starting and spaced 3 to S days apart.If you top the tobacco before sp-aying,
remove any suckers over one inch in length as you top and apply().TAC PLANT CONTACT AGENT after
topping. Becau~(). TAC PLANT CONTACT AGENT is a contact type agent, it is necessary to straighten
I NCJTETOAiYSIClAN:Probablemucosaldamagemaycontn1indicatetheuseofgmritlavage. I
Have the container or !abel with y:ou when catting a pois<m rnntro! center or doctor or going
AGENT® any plants that are leaning so that the emulsion nows down the stalk evenly and contacts each sucker.
0-TAC PLANT CONTACT AGENT usually can be applied any lime during the day, but not to wilted
f~~~~~~:~:~~~~~~i~1Elli~r~~~~f~n~~Jlf~~i~~E~Y~~~~~~:a~
information
plan ls. For best results, it is recommended that you wait until the dew dries before spraying. Do not
spray ah.er the leaves begin to dose in the evening. Because the underside of the !eaves may be
Injured by contact with().TAC PLANT CONTACT AGENT,do not apply when the wind is high enough to
PRECAUTIONARY STATEMENTS
Hazards to Humans and Domestic Animals
CONTACT TOBACCO turn the top leaves over. Do not apply during the rain or when plants are wet. lfhowevl'f,it rairis ah.er
O.TAC PLANT CONTACT AGENT has been on the plants fur over an hour, you should not have to apply
().TAC PLANT CONTACT AGENT again. Do not apply during perlOOs of high heat or if plants are wilted.
DANGER
Cotrosive.C<!ui.es irrC"Versible eye damage. Wear protective eyewear (goggles, face shield, Of safety
glasses).Harmful if absorbed through skin. A~id contact with skin or clothing.Wash thoroughly
SUCKER CONTROL AGENT HOW MUCHO-TAC PlANTCONTACT AGENT TO APPLY:
with soap and water ah.er hllndling and beforeeating,drinking. chewing gum, using tobacco or For each tobacco type listed use the lower rate and apply to untopped plants in the button stage
using toilet. Remove and wash contamin..-ited do thing before reuse. Avoid contact with skin, eyes when plant tissue is tender, then top immediately.U~ the higher rate for the first application when
or clothing. Wear long-sleeved shirt and long pants, socks, shoes, and gloVt.":i (such as or made out plants are more mature and for the second application 3 to S days later followed by
of any waterproof materia!,~!ection cate-gory A) additior1al applications 3 to 5 days apart as needed.
Prolongedorfrequentlyrepeatedskincontactmaycauseallergicreac1iominsomeindividuals. Flue-Cured: For power sprayer - use 2 9<11ions r;T .57 liters) in 48 ga!!ons {182 lite-rs} of
PERSONAL PROTECTIVE EQUIPMENT {PPE)
Some materials that are chemical-resistant to this product a1e m<ldeof barrier laminate, butyl
KEEP OUT OF REACH water,foratotalspraysofutionofSOgallons{189!iters)-4%solution;
or2.Sga11ons(9.4liters)in47.Sgallons(180liters)ofwaterforatotalspray
rubber,nitrile rubber, neoprene rubber, polyvinyl chloride, or vi ton. If you want more options, solution of SO gallons (189 litersl- S% solution
fol!owthe instructions for CATEGORY Con an EPA chemical resistance category selection chart.
Emergency Overview
WARNING!
Form: liquid Color: light yellow Odor: Characteristic Fatty Alcohol Odor
1
0-TAC
Hazardous components
Component I CAS-No.
Octanol/111-87-5
Weight percent
36.2%
c
Decanol/112-30-1 48.2%
Polyoxyethylene sorbitan monooleate/9005-65-6 15.3%
Related compounds (dodecanol C-12)/112-53-8 0.3%
2
0-TAC
Flammable properties
Fire fighting
3
0-TAC
the environment.
Do not flush into surface water or sanitary sewer (
~
system.
Exposure Guidelines
4
0-TAC
Skin and body protection Long-sleeve shirt and long pants or coveralls.
Shoes plus socks.
Remove and wash contaminated clothing before
re-use.
Appearance
Form: liquid
Color: yellow liquid
Odor: Characteristic fatty alcohol odor
Safety Data
5
0-TAC
Toxicological Assessment
Ecotoxicity Effects
Toxicity to Daphnia and other 48 hour LCso to Daphnia magna (water flea):
aquatic invertebrates: 8.24 mg/I
6
0-TAC
Further information:
Dispose of waste material in compliance with all federal, state and local
regulations.
DOT
Not dangerous goods
TOG
Not dangerous goods
IATA
Not dangerous goods
IMDG
Not dangerous goods
RID
Not dangerous goods
California Prop. 65 components: This product does not contain any chemicals
known to the State of California to cause cancer,
birth defects or any other reproductive harm.
7
0-TAC
This information in this Material Safety Data Sheet is correct to the best of our knowledge
and information at the date of its publication. The information provided is designed only as a
guidance document for safe handling, use, processing, storage, transportation, disposal and
release and is not to be considered a warranty or quality specification.
8
l'NITED STATES ENVIRO:'li:\1E!'\TAL PROTECTIOI'\ AGESC'\'
WASHINGTO~. D.C. 20460
Dear Registrant:
The amendment referred to above, submitted in connection with registration under the Federal
(
I Insecticide, Fungicide and Rodenticide Act as amended is acceptable under 3(c) (5).
\
The new product chemistry and acute toxicology studies submitted are acceptable and will be
placed on file. The revised label reflects the new acute toxicology studies and is acceptable
If you have questions concerning this letter, please contact Danza Djapao at 703-305-7269, or via
email at djapao.banza'ti1epa.gov, or myself at 703-308-9443.
i
I
1
HaYethecontaineralabelwilhyouwhencallingapoi50flccnm::ilcenterorcloctCf'orgoingfortreatml!llt N-TACusuallyCMl beappliedilr\(lime dlJingtheday,bw notto wilted plants. Fot beSI ~t5.h Is
Fcremeryencyiofonnillion pertainingtotheproductlll'ld conlil!Ct'Mlfl~cal (919}-467-8352,Mondil'f
rec::ommeoded ttlal )'Qll wait ulllil the dew dries bebfe spraying. Do not spray after the leaws begin lo
tm>ugh Friday 9AM toSPM E5l AAerSPMoillycu Poison CcnodCenterarUll the National Mon Control
Hotlineat1-8l0-222·1222bradditionallnf01Tnation. clo5e In the evening. BecbUSethe undersideotthe leaves maybe !njun!d bycontactwtth N·TAC,do not
applyv.tienthewtrd rs hlgh~ghto tum the tople.wesCNer. Do not apply during the rain or when
planls are ~t lfhoweYer, It rains after N·TAC has been on the plants for over ao hour,)'Qll should not
PRECAUTIONARY STATEMENTS hiwe to apply N-TAC again. Do not apply during perJodsofhlgh heat r:. If plants are wilted.
Hazards to Humans and Domestic Animals
DANGER
CorrosF.le.Cau5es frre11erslb!eeye damage. Wear protective eyewear (goggles.. f.lice shleld,or i.afety HOW MUCH N·TACTO APPLY:
glasses). Harmful If absorbed through skin. Avoid Conla(t with skin ottlothing.Wash thoroughly fOfeachtobao:otypellstedusethelowerratl!andapplytoum~plantslnthebuttonstagewhen
with soap and water after handling and before eating, drinking.chewing gum, using tobacco or
u~ng toilet. RemOYe and wash c:ontaminated ciothlng before reuse. Avoid contact with skin.eyes
pl¥lt tissue Is tender,thent~!mmedialely.Use the Ng her rate b theli!ll appllcatlonwhen planlsare
ordoth!ng. Wear long-sleeved shirt and long pants, socks, shoes, and gloves (wch as ot made out by addltional applic.nions l to 5
IOOfe mature and for the serond appllcatloo 3 to 5 days later lbllowed
ofanywaterproofmatl!rlal,selectionc.ategoryA). dayl.apartasneeded.
Prolonged or frequently repeated sk!o contact may c.au~ allerg!c relletloos In some lndlvlduals
FWE-CUREI>. FOfpov.erspril)'el'-U""!29allonsrJ.571iten.)Jn48gallons(1821i't:ers)
ofwater,foralotalspraysolut!onof50gallons(t89liter.;)-4%solullon;
PERSONAL PROTECTIVE EQUIPMENT (PPE)
Some materials that are chem!cal-reslstantto this product are imde of barrier laminate, butyl
rubber, nltrlle !llbber,neoprene rubber, polyvinyl chloride, or vi ton. If you want more options, follow
the lnstructiOns fot CATEGORY Con an EPA chemic.al resistance categOf)' selection chart.
NOTE:lntheeventof..iexterdedseasoo,laterappl!t:adorlsol'259aflons(9AU~
N-TACln47.5gallons(180U~wa!er(5%CD11a!111ra!ia'\)maybellli!lde.
"""''"
•
•
•
•
Coveralls
Chemkalreslstantglcwes
Shoesplussocks
Protectlveeyewear
BEFIRE USING THIS PRIDUCT. HOWTOAPPLY:
The dilUled em.i!~on Is most easily prep.¥ed by adding the required armunt ofN·TAC to )OU" spray
tank and theri adding the water. In order to obtain the best res.ills, It ls Important that the water be
added to the N-TAC rather tharl the N-TAC IO the water to e11harice mixing and reduce floating.
USER SAFETY RECOMMENDATIONS ACTIVE llGREDIEITS: l% llJWelgbU K)'Qll use a hard-held orbackpadsprayer,lhe dnuted :solutlonmuSlbeapplled a! a rate of2/lto 1
Users should. ounce (20-30mUl!lhen.)per plant(otenoughtoln5Ure rurdO'Ml to the bottom of the p!antj. A coarse
• Wash hands before eaUng,dilnklng,chewlng gum, using IObauo oru~ng toilet. Octanol (C8l 36.2% spray ls recommended, directed doYmwaid at the top of the ~k fn:m 6-8 ll'ldles abcM! the lop leaves,
• Remcwe dothlng/PPE Immediately If pesticide gets Inside.Then wash thoroughly
aind put on c1eandothlng. Decanol (ClO) 48.2% wry litlle tanli; pressure ts required, and In no case shoLid more than 20 pounds be used.
• Users should remcwe PPE. lmn'll'diatl!ly after handlJng lh!s product. Wash outside ofglcwes
before remcw!ng. As woo as possible, wash thoroughly and change Into clean clothing. Related Compounds (dodecanol Cl 2) 0.3% Ytlhen applied with power eqLipmen1,three nozzles per row muSI be U'.ied (TG full cone tips,ot liir'ger,
are satisfactory). one TG-5 noZ21e should be directed downward ewer the centl!rof the row and two
OTHER INGREDIENTS: 15.3% TG-ls should be positioned approxlmately 11 Inches on either :5kle dkKted at or slightly alxwe the top
ENVIRONMENTAL HAZARDS
Do not apply dire<:dy to water.to areas where surf.lice watl!ris present or to lntertJdat areas below
TOTAL 100% of the stalk. The dHuted N-TAC must be applied to the tobaccoasa coane splil'f fn:m a height of 12 to
161n&es abcwe thetopoftt-estalk. lllsrecommended that boom~5Ure be kept at 201~ By~ng
the mean high wat11r mark.Do not contaminate wat11r by deaning equipment or disposal of wast£!. the recommended spray tips, spraying at approximately 20 lbs.pres5Ure,andoperaling a traaot speed
of 25 to 3 mph, you w!ll apply approximately SO gallons of dQuted solution per aae ot tobaccc.
This product contains 2.57 lb.octanol 3.41 lb.decanol and
STORAGE AND DISPOSAL
Doool cornamlnatewater,bxlor feed by mirage llllddlsposat 0.02 lb. dodecanol per gallon. If not used in accordance HOWOFTENTOAPPLY:
1. PESTICIDE S1'0RAGE - Do no! stack over 2paUets Ngh. Store orlginal containers Jn cool dry place
with directions, plant injury, excessive residues, or other l.l!iUally ooe app!Jcatioo ofN-TAC wfll give goOO ccntroJ of both primary and secondary 51.lden and
produce excellelll leaf quality. Howevet,ln rrno;t casesaddil:lonal treatments of N-TAC are recommend-
~fn:mfood,waierandfeed.. undesirable results may occur. ed lto Sdaysapartto allowUme rorune-.oencr~s tobeccme 1.E11form.
2.PEsnaDE DISPOSAL- PeWdde wastl!s rewldng fn:m the U5e of lhls produc.t may be disposed
ofonsltl!otatanapprovedwastedlsposaifadlity. NOTE~
Sold by: 1. Mbcwe!lpriottou~and,ifalla.wdtostanddur1n9theu:1e,mlx
3.CONTAINER DISPOSAL- Noo-1'efillablecontarners. Do not reuse Of raftll this conlalner. fClf ton-
tllnet !ilim ofS pftons orleu, triple rinse as foll~ Empty !he remaining contentslntoappllcallon
equipment or a mix tank and draining for 10 seconds after the flow begins to drip. FPI the container 'A
Fair Praducts, Inc., USA apaln before applying since the clluli'd emulMon may 5eP<1rate on
standing.
IU:1 wilh water and recap. Shake for 10 seconds.Pour rlnsate into application equipment or a mtx tank 2 Do not use oo Bu-ley !obacCD during pericxls othlgh heat arid high humidity.
or store rinsate for later use or disposal. Drain for 1Oseconds after the flow begins to drip. Repeat thl~
Agri-Specialties Division l. Usage ac{:ord!ng lo the dlrectlonsout'IJned hasreSJited inadequatl! sudei
proced~ t-.. more times. Then offer brrecyding If available, or pUlcture and dispose of In a sanitary Post Office Box 386 comro! with very Htt!eot noleaflrl~. Applk:allon not In accordance with
l<wldfill,Oftr,r Incineration, or KaJloY.e:I by state and local authoritles,byOO-ning. lfbumed,Staywtof
the directions may lead to Injury of leaves or Improper sucWr control.
Cary, North Carolina 27512
"""''·
forcvntithM:r!ilimgreaterthlinS91lkln$.trlplerinseas follows: emplytherema!n!ng contents Into Telephone: (919) 467-8352
Makesuresprayequlpme11tlsdearibeforeusJng.
Oonotmlxwlthotherpestk:ides,~rtlllzers,surfactantsot any other materials as
application eqLipment or a mix tank. Fill the container Y• full with water. Replace and tighten closures. plantdamage ordealhmayresLit.
llp container on its side and roll It back and forth, ensuring at least one complete revolution, for 30
seconds. Standthecontalneronltsendandtlpitbackandforthseveraltlmes. Tum the container over
onto Its other end and tip It back and fotth several times. Emply the rinsate Into application equipment
WARRANTY STATEMENT: TotheeXletlt permitted by applicable law,Sel1er\guararnee shall be
MADE IN U.s.A. limited to the terms of ft-e label, and !>Ubject thereto the buyer ~Sl.SneSarr-J fir.Ir. to penons Of proper1)'
or a mix tank or siore fins.ate kir later use Of disposal. Repeat the procedll'e two more times. Then offer
for recyding If available, or puncture and di:;pose ofln a sanitary lanclli!l,or by incineration, or If allowed EPA REG.N0.51873-20 NET CONTENTS: arislngoutofuseothardllng ardaccepts the product oo lhese a:n::!llion'!i.
by state and local authorities, by burning. If Ix.med, stay out of smoke. EPA EST.N0.45671-NC-01 275GALL.ONS
!02102014V-2014Pi 1040.9 LITERS
I
\
N-TAC
(
Material Safety Data Sheet
I
\.
N-TAC
Version: 1.2 Revision Date: 09/07/2012 Print Date: 09/07/2012
Emergency Overview
WARNING!
Form: liquid Color: light yellow Odor: Characteristic Fatty Alcohol Odor
1
N-TAC
Hazardous components
2
N-TAC
Flammable properties
Fire fighting
3
N-TAC
Storage:
Exposure Guidelines
4
N-TAC
Skin and body protection Long-sleeve shirt and long pants or coveralls.
Shoes plus socks.
Remove and wash contaminated clothing before
re-use.
Appearance
Form: liquid
Color: yellow liquid
Odor: Characteristic fatty alcohol odor
Safety Data
5
N-TAC
Toxicological Assessment
Ecotoxicity Effects
Further information:
Dispose of waste material in compliance with all federal, state and local
regulations.
DOT
Not dangerous goods
TOG
Not dangerous goods
IATA
Not dangerous goods
IMDG
Not dangerous goods
RID
Not dangerous goods
California Prop. 65 components: This product does not contain any chemicals
known to the State of California to cause cancer,
birth defects or any other reproductive harm.
7
N-TAC
This information in this Material Safety Data Sheet is correct to the best of our knowledge
and information at the date of its publication. The information provided is designed only as a
guidance document for safe handling, use, processing, storage, transportation, disposal and
(
release and is not to be considered a warranty or quality specification.
·\._ ..
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1NOT TO BE RETURNED• I
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•THIS IS NOT A BILL•
••••••••••••••••••••
PESTICIDE REGISTR\ATION CERTIFICATION
..
THIS CERTIFIES THAT THE BRANDS OR G)tADES OF PESTICIDECS) LISTED BELOW HAVE
BEEN DULY REGISTERED, AND THEIR SALES I~ NORTH CAROLINA AUTHORIZED FOR THE CALENDAR
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OF CHAPTER 143 OF THE GENERAL STATUTES. f ~~9z-gi
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SUBMITTED FORt FAIR PRODUCTS INC .SUBHlTIED BV1 FAIR PRODUCTS INC PHONE: (919)467-1599
0000012~1 RENEE ALLEN 00~001231 RENEE ALLEN.
PO BOX 386 PO BOX 386
CARY NC 27515 CARY . NC 27515
REG ETF REG
EPA REG HO )RAND NAME OF PESTICIDE CAS SHOWN OH LA,EL) NC ID STATUS FEE FEE YEAR
051873-00002- - FAIR PLUS FOR THE PREVENTION OF GROWTH
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TOBACCO SUCKERS 19881729 RENEWAL tl50.DO t50.00 2015
051873-0000~- - ' FAIR.TAC CONTACT ~OBACCO SUCKER CONTROL\AGENT
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200ll99l RENEWAL $150.DO •so.oo 2015
051873-110006- - FST-7 CONTACT & SYSTEHlC TOBACCO SUCKER;coHTROL AGEN~ 19881730 RENEWAL $150.00 t50.00 2015
051873-00007- - FAIR 85 CONTACT TOBACCO SUCKER CONTROL 4GENT 19881728 RENEWAL $150.00 tso.po 2015
051873-00008- - DE.·CUT TO CONTROL & .RETARD PLANT GROWTH jIN ACRES DIF'FICUL'r TO 11AINTAI
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19881731 RENEWAL tl50.00 t25.00 2015
051873-00009- - FAIR 30 FOR THE PREVENTION OF GROWTH OF !TOBACCO SUCKERS
.' 19881732 RENEWAL tl~0.00 $50.00 2015
051873-00017- - FAIR 80 SP FOR THE SYSTEMIC PREVENTION OF TOBACCO
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SUCKER GROWTH . 19:960990 RENEWAL $150.00 tS0.00 2015
0518H-00018- - O·TAC PLANT CONTACT AGENT
'
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051873-00018- - GREEH·TAC PLANT CONTACT AGENT
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20121147 RENEWAL $150.00 $25.00 2015
051873-00020· - H·TAC TO!ACGO SUCKER CONTROL 2on132a RENEWAL $150.00 $25.00 2015
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I '
MASCOL 80
Fatty Alcohol
(
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Substances Physical Properties and Mode Of Action
. Natural Fatty Alcohols, are derived from natural sources generally isolated from
any of a variety of natural occurring fats, oils, and waxes of either animal or
vegetable origin, The most commonly used sources are coconut oil, palm oil, lard
and tallow.
..
The alcohols are prepared by a transesterification of the fatty acids in the
triglycerides found in natural oils and fats followed by--a catalytic hydr6genolysis .
of the resulting esters. purification and fraction of the resulting alcohols is similar
to' the synthetically produced materials. All of the natural alcohols used here are
PKO, sustainably sourced I
The Primary Mode of Action, upon contact of the natural fatty alcohols the axillary
buds/suckers at the leaf axils; the s0lution eentaining-the-ac-tive-substanee quickly-- - -
dissolves the thin underdeveloped cuti{e or waxy area and results in desiccation of
the axillary bud/sucker by rupturing cell walls and rapidly evaporating liquids.
(
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History Of Natural Fatty Alcohols
/
In the Shell higher olefin process, the chain-length distribution in the initial mi};Cture of alken'"
-/-
oligomers is adjusted so as to more closely match market demand. Shell does this by
means of an intermediate metathesis reaction.Ml The resultant mixture Is fractionated and
hydroformylated/hydrogenated in a subsequent step.
Applications
Fatty alcohols are mainly used in the production of detergents and surfactants. They are
components also of cosmetics, foods, and as industrial solvents. Due to
their amphipathic nature, fatty alcohols behave as nonionic surfactants. They find use
as emulsifiers, emollients and thickeners in cosmetics and food industry. About 50% offatty
alcohols used commercially are of natural origin, the remainder being synthetic.ill
Nutrition
Very long chain fatty alcohols (VLCFA), obtained from plant waxes and beeswax have been
reported to lower plasma cholesterol in humans. They can be found in unrefined cereal
grains, beeswax, and many plant-derived foods. Reports suggest that 5-20 mg per day of
mixed C24-C34 alcohols, including octacosanol and triacontanol, lower low-density
Jipoprotein (LDL) cholesterol by 21%-29% and raise high-density Jlpoprotein cholesterol by
8%-15%.lcitation neededJ Wax esters are hydrolyzed by a bile salt-
dependent pancreaticcarboxyl esterase, releasing long chain alcohols and fatty acids that
_are absorbec! l_n the gastroin_testjn~I tra9l Stµdies_ of fatty al9Qho! l]l~f_?!QoJi~IJl..
in fibr~bJasts suggest that very long chain fatty alcohols, fatty. aldehydes, and fatty acids are
reversibly inter-converted in a fatty alcohol cycle. The metabolism of these compounds is
impaired In· several inherited human peroxisomal disorders,
including adrenoleukodystrophy and Sjogren-Larsson syndrome.lfil
Fatty alcohols, derived from natural fats- and oils, are high molecular straight chain primary alcohols.
They include lauryl (Cl2), Myrlstyl (C14), Cetyl (or palmityl: Cl6), stearyl {Cl8}, Oleyl (Cl8, unsaturated),
and Linoleyl (Cl8, polyunsaturated) alcohols. There are synthetic fatty alcohols equivalent ptwsically
and chemically to natural alcohols obtained from oleochemical sources such as coconut and palm
kernel oil. Fatty alcohols are emulsifiers and emollients to make skin smoother and·prevent moisture loss.
Identical fatty esters are used to improve rub-out of formulas and to control viscosity and dispersion
characteristics in cosmetics, personal care products and pharmaceutical ingredients. As chemical
intermediates, the primary use of fatty alcoh~ls are <?S row material for the production of fatty sulfate
salts and alcohol ethoxylates for foaming and cleaning purposes in the field of detergent industry.
Chemical reactions of primary alcohols include esterifications, ethoxylation, sulfation, oxidation and
many other reactions. Their derivatives and end use applications include:
. -;...·-
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5
Manufacturing and Production Process
Fatty Alcohols
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Prepared by:
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Flowchart
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FFBENTERS
THEPLAHT
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TRANSPORTATION OF FFB
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PHYSICAL DEGUMMINQ
(STEAM) AND
REFINING PRE-BLEACHING
!+
FATIY ACID DISTILLATE ... 1
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EARTH DEODORIZATION
BLEACHING
--~------\
/--......... 0 '~\
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Used in
Soap & detergents
Chemical synthesis
Food ·& Feed additives
Cosmetics
Vegetable oils : Pharmaceuticals
__:
.~.·~
palm, coconut, Paints
rapeseed, ~,'.~
sunflower, etc. Textile products ..
Polymer additives
. Rubber additives
Oleochemical plant
/ Paper additives
Ag roe hem icals
CAP RO IC C6 - - - . - 1.3 Tr
STEA RIC C18:0 18.2 4.5 4.8 3.s 1.2 2.7 2.3
ICOSANOIC C20:0 - - - 2 7 Tr
('~.·
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.:f esterification
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I~ Foods, Lubricants,
i-·
{I)
neutralization
~ ESTERS
;.
Coatings
I~
\ Personal Care,
. . s:..:. ~ SOAPS
' Lubricants
<O
(I) -
-·<
U. VI
-·
VI
nitrilation
~ ~.FATTY Lubricants,
AMINES Surfactants
~
:::s METHYL
amidation/ quartenization I AMINOCATION Surfactants
{I)
tD .. I
ESTER
i""" .I amidation/ neutralization . ESTER-AMIDE. Surfactants
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Ll
• HYDROCHLORIDE
,...
c;· hydrogenation
:::s Surfactants,
• ALCOHOL Lubricants
-~
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MEtHYL
The starting materials
ESTERS
Intermediates for
hydrogenation
ALCOHOLS
Surfactants, Lubricants
--(::,;/
.....
,
Sulfonation
MES ·I . Detergents
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,,,,,,----....
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· FATrrY
The starting materials
ALCO OLS '
Dish-washing
Acetalization ;Alylglucosides I · i
detergents ..
low irrit~tion, provide laH ~ring'
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Shampoos
Household detergents
1 Toothpaste
_, ''-
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Palm Kernel Oil Process .Flow ...
Bunch
BUI!Ch
Sterilization
Bunch
ThresbiD:g
Frtiit
Digestion
Pulp Nut
Pressing .Recovery
Oil
. Clarlficatio11
Oil
DJ}'ing
· Kemel
Storage
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· FattvAlcohol Process.Flow
Process Flow
Esterlflcatfon
HydrogenatloJi
.·
Retlnlng I Pollsldn~
.. .·.
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Pagel of
--·····-·c
f~t,-bf··---p;rrr; oil fnfo·--··-·:·-·~·-···--.~·--·--···-~--··-·..-·--·--·--·-~-·---··---·-··-·:....··-:-·-·--~-..
!Date: 1/19/200912:11:27 PM Eastern Standard Time • . ·
iFrom: Iohn:[email protected]
fro: [email protected];corii. [email protected] . .
. mmm~m~\ .
l~~!.~P.!!~.!nt~~-·-·····-:···-···--·-··-·-·:.._._:________._:.....--·--·----·--···-:..:.....:_:_-_____.___.__:..·---·-
Below Is general
. . Information
. regarding the production of palm oil. Our palm oll,·laurfcs and
. related products are widely used rr:i . many Jndustnes lnduding food manufacturing,.
cosmetics and pharmi,ceutlcal Industries.
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Afte'i-,the steam.Ing process, the palm frultlets a~e crushed In a pressing machine to obtain
~ . . .
crude palm oil and palm kernel. Waste. and water Is then deared
. . . .
and separated fi-om the
CPO by means of a cenbifuge. !he cleared crude p~lm c;>ll emerging from the .cenb1fuge Is
then sent for refl~·lng while the pal~ kernel. nut Is seni: for crushing." l'hi: empty frUlt
bunches and
.
. llquld waste
. I
.
arising from' the proces~ are used as fertnlser In the plantations.
..
e palm kernel nut Is ·fracb.f~d causing the palm kernel
=within the shell tocontract away from :the shell. The sheD Is separated from the kernel
. ::through a dav. bath where It- ls used as fuel In th~ boiler room or ~~eneratfo~ plant.
The palm kernel Is furthet crush~d to produce cru~e palm kernel oil and the remaining palm
kernel meal Is used ~s animal feed.
..
Thanksr .
John Schnieder
·.
ICOF America Inc · . ·
10979 Reed Hartman, Suite 109
Cincinnati, OH 45242 .
· Email: [email protected] .
Office: 513-791R1782
Main: 513-791-6813
Mobile:· 513-746-7663
Fax: 51$-791-2767
Internet: www.icofgroup.com
CONFIDENTIALITY NOTICE: this e-mail fs Intended onfy for th.e person(s) to whom
ii Is addressed a11d may .
contain confidential and/or privileged material. Any unauthor,zed review, use, disclosure ordf::mibuting Is
prohibited: If you are not the Intended recipient; please contact the sender by e-mail and destroy all copies of the
ori_ginal message. . · · . . .
_.- /b,
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Natur.al Detergent Alcohols, Niµural ~etergent Alcohol Plant
. ~;··
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•.. .- . . W;..:·p, . . ...
. . ·:=l:~S
. . ~e ·J~ttmJ~s.v.
~;~ttfrat Qet:erget)t .A~cotJols
. . ·,
The D1avy Proc:eSs TeChnology Natural petergentAleohol process converts tatty a~ds to non-
. acidic intem:iediate methyl esters and .hydrogenate$ these to alcohols. M~anol vap~:mr
. passes counter current to the fatty acrd f;lnsuririg almost complete conversion of the fatty acids
to methyl esters. These are fed·directlyto a low pres$ure {40 bar) vapour phase .
hydrogenation process over a fixed bed. of chrome free copper catalyst to produce a high puf:lty
_\ .-
.. crude mDcecl alcohol product ~tream•. The:product alcohol is then.refined before being polished
~
I
' to convert any residual carboriyls (i:>rincipally aldehydes) in the.producUo alcohols. The ..
methanol consumed in the esteiificatiori is recovered fn·tiJe hydrogenation step and recycled;
so the methanol m~ke-up is mininl;:ll•. The C12-C14 product alcohols are removed as a liquid
side-draw from near the top of the column and pumped to product polishing. The C16-C18
product alcohofs .are· removed as a vapour side-draw from .near the· base .of the column •. ·The
. trace aldehydes in the product to alcohol.
product pofishing .system convertS any
.. .
l\.'fethanaf · Hydrogen ~edlate~ .. · . .
.
Fatty~·--..
. ...
!. . ·\·~ ·. "."J:.r:·:~· 1i:/:~ ~.; t . .
~~r~~: :·-~·•..::.~:.,~*~;.;.~·/Refining -:1;' Deter~AlcohoJs
. ...
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This vapour.pJiase proce$s has been licensed around the world in 10 ester·hydrogenatlon
plants with a total Installed Gapacity of 350,000 tonnes per year of alcohols. These p!ants have.
VirtuaHy no effluentS; smaU by-product streams are.recycled and consumed Within the process
so they have minimal environmental impact Pfease contact us for further infmmation. ·
,,.- ..... , .- ...........
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Process Flow· Chart
o:.TAC Agent: Mascol 80. Fatty Alcohol Methyl Esters
I C8C10acid -
Vegel'able oil
1'1"..
--"""';. $pfitter · ---·-:: Acicf Fractionation 1--....;;i.). C12C14 acid -
.....
{CPKO) C16Cf8 ·acid .-
• • ·' iJ'
GlyceritJe
...
Methgnol Hytjrogen ~ ·
1(7 .
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M~scol 80 Oco/I Decyl Alcohc:>I
The traditional and_ still important source of fatty alcohols are fatty acid esters. Fatty :
acid triesters, knoyvn as triglycerides, are obtained from plant and animal sources. ··
Musim Mas uses renewable Palm. K_ernal Oil as the oil feed . These triesters are.
subjected to transesterification to give m·ethyl esters, which in turn are hydrogenated to
the alcohols. Shorter alcohols (C8-C 10) are obtained from coconut oil and palm kemal
oil.
Methanol- MethYf·
Fatty acid + · or
Butanot
+-+ · Ot·
B~thyleater
.
:
- ...
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Gas-Phase Hydrogenation
ihis process requires a vaporized ~ubstrate and is therefore particularly suitable fo·r
me~hyl esters. Ch~racteristics of the process are an ·extremety·targe excess of recycle_
gas (approx. 600 mole of H~ per mole of ester),·high gas velocities and the addition of
methanol to aid evaporation. The product mixture is split into a gas and. a liquid phase;
the hydrogen is recycled, the methanol is stripped from the fatty alcohol and the fatty
alcohol is purified by distillation ·
.
The Davy P.rocess Tec~nology Natural Detergent Alcohol process converts fatty acids
to ."non-acidic intermediate methyl esters and hydrogenates these to alcohols. Methanol -
vapor passes counter: ~urrent to the fatty acid ensuri11g almost complete conversion of
the fatty acids to me.thyl esters. These ~re fed directly to.a low pressure (40 bar) vapor
phase hydroge~ation process over a fIXe~ bed of chrome free copper catalyst to
produce a high purity crude mixed alcohol product stream. The produ"ct alcohol .is then
refined. The methanol consumed in the esterification is recovered in the
hydrogenation step and recycled. ·
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• Polysorbate 80
USP Certificate
Polysorbate 80
LOT GOI359
Molecular Formula
Molecular Weight
(OCH1 CHi)yOH
____ _13_!>_9.G'L __
POl..YSORSATE 80 2 g
CIJITIONI.,_
Do nnl drf- Ms q>el*1g arnPIA,
llora In• lljiH!JcloMd
. aonlalr.. Pnndad"""' Jleht.
. . .
USP certifies that the USP Reference Standards Committee, in accordance with their rules and procedures.
· determined that this USP Reference Standard lot is sµitable to assess compliance with the monograph.standards for
which it is specified. The criti~ cbamcteristics of flrls lot ere usually deterinined indepmdently in three ~r more
Jaboratories. including USP. government, academic,.and ind~ collaboraf:Ors.
\. ·(
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Page 1 of2 09-Apr-2010
\
(• Calculation Value
Unless otherwise stated on the Reference Standard label, a value of 100.0% should be used in USP or NF
compendia! applications for wbii::b. the use o( this Ref~ce Standard is intended. Please refer to ihe specific
Reference Standard label for further information.
Expiration
Current lots are identified in the Official USP Reference Standards catalog. In SODl!' cas~s. the previous lot may still
be considered official. If so, it is identified in the column marked "Previous Lot/Valid Use Date." Ordinarily, the
previous lot i~ carried in official status for about one year after the current Jot enters· ~stribution.
It is the responsibility of each.user to determine that this lot is current when used. To ellS!lI'C up-to-date information.
USP publishes the Official USP Reference Standards. Catalog, which contains official lot designations. This ·
information is also available on the USP web site, at W\vw.usp.org, as well as in the bimanthly subscription
publication. Pharmacopeial Forum.
Non-Monograph Use
The suitability of this Reference Standard for use in nan-compendia! applications is solely the responsibility of the user.
. ...
LEGAL NOTICE
USP. MAKES NO REPRESENTATION OR WARRANTY WITH ~CT . TO THE ACCURACY, .
COMPLETENESS, OR CURREN'INBSS OF THIS CERTIFICATE~ AND USP SPBCIFICALLY DISCLAIMS
.NNY OTHER WARRANTY, EXPRESS, IMPLlED, OR STATUTORY, INCLUDING BUT NOT L1MlTBD TO,
THE IMPLlED W.ARRANTIES OF MERCHANTABILITY AND FITNESS FOR A PARTICULAR PURPOSE.
USP DOES NOT WARJJ.ANT THAT 1HE INFORMATION CONTAINED HBRB1N MEETS THE
CUSTO:MER'S RBQUIRBl:v.1ENTS. USP SHALL NO_T BE LIABLE ON ACCOUNI' OF ANY SUCH ERRORS
OR OMISSiqNS. ·
~hereby the ~~ximwn amount ~£ the additive in the finished sodium chloride
does not exceed 10 parts: per millio~ .
(
. (6) Id-·special dietary foods, as an emulsifie~ for edible fats and oils,
\ with directions f.or use which provide for the ingestion of not· more than
360 milligrams of polysorbate 80 per day.
(?) AS .a solubilizing and dispersing agent for.dill oil in canned spiced.
green beans, not to exceed 30 parts per millio~ •
.(8) As an emuls~fier, alone or in coi:nlJination with polysorbate 60, in
shortenings and edible oils intended for use in foods as·follows, when
standards of identity established under section 401 of the act do not
preclude such use:
.· (i) It is .used alone in an amount not . to exceed l percent of the weight of
the· fini_shed shortening or oil.
(ii) It is used with polys-orbate 60 in any c.ombination providing no more
than 1 percent of polysorbate 80 and no more than 1 percent of polysorbate
60, provided that the ~otal combinatio~ does not exceed l.percent of the
fi~~~h~9 shortening or oil. .
(iii) _;h~ 1-percent limitation specified in paragraph (c) (BJ (i) and (ii)
0£ this section may be exceeded in premix concentrates of shortening or
edibl~ oil if .the labeling complies with the requirements of paragr·aph (d)
of this section.
(9) As an emul~ifier in whipped edible oil to~ping with or without one or
a combination of the ~ollewin~:
(i.) Sorbitan monostearate;
(ii) Polysorbate 60;
.•:
lii~) P9lysorbate 65;
(··-, ~he,repy the maximmn amount "of the additive or additives .used doe.s not
\ exceed·0.4 percent of the weight of the finished whipped-edible oil
t~P,_ping.
:(-10.) It is \.lSed as a we~ting agent in sc::ald water for· poultry
d~featliering~ foilowed by potable water rinse. The concentration of the
ad~tfve in the scald.water does not ex~eed 0.0175 p~rcent .
. ·(11) As a·qispe~sing agent in ge~atin desserts a.nd 1n gelatin dessert
mixes, whereby the amount of the additiv~ does not exceed 0.082 p~rcent on
a dry-weight ba~is.
(12) As an adj~vant added to herbicid~ use and plant-growth regulator use
dil~tions by a grower or applicato~ prior to appl1cation of such dilutions
to the growing ~rop. Residues resulting from such use are exempt from the
.requir~ent of a tolerance. When so used or intehaed fo~ use, the additive
sha1l be exempt .from th~.requirernents of paragraph (d} (1} of -this sect.ion.
(13) As. a defoaming agent in the preparatio~ of the creaming mixture for.
cottage cheese and lowfat cottage cheese, as identified in 133.128 and
133.131 of this chapter, respectively, whereby the'amount of the additive
does not exce~d .008 percent by weight of the fini~hed products.
(14) As a surfactant and wetting agent for natural and artificial colors
for use in barbecue sauce where· the level.of the addit~ve does not exceed
O. o·os percent by weight of the barbecue sauce.
(d) To assure safe use"of ·the additive, in addition to the other·
information required by the Act:
(1) The label 0£ ~he additive and any intermediate premixes shall bear:
(i) The name of the additive.
(ii) A statement of the concentration or strength of the additive in any
intermediate premixes.
(2) The· label or labeling shall bear adequate directions to provide a
final product that.complies with the limitations prescribed in'paragraph
(c) of this section.
[42 FR 14491,, Mar .. 15, 1977, as amended at 4~ F~ ?R71 .T:.T\. ~n
• Polyaotbatii 80
CCl4; sp. Qt. 1.05; HLB 10.5; pour pt 33 C; a'?kl no.~ maX.: sapon. no. 88- Polyso!bate 85 ~\-
98; hyd. no. 44-60; flash JJl (CC) 149 C; Nonloolc • CAS 9005-7~ (generic) .
Toxicology: TOLD (oral, rat) 635 ~g; experimental reproductive elfector; · Synonyms: PEG:20 sorbitan bloleale; POE (20) i.v.u1ll.
TSCADsted ma~ trioleate 300
PmcaQtfon: Weer safety glasses, lab.coa~ and dust resplra\or Deflnitloir. Mixture of oleate esters of soibltol and s0ib11o1
HazarcJous Qebomp. Prods.: }:leated to decomp., emits acrid-smoke and ... 20 moles ethylene oxide ·
lnllaling fumes • Properliw. HLB 11.0: Nonionic
HMIS: Heallh 1, AammabD!ly 1, ReacllvltyO · · Toxlcolow. Human skin lnitant TSCA Dsted .
Uses: Emulslfi.er. dlspersan~ stabilizer in foods, {ca cream, frozen desserts, Uses: S°"olublllzer for navors, vitamin oDs; o/w emulslfler 1
cakes, cake mlxeS/icings.lfilllngs, whipped toppings, coffee whiteners; conblllzerfe~ convenience food appllcs.; we!Ung agent,
defoamer Jn· processing foods · · mloods. • . •
RegulatDry: FDA21CFR §73.1001, 172.838, 173.340, 175.300,.178.3400; RegulstOJy. FDA21CFR§175.300, 178.3400 • .
Europe lisfed;iJK approved; Canada DSL . MB(Jllf.ID!slrib.: Aldrich; ri11ka; Mosselman NV: Sigma· S
ManufJDlstrib.: Fluka; Mosselman NV: Sigma . · Prods.• • I • '
Trade Names! AvapollM 65; CrDlet 35; Durfax® 65; Gfycosi::ierse@ TS-20 Tiade Namss: Alkamuls® PST0-20; Cri!lel 45; Sorbax P
KFG; Kofilen.s/3; Uposorb TS-20; Liposorb TS-201<; lumfsorbm PSTS- 85 .
20K; Sorbax PT6-20: T·Maz® 6SK; lWeen® 65 · Polystyrene • ·
• Trade Names Contain.Ing: Aldosperse® TS-2Q; Aldosperse® TS-20 FG; CAS 9003-53-6; 8NECSJELINCS 202-851-5 • •
· Aldosperse® TS-20 KFG; Aldosperse® TS-40; Aldosperse® TS40 FG; UN2211 .· .
Aldosperse® TS40 KFG S}7Jonyms: Ataclic polystyrene; Benzene, ethenyl·, horn
..P~lysorbate ~o · . · nybenzene homopolymer; Polystyrene latex; Polystyren
CAS 9005-65-6 (generic); 3720().49.-0; 61790-86-1 · rol; PS; Styrene polymer, Styrene, polymerized; Vinylber
FEMA2917; INS433 • Class111catfoil: Hydrocarbon Jio!ymet ·
Synonyms:· PEG-20so!bltan ol~te; POE (20) sorbitan monooleate; Sorbi-· Definition: H~h molecularwelgfitthermoplaslic resin produ
• maciogol oleate 300 lcal polymenzallon of styrene; grades: aysfa!, Impact, ex
Definition: MixtUre of oleale esters of sorbitol and sorbltol anhydrldes, with EmJir1caJ: (CalfJx -. . .
.. 20 moles EO · • · Formula: (CH{Cefi,¥.;HJx ·
Properties! Amber 'ilfsc. Dq.; faint odor; bitter lasta; nonionic; very sol. In ~ Colorless to ylsh. glassy solid or soft colorless
water; sol. In alcohol, fixed o11s, cottonseed 0tl, com oil, ethyl acetate, Ing odor; sol fn alcohol; sl. sol. In water; m.w. 2500-250 o
methanol, toluene; lnsol. In min. on; dens. 1.06-1.1 O; We. 270-430 cSt; k<IJI; RLp. Q'B-91 C; soften. "Pl 80-102 C; ref. Index 1.59·
HLB 15.0; acid no. 2 max.; sapon. no. 45-55; hyd. no. 65-80; pH 5-7 (5% M"Pa: fens. mod. 3900 MPa ·
·T~ .LD50.(oral,.mouse) ~ g/kg, (IP, rats) 6.3_·~. fJ'/. rat) ~79.. 1b_xlcology: TDLo OV. rat, 2 wk lntennlttent) 200 mg/kg, QffiJ
!ts: severe ~ lllttant tnaY cause lrritalfon to mucous,1•1.
. ll'IJJ/k!I; inod. toxlC by Wroute; mildly toxic by lnQ.; eye hrltant question- bi nan:ollc lri hfgft cones.: quesllonable carclnogr i' ·
alile C:arclnogen: eXperlmental tumorlgen, reproduclive effec1s; human lgen l>Y lmplahfTSCA nstea . I \. ..
mulagenlc d8la; TSCA listed • •HtiZtur/Ou$_ Decomp. Prods.: Heated to decomp., ·- -
Hszsrdous Decomp. Prods.: Healed to decomp., emlls aaid smoke and ln:llaUn_g fumes • •
• lrrlla1lng bnes ~ Jon.exchange resin fer purification of foods and
US&B: Dlluent In food colorants; synlheticJlavorlng agent, emulslller, so1u· (removes undeslrable Ions); puifftcallQn of glycerin and er
bB!zer, dispersant, surfactant. wetting agent, stabl1tzer In foods: In ReguJatory:• FDA 21CFR §1'15.105, 175.125, 175.300, m
defoamers fill' beet sugar, yeast proc:eSslng; emulsifier In fee crean, edJ. · 1n.1200• m.1640, 111.2600, 11a.1005
ble fat/olls; solubllzer, Cllspersant In pickles, vitamin-mineral preps., gelir
· tin dessert; surfacfant In prod. ofcoarse ayst NaCl; wetting agent In jloul- =eel;
Manuf.IDJsbib.: A Schulman; taos C>rg •hlvanced Cher
Arkema; Ashland; BASF; BP Ctiemica1S; ChlM<
~; Evonlt< J?egussa GmbH;'Fluka; GE Plastics; GE F
R!fut~ FDA 21~ §73.1: 73.1001, 172.515, 172.840, 172.842, man; ~; Monomer-P~ & Da}ac Labsj Nova 1
: . 173.340, 175.105, 175.3001 176.180, 178.3400, 573.860j USDA9CFR ~~Plaslnt'f.:tics•~
S~ader, Sigma; 'lbtal f>elrocl:leriilcals B1
-§318,7, 381.147(lmltaUon1% alone, 1% total combined with polySO!f)ate - , ...., ... Chems. Ltd
GO>; FEM.( GRAS; Europe fisted; UK approved; FDA approvedk>r ooc- Trade Names: Dlaion® SA20A; Dlalon® SA21A: DlaJ.
cals, 1n1ramuscu1ar lnje(:fsbles, i?J!av.E!nous. parenteralS, ~. Dlalon® UBK550; Dialon® ~1<555; Dlalon® WPJO
orals, olics, rectals, toplcals, vaglrials; USP/NF, BP. EP compllarioe .
ManUf.IDJsfrib.: GarboMer, Chemacon GmbH: CrocU! Chem. ~ ltd;
Po~~ne-co-butadlene). See
Slyrene/buladlene P01Ym1
Pol}'s ne latex; Polystyrene .resin; Polystyrol. Poly See
Fluka; Mallinckrodt Baker. Mosselman N't, SAFC Specialties; Sigma; Po one resin . ·
SpetlrJ.m_QuaDty Prods.; Voigt Global Dlstrib. · CAS 25135-51-3 .
Tl8de Names: .Mamuls® P,SM0,.20; AVBPOI™ "80; AvaPOllM BOK; Canar- ~PSU · . ·
cel TW 80; Cn1let4; Crillet4 HP; Crillet 4 NF; Cn1et 4.Super; Durfax® 80; 15etini1Jon: Amorphous_ engineering lhennoplastic with h'9h r
. Glycosperse®0-20 KFG; Lamesolb®SMQ.20; Llposorb 0-20; Llposorb alcohols and salt sol'ns.; resfst to hea~ oxklatlon, delerger.
Q.20K; Lonzesiil SM0-20; Lumisorb111 PSM0-20 FGK; Ll.lmfsorb1t1 and smoke emission; self..ov11...... d,,1.1ng· good aeep ~
PSMQ.20Ki N'ISSall Nonlon OT·221; Sorbax PM0-20; T-Maz® 80; T· props.; dlmensJonally stabi;-IJ! 'llUli>I U I . •
Maz® 80K; T-Ma$ 80KlM; T0-10V; '!Ween® SOK; Tween® aw PjopertJes: Tl'Ei~sparent hard rigid solid; scil. in aromatic I
Pharma . . kB1ones, chlorinated h)'drocarbons; m:w. 30,000; dens.
Trade Names Contalnlng: PFC}$ 920; Alclosperse® 0-20; Aldosperse®
0-20 KFG; lce#2; Monofreeze 80 · ·
· t=J·~ tens. sir. 70 Wmm2; tens. mod. 2.5 ~
Polysorbate 81 · . Pm:autfon: CombUSIJble, bl.It $Bff-exlinguishing ···:
CAS 9005-65-6 (generic) . : . Uses: In membranes fdl' H11. separations for food processing_
Synonyms: PEGS SOlbltsn oleate; POE (5) soJbilan monoolea!e Reg~ FDA21CFR§177.1655 .
Definition: Mixture of oleale esters of sorbltol and sorbllol anhyclrides,.with Manuf.!Dfslrib.: Acros Oqj.; Aldrich; BASF; CarboMer; GE·e
•5molesEO. Trade Names Containing: Rlmfec®: Fllmtec® BW30400: Fl/r
Propetties: Amber olly Bqu!d;·v1sc. aoo.ooo·c::s; hydroxyl value 134-150; 2540; Fllmfec® BW30-4014· Fllmfec® BW304o-' ... ~,iu .
sapon. value 96-104; acid value 22; HlB 10.0; Nonionic · · 2514; Filmlec®.SW30:-2540; Fdmtd> sW304Mi \
ToxlccJogy: TSCA Bsted 2521;.FBmfd TW30-2026• ~ TW3l).25-. ,_
Uses: Emulsifier for bakery, confeclioneiy. convenience foods; so!ubillzer 2521; Rlmfec® lW30-2540: Fllmtec® TW304014: ,.,_ .
for flavors, vitamin oils; vise. mOdilier; suspending agent for foods 4021; Rlmtec® .TW30-4040; ·Fllmtec® 1W30HI:'1··
Regulatory; FDA21CFR §175.300 . TW30HP-4611; Fllmtec® 1W30HP-4641 · ·'
Trade Names: Cn11et 41; Hetsorb Q.5; Sorbax PM0-5; T-Maz® 81-; Pol~rpene resin. See Terpene resfn · "': .
Tween® Bf Polythene. See Polyethylene · .- ·
..,, o-·
c'
' "
'1
TWEEN™ 80-NV-LQ-(AP)
Polyoxyethyl~ne(20) Sorbitan Monooleate
Mon-hazardous substance
All chemical substanceu In this product are listed on the TSCA Inventory.
CR ODA
1111111111111111·1111111111111111111111111
8047163/BULK Croda Inc
300-A Columbus Circle Edison NJ 08837..3907 US Tel 1-732-417-0800 Fax 1-732-417-0804
Material SaJety Data Sheet
(
\ Version 3 Revision Date 2013.11(
Emergency Overview
NON-HAZARDOUS SUBSTANCE ·
r
r-·
I
Potential Health Effects
Eyes Not an irritant.
Inhalation No toxic effects are known to be associated with inhalation of this material.
