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Pesticides

Pesticide -> EPA IRIS

Acaricides, Insecticides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Pyrethrins/Pyrethroids

Pesticide (Fenvalerate) -> USDA PDB

log Kow = 6.20

6.20

4.4/6.2

1.17 at 23 °C/4 °C

Relative density (water = 1): 1.2

Solubility at 20 °C (g/L): acetone >450; chloroform >450; methanol >450; hexane 77

Moderately soluble in a range of organic solvents.

In water, 2.4X10-2 mg/L at 22 °C (seawater)

Solubility in water: none

1.5X10-9 mm Hg at 25 °C

Vapor pressure at 20 °C: negligible

This chemical does not meet GHS hazard criteria for 2.5% (5 of 198) of reports.

Danger

H301 (89.9%): Toxic if swallowed [Danger Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 198 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

98/270/EC

Fenvalerate: HSNO Approval: HSR002851 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

Combustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.

Allergic contact dermatitis reported in farmers; [Kanerva, p. 1796] Pyrethroids have low toxicity to humans after dermal exposure. Of 573 dermal or ingestion poisoning cases in China, 51 patients had disturbed consciousness and 34 had seizures. Of those, only five were occupationally exposed. Seizures are more commonly related to exposures to fenvalerate, flucythrinate, cypermethrin, deltapermethrin, and fluvalinate. Seizures have not been reported after exposure to permethrin. Pyrethroids may also cause paresthesias after skin contact. Paresthesias (stinging and numbness) usually begin 1-2 hours after contact and resolve within 24 hours. [EPA Pesticides, p. 87-8] Pyrethrins cause liver injury when fed to animals at high doses. [EXTOXNET] A skin, eye, and respiratory tract irritant; May cause skin sensitization; May have effects on the nervous system; [ICSC] Occupational exposure may cause skin sensations and paresthesia; [INCHEM HSG] A skin and strong eye irritant; Toxic by ingestion; [Aldrich MSDS]

Clark JR et al; Toxicity of pyrethroids to Marine Invertebrates and Fish: A Literature Review and Test Results with Sediment-Sorbed Chemicals. Environ Toxicol Chem 8 (5): 393-401 (1989). Data on acute and chronic toxicity of permethrin, fenvalerate, cypermethrin, and flucythrinate to marine invertebrates and fishes are reviewed.

WHO; Environmental Health Criteria 95: Fenvalerate (1990). EHC publications are monographs designed for scientists and administrators responsible for the establishment of safety standards and regulations. This series issued by the International Programme on Chemical Safety (IPCS), provides basic scientific risk evaluation of a wide range of chemicals and groups of chemicals.

In accordance with section 6(f)(1) of the Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA), as amended, EPA is issuing a notice of receipt of requests by the registrants to voluntarily cancel the registrations for all of their products containing 4-chloro-alpha- (1-methylethyl)benzeneacetic acid, cyano(3-phenoxyphenyl)methyl ester (fenvalerate). The requests would terminate the last fenvalerate products registered for use in the United States. EPA intends to grant these requests at the close of the comment period for this announcement unless the Agency receives substantive comments within the comment period that would merit its further review of the requests, or unless the registrants withdraw their requests within this period. Upon acceptance of these requests, any sale, distribution, or use of products listed in this notice will be permitted only if such sale, distribution, or use is consistent with the terms as described in the final order.

Tolerances are established for residues of the insecticide cyano(3-phenoxyphenyl)methyl-4-chloro-alpha-(1-methylethyl) benzeneacetate in or on the following raw agricultural commodities: [Table#6124]

A food additive tolerance of 0.05 parts per million is established for residues of the insecticide cyano(3-phenoxyphenyl)methyl-4-chloro-alpha-(1-methylethyl)benzeneacetate and an isomer, (S)-cyano(3-phenoxyphenyl)methyl-(S)-4-chloro-alpha-(1-methylethyl)-benzeneacetate, as follows: (i) In or on food commodities (other than those already covered by a higher tolerance as a result of use on growing crops) in food-handling establishments where food products are held, processed, or prepared. (ii) Application of cyano(3-phenoxyphenyl)methyl-4-chloro-alpha-(1-methylethyl)benzeneacetate shall be limited to space treatment with a maximum of 0.5 fluid ounce of a 0.05-percent active ingredient solution per 1,000 cubic feet of space, or as a contact spray applied as a coarse wet spray at a maximum of 1 gallon of a 0.2-percent active ingredient solution per 1,000 square feet of surface. Food must be removed or covered during treatment. Spray should not be applied directly to surfaces or utensils that may come into contact with food. Food-contact surfaces and equipment should be thoroughly cleaned with an effective cleaning compound and rinsed with potable water before using. (iii) Application of (S)-cyano(3-phenoxyphenyl) methyl-(S)-4-chloro-alpha-(1-methylethyl)benzeneacetate shall be limited to space treatment with a maximum of 1.0 fluid ounce of a 0.25-percent active ingredient solution per 1,000 cubic feet of space, or as a contact spray applied as a coarse wet spray at a maximum of 1 gallon of a 0.05-percent active ingredient solution per 1,000 square feet of surface, or as a pressurized spot/crack and crevice spray of a 0.25-percent solution. Food must be removed or covered during treatment. Spray should not be applied directly to surfaces or utensils that may come into contact with food. Food-contact surfaces and equipment should be thoroughly cleaned with an effective cleaning compound and rinsed with potable water before using. (iv) To assure safe use of the additive, its label and labeling shall conform to that registered with the U.S. Environmental Protection Agency, and it shall be used in accordance with such label and labeling.

