(Z,Z)-Hexadeca-7,11-dienylacetat

Colorless or light yellow liquid

Yellow liquid

In water, 0.2 mg/L at 25 °C

Soluble in most organic solvents.

130-132 °C

BP: 170-175 °C at 3 mm Hg; 191-195 °C at 4.5 mm Hg; 146 °C at 1 mm Hg

BP: 130-132 °C. Index of refraction: 1.4592 at 21 °C/D /(Z,Z)-7,11-Hexadecadien-1-yl acetate/

BP: 132-134 °C. Index of refraction: 1.4591 at 21 °C/D /(Z,E)-7,11-Hexadecadien-1-yl acetate/

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 66 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

USEPA Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision (RED) for Hexadecadienol Acetates List D, Case 4111 (1994). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the USA.[Available from, as of June 25, 2018: http://www.epa.gov/oppsrrd1/REDs/old_reds/hexadecadienol_acetates.pdf]

The pheromone gossyplure, a 1:1 mixture of (Z,Z)- and (Z,E)-7,11-hexadecadien-1-ol acetate) is exempt from the requirement of a tolerance in or on the raw agricultural commodity cotton, undelinted seed when applied to cotton from capillary fibers.

Based on the reviews of the generic data of the four active ingredient hexadecadienol acetates, the Agency has sufficient information on their potential effects on human health. The Agency has determined that hexadecadienol acetate products, labeled and used as specified in this Reregistration Eligibility Decision, will not pose unreasonable risks or adverse effects to humans or the environment. Therefore, the Agency concludes that products containing hexadecadienol acetates for the currently registered use are eligible for registration.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer safety standards, such as those described in the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. Hexadecadien-1-ol, acetate is found on List D. Case No: 4111; Pesticide type: insecticide; Case Status: RED Approved 03/94; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): hexadecadien-1-ol acetate; Data Call-in (DCI) Date(s): 04/23/93; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) for the case/AI.

Skin Irrit. 2 (100%)

Skin Irrit. 2 (100%)

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

The pheromone gossyplure, a 1:1 mixture of (Z,Z)- and (Z,E)-7,11-hexadecadien-1-ol acetate) is exempt from the requirement of a tolerance in or on the raw agricultural commodity cotton, undelinted seed when applied to cotton from capillary fibers.

LC50; Species: Eisenia fetida (Earthworm) adult; environmental, unspecified exposure (natural soil: 14.6% sand, 38.0% silt, 47.4% clay, pH 7.2, 4.2% organic matter) 489 mg/kg for 7 days /99% purity/

LC50; Species: Eisenia fetida (Earthworm) adult; environmental, unspecified exposure (natural soil: 14.6% sand, 38.0% silt, 47.4% clay, pH 7.2, 4.2% organic matter) 392.4 mg/kg for 14 days /99% purity/

EC50; Species: Pseudokirchneriella subcapitata (Green Algae); Conditions: freshwater, static; Concentration: 723 ug/L for 72 hr (95% confidence interval: 678-778 ug/L); Effect: population, decreased biomass

EC50; Species: Pseudokirchneriella subcapitata (Green Algae); Conditions: freshwater, static; Concentration: >854 ug/L for 72 hr; Effect: population, decreased population growth rate

For more Ecotoxicity Values (Complete) data for Gossyplure (10 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2.5X10+4(SRC), determined from a structure estimation method(2), indicates that gossyplure is expected to be immobile in soil(SRC). Volatilization of gossyplure from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.5X10-4 atm-cu m/mole(SRC), derived from its vapor pressure of 8.25X10-5 mm Hg(3) and water solubility of 0.2 mg/L(3). Gossyplure is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 8.2X10-5 mm Hg(3). Biodegradation data were not available(SRC, 2018).

TERRESTRIAL FATE: Gossyplure soil persistence was analyzed using 10 mg test compound added to flooded Lufkin fine sandy loam exposed to continuous fluorescent light in an environmental chamber held at 32 °C for up to 14 days(1). Only traces remained at the end of the test period; a half-life of approximately 24 hours was calculated with loss being attributed to volatilization(1). A half-life in soil of 1 day has also been reported(2).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2.5X10+4(SRC), determined from a structure estimation method(2), indicates that gossyplure is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.5X10-4 atm-cu m/mole(SRC), derived from its vapor pressure of 8.25X10-5 mm Hg(4) and water solubility of 0.2 mg/L(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 15 hours and 10 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 19 months if adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 2400(SRC), from an estimated log Kow of 7.31(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is very high, provided the compound is not metabolized by the organism(SRC). Hydrolysis is not expected to be an important environmental fate process based on a base-catalyzed second-order hydrolysis half-lives of 9 years and 180 days at pH values of 7 and 8, respectively(2). Biodegradation data were not available(SRC, 2018).

