Structure via PubChem · Public domain (PubChem)
dimethoate
Sign in to saveAlso 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
via PubChem
Research
1,729 papers- Dimethoate residues in Pakistan and mitigation strategies through microbial degradation: a review.Environmental science and pollution research international · 2022
- Dimethoate induces genotoxicity as a result of oxidative stress: in vivo and in vitro studies.Environmental science and pollution research international · 2021
- Carcinogenicity of dimethoate.Environmental research · 1984
- Environmental Fate and Toxicology of Dimethoate.Reviews of environmental contamination and toxicology · 2016
- Dimethoate absorption: A complementary in vitro and in vivo assessment.Environmental toxicology and pharmacology · 2022
via PubMed
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
via Wikidata · CC0
~5 min read
Article
11 sectionsContents
- 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