Fonn liquid
Color yellow-orange
Odor no data available
?~~~/!·~J...:;.:.:;:/},~;.~;<:}::.t;'::.{\Y{i?'.{{:.{~;t:;'.:.::{'.5:/'.J:;;}-{f?-~:.'.:·;:~;-.\.= ~'.(r.i.~;~~\1;.::~:~;\/.~\~.\\fi{:;.,r.;s{~r.~;\Y~?t:.-'.{/~:;/;::;.'~
Alkoxylate 9005-65-6 90 - 100
Eye contact : Immediately flush eye(s) with plenty of water. If eye irritation persists, consult a
Skin contact
.:!. '...:·~,<~s:-..:'-' ,'\~' ~:;,;·., (~;·
:
specialist.
Take off contaminated clothing and shoes immediately. Wash off with soap and
·;: '.':;: . ;;; ·;::.":~.-//.::.,J:=·:'.: 1.f.;~":;.". ':.i':p~ ·for?°, ··'·;~:'.
l_
::·.- ·:. A' ;-.~::.1:-Y...1 ;A.:,·::J!\:~.<::-: · .·,\A:5:\:.':-.·~\ ·:so47H>3 \',.':':. '.--:.!:·. {:.:_:;,5;.:,>:.·
I
Material Safety Data Sheet
Ingestion If large quantities of this material are swall<;>wed, call a physician immediately.
Inhalation If breathed in, move person into fresh air. If symptoms persist, call a physician.
Suitable extinguishing Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
media Use extinguishing measures that are appropriate to local circumstances and the
surrounding environment.
Specific hazards during fire Do not use a solid water stream as it may scatter and spread fire.
fighting Do not allow run-off from fire fighting to enter drains or water courses.
(
\
Special protective In the event of fire, wear self-contained breathing apparatus.
equipment for fire-fighters
Handling Handle in accordance with good industrial hygiene and safety practice.
Exposure Guidelines
no data available
Hygiene measures Handle in accordance with good industrial hygiene and safety practice.
Form liquid
Color yellow-orange
Odor no data available
Odor Threshold no data available
Flash point >148.9 °C (300.0 "F)open cup
pH 6.5-7.5
pour point approximately-20.56 °c (-5.01 °F)
Boiling point > 100 oc (> 212 OF)
Vapor pressur~ no data available
Density no data available
Bulk density no data available
Water solubility no data available
Partition coeffici~nt: n- no data available
octanol/water
Solubility in other solvents Ethanol soluble
lsopropanol soluble
Viscosity, dynamic· approximately425 mPa.s
Viscosity, kinematic 300 - 500 mm2/s at 25 "C (77 "F)
Hazardous decomposition In case of fire hazardous decomposition products may be produced such as:
products Carbon oxides
Sensitiza.pon Humans
Result Did not cause sensitization on laboratory
animals.
. ". Method: Patch Test on humans.
Carcinogenicity:
Not classifiable as a human carcinogen.
Biodegradability 80028
32%
(OECD 301C)
37%
(OECD302B)
static test
100% (-
(OECD static test method) \.
(OECD301C)
Material Safety Data Sheet
52%
(
\ SECTION 13. DISPOSAL CONSIDERATIONS
Notification status
TSCA All chemical .substances in this product are listed on the TSCA Inventory.
DSL All components of this product are on the Canadian DSL.
REACH On the inventory, or in compliance with the inventory
AICS On the inventory, or in compliance with the inventory
NZloC On the inventory, or in compliance with the inventory
IECSC On the inventory, or in compliance with the inventory
ENCS On the inventory, or in compliance with the inventory
( KECI On the inventory, or in compliance with the inventory
PICCS On the inventory, or in compliance with the inventory
l'"_~~gp;.<'\N'':
m,I
tT:!nu,ii;. ·1,r-.2.(·-..A· :-m·)';i:;~:.\
t.11 .• ~ : .,so~
~ 1_;;'"~~ ... '.~,! H
!
,: : .~,.~-~~~
~· ,.
'A• .• 1•
r.\: ·.. , " ·'· :
-" • , • • <
_;·_·
>
Material Safety Data Sheet
J
I -.. ,. Version 3
Revision Date 2013.11.14
SARA302 SARA 302: No chemicals in this material are subject to the reporting requirements
of SARA Title Ill, Section 302.
SARA 313 SARA 313: This material does not contain any chemical components with known
CAS numbers that exceed the threshold (De Minimis} reporting levels established
by SARA Title Ill, Section 313.
California Prop. 65 WARNING! This product contains a chemical known in the State of California to
Ingredients cause cancer.
WARNING: This product contains a chemical known in the State of California to c.·-_
cause birth defects or other reproductive harm.
HMIS® ratings are based on a 0-4 rating scale, with O representing minimal hazards or risks and 4 representing
significant hazard or risks. HMIS® is a registered trademark of the National Paint and Coatings Association. ·
Reactivity: 0
This information is intended solely for the use of individuals trained in the particular- hazard rating system. Additional
information regarding the NFPA rating system is available from the ~ational Fire Protection Agency at www.nfpa.org.
Further information
Material Safety Data Sheet
The information in this publication Is believed to be accurate and is given in good faith, but no representation of
warranty as to its completeness or accuracy is made. Suggestions for uses or applications are only opinions. Users
are responsible for determining the suitability of these products for their own particular purpose. No representation
or warranty, expressed or implied, is made with respect to information or products including, without limitation,
warranties or merchantability, fitness for a particular purpose, non-fringement of any third party patent or other
intellectual property rights including, without limit, copyright, trademark and designs. Any trademarks Identified
herein are trademarks of the Croda group of companies.
.. '" ...--
i
/.
I
\
(
OMRI Listed®
The following product is OMRI ~ed. It may be used in certified organic
production or food processing and handling according to
the USDA National Organic Program Rule.
Product
TWEEN 80-NV·LO·(AP)
Company.
Croda Inc.
Rachel Lafferty
315 Cherry Lane
New Castle, DE 19720
Restrictions
EPA Inert ln&redlents an EPA's List 4 may h used only with EPA realstered pesticides or active Ingredients considered "25b exempt"fram FIFRA registration. Ust 3
inert inaredients may be used only in passive dispensers of EPA reB!stered pheromones•
.ex.;.....R ~
-~ ...... "-•• .
Product review is C011ducted accardln& to Ille policies In the current DMRI Polley Manual' and based cm 1he standards In the current DMRJ Standards Monua/F.
To verifll the curren1 mtus or this or any CMRI Listed pradua, View the most C1Jrrent version ar the DAIRI l'mducu Ust" at OMRl.org. DMRI Ustlna Is not equivalent to
arpnlc certfflcatlon and is not a product endorsement. It cannot be i:onstrued as sucti. Final decisions on thf acceplllblllty of a product for un In a terlified organic
system ;re lhe respoll5ibillty or a USDA accredited certi~callon agent It is lhe operator's responsibnlty to properly Qse the pradllc:t. lntludlng following any restrictions.
(
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(
\~
0-TAC BLEtlDING
Process Ffow Chart
ReJecUruck. Do Not
Unload frto filEllc.
Conlaohsuppllerand
. custi>mer. .
0-TAC BLEHDJNS
· PROCESS
~inlinj'hii)jJ""'iliitbffnnll)
FAIL
· ..
PASS
............·
0-TACtale filring
0-TAC pail ftlling
sfation_
sfaticn.
0-TAC PACKAGhlNG
Process Flow C art
~·:··FAIL
·. · FAIL FAIL
.'
NOT.E: ALL lRANSFER UNES. PUMPS.AND HOS~ USED IN TffE BLENDING MID PAC~GiNG PROCESS
OF O·TAC.AR.E SOLB..Y DEDICAlED FOR lHAT PURPOSE AND ARE CLEARLY MARKED THROUGHOlT.T Ttf
PLANT AND PACKAGJNGAREAS. : (
. . \ "'
!
. .
:;~·eurofins
G·eneScan
. .
Custotner: AgriSystems International
125 West 7th St..
Wind Gap, PA 18091
Attn.£ Thomas B Harding .Jr.
·.
*'nie results shDWJI "tn thls
report relate solely to the Eurofins GeneSc~
item submitted for
~naly.sls.
1Sc:>Jl~"C·'1 'tb2!.i
~
.;.,~•
~•.r1.....,~
Dr. FraiikSpiegelhalter
Executive Vice Pr.esident
T•stlillll Catt. 1940.01
-1~
Eurofins GeneScan Incorporated· 231!;? N. Causeway Boulevard· Suite 200 • Metairie, LA 70001 USA
TI +1504297 4330 •FI +1. 504 297 4335
lNITED STATES ES\'IRO!'CME:-OTAL PROTECTIO!"i AGENCY
WASHINGTON. D.C. 20460
Dear Registrant:
The amendment referred to above, submitted in connection with registration under the Federal
Insecticide, Fungicide and Rodenticide Act as amended is acceptable under 3(c) (5).
The new product chemistry and acute toxicology studies submitted are acceptable and will be
placed on file. The revised label reflects the new acute toxicology studies and is acceptable
If you have questions concerning this letter, please contact Banza Djapao at 703-305-7269, or via
email at djapao.banzalli\epagov, or myself at 703-308-9443.
Tony Kish
Product Manager, Team 22
Fungicide Branch
Registration Division (7504P)
/
I
0-TAC
Emergency Overview
WARNING!
Form: liquid Color: light yellow Odor: Characteristic Fatty Alcohol Odor
1
0-TAC
Hazardous components
Component I CAS-No.
Octanol/111-87-5
Weight percent
36.2%
c
Decanol/112-30-1 48.2%
Polyoxyethylene sorbitan monooleate/9005-65-6 15.3%
Related compounds (dodecanol C-12)/112-53-8 0.3%
2
0-TAC
Flammable properties
Fire fighting
system.
3
0-TAC
the environment.
Do not flush into surface water or sanitary sewer
system.
Storage:
Exposure Guidelines
4
0-TAC
Skin and body protection Long-sleeve shirt and long pants or coveralls.
Shoes plus socks.
Remove and wash contaminated clothing before
re-use.
Appearance
Form: liquid
Color: yellow liquid
Odor: Characteristic fatty alcohol odor
Safety Data
5
0-TAC
Toxicological Assessment
Ecotoxicity Effects
Toxicity to Daphnia and other 48 hour LC50 to Daphnia magna (water flea):
aquatic invertebrates: 8.24 mg/I
6
0-TAC
Further information:
Dispose of waste material in compliance with all federal, state and local
regulations.
DOT
Not dangerous goods
TDG
Not dangerous goods
IATA
Not dangerous goods
IMDG
Not dangerous goods
RID
Not dangerous goods
California Prop. 65 components: This product does not contain any chemicals
known to the State of California to cause cancer,
birth defects or any other reproductive harm.
7
0-TAC
This information in this Material Safety Data Sheet is correct to the best of our knowledge
and information at the date of its publication. The information provided is designed only as a
guidance document for safe handling, use, processing, storage, transportation, disposal and
release and is not to be considered a warranty or quality specification.
8
( l'NITED STATES ENVIRO'.'i:\1E!'\TAL PROTECTION AGESCY
\. WASHINGTO~. D.C. 20460
Dear Registrant:
The amendment referred to above, submitted in connection with registration wider the Federal
Insecticide, Fungicide and Rodenticide Act as amended is acceptable wider 3(c) (5).
\ __
The new product chemistry and acute toxicology studies submitted are acceptable and will be
placed on file. The revised label reflects the new acute toxicology studies and is acceptable
If you have questions concerning this letter, please contact Banza Djapao at 703-305-7269, or via
email at djapao.banzatcl1epa.gov, or myself at 703-308-9443 .
.1
\
N-TAC
N-TAC
Version: 1.2 Revision Date: 09/07/2012 Print Date: 09/07/2012
Emergency Overview
WARNING!
Form: liquid Color: light yellow Odor: Characteristic Fatty Alcohol Odor
1
N-TAC
Hazardous components
2
N-TAC
Flammable properties
Fire fighting
3
N-TAC
Storage:
Exposure Guidelines
4
N-TAC
Skin and body protection Long-sleeve shirt and long pants or coveralls.
Shoes plus socks.
Remove and wash contaminated clothing before
re-use.
Appearance
Form: liquid
Color: yellow liquid
Odor: Characteristic fatty alcohol odor
Safety Data
/
;
\
5
N-TAC
I
Toxicological Assessment \
Ecotoxicity Effects
6
N-TAC
I
Toxicity of honey bees: 48 hour contact LD50 >25 µg/bee
Further information:
Dispose of waste material in compliance with all federal, state and local
regulations.
DOT
Not dangerous goods
TDG
Not dangerous goods
IATA
Not dangerous goods
IMDG
Not dangerous goods
RID
Not dangerous goods
California Prop. 65 components: This product does not contain any chemicals
known to the State of California to cause cancer,
birth defects or any other reproductive harm.
7
N-TAC
This information in this Material Safety Data Sheet is correct to the best of our knowledge
and information at the date of its publication. The information provided is designed only as a
guidance document for safe handling, use, processing, storage, transportation, disposal and
release and is not to be considered a warranty or quality specification.
8
Background Information
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For more Information about Muslm Mas, please visit www.rous.il:!:l!M~~in MVSIMMA~
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Why choose
Musim Mas a·syoursupprychain partner?
.~J·I;p,·r .· GIO.bal
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Presence
Our presence in strategic locations worlawide
means that there will always be someone from
our team, who can provide the professional sa·les
and technical support at your convenience.
Commitme·t1t
to Sustain-ability
We believe In creating economic value that also
creates value for society by addressing its needs
and challenges, also known as the#SharedValues•
approach. ·
()tijaJ~~ty . ..
<C~ir~itrn~©U:fil@rrii ;.s
As a commitment towards manufacturing
excellence, we have third-party audited
certifications for quality assurance.
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September 2013 Musim Mas Group Profile 3
Commitment ta
Manufacturing ExceH·ence
La,rge ·
·. · Oper~tional Scale
We own a significant oil palm plantation area,
making us one of the largest plantation owners in
the palm oil space. We also own one of the lar.gest
palm oil refineries and o~ochemicals plants Jn the
world, and.are among the biggest pmducers in the
palm oil refining and soap manUfacturlng sector.
-I-
Sourcing and developing this suckercide for use by
SFNTC growers has not been easy nor inexpensive.
But, believing that the results will benefit both the
growers and them greatly, SFNTC underwrote the
cost of bringing 0-TAC to the market.
-2- 2
When to Apply 0-TAC How Much 0-TAC to Apply
0-TAC Plant Contact Agent can be applied before or after Flue-Cured
\ topping. The best results are usually obtained by spraying For power sprayer -
the tobacco with 0-TAC before topping in the 6arly to late Use 2 gallons (7.S7 liters) in
button stage and then topping the tobacco immediately 48 gallons (182 liters) of water for a total of SO gallons
followed by additional applications ofO-TAC. (189 liters) for a 4% spray solution.
or
Use 2.5 gallons (9.4 liters) in
47.S gallons (180 liters) of water for a total of SO
gallons (189 liters) for a S% spray solution.
0-TAC usually can be applied anytime during the day, but Note:
not to wilted plants. For the best results, it is recommended *When applied by hand, 1 gallon (3.785 liters) of diluted
that growers wait until the dew dries before spraying. Do 0-TAC will treat approximately 190 plants.
not spray after the upper leaves begin to close in the •If a power sprayer is used, SO gallons (189 liters) of
evening. Because the underside of the leaves may be diluted product should be applied per acre of tobacco.
injured by contact with 0-TAC, do not apply when the
wind is high enough to
turn the top leaves over.
Do not apply during the
rain or when plants are
wet. If, however, it rains
after 0-TAC has been on
the plants for over an hour,
you should not have to
apply 0-TAC again. Do
not apply during periods of
high heat or if plants are
wilted.
3
How to Apply 0-TAC How Often to Apply 0-TAC
The diluted emulsion is most easily prepared by adding the Usually one application of 0-TAC Plant Contact Agent ( ·
required amount of 0-TAC Plant Contact Agent to the will give good control of both primary and secondary \.
spray tank and then adding the water. In ordef to obtain the suckers and produce excellent leaf quality. However, in
best results, it is important that the water be added to the most cases, a dual treatment of 0-TAC is recommended
0-TAC rather than the 0-TAC to the water to enhance 5 to 7 days apart to allow time for uneven crops to become
mixing and reduce floating. uniform. For season long sucker control, apply multiple
treatments of 0-TAC in accordance with label instructions.
When applied with power button stage early flower stage full flower stage late flower stage
equipment, three nozzles per _..,,.__ S-7days ..... 1..- S·7days ..... 1..- S-7days -+-I..-
row should be used {TG full
cone tips, or larger, are satis-
factory). One TG-5 nozzle More Key Points on the Use of
should be directed down- 0-TAC on tobacco
ward over the center of the
row and two TG-3s should 1. Mix well prior to use and, if allowed to stand during the
be positioned approximately use, mix again before applying since the diluted emul-
11 inches on either side directed at or slightly above the sion may separate on standing.
top of the stalk.
2. Do not use on Burley tobacco during periods of high
The diluted 0-TAC should be applied to the tobacco from heat and high humidity.
a height of 12 to 16 inches above the top of the stalk. It is
recommended that boom pressure be kept at 20 lbs. By 3. Use according to the directions outlined has resulted in
using the recommended spray tips, spraying at approxi- adequate sucker control with very little or no leaf injury.
mately 20 lbs. pressure, and operating a tractor speed of Application not in accordance with the directions may
2.5 to 3 mph, approximately 50 gallons of diluted emulsion lead to injury of leaves or improper sucker control.
per acre of tobacco will be applied.
4. Make sure spray equipment is clean before using. (Note{ .
Organic and PRC growers must use dedicated equipment~·
can not have been used for spraying conventional tobacco)
-4- 4
How 0-TAC Plant Contact Agent is Formulated by Fair Products, Inc.
In preparing for handling the new "organic" product,
, \l Fair Products first erected two holding tanks - the
\_ " 35,000 gallon tank holds the palm oil-bast:.d alcohol
and the 10,000-
gallon tank holds
the surfactants
used in the formu-
lation-and painted
them green.
Everything else
from those tanks
throughout the
formulation and
packaging area In the line filling the 5-
are painted green - to indicate where 0-TAC is being gallon containers, two
made to maintain compli- buckets are filled side by
ance with organic stan- side, with a lid placed
dards. over the top of each
bucket. Once it has been
In the chemist's lab in the verified to have precisely
plant, the palm oil-based the 5-gallon amount of 0-
alcohol and tween are test- TAC, the bucket moves
ed using a gas chromato- under an automatic sealer
graph, as well as a UV that securely fastens the
Spectra Photo to check for lid on to the bucket.
\ / pH and other characteristics.
The pallet is then taken
Following confirmation that the ingredients meet by a lift-truck for shrink-
specifications, the surfactants are mixed in the alcohol wrapping and then is
tank. stored ready for distribution.
5
In the line where 0-TAC is packaged in labor-saving Testing the Formulated 0-TAC
275-gallon Mini-Bulk containers, once again, the pre-
cise mix of ingredients enter the top of the large con- Just as samples were tested of the
tainer until filled to the top. An operator then places a ingredients used to make 0-TAC (
cap securely on top of the Mini-Bulk container, and before the formulation was made,
affixes a seal to it. An 0-TAC product label is then testing is also conducted on fm-
attached to the container at that time. ished formulations prior to storage
and ready for distribution. On cer-
tain occasions, samples are also
sent to outside laboratories for eval-
uation. Samples are kept from each
batch of formulated 0-TAC. Each
contains a Code # for potential
tracking of each of product, should
a recall be needed.
container, attaching a pump and meter system 3220 Knotts-Grove Road, Oxford, NC 27565
requires only 2-inch connectors and a proper length (919) 690-0880 Fax: (919) 603-5755
of suction hose. www.sfntc.com
Fatty Alcohols
Background Information
(
Fatty alcohol - Wikipedia, the free encyclopedia http://en.wikipedia.org/Wikl/Fatty_alcohc
Fatty alcohol
From Wikipeclia, the free encycJopedia
i
\
atty alcohols (or Jong-chain alcohols) are usually hlgh-moJecuJar- :· ;·. ::· ..•. : ..:..-_ ..
-:.::::~::~: ::~:'..'"".. .
.~::::·· .:
-··~::.::_::.·'.:.;:::,::::::-_-:::.::: .-.:_·:-.:~ .
weight, straight-chain primary aJcohOJs, but can also range .from as few as
4-6 carbons to as many as 22-26, derived :from natural fats and oils. The
precise chain length varies willl the somce. [l]f21Some commercially
important fatty aJcohoJs are laury~ stearyJ, and oJeyl alcoboJs. They are
OH:
coJomJess oily Jiquids (for smaJJer carbon rnnnbers) or waxy soJids,
aJtbough impure samples may appear yellow. Fatty alcohoJs usua]Jy have
an even mnnber of carbon atoms and a single alcohol group (-OH)
: Fatty alcohol
attached to the terminal carbon. Some are lllJsaturated and some are ;
..--·--·• ... •• ...... ,.._,••• •""•w-·••·--···-••-··- .,.. ••-•,.•·•--.••-•• .. ••• """
branched. They are widely used in industry. As with fatty acids, they are
often referred to generically by the mnnber of carbon atoms in the moJecuJe, such as 11a C12 aJcoboJ", that is an
aJcobolhaving 12 carbons, for example dodecanol.
Contents
• 1 Production and occurrence
• 1.1 From naiuraJ sources
• 1.2 From petrochemical somces
• 2 Applications
• 2.1 Nutrition
• 3 Sa1ety
• 3.1 Human Health
• 3.2 Environment
• 3 .3 Aquatic OrganG:m
• 4 Common names and related cornpmmds
• 5 References
• 6 ExternaJ Jinks
became an nnportant source of chemicaJs, and Kar] Zieg1er had discovered the polymerization of ethy1ene. These
two developments opened the way to synthetic fatty alcohols.
Fatty a1cohoJs are also prepared from petrocbemicaJ sources. In the Ziegler process, ethylene is oligomerized using
triethylaJuminium followed by air oxidation. 'llis process affords even-numbered aJcoboJs:
AJtemativeJy ethylene can be oligomerized to give mixtures of alkenes, which are subjected to hydroformy1ation, this
process affording odd-mnnbered aJdehyde, which is subsequently hydrogenated. For example, from 1-decene,
hydro1onny1ation gives the C 11 a1cobo1:
In the Shell higher o1e1in process, the chaiµ-Jengtb cmtnbution in the initiaJ mixture o1 alkene oJigo:D;lers is adjusted so
as to more closely match market demand. She] does~ by means o1 an intermediate metathesis reaction.C41The
resultant mixture is fractionated '.illd bydroforrny1ated/hydrogenated :in a subsequent step.
Applications
Fatty aJcohoJs are mainly used in the production o1 detergents and surfactants. They are components also of
cosmetics, foods, and as industrial solvents. Due to their amphipathic nature, fatty a1cobo1s behave as nonionic
surfactants. They find use as emulsifiers, emollients and thickeners in cosmetics and food .industry. About 50% of
fatty aJcoho1s used commerciaDy are o1 naturaJ origin, the remalnder being synthetic. [I]
Nutrition
Very Jong chain fatty aJcohoJs (VLCFA), obtained from pJant waxes and beeswax have been reported to Jower (
plasma cboJesteroJ in humans. They can be 1m.md in unre:fined cereal grains, beeswax, and many plant-derived
foods. Reports suggest that 5-20 mg per day o1 mixed C24-C34 alcoboJs, including octacosanoJ and triacontanoJ,
lower ]ow-density Jipoprotein (LDL) cboJesteroJ by 21 o/<t-29% and raise high-density lipoprotein cho1estero1 by
8o/1t-l S%. Wax esters are hydroJyzed by a bl1e sah-dependent pancreatic carboxyJ esterase, releasing Jong chain
P;:imi2of7
Fatty alcohol - Wikipedia, the free encyclopedia http://en.wikipedia.org/wiki/Fatty_alcoho
aJcohoJs and fatty acids that are absorbed in the gastrointestinal tract. Studles o11atty aJcoboJ metabolism in
fibroblasts suggest that very Jong cham fatty alcoboJs, fatty aJdehydes, and fatty acids are reversibly inter-converted
in a fatty alcohoJ cycle. The metabolism o1 these compounds is impaired in several inherited human peroxisomal
\ .. 1orders, incJucling adrenoJeukodys1rophy and Sjogren-Larsson syndrome.f5J
Safety
Human Health
Fatty aJcohoJs are relatively benign materials, with LD50s (ora~ rat) ranging 1rom 3.1-r g/kg 1or hexano1 to 6 -8 g/kg
for octadecanoJ.[IJ For a 50 kg person, these values translate to more than 100 g. Tests o1 acute and repeated
.exposmes have revealed a Jow .level o1 toxicity from inbaJation, oral or dermal exposure of 1atty alcohols. Fatly
aJcohoJs are not very volatile and the acute JetbaJ concentration is greater than the saturated vapor pressure. Longer
chain (C12-Cl6) fatty alcohols produce fewer health effects than short cham (< C12). Short chain 1atty alcohols
are considered eye irritants, while Jong chain alcohols are not.[6] Fatty alcohols exhiblt no skin sensitization.[7]
Repeated exposure to fatty alcohols produce low level toxicity and certain compounds in this category can cause
JocaJ irritation on contact or low-grade liver effects (essentially linear alcohols have a sligbtly higher rate of
occurrence of these effects). No effects on the central neivous system have been seen with inhaJation and oral
exposme. Tests of repeated bolus dosages of 1-he:xanoJ and 1-octanoJ showed potential for CNS depression and
· ·1uced respiratory dEtress. No potential for peripheral neuropatby has been found. In rats, the no obseivabJe
_..tverse effect leveJ (NOAEI..) ranges from 200 mg/kg/day to 1000 mg/kg/day by ingestion. There bas been no
evidence that fatty aJcoboJs are carcinogenic, mutagenic, or cause reproductive toxicity or infertility. Fatty aJcohoJs
are effectively eliminated 1rom the body when exposed, limiting possibility of retention or bioaccmnu1ation.[7]
Margins of exposure resu1ting from consumer uses of these chemicals are adequate for the protection of human
health as determined by the Organization for Economic CoMoperation and Development (OECD) high pr9duction
volume chemicals program.[6J[S]
Environment
Fatty alcohols up to chain length Cl8 are biodegradable, with length up to C16 biodegradingwitbin 10 days
completely. Chains C16 to C18 were found to biodegrade 1rom 62% to 76% in 10 days. Chains greater than C 18
were found to degrade by 37% in 10 days. Field studies at waste-water trea1ment plants have shown that 99% of
fatty alcohols lengths C12-Cl8 are removed.[7]
Fate prediction using :fugacity modeling has shown that fatty aJcoboJs with chain lengths of C10 and greater in water
partition into sediment. Lengths C 14 and above are predicted to stay in the air upon release. Mod~Jing shows that
each type o1 fatty aJcoboJ will respond roepe.rxlently upon environmental release. [7]
(
'\ , ...quatic Organisms
Fish, invertebrates and algae experience similar levels of toxicity with fatty aJcohoJs although it is dependent on chain
Jen.mh wlth the shorter chain having greater toxicity potential. Lon,g.er chain 1enJ?tbs show no toxicity to aquatic
Page 3 of 7
Fatty alcohol - Wikipedia, the free encyclopedia http://en.wikipedia.org/wiki/Fatty_alcohol
organisms. [7]
This categozy of cbenrlcaJs was evaluated under the Organization for Economic Co-operation and DeveJopment
(OECD) high production volume, chemicals program. No unacceptabJe environmentaJ risks were identified.[8]
\.
P;:im~ 4 of7
Fatty alcohol- Wikipedia, the free encyclopedia http://en.wikipedia.org/wikVFatty_alcohc
----- ·----------.. -·-..-----·---·· ·-·-..--r---·---·-1-- -··
: Name j Carbon atoms !Branches/saturated? Formula
1-----·----------·------------··--··-· ·-· -··· -·-··--"--·-·-·-;---·--·-------.
~ f (
·-·-··----·-------+--__.;...;~
PaQe 5 of7
Fatty alcohol - Wikipedia, the free encyclopedia http://en.wikipedia.org/wiki/Fatty_alcohol
References
(
\.,~
I. "a b c d Klaus Noweck, Wolfgang Grafahrend, 'Fatty AlcohoJs" in Ulhnann's Encyclopedia of Industrial Cherr 1
Yutaka Kasai, Andreas Willing, Scott D. Dyer, Kathleen Stanton, Richard Sedlak, (May 2009). ''An overview of
hazard and risk assessment of the OECD high production volume chemical category-Long chain alcohols [C6-
C22] (LCOH)". Ecotoxicology and Environmental &jezy 72 (4): 973-979. doi:l0.1016/j.ecoenv.2008.10.006
(http://dx.aoi.org/10.1016%2Fj.ecoenv.2008.10.006).
External links
• Cyberlipid. 'Fatty Alcohols and Aldehydes 11 (lrt1p://www.cyberlipid.org/simp1e/simp0003.htm). Retrieved
2007-02-06. Genera] overview o1 fatty alcohols, with re1erences.
• CONDEA. 'Dr. Z Presents AD about fatty aJcohoJs"
(http://www.2enitech.com/documents/new%20pdfs/articles/.A1JO/o20about%20fatty%20a1cohoJs%20Condea.
pdf). Retrieved 2007-02-06.
(
• This page was Jast modified on 29 June 2014 at 15:12. \
• Text is available under the Creative Commons Attnbution-ShareAJike License; additionaJ terms may appJy.
By using this site, you agree to the Terms o1 Use and Privacy Policy. W:ikipedia® is a registered trademark
o1 the Wikimedia Fotmdation, Inc., a non-profit organization.
Pono~ nf7
A Word About Fatty Alcohols http://www.mvorganics.com/blogs/mvo/5913859-a-word-about-fatty-alcoho
Sign In i Cieate Aa:ount l Emal! Updates ·, S.earch. fv!YP . Go ,' 0 Rems · $0.00
All the latest natural skin care, anti-aging and healthy lifestyle tips from Marie Veronique Organics.
- ........ - - •-••o• ..• l · • - > , A .. 0 - > • •• ' ____ , _ , . , , , . . , , - • • • • -. . . . . . . . . . . •-··~·-- • -~· .. · - - · " ' " ' ' • , ...... - - - - - - - - . . . ,,• .__. . . . . . . . . . . . . , . . . . . . . ,,., .... - . . - -........... ,-.~-.
There are alcohols and than there are ateohols, especlally when It comes to akin care Ingredients. Chemically, alcohols
are carbon chains with a functional hydroxyl (OH) group attached. On an ingredients llst theywlll usually be the ones ending
In an "ol', as In ethanol, methanol, panthenol. Wille alcohols are used In skin care for their antl-baclllrial properties
alcohols Ilka lsopropyl alcohol, SD alcohol and ethanol can be dr}'lng and ilTflatlng ID the skin. Howe11Br, the fatty alcohols
are a dlfferantcategOlY altogether. with some definitely offering akin benefits such as skin parmeation, moisture retention
and anti-aging support: Fatty aklohols are a m bead bag, though, as awn ones known lo be beneficial can cause skin
lrrffation and should be used with caution •
. There are some others lhatara commonly used In akin care producls lorthelrhumectant properties that organic
companies shy away from using, as their safety prome Is open lo question, and the risks may outweigh the beneli1s. And
then there are some that consumers should awld e\18n though they are deemed sale, and frequenUy show up on
Ingredients fists. Glwn the potential risks. It Is Important lo iead )'Our labels with aoina understanding of the "ols"-what la
their function, whyalB they there, and mostlmportant, do )'Ouwant1hem In products thalwill be absorbed by your body? Marie Veronique Nadeau lound&d Marie
Veronique Organics oyer 10 ~ars ago and is
To help demystify your shopping experience, hare Is a llsl of fatty alcohols thatare commonly USBd In akin care a nallonally recognized fonnulalorand beauty
products. eJ111er1. She collaborates with her daughter,
Jay Nadeau, ph)'llclstand blo-macllcal
engine&r, to carefully choose each ingredient
Common In h&rproducls to address the causes of
Fatty Alcohol Function Benefit Safett
Name aging at the sourte. Marie holds a BS In Math
Passes through the dennis, amoothes anlf Chemistry as well as an eslhetics
the skin and reduces TEWL (trans- license from Paris Beauty College. She Is a
'\/Uamln, May cause skin irritation, and
Vitamin epidennal waler loss). Pro\ldes mother of 2 and a grandmother of one. Wien
Tocopherol Anti- causes allergic rascUons In
she Is not developing culling edge anti-aging
E oxidant eicellcnl anti-oxidant protection, some people. products. she c:an be found reading at her
particularly when used In conjunction local library or foraging for mushrooms with
With "1tam!n C her granddaughter.
Pro-
Vitamin,
\'ltamln Promotes wound healing RECEIVE EMAIL l.POATES
panthenol part of May cause skin llTftallon.
B5
Vllamln B
complex
Sign up for excluslw monthly offers, Marie's
Preeautions: Retlnyl p'alniitate in lalestand skin c:are guides.
Vitamin
day creams and sunscreens
From ~D.M~!"••
Studies show it oontrlbutes 1D rewrsing may encourage cancerous and
raiinoi ViiaminA chemical lhe effects of photo-aging precancerous cell gmwth
family of
Recommendation: Use wtlh
retinolds
caution.
Can be mlldly Irritating, Is
hannlul to marine Ille Sign lip n
,f laul)4
Oodecanol emOlllent From palm kernel or coconut tally acids Recommendation: AIOid If
\ alcohol
possible due to Im
emnronmenlal tmdcHy
steal}'! From stearic acid Stearlc acid is
Emulsifier,
typically derlwd from animal fat, but
Recommendatlon:Awid If acne CONNECT WITH MVO
alcohol,
Octadecanol emollient. prone Check soul'Cll if awlding
oleyl may be obtained from unsaturated
thickener animal produels is desired.
alcohol vegetable oils
Page1of3
A Word About Fatty Alcohols http://www.mvorganics.com/blogs/mvo/5913859-a-word-about-fatty-alcohols
Tetradecanol
M;rlst)I Emulslfter,
alcohol emollient
Prepared from myristic acid
Recommendation: Tends to be
more more Irritating than stear}l.
n FACEBOOK a TWITTER
cetyl alcohol.
Ce~
From the end product of the petroleum
Mldly irritating @ PINTEREST ~ INSTAGRAM
alcohol, Emulslfter, Recommendation: Check
HelC&decenol Industry, or produced from palm oil or
paimlt)I emollient source to avoid petroleum
coconut oil
alcohol products
Propylene Can be a strong lnllant
PG humectant A glycol
glycol Recommendation: Avoid
Considered safe, not an irritant
Recommendation:AcauUous
Butylene
BG humeclant A glycol ewld, simply because there Is
glycol
not much data regarding l1s
safety
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FAQs RESEARCH
...,tm
......
Pi:inP.? nf~
Comparatively Speaking: Fatty Alcohols vs. Fatty Acids vs. Estermttp://www.cosmetlcsandtolletries.com/research/chemistry/97861099.htr.
Cosmetics
/ &Toiletries-
Ke search
Comparatively Speaking: Fatty Alcohols vs. Fatty Acids vs. Esters
. Jul 6, 2010 I \new onllne to Contact Author I By: Anthony J. O'Lenick Jr., Siltech LLC
In the present discussion, Tony O'Lenick recruits Ismail Walele of Phoenix ADVERTISEMENT
Chemical to explain the differences between fatty alcohols, fatty acids and
esters.
Alcohols
Alcohols are alkanes with a hydroxyl group on the terminal carbon, which makes
them primary alcohols. These are also called 1-alcohols, an example being 1-
butanol or n-butanol. Some alcohols have their hydroxyl group on the c.chain,
excluding the terminal primary carbon and making them secondary alcohols.
Butanol has three isomers: n-butanol (1-butanol}, 2-butanol (secondary butanol)
and t-butanol, meaning tert-butanol with hindered hydroxyl on the same
carbon with ~ree methyl groups.
Fatty alcohols are aliphatic alcohols derived from natural fats and oils originating
in plants and animals. Fatty alcohols are derived from fatty acids and have an
even number of carbon atoms. The produdion of fatty alcohols from fatty acids
yields normal-chain alcohols wherein the-OH group attaches to the terminal
carbon. Fatty alcohols, due to their amphipatic nature, ad as non-ionic
surfactants/co-surfactants. Fatty alcohols can be used in cosmetic formulations as emulsifiers, emollients and thickeners.
Generally, alcohols are normal alcohols from natural fats and oils, meaning that they all haye an even number of carbons. They
"!Sn be saturated or unsaturated alcohols. Another f;ype of alcohol is a branched chain alcohol, which is termed a synthetic higher
\ ?oho/ or an oxo alcohol. Branched alcohols can be mono-methyl branched or multi-carbon chained on the side at any or
... .,ecific interior carbon of the main carbon chain: Table 1 proVides the tomrilon names; carbon num bei's and the synthetic
branched counterparts of alcohols.
Named after Inventor M Guerbet, Guerbet alcohols are alkaline condensation reaction products of primary alcohols. They are
primary, alpha branched dimeric alcohols and are 100% defined branched atthe second carbon position.
Oxa alcohols and iso-alcohols are alpha-olefin based and are approximately50% branched atthe second carbon position. Oxo
alcohols are about50% linear. !so-alcohols are 100% multiple methyl branched.
Melting points or pour points are much lower for branched/Guerbet alcohols than for their linear counterparts of the same number
of c-chains. Linear unsaturated alcohols are liquid; however, they suffer from poor heat stability due to unsaturation. The
saturated Guerbet alcohols or branched iso alcohols offer fluidity and also thermal stability and oxidation stability. These
differentiating physico-chemical properties of branched chain alcohols make them Immensely Important in the synthesis and
derivatization into cosmetics and personal care emollients.
- .
Fatty Acids
Fatty acids are organic acids comprised of carbon chains with a carboxyl group at the end. Saturated fatty acids have all carbons
with a full quota of hydrogens. There is a single bond between adjacent carbon atoms. Unsaturated fatty acids have one or more
carbon-carbon double bond in the molecule. Chemically, these double bonds will take up hydrogen, a process termed
hydrogenation, that yields saturated fatty acids. Table 2 gives co!llmon names, IUPAC names, chemical strudures and
abbreviation designating presence or absence of unsaturation for fatty acid.
Saturated and unsaturated fatty acids are different in their form, as unsaturated fatty acids have one or more alkenyl functional
group along the chain. Each alkene substitutes a single bonded CH2-CH2 segment of the chain with a double bonded CH2=CH2.
segment, thus a carbon double-bonded to another carbon. Unsaturated fatty acids such as oleic acid can show two of their
distinct forms (isomers), i.e. cis and trans forms. The cis form has adjacent carbons on the same side of the double bond. The
trans form has adjacent carbons bound to the opposite side of the double bond. The ilBIJS form is more rigid than the cis form.
Oleic acid has one double bond whereas linoleic acid has two double bonds and liolenic acid has three double bonds.
i=atty acids react just like any other carboxylic acid, meaning they can undergo esterification and acid-base reactions. Reduction of
.1 · · 'ty acids gives corresponding fatty alcohols. Unsaturated fatty acids undergo addition reactions, with the most prominent being
\ .. · .. ydrogenatfon. Such hydrogenation is used to convert vegetable oils into margarines. Partial hydrogenation of unsaturated fatty
. acids gives isomers mainly converting cis fonTI to trans form. .
Esters
Esteriflcation is a condensation reaction where an acid molecule reacts with an alcohol molecule, producing an ester and water,
Page 1 of3
Comparatively Speaking: Fatty Alcohols vs. Fatty Acids vs. Estenhttp://www.cosmeticsandtoiletries.com/research/chemistry/97861099.html
as shown in Figure 1.
Esterification is analogous to neutralization in the way that the resultant ester is named as if it Is the alkyl salt of the acid. For
example, sodium benzoate is the sodium salt of benzoic acid while lauryl benzoate is the ester of benzolc acid and taur)-4 alcot(- -,
There are a wide variety of esters due to the wide range of fatty acids and fatty alcohols available. The properties can be vari~' \
due to this wide array of variations.
Media
Tables
Table 1. Alcohols
Alcohols from Natural FatsJOils No. of Carbons Alcohols from Synthetic Origin
Paae 2 of 3
Comparatively Speaking: Fatty Alcohols vs. Fatty Acids vs. Estemttp://www.cosmeticsandtoiletries.com/research/chemlstry/97861099.hln
Figure 1. Esterification
Esterification is a condensation reaction where an acid molecule reacts with an alcohol molecule to produce an ester and
water.
'
\
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c··
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I
I
\
FATTY ALCOHOLS
Aliphatic alcohols occur naturally in free form (component of the cuticular lipids) but
more usually in esterified (wax esters) or etherified form (glyceryl ethers). Several
alcohols belong to aroma compounds which are found in environmental or food
systems (see the website: Elavornet). -
They are found with normal, branched (mono- or isoprenoid), saturated or unsaturated
of various chain length and sometimes with secondary or even tertiary alcoholic
function. An unusual phenolic alcohol is found as a component of glycolipids in
Mycobacteria. Some cyclic alcohols have been described in plants.
A c Iass1"f'1cat'ton accorr1.
umg +..o +h . struc+..ure •1s given
.... e carbon-cham • beI9w.
i. Normal-chain alcohols
( 2. Branched-chain alcohols
\
1 - Normal-chain alcohols
The carbon chain may be fully saturated or unsaturated (with double and/or triple
bonds), it may also be substituted with chlorine, bromine or sulfate groups. Some
acetylenic alcohols have been also described.
• Acetylenic alcohols
• S• tlfated alcohols
- Saturated alcohols
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C18H370H 16-methyl-1-heptadecanol
isoste 1alcohol
Free fatty alcohols are not commonly found in epicutic.ular lipids of insects, although
high molecular weight alcohols have been reported in honeybees (Blomquist GJ et
ai., Insect Biochem 1980, 10, 313). Long-chain aicohols aiso have been reported in
the defensive secretions of scale insects (Byrne DN et al., Physiol Entomol 1988,
13,267). Typically, insects more commonly produce lower molecular weight alcohols.
Honeybees produce alcohols of 17-22 carbons, which induce arrestment in parasitic __ ,
varroa mites (Donze Get al., Arch Insect Biochem Physiol 1998, 37, 129). Two (
,emale-specific fatty alcohols, docosanol (C22) and eicosanof (C20), which have been
found in epicuticle of Triatoma inlestans (a vector of Chagas disease in South
America), are able to trigger copulation in males (Cocchiararo-Bastias Let al., J
Chein Ecol 2011, 37, 246). Hexadecyl acetate is found in the.web of some spiders
(Pholcidae) to attract females (Schulz S, J Chem Ecol 2013, 39, 1).
Long-chain alcohols (C18, C24, C28) from the femoral glands in the male lizard
Acanthodactylus boskianus play a role in chemical communication as a scent marking
pheromone (Khannoon ER et al., Chemoecology 2011, 21, 143).
Various tatty alcohols are found in the wax:y film that plants have qver their leaves and
fruits. Among them, octacosanol (C28:0) is the most frequently cited.
Policosanol is a natural mixture of higher primary aliphatic alcohols isolated and
purified from sugar cane (Saccharum.ollicinarum, L) wax, whose main component is
octacosanol but contains also hexacosanol (C26:0) and triacontanor or melissyl
alcohol (C30:0). Policosanol is also extracted from a diversity of other natural sources
such as beeswax, rice bran, and whe~t germ (lrmak Set al., Food Chem 2006, 95,
312) but is also present in the fruits, leaves, and surfaces of plants and whole seeds(- ,
A complex policosanol mixture has been identified in peanut (Cheri! A 0 et al., J Agric ·~·
·Food Chem 2010, 58, 12143). More than 20 aliphatic alcohols were identified (C14-
C30) and four unsaturated alcohols (C20-24). The total policosanol content of the
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1-0ctanol and 3-octanol are components of the mushroom flavor (Maga JA, J Agric
Food Chem 1981, 29, 1). 3-0ctanol is a volatile infochemical present in fungi and
recognisable by fungivores (Holighaus Get al., Chemoeco/ogy 2014, 24, 57).
Many alcohols in the C10 to C 18 range, and their short-chain acid esters are potent
sex or aggregation pheromones. They are mainly found as components of specialized
defensive glands, pheromone glands or glands of the reproductive system.
1~, 351). Several authors have reported high contents of the 22:0 alcohol in
sediments where an algal origin is plausible. For examples the major alcohol in a /
sample of the lacustrine Green River Shale of Eocene ~ge is also 22:0 which \,
;omprises over 50% of the alcohols present (Sever JR et al., Science 1969, 164,
1052)
Long-chain alcohols are known as major surface lipid components (wa:xes) with chains
from C20 up to C34 carbon atoms, odd carbon-chain alcohols being found in only low
amounts. Very long-chain methyl-branched alcohols (C38 to C44) and their esters with
short-chain acids were shown to be present in insects, mainly during metamorphosis.
A series of long-chain alkanols (more than 23 carbon atoms) were identified in settling
particles and surface sediments from Japanese lakes and were shown to be produced
by planktonic bacteria being thus useful molecular markers (Fukushima Ket al., Org
Geochem 2005, 36, 311).
Cutin and suberin contain as monomer saturated alcohols from C16 to C22 up to 8%
of the total polymers. C18:1 alcohol (oleyl alcohol) is also present.
Phytochemistry 2013, 91, 249). Relatively little is known about the functions of these
compounds in the ecological and physiological fields.
In the leaf cuticular waxes of Myricaria germanica (Tamaricaceae) several alkanediols
were identified (Jetter R, Phytochemistry 2000, 55, 169). Hentriacontanediol (C31)
. with one hydroxyl group in the 12-position and the second one in positions from 2 to
18 is the most abundant diol (9% of the wax). Others were far less abundant : C30-
C34 alkanediols with one hydroxyl group on a primary and one on a secondary carbon
atom, C25-C43 B-diols and C39-C43 y-diols. Very-long-chain 1,5-alkanediols ranging
from C28 to C38, with strong predominance of even carbon numbers, were identified
in the cuticufar wax of Taxus baccata (Vl1en Met al., Phytochemistry 2007, 68, 2563).
The predominant diol had 32 carbon atoms (29% of the total).
Long-chain saturated C30-C32 dials occur in most marine sediments and in a few _.
'nstances, such as in Black Sea sediments, they can be the major lipids (de Leeuw C~ .•·
JW et al., Geochim Cosmochim Acta 1981, 45, 2281). A microalgal source for these
compounds was discovered when Volkman JK et al. (Org Geochem 1992, 18, 131)
Page 4 of25
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The chief lipid fraction in the uropygial gland excretion of the domestic hen is a diester
wax. The unsaponifiable fraction cor:isists of a series of three homologous
compounds, which have been named the uropygiols and identified as 2,3-
alkanediols containing 22-24 carbon atoms. These fatty alcohols are esterified by
saturated normal C22-C24 fatty acids (Haahti E et al., J Lipid Res 1967, 8, 131).
- Unsaturated alcohols
Some fatty alcohols have one double bond (monounsaturated). Their general formula
is:
The un.ique double bond may be found in different positions: at the C6: i.e. cis-6-
octadecen-1-ol (petroselenyl alcohol), C9 i.e cis-9-octadecen-1-ol (oleyl alcohol) and
C11 i.e cis-11-octadecen-1-ol (vaccenyl alcohol). Some of these alcohols have insect
pheromone activity.. As an example, 11-eicosen-1-ol is a major component of the alarm
·.pheromone secreted by the sting apparatus of the worker honeybee. In zooplankton,
the cis-11-docosen-1-ol (22: 1 (n-11) alcohol) is not only present in high proportion in
wax esters (54 to 83%) but may be also predominant in free form (75-94% of free
alcohols) in ctenophores (Graeve Met al., Mar Biol 2008, 153, 643). This presence is
unexplained because pathways for conversi<?n and catabolism of fatty alcohols in
ctenophores are still unknown.
Some short-chain unsaturated alcohols are components of mushroom flavor, such as
1-octen-3-ol, t2-octen-1-ol, and c2-octen-1-ol (Maga JA, J Agric Food Chem 1981, 29,
1). 1-0cten-3-ol is a volatile infochemical present in fungi and recognisable by
fungivores (Holighaus G et al., Chemoecology 2014, 24, 57)
An acetOX"/ derivative of a 16-carbon alcohol with one double bond, gyptol (10-
acetoxy cis-7-hexadecen-1-ol), was described to be a strong attractive substance
secreted by a female moth (Porthetria dispar, "gypsy moth").
OH
Bombycol
BruchinA
HO
Cl
Cl
- Acetylenic alcohols
Natural acetylenic alcohols and their derivatives have been isolated from a wide
variety of plant species, fungi and invertebrates. Pharmacological studies have
revealed that many of them display chemical and medicinal properties.
OH
.
H
QH
v
0
OH
Panaxac-01
Polyacetylenes have been isolated from the stems of Oplopanax elatus (Araliaceae),
plant used in Korean and Chinese traditional medicine for anti-inflammatory and
analgesic purposes (Yang MC et al., J Nat Prod 2010, 73, 801). Among the most
efficient in inhibiting the formation of nitric oxide in LPS-induced cells is a seventeen-
carbon diyne di of with an epoxy cycle, oploxyne A. Other parent compounds without
the epoxy group were also described.
. ........
.
-:.;,. - .
(
,,~
Oplo:xyneA
Page 8 of25
fatty alcohols and aldehydes http://www.cyberlipld.org/slmplelsimp0003.htn
fa.lcarinol
falcarindiol
Falcarinol protects the vegetable from fungal diseases, it showed biphasic activity,
having stimulatory effects between 0.01 and 0.05 µg per ml and inhibitory effects
between 1 and 10 µg per ml, whereas B-carotene showed no effect in the
concentration range 0.001-100 µg per ml (Hansen SL et al., J Sci Food Agric 2003,
83, 1010). Experiments with macrophage cells have shown that falcarinol (and its C-8
hydroxylated d~rivative, falcarindiol) reduced nitric oxide production, suggesting that
these polyacetylenes are responsible for anti-inflammatory bioactivity (Metzger BT et
aL, J Agric Food Chem 2008, 56, 3554). Falcarindiol was first reported as
phytochemicals in carrots (Daucus carota) (Bentley RK et al., J Chem Soc 1969,
685). Besides falcarinol, falcarindiol, and falcarindiol 3-acetate, nine additional
bl~ac~tylen~ al~qh9ls were identifi~Q in Da~~u-~. _car.qta ( $c_h_fT}i~~fl L. et al.,_~ A_gric_
Food Chem 2009, 5 7, 11030).
