Permethrin

Modify Date: 2024-01-01 23:00:23

Permethrin Structure
Permethrin structure
Common Name Permethrin
CAS Number 52645-53-1 Molecular Weight 391.288
Density 1.3±0.1 g/cm3 Boiling Point 465.9±45.0 °C at 760 mmHg
Molecular Formula C21H20Cl2O3 Melting Point 34-35°C
MSDS Chinese USA Flash Point 159.4±27.7 °C
Symbol GHS02 GHS07 GHS09
GHS02, GHS07, GHS09
Signal Word Danger

 Use of Permethrin


Permethrin (NRDC-143) is an insecticide, acaricide, and insect repellent; functions as a neurotoxin, affecting neuron membranes by prolonging sodium channel activation.

 Names

Name permethrin
Synonym More Synonyms

 Permethrin Biological Activity

Description Permethrin (NRDC-143) is an insecticide, acaricide, and insect repellent; functions as a neurotoxin, affecting neuron membranes by prolonging sodium channel activation.
Related Catalog
References

[1]. Xiao X, et al. Exposure to permethrin promotes high fat diet-induced weight gain and insulin resistance in male C57BL/6J mice. Food Chem Toxicol. 2018 Jan;111:405-416.

[2]. Smith LB, et al. CYP-mediated permethrin resistance in Aedes aegypti and evidence for trans-regulation. PLoS Negl Trop Dis. 2018 Nov 19;12(11):e0006933.

 Chemical & Physical Properties

Density 1.3±0.1 g/cm3
Boiling Point 465.9±45.0 °C at 760 mmHg
Melting Point 34-35°C
Molecular Formula C21H20Cl2O3
Molecular Weight 391.288
Flash Point 159.4±27.7 °C
Exact Mass 390.078949
PSA 35.53000
LogP 7.15
Vapour Pressure 0.0±1.2 mmHg at 25°C
Index of Refraction 1.616
Stability Stable. Incompatible with strong oxidising agents.
Water Solubility insoluble

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
GZ1255000
CHEMICAL NAME :
Cyclopropanecarboxylic acid, 3-(2,2-dichlorovinyl)-2,2-dimethyl-, 3-phenoxybenzyl ester, (+-)-, (cis,trans)-
CAS REGISTRY NUMBER :
52645-53-1
LAST UPDATED :
199710
DATA ITEMS CITED :
44
MOLECULAR FORMULA :
C21-H20-Cl2-O3
MOLECULAR WEIGHT :
391.31
WISWESSER LINE NOTATION :
L3TJ A1 A1 B1UYGG CVO1R COR

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rabbit
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
>4 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
383 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LC50 - Lethal concentration, 50 percent kill
ROUTE OF EXPOSURE :
Inhalation
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
485 mg/m3
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1750 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
6600 mg/kg
TOXIC EFFECTS :
Behavioral - tremor Behavioral - ataxia
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>270 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
537 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia Behavioral - coma
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
424 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LC50 - Lethal concentration, 50 percent kill
ROUTE OF EXPOSURE :
Inhalation
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
685 mg/m3
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
429 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
10 gm/kg
TOXIC EFFECTS :
Behavioral - tremor Behavioral - ataxia
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
31 mg/kg
TOXIC EFFECTS :
Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - other Enzymes
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intracerebral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
600 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
680 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia Behavioral - coma
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
4 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
>2 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
4 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Bird - chicken
DOSE/DURATION :
7 gm/kg
TOXIC EFFECTS :
Behavioral - tremor Behavioral - irritability Gastrointestinal - changes in structure or function of salivary glands
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Bird - quail
DOSE/DURATION :
13500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Bird - duck
DOSE/DURATION :
11300 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Bird - domestic
DOSE/DURATION :
32 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
33855 mg/kg/26W-C
TOXIC EFFECTS :
Liver - changes in liver weight
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
72 gm/kg/2Y-C
TOXIC EFFECTS :
Liver - other changes Liver - changes in liver weight Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - other Enzymes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
2800 mg/kg/7D-I
TOXIC EFFECTS :
Peripheral Nerve and Sensation - recording from peripheral motor nerve Behavioral - muscle weakness Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - other Enzymes
TYPE OF TEST :
TCLo - Lowest published toxic concentration
ROUTE OF EXPOSURE :
Inhalation
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1500 ug/m3/24H/13W-C
TOXIC EFFECTS :
Brain and Coverings - recordings from specific areas of CNS Blood - changes in leukocyte (WBC) count Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - phosphatases
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
4 mg/kg/10D-I
TOXIC EFFECTS :
Immunological Including Allergic - decrease in cellular immune response
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Bird - quail
DOSE/DURATION :
1098 mg/kg/7D-C
TOXIC EFFECTS :
Liver - changes in liver weight Nutritional and Gross Metabolic - weight loss or decreased weight gain Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - hepatic microsomal mixed oxidase (dealkylation, hydroxylation, etc.)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
250 mg/kg
SEX/DURATION :
female 6-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
TYPE OF TEST :
Specific locus test
TYPE OF TEST :
Micronucleus test

