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CAS NUMNER: 52645-53-1
EC NUMBER: 258-067-9
MOLECULAR FORMULA: C21H20Cl2O3
MOLECULAR WEIGHT: 391.3
IUPAC NAME: (3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
As a medication, Permethrin is used to treat scabies and lice.
Permethrin is applied to the skin as a cream or lotion.
As an insecticide, Permethrin can be sprayed onto clothing or mosquito nets to kill the insects that touch them.
Use during pregnancy appears to be safe.
Permethrin is approved for use on and around people over the age of two months.
Permethrin works by disrupting the function of the neurons of lice and scabies mites.
Permethrin was discovered in 1973.
Permethrin is on the World Health Organization's List of Essential Medicines.
In 2017, it was the 410th most commonly prescribed medication in the United States, with more than 150 thousand prescriptions
USES OF IT:
-In agriculture, to protect crops (a drawback is that it is lethal to bees)
-In agriculture, to kill livestock parasites
-For industrial and domestic insect control
-In the textile industry, to prevent insect attack of woollen products
-In aviation, the WHO, IHR and ICAO require arriving aircraft be disinsected prior to embarkation, departure, descent, or deplaning in certain countries.
Aircraft disinsection with permethrin-based products is recommended only prior to embarkation.
Prior to departure (after boarding), at the top of descent or on arrival, d-phenothrin-based (1R-trans phenothrin) aircraft insecticides are recommended.
Insect repellent:
As a personal protective measure, permethrin is applied to clothing.
Permethrin is a cloth impregnant, notably in mosquito nets and field wear.
Note that while permethrin may be marketed as an insect repellent, it doesn't prevent insects from landing.
Instead it works by incapacitating or killing insects before they can bite.
Medical use:
Permethrin is available for topical use as a cream or lotion.
Permethrin is indicated for the treatment and prevention in exposed individuals of head lice and treatment of scabies.
For treatment of scabies: Adults and children older than 2 months are instructed to apply the cream to the entire body from head to the soles of the feet.
In general, one treatment is curative.
Pest control / effectiveness and persistence:
In agriculture, permethrin is mainly used on cotton, wheat, maize, and alfalfa crops.
Permethrin's use is controversial because, as a broad-spectrum chemical, it kills indiscriminately; as well as the intended pests, it can harm beneficial insects, including honey bees, as well as cats and aquatic life.
Permethrin kills ticks and mosquitoes on contact with treated clothing.
A method of reducing deer tick populations by treating rodent vectors involves stuffing biodegradable cardboard tubes with permethrin-treated cotton.
Mice collect the cotton for lining their nests.
Permethrin on the cotton instantly kills any immature ticks feeding on the mice.
Permethrin is used in tropical areas to prevent mosquito-borne disease such as dengue fever and malaria.
Mosquito nets used to cover beds may be treated with a solution of permethrin.
This increases the effectiveness of the bed net by killing parasitic insects before they are able to find gaps or holes in the net.
Personnel working in malaria-endemic areas may be instructed to treat their clothing with permethrin as well.
Permethrin is the most commonly used insecticide worldwide for the protection of wool from keratinophagous insects such as Tineola bisselliella.
To better protect soldiers from the risk and annoyance of biting insects, the British and US armies are treating all new uniforms with permethrin.
Permethrin (as well as other long-term pyrethroids) is effective over several months, in particular when used indoors.
International studies report that permethrin can be detected in house dust, in fine dust, and on indoor surfaces even years after the application.
Permethrin's degradation rate under indoor conditions is approximately 10% after 3 months.
Resistance:
Contrary to the most common mechanism of insecticide resistance evolution – selection for preexisting, low-frequency alleles – in Aedes aegypti permethrin resistance has come about through the mechanism common to pyrethroids and DDT known as "knockdown resistance" (kdr) mutations.
García et al 2009 finds a kdr allele to rapidly spread through Mexico and recently become dominant there
Pharmacokinetics:
Permethrin is a chemical categorized in the pyrethroid insecticide group.
The chemicals in the pyrethroid family are created to emulate the chemicals found in the chrysanthemum flower.
Absorption:
Absorption of topical permethrin is minimal.
One in vivo study demonstrated 0.5% absorption in the first 48 hours based upon excretion of urinary metabolites.
Distribution:
Distribution of permethrin has been studied in rat models, with highest amounts accumulating in fat and the brain.
This can be explained by the lipophilic nature of the permethrin molecule.
Metabolism:
Metabolism of permethrin occurs mainly in the liver, where the molecule undergoes oxidation by the cytochrome P450 system, as well as hydrolysis, into metabolites.
Elimination of these metabolites occurs via urinary excretion.
Stereochemistry:
Permethrin has four stereoisomers (two enantiomeric pairs), arising from the two stereocenters in the cyclopropane ring.
The trans enantiomeric pair is known as transpermethrin.
(1R,3S)-trans and (1R,3R)-cis enantiomers are responsible for the insecticidal properties of permethrin.
History:
Permethrin was first made in 1973.
Numerous synthetic routes exist for the production of the DV-acid ester precursor.
