9623. Trichlorfon

Nomenclature

CAS number: 52-68-6
P-(2,2,2-Trichloro-1-hydroxyethyl)phosphonic acid dimethyl ester; O,O-dimethyl-1-hydroxy-2,2,2-trichloroethylphosphonate; O,O-dimethyl 2,2,2-trichloro-1-hydroxyethylphosphonate; chlorofos; metrifonate; trichlorphene; Bayer L 1359; Cekufon (United Phosphorus); Dipterex (Bayer CropSci.); Dylox (Bayer CropSci.).
C4H8Cl3O4P; mol wt 257.44.
C 18.66%, H 3.13%, Cl 41.31%, O 24.86%, P 12.03%.

Description and references

Organophosphorus insecticide; transformed nonenzymatically to the active cholinesterase inhibitor, dichlorvos, q.v. Prepn: W. Lorenz, US 2701225 (1955 to Bayer); W. F. Barthel et al., J. Am. Chem. Soc. 76, 4186 (1954) DOI; W. Lorenz et al., ibid. 77, 2554 (1955) DOI. Insecticidal activity: R. L. Metcalf et al., J. Econ. Entomol. 52, 44 (1959). Transformation and mode of action: E. Reiner et al., Biochem. Pharmacol. 24, 717 (1975) DOI PubMed; I. Nordgren et al., Arch. Toxicol. 41, 31 (1978) DOI PubMed. HPLC determn in plasma: L. K. Unni et al., J. Chromatogr. 573, 99 (1992) DOI PubMed. Determn by 31P-NMR in insecticidal formulations and crop residues: Z. Talebpour et al., Anal. Chim. Acta 576, 290 (2006) DOI PubMed. Clinical trial in Alzheimer's disease: R. E. Becker et al., Alzheimer Dis. Assoc. Disord. 10, 124 (1996) DOI PubMed. Evaluation of carcinogenic risk: IARC Monographs 30, 207-231 (1983). Review of clinical experience in schistosomiasis: H. Feldmeier, E. Doehring, Acta Trop. 44, 357 (1987) PubMed.

Chemical structure

Properties

White crystals, mp 83-84°. d420 1.73. nD20 1.3439. Vapor pressure at 20°: 7.8 × 106 mm Hg. Soly in water (25°): 15.4 g/100 ml. Sol in benzene, ethanol. Poorly sol in CCl4, diethyl ether. Insol in petroleum oils. Dec by alkali. LD50 in rats (mg/kg): 450 orally; 255 i.p.; in mice (ng/kg): 400 s.c.; 500 i.p. (Lorenz).

Derivative

Butanoic acid ester.

Nomenclature

CAS number: 126-22-7
2,2,2-Trichloro-1-(dimethoxyphosphinoyl)ethyl butyrate; butonate; T-113.
C8H14Cl3O5P; mol wt 327.53.
C 29.34%, H 4.31%, Cl 32.47%, O 24.42%, P 9.46%.

Description and references

Prepn: Arthur, Casida, J. Agric. Food Chem. 6, 360 (1958) DOI.

Properties

Liquid. bp0.5 129°.

Use

Insecticide.

Therapeutic Category

Anthelmintic (schistosoma).

Therapeutic Category (Veterinary)

Anthelmintic (Nematodes); ectoparasiticide.

Keywords

Anthelmintic (Schistosoma)