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triflumizole
Fungicide
FRAC 3, G1; DMI: imidazole
NOMENCLATURE
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 Development codes NF-114 (Nippon Soda)
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
COMMERCIALISATION
History Fungicide reported by A. Nakata (Proc. Int. Congr. Pestic. Chem., Kyoto, 5th, 1982). Introduced by Nippon Soda Co., Ltd. Registered in Japan in 1986. Patents JP 79119462; US 4208411; UK 1591212; DE 2814041. Manufacturers Nippon Soda
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 Bipolaris oryzae, Tilletia and Ustilago spp. in cereals. Formulation types EC; FU; WP. Selected products: 'Trifmine' (Nippon Soda); 'Procure' (Crompton); mixtures: 'Pancho TF' (+ cyflufenamid) (Nippon Soda)
OTHER PRODUCTS
'Duo Top' (Siegfried); 'Rocket' (Certis Europe); 'Terraguard' (Crompton) Discontinued products: 'Condor' * (Kwizda)
ANALYSIS
Product analysis by hplc. Residues determined by hplc.
MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for male rats 715, female rats 695 mg/kg. Skin and eye Acute percutaneous LD50 for rats >5000 mg/kg. Mild eye irritant; not a skin irritant. Inhalation LC50 (4 h) for rats >3.2 mg/l air. NOEL (2 y) for rats 3.7 mg/kg diet. ADI 0.0185 mg/kg (Japan) Toxicity class WHO (a.i.) III; EPA (formulation) III
ECOTOXICOLOGY
Birds Acute oral LD50 for male Japanese quail 2467, female Japanese quail 4308 mg/kg. Fish LC50 (48 h) for carp 1.26 mg/l. Daphnia LC50 (3 h) 9.7 mg/l. Bees LD50 for honeybees 0.14 mg/bee.
ENVIRONMENTAL FATE
Animals For details of metabolism in rats, see T. Tanoue et al., IUPAC 7th Int. Congr. Pestic. Chem., 1990, 2, 177. Soil/Environment In soil, DT50 14 d (on clay). Photolytic degradation leads to the metabolite (E)-4-chloro-a,a,a-trifluoro-N-(1-amino-1-yl-2-propoxyethylidene)-o-toluidine. Koc 1083-1663.
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