Azinphos-methyl

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Azinphos-methyl
General
Systematic name	S-(3,4-Dihydro-4-oxobenzo[d]- [1,2,3]-triazin-3-ylmethyl) O,O-dimethyl phosphorodithioate
Other names	Azinphos-methyl AZM Guthion
Molecular formula	C10H12N3O3PS2
SMILES	O=C2N(CSP(OC)(OC)=S) N=NC1=CC=CC=C12
Molar mass	317.32 g mol−1
Appearance	Brown, waxy solid
CAS number	[86-50-0]
Properties
Density and phase	1.44 g cm−3, solid
Solubility in water	28 mg/L
Melting point	73 °C (346 K)
Boiling point	>200 °C (decomp.)
Vapor Pressure	8*10-9 mmHg
LogP	2.75
Structure
Molecular shape	?
Dipole moment	? D
Hazards
MSDS	External MSDS
Main hazards	highly toxic
NFPA 704	2 3 1
Flash point	69 °C
R/S statement	R: R24 R28 S: S28 S36 S37 S45
RTECS number	TE1925000
Supplementary data page
Structure and properties	n, εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
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 disclaimer and 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.

[edit] History and Uses

Azinphos-methyl is a dangerous neurotoxin derived from nerve agents used 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."^[2] 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.^[3]

[edit] References

1. ^ EPA's Interrum Reregistration Eligibility Decesion for Azinphos-methyl
2. ^ ibid.
3. ^ Earthjustice press release announcing the reopening of the azinphos-methyl lawsuit.

[edit] External links

• Compendium of Pesticide Common Names
• EPA's Azinphos-methyl Page
• Extoxnet - Azinphos-methyl
• Pesticideinfo.org - Azinphos-methyl
• Links to external chemical sources