Straight Chain Lepidopteran Pheromones

Product Chemistry, Human Health, Nontarget
UNITED STATES ENVIRONMENTAL PROTECTION AGENCY

**MEMORANDUM SUBJECT**  : Data Requirement

Chain Lepidopteran Pheromones **Registration Review Case #: PC Code**  **s :**  **CAS Numbers: Chemical Class:**  **FROM:** Jacob S Moore , Chemist

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 assessment, and nontarget organisms and environmental fate biopesticide class straight chain lepidopteran pheromones r egistration r eview w ork p lan. Straight Chain Lepidopteran Pheromones Case Number: Chemistry, Human Health, Nontarget

—Registration Review
UNITED STATES ENVIRONMENTAL PROTECTION AGENCY

WASHINGTON, D.C. 20460
3/8/2012 OFFICE OF CHEMICAL SAFETY AND POLLUTION PREVENTION Data Requirement Scoping Document for the Registration Review o Lepidopteran Pheromones . **Registration Review Case #: 8802**  **Multiple, See Table 1 Multiple, See Table 1**  **Biochem ical**  , Chemist /s/ 3/8/12 Biochemical Pesticides Branch Biopesticides & Pollution Prevention Division (7511P) Russell S. Jones, Ph.D., Senior Biologist /s/ 3/8/12 Biochemical Pesticides Branch Biopesticides & Pollution Prevention Division (7511P)

, Regulatory

Action Leader Biochemical Pesticides Branch Biopesticides & Pollution Prevention Division (7511P)

A preliminary

assessment of available information on product chemistry , human health assessment, and nontarget organisms and environmental fate data associated with the

straight chain lepidopteran pheromones in support of the development of a Case Number: 8802

OFFICE OF CHEMICAL SAFETY AND POLLUTION PREVENTION Scoping Document for the Registration Review o f the Straight **Multiple, See Table 1 Multiple, See Table 1** 

, human health data associated with the in support of the development of aStraight Chain Lepidopteran Pheromones Case Number: 8802

**Introduction** A pheromone, defined b y the Agency in 40 CFR §158.2000, is a compound produced b y a livi ng organism or is a s ynthetically derived structure that is structurally similar and functionally identical to a naturall y - 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, aldeh yd e, 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 c rops and post - harvest treatments , or approximately 410 mg of pheromone pe r 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 an y 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 enzy me species present in most living organisms (OECD 2002, Welter 2005). End - use product formulations are typically flakes , granules, traps, or retrievable pol y meric 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 C ontrol 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 miti gate risk to nontarget organisms” . ( SCLP BRAD 2009).Straight Chain Lepidopteran Pheromones Case Number: 8802

Product Chemistry, Human Health, Nontarget

—Registration Review

3 However, in some cases registrants have been required to submit additional information to satisfy human health assessment or nontarget organisms and environmental fate data requirement s. 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. Inlight of this SCLPs are exempted from 40 CFR §158.2050, Biochemical Pesticides Human Health Assessment, and 40 CFR §158.2060, Biochemical Pesticides Nont arget Organisms and Environmental Fate Data Requirements when applied at a maximum of 150 grams active ingredient/acre/ye ar. The onl y exception applies to products rea dil y available to avian species. This exception for products available to avian species a pplies 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 regi stered 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 stra ight 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 update d information. The straight chain lepidopteran pheromones with active registrations are summarized in Table 1 below. In some instances SCLPs have been registered concurrentl y and are alway s used together. These active ingredients are ty picall y 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 13Straight Chain Lepidopteran Pheromones Case Number: 8802

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**(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.**Straight Chain Lepidopteran Pheromones Case Number: 8802

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**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, aldeh yde, 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. Wh ile 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.** **Guide line No.**  **Physical and Chemical Properties**  **Statu s**  **1 Value**  **MRID /**  **Source 830.1100**  Product Identity and

Com position A --

**830.1200** Description of starting

materials, production and formulation process A CBI -- **830.1400** Discussion of formation of

im purities A CBI -- **830.1700** Preliminary analysis A CBI -- **830.6302** Color A Pale Yellow 47423705 **830.6303** Phy sical state A Liquid 47423705 **830.6304** Odor A Fatty 47423705 **830.6313** Stability to normal and

elevated temperatures, metals and me tal 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 P ow = 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.Straight Chain Lepidopteran Pheromones Case Number: 8802

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**Table 3 .**  **Biochemical Pesticides Product Chemistry Data Requirements for SCLP (Z,Z,E)**  **- 7,11,13**  **- Hexadecatrienal.**  **Guideline No. Physical and Chemical**  **Properties Statu**  **s 1**  **Value MRID**  **/ Source**  **830.1100** Product Identity and

Com position A --

**830.1200** Description of starting

materials, production and formulation process A CBI ---- **830.1400** Discussion of formation of

im purities A CBI -- **830.1700** Preliminary analysis A CBI **830.6302** Color A Pale Yellow 47922801 **830.6303** Phy sical 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 P ow > 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**  **Statu s**  **1 Value**  **MRID /**  **Source 830.1100**  Product Identity and

