Straight Chain Lepidopteran Pheromones Registration Review Case No. 8200 

PC Codes: Multiple 

1 

 UNITED STATES ENVIRONMENTAL PROTECTION AGENCY 

 WASHINGTON, D.C. 20460 

 OFFICE OF CHEMICAL SAFETY & POLLUTION PREVENTION 

OFFICE OF PESTICIDE PROGRAMS 

MEMORANDUM

DATE: 19 November 2012

SUBJECT: Non-Target Organism Studies, Hazard Assessment, and Endangered Species 

Assessment for Straight-Chain Lepidopteran Pheromones (SCLPs) in Support of 

Registration Review. 

 Case No.: 8200 

 Chemical Class: Biochemical 

 PC Codes: Multiple (see Table 1) 

CAS Nos. Multiple (see Table 1) 

 Tolerance Exemptions: 40 CFR 180.1153 

FROM: Russell S. Jones, Ph.D., Senior Biologist /s/ 11/19/2012 

 Biochemical Pesticides Branch 

 Biopesticides & Pollution Prevention Division (7511P) 

TO: Colin Walsh, Regulatory Action Leader 

 Biochemical Pesticides Branch 

 Biopesticides & Pollution Prevention Division (7511P) 

EXECUTIVE SUMMARY

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 Straight-Chain Lepidopteran 

Pheromones (SCLPs) will have “No Effect” on any currently listed, threatened, or endangered 

species or any designated critical habitat. 

SCLPs are applied to the environment at concentrations much lower naturally occurring 

background levels and are applied in ways that are not readily accessible to nontarget organisms. 
Straight Chain Lepidopteran Pheromones Registration Review Case No. 8200 

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They are volatile substances that induce highly species specific behavioral responses in males of 

the target pests. Specifically, they disrupt mating by the masking of, or misdirection from 

natural mating pheromone mating plumes emitted by females of the target species. The SCLPs 

are practically non-toxic to mammals, birds, and insects on an acute and dietary basis. In 

laboratory studies, SCLPs range from very highly toxic to practically non-toxic to fish and 

aquatic invertebrates. The SCLPs, however, are practically insoluble in water and would never 

reach concentrations in water where toxicity would occur. In addition, SCLP products are not 

intended for application to aquatic sites. No data are available for plants, however, due to the 

low application rates, high relative volatility, and little to no measureable residues, effects on 

non-target plants are highly unlikely. No adverse effects have ever been reported on plants 

treated with SCLP products after several decades of use in IPM programs for crop protection 

from insect pests. 

DESCRIPTION OF THE ACTIVE INGREDIENTS

Semiochemicals include all substances emitted by plants, animals, and microorganisms that 

elicit behavioral responses in the receptor species. A semiochemical emitted by an individual of 

one species that effects the individuals of other species is defined as an allelochemical; a 

semiochemical emitted by an individual of a species that effects individuals of the same species 

is defined as a pheromone (see review by Jones, 2012). 

Straight Chain Lepidopteran Pheromones (SCLPs) are semiochemicals registered as mating 

disruptants for use on food crops and ornamentals. As defined by EPA at 40 CFR §158.2000, 

a pheromone is either 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, that, alone or in combination with other such compounds, modifies the behavior 

of other individuals of the same species. EPA defines a Lepidopteran pheromone in 40 CFR § 

158.2000 (a)(2)(ii) as an arthropod pheromone produced by a member of the insect order 

Lepidoptera and consist of an unbranched aliphatic chain (between nine and eighteen 

carbons) ending in an alcohol, aldehyde, or acetate functional group. This group can contain 

up to three double bonds in the aliphatic backbone (40 CFR § 158.2000 (a)(2)(iii)). 

