Names | |
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IUPAC name Diethyl 2-[(dimethoxyphosphorothioyl)sulfanyl]butanedioate | |
Other names 2-(Dimethoxyphosphinothioylthio) butanedioic acid diethyl ester Malathion Carbofos Maldison Mercaptothion Ortho malathion | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.004.089 |
KEGG | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C10H19O6PS2 | |
Molar mass | 330.358021 |
Appearance | Clear colorless liquid |
Density | 1.23 g/cm3 |
Melting point | 2.9 °C (37.2 °F; 276.0 K) |
Boiling point | 156 to 157 °C (313 to 315 °F; 429 to 430 K) at 0.7 mmHg |
145 mg/L at 20 °C [1] | |
Solubility | Soluble in ethanol and acetone; very soluble in ethyl ether |
log P | 2.36 (octanol/water) [2] |
Pharmacology | |
P03AX03 ( WHO ) QP53AF12 ( WHO ) | |
Hazards | |
Flash point | 163 °C; 325 °F; 436 K (greater than) [3] |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose) | 290 mg/kg (rat, oral) 190 mg/kg (mouse, oral) 570 mg/kg (guinea pig, oral) [4] |
LC50 (median concentration) | 84.6 mg/m3 (rat, 4 hr) [4] |
LCLo (lowest published) | 10 mg/m3 (cat, 4 hr) [4] |
NIOSH (US health exposure limits): | |
PEL (Permissible) | TWA 15 mg/m3 [skin] [3] |
REL (Recommended) | TWA 10 mg/m3 [skin] [3] |
IDLH (Immediate danger) | 250 mg/m3 [3] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Malathion is an organophosphate insecticide which acts as an acetylcholinesterase inhibitor. In the USSR, it was known as carbophos, in New Zealand and Australia as maldison and in South Africa as mercaptothion.
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. [5] In the US, it is the most commonly used organophosphate insecticide. [6]
A malathion mixture with corn syrup was used in the 1980s in Australia and California to combat the Mediterranean fruit fly. [7] In Canada and the US starting in the early 2000s, malathion was sprayed in many cities to combat west Nile virus. [8] Malathion was used over the last couple of decades on a regular basis during summer months to kill mosquitoes, but homeowners were allowed an exemption for their properties if they chose.[ citation needed ].
In the United Kingdom, malathion was withdrawn from sale in 2002. [9]
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 at the synapse. [10]
Malathion is produced by the addition of dimethyl dithiophosphoric acid to diethyl maleate or diethyl fumarate. The compound is chiral but is used as a racemate.[ citation needed ]
Malathion in low doses (0.5% preparations) is used as a treatment for:
Preparations include Derbac-M, Prioderm, Quellada-M [15] and Ovide. [16]
Malathion is of low toxicity. In arthropods it is metabolized into malaoxon [17] which is 61x more toxic, [18] being a more potent inhibitor of acetylcholinesterase. [19] According to the United States Environmental Protection Agency, no reliable information is available on adverse health effects of chronic exposure. [20]
In 1981, Malathion was sprayed over a 1,400 sq mi (3,600 km2) 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. [21]
Malathion is classified by the IARC as probable carcinogen (group 2A). Malathion is classified by US EPA as having "suggestive evidence of carcinogenicity". [18] 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. [22]
Malathion is toxic to leopard frog tadpoles. [23]
Malathion is of low toxicity; however, absorption or ingestion into the human body readily results in its metabolism to malaoxon, which is substantially more toxic. [24] In studies of the effects of long-term exposure to oral ingestion of malaoxon in rats, malaoxon has been shown to be 61 times more toxic than malathion, [24] and malaoxon is 1,000 times more potent than malathion in terms of its acetylcholinesterase inhibition. [19] Indoor spillage of malathion can thus be more poisonous than expected, as malathion breaks down in a confined space into the more toxic malaoxon. It is cleared from the body quickly, in three to five days. [25]
Because it is an acetylcholinesterase inhibitor, this resistance is a type of AChEI resistance. [17] Malathion resistance is thought to always be due to either increased carboxylesterase concentrations or altered acetylcholinesterases. [17] 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. [17]
Carbaryl is a chemical in the carbamate family used chiefly as an insecticide. It is a white crystalline solid previously sold under the brand name Sevin, which was a trademark of the Bayer Company. The Sevin trademark has since been acquired by GardenTech, which has eliminated carbaryl from most Sevin formulations. Union Carbide discovered carbaryl and introduced it commercially in 1958. Bayer purchased Aventis CropScience in 2002, a company that included Union Carbide pesticide operations. Carbaryl was the third-most-used insecticide in the United States for home gardens, commercial agriculture, and forestry and rangeland protection. As a veterinary drug, it is known as carbaril (INN).
Parathion, also called parathion-ethyl or diethyl parathion and locally known as "Folidol", is an organophosphate insecticide and acaricide. It was originally developed by IG Farben in the 1940s. It is highly toxic to non-target organisms, including humans, so its use has been banned or restricted in most countries. The basic structure is shared by parathion methyl.
Chlorfenvinphos is an organophosphorus compound that was widely used as an insecticide and an acaricide. The molecule itself can be described as an enol ester derived from dichloroacetophenone and diethylphosphonic acid. Chlorfenvinphos has been included in many products since its first use in 1963. However, because of its toxic effect as a cholinesterase inhibitor it has been banned in several countries, including the United States and the European Union. Its use in the United States was discontinued in 1991.