The pathway known as the Kuraray Process uses four steps.
In general, the final step in the total synthesis of any of the synthetic pyrethroids is a coupling of a DV-acid ester and an alcohol.
In the case of permethrin synthesis, the DV-acid cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, ethyl ester, is coupled with the alcohol, m-phenoxybenzyl alcohol, through a transesterification reaction with base.
Tetraisopropyl titanate or sodium ethylate may be used as the base.
The alcohol precursor may be prepared in three steps.
First, m-cresol, chlorobenzene, sodium hydroxide, potassium hydroxide, and copper chloride react to yield m-phenoxytoluene.
Second, oxidation of m-phenoxytoluene over selenium dioxide provides m-phenoxybenzaldehyde.
Third, a Cannizzaro reaction of the benzaldehyde in formaldehyde and potassium hydroxide affords the m-phenoxybenzyl alcohol.
Permethrin is used to treat scabies ('mites that attach themselves to the skin) in adults and children 2 months of age and older.
Over-the-counter permethrin is used to treat lice (small insects that attach themselves to the skin on the head) in adults and children 2 months of age and older.
Permethrin is in a class of medications called scabicides and pediculicides.
Permethrin is registered for use on/in numerous food/feed crops, livestock and livestock housing, modes of transportation, structures, buildings (including food handling establishments), Public Health Mosquito abatement programs, and numerous residential use sites including use in outdoor and indoor spaces, pets, and clothing (impregnated and ready to use formulations).
• According to Agency data, approximately 2 million pounds of permethrin are applied annually to agricultural, residential and public health uses sites.
The majority of permethrin, over 70%, is used in non-agricultural settings; 55% is applied by professionals, 41% is applied by homeowners on residential areas, and 4% is applied on mosquito abatement areas.
• Permethrin is a restricted use pesticide for crop and wide area applications (i.e., nurseries, sod farms) due to high toxicity to aquatic organisms, except for wide area mosquito adulticide use.
Permethrin is a general use pesticide for residential and industrial applications.
• Permethrin also has non-FIFRA pharmaceutical uses as a pediculicide for the treatment of head lice and scabies.
The Food and Drug Administration (FDA) approves use of the pesticidecontaining pharmaceutical under FFDCA.
Permethrin is a pyrethroid insecticide that is similar to the natural insecticide, pyrethrum.
Pyrethrum is found in chrysanthemum
Permethrin is a synthetic pyrethroid and neurotoxin.
Permethrin affects the neuronal membrane by blocking the movement of sodium ions from outside to inside the neuronal cell membrane thereby disrupting the sodium channel current that regulates the polarization of the membrane.
This leads to delayed repolarization and subsequent paralysis of the nervous system.
Permethrin is used to eradicate parasites such as head lice, ticks and scabies from humans and animals.
Permethrin is 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.
Permethrin has a role as a pyrethroid ester insecticide, a pyrethroid ester acaricide, an agrochemical, an ectoparasiticide and a scabicide.
Permethrin is a member of cyclopropanes and a cyclopropanecarboxylate ester.
Permethrin derives from a 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid.
Permethrin is a pale brown liquid. Relatively water insoluble. Used as an insecticide.
Permethrin is a pale brown liquid.
Relatively water insoluble.
Used as an insecticide.
Pure permethrin cis-isomer forms colorless crystals at room temperature but a mixture of cis and trans isomers normally occurs as a liquid, with its appearance depending on the ratio of isomers.
Pure permethrin (40:60) is a colorless, viscous liquid, whereas the technical compound is a yellow to yellow-brown viscous liquid.
Permethrin is a synthetic pyrethroid that has low mammalian toxicity and an insecticidal effectiveness higher that of the natural pyrethrins.
Because of its high ovicidal activity and persistence on hair, a properly applied 1% cream rinse preparation eliminates head lice infestation after a single application.
Permethrin is rapidly metabolized by ester hydrolysis to inactive metabolites which are excreted primarily in the urine.
Permethrin has a potential application for forest protection and vector control for the control of noxious insects in the household and on cattle, for the control of body lice, and in mosquito nets.
General Classification:
• Commercial / Institutional
• Inside the Home
• Landscaping/Yard
• Personal Care
• Pesticides
• Pet Care
Permethrin is used to treat head lice, tiny insects that infest and irritate your scalp.
Permethrin is also used to help avoid infestation in people who have close contact with someone who has head lice.
Permethrin belongs to a class of drugs known as pyrethrins.
Permethrin works by paralyzing and killing lice and their eggs (nits).
Permethrin may also be used for pubic lice.
Permethrin is available under the following different brand names: Nix, Elimite, and Acticin.
Permethrin is a synthetic broad-spectrum insecticide classified as one of the oldest organic insecticides.
While Permethrin is manmade, it resembles naturally occurring chemicals called pyrethroids that are naturally found in chrysanthemums, which have insecticidal properties.
