Permethrin
CAS no.: 52645-53-1
EC / List no.: 258-067-9
Mol. formula: C21H20Cl2O3
m-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
m-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
Permethrin
permethrin (ISO)
permethrin (ISO);m-phenoxybenzyl 3-(2,2-dichorovinyl)-2,2-dimethylcyclopro panecarboxylate
Permethrin is a synthetic broad-spectrum insecticide classified as one of the oldest organic insecticides.
Permethrin is a pyrethroid insecticide commonly used in the treatment of lice infestations and scabies.
Permethrin is an insecticide used to prevent infestation with Sarcoptes scabiei (scabies).
Permethrin, a pyrethroid, is active against a broad range of pests including lice, ticks, fleas, mites, and other arthropods.
Permethrin is an insecticide in the pyrethroid family. Pyrethroids are synthetic chemicals that act like natural extracts from the chrysanthemum flower.
Permethrin is used in a number of ways to control insects. Products containing permethrin may be used in public health mosquito control programs.
They may be used on food and feed crops, on ornamental lawns, on livestock and pets, in structures and buildings, and on clothing.
Permethrin may also be used in places where food is handled, such as restaurants.
Permethrin was first registered with the United States Environmental Protection Agency (U.S. EPA) in 1979, and was re-registered in 2006.
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. It derives from a 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid.
Permethrin is a pale brown liquid. Relatively water insoluble. Used as an insecticide.
What are some products that contain permethrin?
Products containing permethrin may be liquids, powders, dusts, aerosol solutions, sprays, and treated clothing.
Permethrin is used in cattle ear tags and flea collars, or in spot-on treatments for dogs.
There are currently more than 1400 registered products containing permethrin.
Some products are used to treat scabies and head lice on people.
These products are drugs and are regulated by the U.S. Food and Drug Administration (FDA).
Permethrin’ s Mechanism of action: Permethrin acts on the nerve cell membrane to disrupt the sodium channel current by which the polarization of the membrane is regulated.
Delayed repolarization and paralysis of the pests are the consequences of this disturbance.
How does permethrin work?
Permethrin can affect insects if they eat it or touch it.
Permethrin affects the nervous system in insects, causing muscle spasms, paralysis and death. Permethrin is more toxic to insects than it is to people and dogs.
This is because insects can’t break it down as quickly as people and dogs.
Cats are more sensitive to permethrin than dogs or people because it takes their bodies a long time to break it down.
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.
While it is manmade, it resembles naturally occurring chemicals called pyrethroids that are naturally found in chrysanthemums, which have insecticidal properties.
Permethrin kills many different types of insects by paralyzing the nervous system.
It works when ingested or through direct contact and kills adults, eggs, and larvae.
It lasts up to 12 weeks post application.
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.
Depending on the formulation, permethrin is a non-toxic to moderately toxic pesticide
Uses of Permethrin:
Insecticide
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. It 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.[9]
In pet flea preventive collars or treatment (safe for use on dogs but not cats)
In timber treatment
Pest control / effectiveness and persistence
In agriculture, permethrin is mainly used on cotton, wheat, maize, and alfalfa crops.
Its 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.
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.
Its degradation rate under indoor conditions is approximately 10% after 3 months.
Side effects
Permethrin application can cause mild skin irritation and burning.
Permethrin has little systemic absorption, and is considered safe for topical use in adults and children over the age of two months.
The FDA has assigned it as pregnancy category B. Animal studies have shown no effects on fertility or teratogenicity, but studies in humans have not been performed.
The excretion of permethrin in breastmilk is unknown, and it is recommended that breastfeeding be temporarily discontinued during treatment.
Skin reactions are uncommon.
Excessive exposure to permethrin can cause nausea, headache, muscle weakness, excessive salivation, shortness of breath, and seizures.
Worker exposure to the chemical can be monitored by measurement of the urinary metabolites, while severe overdose may be confirmed by measurement of permethrin in serum or blood plasma.
Permethrin does not present any notable genotoxicity or immunotoxicity in humans and farm animals, but is classified by the EPA as a likely human carcinogen when ingested, based on reproducible studies in which mice fed permethrin developed liver and lung tumors.
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.
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.
