Allethrin

302.41

302.41

209-542-4

0X03II877M

0212|0213|0227|0228

11782

2902|3352

DTXSID8035180

29183000

43.4

4.7

Clear amber Viscous Liquid

1.01 g/cm³ @ Temp: 20 °C

4 °C

140 °C @ Press: 0.1 Torr

66 °C

1.515

2 mg l -1

0-6°C

Vapour pressure, Pa at 25°C:

Oral-rat LD50: 425 mg/kg; Oral-Mouse LD50: 330 mg/kg

Flammable; burning produces irritating fumes

Henry's Law constant = 1.04X10-7 atm-cu m/mol at 21 °C (est) /Allethrin I/

Allethrins are sometimes classified as type I pyrethroids, since they lack an alpha-cyano substituent.|Clear, amber-colored, viscous liquid. Miscible with most organic solvents at 20-25 °C /Allethrin I/|Clear, pale yellow liquid. MW: 302.4. Soluble in alcohol, petroleum ether, kerosene, carbon tetrachloride, ethylene dichloride, nitromethane. Index of refraction: 1.5040 at 20 °C/D; 1.5023 at 30 °C/D. BP: 140 °C at 0.1 mm Hg. Vaporizes without decomposition when heated at 150 °C. /Allethrin I/|BP: 281.5 °C at 760 mm Hg. Density: 1.01 at 20 °C. Solubility in water: 4.6 mg/L at 25 °C. Solubility in hexane 0.655 g/mL, methanol 72.0 mL/mL (both 20 °C). VP: 1.2X10-6 mm Hg at 21 °C /Allethrin I/|log Kow = 4.78 /Allethrin I/|Conversion factors Air (25 °C): 1 mg/cu m = 0.081 ppm|Pale yellow liquid /Technical grade Allethrin I/|/TECHNICAL & COMMERCIAL ALLETHRIN/ ... CHEMICAL PROPERTIES ARE AKIN TO THOSE OF PYRETHRINS ... BUT HAVING MORE STABLE SIDE CHAIN IT IS ... MORE PERSISTENT. ...|VP: 2 mPa at 25 °C; water solubility: 4.6 mg/L /Bioallethrin/|Mol. wt. 302.4 MF: C19H26O3. Orange-yellow viscous liquid. The material in D-Trans is an amber viscous liquid. MP: Not applicable; no crystallization observed at -40 °C. BP: Bioallethrin 165-170 °C/0.15 mmHg. VP: 43.9 mPa (25 °C) log Kow = 4.68 (25 °C); Henry's Law constant: 2.89 Pa cu m/mol (calc). Specific gravity/density: 1.012 at 20 °C. Solubility: in water, 4.6 mg/L (25 °C). Completely miscible with chloroform, ethyl acetate, toluene and dichloromethane (20 °C). Specific rotation:-18.5 to -22.5deg at 20 °C (50 g/L toluene). Stability: Degraded by UV light. In aqueous solution, DT50 1410.7 days (pH 5), 547.3 days (pH 7), 4.3 days (pH 9). /Bioallethrin/|Amber colored viscous liquid, slight aromatic odor. Specific gravity of D-trans concn 90% is typically 0.997 at 20 °C. Stable under normal conditions of storage and use. Avoid highly alkaline or acidic situations. Miscible with acetone, benzene, ethanol, hexane, methylene chloride, and refined kerosene. /Bioallethrin/|Composition Esbiol (OMS 3046) contains approximately 95% m/m total isomers, of which approximately 90% is esdepallethrine. Esbiothrin (OMS 3045) contains approximately 93% m/m total isomers, of which approximately72% is esdepallethrine, the remainder being essentially the (R)-cyclopentenyl isomer, with <3% cis- isomers. MW: 302.4; MF: C19H26O3. Form: Orange-yellow viscous liquid. MP: Not applicable; no crystallisation observed at -40 °C. BP: 165-170 °C/0.15 mmHg (OMS 3046); 163-170 °C/0.15 mmHg (OMS 3045). VP: 44 mPa (25 °C). Specific gravity/density: 1.010 at 20 °C. Solubility: Completely miscible with 100% ethanol, acetone, dichloromethane, di-isopropyl ether, toluene, n-hexane, chloroform, ethyl acetate, methanol, n-octanol, and petroleum solvent (20 °C ). Stability: Degraded by UV light. Specific rotation: OMS 3046: -47.5 deg to -55 deg at 20 °C/D (50 g/L toluene); OMS 3045: approximately -37 deg at 20 °C/D (50 g/L toluene) /Esbiol/|Yellow-colored viscous liquid with slight aromatic odor. Specific gravity of esbiol concn 90% is typically 0.98 at 20 °C. Stable under normal conditions of storage use use. Avoid highly acidic of alkaline situations. Miscible with acetone, benzene, ethanol, hexane, refined kerosene, isoparaffinic solvents, and other organic solvents. Insoluble in water. /S-Bioallethrin/|Composition: d-Allethrin is approximately 95% (1R)- isomers and approximately 75% trans isomers; see also bioallethrin. MW: 302.4. MF: C19H26O3. Form Tech. is a pale yellow liquid. BP: 281.5 °C/760 mmHg. VP: 0.16 mPa (21 °C). log Kow = 4.96 (room temperature). Specific gravity/density 1.01 (20 °C). Solubility: Practically insoluble in water. In hexane 0.655 g/mL, methanol 72.0 mL/mL (both 20 °C). Stability: Decomposed by UV light. Hydrolysed in alkaline media. /Pynamin forte/[Tomlin CDS, ed. Allethrin|Hydroxyl radical reaction rate constant = 2.25X10-10 cu cm/molec-sec at 25 °C (est) /Allethrin I/

