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Malathion is an organophosphate insecticide which acts as an acetylcholinesterase inhibitor. In the
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, it was known as carbophos, in
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and
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as maldison and in
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as mercaptothion.


Pesticide use

Malathion is a pesticide that is widely used in agriculture, residential landscaping, public recreation areas, and in public health pest control programs such as mosquito eradication. In the US, it is the most commonly used organophosphate insecticide. A malathion mixture with
corn syrup Corn syrup is a food syrup which is made from the starch of corn (called maize in many countries) and contains varying amounts of sugars: glucose, maltose and higher oligosaccharides, depending on the grade. Corn syrup is used in foods to soft ...
was used in the 1980s in Australia and California to combat the Mediterranean fruit fly. In Canada and the US starting in the early 2000s, malathion was sprayed in many cities to combat west Nile virus. Malathion was used over the last couple of decades on a regular basis during summer months to kill mosquitoes, but homeowners were allowed to exempt their properties if they chose..


Mechanism of action

Malathion is an acetylcholinesterase inhibitor, a diverse family of chemicals. Upon uptake into the target organism, it binds irreversibly to the serine residue in the active catalytic site of the cholinesterase enzyme. The resultant phosphoester group is strongly bound to the cholinesterase, and irreversibly deactivates the enzyme which leads to rapid build-up of
acetylcholine Acetylcholine (ACh) is an organic chemical that functions in the brain and body of many types of animals (including humans) as a neurotransmitter. Its name is derived from its chemical structure: it is an ester of acetic acid and choline. Par ...
at the synapse.


Production method

Malathion is produced by the addition of
dimethyl dithiophosphoric acid Dimethyl dithiophosphoric acid is the organophosphorus compound with the formula (CH3O)2PS2H. It is the processor for production of the organothiophosphate insecticide Malathion. Although samples can appear dark, the compound is a colorless, dist ...
to diethyl maleate or diethyl fumarate. The compound is chiral but is used as a racemate.


Medical use

Malathion in low doses (0.5% preparations) is used as a treatment for: * Head lice and body lice. Malathion is approved by the US
Food and Drug Administration The United States Food and Drug Administration (FDA or US FDA) is a federal agency of the Department of Health and Human Services. The FDA is responsible for protecting and promoting public health through the control and supervision of food ...
for treatment of
pediculosis Pediculosis is an infestation of lice from the sub-order Anoplura, family Pediculidae. Accordingly, the infestation with head lice is named pediculosis capitis, while this with body lice, pediculosis corporis. Although ''pediculosis'' in humans ma ...
. It is claimed to effectively kill both the eggs and the adult lice, but in fact has been shown in UK studies to be only 36% effective on head lice, and less so on their eggs. This low efficiency was noted when malathion was applied to lice found on schoolchildren in the Bristol area in the UK, and it is assumed to be caused by the lice having developed resistance against malathion. *
Scabies Scabies (; also sometimes known as the seven-year itch) is a contagious skin infestation by the mite ''Sarcoptes scabiei''. The most common symptoms are severe itchiness and a pimple-like rash. Occasionally, tiny burrows may appear on the ski ...
Preparations include Derbac-M, Prioderm, Quellada-M and Ovide.


Safety


General

Malathion is of low toxicity. In arthropods it is metabolized into malaoxon which is 61x more toxic, being a more potent inhibitor of acetylcholinesterase. According to the
United States Environmental Protection Agency The Environmental Protection Agency (EPA) is an independent executive agency of the United States federal government tasked with environmental protection matters. President Richard Nixon proposed the establishment of EPA on July 9, 1970; it ...
, no reliable information is available on adverse health effects of chronic exposure. In 1981, Malathion was sprayed over a area to control an outbreak of Mediterranean fruit flies in California. In order to demonstrate the chemical's safety, B. T. Collins, director of the California Conservation Corps, publicly swallowed a mouthful of dilute malathion solution.


Carcinogenicity

Malathion is classified by the
IARC IARC may refer to: * International Aerial Robotics Competition * International Age Rating Coalition * International Agency for Research on Cancer * International Arctic Research Center * Israel Amateur Radio Club The Israel Amateur Radio Club ...
as probable carcinogen (group 2A). Malathion is classified by US EPA as having "suggestive evidence of carcinogenicity". This classification was based on the occurrence of liver tumors at excessive doses in mice and female rats and the presence of rare oral and nasal tumors in rats that occurred following exposure to very large doses. Exposure to organophosphates is associated with non-Hodgkin's lymphoma. Malathion used as a fumigant was not associated with increased cancer risk. Between 1993 and 1997, as part of the Agricultural Health Study, no clear association between malathion exposure and cancer was reported.


Amphibians

Malathion is toxic to leopard frog tadpoles.


Resistance

Because it is an acetylcholinesterase inhibitor, this resistance is a type of AChEI resistance. Malathion resistance is thought to always be due to either increased carboxylesterase concentrations or altered acetylcholinesterases. COE because it metabolizes malathion but into ''non''-malaoxon products, altered AChEs because we mean specifically those altered to be less sensitive to malathion and malaoxon.


See also

* Isomalathion * Pesticide toxicity to bees


References


External links


Malathion Technical Fact Sheet - National Pesticide Information Center

Malathion General Fact Sheet - National Pesticide Information Center


* ttps://web.archive.org/web/20130509193404/http://www.atsdr.cdc.gov/tfacts154.html ATSDR ToxFAQs
CDC - NIOSH Pocket Guide to Chemical Hazards

Re-evaluation of Malathion
by the Pest Management Regulatory Agency of Canada * {{Authority control Acetylcholinesterase inhibitors Antiparasitic agents Endocrine disruptors Insecticides Organophosphate insecticides Phosphorodithioates