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Common name imazalil (BSI, E-ISO, (m) F-ISO, ANSI); chloramizol (Republic of South Africa); enilconazole (BAN, INN)
IUPAC name (?-1-(b-allyloxy-2,4-dichlorophenylethyl)imidazole; (?-allyl 1-(2,4-dichlorophenyl)-2-imidazol-1-ylethyl ether
Chemical Abstracts name (?-1-[2-(2,4-dichlorophenyl)-2-(2-propenyloxy)ethyl]-1H-imidazole
CAS RN [35554-44-0] unstated stereochemistry; [73790-28-0]
PHYSICAL CHEMISTRY
Mol. wt. 297.2 M.f. C14H14Cl2N2O Form Slightly yellow to brown, crystalline mass. M.p. 52.7 ºC B.p. >340 ºC V.p. 0.158 mPa (20 ºC) KOW logP = 3.82 (pH 9.2 buffer) Henry 2.61 ´ 10-4 Pa m3 mol-1 (calc.) S.g./density 1.348 g/ml (26 ºC) Solubility In water 0.18 g/l (pH 7.6, 20 ºC). In acetone, dichloromethane, ethanol, methanol, isopropanol, xylene, toluene, benzene >500, hexane 19 (all in g/l, 20 ºC). Also soluble in heptane and petroleum ether. Stability Very stable to hydrolysis in dilute acids and alkalis at room temperature, in the absence of light. Stable to temperatures up to 285 ºC. Stable to light under normal storage conditions. pKa 6.53, weak base F.p. 192 ºC
APPLICATIONS
Biochemistry Steroid demethylation (ergosterol biosynthesis) inhibitor.
Mode of action Systemic fungicide, with protective and curative action.
Uses Control of a wide range of fungal diseases on fruit, vegetables, and ornamentals, e.g. powdery mildews on cucurbits and ornamentals; powdery mildew on roses; storage diseases (particularly Penicillium, Gloeosporium, Phomopsis, Phoma spp., etc.) of citrus fruit, pome fruit, bananas, and seed potatoes. Also used as a seed dressing, for control of diseases (particularly Fusarium and Helminthosporium spp.) of cereals. It is particularly active against benzimidazole-resistant strains of plant-pathogenic fungi. Typical use rates are: for seed treatment 4-5 g a.i./100 kg seed; for ornamentals and vegetables 5-30 g/hl; and for post-harvest treatment 2-4 g/t fruit.