PRODUCTS

PERMETHRIN

EC / List no.: 258-067-9
CAS no.: 52645-53-1
Mol. formula: C21H20Cl2O3

Permethrin is a medication and an insecticide.
As a medication, it is used to treat scabies and lice.
Permethrin is applied to the skin as a cream or lotion.
As an insecticide, it can be sprayed onto clothing or mosquito nets to kill the insects that touch them.

Side effects include rash and irritation at the area of use.
Use during pregnancy appears to be safe.
Permethrin is approved for use on and around people over the age of two months.
Permethrin is in the pyrethroid family of medications.
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:
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.
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.
In pet flea preventive collars or treatment (safe for use on dogs but not cats)
In timber treatment

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.
Wash off the cream after 8–14 hours.
In general, one treatment is curative.

For treatment of head lice:
Apply to hair, scalp, and neck after shampooing. Leave in for 10 minutes and rinse.
Avoid contact with eyes.

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.

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.
Its degradation rate under indoor conditions is approximately 10% after 3 months

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.

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
Permethrin 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.
Permethrin is also highly persistent in soil.

Why is this medication prescribed?
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 works by killing lice and mites.

How should this medicine be used?
Permethrin comes as a cream to apply to the skin.
Over-the-counter permethrin comes as a lotion to apply to the scalp and hair.
Permethrin cream is usually applied to the skin in one treatment, but occasionally a second treatment is necessary.
Permethrin lotion is usually applied to the skin in one or two treatments, but occasionally three treatments are necessary.
If live mites are seen two weeks (14 days) after the first treatment with permethrin cream, then a second treatment should be applied.
If live lice are seen one week after the first treatment with over-the-counter permethrin lotion, then a second treatment should be applied.
Follow the directions on your prescription label or the package label carefully, and ask your doctor or pharmacist to explain any part you do not understand.
Use permethrin exactly as directed.
Do not use more or less of it or use it more often than prescribed by your doctor.

Permethrin should only be used on the skin or hair and scalp.
Avoid getting permethrin in your eyes, nose, ears, mouth, or vagina.
Do not use permethrin on your eyebrows or eyelashes.

If permethrin gets in your eyes, flush them with water right away.
If your eyes are still irritated after flushing with water, call your doctor or get medical help right away.

To use permethrin cream, follow these steps:
Apply a thin layer of cream all over your skin from your neck down to your toes (including the soles of your feet).
Be careful to apply cream in all skins folds, such as between your toes and fingers or around your waist or buttocks.
For treatment of babies or adults over 65 years of age, the cream should also be applied to the scalp or hairline, temples, and forehead.
You may need to use all of the cream in the tube to cover your body.
Leave the cream on your skin for 8-14 hours.
After 8-14 hours have passed, wash off the cream by bathing or showering.
Your skin may be itchy after treatment with permethrin cream.
This does not mean your treatment did not work.
If you see live mites 14 days or more after treatment, then you will need to repeat the treatment process.
To use the lotion, follow these steps:
Wash your hair with shampoo and rinse with water.
Do not use a conditioner or a shampoo that contains a conditioner because your treatment will not work as well.
Dry your hair with a towel until just damp.
Shake permethrin lotion well right before use to mix the medication evenly.
Use a towel to cover your face and eyes. Be sure to keep your eyes closed during this treatment.
You may need to have an adult help you apply the lotion.
Apply permethrin lotion to your hair and scalp area.
Begin to apply the lotion behind your ears and at the back of your neck and then cover all of the hair on your head and scalp.
Keep the lotion on your hair and scalp for 10 minutes after you finish applying permethrin lotion.
You should use a timer or clock to track the time.
Rinse your hair and scalp with warm water in a sink.
You should not use a shower or bathtub to rinse the lotion away because you do not want to get the lotion over the rest of your body.
Dry your hair with a towel and comb out tangles.
You and anyone who helped you apply the lotion should wash your hands carefully after the application and rinsing steps.
A lice comb may also be used to remove the dead lice and nits (empty egg shells) after this treatment. You may also need to have an adult help you to do this.
If you see live lice on your head 7 days or more after treatment, repeat this entire process.
After using permethrin, sanitize all the clothing, underwear, pajamas, hats, sheets, pillowcases, and towels you have used recently.
These items should be washed in very hot water or dry-cleaned.
You should also wash combs, brushes, hairs clips and other personal care items in hot water.

Ask your pharmacist or doctor for a copy of the manufacturer's information for the patient.

