permethrin
cyclopropanecarboxylic acid, 3-(2,2-dichlorovinyl)-2,2-dimethyl-, 3-phenoxybenzyl ester, (+-)-, (cis,trans)-
Identification
| Name | permethrin |
| CAS Number | 52645-53-1 |
| EINECS | 258-067-9 |
| FDA UNII | 509F88P9SZ |
| Molecular Formula | C21 H20 Cl2 O3 |
| Molecular Weight | 391.29200000 |
| MDL Number | MFCD00041809 |
| Nikkaji Number | J10.127C |
| Beilstein | 4153590 |
| XlogP3 | 6.50 (est) |
Regulatory
Physical Properties
| Appearance | pale brown liquid (est) |
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 34.00 °C. @ 760.00 mm Hg |
| Boiling Point | 465.90 °C. @ 760.00 mm Hg (est) |
| Vapor Pressure | 5.180000 mmHg @ 25.00 °C. (est) |
| Flash Point | 319.00 °F. TCC ( 159.40 °C. ) (est) |
| logP (o/w) | 6.500 |
| Soluble in | water, 0.006 mg/L @ 20 °C (exp) |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | antimicrobial agents |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | oral-chicken LD50 7000 mg/kg |
| Dermal Toxicity | skin-mouse LD50 > 10000 mg/kg |
| Inhalation Toxicity | inhalation-mouse LC50 685 mg/m3 |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | antimicrobial agents |
| Recommendation for permethrin usage levels up to | not for fragrance use. |
| Recommendation for permethrin flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
acticin
ambushfog
anomethrin N
antiborer 3768
bematin 987
chinetrin
coopex
corsair
cosair
cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (3-phenoxyphenyl)methyl ester
cyclopropanecarboxylic acid, 3-(2,2-dichlorovinyl)-2,2-dimethyl-, 3-phenoxybenzyl ester, (+-)-, (cis,trans)-
3-(2,2-
dichloroethenyl)-2,2-dimethyl cyclopropane carboxylic acid (3-phenoxyphenyl) methyl ester
3-(2,2-
dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid, (3-phenoxyphenyl) methyl ester
3-(2,2-
dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid (3-phenoxyphenyl)methyl ester
diffusil H
dragnet FT
ecsumin
ectiban
efmethrin
eksmin
elimite
expar
exsmin
imperator
indothrin
insorbcid MP
kafil
kaleait
kavil
kestrel (pesticide)
lyclear
mitin BC
outflank-stockade
perigen
perigen W
permanone 80
permasect
permethrin
permethrinum
m-
phenoxybenzyl (+-)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
m-
phenoxybenzyl (+1)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
3-
phenoxybenzyl (1RS,3RS;1RS,3SR)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
3-
phenoxybenzyl 2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate
(+-)-3-
phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
m-
phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
3-
phenoxybenzyl(+-)-cis, trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-1-carboxylate
3-(
phenoxyphenyl)methyl (+-)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
(3-
phenoxyphenyl)methyl (+-)cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
(3-
phenoxyphenyl)methyl 3-(2,2-dichlorethenyl)-2,2-dimethylcyclopropanecarboxylate
(3-
phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
picket G
pounce
pramex
pynosect
quamlin
ridect pour-on
stomoxin
stomoxin P
stomozan
talcord
WL 43479
PubMed:
Scabies.
PubMed:
A systematic review of the efficacy of prophylactic control measures for naturally occurring canine leishmaniosis. Part II: topically applied insecticide treatments and prophylactic medications.
PubMed:
Permethrin alters adipogenesis in 3T3-L1 adipocytes and causes insulin resistance in C2C12 myotubes.
PubMed:
HPLC-MS/MS method for the measurement of insecticide degradates in baby food.
PubMed:
Exposures of 129 preschool children to organochlorines, organophosphates, pyrethroids, and acid herbicides at their homes and daycares in North Carolina.
PubMed:
Pesticide residue evaluation in major staple food items of Ethiopia using the QuEChERS method: a case study from the Jimma Zone.
PubMed:
Survival and growth of foodborne pathogens in pesticide solutions routinely used in leafy green vegetables and tomato production.
PubMed:
Fenpropathrin biodegradation pathway in Bacillus sp. DG-02 and its potential for bioremediation of pyrethroid-contaminated soils.
PubMed:
Development of soybean certified reference material for pesticide residue analysis.
