Thiophanate
Title: Thiophanate
CAS Registry Number: 23564-06-9
CAS Name: [1,2-Phenylenebis(iminocarbonothioyl)]biscarbamic acid diethyl ester
Additional Names: 4,4¢-o-phenylenebis[3-thioallophanic acid]diethyl ester; 1,2-bis(3-ethoxycarbonyl-2-thioureido)benzene
Trademarks: Cercobin (Nippon Soda); Topsin (Nippon Soda); Nemafax (Rh>e-Mžieux)
Molecular Formula: C14H18N4O4S2
Molecular Weight: 370.45
Percent Composition: C 45.39%, H 4.90%, N 15.12%, O 17.28%, S 17.31%
Literature References: Prepn: T. Noguchi et al., DE 1806123; eidem, US 4020095 (1969, 1977 both to Nippon Soda Co.). Photodegradation: H. Buchenauer et al., Pestic. Sci. 5, 343 (1973). Activity vs nematode infection in ruminants: Eichler, Br. Vet. J. 129, 533 (1973). Toxicology in animals: idem, ibid. 130, 570 (1974).
Properties: Colorless plates from acetone, dec 194°. LD50 orally in mice and rats: >15 g/kg (Eichler).
Toxicity data: LD50 orally in mice and rats: >15 g/kg (Eichler)
 
Derivative Type: O,O-Dimethyl analog
CAS Registry Number: 23564-05-8
Additional Names: Thiophanate-methyl
Trademarks: Cercobin-M (Nippon Soda); Topsin-M (Nippon Soda)
Molecular Formula: C12H14N4O4S2
Molecular Weight: 342.39
Percent Composition: C 42.09%, H 4.12%, N 16.36%, O 18.69%, S 18.73%
Literature References: Prepn: T. Noguchi et al., loc. cit. Persistence in soil: J. R. Fleeker et al., J. Agric. Food Chem. 22, 592 (1974). Pharmacology, toxicity: Y. Hashimoto et al., Toxicol. Appl. Pharmacol. 23, 606, 616 (1972).
Properties: Colorless prisms, mp 181.5-182.5°. Sol in acetone, methanol, chloroform, acetonitrile; slightly sol in other organics. Practically insol in water. LD50 in rats, mice, guinea pigs, rabbits (g/kg): 3.40, 6.64, 3.64, 2.27 orally (Hashimoto).
Melting point: mp 181.5-182.5°
Toxicity data: LD50 in rats, mice, guinea pigs, rabbits (g/kg): 3.40, 6.64, 3.64, 2.27 orally (Hashimoto)
 
Use: Systemic fungicide.
Therap-Cat-Vet: Anthelmintic (Nematodes).

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