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Permethrin

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CAS:52645-53-1
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Lastest Price from Permethrin manufacturers

  • Permethrin
  • US $249.00 / g
  • 2020-05-17
  • CAS:52645-53-1
  • Min. Order: 1g
  • Purity: ≥97%
  • Supply Ability: 10kg
  • Permethrin
  • US $0.00-0.00 / KG
  • 2020-04-25
  • CAS:52645-53-1
  • Min. Order: 1KG
  • Purity: 99.0%
  • Supply Ability: 600 tons
  • Permethrin
  • US $1.00 / kg
  • 2019-07-06
  • CAS:52645-53-1
  • Min. Order: 1g
  • Purity: 99%
  • Supply Ability: 100KG
Permethrin Basic information
Product Name:Permethrin
Synonyms:(+-)-,(cis,trans)-yleste;(3-phenoxyphenyl)methyl3-(2,2-dichlorethenyl)-2,2-dimethylcyclopropanecarbox;(3-Phenoxyphenyl)methyl-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate;(3-phenoxyphenyl)methyl3-(2,2-dichloroethyl)-2,2-dimethylcyclopropane-carboxy;(3-phenoxyphenyl)methyl-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-carboxy;-1-carboxylate;3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylicacid(3-phenoxyphen;m-Phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
CAS:52645-53-1
MF:C21H20Cl2O3
MW:391.29
EINECS:258-067-9
Product Categories:Herbicide;INSECTICIDE;Intermediates & Fine Chemicals;Pharmaceuticals;AcaricidesMethod Specific;N-PAlphabetic;PER - POLAPesticides;Alpha sort;Endocrine Disruptors (Draft)Pesticides&Metabolites;WELCHOL;stabilizer;EPA;Insecticides;P;Pesticides;Pesticides&Metabolites;Pyrethroids;Endocrine Disruptors (Draft)Alphabetic;PER - POLA
Mol File:52645-53-1.mol
Permethrin Structure
Permethrin Chemical Properties
Melting point 34-35°C
Boiling point bp0.05 220°
density 1.19
vapor pressure 7×10-5 Pa (20 °C)
refractive index 1.6500 (estimate)
Fp 10 °C
storage temp. 0-6°C
form neat
Water Solubility insoluble
Merck 13,7257
BRN 5765325
Stability:Stable. Incompatible with strong oxidising agents.
InChIKeyRLLPVAHGXHCWKJ-UHFFFAOYSA-N
CAS DataBase Reference52645-53-1(CAS DataBase Reference)
NIST Chemistry ReferencePermethrin(52645-53-1)
EPA Substance Registry SystemPermethrin (52645-53-1)
Safety Information
Hazard Codes Xn,N,T,F
Risk Statements 20/22-43-50/53-39/23/24/25-23/24/25-11-51/53-36-20/21/22
Safety Statements 13-24-36/37/39-60-61-45-36/37-16-7-26
RIDADR UN1230 3/PG 2
WGK Germany 3
RTECS GZ1255000
HS Code 29162090
Hazardous Substances Data52645-53-1(Hazardous Substances Data)
ToxicityLD50 orally in female rats: 3801 mg/kg (Metker); LD50 in 8 day old rats, male adult rats (mg/kg): 340.5, 1500.0 orally (Cantalamessa)
MSDS Information
Permethrin Usage And Synthesis
DescriptionYellow-brown to brown liquid, which sometimes tends to crystallize at room temperature (technical grade).
Chemical PropertiesCrystalline Solid
UsesLabelled Permethrin (P288500). Synthetic pyrethroid insectide, more stable to light and at least as active as the natural pyrethrins and with low mammalian toxicity.
