Azinphos-methyl

Title: Azinphos-methyl
CAS Registry Number: 86-50-0
CAS Name: Phosphorodithioic acid O,O-dimethyl S-[(4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl] ester
Additional Names: phosphorodithioic acid O,O-dimethyl ester, S-ester with 3-mercaptomethyl-1,2,3-benzotriazin-4(3H)-one
Manufacturers' Codes: Bayer 17147; ENT-23233; R-1582
Trademarks: Cotnion-methyl (Makhteshim-Agan); Gusathion M (Bayer CropSci.); Guthion (Bayer CropSci.)
Molecular Formula: C10H12N3O3PS2
Molecular Weight: 317.32
Percent Composition: C 37.85%, H 3.81%, N 13.24%, O 15.13%, P 9.76%, S 20.21%
Literature References: Cholinesterase inhibitor. Prepn: Lorenz, US 2758115 (1956 to Bayer). Activity: E. E. Ivy et al., J. Econ. Entomol. 48, 293 (1955). Toxicity study: T. B. Gaines, Toxicol. Appl. Pharmacol. 14, 515 (1969).
Properties: Crystals from methanol, mp 73-74°. d420 1.44; nD76 1.6115. Soly in water at 25°: 33 mg/l. Sol in methanol, ethanol, propylene glycol, xylene, other organic solvents. Solns in ethanol and propylene glycol are stable for at least 3 weeks. Unstable at temperatures >200°. Hydrolyzes in acid or cold alkali. LD50 in female rats (mg/kg): 11 orally; 220 dermally (Gaines).
Melting point: mp 73-74°
Index of refraction: nD76 1.6115
Density: d420 1.44
Toxicity data: LD50 in female rats (mg/kg): 11 orally; 220 dermally (Gaines)
Derivative Type: O,O-Diethyl analog
Additional Names: Azinphos-ethyl
Manufacturers' Codes: Bayer 16259; ENT-22014; R-1513
Molecular Formula: C12H16N3O3PS2
Molecular Weight: 345.38
Percent Composition: C 41.73%, H 4.67%, N 12.17%, O 13.90%, P 8.97%, S 18.57%
Properties: Colorless needles, mp 53°, bp0.001 111°. d420 1.284; nD53 1.5928. Vapor pressure at 20°: 2.2 ´ 10-7 mm Hg.
Melting point: mp 53°
Boiling point: bp0.001 111°
Index of refraction: nD53 1.5928
Density: d420 1.284
CAUTION: Potential symptoms of overexposure to azinphos-methyl are miosis; aching eyes; blurred vision, lacrimation and rhinorrhea; headache; chest tightness, wheezing, laryngeal spasms; salivation; cyanosis; anorexia; nausea, vomiting and diarrhea; sweating; twitching, paralysis and convulsions; low blood pressure, cardiac irregularities. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 22.
Use: Insecticide; acaricide.
Azintamide Azithromycin Azlocillin Azolitmin Azomycin

Azinphos-methyl
Kekulé, skeletal formula of azinphos-methyl
Identifiers
Abbreviations AZM
CAS number 86-50-0 YesY
PubChem 2268
ChemSpider 2181 YesY
UNII 265842EWUV YesY
EC number 201-676-1
UN number 2811
KEGG C11018 YesY
MeSH Azinphosmethyl
ChEBI CHEBI:2953 YesY
ChEMBL CHEMBL530115 YesY
RTECS number TE1925000
Beilstein Reference 280476
Jmol-3D images Image 1
Image 2
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Properties
Molecular formula C10H12N3O3PS2
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 (decomposes)
Solubility in water 28 mg dm-3
log P 2.466
Hazards
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
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 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
NFPA 704.svg
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Flash point 69 °C; 156 °F; 342 K
Related compounds
Related organophosphates Chlorpyrifos

Malathion

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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Azinphos-methyl (Guthion) (also spelled azinophos-methyl) 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.