PubMed:
Community air monitoring for pesticides-part 2: multiresidue determination of pesticides in air by gas chromatography, gas chromatography-mass spectrometry, and liquid chromatography-mass spectrometry.
PubMed:
Impact of land-use on malaria transmission in the Plateau region, southeastern Benin.
PubMed:
Topical ivermectin 0.5% lotion for treatment of head lice.
PubMed:
Molecular target sequence similarity as a basis for species extrapolation to assess the ecological risk of chemicals with known modes of action.
PubMed:
Dietary intakes of pesticides based on community duplicate diet samples.
PubMed:
Dietary predictors of young children's exposure to current-use pesticides using urinary biomonitoring.
PubMed:
Effect of leaf type and pesticide exposure on abundance of bacterial taxa in mosquito larval habitats.
PubMed:
Aqueous pesticide mitigation efficiency of Typha latifolia (L.), Leersia oryzoides (L.) Sw., and Sparganium americanum Nutt.
PubMed:
Laboratory degradation rates of 11 pyrethroids under aerobic and anaerobic conditions.
PubMed:
Skin conditions: emerging drug-resistant skin infections and infestations.
PubMed:
Novel adult feeding disruption test (FDT) to detect insecticide resistance of lepidopteran pests in cotton.
PubMed:
Permethrin resistance in Aedes albopictus (Diptera: Culicidae) and associated fitness costs.
PubMed:
Reduction of pesticide residues in tomatoes and other produce.
PubMed:
Probing the binding of insecticide permethrin to calf thymus DNA by spectroscopic techniques merging with chemometrics method.
PubMed:
Development of apple certified reference material for quantification of organophosphorus and pyrethroid pesticides.
PubMed:
Cancer and non-cancer health effects from food contaminant exposures for children and adults in California: a risk assessment.
PubMed:
Children's exposures to pyrethroid insecticides at home: a review of data collected in published exposure measurement studies conducted in the United States.
PubMed:
Consumption of pesticide-treated wheat seed by a rural population in Malawi.
PubMed:
Advantages of atmospheric pressure chemical ionization in gas chromatography tandem mass spectrometry: pyrethroid insecticides as a case study.
PubMed:
Evaluation of pressurized liquid extraction for determination of organophosphorus and pyrethroid pesticides in soybean.
PubMed:
Pesticide application and detection in variable agricultural intensity watersheds and their river systems in the maritime region of Canada.
PubMed:
A pharmacokinetic model of cis- and trans-permethrin disposition in rats and humans with aggregate exposure application.
PubMed:
Evaluation of microwave-assisted extraction for the analysis of organophosphorus and pyrethroid pesticides in green onions.
PubMed:
Quantifying children's aggregate (dietary and residential) exposure and dose to permethrin: application and evaluation of EPA's probabilistic SHEDS-Multimedia model.
PubMed:
Development of a multianalyte enzyme-linked immunosorbent assay for permethrin and aroclors and its implementation for analysis of soil/sediment and house dust extracts.
PubMed:
Determination of six pyrethroid insecticides in fruit juice samples using dispersive liquid-liquid microextraction combined with high performance liquid chromatography.
PubMed:
Community duplicate diet methodology: a new tool for estimating dietary exposures to pesticides.
PubMed:
Occurrence and toxicity of three classes of insecticides in water and sediment in two Southern California coastal watersheds.
PubMed:
Development of green onion and cabbage certified reference materials for quantification of organophosphorus and pyrethroid pesticides.
PubMed:
Additivity of pyrethroid actions on sodium influx in cerebrocortical neurons in primary culture.
PubMed:
Determination of multi-residue insecticides of organochlorine, organophosphorus, and pyrethroids in wheat.
PubMed:
Head lice.
PubMed:
Degradation of cyhalofop-butyl (CyB) by Pseudomonas azotoformans strain QDZ-1 and cloning of a novel gene encoding CyB-hydrolyzing esterase.
PubMed:
Pesticides on household surfaces may influence dietary intake of children.
PubMed:
In vitro metabolism of trans-permethrin and its major metabolites, PBalc and PBacid, in humans.
PubMed:
Cumulative risk assessment of chemical exposures in urban environments.
PubMed:
Development of an enzyme-linked immunosorbent assay based a monoclonal antibody for the detection of pyrethroids with phenoxybenzene multiresidue in river water.