Chemistry data are summarized below for three SCLPs that are representative of the classes of 

pheromones the Agency considers to be SCLPs. All SCLPs consist of an unbranched long chain 

of 9 to 18 carbons. They differ in the end functional group, which can be an alcohol, aldehyde, or 

acetate, and in the number of double bonds. The carbon chain may be unsaturated or contain up 

to three double bonds. 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 

existing product chemistry database, it does not exempt future registrations from being required 

to satisfy all biochemical product chemistry data requirements. Below are three tables 
Straight Chain Lepidopteran Pheromones Registration Review Case No. 8200 

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summarizing product chemistry data submitted for a specific SCLP from each of the three 

functional group classes. 

Table 1. Biochemical Pesticides Product Chemistry Data for SCLP n-Tetradecyl Acetate. 

Guideline No. Physical and Chemical 

Properties 

Status1 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 Lmol-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 (nOctanol/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. CBI=Confidential Business Information. 
Straight Chain Lepidopteran Pheromones Registration Review Case No. 8200 

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Table 2. Biochemical Pesticides Product Chemistry Data for SCLP (Z,Z,E)-7,11,13-

Hexadecatrienal. 

Guideline No. Physical and Chemical 

Properties 

Status1 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 (nOctanol/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. CBI=Confidential Business Information. 
Straight Chain Lepidopteran Pheromones Registration Review Case No. 8200 

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Table 3. Biochemical Pesticides Product Chemistry Data for SCLP (Z)-11-Tetradecen-1-ol. 

Guideline No. Physical and Chemical 

Properties 

Status1 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 (nOctanol/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. CBI=Confidential Business Information. 

EPA-REGISTERED END-USE PRODUCTS

Regulation of SCLPs predates the founding of the Agency. The first SCLP, (z,z)-11,13-

hexadecadienal, was registered in July 1969. As of this 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 (BRAD) was issued in August 2001 and as new active ingredients have been 

registered the document has been amended with updated information. 

The SCLPs with active registrations are summarized in Table 4 below. In some instances 

SCLPs have been registered concurrently and are always used together as a specific 
Straight Chain Lepidopteran Pheromones Registration Review Case No. 8200 

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pheromone blend. These active ingredients are typically individual components of a 

specific, multi-component insect pheromone and are naturally grouped together. 

Table 4. Straight Chain Lepidopteran Pheromones with Active Registrations. 

SCLP Name PC Code CAS Number Number of 

TGAI/MPs 

Number of 

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 
Straight Chain Lepidopteran Pheromones Registration Review Case No. 8200 

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SCLP Name PC Code CAS Number Number of 

TGAI/MPs 

Number of 

EPs 

(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 

MODE OF ACTION 

Lepidopteran pheromones are used to disrupt the mating behavior of certain moths and 

butterflies whose larvae destroy crops and trees via herbivory. Mating behavior in adults is 

disrupted by making it more difficult for males of the target species to locate mates via the 

masking of, or misdirection from the natural pheromone plumes emitted by females (Carde and 

Minks, 1995; Stelinsky, 2007). Mating disruption is a non-toxic mode of action. 

Pheromones have a high degree of species specificity (see review by Ando et. al., 2004). 

Semiochemical pheromones, such as SCLPs, are “odors” that bind to olfactory sensor receptors 

(OSRs) located in the antennae and maxillary palps of receptor insect species (Sato and Touhara, 

2009; Touhara and Vosshall, 2009). The OSRs are “narrowly tuned receptors” (i.e., have high 

species specificity) that are associated with olfactory sensory neurons (OSNs) (Touhara, 2009), 

which are “neural circuits in the [insect] brain” (Touhara and Voshall, 2009) involved with 

mating. Upon binding of a pheromone to an OSR, neuronal activity is triggered in the OSNs 

results in the mate-seeking behavioral responses of the receiver insect. No mortality occurs in 

the target species. 

ENVIRONMENTAL FATE 

The straight chain lepidopteran pheromones are applied to a variety of crops in various ways. 

