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azinphos-methyl

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Also known as O,O-Dimethyl-S-4-oxo-1,2,3-benzotriazin-3(4H)-ylmethyl phosphorodithioate, Guthion, Methyl azinphos, AZM, Azinphosmethyl, O,O-dimethyl S-[(4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl] dithiophosphate, 3-(mercaptomethyl)-1,2,3-benzotriazin-4(3H)-one, O,O-dimethyl phosphorodithioate, O,O-Dimethyl S-(3,4-dihydro-4-keto-1,2,3-benzotriazinyl-3-methyl) dithiophosphate

Azinphos-methyl (Guthion) (also spelled azinophos-methyl) 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 (and human toxicity) to the fact that it is an acetylcholinesterase inhibitor (the same mechanism is responsible for the toxic effects of the V-series nerve agent chemical weapons). 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 (42 U.S.C

Wikidata facts

Mass
317.006
Has use
acaricide
Show 12 more facts
chemical formula
C₁₀H₁₂N₃O₃PS₂
Commons category
Azinphos-methyl
NIOSH Pocket Guide ID
0681
density
1.44
immediately dangerous to life or health
10
melting point
163
solubility
0.003
vapor pressure
0.000000008
time-weighted average exposure limit
0.2
canonical SMILES
COP(=S)(OC)SCN1C(=O)C2=CC=CC=C2N=N1
found in taxon
Penicillium
Sources (4)

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Encyclopedic overview

14 sections
Contents
  • History and uses
  • Available forms
  • Synthesis
  • Absorption
  • Mechanism of toxicity
  • Efficacy and side effects
  • Detoxification
  • Treatment
  • Indications (biomarkers)
  • Environmental degradation
  • Effect on animals
  • See also
  • References
  • External links

Azinphos-methyl (Guthion) (also spelled azinophos-methyl) 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 (and human toxicity) to the fact that it is an acetylcholinesterase inhibitor (the same mechanism is responsible for the toxic effects of the V-series nerve agent chemical weapons). 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 (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.

== History and uses == Azinphos-methyl is a neurotoxin derived from nerve agents developed during World War II. It was first registered in the US in 1959 as an insecticide and is also used as active ingredient in organophosphate (OP) pesticides. It is not registered for consumer or residential use. It has been linked to health problems of farmers who apply it, and the U.S. Environmental Protection Agency (EPA) considered a denial of reregistration, citing, “concern to farm workers, pesticide applicators, and aquatic ecosystems. The use of AZM has been fully banned in the USA since 30 September 2013, ending a phase-out period of twelve years. Azinphos-methyl has been banned in the European Union since 2006 and in Turkey since 2013. The New Zealand Environmental Risk Management Authority made a decision to phase out azinphos-methyl over a five-year period starting from 2009. In 2014, it was still used in Australia and partly in New Zealand.

Excerpted from Wikipedia’s “azinphos-methyl” article, available under the CC BY-SA 4.0 licence.