913. Azinphos-methyl

Nomenclature

CAS number: 86-50-0
Phosphorodithioic acid O,O-dimethyl S-[(4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl] ester; phosphorodithioic acid O,O-dimethyl ester, S-ester with 3-mercaptomethyl-1,2,3-benzotriazin-4(3H)-one; Bayer 17147; ENT-23233; R-1582; Cotnion (Bayer CropSci.); Gusathion M (Bayer CropSci.).
C10H12N3O3PS2; mol wt 317.32.
C 37.85%, H 3.81%, N 13.24%, O 15.13%, P 9.76%, S 20.21%.

Description and references

Organophosphate insecticide; cholinesterase inhibitor. Prepn: W. Lorenz, US 2758115 (1956 to Bayer). Activity: E. E. Ivy et al., J. Econ. Entomol. 48, 293 (1955). Multi-residue determn by GC-MS: K. S. Liapis et al., J. Chromatogr. A 996, 181 (2003) DOI PubMed. Photodegradation study: M. Ménager et al., J. Photochem. Photobiol. A 192, 41 (2007) DOI. Toxicity study: T. B. Gaines, Toxicol. Appl. Pharmacol. 14, 515 (1969) DOI PubMed.

Chemical structure

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. Poisonous. LD50 in female rats (mg/kg): 11 orally; 220 dermally (Gaines).

Derivative

O,O-Diethyl analog.

Nomenclature

Azinphos-ethyl; Bayer 16259; ENT-22014; R-1513.
C12H16N3O3PS2; mol wt 345.38.
C 41.73%, H 4.67%, N 12.17%, O 13.90%, P 8.97%, S 18.57%.

Description and references

Multi-residue determn by LC-MS/MS: B. Kmellár et al., J. Chromatogr. A 1215, 37 (2008) DOI PubMed.

Properties

Colorless needles, mp 53°, bp0.001 111°. Poisonous. d420 1.284; nD53 1.5928. Vapor pressure at 20°: 2.2 × 107 mm Hg.

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.