Brand names
In Nordic countries and North America, a permethrin formulation for lice treatment is marketed under trade name Nix, available over the counter.
Johnson & Johnson’s UK brand Lyclear covers an assortment of different products, mostly non-insecticidal, but a few of which are based on permethrin.
Stronger concentrations of permethrin are used to treat scabies (which embed inside the skin), compared to lice (which remain outside the skin).
In the U.S. the more concentrated products such as Elimite are available by prescription only.
Other animals
It is known to be highly toxic to cats, fish and aquatic species with long-lasting effects.
Cats
Permethrin is toxic to cats; however, it has little effect on dogs.
Pesticide-grade permethrin is toxic to cats.
Many cats die after being given flea treatments intended for dogs, or by contact with dogs having recently been treated with permethrin.
In cats it may induce hyperexcitability, tremors, seizures, and death.
Toxic exposure of permethrin can cause several symptoms, including convulsion, hyperaesthesia, hyperthermia, hypersalivation, and loss of balance and coordination.
Exposure to pyrethroid-derived drugs such as permethrin requires treatment by a veterinarian, otherwise the poisoning is often fatal.
This intolerance is due to a defect in glucuronosyltransferase, a common detoxification enzyme in other mammals, that also makes the cat intolerant to paracetamol (acetaminophen).
The use of any external parasiticides based on permethrin is contraindicated for cats.
Aquatic organisms
Permethrin is listed as a “restricted use” substance by the US Environmental Protection Agency (EPA) due to its high toxicity to aquatic organisms, so permethrin and permethrin-contaminated water should be properly disposed of.
Permethrin is quite stable, having a half life of 51–71 days in an aqueous environment exposed to light.
It is also highly persistent in soil.
Translated names
(1RS)-cis,trans-3-(2,2-dichlorowinylo)-2,2-dimetylocyklopropanokarboksylan 3-fenoksybenzylu (pl)
(1RS,3RS;1RS,3RS)-3-(2,2-dichlorowinylo)-2,2-dimetylocyklopropanokarboksylan 3-fenoksybenzylu (permetryna) (pl)
(1RS,3RS;1RS,3SR)-3-(2,2-dichlorovinyl)-2,2-diméthylcyclopropanecarboxylate de 3-phénoxybenzyle (perméthrine) (fr)
(1RS,3RS;1RS,3SR)-3-(2,2-Diclorovinil)-2,2-dimetilciclopropanocarboxilato de 3-fenoxibencilo (permetrina) (es)
(1RS,3RS;1RS,3SR)-3-(2,2-diclorovinil)-2,2-dimetilciclopropanocarboxilato de 3-fenoxibenzilo (permetrina) (pt)
(1RS,3RS;1RS,3SR)-3-(2,2-διχλωροβινυλο)-2,2-διμεθυλοκυκλοπροπανοκαρβοξυλικό 3-φαινοξυβενζύλιο (Permethrin/Περμεθρίνη) (el)
(3-fenoxybenzyl)-3-(2,2-dichlóretenyl)-2,2-dimetylcyklopropánkarboxylát (permetrín) (sk)
3-(2,2-diclorovinil)-2,2-dimetilciclopropancarbossilato di m-fenossibenzile (it)
3-(2,2-diclorovinil)-2,2-dimetilciclopropanocarboxilato de m-fenoxibencilo (es)
3-(2,2-diclorovinil)-2,2-dimetilciclopropanocarboxilato de m-fenoxibenzilo (pt)
3-(2,2-διχλωροβινυλ)-2,2-διμεθυλκυκλοπροπανιοκαρβοξυλικό m-φαινοξυβενζύλιο (el)
3-fenoksibentsyyli-(1RS, 3RS; 1RS, 3SR)-3-(2,2-dikloorivinyyli)-2,2-dimetyylisyklopropaanikarboksylaatti (permetriini) (fi)
3-fenoksibenzil (1RS,3RS;1RS,3SR)-3-(2,2-dichlorvinil)-2,2-dimetilciklopropankarboksilatas (permetrinas) (lt)
3-fenoksibenzil (1RS,3RS;1RS,3SR)-3-(2,2-diklorovinil)-2,2-dimetilciklopropankarboksilat (permetrin) (sl)