A regulation is established permitting residues of the insecticide 4-cyano(3-phenoxyphenyl)methyl-4-chloro-alpha- (1-methylethyl)benzeneacetate in or on the following raw agricultural commodity: Soybean, hulls.

For more FIFRA Requirements (Complete) data for FENVALERATE (6 total), please visit the HSDB record page.

A pyrethroid. This compound is an ester and nitrile. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Nitriles may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids).

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

Use water, foam, carbon dioxide, powder.

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Refer for medical attention .

Liquid formulations containing organic solvents may be flammable. Water foam carbon dioxide powder

Extinguish fire using agent suitable for type of surrounding fire. /Pyrethrins/

If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire (Material itself does not burn or burns with difficulty.). Keep run-off water out of sewers and water sources. /Pyrethroid pesticide, solid, toxic/

If material on fire or involved in fire: Use water in flooding quantities as fog. Solid streams of water may be ineffective. Use "alcohol" foam, dry chemical or carbon dioxide. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Keep run-off water out of sewers and water sources. /Pyrethroid pesticide, liquid, flammable, toxic; Pyrethroid pesticide, liquid, toxic, flammable/

If material on fire or involved in fire: Use water in flooding quantities as fog. Use "alcohol" foam, dry chemical or carbon dioxide. Cool all affected containers with flooding quantities of water. Keep run-off water out of sewers and water sources. /Pyrethroid pesticide, liquid, toxic/

Store in an area without drain or sewer access. Keep in a well-ventilated room. Separated from strong oxidants, strong bases, food and feedstuffs

Store in original containers away from food stuffs, animal feed.

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/

Safe Storage of Pesticides. Always store pesticides in their original containers, complete with labels that list ingredients, directions for use, and first aid steps in case of accidental poisoning. Never store pesticides in cabinets with or near food, animal feed, or medical supplies. Do not store pesticides in places where flooding is possible or in places where they might spill or leak into wells, drains, ground water, or surface water. /Residential uses/

Personal protection: filter respirator for organic gases and vapors. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent and remove to safe place.

Environmental consideration - Land spill: Dig a pit, pond, lagoon, or holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, or cement powder. /Pyrethrins/

Environmental consideration - Water spill: If /pyrethrins/ are dissolved, apply activated carbon at ten times the spilled amount in the region of 10 ppm or greater concn. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates. /Pyrethrins/

If a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label./Residential uses/

After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide..To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash. /Residential uses/

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant life; and conformance with environmental and public health regulations.

Incineration would be an effective disposal procedure where permitted. If an efficient incinerator is not available, the product should be mixed with large amounts of combustible material and contact with the smoke should be avoided. /Pyrethrin products/

Group II Containers: Non-combustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) must first be triple-rinsed. Containers that are in good condition may be returned to the manufacturer or formulator of the pesticide product, or to a drum reconditioner for reuse with the same type of pesticide product, if such reuse is legal under Department of Transportation regulations (eg 49 CFR 173.28). Containers that are not to be reused should be punctured ... and transported to a scrap metal facility for recycling, disposal or burial in a designated landfill. /Organic or metallo-organic pesticides/

Safe Disposal of Pesticides. The best way to dispose of small amounts of excess pesticides is to use them - apply them - according to the directions on the label. If you cannot use them, ask your neighbors whether they have a similar pest control problem and can use them. If all of the remaining pesticide cannot be properly used, check with your local solid waste management authority, environmental agency, or health department to find out whether your community has a household hazardous waste collection program or a similar program for getting rid of unwanted, leftover pesticides. These authorities can also inform you of any local requirements for pesticide waste disposal. /Residential uses/

Safe Disposal of Pesticides. An empty pesticide container can be as hazardous as a full one because of residues left inside. Never reuse such a container. When empty, a pesticide container should be rinsed carefully three times and the rinsewater thoroughly drained back onto the sprayer or the container previously used to mix the pesticide. Use the rinsewater as a pesticide, following label directions. Replace the cap or closure securely. Dispose of the container according to label instructions. Do not puncture or burn a pressurized container like an aerosol - it could explode. Do cut or puncture other empty pesticide containers made of metal or plastic to prevent someone from reusing them. Wrap the empty container and put it in the trash after you have rinsed it. /Residential uses/

Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Avoid eye, skin, mouth contact.

SRP: The scientific literature supports the wearing of contact lenses in industrial environments, as part of a program to protect the eye against chemical compounds and minerals causing eye irritation. 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.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

For more Preventive Measures (Complete) data for FENVALERATE (20 total), please visit the HSDB record page.

Following oral exposure, the treatment is symptomatic and supportive and includes monitoring for the development of hypersensitivity reactions with respiratory distress. Provide adequate airway management when needed. Gastric decontamination is usually not required unless the pyrethrin product is combined with a hydrocarbon. Following inhalation exposure, move patient to fresh air. monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. In case of eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. If irritation, pain, swelling, lacrimation, or photophobia persist, the patient should be seen in a health care facility. If the contamination occurs through dermal exposure, Remove contaminated clothing and wash exposed area thoroughly with soap and water. A physician may need to examine the area if irritation or pain persists. Vitamin E topical application is highly effective in relieving parenthesis. (L363)

Fenvalerate, a widely used pesticide, was administered orally to goats at a dose rate of 15 mg/kg body weight, daily for 270 days. After 90 days of dosing, the animals, together with appropriate controls, were vaccinated with Brucella abortus strain 19. The fenvalerate reduced both the humoral and cell-mediated immune responses, as assessed by the standard tube agglutination test and delayed hypersensitivity test, respectively.