Insoluble in water.

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

ALLETHRIN is an ester and ketone. 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. Ketones are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4.

III

6.1(b)

UN 3082

3

20/22-50/53-40

36-60-61-36/37-24/25-23

GZ1925000

Xn;N,N,Xn

Ventilated, low temperature and dry; stored separately from food materials in warehouse

Pyrethrins /are/ stable for long periods in water-based aerosols where emulsifiers give neutral water systems. /Pyrethrins/

P273-P501

H302-H332-H410

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.

Incompatible with alkalies...|Incompatibility: Strong oxidizers. /Pyrethrins/|... Incompatible with lime & ordinary soaps because acids & alkalies speed up processes of hydrolysis. /Pyrethrins/

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.

Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Containers may explode when heated. Runoff may pollute waterways. (ERG, 2016)|Combustible. Liquid formulations containing organic solvents may be flammable.|Combustible. Liquid formulations containing organic solvents may be flammable. Above 65.6 °C explosive vapour/air mixtures may be formed.

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P273, P301+P312, P304+P312, P304+P340, P312, P330, P391, and P501|Aggregated GHS information provided by 270 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Aggregated GHS information provided by 79 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302 (79.77%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, P391, and P501|Aggregated GHS information provided by 257 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302: Harmful if swallowed [Warning Acute toxicity, oral]|H227: Combustible liquid [Warning Flammable liquids]|P210, P260, P261, P264, P270, P271, P272, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P309+P311, P312, P314, P321, P330, P333+P313, P337+P313, P363, P370+P378, P391, P403+P233, P403+P235, P405, and P501

Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Cover with plastic sheet to prevent spreading. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)

Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. (ERG, 2016)|End-Use Products Intended for Occupational Use (WPS and Non-WPS): Applicators and other handlers must wear: long-sleeved shirt and long pants, and shoes and socks|For All Allethrin Uses EXCEPT for Use in Coils and Mats: Applicators using high-pressure handwands in an enclosed area must wear a NIOSH-approved dust mist filtering respirator with MSHA/NIOSH approval number prefix TC-21C or a NIOSH-approved respirator with any N, R, P, or HE filter. ... Applicators using hand-held foggers in an enclosed area must wear a full-face, or helmet/hood-style NIOSHapproved respirator with: -- a dust/mist filtering cartridge (MSHA/NIOSH approval number prefix TC-21C), or -- a canister approved for pesticides (MSHA/NIOSH approval number prefix TC-14G), or -- a cartridge or canister with any N,R, P or HE filter.*Instruction to Registrant: Drop the N type prefilter from the respirator statement, if the pesticide product contains or is used with oil.|PPE required for early entry to treated areas that is permitted under the Worker Protection Standard and that involves contact with anything that has been treated, such as plants, soil or water, is coveralls, shoes and socks, and chemical-resistant gloves made of any waterproof material.

Slight fire hazard.|Combustible

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/

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.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Immediately irritating to the eye. /Pyrethrins/|The chief effect from exposure ... is skin rash particularly on moist areas of the skin. ... May irritate the eyes.

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.

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

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

The substance is irritating to the eyes, skin and respiratory tract.

NO open flames.|NO open flames. Above 65.6 °C use a closed system and ventilation.

PREVENT GENERATION OF MISTS!

Use ventilation, local exhaust or breathing protection.

Protective gloves.

Wear safety goggles.

highly toxic

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.

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.

LD50 Rat male oral 1100 mg/kg|LD50 Rat female oral 685 mg/kg|LD50 Rat (male) oral 709 mg/kg /d-trans-Allethrin/ /From table/|LD50 Rat (female) oral 1042 mg/kg /d-trans-Allethrin/ /From table/|For more Non-Human Toxicity Values (Complete) data for ALLETHRINS (40 total), please visit the HSDB record page.