3-fenoksibenzil 3-(2,2-diklorovinil)-2,2-dimetilciklopropankarboksilat (sl)
3-Fenoksibenzil(1RS,3RS;1RS,3SR)-3-(2,2-dihlorvinil)-2,2-dimetilciklopropānkarboksilāts (permetrīns) (lv)
3-fenoksübensüül-(1RS,3RS;1RS,3SR)-3-(2,2-diklorovinüül)-2,2-dimetüültsüklopropaankarboksülaat (permetriin) (et)
3-fenossibenzil-(1RS)-cis,trans-3-(2,2-diclorovinile)-2,2 dimetilciclopropano carbossilato (Permetrina) (it)
3-fenoxibensyl-(1RS,3RS;1RS,3SR)-3-(2,2-diklorovinyl)-2,2-dimetylcyklopropankarboxylat (Permetrin) (sv)
3-fenoxibenzil (1RS,3RS;1RS,3SR)-3-(2,2-diclorovinil)-2,2-dimetilciclopropancarboxilat (Permetrin) (ro)
3-fenoxibenzil (1RS,3RS;1RS,3SR)-3-(2,2-diklórvinil)-2,2-dimetil-ciklopropán-karboxilát (Permetrin) (hu)
3-fenoxibenzyl-3-(2,2-diklorvinyl-2-dimetylcyklopropankarbamatoxilat (sv)
3-Fenoxybenzyl(1RS,3RS;1RS,3SR)-3-(2,2-dichloorvinyl)-2,2-dimethylcyclopropaancarboxylaat (permethrin) (nl)
3-fenoxybenzyl(1RS,3RS;1RS,3SR)-3-(2,2-dichlorvinyl)-2,2-dimethylcyklopropankarboxylát (permethrin) (cs)
3-fenoxybenzyl-[3-(2,2-dichlorvinyl)-2,2-dimethylcyklopropan-1-karboxylát] (cs)
3-phenoxybenzyl (1RS,3RS;1RS,3SR)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate (Permethrin) (no)
3-Phenoxybenzyl (1RS,3RS;1RS,3SR)-3-(2,2-dichlorvinyl)-2,2-dimethylcyclopropancarboxylat (Permethrin) (de)
3-phenoxybenzyl-(1RS,3RS;1RS,3SR)-3-(2,2-dichlorvinyl)-2,2-dimethylcyclopropancarboxylat (permethrin) (da)
3-феноксибензилов (1RS,3RS;1RS,3SR)-3-(2,2-дихлоровинил)-2,2-диметилциклопропанкарбоксилат (перметрин) (bg)
m-Fenoksibentsyyli-3-(2,2-dikloorivinyyli)-2,2-dimetyylisyklopropaanikarboksylaatti (fi)
m-fenoksibenzil 3-(2,2-diklorovinil)-2,2-dimetilciklopropankarboksilat (hr)
m-fenoksibenzil-3(2,2-dihlorvinil)-2,2-dimetilciklopropānkarboksilāts (lv)
m-fenoksibenzil-3-(2,2-dichlorvinil)-2,2-dimetilciklopropankarboksilatas (lt)
m-fenoksybenzyl-3-(2,2-diklorvinyl)-2,2-dimetylcyklopropankarboksylat (no)
m-fenoksübensüül-3-(2,2-diklorovinüül)-2,2- dimetüültsüklopropaankarboksülaat (et)
m-Fenossibenżil (1RS,3RS;1RS,3SR)-3-(2,2-diklorovinil)-2,2-dimetilċiklopropankarbossilat (Permetrin) (mt)
m-fenoxibenzil 3-(2,2-diclorovinil)-2,2-dimetilciclopropan-carboxilat (ro)
m-fenoxibenzil-3-(2,2-diklórvinil)-2,2-dimetilciklopropánkarboxilát (hu)
m-fenoxybenzyl-3-(2,2-dichloorvinyl)-2,2-dimethylcyclopropaancarboxylaat (nl)
m-phenoxybenzyl-3-(2,2-dichlorvinyl)-2,2-dimethylcyclopropancarboxylat (da)
m-Phenoxybenzyl-3-(2,2-dichlorvinyl)-2,2-dimethylcyclopropancarboxylat (de)
m-феноксибензил 3-(2,2-дихлоровинил)-2,2-диметилциклопропанкарбоксилат (bg)
O-(3-fenoxybenzyl)-3-(2,2-dichlórvinyl)-2,2-dimetylcyklopropánkarboxylát (sk)
permethrin (ISO) (cs)
permethrin (ISO) (da)
Permethrin (ISO) (de)
permethrin (ISO) (el)
permethrin (ISO) (nl)
permetriin (ISO) (et)
Permetrin (hr)
permetrin (no)
permetrin (ISO) (hr)
permetrin (ISO) (hu)
permetrin (ISO) (ro)
permetrin (ISO) (sl)
permetrin (ISO) (sv)
permetrina (ISO) (es)
permetrina (ISO) (pt)
permetrinas (ISO) (lt)
permetrine (ISO) (it)
permetryna (ISO) (pl)
permetrín (ISO) (sk)
permetrīns (ISO) (lv)
perméthrine (ISO) (fr)
perméthrine (ISO);3-(2,2-dichorovinyl)-2,2-diméthylcyclopropanecarboxylate de m-phénoxybenzyle (fr)
перметрин (ISO) (bg)
CAS names
Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (3-phenoxyphenyl)methyl ester
IUPAC names
(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
