Document ID: EPA-HQ-OPP-2012-0127-0003
Agency: epa
Document Type: Supporting & Related Material
Title: 
Posted Date: 2012-07-06T04:00Z

--------------------------------------------------------------------------------

      	UNITED STATES ENVIRONMENTAL PROTECTION AGENCY
       		WASHINGTON, D.C. 20460
      
      
      
      
                                      3/8/2012
                                                                               
                             OFFICE OF CHEMICAL SAFETY AND POLLUTION PREVENTION
MEMORANDUM

SUBJECT:	Data Requirement Scoping Document for the Registration Review of the Straight Chain Lepidopteran Pheromones.  

            Registration Review Case #:		8802
            PC Codes:						Multiple, See Table 1
            CAS Numbers:					Multiple, See Table 1
            Chemical Class:					Biochemical
                                                                  
FROM:		Jacob S Moore, Chemist /s/  3/8/12
            Biochemical Pesticides Branch
            Biopesticides & Pollution Prevention Division (7511P)
            
THRU: 	      Russell S. Jones, Ph.D., Senior Biologist /s/  3/8/12
            Biochemical Pesticides Branch
            Biopesticides & Pollution Prevention Division (7511P)

TO:			Leonard Cole, Regulatory Action Leader
            Biochemical Pesticides Branch
            Biopesticides & Pollution Prevention Division (7511P) 

ACTION REQUESTED
	A preliminary assessment of available information on product chemistry, human health assessment, and nontarget organisms and environmental fate data associated with the biopesticide class straight chain lepidopteran pheromones in support of the development of a registration review work plan.

Introduction

A pheromone, defined by the Agency in 40 CFR §158.2000, is a compound produced by a living organism or is a synthetically derived structure that is structurally similar and functionally identical to a naturally-occurring pheromone, which, alone or in combination with other such compounds, modifies the behavior of other individuals of the same species. In the same section, the Agency defines a lepidopteran pheromone as an arthropod pheromone produced by a member of the insect order Lepidoptera. A subset of lepidopteran pheromones are straight chain lepidopteran pheromones, which:

"Consist[s] of an unbranched aliphatic chain (between 9 and 18 carbons) ending in an alcohol, aldehyde, or acetate functional group and contain[s] up to three double bonds in the aliphatic backbone".

SCLPs are formulated into end-use products at low concentrations that are intended for use as mating disruptants. The tolerance exemption for SCLPs in 40 CFR §180.1153 limits the application rate to 150 grams active ingredient/acre/year on growing crops and post-harvest treatments, or approximately 410 mg of pheromone per acre per day. For comparison, in orchards infested with codling moth the females may emit up to 184 mg of mating pheromone per acre per day. In any growing season, this value is multiplied by multiple arthropod species emitting multiple pheromones in the same area (Jones 2012). Exposure to humans and nontarget organisms from SCLP pesticide products is therefore expected to be much lower than from natural levels. Additionally, arthropod pheromones are volatile, subject to rapid environmental degradation, and are metabolized by enzyme species present in most living organisms (OECD 2002, Welter 2005). End-use product formulations are typically flakes, granules, traps, or retrievable polymeric matrix dispensers.

In most cases the toxicology and environmental data requirements for SCLPs are waived. The Agency references the OECD publication  -  Guidance for Registration Requirement for Pheromones and Other Semiochemicals Used for Pest Control in making this decision (OECD 2002). In addition, the EPA Biopesticide Registration Action Document for SCLPs comments that:

"No risks to human health are expected from the use of lepidopteran pheromones based on the low toxicity in animal testing and the expected low exposure to humans. Furthermore, adverse effects on nontarget organisms are not expected because these pheromones are released in very small quantities in the environment and act on a select group of insects. Appropriate precautionary labeling of end use products will further minimize potential exposure and mitigate risk to nontarget organisms". (SCLP BRAD 2009).

However, in some cases registrants have been required to submit additional information to satisfy human health assessment or nontarget organisms and environmental fate data requirements. A summary of data that has been reviewed by the Agency is summarized in relevant sections below.