AQUATIC FATE: Gossyplure soil persistence was analyzed using 10 mg test compound in aqueous solution exposed to continuous fluorescent light in an environmental chamber held at 32 °C for up to 14 days(1). Less than 10% remained at the end of the test period; a half-life of approximately 14 days was calculated with loss being attributed to volatilization(1). A half-life in water of 7 days has also been reported(2).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), gossyplure, which has a vapor pressure of 8.25X10-5 mm Hg at 25 °C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase gossyplure is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air by the cis-isomer is estimated to be 3 hours(SRC), calculated from its rate constant of 1.3X10-10 cu cm/molecule-sec at 25 °C (1.4X10-10 cu cm/molecule-sec at 25 °C, half-life of about 1 hour for the trans-isomer)(SRC) that was derived using a structure estimation method(3). Particulate-phase gossyplure may be removed from the air by wet or dry deposition(SRC). Gossyplure directly exposed to sunlight for up to 24 hours did not photodegrade(4) and, therefore, it is not expected to be susceptible to direct photolysis by sunlight(SRC).

IDENTIFICATION AND USE: Gossyplure is a colorless or light yellow liquid. It is used as a mating disruptant of pink bollworm in cotton. HUMAN STUDIES: There are no data available. ANIMAL STUDIES: Primary eye irritation - slight iritis and conjunctival irritation. Primary dermal irritation - slight erythema. Dermal Sensitization - not a sensitizer. Not mutagenic in Ames Assay. ECOTOXICITY STUDIES: It was practically nontoxic to bobwhite quail.

/BIRDS and MAMMALS/ Technical hexadecadienol is considered to be practically non-toxic to bobwhite quail with an acute oral LD50 of >2000 mg/kg. The dietary toxicity to bobwhite quail is considered to be practically non-toxic with a dietary LC50 of >5620 ppm. /Hexadecadienol/

Using a structure estimation method based on molecular connectivity indices(1), the Koc of gossyplure can be estimated to be 2.5X10+4(SRC). According to a classification scheme(2), this estimated Koc value suggests that gossyplure is expected to be immobile in soil. In a soil column study of fine sandy loam, gossyplure, applied at 50 mg gossyplure, was not detected in the eluates following washing with 5 liters of distilled water(3).

Gossyplure's isolation may result in its release to the environment through various waste streams; its use as an insect attractant(1) will result in its direct release to the environment(SRC). Specifically, the compound is employed as a mating disruptant of pink bollworm in cotton(2).

An estimated BCF of 2400 was calculated in fish for gossyplure(SRC), using an estimated log Kow of 7.31(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is very high(SRC), provided the compound is not metabolized by the organism(SRC).

The Henry's Law constant for gossyplure is estimated as 1.5X10-4 atm-cu m/mole(SRC), derived from its vapor pressure of 8.25X10-5 mm Hg(1) and water solubility of 0.2 mg/L(1). This Henry's Law constant indicates that gossyplure is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 15 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 10 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The volatilization half-life from a model pond is 19 months when adsorption is considered(3). Gossyplure's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Gossyplure is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

/LABORATORY ANIMALS: Acute Exposure/ Hexadecadienol acetates generally are of low acute toxicity. They are placed in Toxicity Category IV /by EPA/, indicating the lowest level of acute toxicity for acute oral and primary dermal effects. For acute dermal, acute inhalation and primary eye irritation effects, hexadecadienol acetates are placed in Toxicity Category Category III. Since the potential for human exposue to these pesticides is considered negligible, all other standard toxicology studies /were/ waived. /Hexadecadienol acetates/

/LABORATORY ANIMALS: Acute Exposure/ Acute oral LD50 > 5 g/kg; Acute dermal LD50 >2 g/kg; Acute inhalation LC50 >2.5 mg/L; Primary eye irritation - slight iritis and conjunctival irritation; Primary dermal irritation - slight erythema; Dermal Sensitization - not a sensitizer. /From table; no additional information provided/

/GENOTOXICITY/ Not mutagenic in Ames Assay. /From table; no additional information given/