/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

The allergenic properties of pyrethroids /with early pyrethrum preparations/ are marked in comparison with other pesticides. Many cases of contact dermatitis and respiratory allergy have been reported. Persons sensitive to ragweed pollen are particularly prone to such reactions. Preparations containing synthetic pyrethroids are less likely to cause allergic reactions than are the preparations made from pyrethrum powder. /Pyrethroids/|Chronic respiratory disease: In persons with chronic respiratory disease, especially asthma, the inhalation of /pyrethroids/ might cause exacerbation of symptoms due to its sensitizing properities. Skin disease: /Pyrethroids/ can cause dermatitis which may be allergic in nature. Persons with pre-existing skin disorders may be more susceptible to the effects of this agent. ... /Pyrethroids/

The allethrins production may result in their release to the environment through various waste streams(SRC). Their use to control flying and crawling insects in a number of commercial, horticultural and residential applications(1) will result in their direct release to the environment(SRC). The allethrin series of pyrethroid insecticides includes bioallethrin (PC code 004003), esbiol (004004), esbiothrin (004007, formerly 004003/004004), and pynamin forte (004005)(1).

... allethrin is among the least persistent of all pyrethroids and is less persistent than cyallethrins, cyfluthrin, cyhalothrin, deltamethrin, fenvalerate, tefluthrin, and tralomethrin. /Allethrin/

ALLETHRIN DECOMP READILY WHEN SUBJECTED TO IRRADIATION OF SUNLIGHT OR SUN LAMP TO YIELD 11-15 PRODUCTS. PHOTOCHEMICAL CHANGES OCCURRED IN ACID MOIETY AND INVOLVED STEP-WISE OXIDN OF THE TRANS-METHYL GROUP TO THE ALCOHOL, ALDEHYDE, CARBOXYL DERIVATIVES AND OXIDATION OF THE DOUBLE BOND TO A KETO FUNCTION WITH SUBSEQUENT RUPTURE TO FORM TRANS-CARBONIC ACID ESTERS. OTHER ATTACKS EFFECTED AT LEAST 6 ADDITIONAL CHANGES OF ACID MOIETY. ALCOHOL MOIETY UNDERWENT PHOTOCHEMICAL ALTERATIONS ALSO, BUT THE REACTIONS INVOLVED WERE NOT KNOWN.|Photodecomposition of each of the four pyrethroids gave rise to 12-16 products but little ester hydrolysis. Trans- & meso-cis-caronic acids were identified by co-chromatography.|Allethrin is among the least persistent of all pyrethroids(1). Aqueous hydrolysis of pyrethrins is predicted to be slow in natural waters(2); however, allethrin is susceptible to hydrolysis under alkaline conditions(3,4).

There are no food uses for the allethrins currently registered ...

... there is the potential for residential handlers to be exposed to allethrins during pesticide applications from aerosol cans made in indoor and outdoor residential settings to several use sites. For the allethrins, inhalation exposures may occur when consumer-use space spray products, patio foggers, mosquito coils, or fly mats are used

Pyrethrins with piperonyl butoxide are used for topical treatment of pediculosis (lice infestations). Combinations of pyrethrins with piperonyl butoxide are not effective for treatment of scabies (mite infestations). Although there are no well-controlled comparative studies, many clinicians consider 1% lindane to be pediculicide of choice. However, some clinicians recommend use of pyrethrins with piperonyl butoxide, esp in infants, young children, & pregnant or lactating women ... . If used correctly, 1-3 treatments ... are usually 100% effective ... Oil based (eg, petroleum distillate) combinations ... produce the quickest results. ... For treatment of pediculosis, enough gel, shampoo, or solution ... should be applied to cover affected hair & adjacent areas ... After 10 min, hair is ... washed thoroughly ... treatment should be repeated after 7-10 days to kill any newly hatched lice. /Pyrethrins/

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. (See all compounds classified as Insecticides.)

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. ...

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.

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.

Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. (ERG, 2016)

Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim calm and warm. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. (ERG, 2016)

Fresh air, rest.|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.

Skin decontamination. Wash skin promptly with soap and water ... . If irritant or paresthetic effects occur, obtain treatment by a physician. Because volatilization of pyrethroids apparently accounts for paresthesia affecting the face, strenuous measures should be taken (ventilation, protective face mask and hood) to avoid vapor contact with the face and eyes. Vitamin E oil preparations (dL-alpha tocopheryl acetate) are uniquely effective in preventing and stopping the paresthetic reaction. They are safe for application to the skin under field conditions. Corn oil is somewhat effective, but possible side effects with continuing use make it less suitable. Vaseline is less effective than corn oil. Zinc oxide actually worsens the reaction. /Pyrethroids/|Eye contamination. Some pyrethroid compounds can be very corrosive to the eyes. Extraordinary measures should be taken to avoid eye contamination. the eye should be treated immediately by prolonged flushing of the eye with copious amounts of clean water or saline. If irritation persists, obtain professional ophthalmologic care. /Pyrethroids/|Other treatments. Several drugs are effective in relieving the pyrethroid neurotoxic manifestations observed in deliberately poisoned laboratory animals, but none has been tested in human poisonings. Therefore, neither efficacy nor safety under these circumstances is known. Furthermore, moderate neurotoxic symptoms and signs are likely to resolve spontaneously if they do occur. /Pyrethroids/|Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Pyrethrins, pyrethroids, and related compounds/|For more Antidote and Emergency Treatment (Complete) data for ALLETHRINS (6 total), please visit the HSDB record page.

