cyflufenamid
Fungicide
NOMENCLATURE
Common name cyflufenamid (BSI, pa ISO)
IUPAC name (Z)-N-[a-(cyclopropylmethoxyimino)-2,3-difluoro-6-(trifluoromethyl)benzyl]-2-phenylacetamide
Chemical Abstracts name (Z)-N-[[(cyclopropylmethoxy)amino][2,3-difluoro-6-(trifluoromethyl)phenyl]methylene]benzeneacetamide
CAS RN [180409-60-3] Development codes NF-149
PHYSICAL CHEMISTRY
Mol. wt. 412.4 M.f. C20H17F5N2O2 Form White solid with a slight aromatic odour. M.p. 61.5-62.5 °C B.p. 256.8 °C V.p. 3.54 ´ 10-2 mPa (20 ºC, gas saturation method) KOW logP = 4.70 (pH 6.75, 25 ºC) S.g./density 1.347 (20 °C) Solubility In water 5.20 ´ 10-4 g/l (pH 6.5, 20 ºC). In dichloromethane 902, acetone 920, xylene 658, acetonitrile 943, methanol 653, ethanol 500, ethyl acetate 808, n-hexane 18.6, n-heptane 15.7 (all in g/l, 20 ºC). Stability Stable at pH 4 and 7; DT50 288 d (pH9). Aqueous photolysis DT50 594 d. pKa 12.08
COMMERCIALISATION
Patents US 5847005; WO96/19442 Manufacturers Nippon Soda
APPLICATIONS
Mode of action Fungicide with pre- and post-emergence activity. Uses Registered for control of powdery mildew in wheat, top fruit and vegetables, at 2.5 g/100l, in Japan. Under development for control of powdery mildew in wheat and barley, at 25 g/ha, in Europe. Formulation types WG; EW. Selected products: 'Pancho' (Nippon Soda); mixtures: 'Pancho TF' (+ triflumizole) (Nippon Soda)
MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for male and female rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 for male and female rats >2000 mg/kg. Weakly irritating to eyes, non-irritating to skin (rabbits). Inhalation LC50 (4 h) for male and female rats >4.76 mg/l. ADI 0.041 mg/kg (Japan).
ECOTOXICOLOGY
Birds Acute oral LD50 for bobwhite quail >2000 mg/kg. Dietary LC50 for bobwhite quail >5000 ppm. Fish LC50 (96 h) for carp >1.14 ppm. Daphnia LC50 (48 h) >1.73 ppm. Algae EbC50 (72 h) for Selenastrum capricornutum >0.828 ppm; ErC50 (72 h) for Selenastrum capricornutum >0.828 ppm. Bees LD50 (oral and contact) >100 mg/bee. Worms LC50 for earthworm >1000 mg/kg soil. Other beneficial spp. No effect on Orius similis at 50ppm.
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