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fenoxaprop-P-ethyl Chemical Abstracts name ethyl (R)-2-[4-[(6-chloro-2-benzoxazolyl)oxy]phenoxy]propanoate CAS RN [71283–80–2] Development codes Hoe 046360 (Hoechst); AE F046360 (AgrEvo) Smiles code CCOC(=O)[C@@H](C)Oc1ccc(Oc2nc3ccc(Cl)cc3o2)cc1;without stereochemistry:CCOC(=O)C(C)Oc1ccc(Oc2nc3ccc(Cl)cc3o2)cc1 fenoxaprop-P Common name fenoxaprop-P (BSI, E-ISO); fénoxaprop-P ((m) F-ISO) IUPAC name (R)-2-[4-(6-chloro-1,3-benzoxazol-2-yloxy)phenoxy]propionic acid; (R)-2-[4-(6-chlorobenzoxazol-2-yloxy)phenoxy]propionic acid Chemical Abstracts name (R)-2-[4-[(6-chloro-2-benzoxazolyl)oxy]phenoxy]propanoic acid CAS RN [113158–40–0] Development codes Hoe 088406 (Hoechst); AE F088406 (AgrEvo) PHYSICAL CHEMISTRY fenoxaprop-P-ethyl Mol. wt. 361.8 M.f. C18H16ClNO5 Form White, odourless solid. M.p. –91 °C V.p. 5.3 × 10 mPa (20 °C) Kow logP = 4.58 Henry 2.74 × 10 Pa m mol (calc.) S.g./density 1.3 (20 °C) Solubility In water 0.7 mg/l (pH 5.8, 20 °C). In acetone, toluene and ethyl acetate >200, methanol 43 (all in g/l, 20 °C). Stability Fenoxaprop-P-ethyl is stable for 90 d at 50 °C. Not sensitive to light. Hydrolysis DT50 2.8 d (pH 4), 19.2 d (pH 5), 23.2 d (pH 7), 0.6 d (pH 9) (25 °C) (EFSA Sci. Rep. (2007) 121, 1–76). fenoxaprop-P Mol. wt. 333.7 M.f. C16H12ClNO5 Form Light beige, weakly pungent, fine powder. M.p. 155–161 °C V.p. 3.5 × 10 mPa Kow logP = 1.83–0.24 (pH 5–9) Henry 1.91 × 10 Pa m mol(pH 7.0, calc.) S.g./density c. 1.5 (20 °C) Solubility In water 0.27 (pH 5.1), 61 (pH 7.0) (both in g/l, 20 °C). In acetone 80, toluene 0.5, ethyl acetate 36, methanol 34 (all in g/l, 20 °C). COMMERCIALISATION History The herbicidal enantiomer of fenoxaprop was reported by H. P. Huff et al. (Proc. Br. Crop Prot. Conf. - Weeds, 19, 2, 717). Introced by Hoechst AG (now Bayer AG) in 1988. Manufacturers Bayer CropScience; Anhui Huaxing; Cheminova; Fengle; JIE; Jingma; Kajo; Sharda; Sundat; Tide; Zhejiang Hisun APPLICATIONS fenoxaprop-P-ethyl Biochemistry Fatty acid synthesis inhibition in grasses, by inhibition of acetyl CoA carboxylase (ACCase). Rapidly hydrolysed in plants to the acid, which is still herbicidally active. Mode of action Fenoxaprop-P-ethyl is a selective herbicide with contact and systemic action, absorbed principally by the leaves, with translocation both acropetally and basipetally to the roots or rhizomes. Uses Post-emergence control of annual and perennial grass weeds in potatoes, beans, soya beans, beets, vegetables, peanuts, flax, oilseed rape and cotton; and (when applied with the herbicide safener mefenpyr-diethyl) annual and perennial grass weeds and wild oats in wheat, rye, triticale and, depending on ratio, in some varieties of barley. Applied at 40–90 g/ha in cereals (max. 83 g/ha in EU) and at 30–140 g/ha in broad-leaved crops. Phytotoxicity Non-phytotoxic to broad-leaved crops. Formulation types EC; EW; SE. PRODUCTS fenoxaprop-P-ethyl Selected procts 'Furore Super' (Bayer CropScience); 'Foxtrot' (Cheminova); 'Masaldo' (Crop Health); 'Sunfenoxa-P-Ethyl' (Sundat); mixtures 'Hussar' (+ iodosulfuron-methyl-sodium + mefenpyr-diethyl) (Bayer CropScience); 'Puma' (+ mefenpyr-diethyl) (Bayer CropScience); 'Puma Super' (+ mefenpyr-diethyl) (Bayer CropScience). Other procts 'Acclaim Super' (Bayer CropScience); 'Bugle' (Bayer CropScience); 'Depon Super' (Bayer CropScience); 'Option II' (Bayer CropScience); 'Rumpas' (Bayer CropScience); 'Silverado' (Bayer