Experiments with human intestinal cells demonstrate that aliphatic C17-polyacetylenes
(panaxydol, falcarinol,. falcarindiol) are potential anticancer principles of carrots. and
related vegetables (parsley, celery, parsnip, fennel) and that synergistic interaction
between bioactive polyacetylenes may be important for their bioactivity (Purup S et
al., J Agric Food Chem 2009, 57, 8290). Compounds very similar to falcarinol and
extracted from Panax japonicus are potent a-glucosidase inhibitors (Chao HH et al,
Phytochemistry 2010, 71, 1360). These inhibitors may potentially reduce the
progression of diabetes by decreasing digestion and absorption of carbohydrates.
The water dropwort (Oenanthe crocata), which lives near streams in the Northern
Hemisphere, contains a violent toxin, cicutoxin, resulting in convultions and
respiratory paralysis ( Uwai K et al., J Med Chem 2000, 43, 4508).
HO
Cicutoxin
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fatty alcohols and aldehydes http://www.cyberlipid.org/simple/simp0003.ht
Many other polyacetylenic alcohols were found in primitive marine organisms, such as
sponges and ascidians. These invertebrates have no physical defenses and thus they
have developed efficient chemical mechanisms such as polyacetylenic metabolites to
resist predators and bacteria.
Several polyacetylenic alcohols with 22 carbon atoms were isolated and identified .
in lipid extract from a Red Sea sponge, Cally'spongia sp (Youssef DT et al., J Nat (_
Prod 2003, 66; 679). Their physicaf study revealed the presence of 4 triple bonds and
one, two or three double bonds. The structure of one of these Callyspongenols is
given below.
HO
Several polyacetylenic alcohols with 21 carbon atoms were isolated from a marine
ascidian (Polyclinidae) and were determined to have two triple bonds combined with a
conjugated dienyne group (Gavagnin Met al., Lipids 2004, 39, 681). Some of them
.,ave an additional hydroxyl group or only three double bonds. The structure of one o/'
these molecules is given below. \_ ·
Page 10 of25
fatty alcohols and aldehydes http:/twww.cybertipid.org/simple/simp0003.htn
OH
Several brominated polyacetylenic diols with cytotoxic properties were isolated from a
Philippines sponge Diplastrel/a sp (Lerch ML et al., J Nat Prod 2003, 66, 667). One of
these molecules is shown below.
OH
OH
- Sulfated alcohols
Long-chain di-hydroxy alcohols in which both the primary and secondary hydroxyl
groups are converted to sulfate esters and one to five chlorine atoms are introduced
( at various places have been discovered in the alga Ochromonas danica .
(Chrysophyceae, Chrysophyia) where.they-constitute 15% of the total lipids (Haines
TH, Biochem J 1969, 113, 565). An example of these chlorosulfolipids is given
below. There may be several types of chlorine addition: one at R1, two at R3 and R5
or R1 and R2, five at R1 to R5 and six at R1 to Ra.
Phytochemistry 1979, 18, 457), and other microalgal species (Mercer El et al.,
Phytochemistry 1975, 14, 1545).
3ome fatty alcohols, such as dodecanol (lauryl or dodecyl alcohol), are used for the
manufacture of detergents after sulphonation (by action of 803 gas). The salt sodium
laurylsulfate (or sodium dodecylsulfate) is a detergent and strong anionic surfactant,
used in biochemistry and in the composition of cosmetic products (shampoos,
tooth pastes).
2 - Branched-chain alcohols
- Mono·-methylated alcohols
They are components of the waxes found in several species of Mycobacterium but
are not present in other actinomycetes (Minnikin DE et al., Chem Biol 2002, 9, 545).
These alcohols are named phthiocerols. Among that family of long-chain secondary
alcohols, phthiocerol A, phthiodiolone A and phthiotriol are shown below.
QH QH H1r ClCH 1
t 1 ·. I I
f'li'] ~{ttt, 1-:0,ll-C:-H ~('ff~~CU-cClf 1.I• -f"H-rn-nt:-t'.'H,, (
Phlh~totB \.
o'I H OH
I
H,r
l
o .
II
CHi-{CH:lh1.u-CH-CHi-CH-C(1i :1.a. -t'I f =(' "CH:-l:'~f A
l:lhthlodiofl'.lt'llf A..
- Polyisoprenoid alcohols
These compounds are fatty alcohols built of several isoprenoid units (C5). They are
widespread among eukaryotes and prokaryotes and play important roles. in cell
function. They have been also found in geological sediments under saturated forms.
lsopranols
. . OH . .
n
CH,
I ,
phytt:mol H-ICH2CHCII2CI!i.Ji-OH
{ClOH,,iO) 3.7.ll .15·tctromethy1-1-hcicsdccarwl
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fatty alcohols and aldehydes http://www.cyberlipid.org/simple/simp0003.hl
Polyprenols
OH
n
These molecules consist of several up to more than 100 isoprene residues linked
head-to-tail, with a hydroxy group at one end (a-residue) and a hydrogen atom at the
other (ro-end).
lsoprenoid alcohols are ~lso known as terpenols. Search for polyisoprenoid alcohols
was initiated with the accidental discovery of solanesol in tobacco leaves (Rowland
RL et al., J Am Chem Soc 1956, 78, 4680) and isolation of several polyprenols (C30-
C45) in cellulose pulp extracts (Lindgren BO, Acta Chem Scan 1965, 19, 1317).
Pioneer studies were summarized in a review by Hemming FW (Biochem Cell Biol
1992, 70, 377).
Head-to-tail assembly of the isoprenyl units produces polymers differing not only in
chain length but in geometrical configuration. ·
Polypren~ls are present in several bacteria, where they act as lipid carriers in the r·-
·.,iosynthesis of cell surface polymers (Rezanka et al., J Chromatogr A 2001, 936, 961 • /
They -have also been described from cyan.obacteria." the presence of C35-C45.
polyprenols has been described in unicellular and filamentous cyanobacteria
(Bauersachs T et al., Org Geochem 2010, 41, 867).
OH
trans-P olyprenol
I'Ls~III
7
9 II 45
II Solaneool 'I
10 II 50 I Spadicol I
Long-chain trans-polyprenol (n>8) have been characterized from Eucommia
ulmoides.
Geraniol (from rose oil) is a monoterpene (2 isoprene units). It has a rose-like odor
and is commonly used in perfumes and as several fruit flavors. Geraniol is also an
effective mosquito repellent. Inversely, it can attract bees as it is produced by the
scent glands of honey bees to help them mark nectar-bearing flowers and locate the
entrances to their hives.
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fatty alcohols and aldehydes http://www.cyberlipld.org/slmple/simp0003.ht
Cf'3 CH3
I t
H-[CH2CHCH2CH2h-CH2C=C;HCH2 0H
J ,7, 11. J5-tef.n1 mcthylhe.xadec-2-en-1-ol
Bacteriaprenol type
Betulaprenols with n = 3-6 were isolated from the woody tissue of Betula verrucosa
(Wei/burn AR et al., Nature 1966, 212, 1364), and bacterial polyprenol with n = 8
were isolated from Lactobacillus plantarum (Gough DP et al., Biochem J 1970, 118,
167). Betulaprenol-Iike species with 14 to 22 isoprene units have been discovered in
·leaves of Ginkgo biloba (Jbata Ket al., Biochem J 1983, 213, 305).
Polyisoprenoid alcohols are accumulated in the cells most often as free alcohols
and/or esters with carboxylic acids. A fraction of polyisoprenoid ph9sphates has also
been detected, and this form is sometimes predominant in dividing cells and
Saccharomyces cerevisiae (Adair WL et al., Arch Biochem Biophys 1987, 259, 589).
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Ficaprenol typ_e
In plants, the diversity of polyprenols is much broader, their chain length covers the
broad spectrum of compounds ranging from 6 up to 130 carbon atoms (Rezanka T et
al., J Chromatogr A 2001, 936, 95).
Most eukaryotic cells contain one type of polyisoprenoid alcohols with one a-saturated
isoprenoid unit (2,3-dihydro polycis-prenols) which have been called dolichol by
Pennock JF et al. (Nature 1960, 186, 470), a derivative of prenols. Most of these carry
two trans units at them-end of the chain.
Dolichols (fro the Greek dolikos: long) have the general structure :
Dolichols
·OH
n
Dolichols isolated from yeast or animal cells consist mainly of seven to eight
compounds, those with 16, 18, or 19 isoprenoid units being the most abundant (Ragg
SS, Biochem Biophys Res Comm 1998, 243, 1). In human, dolichol-19 (019,
containing 19 isoprene units) is the most abundant species. Dolichol amount was
shown to be increased in the brain gray matter of elderly (Pullarkat RK et al., J Biol
Chem 1982, 257, 5991). Dolichols with 19, 22 and 23 isoprenoid units were described
as early as 1972 in marine invertebrates (Walton MJ et al., Biochem J 1972, 127,
471). Furthermore, the pattern of their distribution may be considered as a
chemotaxonomic criterion. It has been reported that a high proportion of dolichols is
esterified to fatty acids. As an example, 85-90% of doJichols are esterified in mouse
(
testis (Potter Jet al., Biochem Biophys Res Comm 1983, 110, 512). In addition,
\ dolichyl dolichoate has been found in bovine thyroid (Steen L et at, Biochim Biop1;_
Acta, 1984, 796, 294).
A characteristic shortening of plasma and urinary dolichols in retinitis pigmentosa
P~OA 17 of ?S
fatty alcohols and aldehydes http://www.cyberllpld.org/simple/simp0003.hf
patients was observed (Wen R et al., J Lipid Res 2013, 54, 3516). DolichoJ-18 (018)
became the dominant dolichol species in patients instead of dofichol-19 (019) in ( ·
normal individuals.
f hey are weJI known for their important role as glycosyl carrier in a phosphorylated
form in the synthesis of polysaccharides and glycoproteins in yeast cells, and animals.
Oolichyl phosphate is an obligatory intermediate in the biosynthesis of N-glycosidically
linked oligosaccharide chains. Conversely, they have been identified as the
predominant isoprenoid form in roots (Skou1pinska-Tudek Ket al., Lipids 2003, 38,
981} and in mushroom tissue (Wcjtas M. et al., Chem Phys Lipids 2004, 130, 109).
Similar compounds (ficaprenols) have the same metabolic function in plants.
The repartition of the various types of polyisoprenoid alcohols between plants and
animals and their metabolism have been extensively discussed (Swiezewska E et al.,
Prog Lipid Res 2005, 44, 235). Biosynthesis of polyisoprenoid alcohols and their
bioJogical role have been reviewed in 2005 (Swiezewska E et al., Prog Upid Res
2005# 44, 235).
3 - Phenolic alcohols
Among the simple phenolic alcohols, monolignols are the source materials for (
;>iosynthesiS. o.f both Jignans. and Jignin .. The starting material for production of
monolignols (phenylpropanoid) is the amino acid phenylalanine. There are two main
monolignols: coniferyl alcohol and sinapyl alcohol.. Para-coumaryl alcohol is similar
to conipheryl alcohol but without the methoxy group.
Comp.heryt alcohol
OH
Sinspyl .alcohol
HO
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Phytochemistry 2008, 69, 1179). These compounds displayed an agonist activity for
/
'
transient receptor potential vanilloid 1 (capsaicin receptor) as the well known
\ __
capsaicinoids present in these plant species.
An analogue component but with a ketone group instead of the metho:xy group, a
phenolphthiodiolone, has been detected in mycoside A (Fournie JJ et al., J Biol Chem
1987, 262, 3174).
4 - Cyclic alcohols
OH
H3 C
3-(4-methylfuran-3-yl)propan-1-ol
Some cyclic alkyl polyols have been reported in plants. Among the various form
present in .an Anacardiaceae, Tapirira guianensis, from South America, two displayed
anti-protozoa! (Plasmodium talciparum) and anti-bacterial (Staphylococcus spp)
activities (Roumy V et al., Phytochemistry 2009, 70, 305). The structure shown below
is that of a trihydro:xy-alcohol containing a cyclohexene ring.
P:inP. rn of 2/'i
fatty alcohols and aldehydes http:J/www.cyberlipid.org/simple/slmp0003.ht
(
OH
4,6,2'-trihydroxy-6-[1 O'(Z)-heptadeceny0-1-cyclohexen-2-one
As emphasized by the authors, external application of the active plant extract or of the
purified cor:npounds could represent an accessible therapeutic alternative to classical
medicine against leishmaniasis.
FATTY ALDEHYDES
Long-chain aldehydes are found in free form, but also in the form of vinyl ether (known
as alk-1-enyl ether) integated in glycerides and phospholipids (plasmalogens).
The free aldehydes can be as fatty acids saturated or unsaturated. They have a ( ,
Jen~ral formula CH3(CH2)nCHQ wit~ n=6 to 20 or gre~ter. The most common is \
palmitaldehyde (hexadecanal) with a 16 carbon chain. Normal monoenoic aldehydes
are analogous to the monoenoic fatty acids.
It must be noticed that an aldehyde function may be found at a terminal (co) position
while an acid function is present at the other end of the carbon chain (om fatty acids).
These compounds have impoi:tant signaling properties in plants.
Long-chain aldehydes have been described in the waxes which impregnate the matrix
covering all organs of plants (Vermeer CP et al., Phytochemistry 2003, 62, 433).
These compounds forming about 7% of the leaf cuticular waxes of Ricinus communis
were identified as homologous unbranched aldehydes ranging from C22 to C28 with a ,
hydroxyl group at the carbon 3. Long-chain 5-hydroxyaldehydes with chain lengths
from C24 to C36, the C28 chain being the most abundant, were identified in the
cuticular wax of Taxus baccata needles (Wen Met al., Phytochemistry 2007, 68,
2563). Long-chain aliphatic aldehydes with chain-length from C22 'to C30 are also
present in viigin olive oils, hexacosanal (C26) being the most abundant aldehyde
(Perez-Camino MC et al., Food Chem 2012, 132, 1451).
/
Aldehydes may be produced during decomposition of fatty acid hydroperoxides \_ '
following a pero:xidation attack. Several aldehydes (hexanal, heptanal..) belong to
aroma compounds which are found in environmental or food systems (see the
website: Flavornet). Aldehydes (mono- or di-unsaturated) with 5 to 9 carbon atoms are
Page 20 of25
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Cl
2-Chloro-hexadecanal
Both these chloro-fatty aldehydes have been detected in neutrophils activated with
PMA (Thukkan.i AK et at, J Biol Chem 2002, 277, 3842) and in human atherosclerotic
lesions (Thukkani AK et al, Circulation 2003, 108, 3128). Furthermore, 2-
chlorohexadecanal was shown to induce COX-2 expression in human coronary artery
endothelial cells (Messner MC et al., Lipids 2008, 43, 581). These data suggest that
2-chlorohexadecanal and possibly its metabolite 2-chlorohexadecanoic acid, both
produced during leukocyte activation, may alter vascular endothelial cell function by
upregulation of COX-2 expression.
(.
Long after the demonstration of the presence of iodinated lipids in thyroid (besides \_
·iodinated aminoacids), if was shown that the major iodinated lipid formed in thyroid
when incubated in vitro with iodide was 2-iodohexadecanal (Pereira A et al, J Biol
Chem 1990, 265,-17018). In rat and dog thyroid, 2-iodooctadecanal was determined
to be more abundant .that the 16-carbon aldehyde. These compounds, which are
thought to play a role in the regulation of thyroid function, were recently shown to be
formed by the attack of reactive iodine on the vinyl ether group of PE plasmalogen.
This attack generates an unstable iodinated derivative which breaks into
lysophosphatidylethanolamine and 2-iodo aldehydes (Rannee/s \Let al, J Biol Chem
1996, 271, 23006).
Several fatty aldehydes are known to have pheromone functions. Studies in African
and Asian countries have shown that the use of 10, 12-hexadecadienal could be
effective for control of the spiny bollworm Earias insulana, a cotton pest. The sex
pheromone of the navel orange worm, Amyelois transitel/a, 11, 13-hexadecadienal, is
usually used in the control of this citric pest.
A branched saturated aldehyde (3,5,9-trimethyldodecenal, stylopsal) has been
identified as a female-produced sex pheromone in Sty/ops (Strepsiptera), an
entomophagous endoparasitic insect (Cvacka Jet al., J Chem Ecol 2012, 38, 1483).
Page 22 of25
fatty alcohols and aldehydes http://wNw.cyberlipid.org/simple/simp0003.htr
CHO
Stylopsal
CH3 <;H3
r
I
neral CH3C=CH(CH2hC--CH
(C1oH160) I
CHO
(
3,7--dimethyl-trans-2,6-octadienal
CH:3 CH3
1 I
citronella/ CH3C=CH(CH2)2CffCH2CHO
(C1oH1sO) 3,7..dime,thyl-6-octenal
These three terpenic aldehydes are produced in large amounts by the mandibular
glands of ants and may function as defensive repellents (Regnier FE et al., J Insect
Physiol 1968, 14, 955}. In contrast, the same molecules have a role of recruiting
pheromones in honeybees
Citral, a mixture of the tautomers geranial (trans-citral} and neral (cis-citral} is a major
component (more than 60%} of the lemongrass (Cymbopogon flexuosus} oil.
Lemongrass is widely used,· particularly in Southeast Asia and Brazil, as a food
flavoring, as a perfume, and for its medicinal properties (analgesic and anti-
inflammatory}. It was found that citral is a major suppressor of COX-2 expression a
an activator of PPARa. and y (Katsukawa Met al., Biochim Biophys Acta 2010, 1801,
1214}.
Paae 23 of25
fatty alcohols and aldehydes http://www.cyberlipid.org/simple/simp0003.~
It was demonstrated that damaged leaves released 2-hexenal, among other C6-
volatile aldehydes, produced from the catalytic activity of hydroperoxide lyase (
(Turliags TC et al., Proc Ntl Acad Sci USA 1995, 92, 4169). These compounds, \.
::onsidered as signal molecules, can trigger several responses in neighboring plants
and may also act as antimicrobial agents· (Farmer EE, Nature 2001, 411, 854).
One important constituent of this group of aldehydes is retinal, one active form of
vitamin A involved in the light reception of animal eyes but also in bacteria as a
component of the proton pump.
CHO
Retinal exist in two forms, a cis and a trans isomer. On illumination with white light, the
visual pigment, rhodopsin is converted to a mixture of a protein ( opsin) and trans- (
retinal. This isomer must be transformed into the cis form by retinal isomerase before~
it combines again with opsin (dark phase). Both isomers can be reduced to retinol
(vitamin A) by a NADH dependent alcohol dehydrogenase. Retinal is stocked in retina
mainly in an acylated form. ·
Cinnamic aldehyde
Page 24of25
fatty alcohols and aldehydes http://www.cyberlipld.org/slmpleJsimp0003.htn
(
IJJ
\
Paae 25 of25
(
6
Use of Fatty Alcohols
Principles of
Flue-Cured Tobacco
Production
. ·.· .
..:
'::·
.: "o,\ :··
...· . . ;-
.. .
.. ···\--"..
. :...-
·.·.: ·::'·'
-: .
~- ,.
Principles of Tobaao Produ.ction
r····
,....-.~, ,
'Ihe tobacco plant produces a hormone in the terminal bud Figure 32. Toppmg and sucker control (R) provide many
that inhibits the growth of suckers. When this source of the benefits compared to not topped (L). ·
inhibition is removed the sucker buds begin to grow. At
first: the upper three to four Stickers develop. Tue terminal
buds of tliese suckers also produce this hormone. If these their cheniistry. especially those produced in the upper leaf
are removed, additi.oI;lal suckers will develop down the positions.
stalks as well as secoD.dary suckers at the u!>Per leaf axils. A
tobacco plant has the potential ofproducing three suckers TOPPING
at each leaf axil particularly at upper stalk positions. Under ·
most cultural practices, howe'Ver, we 1:JSWilly have only two Whether or not a plant is topped, and if topped, the time of - /- ·
1
that are of any consequence. topping can have a pronounced effect-on the cured lea£ ~. \.
Most growers and buyers have found tlUtt removal of the -'Ihe data in Table 51 indicate that topPmg improves yield.
tops dong with the removal or restriction of growth of increases.price and value per acre. and increases the alka-
suckers results in certain desirable changes in the eured leaf loid and sugar content of the cured ;Lea£ 'Ihe yield increase
fuper:imentS have shown that manual topping and hand is much greater for topphig plus suckering than for topping
suckering lead to an increase in root growth. 'Ihisl in tum, and not suckering when compared to the not-topped plant
increases the plant's potential to absorb water and nutd- 'Ihe same is true for the allcaloid and sugar content ofthe .
ents and to synthesize nicotine. Also, topping and ~clcer cured leaf. For maximum yield and dollar return, the plants
ing reduce the weight at the top of the plant which makes should be topped and the suckers must be controlled either
the plant less likely to blow aver during windstorms. 'Ihe by hand or with plant growth regulators (chemicals).
practice of topping and suckering reduces the drain on the
leaves of certain organic and inorganic compounds used for 'Ihe time·of topping with manual sucker control Will ioflu-
growth by the plant; therefore, this' practice can be expected ence the yield and the quality of a tobacco crop as shown
to increase the weight and body of the leaves and to change in Table 52 where manual sucker control was practiced ·and
in Table 53 and Figure 33 with maleic
Table 51. Effect of Topping and Hand Suc:kedng on Yield, Price, Total hydrazide used for sucker co_ntrol
Alkaloids. and Reducing Sugars.u
. 1960-62 1962 'Ihe data in Table 52 show there was a
% % marked reduction in yield and price/
Yield Price Value Total ReduQn.g cwt. when topping was delayed beyond
Treatment ()bs!A) ($/cwt.) $/A Alkaloids Sugars the early flower stage. Yield was lowered
Not topped or suckered 1390 63.99 890 1.76 13.30 an average of 15 pounds per day. Total
Topped.-notsuckered 1487 64.99 966 2.36 17.~0
alkaloid content was reduced as topping
Topped and suckered 1806 65.65 1186 2.80 18.20 time was delayed, except from the full to
11
Tests conducted by J.P. Chaplin, Z.T. Ford, and R.E. Currin, Agrtcultural Ex- late flower stage, and sugar content~
periment Station, South Carolina. lowered with delayed toppmg after the
early flower stage. Total nitrogen content
Topping and Suckering
Table53. Effects of Time (Flower Stage) ofToppingFlue-Cured Tobacco with Manual Sucker
Control, 1958-59. 11
Pulled % %
Yield Price Suckers Wt./pl %'lbtal Reducing Total
'D:ea:tment . Ths/A $/cwt. No./pl (grams) Alkaloids Sugars Nitrogen
Button stage 1910 56.49 15.0 124 2.59 21.8 2.0
Early flower stage 1890 57 .39 12.2 68 2.02 22.8 1.9
Full flower stage 1774 54.41 6.4 32 1.86 21.8 1.9
Late flower stage 1676 54.43 6.0 10 1.95 20.0 1.9
tfTests conducted by H.V. Marshall. Jr.. and Heinz Seltmann, N. C. State University.
.. Note: When the plants Were topped in the button ~e the first fl.oral buds were well funned but no
/ : flowers were. opened. '!here was a time lapse of 7 days between each of the 4 stages. All treatments
were hand ~ckered.
button stilge orly flower stllge full flower stllge late flower
---1~~~14----7DA't'S---~Jloil•..----7DAYS----111Jlo*'l~----'IDAYS----1111o~1~-
yleld: pounds per acre .
2,305 2,122 l,902 1,741
Figure 33. Pour s):ages of flowering with yield for suclcer control
79
Principles of Tobacco Production
I:· (
There are several other benefits of topping in the button Chemically topped plants appear to b~ injured; however,
stage. Topping is completed before harvest begins. This there are several importarit benefits obtained from chez¢-
helps spread the workload away from the peak harvest pe- . cal topping. First, when chemical topping is observed on a
riod. '!he chance of plants being blown over in a windstorm percentage of plants in the field, a high degree of sucker kill
is reduced when they are topped. Tue populations of certain is obtained, even on plants that were not chemically topped.
insects are lowered because eggs and larvae survival is nil The two sucker buds in contacted leaf axils are killed in
on floral p~ which are removed from the plants. The egg- most of the leaf axils.
laying moths of certain harmful insects are more attracted
to the floral parts of the plant than older leaf tissue. If these Second, results from on-farm tests show plants topped in ..
eggs. and larva can be effectively destroyed by topping. then the prebutton stage yidd more than if topped later. 'Ih( ··· ..{
costs, chemical residues, and possible hazards of insecti- an appreciable amount of tissue destroyed in the buttoi ·,,~
cides are reduced, when plaDts are chemically toiyed. The remaining leaf La.. •
..•.....
~
80 --- ~ -
Topping and Suckering
,. .
I
r
I "-
;
si.JCKBR CONTROL
Table 56. Effect of Degree of Sucker Control on Yield and Price.1' 1 wo
1be. degree of sucker control and yield are locations, 1965-66.
closely correlated. lhe higher degree of control %
i.
:~ ~ normally results in a higher yield. 'Ihe data in Suck.er Yield Price %
j: Th.hie 56 show the effect of removing suckers of 'Ii:eatme.nt Control lbs/A $/cwt Nicotir
:,·: different lengths on yield and price of ~obacco. Not suckered· 1409 65.61 1.56
\: ·.
Suckers were removed by hand when they were Topped not suckered 0 1566 65.00 2.03
12~ 8~ and 4" long and in one treatment they
j<·
'· ·'
'·: were "rubbed out" almost daily so that there (Topped and Hand Suckered)
J~ ..
.; was very limited growth. 'Ihe degree of control 12 inch suclcers 42 1847 67.75 2.61
· .. had a very definite effect on yield, but a less 8 inch suckers 53 1903 66.79 2.79
;;.:.
pronounced effect on price. 'Ib.e higher p~cent
'..
~
sucker control also increased the body and
4 inch suckers 73 1926 66.73 3.10
! :.
Suckers rubbed out 99 2111 .65.61 3.41
: .
nicotine content of the cured leaf. ll'fests conducted by Gerald Peedin and Heinz Seltmann, N.C. State Unive
; .
sity.
I·.
; .. Removing suckers by hand has always been a
I<
difficult and time-consuming job. In a 1978
study; Dr. Heinz Seltmann found that app:ri:oo- Thble 57. Effect of Malek Hyd:razide on Sucker Control, Yield, and Pric
mately 60 worker hours of labor were required ofFlue-Cured Tobacco. 7locations, 1967. 11
to hand sucker an acre of flue-cured tobacco Sucker Suckers
·when the suclcers were removed when they Control Suckers Green Wt/pl Yield Prfo
were four to eight inches long. 'Ibis job is not 'freatment · (%) NoJpl (grams) llisl!{ - (
only tiresome and monotonous, but it occurs Topped not suckered 0 6.0 726 1672°, '-,.
during the harvest season which is a peaklabor · Topped hand suckered 42 20.6, 418 2024 u/ .91
require.Illent period. MH, 170 mg. . 74 ' 6.2 186 ~o 683!
llR.egional sucker contl'ol tests conducted in Florida, Georgia, Solith Caro-
Clumlcal Sucker.Control lina, North Carolina, and VIrginia.
~
nation of two of these chemicals. · Gallons Percent Suckers per Acre
,,·f Contact Water Contact Number Pounds
An understanding of how the various sucker
1 49 .2 29,900 6,256
control chemicals work is necessary to know
1.5 48.5 3 15,600 4,794
the correct application technique for any sucker
2 48 4 . 7,800 1,950
control chemical Many factors are involved;
Tests conducted byW.K Collins with Off-Shoot-T.
however, the time ofleaf and floral develop-
.82
Topping ~d Suckering
( ment that is desirable for a given chemical is of paramount the sucker will discolor. After several hours, the sucker will
\ (--,, iinportance. · become brown and even black by the next day. Tue concen-
tration of the solution is very important! Jf the concentta-
Sucker control chemicals can be classified into the following tion is too weak, sucker control is reduced; if the concentra-
four groups based upon how they must be used and how tion is too strong, the leaves can be burned or leaf axils can
they affect the plant and sucker growth. be weakened which can cause leaf drop or .an entry site for
certain disease organisms.
Contacts: normal fatty alcohols (C10 or a mixture of
C6-C12 alcohols}. Weak contact solutions, those that are less than 4 percent
·• Systemic:: maleic hydrazide (pptassiwn salt). -1 ofC1 - Ci0 fattyalcohol, often visUally do an acceptable job;
FST-7: (a combination of C 1D fatty alcohol and potas- however, experience has shown the secondary suckers grow
sium salt maleic hydrazide). rapidly and become too large for the second application
Contact-local-systemic: flumetralin (Prime+), of the contact to provide control Then the sucker growth
butralin ('Thtaex), DCPA (Razor), and peD.dimethalin on vigorous growing tobacco cannot be controlled with
(Stomp). the suggested rates of systemic-acting chemicals. A rule of
thumb to use is to apply a contact solution that chemically
Alcohol Contact S~lutions must wet the small suckers to tops 5 to 10 percent of the small, late plants in a field. Jf no
be effective. When the spray solution wets the more tender plants are chemically topped during the first application,
sucker tissues, it destroys the "waterproofing" layers by a the solution may be too weak to provide maximum sucker
di'}'iiig action• .& these cell membranes are being destroyed, · control
,, _
The :first application of a contact should be made when
83
Principles of Tobacco Production
Table 60•. Sucker Control Treatments Used in On-Farm Tusts Conducted by the N. C.
Cooperative Extension Service in Alexander, Brunswick, Cumberland, Durham, Lenior,
Gran~e, Person, Surry, and Yadkin Counties.
Time ofTopPing"
About7Days Yield21 Qualltf' Suckers/Acre
'n:eatment Button 3-5 days After No. 2 lbs/A Index3' ·No. Lbs.
A OST4%41 OST 4% RMH 1.5 ga1JA51 2434 36.6 2029 170
B OST4% OST 5% RMH 1.5 gal/A 2483 36.8 1049 66
ll'Ihe first application of contact agents applied with top on and plants topped immediately;
21No data from Granville and Yadkin Counties.
"Quality Index is a 1-99 rating b~d on government grades. Higher ratings indicated better
quality.
41
=
0ST Off-Shoot-T.
s'RMH =Royal MH-30.
about 50-60 percent of the plants are in the button stage, es the chan.ce of the spray spluiion corning in contact with
the time when sucker buds are small and tender. A secon~ the suck.er, especially where it is difficult to correctly apply
application of the contact three to five days later will in- contacts with mechanical sprayers. One hand application
crease the chances that control will be effective on all suck- of a coiitact solution is usna11y adequate before a systemic
ers. A 5 percent solution of the contact at this stage usually chemical is applied.
increases the effectiveness. · .. -~·-·- ,,,--
The contact solutions do not move into the plant leaves andi \
A 5"Percent strength is suggested because the plant is usu• interfere with growth; therefore, leaf development continues ·.
ally~ore developed and leaf tissue is thicker and able to and the production ofgood. mediuin-bodied tobacco is
withstand the increased concentration. Also sucker growth maximized. '!he chief role of a contact solution is to sup-
is likely to be leSs tender than at the time of the :first applica- press sucker growth for one to two weeks after early topping
tion. (since yields are riuaimjzed. by topping in the button stage),
which allows immature, upper leaves to develop enough so
·an
Make sure solutions are kept mixed because the active that other cheuiicals that inhibit cell diVmon can be applied
ingredients (fatty alcohols) are lighter than water; therefore, without leaf damage. ·
they tend to fl.oat and must be co~tly agitated to prevent
· separation. Because fatty alcohols are lighter than water, it is Mlllek Hydrazlde (MHJ
suggested that~ be added to the spray tank while simul-
taneously adding water. MH is one of the oldest pesticides in use today. It was
synthesized and the plant growth inhioiting properties were
Some growers are applying a third contact application on discovered in 1947. MH is the only true systemic plant
irregular flowering aops three to five days after the second growth regulator used for sucker control on tobacco. ·Once
application. A 5 percent solution should be used when a absorbed by the plant, MH is freelytranslocated in the sym-
third contact application is made. plast to active growing points in th-e plant where its mecha-
nism r:>f action is a uracil antimetabolite. 'IIanslocation is
If a contact solution is applied to a wet plant. the wat.er pres- more effective downward and once in gro~points, MH
ent will dilute the solution, resulting in weaker concentra- inhibits cell division. Cell elbngati?n remaills unaffected.
tion than planned.
For these reasons, small suckers are stopped after MH treat-
'!he use of strong contact solutions increases the chance of ment. Slightly larger suckers develop at a greatly reduced
leaf drop; ·however, this is rarely a problem unless excess rate but with very narrow leaves, and upper leaves that are\
nitrogen· has been applied. 10 to 12 inches long will develop to their normal size.
fi Some growers apply their contact solutions with hand-oper- MH is most effective when applied on a crop growing under
II
11 ated applicators. This method of application greatly increas- . good ?1oistuxe conditions. This is because the cuticle of the
- rt.
Topping and Suckering
/
.r~
I '
Figure 37. 1iiple nozzle atrangementfor spraying contact- Figure 38. Application of contact-type solution with.hand-
type solutions. opera.~ed applicators.
leaf is easier to penetrate when the.plant is actively growing. is not metabolized which also leads to a high percentage of
'Therefore. MH is more readily absorbed when conditi_ons applied chemical remaining. ·
exist that favor good growth. Preferably, MH should be
applied in the morning to dry plants about a week after the These factors result in a higher percentage of the chemical
button stage. in and on the cured leaf than is the case with most p~
ddes. However, MH has a water solubility of 6,000 ppm ·
Under normal conditions, MH can be expected to .provide which is very high. 'Iliere:fore, rainfall and/or irrigation
suckf?I' control for only ab~ut six w~ after application. plays a sign.ifi.cant role in contrcil of suckers and resulting
However, proper-use of two contact solutions.before MH is ~residues. Rainfall too soon after application can reduce
. a~li~ illows for late application o~MH. which lengthens effectiveness of MH but rainfall after MH is absorbed has
the period of e1fective su~ control no effect on control but greatly reduces leaf residues.
'The tis~ of a contact-local systemic before, after. or in a For this reason. MH should be used according to the label,
tanlonix with MH can extend sucker control well beyond · especially the precaution 'which states to wait at least seven
1he point at which.control with MH alone would start days after application before the next harvest Hopefully, a
to breakdown. 'Ibis can be important because varieties· · rain or irrigation or some dews will wash off the unb~und
developed in the last several years tend to mature lat~ and MH left on the leaf surfaces and reduce those residues as
remain in the field much longer than older varieties. There- shown in Thble 61.
fore, extended control is often needed.
FST-7 whi~ contains both. a fatty alcohol (contact) .and
MH residues are significantly higher than other peStlddes MH should be applied at the same stage of plant develop-
~~don tobacco. 1here are several reasons why this is the ment as MH; but because it contains a contact, the mixture
case. High residues can be explained by chemical prop- ·
erti.es of the MH molecule and use pattems by growers. Table 61. MH Residue Levels on Mid-Stalk Tobacco
Chemically, MH is a very stable molecule in and on plants. Between 0 and 4 Days After Application of MH at upper
Several of the degradation ~or transfer processes for Piedmont Research Station.11
organic chemicals do net affect MH. For example, MH is HARVEST TIME
resis+..ant to decomposition by ultraviolet irradiation (UV) ~(D_._,ays..__After
__ A_pP_li_·c_ati_on~)...__ _,_PP_,_
,_m _ _% Reduction
which is a major route of degradation for many pesticides. 0 140 0
'l;he decomposition temperature for MH is 260°C which is
much higher than the maximum temp~ture that is used 1 1~ u
for stem drying flue-cu.red leaf, which is approximately 3:11 107 24
74°C. In addition. the vapor pressure ofMH is essentially 4 48 66
zero. 'Iherefore, the amount of MH lost to volatilization is
11
Conducted by Dr. T. J. Sheets (1978).
21
insignificant. Once :inside the plant, MH becomes fixed and 2.2 inch rain on Day 3.
85
Principles of Tobacco Production
/'
i r-· I 0-
Topping and Suckering
,/
Step 6. (Needed only if sucker regrowth is anticipated late treat with Prime+. As the remainder of the plants
in the season) reach th,is stage, they should be topped, large suckers
removed and treated, being careful not to treat any
Alternative A previously treated plants or use more solution than
Apply a 5% contact solution {2.5 gals in 47.5 gals) necessary to reach the bottom of the stalk
using the standard application procedure for contacts.
'Ibis should be doµe 3-4 weeks after MH application Altemative B
when suckers are small and susceptible to cont~t Apply a contact solution at the button stage. When
bUm. Large suckers (greater than 1 inch) should be 50% of the plants reach the elongated button-to-
removed by hand. eatlyflower stage, apply Prime+ preferably with the
dropline method as in Alternative A, Program II .
Alternative B above, or use a power sprayer to apply 30-50 gals/A of
Apply 2 qU:arts/A of Prime+ using the standard appli- Prime+ solution made by :arlxing 2 quarts of Prime+
. cation procedure for contacts. (SO gals total solution/ with 49.5 gals of water. The purpose of the initial
acre, 3 nozzles/row, low pressure. etc). 'Ibis should be contact is to allow the smaller plants to become more
initiated 3-4 weeks after MH application. Large suck- mature before Prime+ application. However, spray-
ers (greater than 1 inch) should be removed by hand. ing Prime+ may cause distortion of upper leaves on
H Prime+ was used earlier for sucker control, allow 1 young plants, so a judgement must be made to spray
week between Prime+ applicatlon and harvest. . Prime+, use the. dropline with Prime+, or another
alternative in Program I based on the amount of un-
Soil residues of Prime+ from the previous tobacco evenness in the crop.
crop may contribute to ~early-season growth
of following crops, especially small grains and com 'Ihe Use of Smfactan~ with Prime+. In on-farm
but may also include nonrotated tob~cco, especially tests, 0.25% X-77 (1 pt/50 gal) is often added to the
if the full labeled rate of Prime+ is used for sucker spray solution where Prime+ is used alone. Some
control To minimizepossibleinjuryto crops planted other surfactants have been phytoto:ric to tobacco
in the fall or following spring. follow labeled mixing when added to Prime+. Tue use of smfactmts other
instructions and do not apply an excessive yolume to than X-77 with Prime+ is discomaged due to some
the point of runo1f. Also. after the last priming, follow surfactants showing phytoto:ricity and also a lack of
stalk and root destruction practices, and two weeks research data to indicate which surfactants can be
iater bury the stalks and roots using a moldboard successfully used. [SUrfactants or adjuvants, includ-
· .plow set at a depth of 5-6 inches. Disk 1 or 2 times ing X-77, should never be added to the tanJcitrix of
befoxe planting a small grain cover crop. Prime+ and MH].
In recent years, carryover of Prime+ has not been .Ailditional Items to Consider
observed where the 2 qt/acre rate of Prime+ has been
used. Current recommended sucker control programs (1) Large suckers missed bythe contact or conta.ct-local-
include Prime+ at 2 qts/acre. Frc;>m both a sucker systemic chemical have to be remaved by hand. .
control and carryover standpoint. growers are advised
not to exceed 2 qts/~cre of Prime+ per crop per year. (2) MH should be applied only once, according to label,
unless there is a ~-off" within 6 hours after ap-
Program II (Hand or DropJine Applkation) plication.
II- 87
Principles of Tobacco Production
(5) MH will tend to make the upper leaves turn yellow or Chapter XIII
bro'nze. espc:cially if applied too early cir if excessive
amounts are used. Bronzing is a result of destruction HARVESTING AND CURING
of chlorophyll and does not mean that the leaves are
ripe. There are two major objectives in curing flue-cured tobacco:
(~ Prime+ and
other local-systemics may tend to keep (1) to provide temperature and humidity conditions
upper leaves green longer. which will en~ourage certain desirable chemical and
biological changes to take place, while using mini'-
(7) · MH has been observed to greatly reduce broonirape mum quanP,ties of fuel and
(OROBANCHE) when sprayed on tobacco in :fi~ds (2) . to preserve the leaf by timely drying to retain the
infested with this parasite. potential quality. Curing is more than drying the leaf.
It involves chemical and physical changes which are
necessary for high quality to.bacco suitable for manu-
facturer and consumer acceptance.· •
HARVESTING
f -\.
)
" .....
~ :' :: ··': ...
.·
Recommendations for the use of agricultural chemicals are Included in this publication as
a convenience to the reader. The use of brand names and any mention or listing of com-
mercial products or services in this publication does not imply endorsement by North
Carolina State University nor discrimination against similar products or services not men-
tioned. Individuals who use agricultural chemicals are responsible for ensuring that the in-
tended use complies with current regulations and conforms to the product label. Be sure
to obtain current information ·about usage regulations and examine a current product ~1E--CURED
'~;~a Guide
label before applying any che~ical. For assistance, contact your county Cooperative
Extension Center.
\I~i~J~iQ~~' '
A PRECAUTIONARY STATEMENT ON PESTICIDES
Pesticides must be used carefully to protect against human lnJury and harm
.,,
to the environment. Diagnose your pest problem, and select the proper pes-
ticide if one Is needed. Follow label use dlre!=tlons, and obey all federal, state, >I_~:" • ~;
and local ·pesticide laws 21nd regulations.
Published by
North Carolina Cooperative· Extension Service
Printed by Data Reproductions Corp.
S,SOO copies af this public tfocumentwere prinWJ at a cost of SS,995 or $1.09 per copy.
COLLEGf Of
AGRICULTURE&l1FESCIENCES
ACADEMICS• RESEARCH .. EXTENSION
AG-187 (Revised) 12/09-5.SM-BS El0-51847
Dlstrlbuted rn furtherance of the ~cts of Congress of May 8 and June 30, 1914. North Carolina State University and
., ,, ,,... 1• ..... . _ . . . . . . •• • .. •• •• i • ••• •• • ' • •• "
.,~ · · ... Table 1...4. Flue-cured tobacco-machine harvest-piedmont North Carolina:
"_,. 2010 estimated costs per acre
1. Gross recelots
Unit
, E c-· --··•• I ~· nuc I
Your
Farm
.: .·. . ·'. .·
~·
· : ':: · . _ Unit
I Price/Cost
r Unit
Total Your
Farm
Stalk DOSition -- -- --- . - --· -
Yield Price/lb Stalk oosition Yield Price/lb
Luas
o.oo <······
lb so.oo
S0.00 .::..:.. ·.: Luas fb 0.00 SO.DO so.oo
Cutter
Leaf
lb ·o.oo so.oo so.oo .. •· Cutter lb 0.00 so.oo $0.00
Tios
lb o.oo
10.00 10.00 :( :;>.. . Leaf lb 0.00 so.oo $0.00
Total receints
lb o.oo
S0.00 so.oo Tlos lb 0.00 SO.OD SO.DO
2. Variable costs so.oo Total recefots S0.00
Plants (areenhouse) '.: · ·2. Variable costs
thou 6.20 $34.00 $210.80 Plants (areenhouse) thou. 6.20 $210.80
Multioumose fumiaation aal $34.00
10.SO 113.00 $736.50 Multiouroose fumiaatfon aaf 10.50 J13.00 S136.SO
Fertilizer .,,.
.s-.: Fertlfizer
B-16·24
15.5-0-0
lb 7.00 $25.19 $176.33 .. ....
...
8-16-24 lb 7.00 S25.19 S176.33
lime fororatedl
lb 300.00 S0.33 $99.00 .,, . 30% UAN lb 760.00 S0.32 SS1.20
ton 0.33 $51.75 Stl.08 Lime (ororated) ton 0.33 $51.75 $17.08
Herbicides acre 1.00 S40.5S $40.55 Herbicides acre LOO $40.55 $40.55
fnsectlddes acre 1.00
Funaicides
S36.59 S36.59 . ·1nsectiddes acre 1.00 $36.59 $36.59.
acre 1.00 20.31 20.31 Sucker control acre 1.00 $109.26 $109.26
Sucker control acre 1.00 $109.26 $109.26 ."
Haufina . Haulina lb 2.500.00 $0.04 $100.00
lb 2 400.00 .. .. ·::·~·
'
~
Covercroe acre 0.00
S0.04
$75.00
$96.00
so.oo
~
:.· . ·
. lrrlaation
Covercroo
times
acre
3.00
0.00
$26.47
$15.00
$79.41
$0.00
Curina fuel aaf 275.00
Electridtv S1.30 $357.50 Curina fuel oaf 275.00 $1.30 $357.50
kwh 1.580.00 SO.OB 1126.40 E/ectrfcitv kwh 1.580.00 SO.OB $726.40
Cron insurance $ 1.00 $65.00
·t'.:· .
$65.00 ··..:·::.: . Croo insurance $ 1.00 $65.00 $65.00
Balfna suon/fes
Tractor/machinerv
$ 2400.00
acre
S0.003 . Sl.20 ... BalfnQ SUDDfies 1 2.500.00 S0.003 S7.50
1.00 S227.33 $227.33 ..... ·:. . Tractor/machlnerv acre 1.00 $203.78 $203.78
Labor ~
Labor
Preharvest . hr 29.00 SB.85 $256.65
:b !' ..
I.. ·:..:::..
6. Net returns to land. risk and manaaement
......... ~. 5. Total costs
. ......
$3,238.09
.. Crop Insurance: 6596 based premfuim. No disaster subsidies. 6. Net return$ to land risk, and manaaement
• Producers who employ guest workers should also lndude other expenses (such as
housing, and transportation) assodated with labor. . • Crop insurance: 65% based premiulm. No disaster subsidies.
• Please note: This budget is for planning purposes only.
• May need two applications of.Rldomll for black shonk @ S40/appllcatlon.
Prepared by Gary Bullen, Loren Rsher, and Emily Weddington, N.C State Unlvenlt)?
Departmer• ,,-..-irlculturaf and Resourr:e Economla.
·l . :
f.. . . .
'
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* Producers who employ guest workers should al~o indude other expenses (housing,
transportation, etc.) assodoted with labor.
" . Please note: This budget Is for planning purposes only.
Prepared by: Gary Bullen, Loren Fisher, and Emily Weddington, N.C. State University,
Department of Agriwltura/ and Resource Economics . --.......
i )
16
t· J-'11
Sout~~t Farm Press
May;t:;J. 1983
~
It has been know for a long time that good sucker control reduces the supply
of tender foliage which is a major food supply for insect buildups. In fact,
many people believe the degree of sucker control achieved with MH containing
products has played a significant role in sharply reducing hornworm populations.
The R-9-P Program of early stalk and root destruction reduces food supplies
for certain insects and diseases to build up on after harvest. Good sucker.
control does a similar thing even while tobacco is still in the field.
Early topping of tobacco is known to help control budworms and reduce the
need for insect applications just before harvest.
Early topping reduces the attractiveness of tobacco plants to budworm moths
looking for a place to lay their eggs, and removes many larvae already present.
By reducing the need for pesticides, early topping increases worker safety
and protects beneficial insects and the environment in general. Also, potential
residues on the cured leaf are reduced.
Tobacco budworms do most of their damage to tobacco before flowering occurs.
But tobacco budworm moths prefer buttons and flowers to leaves as sites to
I
deposit eggs, and the moths are strongly inclined to lay eggs after the buttons
appear.
Eggs laid by the moths hatch into tiny larvae in about three days. If
topping is done early, many eggs and recently hatched larvae are thrown to the
ground with the tops. Research shows that the survival rate of these eggs and
larvae is practically nil.
Most growers could top their tobacco earlier than they do and get this
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important job completed before harvest begins. And when topping is done in the
-2-
button stage, the stems are easter to break than later when the seedhead is more
mature. If topping is done with a machine it is suggested to run the topping
machine over the field several times.
Tops in tobacco tend to suppress sucker growth. down the sta 1k, however. So
when tops are removed, suckers must be controlled, or rapid and profuse sucker
growth is likely to occur. Sucker growth limits development of upper leaves,
which are by far the most profitable ones on the plant. Also, suckers provide
food for young budworms and hornworms in addition to supplying a preferred site
for hornworm egg laying.
Contact sucker control agents that have come into widespread use during the
last 10 years are the answer to controlling early sucker growth. These chemicals
hold down sucker development until a systemic acting chemical is applied. The
contact solution does not interfere with development o".: '.1arvestable leaves or
leave objectionable chemical residues.
Most growers using contact sucker control agents are not applying them early
enough or in solutions that are strong enough to kill both of the suckers in the
leaf axils contacted.
Contact solutions should be applied just prior to topping when the tobacco is
in the button stage. Tops tend to intercept spray patterns and increase the amount
of rundown into the leaf axils. This is parttcularly needed to increase the
degree of sucker control in upper leaf axils. Plants should be topped as soon as
possible after spraying the contact sucker control agent.
Here is a list of reasons why you should top early:
- Yields are increased 20 to 25 pounds per acre per day for each day plants
are topped in the button stage compared to later topping. There is some,
but much smaller, yield increase by topping before the button stage.
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Southeast Farm Press
May 18, 1983
Growers are more concerned about controlling production costs in this crop
than in previous years. One of the best ways to control production costs is by
producing a high yield of tobacco that buyers find has high useability.
Many factors influence yield but one of the major ones is your topping and
sucker control program. When you make decisions about topping and suckering most of
your yield is made. However, too many people overlook the opportunity to greatly
increase yield and value at this stage of production. They should not because
the economics of an early toppfog and good sucker control program are fantastic
not to mention the numerous other advantages.
Early topping and a good sucker control program make it possible for you
to get some extra pounds at a relatively low cost. The table below shows a
137-pound-per-acre advantage for topping in the button stage compared to topping
a week later in the early flower stage. Tobacco in the on-farm tests was topped
in the button stage, treated with two applications of a contact chemical, and
then treated again with a MH-containing product about a week later. Plants in
the other treatment were topped in the early flower stage and treated only with
a contact-local-systemic sucker control product.
Here is how much you might expect net profits to increase using a sug-
gested topping and sucker control program. Figure the increase (137 pounds per
acre) in yield sells for $1.90 per pound or $260 extra per acre. This is gross
return from which some costs should be subtracted. However, you will be sur-
prised at the low costs involved because many of them are already spent on the crop
regardless of yield.
