Malathion

Malathion

Names
IUPAC name Diethyl 2-[(dimethoxyphosphorothioyl)sulfanyl]butanedioate
Other names 2-(dimethoxyphosphinothioylthio) butanedioic acid diethyl ester Malathion Carbofos Maldison Mercaptothion Ortho malathion
Identifiers
CAS Number	121-75-5 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:6651 Y
ChEMBL	ChEMBL1200468 N
ChemSpider	3864 Y
DrugBank	DB00772 Y
ECHA InfoCard	100.004.089
KEGG	D00534 Y
PubChem	4004
UNII	U5N7SU872W Y
InChI InChI=1S/C10H19O6PS2/c1-5-15-9(11)7-8(10(12)16-6-2)19-17(18,13-3)14-4/h8H,5-7H2,1-4H3 Y Key: JXSJBGJIGXNWCI-UHFFFAOYSA-N Y InChI=1/C10H19O6PS2/c1-5-15-9(11)7-8(10(12)16-6-2)19-17(18,13-3)14-4/h8H,5-7H2,1-4H3 Key: JXSJBGJIGXNWCI-UHFFFAOYAK
SMILES O=C(OCC)C(SP(=S)(OC)OC)CC(=O)OCC
Properties
Chemical formula	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
Solubility in water	145 mg/L at 20 °C
Solubility	Soluble in ethanol and acetone; very soluble in ethyl ether
log P	2.36 (octanol/water)
Pharmacology
ATC code	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)
LC50 (median concentration)	84.6 mg/m3 (rat, 4 hr)
LCLo (lowest published)	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 YN ?)
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.