The rate constant for the vapor-phase reaction of cis-gossyplure with photochemically-produced hydroxyl radicals has been estimated as 1.3X10-10 cu cm/molecule-sec at 25 °C (1.4X10-10 cu cm/molecule-sec at 25 °C for the trans-isomer)(SRC) using a structure estimation method(1). These values correspond to an atmospheric half-life of about three hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of cis-gossyplure with ozone has been estimated as 2.6X10-16 cu cm/molecule-sec at 25 °C (4.0X10-16 cu cm/molecule-sec at 25 °C for the trans-isomer)(SRC) that was derived using a structure estimation method(1). These values correspond to an atmospheric half-life of about one hour at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). A base-catalyzed second-order hydrolysis rate constant of 4.6X10-2 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 9 years and 175 days at pH values of 7 and 8, respectively(3). Gossyplure applied to slides and directly exposed to sunlight for up to 24 hours did not photodegrade, with loss being attributed to volatilization(4); therefore, gossyplure is not expected to be susceptible to direct photolysis by sunlight(SRC).

Occupational exposure to gossyplure may occur through inhalation and dermal contact with this compound at workplaces where gossyplure is produced or used. Use data indicate that the general public is not likely to be exposed to gossyplure. (SRC)

The pheromone gossyplure, a 1:1 mixture of (Z,Z)- and (Z,E)-7,11-hexadecadien-1-ol acetate) is exempt from the requirement of a tolerance in or on the raw agricultural commodity cotton, undelinted seed when applied to cotton from capillary fibers.

Based on the reviews of the generic data of the four active ingredient hexadecadienol acetates, the Agency has sufficient information on their potential effects on human health. The Agency has determined that hexadecadienol acetate products, labeled and used as specified in this Reregistration Eligibility Decision, will not pose unreasonable risks or adverse effects to humans or the environment. Therefore, the Agency concludes that products containing hexadecadienol acetates for the currently registered use are eligible for registration.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer safety standards, such as those described in the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. Hexadecadien-1-ol, acetate is found on List D. Case No: 4111; Pesticide type: insecticide; Case Status: RED Approved 03/94; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): hexadecadien-1-ol acetate; Data Call-in (DCI) Date(s): 04/23/93; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) for the case/AI.

For 7,11-hexadecadien-1-ol, acetate (USEPA/OPP Pesticide Code: 114103) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

For (Z,E)-7,11-hexadecadien-1-yl acetate (USEPA/OPP Pesticide Code: 114101) ACTIVE products with label matches. /SRP: Registered for use in the USA but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./ /(Z,E)-7,11-Hexadecadien-1-yl acetate/

For (Z,Z)-7,11-hexadecadien-1-yl acetate (USEPA/OPP Pesticide Code: 114102) ACTIVE products with label matches. /SRP: Registered for use in the USA but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./ /(Z,Z)-7,11-Hexadecadien-1-yl acetate/

Insect attractant

For more Uses (Complete) data for Gossyplure (6 total), please visit the HSDB record page.

Frustrate PBW Bands are hand-applied polymer controlled release bands in sprayable formulation.

PB Rope L (Pacific Biocontrol Corporation): Active ingredient: 7,11-hexadecadien-1-ol, acetate, (E,Z)- 44.1% and 7,11-hexadecadien-1-ol, acetate, (Z,Z)- 46.7%. /(E,Z)-7,11-Hexadecadien-1-ol, acetate; (Z,Z)-7,11-Hexadecadien-1-ol, acetate/

Nomate PBW MEC (Scentry Biologicals, Inc.): Active ingredient: 7,11-hexadecadien-1-ol, acetate, (E,Z)- 10.0% and 7,11-hexadecadien-1-ol, acetate, (Z,Z)- 10.0%. /(E,Z)-7,11-Hexadecadien-1-ol, acetate/

Checkmate (R) PBW (Suterra LLC): Active ingredient: 7,11-hexadecadien-1-ol, acetate, (E,Z)- 40.4% and 7,11-hexadecadien-1-ol, acetate, (Z,Z)- 40.4%. /(E,Z)-7,11-Hexadecadien-1-ol, acetate/

For more Formulations/Preparations (Complete) data for Gossyplure (6 total), please visit the HSDB record page.

7,11-Hexadecadien-1-ol, 1-acetate: ACTIVE

There is no ISO common name for this substance; the name gossyplure is approved in China ... This substance is named after the insect from which it was isolated, Pectinophora gossypiella (Saunders) (Gelechiidae, Lepidoptera).

The natural and commercial pheromone is a mixture of (Z,Z)- and (Z,E)- isomers in the ratio of 1:1