Chlorpyrifos (CPS), also known as chlorpyrifos ethyl, is an organophosphate pesticide that has been used on crops, animals, and buildings, and in other settings, to kill several pests, including insects and worms. It acts on the nervous systems of insects by inhibiting the acetylcholinesterase enzyme. Chlorpyrifos was patented in 1966 by Dow Chemical Company.
Ethion (C9H22O4P2S4) is an organophosphate insecticide. Ethion is known to affect a neural enzyme called acetylcholinesterase and prevent it from working.
Diazinon, a colorless to dark brown liquid, is a thiophosphoric acid ester developed in 1952 by Ciba-Geigy, a Swiss chemical company. It is a nonsystemic organophosphate insecticide formerly used to control cockroaches, silverfish, ants, and fleas in residential, non-food buildings. Diazinon was heavily used during the 1970s and early 1980s for general-purpose gardening use and indoor pest control. A bait form was used to control scavenger wasps in the western U.S. Diazinon is used in flea collars for domestic pets in Australia and New Zealand. Diazinon is a major component in the "Golden Fleece" brand sheep dip. Residential uses of diazinon were outlawed in the U.S. in 2004 because of human health risks but it is still approved for agricultural uses. An emergency antidote is atropine.
Fenthion is an organothiophosphate insecticide, avicide, and acaricide. Like most other organophosphates, its mode of action is via cholinesterase inhibition. Due to its relatively low toxicity towards humans and mammals, fenthion is listed as moderately toxic compound in U.S. Environmental Protection Agency and World Health Organization toxicity class.
Azinphos-methyl (Guthion) is a broad spectrum organophosphate insecticide manufactured by Bayer CropScience, Gowan Co., and Makhteshim Agan. Like other pesticides in this class, it owes its insecticidal properties to the fact that it is an acetylcholinesterase inhibitor. It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act, and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.
Dichlorvos is an organophosphate widely used as an insecticide to control household pests, in public health, and protecting stored products from insects. The compound has been commercially available since 1961. It has become controversial because of its prevalence in urban waterways and the fact that its toxicity extends well beyond insects. Since 1988, dichlorvos cannot be used as a plant protection product in the EU.
Phosmet is a phthalimide-derived, non-systemic, organophosphate insecticide used on plants and animals. It is mainly used on apple trees for control of codling moth, though it is also used on a wide range of fruit crops, ornamentals, and vines for the control of aphids, suckers, mites, and fruit flies.
Dimethoate is a widely used organophosphate insecticide and acaricide. It was patented and introduced in the 1950s by American Cyanamid. Like other organophosphates, dimethoate is an acetylcholinesterase inhibitor which disables cholinesterase, an enzyme essential for central nervous system function. It acts both by contact and through ingestion. It is readily absorbed and distributed throughout plant tissues, and is degraded relatively rapidly. One of the breakdown products of dimethoate is omethoate, a potent cholinesterase inhibitor, is ten times more toxic than its parent compound.
Organophosphate poisoning is poisoning due to organophosphates (OPs). Organophosphates are used as insecticides, medications, and nerve agents. Symptoms include increased saliva and tear production, diarrhea, vomiting, small pupils, sweating, muscle tremors, and confusion. While onset of symptoms is often within minutes to hours, some symptoms can take weeks to appear. Symptoms can last for days to weeks.
Disulfoton is an organophosphate acetylcholinesterase inhibitor used as an insecticide. It is manufactured under the name Di-Syston by Bayer CropScience. Disulfoton in its pure form is a colorless oil but the technical product used in vegetable fields is dark and yellowish with a sulfur odor. Disulfoton is processed as a liquid into carrier granules, these granules are mixed with fertilizer and clay to be made into a spike, designed to be driven into the ground. The pesticide is absorbed over time by the roots and translocated to all parts of the plant. The pesticide acts as a cholinesterase inhibitor and gives long lasting control.
Propoxur (Baygon) is a carbamate non-systemic insecticide, produced from catechol, and was introduced in 1959. It has a fast knockdown and long residual effect, and is used against turf, forestry, and household pests and fleas. It is also used in pest control for domestic animals, Anopheles mosquitoes, ants, gypsy moths, and other agricultural pests. It can also be used as a molluscicide.
Naled (Dibrom) is an organophosphate insecticide. Its chemical name is dimethyl 1,2-dibromo-2,2-dichloroethylphosphate.
Sulfotep (also known as tetraethyldithiopyrophosphate and TEDP) is a pesticide commonly used in greenhouses as a fumigant. The substance is also known as Dithione, Dithiophos, and many other names. Sulfotep has the molecular formula C8H20O5P2S2 and belongs to the organophosphate class of chemicals. It has a cholinergic effect, involving depression of the cholinesterase activity of the peripheral and central nervous system of insects. The transduction of signals is disturbed at the synapses that make use of acetylcholine. Sulfotep is a mobile oil that is pale yellow-colored and smells like garlic. It is primarily used as an insecticide.
Terbufos is a chemical compound used in insecticides and nematicides. It is part of the chemical family of organophosphates. It is a clear, colourless to pale yellow or reddish-brown liquid and sold commercially as granulate.
Triamiphos (chemical formula: C12H19N6OP) is an organophosphate used as a pesticide and fungicide. It is used to control powdery mildews on apples and ornamentals. It was discontinued by the US manufacturer in 1998.
Profenofos is an organophosphate insecticide. It is a liquid with a pale yellow to amber color and a garlic-like odor. It was first registered in the United States in 1982. As of 2015, it was not approved in the European Union.
An extensive re-evaluation of malathion was completed by the US Environmental Protection Agency in 2000. The PMRA has also re-evaluated malathion and approved its use as a mosquito adulticide.