3976. Fenitrothion

Nomenclature

CAS number: 122-14-5
Phosphorothioic acid O,O-dimethyl O-(3-methyl-4-nitrophenyl) ester; O,O-dimethyl O-4-nitro-m-tolyl phosphorothioate; O,O-dimethyl O-(3-methyl-4-nitrophenyl) phosphorothioate; O,O-dimethyl O-4-nitro-m-tolyl thiophosphate; MEP; metathion; Bayer 41831; Bayer S 5660; ENT-25715; OMS-45; AC-47300; Sumithion (Sumitomo).
C9H12NO5PS; mol wt 277.23.
C 38.99%, H 4.36%, N 5.05%, O 28.86%, P 11.17%, S 11.57%.

Description and references

Organophosphate insecticide; cholinesterase inhibitor. Prepn: BE 594669 (1960 to Sumitomo); BE 596091 (1960 to Bayer). Activity: Y. Nishizawa et al., Agric. Biol. Chem. 25, 605 (1961). Toxicity study: G. Schrader, Angew. Chem. 73, 331 (1961) DOI. HPLC determn in water: A. Sánchez-Ortega et al., J. Chromatogr. A 1094, 70 (2005) DOI PubMed. GC determn in stored barley: U. Uygun et al., Food Chem. 100, 1165 (2007) DOI.

Chemical structure

Properties

Yellow oil. bp0.05 118°. nD25 1.5528. d425 1.3227. Log P (octanol/water): 3.43. Vapor press at 20°: 6×10-6 mm Hg. uv max: 269.5 nm (ε 6756). Practically insol in water. Low soly in aliphatic hydrocarbons; sol in most organic solvents. LD50 orally in rats: 250 mg/kg (Schrader).

Use

Agricultural insecticide.