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퍼메트린 구조식 이미지
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퍼메트린 속성

끓는 점
bp0.05 220°
7×10-5 Pa (20 °C)
1.6500 (estimate)
10 °C
저장 조건
물리적 상태
Stable. Incompatible with strong oxidising agents.
CAS 데이터베이스
52645-53-1(CAS DataBase Reference)
Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2, 2-dimethyl-, (3-phenoxyphenyl)methyl ester(52645-53-1)
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 Xn,N,T,F
위험 카페고리 넘버 20/22-43-50/53-39/23/24/25-23/24/25-11-51/53-36-20/21/22
안전지침서 13-24-36/37/39-60-61-45-36/37-16-7-26
유엔번호(UN No.) UN1230 3/PG 2
WGK 독일 3
RTECS 번호 GZ1255000
HS 번호 29162090
유해 물질 데이터 52645-53-1(Hazardous Substances Data)
독성 LD50 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)
신호 어: Danger
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H225 고인화성 액체 및 증기 인화성 액체 구분 2 위험 P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H302 삼키면 유해함 급성 독성 물질 - 경구 구분 4 경고 P264, P270, P301+P312, P330, P501
H312 피부와 접촉하면 유해함 급성 독성 물질 - 경피 구분 4 경고 P280,P302+P352, P312, P322, P363,P501
H317 알레르기성 피부 반응을 일으킬 수 있음 피부 과민성 물질 구분 1 경고 P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 P264, P280, P305+P351+P338,P337+P313P
H332 흡입하면 유해함 급성 독성 물질 흡입 구분 4 경고 P261, P271, P304+P340, P312
H370 장기(또는, 영향을 받은 알려진 모든 장기를 명시)에 손상을 일으킴(노출되어도 특정 표적장기 독성을 일으키지 않는다는 결정적인 노출경로가 있다면 노출경로를 기재) 특정 표적장기 독성 - 1회 노출 구분 1 위험 P260, P264, P270, P307+P311, P321,P405, P501
H410 장기적 영향에 의해 수생생물에 매우 유독함 수생 환경유해성 물질 - 만성 구분 1 경고 P273, P391, P501
H411 장기적 영향에 의해 수생생물에 유독함 수생 환경유해성 물질 - 만성 구분 2
P210 열·스파크·화염·고열로부터 멀리하시오 - 금연 하시오.
P260 분진·흄·가스·미스트·증기·...·스프레이를 흡입하지 마시오.
P261 분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.
P273 환경으로 배출하지 마시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P305+P351+P338 눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.
P333+P313 피부자극성 또는 홍반이 나타나면 의학적인 조치·조언를 구하시오.
P370+P378 화재 시 불을 끄기 위해 (Section 5. 폭발, 화재시 대처방법의 적절한 소화제)을(를) 사용하시오.
P501 ...에 내용물 / 용기를 폐기 하시오.

퍼메트린 C화학적 특성, 용도, 생산

화학적 성질

Crystalline Solid


antihyperlipidemic, cholesterol sequestrant


Labelled Permethrin (P288500). Synthetic pyrethroid insectide, more stable to light and at least as active as the natural pyrethrins and with low mammalian toxicity.




For the treatment of infestation with Sarcoptes scabiei (scabies).


ChEBI: 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.


Elimite (Allergan); Nix (GlaxoSmithKline).

일반 설명

Pale brown liquid. Relatively water insoluble. Used as an insecticide.

공기와 물의 반응

Insoluble in water.

반응 프로필

A pyrethroid derivative.

색상 색인 번호

Pyrethroids, 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.

Clinical Use

Permethrin 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 Profile

Poison 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 Treatments

Permethrin 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.


Soil. 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

신진 대사 경로

Permethrin 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.


Permethrin 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.

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