2-Methyl-4-oxo-3-(prop-2-inyl)cy-clopent-2-en-1-yl-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropan-carboxylat

Wear self contained breathing apparatus for fire fighting if necessary.

Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Fire-fighting: Self-contained breathing apparatus with a full facepiece operated in pressure-demand or other positive-pressure mode.

Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Recommended storage temperature: 2 - 8 °C.

Pyrethrins with piperonyl butoxide topical preparations should be stored in well-closed containers at a temperature less than 40 °C, preferably between 15-30 °C. /Pyrethrins/

Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.

Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed containers for disposal.

Wear respiratory protection. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. 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 soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.

Chemical packaging: Dispose of as unused product.

Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling the product.

Avoid contact with skin and eyes. Avoid inhalation of vapor or mist.

Control of environmental exposure: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.

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.

(1) A tolerance of 1.0 ppm is established for residues of the insecticide prallethrin (RS)-2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl (1RS)-cis, trans-chrysanthemate as follows: (2) In or on food commodities in food handling establishments where food and food products are held, processed, prepared and/or served. (3) Application shall be limited to space, general surface, and spot and/or crack and crevice treatment in food handling establishments where food and food products are held, processed, prepared and/or served. General surface or space spray applications may be used only when the facility is not in operation provided exposed food has been covered or removed from the area being treated prior to application. Spot and/or crack and crevice application may be used while the facility is in operation provided exposed food is covered or removed from the area being treated prior to application. Spray concentrate shall be limited to a maximum of 2.0% active ingredient. Contamination of food or food contact surfaces shall be avoided. Food contact surfaces and equipment should be throughly washed with an effective cleaning compound and rinsed with potable water after use of the product.

Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Skin protection: Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.

Employees should be provided with and required to use dust- and splash-proof safety goggles where /pyrethroids/ ... may contact the eyes. /Pyrethroids/

Body protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.

For more Personal Protective Equipment (PPE) (Complete) data for Prallethrin (6 total), please visit the HSDB record page.

The effects of pyrethroids were studied on phosphoinositide breakdown in guinea pig synaptoneurosomes. Similar to other agents that activate voltage-dependent sodium channels, type I and type II pyrethroids stimulated phosphoinositide breakdown. Type II pyrethroids, like deltamethrin and fenvalerate, were more potent and, at least for deltamethrin, more efficacious than type I pyrethroids, like allethrin, resmethrin and permethrin. The effects of type II pyrethroids could be partially inhibited by the sodium channel blocker tetrodotoxin. The effects of allethrin and resmethrin were not affected by 5 microM tetrodotoxin. Stimulation of phosphoinositide breakdown by fenvalerate was additive to the stimulation elicited by the receptor agonists carbamylcholine and norepinephrine, but not to the stimulation elicited by sodium channel agents (batrachotoxin, scorpion venom and pumiliotoxin B). Stimulation by allethrin was not additive to the stimulation elicited either by receptor agonists or sodium channel agents. A submaximal concentration of allethrin, a type I pyrethroid, did not greatly affect the dose-dependent stimulation elicited by a type II pyrethroid, deltamethrin, while a higher concentration of allethrin prevented further stimulation by type II pyrethroids. A local anesthetic, dibucaine, which inhibits sodium channel activation, inhibited phosphoinositide breakdown induced by type II, but not by type I pyrethroids, except at higher concentrations. Thus, type II pyrethroids appear to stimulate phosphoinositide breakdown in synaptoneurosomes in a manner analogous to other sodium channel agents, while type I pyrethroids elicit phosphoinositide breakdown by a different mechanism, probably not involving sodium channels.

/Pyrethroid/ detoxification ... important in flies, may be delayed by the addition of synergists ... organophosphates or carbamates ... to guarantee a lethal effect. ... /Pyrethroid/

Piperonyl butoxide potentiates /insecticidal activity/ of pyrethrins by inhibiting the hydrolytic enzymes responsible for pyrethrins' metabolism in arthropods. When piperonyl butoxide is combined with pyrethrins, the insecticidal activity of the latter drug is increased 2-12 times /Pyrethrins/

LC50; Species: Colinus virginianus (Northern Bobwhite Quail) age 10 days; diet (chemical incorporated into food) >5620 ppm for 8 days

LD50; Species: Colinus virginianus (Northern Bobwhite Quail) age 19 wk; oral via capsule 1171 mg/kg (95% confidence interval: 835-1835 mg/kg)

LC50; Species: Anas platyrhynchos (Mallard Duck) age 10 days; diet (chemical incorporated into food) >5620 ppm for 8 days