The most common distribution methods are in dispensers (active and passive), flakes, 

microencapsulated beads, or granular formulations. 
Straight Chain Lepidopteran Pheromones Registration Review Case No. 8200 

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The SCLPs are, as a group, insoluble in water and are of intermediate volatility. 

Volatility is key to the efficacy of SCLPs (Barth, 2001) and allows small amounts to be 

placed in the environment, resulting in low exposure to the active ingredient when used 

as a pesticide for mating disruption. Studies of the fate of SCLPs on moistened soil and 

water show rapid dissipation via volatilization and environmental degradation. 

Volatilization of the parent compounds occurs rapidly in water with half life varying 

from 29 hours to 7 days (Henson, 1977; Shaver, 1983). The SCLPs also readily undergo 

photo-oxidation (OECD, 2002) and are transformed by beta-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). 

The following specific examples are illustrative of the rapid environmental degradation 

of SCLPs. The half-life of the Gypsy moth pheromone, gossyplure [(Z,Z)- and (Z,E)- 

7,11-Hexadecadien-1-ol acetate), was measured to be 1 day on soil and 7 days on water 

at 32 oC (Henson, 1977). The half lives of the components of the tobacco budworm 

pheromone, (Z)-9-Tetradecenal and (Z)-11-Hexadecenal, were observed to be 

respectively, 29 and 50 hours in soil at 22 oC, and 30 and 90 hours in water at 24 oC 

(Shaver, 1983). In addition, a review of the existing data by OECD (2002) demonstrated 

that due to rapid volatilization and degradation, atmospheric concentrations of applied 

SCLPs are unlikely to exceed several ng/m3 in the aerial compartment in and around the 

treated crops. 

Based on a large body of existing data, the Agency determined that additional environmental fate 

data are not required for registration SCLP products intended for applications at a rate of no 

more than 150 grams active ingredient/acre/year per 40 CFR §158.2060, except those SCLP 

products 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 and is used to 

address the potential toxicity of the other (inert) ingredients in the end-use products, not the 

SCLP active ingredients which have been demonstrated to be practically non-toxic to birds on an 

acute and dietary basis (see Table 5 below). Environmental fate testing is typically required 

when results from Tier I TGAI testing indicate potential adverse effects. This has not been the 

case with the currently registered SCLPs. 

EXPOSURE ASSESSMENT

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, it has been estimated that in orchards infested with Codling moth, the 
Straight Chain Lepidopteran Pheromones Registration Review Case No. 8200 

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females may emit up to 184 mg of mating pheromone per acre per day (Jones, 2012). 

Higher estimates (see review by Touhey, 1990) estimated that a Codling moth infestation 

may result in emission levels of up to 91.2 mg/A/hour (or 2188.8 mg/A/day). In any 

growing season, these values may vary but are likely significantly increased by the 

presence of multiple arthropod species emitting multiple pheromones in the same area 

(Jones, 2012). 

The effectiveness of SCLP products are dependent upon Lepidopteran olfactory receptor 

systems (i.e. the OSR/OSN complex) that are most sensitive to natural emission rates that 

are within a discrete range for the receptor species (Ando et. al., 2004). At higher rates 

of release, SCLP pheromones become much less, or even ineffective (Howse et. al., 

1998). Therefore, in contrast to natural levels of SCLP emissions, exposure to humans 

and nontarget organisms from SCLP pesticide products is therefore expected to be much 

lower than from the collective natural background levels of lepidopteran pheromones. 

The SCLP pheromone delivery systems are designed to emit the active ingredients in the 

low nanogram range (Mayer and Mitchell, 1998). 

The SCLP end-use products are typically applied via dispensers (active and passive), and 

foliar applications of microencapsulated flakes, beads, or granules. Residues on edible 

fruit (grapes) were undetectable when SCLPs were applied in the field via passive 

dispensers at up to 141 g a.i. per acre with a detection limit of 2-5 ppb (OECD, 2002). 