PubMed:
Cytotoxic effects of permethrin in oocytes of Rhipicephalus sanguineus (Acari: Ixodidae) fully engorged females: I. Direct or indirect action of the acaricide in germ cells?
PubMed:
Laboratory evaluation of verbutin as a synergist of acaricides against larvae of Rhipicephalus (Boophilus) microplus (Acari: Ixodidae).
PubMed:
A simple HPLC method for determination of permethrin residues in wine.
PubMed:
Deltamethrin: the cream of the crop.
PubMed:
Survey of pesticide residues in maize, cowpea and millet from northern Cameroon: part I.
PubMed:
High levels of miticides and agrochemicals in North American apiaries: implications for honey bee health.
PubMed:
Contact toxicity of insecticides for attract-and-kill applications against adult Plodia interpunctella (Hübner) (Lepidoptera: Pyralidae).
PubMed:
Development, validation and application of a methodology based on solid-phase micro extraction followed by gas chromatography coupled to mass spectrometry (SPME/GC-MS) for the determination of pesticide residues in mangoes.
PubMed:
Isotope dilution gas chromatography/mass spectrometry method for determination of pyrethroids in apple juice.
PubMed:
Permethrin-induced morphological changes in oocytes of Rhipicephalus sanguineus (Acari: Ixodidae) semi-engorged females.
PubMed:
Influences on transfer of selected synthetic pyrethroids from treated Formica to foods.
PubMed:
Pyrethroid and organophosphorus pesticides in composite diet samples from Atlanta, USA adults.
PubMed:
Acute toxicity to zebrafish of two organophosphates and four pyrethroids and their binary mixtures.
PubMed:
Comparing water, bovine milk, and indoor residual spraying as possible sources of DDT and pyrethroid residues in breast milk.
PubMed:
Head lice.
PubMed:
Analysis of permethrin isomers in composite diet samples by molecularly imprinted solid-phase extraction and isotope dilution gas chromatography-ion trap mass spectrometry.
PubMed:
Ovicidal and adulticidal activities of Origanum majorana essential oil constituents against insecticide-susceptible and pyrethroid/malathion-resistant Pediculus humanus capitis (Anoplura: Pediculidae).
PubMed:
Effects of black carbon on pyrethroid availability in sediment.
PubMed:
Genetics and mechanisms of permethrin resistance in the Santa Luiza strain of Boophilus microplus (Acari: Ixodidae).
PubMed:
Biological monitoring of exposure to pyrethrins and pyrethroids in a metropolitan population of the Province of Quebec, Canada.
PubMed:
Extraction and analysis methods for the determination of pyrethroid insecticides in surface water, sediments and biological tissues at environmentally relevant concentrations.
PubMed:
Examining the single and interactive effects of three insecticides on amphibian metamorphosis.
PubMed:
Scabies.
PubMed:
Multimedia measurements and activity patterns in an observational pilot study of nine young children.
PubMed:
Toxicity and efficacy of selected pesticides and new acaricides to stored product mites (Acari: Acaridida).
PubMed:
Abiotic enantiomerization of permethrin and cypermethrin: effects of organic solvents.
PubMed:
Toxicity of insecticides to the sweetpotato whitefly (Hemiptera: Aleyrodidae) and its natural enemies.
PubMed:
Identification and quantitation of pyrethroid pesticide residues in vegetables by solid-phase extraction and liquid chromatography/electrospray ionization ion trap mass spectrometry.
PubMed:
Enantiomeric differences in permethrin degradation pathways in soil and sediment.
PubMed:
Determination of eight synthetic pyrethroids in bovine fat by gas chromatography with electron capture detection.
PubMed:
Enantioselective degradation and chiral stability of pyrethroids in soil and sediment.
PubMed:
Removal of carbaryl, linuron, and permethrin by Lupinus angustifolius under hydroponic conditions.
PubMed:
Pesticides and their metabolites in the homes and urine of farmworker children living in the Salinas Valley, CA.
PubMed:
Effects of dissolved organic matter on permethrin bioavailability to Daphnia species.
PubMed:
Response of Argentine ants and red imported fire ants to permethrin-impregnated plastic strips: foraging rates, colonization of potted soil, and differential mortality.
PubMed:
GerES IV pilot study: assessment of the exposure of German children to organophosphorus and pyrethroid pesticides.