The ability of 3 mg/kg/day diazepam to alter the neurobehavioral and neurochemical consequences of perinatal exposure to Ambush and Pydrin was examined. Seventy-two pregnant female rats served as subjects. Half of the subjects were treated with diazepam and the other half were treated with the vehicle via subcutaneous osmotic pumps for 33 days starting on gestational day 1 Each group was further divided into six gavage treatment groups: corn oil, corn oil + 96% xylene, 1.25 or 0.125 mg/kg Pydrin, and 4.0 or 0.4 mg/kg Ambush. Behavioral evaluations were conducted on half the pups in each litter and the other pups were used for the neurochemical assays. Behavioral evaluations included locomotor activity, screen testing, and passive avoidance learning. Brains for neurochemical analysis were extracted and sectioned into frontal cortex, caudate, hippocampus and cerebellum. Neurochemical assays assessed levels of DA, DOPAC, 5-HIAA, 5-HT, HVA, aspartate, glutamate, glutamine, glycine, GABA, and taurine. Diazepam treatment did produce some neurotoxicity in the control pups but diazepam exposure did reverse elevations in amino acid levels in the cerebellum produced by both pyrethroids. In addition diazepam reversed the pyrethroid effects on activity and muscular coordination. These diazepam effects were not specific to Type I or Type II pyrethroids.

This investigation explored the behavioral and neurochemical toxicity of perinatal oral exposure to Ambush (Type I) and Pydrin (Type II), two pyrethroid formulations. Thirty-six female rats were mated and exposed to various pyrethroid formulations by oral gavage from the first gestational day until their pups (culled to 8/litter) were 12 days old. Six mothers were exposed daily to one of the following treatments: corn oil control, corn oil+96% xylene, 1.25 mg/kg Pydrin (pesticidal ingredient fenvalerate), 0.125 mg/kg Pydrin, 4.0 mg/kg Ambush (pesticidal ingredient permethrin), or 0.4 mg/kg Ambush. Behavioral evaluations of locomotor activity, muscular coordination and passive avoidanc learning were conducted on half of the pups from each litter (N = 24 pups/treatment condition). The other pups were sacrificed, brains were removed and sectioned into frontal cortex, hippocampus, caudate, and cerebellum for neurochemical assessment. The monoamines DA, DOPAC, 5-HIAA, 5-HT and HVA levels were determined and the amino acids aspartate, glutamate, glutamine, glycine, GABA, and taurine were determined for each of the brain regions. Gestational duration was shortened by exposure to the high doses of Pydrin and Ambush but only pups from the 4.0 mg/kg Ambush group were significantly lighter. No physical malformations were observed in pups from any of the treatment conditions, although the high Pydrin exposure condition resulted in a 4% death rate. Behavioral changes were seen for both locomotor activity and muscular coordination. The shape of across-session habituation of locomotion was different for the xylene and corn oil and the high dose Ambush groups. Both groups were less active on day 1 and more active on days 2 and 3 than the other pups. The high doses of Ambush and Pydrin produced slower intrasession habituation. Muscular coordination was improved slightly following low dose exposure to both pesticides and reduced following high dose exposures. Regional brain weights were normal for the cortex, cerebellum and caudate but the hippocampus was 64% heavier for pups treated with 4.0 mg/kg Ambush. Amino acid determinations indicated that the cerebellum was most affected where glutamate, glutamine, aspartate and taurine were reduced following xylene or pyrethroid exposure. The biogenic amine transmitter 5-HT was reduced in several brain regions following pyrethroid exposures. These data suggest that levels of Ambush and Pydrin as low as the LD50/10,000 can alter behavior and neurotransmitter functioning.

Following the administration of a single or repeated doses of dimethoate, carbaryl, and fenvalerate, the activities of tryptophan-2,3-dioxygenase, indoleamine-2,3-dioxygenase, kynurenine, kynureninase, kynurenine-transaminase, and pyridoxal-phosphokinase were determined in the liver, kidney and lung of male Wistar rats. Treatment consisted of 10% of the median lethal dose of each insecticide given orally for the single dosing investigations and 5% of the median lethal dose was given orally for 5 consecutive days as repeated doses. Weight losses in both body and organ were noted only after repeated dose of dimethoate. Significant decreases in the activity of kynurenine-3-hydroxylase, kynurenine-2-oxoglutarate-transaminase, kynurenine-pyruvate-transaminase, and pyridoxal-phosphokinase were noted following repeated administration of dimethoate. Carbaryl in repeated doses caused significant decreases in the activity of apo-tryptophan-2,3-dioxygenase, kynurenine-2-oxoglutarate-transaminase, kynurenine-pyruvate-transaminase, and serine-glyoxylate-transaminase. An inhibition was noted in tryptophan-2,3-dioxygenase following external addition of insecticides at different concn to an incubation mixture. Other enzymes demonstrated no change in their activities following this treatment.

For more Interactions (Complete) data for FENVALERATE (14 total), please visit the HSDB record page.