LD50; Species: Anas platyrhynchos (Mallard Duck) age 19 wk; oral via capsule >1000 mg/kg

For more Ecotoxicity Values (Complete) data for Prallethrin (13 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), reported Koc values of 1,318(2) and 2,533(3), and an estimated Koc value of 3082(SRC), determined from a structure estimation method(4), indicates that prallethrin is expected to have low to slight mobility in soil(SRC). Volatilization of prallethrin from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.6X10-6 atm-cu m/mole(SRC) estimated from its vapor pressure, 3.5X10-5 mm Hg(5), and water solubility, 8 mg/L(6), in combination with strong soil adsorption. Prallethrin is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure. The photodegradation half-life of prallethrin on soil surfaces was measured as 24.8-26.9 days using EPA Guideline 161-3(7). Using an unspecifed aerobic biodegradation test, prallethrin was found to be not biodegradable in 28 days(8), suggesting that biodegradation is not an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), reported Koc values of 1,318(2) and 2,533(3), and an estimated Koc value of 3082(SRC), determined from a structure estimation method(4), indicates that prallethrin is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is possible(5) based upon an estimated Henry's Law constant of 1.6X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 3.5X10-5 mm Hg(6), and water solubility, 8 mg/L(7). Using this Henry's Law constant and an estimation method(5), volatilization half-lives for a model river and model lake are 40 and 299 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 approximately 10 years if adsorption is considered(8). According to a classification scheme(9), a measured BCF of 1,160 in Bluegill fish (Lepomis macrochirus)(10) suggests the potential for bioconcentration in aquatic organisms is very high(SRC). The photolysis half-life of prallethrin in sterile water at 22 to 27 °C at pH 5 in natural sunlight was 13.6 hours(11). The hydrolysis half-life of prallethrin at pH 9 and 23.5-25 °C was measured as 118 hours(11); significant degradation was not observed during 30 days a pH 5 or pH 7(11). Using an unspecifed aerobic biodegradation test, prallethrin was found to be not biodegradable in 28 days(12), suggesting that biodegradation is not an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), prallethrin, which has a vapor pressure of 3.5X10-5 mm Hg at 20 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase prallethrin is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2 hours(SRC), calculated from its rate constant of 2.0X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Vapor-phase prallethrin is also degraded in the atmosphere by reaction with ozone(SRC); the half-life for this reaction in air is estimated to be 18 minutes(SRC), calculated from its rate constant of 9.1X10-16 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Prallethrin directly photolyzes when exposed to sunlight(4). Particulate-phase prallethrin may be removed from the air by wet and dry deposition(SRC).

EPA has released the first beta version (version 0.5) of the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The beta version of the iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays; See the data in Chemical Explorer/[USEPA; ICSS Dashboard Application; Available from, as of March 28, 2014: http://actor.epa.gov/dashboard/]

Koc values of 1,318(1) and 2,533(2) have been reported for prallethrin. Using a structure estimation method based on molecular connectivity indices(3), the Koc of prallethrin can be estimated to be 3082(SRC). According to a classification scheme(4), these Koc values suggests that prallethrin is expected to have low to slight mobility in soil. Prallethrin is reported to be readily adsorbed into soil(5). Very little movement of prallethrin through soil columns was observed using radio-labeled material(6).

INDOOR AIR: Air samples collected from an indoor room within 30-45 minutes after application of an aerosol insecticide containing prallethrin had a prallethrin concentration of 0.0138 ppm(1); after 6 hours, air residue levels were <0.0001 ppm(1).

/HUMAN EXPOSURE STUDIES/ Changes in biochemical composition in erythrocyte membrane, erythrocytic osmotic haemolysis, and nitrite and nitrate levels in plasma were analyzed in 12 human volunteers who were exposed regularly to prallethrin, a type I pyrethroid mosquito repellent. The results revealed a decrease in cholesterol (C) and phospholipid (P) moieties in erythrocyte membrane with no consequent change in C:P ratio. Further, a significant decrease in the content of phosphatidyl serine suggested that PS is a sensitive phospholipid species to the pyrethroid action. Significant decrease in membrane lipid peroxidation and enhanced levels of nitrite and nitrate in plasma and erythrocyte indicate that increased generation and availability of nitric oxide might have rendered tolerance to erythrocyte membrane by protecting the cells from hemolysis. Increased NO(2) and NO(3) may be due to increased activity of nitric oxide synthase (NOS) and/or expression of isoforms of NOS. A possible involvement of free radical scavenging and antioxidant effects of nitric oxide might have contributed to the observed decrease in lipid peroxidation in the present study.

