Fungistin

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Fungicide: Benzimidazole

NOMENCLATURE
Common name carbendazim (BSI, E-ISO); carbendazime ((f) F-ISO); carbendazol (JMAF)
IUPAC name methyl benzimidazol-2-ylcarbamate
Chemical Abstracts name methyl 1H-benzimidazol-2-ylcarbamate
Other names MBC; BMC CAS RN [10605-21-7] EEC no. 234-232-0 Development codes BAS 346F (BASF); Hoe 017411 (Hoechst); DPX-E 965 (Du Pont)

PHYSICAL CHEMISTRY
Mol. wt. 191.2 M.f. C9H9N3O2 Form Crystalline powder. M.p. 302-307 A C (decomp.) V.p. 0.09 mPa (20 A C); 0.15 mPa (25 A C); 1.3 mPa (50 A C); separate study gives <0.0001 mPa (20 A C) KOW logP = 1.38 (pH 5), 1.51 (pH 7), 1.49 (pH 9) Henry 3.6 A' 10-3 Pa m3 mol-1 (calc.) S.g./density 1.45 (20 A C) Solubility In water 29 mg/l (pH 4), 8 mg/l (pH 7), 7 mg/l (pH 8) (24 A C). In dimethylformamide 5, acetone 0.3, ethanol 0.3, chloroform 0.1, ethyl acetate 0.135, dichloromethane 0.068, benzene 0.036, cyclohexane <0.01, diethyl ether <0.01, hexane 0.0005 (all in g/l, 24 A C). Stability Decomposes at m.p.; stable for at least 2 y below 50 A C. Stable after 7 d at 20 000 lux. Slowly decomposed in alkaline solution (22 A C); DT50 >350 d (pH 5 and pH 7), 124 d (pH 9). Stable in acids, forming water-soluble salts. pKa 4.2, weak base

APPLICATIONS
Biochemistry Reported to inhibit beta-tubulin synthesis. Mode of action Systemic fungicide with protective and curative action.