Allethrins

Agrochemicals -> Pesticide active substances

Active substance -> EU Pesticides database: Not approved

Pesticides -> Pyrethrins/Pyrethroids

Pesticide

Pesticide (Allethrin) -> USDA PDB

4.78

4.78

Relative density (water = 1): 1.01

Relative density (water = 1): 1.01

Solubility in water: none

Solubility in water: none

GREATER THAN 140 °F

130 °C

165-170

BP: 140 °C at 0.1 mm Hg. Vaporizes without decomposition when heated at 150 °C.

at 0.013kPa: 140 °C

Pale, yellow, oily liquid. Specific gravity, d 20/4: 1.005-1.015. Vapor pressure: 1.2X10-4 mm Hg at 30 °C. Miscible with most organic solvents at 20-25 °C. /Pynamin forte/

Vapor pressure, Pa at 20 °C:

Allethrin appears as a clear amber-colored viscous liquid. Insoluble and denser than water. Toxic by ingestion, inhalation, and skin absorption. A synthetic household insecticide that kills flies, mosquitoes, garden insects, etc.

D-trans-allethrin is a clear to amber viscous liquid. A synthetic insecticide structurally similar to pyrethrin.

Yellow liquid with a mild aromatic odor; [EXTOXNET]

PALE YELLOW VISCOUS LIQUID.

VISCOUS LIQUID.

Warning

H302+H332 (20.4%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oral; acute toxicity, inhalation]

P261, P264, P270, P271, P273, P301+P317, P304+P340, P317, P330, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 142 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H302 (48.5%): Harmful if swallowed [Warning Acute toxicity, oral]

Hazard Traits - Developmental Toxicity; Endocrine Toxicity; Reproductive Toxicity

Allethrins is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

2002/2076

Allethrin: HSNO Approval: HSR003289 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.)

IMAP assessments - Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl ester, [1R-[1.alpha.(S*),3.beta.]]-: Environment tier I assessment

IMAP assessments - Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl ester: Environment tier I assessment

Poison

Class 9

Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

Combustible. Liquid formulations containing organic solvents may be flammable.

Combustible. Liquid formulations containing organic solvents may be flammable.

Slight fire hazard.

Combustible

Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

Slightly toxic after skin absorption or ingestion with an oral LD50 of 1100 mg/kg in male rats; Liver injury is detected in animal experiments with high oral doses. [EXTOXNET] See Bioallethrin, RN: 584-79-2, with LCLo (rats) = 13,800 mg/m3/4H and a vapor pressure = 0.0000012 mm Hg. [ChemIDplus] 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]

Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters

Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters

Symbol: Xn, N; R: 20/22-50/53; S: (2)-36-60-61; Note: C

Symbol: Xn, N; R: 20/22-50/53; S: (2)-36-60-61; Note: C

UN Hazard Class: 6.1; UN Pack Group: III

UN Hazard Class: 6.1; UN Pack Group: III

USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision for Allethrins 167pp. EPA 738-R-07-001 (June 2007). This document provides a thorough review of the scientific data underlying allethrin isomers' registration and fulfills the EPA's requirement to determine whether pesticides containing the active ingredients are eligible for reregistration before calling in data on products.

Papadopoulou-Mourkidou E; Residue Rev 89: 179-208 (1983). A review with many references on analysis of allethrin & other pyrethroid insecticides.

WHO; Environmental Health Criteria 87: Allethrins - Allethrin, d-Allethrin, Bioallethrin, S-Bioallethrin (1989). 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.

The Agency has completed its assessment of the human health and ecological risks associated with the use of pesticide products containing the allethrins. The Agency has determined that allethrin-containing products are eligible for reregistration provided that label amendments are made as outlined in Chapter V. ... Based on its evaluation of the allethrins, the Agency has determined that products containing allethrins, unless labeled and used as specified in this document, would present risks inconsistent with FIFRA. Accordingly, should a registrant fail to implement any of the risk mitigation measures identified in this document, the Agency may take regulatory action to address the risk concerns from the use of the allethrins. If all changes outlined in this document are incorporated into the product labels, then all current risks for the allethrins will be adequately mitigated for the purposes of this determination under FIFRA.