/HUMAN EXPOSURE STUDIES/ Continuous exposure of humans to pyrethroid-based mosquito repellents for longer durations may lead to adverse health effects. No information is available on long-term use of these mosquito repellents pertaining to the biochemical changes in human subjects. Therefore, the present study is an attempt to evaluate the status of health in human volunteers exposed to two commercially available mosquito repellent pyrethroids, allethrin and prallethrin, in terms of changes in plasma biochemical profile. Results of this study showed less but significant increase in the levels of plasma glucose, phospholipids, nitrite and nitrate, lipid peroxides with a decrease in plasma cholesterol. No significant changes were observed in the contents of total protein, albumin, globulin, HDL-C /(High-density lipoprotein-C)/ and LDL-C /(Low-density lipoprotein-C)/. However, SGPT /(Serum glutamate pyruvate transaminase)/ activity increased significantly in persons exposed to only allethrin. Though the present investigation involving a limited number of human subjects indicates the onset of both protective changes as well as derangement in metabolism, a detailed and rigorous study is greatly warranted to arrive at a definite conclusion about the effects of pyrethroid mosquito repellents.

/HUMAN EXPOSURE STUDIES/ In Sweden 33% of workers polled reported skin and eye irritation following occupational exposure.

/SIGNS AND SYMPTOMS/ The allergenic properties of pyrethroids /with early pyrethrum preparations/ are marked in comparison with other pesticides. Many cases of contact dermatitis and respiratory allergy have been reported. Persons sensitive to ragweed pollen are particularly prone to such reactions. Preparations containing synthetic pyrethroids are less likely to cause allergic reactions than are the preparations made from pyrethrum powder. /Pyrethroids/

A log BCF of 3.0645 (BCF of 1,160) was measured in Bluegill fish (Lepomis macrochirus) using a 28-day flow-through tank exposure method(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is very high(SRC).

(1) A tolerance of 1.0 ppm is established for residues of the insecticide prallethrin (RS)-2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl (1RS)-cis, trans-chrysanthemate as follows: (2) In or on food commodities in food handling establishments where food and food products are held, processed, prepared and/or served. (3) Application shall be limited to space, general surface, and spot and/or crack and crevice treatment in food handling establishments where food and food products are held, processed, prepared and/or served. General surface or space spray applications may be used only when the facility is not in operation provided exposed food has been covered or removed from the area being treated prior to application. Spot and/or crack and crevice application may be used while the facility is in operation provided exposed food is covered or removed from the area being treated prior to application. Spray concentrate shall be limited to a maximum of 2.0% active ingredient. Contamination of food or food contact surfaces shall be avoided. Food contact surfaces and equipment should be throughly washed with an effective cleaning compound and rinsed with potable water after use of the product.

New Active Ingredients ... includes chemicals not previously registered as pesticides, as well as pesticide active ingredients initially registered after November 1, 1984 and that currently have active product registrations. By law, these pesticides must meet new safety standards, such as those described in the Food Quality Protection Act of 1996 and, if new safety standards are met, will be reviewed again on a 15-year cycle. Prallethrin is designated by EPA as a New Pesticide Active Ingredient. Active Ingredient Number: 128722; Type of Pesticide: Conventional - insecticide; Use Site: Non-food/domestic, animals, industrial, commercial, and other non-food use; Year: 1995.

For prallethrin (USEPA/OPP Pesticide Code: 128722) 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./

Flying and crawling insect control for industrial locations and outdoor use.

Prallethrin is a synthetic pyrethroid with fast knock-down activity against household insect pests. It is used in household insecticide products against mosquitoes, houseflies and cockroaches. Prallethrin also has veterinary uses in the treatment of domestic pets.

Aerosol, emulsifiable concentrate, mosquito coil/mat, vaporizer liquid, oil liquid.

Commercially formulated as a mixture of (4S,1R)-trans and (4S,1R)-cis isomers in a ratio of approximately 4:1.

Ortho Roach, Ant and Spider Killer (The Scotts Company): Active ingredient: MGK 264 0.2870%; esfenvalerate 0.0500%; and prallethrin 0.0300%.

Ortho Roach, Ant and Spider Killer (The Scotts Company): Active ingredient: prallethrin 0.0300% and bifenthrin 0.0500%.

For more Formulations/Preparations (Complete) data for Prallethrin (78 total), please visit the HSDB record page.

The WHO Recommended Classification of Pesticides by Hazard identifies prallethrin (technical grade) as Class II: moderately hazardous; Main Use: insecticide.

Synthetic pyrethroid; propynyl analog of allethrin. Of the 8 possible stereoisomers, the (4S,1R)-trans isomer has the most insecticidal activity.