The Agency has an understanding developed over time that straight chain lepidopteran pheromones are subject to a reduced data set and that no unreasonable adverse effects will result from the use of SCLP products according to good agricultural practices. In light of this SCLPs are exempted from 40 CFR §158.2050, Biochemical Pesticides Human Health Assessment, and 40 CFR §158.2060, Biochemical Pesticides Nontarget Organisms and Environmental Fate Data Requirements when applied at a maximum of 150 grams active ingredient/acre/year. The only exception applies to products readily available to avian species. This exception for products available to avian species applies to the SCLPs after they are formulated into end-use products (40 CFR §158.2060(e)(1)).

Regulatory History
Regulation of straight chain lepidopteran pheromones predates the founding of the Agency. The first SCLP, (z,z)-11,13-hexadecadienal, was registered in July 1969. As of this scoping document, the Agency has thirty five SCLPs with active registrations. On August 30, 1994, the Agency issued a final rule establishing an exemption from the requirement of a tolerance for residues from the use of straight chain lepidopteran pheromones in 40 CFR §180.1153. An SCLP Biopesticide Registration Action Document was issued in August 2001 and as new active ingredients have been registered the document has been amended with updated information.

The straight chain lepidopteran pheromones with active registrations are summarized in Table 1 below. In some instances SCLPs have been registered concurrently and are always used together. These active ingredients are typically individual components of a specific insect pheromone and are naturally grouped together.

                                   SCLP Name
                                      PCC
                                  CAS Number
                                Number TGAI/MPs
                                  Number EPs
(z,z)-11,13-hexadecadienal
                                                                         000711
71317-73-2
                                                                              2
                                                                              5
lauryl alcohol
                                                                         001509
112-53-8
                                                                              1
                                                                             13
myristyl alcohol
                                                                         001510
112-72-1
                                                                              1
                                                                              7
(e,z,z)-3,8,11-tetradecatrienyl acetate
                                                                         011472
163041-94-9
                                                                              1
                                                                              7
(z,z,e)-7,11,13-hexadecatrienal
                                                                         029000
888042-38-4
                                                                              1
                                                                              1
(e)-5-decen-1-ol & (e)-5-decenyl acetate
                                                                 078038, 117703
56578-18-8, 38421-90-8
                                                                              3
                                                                             13
(z,e)-7,11-hexadecadien-1-yl acetate & (z,z)-7,11-hexadecadien-1-yl acetate
                                                                 114101, 114102
53042-79-8, 52207-99-5
                                                                              1
                                                                              6
cis-7,8-epoxy-2-methyloctadecane
                                                                         114301
29804-22-6
                                                                              2
                                                                              4
(z,e)-9,12-tetradecadienyl acetate
                                                                         117203
31654-77-0
                                                                              2
                                                                              5
(e,z)-2,13-octadecadien-1-yl acetate & (e,z)-2,13-octadecadien-1-ol
                                                                 117242, 117244
86252-65-5, 123551-47-3
                                                                              1
                                                                              1
(z)-11-hexadecenal
                                                                         120001
53939-28-9
                                                                              3
                                                                             31
(z)-11-tetradecenal
                                                                         120011
35237-64-0
                                                                              0
                                                                              1
(z)-4-tridecen-1-yl acetate & (e)-4-tridecen-1-yl acetate
                                                                 121901, 121902
65954-19-0, 72269-48-8
                                                                              2
                                                                              4
(e,e)-9,11-tetradecadien-1-ol
                                                                         128000
54664-98-1
                                                                              1
                                                                              8
n-tetradecyl acetate
                                                                         128002
638-59-5
                                                                              1
                                                                              1
(z)-8-dodecen-1-yl acetate
                                                                         128906
28079-04-1
                                                                              4
                                                                             24
(e)8-dodecen-1-yl acetate
                                                                         128907
38363-29-0
                                                                              4
                                                                             24
(z)-8-dodecen-1-ol
                                                                         128908
40642-40-8
                                                                              4
                                                                             24
(z)-11-tetradecenyl acetate & (e)-11-tetradecenyl acetate
                                                                 128980, 129019
20711-10-8, 33189-72-9
                                                                              2
                                                                             13
(z)-9-dodecenyl acetate
                                                                         129004
16974-11-1
                                                                              1
                                                                              2
(z)-11-tetradecen-1-ol
                                                                         129021
34010-15-5
                                                                              0
                                                                              1
(e,e)-8,10-dodecadien-1-ol
                                                                         129028
33956-49-9
                                                                              5
                                                                             29
(z)-6-heneicosen-11-one
                                                                         129060
54844-65-4
                                                                              0
                                                                              1
(z)-11-hexadecenyl acetate
                                                                         129071
34010-21-4
                                                                              1
                                                                              2
(z)-9-tetradecen-1-yl acetate
                                                                         129109
16725-53-4
                                                                              0
                                                                              2
(e,z)-3,13-octadecadien-1-ol
                                                                         129117
66410-28-4
                                                                              1
                                                                              1
(z,z)-3,13-octadecadien-1-ol
                                                                         117241
66410-24-0
                                                                              0
                                                                              1
(z,e)-7,9-dodecadien-1-ol
                                                                         011471
55774-32-8
                                                                              0
                                                                              1

