Azinphos-methyl

Azinphos-methyl
IUPAC name O,O-Dimethyl S-[(4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl]dithiophosphate[citation needed]
Other names Guthion
Identifiers
Abbreviations	AZM
CAS number	86-50-0 Y
PubChem	2268
ChemSpider	2181 Y
UNII	265842EWUV Y
EC number	201-676-1
UN number	2811
KEGG	C11018 Y
MeSH	Azinphosmethyl
ChEBI	CHEBI:2953 Y
ChEMBL	CHEMBL530115 Y
RTECS number	TE1925000
Beilstein Reference	280476
Jmol-3D images	Image 1 Image 2 Image 3
SMILES COP(=S)(OC)SCn1nnc2ccccc2c1:o COP(=S)(OC)SCN1N=NC2=CC=CC=C2C1=O O=C2N(CSP(OC)(OC)=S)N=NC1=CC=CC=C12
InChI InChI=1S/C10H12N3O3PS2/c1-15-17(18,16-2)19-7-13-10(14)8-5-3-4-6-9(8)11-12-13/h3-6H,7H2,1-2H3 Y Key: CJJOSEISRRTUQB-UHFFFAOYSA-N Y
Properties
Molecular formula	C10PN3H12S2O3
Molar mass	317.324 g mol-1
Appearance	Pale, dark orange, translucent crystals
Density	1.44 g cm-3
Melting point	73 °C, 346 K, 163 °F
Boiling point	>200 °C (decomposes)
Solubility in water	28 mg dm-3
log P	2.466
Hazards
MSDS	External MSDS
GHS pictograms	[1]
GHS signal word	Danger
GHS hazard statements	H300, H311, H317, H330, H410[1]
GHS precautionary statements	P260, P264, P273, P280, P284, P301+310[1]
EU Index	015-039-00-9
EU classification	T+ N
R-phrases	R24, R26/28, R43, R50/53
S-phrases	(S1/2), S28, S36/37, S45, S60, S61
NFPA 704	2 3 1
Flash point	69 °C
Related compounds
Related organophosphates	Chlorpyrifos Malathion
Y (verify) (what is: Y/N?) 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.^[2] 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".^[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]

Azinphos-methyl has been banned in the European Union since 2006.^[4]

The New Zealand Environmental Risk Management Authority made a decision to phase out azinphos-methyl over a five year period starting from 2009.^[5]

See also

• Azinphos-ethyl
• Colony collapse disorder

References

External links

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