Other uses for this medicine
This medication may be prescribed for other uses; ask your doctor or pharmacist for more information.

What is permethrin?
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.

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).

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.

How might I be exposed to permethrin?
People can be exposed to pesticides by eating them, breathing them in, getting them on their skin, or getting them in their eyes.
Permethrin may be breathed in if a spray or fogger is used indoors, or if wind causes a spray or dust to be blown in someone's face.
Dogs may be exposed to permethrin in products that are applied to their skin for flea and tick treatments.
People can have skin exposure or breathe in products containing permethrin while applying the products, or during public health mosquito control efforts.
Permethrin may be eaten if people forget to wash their hands after using products that contain permethrin. Exposure to permethrin can be limited by reading the pesticide label and following all of the directions.

What happens to permethrin in the environment?
If permethrin gets into the soil, it is broken down by microorganisms.
Sunlight may also break down permethrin on the soil surface and on the surface of water.
Permethrin does not mix well with water.
When permethrin gets into surface water like lakes or streams, it sticks very strongly to sediment and can stay there for more than a year.
Since permethrin sticks to sediment and does not mix well with water, it won't usually contaminate groundwater.
Permethrin does not evaporate very easily when it is applied to surfaces.
Permethrin was applied indoors near a window in an experiment where it was exposed to daylight.
After 20 days, 60% of the permethrin that was applied was still on the surface.

This medication is for use on the skin only.
Apply this medication as soon as possible after it is prescribed.
Apply the medicine from your head to the soles of your feet, including under your nails and in skin folds such as between the toes, as directed. Massage the cream into the skin.
Do not use more medication than prescribed. Wash off the cream after 8-14 hours by showering or taking a bath.

Avoid getting the cream into your eyes, nose, mouth, or vagina.
If the medication gets in your eyes, flush the eyes with plenty of water. Consult your doctor if irritation persists.

Symptoms of scabies include an intense itching that is usually worse at bedtime.
You may also see small, fine, wavy lines on the skin with a tiny insect at the end (a burrow).
Burrows are usually found on finger/toe webs, wrists, elbows, armpits, belt line, lower buttocks, female nipples, or male genitals.
Even if permethrin kills all the scabies, the dead mites can still make you itch for up to 4 weeks after treatment.
Ask your doctor about other medications that may be used to soothe the itching.
Inform your doctor if your condition persists or worsens 2 weeks after treatment.
Your doctor may need to look for living mites and recommend more treatment.

Yellow-brown to brown liquid, which sometimes tends to crystallize at room temperature (technical grade).

Permethrin, a pyrethroid insecticide with little mammalian toxicity, has been marketed as a tick repellent. Permethrin is the only synthetic pyrethroid that is used worldwide for head lice. The spray formulation is the most widely available form. Once applied to clothing, it is stable through several wash cycles. Permethrin is also suitable for treating sleeping bags, tents, and fabric used for insect screening. A liquid concentrate has been used to impregnate fabric for as long as the life of the garment. Permethrin is particularly helpful in the prevention of tick and chigger bites. These crawling arthropods must travel across the treated fabric, whereas flying insects tend to be attracted directly to exposed skin. The combination of a DEET-containing repellent and permethrin-treated clothing is generally highly ffective against a wide range of biting arthropods.

Chemical Properties
Crystalline Solid

Uses:
Permethrin is a synthetic pyrethroid active against lice, ticks, mites, and fleas.
Permethrin acts on neural cellmembranes, delaying repolarization and causing paralysis.
The compound has no reported adverse properties, is heat and light stable, has 70% to 80% ovicidal activity, and leaves an active residue on the scalp.
Permethrin is 26 times less toxic than lindane and 3 times less toxic than pyrethrins.
A 1% permethrin cream rinse (Nix) preparation with a single application was determined to be more effective than treatment with RID.
Permethrin-treated military uniforms are effective against human body lice.
Apply the cream rinse for 10 minutes and rinse off with water.
Localized pruritus may be reported with use of this product.
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); antihyperlipidemic; cholesterol sequestrant.

Indications
Permethrin is a synthetic pyrethroid active against lice, ticks, mites, and fleas.
Permethrin acts on neural cellmembranes, delaying repolarization and causing paralysis.
The compound has no reported adverse properties, is heat and light stable, has 70% to 80% ovicidal activity, and leaves an active residue on the scalp.