The costs of the sucker control treatments are considered to be the same.
Therefore, the only extra costs associated with the extra yield are for curing
fuel, marketing to include the 7¢ per pound assessment costs, and the value of
the quota.
Curing @12¢/lb X 137 lbs $ 16.44
Selling@ 12¢/lb X 137 lbs 16.44
Value quota @60¢/lb X 137 lbs 82.20
TOTAL INCREASED COSTS $115 .08
I
Some costs are actually reduced. It takes only about half the labor for \ -
"cleaning up 11 and topping at the button stage as compared with doing this job
later in the early flower stage. And insecticide costs may be lowered because
certain insect populations are lowered more by early topping than performing
this practice later.
To compute the net profits per acre, subtract the total costs ($115.08}
from the gross return ($260.00) and you have $144.92. Divide this by your
anticipated yield and you will have the net increase per pound of tobacco.
If your yields are 2354 pounds per acre, divide them into $144.92 and you
will see net returns are increased 6.2¢ per pound.
A frequently asked question is, "Aren't harvesting costs increased for
the extra (137 pounds per acre) yield?" The answer is no, because no additional
1eaves are harvested to obtain the extra yield. The extra weight comes from
-3-
an increase in size and weight of the leaves. Harvest costs are directly re-
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lated to the nurrber of leaves handled.
A contact-type sucker control solution should be applied at 4 percent con-
centration just before plants are topped in the button stage. A second application
of a contact at 5 percent concentration should be made 3 to 5 days after the
first application. Then apply a systemic acting chemical.
The use of contact solutions provide sucker control during the period when
the numerous advantages from early topping can be obtained and to allow time
for sufficient upper leaf development before a systemic acting chemical should
be applied.
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Southeast Farm Press
May 11, 1983
After tobacco plants reach the button stage, potential yield is reduced
20 to 25 pounds per acre per day for each day the seed producing floral part
remains on the plant. And, the body of the tobacco is reduced. The best
market outlook in 1983 is for good, medium-bodied mature leaf. Tobacco is grown
for the leaves, not seed; the~efore, top your tobacco early to increase
chances for leaf growth. Topping followed by good sucker control decreases
the opportunity for the plant to use plant resources for top growth aimed at
seed production .
.Plants go through two stages of development. One is the vegetable stage
and the second is the reproductive or seed producing stage.
When plants are in the reproductive stage most of their resources are
directed into the flower portion of the plant. When plants are topped, the
reproductive phase is temporarily stopped and the energy of the plant redirected to
foliage production, either leaf or sucker growth.
The development of a tobacco plant at a given time is directed primarily
to either vegetative or reproductive growth but not equally to both at the same
time.
The growth emphasis of tobacco plants can be kept on leaf development by
early topping and good sucker control practices.
Early topping should be practiced under all growth conditions. Although
early topping is important at all times, it is more important to top plants
early under adverse growing conditions. For example, plants that reach the
button stage in dry weather should be topped immediately to shift the available
plant resources to the leaves.
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Some growers hesitate to top plants in dry weather because of their con- (
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cern about a shortage of leaves for future growth. But leaf number at this stage
has already been determined, and topping will not affect the number of leaves
the plant will have.
Some growers do not top in dry weather because they fear the possible effects
of loss of water from where the stem is broken for a short time until the area
heals over. This quantity of water loss is relatively small compared to the
amount of water and other plant resources used 'and lost in flower development.
Plants that flower prematurely may be cut back or topped. Unless more than
10 percent of the plants have premature flowered, usually the best practice is
to do nothing. If premature flowering plants are topped, a vigorously growing
sucker should be turned out so additional leaves can form. Prematurely flowered
plants should be topped low enough so the upper remaining leaf will get large
enough to harvest. This may mean cutting the plant off fairly close to the
ground.
Care should be taken to prevent the spread of mosaic when working with pre-
mature flowered plants. Avoid the use of tobacco products and use the milk
treatment during the operation.
Plants that have a restricted root system because of wet soils should be
topped as soon as flowering begins and topped with fewer than the normal number
of leaves. Topping stimulates root development and will help plants recover
from this adverse situation as soils dry out.
Plants that are growing with a deficient nitrogen supply should be topped
as soon as flowering commences. This will promote the use of available nitrogen
for leaf development instead of top growth.
Topping and good sucker control increase body and nicotine accumulation.
Under present market conditions, good-bodied u.s~grown tobaccos are in strong (
-3-
demand. Much of this demand is related to the prices of our tobaccos and the use
of U.S. tobaccos with lower price tobaccos that have less flavor and aroma.
Yield and value data collected in five on-farm tests in 1982 show a yield
increase of 137 pounds per acre for topping in the button stage compared to
topping one week later in the early flower stage. Such a yield increase is
largely a bonus for net profits because the only added costs for this 137 pounds
of tobacco are: curing, marketing, and value of the quota.
Many growers plan to top their tobacco this year several leaves lower than
in previous years to increase the chances for producing good bodied tobacco.
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lj Southeast Farm Press
J ,/ ..<. ;/
I J~JRei2, 1983
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HOLD DOWN MH RESIDUES IN 1983 j '. • ' (. ·"?
W. K. Collins
11fv
MH residues on the last two tobacco crops were lower than in 1980. This
is good news because important foreign buyers have often expressed concern
about MH residues of our cured leaf.
According to ASCS findings the average MH residue was 98 ppm. This is
still higher than the 80 ppm 1imit cigarette manufacturers in Hest Germany
have agreed not to exceed in their products.
MH is not permitted to be used for sucker control in some countries
such as Brazil, Zimbabwe (Rhodesia), and Canada. These are important competi-
tors in domestic and inte.rnational markets.
Two new sucker control products, Prime+ and Bud Nip, provide growers
alternatives to the use or excess use of MH. These products do not contain MH.
\. -
All MH labels now prohibit the use of more than one application of MH at
the suggested rate unless a wash off occurs within 6 hours after application.
Therefore, multiple applications of MH is unlawful in most cases.
Suckers can be controlled with the aid of MH as prescribed on new MH labels.
However, to do this nitrogen fertility and the degree of sucker kill obtained
with contact-type sutker control products will have to receive more attention
than in the past.
The following seven-step program is suggested to obtain acceptable sucker
control and cured leaf with acceptable MH residues.
- Apply 50 to 80 pounds of nitrogen per acre plus adjustments for leaching.
Excess nitrogen stimulates excess sucker growth, delays maturity, re-
duces curability, and market price.
- Apply a contact-type sucker control chemical at 4% concentration when
about 50% of the plants reach the button stage.
-2-
/
- Top plants ready for topping. \
Improved sucker control with the contact-type sucker control products will
be essential for many growers if the suggested program works satisfactorily. An
important factor to obtaining better control with contact solutions is to mix
the product with water so that the solution is at least 4% strength. These products
should be mixed at the rate of 2.0 gallons of chemical in 48 gallons of water
to make a 4% solution. Some growers are increasing the strength of their contact
(
solutions by mixing more than 2.0 gallons of the product with 48 gallons of \
water, especially for the second application of the contact solution. The reason
for the emphasis on the proper strength of the contact solution is that weak
solutions often only kill one of the two tiny suckers in each leaf axil. Hhen
thi.s occurs, the sucker growth is only temporarily suppressed. Later this sucker
growth becomes vigorous and encourages the misuse of MH.
The application technique with contact solutions also needs to be improved
on many farms. Operating the sprayer through the field too fast is a co111110n
mistake. To obtain good results the sprayer should be operated about 2~ mph
so that 50 gallons per acre of the solution are applied. A triple-nozzle
arrangement should be used with 20 psi pressure about 12 inches directly above
the button. The objective is to apply enough solution in the top of the plant
so there is sufficient rundown to kill two sucker buds in as many leaf axils as possible
-3-
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Southeast Farm Press
June 8, 1983
Jt '"' '·
-,)A. ;/ ft« .• _ t
The mix rate of contact product to the water is extremely critical in re-
lation to the degree of sucker control obtained with contact solutions. The
objectiv.e is to make the solution strong enough to kill both suckers in each
leaf axil and not cause more leaf injury than is acceptable. Some chemical
topping and injury to the upper several leaves is considered acceptable.
A standard dilution rate for the first application of contact solution
is to make a 4 percent strength solution. This is done by mixing at the rate
of 2 gallons of contact sucker control product with 48 gallons of water.
Solutions for second applications should be stronger such as a 5% strength.
If the two gallons of product are mixed with 65 gallons of water, the
solution is 3% strength and is too weak to kill the secondary suckers. On the
other hand, if the 2 gallons of product are mixed with, for example 35 gallons of
water, the strength is nearly 6% and so strong unacceptable leaf injury may re-
sult. About 50 gallons of solution per acre should be applied to have enough
solution to rundown the entire stalk.
A good understanding of how contacts work will help you understand why the
mix rate may vary and yet achieve the objective of good sucker control and not
too much leaf injury.
Contact sucker control solutions kill suckers by evaporating the water from
the small suckers faster than the plant can replace the water. The suckers are
dried out until they are killed. The smaller and the more tender the sucker,
the less concentrated the solution has to be to obtain the desired kill. How-
ever, as the dilution or strength of the solution drops below the suggested 4%,
I
( chances are reduced of killing the embedded secondary sucker. This sucker is
located behind the first sucker.
-2-
the contact solution is strong, it will dry up the base of the first sucker and
wound the leaf axil enough to kill many of the secondary suckers.
Weak contact solutions, those that are less than 4%, often visually do
an acceptable job; however) experience has shown the secondary suckers grow
rapidly and become too large for the second application of the contact to pro-
vide control. Then the sucker growth on vigorous growing tobacco cannot be
controlled with the labelled rates of systemic acting chemicals such as MH.
Because contacts kill suckers by a drying action, certain weather con-
ditions such as a bright warm day favor increasing the degree of sucker control
obtained with a given solution. Contact solutions sprayed on cool days or cloudy
days are considerably less effective than those applied on bright warm days. This
is one reason the mix rate of contact product to water should be adjusted as
weather conditions may vary.
The mix of product to water should also vary according to the tenderness of
the tobacco. Less than a 4% solution may provide suitable sucker control on the
first application on a very young, tender crop. Most second applications which
should be applied 3 to 5 d~ys after the first application and all third appli-
cations (3 to 5 days after the second application) should be applied at 5% strength.
This is 2.5 gallons of product mixed with 47.5 gallons of water. The 5% strength
is suggested because the plant is •.1sually more developed and leaf tissue is
thicker and able to withstand the increase of concentration. Also sucker growth
is likely to be less tender than at the time of the first application.
A rule of thumb to use is to apply a contact solution that chemically tops
5 to 10% of the small, late plants in a field. If no plants are chemically
. I
topped during the first application, the solution is too weak to provide maximum
sucker controli.
-3-
Chemically topped plants are usually late less vigorous plants. The
chemical topping maximizes the chances of these plants to produce leaves that
have an acceptable level of body rather than to be extremely thin and chaffy.
Some growers apply weak contact solutions such as 1.0 gallon of contact in
49 gallons of water •. About the same degree of contact sucker control is ob-
tained as might be expected with application of one-half the rate of MH. The
sucker control with both of these comparisons appear acceptable for a while,
then there is sucker growth.
There is considerable evidence that late sucker growth is related to the
use of excess nitrogen fertilizer and use of weak contact solutions. The use
of contact solutions at the correct strengths can be expected to greatly in-
crease the up-front sucker control and make it possible for the labelled rate
of systemic acting products such as MH to provide full season control even
where excess nitrogen was used.
The use of strong contact solutions increases the chance of leaf drop;
however, this is rarely a problem unless excess nitrogen has been applied.
Some growers apply their contact solutions with hand-operated applicators.
This method of application greatly increases the degree of contact sucker con-
trol, especially in the Piedmont where it is difficult to correctly apply con-
tacts with tractor sprayers .. One hand application of a contact solution is
usually adequate before a systemic acting product is applied.
Tops should be in the plants when the first application of a contact chemi-
cal is applied. The top will intercept the spray pattern and increase the
chances of solution rundown and kill of tiny suckers.
(
HOW TO LOWER MH RESIDUES
W. K. Co11 ins
tobacco without using MH. As the MH residue levels increase, our flue-cured tobacco 1·
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becomes less competitive in world markets because foreign buyers have the alternative
of buying tobacc?s without residues from other countries. The U.S. shar.e of
world production of flue-cured tobacco has dropped from 41 percent in the late
1950 1 s to 19 percent in 1979. Some of this may be attributed to increased MH
residues; however, it must not be .overlooked that the quality difference between
U.S. flue-cured tobacco and certain fore_i gn flue-cured tobaccos has decreased.
In addition, new manufacturing technology available within the international to-
bacco industry makes it possible to make products that are acceptable to consumers
wi.th a wider range of tobacco than only a few years ago.
Contact-type sucker control chemicals alter the water proofing layers of the
sucker tissues to a point where the moisture in the tissues escapes. This loss of
-4-
moisture kills the tender· sucker tissue. Mature leaf tissue is not damaged because
the water proofing layers on the upper leaf surfaces are thicker and consequently
are not completely altered. However, high concentrations of the contact can destroy
leaf tissue, especially it is is very tender like when it has been grown with ex~
.cessive nitrogen.
The use of less than the suggested ratio of chemical to water often kills or
damages no more than one of the two sucker buds at the leaf axil. The degree of
sucker control is related to tendern.ess of the plant a~d. growth conditions. If
.growth is tender, the sucker control will be ll)UCh higher tha,n if growing conditions
are unfavorable such as under dro_ught conditions. Grower experience tends to verify
this observation. Some growers are applying contact solutions that contain as much
as 5 percent of the formulated products on less tender crops.
There is concern among growers about leaf drop with strong contact solutions.
-This is not likely to be a problem unless t~e crop has an excessive amount of avail-
able nit~ogen and the season is unusually wet for several days after application.
)f l~eaf drop occurs it most 1ikely will be from the lower part of the stalk where
there is.high humidity due to lack of sunlight and air movement. These factors
encour~ge survival and spread of soft rot bacteria which enters the wounds in the
leaf axils.
Good equipment and timely applications are musts for good sucker control.
It is essential to have properly adjusted, accurately calibrated equipment with
adequate .agitation to obtain satisfactory sucker control without injurying the
leaves. Many growers would increase the degree of contact sucker control by operating
:thefr sprayers at 2 to 2~ mph? especially where application conditions are less .
-o-
!
than desirable. Futhennore, apply the materials at the correct st.age of plant de-
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velopment, button, for contact-type materials and about a week later for those that
control by systemic action, fpr best results. Under nonnal growing conditions,
· with the suggested rate of nitrogen applied, the following topping and sucker con-
trol program has consistently given acceptable sucker control where materials were
properly applied.
1) Apply a contact sucker control chemical at the proper concentration be-
fore topping when about 50 percent of the plants reach the button stage.
To obtain the proper concentration, mix tw~ gallons ·of product in 48
gallons of water to make a ~ percent solution. Concentrations lower than
4 percent .may provide little, if any, control of secondary suckers. and
make it difficult for MH to provide full-season sucker control. Contact
solutions with concentrations higher than su.ggested may cause some leaf
injury; however, chemical topping of about 5 percent of the plants indicates
the timi.ng of. the application and concentration of solution are correct.
The chemically topped plants are usually late-develop1nQ' plants. Topping
these plants early and below thenonnal number of leaves reduces the amount
of thin, chaffy, cured leaf produced.
Toppi.ng height is also very important. Plants should be topped at
about 19 harvestable leaves in view of the demand for good-bodied leaves.
Having to delay the MH application to allow for higher topping increases
the likelihood of sucker problems. The proper use of a contact-type
sucker control chemical makes it possible to obtain the numerous benefits
of early topping before plants develop enough for MH to be applied without
reducing leaf desirability. Also early applied MH often does not provide
full-season sucker control.
2) Apply a second· application of a contact sucker control solution 3 to 5
(,.·
days after the first application in fields that have irregular growth
and floweri_ng. Later applications of contact-type solutions provide re-
duced control because the few suckers missed with the first contact
spr~ing grow extremely fast and become too large for a contact to kill.
Plants that were not topped after the first contact was applied should be
topped followi_ng the second application.
3) Apply a product containing only MH or apply FST-7 (contains both MH and
a contact) about 7 days after the last contact application preferably in
the morning about two do_ys after a rain or irrigation. For maximum.effect,
apply MH in the forenoon to- plants ·having good- soil moisture.
Only the recorrunended rate of MH should be applied to help avoid problems asso-
ciated with high MH residu~s. Labels on all MH products now prohibit more than
one application unless a wash--off occurs the first 6 to 12 hours after application.
Tests have shoWn that as the rate· of applied MH is increased, the residue on the
cured leaf can be expected to increase~ One application of MH at the recommended
rate can be expected to leave a MH residue of about 80 parts per million. FST-7,
a MH-containing product, when applied at the s_u_ggested rate, provides 11 percent
less MH than the recommended rate of other MH-containing products; consequently,
its use would be expected to reduce MH residues somewhat, but it may also affect
control from the reduced MH. appl i.ed if there is excess nitrogen.
Use of problems containi_ng MH just prior to harvest must be avoided so that
chemical residues will be at the mi.nimum. MH residues are related to the number
of dczys between sprayi_ng and harvest. Labels on MH products require at least a
7-day waiting period between MH application and harvest. The lo.nger the time
between MH application and harvest, the lower th.e MH residues. Some of the MH
sprayed on the plants stays on the surface of the leaves. This surface MH can
-7-
HARVEST TIME
Days After Application ID!!! % Reduction
0 140 0
1 115 18
2 107. -24
. 4 2/ 48 66
reduction of 20 to 25 pounds of cured leaf per acre per day. There is evidence
this principle of increased yield with early topping applies to the pre-button
stage.
Third, the body of the remaining leaves on chemically topped plants will
increase compared to topping them later by hand or mechanically. Usually this
will increa.se the desirability of these leaves as compared to thin-bodied
chaffy leaves normally produced by late developing plants which are most likely
to be chemically topped.
The market outlook ·far the 1983 season indicates a strong preference for
good-bodied tobacco. Early topping will contribute to this. Delayed topping
is known to be related to the production of l1i ght-bodied, thin tobacco. Buyers
can purchase light-bodied leaf which lacks flavor and aroma from other markets at
considerably lower prices than available in the U.S.
Floral parts on tobacco plants should be looked at as pests. They rob the
plant of its resources and reduce yield and leaf useability. Tops in tobacco
plants are the major pests in tobacco fields in North Carolina. They are on
every plant in every field without exception. Therefore, time of topping is
a ~anagement decision required every year. However, obtaining some chemical
topping .when the first contact spray is applied should be an objective each
season.
There are several other benefits of topping in the button stage. Topping
is completed before harvest begins. This helps spread the workload away from
the peak harvest period. The chance of plants being blown over in a windstorm
is reduced when plants are topped. The populations of certain insects are
lowered because eggs and larvae survival is nil on floral parts removed from the
plants. The moths of certain harmful insects are more strongly attracted to lay
eggs on the floral parts of the plant than on older leaf tissue. If these eggs
-3-
and larva can be effectively destroyed when topping, then the need, costs and
possible hazards of chemical control are reduced.
Early topping is always important; especially when the plants grow under
adverse conditions. Plants that reach the button stage in dry weather should
be topped immediately to shift the available plant resources to the leaves.
Chemical·Topping
l:l:Y W:K. ~6llins. ?11ort1iCai-0~F.:~tensi<!nqjoba&!l.S(iecialist · . . · ·.
It is desirable to chem1cal· ·· cro~s' ~$ ·jttegillar .growth tr!l~ion) ()f the contac.t spiay Fiist, usually an extremely
ly top 5 percent to 10 plli:- anCf".floW.ering. was i:On'eetfiir thesituation. high degrP.e of sucker kill is
cent of the plants with th~ W!t,en sq!l\e of the pJilnts · · Chemic8lly topped plants obtained when chemical top-
first application of a contact areCJ!emlcal)y toPped_by'the . •!'PPear·· to. bl! injured; pmg · is observed. Both
typl! suck'!? control solutiQJ'. conta~t. solution, thi.~. irr· liQ:weyl!r, .t!>arl>. !U'e s9v"1'al primary and secondary
Chemical 1:9pping 1>f some. mcaMS. the ~e :o.f '!pI?lica· iltlliQrtant benefits o.btaine<i sucker buds in contacted
plants sh<iuld ~-expeCted in tion ·Qiid !l~h .f¢on:cen: .ft'~ltl. chemlcii.l topping. leaf axils are killed in most
· of the leaf axils on the
well as tru•
.............-"'!'................._. . ._."!"'......._.......,...,. .- - - - - - - - - - - - - - - - - - - - - - - - - - - - - -.... • chemicallytoppedplantaas
othl!r 'plants in
C. o·.· ···u···N···.........LJIBM'. .· ..
the field.
Second, restilts from on-
.· 1FYOUDVl1fer·
farm tests show plants top-
·ped In the pre-buttoo stage
Yield more than if topped
any time law. There is an
!l.P,preclable amount of tissue
'l>urned out in the button
. area. when plants are
~y topped.· The re-
~ le&f tissue con-
MOff!. th!ln 260,QOO ~ucker$per acre .tliluea to develop and pro-
.are .wait;ng _to steaJ.ypi,ir.f1t!rd~~p~fi~ .~ ~ bodied !eat. This
pon!'"tGive.$.1,1ckers•At;nane.~.t is the type 9f leaf expected
·to ha\ie highest demand at
FAIR"-85® ·contr()}s tf)em• effecti.v.ely ·the·warehouee.
and econofflicaiftt. · ·· Leaf tissue aild .the stem
of the plant that is topped
out l>Y hand .or by a topping
maChlne. is a sure loss or
:reduction from maximum
-Y,ield. Early cheinical topp-
ing Sl:Qps . the plant from
: cll:anneling plant rssources
"·•mto;Certai.n leaf tissue.and
. .hciril parts thiit are not sav·
.e<kfOr ·market but rather
discarded on the ground.
Thi~· plant material. is a real
and significant loss.
Research shows that after
· plait.ts reach the button
~; yiel\I potential of un·
tQppiid plants is ~educed by
1. Pl!?OODt per acre per day.
For· many growere this is a
.**Kill11.a1.1¢keiswithio a howr
Doeiln't:StQp cell:division
j. P~rtic1:1fariY' hefpflil on
reduction Of 20 to 25 pounds
of curj!d leaf psr acre per
· day. There is eyidence this
P!inciple of increased yield
with early toppmg applies to
· • im'!iv!ii;i .c;~op,s . the preb11ttllll stage.
*C>anbe,.ar:>p!!ed earlyrapid
syckers·star;'t their
before.
·
Third. the biidy of the re-
maining leaves on chemical·
1y topped plants will in-
gto>Jvth, · · crease. compared to tqppmg
theiii · later by hand or
Take thatfir.stlm,p()rtant ~fflk;t.il~tqs;[.nolf()~tqiit
~cally. Usually this
· will increase the desirability
on tl!/e.•W!Jtehot1$ello.Oc. Apply .fAIR~$5r · of these leaves as compared
tO thin bodied chaffy leavss
the proven i:ontr1.r:t~t1t;/fer~~nflto/:ptQ(li;fet, •. · norm8lly produced by lat.e
developing Plants which are
·. , at the bu'ttQQ·~tl!J;§e.
- .
·· · '·· · mostlikely to be chemically
top~.
,' ; " -
/
'
Mayl985 MODEml 'f()BAOOQ GROWER Page5
the nomial lltligh~ r11~,et 01! most farms. plants ts~ solution Jll!IYs an impor-
t;Julli l#gher ~ ,norma,J. shotil!f be t:Qpped when they tsnt !'Qle in the degree of
Thin l11avee; :have" ·OOOn, ha~ 18 t:O 20 harve8table chllDlical topping. Weak
ass<>ciiite'd . with ' hc'ess leaves. Plants usually ha~e solutions are unlikely ,to pro-
nitrQg~. Bec;a.~ of the $JX· thiS many . harve.stable Vide any chemical topping•
tra num~ of..le,B.~·.o!> high .lea~s in the . prebu~ton A 4 percent solution (
· t:Qppid, · plant$ 'tile ·•Iliives stage: . ·.From a practical prepared by mlxlng at the
?iiAY. bii ~ ~ .the waY. lo Ylemioint: ChemiCal tOppmg rate of two gallons of con-
.tit~ t;op 11f'the 11lan.h When js t!\~ onl:Y way tqpping can f:!tct s~ker cilntrol product
\
plagts, thet'.&1'8 Jiv'er fe~ .be 'aooorhplished . at· .this with 48 gallons of water nor-
:with nitrQgei\ : l!ril tQpped st,'!.ge .of · 11lant . growth. .mally is strong enough. Be
'" nromally, tlte leave& ·Wilf lie Clielllic!i! topping: max, llUre to operate the ' pump
thin at fil'at. ~use of rapid . imiztiii the· many · .ben<lfits .prilsSU?e at no more .than 20
gi:ojyj;li ' t!!eY .ha,,.e asa<iclated' wilh early topp- psi an<\ 9.P&r&te the spray
r.wr ex iin~.r .Will ·mg. · · lloQuf ,about one foot. abrive
'the s~~gt;h />f the· con- thebutt;On.
.. --· >4---·-·
-·~-·-·-----.-·~,.~
(
\
1'$ge 12 MODERN TOBACCO GROWER March 1988
~~%~i~J~~]~· ~::::~:::~~u:-
. p;; ft W:il! uSJially tion .feqliires many manage.
Ear). . . encourp_ges. take iib:Q)J.t .thri>e ?111~ as.: 111~t.decisions. Toppinge&r,
thU. ii't~; e:•n root ·1!1'.'Qvitli long, Ip tpp ·after ~e full . ly n:u\y bl!. one of th.e. most
Ridomil·cont(ols blue mold and bla'* · t,o. OC:cur..eii~lier;. q)his aili>ws ' flpw,;r:.:'!~g "'" ·coi)lpa~ t:<> profi~blll . lfecjsions that a
Shani< ihyour tob!lOO). But forRidomil to
do·lts bestwork;lt:shoutd be applied to· the; plaiit'·tl). in:od\ie n'io~e tlie l>\ltton }>~ ·'!B"i'Y flower p;r.Qwer can make.
the soil before 1ransplanting. .. ·. .
Ridomil destroys diseases present in !he
soil. Then iUsJiibS,Orbed by the. roots and
moved systemically throughput the plant
to protectyourfobaccb as it grows. .
Forthe b~t twq-way action against blue
mold and black shank. follow your label
·Trallsplant
directions-use Rh;lomil in the soil:
. Aidomil' -O!Ci>ac:Geigyk>rmel-~.
Performance
CfelliNAi~.·.··
. •. ·.~EMICAlS, '.NC.
Klnoton North C8roll1111 --wi.i.i-, North ~lne
Tobacco growers wart not perform well in the field
plants .to re'siime. rapid even wider .favorable grow-
growth quickly . after .ing conditions. However,
· tt:ai:t5planting. Miitlinizati.(>n even· top quality ~ ·
Phone't1MU·1181 · Pl>oM91•7M-4117 · <if transpl~f stress l:an h!llP \Viii perform poorly in the·
~, '40rth carolll'lll : yoling tobacco plants .avoid field if certain production
Pltone tlt-944-7878 . msOO:t and disease problems practices . ere not followed
ant\a'ttliininaitimumgrowth before. and after
11n'i:l .yield; The first srep In transplapting. · .
Rl'.t.ti'li\'.plants off to a ·qujck, First, if a disease is pre-
. J\ea'lth;Y .start in: the field is :sent iii a specific field, •.elect
. toiprjjduce healtl)y;»viRQ•o.us a variety (if available} that.
':see'd.liii~ in the plant beQ, has .. resistance to . that
Poor qu11lity seedlings Will · .. Continued on page 19
(
\.
March 1988 MODERNT013A.CCO G~Q~ Pagel3
Continued 6om page 12 Growers should also pay field. .water to the plant r 00t zone growth, whereas tobacco set
disease or combination of attention to fertilization ·Minimization. oJ duting:thesiitting·operation. toolatewilloi'tenbeexposed·
diseases. Diseases can rates .. Excessive fertilizer transplant stress. is 11#. irtl;, <\;tleast3QQ gl!ll!ins.ofwater t.o increased .transplant.
r~uce the perf9rmanre_ of. ari!Vor· fert;i!izer plac,ed too pottant· part ·· · · · · ··f!'ll" ·acie is si!ggested for stressffom hot weather. /
the very l:iest transplants, .Clolleto.the•foot.systern can ptrlanspants tan"ti!\".n?gw
Burley gro:wers · l),ave· aeiionsfy ·injure "or kill 1
..·." ...·.·_=...~~ . · . · e · · ~
.,.,,.". •. 9. 6. . .. ..,
. · . · ..
....:'i.·t.!'
. w . ·u)pter.·.,_··.~~.·.Ad
8 Yso
,0 80
•. f,oar Finall.JI', a cul_tivation soon
after transplanting will
(
ayailable a new variety, "TN newly'set tobacco ,plants. stress. can..be . . .. :light lir)gatiQ'n soon after loosen and aeraJ;!L.thi!._!<>il
86," which was released in ~ in burley tobacco thoroughly wetting. the t~planting can further a.11d.--heip-"the toung---...- \
1986 by the UniversiW. o.f fertilization has shown that plant bed. before..i>ullih.g: .~lice• tr'B$plant- stress, transplants resume growth
Tennessee Tobaeco Experi· ma:tiniuin yields will pla!lts. Tl!i.11; pernlit1r •plait~ ei;p)lcially'linder diy. soil con· quickly.
ment Station in Greeneville. generany be obtained by the roots· to· retain ·moist .soil- 'ditfons: · ·· · . Tobacco ·growers . who
TN 86 is the only commer,· applieation of no more than when pulled Pulljld •see~!- · BU:,,ley ·tobaeco in Ten: follow these praetices will in·
cial burley variety with approXimately 150 to 200 ing's should be .~ept '!lllt' o~: neiis~ 9hot!ld: uSila\ly be crease theif chances of get-
resistl)nce to viruses .other pounds 9f:nitrogen per acre. the· ·sun -p-i·io;r' ·, t9• ~r,ansi>lanteli"dUrilig May 1.0 ting plants grOwing quickly.
than tobacco mosaic virus. Ph<>spliate and potash rates transplantll;ig. ! Tpeij.... i:i1iuui·: t\>.,J)ihe.- .);. 'rol!acco set ;too aftci' transplanting and en-:
TN 86 has high resistance. to should, be applied acc<irding s\ire · th~ ttansl>latiter. 8uP- . el!l'lY .w;u u!riililly/enco~ntm' .Sl!re ·mamnuni ·perforinance
tob!lcco veiri mottling virus, to soil test results for ~ch Jill.es,-a ~ent.~~f.9f : c&\1_. f~tliei\, ..~lilch ·~lows of.transpil!nted seedlings.
inedium.r\!istl¢ce to tQbacco .........,........----..--.,_..-....,..;..-...,...,....,_...,._ _ _..,.._""'"_""""...._ _~--------.
~~~
medium resistance to black
shank, !Jigh resistance to.
tOUNt"TREllFVOU DIRE!
·
.. . · · .. ·
..
·: .- . . • :: '!.
· · ·
·. · ·cc. · .
.I. .. I~
ly season insects s\lch .as
wireworms, cutworms and
flea beetles. A preplant,
systemic fungicide can help
control l!lU:e mold and black . Throughout Tobacco Growing Areas
·shank disease ·problems. · Aval.· ... ·e
..Fro.·m··· Lea.di·."·g. D..e.. al•...e.·rs
Preplant herbicides shquld
be. applied at the ~roper
ra~ and be properly incor·
porated into the .soil to con-
a,ir proiduct~, inc:.
trol. weeds effectively
without injuring the newly·
set_ tobacco plants.·
North Carolina State University (NCSU)
(
\.
Summary of Sucker Control Trials on B~rley Tobacco with N-Tac Sucker Control
Report Submitted to
British Americ~n Tobacco Company
By
Dr. Bob Pearc·e
University of Kentucky
Purpose: To test the efficacy of an organic contact sucker control (N-TAC) for controlling sucker
·growth in burley tobacco. Second was to determine the best use patterns including rates and
application timing for the -use of N-TAC for burley tobacco sucker control.
Methods: Study was conducted over two years with two locations each year. Study locations
each year were Splndeltop Research Farm near Lexington, KY and the Woodford County Animal
Research Center near Versailles, KY. Both locations are research farms that are part of the
Kentucky Agricultural Experiment Station. Burley tobacco (variety KT 210LCj was grown
following recommended practices as described in the Kentucky and Tennessee Tobacco
P.roduction Guide (UK Cooperative Extension Publication ID-160). Sucker Control treatments
were initiated immediately after topping. Treatments for each .season are shown in tables 1
and 2 and there were 4 replications of each treatment. Shortly before harvest sucker control
was evalua~ed by removing, counting and weighing all the suckers on 10 plants per plot. Pl.ots
were harvested by stalk cutting and the tobacco was allowed to cure in a standard burley cu.ring
. barn. After curing the leaves were removed and separ~ted by stalk position and weighed to
estimate leaf yiel~ for each plot. All .data were analyzed. with the GLM proced.ure in SAS 9.3
with means separated at the p=0.1 level. Dates· of important field operations are shown in
table 3.
Results: Since treatments were different between the two years of the test each year's data
were analyzed and are presented separately. In 2013 follow-up applications of contact sucker
control were made based on the number of days between applications as shown in table 1. In
2014 follow-up applications were made based on observati~ns of leaf axils. At l~ast ten plants
were inspected at roughly two day intervals; when the majority of the plants had signs of lateral
bud growth the next application was triggered. The statistical analysis indicated there were no
significant location x treat~ent interactions so the data are presented below averaged across
locations.
. .
For 2013 all treatments provid~d good sucker control (table 4). Only the untreated check was
significantly different. There were a just a lim,ted number of s·ucker escapes in some
treatments. The untreated check had a significantly lower leaf yield than ·all other treatments.
( There were some significant difference
- among
. the treatments for yield,. but
. most treatments
were no different than the highest yielding treatment. One treatment for which a lower yield
was recorded was the highest rate ofN-TAC (15% solution'). At one lo.c.ation in 2013 significant
leaf drop of lower leaves was observed for that treatment. Other treatmehts that were
significantly lower than the highest yielding treatments included the two flumetralln only
treatments. It is possible that the flumettralin resulted in some stunfing of the smaller upper
leaves, thought this effect was not measured in this study.
For 2014 again all the treatments provided sucker control that was significantly better than the
check (table 5). Though there was some. variability _among treatments in 2014, the majority of
treatments were at least as good as the best treatment. Evaluations of the need for follow-up
treatments revealed that the time between applications c<?uld be stretched beyond the
recommended 5 to 7 days for contact sucker control. There also appeared to be a rate effect
with the. time between applications being longer when higher concentrations of the contact
material was used_ (data not shown). The yields were not significantly .different from the
highest yield in the test ~cept for the check plot and treatment receiving 3 appJications of Fair
85~ No leaf drop w~s observed in ~014 to explain the yield loss for that treatment.
Concl.usions: Based on these trials N-Tac appears to be a viable method of sucker control for
burley tobacco. Burley tobacco tolerated higher concentrations of the contact material than
was previously reported.· Rates up to 7% did not result In leaf drop. At the highest rates of 10
to 15% some leaf drop and possible loss of yield was observed. The time between applications ,,r···· '\/_.__
could be stretched out to potentially reduce the total number of applications needed betWeen ·
topping and harvest. In many cases two applications of contact provided sucker control and
\
yields.that were just as good as three applications, thought lt would be recommended that
growers keep a close watch to determine if sucker regrowth was occurrjng. From these stt1dies
a recommended program for organic sucker control would be N-'fAC at 5 to 7% solution applied
immediately after topping and at Intervals of 7 to lO days or when sucker regrowth is visible in
leaf axiis.
Table 1. Sucker control treatments applied to burley tobacco during the 2013.season
.
Ta bf e 2 Suc ker Cont ro I trea t men t s app,r1edt. o b.urIey t o b acco d unng
. th e 2014 season
TRT .~ Application Notes
·r,
1 .\1, Topped, but no chemical sucker control .. Used to calculate % sucker control
2 ··!:;' Flumetralin 2.SL/ha (lqt per acre) · Single application after topping
3 ,:
,. N-TAC 5%: two applications Applications "as needed"
:; N-TAC 5%: three applications Applications "as needed''
4
5 ·~i, .N-TAC 7%: two applications Applications "as needed''
6 " N-TAC 7%: three applications Applications "as needed}'
7 N-TAC 10%: two applications Applications "as needed".
8 · N-TAC 10%: th.ree appDcations Applications "as needed".
9. N-TAC 12%: two applications Applications "as needed"
10 N-TAC 12%: three applications Applications "as needed"
11 Fair 85 5%: three applications Applications "as needed"
12 Fair 85 7%: three applications Applications "as needed'}
13 Fair 85 10%: three applications Applications "as neeaed"
14 i Gallon MH plus 0.5 Gallon Flumetralin ·· Single application after topping
All treatments were applied by hand with a back-pack pump sprayer using a volume control
nozzle cal.ibrat~d to deliver .18 ml of solution to the top of the plant. ·
"as needed" applications were applied when close inspection of the leaf axil area revealed
I• •
active suckef:.growth. .:
Table 3. Dates of important field operations.
Operation 2013 2014
Spindletop Woodford Spindletop Woodford·
Transplanting May24 fone 21 June 4 June 17
Topping July 26 August 29 . . August 13 August 25
Initial Application July 26 August 29 . August 13. August 26
Sucker Evaluation August 22 Sept 23 Sept 15 Sept 22
Harvest ·August 23 Sept 24 Sept 17 Sept 29
Table 4. Sucker control and yield data for 2013.averaged across locations.
.. #/plant . % "Kg/ha
Topped, but no chemical sucker
6.12 a O.Ob 2678 e .
control
· Flum~tralin 2.5!-fha (lqt per
0.26 be 98.0a 3028d
acte) ;. .
FlµmetralinlOL/ha. (1 Gallon
1;•"
0.04c 99.Sa 3225 bed
. per acre)
N-TAC4%: two applications 0;29 be 98.7a 3061cd
N-TAC4%: three applications 0.08 be 99.4a 3277 abed
N-l}AC 5%: two applications O.OSc 99.9a 3597a
N:..TAC 5%: three applications 0.03c 99.9a 3358 abed
N-TAC 6%: two applications 0.19 be 97.3a 3424abc
N..,TAC 6%: three aoolications O.Oc lOOa 3309 abed
N-TAC 10%: two applications 0.43 b .99.4a . 3370abc
N-TAC 15%: two applications -0.0lc 99.7 a 3224 bed
1 Gallon MH plus 0.5 Gallon
0.0Sc 99.9 a 3340 abed
Flumetralin
LSD p=0.1 0.35 4.0 335
Table 5. Sucker control and yield data for 2014 averaged across locations.
/
·r-- . Interim _x_ Final
2014 Report
to the
From The
For The
. '
LEAD~"ft(S):loren Fisher
...
-=:
::-. .
;"
DEPARTMENT(S}:Departmen.t of ~rop Scfence
REPORT:
1-
-- I
Research was conducted in 2013 and 2014 to evaluate drop-line applications of N-Tac, an organically
approved fatty alcohol tobacco. sucker control material from Fair Products Inc. ·Research was conducted
at the Cunningham Research Station in Kinston, NC and the Oxford Tobacco Research Station in Oxford,
NC both years.
"l
.j
~-
')-/
/
\. ,.--....,
All treatments were applied wlth a drop-line except for in year two where the MH/flumetralin tank mix
was applied as a broadcast spray. The dropline treatments were applied with a nozzle suppJied by BAT
that is commonly.used in Brazil, ~hich delivered approximately 20 ml of solution per plant. The
exception was the flumetralin treatment in 2013 when the 2qt/50 gallon concentration was applied at
30 ml per plant as a comparis9n to a standard US application rate and method. The. first application was
made either just before or just after topping and subsequent applications were made at 5-7 day
inter'Vals for the first three applications. In plots receiving more than three applications of N-tac, the
fourth or fifth application was made 10-14 days after the third or fourth application. The time span
from topping till final harvest ranged from 9-13 weeks across years, and was deperident on rainfall.
In 2013, significant leaf drop was observed with the 15% N-tac concentration at the Kinston location and
to a lesser extent at the Oxford location .. Leaf drop was caused by injury to the leaf axil with the high N-
tac concentration and also resulted in poor sucker control because leaves were not present to catch the
spray solution at the second application timing. Therefore, the 15% concentration Vl{as not evaluated in
2014. Very minor leaf lamina injury was observed either year regardless of application concentra_tion.
Sucker control was evaluated by counting and weighing suckers from 10 representative plants from each
plot.·sucker weights were compared to a control plot whe·re plants were topped, but no sucker control
was performed, either by hand or with chemical methods. The control plot was used to determine
maximum sucker pressure and the comparison allowed calculation of percent sucker control.
Regardless of N-tac conce.ntratfon, sucker control was improved as number of applications lnc~ased. In ·
fact, number of applications had a greater positive impact on sucker control than concentration (Tables
1 and 2). Four or more applications of N-tac gave 95% sucker control when averaged over locations and
N-tac·conce~trations (Table 1), but increasing N-tac concentration did not improve sucker control when
averaged over number of applications (Table 2.) However, it should be noted that higher concentrations
were only evaluated a~ a maximum of two applications when computing these averages over N-tac rates.
Multiple applications at high rates were avoided to prevent leaf drop.
Tables.3-5 show sucker control from each individual treatment. The trend for improving sucker control
with increased number of applications is consistent and there are few differences in sucker control
across N-tac rates with a similar number of applications. Yield was directly related to level of sucker
control.
The environment at the Oxford location In 2014 most represents expected sucker pressure in a normal
production year for flue-cured tobacco in NC. In that environment, the positive effects of3 or more N-
tac applications and the limitations of contact-only sucker co"ntrol programs were observed. In seasons
where there is an extended period from topping to final harvest (more than 9 weeks) and normal rainfall,
(
five C?r more applications of contact will be needed to maximize sucker control. Regardless of ~ucker
,~/
pressure or length of season, no advantage was seen with increasing cont~ct rates above 5%. It Is likely ( \-
that one or two contact applications do not sufficiently control secondary and tertiary suckers in the leaf.
axils. This is likely because those suckers are not developed at the tim.e of contact application and are
difficult to reach with the contact soluti9n. In addition, the 5% solution provided sufficient desiccation
of the sucker and higher rates were not necessary.
Table 1. Sucker Control and Yield ba.sed on total number of Applications, averaged
over N-tac rates.
6 2 2 56
6 3 2 87
7 2 4 59
7 3 6 66
10 2 4 51
10 3 4 59
12 1 2 49
12 2 2 51
15 2 2 72
__/
( \
'. .•---,
Table 5. Sucker Control and Yield Combined Over Two Locations, 2014
Total Sucker
Product Concentration Apps Control Yield
No. % lbs/A
Flumetralin 1qt/32 gal 1 89 3024
N-Tac 5 2 42 2985
N-Tac 5 3 50 3230
N-Tac 7 2 53 2889
N-Tac 7 3 53 2990
N-Tac 10 2 49 2943
N-Tac 10 3 59 3065
N-Tac 12 1 49 2924
N-Tac 12 2 51 3152·
Fair-85 5 3 49 3048
Fair-85 7 3 55 3060
Fair-85 10 3 59 3281
MH and Flu 1 gal/2qts 50 100 3036
gal 1
8/20/14 (BATK-14) ARM 2014.2 Assessment Data Summary Page 1 o1
.North Carolina State Universit
Evaluation of MH, Flumentralin and N-Tac (Contact) In a Drop Lfri~ Application Method
Title No. 2: Loren· Fi.sher Matthew Vann Joe Priest Scott Whitley
Trial ID:BATK-14 Location:Kinston NC Trial2014
' Year:
Protocol JD:BATK-14 Investigator.Joseph A Priest
Project ID: Study Director:Loren Fisher
Sponsor
ContactRoger Black
rop Code
rop Variety
escription
art Rated
ating Date 8/15/14 8/15/14
umber of Decimals ·
rt Treatment Rate
a.Name Rate Unit Pio
1Topped, Not Suckered 101
21
301
41
Mean
Flumentralin (0.25 GP~) (31.7 .
2GPA) 0.3lb ai/a
" ·
/ --
3N-Tac 5% 1.6 GPA (31.7 GPA)
N-Tac 5% 1.6 GPA
. .(31.7
. GPA)
(
\
SN-Tac 10% 3.2 GPA (31.7 GPA)
N-Tac 10% 3.2 GPA (31.7 GPA)
·N-Tac 10% 3.2 GPA (31:7 GPA)
8/20/14 (BATK-14) · ARM 2014.2 Assessment Data Summary Page 2 of 5
------__;,____N_o_rt_·h_C_·a_r_o_li_n_a_S_ta_t_e_·u_n_i_v_e_rs_i__.t L . - __ _ _ _
1
.---
_. . . -J\
( 1·
Evaluation of MH, Flumentralin and N-Tac (Contact) in a Drop Line Application Method
Title No. 2: Lore_n .Fisher Matthew Vann Joe Priest Scott Whitley
. Trial
Trial ID:BATK-14 Location;Kinston, NC Year.2014
Protocol ID:BATK-14 · ... Investigator.Joseph A Priest
Project ID: Study Director:Loren Fisher
· . · . ·· : ·: SponsorRoger Black
·· Contact ·
ropCode
rop Variety
escription
art Rated
ating Date
umber of Decima.ls
rt Treatment · Rate
o. Name . Rate Unit Pio 1 2
9N-Tac 12% 3.85 GPA (31.7 GPA) 23.141b ai/a 10
201
. . ·... 30
40
Mean
10N-Tac 12%.3.85 GPA.(31.7 GPA) 23.141b ai/a 11
N-Tac 12%·3:S5.GP.A(31.( Gf>A) 23.141b ai/a 20
30
. 40
Mean
11Fair85 5% 1.6 GPA (3·1, 7 GPA)' 9.621b ai/a 111
Fair85 5% 1.6 GPA (31.7 GPA) . 9.62lb ai/a 21
Fa!r85 5% 1.6 ~PA (3_1:7 GPA) 9.621b ai/a 31
40
Mean
12Fair 85-7%.2_.25 GPA (31.7 GPA) 13.521b ai/a 11
Fair 85 7% 2.25 GPA (31:7 GPA) 13.521b ai/a 21
Falr 85 7% 2.25 GPA . (31.7 GPA) 13.521b ai/a 30
. . . ·. . 4.11
· · Mean
13Fair85 10% 3.2 GPf\ (31.7 GPA) 19.231b ai/a 11
Fair85 10% 3.2 (3PA..'(31.7 GPA)' 19.231b ai/a 20
Fair8510%·3~2.GPA(31.7.GPA): 19.23lbai/a 30
40
Mean-
14{MH 1.0 GPA~. .. . · 1.51b ai/a 11
Flumentralln 0:5 GPA)· TM 0.61b aila 20
(Overall Spray) gm_G~A) 31
40
Mean
8/20/14 (BATK-14) ARM 2014.2 AOV Means Table Page 3 of
Eval~ation of_MH, Flumentralin and N-Tac (Contact) In a Drop Line Application Method
Title No. 2: Loren F!sher Matthew Vann Joe Priest Scott Whitley
Trial ID:BATK-14 . . · '.: Location:Kinston NC Trlal2014
· · ' Year:
Protocol ID:BATK-14 . . ·investigator.Joseph A Priest
Project ID: · Stuqy Director:Loren Fisher
Sponsor
Contact:Roger Black
.Eval~~tlo~ ·of MH, Flumentraiin and N-Tac (Contact) in a Drop Line Application Method
. Title No. 2: Lqren" Fisher Mattl:Jew Vann Joe Priest Scott Whitley
Trial ID:BATK-.14 :; · :Location:Klnston, NC Trial2014
. . Year:
Protocol IO:BATK-<14 ·. Investigator.Joseph A Priest
Project ID: · .: .. · Study Director.Loren Fisher
. . · · '. SponsorRoger Black
Contact:
rop Code
rop Variety ....
. . .· .
escription
art Rated
ating Date . · ... 8/15/14
umber of Decimals · .
rt Treatment- ·· Rate
o. Name , . Rate Unit 1 2 3 4
14(MH 1.0 GPA~ .. ._ . . ·: · · - 1.51b ai/a O.Oe O.Oe O.Oe 100.0a
Flumentralin..0.5 GPA) TM O.Slb ai/a
Overalls ra · 50 GPA·
SD (P=.05) .· : -..: · . -.:--: :. 2.61 6.43
ndard Deviatiorr · · :· · · · . 1.82 4.5
v 24.7 5.2
artlett's X2 .·· 11.911 14.48
{Bartlett's X2) 0.45 . 0.20 --~(
kewness -0.2471 ..S.0113 (
"··
.. ·
i
\.
8/20/14 (BATK-14)-. · . ARM 2014.2 AOV Means Table Page s of
·North Carolina State Universit ·
!
Evalu~tlon of.Mli, Flumentralin and N-Tac {Contact) in a Drop Line Application Method
Title No. 2: Loren Fishe~ Matthew Vann Joe Priest Scott Whitley ·
Trial ID:BATK-14 .· .· ...·· location~Kinston, NC v:~~~2014
Protocol ID:BATK-14 . . . lnvestigator:Joseph A Priest
Project ID:. · Study Director:Loren Fisher
· ·Sponsor ·
· · Con~ct:Roger Black
Randomized Complete Bfock (RCB) AOV For GREEN WT PLANT (GRAMS) 8/15/14 (Data Column 1)
source OF · ··,.. : · ·$1:'m. ~f Mean Squ~re F Prob(F)
· · ·8 quares
Total. 551094140.553571
Replicate 3 . · 6579.482143 2193.-160714 3.027 0.0408
· Treatment 13105S307.8035718.14a5.215659 112.480 0.0001
Error 39 28453.261857 724.442766
I Randomized C9mpl~te Bl~ck (RCa) AOV For NUMBER I PLANT 8/15/14 1 (Data Column 2)
· Sum of · Mean
Source OF Squares Square F Prob(F)
Total 55 . · ·37.888a93
Replicate 3 · 0.93S393 0,311131 3.508 0.0241
Treatment 13 33.495893 2.576607 29.050 0.0001
Error 39 . : , 3:459107 0.08.8695
I Randomized comprete ·s1~ck.{RCB) AOV For GREEN WT SUCKER (GRAMS) 8/15/14 (Data Column '3)
· .· · · Si.Im of · Mean ·
( source DF __ :.. s_qiJares . . Square F Prob(F)
Total 55 ... 519.107.~77
Replicate · 3. ·..:. · 7.181505 2.395835 0.720 0.5461
Treatment 13 . 382."156094 29~396623 8.835 0.0001
Error 39 · 129.764378 3.327292
I Randomized Complete B!ock (RCB} AOV For PERCENT SUCKER CONTROL 8/15/14 1 (Data Column 4)
·· .:Sum of Mean
Source OF Squi:ires Square F Prob(F)
Total 55 34121.2a1~9e
Replicate 3 108:226363 36.075454 1.780 0.1669
Treatment 13. ·.33228.790523 2556.060809126.143 0.0001
Error 39. . 790.264712 . 20.263198
(
l
/. RESEARCH NOTE.
