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dimethoate

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dimethoate

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Also known as O,O-dimethyl S-[2-(methylamino)-2-oxoethyl] dithiophosphate, Phosphorodithioic acid, O,O-dimethyl S-(2-(methylamino)-2-oxoethyl) ester, 2-Dimethoxyphosphinothioylthio-N-methylacetamide, Phosphamide

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.

Chemical data

Formula
C5H12NO3PS2
Molecular weight
229.3 g/mol
IUPAC name
2-dimethoxyphosphinothioylsulfanyl-N-methylacetamide
SMILES
CNC(=O)CSP(=S)(OC)OC
InChIKey
MCWXGJITAZMZEV-UHFFFAOYSA-N
XLogP
0.8
Polar surface area
105 Ų
H-bond donors
1
H-bond acceptors
5
Formal charge
0

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Research

1,729 papers

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Wikidata facts

Mass
229
Show 5 more facts
MCN code
2930.90.54
chemical formula
C₅H₁₂NO₃PS₂
isomeric SMILES
C/N=C(\CSP(=S)(OC)OC)/O
canonical SMILES
CNC(=O)CSP(=S)(OC)OC
Commons category
Dimethoate
Sources (4)

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Article

11 sections
Contents
  • Uses
  • Environment
  • Health effects
  • Routes of exposure
  • Acute exposure in humans
  • Chronic exposure in humans
  • Fruit fly control efforts
  • Trade names
  • Poisoning incidents
  • References
  • External links

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.

== Uses == Dimethoate is a general use insecticide for combatting insects such as aphids, mites, beetles, weevils, and leafhoppers. Dimethoate is formulated as emulsifiable concentrates or wettable powders to be applied primarily as foliar sprays. The majority of the approximately 800.000 kg (1.8 million pounds) of dimethoate used annually in the U.S. is accounted for by applications on alfalfa, wheat, cotton, and corn crops. In 2005, dimethoate usage was cancelled in the U.S. for use on apples, broccoli raab, cabbage, collards, grapes, head lettuce, and spinach due to being identified as significant dietary risk contributors. Dimethoate also has applications as a form of botfly and mite control in livestock. As of 2000, dimethoate is cancelled for usage in residential and non-agriculture applications in the U.S

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