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 future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Allethrin is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA, as amended in 1988. Case No: 0437; Pesticide type: insecticide; Registration Standard Date: 03/24/88; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): Allethrin; AI Status: The active ingredient is no longer contained in any registered products. Thus, we characterize it as "cancelled."

Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

Use powder, AFFF, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

Use powder, AFFF, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

Fresh air, rest.

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.

Fresh air, rest. Refer for medical attention.

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

Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

Provision to contain effluent from fire extinguishing. Separated from food and feedstuffs. Keep in a well-ventilated room.

Provision to contain effluent from fire extinguishing. Separated from food and feedstuffs. Keep in a well-ventilated room.

Use carbon dioxide, foam, or dry chemical /on fires involving pyrethroids/. /Pyrethrum/

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

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/

Store in a closed drum in a cool, dry place.

Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

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.

This pesticide is toxic to fish and aquatic invertebrates. Do not discharge effluent containing this product into lakes, streams, ponds, estuaries, oceans, or other waters unless in accordance with the requirements of a National Pollutant Discharge Eliminations System (NPDES) permit and the permitting authority has been notified in writing prior to discharge. Do not discharge effluent containing this product to sewer systems without previously notifying the local sewage treatment plant authority. For guidance, contact your State Water Board or Regional Office of the Environmental Protection Agency

Do not apply directly to water, or to areas where surface water is present, or to inter-tidal areas below the mean high water mark. Do not contaminate water when cleaning equipment or disposing of equipment washwater or rinsate.

It could be ... buried in noncrop land away from water. In each of these cases it would be better to mix the product with lime. Incineration would be an effective disposal procedure where permitted. If an efficient incinerator is not available, the product should be mixed with large amt of combustible material. Recommendable methods: Incineration & landfill.

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

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

Follow manufacturer's instructions for cleaning/maintaining PPE. If no such instructions for washables exist, use detergent and hot water. Keep and wash PPE separately from other laundry.

Discard clothing or other absorbent materials that have been drenched or heavily contaminated with this product's concentrate. Do not reuse them.

Users should wash hands before eating, drinking, chewing gum, using tobacco, or using the toilet.

Users should remove clothing/ PPE immediately if pesticide gets inside, then wash thoroughly and put on clean clothing.

For more Preventive Measures (Complete) data for ALLETHRINS (11 total), please visit the HSDB record page.

Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

Wear safety goggles.

Wear safety goggles.

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)

INSECTICIDAL ACTIVITIES OF ALLETHRIN ARE ENHANCED BY PYRETHRIN SYNERGISTS SUCH AS PIPERONYL BUTOXIDE OR BIS(2,3,3,3-TETRACHLOROPROPYL) ETHER, OR N-(2-ETHYLHEXYL)-8,9,10-TRINORBORN-5-ENE-2,3-DICARBOXIMIDE.

Diazepam delayed the onset of action of deltamethrin, but not of allethrin, in both the mouse and cockroach.

... The ability of agents which alter neurotransmission to prevent or potentiate the effect of convulsive doses of technical grade (15.5% cis, 84.5% trans) allethrin was examined. Intraperitoneal pretreatment with drugs which block noradrenergic receptors or norepinephrine synthesis such as pentobarbital, chlorpromazine, phentolamine, and reserpine depressed the tremor induced by allethrin. The inhibitory effect of reserpine was reversed by phenylephrine. Both the serotonergic blocker, methysergide and the serotonin depletor, p-chlorophenylalanine potentiated the effect of allethrin. Thus, allethrin produces its neurotoxic responses in mice by acting on the brain and spinal levels. Furthermore, adrenergic excitatory and serotonergic inhibitory mechanisms may be involved in the neural pathway through which the allethrin-induced tremor is evoked.

Synergists for pyrethroid /insecticidal activity/ may include the following: sesamin, sesamolin, piperonyl-butoxide, Tropital, Sesamex, propyl-isomer, satroxan, sulfoxide, piperonylcyclonene, MGK 264, Synepirin 500, and SKF 5254. /Pyrethroids, data derived from table/

For more Interactions (Complete) data for ALLETHRINS (8 total), please visit the HSDB record page.