Unwashed tomatoes field-treated with an SCLP (tridecenyl acetate) formulated into 35 

um microcapsules, had residues of 21-72 ppb on the day of application, declining to 0.9-

6.8 ppb by day 15 post-application, and 0.29-1.2 ppb by day 30 (OECD, 2002). Washing 

the tomatoes lowered the SCLP residues below the limits of detection. Even on the day 

of application, the highest residue levels were well below natural background levels of 

lepidopteran pheromones. 

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. Regardless, the insolubility of SCLPs, together with their volatility (see Tables 1-3 

above), renders exposure to aquatic organisms highly unlikely. 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), orders of 

magnitude below the lowest known endpoints for fish [96-hr LC50 = 2.8 ppm (Bluegill sunfish) 

to 3.7 ppm (Rainbow trout) (Beroza et. al. 1975); and aquatic invertebrates [0.45 ppm to 1.3 ppm 

(Daphnids) (Touhey, 1990). 
Straight Chain Lepidopteran Pheromones Registration Review Case No. 8200 

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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. 

Table 5 . Summary of Non-Target Organism Data 

Study Type/OPPTS 

Guideline

SCLP Test Substance LD50/LC50/EC50 Results Toxicity 

Category

Reference or 

MRID 

Acute Oral Toxicity(rat) 

/OPPTS 870.1100 

All known tested LD50 >5,000 mg/kg IV 

Practically 

non-toxic 

FR Notice 

1/26/94 

 

Avian Acute Oral Toxicity 

/OPPTS 850.2100 

 

 

 

 

(Z)-11-Hexadecanal (91.9%) 

(Z)-9-Tetradecenal (6.1%) 

LD50 >2000 ppm (Bobwhite quail) Practically 

non-toxic 

Touhey, 1990 

(Z)-11-Hexadecen-1-ol 

(0.01%) 

1-Tetradecenal (8.25%) 

(Z)-9-Tetradecenal (8.82%) 

1-Hexadecenal (17.4%) 

(Z)-7-Hexadecanal (0.63%) 

(Z)-9-Hexadecanal (0.63%) 

(Z)-11-Hexadecanal (62.3%) 

LD50 >2000 ppm (Mallard duck) Practically 

non-toxic 

Touhey, 1990 

& 

MRID 

00073644 

(Z)-9-Dodecen-1-ol acetate 

(80%) 

(E)-9-Dodecen-1-ol acetate 

(20%) 

LD50 >2000 ppm (Mallard duck) Practically 

non-toxic 

Touhey, 1990 

(Z)-4-Tridecen-1-ol acetate 

(4%) 

(E)-4-Tridecen-1-ol acetate 

(96%) 

LD50 >2000 ppm (Mallard duck) Practically 

non-toxic 

Touhey, 1990 

(Z,Z)-7,11-Hexadecadien-1-ol 

acetate (49.8%) 

(Z,E)-7,11-Hexadecadien-1-ol 

acetate (47.2%) 

LD50 >10000 ppm (Mallard duck) Practically 

non-toxic 

Touhey, 1990 

& 

MRID 

00070563 

 

Avian Dietary Toxicity 

/OPPTS 850.2150 

 

(Z,Z)-7,11-Hexadecadien-1-ol 

acetate (49.8%) 

(Z,E)-7,11-Hexadecadien-1-ol 

acetate (47.2%) 

8-day LD50 >10000 ppm 

 (Mallard duck) 

Practically 

non-toxic 

Touhey, 1990 

& 

MRID 

00083062 

(Z,Z)-7,11-Hexadecadien-1-ol 

acetate (49.8%) 

(Z,E)-7,11-Hexadecadien-1-ol 

acetate (47.2%) 

8-day LD50 >10000 ppm 

 (Bobwhite quail) 

Practically 

non-toxic 

Touhey, 1990 

& 

MRID 

00083062 

(Z)-7-Dodecen-1-ol LC50 = 3.7ppm (Rainbow trout) 

