13-03066. Dicapthon [Archived]

Nomenclature

CAS number: 2463-84-5
Phosphorothioic acid O-(2-chloro-4-nitrophenyl) O,O-dimethyl ester; O,O-dimethyl O-(2-chloro-4-nitrophenyl)phosphorothioate; O,O-dimethyl-O-(2-chloro-4-nitrophenyl)thionophosphate; p-nitro-o-chlorophenyl dimethyl thionophosphate; isochlorothion; American Cyanamid 4124; insecticide ACC 4124; Dicaptan.
C8H9ClNO5PS; mol wt 297.65.
C 32.28%, H 3.05%, Cl 11.91%, N 4.71%, O 26.88%, P 10.41%, S 10.77%.

Description and references

Prepn: J. H. Fletcher, US 2664437; Geoghegan, McPherson, US 2784207 (1953, 1957 both to Am. Cyanamid); Schrader, Angew. Chem. 66, 265 (1954); idem, Die Entwicklung neuer insektizider Phosphorsure-Ester (Verlag Chemie, 3rd ed., 1963) pp 289-291. Toxicity study: T. B. Gaines, Toxicol. Appl. Pharmacol. 14, 515 (1969).

Chemical structure

Properties

Crystals from methanol, mp 53°. Sol in acetone, cyclohexanone, ethyl acetate, toluene, xylene, ethylene glycol, propylene glycol, some oils. Practically insol in water. LD50 in male, female rats (mg/kg): 400, 330 orally; 790, 1250 dermally (Gaines).

Caution

Cholinesterase inhibitor.

Use

Insecticide.

Status

This monograph has been retired and is no longer subject to revision or update.