3087. Dicrotophos

Nomenclature

CAS number: 141-66-2
Phosphoric acid 3-(dimethylamino)-1-methyl-3-oxo-1-propenyl dimethyl ester; phosphoric acid dimethyl ester, ester with cis-3-hydroxy-N,N-dimethylcrotonamide; 3-(dimethoxyphosphinyloxy)-N,N-dimethyl-cis-crotonamide; dimethyl 2-dimethylcarbamoyl-1-methylvinyl phosphate; dimethyl 1-dimethylcarbamoyl-1-propen-2-yl phosphate; C-709; ENT-24482; SD-3562; Bidrin (Amvac).
C8H16NO5P; mol wt 237.19.
C 40.51%, H 6.80%, N 5.91%, O 33.73%, P 13.06%.

Description and references

Cholinesterase inhibitor. Prepn of diethyl ester: Whetstone, Stiles, US 2802855 (1957 to Shell). Activity: R. A. Corey, J. Econ. Entomol. 58, 112 (1965). Metabolism and degradn: R. I. Beynon et al., Residue Rev. 47, 55 (1973). Toxicity data: T. B. Gaines, Toxicol. Appl. Pharmacol. 14, 515 (1969).

Chemical structure

Properties

Liquid, commercial grade is brown. bp760 400°. d1515 1.216. nD23 1.468. Misc with water, ethanol, xylene; somewhat sol in kerosene. Dec at 90° after 7 days; at 75° after 31 days. LD50 in female, male rats (mg/kg): 16, 21 orally; 42, 43 dermally (Gaines).

Caution

Potential symptoms of overexposure are headache, nausea, dizziness, anxiety, restlessness, muscle twitching, weakness, tremor, incoordination, vomiting, abdominal cramps, diarrhea; salivation, sweating, lacrimation, rhinitis; anorexia, malaise. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 102.

Use

Insecticide.