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 ºC (decomp.) V.p. 0.09 mPa (20 ºC); 0.15 mPa (25 ºC); 1.3 mPa (50 ºC); separate study gives <0.0001 mPa (20 ºC) KOW logP = 1.38 (pH 5), 1.51 (pH 7), 1.49 (pH 9) Henry 3.6 ´ 10-3 Pa m3 mol-1 (calc.) S.g./density 1.45 (20 ºC) Solubility In water 29 mg/l (pH 4), 8 mg/l (pH 7), 7 mg/l (pH 8) (24 ºC). 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 ºC). Stability Decomposes at m.p.; stable for at least 2 y below 50 ºC. Stable after 7 d at 20 000 lux. Slowly decomposed in alkaline solution (22 ºC); 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. Absorbed through the roots and green tissues, with translocation acropetally. Acts by inhibiting development of the germ tubes, the formation of appressoria, and the growth of mycelia. Uses Control of Septoria, Fusarium, Erysiphe and Pseudocercosporella in cereals; Sclerotinia, Alternaria and Cylindrosporium in oilseed rape; Cercospora and Erysiphe in sugar beet; Uncinula and Botrytis in grapes; Cladosporium and Botrytis in tomatoes; Venturia and Podosphaera in pome fruit and Monilia and Sclerotinia in stone fruit. Application rates vary from 120-600 g/ha, depending on crop. A seed treatment (0.6-0.8 g/kg) will control Tilletia, Ustilago, Fusarium and Septoria in cereals, and Rhizoctonia in cotton. Also shows activity against storage diseases of fruit as a dip (0.3-0.5 g/l). Formulation types OP; SC; SL; WG; WP; Seed treatment. Compatibility Incompatible with alkaline materials.
