N,N-diethyl-m-toluamide, abbreviated DEET, is an insect repellent chemical. It is intended to be applied to the skin or to clothing, and is primarily used to protect against insect bites. In particular, DEET protects against tick bites (which transmit Lyme disease) and mosquito bites (which transmit dengue fever, West Nile virus, Eastern Equine Encephalitis (EEE), and malaria). In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... Mosquito on a bottle of herbal mosquito repellent. ... Orders Subclass Apterygota Archaeognatha (bristletails) Thysanura (silverfish) Subclass Pterygota Infraclass Paleoptera (Probably paraphyletic) Ephemeroptera (mayflies) Odonata (dragonflies and damselflies) Infraclass Neoptera Superorder Exopterygota Grylloblattodea (ice-crawlers) Mantophasmatodea (gladiators) Plecoptera (stoneflies) Embioptera (webspinners) Zoraptera (angel insects) Dermaptera (earwigs) Orthoptera (grasshoppers, etc) Phasmatodea (stick insects) Blattodea (cockroaches) Isoptera (termites) Mantodea (mantids) Psocoptera... Families Ixodidae - Hard ticks Argasidae - Soft ticks Nuttalliellidae - ????? ticks Wikispecies has information related to: Ixodoidea Tick is the common name for the small arachnids that, along with other mites, constitute the order Acarina. ... Common bullseye rash pattern associated with Lyme Disease. ... For other uses, see Mosquito (disambiguation). ... Dengue fever (IPA: ) and dengue hemorrhagic fever (DHF) are acute febrile diseases, found in the tropics, with a geographical spread similar to malaria. ... West Nile virus (WNV) is a virus of the family Flaviviridae; part of the Japanese encephalitis (JE) antigenic complex of viruses, it is found in both tropical and temperate regions. ... Eastern equine encephalitis virus (EEEV), commonly called sleeping sickness or Triple E, is a zoonotic alphavirus and arbovirus present in North, Central and South America and the Caribbean. ... Malaria is a vector-borne infectious disease caused by protozoan parasites. ...

DEET is believed to work by blocking insect receptors (notably those which detect carbon dioxide and lactic acid) which are used to locate hosts. DEET effectively "blinds" the insect's senses so the biting/feeding instinct is not triggered by humans or animals which produce these chemicals. Carbon dioxide is a chemical compound composed of two oxygen atoms covalently bonded to a single carbon atom. ... For the production of milk by mammals, see Lactation. ...

History

DEET was developed by the United States Army, following its experience of jungle warfare during World War II. It entered military use in 1946 and civilian use in 1957. The United States Army is the largest and oldest branch of the armed forces of the United States. ... Jungle warfare is a term used to cover the special techniques needed for military units to survive and fight in jungle terrain. ... Combatants Allied powers: China France Great Britain Soviet Union United States and others Axis powers: Germany Italy Japan and others Commanders Chiang Kai-shek Charles de Gaulle Winston Churchill Joseph Stalin Franklin Roosevelt Adolf Hitler Benito Mussolini Hideki Tōjō Casualties Military dead: 17,000,000 Civilian dead: 33,000... Year 1957 (MCMLVII) was a common year starting on Tuesday (link displays the 1957 Gregorian calendar). ...

Chemistry

A slightly yellow liquid at room temperature, it can be prepared from m-methylbenzoic acid and diethylamine. This can be achieved by preparing the acid chloride and subsequently reacting that with the diethylamine. It can be distilled under vacuum: b.p. 111 ^oC at 1 mm Hg. It is considered a mild irritant. Diethylamine is a secondary amine with the molecular structure CH3CH2NHCH2CH3. ...

