Trichlorfon
Title: Trichlorfon
CAS Registry Number: 52-68-6
CAS Name: (2,2,2-Trichloro-1-hydroxyethyl)phosphonic acid dimethyl ester
Additional Names: O,O-dimethyl-1-hydroxy-2,2,2-trichloroethylphosphonate; O,O-dimethyl 2,2,2-trichloro-1-hydroxyethylphosphonate; chlorofos; metrifonate; trichlorphene
Manufacturers' Codes: Bayer L 1359
Trademarks: Bilarcil (Bayer); Cekufon (Cequisa); Combot (Miles); Danex (Makhteshim-Agan); Dipterex (Bayer); Dylox (Bayer); Neguvon (Bayer); ProMem (Bayer); Proxol (AgrEvo); Tugon (Bayer)
Molecular Formula: C4H8Cl3O4P
Molecular Weight: 257.44
Percent Composition: C 18.66%, H 3.13%, Cl 41.31%, O 24.86%, P 12.03%
Literature References: Slow release cholinesterase inhibitor; transformed nonenzymatically to the active compd, dichlorvos, q.v. Prepn: W. Lorenz, US 2701225 (1955 to Bayer); W. F. Barthel et al., J. Am. Chem. Soc. 76, 4186 (1954); W. Lorenz et al., ibid. 77, 2554 (1955). Insecticidal activity: R. L. Metcalf et al., J. Econ. Entomol. 52, 44 (1959). Toxicity study: T. B. Gaines, Toxicol. Appl. Pharmacol. 14, 515 (1969). Transformation and mode of action: E. Reiner et al., Biochem. Pharmacol. 24, 717 (1975); I. Nordgren et al., Arch. Toxicol. 41, 31 (1978). HPLC determn in plasma: L. K. Unni et al., J. Chromatogr. 573, 99 (1992). Clinical pharmacokinetics: L. C. Pettigrew et al., J. Clin. Pharmacol. 38, 236 (1998). Clinical trial in Alzheimer's disease: R. E. Becker et al., Alzheimer Dis. Assoc. Disord. 10, 124 (1996). 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); in Alzheimer's disease: B. R. Williams, Am. J. Health-Syst. Pharm. 56, 427 (1999).
Properties: White crystals, mp 83-84°. d420 1.73. nD20 1.3439. Vapor pressure at 20°: 7.8 ´ 10-6 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 male, female rats (mg/kg): 630, 560 orally (Gaines).
Melting point: mp 83-84°
Index of refraction: nD20 1.3439
Density: d420 1.73
Toxicity data: LD50 in male, female rats (mg/kg): 630, 560 orally (Gaines)
 
Derivative Type: Butanoic acid ester
CAS Registry Number: 126-22-7
Additional Names: 2,2,2-Trichloro-1-(dimethoxyphosphinoyl)ethyl butyrate; butonate
Manufacturers' Codes: T-113
Molecular Formula: C8H14Cl3O5P
Molecular Weight: 327.53
Percent Composition: C 29.34%, H 4.31%, Cl 32.47%, O 24.42%, P 9.46%
Literature References: Prepn: Arthur, Casida, J. Agric. Food Chem. 6, 360 (1958).
Properties: Liquid. bp0.5 129°.
Boiling point: bp0.5 129°
 
Use: Insecticide.
Therap-Cat: Anthelmintic (schistosoma).
Therap-Cat-Vet: Anthelmintic (Nematodes); ectoparasiticide.
Keywords: Anthelmintic (Schistosoma).

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