LC50 = 2.8 ppm (Bluegill sunfish) 

Highly 

toxic 

Beroza et. al., 

1975 
Straight Chain Lepidopteran Pheromones Registration Review Case No. 8200 

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Study Type/OPPTS 

Guideline

SCLP Test Substance LD50/LC50/EC50 Results Toxicity 

Category

Reference or 

MRID 

Freshwater Fish Acute 

Toxicity, 96 hr 

/OPPTS 850.1075 

 

 

(Z)-7-Dodecen-1-ol acetate LC50 >100 ppm (Rainbow trout) 

LC50 >100 ppm (Bluegill sunfish) 

Practically 

non-toxic 

Beroza et. al., 

1975 

(Z)-11-Hexadecanal (91.9%) 

(Z)-9-Tetradecenal (6.1%) 

LC50 = 320 ppm (Rainbow trout) 

Practically 

non-toxic 

Touhey, 1990 

(Z)-9-Dodecen-1-ol acetate 

(80%) 

(E)-9-Dodecen-1-ol acetate 

(20%) 

LC50 >300 ppm (Bluegill sunfish) 

Practically 

non-toxic 

Touhey, 1990 

(Z)-4-Tridecen-1-ol acetate 

(4%) 

(E)-4-Tridecen-1-ol acetate 

(96%) 

LC50 >300 ppm (Bluegill sunfish) 

Practically 

non-toxic 

Touhey, 1990 

 (E)-11-Tetradecen-1-yl acetate 

(9.5%) 

(E,E)-9,11- Tetradecen-1-yl 

acetate (0.5%) 

LC50 >187 ppm (Rainbow trout) 

LC50 >187 ppm (Fathead minnow) Practically 

non-toxic 

USDA/APHIS, 

2011 

Aquatic Freshwater 

Invertebrate Toxicity, 48-hr 

/OPPTS 850.1010 

 

(Z)-11-Hexadecanal (91.9%) 

(Z)-9-Tetradecenal (6.1%) 

LC50 >0.45 ppm (Daphnia magna) 1 Very 

highly 

toxic 

Touhey, 1990 

(Z)-9-Dodecen-1-ol acetate 

(80%) 

(E)-9-Dodecen-1-ol acetate 

(20%) 

LC50 = 1.3 ppm (Daphnia magna) 1 Highly 

toxic 

Touhey, 1990 

(Z,Z)-7,11-Hexadecadien-1-ol 

acetate (49.8%) 

(Z,E)-7,11-Hexadecadien-1-ol 

acetate (47.2%) 

LC50 = 6.8 ppm (Daphnia magna) Highly 

toxic 

Touhey, 1990. 

 (E)-11-Tetradecen-1-yl acetate 

(9.5%) 

(E,E)-9,11- Tetradecen-1-yl 

acetate (0.5%) 

96-hr LC50 >187 ppm (Ceriodaphnia 

dubia) Practically 

non-toxic 

USDA/APHIS, 

2011 

Non-target Plants - 

No direct toxicity reported or 

expected for any product due to low 

application rates, high volatility, and 

minimal to no measurable residues . 

Practically 

non-toxic 

USDA/APHIS, 

2011 

Non-target Insects (Honey 

Bee Acute Oral Toxicity, 

48-hr)/OPPTS 850.3020 

(E)-11-Tetradecen-1-yl acetate 

(9.5%) 

(E,E)-9,11- Tetradecen-1-yl 

acetate (0.5%) 

No mortality with contact exposure 

of up to 0.91 g/300bee (1.0% soln); 

up to 10x the field app. rate

Practically 

non-toxic 

Monheit et. al., 

2008 

Non-target Insects (Honey 

Bee Contact Toxicity, 48-

hr)/OPPTS 850.3020 

(E)-11-Tetradecen-1-yl acetate 

(9.5%) 

(E,E)-9,11- Tetradecen-1-yl 

acetate (0.5%) 

