Difference between revisions of "DEET" - New World Encyclopedia
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| − | '''DEET''' is a | + | '''DEET''' is a chemical, '''''N'',''N''-Diethyl-''m''-toluamide''', that acts as an [[insect repellent]] to prevent bites from [[mosquito]]es, [[flea]]s, biting [[fly|flies]], and other [[insect]]s, as well as [[tick]]s ([[arachnid]]s). It is the most common active [[ingredient]] in insect repellents, popular in liquid sprays, lotions, and sticks, and is intended to be applied to the [[skin]] or to [[clothing]]. |
| − | In addition to being a nuisance, the bites of a number of insects and ticks pose health risks. For example, ticks bites may transmit [[Lyme disease]], several [[rickettsiosis|rickettsioses]], [[tick-borne meningoencephalitis]], and other [[tick-borne disease]]s), and [[mosquito]] bites may transmit [[malaria]], [[dengue fever]], [[West Nile virus]], and [[eastern equine encephalitis]]. Therefore, the use of an insect repellent is an important measure | + | In addition to being a nuisance, the bites of a number of insects and ticks pose health risks. For example, ticks bites may transmit [[Lyme disease]], several [[rickettsiosis|rickettsioses]], [[tick-borne meningoencephalitis]], and other [[tick-borne disease]]s), and [[mosquito]] bites may transmit [[malaria]], [[dengue fever]], [[West Nile virus]], and [[eastern equine encephalitis]]. Therefore, the use of an insect repellent is an important measure for prevention of these [[disease]]s. DEET is one of the most effective insect repellents known, and is considered safe when used properly, although the American Academy of Pediatrics recommends not using on infants less than two months old (CDC 2008). |
| − | == | + | ==Overview and description== |
| − | DEET was developed by the [[United States Army]], following its experience of [[jungle warfare]] during [[World War II]]. It entered military use in 1946 | + | Deet is a slightly yellow, almost colorless liquid at [[room temperature]]. Its [[IUPAC]] name is ''N,N''-Diethyl-3-methylbenzamide and it also is known as ''N,N''-Diethyl-''m''-toluamide. It can be prepared from [[M-toluic acid|''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]]: boiling point 111°C at 1 [[mm Hg]]. The chemical formula of DEET is C<sub>12</sub>H<sub>17</sub>NO. |
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| + | DEET was developed by the [[United States Army]] for protection of soldiers, following its experience of [[jungle warfare]] during [[World War II]]. It entered military use in 1946 and civilian use in 1957. Originally tested as a pesticide on farm fields, the United States Government applied it for war time usage, particularly when in Vietnam and around that region of Asia. | ||
==Mechanism of action== | ==Mechanism of action== | ||
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==Concentrations== | ==Concentrations== | ||
Revision as of 22:18, 4 August 2008
| DEET | |
|---|---|
| |
| IUPAC name | N,N-Diethyl-3-methylbenzamide |
| Other names | N,N-Diethyl-m-toluamide |
| Identifiers | |
| CAS number | [] |
| SMILES | CCN(CC)C(=O)C1=CC(=CC=C1)C |
| Properties | |
| Molecular formula | C12H17NO |
| Molar mass | 191.27 g/mol |
| Density | 0.998 g/mL |
| Melting point |
-45 °C |
| Boiling point |
288-292 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
DEET is a chemical, N,N-Diethyl-m-toluamide, that acts as an insect repellent to prevent bites from mosquitoes, fleas, biting flies, and other insects, as well as ticks (arachnids). It is the most common active ingredient in insect repellents, popular in liquid sprays, lotions, and sticks, and is intended to be applied to the skin or to clothing.
In addition to being a nuisance, the bites of a number of insects and ticks pose health risks. For example, ticks bites may transmit Lyme disease, several rickettsioses, tick-borne meningoencephalitis, and other tick-borne diseases), and mosquito bites may transmit malaria, dengue fever, West Nile virus, and eastern equine encephalitis. Therefore, the use of an insect repellent is an important measure for prevention of these diseases. DEET is one of the most effective insect repellents known, and is considered safe when used properly, although the American Academy of Pediatrics recommends not using on infants less than two months old (CDC 2008).
Overview and description
Deet is a slightly yellow, almost colorless liquid at room temperature. Its IUPAC name is N,N-Diethyl-3-methylbenzamide and it also is known as N,N-Diethyl-m-toluamide. 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: boiling point 111°C at 1 mm Hg. The chemical formula of DEET is C12H17NO.
DEET was developed by the United States Army for protection of soldiers, following its experience of jungle warfare during World War II. It entered military use in 1946 and civilian use in 1957. Originally tested as a pesticide on farm fields, the United States Government applied it for war time usage, particularly when in Vietnam and around that region of Asia.
