Title: Thiabendazole
CAS Registry Number: 148-79-8
CAS Name: 2-(4-Thiazolyl)-1H-benzimidazole
Additional Names: 4-(2-benzimidazolyl)thiazole
Manufacturers' Codes: MK-360
Trademarks: Equizole (Merial); Mertect (Syngenta); Mintezol (Merck & Co.); Tecto (Syngenta)
Molecular Formula: C10H7N3S
Molecular Weight: 201.25
Percent Composition: C 59.68%, H 3.51%, N 20.88%, S 15.93%
Literature 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: Colorless crystals, mp 304-305°. uv max (methanol): 298 nm (e 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).
Melting point: mp 304-305°
Absorption maximum: uv max (methanol): 298 nm (e 23330)
Toxicity data: LD50 in mice, rats, rabbits (g/kg): 3.6, 3.1, >3.8 orally (Robinson)
Derivative Type: Hypophosphite
CAS Registry Number: 28558-32-9
Trademarks: Arbotect (Syngenta)
Properties: Amber liquid. d25 1.103.
Density: 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.
Therap-Cat: Anthelmintic (Nematodes).
Therap-Cat-Vet: Anthelmintic, fungicide.
Keywords: Anthelmintic (Nematodes). |