(CIS+TRANS)-3-PHENOXYBENZYL 3-(2,2-DICHLOROETHENYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLATE
3-phenoxybenzyl (1RS)-cis,trans-3-(2,2-dichlorovinyl)- 2,2-dimethylcyclopropanecarboxylate
3-phenoxybenzyl (1RS)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
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 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
[3-(phenoxy)phenyl]methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
[3-(phenyloxy)phenyl]methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
Cyclopropanecarboxylic acid *3-(2,2-dichloroethenyl)-2,2-dimethyl-, (3-phenoxyphenyl)methylester
m-phenoxybenzyl (1RS,3RS,1SR,3SR-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
m-Phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
m-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
Permethrin
permethrin
permethrin (ISO
permethrin (ISO)
Permethrin(ISO);m-phenoxybenzyl3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
Permethrin
52645-53-1
Ambush
Transpermethrin
Pounce
Elimite
Imperator
NRDC-143
(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
UNII-509F88P9SZ
Hemoglobin atlanta-coventry
(+)-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
Ridect pour-on
CHEBI:34911
509F88P9SZ
1RS cis-Permethrin
52341-32-9
1RS,cis-Permethrin
NCGC00159390-02
1RS-trans-Permethrin
Kudos
Transpermethrin [ISO]
(+-)-cis-Permethrin
DSSTox_CID_2292
3-phenoxybenzyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
trans-(+-)-Permethrin
DSSTox_RID_76537
DSSTox_GSID_22292
3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid, (3-phenoxyphenyl) methyl ester
Permethrinum
S-3151
Chinetrin
Ecsumin
Efmethrin
Indothrin
Lyclear
NRDC 146
NRDC 148
Quamlin
Stomoxi
Cosair
Exmin
Exsmin
Ipitox
SBP-1513
(+-)-trans-Permethrin
Permethrine,c&t
(+-)-cis-Fmc 33297
Diffusil H
Insorbcid MP
Stomoxin P
Outflank-stockade
Perigen W
Dragnet FT
Picket G
Permethrin,racemic
[3-(phenyloxy)phenyl]methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
Mitin BC
Permanone 80
Permasect-25EC
FMC 35171
93389-07-2
SMR000778043
Kestrel (pesticide)
LE 79-519
Antiborer 3768
CAS-52645-53-1
Bematin 987
NRDC 143
Permethrinum [Latin]
Permetrin (Hungarian)
Permitrene (Hungarian)
Permetrina [Portuguese]
Caswell No. 652BB
FMC 33297
NIA 33297
PP 557
Permethrine [ISO-French]
BRN 4153590
Permethrn
SBP-1513TEC
Permethrin [USAN:INN:BAN]
AI3-29296
CCRIS 2001
ICI-PP 557
MP79
SBP 15131TEC
3-Phenoxybenzyl 2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate
HSDB 6790
m-Phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
BW-21-Z
S 3151
Cyclopropanecarboxylic acid, 3-(2,2-dichlorovinyl)-2,2-dimethyl-, (3-phenoxyphenyl)methyl ester, (1R-trans)-
OMS 1821
Hb Atlanta-coventry
EINECS 258-067-9
Elimite (TN)
FMC 41655
Hb At-Co
EPA Pesticide Chemical Code 109701
JF 7065
BRN 2063148
WL 43479
AI3-29158
Permethrin (USAN/INN)
CHEMBL1525
SCHEMBL26543
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-(+-)-
MLS001332525
MLS001332526
Permethrin [ANSI:BSI:ISO]
Permethrin cis/trans ~ 1:1
Permethrin, analytical standard
DTXSID8022292
SCHEMBL15218274
HMS2232L22
HMS3264N07
HMS3369D10
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)-
HY-B0887
Tox21_111627
Tox21_201586
Tox21_300691
BBL005484
MFCD00041809
NSC760105
s6461
STL135986
AKOS005746953
CCG-213703
DB04930
KS-5079
MCULE-1256227237
NSC 760105
NSC-760105