Pyrethroid effects typically include rapid onset of aggressive behavior and increased sensitivity to external stimuli, followed by fine tremor, prostration with coarse whole body tremor, elevated body temperature, coma, and death. Paresthesia, severe corneal damage, hypotension and tachycardia, associated with anaphylaxis, can also occur following pyrethriod poisoning. (L857)

LC50 Anas platyrhynchos (Mallard duck) diet 5502 ppm for 8 days (95% confidence interval: 3194-9470 ppm)

LD50 /Anas platyrhynchos/ (Mallard duck) oral 9932 mg/kg

LC50 Colinus virginianus (northern bobwhite) diet >5000 ppm for 8 days

LD50 Colinus virginianus (northern bobwhite, age 5 weeks) oral 1785 mg/kg (95% confidence interval: 1100-3573 mg/kg)

For more Ecotoxicity Values (Complete) data for FENVALERATE (118 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 5,300(2), indicates that fenvalerate is expected to be immobile in soil(SRC). Volatilization of fenvalerate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.4X10-8 atm-cu m/mole(SRC), based upon its vapor pressure, 1.5X10-9 mm Hg(3), and water solubility, 2.4X10-2 mg/L(4). Fenvalerate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Using a mineral and an organic soil, 92-98% of applied fenvalerate degraded after an 8-week incubation period(5) suggesting that biodegradation is an important environmental fate process in soil(SRC). The average half-life in southern US forests where the compound was been used in silviculture applications is 35 days with loss attributed to photodegradation, biodegradation and hydrolysis(6).

AQUATIC FATE: Based on a classification scheme(1), a Koc value of 5,300(2), indicates that fenvalerate is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 3.4X10-8 atm-cu m/mole(SRC) derived from its vapor pressure, 1.5X10-9 mm Hg(4), and water solubility, 2.4X10-2 mg/L(5). According to a classification scheme(6), a BCF range of 570 to 1,100(7) suggests that bioconcentration in aquatic organisms is high to very high, provided the compound is not metabolized by the organism(SRC). Research indicates that hydrolysis of pyrethroid compounds is restricted to alkaline pH and generally results in polar products such as acids and aldehydes; these are expected to be more soluble than the neutral parent compounds(8). A biodegradation half-life of 34 days using sediment and seawater inoculum(7) suggests that biodegradaton may be 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), fenvalerate, which has a vapor pressure of 1.5X10-9 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase fenvalerate may be removed from the air by wet or dry deposition(SRC). Thin films of fenvalerate on glass exhibited an initial photodegradation half-life of 4 days when exposed to sunlight(3) and therefore it may be susceptible to direct photolysis by sunlight(SRC). Photodegradation in UV light yields 3-phenoxybenzoyl cyanide and 3-phenoxybenzyl cyanide(4).

According to compiled results of the US Food and Drug Administration's pesticide residue monitoring programs (including the Total Diet Study) for fiscal years 1978-1986, fenvalerate has been detected as a pesticide residue in American foods(1,2); the frequency of occurrence or concentrations of fenvalerate detected were not reported(SRC). During a 5-yr period from 1982-1986, the US FDA's Los Angeles District Laboratory analyzed 19,581 samples of domestic and imported food and feed commodities for pesticide residues(3); fenvalerate was detected in 25 samples at concentrations of 0.05-1.0 ppm(3). For fiscal years 1988 and 1989, 27,065 food samples were collected and analyzed for pesticide residues by 10 state laboratories (CA, NY, FL, IN, MA, MI, NC, OR, VA and WI)(4); fenvalerate was detected in 54 samples (concentrations not reported)(4). According to compiled results of the US Food and Drug Administration's pesticide residue monitoring programs in domestic infant and adult foods for fiscal years 1985-1991, fenvalerate was detected as a pesticide residue in 11 of 2,464 apple samples, maximum residue 0.19 ppm and in 1 of 571 pear samples, maximum residue 0.08 ppm(5). Fenvalerate was not detected in 234 items making up diets of 8 population groups as a result of an FDA Total Diet Study conducted from July 1986 through April 1991(6). A US Food and Drug Administration 1992-1993 survey of 710 domestic and 949 imported pears resulted in detection of fenvalerate in two domestic samples at a maximum concentration of 0.08 ppm and one imported sample at 0.05 ppm; a survey of 1,219 domestic and 144 imported tomatoes resulted in detection of fenvalerate in three domestic samples at a trace concentration; it was not detected in imported tomato samples(7). A US Food and Drug Administration 1993-1994 survey of 769 domestic and 1,062 imported apples resulted in detection of fenvalerate in one imported sample at 0.81 ppm; it was not detected in domestic samples(8).

Of a total of 946 samples analyzed in the 1984-1989 Canadian national surveillance program, 7 were found to contain fenvalerate residues, at levels of 0.02-0.096 mg/kg(1); most were in pears (6/114 samples) and one in lettuce (1/11 samples)(1). In Sweden, 163 of 165 samples of imported fruit and vegetables contained residues up to 0.2 mg/kg(1); one had a residue of 0.54 mg/kg(1). As a result of a Danish survey of food commodities conducted from January 1995 to December 1996, fenvalerate was not detected in unspecified fruits and vegetables and cereals(2). As a result of food monitoring studies conducted in Karachi, Pakistan from 2000-2003, fenvalerate residues were detected in 15 of 206 samples of 27 market basket vegetables, with positive detections were reported in onion, mint, salad, spinach, chillies, french bean, cucumber, tomato, cabbage, and cauliflower(3). Four samples exceeding the FAO/WHO limit(3) of acceptable daily intake of 0-0.02 mg/kg body weight established in 1986(4). Fenvalerate residues were reported in 765 agricultural products (478 domestic, 287 imported) in the Hyogo Prefecture Japan, sampled from April 1995 through March 2000); 12 of 291 domestic lettuce samples positive, 4 at <0.01 ug/g, 3 at <0.05 ug/g, 3 at <0.1 ug/g, 2 at <0.5 ug/g; 5 of 106 Japanese persimmon samples positive, 2 at <0.01 ug/g, 1 at <0.05 ug/g, 1 at <0.1 ug/g, 1 at <0.5 ug/g(5). Fenvaerlate was detected in 4 of 55 imported broccoli samples, 2 at <0.01 ug/g, 2 at <0.5 ug/g(5).