CropScience); 'Starice' (Bayer CropScience); 'Triumph' (Bayer CropScience); 'Whip 360' (Bayer CropScience); 'Whip Super' (Bayer CropScience); 'Felmon' (Efthymiadis); 'Jupiter' (P I Instries); 'Orion' (Biostadt); 'Ralon' (Nufarm Deutschland); mixtures 'Baghera' (+ diclofop-methyl + mefenpyr-diethyl) (Bayer CropScience); 'Cheetah Super' (+ mefenpyr-diethyl) (Bayer CropScience); 'Cheyenne' (+ MCPA-2-ethylhexyl) (Bayer CropScience); 'Corniche' (+ diclofop-methyl + mefenpyr-diethyl) (Bayer CropScience); 'Dakota' (+ MCPA-2-ethylhexyl) (Bayer CropScience); 'Djinn' (+ isoproturon + mefenpyr-diethyl) (Bayer CropScience); 'Dopler' (+ diclofop-methyl + mefenpyr-diethyl) (Bayer CropScience); 'Horizon 2000' (+ fluazifop-P-butyl) (Bayer CropScience); 'Hussar OF' (+ iodosulfuron-methyl-sodium + mefenpyr-diethyl) (Bayer CropScience); 'Podium S' (+ clethodim) (Bayer CropScience); 'Preclaim' (+ pendimethalin) (Bayer CropScience); 'Proper energy' (+ mefenpyr-diethyl) (Bayer CropScience); 'Puma Extra' (+ isoproturon) (Bayer CropScience); 'Puma Power' (+ mefenpyr-diethyl) (Bayer CropScience); 'Puma S' (+ mefenpyr-diethyl) (Bayer CropScience); 'Puma X' (+ isoproturon) (Bayer CropScience); 'Ricestar' (+ isoxadifen-ethyl) (Bayer CropScience); 'Ricestar xtra' (+ ethoxysulfuron) (Bayer CropScience); 'Tigress Ultra' (+ diclofop-methyl) (Bayer CropScience); 'Tiller' (+ 2,4-D-2-ethylhexyl + MCPA-2-ethylhexyl) (Bayer CropScience); 'Tiller Gold' (+ ethoxysulfuron) (Bayer CropScience); 'Turbo' (+ ethoxysulfuron + isoxadifen-ethyl) (Bayer CropScience); 'Wildcat' (+ mefenpyr-diethyl) (Bayer CropScience); 'Zeus' (+ diclofop-methyl + mefenpyr-diethyl) (Bayer CropScience); 'Bledor' (+ diclofop-methyl + mefenpyr-diethyl) (Siapa); 'Fenuron Super-Set' (+ chlorotoluron) (Nufarm Deutschland); 'Fusion' (+ fluazifop-P-butyl) (Bayer CropScience, Syngenta); 'Ralon Super' (+ mefenpyr-diethyl) (Nufarm Deutschland). Discontinued procts 'Silban' * (IPESA); mixtures 'Tigress' * (+ diclofop-methyl) (AgrEvo); 'Tiller' * (+ 2,4-D-isoctyl + MCPA-2-ethylhexyl) (AgrEvo); 'Twister' * (+ fluazifop-P-butyl + fomesafen-sodium) (Syngenta). ANALYSIS Proct analysis by hplc with uv detection; enantiomeric purity by chiral phase separation, followed by uv detection (CIPAC Handbook, 2000, J, 51). Details are also available from Bayer CropScience. TOXICOLOGICAL & ENVIRONMENTAL REVIEWS EFSA Sci. Rep. (2007) 121, 1–76. 91/414/EC Annex I status Included, 2008/66/EC. MAMMALIAN TOXICOLOGY fenoxaprop-P-ethyl Oral Acute oral LD50 for rats 3150–4000, mice >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Inhalation LC50 (4 h) for rats >1.224 mg/l air. NOEL (90 d) for rats 0.75 mg/kg b.w. daily (10 ppm), for mice 1.4 mg/kg b.w. daily (10 ppm), for dogs 15.9 mg/kg b.w. daily (400 ppm). ADI/RfD (EC) 0.01 mg/kg b.w. [2008]. ECOTOXICOLOGY fenoxaprop-P-ethyl Birds Acute oral LD50 for bobwhite quail >2000 mg/kg. Fish LC50 (96 h) for bluegill sunfish 0.58, rainbow trout 0.46 mg/l. Daphnia LC50 (48 h) 0.56 (pH 8.0–8.4), 2.7 (pH 7.7–7.8) mg/l. Algae LC50 (72 h) for Scenedesmus subspicatus 0.51 mg/l. Bees LC50 (oral) >199 μg/bee; (contact) >200 μg/bee (EFSA Sci. Rep.). Worms LC50 (14 d) for Eisenia foetida >1000 mg/kg soil. ENVIRONMENTAL FATE Plants In plants, fenoxaprop-P-ethyl is metabolised via fenoxaprop-P to 6-chloro-2,3-dihydrobenzoxazol-2-one. Soil/Environment In soil, fenoxaprop-P-ethyl is rapidly hydrolysed to fenoxaprop-P (A. E. Smith, J. Agric. Food Chem., 1985, 33, 483); DT50 1–10 d.