Concentrations

DEET is available in many insect repellents

DEET is often sold and used in concentrations up to 100%. Consumer Reports found a direct correlation between DEET concentration and hours of protection against insect bites. 100% DEET was found to offer up to 12 hours of protection while several lower concentration DEET formulations (20%-34%) offered 3-6 hours of protection.^[1] Other research has corroborated the effectiveness of DEET.^[2] USDA photo by Scott Bauer. ... USDA photo by Scott Bauer. ... Consumer Reports is an American magazine published monthly by Consumers Union. ...

Effects on health

DEET is the most common active ingredient in insect repellents.

The American Academy of Pediatrics found no difference in safety for children, between products containing 10% and 30% DEET, when used as directed, but recommends that DEET not be used on infants less than two months old.^[3]

As a precaution, manufacturers advise that DEET products should not be used under clothing, on damaged skin, and that preparations be washed off after they are no longer needed or between applications.^[3] In rare cases, it may cause skin reactions.^[3]

In the DEET Reregistration Eligibility Decision (RED) the EPA reported 14 to 46 cases of potential DEET associated seizures, including 4 deaths. The EPA states: " ..it does appear that some cases are likely related to DEET toxicity," but observed that with 30% of the US population using DEET, the likely seizure rate is only about one per 100 million users.^[4] EPA redirects here. ... This article is about the medical condition. ... // Toxic and Intoxicated redirect here – toxic has other uses, which can be found at Toxicity (disambiguation); for the state of being intoxicated by alcohol see Drunkenness. ...

The Pesticide Information Project of Cooperative Extension Offices of Cornell University states that "Everglades National Park employees having extensive Deet exposure were more likely to have insomnia, mood disturbances and impaired cognitive function than were lesser exposed co-workers". ^[5] “Cornell” redirects here. ... Everglades National Park preserves the southern portion of the Everglades (all south of Tamiami Trail), but represents only 20 % of the original wetland area. ...

Effects on materials

DEET is an effective solvent which may dissolve (part of) some plastics, rayon, spandex, other synthetic fabrics, leather, and painted or varnished surfaces.^{[citation needed]} A solvent is a liquid that dissolves a solid, liquid, or gaseous solute, resulting in a solution. ... The term plastics covers a range of synthetic or semi-synthetic organic condensation or polymerization products that can be molded or extruded into objects or films or fibers. ... Rayon is a manufactured regenerated cellulosic fiber. ... Example of spandex Spandex or elastane is a synthetic fiber known for its exceptional elasticity (stretchability). ... Synthetic fibers are the result of extensive research by scientists to increase and improve upon the supply of naturally occurring animal and plant fibers that have been used in making cloth and rope. ... Modern leather-working tools Leather is a material created through the tanning of hides and skins of animals, primarily cattlehide. ... Varnish is a transparent, hard, protective finish or film primarily used in wood finishing but also for other materials. ...

Effects on the environment

Although few studies have been conducted to assess possible effects on the environment, DEET is a moderate chemical pesticide and may not be suitable for use in and around water sources. Though DEET is not expected to bioaccumulate, it has been found to have a slight toxicity for coldwater fish such as the rainbow trout^[6] and the tilapia ^[7], and it has also been shown to be toxic for some species of freshwater zooplankton.^[8] DEET has been detected in significant levels in waterbodies as a result of production and use, such as in the Mississippi River and its tributaries, where a 1991 study detected levels varying from 5 to 201 ng/L. ^[9] A cropduster spreading pesticide. ... If the input of a toxic substance to an organism is greater than the rate at which the substance is lost, the organism is said to be bioaccumulating that substance. ... For other uses, see Fish (disambiguation). ... It has been suggested that Steelhead be merged into this article or section. ... Genera Oreochromis (about 30 species) Sarotherodon (over 10 species) Tilapia (about 40 species) and see text Tilapia is the common name for nearly 100 species of cichlid fishes from the tilapiine cichlid tribe. ... Photomontage of plankton organisms Plankton is the aggregate community of weakly swimming but mostly drifting small organisms that inhabit the water column of the ocean, seas, and bodies of freshwater. ... For the river in Canada, see Mississippi River (Ontario). ... The nanogram is an SI unit of mass (symbol ng) defined as: 1 ng = 1 × 10-12 kilogram (1 × 10-9 gram) A nanogram is one billionth (1/1,000,000,000) of a gram. ...