Fenvalerate residues in green gram (Vigna radiata) foliage, a staple food crop of India, were 13.1, 6.8, 2.6. and 1.7 ppm at 1 hr, 5, 10, and 15 days, respectively, following commercial application, corresponding to a half-life of 5.0 days and safe waiting period of 19 days(1). Levels in okra fruits remaining following spraying with low application of 300 ml/ha (ppm, time after treatment) were: 1.38, 1 hr; 1.09, 1 day; 0.40, 3 days; 0.28, 7 days; 0.10, 10 days; not detected, 25 days(2). At medium application of 375 ml/ha, residues were (ppm, time after treatment): 2.76, 1 hr; 1.31, 1 day; 0.69, 3 days; 0.51, 7 days; 0.02, 10 days; not detected, 25 days(2). At high application of 500 mL/ha, residues were (ppm, time after treatment): 4.54, 1 hr; 2.52, 1 day; 1.27, 3 days; 0.67, 7 days; 0.04, 10 days; not detected, 25 days(2). These results suggest a waiting period of 10 days before residues fall below the maximum allowable residue limit of 0.2 ppm(2).

The average fenvalerate concentration in farmgate samples of eggplant was 0.16 ug/g, sampled in India(1). As a result of a US ten-year study of ready-to-eat foods conducted from 1982-1991, fenvalerate was detected in canned green beans, 1 sample, 0.0410 ug/g and in canned spinach 1 sample, 0.0570 ug/g; samples were of 37 market baskets, each containing 234 food items representing 5,000 food types in American diets(2). Fenvalerate was analyzed for in 1,579 Egyptian fruit and vegetable samples in 1996; it was detected in one cucumber sample, concentration of 0.14 mg/kg(3).

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion.

Oral (L96) ; inhalation (L96) ; dermal (L96)

... Two Holstein cows were fed fenvalerate at 5 and 15 mg/kg diet for 4 days and were then given a clean diet for 6 days. Total excretion of fenvalerate in milk amounted to 0.44 and 0.64% of the total dose for the 5 and 15 mg/kg levels, respectively ... .

Three lactating cows were fed (14)C-(acid-labelled)-fenvalerate at a dose level of 0.11 mg/kg diet daily for 21 days and sacrificed 12 hr after receiving the last dose. The recovery of (14)C in the milk was less than 1% and the levels ranged from < 0.0006 to 0.0019 ug/litre, with a plateau occurring after 1 week of feeding. ... In another study, fenvalerate was sprayed on cows at a rate of 0.2, 0.4, or 2 g/animal. ... Maximum residue /was/ ... 0.02 mg/kg in milk at the dose rate of 2 g/cow ... .

EXPERIMENTAL: Two Holstein cows were treated with 0.5 g of fenvalerate per cow in three consecutive topical treatments at 14-day intervals(1); residues in whole milk were at a max 6 hr after treatment and declined to less than 0.2 ug/L over 21 days(1); only 0.03-0.06% of applied fenvalerate appeared in the milk as the intact insecticide(1). Fenvalerate concentrations in dairy products were found to increase with fat content; retention was 23.43, 30.5 and 54.89% in cheese, cream and butter, respectively, originating from spiked buffalo milk samples(2).

Both type I and type II pyrethroids exert their effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. They appear to bind to the membrane lipid phase in the immediate vicinity of the sodium channel, thus modifying the channel kinetics. This blocks the closing of the sodium gates in the nerves, and thus prolongs the return of the membrane potential to its resting state. The repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential produces effects quite similar to those produced by DDT, leading to hyperactivity of the nervous system which can result in paralysis and/or death. Other mechanisms of action of pyrethroids include antagonism of gamma-aminobutyric acid (GABA)-mediated inhibition, modulation of nicotinic cholinergic transmission, enhancement of noradrenaline release, and actions on calcium ions. They also inhibit calium channels and Ca2+, Mg2+-ATPase. (T10, T18, L857)

In accordance with section 6(f)(1) of the Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA), as amended, EPA is issuing a notice of receipt of requests by the registrants to voluntarily cancel the registrations for all of their products containing 4-chloro-alpha- (1-methylethyl)benzeneacetic acid, cyano(3-phenoxyphenyl)methyl ester (fenvalerate). The requests would terminate the last fenvalerate products registered for use in the United States. EPA intends to grant these requests at the close of the comment period for this announcement unless the Agency receives substantive comments within the comment period that would merit its further review of the requests, or unless the registrants withdraw their requests within this period. Upon acceptance of these requests, any sale, distribution, or use of products listed in this notice will be permitted only if such sale, distribution, or use is consistent with the terms as described in the final order.