J
Systemic Chemical
Fatty-Alcohol a Maleicb Malefc Hydrazidec Maleic Hydrazida
Concentration Hydrazide +Fatty-Alcohol I Chlorphropham Fltmietral foe
i (2.7 k9/ha) (2.4 kg/ha,2.0%) (2.7 + 1.2 kg/ha) ( 1.4 kg/ha)
1st 2nd
Applic Applic
---%--- ~ - - - .. - · Suckers, no. /p 1ant f -
- . - - - - - -- ~
1-decanql Illixture) and fout treatments with systemic chemicals Systfmics within.fatty-alcohol ·: ( .1
in a factorial arrangement for a total of 16 treatment$ (Table l). FJUJJletJalin .resµlted ih. the lowest sucker nUUlber within all·--
Each treatlllent was replicated thr~ times in a randomized com· fatty-~~ho) .tr~•ts. (Table 1). MH/cblorprbpham resulted
pletc block design. Bat:h plot cc>nsisted of a ~gle ~ow of tobac. in fl'We,i 8uokcril th~ MH and MH +fatty-alcohol when the
co 7 .om long. NictJtiana tobacum L. cvs. 'Speight 0-70' and 'Nor·. relatively wc;ak I. 711/a + 1. 70fo fatty-alcohol ~Un.ent was used.
thrup King 1:~326' w~e used in 1983 and 1984-85, respectively. For trea~ents which inclu~e4 ~ second fatty-alcohol applica-
Materials were apPlied with co.
pres~ back-pack sprayer tion of 3.4'l• or: 3.80/o the sequenti.al ~pplication ofMH/cblor-
utilizing ·three spray nozdes over the row. Fatty-alcohol, prophii.m di~ not significantly decleaSC sucker I!\ll!lber as COin•
flumetralin, ~d cblorprophain applications we.re applied with pared to MlI and MH + f~-alcohol. There were no differe!lces
three T0-3 nozzles at 173 ·JcPa for a solution volume of 487 µha, in Sllcicer number between plants sprayed with MH or MH +fatty.
Products containing :MI-I were applie4 with three 8003 no.zil.es alcohol regardless of the fatty-al~hol trcatinent, ·
at 345 kPa for a solution volUm.e of 542 L/ha, Rate~ of the · ~wnetralin application resulted in the lowest sucker weight
c:hemical~ used are shown in Table I. Tb¢irst fatty--alcohol ap- perplantfoll~wms the J.7o/a + 1.7%, 0 +3.411/e, and 1.7% +
plications were when SOii/a of the tobacco p~ts in ·each plot w~ 3.417/o fatty-alcohol treatments (Table 1), l{owevcr, when follow.
in the button stage of floral development. The second fatty- mg the relatively strona 3.411/o + 3.8% fatty-alcohol treatment
alcohol applications :were 5 dJYB after the first. Systemic applica- fluometratin resulted in less $licker weight per'plant than:MH
tions were 7 days after the second contact applications; Plants but did not differ significantly from. MH+fatty-alcohol and
were topped inunediately before the application of systemic MH/cblorpropham. MH/chlozpropham resulted in less sucker
treatments. · weight per plant·than MH following all fatty-alcohol treatments
Treatments were evaluated the day following harvest comple- except the 3.4Dfo + 3.811/o treatmC!lt; and less sucker weight per
tion, Suckers were counted and weighed from ~ consecutive plant than MH +fatty-alcohol following the 0 + 3.4o/a and J.7%
plants in each plot. Sucker num~ Jnd fresh weight per p1'mt +3.4% fatty-alcohol treatments. There were no differences in
were calculated and analyzed by analysis of variance teclmiques sucker weight per plant between ~cblorpropham and
(.5) for each year oftlie study. The combined data over the three MH +fatty-alcohol following the relatively weak I.7% + l. 7%
years were also analn;ed. Duncan's muhiple range test was utilized or strong 3.4'1• + 3.80/o fatty-alcohol treatments. MH+fatty-
. to separate treatJDent me1U1B when the analysis of variance in- a1cohol did not differ significantly from MH as measwed by
diCflte(l significa'Qt (P $ O.OS) treatment differences. sucker weight per PllUlt following any fatty-alcohol treatment
RESULTS
Fatty-alcohols within systemics
The combined analysis of variance over three years indicated Sucker number per plant did not differ significantly due to
a significant interaction among fatty-alcohol Slld systemic fatty-alcohol treatment when MH was the systemic treatment
treatments. Year by fatty-alcohol, year by systemic, and year by (Table 1). When MH +fatty-alcohol or MH/chlorpropham was
fatty-alcohol by systemic effects were not significant. Significant the systemic treatment the 0 + 3.4%;, 1.7% + 3.4%, and 3.4
differences . among systemic treatments within fatty-alcohol +3.8% treatments resulted in fewer suckers per plant tlian the
treato;lents were observed. Fatty-alcohol treatments also differed 1.7% + 1.7% fatty-alcohol treatment. The 3.4% + 3.80/o fatty-
significantly when analyzed within ~temic treatments. alcoho~ treatment resulted in more suckers per plant than 1. 7%
l I;
~ :
DISCUSSION
~cKNOWLEDGEMENTS
'
fatty-alcohol treatments were used; however, there were no dif-
ferences in .sucker number or fresh Weight followmg the 3.40/o
State University, Raleigh. 1983.
3. Peedin, G.F., W.K. Collini, W.D. Smith, N.T • Powell, R.W •
+ .3.8% contact treatment. These results indicate that the addi- Watkins, P .S. Southern, and W~D. Toussaint. Tobaa:o Infonnation 1986.
.i tional application of cblorpropham is not warranted when tobac- N.C. Agrlc. Ext. Serv. BuD.=-187 (Revised). 1985.
4. PrieAt, J .A., and H. Sel
.
. Combination of growth inln'bitors
.i co growers utilize the standard su~er control progriµn (3) of 2 for tobacco sucker control: c hydrazide and ~orpro~. Tob.
~ fatty·alcohol applications at 3.40/o and 3.80/o concentrations Bel. 27:1S6-1S7. 1983.
5. ·St eel, R.O.D., and J.H. Torrie . Principlea and Proctduw· ' ...
'
followed by MH application. ·
(
F'liunetralin provided.~tter sucker cotitrol than othe1"systemics S~cs, McGraw-Hill Boole Cmnpany, m~., New Ycirk, 48lp~ I
6. Steffims, 0.L. Growth regulator cott1binatlons for tobacco sue
when following fatty-alcohol treatments of 1.711/o + 1.7%, 0
.t
:t
·1
.
+ ~.~ozi. ~ P?' + 3.4%. Sucker control with ~umetralin was
control: Malek: hydri.zide and N-benzyldlntro~ (CGA-4106.S). 'I~
Sci. 24:10~-104. 1980.
···:
:~ ... :
'l
.~·
0 Payment enclosed
0 8111 me
0 Biii my eompany
Company
Dccaplt•llon (lopping} at onset of fluwcrh1i; i.!11 • Tobnno Plnuts: Three lypes of tobacco (Niroti1111a
standard pncllcv in 1he producllon ol tohacco. Sub· t11bnc11111 L) were uspd In 'this study, Including cv, Ma~
uqu.,nlly. axillary buds •viU srow Into bran<hes, !m11wn fanJ Caiic:rlon, iJuriey ;u, nnd N.C. 91· The llrsl hva
llJ suckcn, l>ccnu•• of the r.-mov.al nf apical duminancc. rcpn:scnt Maryland and Burley types •nd were grol'ln
Th" opcralion lor 1hc rcn1ovnl of lhuc 1utitcrs Is c;ilfod 11nd alM:ured .at Beltnllle, Macyland. and the last one
•suckt'l'lnJ(. Malerials used to Inhibit the grnivlh oE rc:prcsrnts Bright lype tobacco, arown utd nue-curcd
nxJllary buds inlo suckers arc lermod .. , •stickerlni; al Oxford, Nozth Carolina.
agents•. Tho m•Jorlly of lhC' suclcering •11cnts arc clth•r }"hcse pLmtr Wl!re .lleld-grown under regular cult11re
lost or dc~'Umposcd during the period of lobiicro Rrow1h , prnctiCC's and cured a1:i:ording to typ... ro~ sucker
rutd curing, but ~11mc may rr.rnain In or on the <llrcJ d1c:m!arl lesls of Muyland and Burley types, three
lraf. This p.lper reports the rcsidurs 11f fatly cskr nnd pl11nts \vere U5cd !or ui:h ln!alment. Eadi plmtl rcccivrd
01lcohol used as sudterin11 ~gents in the llo!J lYhiclt 1h11. chemkals once and wa.s harvested two week$ aftrr
remained in 1111 cured leaves of Maryland, Burley, and treatment. The illr·cured lawcs from thrtt plants wllhin
Urii;ht t'~pcrimental tobaccos, c;nh lrcalmc:nt we"' comblmcl. 1111d grouped lnlo 1hree.
Many hn•cr ~lkyl esters And alcohols sbnwcJ vorinus composite .sninp~s according ID top, middlr. illld boltom
d~itcs of dTectlve!'us for .sucker lnhlbilin.n (.fl• 11.e slnll positions. For Bright l-yp" lob1ccu, Rn pliinl1
mast effective ODeS ere SDtur.alc:d, 8 to 12 airbon .slr.alght >Vere used for each tn:almen t. 'Each plnnl m:c:lved th•
i:haln r:slcrs and alcohols, cspedally ihof;C' ••ith 10 car- . d1rmluls twice, lhe 'eCQlld applialion wns applied two
bons (:, 3). The commonly used ester for OclJ applica- •vcclcs after the Jirrl. This type of tolnm> wu h111vnted
, lfan is methyl ciprillO', and the t'Ommonly used alcoht>I by Je11f priming and tit~ WH nae-cu~d. Tlte llrsl
Is n mixture of 1-oct:inol and J•clccn11t1I. Tl1c surfodant , rrln1l11g was madit one werk after th" lirst tnntmirol,
for cslc:r Is pulyoxyrthykne (201 s:arbil~n nwnul.mr•I" 1h11 second ptlmlna was lhree. we11'ks ahtt &nt trratm•nt
(T•vRn 20) 0 , and that for alcohol ls polyoxycthylme (or Dru! wuk al\ er second treatment), and lh" .third or
fzo} sorbilnn monoolc:alt' (Tween aa). S'mce fatly rom· last priming WU I\\'! weeks aAer the firs! lnalment (or
pounds arc naturally occurring producls in tobacco, ihn:e weeks •fter second tmilm2nt). Laaves frurn live
labeled m:ircrlals were used •s tr.ic•n; in this rcrovcry pl.an15 of same :priming Within ""ch treatment werr
study. I 'C laurk acid di:rivnlives Wt'l'C u5Cd as they combined into one composite s11111ple.
••tte ,.,adily available. The T•Yl:cn surfocl•nls \Vlth
"C·labcllnn were supplied to us os " courtasy of JCI S11dreri11g Mtiltrials nnd l=icltl Trmrmruls: Chamlcals
Unili:d Slal"'5, lnc. [futrr1l'l'ly 1hc l\llas Cht'micil u..d indudcd the lollowlng: Methyl capr.ale, a mixture
Jndustn.,,., Jnc.). · of -x-octanol nnd 1-dec;inol (:rpproximaUly o-n),
methyl faur.att. l~usyl •kohal, !auric ncld-1-"C m1lhyl
" kk1111•nl f,.. p.Llic,.aw•"a JII. ?t~r. l9Jl. 6lcr, lauryl-alcuhol-1-llC, Tween zot T>Vten 20-l"C:
•• Mnn""" .J a 1•:.l~rl ar l'N1'ti1nr' Jl(•.luu .lllW'I. llPt u•nilDlc a (rilh« llC-i-hlly acid, or IJC-U-elb:rlime oxide), Twel!D
,_arBtn ., •arrar'lll th ...r ..,..J.,... •r
tire U. S. 1).tp.ari•n' •I
{lo, and Tween 8o-11 C {dlh"r ·11c.1-folly aciJ; or
"='"'
tal•tw~ ...-J .._. • .,. ;,..,.1,.
tn •rl'f.11•.al ia "'" «111d11d1J111 -el 11tlu
•~C-U-ethylene oxide).
,,...._,," 11.11 ""11" .if'4'1 J,r wit.at.Jc. ·
Table 1, D ucrlpUon or malerl•I• and dosage und for each planl.
11 C·BCIMty (CPMJ
Trealment
cocle
Materfals and comblnallon·
Maryl~~! Burley I !'tl11hl lype
- The c:aid combinallon cf lhcse acllve malrrials ani:t m11lerlals of thre1 pl.ant. Er~m Maryland and Burley
•Urfactan?s, lhe rale of appllcalion, and lhc lolnl level l;ypes, and live plants from !he Bright type. The
of llC-acllvily arc $hown in Tobie 1, toscthor with "C-acUvily of composite sample from e..dt type and
· the aninned <WR for eocl1 lrcnlmenl, the l"'rcenl~ge of 11 C·recovery are listed In Tllblcs 3,
4, and :; for Maryland, Durley, and Brighi tobaccos,
R<'i!1111:: Dckm1i1111/icJ11: The cornbln ..d cu~ lcof
rt'SpccUvely. Generally, the average ncovery of •~c
· PmplC5 were ground and wrll mixed. A Jo g sub-
actMly w.s low. The 1'C-labeleil ethylme oxide moiely
sample from ·cam treatment w11.1 cxtrnci.J willi -.oo ml
of Twrm cD111p01lnd1 appnrrd to be more stable lhan
70 •/1 clhanoJ jn a \-Ynring Bltnder lor 1 o mlnulu.
"C-labelcd fatly add moiety of the same compounds
following r.Jlr.ilian nnd conanlratlon, nn aliquot replt'-
and thus resulled Jn an apparrntly higher NC-recovery
scatlns; 100 111g uf original tobarco sample was used of IN former lnalmenls.
for "C-counling In " toluene C<ld<l•iL Data obbincd
from lrealme11ta codes 1, .2, ;, •nd 4 were usccl fut The 1 'C-r«OVel)' for Maryland and Burley types was
~re bodcground correc;lion of corresponding lrea.tments. the highest in top leaves where moJt of the chemlal
spnys wu-e dluclly appUed. As exptcled, the percen-
Resldue data ate c:olcubited based .on llC-rcmvery. tug~ of ncovery was gradually reduced towud rnlddle
portion of the plant, and the lowest m:onry was
RESULTS obt;Uned for lhe bollom leaves, However, the highest
• "'C·ncovery for Bright IYJ't tobacco w11 U•ually Jn the .
Total yield of aired Inf from e;ich treatment 19 IJstal stcond priming oc_ at the middle po&i.Uon. This result
In 'fable .:i. Thrse composile s.mpli:!i 1cprcsenlcd may hne 1dlecled the dftet of tht cecancl chemical
Table .'L Vield or· cornpl>SJla samples !ram each trnlm•nt •c=rdln.11 lo afallc PD•lllans or prbnlngs.
Burley 21
Maryland cenarron N. C.95
..
Treat· -
man!
code• eo~om I Mldclle
g
Top
g
Tofil
g
~Ml~
g
Top
g
Total
g
1•1
PT!mlllQ
9
2nd ~, Total
PlfJnillg p~ing
g g
• Sea Tablo 1.
142
/ d'/
'v-
(
\
I
/.{ l ,.
'"fr-...,.-
Tabla 3. "C-aclMly of composll1 Maryland lobac:co s11111pte~,
i
.
I Bonam Middle
I (,:Z
Top
I
I
Treatment
coda•
j
I.
··
100 mg
1·
Tola.I CPM
'I
I ··
R~~ety c';~e
100 mg f -
Total CPM A
0 1
ry 100mgl
sample
CPM
Total CPM Recovery
r/o)
Ave1ag1
llCOVBI)'
r'/.l
\ I
Tr::~~~nl ~- T~I:;-
Bollom
-100
MiCldla Top
Average
I ·~P~
·--;.;;,
1
CPM
,;:,-:;
. (9/oJ
sample
Cl'M
mg
Tol1I
CPM
Recovery 100 mg
('!.)
aampla
CPM
Total
CPM ,.,,, '''ritry
Reoovery
2Q.3 1.70 :•: 10' 21.9 1.5T x 1o> 16.1 .1.36 x 101
2 22.5 1.93 :< 10' 20.0 1.66 )( 10' 111.9 1.82 x 101
3 22..4 2.44 x 101 3.4 3.74;.: 101 14.8 t.22 x 10'
A 23..5 2.118 ~ 1o' 19.1 2.35 )( 10' 16.3 1.93x10;
s 43.1 4.52 )( 10' .DO:! 8D.7 6.81x10' .am 177.1 1.77 x 1D' .fl09 .004
8 152.4 1.48 )( 10' .004 220.0 1.89 :< 10' .Ollll 940.3 1.57 x 1D' ~ .017
7 51.I 4.70 'I 101 .001 148.2 1.()8 ·< 10' .DOS 347..4 '4.112x10' .Q211 .003
8 75;8 8.84 x 10' .003 137.4 1Ji3 Y. 10' .11117 354..1 6.10 x 10' .029 .013
9 74.S 9.63 x 10' .004 153.8 1.79 ;: 10' .009 721.B 8..68)(10' .054 .022
10 102.6' 9.94 )( 10' .004 . 207.4 1.78 Y. 10' .008 -469.7 4~x10• .D24 .D12
Tre11111en1 Averave
C:odD" Recovery racovery
!'/•) f/1)
• Se• T1ble I,
(
\
Tablo I. Calc:ulaled , ..Jdu•I lneb D/ l••I 111al11tl•I• In lobacca leaf.
-· Tta~l111enl
cads·
I
I
we.labeled lesl Jml•ual
Maryland Caltetton
Recovery
of malortol
j
J
.Residue
on IHI
Recovery
ol malerl:d
I
Bu1le7 21
. .... - -----...-----1·----
Residuo
--- --
Recovery / Residua
on feal
N. c. 95
al malerlal on loal
l lmgJ (ppm) (mgJ . (ppmJ (mg) (pprn)
5 Twaan :o!O •'C-1-la lly acid 0.087 0.383 0:038 0.138 D.368 D.$27
6 Tween 20 "C-LJ-elhyfane·ox1de 11.269 1.227 0.163 0.413 2.192 <f.D44
7 Tween e'O "C· Mal!!' aad 0.1H 0.592 0.115 0.409 0.936 1.228
a Tweun SO "C·U·tlhylene oxide 0.259 D.748 0.187 0.477 1.200 1.449
9 "C·1·1aurlc acid melhyl ular 0.461 1.445 0.633 1.134 0.432 0.748
10 "C-1-lautyf alcohol 0.427 1.348 IU7D D.985 0.712 1.007
·a .. T"11e 1.
tn:Jlntenr wltkh was applied only unc week biiforc this lulal is about 2.6 ppm residue level whim is much
priming. 111' .wera11e residue levels nm.lining w1 lu- lower than earliu f111dings.
b•rro IL-of '""re <:•kllfoleJ, •• shown In T~ble 6. 111e l'he nalurally occurring fatty add derivaUves iJ1 c:ured
cakulilliun was based on percml of 1 'C·recuvrry from leaf lobacc:o •re around 7,000 ppm (~). The lotal lipid
ench trc-atmenl of eJdt tobait:o type. Liurlc ncid methyl fraction In leaf tobacco Is approxlmotely len times
e~lcr reslJucs >vcre J.~s. 1.7J, anJ 0.15 ppm, anti i;re•ler than the level of /ally c:ompounds. It is •pparenl
Jauryl alcohol reskh1es were 1.35, 0.99, nnd 1.01 ppm !hat lhe residue level pf laity coatpounds URd as
for M4rylanJ. Burley, 1111d Urlght tobaccu, respectively. S11ckerlng agent, In the range nporled in this paper.
Calcufaled residue levels for the Tween m•krlols varied wotdd not affect leaf quality or usabillly,
wiJdy doponJlng on poslliun Df flC-fobcling; r•n~"
wa bctwmt o.1<f and ~-o~ ppm. The golll!ral :werage
for the rosiJue fovcl of T•"l!on compounds wo\·
SUMMARY
approximately 0.5 ppm bnsed un lolly acid niuicty, and
1 -4 ppm based un ethylene oxide molely.
F;ilty compounds includins Jauryl alcohol and methyl
burale and Tween 2.0 sur.fai:tant (polyoxyethyJene (;ro]
DISCUSSION AND CONCLUSION · sorbJran monolJurate) and Tween aa 1urlaclant (pol)-
axyelhylen• [20] sorbiliinniDJ100lu1e) with "ClabellnJr
A epara~ study on lhc fJle uf fatty compounds and at various pos!Uons were used as suckering ~sents !or ( ..- .,/
M;uylAncf, Burley, and Bright to&.cco typ., (:Nicolfnna
surlact:mls applied on tobacco (1) revcllltd that there
was lnten:lllWerslon among m'ethyl laurate, lauryl tnbm:m11 L) and their icsidues on the tobGcco deter- . '"·
akohul, and !auric ncld during lhe 16 and J.f<f huur mined.. An av1ng1 resld111t of 1.61 ppm of ftilly com-
sampling of fr9h tobatta m•lerfals. Since results pounds and 1.0 :PPrn of surfactanb were found. The
eeport~ ltere Wen> baJ<td on =o\ll:ry of 11C-iict!vlty combined lotnl of ;r.5 ppm residilt due to these sucker-
whidt wos labeled ~I lhe J•pasjlion lo cMbonyl or ing 11genb is far below an earller prtllminnry tr.st of
11lcuholic hydroxyl groups, the c;1kula1ed fatly residues 4.B ppm of rr.sldue 'In comparison with 7 .ooo ppm
. n1ay, lherdore, ·Include the summation of •cid, alcuhol. natur•lly 11CCUrring fatty compounds Jn tobacco.
~ma cstrr rasultlng from rnteminvtni1>n of the applied
nlakrlnl. Jt w•s also found that all the Tween rnaluC.ls
rc1>1alnins un lhe tobacco >Yl'fl! hydrolyzccl 111 al/11 (1). ZUSAMMENFASSUNG
Thi! rnlculatcd 1'1?5lduiil dat;i from Tw~s teporlcd here
may dther n:llC!\'t fJtly ester {l:iurate ur ol~ate), or FettarUge Verbindungen wU. Laurylalkohol und Methi-1·
pulyelhuxylati:d polyul, clcpendins on whether lhe ·1aurat sowie die oberllit:henektivenSubslanzen Twem2.0
lnbcllnlf was nt fatty acicl ur ethylene o:ckJa moiety, (Polyoxyithylen[20Jsorblt&n-1nonolaural) und Twem 80
nisp.-cllvcly. The maximum t11lculoll!d recuv~ ofTwem (Polyoxyilhylen[ioJsorbltm-monoolnt) mlt llC-Mar-
material ubserved Jn thes., tuts WM .f pp111; hydrolyzed . kfuung In versd1i1denen Poslllonen Wurden als MilteJ
fatty materials orlglnated from Tweens would be only 7.ur Kantrolle des Celzmwachstums .bri MarylDtd-,
•small fo1ctiun of thr Twcens. llurley- und Bright·Tahalcen (Nicolinnn tnbncum L)
In 1>ne of our P""liminary teats in""lvlng Maryland a.nd benvtzt und lhre RDcbtinde Im Ta~lc unlersuchl Der
Uurlcy tobncco types· with which we used llC-labelcd durchsdtn!tlliche Riickstandsgehalt. belief sllh auf 1,61
mctJ1yl l•i.irale ;ind Ja11ryl alcohol, we fD\mtl an avernce ppm bei den fottarUpn Verblndwigth und auf 1.0 ppm
t>f -1.8 PJ•m rt'sioluc. The prennt study shuwed lln bcl den oberHlichmali.tlven Substanzen. Der Geu111t-.1
aYt.-r.1r.e •t'lli•luc uf unly 1.6 pp111 folly cun1pouml ond ~on 2,15 ppm fUr Rii&stinde dleser WodJStu!ftsregler
.ippruxlm.itely 1.0 ppm T•vecn rnlduc.· The combined lacgt welt unter dem £rgebnis clnes Eriihuen Vorver-
v\ ./
,-
/
6!i ........ ~.
.·
such.s mlt 4,8 ppm im Vtrglelch t.u dem n~tnriichen Vor- 1. Slcffons, C. L~ T, C. Tso, ~nd D. W. Sp•ulJlnr.:
kommrn von fetUrtlgen Verblndungen im T~bak in fJlly •kohol inhibition uf tob~cco axill•ry anJ 1er-
Hiihe von 7000 ppm. 1nin~I buJ growth: Agriculture and Food 01cmistry
IS (1967) 972-5".
3. Tso, T. C.: Plant growlh inhib1t1011 of some folly
RESUME acids anJ th~ir analogues; Nature :.01 (196~) 5 11 -1.i.
4. Tso, T. C.: Physiology .nnd biod11!mis1ry 1>f tub.icco
On ~ rmploye comme agents pour l'ebourgeonnemenl plants; Dowden,. Hutchinson anJ Ross, Strou>burg,
de tab•c Maryland, Burley et Bright (Nicaliann lnli11· Pa., 1971, PP• 129-139 am! pp.27.!-281.
cum L) Jes composes gras sulvanls: alcool lauryllque,
Jauute de mclhy~, Tween 10 surfactant (polyoxy-
ethylene[2o]monolaurale de 5orbit1n} et TweH1 So
surfactant (polyoxyfthyll:nef10Jmono-olhte de 50rbl•
tan) marques au carbane 14 l difflrentes positions. On •
a dEtmnlnc Jeur n!sidu daru le tabac. Des r~dus Ackncno1c.tgmml
moyens de i,15, ppm de comp<!s~s gras, d ~,a ppm de
We 11i1111k. tl•e TC1 ll11ilcd StJJIH, l11c. ({01111,•rly At/,u
surfacta.nts ant el~ retrouvk Le r61du tot•I C"OmblnE
de 1,6 ppm dil aux ~gents d'ebourgeonnement en Ch1m1ical J111l11slril'S, Jni:.) for provlilI11s lo1l•tl••1I '"'
question est de beaucoup lnferieur ~ 4,8 ppm lrouv6 rnmJ>Dl1J11u, m11f Frtmk Sl1nrp """ Mnry E. '£11.'(l'll11111pl
for ihelr tromiml assisltJJ1u.
dans des test5 prillminalres, surtoul .si )'on compare
au 7.000 ppm des COrPS gras se trouvant n>'ltun!lhnenl
dam le tabat".
REFERENCES
. TT11 1ii1Jhors 11tftl1yn1
'L T5o, T. C., Md H. Otu: The fate of fatty compounds Bt!llFVille A¢c11/111re Ruenrdr CrJJler, Nortl•r111111rn
and i;urfactanls used u sucker control agenls on R··~ion, A.vimllra11I ll.P$enn:l1 Stn•irr,
lleld tobacco; ~974• in preparation. ll.S. Dept. of Agrlc11/111~. Bell$1•ille, Maryl11111i, :i.0;05.
5
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The 3 acre field of tobacco NC196 was planted on 5-28-13 to be used in a flue cured wood barn for a
hfstorlcal demonstration at the N.C. state fair. The tobacco first went through somewhat of a drought
but eventually the rain started coming regularly makfng the crop all uniform. Then we come Jn on 8-23·
13 and were able to top the field 100 percent .Then the following day 8·24-13 we walked over the fleld
to make sure that we had got 1 Inch or longer suckers. Then on 8-26-13 we applied our first application
of n-tac at a rate of 2.5 gal. to 48 gals. of water. Then l kept check on the burn down of the following
smaller suckers weeks after the first application. We had such a great burn control of suckers from n-tac
even holding the next set suckers from coming. Then I come in on 9-17 13 and made another application
of n-tac 2.5 gal. to 48 gals. of water and observes the followlng days of control we have gotten .Then 1.
was thinking about a MH application but the following weeks proved I didn't need It because of the
control I had with 2 applications of n-tac for the tobacco to hold untll 10·18-13 with great control of
suckers. The burn down of the sucker and hold ability were amazing using n-tac.
Sincerely,
/
Carl Watson
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OLD BELT TOBACCO GROWERS' PROFITS UP IN 2010
David Hartman, Walnut Cove, NC, flue-cured and burley tobacco grower says his
tobacco profits were up last year compared to previous years.
Hartman and his brother grew 34 acres of flue-cured and 6 acres of burley in 201 O. Their
tobacco profits were greater with 40 acres than when they planted more than 100 acr~ of
....
tobacco. And, the smaller tobacco crop allowed them time and resomces ·to de\!el6p
--
other profitable enterprises on the farm.
Hartman says they controlled production costs, produced better quality leaf with higher
grades and had a year with more favorable rains. Their contract buyer increased and their
· growing contract for 2011 and he and his family look forward to another profitable crop
in2011.
As a result of the production practices used and good weather and the quality of his cured
leaf, his contractor rewarded him for the high quality of his cured leaf and increased his
( contract for 2011. ·.
!
All of Hartman bales received number 1or2 grades except that 5 in 6 bales graded 3. He
found the grades received to be a big plus for profits compared to when his leaf graded
muchlower..
After the 2009 season one of his two contractors dropped him. After the 2010 season the
:remaining contractor gave him an increase for 2011. His family has about all they want
to grow.
Production costs in the Hartman operation are reduced several ways to help profits.
Heading the list is controlling labor costs by using only 4 or 5 local people only when
needed with the remainder being family labor. He found the overhead cost of migrant
worl~ers was more than he could pay and be profitable.
Tue biggest reduction in costs of production was very low curing fuel costs. Hartman
cures with a boiler-type system where the water is heated with wood fuel. The fuel
source· is scrap wood from a logger and wood from landscape companies. There is a
logging operation near the Hartman farm that delivers scrap wood from as far away as 20
miles. Tue other big source of scrap wood is from about 15 lHn.dscape companies.
\.
Hartman has adequate land for a 4-year rotation. Being able to use a long rotation saves
him a lot on chemicals for soil home diseases and, the rotation allows him to plant a
range ofvarieties which may stay in the field different times. This year he plans to plant
15 acres of his K326 on land that has not been planted in tobacco for many years.
Hartman has had a problem with weeds in his tobacco fields and plans to use more
herbicides this season. He does not like to chop morning glories and other weeds.
Fertilizer use is another big area that Hartman has relatively low costs. Fertilizer costs
are about 6 cents per pound of cured leafl First, he controls the rate nitrogen to 65
pounds per acre for the flue-cured tobacco and about double this for the burley plus a
little starter fertilizer in the transplant in water.
Hartman gets the maximum use from his fertilizer by applying some of the fertilizer by
hand as well as some mechanically. He drops the fertilizer on the soil close to the base of
the plant He figures out how many plants should be fertilized with a handful of the
fertilizer being applied (Many growers use fertilizer programs that cost 12-15 cents per
pound of cmed leaf.) Hartman reduces fertilizer rates applied if timely rains do not
come. He works with his county extension agent in the fertilization program or 8-16-24 (
or 6-12-18 and ammonium nitrate.
·Sucker control is an area that Hartman is studying for 2011. He believes his· contractor
will soon want to buy only MH free leaf. Hartman is trying to determine how he will
respond to these buyer needs. He has been applying two applications of a contact-type
chemical applied at 4 percent concentration the :first application and 5 percent the second
application. These applications were followed with Prime Plus and M?·
Supplemental income comes from Ag tourism and a wholesale and retail meat market.
David Hartman
1095 Anie Lane
Walnut Cove, NC 27052
Cell: 336-972-1590
Email: DavidHartman966@ho~ai1.com
Bill [email protected]
-- 2~
1. A Petition Justification Statement:
Inclusion ofa Synthetic on the National List 205. 601 (k) (2)
• Explain why the synthetic substance is necessary for the production of an organic
product?
The Fatty Alcohols being petitioned for use in organic crop productions, have beeen used
on farms for several decades with a positive and effective use history, has an excellent
record in the field, the environment, and human safety; with cultural benefits.
Proper crop use of these Fatty Alcohols reduces overall insect/pest pressures and
chemical use, farm labor exposure, farm labor cost and energy. Through carefully timed
applications as required, it reduces crop hand topping and suckering, this activity benefits
the overall farm resources management, during the pre-and- post harvest peiords.
When used in conjuinction with traditional cultural practices, Fatty Alcohols, increases
crop yield, quality and marketability and has been shown to increase gross yield by
several hundreds pounds per acre, with a substandial income increase in crop value for
the farmer!
Additionally, clean sucker and foliage control enables machine harvesting, once again
increasing crop yield and quality, and providing major energy and labor savings.
Following are a few benefits realized by the farmer when using Fatty Alcohols:
• Increase crop quality and yields and gross income margins to the farmer.
In summary, the proper use of Fatty Alcohols on organic crops increases crop quality, yield,
and value-added components, at substantial labor and energy reductions, which contribures
significantly to the farm gross/net income of the family farm unit!
(.
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BE PEBSOWAL care market is Rachel Wright entire fun:nalation, and if desired, the
without doubt caught. up in :furmulation can be certified orgaxrlc by
Croda EuroP.e
. .
the global wlrlrlwind of
. non-govermnent organizations. Yet
many consumers o not realize that
industry may say that tb.e organic clain_is for cosmetics and per-
trend is still in its infancy, share with home grown brands such as sQnal care products :fBll outside EU leg-
but it is by no means Gaia Skin Naturals, Natures Organic islation af orgaxrlc labelling as they are
msignfficant. rn fact. it is and Eco Store. Natural and organic not fur human COllSUillption. -
increasing rapidly: the glob- claims are less prominent in other "Free from• is a cpmmon :fbod indus-
al natmal and organic mar- Asian countries, as they tackle the try claim which is also inereasing1y
ket is growiog a ~ lC>-16% a green trend with the use of traditional used in-the penional care lndustry. Free
year, accordlng to Organic Monitoc. ~e nataral ingrerlients, cold processing from claims have bee.u c::riticlzed fur
global natural and organic market was and recyclable and refillable paclraging their use in cosmetics, as they can
· valued at $8 billion in 2008, with the· claims. . sqmetimes be misle~. These claims
most developed regi.OllS being North Green: claimB used across the global can imply that the free from ingredient
America and Western Europe. which personal care industcy can include any is in some way undesirable. but the
aci:onnted fur a significant 65.% and of the fo1low:ing: undesirable attributes often lack tech·
28% respectively. HIJWever, growth is Natural claims can be Cited for ni.cal data to justify this perception. ...
not as~ in Asia Pacific, wlrlch bas either an :individual ingredient or group Social and ethical claims SllC'h as ~
less than 3% maz:&:ei share. of:ing:redients; e.g., can.tams lOO'lf, natu- :firlr trade and not tested on. animals can
7
samer awareness, the term green· is ingredients. While na:tura1 claims are ment; oihers are concerned with assist,. f
beingueed:in so Jil8DY sceDarios and, as unregulated, formulations can also be :ing either the local economy or localized. t
· a result, there are many d:i:ffiD:ent defi- ~ natural by a number of non.- commuDities. often :in remote areas. .e
nitions. W"ztb. no official defmition, government orgs.niza~ such. as · Biodegradabili:ty claims are
t:ranalstiOD and mt.erpref;atimi of the Germania BDm or France's Ecoce:rt. uncommon, but growjng in populatlty. Ji
meaning of green can depend on many ()Jiganic claims can also be made According to GNPD Mint.el, there were ti
factors, in.eluding the indUstry in ques- either for a specific :ingredient or for the 1hree times as many products launched u
tion and the ~s social and envi- with biodegradability claims in 2008 BS l'l
ro:mnental awareness. there were in 2007~ Itis an area of focus st
In lXlSDY developed markats, green for rins&off farmulations such as show- bt
claims me risblg sigDllicantly, especial- er gels, shampoos and hand washes, as of
ly in Europe, a market in which. these product.ii gn more clirec:tJ,y down Fe
Min.tel data :indicates that one in our drains and: into C1lll" ecosystem. .t·. OJ)
seven~ care products had Carbon footprints measure 01')
at least one green claim. an the greetlhouse gas emissions of a fie
G. re en
iDcrease from -1 in 10 during prodnct throughout its lifecycle taj
2007. However, these claims in order to ~tify areas fur car- .P
extend beyond natural and ban reductions. Jn the ux, the ~ by
Carbon Trust bas peen piloting t gn
organic to include petrocb.emi- .
cal-ftee,presarvative-:free.local- : . :,. a plan cm a p.umber of di1ferenf ' clal
J.y produced. fair trade, not teat-
ed On animals, bio-degradable,
sust.ainab1y sourced :ingredients,
. Gu,. de ..,!JJ
Ov
products from several industry
sect.ors. Boots' Botanics shampoo
l'8Ilg9 was one of the first in per-
CeJ
Nat
:p1J'1~t;;:-'1 ~b.gl>. ~e~- ... ·~~ . .. . . (} .. sonal care to tdsl- the concept in ,.'·.:.. . .. ou.s
2006, resulting in 20% redw:Qon in f itor
In the .Asia-Pacific region, the green t9 1b. ~~ the range's ca:cbon footpr:int. 1 Since the can
m.srket is quite diversffied. Australia '['e-ht Cho\c.e pilot, and at the request of the project mru:
and New Zeala:nd have the majority sponsors (Carbon Trust and
Asia-PscHlc: National Association for Sustainable Asla·Paclflt:: Korea Eco-label, Environmental Choice,
Agriculture, Australia (NASM) Australia ·
. LaUn AmBllca:"IBD Certifie:d Organic, IBD Natural Latia America: IBD EcoSocial
Ingredients
==
with Pricepne 9091, slowly add water classes of CODSUmers in North America
Europe. other green paramet.ers are· with stirring and stir until fully (i7gure .V.LOHAS (Lifestyles ofHealt.b.
IPISSe~~damo= ~~~=i~~
often considered by manufacturers,
·EiSPeci!illY fu A6ia where gOing greeii is.
an energy ar waste saVing emtcise and and add to water blend while stining at rounding their health and envjronment
i~;'.
\., ; thoughts ere more iJiline with the 12 400rpm. Homogenize for two minutes and play a big role in susteining the !:
_.Principles of Green Chemistry! at 10,000zpm. Stir at 400-500rpm for a · trend. Naturalitee also account for 19%, ;
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Des 'ite the lobal downturn, consume·rs.are still
choosing detergents with a green twist
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! lots of.infurmation about prodiJ9: l..
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more. 'Under growingp~to
~-------~-----------------------------------..;...----------_.J
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mass-market retail~ says Sansp.Di by4.8% year on year to $1.75bn. Sales for the
And~ the punishing ecxmomic first nine months were down by nearly 4%.
conditions -which have led to a surge in Meattwbile, Henkel, of Germany. saw a Q3
popularity fonialue brands - there is still dip ofnearly 3% in its Laundry & Home Care ·
ail appetite fur th~e higher-priced products cliYision..: keeping sale& just~ €lbn -
with green credentials. "I think this segment though it claimed. organic growth of2.4%.
ofthe~is here to 11my: he saya. '"In Western Europe and North America,
..
:1 recent!.yposted ~int-quarter (Ql) results: is partly linked to 1he rise in pOpularity of
its Fabric Care Br Home Care div.tsion, which show.er1 over baths. . ·
includes laundry~d dishwasher detergents -r.iquid soaps have now gone beyond the
than anllJ;lal tits and p1Im oil. ·
. "The .i:Darlcetis driven to an extent liy con.-
sumen - but alsp byrawmateriai variability
..
and fubric softencr1, reported a 596 dip in
. sales;to-S&lbn~.
h Anglo-Dutdt rival Unilever :&red little
betti:r: Q3 sales in its home care division -
· kitchen, and moved upstaixs.tothc bath-·
room:' aaysH~cm. '. ·
more chance to-Md value, witlinew for·
·
Liquid ~IJ.Ps also give JnaDUf1,ctu:rers
margins:' he·· · · ·. ·•
~ bymmufucturers' desire.to increase
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Nissan
. Chemical
Amerloa Corporation
=
Xtra
I '-. ofWaterrequjredfor cleaning
CH.9 CHa · CH -COOH arctbewaytogo.
I . / Procter&:Gemble, the 3%
CHs- c. --CHt-CH Purex
SocHb gorlllafn the laundry (HenkellD!aO
I . I . . detergent aisle with its'l1cle
ala CHa
tso-Stearlc Acid .
line,isllOtfceablymissiDgfrom
those. promotlngcleanersbued
6%
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onmitural!Dgredients.Lauren
.•. Properties 'J.'hauwl. a publk:afrafts spe-
clalistwho band1ea sustainabil-
·• Branched, saturated long alkyl ityissuesforP&:G'siilbtlc cm:e ·
·chain · bwdness, explainathartbfsfs
• Uquld freezing ~Int <-30° C because the c:ompanywantsto
..... -~bebind::--......... · NOTl!salaslnfood.ctnig.and..._mercllaudlsellolwi,~
• HydrophHlc and hydrophobic Bee ~ ,.., .,..,.......... lrwYlllMart. fartbe!i211HkPllbl enclnaDec.28,2008. Pac•
abilltyclalms. Procter" GamblL SOUllCQ lnfll111'11d11111 !asoLn:eS ..
balance for specialty esters ·
"We'remnunfttedtobavillg
a science-based approach to sostablahll-
·Typ~ ity." ThlU?Ulllsays. ~beamseft>snatural
• c 1 ~Alcohol and c;e-Acid doesn'tm.eanft>sBllStaiDahle. WehavetU-
• l-C15H31CH20H en alife-cycle analysis approachto ensure
• i-Ctstia1COOH we arexnaklngclaimstbataremeaningful
· . andmeasureable.•
e Applications Inlaundryprodµcts,P&G'smsinsustain·
·abilityeffortshavebeeninconcenttatiing
• Various f;ypes eater itsdeteigentstosave onuansportatirin
• Hlg~ perfomiance lubricants andpacbgiDgcostsandinJaunrbfngde-
•Cosmetics te?geDtSsuchas~ColdwaterandArlel
•Personal Care~ Cool Clean that save enezgybycleanfngwell
• Specialty soaps· and.cleanser5 adowerwasht'elnperlltUreBlnbothcases,
• Offset Ink Printing · ·P&G saysftcanqu.antifyitsnewproducts'
reduced ~enml.fooq>dnt.
Nissan Chemical America Corporation. 'T:mIJOtgofngtorommentonwhetberor
10777 Westhellrier, Suite 830 notourcompetitomaredoingtb.at."'Jllan:iau
Houston, TX 77042 says. "bm:Iwfilteilycu thatuntilbebJgable
1osaysomeihlngfli'nattmd'means!tJsmore·
Phone: 713-532-4745
Fax: 713-532--0363
sustainable, wewfilnatdothat."
ic'
[email protected] uJust b4!CC1use· it's na~ural doesn't
www.nis.sanchem-usa.com mean it's· sustainable:'
WWW.CEN•ONLINE.ORG 14 JANUARY 26, 2009
Rhodoclean, asurlilctaJittbatlinks ethyl- with the Purex Natural Elements line, but
ene oxide orjiropyleneaxide to J>pinene Purexis a set:9lld-de.rbrand that doesn't
extraetedfrompine oil. have the same reputation as Tide does.ID
Europe. where HeDk.el's PeIBllls the gold
ALTHOUGH COMPANIES sucliuP&G standard, the companyhasn'tlaunched a
mayhave soundsclentlftcreasonsto smy green~ion. .
offthe "all-catllial"bandwago:n. theyhave . Goingall-natmal would compromise the
H~~f&
policy,Milllcr--Bhscbbanmsaya,Henkel
notonlycooperateswithrawmaterlal
suppllers~researchinst:itntes but8lso
0 licenses innovations from f:tsrlvals.
5,12-Naphthacenequlnone 3,4'-Dlamlnodiphenylmethane
CASI 109().13-7 lN0603J CASt1943o-83-2 [01684]
While Heilkel usedlow-temperatUre
effectiveness to improve tbesnstahlabil·
eyofits inarquee Enropeuibtands, the
TCI AMERICA · TCI EUROPE company also createdanewbrmdldmed
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• Certlflca11ons such as the USDA i. ,:;::;·(~~:. ...:: whidutandard is best $llited for your brand. it com.es down to one simple
NOP certlllcatlon, Mllle awell-known :.:P,:{';f~¢:~~pe of any and all certification is marketability. De.signing a product using
organic Industry standard, can be ·:~(~~~~;~ents. m>fdiDghot button problematic ingredients and utilizing a generally
··:! · •· ~~ent profile is a noble cause, and. in many cases. sales Will do just fine. But .
problema.1ic as they werent developed ,i._';.. .: *.:Wiesti.cin
arises, "Whatwill. a certification add to the value ofthe brand?"
with the beauty Industry In mind and. ·
often require experSv0 marufacturing
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And it is simple-the more heavily organic ingredients" claim must be become inaeas.ingly popular due to
marlceted the standard is, the more it will certifie·d to the NSF 305 ANSI Standard widespread awareness of GMO foods.
add value to your brand. So far, most for Organic Personal Care products, During the non-GMO verffiC8tlon
natural and organic standards have been a consensus-based industry standard process, beauty brand owners need to assess
beyond reproach due to their well-written accepted by the Ameqcan National both the ingredients used in thelrproducts
nature. So choosing the "'wron( standard Standards Institute and n:ianaged by NSF and the ingredients of an ingredient-
based on lack of strictness is relatively International. (Whole Foods' guidelines leading all the way back to the source
unheard of. However; there are nmltiple also state •all products making an 'organic' material-in order to dO a proper audit
options that beauty brands pursue in. green product claim must be certified to the In some cases. this can be a dllliculttask,
certifications. · USDA NOP standard, the same standard as source material suppliers can be closely
under u.s.1aw.•) them to be difficult to track.
Setting Standards 'Ihe fascinating part of the NSF
International standard is its approval
'Ibuc:hing on a few standards I have been
intimately involved with. I can offer a
approach. Rllther than ha~ a med list of · Weighing Your Options
acceptable iri.gredients to work with, this
firsthand perspective. Overall, beauty brand owners will
standard has an acceptable list of processes
The us. Department of Agriculture's COD.tlnue to find new ways to differentiate
of how these ingredients are made-ie.
National Organic Program {USDA · themselves from all other productllnes.
you can have two ingredients fr.om the
NOP} is what many consider to 'be the . '!he use of green-certified standards has
same source and within the same end .
pinnacle ¢any green/organic standard been an invaluable tool to verify and lend
product but one could be ~pproved and .
'Ibis is likely due to it being the most .defimti~ to natural products, buti:Dany
the other not lllmply due to its ~owable
heavily recognized and branded of any . procesa. barriers remain to certification. 'Ihese
standatd-and not because it is S\1ited baniers include cost, recognizability of the
' With this stanfud. certain original
.. and designed for personal care. Using
ingredients such BS sulfate-based . certification standard and the formulation
USDA-certified organic in.gredients in aver ~of using a green certification
' place of conventional ingredients will
surfactants became allowable newer,
standard that may not have a wide~
...
novel surfact8nts bec:anse the process to
generally increase a product's stature. but.
make the original iurfaCtant wu far more of ccismetic ingredients or ingredient · \ ·\ _.
in. some cases, tuming your product into
a full USDA organic certified prodlict is a
natural thml some newer ones. However, . synthesis processes available·yet.
. · Brand owners must carefullylft:lgh the!r
the success of the NSF certification fa not
challenge dne to the many limitations of choices to make sore that adhering to any.
all in its originality. It is far more marketed
this standard and applyiDg it to produce a green. certification standard w.iD. be giving
and rea>gD.ized ~an many other standards
quali~ stable product meant for retail theh' brand the advantages and positioning
of its caliber thanks to its retail support.
A product that Is allowed to carry the that they are looking fur witho.uthurtfng
USDA seal of an organic product has overall quality. • GCI
atleast 9596 ofits solids derimlfrom The GMO Debate
organic ingredients, aclwling water and
salt 'Ihe Certification process also involves .Another growing area of the green DR. SUNDEEP GIU. bas been
a detailed label and formula review; as movement is genetically modified twwid Mil tile b!l&ul¥ and CllBll1ellc
well as ensuring the.product is made in organisms, or GMOs. GMO awareness lnilstly for manyYaara, lbatwarldng for
a USDA organic certified facllity. 'Ihe has gained momentnm in recent yeatBi Carma Qiamallcs In NcMdl\ Cllfomla.
