Structural Formula Vector Image
Title: EPN
CAS Registry Number: 2104-64-5
CAS Name: Phenylphosphonothioic acid O-ethyl O-(4-nitrophenyl) ester
Additional Names: ethyl p-nitrophenyl benzenethiophosphonate; O-ethyl O-p-nitrophenyl phenylphosphonothioate
Molecular Formula: C14H14NO4PS
Molecular Weight: 323.30
Percent Composition: C 52.01%, H 4.36%, N 4.33%, O 19.80%, P 9.58%, S 9.92%
Literature References: 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: R. L. McGarr, A. J. Chapman, J. Econ. Entomol. 59, 1529 (1966); D. A. Wolfenbarger et al., ibid. 63, 1568 (1970). Determn by HPLC: J. M. Lasker et al., Anal. Biochem. 109, 369 (1980); X.-D. Ding, I. S. Krull, J. Agric. Food Chem. 32, 622 (1984). Inhibition of acetylcholinesterase: O. Awad et al., Arzneim.-Forsch. 22, 1035 (1972); O. M. E. Awad, Enzyme 32, 193 (1984). Metabolism in animals: R. L. Chrzanowski, A. G. Jelinek, J. Agric. Food Chem. 29, 580 (1981). Toxicological study: H. C. Hodge et al., J. Pharmacol. Exp. Ther. 112, 29 (1954). Teratogenic evaluation in mice: K. D. Courtney et al., J. Environ. Sci. Health 20B, 373 (1985). Study of delayed neurotoxicity: B. M. Francis, Bull. Environ. Contam. Toxicol. 38, 283 (1987). Toxicity data: T. B. Gaines, Toxicol. Appl. Pharmacol. 2, 88 (1960).
Properties: Light yellow oil, aromatic odor. d25 1.268. nD25 1.6021. Practically insol in water. Miscible with benzene, toluene, xylene, acetone, isopropanol, methanol. LD50 in female, male rats (mg/kg): 7.7, 36 orally; 25, 230 dermal (Gaines).
Index of refraction: nD25 1.6021
Density: d25 1.268
Toxicity data: 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. See also Clinical Toxicology of Commercial Products, R. E. Gosselin et al., Eds. (Williams & Wilkins, Baltimore, 5th ed., 1984) Section II, p 294.
Use: Insecticide; acaricide.

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