As for every type I pyrethroid, allethrin 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 can also occur after dermal exposure to allethrin. It is likely to be a human carcinogen by the oral route. (L857)

LD50 /Anas platyrhynchos/ (Mallard duck, male, 3-4 months old) oral <2000 mg/kg

LC50; Species: Gammarus lacustris (Scud, age 2 months); Conditions: freshwater, static, 21.1 °C, pH 7.1, alkalinity 30 mg/L CaCO3; Concentration: 38 ug/L for 24 hr (95% confidence interval: 30-49 ug/L) /formulated product/

LC50; Species: Gammarus lacustris (Scud, age 2 months); Conditions: freshwater, static, 21.1 °C, pH 7.1, alkalinity 30 mg/L CaCO3; Concentration: 20 ug/L for 48 hr (95% confidence interval: 14-28 ug/L) /formulated product/

LC50; Species: Gammarus lacustris (Scud, age 2 months); Conditions: freshwater, static, 21.1 °C, pH 7.1, alkalinity 30 mg/L CaCO3; Concentration: 11 ug/L for 96 hr (95% confidence interval: 8-15 ug/L) /formulated product/

For more Ecotoxicity Values (Complete) data for ALLETHRINS (136 total), please visit the HSDB record page.

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

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

Inhalation (L858) ; oral (L858) ; dermal (L858) ; eye contact (L858).

IDENTIFICATION AND USE: Allethrins is a clear to amber colored viscous liquid which is miscible with most organic solvents. It is completely soluble with chloroform, ethyl acetate, toluene and dichloromethane and it is stable under normal conditions and use. Allethrins are a mixture of isomers and the product is used as an insecticide. HUMAN EXPOSURE and TOXICITY: Despite their extensive world wide use, there are relatively few reports of human pyrethroid poisoning. In individuals exposed to pyrethroids, dermal; application to the skin has resulted in paresthesia and may be stimulated by increases in heat, sunlight, scratching, humidity, or the application of water. Pyrethroid ingestion can cause sore throat, nausea, vomiting and abdominal pain. Dizziness and fatigue are common, and palpitations, chest tightness and blurred vision have also occurred. Contact allergy to pyrethroids has also been noted. Upper respiratory tract symptoms can include rhinitis, sneezing, scratchy throat, oral mucosa and laryngeal edema; lower respiratory symptoms can include cough, shortness of breath, wheezing and chest pain and an asthma like condition. S-bioallethrin caused an inhibition of human lymphocyte proliferation in 72 hr culture in a concentration dependent manner. Pyrethroids are not cholinesterase inhibitors. Pyrethrins are irritating to the eye. Skin rash on moist areas of the body have been observed. Employees with chronic respiratory and skin diseases may be at increated risk to pyrethrum exposure. Persons sensitive to rag weed may show sensitiziation to pyrethroids. Individuals may be exposed to allethrins during pesticide applications and inhalation exposures may result when consumers use space spray products, patio foggers, mosquito coils and fly mats. ANIMAL STUDIES: When undiluted and diluted technical allethrin in olive oil were applied to the dorsal skin of rabbits. No differences were noted between treated and control animals. Solutions of different concentrations of allethrin applied to the eyes of rabbits produced eyelid closure, slight conjunctival hyperemia and lacrimation. Allethrin solution applied topically to the backs of male guinea pigs and then rechallenged showed a sporadic pink color on the site of application. Histological examination revealed slight lymphocytic and monocytic infiltration of the dermis in allethrin treated animals. Bioallethrin did not produce any irritation, but produced slight sensitization in guinea pigs. It was also a slight irritant to the skin of rabbits. Rats exposed to allethrin mosquito repellant had significant increases in weights livers and adrenal gland in males, brain and thyroid in females. Changes in liver enzymes were also noted. Allethrin administered in the diets to male Wistar rats a decrease in body weight gain, and increases in liver and kidney weights were observed. Bile ductile proliferation was also noted. ICR mice exposed to a mist of d-allethrin or S-bioallethrin. No significant effects were noted in pregnant ICR mice exposed to d-allethrin or S-Bioallethrin on gestation days 7-12. Allethrin given allethrin by intubation to pregnant albino rabbits there was no evidence of compound related effects. Allethrin was strongly positive at low doses. The mutagenic potential of allethrin was examined in a wide range of tests including in vitro/in vivo gene mutation, DNA damage and repair, and in vitro/in vivo structural aberration the results of the tests were negative. Allethrin was found to be mutagenic in Salmonella typhimurium reversion assay systems in TA 100, TA 104 and TA 97 strains and required metabolic activation. Allethrin did not show evidence of treatment related effects on micronuclei frequency in mouse bone marrow smears. Fish are sensitive to allethrin toxicity when they are exposed to this insecticide in elevated water temperatures/ In plants allethrin is not phototoxic.