/SIGNS AND SYMPTOMS/ Despite their extensive world-wide use, there are relatively few reports of human pyrethroid poisoning. Less than ten deaths have been reported from ingestion or following occupational exposure. Occupationally, the main route of pyrethroid absorption is through the skin. Inhalation is much less important but increases when pyrethroids are used in confined spaces. The main adverse effect of dermal exposure is paresthesia, presumably due to hyperactivity of cutaneous sensory nerve fibers. The face is affected most commonly and the paresthesia are exacerbated by sensory stimulation such as heat, sunlight, scratching, sweating or the application of water. Pyrethroid ingestion gives rise within minutes to a sore throat, nausea, vomiting and abdominal pain. There may be mouth ulceration, increased secretions and/or dysphagia. Systemic effects occur 4 to 48 hours after exposure. Dizziness, headache and fatigue are common, and palpitations, chest tightness and blurred vision less frequent. Coma and convulsions are the principal life-threatening features. Most patients recover within 6 days, although there were seven fatalities among 573 cases in one series and one among 48 cases in another. Management is supportive. As paresthesia usually resolve in 12 to 24 hours, specific treatment is not generally required, although topical application of dl-alpha tocopherol acetate (vitamin E) may reduce their severity. /Pyrethroids/|/SIGNS AND SYMPTOMS/ Contact allergy from pyrethroids ... has not been observed. /Pyrethroids/|/SIGNS AND SYMPTOMS/ The allergenic properties of pyrethroids /with early pyrethrum preparations/ are marked in comparison with other pesticides. Many cases of contact dermatitis and respiratory allergy have been reported. Persons sensitive to ragweed pollen are particularly prone to such reactions. Preparations containing synthetic pyrethroids are less likely to cause allergic reactions than are the preparations made from pyrethrum powder. /Pyrethroids/|/SIGNS AND SYMPTOMS/ The clinical manifestations of inhalation exposure to pyrethrins can be local or systemic. Localized reactors confined to the upper respiratory tract include rhinitis, sneezing, scratchy throat, oral mucosal edema, and even laryngeal mucosal edema. Localized reaction of the lower respiratory tract include cough, shortness of breath, wheezing, and chest pain. An asthmalike reaction occurs with acute exposures in sensitized patients. Hypersensitivity pneumonitis characterized by chest pain, cough, dyspnea, & bronchospasm may occur in an individual chronically exposed. /Pyrethrum and synthetic pyrethroids/|For more Human Toxicity Excerpts (Complete) data for ALLETHRINS (11 total), please visit the HSDB record page.

Allethrin

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

Cough.

Redness.

Redness.

Less than 30,000 lbs are marketed on average per year /Allethrins/

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.

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.

EAD Method 1660. The Determination of Pyrethrins and Pyrethroids in Municipal and Industrial Wastewater by High-Performance Liquid Chromatography. Detection limit=2 ug/l.|AOAC Method 953.05. Allethrin (Technical) and Pesticide Formulations by Titrimetric Method. Method: AOAC 953.05; Procedure: titrimetric method; Analyte: allethrin (technical); Matrix: pesticide formulations; Detection Limit: not provided.[Association of Official Analytical Chemists. Official Methods of Analysis. 15th ed. and Supplements. Washington, DC: Association of Analytical Chemists, 1990, p. V1 164] **PEER REVIEWED**|AOAC Method 973.12. D-trans Allethrin in Pesticide Formulations by Gas Chrromatagraphic Method.|A method for the detection of allethrin ... in mosquito coils was developed by the combination of shaking extraction /with toluene and formic acid/ and gas chromatography . ... The recovery of allethrin in various contents from the coils was 96.6-97.1% with a 1.2-1.5% coefficient of variation.|For more Analytic Laboratory Methods (Complete) data for ALLETHRINS (7 total), please visit the HSDB record page.

Colorimetric method for allethrin residues in milk and meat. Determination involves solvent extraction, concentration, and reaction with highly acidic mercuric oxide-sulfuric acid reagent to produce a red color. Method reported accurate to 0.1 ppm or 10 mg/100 g sample.

Agrochemicals -> Insecticides|INSECTICIDES|ANTIMICROBIAL AGENTS