Table 1. Straight Chain Lepidopteran Pheromones with Active Registrations.

Product Chemistry Summary
The Agency has conducted a review of the available product chemistry data and information. These data are summarized below for three SCLPs that are representative of the classes of pheromones the Agency consider SCLPs. All SCLPs have an unbranched long chain consisting of 9 to 18 carbons. They differ in the end functional group, which can be an alcohol, aldehyde, or acetate, and the number of double bonds. The Agency allows up to three double bonds in the classification. For these reasons the SCLPs are structurally similar to one another and the product chemistry data follow similar patterns. While the Agency is satisfied with the product chemistry data on hand this does not exempt future registrations from being required to satisfy all biochemical product chemistry data requirements. This is especially pertinent for the submission of UV/Visible light absorption data. Below are three tables summarizing product chemistry data submitted for a specific SCLP, one from each functional group class. 

Table 2. Biochemical Pesticides Product Chemistry Data Requirements for SCLP n-Tetradecyl Acetate.
                                 Guideline No.
                       Physical and Chemical Properties
                                   Status[1]
                                     Value
                                     MRID/
                                    Source
830.1100
Product Identity and Composition
                                       A

--
830.1200
Description of starting materials, production and formulation process
                                       A
CBI
--
830.1400
Discussion of formation of impurities
                                       A
CBI
--
830.1700
Preliminary analysis
                                       A
CBI
--
830.6302
Color
                                       A
Pale Yellow
47423705
830.6303
Physical state
                                       A
Liquid
47423705
830.6304
Odor
                                       A
Fatty
47423705
830.6313
Stability to normal and elevated temperatures, metals and metal ions
                                       A
Stable
47423705
830.7000
pH
                                       A
5.5-7.0 @20°C
47423705
830.7050
UV/Visible light absorption
290 nm
                                       A
Molar Absorptivity (ε)
0.72 L[mol-1cm-1]
47423705
830.7200
Melting point/melting range
                                       A
2-4°C
47423705
830.7220
Boiling point/boiling range
                                       A
142-146°C @3 mmHg
47423705
830.7300
Density (specific gravity)
                                       A
0.866 @20°C
47423705
830.7520
Particle size, fiber length, and diameter distribution
                                      N/A
--
47423705
830.7550
830.7560
830.7570
Partition coefficient (n-Octanol/Water)
                                       A
Log Pow = 6.76 @25°C
BRAD
830.7840
Water solubility 
                                       A
Insoluble
47423705
830.7950
Vapor pressure
                                       A
3.6-4.5x10[-4] mmHg @20°C
47423705
   1. A=Acceptable. N/A=Not Applicable. N/D=Not Determined. CBI=Confidential Business Information.

