3626. EPN

Nomenclature

CAS number: 2104-64-5
P-Phenylphosphonothioic acid O-ethyl O-(4-nitrophenyl) ester; ethyl p-nitrophenyl benzenethiophosphonate; O-ethyl O-4-nitrophenyl phenylphosphonothioate.
C14H14NO4PS; mol wt 323.30.
C 52.01%, H 4.36%, N 4.33%, O 19.80%, P 9.58%, S 9.92%.

Description and references

Organophosphate insecticide; cholinesterase inhibitor. Prepn: A. G. Jelinek, US 2503390 (1950 to du Pont). Manufacturing process: N. Shindo et al., US 3327026 (1967 to Nissan). Insecticidal activity: D. A. Wolfenbarger et al., J. Econ. Entomol. 63, 1568 (1970). Cholinesterase inhibition and toxicology: H. C. Hodge et al., J. Pharmacol. Exp. Ther. 112, 29 (1954) PubMed. Toxicity data: T. B. Gaines, Toxicol. Appl. Pharmacol. 2, 88 (1960) DOI PubMed. Metabolism in animals: R. L. Chrzanowski, A. G. Jelinek, J. Agric. Food Chem. 29, 580 (1981) DOI PubMed. Multiresidue determn in rice by GC-MS: S.-K. Cho et al., Biomed. Chromatogr. 21, 602 (2007) DOI PubMed.

Chemical structure

Properties

Light yellow oil, aromatic odor. d25 1.268. nD25 1.6021. Practically insol in water. Miscible with benzene, toluene, xylene, acetone, isopropanol, methanol. Poisonous. LD50 in female, male rats (mg/kg): 7.7, 36 orally; 25, 230 dermal (Gaines).

Caution

Potential symptoms of overexposure are miosis, lacrimation; rhinorrhea; headache; tight chest, wheezing and laryngeal spasm; salivation; cyanosis; anorexia, nausea, abdominal cramps and diarrhea; paralysis, convulsions; low blood pressure; cardiac irregularities; irritation of skin and eyes. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 128.

Use

Insecticide; acaricide.