Permethrin 0.5% spray kills ticks and repels mosquitoes and stable flies.
Permethrin is broken down when applied to skin and, hence, should be applied to clothing, shoes, tents, and so on. Spray only enough to moisten the material. Spray on clothing at least 2 hours before wearing. One treatment should last through a few washings.

Pharmacology
Permethrin is a synthetic pyrethroid that interferes with the influx of sodium through cell membranes, leading to neurologic paralysis and death of the mite.
There is minimal percutaneous absorption (<2%), which is rapidly hydrolyzed and excreted in the urine.
Permethrin 5% dermal cream (Elimite) is applied for 8 to 12 hours to the entire body from the chin down and is then washed off.

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.
Permethrin 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.
Permethrin acts on the nerve cell membranes of the parasitesto disrupt sodium channel conductance.
Permethrin 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.

Metabolic pathway
Permethrin was one of the first photostable pyrethroids suitable for field use.
Permethrin 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.
Permethrin 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.

Degradation
Permethrin is stable as a solid but it is readily hydrolysed in solution under alkaline conditions; it is most stable at pH 4.
Permethrin is relatively resistant to photodegradation in the context of field use but it undergoes facile photoisomerism (Holmstead et al., 1978).
Permethrin 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.

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.

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

SYNONYMS:
(+-)-,(cis,trans)-yleste
(3-phenoxyphenyl)methyl3-(2,2-dichlorethenyl)-2,2-dimethylcyclopropanecarbox
(3-Phenoxyphenyl)methyl-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
(3-phenoxyphenyl)methyl3-(2,2-dichloroethyl)-2,2-dimethylcyclopropane-carboxy
(3-phenoxyphenyl)methyl-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-carboxy
-1-carboxylate
3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylicacid(3-phenoxyphen
SPARTAN
PERMETHRIN-25EC
TRANS-PERMETHERIN
(3-PHENOXYPHENYL)METHYL(+-)CIS,TRANS-3-(2,2-DICHLOROETHENY.
BIOMIST
permethrin (ISO) m-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
M-(Phenoxy-d5)benzyl 3-(2,2-Dichlorovinyl)-2,2- diMethylcyclopropanecarboxylate
NIA-33297-d5
PerManone-d5
PerMethrin-d5 (cis/trans Mixture)
Spartan-d5
3-Phenoxybenyl-3(-2,2-dichlorinyl-2,2-(dimethylcyclopropane carbonate
perMetrhrin
m-Phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
PERMETHRIN
PERMETHRINE (CIS/TRANS)
(.+/-.)-3-Phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
(.+/-.)-m-Phenoxybenzyl-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-carboxylate
3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylicacid,(3-phenoxyphen
3-(2,2-dichlorovinyl)-2,2-dimethyl-cyclopropanecarboxylicaci3-phenoxybenz
3-(Phenoxyphenyl)methyl
3-(phenoxyphenyl)methyl(+-)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyc
3-Phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
3-phenoxybenzyl(+-)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylat
3-phenoxybenzyl(+-)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane
3-phenoxybenzyl(1rs)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanec
3-phenoxybenzyldl-cis/trans-3-(2,2-dichlorovinyl)-2,2-dimethyl-1-cyclopropan
PERMETHRIN, 250MG, NEAT
EPA PERMETHRIN CIS/TRANS ISOMERS 1X1ML M EOH 1000UG/ML
PERMETHRIN MIXTURE OF CIS AND TRANS ISOM
PERMETHRIN, 100MG, NEAT
3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropancarboxylicacid(3-phenoxyphenyl)methylester
Outflank[R]
Permasect[R]
Talcord[R]
FMC-33297, NIA-33297, NRDC-143, PP-557, SBP-1513, Ambush, Corsair, Dragnet, Ectiban, Eksmin, Nix, Pounce, Permasect, Ridect,
Permethrin (cis / trans mixture)
PENMETHRIN
permethrin (bsi,iso,ansi,esa,ban)
permethrin (isomers)
permethrin (isomers) solution
Adion
ai3-29158
Ambushfog
anomethrinn
antiborer3768
Atroban
bematin987
Bio flydown
bw-21-z
chinetrin
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-stockad
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 415390
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
Cyclopopanecarboxylic 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-(+-)-
Permethrin [ANSI:BSI:ISO]
Permethrin cis/trans ~ 1:1
Permethrin, analytical standard
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
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
Total Permethrin 100 microg/mL in Acetone
Permethrin, PESTANAL(R), analytical standard
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
Cyclopropancarboxylic 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