Mechanism of action
DEET is believed to work by blocking insect olfactory receptors for 1-octen-3-ol, a volatile substance that is contained in human sweat and breath. DEET effectively "blinds" the insect's senses so that the biting/feeding instinct is not triggered by humans or animals which produce these chemicals. DEET does not appear to affect the insect's ability to smell carbon dioxide, as had been suspected earlier.[1][2]
Concentrations
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.[3] Other research has corroborated the effectiveness of DEET.[4] The Center for Disease Control recommends 30-50% DEET to prevent the spread of pathogens carried by insects.[citation needed]
Effects on health
As a precaution, manufacturers advise that DEET products should not be used under clothing or on damaged skin, and that preparations be washed off after they are no longer needed or between applications.[5] DEET can act as an irritant;[1] in rare cases, it may cause skin reactions.[5]
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.[6]
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". [7]
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.[5]
Effects on materials
DEET is an effective solvent,[1] and may dissolve (part of) some plastics, rayon, spandex, other synthetic fabrics, leather, and painted or varnished surfaces.
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.[citation needed] Though DEET is not expected to bioaccumulate, it has been found to have a slight toxicity for coldwater fish such as the rainbow trout[8] and the tilapia [9], and it has also been shown to be toxic for some species of freshwater zooplankton.[10] 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. [11]
Alternatives
Studies have shown eucalyptus-based repellents which contain the natural oil eucalyptol to be a highly effective and nontoxic alternative to DEET.[12]
Icaridin is another insect repellent of strength comparable to DEET, but it is less irritating and doesn't dissolve plastics.[citation needed]
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, whereas the natural repellent products tested were most effective for the first 30-60 minutes and then 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 repellency duration of DEET is much greater.[18] While most essential oil based repellents are not as effective as DEET,[18][19] research also shows that some essential oil based formulas can be comparable to DEET, and somewhat better specifically as mosquito repellant. [20]
Research suggests that distilled nepetalactone, the active ingredient in catnip, repels mosquitoes ten times more effectively than DEET,[21] but that it is not as effective a repellent on skin.[22]
See also
- Icaridin
- Permethrin, a pyrethroid
- Citronella oil
- Beautyberry
ReferencesISBN links support NWE through referral fees
- M. S. Fradin (1998). Mosquitoes and Mosquito Repellents: A Clinician's Guide. Ann Intern Med 128 (11): 931–940.
- ↑ 1.0 1.1 1.2 Anna Petherick (2008-03-13). How DEET jams insects' smell sensors. Nature News. Retrieved 2008-03-16.
- ↑ Mathias Ditzen, Maurizio Pellegrino, Leslie B. Vosshall (2008). Insect Odorant Receptors Are Molecular Targets of the Insect Repellent DEET. Sciencexpress 319: 1838.
- ↑ 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.
- ↑ University of North Carolina (3 July 2002). Independent study: DEET products superior for fending off mosquito bites. Press release.
- ↑ 5.0 5.1 5.2 Insect Repellent Use and Safety. West Nile Virus. Centers for Disease Control and Prevention (2007-01-12).
- ↑ "Reregistration Eligibility Decision: DEET." U.S. Environmental Protection Agency, Office of Prevention, Pesticides, and Toxic Substances. September 1998. pp39-40
- ↑ DEET. Pesticide Information Profile. EXTOXNET (October 1997). Retrieved 2007-09-26.
- ↑ 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.
- ↑ 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..
- ↑ 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.
- ↑ Errol Zeiger, Raymond Tice, Brigette Brevard, (1999) N,N-Diethyl-m-toluamide (DEET) [134-62-3] - Review of Toxicological Literature (PDF). Retrieved July 20.
- ↑ "The Claim: Listerine Can Ward Off a Swarm of Mosquitoes".
- ↑ Test: Mosquito repellents. CHOICE (December 2005). Retrieved 2007-09-26.
- ↑ Citronella (Oil of Citronella) (021901) Fact Sheet. U.S. Environmental Protection Agency (November 1999). Retrieved July 20, 2007.
- ↑ 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.
- ↑ 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.
- ↑ Trongtokit Y, Rongsriyan Y, Komalamisra N, Apiwathnasom L (2005). Comparative repellency of 38 essential oils against mosquito bites. Phytother Res. 19 (4): 303–9.
- ↑ 18.0 18.1 M. S. Fradin and J. F. Day (2002). Comparative Efficacy of Insect Repellents against Mosquito Bites. N Engl J Med 347 (1): 13–18.
- ↑ Collins, D.A. and Brady, J.N.; Curtis, C.F. (1993). Assessment of the efficacy of Quwenling as a Mosquito repellent. Phytotherapy Research 7 (1): 17–20.
- ↑ Trongtokit Y. and 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 mosquito vectors. Southeast Asia J, Trop Med Public Health 35 (2): 325–33.
- ↑ Dennis Loney (2001-08-28). Mosquito Repellents. American Chemical Society. Retrieved 2007-08-28.
- ↑ Chauhan, K.R. and 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.
External links
- DEET General Fact Sheet - National Pesticide Information Center
- West Nile Virus Resource Guide - National Pesticide Information Center
- Health Advisory: Tick and Insect Repellents, New York State
- 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)
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