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)

/AQUATIC SPECIES/ The biological activity in fish is affected by temperature. The toxicity of 1R or (+)- trans-allethrin for the bluegill was about 1.5 times higher at 22 °C than at 12 °C ... . Water hardness and pH did not have any significant effects on the toxicity for fish ... . Allethrin is generally less toxic in arthropods than in fish, with the exception of the stonefly, which is the most susceptible insect ... .

/AQUATIC SPECIES/ A search of the EIIS (Environmental Incident Information System) database for ecological incidents (run on Dec. 2, 2005) identified a total of one ecological incident involving an allethrin (allethrin; PC Code: 004001). The allethrin involved in the incident is no longer registered (i.e., all of its uses have been cancelled). The incident occurred on a fish farm in Ventura County, CA, in Dec. 2000, and it involved the death of 13,000 rainbow trout. The reported cause of the incident was an act of sabotage (i.e., it was the result of intentional misuse). The certainty index was reported as highly probable and it was reported that, there seemed to be no doubt about the cause of the fish kill, although no tissue or water samples were reported.

/AQUATIC SPECIES/ The toxicity of natural pyrethrins and five pyrethroids was determined with coho salmon (Oncorhynchus kisutch), steelhead trout (Salmo gairdneri), fathead minnow (Pimephales promelas), channel catfish (Icatlurus punctatus), bluegill (Lepomis macrochirus), and yellow perch (Perca flavescens). The 96-hour LC50s in static tests at 12 degrees C ranged from 24.6 to 114 ug/L of natural pyrethrins and from 0.110 to 1,140 ug/L of pyrethroids. Two pyrethroids, RU-11679 and SBP-1382 (R), were over 10 times more toxic than pyrethrum extract in the flow-through tests. Coldwater species of fish were more sensitive than warmwater species to all the compunds. Temperature (12-22 degrees C) influences the toxicity of natural pyrethrin and the pyrethroids. The natural pyrethrin was more toxic to fish in pH 6.5 than in pH 9.5 water, but the toxicity of pyrethroids was not influenced in the pH range. The two most toxic pyrethroids, RU-11679 and SBP-1382, were deactivated more rapidly in water solutions than natural pyrethrins, S-bioallethrin, dimethrin, and d-trans allethrin. /S-bioallethrin, d-trans allethrin, other pyrethrins and pyrethroids/

/PLANTS/ Non-phytotoxic

Cough.

Redness.

Redness.

Cough.

Redness.

Redness.

Chemical: ALLETHRIN

Chemical: DOWICIL 75

Chemical: D-TRANS ALLETHRIN

The Agency has completed its assessment of the human health and ecological risks associated with the use of pesticide products containing the allethrins. The Agency has determined that allethrin-containing products are eligible for reregistration provided that label amendments are made as outlined in Chapter V. ... Based on its evaluation of the allethrins, the Agency has determined that products containing allethrins, unless labeled and used as specified in this document, would present risks inconsistent with FIFRA. Accordingly, should a registrant fail to implement any of the risk mitigation measures identified in this document, the Agency may take regulatory action to address the risk concerns from the use of the allethrins. If all changes outlined in this document are incorporated into the product labels, then all current risks for the allethrins will be adequately mitigated for the purposes of this determination under FIFRA.

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 future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Allethrin is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA, as amended in 1988. Case No: 0437; Pesticide type: insecticide; Registration Standard Date: 03/24/88; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): Allethrin; AI Status: The active ingredient is no longer contained in any registered products. Thus, we characterize it as "cancelled."