Tolerances are established for residues of the insecticide cyano(3-phenoxyphenyl)methyl-4-chloro-alpha-(1-methylethyl) benzeneacetate in or on the following raw agricultural commodities: [Table#6124]

A food additive tolerance of 0.05 parts per million is established for residues of the insecticide cyano(3-phenoxyphenyl)methyl-4-chloro-alpha-(1-methylethyl)benzeneacetate and an isomer, (S)-cyano(3-phenoxyphenyl)methyl-(S)-4-chloro-alpha-(1-methylethyl)-benzeneacetate, as follows: (i) In or on food commodities (other than those already covered by a higher tolerance as a result of use on growing crops) in food-handling establishments where food products are held, processed, or prepared. (ii) Application of cyano(3-phenoxyphenyl)methyl-4-chloro-alpha-(1-methylethyl)benzeneacetate shall be limited to space treatment with a maximum of 0.5 fluid ounce of a 0.05-percent active ingredient solution per 1,000 cubic feet of space, or as a contact spray applied as a coarse wet spray at a maximum of 1 gallon of a 0.2-percent active ingredient solution per 1,000 square feet of surface. Food must be removed or covered during treatment. Spray should not be applied directly to surfaces or utensils that may come into contact with food. Food-contact surfaces and equipment should be thoroughly cleaned with an effective cleaning compound and rinsed with potable water before using. (iii) Application of (S)-cyano(3-phenoxyphenyl) methyl-(S)-4-chloro-alpha-(1-methylethyl)benzeneacetate shall be limited to space treatment with a maximum of 1.0 fluid ounce of a 0.25-percent active ingredient solution per 1,000 cubic feet of space, or as a contact spray applied as a coarse wet spray at a maximum of 1 gallon of a 0.05-percent active ingredient solution per 1,000 square feet of surface, or as a pressurized spot/crack and crevice spray of a 0.25-percent solution. Food must be removed or covered during treatment. Spray should not be applied directly to surfaces or utensils that may come into contact with food. Food-contact surfaces and equipment should be thoroughly cleaned with an effective cleaning compound and rinsed with potable water before using. (iv) To assure safe use of the additive, its label and labeling shall conform to that registered with the U.S. Environmental Protection Agency, and it shall be used in accordance with such label and labeling.

A regulation is established permitting residues of the insecticide 4-cyano(3-phenoxyphenyl)methyl-4-chloro-alpha- (1-methylethyl)benzeneacetate in or on the following raw agricultural commodity: Soybean, hulls.

For more FIFRA Requirements (Complete) data for FENVALERATE (6 total), please visit the HSDB record page.

QP - Antiparasitic products, insecticides and repellents

QP - Antiparasitic products, insecticides and repellents

In intact locusts and neuromuscular preparations of locusts, fenvalerate caused (a) prolonged firing in the crural nerve without associated muscle contractions; (b) sustained muscle contractions; and (c) a block of neurally evoked muscle contractions at low concentrations (1x10-8 to 1x10-5 mol/l). However, fenvalerate did not cause repetitive firing and after-discharges with associated muscle contractions. The fenvalerate steroisomers with an (S) configuration in the alcohol moiety are more active pharmacologically and toxicologically than those with the (R) configuration or the racemate (R,S). It is also apparent that steroisomers with the (S) configuration in the acid moiety are more active than those with the (R) configuration or the racemate (R,S).

Phosphoinositide breakdown in guinea pig cerebral cortical synaptoneurosomes induced by the Type-I pyrethroids allethrin, resmethrin, and permethrin, and the Type-II pyrethroid deltamethrin and fenvalerate were investigated with various receptor agonists as well as sodium channel blockers and agents. Phosphoinositide breakdown was determined from inositol-phosphate formation by tritiated inositol labeled synaptoneurosomes. All five pyrethroids dose dependently induced phosphoinositide breakdown. Type II pyrethroids exhibited higher potency and deltamethrin was more efficacious than the Type I pyrethroids. Five uM tetrodotoxin, a blocker of voltage dependent sodium channels, partially inhibited deltamethrin (85 percent) and fenvalerate (60 percent) responses but not allethrin or resmethrin. Fenvalerate induced stimulation of phosphoinositide was additive with stimulation elicited by the receptor agonists carbamylcholine (1 mM) and norepinephrine (1000 uM) but less than additive with the sodium channel agents batrachotoxin, pumiliotoxin-B, and scorpion venom. Allethrin (100 uM) was less than additive with receptor agonists or sodium channel agents and actually significantly inhibited response to scorpion venom. Effects for 100 uM allethrin with either fenvalerate or deltamerthrin were not different from allethrin alone. Ten uM allethrin slightly decreased response to 10 to 100 uM deltamethrin. The local anesthetic dibucaine, a sodium channel activation inhibitor, completely blocked deltamethrin induced phosphoinositide breakdown but was much less effective in inhibiting allethrin response. It appears likely that Type I pyrethroids induce phosphoinositide breakdown through a mechanism other than sodium channel activation while Type II pyrethroids act in a manner analogous to other sodium channel agents.

Eight different synthetic pyrethroids were examined to determine their effects on the excitability of hippocampal granule cells in urethane anesthetized rats. A paired stimulus approach was used. All eight prolonged the depression of granule cells excitability that follows stimulation of their major synaptic input, the perforant path. The magnitude of this effect depended upon the class to which the pyrethroid belonged. Type I pyrethroids (those primarily producing tremor) prolonged the depression of granule cell excitability for shorter periods than did type II pyrethroids (those primarily producing salivation and choreoathetosis) or pyrethroids producing a mixed type of intoxication. No overlap was found between groups. To determine whether the difference observed between type I and type II pyrethroids was the result of an infelicitous selection of doses, cismethrin (type I) was tested over a dose range of 1.5-24 times the conscious rat iv LD50. Even at the highest dose, the prolongation remained well below that produced by type II pyrethroids. The effect of deltamethrin was shown to be consistent with the production or potentiation of a surmountable inhibitory response. This action of deltamethrin was antagonizable by mephenesin and lidocaine, but not by picrotoxin or halothane. The type of effect, its time course, and the anatagonism data suggest that type II pyrethroids enhance inhibition in the dentate gyrus. This action does not appear to be mediated by GABA receptors.