No mortality with contact exposure 

of up to 1.13g/300bee (0.1% soln) ); 

up to 10x the field app. rate

Practically 

non-toxic 

Monheit et. al., 

2008 

1. Mortality likely due to entrapment of test organisms in oily surface film 
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RISK ASSESSMENT

Risk Quotients (RQs) and Levels of Concern (LOCs) were assessed using the highest known 

values for SCLP residues on field-treated crops via active and passive dispensers: unwashed 

tomatoes field-treated with an SCLP (tridecenyl acetate) formulated into 35 um microcapsules, 

had residues of 21-72 ppb on the day of application, declining to 0.9-6.8 ppb by day 15 postapplication, and 0.29-1.2 ppb by day 30 (OECD, 2002). The residue value of 72 ppb (0.072 

ppm) was used for all subsequent calculations on terrestrial taxa. 

Terrestrial vertebrates: Numerous studies have demonstrated that SCLPs are practically nontoxic (Toxicity Category IV) in acute oral and acute dermal routes of exposure (LD50 > 5000 

mg/kg) (see review by OECD, 2002; & USEPA, 2007 & 2008). Mammalian RQs are estimated 

as: 

Mammalian RQ = 0.072/5000 <0.01 

The RQ for mammals are well below any levels of concern for non-target mammals, including 

threatened and endangered species. 

Birds: It has been demonstrated that SCLPs are practically non-toxic to birds on both an acute 

(>2000 mg/kg to > 10000 mg/kg) (Table 5). Using the lowest non-definitive endpoint for birds 

exposed to residues via active/passive dispensers, RQs are estimated as: 

Avian RQ = 0.072/2000 <0.01 (acute and dietary) 

Oral exposure to birds via flakes or granules is not expected to be a significant route of exposure 

to SCLPs (which make up only a tiny percentage of the products on a w/w basis). Based on the 

low exposure and minimal toxicity (Table 5), the Agency has exempted the requirements for 

non-target bird data for granular product, except for end-use formulations (see 40 CFR 

158.2060). This requirement is used to assess the potential for effects on birds resulting from the 

inert ingredients in the granular products, not for the active ingredient. Effects on birds resulting 

from potential consumption of granular end-use formulations will be assessed on a case-by-case 

basis as these products are reviewed for registration. Otherwise, the RQs are well below any 

levels of concern for non-target birds, including threatened and endangered species. 

Fish and Aquatic Invertebrates: Effects on fish in laboratory studies are somewhat variable, but 

the majority of studies indicate that SCLPs are practically non-toxic to fish (> 100 ppm; Beroza, 

1975), except for one study using the SCLP (Z)-7-Dodecen-1-ol as a test substance which 

reported LD50s respectively of 3.7 ppm and 2.8 ppm for Rainbow trout and Bluegill sunfish (both 

Highly toxic) (Beroza, 1975). Effects on aquatic invertebrates also were variable, ranging from 

>0.45 ppm to 6.8 ppm (Very highly toxic to Highly toxic) in laboratory studies (Touhey, 1990; 

USDA/APHIS, 2011; Table 5). For aquatic exposure, the Agency estimated environmental 
Straight Chain Lepidopteran Pheromones Registration Review Case No. 8200 

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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; or 0.000308 ppm). Based on the 

lowest known LD50 for fish (2.8 ppm for Bluegill sunfish), the RQ is estimated as: 

Fish RQ = 0.000308/2.8 <0.01 

Similarly, based on the lowest known LD50 for aquatic invertebrates (0.45 ppm for Daphnia), the 

RQ is estimated as: 

Aquatic invertebrate RQ = 0.000308/0.45 <0.01 

The RQs are well below any levels of concern for non-target aquatic organisms, including 

threatened and endangered species. 

The Agency notes that the LD50s reported in laboratory studies, where the test substance was 

artificially rendered water soluble via the use of solvents, are at concentrations that are well 

above the solubility of SCLPs (practically insoluble in water) in a natural aquatic environment. 

