haloxyfop-P
Herbicide
HRAC A WSSA 1; aryloxyphenoxypropionate
NOMENCLATURE
haloxyfop-P
IUPAC name (R)-2-[4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy]propionic acid
Chemical Abstracts name (R)-(+)-2-[4-[[3-chloro-5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic acid
CAS RN [95977-29-0]
haloxyfop-P-methyl
IUPAC name methyl (R)-2-[4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy]propionate
Chemical Abstracts name methyl (R)-(+)-2-[4-[[3-chloro-5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoate
Other names haloxyfop-R CAS RN [72619-32-0] EEC no. 406-250-0 Development codes DE-535 (Dow)
PHYSICAL CHEMISTRY
haloxyfop-P
Mol. wt. 361.7 M.f. C15H11ClF3NO4 Form Colourless crystals. M.p. 70.5-74.5 °C V.p. 3.5 ´ 10-3 mPa (25 °C) KOW logP = 0.27 (pH 7) Solubility In water 375 mg/l (20 ºC). In acetone, dichloromethane, methanol, xylene >639 g/l (20 ºC). pKa 4.27
haloxyfop-P-methyl
Composition The (R)- isomer of haloxyfop-methyl. Mol. wt. 375.7 M.f. C16H13ClF3NO4 Form Clear brown, odourless liquid. B.p. >280 ºC V.p. 0.328 mPa (25 ºC) KOW logP = 4.00 Henry 1.1 ´ 10-3 Pa m3 mol-1 (20 °C, calc.) S.g./density 1.372 (20 °C) Solubility In water 9.08 mg/l (25 ºC). In acetone, cyclohexanone, dichloromethane, ethanol, methanol, toluene, xylene >1 kg/l (20 ºC). Stability DT50 in water 100 d (pH5), 48 d (pH7), 52 h (pH9) (all 25°C). F.p. 186 °C
COMMERCIALISATION
History The methyl ester reported by Bayer S.A. (M. C. Botte et al., Proc. 15th Columa Conf., 1992, 1, 397) and introduced by DowElanco (now Dow AgroSciences). Manufacturers Dow AgroSciences
APPLICATIONS
Biochemistry Fatty acid synthesis inhibitor, by inhibition of acetyl CoA carboxylase (ACCase). Mode of action Haloxyfop-P-methyl is a selective herbicide, absorbed by the foliage and roots, and hydrolysed to haloxyfop-P, which is translocated to meristematic tissues, and inhibits their growth. Uses Haloxyfop-P-methyl is used post-emergence for control of annual and perennial grasses in sugar beet, fodder beet, oilseed rape, potatoes, leaf vegetables, onions, flax, sunflowers, soya beans, vines, strawberries, and other crops. Applied at 52-104 g a.e./ha. Formulation types EC.
haloxyfop-P-methyl
Selected products: 'Gallant Super' (Dow AgroSciences)
OTHER PRODUCTS
haloxyfop-P-methyl
'Eloge' (Dow AgroSciences, Bayer CropScience); 'Galant' (Dow AgroSciences); 'Zellek Super' (Dow AgroSciences)
ANALYSIS
Product analysis by hplc. Residues determined by glc. Details available from Dow AgroSciences.
MAMMALIAN TOXICOLOGY
haloxyfop-P-methyl
Oral Acute oral LD50 for male rats 300, female rats 623 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Non-irritant to skin; slightly irritating to eyes (rabbits). NOEL (2 y) for rats 0.065 mg/kg b.w. daily; no increase in hepatotoxicity. ADI As haloxyfop. EC classification Xn; R22| N; R50, R53
ECOTOXICOLOGY
haloxyfop-P
Birds Acute oral LD50 for bobwhite quail 414 mg/kg. Fish LC50 (96 h) for rainbow trout >50 mg/l. Daphnia LC50 (48 h) >100 mg/l. Algae EC50 (96 h) >70 mg/l. Bees LD50 (48 h, oral and contact) >100 mg/bee.
haloxyfop-P-methyl
Birds Acute oral LD50 for bobwhite quail 1159 mg/kg. Fish LC50 (96 h) for rainbow trout 0.7 mg/l. Daphnia LC50 (48 h) 6.12 mg/l. Algae EC50 (5 d) 1.72 mg/l. Bees LD50 (48 h, oral and contact) >100 mg/bee. Worms LC50 (14 d) 1343 mg/kg.
ENVIRONMENTAL FATE
haloxyfop-P-methyl
Animals In mammals, rapidly converted to the parent acid and eliminated. Plants Hydrolysed to haloxyfop, terminal residue haloxyfop, or conjugates. Soil/Environment DT50 <24 h, forming the parent acid, which is then microbially degraded. Haloxyfop acid degradation approximates to first order kinetics and involves degradation to the pyridinol and other minor metabolites. DT50 9 to 20.5 d, average 14 d (various soil types).
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