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Kekulé, skeletal formula of azinphos-methyl
IUPAC name
O,O-Dimethyl S-[(4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl]dithiophosphate[citation needed]
Other names
Guthion, azinphosmethyl, azinphos
Abbreviations AZM
86-50-0 YesY
ChEMBL ChEMBL530115 YesY
ChemSpider 2181 YesY
EC number 201-676-1
Jmol-3D images Image
KEGG C11018 YesY
MeSH Azinphosmethyl
PubChem 2268
RTECS number TE1925000
UNII 265842EWUV YesY
UN number 2811
Molar mass 317.32 g·mol−1
Appearance Pale, dark orange, translucent crystals
Density 1.44 g cm−3
Melting point 73 °C; 163 °F; 346 K
Boiling point > 200 °C (392 °F; 473 K) (decomposes)
28 mg dm−3
log P 2.466
MSDS External MSDS
GHS pictograms The skull-and-crossbones pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The environment pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)[1]
GHS signal word Danger
H300, H311, H317, H330, H410[1]
P260, P264, P273, P280, P284, P301+310[1]
EU Index 015-039-00-9
EU classification Very Toxic T+ Dangerous for the Environment (Nature) N
R-phrases R24, R26/28, R43, R50/53
S-phrases (S1/2), S28, S36/37, S45, S60, S61
NFPA 704
Flammability code 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 fuel Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calcium Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 69 °C (156 °F; 342 K)
US health exposure limits (NIOSH):
TWA 0.2 mg/m3 [skin][2]
Related compounds


Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY verify (what isYesY/N?)
Infobox references

Azinphos-methyl (Guthion) (also spelled azinophos-methyl) is a broad spectrum organophosphate insecticide manufactured by Bayer CropScience, Gowan Co., and Makhteshim Agan.[3] 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[edit]

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".[3] 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.[4]

Azinphos-methyl has been banned in the European Union since 2006.[5]

The New Zealand Environmental Risk Management Authority made a decision to phase out azinphos-methyl over a five-year period starting from 2009.[6]

See also[edit]


External links[edit]