PHYSICAL PROPERTIES:
-Molecular Weight: 391.3
-XLogP3: 6.5
-Exact Mass: 390.0789499
-Monoisotopic Mass: 390.0789499
-Topological Polar Surface Area: 35.5 Ų
-Physical Description: YELLOW-BROWN-TO-BROWN VISCOUS LIQUID OR CRYSTALS
-Color: Colorless, white to pale yellow
-Form: crystals to a viscous liquid
-Boiling Point: 220 °C at 5.00E-02 mm Hg
-Melting Point: 34 °C
-Solubility: 0.006 mg/L
-Density: 1.2
-Vapor Pressure: 2.18e-08 mmHg
-LogP: 6.5
-Henrys Law Constant: 2.4X10-6 atm-cu m/mol
-Corrosivity: Does not corrode aluminum
Only use permethrin when you have an insect problem and only on recommended plants.
Permethrin is available under many trade names in various incarnations.
Always read the manufacturer’s instructions regarding application and safety before use.
Permethrin is more commonly available as spray, dust, emulsion concentrate, and wettable powder formulations.
General instructions for spray products are to spray on a calm day and apply to all areas of the plant thoroughly, including the underside of the leaves. Again, refer to the manufacturer’s instructions for frequency of application.
Permethrin can irritate eyes and skin so wear goggles, long pants, and a long-sleeved shirt when using in the garden.
Do not dump this insecticide in a body of water or on soil near water.
CHEMICAL PROPERTIES:
-Heavy Atom Count: 26
-Formal Charge: 0
-Complexity: 521
-Isotope Atom Count: 0
-Defined Atom Stereocenter Count: 0
-Undefined Atom Stereocenter Count: 2
-Defined Bond Stereocenter Count: 0
-Undefined Bond Stereocenter Count: 0
-Covalently-Bonded Unit Count: 1
-Compound Is Canonicalized: Yes
-Hydrogen Bond Donor Count: 0
-Hydrogen Bond Acceptor Count: 3
-Rotatable Bond Count: 7
SYNONYMS:
Permethrin
Ambush
Transpermethrin
Pounce
Elimite
Imperator
(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
(+)-trans-Permethrin
Permethrine
Permetrina
Acticin
Ambushfog
Corsair
Dragnet
Ectiban
Kaleait
Kestrel
Outflank
Perigen
Permasect
Perthrine
Stomoxin
Stomozan
Coopex
Eksmin
Picket
Expar
Kafil
Kavil
Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (3-phenoxyphenyl)methyl ester
Anomethrin N
1RS cis-Permethrin
1RS,cis-Permethrin
1RS-trans-Permethrin
Kudos
Transpermethrin [ISO]
(+-)-cis-Permethrin
3-phenoxybenzyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
trans-(+-)-Permethrin
3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid, (3-phenoxyphenyl) methyl ester
Permethrinum
S-3151
Chinetrin
Ecsumin
Efmethrin
Indothrin
Lyclear
Quamlin
Stomoxi
Cosair
Exmin
Exsmin
Ipitox
(+-)-trans-Permethrin
Permethrine,c&t
(+-)-cis-Fmc 33297
Diffusil H
Insorbcid MP
Stomoxin P
Perigen W
Dragnet FT
Picket G
Permethrin,racemic
[3-(phenyloxy)phenyl]methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
Mitin BC
Antiborer 3768
Bematin 987
Permetrina
3-Phenoxybenzyl 2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate
m-Phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
Cyclopropanecarboxylic acid, 3-(2,2-dichlorovinyl)-2,2-dimethyl-, (3-phenoxyphenyl)methyl ester, (1R-trans)-
Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (3-phenoxyphenyl)methyl ester, cis-(+-)-
Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (3-phenoxyphenyl)methyl ester, trans-(+-)-
Pharmakon1600-01504932
Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (3-phenoxyphenyl)methyl ester, (1R,3S)-rel-
Cyclopropanecarboxylic acid, 3-(2,2-dichlorovinyl)-2,2-dimethyl-, (3-phenoxyphenyl)methyl ester, (1R-cis)-
(+-)-3-Phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
(3-Phenoxyphenyl)methyl 3-(2,2-dichlorethenyl)-2,2-dimethylcyclopropanecarboxylate
3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid (3-phenoxyphenyl)methyl ester
3-Phenoxybenzyl (1RS)-cis-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
3-Phenoxybenzyl (1RS,3RS;1RS,3SR)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
3-Phenoxybenzyl(+-)-cis, trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-1-carboxylate
m-Phenoxybenzyl (+-)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
m-Phenoxybenzyl (+1)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
(3-Phenoxyphenyl)methyl (+-)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
3-(Phenoxyphenyl)methyl (+-)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
(1RS,3SR)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclo-propanecarboxylate
3-phenoxybenzyl 2-(2,2-dichlorovinyl)3,3-dimethylcyclopropanecarboxylate
3-Phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
(3-phenoxyphenyl)methyl 3-(2,2-dichlorovinyl)-2,2-dimethyl-cyclopropanecarboxylate
(3-phenoxyphenyl)methyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxyl ate
3-phenoxybenzyl (1RS)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
m-phenoxybenzyl 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropanecarboxylate
(3-Phenoxyphenyl)methyl (+-)cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
(3-Phenoxyphenyl)methyl (+/-)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