Natural alternatives

Some essential oil based insect repellents offer an alternative to DEET. While most are not as effective as DEET,^[10][11] research shows that other essential oil based formulas are comparable to DEET, and somewhat better. ^[12] An essential oil is a concentrated, hydrophobic liquid containing volatile aromatic compounds from plants. ...

A test of various marketed insect repellents by an independent consumer organization found that synthetic repellents, including DEET, were more effective than repellents with ‘natural’ active ingredients. All the synthetics gave almost 100% repellency for the first 2 hours, where the natural repellent products were most effective for the first 30-60 minutes and required reapplication to be effective over several hours.^[13]

Citronella oil has been used as an insect repellent for 60 years.^[14] Its mosquito repellency qualities have been verified by research,^{[15] [16][17]} however, the efficiency of DEET is much greater.^{[citation needed]} Citronella oil is one of the important essential oils obtained from different species of Cymbopogon. ...

Products marketed against mosquito bites include catnip, but this product does not significantly reduce mosquito bites.^[18] It has been suggested that this article or section be merged with Nepeta. ...

References

• M. S. Fradin (1998). "Mosquitoes and Mosquito Repellents: A Clinician's Guide". Ann Intern Med 128 (11): 931-940. 

1. ^ Matsuda, Brent M.; Surgeoner, Gordon A.; Heal, James D.; Tucker, Arthur O.; Maciarello, Michael J. (1996). "Essential oil analysis and field evaluation of the citrosa plant "Pelargonium citrosum" as a repellent against populations of Aedes mosquitoes.". Journal of the American Mosquito Control Association 12 (1): 69-74. 
2. ^ University of North Carolina (3 Jul 02). Independent study: DEET products superior for fending off mosquito bites. Press release.
3. ^ ^{a b c} Insect Repellent Use and Safety. West Nile Virus. Centers for Disease Control and Prevention (12 Jan 07).
4. ^ "Reregistration Eligibility Decision: DEET." U.S. Environmental Protection Agency, Office of Prevention, Pesticides, and Toxic Substances. September 1998. pp39-40
5. ^ http://pmep.cce.cornell.edu/profiles/extoxnet/carbaryl-dicrotophos/deet-ext.html
6. ^ U.S. Environmental Protection Agency. 1980. Office of Pesticides and Toxic Substances. N,N-diethyl-m-toluamide (Deet) Pesticide Registration Standard. December, 1980. 83 pp.. Retrieved on July 20.
7. ^ Mathai, AT; Pillai, KS; Deshmukh, PB (1989). "Acute toxicity of deet to a freshwater fish, Tilapia mossambica : Effect on tissue glutathione levels.". Journal of Environmental Biology 10 (2): 87-91.. 
8. ^ J. Seo, Y. G. Lee, S. D. Kim, C. J. Cha, J. H. Ahn and H. G. Hur (2005). "Biodegradation of the Insecticide N,N-Diethyl-m-Toluamide by Fungi: Identification and Toxicity of Metabolites". Archives of Environmental Contamination and Toxicology 48 (3): 323-328. DOI:10.1007/s00244-004-0029-9. 
9. ^ Errol Zeiger, Raymond Tice, Brigette Brevard, (1999) N,N-Diethyl-m-toluamide (DEET) [134-62-3 - Review of Toxicological Literature]. Retrieved on July 20.
10. ^ M. S. Fradin and J. F. Day (2002). "Comparative Efficacy of Insect Repellents against Mosquito Bites". N Engl J Med 347 (1): 13-18. DOI:10.1056/NEJMoa011699. 
11. ^ Collins, D.A.; Brady, J.N.; Curtis, C.F. (1993). "Assessment of the efficacy of Quwenling as a Mosquito repellent". Phytotherapy Research 7 (1): 17-20. 
12. ^ Trongtokit Y.; Rongsriyam Y, Komalamisra N, Krisadaphong P, Apiwathnasorn C, Krisadaphong P, Apiwathasorn C, (2004). "Laboratory and field trial of developing medicinal local Thai plant products against four species of misquito vectors". Southeast Asia J, Trop Med Public Health 35 (2): 325-33. PMID 15691131. 
13. ^ "Test: Mosquito Repellents, The Verdict" Choice, The Australian Consumers Association
14. ^ Citronella (Oil of Citronella) (021901) Fact Sheet. U.S. Environmental Protection Agency (Nov 1999). Retrieved on July 20, 2007.
15. ^ Jeong-Kyu KIM, Chang-Soo KANG, Jong-Kwon LEE, Young-Ran KIM, Hye-Yun HAN, Hwa Kyung YUN (2005). "Evaluation of Repellency Effect of Two Natural Aroma Mosquito Repellent Compounds, Citronella and Citronellal". Entomological Research 35 (2): 117-120. DOI:10.1111/j.1748-5967.2005.tb00146.x. 
16. ^ Ibrahim Jantan, and Zaridah Mohd. Zaki, Development of environment-friendly insect repellents from the leaf oils of selected Malaysian plants, ASEAN Review of Biodiversity and Environmental Conservation (ARBEC), May 1998.
17. ^ Trongtokit Y, Rongsriyan Y, Komalamisra N, Apiwathnasom L (2005). "Comparative repellency of 38 essential oils against mosquito bites". Phytother Res. 19 (4): 303-9. DOI:10.1002/ptr.1637. 
18. ^ Chauhan, K.R.; Klun, J.A.; Debboun, M.; Kramer, M. (2005). "Feeding Deterrent Effects of Catnip Oil Components Compared with Two Synthetic Amides Against Aedes aegypti". Journal of Medical Entomology 42 (4): 643-646. DOI:10.1603/0022-2585(2005)042[0643:FDEOCO]2.0.CO;2. 

