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Malathion

Malathion
Skeletal formula of malathion
3D representation of malathion
filling model of malathion, showing van der Waals radii for each atom
Names
IUPAC name
Diethyl 2-[(dimethoxyphosphorothioyl)sulfanyl]butanedioate
Other names
2-(dimethoxyphosphinothioylthio) butanedioic acid diethyl ester
Malathion
Carbofos
Maldison
Mercaptothion
Ortho malathion
Identifiers
121-75-5 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:6651 YesY
ChEMBL ChEMBL1200468 N
ChemSpider 3864 YesY
DrugBank DB00772 YesY
ECHA InfoCard 100.004.089
KEGG D00534 YesY
PubChem 4004
UNII U5N7SU872W YesY
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
Solubility Soluble in ethanol and acetone; very soluble in ethyl ether
log P 2.36 (octanol/water)
Pharmacology
P03AX03 (WHO) QP53AF12 (WHO)
Hazards
Flash point 163 °C; 325 °F; 436 K (greater than)
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)
84.6 mg/m3 (rat, 4 hr)
10 mg/m3 (cat, 4 hr)
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 15 mg/m3 [skin]
REL (Recommended)
TWA 10 mg/m3 [skin]
IDLH (Immediate danger)
250 mg/m3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references


Malathion is an organophosphate insecticide of relatively low human toxicity. In the former 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. In the US, it is the most commonly used organophosphate insecticide.

Malathion as a mixture with corn syrup was used in the 1980s in Australia and California to combat the Mediterranean fruit fly. In Canada and the US, 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. Today, Winnipeg is the only major city in Canada with an ongoing malathion adult-mosquito-control program.

Malathion is a cholinesterase inhibitor, a diverse family of chemicals that includes sarin and carbaryl. Upon uptake into the target organism, it binds irreversibly to several, random serine residues on the cholinesterase enzyme, with a peroxide as the leaving group. 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.

It is produced by the addition of dimethyl dithiophosphoric acid to diethyl maleate. The compound is chiral but is used as a racemate.


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