1431. Bromophos

Nomenclature

CAS number: 2104-96-3
Phosphorothioic acid O-(4-bromo-2,5-dichlorophenyl) O,O-dimethyl ester; O-(4-bromo-2,5-dichlorophenyl)-O,O-dimethylphosphorothioate; O,O-dimethyl-O-(2,5-dichloro-4-bromophenyl)thiophosphate; bromofos; bromophos-methyl; ENT-27162; OMS-658; S-1942; Nexion (BASF).
C8H8BrCl2O3PS; mol wt 366.00.
C 26.25%, H 2.20%, Br 21.83%, Cl 19.37%, O 13.11%, P 8.46%, S 8.76%.

Description and references

Organophosphate insecticide; cholinesterase inhibitor. Prepn: BE 625198; R. Sehring, K. Zeile, US 3275718 (1963, 1966 both to Boehringer, Ing.). Crystal structure: R. G. Baughman, R. A. Jacobson, J. Agric. Food Chem. 24, 1036 (1976) DOI PubMed. Metabolism in rats: M. Stiasni et al., ibid. 15, 474 (1967) DOI. Toxicity study: T. B. Gaines, Toxicol. Appl. Pharmacol. 14, 515 (1969) DOI PubMed. TLC determn in food crops: S. Traore, J. J. Aaron, Talanta 28, 765 (1981) DOI PubMed. Review: D. Eichler, Residue Rev. 41, 65-112 (1972) PubMed.

Chemical structure

Properties

Yellow crystals, mp 53-54°. bp0.01 140-142°. Vapor pressure at 20°C: 1.3 × 104 mm Hg. Soly in water at 25°: 40 mg/l. Sol in CCl4, ether, toluene. Stable in soln up to pH 9. Non-corrosive. LD50 in male, female rats (mg/kg): 1600, 1730 orally (Gaines).

Derivative

O,O-Diethyl analog.

Nomenclature

Bromophos-ethyl; ENT-27258; OMS-659; S-2225; Nexagan.
C10H12BrCl2O3PS; mol wt 394.05.
C 30.48%, H 3.07%, Br 20.28%, Cl 17.99%, O 12.18%, P 7.86%, S 8.14%.

Properties

Colorless to pale yellow oil, bp0.001 122-133°. Vapor pressure at 30°: 4.6 × 105 mm Hg. Soly in water at 25°: 2 mg/l.

Use

Insecticide; acaricide.