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 Image File history File links Size of this preview: 800 × 264 pixelsFull resolution (1100 × 363 pixel, file size: 21 KB, MIME type: image/png) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Permethrin ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... The International Union of Pure and Applied Chemistry (IUPAC) is an international non-governmental organization devoted to the advancement of chemistry. ... Chemical Abstracts Service (CAS) is a division of the American Chemical Society, and produces Chemical Abstracts, and related products. ...
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	0 1 0
Flash point	?°C
R/S statement	R: R36 R37 R38 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) Infobox disclaimer and references

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. This article does not cite any references or sources. ... This article or section does not cite any references or sources. ... Color is an important part of the visual arts. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... In physics, density is mass m per unit volume V. For the common case of a homogeneous substance, it is expressed as: where, in SI units: ρ (rho) is the density of the substance, measured in kg·m-3 m is the mass of the substance, measured in kg V is... In the physical sciences, a phase is a set of states of a macroscopic physical system that have relatively uniform chemical composition and physical properties (i. ... Solubility refers to the ability for a given substance, the solute, to dissolve in a solvent. ... This article describes water from a scientific and technical perspective. ... Parts per million (ppm) is a measure of concentration that is used where low levels of concentration are significant. ... The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ... Italic text This article is about the boiling point of liquids. ... An example MSDS in a US format provides guidance for handling a hazardous substance and information on its composition and properties. ... The examples and perspective in this article or section may not represent a worldwide view. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... Image File history File links NFPA_704. ... The flash point of a flammable liquid is the lowest temperature at which it can form an ignitable mixture with air. ... Risk and Safety Statements, also known as R/S statements, R/S numbers, R/S phrases, and R/S sentences, is a system of hazard codes and phrases for labeling dangerous chemicals and compounds. ... R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... A pyrethroid is a synthetic chemical that kills most insects. ... Bifenthrin or (2-methyl-1,1-biphenyl-3-y1)-methyl-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl cyclopropanecarboxylate (CAS number 82657-04-3) is a pyrethroid insecticide that affects the nervous system of insects. ... Deltamethrin is a pyrethroid ester insecticide. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... In chemistry, chemical synthesis is purposeful execution of chemical reactions in order to get a product, or several products. ... An insecticide is a pesticide used against insects in all developmental forms. ... Families Tetranychidae - Spider mites Eriophyidae - Gall mites Sarcoptidae - Sarcoptic Mange mites The mites and ticks, order Acarina or Acari, belong to the Arachnida and are among the most diverse and successful of all the invertebrate groups, although some way behind the insects. ... Commercial insect repellents A mosquito biting a human An insect repellent is a substance applied to skin, clothing, or other surfaces which discourages insects (and arthropods in general) from landing or climbing on that surface. ... A pyrethroid is a synthetic chemical that kills most insects. ... A neurotoxin is a toxin that acts specifically on nerve cells – neurons – usually by interacting with membrane proteins and ion channels. ... Drawing by Santiago Ramón y Cajal of neurons in the pigeon cerebellum. ... The cell membrane (also called the plasma membrane, plasmalemma or phospholipid bilayer) is a semipermeable lipid bilayer common to all living cells. ...

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. Cotton ready for harvest. ... Species T. aestivum T. boeoticum T. compactum T. dicoccoides T. dicoccon T. durum T. monococcum T. spelta T. sphaerococcum T. timopheevii References:   ITIS 42236 2002-09-22 For the indie rock group see: Wheat (band). ... “Corn” redirects here. ... Binomial name Medicago sativa L. Subspecies subsp. ... A parasite is an organism that spends a significant portion of its life in or on the living tissue of a host organism and which causes harm to the host without immediately killing it. ... This article or section does not adequately cite its references or sources. ... This article or section does not cite its references or sources. ... The term broad-spectrum antibiotic refers to an antibiotic with activity against a wide range of disease-causing bacteria. ... The honeybee is a colonial insect that is often maintained, fed, and transported by farmers. ... Feral mouse A mouse (plural mice) is a rodent that belongs to one of numerous species of small mammals. ...

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, www.ticktubes.com. Mice collect the cotton for lining their nests, and the pesticide on the cotton kills any immature ticks that are feeding on the mice.^[2] Families Ixodidae - Hard ticks Argasidae - Soft ticks Tick is the common name for the small wingless arachnids that, along with mites, constitute the order Acarina. ...

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. The head louse Head lice (Pediculus humanus capitis) are one of the many varieties of sucking lice (singular louse) specialized to live on different areas of various animals. ... Subfamilies Aenictogitoninae Agroecomyrmecinae Amblyoponinae (incl. ... Families Mastotermitidae Kalotermitidae Termopsidae Hodotermitidae Rhinotermitidae Serritermitidae Termitidae Termites, sometimes known as white ants, are a group of eusocial insects usually classified at the taxonomic rank of order, Isoptera. ...

