9289. Thiabendazole
Nomenclature
Description and references
Prepd by the reaction of 4-thiazolecarboxamide with o-phenylenediamine in polyphosphoric acid: H. D. Brown et al., J. Am. Chem. Soc. 83, 1764 (1961); L. H. Sarett, H. D. Brown, US 3017415 (1962 to Merck & Co.). Synthesis of labeled thiabendazole: D. J. Tocco et al., J. Med. Chem. 7, 399 (1964). Alternate route of synthesis: V. J. Grenda et al., J. Org. Chem. 30, 259 (1965). Anthelmintic props: H. D. Brown et al., loc. cit.; K. C. Kates et al., J. Parasitol. 57, 356 (1971). Fungicidal props: H. J. Robinson et al., J. Invest. Dermatol. 42, 479 (1966). Systemic props in plants: D. C. Erwin et al., Phytopathology 58, 860 (1968). Toxicity: H. J. Robinson et al., Toxicol. Appl. Pharmacol. 7, 53 (1965). Residue analysis: IUPAC Appl. Chem. Div., Pure Appl. Chem. 52, 2567 (1980). Comprehensive description: V. K. Kapoor, Anal. Profiles Drug Subs. 16, 611-639 (1986).
Properties
White to off-white, odorless powder, mp 304-305°. uv max (methanol): 298 nm (ε 23330). Fluorescence max in acid soln: 370 nm (310 nm excitation). Max soly in water at pH 2.2: 3.84%. Soluble in DMF, DMSO. Slightly soluble in alcohols, esters, chlorinated hydrocarbons. LD50 in mice, rats, rabbits (g/kg): 3.6, 3.1, >3.8 orally (Robinson).Derivative
Monophosphinate.Nomenclature
Properties
Amber liquid. d25 1.103.Use
Fungicide for spoilage control of citrus fruit; for treatment and prevention of Dutch elm disease in trees; for control of fungal diseases of seed potatoes.Therapeutic Category
Anthelmintic (Nematodes).
Therapeutic Category (Veterinary)
Anthelmintic, fungicide.Keywords
Anthelmintic (Nematodes)