MUTATION DATA

TEST SYSTEM :
Rodent - mouse
DOSE/DURATION :
150 mg/kg
REFERENCE :
PHABDI Proceedings of the Hungarian Annual Meeting for Biochemistry. (Magyar Kemikusok Egyesulete, Anker Koz 1, 1061 Budapest, Hungary) V.1- 1961- Volume(issue)/page/year: 21,227,1981 *** REVIEWS *** IARC Cancer Review:Animal Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 53,329,1991 IARC Cancer Review:Human No Available Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 53,329,1991 IARC Cancer Review:Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 53,329,1991 *** U.S. STANDARDS AND REGULATIONS *** EPA FIFRA 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATION FEREAC Federal Register. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) V.1- 1936- Volume(issue)/page/year: 54,7740,1989

 Safety Information

Symbol GHS02 GHS07 GHS09
GHS02, GHS07, GHS09
Signal Word Danger
Hazard Statements H225-H302-H312-H319-H332-H411
Precautionary Statements P210-P273-P280-P305 + P351 + P338
Personal Protective Equipment Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter
Hazard Codes Xn: Harmful;N: Dangerous for the environment;T: Toxic;F: Flammable;
Risk Phrases R20/22
Safety Phrases S13-S24-S36/37/39-S60-S61-S45-S36/37-S16-S7-S26
RIDADR UN1230 3/PG 2
RTECS GZ1255000
HS Code 2916209022

 Synthetic Route

~76%

Permethrin Structure

Permethrin

CAS#:52645-53-1

Literature: Sagami Chemical Research Center Patent: US4214097 A1, 1980 ;

~93%

Permethrin Structure

Permethrin

CAS#:52645-53-1

Literature: Bayer Aktiengesellschaft Patent: US4225704 A1, 1980 ;

~95%

Permethrin Structure

Permethrin

CAS#:52645-53-1

Literature: Nakatsuji, Hidefumi; Morita, Jun-Ichi; Misaki, Tomonori; Tanabe, Yoo Advanced Synthesis and Catalysis, 2006 , vol. 348, # 15 p. 2057 - 2062

~%

Permethrin Structure

Permethrin

CAS#:52645-53-1

Literature: Kuraray Co., Ltd. Patent: US4113968 A1, 1978 ;

~%

Permethrin Structure

Permethrin

CAS#:52645-53-1

Literature: Sumitomo Chemical Company, Limited Patent: US6441220 B1, 2002 ;
Detail
Literature: Sagami Chemical ResearchCenter Patent: US4500733 A1, 1985 ;

~%

Permethrin Structure

Permethrin

CAS#:52645-53-1

Literature: Sumitomo Chemical Company, Limited Patent: US6531626 B1, 2003 ;

~%

Permethrin Structure

Permethrin

CAS#:52645-53-1

Literature: Sumitomo Chemical Company, Limited Patent: US6531626 B1, 2003 ;

 Customs

HS Code 2916209022

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 Synonyms

Anomethrin N
3-(Phenoxyphenyl)methyl (±)-cis,trans-3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
kudos
Ambushfog
Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (3-phenoxyphenyl)methyl ester
Peregin
Stomozan
Perigen
Kestrel
Pounce
Peregin W
SBP 15131TEC
3-Phenoxybenzyl-3-(2,2-dichlorethenyl)-2,2-dimethylcyclopropancarboxylat
Chinetrin
Outflank
L3TJ A1 A1 BVO1R COR&& C1UYGG
Permanone 80
ICI-PP 557
Picket G
1RS,3SR)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
Exmin
EXPAR
3-Phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
Eksmin
Kafil
Stomoxin
3-phenoxybenzyl (1RS,3RS
Indothrin
Cosair
BW-21-Z
Quamlin
Ambush
Kavil
Ridect Pour-On
Talcord
(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
Outflank-stockade
3-Dichloroacetyl-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline
Insorbcid MP
MFCD00041809
Efmethrin
(3-Phenoxyphenyl)methyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
Lyclear
Ecsumin
Perigen W
Diffusil H
m-Phenoxybenzyl (±)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
[3-(phenyloxy)phenyl]methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
Permethrin
(±)-3-Phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
(3-Phenoxyphenyl)methyl 3-(2,2-dichlorethenyl)-2,2-dimethylcyclopropanecarboxylate
Imperator
Coopex
m-Phenoxybenzyl (±)-cis,trans-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
Stomoxi
Permethrin (cis/trans)
Acticin
Picket
Permasect-25EC
3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid (3-phenoxyphenyl)methyl ester
Bematin 987
Permasect
SBP-1513TEC
Pynosect
Exsmin
3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid, (3-phenoxyphenyl)methyl ester
MP79
Permethrin (isomers)
3-phenoxybenzyl (1RS)-cis-trans-3-(2,2-dichlorovinyl)-2,2- dimethylcyclopropanecarboxylate
(3-Phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
LE 79-519
(3-phenoxyphenyl)methyl (1Ξ,3Ξ)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
Antiborer 3768
Kaleait
3-Phenoxybenzyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
EINECS 258-067-9
Stomoxin P
Dragnet FT
Ectiban
Mitin BC
(3-Phenoxyphenyl)methyl (±)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
Ipitox
Pramex
3-Phenoxybenzyl (1RS)-cis-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
Corsair
NIX
Dragnet
3-Phenoxybenzyl 2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate
Cooper
Perthrine
SBP-3246
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