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." ^[3]

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. Diversity 41 genera Genera See text. ... Dengue fever (IPA: ) and dengue hemorrhagic fever (DHF) are acute febrile diseases, found in the tropics, with a geographical spread similar to malaria. ... Malaria is a vector-borne infectious disease that is widespread in tropical and subtropical regions, including parts of the Americas, Asia, and Africa. ...

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: The head louse Head lice (Pediculus humanus capitis) are one of the many varieties of sucking lice (singular louse) specialized to live on different areas of various animals. ... Suborders Anoplura (sucking lice) Rhyncophthirina Ischnocera (avian lice) Amblycera (chewing lice) Lice (singular: louse) (order Phthiraptera) are an order of over 3000 species of wingless parasitic insects. ... The head louse Head lice (Pediculus humanus capitis) are one of the many varieties of sucking lice (singular louse) specialized to live on different areas of various animals. ... Genera Genus Cimex Lectularius Hemipterus (Rotundatus) Pilosellus Pipistrella Genus Leptocimex Boueti Genus Haematosiphon Inodora Genus Oeciacus Hirudinis Vicarius Bedbugs (or bed bugs) are small nocturnal insects of the family Cimicidae that feed on the blood of humans and other hosts. ... Families Tetranychidae - Spider mites Eriophyidae - Gall mites Sarcoptidae - Sarcoptic Mange mites The mites and ticks, order Acarina or Acari, belong to the Arachnida and are among the most diverse and successful of all the invertebrate groups, although some way behind the insects. ... An American-looking gaff cutter with a genoa jib set This French yawl has a gaff topsail set. ...

• Raid fumigator

Image:RAID ant and roach. ...

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. Main article: stereochemistry Stereoisomerism is the arrangement of atoms in molecules whose connectivity remains the same but their arrangement in space is different in each isomer. ... In chemistry, enantiomers (from the Greek ἐνάντιος, opposite, and μέρος, part or portion) are stereoisomers that are nonsuperimposable complete mirror images of each other, much as ones left and right hands are the same but opposite. ... A stereocenter in organic chemistry generally refers to a carbon atom in a chemical compound that has four different types of atoms or groups of atoms attached to it. ... Molecule structure formula of cyclopropane Cyclopropane is a cycloalkane molecule with the molecular formula C3H6 consisting of three carbon atoms linked to each other to form a ring, with each carbon atom bearing two hydrogen atoms. ... Trans is a Latin noun or prefix, meaning across, beyond or on the opposite side [of] . It is the opposite of cis, which means on the same side [of]. In chemistry, a double bond (or ring) not subject to free rotation in which the greater radical on both ends is...

(1R)-trans-acid moiety, known as biopermethrin

(1S)-trans-acid moiety

one cis enantiomer

the other cis enantiomer

Image File history File links Size of this preview: 800 × 265 pixelsFull resolution (1100 × 364 pixel, file size: 21 KB, MIME type: image/png) Afterwards please add the following code to : (Please review the discussion here. ... Image File history File links This is a lossless scalable vector image. ... Image File history File links Size of this preview: 800 × 264 pixelsFull resolution (1100 × 363 pixel, file size: 21 KB, MIME type: image/png) Afterwards please add the following code to : (Please review the discussion here. ... In chemistry, enantiomers (from the Greek ἐνάντιος, opposite, and μέρος, part or portion) are stereoisomers that are nonsuperimposable complete mirror images of each other, much as ones left and right hands are the same but opposite. ... Image File history File links Size of this preview: 800 × 264 pixelsFull resolution (1100 × 363 pixel, file size: 21 KB, MIME type: image/png) Afterwards please add the following code to : (Please review the discussion here. ...

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. Fipronil is the active ingredient in Frontline, a topical flea control commonly used on dogs and cats. ...

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)^[4]. 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 ^[5][6]. However, these results are seen as preliminary and marginal, at best.

References

1. ^ "Aquatic Organisms and Pyrethroids" Journal of Pest Management Science
2. ^ Protecting Property from Tick Infestation: Damminix [1] University of Maryland Medical Center
3. ^ Tick bite prevention Connecticut Department of Public Health
4. ^ [2]US EPA List of Chemicals Evaluated for Carcinogenic Potential
5. ^ M. Tisch, P. Schmezer, M. Faulde, A. Groh, Heinz Maier, Genotoxicity studies on permethrin, DEET and diazinon in primary human nasal mucosal cells, European Archives of Oto-Rhino-Laryngology, V. 259 No. 3, March 2002.
6. ^ K. Hakoi, Dr. R. Cabral, T. Hoshiya, R. Hasegawa, T. Shirai, Dr. N. Ito, Analysis of carcinogenic activity of some pesticides in a medium-term liver bioassay in the rat, Teratogenesis, Carcinogenesis, and Mutagenesis, V. 12 No. 6, published on-line Sept. 9, 2005.

See also

• Methoprene

Methoprene is a general use insecticide that acts as a growth regulator. ...

External links

• Permethrin chemical data
• Example of permethrin river poisoning