(+-)-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
Permethrin 10 microg/mL in Cyclohexane
Permethrin 100 microg/mL in Cyclohexane
(3-Phenoxyphenyl)methyl (+-)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
3-(Phenoxyphenyl)methyl (+-)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
52341-33-0
Permethrin (isomers), analytical standard
DB-052153
Total Permethrin 100 microg/mL in Acetone
Permethrin, PESTANAL(R), analytical standard
D05443
AB00918441_05
645P531
Q411635
J-523915
Permethrin (25:75), EuropePharmacopoeia (EP) Reference Standard
(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
Permethrin for system suitability, EuropePharmacopoeia (EP) Reference Standard
(3-Phenoxyphenyl)methyl (+-)cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
(3-Phenoxyphenyl)methyl (+/-)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
Cyclopropanecarboxylic acid, 3-(2,2-dichlorovinyl)-2,2-dimethyl-, 3-phenoxybenzyl ester, (+-)-, (cis,trans)-
Permethrin (isomers) solution, 100 mug/mL in acetonitrile, PESTANAL(R), analytical standard
Permethrin (isomers) solution, cis/trans isomers, 1000 mug/mL in methanol, analytical standard
Factory-Treated Clothing to Repel Insects
The only insect repellent currently used for factory treatment of clothing is permethrin.
Permethrin is a broad spectrum, non-systemic, synthetic pyrethroid insecticide that targets adults and larvae of many species of biting, chewing, scaling, soil, and flying invertebrates.
Permethrin is registered by the EPA as an insecticide for use in a variety of settings.
When used to pre-treat clothing, it is an insect repellent.
Permethrin has been registered since 1979.
Permethrin was first registered in 1990 for use as a repellent on clothing by the military.
At about the same time, we also approved permethrin as a spray for use on clothing and gear by consumers, as well as for commercial factory treatment of clothing and various types of gear.
In 2003, we first registered consumer-oriented, permethrin factory-treated clothing products.
More products have been approved since then.
Permethrin has been registered by the EPA since 1979.
Permethrin is currently registered and sold in a number of products such as residential indoor and outdoor insect foggers and sprays, treated clothing, flea products for dogs, termite treatments, agricultural and livestock products, and mosquito abatement products.
It is also regulated by the Food and Drug Administration as a treatment of head lice and scabies.
Permethrin is the most widely used mosquito adulticide in the U.S. and is used to treat 9 to 10 million acres annually (out of 32-39 million acres treated with a mosquito adulticide).
Permethrin’s widespread use can be attributed to its low cost, high effectiveness, low incidence of pest resistance, and broad labeling.
Permethrin is a pyrethroid insecticide that is similar to the natural insecticide, pyrethrum.
Pyrethrum is found in chrysanthemums. Permethrin can kill a broad range of pests, such as fleas, ticks, cockroaches, flies, and mosquitoes.
Products with permethrin commonly contain piperonyl butoxide (PBO).
The PBO increases the permethrin’s ability to control insects.
Permethrin and other pyrethroids work by overexciting the nervous system of insects, eventually causing the insect to die.
Where, when and how much permethrin may be applied?