Table 3. Biochemical Pesticides Product Chemistry Data Requirements for SCLP (Z,Z,E)-7,11,13-Hexadecatrienal.
                                 Guideline No.
                       Physical and Chemical Properties
                                   Status[1]
                                     Value
                                     MRID/
                                    Source
830.1100
Product Identity and Composition
                                       A
                                       
--
830.1200
Description of starting materials, production and formulation process
                                       A
CBI
----
830.1400
Discussion of formation of impurities
                                       A
CBI
--
830.1700
Preliminary analysis
                                       A
CBI

830.6302
Color
                                       A
Pale Yellow
47922801
830.6303
Physical state
                                       A
Liquid
47922801
830.6304
Odor
                                       A
Mild/waxy
47922801
830.6313
Stability to normal and elevated temperatures, metals and metal ions
                                       A
Stable
47922801
830.7000
pH
                                      N/A
insoluble
47922801
830.7050
UV/Visible light absorption
290 nm
                                       A
λmax = 232 nm
47922801
830.7200
Melting point/melting range
                                      N/A
--
47922801
830.7220
Boiling point/boiling range
                                       A
341 +- 21°C
47922801
830.7300
Density (specific gravity)
                                       A
0.865 @25°C
47922801
830.7520
Particle size, fiber length, and diameter distribution
                                      N/A
--
47922801
830.7550
830.7560
830.7570
Partition coefficient (n-Octanol/Water)
                                      N/A
Log Pow >  5.35 @25°C
48231701
48231702
48231703
830.7840
Water solubility 
                                       A
Insoluble 
47922801
830.7950
Vapor pressure
                                       A
8.23x10[-4] torr @25°C
47922801
   1. A=Acceptable. N/A=Not Applicable. N/D=Not Determined. CBI=Confidential Business Information.

Table 4. Biochemical Pesticides Product Chemistry Data Requirements for SCLP (Z)-11-Tetradecen-1-ol.
                                 Guideline No.
                       Physical and Chemical Properties
                                   Status[1]
                                     Value
                                     MRID/
                                    Source
830.1100
Product Identity and Composition
                                       A

--
830.1200
Description of starting materials, production and formulation process
                                       A
CBI
--
830.1400
Discussion of formation of impurities
                                       A
CBI
--
830.1700
Preliminary analysis
                                       A
CBI
--
830.6302
Color
                                       A
Pale Yellow
46832301
830.6303
Physical state
                                       A
Liquid
46832301
830.6304
Odor
                                       A
Fatty
46832301
830.6313
Stability to normal and elevated temperatures, metals and metal ions
                                       A
Stable
46832301
830.7000
pH
                                       A
5.4
46832301
830.7050
UV/Visible light absorption

                                       A
See MRID
46832301
830.7200
Melting point/melting range
                                      N/A

46832301
830.7220
Boiling point/boiling range
                                       A
138-140 @520 Pa
46832301
830.7300
Density (specific gravity)
                                       A
0.875 @20°C
46832301
830.7520
Particle size, fiber length, and diameter distribution
                                      N/A
--
46832301
830.7550
830.7560
830.7570
Partition coefficient (n-Octanol/Water)
                                       A
Log Pow = 4.6 @25°C
46832301
830.7840
Water solubility 
                                       A
<0.0004 g/l
46832301
830.7950
Vapor pressure
                                       A
0.16-0.20 Pa @20°C
46832301
   1. A=Acceptable. N/A=Not Applicable. N/D=Not Determined. CBI=Confidential Business Information.
                                       
Human Health Assessment Summary

   1. Toxicology Assessment
40 CFR §158.2050 states that the "data in this section [Biochemical Pesticides Human Health Assessment Data Requirements] are not required for straight chain lepidopteran pheromones when applied up to a maximum use rate of 150 grams active ingredient/acre/year." The Agency has no registered SCLPs that exceed this use rate according to label instructions.