 

Non-Target Plants: Exposure to plants is expected to be minimal and would occur via contact 

resulting from atmospheric exposure to SCLPs volatilized from active and passive dispensers, or 

volatilized from foliarly applied flakes or granules containing SCLPs. Residues on edible fruit 

(grapes) were undetectable when SCLPs were applied in the field via passive dispensers at up to 

141 g a.i. per acre with a detection limit of 2-5 ppb (OECD, 2002). Unwashed tomatoes fieldtreated with an SCLP (tridecenyl acetate) formulated into 35 um microcapsules, had residues of 

21-72 ppb on the day of application, declining to 0.9-6.8 ppb by day 15 post-application, and 

0.29-1.2 ppb by day 30 (OECD, 2002). Due to the low application rates, high relative volatility, 

and little to no measureable residues, effects on non-target plants are highly unlikely. No 

adverse effects have ever been reported on plants treated with SCLP products after several 

decades of use in IPM programs for crop protection from insect pests. There are no concerns for 

non-target plants, including threatened and endangered species. 

Non-Target Insects: Lepidopteran pheromones are used to disrupt the mating behavior of certain 

moths and butterflies whose larvae destroy crops and trees via herbivory. Mating behavior in 

adults is disrupted by making it more difficult for males of the target species to locate mates via 

the masking of, or misdirection from the natural pheromone plumes emitted by females (Carde 

and Minks, 1995; Stelinsky, 2007). Mating disruption is a non-toxic mode of action. Unique 

suites of pheromones exist for each species of insect (Ando et. al. 2004; Roelofs, 1995; 

Stelinsky, 2007) and pheromones eliciting a response in one species are highly unlikely to elicit 

a response in an unrelated species. 
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Few studies have been conducted to determine contact or oral toxicity to insects. One available 

study (Monheit et. al., 2008), demonstrated that the SCLP used in the control of Light Brown 

Apple moth (LBAM) (Table 5), was non-toxic to honey bees on a dietary and on a a contact 

basis at up to 10x the field applied rate. The Agency notes that dietary exposure to bees or other 

pollinators via nectar or pollen is highly unlikely because SCLPs are not systemic in plants. 

There are no concerns for non-target insects, including threatened and endangered species. 

Overall Risk Assessment: Based on the application methods of end-use products containing 

straight chain lepidopteran pheromones as their active ingredient, there is little or no exposure of 

SCLPs to nontarget terrestrial and aquatic organisms. As discussed above, SCLPs are applied 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 

Ando, T., S. Inomata, and M. Yamamoto. 2004. Lepidopteran sex pheromones. Topics in 

Current Chemistry 239: 51-96. 

Barth, F.G and A. Schmid. 2001. Ecology of Sensing. Springer. 

Beroza, M., M. N. Inscoe, P. H. Schwartz, M. L. Keplinger, and C. W. Mastri. 1975. Acute 

toxicity studies with attractants. Toxicology and Applied Pharmacology 31: 421-429. 

Carde, R. T. and A. K. Minks. 1995. Control of moth pests by mating disruption: successes and 

constraints. Annual Review of Entomology 40: 559-585. 

Esmeralda, R., C. Barata, J. Damásio, and M. P. Bosch, and A. Guerrero. 2006. Aquatic 

ecotoxicity of a pheromonal antagonist in Daphnia magna and Desmodesmus subspicatus. 

Aquatic Toxicology 79: 296-303. 

Jones, R. S. 2012. Biochemical Pesticides: Green Chemistry Designs by Nature. In: Green 

Processes Volume 9: Designing Safer Chemicals. R. Boethling and A. Voutchkova, eds. WileyVCH, 2011. pp. 329-347. 
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Henson, R. D. 1977. Environmental fate of gossyplure. Environmental Entomology 6: 821-

822. 

