Azinphos-methyl

Azinphos-methyl
IUPAC name	O,O-dimethyl S-[(4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl] dithiophosphate
Other names	Azinphos-methyl AZM Guthion
Identifiers
CAS number	86-50-0
RTECS number	TE1925000
SMILES	O=C2N(CSP(OC)(OC)=S) N=NC1=CC=CC=C12
ChemSpider ID	2182
Properties
Molecular formula	C10H12N3O3PS2
Molar mass	317.32 g mol−1
Appearance	Brown, waxy solid
Density	1.44 g/cm3, solid
Melting point	73 °C (346 K)
Boiling point	>200 °C (decomp.)
Solubility in water	28 mg/L
Hazards
MSDS	External MSDS
R-phrases	R24 R28
S-phrases	S28 S36 S37 S45
NFPA 704	2 3 1
Flash point	69 °C
Related compounds
Related organophosphates	malathion chlorpyrifos
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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

• Colony collapse disorder

References

External links

• Compendium of Pesticide Common Names
• EPA's Azinphos-methyl Page
• Extoxnet - Azinphos-methyl
• Pesticideinfo.org - Azinphos-methyl