Straight Chain Lepidopteran Pheromones are exempt from the requirement of a tolerance under 40 CFR §180.1153, which states:

"Lepidopteran pheromones that are naturally occurring compounds, or identical or substantially similar synthetic compounds, designated by an unbranched aliphatic chain (between 9 and 18 carbons) ending in an alcohol, aldehyde or acetate functional group and containing up to 3 double bonds in the aliphatic backbone, are exempt from the requirement of a tolerance in or on all raw agricultural commodities. This exemption only pertains to those situations when the pheromone is: Applied to growing crops at a rate not to exceed 150 grams active ingredient/acre/year in accordance with good agricultural practices; and applied as a post-harvest treatment to stored food commodities at a rate not to exceed 3.5 grams active ingredient/1000 ft[2]/year (equivalent to 150 grams active ingredient/acre/year) in accordance with good agricultural practices. [71 FR 45399, Aug. 9, 2006]".

   2. Food Quality Protection Act (FQPA) Consideration
         a. Dietary Exposure and Risk Characterization
In accordance with 40 CFR §180.1153, SCLPs are exempt from the requirement of a tolerance. As discussed previously, the active ingredients pose negligible toxicological hazard, including dietary hazard. Given use patterns registered with the Agency, there is limited dietary exposure from SCLPs. This is consistent with the conclusions reached by the OECD, which has determined that consumption of food containing residues of SCLPs presents no risk. (OECD, 2002).

         b. Drinking Water Exposure and Risk Characterization
No significant drinking water exposure or residues are expected from the SCLPs when they are used according to precautionary label language. SCLPs are typically contained inside dispensers or traps, or are applied to terrestrial areas only. Studies of the fate of SCLPs on moistened soil and water show rapid dissipation. This is due to the volatilization of the parent compounds with half life in water varying from 30 hours to 7 days (Shaver, 1983; Henson, 1977).

         c. Occupational, Residential, School, and Day Care Exposure and Risk Characterization
SCLPs are specifically targeted toward modifying the behavior of lepidopteran species. The expected exposure to humans and food/feed crops is low due to low application rates (>=150 g ai/acre/year) which, as mentioned above, are comparable or less than pheromone levels found naturally. Appropriate signal word and precautionary statements are also utilized to minimize exposure and misuse of SCLP products.

No outdoor or indoor residential, school, or day care uses are currently approved for products containing straight chain lepidopteran pheromones.

   3. Cumulative Effects
Section 408(b)(2)(D)(v) of the Federal Food, Drug, and Cosmetic Act requires the Agency to consider the cumulative exposure of SCLPs as they are registered. These considerations include the possible cumulative effects of such residues on infants and children. SCLPs have a non-toxic mode of action and there is no indication or evidence to suggest that these biochemical pesticides share a common mechanism of toxicity with any other substances. Therefore, cumulative exposure concerns are not anticipated for the SCLPs.

   4. Incidents
Incident data were reported for the SCLPs associated with the light brown apple moth, (z)-11-tetradecenyl acetate and (e)-11-tetradecenyl acetate. On October 12, 2007, the EPA issued a response to concerns arising from a temporary restraining order issues by the California Supreme Court suspending the use of these SCLPs in ground and aerial applications. After a careful review, the Agency concluded that the use of these products presented negligible risks to human health and the environment due to a non-toxic mode of action, classification as SCLP with known low mammalian/human toxicity, no evidence of mutagenicity, history of exposure to humans and the environment as a pesticide with no known effects, and low exposure (EPA).

   5. Risk Characterization
SCLPs, as mentioned above, are arthropod pheromones that act via a non-toxic mode of action on specific insect pests. Given the low toxicity of lepidopteran pheromones in animal testing and the expected low exposure to humans, no risk to human health is expected form use of SCLP products (OECD 2002). It has been determined that there are no acute mammalian toxicity at the limit dose levels of the following studies: acute oral toxicity (LD50>5000 mg/kg  -  category IV, nontoxic); acute dermal toxicity (LD50>2000 mg/kg  -  category III, nontoxic); acute inhalation toxicity (LD50 generally > 5 mg/L  -  category III-IV, practically nontoxic), no evidence of mutagenicity (Ames Salmonella assay), and limited eye and skin irritation (category IV). Pheromones are also not likely to be dermal sensitizers (Beuhler hypersensitivity test) (Jones 2003). The Agency has considered the various routes of exposure and potential risks of the active ingredients and determined that the proposed use of the active ingredient does not pose significant risk to all populations, including infants and children. 

