Ads by Google
NOMENCLATURE Common name: fluazifop-P-butyl
Classification: agriculture herbicide
IUPAC name: butyl (R)-2-[4-(5-trifluoromethyl-2-pyridyloxy)phenoxy]propionate
Chemical name :butyl (R)-2-[4-[[5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoate
CAS RN [79241-46-6] Development codes PP005; ICIA0005 (both ICI); SL-118 (Ishihara Sangyo)
PHYSICAL CHEMISTRY Composition Tech. is ³90% pure. Mol. wt. 383.4 M.f. C19H20F3NO4 Form Colourless liquid. M.p. -20 ºC (glass-like) B.p. 154 ºC/0.02 mmHg V.p. 0.033 mPa (20 ºC) KOW logP = 4.5 (20 ºC) Henry 1.1 ´ 10-2 Pa m3 mol-1 S.g./density 1.22 (20 ºC) Solubility In water 1.1 mg/l (20 °C). Miscible with acetone, hexane, methanol, dichloromethane, ethyl acetate, toluene, and xylene. Stability Fluazifop-P-butyl is stable to u.v. light. Hydrolysis DT50 >30 d (pH 5), 78 d (pH 7), 29 h (pH 9). Aqueous photolysis DT50 6 d (pH 5). pKa -3.1 (calc.) F.p. 83 °C
Mol. wt. 327.3 M.f. C15H12F3NO4 Form Pale yellow, glass-like material. M.p. Glass transition temperature 4 °C V.p. 7.9 ´ 10-4 mPa (20 °C) KOW logP = 3.1 (pH 2.6, 20 °C), -0.8 (pH 7, 20 °C, est.) Henry 3 ´ 10-7 Pa m3 mol-1 (calc.) Solubility In purified water 780 mg/l (20 °C). Stability No significant hydrolysis at pH 5, 7 and 9 (25 °C). pKa 2.98
APPLICATIONS Biochemistry Fatty acid synthesis inhibitor, by inhibition of acetyl CoA carboxylase (ACCase). Mode of action Fluazifop-P-butyl is quickly absorbed through the leaf surface, hydrolysed to fluazifop-P and translocated through the phloem and xylem, accumulating in the rhizomes and stolons of perennial grasses and the meristems of annual and perennial grasses. Uses Post-emergence control of wild oats, volunteer cereals, and annual and perennial grass weeds in oilseed rape, sugar beet, fodder beet, potatoes, vegetables, cotton, soya beans, pome fruit, stone fruit, bush fruit, vines, citrus fruit, pineapples, bananas, strawberries, sunflowers, alfalfa, ornamentals, and other broad-leaved crops. Applied at 125-375 g/ha. Phytotoxicity Non-phytotoxic to broad-leaved crops. Formulation types EC; EW.
MAMMALIAN TOXICOLOGY Oral Acute oral LD50 for male rats 3680, female rats 2451 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits >2000 mg/kg. Slight skin and mild eye irritant (rabbits). Not a skin sensitiser (guinea pigs). Inhalation LC50 (4 h) for rats >5.24 mg/l. NOEL NOAEL (2 y) for rats 1.0 mg/kg b.w. daily (10 mg/kg diet); (1 y) for dogs 25 mg/kg b.w. daily; (90 d) for rats 9.0 mg/kg b.w. daily (100 mg/kg diet). Multi-generation study (rats) 0.9 mg/kg b.w. daily (10 mg/kg diet); developmental toxicity for rats 5 mg/kg b.w. daily, for rabbits 30 mg/kg b.w. daily. ADI (EPA) 0.01 mg/kg. Other Genotoxicity negative. Toxicity class WHO (a.i.) III
ECOTOXICOLOGY Birds Acute oral LD50 for mallard ducks >3500 mg/kg. Fish LC50 (96 h) for rainbow trout 1.3 mg/l. Daphnia EC50 (48 h) >1.0 mg/l. Algae EC50 (72 h) for Navicula pelliculosa 0.51 mg/l. Bees Very low toxicity to bees. LD50 (oral and contact) >0.2 mg/bee. Worms LC50 >1000 mg/kg.
Fish LC50 (96 h) for rainbow trout 117 mg/l. Daphnia EC50 (48 h) 240 mg/l. Algae EC50 (72 h) for Selenastrum capricornutum >56 mg/l.
ENVIRONMENTAL FATE Animals In mammals, fluazifop-P-butyl is metabolised to fluazifop-P, which is rapidly excreted. Plants In plants, fluazifop-P-butyl is rapidly hydrolysed to fluazifop-P, which is then partly conjugated. Ether cleavage gives the pyridone and propionic acid metabolites, which may both be further metabolised or conjugated. Soil/Environment Koc 5800. In moist soils, rapid degradation of fluazifop-P-butyl occurs, DT50 <24 h. The major degradation product is fluazifop-P, which is hydrolysed to 5-trifluoromethylpyrid-2-one, and 2-(4-hydroxyphenoxy)propionic acid, both of which are further degraded, ultimately to CO2. Soil/Environment In laboratory soil (40% MHC, pH 5.3-7.7), DT50 2-9 d (20 °C). Field DT50 <4 w. Koc 39-84. For degradation route, see fluazifop-P-butyl.
fluazifop-p-butyl 15%EC