UsesPermethrin is a synthetic pyrethroid active against lice, ticks, mites, and fleas. It acts on neural cellmembranes, delaying repolarization and causing paralysis. The compound has no reported adverse properties, is heat and light stable, has 70% to 80% ovicidal activity, and leaves an active residue on the scalp. Permethrin is 26 times less toxic than lindane and 3 times less toxic than pyrethrins. A 1% permethrin cream rinse (Nix) preparation with a single application was determined to be more effective than treatment with RID. Permethrin-treated military uniforms are effective against human body lice. Apply the cream rinse for 10 minutes and rinse off with water. Localized pruritus may be reported with use of this product.
UsesFor the treatment of infestation with Sarcoptes scabiei (scabies); antihyperlipidemic; cholesterol sequestrant.
DefinitionChEBI: A cyclopropanecarboxylate ester in which the esterifying alcohol is 3-phenoxybenzyl alcohol and the cyclopropane ring is substituted with a 2,2-dichlorovinyl group and with gem-dimethyl groups.
IndicationsPermethrin is a synthetic pyrethroid active against lice, ticks, mites, and fleas. It acts on neural cellmembranes, delaying repolarization and causing paralysis. The compound has no reported adverse properties, is heat and light stable, has 70% to 80% ovicidal activity, and leaves an active residue on the scalp.
Permethrin 0.5% spray kills ticks and repels mosquitoes and stable flies. It is broken down when applied to skin and, hence, should be applied to clothing, shoes, tents, and so on. Spray only enough to moisten the material. Spray on clothing at least 2 hours before wearing. One treatment should last through a few washings.
Brand nameElimite (Allergan); Nix (GlaxoSmithKline).
General DescriptionPale brown liquid. Relatively water insoluble. Used as an insecticide.
Air & Water ReactionsInsoluble in water.
Reactivity ProfileA pyrethroid derivative.
Contact allergensPyrethroids, also called pyrethrinoids, are neurotoxic synthetic compounds used as insecticides, with irritant properties. Cypermethrin and fenvalerate have been reported as causing positive allergic patch tests, but only fenvalerate was relevant in an agricultural worker.
PharmacologyPermethrin is a synthetic pyrethroid that interferes with the influx of sodium through cell membranes, leading to neurologic paralysis and death of the mite. There is minimal percutaneous absorption (<2%), which is rapidly hydrolyzed and excreted in the urine. Permethrin 5% dermal cream (Elimite) is applied for 8 to 12 hours to the entire body from the chin down and is then washed off.
Clinical UsePermethrin is 3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarboxylicacid (3-phenoxyphenyl)methylester or 3-(phenoxyphenyl)methyl (±)-cis, trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate(Nix). This synthetic pyrethrinoid compound is more stablechemically than most natural pyrethrins and is at least as activeas an insecticide. Of the four isomers present, the1(R),trans and 1(R),cis-isomers are primarily responsiblefor the insecticidal activity. The commercial product is amixture consisting of 60% trans and 40% cis racemic isomers.It occurs as colorless to pale yellow low-melting crystalsor as a pale yellow liquid and is insoluble in water butsoluble in most organic solvents.
Permethrin exerts a lethal action against lice, ticks, mites,and fleas. It acts on the nerve cell membranes of the parasitesto disrupt sodium channel conductance. It is used as apediculicide for the treatment of head lice. A single applicationof a 1% solution effects cures in more than 99% ofcases. The most frequent side effect is pruritus, which occurredin about 6% of the patients tested.
Safety ProfilePoison by inhalation, intravenous, and intracerebral routes. Moderately toxic by ingestion. Experimental reproductive effects. Mutation data reported. A skin irritant. When heated to decomposition it emits toxic fumes of Cl-. See also ESTERS
Veterinary Drugs and TreatmentsPermethrin is synthetic pyrethroid that acts as an adulticide insecticide/miticide. It has knockdown activity against fleas, lice, ticks, and certain mites (e.g., Cheyletiella, Sarcoptes scabiei) and also has repellant activity. In small animal medicine, it is used primarily for fleas and ticks on dogs. In large animal and food animal medicine, there are many products (not listed below) available for pour-on, dusting, and spray use for flies, lice, mites, mosquitoes, ticks and keds.
