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Herbicides

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Bispyribac Sodium

HRAC B WSSA 2 pyrimidinyloxybenzoic

NOMENCLATURE
Common name bispyribac (BSI, E-ISO, (m) F-ISO, for the carboxylic acid) IUPAC name sodium 2,6-bis(4,6-dimethoxypyrimidin-2-yloxy)benzoate
Chemical Abstracts name sodium 2,6-bis[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzoate CAS RN [125401–75–4] acid; [125401–92–5] sodium salt Development codes KIH-2023; KUH-911 (both Kumiai); V-10029 Smiles code [Na+].COc1cc(OC)nc(Oc2cccc(Oc3nc(OC)cc(OC)n3)c2C(=O)[O-])n1
PHYSICAL CHEMISTRY
Composition Tech. is >93%. Mol. wt. 452.4 M.f. C19H17N4NaO8; C19H18N4O8 (acid) Form White odourless powder. M.p. 223–224 °C V.p. 5.05 × 10-6 mPa (25 °C) Kow logP = –1.03 (23 °C) Henry 3 × 10-11 Pa m3 mol-1 (calc.) S.g./density 1.47 Solubility In water 68.7 g/l (20 °C, distilled water). In methanol 25 g/l (20 °C); in ethyl acetate 6.1 × 10-2, n-hexane 8.34 × 10-3, acetone 1.4, toluene <1.0 × 10-6, dichloromethane 1.3 (all in mg/l, 25 °C). Stability Decomposes at 223 °C. Hydrolysis DT50 >1 y (pH 7 and 9, 25 °C), 88 d (pH 4, 25 °C). Aqueous photolysis DT50 42 d in natural water, 499 d in distilled water (both 25 °C, 1.53 W/m2, 260–365 nm). pKa 3.35 (20 °C)
COMMERCIALISATION
History Discovered in 1988. Reported by Kumiai Chemical Industry Co., Ltd (M. Yokoyama et al., Proc. Br. Crop Prot. Conf. - Weeds, 1993, 1, 61). Developed jointly by Kumiai and Ihara Chemical Industry Co., Ltd and introduced in 1997. Patents US 4906285; EP 321846 Manufacturers Kumiai; Fertiagro; Heben; AGROFINA; Shandong Qiaochang
APPLICATIONS
Biochemistry Branched chain amino acid synthesis (ALS or AHAS) inhibitor. Mode of action Selective, systemic post-emergence herbicide, absorbed by foliage and roots. Uses Control of grasses, sedges and broad-leaved weeds, especially Echinochloa spp., in direct-seeded rice, at rates of 15–45 g/ha. Also used to stunt growth of weeds in non-crop situations. Formulation types AL; SC; SL.
PRODUCTS
Selected products ‘Ectran’ (AGROFINA) ; ‘Grass-short’ (non-crop land) (Kumiai) ; ‘Nominee’ (Bayer CropScience, Kumiai) ; ‘Paladin’ (Baocheng) ; ‘Short-keep’ (non-crop land) (Riken Green) ; ‘Sunbishi’ (Sundat) Other products ‘Regiment’ (Kumiai, Valent) ; ‘Velocity’ (Valent) ; ‘Tradewind’ (Valent)
ANALYSIS
In soil by gc with MSD (Environ. Chem. Methods). In water by hplc with uv detection (ibid.). Metabolites in soil or water by hplc with uv detection (ibid.). Details available from Kumiai.
ENVIRONMENTAL FATE
Animals >95% of dose applied to rats was excreted in urine and faeces within 7 d. Plants Following application to foliage and soil at 5-leaf stage of rice plants, c. 10% of carbon label was distributed between straw and roots at harvest. Soil/Environment In soil, DT50 <10 d (flooded and upland conditions).
TOXICOLOGICAL & ENVIRONMENTAL REVIEWS
EU Rev. Rep. SANCO/13263/2010 (2011); EFSA Jou. 2010,8(10):1692. EU 1107/2009 Annex B Status Included, (EU) 740/2011; (2011/22/EU).
MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for male rats 4111, female rats 2635, male and female mice 3524 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Non-irritating to skin; slightly irritating to eyes (rabbits). Inhalation LC50 (4 h) for rats >4.48 mg/l. NOEL (2 y) for male rats 20 mg/kg diet (1.1 mg/kg b.w. daily), female rats 20 mg/kg diet (1.4 mg/kg b.w. daily), male mice 14.1 mg/kg b.w. daily, female mice 1.7 mg/kg b.w. daily. ADI 0.011 mg/kg. Other Non-mutagenic in the Ames test, and non-teratogenic to rats and rabbits. Toxicity class WHO (a.i.) U.
ECOTOXICOLOGY
Birds Acute oral LD50 for bobwhite quail >2250 mg/kg. Dietary LC50 (5 d) for bobwhite quail and mallard ducks >5620 mg/kg diet. Fish Acute LC50 (96 h) for rainbow trout and bluegill sunfish >100 ppm, for carp >952 mg/l. NOEC (32 d) for fathead minnow 10 ppm. Daphnia LC50 (48 h) >100 ppm. NOEC (21 d) 110 ppm. Algae EC50 (72 h) for Selenastrum capricornutum 1.7 mg/l; EC50 (120 h) for S. capricornutum 3.4 mg/l, NOEC 0.625 mg/l. Other aquatic spp. ErC50 (7 d) for Lemna gibba 0.0204 ppm. Bees LD50 (oral, 48 h) >200 μg/bee; LC50 (contact) >7000 mg/l spray. Worms NOEL (14 d) for Eisenia foetida >1000 mg/kg soil. Other beneficial spp. LC50 for Bombyx mori >1000 ppm; LC50 (48 h) for Orius strigicollis and Phytoseiulus persimilis >300 g/ha.

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