Environmental Assessment

   1. Environmental Chemistry and Fate Assessment
The straight chain lepidopteran pheromones are applied to a variety of crops in various ways. The most common distribution methods are in dispensers, flakes, microencapsulated beads, or granular formulations.

The SCLPs are, as a group, insoluble in water and are of intermediate volatility. This medium volatility is key to the efficacy of SCLPs (Barth 241) and allows small amounts to be placed in the environment, resulting in low exposure to the active ingredient. Studies of the fate of SCLPs on moistened soil and water show rapid dissipation. This is due to the volatilization of the parent compounds with half life in water varying from 30 hours to 7 days (Shaver, 1983; Henson, 1977). According to the OECD, SCLPs readily undergo photo-oxidation. SCLPs are transformed by oxidation of the double bonds in the carbon chain and other types of oxidative degradation. The enzymes operative during the degradation of SCLP residues are ubiquitous in nature (OECD 2002). 

Environmental fate data are not required for SCLPs being applied at a maximum rate of 150 grams active ingredient/acre/year per 40 CFR §158.2060, except those SCLPs expected to be available to avian species. This exception for products available to avian species applies to the SCLPs after they are formulated into end-use products. Environmental fate testing is typically required when results from Tier I testing indicate potential adverse effects. This has not been the case with the currently registered SCLPs. Straight chain lepidopteran pheromone products are not intended to be applied directly to aquatic environments and label language provides specific instructions to avoid direct applications to water. 

   2. Ecological Effects and Hazard Assessment
According to 40 CFR §158.2060 (a)(2), SCLPs applied up to a maximum use rate of 150 grams active ingredient/acre/year in formulations not expected to be available to avian species are not required to address nontarget toxicity data requirements. In instances where the products are expected to be available to avian species, as in granular formulations, the Agency has typically required the registrant to submit Tier 1 Avian Testing as outlined in 40 CFR §158.2060 and/or other relevant data. For example, in a review to A. Leslie from N. Rappaport PhD, dated 03/96, the Agency concluded that a SCLP product formulated into a bead product posed no risk to birds due to low toxicity, low exposure, and selectivity of seed-eating birds. Other studies have determined that SCLP pheromones are practically nontoxic to birds (Maciorowski 1994). In a review of a blend of lauryl and myristyl alcohol, the Agency determined an LD50 >2150 mg/kg to the bobwhite quail (Mossler 1994, 1). In laboratory settings SCLPs have shown moderate toxicity to D. magna, but are not considered toxic when formulated into dispenser or limited to 150 grams active ingredient/acre/year (Esmeralda 2006, Weatherson 1995). A 96-hour LC50 of >72 mg/l classified a product containing (e,e)-8,10-dodecadien-1-ol, 1-dodecanol, and 1-tetradecanol as slightly toxic to rainbow trout. The NOEC was 43 mg/L (Mossler 1994, 2).

   3. Measure of Ecological Exposure
Measures of exposure are based on aquatic and terrestrial models that predict estimated environmental concentrations of a pesticide using maximum labeled application rates and methods of application. The use patterns for SCLPs vary from end-use products inside dispenser and other enclosed traps, flakes, encapsulated beads, or granules. Combined with a low solubility in water and label language prohibiting application directly to water, runoff and spray drift are not likely transport mechanisms of SCLPs to nontarget aquatic and terrestrial sites. For aquatic exposure, the Agency estimated environmental concentrations of (z,e)-7,11-hexadecadien-1-yl acetate and (z,z)-7,11-hexadecadien-1-yl acetate by applying a Tier I aquatic model, GENEEEC Version 2.0 (Appendix A). The GENEEC model predicts very low environmental concentrations, with a peak generic estimated environmental concentration of 308 ppt (parts per trillion).