The transmitter activated ion channels are known to be important target sites of a variety of therapeutic and toxic agents. The GABA activated chloride channel has been shown to be modulated by general anesthetics, alcohols, and the pyrethroid, cyclodiene and lindane insecticides. The general anesthetics halothane, enflurane and isoflurane greatly augmented the GABA activated current before desensitization took place, and suppressed it after desensitization at clinically relevant concn equivalent to 1-2 minimum alveolar concn. The stimulating effect appears to be a mechanism of general anesthesia. It seems that general anesthetics have a specific affinity for the GABA receptor-channel complex. Ethanol also augmented the GABA activated peak chloride current with little or no effect on the desensitized sustained current. Longer chain alcohols n-butanol, n-hexanol, n-octanol, and n-decanol also exerted the same type of effect, with the potency and efficacy increasing with lengthening of the carbon chain. The GABA receptor-channel complex has also been shown to be an important target site of certain insecticides. The type II pyrethroids deltamethrin and fenvalerate augmented the GABA activated peak chloride current when applied concurrently with GABA, but the effect was diminished as the pyrethroids were applied for long periods of time prior to GABA application. The latter effect might explain the controversy in the literature regarding the pyrethroid action on the GABA system. The type I pyrethroid allethrin suppressed the GABA activated peak chloride current when co-applied with GABA. Both types of pyrethroids suppressed the N-methyl-d-aspartate induced current. Lindane and the cyclodienes dieldrin, endrin, heptachlor epoxide, and isobenzan suppressed the GABA activated chloride current. These effects can account for the convulsant action of lindane and the cyclodienes.

For more Mechanism of Action (Complete) data for FENVALERATE (22 total), please visit the HSDB record page.

When carp (Cyprinus carpio) was exposed to ((14)C-CN)-(2S, alphaRS)-fenvalerate (0.8 ug/litre) under semi-static conditions for 7 days, the radioactivity in fish increased to a level of 922 ug/kg. Once the fish were transferred to fresh water, the levels of radioactivity in the fish decreased with an initial half-life of 5 days ... . /(2S, alphaRS)-Fenvalerate/

Elimination from body fat is slow, with a half-life of 7-10 days; elimination from brain is less slow, with a half-life of 2 days (Marei et al., 1982), presumably due to the more effective perfusion of brain and the presence of esterases in brain tissue.

Metabolism in dogs was studied with ((14)C-chlorophenyl)- or ((14)C-phenoxybenzyl)-fenvalerate administered as a single oral dose of 1.7 mg/kg bw, dissolved in corn oil, in gelatine capsules. Excreta and blood were collected daily for 3 days and analysed for radioactivity by liquid scintillation counting. ... More total radioactivity was recovered in animals given ((14)C-chlorophenyl)-fenvalerate than in those given ((14)C-phenoxybenzyl)-fenvalerate, and the half-lives were 1 day and 0.7 day, respectively. ...

Fenvalerate undergoes hydroxylation to give 2'- or 4'- hydroxylated phenoxy esters and hydrolysis to give 3-phenoxybenzoic acid and its hydroxy derivatives (free and conjugates), 3-(4-chlorophenyl)-isovaleric acid and its hydroxy derivatives (free, lactones, and conjugates), thiocyanate, and CO2.

The fate of fenvalerate in rats and mice has been studied using fenvalerate radiolabelled in the acid moiety or benzyl or cyano groups. The administered radioactivity, except that of the cyano-labelled compounds, is readily excreted (up to 99% in 6 days). The major metabolic reactions are ester cleavage and hydroxylation at the 4' position. Various oxidative and conjugation reactions that lead to a complex mixture of products have been shown to occur. When studies were carried out with fenvalerate radiolabelled in the cyano group, elimination of the radioactive dose was less rapid (up to 81% in 6 days). The remaining radioactivity was retained mainly in the skin, hair, and stomach as thiocyanate. A minor, but very important, metabolic pathway is the formation of a lipophilic conjugate of (2R)-2-(4-chlorophenyl)isovalerate. This congugate, which is implicated in the formation of granuloma, has been detected in the adrenals, liver mesenteric lymph nodes of rats, mice, and some other species.

Despite its lack of a cyclopropane ring in the acid, fenvalerate is rapidly metabolized in rats by ester cleavage and hydroxylation, as are the more traditional pyrethroids.

On a single oral dose or five consecutive oral doses of (14)C-esfenvalerate or (14)C-fenvalerate labeled in the acid moiety to 13-day pregnant rats at rates of 2.5 and 10 mg/kg/day, respectively, the maternal blood and placenta generally showed higher (14)C levels as compared with the fetus and amniotic fluid. Both compounds and their metabolites did not transfer readily from the maternal blood to the fetus, the amount of (14)C transferred being less than 0.07% of the dose. There were no substantial differences in the fetal (14)C level and the transfer ratio ((14)C tissue level/(14)C maternal blood level) between both labeled preparations. Major (14)C-compounds in the fetus, maternal blood and placenta were the parent compounds, CPIA (2-(4-chlorophenyl)isovaleric acid) and CPIA-hydroxylated derivatives and there was no qualitative difference in metabolic fates between the two compounds, except that a trace amount of CPIA-cholesterol ester (cholesteryl (2R)-2-(4-chlorophenyl)isovalerate] was detected in the maternal blood and placenta only with fenvalerate. CPIA-cholesterol ester did not seem to transfer from the maternal blood to the fetus. Overall, esfenvalerate and fenvalerate seem to behave in the same manner as far as placental transfer was concerned.