. h 1987, where ha stnd ix01,tlle qually
certifu:ation process for a USDA facility partially due to the narrow loss of . conlrD! lab. He soon WOdllld Im WI'/ i,p
involves manypolid.es and procedures to Callfomia Proposition 37-a statute voted ID a l8Se8R:h chemist, and In 1lia posllkin, ha learned lhe
comply with the complex t:raddclg systems down in November 2012 that would have P!>SSiblllUes Of c:reallng nahnJ plDllUclB based Cll aclence-
required by the USDA. and. in many cases; required labeling ofgenetically engineered Mlen lngrdenls. A1Bw years lalet SUn Deep Cosme11cs
~ llB tl8llllllllUfilCIUr ~ In Hayward. Qdiforda.
manu:&.cturers must weigh if certifi.cation food, with exceptions. n also would 11811111& 611 was Blil ID put his Cl88lt.oe llklla 1n1o mo11on,
is a viable equity to their facility. es it can have dlsallciwed the ~ctice of labeling develqJlng JJOPUlar personal care pnWcls In Iha nalllllil
be very costly to upgrade to the necessary genetically engineere4 food with the word prtdJclB lncllmtry. Dr. Gii allBnded Ile llMnl'1 dllle Paclllc,
standards. "natural.. where he attained his bachekn - and dllmateJy his
. 'Ihe NSP International organic GMO verification in beauty products OOcllJ' rt pharmacy degree. Soon aflar, he CDllpated an
lnbmlNp aixl lllSldency at Slanfanl ~ L1dB Pacl!a!tl
certilication is another green certification relies on simply not using feedstock from
Chldren's ltJspltal and lhu Vebnns llcapllal.lJrqti 1hb
standard that has seen recent success. plants that have been geneticaJlr. modified wmkDr. 6lll pWllslied 88\181118111cles Ill~
and typically 1s J;ll~ feasible for the or crossbred with other sp~es in the and drug delNeiy lllll 118$1sted In 88V!llBI clnk:al ~
production of a functional and stable product's ingredients. .Although no clear invoM1g loplcal drug delVQly and~. IJr. 611 ls B
product.. 'Ibis standard saw most of its difference has ever been substantiated reglsl8rad JOumaclst and 8611 pradlces BS BCUn1caJ jQllmB-(
success when. in 2010, Whole Foods between an ingredient derived from aqlstwhen he Is nat worldng as a persmat care RIS8IRll \
diemlst. And en IYld educallr; Dr. 611 BUii ~to doctDr
enfotced that personal care products sold ·non-GMO ingredients versus ingredients of pharmacy c:andldales Bl'Dllld lhe ~ He Clllldly Ives
on its shelves and maldng a ·contains derived from GMOs, this standard has In San Ramoo, C&llftmla, with his wife and1hree daug!Dn.
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USDA Agricultural
Marketing
1400 Independence Avenue, SW.
Room 2648-S, STOP 0268
Service Washington, DC 20250-0268
Thank you for your petition of June 24, 2015 which requests the inclusion of natural fatty alcohols in
section 205.601 of the National Organic Program's (NOP) National List of Allowed and Prohibited
Substances (National List).
We have reviewed your petition for natural fatty alcohols and determined that it cannot proceed in
the petition process because it does not provide sufficient information to address each item specified
in 72 FR 2167 "National Organic Program - Submission of Petitions of Substances for Inclusion on
or Removal from the National List of Substances Allowed and Prohibited in Organic Production and
Handling." This notice provides information such as what can be petitioned, how substances should
be petitioned, and what information should be addressed in a petition.
To assist you in the development of your petition, we recommend that you modify your current
petition to address the following items:
We noted that the petition requests addition of natural fatty alcohols, specifically, octanol and
decanol, to section 205.60l(a) of the National List.
Based on the requested uses of these substances as growth regulators, we anticipate that they will be
considered by the National Organic Standards Board under section 205.601(k) rather than section
205.601(a).
A final determination will be made by the NOSB during the course of review. However, if an
alternative listing at section 205.601(k) does not meet the intent of the petition, you may wish to
provide additional information on why paragraph (a) of 205.601 if preferred. We noted that
paragraph (a) includes other alcohols; however, it also includes the following text: "As algicide,
disinfectants, and sanitizer, including irrigation system cleaning systems." Paragraph (k) includes
growth regulations that are allowed for organic crop production.
Page2
/
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\
We noted multiple names used for the petitioned substance, including the following: natural fatty
alcohols, fatty alcohols, octanol, and decanol. In addition, the citation provided to FDA regulations at
21 CFR 172.864 uses the term "synthetic fatty alcohols."
Based on our review of the product labels provided, the active ingredients included on the EPA
approved labels are identified as "octanol" and "decanol." To facilitate the review and reduce
potential confusion, we suggest providing additional clarification on the names used within the
petition.
The petition should also clearly indicate why a single petition is needed for the fatty alcohols mixture
(i.e., blend of octanol and decanol) instead of separate petitions for octanol and decanol as individual
active ingredients.
Please also note that natural substances are allowed for use in organic crop production, unless
prohibited at section 205.602 of the National List. The classification for octanol and decanol as
natural or synthetic will be determined by the National Organic Standards Board during the review of
the petition.
We noted that information regarding previous reviews of fatty alcohols by OMRI and other (.
organizations was included in the supplemental tabs. Thank you for this information. For the
response to Item B6 provided at Page 3 of the petition, you may want to provide a brief summary of
this information.
We have reviewed the intended use of the substance against the product labels provide in the petition.
We have noted that the products 0-Tac Plant Contact Agent and N-Tac are labeled only for use on
tobacco. We have also noted the inclusion of email correspondence from EPA staff regarding the
registration of these products for other crops.
From the information provided, we have been unable to verify that the following petitioned uses of
fatty alcohols are currently permitted by the EPA:
• Sucker control on tomatoes
• Meristematic regrowth on vegetable grafts
• Desiccant/defoliant on cotton
For the revised petition, please provide additional information, such as EPA approved product labels,
and/or citations to EPA regulations that confirm that these intended uses of octanol and decanol fatty
alcohols are permitted by EPA. If the intended uses are not currently permitted by EPA, you will
(
Page3
i
I
\ need to amend the petition to remove these uses or wait until EPA registration is granted before
resubmission.
Resubmission:
Please note that electronic submission (by disk or email) is preferred to facilitate posting of petitions
on the NOP website.
If only part(s) of the original hard copy petition need to be updated, submission of only those parts
may be sufficient. If submitting in part, please clearly indicate which section(s) are replaced and
which section(s) can be retained as originally submitted.
Additional information on the petition process is available on the NOP website at How to File a
Petition.
If you have any questions, please contact me by phone at (202) 821-9683 or email
lisa. [email protected].
Sincerely,
x~·~'-13~
Lisa M. Brines, Ph.D.
National List Manager
National Organic Program
CD
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TAB9
PENDING PETITION
INFORMATION
(CORRESPONDENCE)
PERTAINING TO OTHER
PROPOSED USES
'-
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Pesticide Registration
Improvement Act -
PRIA 3: Proposed
petition for adding
Cotton to product labels
, (N-TAC, EPA Reg. No.
51873-20, 0-TAC
PLANT CONTACT
AGENT, EPA Reg. No.
51873-18 and FAIR 85,
PA Reg. No. 51873-7)
Fair Products, Inc .
March s. 2015
Subject: Pesticide Registration Improvement Act - PRIA 3: Proposed petition for adding Cott.on
to product labels (N-TAC, EPA Reg. No. 51873-20, 0-TAC PLANT CONrACT AGENT, EPA
Reg. No. 51873-18 and FAIR 85, EPA Reg. No. 51873•7),
Confinning our communications with you we are providing the following information pert8iliing
to the subject:
1. Proposed Use: Use of Fatty Alcohols to assist with defoliation and desiccation of Cotton
prior to harvest.
4. Proposed Directions for Use: Proposednewuse for the Fatt;y Aleohol Products, (N•TAC,
EPA Reg. No. 51873-20, 0-TAC PLANT CONTACT AGENT, EPA Reg. No•.51873-18
and FAIR 85, EPA Reg. No. 51873-7) consist$ of application to cotton prior to harvest
as a.defOJiant mid .desiccant. The spray so11(1ion showd be, applied as a broadcast spray
12 inches over the top of plants using 2 flat fan. nozzles per row approximately 19 inches
apart that~ 20 gallons ofspray solution per~- ~spray solution consists of
15 to 25% volume/volume (3 to S gallons ofN-TAC, Fair SS and 0-TAC PLANT
CONTACT AGENT) per acte will aid in providing desiccation and defoliation of cotton
leaves when used alone or a tank mix combination with sodium chlorate (6 lbai/a).
We appreciate your review and comments regarding this infonnation for adding this use to our Fatty
Alcohol Product Labels. Let us know if any further information is required at 1his time.
Sincerely,
Carla Hull
Administrative Assistant
Product Registmtion
Carla,
The 2012 test turned out to be just a strip trial because of space that was available. I figured out that was why I had so
much trouble finding the Info on the 2012 test. Unfortunately, there Is very little, if any, information from the 2012
trial. I think we'll need to go with the 2013 and 2014 replicated trials.
Thanks,
Sandy
Sandy Stewart
Research Stations Division Director
NCDA and NC State University
(OJ 91.9-707-3237
(M) 919-414-4863
2 West Edenton Street, Raleigh, NC 27601
1001 Mall SeTVlce Center, Raleigh, NC 27699-10001
NOTICE: E-mail correspondence to andfrom this address may be subject to the North Carolina Public Records Law and
may be disdosed to third parties by an authorized state o/ffclal
Sandy,
NeedASAPI
Thanks,
Carla Hull
FAIR PRODUCTS, INC.
919-467-1599
919-467-9142 FAX
[email protected]
1
(
Alexander M. "Sandy" Stewart, Ph.D.
228 McLeod's Corner
Carthage, NC 28327
over the past three years, I have evaluated 0-TAC fatty alcohol for its activity as a cotton defoliant in
organic systems. I have experience in doing so for many products as a cotton researcher and former
Extension Cotton Specialist for the lSU AgCenter. My evaluations.of 0-TAC have taken pla9e in field
trials in North Carolina cotton from 2011through2014. , (
!
a-TAC has some activity and utility as a cotton defoliant. Although the exact mode of action is not
known, it can be reasonably expected that the fatty alcohol in 0-TAC desiccates the leaf, thereby
rupturing cell walls and stimulating the cotton plant's natural production of ethylene. Ethylene
production is important for forming the abscission layer at the base of the leaf petiole, ·resulting in leaf
drop. This is a very similar mode of action to commercially available cotton defoliants in conventional
cotton production. ·
Results from three field trials over three years in North Carolina have shown 0-TAC to have activity as a
defoliant for cotton production. 0-TAC applied In a single application at in a 15% solution generally
resulted in about 30-40% leaf drop in field grown cotton. Sequential applications do enhance leaf drop,
although results are variable. Tank-mixtures of 0-TAC and ammonium sulfate have typically enhanced
defoliation. However, it should be noted that the optimum rate for application of 0-TAC as a cotton
· · aerollant,.eltneralone or Tri comolnatioh" wrt:n iimmonium .su1rat:e:1s"'iiol: known aftfiis time. Research is
ongoing end additional field trials are needed.
Cotton defoliation is critical to facilitating mechanical harvest with a spindle picker. The removal of
green foliage on a mature cotton crop reduces stain from green leaf and harvest losses with a
mechanical picker. In organic cotton production, the preparation of the crop for mechanical harvest has
always been a barrier to production. Although the overall activity of 0-TAC as a cotton defoliant and
harvest aide is less than conventional products, it does show promise for organic production. The value
of organic cotton dictates that even a small increase in the efficiency of mechanical harvest is
worthwhile. Continuing research with 0-TAC will focus on refining the appropriate rate as well as
exploring appropriate organic tank-mix partners for cotton defoliation.
I look forward to continuing to work with you and Fair Products in the investigation of 0-TAC as a cotton
defoliant and harvest aide. Please let me know if I can be of any assls~nce."
Best Regards,
(
Application Info.
Cotton Trials - 2013
(
Crop Stage at Application 65% Open Bolls
Application Equipment Backpack sprayer with 002 for propellant
Carrier Water
Boom Configuration Two rows, two nozzles per row
Nozzle Type Tee-Jet 110-03 Flat Fan
Nozzle Spacing 19-lnches for two nozzles per row in 38-inch rows
Application Volume 20 Gallons per acre
Height Above Canopy 12 inches
PlotSJze 4 rows, 40 feet long, 38-inch rows
Treated Area Inside two rows in order to utilize a "running check" for each plot
Replications 4 replications
Experimental Design Randomized complete block
3/3/2015
Treatment list
Cotton Trials - 2013
'
3/3/2015
Raw Data
Cotton Trials ~ 2013 (
\
10/24/2013 10/24/2013 10/31/2013 10/31/2013
Defoliation Desiccation Defoliation Desiccation
TRT Treatment Name f!2! Defol7DAT Dess7DAT Defol14DAT Dess14DAT
1 OTAC10% 101 21 15 25 15
2 OTAC 10% +Sodium Chlorate 102 50 25 65 20
3 OTAC15% 103 20 25 25 20
4 OTAC 15% +Sodium Chlorate 104 65 20 65 15
5 Sodium Chlorate 105 so 20 55 25
5 Sodium Chlorate 201 55 25 65 25
1 OTAC10% 202 20 10 25 12
4 OTAC 15% +Sodium Chlorate 203 55 25 65 25
2 OTAC 10% +Sodium Chlorate 204 45 20 55 20
3 OTAC15% 205 25 15 25 25
4 OTAC 15% +Sodium Chlorate 301 50 25 65 20
5 Sodium Chlorate 302 55 25 65 20
2 OTAC 10% +Sodium Chlorate 303 35 20 45 25
3 OTAC15% 304 30 15 40 20
1 OTAC10% 305 15 10 20 10
5 Sodium Chlorate 401 55 25 65 25
2 OTAC 10% +Sodium Chlorate 402 35 15 50 20
1 OTAC10% 403 20 10 20 15
3 OTAC15% 404 35 20 40 10
4 OTAC 15% +Sodium Chlorate 405 65 25 65 20
3/3/2015 c
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,,---.•.
Summary
Cotton Trials - 2013
TRT JAii)_ _ _ _ _ __
Treatment ~a.!!'e .A~~ ~f Dafol.!~~T- t'~".81~.of ~!.!>AT_Av~~-~ De~I ~~~'!. Av_er~g~ r!f Dess 1~~AT_
OTAC 15% 27.5 18.8 32.S 18.8
OTAC 15% +Sodium Chlorate 58.8 23.8 65.0 20.0
Sodium Chlorate 53.8 23.8 62.S 23.8
OTAC 10% 19.0 11.3 22.S 13.0
OTAC .10%
Mun
-·. +Sodium
...• -
----·-Chlorate
------- -- --- ------
41.3
~.1
20.0
19.S
53.8
47.3
------··· 21.3-
19.4
3/3/2015
Application Info
Cotton Trials - 2014 ( '
\_,/
Crop Stage at Application 65% Open Bolls
Application Equipment Backpack sprayer With C02 for propellant
Carrier Water
Boom Configuration Two rows, two nozzles per row
Nozzle Type Tee-Jet 110-03 Flat Fan
Nozzle Spacing 19-inches for two nozzles per row in 38-lnch rows
Application Volume 20 Gallons per acre
Height Above Canopy 12inches
Plot Size 4 rows, 40 feet long, 38-lnch rows
Treated Area Inside two rows in order to utilize a "running check" for each plot
Replications 4 replications
Experimental Design Randomized complete block
( __ _
\.__
3/3/2015
Summary
Cotton Trials - 2014
TRT JAii).___ _ _ __
3/3/2015
...._ ___/
Carla Hull
From: Balan, AsWathy <[email protected]>
Sent Thursday, February 19, 2015 8:09 AM
To: [email protected]
Subject: RE: Pre-application 51873PA1 - 493158
Thanks for your email and I apologize for not getting back to you sooner. We were having some Internal discussions to
determine the best way to move forward. Before getting Into the specifics of the PRIA category, we would like to obtain
some more Information.
I understand you would like to come Jn with one submission for the vegetable rootstalk and another one for the cotton
use. Could you send me a draft proposal of your petition for both uses. The one for rootstock use should list out all the
use sites (right now I know of tomatoes and cucurbits) that you would like to have for that use. Including all the
applicable sites In the initial application itself wlll be advantageous for you. Also provide the widest range of application
rates that would be used.
If you have any questions or concerns please do not hesitate to contact me.
Thanks,
Aswathy
Lindsay Roe had briefed you on the recent activity involving the proposed use of fatty alcohol for control of merlstematic
regrowth on vegetable rootstock, as well as a proposed use as a defoliant/dessicant on cotton. As we proceed, Lindsay
has Informed us that further action will require separate submissions for these.
In EPA's review report (Decision 493158) that proposed use on vegetable rootstock Is exempt from the requirements for
tolerance; therefore, the use is exempt from the residue chemistry data requirements associated with a petition for
tolerance. Likewise, as Lindsay pointed out In her 12/19/14 correspondence, "since cotton use Is classified as non-food,
the tolerance exemption will not have any bearing on that use."
Thus, we are ready to proceed with preparing for two separate submissions (vegetable rootstock and cotton) with a
separate risk assessment for each. Based on the conference call we
1
had with Lindsay and Tony Kish on 12/11/14, it appears that a R-170 submission Is the approach for us to take.
\ can you please provide us the detailed steps and documentation requirements In preparing the R-170 submission. We
are currently preparing risk assessment documentation for each
Thanks you for your assistance on this matter and we look forward to working with you in the furfure.
Roland cargill
By;
Carla Hull
FAIR PRODUCTS, INC.
919-467-1599
919-467-9142 FAX
[email protected]
www.falrproductslnc.com
HI, carla.
\
I just had a handover meeting with the team that will be taking over 1-octanol and 1-decanol. Aswathy Balan Is the risk
manager In the Fungicide/Herbicide Branch that you will be working with, and her product manager Is Shaja Joyner. I
have cc'ed them on this email, so you have their conta.ct information. I briefed both of them on the recent activity with
Fair's proposed product, so feel free to go to them with any questions that you have.
Best regards,
Lindsay
carla-
The Registration Division reorganized in October. Many products and people stayed In the same branches as always, but
a couple of new branches were added and a couple were consolidated, shifting some people and chemicals around. The
Fungicide/Herbicide Branch (one of the new branches) now handles the fatty alcohols but not all plant growth
regulators. Rachel Holloman Is the branch chief. I have already contacted her to find out which specific reviewer, or at
least which team, has been assigned to these chemicals.
\
2
-Lindsay
Lindsay,
Thank you for your prompt response. We were not aware of the reorganization of the Registration Division. Who is the
head of the branch that handles PGR's (ie fatty alcohols)?
Thanks again,
Carla Hull
FAIR PRODUCTS, INC.
919-467-1599
919-467-9142 FAX
[email protected]
www.fairproductslnc.com
HI, Carla.
I talked to Tony about your proposed approach to the no hazard rationale, and before we came to a clear decision (it
might be alright but I honestly don't know- this Is the first no hazard rationale I have ever dealt with), Tony realized that
aliphatic alcohols are no longer handled In our branch as of the reorganization In the Registration Division that took
place several months ago. I am going to have to coordinate a hand-off to another team. I will talk to the branch chief of
the Fungicide/Herbicide Branch and find out who the new risk manager will be. Once I've done that I will talk to the new
risk manager about where we stand regarding this product and put the two of you In contact.
Sorry to be giving you the run-around on this. I should be back to you within a couple of days with information on who
you will be dealing with now.
Best regards,
Lindsay
Hello Lindsay,
We hope that you has a relaxing Holiday. After further thought on the preparation of the Risk Assessment document, ,,
we have decided to take the following approach. As you may be aware, the EPA produced and published risk (_
assessment documentation (human health, environmental, ecotoxicological) in its Reregistration Eligibility Decision
3
(RED) for aliphatic alcohols; Case No. 4004, March 2007. We see no need to "reinvent the wheer', so much of the
documentation that we are providing comes directly from EPA's already published documentation. Of course, we
explicitly note this in tour documentation at the very start of the document, as well as Including the appropriate
citations in our document.
Do you have any comments on our approach?
Carla Hull
FAIR PRODUCTS, INC.
919-467-1599
919-467-9142 FAX
[email protected]
www.falrproductslnc.com
Hi Carla and Roland. There Is no template available, but I will ask around to see If there is an example that we can
release to you. There's quite a shortage of people In the office right now, so I'll get back to you in the next week or so.
Lindsay
Lindsay,
We have a question about preparing a risk assessment. Since we have no experience to date in preparing a risk
assessment, can you please provide to us the rationale, requirements, format, etc. for this documentation so that we
can determine If we have the capability of preparing one ourselves. Thanks once again for your assistance.
Roland Cargill
By
Carla Hull
FAIR PRODUCTS, INC.
( 919-467-1599
' 919-467-9142 FAX
4
[email protected]
www.fairproductslnc.com
HI, carla.
I have emailed one of our contacts at TSG to see If they would mind us referring you to them and if there Is anyone In
particular that you should contact. I will let you know about that once we hear back from TSG. Expect to hear from us In
the next few weeks (but not TOO quickly with the holidays coming up).
Cotton could not be Included In the list of crops because the list of crops will only apply to one use- application to
rootstock of grafted plants. Since Jn the cotton use, product will be applied to growing plants, it will need to undergo a
separate risk assessment, and would thus be charged a separate PRIA fee. These new uses could still be submitted at the
same time, but they should be submitted as two distinct new uses. In addition, since cotton use is classified as non-food,
the tolerance exemption will not have any bearing on that use.
Hope that you and yours have a great holiday. I'm sure we'll be back In touch soon, and don't hesitate to contact us If
you have any more questions.
Best regards,
Lindsay
We thank you both for spending the time with us last Friday to discuss the results of the pre-application (R-124)
' evaluation for use of fatty alcohols to control meristematic regrowth of vegetable rootstock, post-grafting. We have
received the EPA review on this subject. Thank you.
Our current thinking on this subject leans towards taking option 2 that you presented, I.e. the Food Route. We
understand that a rationale for no hazard finding should be developed. You mentioned that TSG has done such a
study/report. Is this something that could be shared with us and/or do you have any contact Information for TSG?
In the meantime, another question has surfaced regarding the use of fatty alcohol on cotton as a desiccant/control of
vegetative growth prior to harvest. Field trials were conducted in Arizona many years ago ( by yours truly) and showed
good activity. More recently, field trials have been conducted in North carolina the last two years and we are currently
awaiting the North Carolina State University Agronomist's report. Could this crop be Included In the broad scope of
crops in option 2 (Food Route) without having to conduct residue studies because of the tolerance exemption?
We look forward to your feedback as we proceed In deciding the best approach for these added uses for fatty alcohol
products.
( ~: '.
5
Thank you and Happy Holidays,
\
Roland Cargill
by
Carla Hull
FAIR PRODUCTS, INC.
919-467-1599
919·467-9142 FAX
[email protected]
www.falrproductsinc.com
As we discussed in our meeting this morning, I am sending you the Health Effects Division's evaluatlon of pre-application
51873PA1 submitted 7/2/2014.
If you would like a hard copy malled to you or if you have any questions, let me know.
Lindsay Roe
EPA/OCSPP
Office of Pesticide Programs
Registration Division, Fungicide Branch
[email protected]
(703) 347-0506
6
( I
-...., ____ -
I Introduction
1bis risk assessment document is prepared to support the proposed new use of fatty alcohol
products to aid in providing defoliation and desiccation of cotton prior to harvest. The only
currently registered use of fatty alcohols is for contact tobacco sucker control. There are no
residential uses. Most of the risk assessment information contained in this document was
prepared by EPA in the following documents:
1. Reregistration Eligibility Decision for Aliphatic Alcohols; EPA 738 -R-07- 004;
March 2007; 23pp.
2. Hwnan Health Risk Assessment; Aliphatic Alcohols; Human Health Chapter of the
Reregistration Eligibility Decision (RED) Document. Reregistration Case Number 4004.
June 30, 2006.
4. Aliphatic Alcohols (1-octanol; 1-decanol): Tier 2 Aquatic Exposure Model (PRZM and
EXAMS) Estimates and Characterization. November 28, 2006.
This document summarizes EPA' s human health and ecological risk assessments and consists of
an overview of the fatty alcohols (aliphatic alcohol) and profile ofits intended use and current ·
uses, as well as the human health and ecological risk assessments.
1
II Chemical Overview
A. Regulatory History
Reregistration case number 4004 consists of straight chain aliphatic alcohols with 6 to 16 carbon
atoms in the chain, which has been abbreviated in previous documents as aliphatic alcohols (Cx-
Cxx) or (C6-Cl6). CWTently, case 4004 consists of four active ingredients. Three of these active
ingredients are used as plant growth regulators on tobacco. These are described as fatty alcohol
blend (PC code 079029), 1-octanol (079037) and 1-decanol (079038). The fatty alcohol blend
under PC code 079029 is predominantly a mixture of 1-octanol and 1-decanol, although some
labels list 0.5% 1-hexanol (C6) and 1.5 % dodecanol (Cl2) among the active ingredients. The
single product listed under PC code 079037, although listed as 1-octanol, is also in fact a mixture
of 1-octanol and 1-decanol. The earliest registered label for use of aliphatic alcohols for tobacco
sucker control included in the Agency's Pesticide Product Label System (PPLS) was issued to
Uniroyal in 1964.
B. Chemical Identification
The aliphatic alcohols are considered primary alcohols (i.e., the -OH group in the C-1 position). The
aliphatic alcohols 1-octanol (PC code 079037) and 1-decanol (PC code 079038) are also known by
many other common names, and the fatty alcohol blend (PC code 079029) is a generic term meaning
that the compound is obtained by the hydrolysis of fatty acid esters. The registrations under the name
fatty a1cohol blend (PC code 079029) are considered a mixture of the linear, straight chain chemicals
I-octanol and 1-decanol. Tables I - 3 provide the chemical identification for 1-octanol, 1-deca.nol,
and J.;dodecanol, respectively.
2
(
Table 2. Chemical Identification of 1-Decanol
Tvne of Information Information for this Chemical
IUPACName l·Decanol
CASRest. No. 112-30-1
Other Names Decyl alcohol; n-Dccan-1-ol; n-Decanol; n-DccyI alcohol; Alcohol
CJO; Caprlc alcohol; Caprinic alcohol; Decanol; Nonylcarbinol;
Decylic Alcohol: Dccan-1-ol; Decanol-(l); Dccyl, n- alcobol 22;
Primarv decvl alcohol; Nonyl carbinol
Empirical Formula C,"HTJ.O
Molecular Weight Number of Carbons 158.28
The number of carbons is I 0
Chemical StructlU'e C-C-C-C-C-C-CC-C-COH
The aliphatic alcohols 1-octanol and 1-decanol are applied as water-based sprays to burley, flue
cured and dark tobacco by hand using a back pack sprayer, or to tobacco plants by a boom. The
aliphatic alcohols are applied to tobacco at the button or early flower stage and act as chemical
pinching agents to control sucker shoots. The aliphatic alcohols dissolve the layer of waxy cuticle on
the plant, causing dehydration of the young sucker. Because these aliphatic alcohols are applied
solely on tobacco. its use is limited to the tobacco growing states, mainly on the east coast
(Connecticut, Pennsylvania, Virginia, North Carolina, South Carolina, Georgia, and Florida). but also
in Kentucky and Tennessee. Between 1.5 and 2 milJion pounds of aliphatic alcohols are applied
annually.
Recommended application rates range from approximately 8.5 lbs ai/acre up to approximately 21 lbs
active ingredient/acre, at 1to3 applications per year. However, 1-octanol and 1-decanol have
estimated volatilization half-lives of3.5 and 1.0 minutes, respectively. Therefore, the amount of the
aliphatic a1cohol available for runoff or for chronic exposure to terrestrial animals is likely to be
lower than the maximum label rates. As described below, the ecological risk assessment took this
into account when estimating potential exposure.
3
Proposed Directions for Use: Proposed new use for the Fatty Alcohol Products, (N-TAC, EPA
Reg. No. 51873-20, 0-TACPLANTCONTACT AGENT, EPA Reg. No. 51873-18 and FAIR
85, EPA Reg. No. 51873-7) consists of application to cotton prior to harvest as a defoliant and
desiccant. The spray solution should be applied as a broadcast spray 12 inches over the top of
plants using 2 flat fan nozzles per row approximately 19 inches apart that delivers 20 gallons of
spray solution per acre. The spray solution consists of 15 to 25% volume/volume (3 to S gallons
ofN-TAC, Fair 85 and 0-TAC PLANT CONTACT AGENT) per acre will aid in providing
desiccation and defoliation of cotton leaves when used alone or a tank mix combination with
sodium chlorate (6 lbai/a).
The aliphatic alcohols are used in, or can be naturally found in various food items. The Food and
Drug Administration pennits the use of aliphatic alcohols as a food additive, wider certain
conditions. The aliphatic alcohols have been found to be natural components of apples and oranges,
and have been reported as a component of edible seeds, oils and fermented beverages.
EPA has conducted a risk assessment of the tobacco plant growth inhibitor use of the aliphatic
alcohols. EPA's screening level assessment was conducted using data submitted by the registrants
and published in the open literature.
A. Executive Summary
(
This document represents the human hea1th risk assessment chapter of the Reregistration
Eligibility Decision (RED) document for the aliphatic alcohols, which include N-decanol,
Cx.-Cxx alcohols. and fatty alcohols. Aliphatic a1cohols are contact sucker control agents
used primarily on tobacco. There are no tolerances or tolerance exemptions established
for residues of aliphatic alcohols on food.
Based on the supported tobacco use, there are no residential uses for the aliphatic alcohols. In
addition, the pesticidal uses of the aliphatic alcohols do not involve use on food and,
therefore, are not subject to the Food Quality Protection Act (1996).
The available acute toxicity studies indicate the aliphatic alcohols are of low oral and
dennal toxicity. Acute inhalation studies with the rat resulted in LDso estimates above
the limit concentration of2 mglL. Eye irritation studies. however, resulted in severe and
sometimes non-reversible eye irritation. Denna! irritation studies revealed slight to
moderate irritation in rabbits. The aliphatic alcohols generally did not produce
sensitization in tests with guinea pigs.
A 90-day dermal rat study (fatty alcohol blend) resulted in irritation at lower
concentrations and before the development of any marginal systemic effects. Slight
changes in hematology, clinical chemistry, and organ weights were noted at the limit
dose of 1000 mg/kg/day. Severe irritation including fissuring of the skin occurred in
40% of the animals at I 00 mg/kg/day and in 80% of the animals at the limit dose.
Avai1able developmental toxicity studies (rat) via the inhalation (1-decanol) and oral
(fatty alcohol blend) routes of exposure resulted in no adverse effects when examined at
the maximum attainable vapor concentration (100 mg/m)) and oral limit dose (1000
4
mg/kg/day) based on fetal and maternal parameters. Genotoxicity and mutagenicity
studies available were negative and long-tenn rodent studies to inform the carcinogenic
potential of the aliphatic alcohols are not available. However, as a class, the straight
chain aliphatic alcohols are generally not carcinogenic. Neurotoxicity information is
cutrently not available, however, there were no clinical signs in any of the acute,
subchronic. or developmental toxicity studies to suggest the aliphatic alcohols elicit a
neurotoxic effect Currently there is insufficient hazard concern to warrant a dose response
evaluation or endpoint selection for quantitative risk estimates. Therefore, no
acute or chronic endpoints have been identified.
An exposure assessment considers the different pathways {food, water, occupational. and
residential) through which exposure to the aliphatic alcohols may occur. Oral exposure
through food is not expected since the aliphatic alcohols have no food uses and there are
no residential uses. Drinking water is not of concern due to: a) the high vapor pressure
and likely volatilization in air; b) atmospheric degradation by reaction with
photochemically produced hydroxyl radicals; c) lack of hazard for the oral route of
exposure; and d) lack of systemic endpoints based on the available studies. Acute and
chronic dietary endpoints have not been selected. Therefore, based on the low hazard
concern, lack of food uses, along with no quantitative toxicological endpoints, a dietary
(food and water) risk assessment is not required.
Since a quantitative dermal endpoint was not identified, no quantitative post application
dennal risk was assessed. For uses within the scope of the Worker Protection Standard
for Agricultural Pesticides (40 CFR 170), a restricted entry interval (REI) was
established. The REI was based on the category assigned to the acute dennal
toxicity, skin irritation potential. and eye irritation potential of the active ingredient. The
appropriate REI is 48 hours if any of the three categories are classified as toxicity
category one.
Based on the lack of food and residential uses and low hazard via the oral, dermal, and
inhalation routes of exposure, quantitative dietary (food and water) and
occupational/residential exposure assessments have not been conducted.
Additionally, the aliphatic alcohols are 'non-food use' chemicals and are not subject to
the amendments to the Federal Food, Drug, and Cosmetic Act (FFDCA) promulgated
under the Food Quality Protection Act (FQPA) of 1996, and an aggregate risk
assessment is not required.
B. Introduction
2. Ingredient Profile
The review of the product chemistry for the aliphatic alcohols was not based on a single
chemical or pc code but rather based on the collective nature of the aliphatic alcohols.
6
59.3 mmHg at 25°C Daubert, TE & Danner, RP
Daubert, TE & Danner, RP (1985); (1989)
MSDS
15.9 at from OH group) Not renorted
Table 2. Phvslcochemical Prooertles AllDhatic Alcohols
Simple Aliphatic Alcohol Aliphatic Alcohol:
Parameter Value/Reference 1-Deconol
Value/Reference
Dissociation constant. PK. Hansch, c et al. (1995)
Octanollwater partition Log Kow Log P= -0.14 Log Kow Log P - 3.79
coefficient Hansch, c et al. (1995) Hansch, c et al. (1995)
UV/visible absorption Data Gap Data Gap
soectrum
Refer to http://www.epa.go,·/athens/researchlregsupportlproperties,btml for further detalla relating to
physical and chemical chemistry
4. Tolerances
As the aliphatic alcohols are not registered for use on food crops, there are no tolerances
established for residues on food. Similarly, there are currently no tolerance exemptions
for the aliphatic alcohols.
The available toxicity database for the aliphatic alcohols consists of acute toxicity,
irritation, and sensitization studies. In addition, there are developmental rat (oral and
inhalation} toxicity studies and a 90-day rat (dennal) study. Mutagenicity studies
available include the Ames, micronucteus, and gene mutation assays. Sources from the
published literature are also included in this hazard assessment. The combination of the
published literature and submitted toxicity studies are sufficient to assess the pesticidal
nonfood uses of the aliphatic alcohols. Based on the low hazard concern via the oral,
dermal, and inhalation routes of exposure, a qualitative hazard assessment is appropriate
for the aliphatic alcohols.
1-Decanol has been found as a natural component in apples and oranges and has been
reported in essential oils of ambrette seeds, almond flowers, citrus oils and fennented (
\
7
beverages (as cited in HSDB. 2005). 1-Decanol is also a pennitted food additive for
direct addition to food for human consumption as a synthetic flavoring substance and
adjuvant in accordance with the following FDA conditions: 1) the quantity added to food
does not exceed the amount reasonably required to accomplish its intended physical,
nutritive, or other technical effect in food, and 2) when intended for use in or on food it is
of appropriate food grade and is prepared and handled as a food ingredient (21 CFR
172.515). There is currently no known mode of action for the aliphatic alcohols. There
are currently no guideline metabolism studies in rats available for the aliphatic alcohols.
The acute toxicity studies available for all three of the aliphatic alcohols (PC Codes
079038, 079029, 079059) are listed in Table AI. The available acute toxicity studies
indicate the aliphatic alcohols are oflow oral and dermal toxicity (Toxicity Categories III
and IV). Acute inhalation studies with the rat resulted in LOSO estimates above the limit
concentration of2 mg/L. However. eye irritation studies resulted in severe and
sometimes non-reversible eye irritation (Toxicity Category I, JI, and III). Dermal
irritation studies revealed slight to moderate irritation in rabbits (Toxicity Category III
and IV). The aliphatic alcohols generally did not produce sensitization in tests with
guinea pigs. More recent acute toxicity data are presented in Table B 1 for the fatty alcohol blend
Active Substance (Alfol 810) and the end use product (N-TAC).
Oral subchronic toxicity studies are not available for the aliphatic alcohols. However, a
90-day dermal toxicity study in the rat is available (MRJD 43701201). Results of the
dennal exposure to a fatty alcohol blend (56.7% decanol, 42.7% octanol) at O. I00,300,
or J000 mg/kg for 5 days/week for 13 weeks included ecythema, edema, desquamation,
eschar formation and exfoliation of all treated animals. The irritation occurred early
\
(within two weeks of the application process) with irritation apparent in a dose-response
fashion. Fissuring of the skin occurred in 40% of animals at 100 mg/kg/day while in
80% of animaJs at the limit dose of 1000 mg/kg/day. Decreased body weight was also
observed at the limit dose (-19% M, -13% F). Slight changes in hematological
parameters, clinical chemistry, and organ weight changes were apparent at the limit dose.
No other gross or histopathological organ pathology was associated with the skin
application of the fatty alcohol blend. The dennal irritation NOAEL was not established
with an irritation LOAEL of 100 mg/kg based on severe irritation. The systemic NOAEL
was 300 mglkgfday w:ith systemic LOAEL of l 000 mg/kg/day, based on hematological,
clinical chemistry, and organ weight changes.
Developmental toxicity studies via the inhalation (1-decanol) and oral (fatty alcohol
blend) routes of exposure resulted in no adverse effects based on fetal and maternal
parameters. A developmental inhalation study exposed Sprague-Dawley rats (J 5) to 15
3ppm (100 mg/m) 1-decanol for 7 hours per day on GD 1-19 (Nelson et al.. 1990a;
Nelson et al. . 1990b). The concentration of 1-decanol selected was based on the highest
concentration that could be generated as a vapor at an average daily chamber temperature
of70-80°F. No treatment-related effects were observed in pregnant females or fetuses
including frequency of resorptions, fetal weights, or skeletal/visceral malformations. An
oral developmental study exposed 25 female Sprague-Dawley rats/dose at O, 125,375. or
1000 mg/kg/day to a fatty alcohol blend (55% decanol; 40.T>/o octanol) on GD 6-16
(MRID 42609301). The maternal NOAEL was 375 mg/k/day and LOAEL was 1000
Mg/kg/day (limit dose), based on increased incidence of salivation (67%). No adverse
effects were observed in the offspring. The developmental NOAEL was 1000 mg/kg/day
(Hl)D with no LOAEL being established.
(
\
8
Genotoxicity and mutagenicity studies available were negative for reverse gene mutations
in Salmonella -ryphimurium, not mutagenic in 2 independent assays with/without
activation at levels ranging from 9.4 µg/ml to 37.5 µ/ml, and negative for mictonucleus
induction in bone marrow cells of male and female CD-I mice harvested 24 or 48 hrs
post-administration of3 daily doses of SOD, 1000, or 2000 mg/kg/day. There is cu1Tently
no long-tenn rodent infonnation regarding the carcinogenic potential for the aliphatic
alcohols.
D. Endpoint Selection
Based on the available data, there is no evidence to suggest that the aliphatic alcohols
cause increased susceptibility in infants and children. Furthennore, based on. the low
hazard concern from the available studies, no endpoints of toxicological concern have
been identified for risk assessment purposes.
E. Exposure Assessment
An exposure assessment considers the different pathways (food, water, occupational, and
residential) through which exposure to the aliphatic alcohols may occur. Drinking water
is not of concern due to: a) the high vapor pressure and likely volatilization in air; b)
atmospheric degradation by reaction with photochemical1y produced hydroxyl radicals
(HSDB, 2005); c) lack ofhamrd for the oral route of exposure; and d) lack of systemic
endpoints based on the available studies. Acute and chronic dietary endpoints have not
been selected. Therefore, based on the lack of food uses and the low hazard concern of
the aliphatic alcohols along with no acute or chronic dietary endpoints being identified, a
dietary (food and water) risk assessment is not appropriate.
Aliphatic alcohols are contact sucker control agents used primarily on tobacco
[N - decanol, alcohols (Cx-Cxx), fatty alcohols). CU1Tently there are no residential uses for
the aliphatic alcohols. There is potential for exposure of occupational mixers, loaders,
applicators, and post-application workers to aliphatic alcohol formulations . However,
due to the low hazard concern of the aliphatic alcohols. no dermal, oral, or inhalation
endpoints of toxicological concern have been identified for the aliphatic alcohols.
Therefore, an occupational/residential exposure assessment is not required.
N-Decanol, alcohols (Cx-Cxx). and fatty alcohols are formulated as liquids and are
applied via the following methods: groundboom sprayer, backpack sprayer, handgun
sprayer, high pressure handwands and low pressure handwands.
9
Available dermal studies indicate that aJiphatic alcohols are acutely irritating with any
possible stress related changes systemically occurring at higher concentrations and over
repeated dermaJ exposure. Mammals are, therefore, more sensitive to irritation than to
any systemic effects and so dermal exposure should be avoided. Available inhaJation
toxicity studies indicate that aliphatic alcohols are oflow toxicity via the inhalation route.
Due to the low hazard profile and lack of endpoint selection for the dennal route of
exposure. no post application dennal risk was assessed. For uses within the scope of the
Worker Protection Standard for Agricultural Pesticides (40 CFR 170), a restricted entry
intexval (REI) was established. The REI was based on the category assigned to
the acute dermal toxicity, skin irritation potential, and eye irritation potential of the active
ingredient. The appropriate REI is 48 hours if any of the three categories are classified as
toxicity category one.
Table 3 Summarv of Maximum Aoollicatlon Rates for Re' lstered Aliphatic Alcohol Products
Chemical Crop Target Formulation Maximum Max#of Application
Application applications Equipment
Rate
N-Decanol Tobacco Foliar EC 21.5 lbs 2 Groundboom
ai/acre for sprayer,
hand sprayer backpack
18.9Jbs sprayer,
ai/acre for handgun
ground boom sprayer, high
pressure
handwands
and low
pressure
handwands
Alcohols Tobacco Foliar Liquid 21.7 Jbs 3
(Cx-Cxx) (EC,SC) ai/arcre
Fatty Tobacco Foliar EC 14.19 lbs 2
Alcohols ai/acre
10
Table 4: Summarv of Maximum aoolication for Proposed uses of Fattv Alcohol Products I
CHEMICAL CROP TARGET FORMULATION MAXIMUM MAXIMUM OF METHOD
APPLICATION APPLICATION
RATE%
Fatty Cotton Broadcast EC 25% 1 Ground
Alcohol application boom
Blend (5 gal I A sprayer
(N-TAC) product) using20
gallons of
spray
solution per
acre
F. Cumulative Exposure
As the aliphatic alcohols are not registered for use on food crops, the requirements of
FQPA are not applicable and a cumulative risk assessment is not appropriate.
G. Summary
1-Decanol has been found as a natural component in apples and oranges and has been
reported in essential oils of ambrette seeds, almond flowers, citrus oils and fennented
beverages. 1-Decanol is also a permitted food additive for direct addition to food for
hwnan consumption as a synthetic flavoring substance and adjuvant in accordance with
the FDA. Aliphatic alcohols are contact sucker control agents used primarily on tobacco
[N-decanol, alcohols (Cx.-Cxx), fatty alcohols]. Currently there are no residential uses
for the aliphatic alcohols.
Based on the hazard profile for dermal exposure to aliphatic alcohols, no post-application
dermal risk was assessed. For uses within the scope of the Worker Protection Standard
for Agricultural Pesticides (40 CFR 170), a restricted entry interval (REI) was
established. The REI was based on the category assigned to the acute dermal
toxicity. skin irritation potential, and eye irritation potential of the active ingredient. The
appropriate REI is 48 hours ifany of the three categories are classified as toxicity
category one,
11
/
Due to the toxicity profile of the aliphatic alcohols, toxicological endpoints of concern
were not warranted for risk assessment purposes. Quantitative dietary (food and
water) and occupational/residential exposure assessments, therefore, have not been
conducted. Additionally, as the aliphatic alcohols are 'nonfood use' chemicals and are
not ubject to FQPA, an aggregate risk assessment is not required.
12
(1
(rabbit) Conjunctive irritation
until 7 and 14 days.
lrreveml>le
vascularisation in one eye
until Day 21.
Table A1: Acute Toxicitv Data for Aliphatic Alcohols
GUIDELINE STUDY PC CODE MRID RESULTS TOXICITY
NO. TYPE CATEGORY
870.2400 Acute eye 079038 46004604 79%decanol III
81-4 initation 1-decanoJ Corneal opacity. irritation
cleared by 6 days.
(rabbit)
Conjunctive imtation,
redness. cbemosis cleared
by 6 days. Moderately
initatinl!.
870.2400 Acute eye 079038 45517902 37.98% decanol III
81-4 ittitation 1-decanoJ Corneal involvement or
(rabbit) initation clearing in 7 days
or Jess
870.2400 Acute eye 079029 44340701 100% fatty alcohols, U-lll
81-4 irritation Fatty Alcohols All 6 rabbits showed
(rabbit) moderate to severe
irritation. Opacity up to 7
days. Slight iritis with
conjunctival redness to Day
6, slight chemosis to Day 7
and slight to severe
dfscharoe to Dav 8.
870.2400 Acute eye 079038 - 78.4% decanol, irreversible
corneal opacity In all 6
I
81-4 irritation 1-decanol
(rabbit) animals. Severe eye
irritation.
870.2500 Acute dennal 079038 44407601 79.2% d11Canol Ill
81-5 irritation 1-decanol 44460405 Primary irritation index 4.0.
(rabbit) Moderate Irritation.
870.2500 Acute dermal 079038 46004605 79% decanol iv
81-5 irritation I-decanol Primary irritation index 0.0
(rabbit)
870.2500 Acute dennal 079038 45517903 37.98% decanol IV
81·5 irritation 1-decanol Primary irritation index 0.0.
(rabbit) Non-irritant.
870.2500 Acute dennal 079038 - J>IS 2.04. Erythema, eschar
formation and edema
Ill
81·5 irritation 1-decanol
(rabbit) evident am hrs. Mild
irritant.
870.2600 Skin 079029 43386201 Fatty alcohol blend C6-CJ2 NA
81-6 Sensitization Fatty Alcohols (99%) All animals
(guinea pig) survived. No adverse effect
on body weight. Not a
dennal sensitizer
870.2600 Skin 079038 44407602 79.2% decanol NA
81-6 Sensitization 1-decanol 44460406 No change in body weight.
(guinea pig) 55% (11120) sensitization
rate.
870.2600 Skin 079038 46004606 79%decano1 NA
81-6 Sensitization 1-decanol Not a dennal sensitizer
13
(euinea nig)
870.2600 Skin 079038 45507903 37.98% decanol NA
81-6 Sensitization 1-decanol Not a dennal sensitizer
(miinea pig)
Table Bl:
TOXICOLOGICAL PROFILE FOR FATTY ALCOHOL BLEND END USE
PRODUCT <N-TAC) AND TECHNICAL SUBSTANCE (ALFOL 810)
*N-TAC
FATTY ALCOHOL BLEND (END USE PRODUCT)
Octanol - 36.2%
Decanol - 48.2%
Related compounds (dodecanol)- 0.3%
Other ingredients (Tween 80)-15.3%
14
Table A2: Subchronlc, Chronic, Developmental, Reproductive and Other Toxicity Profile on the Fatty
Alcohols
Guideline Study MRID Classification Results
No. Twe (Doses)
870.3250 90-day 43701201 1 0-Spraque- Fatty alcohol blend (56.7% decanol, 42.7%
82-3 dennal (1995) Dawley octanol) Primary adverse clinical signs included
rats/sex/dose of 0, eiythema, edema, desquamation, eschar formation
toxicity
and exfoliation of all toxicity treated animals.
100, 300 or 1000 Irritation apparent within 2 weeks after dermal
mg/kgfor5 application. Fissuring of skin observed in 40% of
days/week for 13 animals in low dose while 80% of animals in high
weeks dose. High doses animals exhibited vocalization
and hypersensitivity to touch. Body weight was
reduced in high dose (-19% M, -13% F) animals.
Marginally increased adrenal glands in high-dose
animals, slightly reduced RBC counts, hematocrit.
and increased WBC and platelet counts Jn high-
dose animals. No gross or histological alterations
other than severe irritation.
15
(
\
Table A2: Subchronic, Chronic, Developmental, Reproductive and Other Toxicity Profile on the Fatty
Alcohols
Guideline Study Type MRID Classification Results
No. (Doses)
Develop- Nelson et al., 1990a. Dams weighed daily for first week and weekly
mental 1990b thereafter. Rats sacrificed on GD 20.
Toxicity (rat) 100 mg/m; (max
vapor achievable No treatment related effects observed in
15" F Sprague- pregnant females, frequency of resorptions, fetal
Dawieyn hrs/day on weights, or skeletal/visceral malfonnations.
GD 1-19
870.5100 Gene 42372002 Acceptable/Guideline Negative for reverse gene mutations in
84-2 Mutation (1992) (S5.3% decanol, Salmonella typhimurium TA 1S35. TA 1537, TA
(Salmonella 40. 7% octanol) 1538, TA98, and TA 100 in presence or
ryphimurium) absence ofS9 activation to 6 doses from 1.5
µg/plate to 500 µg/plate (2 independent trials).
Cytotoxicity was apparent for all strains at
500 u.l?/olate +/- 89.
870.5300 Gene 42372003 Acceptable/Guideline Not mutagenic in 2 independent assays
84-2 Mutation (1992) (55,3% decanol, with/without activation. Initial assay non-
(mouse 40.7% octanol) activated & S9 levels ranged from 9.4 µg/ml to
lymphoma 37.5 µglml; doses of37.S }lg/ml severely
cells) cytotoxic. Confirmatory assay with I0-50 µg/ml
- S9 and 30-70 µgtml +S9 were evaluated with
severe cytotoxicity observed at non-activated
levels (60 n~mJ and at S9 activation 80 nl!'/ml).
870.5395 Micronuc1eus 42372001 Acceptable/Guideline Negative for micronucleus induction in bone
84-2 (mouse) (1992) (55.3% decanol, marrow cells of Male and Female CD-I mice
40.7% octanol) harvested 24 or 48 hrs post-administration of 3
daily doses ofSOO, 1000, or 2000 mglk.glday. No
overt toxicity in any treated animal or target
oman in anv treatment omun.
References:
Nelson BK. Brightwell WS, Khan A, Krieg EF Jr, and Hobennan AM (1990b).
Developmental toxicology assessment of 1 -octanol, 1-nonanol, and 1-decanol
administered by inhalation to rats. Journal of the American College of Toxicology. Vol
9(1): 93-97.
HSDB, 2005. Hazardous Substances Data Bank. National Library of Medicine. Search
Tenn: 1-Decanol. http://toxnet.nlm.nih.gov/cgi-bin/sis/search/f? Jtempl-tK9cOq: l
Reaves, Elissa and Recore, US EPA Memorandum: Aliphatic Alcohols; Human Health
16
Chapter of the Reregistration Eligibility Decision (RED) Document. Reregistration Case
Number 4004. June 30, 2006; 13 pp.
N. Conclusion
The proposed addition for the use of fatty alcohol products is as a defoliant/dessicant on cotton
prior to harvest. The proposed use rates of 15-25% volume/volume or 3 to 5 gallon of product/
A (l 8·30 lbasi IA) are similar to the use pattern in tobacco and thus the risk assessment
documentation should apply to this proposed use pattern; i.e. this new use represents no added
risk to hwnans or the environment..