PubMed:
Molecular cloning, purification, and biochemical characterization of a novel pyrethroid-hydrolyzing esterase from Klebsiella sp. strain ZD112.
PubMed:
Vapor phase toxicity of marjoram oil compounds and their related monoterpenoids to Blattella germanica (Orthoptera: Blattellidae).
PubMed:
Purification and characterization of a novel pyrethroid hydrolase from Aspergillus niger ZD11.
PubMed:
Effects of single and repeated exposure to biocidal active substances on the barrier function of the skin in vitro.
PubMed:
Chiral stability of synthetic pyrethroid insecticides.
PubMed:
Potential estrogenic and antiandrogenic effects of permethrin in rats.
PubMed:
Determination of pyrethroid residues in agricultural products by an enzyme-linked immunosorbent assay.
PubMed:
[Inhibitory effect of zinc on beta-hexosaminidase release from RBL-2H3 cells by synthetic chemicals].
PubMed:
Hapten and antibody production for a sensitive immunoassay determining a human urinary metabolite of the pyrethroid insecticide permethrin.
PubMed:
Determination of solid-liquid partition coefficients (K(d)) for diazinon, propetamphos and cis-permethrin: implications for sheep dip disposal.
PubMed:
Solid-phase microextraction (SPME) of permethrin residues from cucumber using a silica-bonded phase-coated stainless steel fibre.
PubMed:
Attractancy and toxicity of an attracticide for Indianmeal moth, Plodia interpunctella (Lepidoptera: Pyralidae).
PubMed:
Relationship of treatment-resistant head lice to the safety and efficacy of pediculicides.
PubMed:
Assessing estrogenic activity of pyrethroid insecticides using in vitro combination assays.
PubMed:
Development of an enzyme-linked immunosorbent assay for the pyrethroid cypermethrin.
PubMed:
Determination of pyrethrin and pyrethroid pesticides in urine and water matrixes by liquid chromatography with diode array detection.
PubMed:
Determination of enantiomers of synthetic pyrethroids in water by solid phase microextraction - enantioselective gas chromatography.
PubMed:
Transfer efficiencies of pesticides from household flooring surfaces to foods.
PubMed:
[Utilization of school lunch dietary data to estimate theoretical maximum daily intake (TMDI) of selected pesticide residues].
PubMed:
Review of common therapeutic options in the United States for the treatment of pediculosis capitis.
PubMed:
Application of solid-phase microextraction for the determination of pyrethroid residues in vegetable samples by GC-MS.
PubMed:
Determination of pyrethroid pesticide residues in processed fruits and vegetables by gas chromatography with electron capture and mass spectrometric detection.
PubMed:
Recovery of synthetic pyrethroids in water samples during storage and extraction.
PubMed:
Single-dose topical exposure to the pyrethroid insecticide, permethrin in C57BL/6N mice: effects on thymus and spleen.
PubMed:
Comparison of five extraction methods for determination of incurred and added pesticides in dietary composites.
PubMed:
Enzyme-linked immunosorbent assay for the pyrethroid deltamethrin.
PubMed:
Multiresidue method for the analysis of multiclass pesticides in agricultural products by gas chromatography-tandem mass spectrometry.
PubMed:
System-level responses of lake ecosystems to chemical stresses using exergy and structural exergy as ecological indicators.
PubMed:
Effect of insecticides used in corn, sorghum, and alfalfa on the predator Orius insidiosus (Hemiptera: Anthocoridae).
PubMed:
Determination of residues of pyrethroid and organophosphorous ectoparasiticides in foods of animal origin.
PubMed:
Evaluation of certain veterinary drug residues in food.
PubMed:
Characterization of acaricide resistance in Rhipicephalus sanguineus (latreille) (Acari: Ixodidae) collected from the Corozal Army Veterinary Quarantine Center, Panama.
PubMed:
Topical permethrin exposure inhibits antibody production and macrophage function in C57Bl/6N mice.
PubMed:
Reduction of pesticide residues on produce by rinsing.
PubMed:
Enzyme-linked immunosorbent assay for the pyrethroid permethrin.
PubMed:
The effects of pyridostigmine bromide and permethrin, alone or in combination, on response acquisition in male and female rats.
PubMed:
A consideration of age-dependent differences in susceptibility to organophosphorus and pyrethroid insecticides.
PubMed:
Binding capacity of various fibre to pesticide residues under simulated gastrointestinal conditions.