Mosquito control programs carried out or guided by state or local agencies may apply permethrin from backpack sprayers, or sprayers mounted to trucks, or aircraft.
These programs apply permethrin as an ultra‐low volume (ULV) spray.
ULV sprayers put out very fine droplets that are small enough to stay airborne.
Permethrin kills mosquitoes when they contact the droplets.
The small droplet size improves the insect control, and also decreases the amount that may settle on surfaces where someone may contact it.
ULV sprayers use small amounts of permethrin to treat large areas
Generic Medicine Info
Indications and Dosage
Topical/Cutaneous
Head pediculosis
Adult: As 1% cream rinse or lotion: Before application, wash hair with a mild regular shampoo and towel dry. Apply sufficient amount to completely saturate the hair and scalp (especially behind the ears and nape of the neck). Leave on the hair for 10 minutes then rinse thoroughly with water; remove nits with fine-toothed comb as necessary. May repeat treatment 7-10 days after initial application if live lice or nits are found. Dosage and treatment recommendations may vary among individual products or between countries (refer to detailed product guideline).
Topical/Cutaneous
Scabies
Adult: As 5% cream: Apply a thin layer of up to 30 g to the whole body including the neck, palms of the hands and soles of the feet. The head and face may be left untreated unless indicated. As 5% lotion: Apply up to 50 mL from the neck to the soles of the feet. Re-apply if the cream or lotion on hands is washed with soap and water within 8 hours during the treatment period. Leave on the skin for approx 8-14 hours before washing off thoroughly. Generally, a single application is curative; but may repeat treatment at least 7 days after initial application if original lesions have no signs of healing, if live mites are present, or new skin lesions appear. Alternatively, re-treatment may be needed 14 days after 1st therapy if living mites are present. Dosage and treatment recommendations may vary among individual products or between countries (refer to detailed product guideline).
Child: As 5% cream: 2 months to <1 year Up to 3.75 g; ≥1-5 years Up to 7.5 g; 6-12 years Up to 15 g; >12 years Same as adult dose. As 5% lotion: 2 months to 1 year Up to 1/8 of a 50 mL bottle; 2-5 years Up to 1/4 of a 50 mL bottle; 6-12 years Up to 1/2 of a 50 mL bottle; >12 years Same as adult dose. Apply thinly to the whole body including the neck, palms of hands and soles of feet; infants should also be treated on the scalp, hairline, temple, ears, forehead and face. Leave on the skin for approx 8-14 hours before washing off thoroughly. Generally, a single application is curative; but may repeat treatment at least 7 days after initial application if original lesions have no signs of healing, if live mites are present, or new skin lesions appear. Alternatively, re-treatment may be needed 14 days after 1st therapy if living mites are present. Dosage and treatment recommendations may vary among individual products or between countries (refer to detailed product guideline).
Elderly: As 5% cream: Same as adult dose. Additionally, apply a thin layer on the scalp, hairline, forehead, temple, ears or face.
Topical/Cutaneous
Pediculosis pubis
Adult: As 5% cream: Apply sufficient amount (up to 30 g) to cover the pubic and peri-anal area, inner thighs down to the knee, and any hair that grows from the pubic area up to the stomach or chest. Allow the cream to dry then wash off thoroughly after 12 hours or after leaving on overnight. Dosage and treatment recommendations may vary among individual products or between countries (refer to detailed product guideline).
Contraindications
Hypersensitivity to permethrin, other pyrethroids, or pyrethrin.
Special Precautions
Scabies therapy: Persistent pruritus may be experienced after treatment; this reaction is usually not a sign of treatment failure and not a cause for re-treatment. Children (≥2 months) and elderly. Pregnancy and lactation.
Adverse Reactions
Significant: Hypersensitivity reactions; may temporarily exacerbate symptoms, such as oedema, that accompany scabies (5% cream).
General disorders and administration site conditions: Application site reactions (e.g. transient burning, numbness, stinging or tingling sensation).
Nervous system disorders: Paraesthesia.
Skin and subcutaneous tissue disorders: Pruritus, erythema, dry skin, rash.
OTHER PRODUCTS OF ATAMAN KIMYA THAT MIGHT BE OF INTEREST:
Benzyl benzoate
DEET