Permethrin acts by disrupting the sodium channel current in arthropod nerve cell membranes, resulting in paralysis and death.
Environmental FateSoil. Permethrin biodegraded rapidly via hydrolysis yielding 3-(2,2-dichloroethenyl)- 2,2-dimethylcyclopropanecarboxylic acid and 3-phenoxybenzyl alcohol (Kaufman et al., 1981). The reported half-life in soil containing 1.3–51.3% organic matter and pH 4.2–7.7 is <38 days (Worthing and Hance, 1991)
In lake water, permethrin degraded more rapidly than in flooded sediment to transand cis-(dichlorovinyl)dimethylcyclopropanecarboxylic acid. The cis isomer was more stable toward biological and chemical degradation than the trans isomer (Sharom and Solom
Plant. Metabolites identified in cotton leaves included trans-hydroxypermethrin, 2′- hydroxypermethrin, 4′-hydroxypermethrin, dichlorovinyl acid, dichlorovinyl acid conjugates, hydroxydichlorovinyl acid, hydroxydichlorovinyl acid conjugates, phe
Dislodgable residues of permethrin on cotton leaves 0, 24, 48, 72 and 96 hours after application (1.1 kg/ha) were (cis:trans): 0.26:0.38, 0.24:0.34, 0.22:0.32, 0.16:0.24 and 0.15:0.21 μg/m2, respectively (Buck et al., 1980).
Photolytic. Photolysis of permethrin in aqueous solutions containing various solvents (acetone, hexane and methanol) under UV light (λ >290 nm) or on soil in sunlight initially resulted in the isomerization of the cyclopropane moiety and ester cl
Metabolic pathwayPermethrin was one of the first photostable pyrethroids suitable for field use.It served as a precursor for others such as its α-cyano analogue, cypermethrin. As it lacks the cyano group it has no chirality at the acarbon atom and therefore consists of a mixture of only four isomers. It is hydrolysed more readily than cypermethrin because it is an ester of a primary alcohol.
Much of the early research on the metabolism of the synthetic, photostable pyrethroids was conducted by Casida and co-workers on permethrin. The published results greatly assisted subsequent work on the analogues. This is stressed because some of the information reported below will draw on the metabolic schemes given in the cypermethrin entry.
The environmental fate of permethrin and its metabolism in plants, insects, animals and fish have been reported. The insecticide is metabolised by ester cleavage to its constituent acid and alcohol and subsequent conjugation of these. The primary metabolites are also subject to oxidation prior to conjugation. Permethrin itself is also subject to oxidation, the cisisomers more so than the trans-isomers because the former is more slowly hy droly sed.
DegradationPermethrin is stable as a solid but it is readily hydrolysed in solution under alkaline conditions; it is most stable at pH 4. It is relatively resistant to photodegradation in the context of field use but it undergoes facile photoisomerism (Holmstead et al., 1978). It can be degraded under laboratory conditions affording DCVA (2) and 3-phenoxybenzyl alcohol (3PBAlc, 3). Under appropriate conditions, trans-permethrin affords 29% trans-DCVA and 13% cis-DCVA. The mechanisms of these reactions have been reviewed in detail by Ruzo (1982). Permethrin is resistant to photo-oxidation; other reactions, such as dechlorination, are of minor importance. The degradation products are shown in Scheme 1.
Toxicity evaluationAcute oral LD50 for rats: 430-4,000 mg/kg (cis:trans ca. 40:60); ca. 6,000 mg/kg (cis:trans ca. 20:80)
Tag:Permethrin(52645-53-1) Related Product Information
CHLORODIMETHYLVINYLSILANE Cyhalothrin SUPERCYPERMETHRIN Bifenthrin p-Dichlorobenzene alpha-Cypermethrin Cyhalothrin Cyclopropanecarboxylic acid Cypermethrin 2,4-Dichlorobenzyl chloride Etofenprox Permethrin Folic acid Vinyl ester resin 2,4-Dichlorophenol Vinyl resin Citric acid Phenothrin