PubMed:
Rapid preconcentration method for the determination of pyrethroid insecticides in vegetable oils and butter fat and simultaneous determination by gas chromatography-electron capture detection and gas chromatography-mass spectrometry.
PubMed:
Multiresidue gas chromatographic method for determining synthetic pyrethroid pesticides in agricultural products: collaborative study.
PubMed:
Modulation of K+ transport across synaptosomes of rat brain by synthetic pyrethroids.
PubMed:
Biological activity of permethrin, phenothrin/allerthrin and D-phenothrin on Periplaneta americana and Blattella germanica cockroaches.
PubMed:
Capillary gas chromatographic determination of permethrin insecticide by transesterification.
PubMed:
The role of the family physician in the day care setting.
PubMed:
Determination of total free and glucose-conjugated 3-phenoxybenzyl alcohol residues in foods by gas chromatography with electron capture detection.
PubMed:
A self-medicating applicator for control of ticks on deer.
PubMed:
Modification of AOAC multiresidue method for determination of synthetic pyrethroid residues in fruits, vegetables, and grains. Part I: Acetonitrile extraction system and optimization of florisil cleanup and gas chromatography.
PubMed:
Multiresidue liquid chromatographic method for simultaneous determination of pyrethroid insecticides in fruits and vegetables.
PubMed:
Modulation in acetylcholinesterase of rat brain by pyrethroids in vivo and an in vitro kinetic study.
PubMed:
Cleanup with two Florisil columns for gas chromatographic determination of multiple pyrethroid insecticides in products of animal origin.
PubMed:
Inhibition of monoamine oxidase-A of rat brain by pyrethroids--an in vitro kinetic study.
PubMed:
Monitoring air, soil, stream and fish for aerial drift of permethrin.
PubMed:
Toxicity of microencapsulated permethrin to selected nontarget aquatic invertebrates.
PubMed:
Comparison of crotamiton 10% cream (Eurax) and permethrin 5% cream (Elimite) for the treatment of scabies in children.
PubMed:
[Residue analysis of pyrethroid insecticides in cereal grains, milled fractions and bread].
PubMed:
Comparative effects of synthetic insecticides--endosulfan, phosalone and permethrin--on Chlamydomonas reinhardtii algal cells.
PubMed:
Pyrethroid effects on schedule-controlled behavior: time and dosage relationships.
PubMed:
Effects of pyrethroid insecticides on operant responding maintained by food.
PubMed:
Permethrin and its two metabolite residues in seven agricultural crops.
PubMed:
Variation in cutaneous sensation between synthetic pyrethroid insecticides.
PubMed:
Primary irritant contact dermatitis from synthetic pyrethroid insecticide exposure.
PubMed:
[Effect of permethrin and borax in food poisons on selected insects of hygienic importance].
PubMed:
Application of a high-performance liquid chromatographic system with an on-line infrared detector to the residue analysis of permethrin.
PubMed:
Pyrethroid effects on operant responding and feeding.
PubMed:
Acute toxicity, bioconcentration, and persistence of AC 222,705, benthiocarb, chlorpyrifos, fenvalerate, methyl parathion, and permethrin in the estuarine environment.
PubMed:
Application of the AOAC multi-residue method to determination of synthetic pyrethroid residues in celery and animal products.
PubMed:
Analysis and persistence of permethrin, cypermethrin, deltamethrin, and fenvalerate in the fat and brain of treated rats.
PubMed:
Metabolites of cis- and trans-permethrin in lactating goats.
PubMed:
In vitro metabolism of permethrin isomers by carp and rainbow trout liver microsomes.
PubMed:
Metabolism of trans- and cis-permethrin, trans- and cis-cypermethrin, and decamethrin by microsomal enzymes.
PubMed:
Distribution and metabolic fate of trans- and cis-permethrin in laying hens.
PubMed:
Distribution and metabolism of trans- and cis-permethrin in lactating Jersey cows.
PubMed:
Synthesis of isomeric 3-(2,2-dichlorovinyl)-2-hydroxymethyl-2-methylcyclopropanecarboxylic acids and other permethrin metabolites.
PubMed:
Distribution and excretion rates of 14C-labeled permethrin isomers administered orally to four lactating goats for 10 days.
PubMed:
Radiosynthesis and metabolism in rats of the 1R isomers of the insecticide permethrin.
PubMed:
Permethrin metabolism in rats.