17
c
Subject: Pesticide Registration
Improvement Act (PRIA 3):
Action Code R124; Conditional
Ruling on Pre-application Study
Waivers: Product: N-TAC
(EPA Reg. No. 51873-20), 0-
TAC PLANT CONTACT
AGENT (EPA Reg. No. 51873-
18), Fair 85 (EPA Reg. No.
51873-7)
(Cs-C10 fatty alcohol)
During our original discussions with Tony Kish and Lindsay Roe, we provided the following
information (see March 26, 2015 letter to Tony Kish) pertaining to the use of Fatty Alcohols to
control Meristematic Regrowth on Vegetable Rootstock. ·
Subsequently, we prepared our R-124 Reapplication proposal. In this current draft petition
proposal we are providing the same documentation as provided in the R-124 application. We
have added the following information:
Fair Products, Inc. 0 Agri-Specialties Division c Post Office Box 386 e Cary North Carolina 27512-0386
Telephone: (919) 467·8352@ Fax (919) 467-9142
C. Updated proposed wording for the label that broadens the vegetable crops covered as
follows:
A proposed new use for the fatty alcohol products Fair 85, N-TAC and 0-TAC PLANT
CONTACT AGENT consists of application to control meristematic regrowth on
vegetable rootstocks used for grafting other vegetable crops that are members of the
following plant families; Solanaceae (e.g.. tomato, eggplant, peppers, potato),
Cucurbitaceae (e.g. watermelon, cucumbers, melons, squash, cantaloupe), Brassicaceae
(e.g. broccoli, cauliflower, cabbage and turnips).
We appreciate your review and comments regarding this information for adding this use
to our Fatty Alcohol Product Labels.
Sincerely,
Carla Hull
Administrative Assistant
Product Registration
Subject: Pesticide Registration Improvement Act (PRIA 3): Action Code Rl24; Conditional
Ruling on Pre-application Study Waivers: Product: N-TAC (EPA Reg. No. 51873-20), 0-TAC
PLANT CONTACT AGENT (EPA Reg. No. 51873-18), Fair 85 (EPA Reg. No. 51873-7)
(Cs-C10 fatty alcohol)
References
1. Grafting Methods for Watermelon Production-Richard L Hassell and Frederic Memmott;
HortScience Vol. 43 (6) October 2008.
7. The Effect of Rootstock Age on Grafting Ability, Re-rooting and Field Performance of
Grafted Watermelon Transplants - Abstract.
8. Watermelon Grafting: Progress Update- Shawna Daley and Richard Hassell, Clemson
University CREC, 3/24/14; 9pp.
C. Rationale as to why Fair Products, Inc. believes that this use should be classified u
a nop-food use:
1. The fatty alcohol product is applied to the meristematic tissue on the rootstock before the
graft of the scion is made to the rootstock; thus, the fatty alcohol does not come in contact
with the scion/ grafted plant tissue.
2. The fatty alcohol is not systemic (contact only) and thlis would not translocate to the
scion from the rootstock application. (see page 14 ofEPA•HD-OPP-2007-0134-005,
Ecological Risk Assessment: Aliphatic Alcohols Considered in Registration Case 4004;
by Colleen M. Flaherty and Silvia C. Tenn.es, September 8, 2006 which states regarding
the mode of action of fatty alcohols: "As non-systemic growth regulators, the alcohols are
not translocated in the plant."
3. Fatty alcohols are natural component of plants and studies conducted in tobacco show no
increased residue (see attached article by Tso and Chu.)
Reference:
Residue Levels of Fatty Compounds and Surfactants as Suckering Agents on Tobacco -
T.C. Tso, H. Chu. and D.W. DeJong; Beitrllge zur Tabakforschung Band 8. Heft 4.
December 1975, 241-245.
2
Studies of residue levels of fatty alcohols showed that they could not be detected 26 days
after treatment. Tancogne <1>indicates that C8 and C10 alcohols rapidly decreased even in
the absence of rainfall and high temperatures. Tso et. al. <II. Ill) report that residues of 14C
labeled fatty alcohol were about l ppm compared to a 7000 ppm natural fatty acid
:fraction.
References:
III. Tso, T.C. and Chu, H. (1977). The fate of fatty compounds and surfactants
used as sucker control agents on field tobacco. Beitr. Zur Tabakforschung 9:
58-62.
4. Fatty alcohols are generally accented as biodegradable under both aerobic and anaerobic /
conditions (Steber et al., 1988) {IV). and the breakdown or assimilation by microbial ;\
organisms is rapid and complete. Dissipation of C6-C12 fatty alcohols under field tates
and conditions is rapid and complete. Half-lives as short as a matter of hours could be
possible and would not be expected to exceed 3 to 5 days. (MRID 42135801)
References
IV. Steber, J., P. Gode, W. Guhl. 1988. Fatty alcohol sulfates: The ecological
evaluation of a group of important detergent surfactants. Fett Wissenschaft
Technologie. 90(1): 32-38.
MRID 42135801- Literature review on Fatty alcohol compounds: Lab Project number:
FATF-9101. Unpublished study prepared by compliance Services International. 60pp;
1211811991.
3
further discloses ''Because in general, the biodegradation half-life in aerobic soil is one-
half (1/2) of the half-life in water, the half- life of biodegradation of the three alcohols
(i.e. CS, Cl 0, C12) in aerobic soils is estimated as 4.33 days for ultimate biodegradation.
·The primary biodegradation (I.e. biodegradation to the minimum extent necessary to
change the identity of the compound) half-life is estimated at 2.33 days (aerobic soil) for
1-octanol and 1-decanol, but longer for dodecanol (7.5 days) (EPI Suite User Guide)."
In addition, the following reference (page 2), the Volatilization from Surface of Soil Data
that the half-life for 1-octanol and 1-decanol is estimated at 3.45 minutes and 1 minute,
respectively, using the Dow Method. ·
Reference:
USEPA Memorandum;
Subject: Aliphatic Alcohols (1-octanol; 1-decanol)
Addendum to PRZM and EXAMS refinement of environmental concentrations in surface
water (DP Barcode D334066; 11/28/2006).
Thus, with the grafts being made to the rootstocks 5 to 21 days after the fatty alcohol was
applied to control meristematic growth of the rootstock, the fatty alcohol would be
volatili7.ed or biodegraded by the time grafting takes place.
5. It is important to note that both the active ingredient (fatty alcohol)(V) and the inert
ingredient (polyoxyethyene sorbitan monooleate)- (polysorbate 80)(VJ> are both approved
as food additives by the US FDA.
Reference
D. Application Locations:
Greenhouse,headhouseforgreenhouseoperations
4
(
E. Proposed directions for use: \
Our initial proposed wording for the label instructions could be as follows
(Fatty Alcohol Product Name eg. Fair 85, N~TAC, 0-TAC PLANT CONTACT AGENT)
Application to Control Meristematic Regrowth on Vegetable Rootstocks Used for Grafting
other Vegetable Crops Such as, Watermelon, Cucumbers, Melon, Squash, Cantaloupe and
Tomato.
Vegetable grafting is an alternative approach to reduce crop damage resulting from soil borne
pathogens and increase plant abiotic stress tolerance, which increases crop production - and fruit
quality.
Application of (Fatty Alcohol Product Name eg. Fair 85, N-TAC, O•TAC PLANT CONTACT
AGENT) to rootstock meristems can control rootstock meristematic regrowth, thus decreasing
the cost of producing grafted vegetable transplants by reducing the labor to remove the
meristematic growth by hand.
Apply (Fatty Alcohol Product Name eg. Fair 85, N-TAC, 0-TAC PLANT CONTACT AGENT)
solution (5.0 - 6.25% concentration) to the rootstock by dipping or direct application when the
rootstock seeding cotyledons unfold (5.0%) or when completely unfolded and the first true leaf is
visible (625%) - (generally 5 to 8 days after seeding). · (
'.
5
7. The Effect of Rootstock Age on Grafting Ability, Re-rooting and Field Perfonnance of
Grafted Watermelon Transplants - Abstract.
8. Watennelon Grafting: Progress Update- Shawna Daley and Richard Hassell, Clemson
University CREC, 3/24/14; 9pp.
10. Tso, T.C. and Chu, H. (1977). The fate of fatty compounds and surfactants used as
sucker control agents on field tobacco. Beitr. Zur Tabakforschung 9: 58-62.
11. MRID 42135801 - Literature review on Fatty alcohol compounds: Lab Project number:
FATF-9101. Unpublished study prepared by compliance Services International. 60p;
12/18/1991.
Sincerely,
,{!t?('~
Roland L. Cargill
Product Registration Specialist
6
UNITED STA TES ENVIRONMENTAL PROTECTION AGENCY
WASHINGTON, DC 20460
Roland L. Cargill
Product Registration Specialist
Agri-Specialties Division
Fair Products, Inc.
P0Box386
Cary, NC27512
The EPA has completed an evaluation of your proposal to apply 1-Decanol and 1-0ctanol to
cucurbit vegetables and tomato during the grafting process to control meristematic regrowth.
This evaluation is not an official registration decision but may be used as a tool in planning
further actions associated with these chemicals. You will find the review attached.
If you have any questions, please contact Lindsay Roe by phone at 703-347-0506, or via email at
[email protected].
Sincerely, / ...../ / ·:
~]i~ G.?Pi
ny Kish, P oduct Manager 22
Fungicide Branch
Registration Division (7505P)
Office of Pesticide Programs
[Attachment]
1-Decanoll l-Octanol Preapplication Study DP#: 421961
(
\,
MEMORANDUM
Date: 10/07120 l 4
Background
Fair Products Inc. has proposed the use of n-octanol (capryl alcohol) and n-decanol (capric
alcohol) in the grafting process for cucurbit vegetables and tomato. The root stock is treated with
a 2 - 6% (v/v) aqueous solution of the fatty alcohols 1 - 2 J days prior to grafting the watermelon
or other cucurbit scion. The use is also proposed for tomato, although details are not provided.
The plants are maintained initially under greenhouse conditions and then transplanted to the
field.
1
1-Decanol/1-0ctanol ?reapplication Study DP#: 421961
HED has been requested to evaluate the process and specifically to determine if the use is (
I
food/feed (requiring tolerance) or non-food/non-feed (exempt from the data requirements for \
food and feed use).
The use of n-octanol and n-decanol in the grafting process for cucurbits and tomatoes is a food
use. The information supplied is insufficient to ascertain that no residues will result in the raw
agricultural commodities. However, the use is exempt from the requirements for tolerance. A
tolerance and the requirements associated with the tolerance petition are not needed. Therefore,
the use is exempt from the residue chemistry data requirements associated with a petition for
tolerance. Note that this decision applies only to the two fatty alcohols when used for the
grafting procedure described and does not apply to the general process of treating root stock
(with unspecified chemicals} for grafting. The reasons for the classification as exempt from
tolerance and not non-food use are as follows:
(l) N-octanol and n-decanol are approved inerls (solvent or co-solvent} for pesticide
formulations, and therefore exempt from the requirements for a tolerance
(40CFR§ 180.910). This exemption specifically notes that the inerts may on occasion be
used as an active ingredient, as in this situation.
(2) N-octanol and n-decanol are approved food additives (20CFR§ 172.864- synthetic fatty
alcohols) for direct addition to food for human consumption.
(3) N-octanol and N-decanol (or their ester derivatives) are naturally occurring chemicals.
(4) The 6% solution is applied by dip or spray to each root stock. Dilution upon growth and
development of the plants would lead to very low levels in the cucurbits. However, it is
not possible to conclude with certainty that the residues would be non-quantifiable, a
criterion for non-food use designation.
If the petitioner prefers to pursue a non-food designation, further information and/or studies will
be needed. A calculation of the residue level on the cucumber raw agricultural commodity
(RAC) should be presented based on the proposed label GAP, verifiable data on the translocation
of n-octanol/n-decanol, and horticultural and production conditions for cucurbits. Should the
calculation be equivocal, a radiolabeled study conducted under GAP conditions would be needed
to clearly demonstrate the total radioactive concentrations in the cucumber RAC. If significant
levels are fo\Uld (>5 ppb), it would be necessary to identify the residue as either the fatty alcohols
or as incorporation of the radioactivity into naturally occurring compounds or degradates of no
toxicological concern.
Details
Process-
Watermelon (and other cucurbit) grafting is an important technique for cucurbit production to
avoid soil-borne diseases and as an alternative to soil fumigation. Cucurbit grafting is claimed to
promote plant vigor, to provide increased yield in the presence of disease, and to impart a
tolerance to abiotic stresses (North Carolina State University). For example, hybrid squash or
2 (
\
1-Decanolfl-Octanol Preapplication Study DP#: 421961
bottle gourd rootstock is grafted with seedless watermelon scion. Typical spicing techniques are
as follows:
r
• '·
rr~
..:>-
I
I
..
.
I·~
.
/ ct.v·,_,
\I~
\
~
~tf)
,Ir.·"""---.
]
-~·
clip
··2
Orlll~
.,,
G'~ ~
.::::: ~."
~- dilJ
~.'~
l-·
.--
. I
---
.
, .. ,
or pin
<,If) <.I) CJ)
(q tongue approach grafting
(F, G) cleft grafting
(Jung-Myung Lee, C Kubota, SJ. Tsao, et al.Current status of vegetable grafting: Diffusion, grafting techniques,
automation. Science Horticulturae, 2010. V(127) Iss. 2, P93-I05).
Technique J, splice grafting, is used in the current proposal with the alcohols. There is an
alteration from one cotyledon to zero cotyledon (cotyledon devoid method). Only the hypocotyl
stem is used. After the grafting is completed, the new plants (with old roots cut) typically are
placed in a fresh soil medium in a healing chamber with 95% relative hwnidity and temperatures
of28 -29°C for about seven days. Healing chambers are typically in greenhouse settings.
Fair Products Inc. has obtained a patent (US 8,629,330 B2, 0111412014) for the use of the
alcohols on cucurbit rootstock. The alcohols inhibit meristematic growth on the rootstock
(growth of shoot apical meristem) and also encourage the accumulation of carbohydrates in the
rootstock. Meristematic growth of the rootstock is undesirable, as this leads to competition of
the rootstock growth with the desirable growth from the scion. The accumulation of
carbohydrates helps promote the survival and vitality of the grafted plant.
3
1-Decanol/ 1-0ctanol Preapplication Study DP#: 421961
The proposed directions for grafting with the fatty alcohols include use on watermelon,
cucumbers, squash, cantaloupe, and tomato. The Fair 85 formulation, 5.0- 6.25% concentration, \
is to be applied to root stock by dipping or direct application (spraying, misting, and painting)
when the rootstock seeding cotyledons unfold (5.0%) or when completely unfolded and the first
true leafis visible (6.25%), which is generally 5 - 8 days after seeding.
While no other specifics are provided in the proposed directions, the results of the experiments
(Clemson University) demonstrate that the optimal fatty alcohol concentration is around 6%.
This controls regrow1h from the root stock with no adverse effect on grafting success. Higher
application rates do not significantly increase regrowth suppression but do lead to grafting
failures. Also, rootstock seedlings develop up to 21 days after treatment, suggesting that the
grafting process should be conducted within 3 weeks of treatment.
Some fatty alcohol derivatives are classified as fungicides. An example is potassium oleate (C1s
unsaturated acid), registration number 53219-6. Octanol and decanol are registered as growth
regulators for tobacco, for example, registration number 400-451.
The Reregistration Eligibility Decision for Aliphatic Alcohols was issued in March 2007. 1-
0ctanol and 1-Dexanol are registered as growth regulators for tobacco. It was concluded that
" ... there is no known mode of toxicological action for the aliphatic alcohols. Based on the low
hazard concern via the oral, dermal, and inhalation routes of exposure, a quantitative risk
assessment for the aliphatic alcohols is not appropriate."
N-decyl alcohol (1-decanol) and N-octyl alcohol {l-octanol) are "exempted from the requirement
of a tolerance when used in accordance with good agricultural practice as inert (or occasionally
active) ingredients in pesticide formulations applied to growing crops or to raw agricultural
commodities after harvest" (40CFR§l80.910; Federal Register, 76 (24), 02/04/2011, p 6342).
Both are listed as solvents for pesticide formulations. The Decision Document (Petition 9E7671,
A. Debesai, 01114/2010) included a human health risk assessment which concluded that there is a
reasonable certainty that no harm will result to the general population or to infants and children
from aggregate exposure to n-octyl and n-decyl alcohol inert ingredients.
Concentrations of the alcohols in the final spray mixture from use as an inert solvent would be in
a similar range as that of the proposed use. For example, a formulation that is 50% alcohol and
used at 4 fl oz per gallon of water, would have a 1.5% alcohol concentration is the spray mix.
Moreover, the spray mix might be applied to the entire plant, including edible parts, whereas the
grafting use (6% v/v) involves application to the root stock very early season long before
flowering and formation of the edible commodities.
N-Octanol and N-Decanol are also approved by FDA as additives for foods consumed by
humans. 21CFR§172.864 Synthetic Fatty Alcohols may be safely used in food. 1-0ctanol and
1-Decanol are specifically named components of synthetic fatty alcohols. They may be used as
substitutes for the corresponding naturally derived fatty alcohols permitted in food in parts 172
or 173.
4
1-Decanol/1-0ctanol Preapplication Study DP#: 421961
Both alcohols occur as esters in essential oils. The longer chain lauric acid (C 12) and caprylic
acid, the oxidation product of octanol, occur naturally in some food commodities, including milk,
coconut, palm kernel, plum, and watennelon. N-decanol and/or n--ocatanol is found in apples
and oranges. For example, in citrus oil 1-octanol is up to 0.3% and 1-decanol is up to 0.08%
(Citrus Essential Oils: Flavor and Fragrance, M. Sawamura, John Wiley & Sons, Inc., 2010). It
is ubiquitous in the environment (EFSA, DAR, 2010).
N-octanol and n-decanol are reputed to be non-systemic when used as plant growth regulators on
tobacco (EPA-HD-OPP-2007-0134-005, C. Flaherty, EFED, 08/08/2006). EFSA has concluded
that 1-decanol is non-systemic based on its chemical nature (EFSA Journal 201 O; 8(9): 1715). It
can be speculated that significant translocation into the scion and new growth is not anticipated.
Application is very early season, within days of seeding and long before flowering and/or the
formation of edible parts. From the patent application and Clemson University report, each root
stock is treated with 20 µL of 6% (v/v) solution, or about 1 mg fatty alcohol. Transfer of 100%
of the alcohols to one cucumber of0.2 kg weight (from the many cucumbers on the plant;
average weight of English cucumber is 0.3 kg) would give an alcohol concentration of about 5
ppm. Transfer (100%) to all cucumbers over the growing season would yield about 0.14 ppm
alcohol concentration in the cucumbers. This assumes 2 lbs of cucumber production per plant
per week over a 8 week season per plant, or 16 lbs (7.3 kg) total (University of Florida, IFAS
Extension). The 0.14 ppm is an exaggeration, as the alcohols (1) would not 100% translocate;
and (2) would distribute throughout the plant and would not locate only in the cucumbers fruits.
The degree of exaggeration cannot be quantitated with the available information.
References
PC Code: 879037 and 879038,· Decision Document/or Inert Ingredients Petition number
9E767 l; n-Ocry/ alcohol (CAS Reg. No. 111-87-5) and n-Decyl alcohol (CAS Reg. No. I I 2-30-1)
to Support the Proposed Exemption from the Requirement ofa Tolerance under 40 CFR
180.910. A. Debesai, Petition 9E767J, 11114/2010.
Reregistration Eligibility Decision for Aliphatic Alcohols, D. Edwards, 03/2007, EPA 738-R-07-
004.
Draft Assessment Report (DAR): 1-Decanol. RMS Italy for EFSA. 2008.
Citrus Essential Oils: Flavor and Fragrance, M. Sawamura, John Wiley & Sons, Inc., 2010
5
J-Decanol/1-0ctanol Preapplication Study DP#: 421961
Ecological Risk Assessment: Aliphatic Alcohols Considered in Registralion Case 4004. EPA·
HD-OPP-2007-0134-005, C. Flaherty, EFED, 08/08/2006.
Conclusion of the peer review ofthe pesticide risk assessment ofthe active substance 1-decanol.
European Food Safety Authority, Panna, Italy, 2010 [EFSA Journal 2010:8(9):1715]
~..
6
(
\
Row Crop Research and Production
I '
The Effect of Rootstock Age on Grafting Ability, Re-rooting, and Field Performance of Grafted
Watermelon :Transplants
Fatty alcohol treatment is a useful technology that prevents rootstock regrowth in Bottle.Gourd
(Lagenaria siceraria) and lnterspecific Hybrid Squash (Cucurbita maxima x C. moschata) rootstocks.
During a three-week period after treatment, rootstock carbohydrates have been shown to increase.
This increase could provide energy to improve graft healing and rootstock re-rooting. This positive
effect on transplant quality could lead to an eventual improvement in overall fruit quality and yields. A
greenhouse grafting experiment and an ope~-fleld trial were conducted to characterJie this effect.
Bottle Gourd (cv. 'Macis;) and lnterspecific Hybrid Squash (cV. 'Carnivor') rootstock seed were sown in
subseque.nt weekly plantings to achieve rootstock ages of 1, 7, 14, and 21 days after fatty alcohol
application. All rootstocks were grafted using Tri-X 313 scion. The age of the scion was the same for all
rootstock types, and the grafting was done on the same day usi~g the one-cotyle~on grafting method.
weights were rec9rded. Percent ro~ting~ root length density (RLD) and surface area (SA) were also
.measured. Increases for both cultivars were observed as rootstock age Increased. Grafted plants were
also planted in a field at the Clemson University Coastal Research Station In Charleston, SC. Transplant
survival was recorded and aerial tissue fresh and .dry weights from two plants per plot were measured.
Yield data, including number and weight of fruit produced per plot and number of harvest~ per plot, was
also collected. Significant effects in both plant growth and fruit yields were observed depending on the
I
t.
-1-
(
Poster:
Rootstock Age Affects Grafting Ability and Rootstock Re-rooting of Grafted Watermelon Transplants
Regrowth from the rootstock of a grafted watermelon competes with the scion for nutrients and
sunlight, and could cause yield Joss and scion abortion. Control of regrowth is costly and labor-intensive.
Fatty alcohol treatment of the merfstem is a useful technology that prevents rootstock regrowth, thus
reducing overall transplant costs. During a three-week period after treatment, rootstock. carbohydrates
increase while pla~t growth is prevented. This increase could pro~ide needed energy to improve graft
healing of the scion and encourage rootstock re-rooting. Agreenhouse grafting experiment was
conducted to determine the effect of rootstock age after fatty alcohol treatment on graft healing and re-
rooting. Bottle Gourd (Lagenaria siceraria OJ. 'Macis') and lnterspecific Hybrid Squash (Cucurbita
maxima x C. moschata cv. 'Carnivor') rootstock seed were sown in subsequent weekly plantings to
achieve rootstock ages of 1, 7, 14, and 21 days after fatty alcohol application. All rootstocks were
grafted using·Tri-X 313 scion. The age of the scion was the.same for all rootstock types, and the grafting
was done on the same day using the one-cotyledon grafting method. Two weeks after grafting, the
percentage of healed grafts, scion fresh and dry weights, percent rooting, root length density (RLD),
surface area (SA), and number of forks were measured. Significant effects of scion and rooting
characteristics were observed over changes In rootstock age after fatty alcohol treatment.
. J I.. • -
3/24/2014
Watermelon
Grafting:
Progress Update
f!·J1ft!t'J't?f': r>aley & Dr. Rllchard KRSseH
Cfl!m!i'on University c~c
Coe:1r iE.'fit<•n, Sctuth ~roflr-Lf US/~
Our Concentration
Control of rootstock
regrowth
ACompetes for
· space In the field.
<Stunts scion
growth
1
3/24/2014
(
Chemical Control
Preliminary Research
2
3/24/2014
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2 products, 9 rates
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3/24/2014 r
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4
3/24/2014
Observations
Rootstock seedlings
Increase In size
over time after
treatment.
Hypothesize an
Increase In stored
carbohydrates.
(
'
s
3/24/2014
Rootstock Analysis
1, 7, 14, and 21 days.
2 rootstocks
Results: Hypocotyl
Development
1llble S. Effect of time lftlrfltty akdlal ftatmenl'I on 'Emphufs' Ind 'Clmlvor' rootstock
lwPomtvl' dMlopment
.......
.....
.....
.......... ,.......
-·1 ....-·1
.........Ii !!!r;IMll&litfll '-"'el Wlhl!!!!!l
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7 ......
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11.41.
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lot MlllS. II.ISi. IS.a •
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DllllelQ 1111t IP 'D.1151
6
3/24/2014
Results: Cotyledon
Development
i.ble 4. Bli!ct af time after fatty alcohol trntmenl' on 'Emphasis' and 'Clmlvor' rootstodl
mtyfedonY dMlopment
Colyledon
'l
Fresh Wef&ht DryWeJ&ht Len&lb Width 1hldcnea
RoCllstadc IW Ill II! f!!!!!!I !mml fan2!.ll
=~1
fm!lhl* 1 (Wltar) 0.0218 311.U • G.1159 I
1 O.G225 b 15.42 b 28.n I ll.0&7 I
7 CJ.3539 b G.0595 I D
IT.29Hb 21.41 I 1UJ1i5 I
14 0.4712 I ll.Cl&llli • 42.49 lb 22.92 • 11J1112 I
21 o.ms • 0.11191 I 44.55 I 24.15 • 0.070 I
RESULTS: CARBOHYDRATES
Tlble s. Effect of time lfterfltly 1lmhol trutment' on 'Emphasts' llld 'Camlvor' rootstockTUllll
Soluble Su&ll" (TSS) llld Stlrdf mntellt I!!: HlPamtvl llnd Cotyledon
Hypacolyl" Colyledon'
°"'5Afllr 1SS 5tlrdl 1SS Slmdl
Rootstac:t Tllllment Bl (Ill) WI} (pf/I)
Eqlhuls l(Wltlrj 1.017 llr;9 O.D23 b 0.&63 b Cl.OR c
1
7 3 32 9, 109
14 1.931 lb 0.469 lb 4.530 I 2.1&6 b
21 1.521 I 0.724 I 5.930 I 3.487 I
7
3/24/2014 ( \
\.
Analysis Conclusions
• Rootstock seedlf ngs continue to develop and expand
over 21 days after fatty alcohol treatment.
• Seedlfngs Increase In carbohydrate content, most
notably starch.
(·.
\ ...
8
3/24/2014
/
\
Grafting Trial
Determine effect of Increased starch on grafting
success and rootstock re-rooting
Experiment l
, One-Cotyledon Method
Experiment 2
· Hypocoytl-Only Method
9
3/24/2014 (
I
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Applications
Expanded grafting
window
from 2·3 days to
2·3 weeks
Acknowledgements
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10
Grafting Methods for Watermelon Production
Richard L. Hassell1 and Frederic Memmott
Clemson University, CREC, 2700 Savannah Highway, Charleston, SC 29414
Dean G. Liere
Syngenta Seeds, Inc., 5355 Monterey Frontage Road, Gilroy, CA 95020
Additional index words. cucurbit, rootstock, scion
Abstract. Vegetable grafting is most common in European and Asian countries where crop rotation is no longer an option
and available land is under intense use. Grafting is an alternative approach to reduce crop damage resulting from soil borne
pathogens and increase plant abiotic stress tolerance, which increases crop production. We discuss and outline four grafting
methods that are available for vegetable production in cucurbits: tongue approach grafting, hole insertion grafting, one
cotyledon grafting, and side grafting.
The initial grafting method used for done by growers adapting to their particular MATERIAL AND GRAFTING
melon was cleft grafting (Ishibashi, 1959), operation. The tongue approach technique, METHODS
but after the introduction of the tongue which has a high survivor rate in general, is
approach grafting method, its use diminished chosen by nonexperienced farmers who are Quality seed and proper plant growth
greatly. The tongue approach method became looking into grafting for the first time and procedures of both rootstocks and scion
widespread in Asia because of its higher have plenty of space and adequate labor. One material are critical for grafting to be success-
success rate and the uniform growth of cotyledon and hole insertion grafts require ful.High-quality seed with a uniform germi-
grafted seedlings. In Italy, the most common specialized tools and a healing chamber for a nation is a must. If primed seed is available,
have been the approach and cleft methods high survivor rate and require time to learn. In take advantage of it. This seed germinates
(Bianco, 1990; Buzi et al., 2002; Morra, addition, the graft junction needs to be above- sooner and with greater uniformity. If seed-
1997), but currently the one cotyledon ground during grafting and healing to avoid less watermelon seed is used as the scion
method and the hole insertion method are the direct contact between the scion and soil material, use the methods for uniform seed
used (Amadio, 2004). In Spain, a high pro- because adventitious root are easily stimu- germination described by Hassell and Schul-
portion (more than 90%) of watermelon lated, which will defeat the purpose of the thesis (2002). Rootstock seed is generally
plants are grafted using the one cotyledon graft. sown 5 to 7 d before scion seed regardless if
method (Miguel and Maroto, 2000). In In automatic (machine-driven) grafting, they are grown in cell trays or germination
France, both the side insertion and the tongue the requirements for the growth of the root- beds. The cotyledon of rootstocks should be
/ approach have been used in cucurbits stock and scion are just as critical as in fully expanded when the scion emerges,
\ (Brajeul and Letard, 1998). Top insertion manual grafting. Uniformity in both germi- keeping the scion at low relative humidity
grafting is the most popular method used in nation and growth of the rootstock and scion before grafting can minimize pathogen dis-
China, because it is suitable for Lagenaria are more critical for the robotic-driven eases. Watermelon scion are harvested (I or
and interspecific squash as rootstocks machines. Machine grafting is done using a 2 d) after they emerge, rinsed with clean
and requires few materials, has a high effi- simple machine or a grafting robot, which is water, and then treated with fungicides or
ciency, 1500+ plants/day/worker, and sim- expensive. New machines are currently being disinfectant, e.g., Physan 20 or peroxyacetic
pler management requirements (Lee and developed in Japan and Korea that are much acid/hydrogen peroxide, to minimize the micro-
Oda, 2003). more forgiving and require less labor to organism damage to the graft. The rootstock
operate. The grafting method generally used should have good tolerance to abiotic stress,
GRAFTING TECHNIQUES by these machines is the one cotyledon graft. resistance to soilborne diseases, and not
It is well adapted for machine operation and negatively affect fruit quality. The compati-
There are two techniques used in grafting, has a high rate of success. However, there are bility between rootstock and scion should be
manual and machine (robotic grafting). In constant adjustments being made to the high and stable. In general, grafting compat-
manual grafting, the grafting and postgrafting machine at the cutting arm to adjust for the ibility is related to taxonomic affinity. For
operations require three to four people, each variation in hypocotyl thickness or lack example, luffa and melon have higher com-
assigned to a specific step in the process (Lee thereof. Removal of one of the cotyledons patibility with nettle melon compared with
and Oda, 2003). Cucurbits are usually grafted from the hypocotyl at just the right depth and chinese pumpkin and wax gourd (Wei et al.,
once the first true leaf appears but before it angle is critical for the take of the graft and 2006). Grafting incompatibility can occur at
reaches full development both in the root- also for preventing shoot development from an early stage because vascular connection
stock and scion seedlings. To reach this stage the rootstock. The first semiautomatic graft- cannot form properly after grafting. Grafting
for both the scion and the rootstock, planting ing system for cucumber was commercial- incompatibility can also be delayed until
dates will vary depending on the rootstock ized in 1993 and numerous others have been fruiting stage when massive amounts of
and scion chosen, greenhouse temperatures, developed since then. A simple grafting nutrition and water are needed. Grafted plants
and seed germination criteria. Different graft- machine can produce 600 grafts per hour then decline early and successful harvesting
ing approaches have been adapted depending with two operators as compared with manual is impossible. There is a positive correlation
on scion and rootstock purpose, grafting grafting making ~ 1000 grafts per person between the vigor of grafted watermelon
technique, grower experience, and postgraft- per day (Lee and Oda, 2003; Masanao and and the similarity of protective isozymes,
ing management condition. The tongue Hisaya, 1996; Suzuki et al., 1998). In Spain, e.g., peroxidase and superoxide dismutase,
approach, hole insertion, and one cotyledon the automated methods represent less than between grafted and regular seedlings
grafting are the currently preferred methods. the 5% of the total cucurbits but may be as (Zhang et al., 2006). The age of the rootstock
Modifications to these methods have been high as 10% in Japan and China. At present, and scion also plays an important role in
40% of watermelon grafting in Japan is compatibility. Optimal seedling age varies
done by the automated method (Lee and for species and different grafting methods. If
1
To whom reprint requests should be addressed; Oda, 2003; Masanao and Hisaya, 1996; Suzuki seedlings are too young, they are too tender to
e-mail [email protected] et al., 1998). handle during the grafting process and if they
/
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Abstract
Watermelon grafting methods vary from Europe and Asia and are based on
efficiency, skill and needs. China mainly practices the whole insertion grafting method
where as Europe and Japan employs the splice/slant-cut grafting method. These
methods are not suitable for grafting production in the U.S. due to the intense amount
of labor cost necessary to successfully produce grafted watermelon transplants. This
paper introduces a modified grafting technique called the "cotyledon devoid" method.
Both rootstock cotyledons are removed at time of grafting to eliminate any potential
rootstock regeneration. By allowing the rootstock and scion material to develop, to the
appearance of the second or third true leaf before grafting, (employing the complete
removal of both cotyledons) grafting success greatly increase. Furthermore by
removing the need to maintain an active root system by excising the root, hypocotyl
energy reserves can be conserved to initially heal the graft union and then generate
new roots as needed. Grafting was performed on ten plants in five replications using
four different rootstocks: Lagenaria siceraria 'Emphasis', Citrullus lanatus var.
citroides 'Ojakkyo', Cucurbita moschata x Cucurbita maxima 'Strongtosa', and
Citrul/us lanatus var. lanatus 'Tri-X 313'. All scion material was Citrul/us lanatus var.
lanatus 'Tri-X 313'. Rootstocks and scion material was allowed to develop conjointly
to the appearance of the first, second and third true leaf whereupon both cotyledons
were removed and grafting was performed at each respective developmental stage. A
65° angle was cut below and half an inch below the rootstock and scion cotyledons
respectively. Opposing cuts were matched together and secured with a plastic clip.
Roots were subsequently excised from the rootstock at soil base and inserted into fresh
media for rooting. Grafts were randomly placed inside a healing chamber for 7 days.
INTRODUCTION
Watermelon grafting is an important part of watermelon production to avoid soil-
borne diseases and/or chemical fumigation in areas where land rotation is not feasible.
Current commercial grafting practices depend on maintaining at least one rootstock
cotyledon during the healing period following grafting for high survival (Cushman, 2006;
Lee, 1994; Lee and Oda, 2003; Oda, 1995). Rootstock re-growth originating from
meristematic tissue next to the remaining cotyledon is one main contributing barrier
preventing affordable costs which prevent its introduction into the United States
agricultural system (Edelstein, 2004). With the phase-out of methyl bromide fumigant
new interests are being reviewed for potential alternatives (Cohen et al., 2007; Davis et
al., 2008). For many years grafting in watermelons has been viewed as an option solely in
areas where labor costs are minimal. This benefit has great potential to have a very
positive effect for commercial production in the United States by improving the plants
overall environmental efficiency and overcoming soil-borne pathogens. An alternative
grafting method which eliminates potential re-growth is needed in order for grafting
technology and benefits to progress into the United States. Removal of both cotyledons in
a one step fashion at time of grafting eliminates all potential re-growth and greatly
reduces overall grafting costs. Observations indicate however that the rootstock hypocotyl
begins to yellow and declines until death when grafted at the I st leaf stage or younger
(
Proc. 4th IS on Cucurbits
Ed.: Xiaowu Sun 389
Acta Hort. 871, ISHS 2010
which is customary for current commercial grafting techniques. The yellowing and steady
decline of the hypocotyl, which results in rootstock death, simulates leaf senescence and
suggests that insufficient nutrient reserves were available to the hypocotyl prior to
grafting. Without sufficient stored carbohydrates, the hypocotyl cannot sustain itself long
enough before receiving photosynthates from the newly grafted vegetative tissue. When
plants are allowed to mature to the appearance of the 2nd or 3rd leaf, hypocotyl
deterioration is not observed, suggesting perhaps that more reserves are available with
maturity to maintain the rootstock until graft healing is complete.
390
which was located inside the greenhouse. The healing chamber was constructed with a
rectangular wooden box with the following dimensions: width of 86 cm, a length of 300
cm, and a depth of 14 cm and covered with polyethylene sheet. The humidity was
maintained using the 707U-duct mount centrifugal atomizer humidifier (Herrmidifier,
Effingham, Illinois).
CONCLUSION
Larger hypocotyls suggest an increase in stora~e capaciP' or an overall increased
carbohydrate reserves from the 1st leaf stage to the 2 d and 3r due to larger hypocotyl
size. Results indicate that this new method could be used to reduce costs by eliminated
rootstock side shoots only if performed when the rootstock has developed to the 2°d or 3rd
true leaf stage. We also found that using scion material at the 3 r leaf stage may be
another contributing factor to increase grafting success.
Literature Cited
Cohen, R., Burger, Y. and Horev, C. 2007. Introducing grafted cucurbits to modem
agriculture an Israeli experience. Plant Disease 91 :916-923.
Cushman, K. 2006. Grafting Techniques for Watermelon. University of Florida Institute
of Food and Agricultural Sciences HS1075, 1-5.
Davis, A.R., Perkins-Veazie, P., Sakata, Y., Lopez-Galarza, S., Maroto, J.V., Lee, S.-G.,
Huh, Y.-C., Miguel, A., King, S.R., Cohen, R. and Lee, Y.-M. 2008. Cucurbit Grafting.
Critical Reviews in Plant Sciences 27:50-74.
Edelstein, M. 2004. Grafting vegetable-crop plants: Pros and cons. Acta Hort. 659:235-
238.
Lee, J.-M. 1994. Cultivation of grafted vegetables I. Current status, grafting methods, and
benefits. Hort Sci. 29:235-239.
Lee, J.-M. and Oda, M. 2003. Grafting of herbaceous vegetable and ornamental crops
Horticultural Reviews 28:61-123.
Oda, M. 1995. New grafting methods for fruit-bearing vegetables in Japan. J ARQ 29: 187-
194.
391
c
Table 1. Grafting success and hypocotyl growth of seedless watermelon grafted on
various rootstocks at different leaf stages of development.
Table 2. Pearson correlation coefficients (R2) between rootstock hypocotyl area, diameter
or length and grafting success.
Rootstock HypocotylY
Cultivar Type Area Diameter Length
(cm 2) (mm) (mm)
Ojakkyo Wild watermelon 0.781 z 0.681 0.565
Strong Tosa Interspecific hyb. 0.784 0.655 0.828
Emphasis Bottled gourd 0.825 0.655 0.676
Tri-X 313 Seedless watermelon 0.721 0.874 0.630
YHypocotyl measurements represent a total ofa ten plant sample replicated five times.
'Values are significant at P=0.05.
392
Figures
4. 5.
Fig. 1. Cotyledon devoid method described as a five step process (Hassell et al., 2008). 1)
Both cotyledons are cut from the rootstock at an approximate 65° angle; 2) The
scion is cut at an approximate 65° opposing slant to the rootstock; 3) The scion
and rootstock wounded regions are joined and secured with a clip; 4) The
rootstock hypocotyl is cut just below the baseline; and 5) The grafted seedling is
then re-stuck in a new cell with fresh soil media.
393
(
394
CROP PRODUCTION
1 Improvement of Grafted Watermelon Transplant Survival over Time by Rootstock Fatty Alcohol
2 Treatment
1
4 Shawna L. Daley
5 Department of Plant and Environmental Sciences, Clemson University Coastal Research and Education
7 Jeffrey Adelberg
8 School of Agricultural, Forest, and Environmental Sciences, Clemson University, 275 Poole Agricultural
10 Richard L. Hassell
11 Department of Plant and Environmental Sciences, Clemson University Coastal Research and Education
1
13 Corresponding Author. Email address [email protected]
14
(
2
16 Improvement of Grafted Watermelon Transplant Quality over Time by Rootstock Fatty Alcohol
17 Treatment
18
19 Additional index words. cucurbit grafting, interspecific hybrid squash, Cucurbita maxima x C. moschata,
21
22 Summary. Rootstock fatty alcohol treatments have been shown to increase the efficiency of producing
23 grafted transplants by controlling cucurbit rootstock meristematic regrowth and by allowing the
24 rootstocks to accumulate carbohydrates, especially starch, over time in the hypocotyl and cotyledon. A
25 grafting experiment was conducted to determine the effect of increased carbohydrates over time on
26 transplant quality of watermelon grafts using standard grafting procedures. lnterspecific hybrid squash
27 (Cucurbita maxima x C. moschata 'Carnivor') and bottle gourd (Lagenaria sicereria 'Macis'J rootstocks at
28 1, 7, 14, and 21 days after fatty alcohol treatment were grafted with seedless watermelon cultivar Tri-X
29 313 (Citrul/us lanatus var. lanatus) using the one-cotyledon method. Graft quality on 'Carnivor'
30 rootstocks was acceptable or significantly increased up to day 14, with a slight decrease at day 21. Graft
31 quality on 'Macis' rootstock was also acceptable up to day 21, with a significant increase between days 1
32 and 7. The second experiment was conducted to determine whether the increased carbohydrates
33 provide sufficient energy to successfully graft without the rootstock cotyledon, a method that has
34 previously shown inconsistent results. Graft survival was improved by 90% using treated 'Carnivor'
35 rootstock 7 days after fatty alcohol treatment and 'Macis' rootstock 14 days after fatty alcohol
36 treatment. Adoption of the hypocotyl-only graft method in commercial production may increase
3
37 efficiency by better-utilizing greenhouse space, and could decrease disease probability by removing the
(
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38 cotyledons before grafting.
39
40 Grafting watermelon [Citrullus lanatus (Thunb) Matsum and Nakai] onto disease-resistant rootstocks can
41 confer resistance to soil borne diseases such as Fusarium wilt (Fusarium oxysporum f. sp. niveum) and
42 Monosporascus root rot (Monosporascus cannonballus), (Beltran et al., 2008, Guan et al., 2012, Louws
43 et al., 2010). With the loss of methyl bromide as part of the Clean Air Act (U.S. Department of
44 Agriculture (USDA), National Agricultural Statistics Service, 2012), watermelon grafting is currently the
45 most promising method of Fusarium wilt control (Louws et al., 2010). While only five percent of
46 watermelon acreage in the U.S. is currently reported to be affected by this disease (D. Liere, personal
47 communication), arable land for rotation is decreasing, and the cost of traveling to disease-free soil is
48 difficult for growers to overcome. Although the demand for commercially-produced grafted plants is
\.
49 apparent, high production cost remains a major impediment to grafted transplant adoption in United
50 States production.
51 The two most common commercially-used grafting methods (over 90%) are the hole-insertion and the
52 one-cotyledon method (Hassell et al., 2008). These methods require at least one cotyledon to remain
53 intact to ensure graft success (Hassell et al., 2008), and both require manual meristem removal with a
54 blade during grafting and even prior to transplanting of grafted plants. Manual meristem removal often
55 removes the meristem only partially, allowing meristem regeneration to occur. Our previous studies
56 have demonstrated the success of fatty alcohol rootstock treatments in controlling meristematic
57 regrowth (Daley and Hassell, In press). Fatty alcohol products are traditionally used in tobacco
58 (Nicotiana tabacum L.) production to remove axillary meristems and promote growth of remaining
(
\ .59 leaves. When fatty alcohol products are applied to rootstocks used for grafting watermelon, the
4
60 rootstock meristematic tissue is destroyed and the rootstocks remain viable for grafting (Daley and
(
61 Hassell, In press).
62 In addition to regrowth control, rootstocks treated with fatty alcohol continue to live and
63 photosynthesize, as the cotyledons are also functional leaves (Bisognin et al., 2005). Rather than putting
64 energy into new growth, carbohydrates are stored in the hypocotyl and cotyledons of the rootstocks
65 (Daley and Hassell, 2014). Previous experiments have revealed a starch increase of 100- and 200-fold in
66 hypocotyls of bottle gourd (Lagenaria sicereria) and interspecific hybrid squash (Cucurbita maxima x C.
67 moschata) rootstocks, respectively, over 21 dafter fatty alcohol treatment (Daley et al., 2014). We
68 hypothesize that this increase of stored energy in the rootstock could be harnessed by the plant to
69 improve current grafting methods by providing sufficient energy to increase graft survival, rootstock
70 rooting, and overall grafted transplant quality. The first experiment outlined in this paper was designed
71 to determine the effect of increased rootstock carbohydrate content on graft survival and rootstock re-
73 With current grafting methods, at least one cotyledon is left on the rootstock during grafting. Because
74 the rootstock cotyledons are larger than the cotyledons of watermelon seedlings, the rootstocks require
75 an increase in individual tray cell size over standard cell size for grafted watermelon transplant
76 production. This larger cell size is needed to accommodate the rootstock cotyledon when grafting. In
77 addition to requiring a greater cell size, the large rootstock cotyledons can also harbor foliar disease
78 such as powdery mildew (Podosphaera xanthii) (Kousik et al., 2008) that can prevent successful graft
80 Decreasing the tray cell size and preventing the spread of disease via the rootstock cotyledon is an
81 important objective in improving the efficiency of grafted transplant production. The development of a
82 successful grafting method that removes both cotyledons would be advantageous to commercial
c
5
83 production; however, results of previous studies on this type of method proved to be rather inconsistent
84 for commercial application (Memmott, 2010). Because the cotyledon has been shown to provide energy
85 to the developing rootstock seedling (Bisognin et al., 2005), we hypothesize that the inconsistencies in
86 previous attempts to graft without the cotyledons were a result of a lack of energy in the hypocotyl to
87 support the graft healing and re-rooting of the transplant. The increased starch reserves in rootstocks
88 treated with fatty alcohol over time may provide the required energy to overcome the reliance on the
89 cotyledon and make grafting to the rootstock hypocotyl without the cotyledons feasible, (Daley et al.,
90 2014). Thus, a second experiment was conducted to test this hypothesis and demonstrate the effect of
91 rootstock age after fatty alcohol treatment on graft survival and rootstock re-rooting using the
( 94 Experiment 1. The first experiment consisted of 2 rootstocks: bottle gourd 'Macis' (Lagenaria sicereria)
95 (Nunhems USA, Parma, ID) and interspecific hybrid squash 'Carnivor' (Cucurbita maxima x C. moschata)
96 (Syngenta Seeds, Boise, ID). When the cotyledons had unfolded but not expanded (approximately 6-8 d
97 and 8-10 dafter seeding for 'Carnivor' and 'Macis' rootstock, respectively) seedlings were individually
98 treated with 20 µL 6.25% fatty alcohol (Fair 85; Fair Products, Cary, NC) applied to the meristem of the
99 rootstock, as described by Daley and Hassell (in press). Rootstocks were held in the greenhouse for 1, 7,
100 14, or 21 days after treatment (DAT) before grafting. Rootstock seeding and treatment dates were
101 scheduled weekly such that grafting for all treatments occurred on the same date. Seedless watermelon
102 cultivar Tri-X 313 (Citrullus lanatus var. lanatus) (Syngenta Seeds Boise, ID) was used as scion, and seeds
103 were sown, following growing procedures outlined by Hassell and Schultheis (personal communication),
104 on the same day as the 14-day rootstocks. This timing ensured that the scion age (2 weeks after
105 seeding) was the same for all treatments. Each rootstock treatment consisted of 10 plants, and was
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6
106 replicated 4 times. The entire experiment was repeated twice, with grafting occurring in April and July of
107 2013. Grafting was performed using the one-cotyledon method as described by Hassell et al. (2008).
108 Because roots require energy to maintain and continue growth (Esau, 1953), rootstock hypocotyl was
109 separated from roots and re-rooted in soilless mix to maintain energy reserves to heal the graft before
110 re-rooting.
111 Experiment 2. The second experiment also utilized both 'Mads' and 'Carnivor' rootstock cultivars, which
112 were treated with fatty alcohol in the same manner as experiment one. Prior to grafting, all rootstocks
113 remained in the greenhouse for 1, 7, 14, or 21 DAT. Rootstocks were sequentially seeded to provide
114 rootstocks of each time after fatty alcohol treatment to graft on the same day. An additional rootstock
115 treatment was also seeded on the same day as the 1 DAT rootstocks, omitting the fatty alcohol
116 treatment to provide an untreated control. Seedless watermelon cultivar Tri-X 313 was also used as
117 scion material, and was sown on the same day as the 14-day rootstock to ensure that scion was the
118 same age for each treatment. Each rootstock treatment consisted of 12 plants, and was replicated 5
(
119 times. The entire experiment was repeated twice, with grafting occurring in October and December of
120 2013. Grafting was performed using the hypocotyl-only method, consisting of removing both
121 cotyledons from the hypocotyl, making a 30 degree angled cut down the side of the hypocotyl, and
122 securing the scion to the hypocotyl using a silicone grafting clip (Hydro-Gardens, Colorado Springs, CO).
123 Rootstock hypocotyls roots were removed in the same manner as experiment one to conserve hypocotyl
125 Growing Conditions. Rootstock seeds were sown in 72-cell plug trays with a 1 inch diameter (TLC
126 Polyform, Minneapolis, MN) using a nutrient-free, soilless mix (75% sphagnum peat, 25% perlite) (Sun
127 Gro Horticulture, Agawam, MA). Seeds were sown following standard greenhouse production practices
128 (Rutledge, 2009). Scion seeds were sown according to guidelines outlined by Hassell and Schultheis
7
129 (personal communication). All seedlings were grown in a standard, double-layer polyethylene
I
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130 greenhouse covered with a double layer of 6 mil clear plastic (K50 Clear; Klerks Hyplast, Chester SC).
131 The greenhouse contained a gas heating system to supply heat and exhaust fans to remove heat.
132 Minimum temperatures were set at 60 °C and the exhaust fans were set to power on when greenhouse
134 Data Collection. All grafted plants remained in the healing chamber for 7 d following grafting, at which
135 time the plants were removed to the greenhouse for a final week of growth and development. Healing
136 chamber was a 36 x 122 inch wooden tray enclosed with 6 mil plastic on hoop frames. A duct-mount
137 centrifugal atomizer humidifier (707U, Herrmidifier, Sanford, NC) was used to maintain humidity in the
138 healing chamber. At the end of the final week in the greenhouse, graft survival data was recorded.