Bioallethrin, like other pyrethroids, binds to voltage gated sodium channels in their closed state and modifies the gating kinetics. Channel opening appears to increase affinity of the channel for pyrethroids like bioallethrin. Once bound pyrethroids slow both the opening and closing of the sodium channel resulting in a need for stronger excitatory potentials to produce an action potential and a delay in repolarization. The these changes make the neuron more susceptible to large action potentials and repeated firing by both increasing the initial threshold and reducing the input needed for after-potentials. When repeated firing does occur, the nerve terminal will release more neurotransmitter which can produce muscle paralysis through tetanus. This paralysis stops the breathing of lice and scabies parasites resulting in death. Some pyrethroids act on calcium channels to increase intracelllular calcium. Bioallethrin produces a very small increase in intracellular calcium in mouse neocortical neurons by acting on N-type calcium channels but the effect returns to baseline within 2 min. In contrast bioallethrin has been found to block L T, and P/Q-types of voltage gated calcium channels in human embryonic kidney cell cultures. Bioallethrin has been found to inhibit both sodium-calcium dependent and magnesium-calcium ATP hydrolysis in insects although it, along with other type I pyrethroids, has a greater effect on sodium-calcium dependent hydrolysis. Bioallethrin may stimulate phosphoinositol breakdown in synaptoneuromes as other type I pyrethroids have been observed to do so. Other type I pyrethoids have also been found to bind to kainate receptors.

Mode of Action: The allethrins are a type I pyrethroid (i.e., lacking a cyano group at the alpha carbon position of the alcohol moiety). The allethrins are axonic poisons that block the closing of the sodium gates in the nerves, and, thus, prolong the return of the membrane potential to its resting state leading to hyperactivity of the nervous system which can result in paralysis and/or death.

The mechanisms by which pyrethroids alone are toxic are complex and become more complicated when they are co-formulated with either piperonyl butoxide or an organophosphorus insecticide, or both, as these compounds inhibit pyrethroid metabolism. The main effects of pyrethroids are on sodium and chloride channels. Pyrethroids modify the gating characteristics of voltage-sensitive sodium channels to delay their closure. A protracted sodium influx (referred to as a sodium 'tail current') ensues which, if it is sufficiently large and/or long, lowers the action potential threshold and causes repetitive firing; this may be the mechanism causing paraesthesiae. At high pyrethroid concentrations, the sodium tail current may be sufficiently great to prevent further action potential generation and 'conduction block' ensues. Only low pyrethroid concentrations are necessary to modify sensory neurone function.

The interactions of natural pyrethrins and 9 pyrethroids with the nicotinic acetylcholine (ACh) receptor/channel complex of Torpedo electronic organ membranes were studied. None reduced (3)H-ACh binding to the receptor sites, but all inhibited (3)H-labeled perhydrohistrionicotoxin binding to the channel sites in presence of carbamylcholine. Allethrin inhibited binding noncompetitively, but (3)H-labeled imipramine binding competitively, suggesting that allethrin binds to the receptor's channel sites that bind imipramine. The pyrethroids were divided into 2 types according to their action: type A, which included allethrin, was more potent in inhibiting (3)H-H12-HTX binding and acted more rapidly. Type B, which included permethrin, was less potent and their potency increased slowly with time. The high affinities that several pyrethroids have for this nicotinic ACh receptor suggest that pyrethroids may have a synaptic site of action in addition to their well known effects on the axonal channels.

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 micromolar tetrodotoxin, a blocker of voltage dependent sodium channels, partially inhibited deltamethrin (85%) and fenvalerate (60%) responses but not allethrin or resmethrin. Fenvalerate induced stimulation of phosphoinositide breakdown 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 deltamethrin were not different from allethrin alone. Ten micromolar 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.

For more Mechanism of Action (Complete) data for ALLETHRINS (13 total), please visit the HSDB record page.