   4. Risk Characterization
Based on the application methods of end-use products containing straight chain lepidopteran pheromones as their active ingredient, there is no little exposure of SCLPs to nontarget terrestrial and aquatic organisms. As discussed above, SCLPs are exposed to the environment at concentrations lower than that found naturally and are presented in the environment in ways that are not readily accessible to nontarget organisms. Based on the expected very low exposure to aquatic organisms, low toxicity to birds, and on its use patterns and use instructions, the Agency has determined that it will have "No Effect" on any currently listed, threatened, or endangered species or any designated critical habitat.

                                  References
                                       
Barth, F.G., Schmid, A. Ecology of Sensing. Springer, 2001.
                                       
Esmeralda, R., Barata C., Damásio, J., Bosch, M.P., Guerrero, A. Aquatic ecotoxicity of a pheromonal antagonist in Daphnia magna and Desmodesmus subspicatus. Aquatic Toxic 79 (2006) 296-303.

EPA BRAD.  Straight Chain Lepidopteran Pheromones. 02/27/2009.
                                       
EPA. Quarantine Exemptions for Light Brown Apple Moth Pheromones. http://www.epa.gov/region9/pesticides/light-brown-moth.html. Accessed 02/29/12.

Jones, R. "Biochemical Pesticides: Green Chemistry Designs by Nature". Green Processes Volume 9: Designing Safer Chemicals. Boethling, R., Voutchkova, A. Wiley-VCH, 2011. Pg. 341.

Jones, R. EPA Memo to A. Bryceland dated 11/18/2003.

Maciorowski, A. EPA Memo to P. Hutton dated 10/3/1994.

Mossler, M (1). EPA Review of Avian Oral LD50 Test on Bobwhite Quail Study.

Mossler, M (2). EPA Review of Freshwater Fish Static Acute Toxicity Test.

OECD Series on Pesticides, Number 12. Guidance for Registration Requirements for Pheromones and Other Semiochemicals Used for Arthropod Pest Control.

Weatherson, I., Minks, A.K. Regulation of semiochemical -- global aspects. Int. Pest Manage. Rev. 1 (1995) 1-13.

Welter, S.C., Pickel, C., Millar, J., Cave, F., Van Steenwyk, R.A. and Dunley, J. Pheromone mating disruption offers management options for key pests. Calif. Agric., 59 (1), 16-22 (2005).

Appendix A: GENEEC Run for (z,e)-7,11-hexadecadien-1-yl acetate and (z,z)-7,11-hexadecadien-1-yl acetate
                                       
RUN No.   3 FOR 114101           ON   cotton        * INPUT VALUES * 
   --------------------------------------------------------------------
    RATE (#/AC)   No.APPS &   SOIL  SOLUBIL   APPL TYPE NO-SPRAY INCORP
     ONE(MULT)    INTERVAL    Koc   (PPM )    (%DRIFT)   (FT)     (IN)
   --------------------------------------------------------------------
   .022(   .022)  10  25        .0  120.0   GRANUL(   .0)     .0    .0

   FIELD AND STANDARD POND HALFLIFE VALUES (DAYS) 
   --------------------------------------------------------------------
   METABOLIC  DAYS UNTIL  HYDROLYSIS   PHOTOLYSIS   METABOLIC  COMBINED
    (FIELD)   RAIN/RUNOFF   (POND)     (POND-EFF)    (POND)     (POND) 
   --------------------------------------------------------------------
      1.00        2          N/A       .00-     .00     2.00      2.00

   GENERIC EECs (IN NANOGRAMS/LITER (PPTr))     Version 2.0 Aug 1, 2001
   --------------------------------------------------------------------
       PEAK      MAX 4 DAY     MAX 21 DAY    MAX 60 DAY    MAX 90 DAY
       GEEC      AVG GEEC       AVG GEEC      AVG GEEC      AVG GEEC
   --------------------------------------------------------------------
      308.88      237.37         83.20         29.66         19.77