For more Metabolism/Metabolites (Complete) data for FENVALERATE (23 total), please visit the HSDB record page.

Esfenvalerate has known human metabolites that include 2'-hydroxy-esfenvalerate and 4'-hydroxy-esfenvalerate.

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.

Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics.

Metabolism and bioaccumulation of fenvalerate and its fenvalerate its metabolites in liver, kidney and brain of rat following the oral administration of a sub-lethal dose (15 mg/kg) of the pesticide for 7, 15 and 30 day periods was investigated by high-performance liquid chromatography (HPLC) in terms of the relative mole concentrations in rat tissues. The cleavage of the ester linkage in fenvalerate yielding two metabolites was found to be primary step in the biodegradation of fenvalerate in rat organs. These metabolites were purified to homogeneity by HPLC and characterized by infra-red spectroscopy as 4-chloro-alpha-(1-methylethyl) benzeneacetic acid and 3-phenoxy benzoic acid.

The disposition kinetics of fenvalerate were studied in goats after dermal application of 100 mL of 0.25% (w/v) solution. The insecticide persisted in the blood for 72 hr. The mean (+/- SEM) Vd(area) and apparent t 1/2 (beta) were 9.92 +/- 1.44 L/kg and 17.51 +/- 2.65 hr, while the AUC and ClB values were respectively 82.15 +/- 7.40 ug hr/mL and 0.56 +/- 0.05 L/(kg hr). Four days after the dermal application, the highest concentration of fenvalerate residues was found in the adrenal gland, followed by the biceps muscle, omental fat, liver, kidney, lung and cerebrum in that order. Fenvalerate caused hyperglycaemia but had no effect on serum protein and cholesterol levels. Serum acetylcholinesterase activities were increased after 24 hr but were below the initial values from 48 to 120 hr.

Poorly absorbed through rabbit skin.

Elimination from body fat is slow, with a half-life of 7-10 days; elimination from brain is less slow, with a half-life of 2 days, presumably due to the more effective perfusion of brain and the presence of esterases in brain tissue.

For more Absorption, Distribution and Excretion (Complete) data for FENVALERATE (21 total), please visit the HSDB record page.

Used as an insecticide and medication; [HSDB]

US registration voluntarily cancelled by registrants in 2008; [EPA]

Farming (Pesticides) [Category: Industry]

For fenvalerate (USEPA/OPP Pesticide Code: 109301) ACTIVE products with label matches. /SRP: Registered for 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./

Fenvalerate is a synthetic pyrethroid insecticide which is used to control insects and related organisms, mollusks, fouling organisms and miscellaneous invertebrates on agricultural, pet care, domestic home and garden (domestic), and commercial/industrial/food and non-food/mosquito abatement (commercial) sites. These are the last fenvalerate products registered for use in the United States.

Highly active contact insecticide effective against a wide range of pests, including strains resistant to organochlorine, organophosphorus, and carbamate insecticides. It controls insects that attack leaves or fruits on various crops, including cotton, fruit, vegetables and vines at 25-250 g ai/ha, and is persistent under various field conditions. It is also used in public health and animal husbandry, controlling flies in cattle sheds for 60 days at 100 mg/sq m wall, and is effective against Boophilus at 200-300 mg/L.

Fenvalerate ... is prepared by the esterification of (2RS)-2-(4-chlorophenyl)-3-methylbutyric acid (also known as (2RS)-2-(4-chlorophenyl)isovaleric acid, CPIA, or Cl-Vacid) with (alphaRS)-alpha-cyano-3-phenoxybenzyl alcohol ... .

Fenvalerate can be prepared by esterification of 3-phenoxybenzaldehyde cyanohydrin with 2-(4-chlorophenyl)isovaleroyl chloride, or by condensation of 3-phenoxy-alpha-halobenzyl cyanide with the isovaleric acid in the presence of a base such as potassium carbonate. More conveniently, fenvalerate can be provided by the Francis reaction using the isovaleroyl chloride, the aldehyde and sodium cyanide.

Emulsifiable concentrate, dust, flowable, granules, wettable powder.

Technical grade 90% min of fenvalerate.

An emulsifiable concentrate, marketed as Pydrin 2.4 EC Insecticide, is comprised of 32% technical Pydrin and 68% aromatic hydrocarbon solvents and emulsifiers.

Ectrin 8%

For more Formulations/Preparations (Complete) data for FENVALERATE (37 total), please visit the HSDB record page.

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

A synthetic pyrethroid insecticide without the usual cyclopropane ring.

/Pyrethroids/ are modern synthetic insecticides similar chemically to natural pyrethrins, but modified to increase stability in the natural environment. /Pyrethroids/

Fenvalerate is a mixture of four stereoisomers (RR, RS, SR, SS) due to the two asymmetric carbon atoms in the molecule. It has an alpha-cyanogroup on the 3-phenoxybenzyl alcohol and is a type II pyrethroid. The SS stereoisomer is the most biologically active and is sold as esfenvalerate.

For more General Manufacturing Information (Complete) data for FENVALERATE (9 total), please visit the HSDB record page.