PERMETHRIN

Permethrin
Chemical structure of permethrin
'General'
Systematic name	IUPAC: 3-Phenoxybenzyl (1RS)-cis,trans-3-(2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate CAS: (3-Phenoxyphenyl)methyl (1RS)-cis,trans-3-(2,2-dichloroethenyl) -2,2-dimethylcyclopropanecarboxylate
SMILES	c3ccccc3Oc(c2)cccc2COC(=O) C1C(C1(C)C)C=C(Cl)Cl
Chemical formula	C21H20Cl2O3
Appearance	Colourless crystals
Molar mass	391.28 g/mol
Properties
Density and phase	1.19 g/cm³, solid
Solubility in water	Insoluble (5.5 x 10-3 ppm)
Melting point	34 °C (307 K)
Boiling point	200 °C (473 K)
Hazards
MSDS	External MSDS
Main hazards	Irritating to skin and eyes, damaging to lungs
NFPA 704
Flash point	?°C
R/S statement	R: S: ?
RTECS number	?
Related compounds
Related pyrethroids	Bifenthrin Deltamethrin
Related compounds	?
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

'Permethrin' is a common synthetic chemical, widely used as an insecticide and acaricide and as an insect repellent. It belongs to the family of synthetic chemicals called pyrethroids and functions as a neurotoxin, affecting neuron membranes by prolonging sodium channel activation.

Contents

Uses

Products containing permethrin

Stereochemistry

Toxicity

References

See also

External links

Uses

In agriculture, Permethrin is mainly used on cotton, wheat, maize, and alfalfa crops, and is also used to kill parasites on chickens and other poultry. Its use is controversial since, as a broad-spectrum chemical, it kills indiscriminately; as well as the intended pests, it can harm beneficial insects including honey bees, aquatic life,^[1] and small mammals such as mice.
However, permethrin can be used in a targeted manner as well. This is the basis for a method of reducing populations of the deer tick ''Ixodes scapularis'' (''I. dammini''). Biodegradable cardboard tubes stuffed with permethrin-treated cotton, are sold under the brand name ''Damminix'',^[2] Mice collect the cotton for lining their nests, and the pesticide on the cotton kills any immature ticks that are feeding on the mice.^[3]
Permethrin is also used in healthcare, to eradicate parasites such as head lice and mites responsible for scabies, and in industrial and domestic settings to control pests such as ants and termites.
Permethrin kills ticks on contact with treated clothing. According to the Connecticut Department of Public Health, it "has low mammalian toxicity, is poorly absorbed through the skin and is rapidly inactivated by the body. Skin reactions have been uncommon." ^[4]
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. Military personnel training in malaria-endemic areas may be instructed to treat their uniforms with permethrin as well. An application should last several washes.
Recently, in South Africa, residues of permethrin was found in breast milk, together with DDT, in an area that experience DDT treatment for malaria control, as well as the use of pyrethroids in small-scale agriculture.^[5]

Products containing permethrin

Products containing 0.5% permethrin:

★ Repel Permanone

★

★ Permethrin Tick Repellent

★ Bonide Ant Dust (0.25%)

★ Nix 1% shampoo for head lice.

★ Elimite 5% skin cream or generic equilvalent for scabies, lice, head lice, bird mites, tropical rat mites, bed bugs, and other mites.

★ Most flea and tick repellant for dogs (Adams, Bio-Spot, K9-Advantix, Cutter)

★ Dragnet, a pesticide for home use, also contains permethrin.

★ Cutter Bug Free Backyard


Products containing 12.6% permethrin:

★ Raid fumigator

Stereochemistry

Permethrin has four stereoisomers (two enantiomeric pairs), arising from the two stereocentres in the cyclopropane ring. The ''trans'' enantiomeric pair is known as 'transpermethrin'.

Toxicity

Permethrin is extremely toxic to fish. Extreme care must be taken when using products containing permethrin near water sources.
Permethrin is also highly toxic to cats. Flea and tick repellent formulas intended (and labeled) for dogs may contain permethin and cause feline permethrin toxicosis in cats: specific flea and tick control formulas intended for feline use, such as those containing fipronil, should therefore be used for cats instead.
Currently, permethrin is not considered a carcinogen by any recognized authoritative body, but a few studies have lead the US EPA to classify the substance as a Category C carcinogen: Possible human carcinogen (the data show limited evidence of carcinogenicity in the absence of human data)^[6]. Carcinogenic action in nasal mucosal cells for inhalation exposure is suspected due to observed genotoxicity in human tissue samples, and in rat livers the evidence of increased preneoplastic lesions lends concern over oral exposure.^[7][8] However, these results are seen as preliminary and marginal, at best.

References

1. Aquatic organisms and pyrethroids, R. H. Ian, , , Pesticide Science, 1989
2. Damminix Tick Tubes (Official site)
3.
4. Tick Bite Prevention Kirby C. Stafford III
5. Simultaneous presence of DDT and pyrethroid residues in human breast milk from a malaria endemic area in South Africa, H. Bouwman, B. Sereda and H. M. Meinhardt, , , Environmental Pollution, 2006
6. [1]US EPA List of Chemicals Evaluated for Carcinogenic Potential
7. Genotoxicity studies on permethrin, DEET and diazinon in primary human nasal mucosal cells, M. Tisch, P. Schmezer, M. Faulde, A. Groh and H. Maier, , , European Archives of Oto-Rhino-Laryngology, 2002
8. Analysis of carcinogenic activity of some pesticides in a medium-term liver bioassay in the rat, K. Hakoi, R. Cabral, T. Hoshiya, R. Hasegawa, T. Shirai and N. Ito, , , Teratogenesis, Carcinogenesis, and Mutagenesis, 1992

See also

★ Methoprene

External links

★ Permethrin chemical data

★ Example of permethrin river poisoning