Metabolism of bioallethrin in both rats and humans is considered to be virtually 100% oxidative. This is because bioallethrin is very resistant to hydrolysis of its ester group although a negligible amount of hydrolysis may occur. In humans bioallethrin is metabolized primarily by CYP2C19 with some metabolism by CYP2C8, CYP3A4, and CYP2C9*2. The metabolites produced include primary alcohols via allylic oxidation near the cyclopropane group and subsequent oxidation to carboxylic acid, formation of a primary alcohol via oxidation of a methyl group to located on the cyclopropane portion of the molecule, formation of a primary alcohol via allylic oxidation near the 5-membered ring or formation of an epoxide at this location and subsequent hydrolysis to a diol. In rats bioallethrin has been found to be metabolized mainly by CYP2C6, CYP2C11, and CYP3A1 with some contribution from CYP1A1, CYP2A1 and CYP3A2. Rats appear to metabolize bioallethrin at about 15 times the rate of humans.

AFTER ADMINISTRATION OF LABELED ALLETHRIN TO MALE RATS, THE MAJOR METABOLITES FOUND WERE ALCOHOL-ACIDS. FROM NMR AND MASS SPECTRA A THIRD METABOLITE WAS IDENTIFIED AS ALLETHRIN WITH ONE CYCLOPROPANE METHYL HYDROXYLATED AND OXIDATION OF THE TRANSMETHYL TO A CARBOXYL GROUP. ...

/IN STUDYING THE METABOLISM OF ALLETHRIN IN HOUSEFLIES, IT WAS FOUND THAT IN/ ALLETHRIN LABELED IN THE KETOCYCLOPENTENYL PORTION OF THE MOLECULE, A METABOLITE THAT BEHAVED AS KETOCYCLOPENTENOL WAS ISOLATED BY PAPER CHROMATOGRAPHY. ... INVESTIGATORS USING ALLETHRIN LABELED IN CHRYSANTHEMUMIC ACID PORTION OF MOLECULE WERE ABLE TO DETECT ONLY TRACES OF ACID IN HOUSEFLY HOMOGENATES OR EXCRETA. ... ONLY TRACES OF UNCHANGED ALLETHRIN WERE RECOVERABLE AND THE BULK OF THE RECOVERED MATERIAL MUST BE A DERIVATIVE OF THE INTACT ESTER OR OF THE ACID.

Allethrin is oxidized not only at the chrysanthemate isobutenyl moiety to the corresponding primary alcohol but also at the allyl group to 1'-hydroxyprop-2'-enyl and 2',3'-dihydroxy-propyl derivatives, or at a methyl group on the cyclopropyl moiety to a hydroxy derivative. Allethrin is also converted to chrysanthemum dicarboxylic acid and allethrolone.

When allethrin was applied topically to houseflies, chromatography indicated the presence of allethrone and chrysanthemic acid in addition to allethrin and three unidentified compounds.

For more Metabolism/Metabolites (Complete) data for ALLETHRINS (10 total), please visit the HSDB record page.

Pyrethroids are excreted in both the feces and urine but values specific to bioallethrin are not available.

WHEN RADIOACTIVE PYRETHROID IS ADMIN ORALLY TO MAMMALS, IT IS ABSORBED FROM INTESTINAL TRACT OF THE ANIMALS & DISTRIBUTED IN EVERY TISSUE EXAMINED. EXCRETION OF RADIOACTIVITY IN RATS ADMIN TRANS-ISOMER: DOSAGE: 500 MG/KG; INTERVAL 20 DAYS; URINE 36%; FECES 64%; TOTAL 100%. /PYRETHROIDS/

Pyrethrins are absorbed through intact skin when applied topically. When animals were exposed to aerosols of pyrethrins with piperonyl butoxide being released into the air, little or none of the combination was systemically absorbed. /Pyrethrins/

Although limited absorption may account for the low toxicity of some pyrethroids, rapid biodegradation by mammalian liver enzymes (ester hydrolysis and oxidation) is probably the major factor responsible. Most pyrethroid metabolites are promptly excreted, at least in part, by the kidney. /Pyrethroids/

There were no major /metabolic/ differences between sexes, between low and high dose groups, nor between single-dose groups and repeated dose groups. The majority of radioactivity was eliminated within 3 days. Urinary elimination ranged from approximately 25 - 50% and fecal elimination ranged from 50 - 70%. There was no bioaccumulation of residue in tissues. ... /d-trans-Allethrin/

