7337. Phosphamidon

Nomenclature

CAS number: 13171-21-6
Phosphoric acid 2-chloro-3-(diethylamino)-1-methyl-3-oxo-1-propen-1-yl dimethyl ester; phosphoric acid dimethyl ester, ester with 2-chloro-N,N-diethyl-3-hydroxycrotonamide; 2-chloro-2-diethylcarbamoyl-1-methylvinyl dimethyl phosphate; Ciba 570; ENT-25515; Kinadon (United Phosphorus).
C10H19ClNO5P; mol wt 299.69.
C 40.08%, H 6.39%, Cl 11.83%, N 4.67%, O 26.69%, P 10.34%.

Description and references

Organophosphate insecticide; cholinesterase inhibitor. Commercial product consists of 73/27 mixture of cis (Z)/ trans (E) isomers. Prepn: Beriger, Sallmann, US 2908605 (1959 to Ciba); Anliker et al., Helv. Chim. Acta 44, 1622 (1961) DOI. GC determn: W. E. Westlake et al., J. Agric. Food Chem. 21, 846 (1973) DOI PubMed. Toxicity data: T. B. Gaines, Toxicol. Appl. Pharmacol. 14, 515 (1969) DOI PubMed. Review: Residue Rev. 37, 1-202 (1971) PubMed PubMed.

Chemical structure

Properties

Oil. Poisonous. d425 1.2132. nD25 1.4718. bp1.5 162°; bp0.001 120°. mp -45°. Vapor pressure at 20°: 2.5 × 10-5 mm Hg. Misc with water and most organic solvents except saturated hydrocarbons. One gram dissolves in ≈30 g hexane. Stable in neutral or acid media; hydrolyzed by alkali. LD50 orally in rats: 24 mg/kg (Gaines).

Use

Insecticide.