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Azinphos-methyl

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Azinphos-methyl
{Azinphos-methyl
Names
IUPAC name
O,O-dimethyl S-[(4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl]dithiophosphate
Other names
Azinphos-methyl
AZM
Guthion
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.524 Edit this at Wikidata
RTECS number
  • TE1925000
  • O=C2N(CSP(OC)(OC)=S)
    N=NC1=CC=CC=C12
Properties
C10H12N3O3PS2
Molar mass 317.32 g·mol−1
Appearance Brown, waxy solid
Density 1.44 g/cm3, solid
Melting point 73 °C (163 °F; 346 K)
Boiling point >200 °C (decomp.)
28 mg/L
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 highly toxic
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
3
2
1
Flash point 69 °C
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Azinphos-methyl (Guthion) is a broad spectrum organophosphate insecticide manufactured by Bayer CropScience, Gowan Co., and Makhteshim Agan.[1] Like other pesticides in this class, it owes its insecticidal properties (and human toxicity) to the fact that it is an acetylcholinesterase inhibitor.

History and uses

Azinphos-methyl is a neurotoxin derived from nerve agents developed during World War II. In the US, it is registered for use on select nut trees, vegetable crops, and fruit trees. 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".[1] After settling a 2004 lawsuit brought by the United Farm Workers of America and other groups, the EPA accounced it would begin phasing out the remaining uses of the pesticide in 2007 with all uses ending in 2012. In January 2007, the suit was reopened, with the plaintiffs seeking a quicker phaseout.[2]

Azinphos-methyl has been banned in the European Union since 2006.[3]

The New Zealand Environmental Risk Management Authority made a decision to phase out azinphos-methyl over a five year period starting from 2009.[4]

See also

References

  1. ^ a b EPA's Interrum Reregistration Eligibility Decesion for Azinphos-methyl
  2. ^ Earthjustice press release announcing the reopening of the azinphos-methyl lawsuit.
  3. ^ Scott, Alex (August 4, 2008). "Europe Rejects Appeal for Use of Azinphos-methyl Pesticide". Chemical Week. Retrieved 2008-08-11.
  4. ^ ERMA - press release


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