When allethrin labelled with (14)C in the acid moiety or with (3)H in the alcohol moiety was administered orally to male Sprague Dawley rats at levels ranging from 1 to 5 mg/kg body weight, the radiocarbon and tritium from the acid- and alcohol-labellings were eliminated in the urine (30% and 20.7%, respectively) and feces (29% and 27%, respectively) in 48 hr. ... Most of the metabolites excreted in the urine were ester-form metabolites together with two hydrolyzed products, chrysanthemum dicarboxylic acid (CDCA) and allethrolone. ...

Used in homes and gardens to kill flies and mosquitoes; The d-trans isomer is a more potent insecticide used to control animal parasites. Sold as mosquito coils, mats, oil formulations, and sprays; [EXTOXNET]

Farming (Pesticides) [Category: Industry]

For Allethrin /(the product that is a mixture)/ (USEPA/OPP Pesticide Code: 004001) 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./ /Allethrin/

For bioallethrin (USEPA/OPP Pesticide Code: 004003) 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./ /Bioallethrin/

For S-bioallethrin (USEPA/OPP Pesticide Code: 004004) 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./ /S-Bioallethrin/

For d-trans-allethrin (USEPA/OPP Pesticide Code: 004003) 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./ /d-trans-Allethrin/

Allethrin is prepared by the esterification of (1RS, 3RS or cis, trans)-2,2-dimethyl-3-(2,2-dimethylvinyl) cyclopropanecarboxylic acid or chrysanthemic acid with (1RS)-3- allyl-2-methyl-4-oxocyclopent-2-ene-1-ol or allethrolone ... .

2-Allyl-3-methyl-2-cyclopenten-4-ol-1-one (allethrone) and chrysanthemum monocarboxlic anhydride in dibutyl ether at 150-175 °C for 3-6 hr are reacted. Upon cooling, the solution is diluted, the chrysanthemum moncarboxlic acid byproduct is removed by saponification, the organic phase is washed with water, and the solvent evaporated.

USEPA/OPP Pesticide Code: 004001; Trade Names: ENT 16275, ENT 17510, FDA 1446, FMC 249, NIA 249, Pyresin, Pynamin, Exthrin.

Aerosol dispenser; emulsifiable concentrate; dispersible powder; wettable powder; Coil

d-Allethrin is greater than/equal to 95% (1R)-isomers and greater than/equal to 75% trans isomers

Grades: 90% technical (approx 90% pure, with 10% of isomers or related cmpd); 20% technical, 2.5% technical.

For more Formulations/Preparations (Complete) data for ALLETHRINS (268 total), please visit the HSDB record page.

Information on 9 consumer products that contain d-trans-Allethrin in the following categories is provided:

Information on 21 consumer products that contain d-trans Allethrin in the following categories is provided:

Information on 5 consumer products that contain d-cis,trans-Allethrin in the following categories is provided:

INSECTICIDES

ANTIMICROBIAL AGENTS

INSECTICIDES

Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)-, 2-methyl-4-oxo-3-(2-propen-1-yl)-2-cyclopenten-1-yl ester: ACTIVE

The WHO Recommended Classification of Pesticides by Hazard identifies Allethrin (technical grade) as Class III: slightly hazardous; Main Use: insecticide.

The first pyrethroid pesticide, allethrin, was identified in 1949. Allethrin and other pyrethroids with a basic cyclopropane carboxylic ester structure are type I pyrethroids. ... All pyrethroids can exist as at least four stereoisomers, each with different biological activities. They are marketed as racemic mixtures or as single isomers. In commercial formulations, the activity of pyrethroids is usually enhanced by the addition of a synergist such as piperonyl butoxide, which inhibits metabolic degradation of the active ingredient.

ALLETHRIN IS ALLYL HOMOLOG OF CINERIN I, WHICH IS ONE OF THE CONSTITUENTS OF PYRETHRUM, OLDEST KNOWN INSECTICIDE.

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

For more General Manufacturing Information (Complete) data for ALLETHRINS (11 total), please visit the HSDB record page.