Howse, P. E., I. D. R. Stevens, and O. T. Jones. 1998. Insect Pheromones and their Use in Pest 

Management. Chapman and Hall, London, 369 pp. 

Mayer, M. S. and E. R. Mitchell. 1998. Rapid measure of sex pheromone emission from plastic 

rope dispensers: example of utility in sexual communication disruption of the Diamondback 

moth, Plutella xylostella. Phytoparasitica 26(2): 1-9. 

Monheit, S., E. C. Mussen, and M. L. Johnson. 2008. Effects of Contact and exposure to 

formulated CheckMate and LBAM-F and unformulated LBAM mating pheromones on honey 

bees, Apis mellifera (Hymenoptera: Apidae). Final Report, Nov 18. 

http://www.cdfa.ca.gov/plant/pdep/lbam/docs/HoneyBee_Checkmate_ToxicityRpt%20_Nov_08.

pdf

Organisation for Economic Cooperation and Development (OECD). 2002. Guidance for 

registration requirements for pheromones and other semiochemicals used for arthropod pest 

control. OECD Series on Pesticides, No. 12. Environmental Directorate, Joint Meeting of the 

Chemical Committee and the Working Party on Chemicals, Pesticides, and Biotechnology. 

ENV/JM/MONO(2001)12. Roelofs, W. L. 1995. Chemistry of sex attractants. Proceedings of 

the Ntional Academy of Sciences 92: 42-49. 

Roelofs, W. L. 1995. Chemistry of sex attractants. Proceedings of the National Academy of 

Sciences 92: 42-49. 

Sato, K. and K. Touhara. 2009. Insect olfaction: receptors, signal transduction, and behavior. 

Chemosensory Systems in Mammals, Fishes, and Insects, Results and Problems in Cell 

Differentiation 47:121-138. 

Shaver, T. N. 1983. Environmental fate of (Z)-11-hexadecenal and (Z)-9-tetradecenal, 

components of a sex pheromone of the tobacco budworm (Lepidoptera: Noctuidae). 

Environmental Entomology 12: 1802-1804. 

Stelinsky, L. L. 2007. On the physiological and behavioral mechanisms of pheromone-based 

mating disruption. Pestycydy 3-4: 27-32. 

Touhey, J. G. 1990. White Paper. A review of the current bases for the United States 

Environmental Protection Agency’s policies for the regulation of pheromones and other 

semiochemicals, together with a review of the available relevant data which may impact the 

assessment of risk for these classes of chemicals. Part No. I. Straight chain alcohols, acetate 

esters and aldehydes. (USEPA, unpublished). 
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Touhara, K. 2009. Insect olfactory receptor complex functions as a ligand-gated ionotrophic 

channel. New York Academy of Sciences 1170: 177-180. (Abstract Only). 

Touhara, K. and L. B. Voshall. 2009. Sensing odorants with pheromones and chemosensory 

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http://www.aphis.usda.gov/plant_health/ea/downloads/2011/EGVMPesticideEnvironmentalRisk

Assessment.pdf

USEPA. 2007. Quarantine Exemptions for Light Brown Apple Moth Pheromones. 

http://www.epa.gov/region9/pesticides/light-brown-moth.html

USEPA. 2008. Straight Chain Lepidopteran Pheromones, Biopesticide Registration Action 

Document. http://www.epa.gov/pesticides/chem_search/reg_actions/registration/decision_G109_02-Oct-08.pdf

Weatherson, I. and A. K. Minks. 1995. Regulation of semiochemicals - global aspects.. 

International Pest Management Review 1: 1-13. 

Welter, S.C., C. Pickel, J. Millar, F. Cave, R. A. Van Steenwyk, and J. Dunley. 2005. 

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59(1): 16-22 (2005). 

cc: R. S. Jones, C. Walsh, BPPD Subject File/IHAD 

 R. S. Jones, Sr. Biologist, FT, OPY: 11/19/2012 
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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 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