Com position A -- **830.1200** Description of starting

materials, production and formulation process A CBI -- **830.1400** Discussion of formation of

im purities A CBI -- **830.1700** Preliminary analysis A CBI --Straight Chain Lepidopteran Pheromones Case Number: 8802

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**830.6302** Color A Pale Yellow 46832301 **830.6303** Phy sical 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 P ow = 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. Strai ght Chain Lepidopteran Pheromones are exempt from the requirement of a tolerance under 40 CFR §180.1153, which states: “Lepidopteran pheromones that are naturall y occurring compounds, or identical or substantially

similar sy

nthetic compounds, designated b y 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 ft2 /year (equivalent to 150 grams active ingredient/acre/year) in accordance with good agricultural practices. [71 FR 45399, Aug. 9, 2006]”.Straight Chain Lepidopteran Pheromones Case Number: 8802

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**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 previousl y, 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 res idues of SCLPs presents no risk. (OECD, 2002). **b. Drinking Water Exposure and Risk Characterization**  No significant drinking water exposure or residues are expected from th e SCLPs when they are used according to precautionary label language . SCLPs are typically contained inside dispen sers 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 day s (Shaver, 1983; Henson, 1977).

**c. Occupational, Residential, School, and Day Care Exposure and Risk**  **Characterization** SCLPs are specificall y 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/ye ar) which, as mentioned above, are comparable or less than pher omone 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 currentl y approved for products containin g 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 poss ible 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 an y other substances. Therefore, cumulative exposure concerns are not anticipated for the SCLPs. **4. Incidents**  In cident data were reported for the SCLPs associated with the light brown apple moth, (z) - 11 - tetradecen ylacetate and (e) - 11 - tetradecenyl acetate. On October 12, 2007, the EP A issued a response to concerns arising from a temporary restraining order issues b y 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 produc ts 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 toStraight Chain Lepidopteran Pheromones Case Number: 8802

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humans and the environment as a pestici de 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 testi ng 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 (LD 50 >5000 mg/kg

– category IV, nontoxic); acute dermal toxicity (LD 50 >2000 mg/kg

– category I II, nontoxic); acute inhalation toxicity (LD 50 generall y > 5 mg/L

– category I II - 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 h ypersensitivity test) (Jones 2003). The Agency

has considered the various routes of exposure and potential risks of the active ingr edients 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 ch ain lepidopteran pheromones are applied to a variety of crops in various way s. 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 volatil ity . 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 dissip ation. This is due to the volatilization of the parent compounds with half life in water varying from 30 hours to 7 day s (Shaver, 1983; Henson, 1977). According to the OECD, SCLPs readil y undergo photo - oxidation. SCLPs are transformed by oxidation of the d ouble bonds in the carbon chain and other ty pes of oxidative degradation. The enzy mes 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/ye ar 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. Env ironmental fate testing is typicall y required when results from Tier I testing indicate potential adverse effects. This has not been the case with the currentl y 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.Straight Chain Lepidopteran Pheromones Case Number: 8802

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**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/ye ar in formulations not expected t o be available to avian species are not required to address nontarget toxicity data requirements. Ininstances where the products are expected to be available to avian species, as in granular formulations, the Agency has typicall y 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. L eslie 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 practicall y nontoxic to birds (Maciorowski 1994 ). In a review of a blend of lauryl and m yrist ylalcohol , the Agency determined an LD 50 >2 150 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 dispense r or limited to 150 grams active ingredient/acre/ye ar (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 slightl y t oxic 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 applicati on. 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 appli cation directly to water, runoff and s pray 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 - ylacetate by appl yi ng 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 envir onment at concentrations lower than that found naturall y and are presented in the environment in ways that are not readil y accessible to nontarget organisms. Based on the expected very low exposure to aquatic organisms, low toxicity to birds, and on its us e patterns and use instructions, the Agency has determined that it will have “ **No Effect** ” on any currentl y listed, threatened, or endangered species or an y designated critical habitat.Straight Chain Lepidopteran Pheromones Case Number: 8802

11 **References** Barth, F.G., Schmid, A. Ecology of Sensing. Springer, 200 1. 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 L ight 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 LD 50 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 Steenwy k, R.A. and Dunley , J. Pheromone mating disruption offers management options for key pests . Calif. Agric., **59** (1), 16 - 22 (2005).Straight Chain Lepidopteran Pheromones Case Number: 8802

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**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 APPLTYPE NO - SPRAY INCORP ONE(MULT) INTERVALKoc (PPM ) (%D RIFT) (FT) (IN)

-------------------------------------------------------------------- .022( .022) 10 25 .0 120.0 GRANUL( .0) .0 .0 FIELD AND STANDARD POND HALFLIFE VALUES (DAYS)

----------------------------------- --------------------------------- METABOLIC DAYS UNTIL HYDROLYSI S PHOTOLYSI S METABOLIC COMBINED (FIELD) RAIN/RUNOFF (POND) (POND - EFF) (POND) (POND)

-------------------------------------------------------------------- 1.00 2 N/A .00 - .00 2.00 2.00 GENERI C 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