The University of North Carolina is a sixteen-university system which comprises all public four-year universities in North Carolina, United States. ... A press release (sometimes known as a news release or press statement) is a written or recorded communication directed at members of the news media for the purpose of announcing something claimed as having news value. ... The Centers for Disease Control and Prevention (CDC) in Atlanta, Georgia, is recognized as the leading United States agency for protecting the public health and safety of people. ... is the 201st day of the year (202nd in leap years) in the Gregorian calendar. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... is the 201st day of the year (202nd in leap years) in the Gregorian calendar. ... The New England Journal of Medicine (NEJM) is a peer-reviewed medical journal published by the Massachusetts Medical Society. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... The mission of the United States Environmental Protection Agency (EPA) is to protect human health and to safeguard the natural environment: air, water, and land. ... is the 201st day of the year (202nd in leap years) in the Gregorian calendar. ... Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ...

See also

• Beautyberry
• Icaridin
• Permethrin, a pyrethroid
• Citronella oil

Species About 40; see text Beautyberry (Callicarpa) is a genus of shrubs and small trees in the family Verbenaceae; between 40_150 species are accepted by different botanists. ... Icaridin, also known as picaridine, KBR 3023, Bayrepel, and hydroxyethyl butyl piperidine carboxylate is an insect repellent owned and manufactured by Lanxess AG. It has a broad efficacy against different insects and is almost colorless and odorless. ... Permethrin is a common synthetic chemical, widely used as an insecticide and acaricide and as an insect repellent. ... A pyrethroid is a synthetic chemical that kills most insects. ... Citronella oil is one of the important essential oils obtained from different species of Cymbopogon. ...

External links

• US Centers for Disease Control information on DEET
• US Environmental Protection Agency information on DEET
• Review of scientific literature on DEET (from a RAND Corporation report on Gulf War illnesses)