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Common name triflumizole (BSI, JMAF, draft E-ISO, (f) draft F-ISO)
IUPAC name (E)-4-chloro-a,a,a-trifluoro-N-(1-imidazol-1-yl-2-propoxyethylidene)-o-toluidine
Chemical Abstracts name (E)-1-[1-[[4-chloro-2-(trifluoromethyl)phenyl]imino]-2-propoxyethyl]-1H-imidazole
CAS RN [99387-89-0] (E)- isomer; [68694-11-1] unstated stereochemistry
PHYSICAL CHEMISTRY
Mol. wt. 345.7 M.f. C15H15ClF3N3O Form Colourless crystals. M.p. 63.5 ºC V.p. 0.186 mPa (25 ºC) KOW logP = 5.06 (pH 6.5), 5.10 (pH 6.9), 5.12 (pH 7.9) Henry 5.6 ´ 10-6 Pa m3 mol-1 (25 °C, calc.) Solubility In water 12.5 g/l (20 ºC). In chloroform 2220, hexane 17.6, xylene 639, acetone 1440, methanol 496 (all in g/l, 20 ºC). Stability Unstable in highly alkaline and acidic media. Aqueous solutions degraded by sunlight, DT50 29 h. pKa 3.7 (25 ºC), weak base
APPLICATIONS
Biochemistry Steroid demethylation (ergosterol biosynthesis) inhibitor.
Mode of action Systemic fungicide with protective and curative action.
Uses Control of Gymnosporangium and Venturia spp. in pome fruit, against powdery Erysiphaceae in fruit and vegetables, and against Fusarium, Fulvia and Monilinia spp. Application at 180-300 g/ha in vegetables, and 700-1000 g/ha in orchards. It is also used as a seed treatment against Helminthosporium, Tilletia and Ustilago spp. in cereals.