139 Healed transplants that had re-rooted successfully (i.e., root balls were adequately developed to
140 prevent smooth removal of the hypocotyl from the tray) were considered surviving transplants. The
\ ,,
141 mix was washed from the roots, which were then separated from the hypocotyl and weighed using an
142 analytical scale (Sartorius A 120 S; Data Weighing Systems, Elk Grove, IL). Root tissue was dried for 5-7 d
143 at 21 °C using an incubator (320-6 1000 Series; Napco Industrial Partner, Richardson, TX). Following the
144 drying, roots were individually weighed to determine the root dry weight.
145 Data Analysis. For both experiments, a randomized complete block design was used, with replication as
146 the blocking factor. Graft survival and root fresh and dry weights were analyzed with a linear mixed
147 model using the fit model platform of JMP Pro 10® Software (SAS Institute, Cary, NC). The percentage of
148 surviving plants was calculated and used in data analysis. Because statistically significant differences
149 were observed between the two rootstock types, rootstock data was analyzed separately. The model
150 was a complete factorial model including all combinations and interactions between and among the
8
151 fixed effects of rootstock age (in DAT) and planting date. Random effects included replication and the
(
152 interactions among rep and the fixed factors, with planting date nested within the remaining factors. \.
154 Experiment 1
155 ANOVA Analysis. There were significant effects of rootstock age, as well as some significant effects of
156 planting date and two-way interactions, on graft survival and root growth for rootstocks grafted using
158 Graft Survival. Using 'Carnivor' rootstock, we observed no significant differences in graft survival
159 between 1, 7, and 14 DAT (Figure 1). In both planting dates, there were significant decreases in graft
160 survival at 21 DAT. In past experiments, a similar decrease in rootstock vigor and carbohydrate content
161
162
was observed in rootstock 21 DAT (Daley & Hassell, 2013), indicating that 'Carnivor' rootstock
164 there were no significant differences in starch between rootstocks at 14 and 21 DAT, which paralleled a
165 similar pattern of starch accumulation in previous research (Daley & Hassell, 2013). This data indicates
166 that that 'Macis' rootstocks are more able to maintain their carbohydrate reserves than 'Carnivor'. The
167 trend of increasing graft survival as time after fatty alcohol treatment progresses illustrates the benefits
168 of the fatty alcohol treatment in improving the efficiency of standard grafting methods by increasing the
169 grafting window of rootstocks from just a few days (Hassell et al., 2008) to at least two weeks.
170 There was no significant effect of planting date on graft survival in 'Carnivor'rootstock, but we observed
171 significantly lower graft survival in the August planting of 'Macis' rootstock (Figure 1). Lagenaria
172 rootstock is, in our experience, a more variable rootstock that is sensitive to excessive moisture. The
9
173 decreased grafting success observed on 1 and 7 DAT in the August planting may be due to the increased
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'174 amount of watering that occurred within the greenhouse to maintain live plants.
175 Rootstock Re-rooting. There was no effect of DAT observed in 'Carnivor' rootstock root fresh and dry
176 weights (Figures 2). Because the cotyledon remained attached to the rootstock and provided the
177 required energy to heal the grafts and produce new roots, the effect of the increased carbohydrates in
178 the hypocotyl may have been masked in this rootstock. There was a significant DAT effect on root fresh
179 and dry weights in 'Macis' rootstocks. There was a significant increase on 7 DAT in both planting dates
180 (Figures 2A and 2B), and no significant differences on 7, 14, and 21 DAT in the May planting. Root fresh
181 weight was significantly lower on 21 DAT in the August planting of 'Macis' rootstocks (Figure 2A).
182 Experiment 2.
183 ANOVA Analysis There was a significant effect of rootstock age on graft success of both 'Carnivor' and
' ,.84 'Macis' rootstocks, and significant two-way interactions of rootstock age and grafting date on root fresh
185 and dry weights for 'Macis' graft survival. There was also a significant effect of day on root fresh and dry
187 Graft Survival. Using the hypocotyl only graft, we observed no significant difference in graft survival
188 between the untreated control rootstocks and the treated rootstocks that were 1 DAT with both
189 cultivars, indicating that there was no detrimental effect of the fatty alcohol treatment on graft survival.
190 All cultivars increased significantly in graft success from 1 to 7 DAT, with 'Carnivor' rootstocks increasing
191 to about 90% survival, and 'Macis' rootstocks increasing to over 45% and 70% in the August and
192 December plantings, respectively (Figure 3). There were no significant changes in graft survival for
193 'Carnivor' rootstocks at 14 and 21 DAT, with the exception of day 21 of the October planting, where
194 graft survival decreased to about 70%. This decrease follows the pattern of starch decrease at 21 DAT in
J'.95 'Carnivor' rootstocks observed in previous experiments (Daley et al., 2014). 'Macis' rootstock graft
10
196 survival percentages continued to increase significantly to about 90% survival at 14 DAT in both planting
197 dates. This also parallels the pattern of starch accumulation observed previously (Daley et al., 2014).
(
198 No significant differences were observed in 'Macis' rootstock between 14 and 21 DAT in the October
199 planting, but survival increased significantly to 98% at 21 DAT during the December experiment. This
200 pattern of survival indicates that 'Carnivor rootstock increases in graft survival earlier than 'Macis'
201 rootstock.
202 Rootstock Re-rooting. For both rootstock cultivars, there were no significant differences between the
203 root fresh and dry weights of the untreated control and the rootstocks 1 DAT, indicating that there are
204 no effects of the fatty alcohol treatment on the rootstocks, and illustrating the inability of the rootstocks
205 to successfully heal the graft and re-root without taking the time to accumulate energy reserves
206 following the fatty alcohol treatment (Figures 4A and 4B). With both 'Carnivor' and 'Macis' rootstocks,
207 we observed a significant increase in root fresh and dry weight at 7 DAT, with the greatest increase
208 observed in 'Carnivor' rootstocks planted in October (Figures 4A and 4B). 'Macis' rootstocks in the
(
209 December planting increased the least, from 0.0 g to nearly 0.2 g fresh weight at 7 DAT (Figure 4A). In
210 both cultivars, root fresh weight did not significantly change 7 and 14 DAT, with the exception of 'Macis'
211 rootstocks planted in December. In this planting, root fresh weight increased by 0.1gat14 DAT. Root
212 fresh weight of 'Carnivor' rootstocks from the October planting increased significantly to nearly 0.9 g at
213 21 DAT. 'Macis' rootstock from the December planting also significantly increased from 0.3 g at 14 DAT
214 to almost 0.5 g at 21 DAT. Both rootstock cultivars produced significantly lower root fresh weights in the
215 December plantings, suggesting that lower temperatures in the winter months decrease re-rooting
217 Similar trends were observed in root dry weights of both cultivars. In each cultivar, there was a
218 significant increase in root dry weight using 7 DAT rootstocks {Figure 4B). 'Carnivor' rootstocks from the
11
219 October planting exhibited the greatest increase, reaching 0.08 g 7 DAT. The least amount of increase 7
1
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220 DAT was in 'Macis' rootstock from the December planting. Root dry weights of both rootstock cultivars
221 on both planting dates, with the exception of 'Carnivor' in the October planting, also significantly
222 increased at 14 DAT (Figure 4B). Root dry weights of both 'Macis' and 'Carnivor' rootstocks did not
223 significantly change on 21 DAT in October, but each rootstock cultivar increased significantly on the
224 same day of the December planting. One possible explanation for this was that the more optimal
225 weather in the October planting allowed the rootstocks to reach their peak starch storage by day 14, but
226 since the weather in December was cooler than optimal, the rootstocks required a greater amount of
227 growing time to accumulate the required energy, and did not have the reserves necessary to produce as
229 The hypocotyl-only grafting method has not, until now, been successfully performed with consistent
230 success. Based on our data, we conclude that the fatty alcohol treatment overcomes the need for a
231 cotyledon in cucurbit grafting by increasing the amount of energy reserves in the rootstock hypocotyl.
232 After a fatty alcohol treatment, the increased carbohydrate reserves in the rootstock overcome the
233 reliance on the cotyledon to produce energy sufficient for graft survival and re-rooting, and make
234 grafting with the hypocotyl possible at 7 DAT for interspecific hybrid rootstocks, or at 14 DAT for bottle
236 Conclusions. The physiological differences between the two rootstocks support their differing responses
237 to the fatty alcohol treatment in graft survival. As a hybrid, 'Carnivor' rootstock is typically more
238 vigorous, with a deeper root system, and has recently become a more preferred rootstock in the
239 grafting industry (King et al., 2010). The increased vigor of this rootstock continues to be evident in the
240 rootstock's response to fatty alcohol treatment: compared to bottle gourd rootstocks, 'Carnivor'
/ '241 rootstock requires a greater concentration of fatty alcohol to destroy the meristem (Daley and Hassell,
12
242 in press), and also accumulates a greater amount of starch in the hypocotyl (almost 300-fold compared
243 to 30-fold) than 'Mads' rootstocks (Daley et al., 2014). As the rootstocks are from two separate genera
244 within the Cucurbitaceae family, it is expected that their respective responses to fatty alcohol treatment
246 Matching hypocotyl diameter is essential to graft success (Davis et al., 2008). We observed that graft
247 survival decreased at 21 DAT with 'Carnivor' rootstock, possibly because of a cambial mismatch once
248 rootstocks reached that age. 'Carnivor' hypocotyls have previously been shown to double in diameter
249 over 21 DAT (Daley and Hassell, 2014). The difference in hypocotyl diameter between the watermelon
250 scion and the 'Carnivor' rootstock may have prevented graft survival.
251 Fatty alcohol rootstock treatments can improve success and efficiency of current methods by increasing
252 graft survival and increasing the time period that rootstocks remain suitable for grafting. Grafting in
253
254
ideal conditions and seasons could further increase the success of the one-cotyledon grafting method.
In addition, fatty alcohol treatment allows for successful use of the hypocotyl-only grafting method.
c
255 Removal of the cotyledons with the hypocotyl-only method may decrease chances of disease, because
256 the cotyledon could become a harbor for disease as it ages. Complete cotyledon removal also increases
257 production efficiency by decreasing the space requirement of each grafted plant. Doing so will increase
258 the number of grafted plants that can be produced utilizing finite greenhouse spaces, and thus decrease
260
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Monosporascus root rot and vine decline in muskmelon, watermelon, and grafted watermelon crops.
Bisognin, D.A., L. Velasquez, and I. Widders. 2005. Cucumber seedling dependence on cotyledonary
Daley, S., W.P. Wechter, and R.L. Hassell. 2014. Fatty alcohol blinding causes watermelon rootstock
Daley, S. and R.L. Hassell. 2014. Fatty alcohol application to control meristematic regrowth in bottle
gourd and interspecific hybrid squash rootstocks used for grafting watermelon. HortScience. (In Press)
Davis, A.R., P. Perkins-Veazie, Y Sakata, S. Lopez-Galarza, J.V. Ma rot, S. Lee, Y. Huh, Z. Sun, A. Miguel, S.R.
King, R. Cohen, and J. Lee. 2008. Cucurbit grafting. Crit. Rev.Plant Sci. 27(1):50-74
Esau, K. 1953. The Root, p.470-529. In: Esau, K. Plant Anatomy. Wiley, New York, N.Y.
Guan, W., X. Zhao, R. Hassell, and J. Thies. 2012. Defense mechanisms involved in disease resistance of
Hassell, R.L., F. Memmott, and D.G. Liere. 2008. Grafting methods for watermelon production.
HortScience 43(6):1677-1679.
King, S.R., A. R. Davis, X. Zhang, and K. Crosby. 2010. Genetics, breeding and selection of rootstocks for
Kousik, C.S., A. Levi, K. Ling, and W.P. Wechter. 2008. Potential sources of resistance to cucurbit
Louws, F.J., C.L. Rivard, and C. Kubota. 2010. Grafting fruiting vegetables to manage soilborne
Memmott, F.D. 2010. Refinement of innovative watermelon grafting methods with appropriate choice
of developmental stage, rootstock genotype, and root treatment to increase grafting success. MS Thesis,
Memmott, F.D. and R.L. Hassell. 2010. Watermelon (Citrullus lanatus) grafting method to reduce labor
(
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. 15
Table 1: ANOVA analysisz of the effects of rootstock agev after fatty alcohol treatmene on graft survivalw and root weights of transplants grafted
Carnivor Macis
Degrees of
Response Effect Freedom F Ratio P Value F Ratio P Value
Graft Survivalv Rootstock Age 3 8.8365 0.0044* 43.2486 <0.0001 *
Planting Date 1 4.8805 0.0547 27.9409 0.0002*
Planting Date by Planting Date 3 3.8706 0.0490* 6.3383 0.0076*
Root Fresh Rootstock Age 3 88.4718 <0.0001* 52.2324 <0.0001*
Planting Date 1 26.6894 <0.0001* 5.7128 0.0178*
Planting Date by Planting Date 3 1.5528 0.1885 20.8728 <0.0001 *
Root Dry Weight Rootstock Age 3 314.6308 <0.0001* 90.3396 <0.0001*
Planting Date 1 2.6405 0.1058 12.9713 0.0004*
Planting Date by Planting Date 3 3.6716 0.0066* 17.5340 <0.0001*
z P ~ 0.05 considered significant
v Grafting was performed at 1, 7, 14, and 21 days following rootstock fatty alcohol treatment
Table 2: Results of ANOVA analysisz of the effects of rootstock ageY after fatty alcohol treatmentx on graft survivalw and root weights of
Carnivor Macis
Response Effect Degrees of F Ratio P Value F Ratio P Value
Graft Success Rootstock Agew 4 294.6396 <0.0001 * 354.4546 <0.0001 *
Planting Datev 1 0.7680 0.3912 6.7477 0.0172*
Planting Date by Rootstock Age 4 1.6211 0.2080 3.9440 0.0161 *
Root Fresh Rootstock Age 4 240.2385 <0.0001 * 239.1051 <0.0001 *
Planting Date 1 42.9908 <0.0001 * 95.2659 <0.0001 *
Planting Date by Rootstock Age 4 8.3786 0.0009* 15.4225 <0.0001 *
Root Dry Weight Rootstock Age 4 168.5139 <0.0001 * 213.6674 <0.0001 *
Planting Date 1 117.9220 <0.0001 * 297.0647 <0.0001 *
Planting Date by Rootstock Age 4 20.0910 <0.0001 * 47.1811 <0.0001 *
v Grafting was performed at 1, 7, 14, and 21 days following rootstock fatty alcohol treatment.
' .
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17
FIGURE CAPTIONS
Figure 1. Graft survival using the one-cotyledon method evaluated as a percent graft healing and
rootstock re-rooting. 'Carnivor' and 'Macis' rootstocks were grafted at 1, 7, 14, and 21 days after fatty
alcohol treatment in May (solid lines) and August (broken lines) of 2013. For 'Carnivor' rootstock
cultivars, graft survival significantly (P ~ 0.05) decreased on day 21, while 'Macis' rootstock increased
Figures 2A and 28. Root fresh (A) and dry (B) weights of 'Carnivor' and 'Macis' rootstocks grafted at 1, 7,
14, and 21 days after fatty alcohol treatment using the one-cotyledon grafting method in May (solid
lines) and August (broken lines) of 2013. Statistically significant (P ~ 0.05) increases were observed
between day 1 and day 7 of 'Macis' rootstock root fresh weight (A) in both plantings. Significant
increases in root dry weight were also observed between days 1 and 7 in all rootstocks except 'Carnivor'
planted in August.
Figure 3. Graft survival using the hypocotyl only method evaluated as percent graft healing and
rootstock re-rooting. Untreated 'Carnivor' and 'Macis' rootstocks (day O) are used as a control to
determine whether deleterious effects of the treatment exist. In addition to the controls, 'Carnivor' and
'Macis' rootstocks were grafted at ages of 1, 7, 14, and 21 days after fatty alcohol treatment. The
experiment was conducted twice in October (solid lines) and December (brokenlines) of 2013. 'Carnivor'
graft success significantly increased (P ~ 0.05) on day 7 and decreased significantly on day 21, while
Figures 4A and 48. Root fresh (A) and dry (B) weights of 'Carnivor' and 'Macis' rootstocks grafted at 0
(untreated), 1, 7, 14, and 21 days of fatty alcohol treatment using the hypocotyl-only grafting method in
October (solid lines) and December (broken lines) of 2013. There were no stastically significant (P ~
0.05) differences observed between untreated control rootstock and 1-day rootstock. Significant
18
increases were observed in fresh weights of both cultivars day 7, and 'Macis' at day 14. Significant dry
weight increases were also observed for both cultivars on days 7 and 14, with the exception of 'Carnivor'
grafted in October.
19
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Figure 1. Graft survival using the one-cotyledon method evaluated as a percent graft healing and
rootstock re-rooting. 'Carnivor' and 'Macis' rootstocks were grafted at 1, 7, 14, and 21 days after fatty
alcohol treatment in May (solid lines) and August (broken lines) of 2013. For 'Carnivor' rootstock
cultivars, graft survival significantly (P ~ 0.05) decreased on day 21, while 'Macis' rootstock increased
significantly on days 7 and 14.
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Days After Rootstock Fatty Alcohol Treatment
B o.o9
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Figures 2A and 28. Root fresh (A) and dry (B) weights of 'Carnivor' and 'Macis' rootstocks
grafted at 1, 7, 14, and 21 days after fatty alcohol treatment using the one-cotyledon grafting
method in May (solid lines) and August (broken lines) of 2013. Statistically significant (P ~ 0.05)
increases were observed between day 1 and day 7 of 'Macis' rootstock root fresh weight (A) in (
both plantings. Significant increases in root dry weight were also observed between days 1 and \
7 in all rootstocks except 'Carnivor' planted in August.
21
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Days After Rootstock Fatty Alcohol Treatment
Figure 3. Graft survival using the hypocotyl only method evaluated as percent graft healing and
rootstock re-rooting. Untreated 'Carnivor' and 'Macis' rootstocks (day O) are used as a control to
determine whether deleterious effects of the treatment exist. In addition to the controls, 'Carnivor'
and 'Macis' rootstocks were grafted at ages of 1, 7, 14, and 21 days after fatty alcohol treatment. The
experiment was conducted twice in October (solid lines) and December (brokenlines) of 2013.
'Carnivor' graft success significantly increased (P s 0.05) on day 7 and decreased significantly on day
21, while 'Macis' rootstock increased significantly on day 7 and day 14.
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...,._ Carnivor-October - Macis-October •••A•• Carnivor-December • • ·•· • Macis-December
Figures 4A and 48. Root fresh (A) and dry (B) weights of 'Carnivor' and 'Macis' rootstocks
grafted at 0 (untreated), 1, 7, 14, and 21 days of fatty alcohol treatment using the hypocotyl-
only grafting method in October (solid lines) and December (broken lines) of 2013. There
were no stastically significant (P :s; 0.05) differences observed between untreated control
rootstock and 1-day rootstock. Significant increases were observed in fresh weights of both
cultivars day 7, and 'Macis' at day 14. Significant dry weight increases were also observed for
both cultivars on days 7 and 14, with the exception of 'Carnivor' grafted in October.
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Carla Hull
( From: Renee Allen < [email protected]>
.ient: Monday, October 19, 2015 2:03 PM
To: 'Carla Hull'
Subject: FW: images of tomato root plugs
Attachments: photojpg
Renee' Allen
FAIR PRODUCTS, INC
www.fairproductsinc.com
(919) 467-1599
-Original Message-
From: Grant Ohman Jmailto:[email protected])
Sent: Tuesday, March 18, 2014 7:09 PM
To: 'Renee Allen'
Subject: images of tomato root plugs
HI Frank,
('"\. This is a small representation of the 1.2 million plugs of the grafted proprietary tomato seed we propagated for a
. _ustomer in california. •
It probably appears to be a lot to anyone but when you consider there are over 1 billion tomato plants rooted in soil it
gives you an idea of the size of the market.
We've been doing R & 0 on this for three years and hit the nail on the head as far as success rate goes. Now all that is
left to do Is see how well It takes in the fields of Callfomla,
Grant
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Carla Hull
\
From: Renee Allen < [email protected]>
Sent Monday, October 19, 2015 2:20 PM
To: 'Carla Hull'
Subject: FW: shipping boxes
Attachments: photo (S)jpg
Renee' Allen
FAIR PRODUCTS, INC
www.fairproductsinc.com
{919) 467-1599
--Original Message-
From: Grant Ohman fmailto:[email protected]]
Sent: Tuesday, March 18, 2014 7:22 PM
To: 'Renee Allen'
Subject: shipping boxes
1
..,1-
1
Cotyledonary Axillary Shoot Control by Fatty Alcohol Application for Grafting Tomato
1
Corresponding Author. E-mail address: [email protected]
(
\
2
3 Cotyledonary Axillary Shoot Control by Fatty Alcohol Application for Grafting Tomato
5 Additional index words. sucker control, chemical control, axillary buds, meristems,
6 Solanum lycopersicum
9 below rootstock cotyledons to avoid undesirable axillary shoots growing out from the
11 assure adequate distance between grafted union and soil line, only if there is no potential
13 alcohol compound was tested as a potential chemical control means against cotyledonary
16 using various application methods. When fatty alcohol was applied directly to
17 cotyledonary axillary buds, the seedlings were then pinched to force-induce the
18 cotyledonary axillary shoot extension in order to assure the efficacy of the fatty alcohol
19 treatment. High concentrations (10 and 15 %) of fatty alcohol killed the buds and
20 suppressed axillary shoot extension at level lower than 7 %. However, when applied over
22 alcohol caused plant collapse because the excess fatty alcohol trickled down the stem and
23 presumably damaged the root system. When fatty alcohol was applied over true leaves
(
\ ___ ,
3
27 effective concentrations of fatty alcohol is applied exclusively to the target buds (10-15
30 Since use of methyl bromide for soil fumigation has been limited by the Montreal
31 Protocol, there is an increasing need to find an alternative method to manage soil borne
32 pathogens and pests in open-field vegetable production. One of the proposed alternative
33 methods is the use of grafting rootstock that is resistant to soil borne diseases (Kubota et
34 al., 2008). Although vegetable grafting has been widely used in many countries such as
35 Asia and Europe to manage soil borne diseases, the use of vegetable grafting is still
36 limited in the United States (Lee et al., 2010, Louws et al., 2010). One issue limiting the
37 use is the large number of seedlings needed for large-scale, open-field production
38 systems, and another issue is the high cost of grafted seedlings compared to conventional
40 fumigation with methyl bromide is now attracting growing interest in the United States
41 (Colla, 2010).
42 In vegetable grafting, the position of the graft union must be high enough to
43 prevent the vulnerable scion from coming into direct contact and exposure with the soil,
44 especially when the grafted plants are transplanted by machines in large-scale, open-field
45 production system. For tomato (Solanum lycopersicum), while grafting above the
47 union and soil line, potential grow-out of axillary shoots from rootstock cotyledons can
48 be problematic because it requires additional labor cost to manually prune the axillary
49 shoots in the field as well as at the propagation stage (Hausher, 2011). Therefore, the use
50 of chemical to inhibit the cotyledonary axillary shoot growth from rootstock could allow
51 grafting above cotyledons and reduce the additional management cost of grafted tomato
S3 Fatty alcohol and fatty acid methyl ester with chain lengths from Cs to C 12 ,
S4 emulsified with appropriate surfactants, have been reported to kill the rapidly dividing
SS meristematic tissues such as apical and axillary buds without damaging mature leaf or
S6 stem tissues in variety of plants (Cathey et al., 1966; Maw, 1977; Steffens et al., 1967;
S7 Tso, 1964; Tso et al., 1965; Tucker and Maw, 1975). The mechanism of selective killing
S9 property of the well-developed cuticlar layer over mature tissue that acts a penetration
60 barrier to these chemicals compared with young tissue (Nelson and Reid, 1971 ). Once
61 penetrating thorough the meristematic tissue, these chemicals disrupt the plasma
62 membranes and cause desiccation of the tissue (Wheeler et al. 1991). In tobacco
63 production, commercially available fatty alcohols, usually mixtures of Cs and C10 fatty
64 alcohols, formulated with surfactants, have been used to control axillary shoot (sucker)
,/'
6S growth after decapitation (Steffens, 1979). Decapitation and sucker control of tobacco
66 improves yield and the concentration of nicotine of leaf to be harvested, by reducing the
68 compound used on tobacco was demonstrated to be a part of new grafting method for
70 grafted seedlings (Daley, 2014; Daley and Hassell, 2014). For tomato, Maw (1977)
71 demonstrated effective use of fatty alcohol for controlling axillary shoot on young tomato
72 plants grown in greenhouse, although the fatty alcohol had to be applied exclusively to
73 the axillary shoots otherwise it caused chemical damages on leaves and stems. These
74 studies suggest that fatty alcohol could control growth of cotyledonary axillary shoot for
76 concentration and application methods of fatty alcohol for tomato rootstock seedlings
80 experiments were conducted. Experiment 1 and 2 were to examine the effects of fatty
82 tomato seedlings at three-true-leaf stage. In these experiments, fatty alcohol was applied
84 shoots (in length from 1.8 to 3.2 cm) from cotyledons (Expt. 2). To test a more practical
85 application method, a conventional spray bottle was employed in Experiment 3 and the
86 phytotoxic effects of fatty alcohol applied on true leaves and stems were studied.
87
90 'Roma VF' tomato (Westar Seeds International, Inc., CA) was used in this study.
91 'Roma VF' is not a commercial rootstock but we employed this cultivar for our study as a
92 model system due to the availability of seeds. Seeds were sown into 98- cell seedling
93 trays (tray size; 28 cm x 55 cm; one seed per cell) filled with moist commercial substrate
94 (SunGro Sunshine Professional Mix 3, Bellevue, WA) covered with a thin layer of
95 vermiculite. The seeded trays were then covered with a thin plastic film and placed for
96 two days under darkness in a growth chamber (Model 2015; VWR International,
97 Cornelius, OR) controlled at 29 ± 1 °C air temperature. Two days after seeding, the trays
98 were placed in the greenhouse and irrigated every two days with tap water. After the 11th ( '
7
/
99 day, the plants were irrigated daily with tap water and twice weekly with nutrient solution
\
100 (electrical conductivity 2.0 to 2.4 dS·m- 1, pH 5.9 to 6.3) containing 90 nitrogen (all in
101 nitrate form) 47 phosphorus, 144 potassium, 160 calcium, 60 magnesium and 113 sulfur
102 (mg· L- 1) as well as micronutrients. The greenhouse used in the present experiments was
103 located in Tucson, AZ, covered by double-layered acrylic roof and walls, and equipped
104 with pad-and-fan cooling and overhead gas heating systems. The daytime and nighttime
105 set points of air temperature were 28 and 21 °C, respectively using a commercial
106 greenhouse controller (Wadsworth Control Systems Inc., Arvada, CO). After 17 to 19
107 days from seeding, when seedlings were at the three-true-leaf stage, 10-15 uniform
110 A commercially available fatty alcohol compound, N-TAC® (Fair Products, Inc.,
111 Cary, NC), consisting of 36.2 % C8, 48.2 % C 10 , 0.3 % C 12 fatty alcohol and 15.3 % other
112 ingredients, was used in this study. Fatty alcohol was diluted with ion-exchanged water to
113 prepare emulsions having product concentrations from 0.5 to 15 % (VN) for the
116 After 17 days of seeding (May 5th, 2014), plants were treated with 0, 2, 5, 10 or
118 emulsion was applied carefully to each cotyledonary axil area of all the seedlings. The
119 application volume was selected so that it thoroughly covers the axillary bud without
120 overflowing to trickle down the stem. To assess the effectiveness of the fatty alcohol
121 treatment, plants were pinched 1 cm above cotyledons one day after the treatment to
\.
8
122
123
force undamaged axillary buds to develop shoots. Plants were visually inspected for any
sign of chemical damage or axillary shoot extension 1, 7, 14 and 22 days after treatment.
c·
124 In order to examine the degree of damage on the axillary buds caused by fatty alcohol
125 treatment, the axillary buds of three to five representative plants per treatment were
126 observed under stereomicroscope (Vista Vision; VWR International, Cornelius, OR).
128 After 18 days of seeding (May 6th, 2014), plants were pinched about 1 cm above
129 cotyledons to force cotyledonary axillary shoots to develop. Seven days after pinching,
130 axillary shoots in length from 1.8 to 3.2 cm were treated with 0, 0.5, 1, 2, 4 or 5 % (VN)
132 experiment were selected based on the phytotoxicity observed in the Experiment 1. Using
133 a pipette, 250 µL of the emulsion was applied to each axillary shoot. The application
134 volume was selected so that the axillary shoot was covered thoroughly with emulsion.
135 Plants were visually inspected for any sign of chemical damage and axillary shoot growth
137 Phytotoxicity Evaluation over True Leaves and Stems (Experiment 3).
138 A fully unfolded true leaf and a 1-2 cm section of stem close to cotyledonary axils
139 of each plant were subject to the spraying treatment with 0, 0.5, 1, 2, 4 or 5 % (VN)
140 concentration of fatty alcohol emulsions after 19 days of seeding (May 7th, 2014).
141 Approximately 1 mL of the emulsion was applied to each of the true leaf and the stem
142 section using an ordinary 16 oz. (473 mL) sprayer. Plants were visually inspected for
143 damage on the true leaves and the stem sections 1, 7, 14, and 21 days after treatment.
145 This study was conducted during April 18 - June 3, 2014. For Expt. 1 and 2, the
146 treatments were repeated three times using seedling tray (98 cells) as a replication. Each
147 treatment consisted of 10-15 plants. For Expt. 3, each treatment was replicated once with
148 10 plants per treatment. Positions of treatment within each tray as well as positions of
149 three trays over the bench inside the greenhouse were randomized. JMP Pro (version 9.0,
150 SAS Institute) was used to analyze data. Percent data were arcsine-transformed and their
151 means were separated by Tukey's honest significant difference test at P::; 0.05.
152
155 Average day/night air temperatures in the greenhouse were 24.6 ± 2.4/18.5 ± 2.1
156 °C in Expt. 1, 25.2 ± 2.7/19.0 ± 2.4 °C in Expt. 2 and 24.8 ± 2.5/18.6 ± 2.2 °C in Expt. 3.
/
i
',,
157 Average DLis in the greenhouse were estimated from the solar radiation recorded in the
159 the predetermined greenhouse light transmission of 42 %: 25.2 ± 2.6 mol·m- 2·d- 1 in Expt.
160 1, 25.0 ± 3.2 mol·m- 2·d- 1 in Expt. 2 and 25.3 ± 2.6 mol·m- 2 ·d- 1 in Expt. 3.
161 Expt. 1.
162 Seven days after fatty alcohol treatment, the control plants (treated with 0 % fatty
163 alcohol) had 100 % of plants with axillary shoot extension, induced by pinching (Table 1;
164 Fig. lA). The high concentrations (10 and 15%) of fatty alcohol treatment maintained the
165 percentage of plants with axillary shoot extension below 7% throughout the experiment
166 (Table 1). At 2 and 5% concentrations, the percentage of plants with axillary shoot
167 extension increased over the first 14 days but remained the same after 22 days (Table 1).
10
168 The percentage of plants with axillary shoot extension at 2% fatty alcohol concentration
169 was non-significantly different from that in the control and it was significantly lower at
170 5% than that in the control but unacceptable level (23.3% after 22 days). Under the
171 stereomicroscope, the plants with no axillary shoot extension had the necrotic and
173 In contrast, 14 days after treatment, adventitious secondary shoots were observed
174 in some plants with no axillary shoot extension (data not shown). Those adventitious
175 shoots appeared to develop at either the pinched surface or the stem between the cut stem
176 end and cotyledons, and usually they grew in clumps (Fig. 1C), unlike the axillary shoots
177 developed from cotyledons (Fig. lA). At day 22, the number of plants with adventitious
178 shoots increased, and almost all plants with no axillary shoot extension had these
179 adventitious shoots (data not shown). The adventitious shoot development observed in
180 this experiment was presumably due to the lack of active apical and axillary meristems c
181 that produce auxin. Tomato seems to produce many adventitious shoots from cut surfaces
182 of stems when apical and axillary meristems were removed. For example, tomato in-vitro
183 explants grown on solid tissue culture medium without growth regulators regenerated
184 2.9-5.3 shoots on the cut surface after removing the apical and axillary meristems
185 (Pozueta-Romero et al., 2001 ). Also tomato plants grown in a greenhouse reportedly
186 regenerated many adventitious shoots from the cut surface of the stem and axillary shoots
187 after the plants were decapitated and the axillary shoots emerged after decapitation were
188 excised (Harada et al., 2005; Johkan et al., 2008). For rootstock plants, adventitious
189 shoots could be avoidable when grafted successfully to the scion which could continue to
190 grow and provide the source of auxin to prevent adventitious shoot development. Tezuka
11
191 et al. (2011) showed that adventitious shoot regeneration after decapitation was inhibited
/
\
19 2 by the presence of axillary shoots or by application of 1-naphthaleneacetic acid in
193 decapitated tomato plants grown in a greenhouse. However, Bausher (2011) found that
194 rootstock shoot regrowth from cotyledons recurred even after original axillary shoots
195 were pruned in grafted tomato plants when grafted above the rootstock cotyledons.
196 Therefore, adventitious shoots might occur even in successfully grafted plants treated
198 alternative methods might be required to control axillary shoot and adventitious shoot
199 growth from rootstock. Further study is needed to investigate possible development of
200 rootstock adventitious shoots long after fatty alcohol treatment using grafted tomato
201 plants.
202 The chemical damages on the plants other than the axillary buds by fatty alcohol
203 treatment, such as the stem scar and the cotyledon damage (Fig. lD), were observed one
204 day after treatment. After 22 days of treatment, the plants treated with 2, 5, 10, and 15 %
205 fatty alcohol had 30.0, 76. 7, 100 and 100 % incidence of the plants exhibiting stem scar,
206 respectively (Table 1). For the 5, 10 and 15 % fatty alcohol treatments, 10.0, 33.3 and
207 50.0 % of the plants had cotyledon damage, respectively. However, retaining cotyledons
208 is not needed for tomato grafting. Also stem scar and cotyledon damage did not seem to
209 affect the ability to grow of plants after the fatty alcohol treatment in our experiment,
210 suggesting that the damages observed in this experiment may not affect grafting success
211 and therefore may be acceptable. Even with cotyledons being damaged by fatty alcohol,
212 bottle gourd (Lagenaria sicereria) and interspecific hybrid squash (Cucurbita maxima x
213 Cucurbita moschata) rootstocks could be used successfully for grafting watermelon.
12
214 Further study is needed to confirm the influence of the damages observed in the present
217 concentrations ( 10 and 15 %) killed cotyledonary axillary buds and suppressed the
218 percentage of plants with cotyledonary axillary shoot extension at a level lower than 7 %
219 and therefore, might be a useful chemical tool to control cotyledonary axillary shoot from
221 Expt. 2.
222 After seven days of fatty alcohol treatment, the control plants (treated with 0 %
223 fatty alcohol) had 100 % of plants with surviving cotyledonary axillary shoots {Table 2;
224 Fig. 2A). Nearly 100% of plants treated with 2 % or lower concentration fatty alcohol
225 had surviving axillary shoots, suggesting that the concentrations or dose of fatty alcohol
226 was not enough to kill extended axillary shoot {Table 2). Fatty alcohol treatments at 4 and
227 5 % concentrations significantly reduced axillary shoot survival and suppressed axillary
228 shoot growth during 21 days after treatment, and the percentage of plants with surviving
229 axillary shoots were 40.0 and 20.0 %, respectively, 21 days after treatment {Table 2; Fig
230 2B). However, these percentages are unacceptably high for controlling cotyledonary
231 axillary shoot from rootstock. This result indicates that fatty alcohol concentration needs
233 was observed that the axillary shoots with no growth had necrotic shoot tip, leaves, and
236 treatment (Figure 2D). The plants treated with 0, 0.5 and 1 % fatty alcohol had no plants
13
237 that collapsed during 21 days of observation (Table 2). For the 2, 4 and 5 % fatty alcohol
\
238 treatments, 16.7, 30.0, and 43.3 % of the plants collapsed after 21 days (Table 2). These
239 levels of damage are unacceptably high even though they were non-significantly different
240 from that of the control except for 5% treatment. These plants collapsed at the base of the
241 stem, likely due to that excessive amount of fatty alcohol trickled down the stem to the
243 This collapse was observed in Expt. 2 but not in Expt. 1, despite that higher
244 concentrations were applied in Expt. 1. This is probably because the amount of fatty
245 alcohol applied to the plants in Expt. 2 was greater than that in Expt. 1. In Expt. 2, 250
246 µL of fatty alcohol emulsion was applied to cover the axillary shoot thoroughly and it
24 7 was observed that fatty alcohol emulsion trickled down the stem, which was not observed
248 in the Expt. 1 where only 5 µL was applied to the target axil. From these experiments, it
249 is suggested that the degree of chemical damage may differ depending on the dose and
250 application method of fatty alcohol. Two percent and higher concentration fatty alcohol
251 could cause collapse at a higher than 10 % chance when fatty alcohol spills from the
254 axillary shoots with fatty alcohol, because effective concentration in this type of
255 application seems to be higher than 5%, what examined in this experiment, yet enough to
256 kill the whole plants due to the amount of fatty alcohol required to cover the axillary
257 shoots. The effective concentration of fatty alcohol has to be applied exclusively target
259 Expt. 3.
14
260 The damages on true leaves by fatty alcohol spray treatment were observed one
261 day after treatment. After 14 days of treatment, slightly yellowish and necrotic tissues
262 were observed even in the leaves of control plants (treated with 0 % fatty alcohol) most
263 likely due to leaf senescence. For this reason, true leaf damage was evaluated after seven
264 days of treatment instead of 14 or 21 days. Seven days after treatment, the true leaf
265 damages were visually assessed and classified into four levels. These were 1) no visible
266 damage (Figure 3A), 2) minor leaf mottling (Figure 3B), 3) marginal necrosis (Figure
267 3C) and 4) withering (severest, Figure 3D). The leaves treated with 0 or 0.5 % fatty
268 alcohol had no visible damage (Figure 4). In 1 % and higher concentration fatty alcohol
269 treatment, all leaves treated with fatty alcohol had some level of visual damages (Figure
270 4). For 1 or 2 % fatty alcohol treatment, most leaves had minor mottling (Figure 4). Most
271 leaves treated with 4 or 5 % fatty alcohol had marginal necrosis (Figure 4). For 5 % fatty
2 72 alcohol treatment, a small percent of plants exhibited severe withering lea£ This result
273 indicates that true leaves in contact with 1 % or higher concentration of fatty alcohol can
274 get some damage and 5 % and higher concentration of fatty alcohol can cause withering.
275 Maw (1977) reported that the mature leaves treated with 1 % (WN) Off-Shoot-T, another
276 commercial fatty alcohol compound with similar components (26.5 % C8 and 35.3 % C 10
277 fatty alcohol) as the compound employed in our experiment, had minor damage (a few
2 78 small necrotic patches per leaf) in tomato seedlings at age of five or six weeks, which
280 For stem damage, the stems treated with 1% or lower concentrations of fatty
281 alcohol had no visible damage during 21 days of observation (Figure 5). For 2 % and
282 higher concentration fatty alcohol treatments, the damages on stems were found one day
15
after treatment and more than half of plants collapsed by day 21 (Figure 5). The
remaining plants had either stem scar or cotyledon damage (Figure 5). The collapse
excessive fatty alcohol was observed similarly as in Expt. 2, likely damaging the stem
base or the roots. This result indicates that spraying fatty alcohol to stems at 2 % or
higher concentration can cause some damage on stems or roots and more than half plants
can collapse.
Steffens et al. (1967) showed that fatty alcohol effectively damaged meristematic
tissues, but caused little or no visible injury to more mature tissues in tobacco with the
sucker growth after decapitation. The tobacco decapitation and sucker control are applied
seeding), 5 % and lower concentration of fatty alcohol did not suppress cotyledonary
axillary shoot growth sufficiently in pinched plants but caused true leaf damages and
significant percent plant collapse despite of the inclusion of surfactant in the fatty alcohol
product. This indicates that the controlling cotyledonary axillary shoot growth by fatty
alcohol treatment without damaging true leaves and stems is difficult possibly due to the
relatively young stage of plants upon application. However, the previous reports showed
that fatty alcohol must be applied exclusively to leaf axils, to control axillary shoot
growth without injury to mature leaves in tomatoes at age of five or six weeks, suggesting
that tomato plants are susceptible to this type of chemical regardless of physiological age
16
306 of tissue, or that surfactants used in fatty alcohol products for tobacco do not work for
307 protecting mature tissue of tomato. Steffen and Cathey (1969) reported that the selective
308 action of fatty acid methyl ester and fatty alcohol as chemical pruning agents and tobacco
309 sucker control agents depends on the class and amount of surfactant used to emulsify
310 these chemicals. The appropriate ratio of fatty ester or alcohol to surfactants, emulsion
311 concentration and surfactant type may be different among plant species or even cultivars.
312 To protect mature tissues, Maw (1977) used a small brush and a felt tip marker to
313 apply fatty alcohol only to the axillary shoots in five to six weeks of tomatoes without
314 injury to other parts of plant. Logendra et al. (2004) used a syringe attached to a pipette to
315 apply fatty acid methyl ester or fatty acid only to leaf axils of tomato plants after 45 or 55
316 days of seeding. For controlling axillary shoot growth from tomato rootstock cotyledon in
317 commercial propagation setting, an innovative, rapid and effective application method
318 targeting the cotyledonary axils or young axillary shoots without excessive fatty alcohol
321
322 Conclusion
324 alcohol effectively killed cotyledonary axillary buds and effectively suppressed
325 cotyledonary axillary shoot extension in pinched tomato seedlings. Therefore fatty
326 alcohol might be a useful means to control axillary shoot growth from tomato rootstock
327 cotyledons. However, to avoid undesirable damage on stems and true leaves that could
328 occur even at a concentration as low as 1%, high concentration of fatty alcohol has to be
17
329 applied exclusively to the target buds or young shoots. Innovative application method
\
330 targeting the cotyledonary axillary buds or young cotyledonary axillary shoots needs to
331 be developed to use fatty alcohol for controlling axillary shoot from rootstock cotyledons.
332 Further studies are required to evaluate the influence of fatty alcohol application on
333 grafting success as well as recurring rootstock adventitious shoot growth for the course of
335
336 Acknowledgements
337 This project was funded by USDA NIFA SCRI (Award Number 2011-51181-
338 30963). Authors would like to thank Mark Kroggel at University of Arizona for
339 providing technical support, and Richard Hassel and Shawana Daley at Clemson
340 University for providing technical consultation. We are grateful to Fair Products, Inc.
/
341 (North Carolina, USA) for providing N-TAC for our experimental use.
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18
345 Cathey, H. M., G. L. Steffens, N. W. Sturt, and R.H. Zimmerman. 1966. Chemical
347 Colla, G. 2010. Preface to special issue of vegetable grafting. Scientia Hort. 127:91-92.
348 Daley, S. 2014. Chemical control of rootstock regrowth in grafted watermelon and its
349 effects on plant growth and development. Clemson Univ., All Theses. Paper 1999.
350 Daley, S. L., and R. L. Hassell. 2014. Fatty alcohol application to control meristematic
351 regrowth in bottle gourd and interspecific hybrid squash rootstocks used for grafting
353 Harada, M., M. Oda, G. Mori, and H. Ikeda. 2005. Mass regeneration of shoots from cut
354 surfaces of stems in tomato stock plants. J. Jpn. Soc. Hort. Sci. 74:479-481.
355 Johkan, M., G. Mori, K. Mitsukuri, K. Mishiba, T. Morikawa, and M. Oda. 2008. In vivo
356 shoot regeneration promoted by shading the cut surface of the stem in tomato plants.
359 2008. Vegetable grafting: history, use, and current technology status in North America.
361 Lee, J.M., C. Kubota, S. J. Tsao, Z. Bie, P. Hoyos Echevarria, L. Morra, and M. Oda.
19
362 2010. Current status of vegetable grafting: diffusion, grafting techniques, automation.
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363 Scientia Hort. 127:93-105.
364 Logendra, L. S., T. J. Gianfagna, and H. W. Janes. 2004. Preventing side shoot
365 development with C8/Cl0 fatty acids increases yield and reduces pruning time in
367 Louws, F. J., C. L. Rivard, and C. Kubota. 2010. Grafting fruiting vegetables to manage
368 soilborne pathogens, foliar pathogens, arthropods and weeds. Scientia Hort. 127: 127-146.
369 Maw, G. A. 1977. Aliphatic alcohols as pruning-agents for tomato side shoots. Scientia
371 Moore, J.M. 2012. Topping and chemical sucker control programs for Georgia. In: J.M.
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372 Moore (ed.). 2013 Georgia tobacco grower's guide. 9 July 2014.
374 Nelson, P. V. and R. K. Reid. 1971. Selectivity mechanism for the differential destruction
376 Pozueta-Romero, J., G. Houlne', L. Cafias, R. Schantz, and J. Chamarro. 2001. Enhanced
379 Steffens, G.L., T.C. Tso, and D.W. Spaulding. 1967. Fatty alcohol inhibition of tobacco
380 axillary and terminal bud growth. J. Agr. Food Chem. 15:972-975.
381 Steffens, G. L. and H. M. Cathey. 1969. Selection of fatty acids derivatives: surfactant
20
382 formulations for the control of plant meristems. J. Agr. Food Chem. 17:312-317.
(
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383 Steffens, G. L. 1980. Applied uses of growth substances - Growth inhibitors, p.397-408.
384 In: F. Skoog (ed.). Plant Growth Substances 1979. Springer-Verlag Berlin Heidelberg.
385 Tezuka, T., M. Harada, M. Johkan, S. Yamasaki, H. Tanaka, and M. Oda. 2011. Effects
386 of auxin and cytokinin on in vivo adventitious shoot regeneration from decapitated
388 Tso, T. C. 1964. Plant-growth inhibition by some fatty acids and their analogues. Nature
389 202:511-512.
390 Tso, T. C., G. L. Steffens, and M. E. Engelhaupt. 1965. Inhibition of tobacco axillary bud
391 growth with fatty acid methyl esters. J. Agr. Food Chem. 13:78-81.
392 Tucker, D.J. and G.A. Maw. 1975. Chemical control of side shoots in the tomato.
c·
393 Scientia Hort. 3:331-338.
394 Wheeler, J. J., H. Seltmann, and A.G. Motten. 1991. The mode of action of fatty alcohols
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21
Table 1. Effects of fatty alcohol treatment to cotyledonary axillary buds on the percentage of
plants with cotyledonary axillary shoot extension (7, 14 or 22 days after treatment) and the
percentage of plants with chemical damage (22 days after treatment) (Expt. 1).
Y Mean values in columns followed by different letters are significantly different by Tukey's
/
\
22
Table 2. Effects of fatty alcohol treatment to extended cotyledonary axillary shoots on the
percentage of plants with surviving axillary shoot (after 7, 15 or 21 days after treatment)
and the percentage of plants collapsed (21 days aftertreatment) (Expt. 2).
Y Mean values in columns followed by different letters are significantly different by Tukey's
(
23
Figure 1. Tomato plants applied with fatty alcohol to cotyledonary axillary bus and pinched
(Expt. 1). (A) A plant with axillary shoot extension from cotyledons. (8) A plant with no
axillary shoot extension from cotyledons and with necrotic axillary buds. (C) A plant with
Figure 2. Tomato plants applied with fatty alcohol over extended cotyledonary axillary
shoots (Expt. 2). (A) A plant with surviving cotyledonary axillary shoots, showing growth.
(B) A plant with damaged cotyledonary axillary shoots, showing no growth. (C)
Cotyledonary axillary shoots with necrotic shoot tip, leaves and petioles. (D) A plant
collapsed.
24
Figure 3. Tomato true leaves sprayed with fatty alcohol (Expt. 3). (A) A leaf with no visible
damage. (B) A leaf with minor mottling. (C) A leaf with marginal necrosis. (D) A leaf with
withering.
*-
100
Q) 90
bO
....c:
ro
80
Q)
u 70
....
Q)
60 D No visible damage
c.
Q)
bO so D Minor mottling
ro
E 40 • Marginal necrosis
ro
"'C 30 •Withering (severest)
......
ro
Q) 20
ro 10
:J
VI
> 0
0 0.5 1 2 4 s
Concentration of fatty alcohol (%)
Figure 4. Effects of spraying fatty alcohol to true leaves on leaf damage seven days after
-
'ii
Q)
b.O
100
90
....cro 80
Q)
u 70 D No visible damage
'-
Q)
Q. 60 CStem scar
OJ
b.O
ro so •Cotyledon damage
E 40
ro
"'O •Collapse (severest)
30
E
....OJ
Ill
20
ro 10
:::I
Ill 0
> 0 0.5 1 2 4 s
Concentration of fatty alcohol (%)
Figure 5. Effects of spraying fatty alcohol to stem sections on stem damage 21 days after
Figure Captions
Figure 1. Tomato plants applied with fatty alcohol to cotyledonary axillary bus and pinched
(Expt. 1). (A) A plant with axillary shoot extension from cotyledons. (B) A plant with no
axillary shoot extension from cotyledons and with necrotic axillary buds. (C) A plant with
Figure 2. Tomato plants applied with fatty alcohol over extended cotyledonary axillary
shoots (Expt. 2). (A) A plant with surviving cotyledonary axillary shoots, showing growth.
(B) A plant with damaged cotyledonary axillary shoots, showing no growth. (C)
Cotyledonary axillary shoots with necrotic shoot tip, leaves and petioles. (D) A plant
collapsed.
Figure 3. Tomato true leaves sprayed with fatty alcohol (Expt. 3). (A) A leaf with no visible
damage. (B) A leaf with minor mottling. (C) A leaf with marginal necrosis. (D) A leaf with
withering.
Figure 4. Effects of spraying fatty alcohol to true leaves on leaf damage seven days after
Figure 5. Effects of spraying fatty alcohol to stem sections on stem damage 21 days after