Beflubutamid 氟丁酰草胺


中文通用名称: 氟丁酰草胺
英文通用名称: beflubutamid
试验代号: UBH-820
CAS No:113614-08-7
化学结构类型: 苯氧酰胺类
作用机理: 胡萝卜素生物合成抑制剂
应用: 主要用于小麦田苗后防除重要的阔叶杂草,使用剂量为170~251克有效成分/公顷,同异丙隆混用除草效果尤佳。
开发公司: 日本宇部产业公司.

该产品是由日本宇部兴株式会社研发的选择性除草剂,1999年首次在英国布莱顿植保会议上报道。该除草剂在作物芽后早期施用,对小麦、大麦、黑麦和黑小麦等作物田间的阔叶杂草如阿拉伯婆婆纳、野芝麻和地堇菜等有卓越的防效。主要用于小麦田苗后防除重要的阔叶杂草,使用剂量为170-251克/公顷,比异丙隆效果更好。   Herbaflex ( Ube 工业公司的beflubufamid 85%g/l+异丙隆500g/l)是芽后谷物除草剂,可用于冬小麦、大麦、黑麦和黑小麦。防除窄叶和阔叶杂草,包括宝盖草、猪殃殃等。田间试验用量2-3l/ha,该产品已经获得德国批准。   
最近,德国农药生产商Staler 公司已收购了日本Ube 公司的除草剂品种氟丁酰草(beflubutamid) 。该次收购涉及到氟丁酰草胺的全球开发和销售权。Staler 公司享有氟丁酰草胺在欧洲数年的开发权。2007 年8 月氟丁酰草胺已获欧盟批准。氟丁酰草胺用于谷类作物中防治阔叶杂草和常见禾本科杂草, 其在欧洲市场以混剂产品Herbaflex( 氟丁酰草胺+异丙隆) 销售。Staler 公司于2003年在德国首次获得氟丁酰草胺全球登记, 此后在奥地利、比利时、保加利亚、克罗地亚、捷克、匈牙利、卢森堡、斯洛伐克和斯洛文尼亚获准登记。该公司计划以氟丁酰草胺与其他农药混配的形式投于欧洲市场, 并预计5 年内年产值1000 万欧元( 1400 万美元) 的规模。   


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Common name beflubutamid (BSI, pa ISO)
IUPAC name N-benzyl-2-(a,a,a,4-tetrafluoro-m-tolyloxy)butyramide
Chemical Abstracts name 2-[4-fluoro-3-(trifluoromethyl)phenoxy]-N-(phenylmethyl)butanamide
CAS RN [113614-08-7] Development codes UBH-820; UR50601; ASU 95510H (mixture with isoproturon)

Composition Tech. is >97%. Mol. wt. 355.3 M.f. C18H17F4NO2 Form Fluffy white powder. M.p. 75 °C V.p. 1.1 ´ 10-2 mPa (25 °C) KOW logP = 4.28 Henry 1.1 ´ 10-4 Pa m3 mol-1 S.g./density 1.33 Solubility In water 3.29 mg/l (20 °C). In acetone >600, 1,2-dichloroethane >544, ethyl acetate >571, methanol >473, n-heptane 2.18, xylene 106 (all in g/l, 20 °C). Stability Stable at 130 °C for 5 h. Stable at pH 5, 7 and 9 for 5 d (21 °C). Fairly stable to photolysis.

History Reported by S. Takamura et al., Proc. Br. Crop Prot. Conf. - Weeds, 1999, 1, 41. Under development by Ube Industries Ltd; mixture with isoproturon under development by Ube and Stähler Agrochemie GmbH. Patents EP 239414 Manufacturers Ube

Biochemistry Blocks carotenoid biosynthesis, by inhibition of phytoene desaturase. Uses Under development, alone and in mixture with isoproturon, for pre- and early post-emergence control of broad-leaved weeds, such as Veronica persica, Lamium amplexicaule and Viola arvensis, in wheat and barley at 170-255 g/ha. Formulation types SC. Selected products: mixtures: 'Herbaflex' (+ isoproturon) (Stähler, Ube)

Oral Acute oral LD50 for rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Non-irritating to skin and eyes (rabbits); not a skin sensitiser (guinea pigs). Inhalation LD50 (for rats) >5 ml/l. NOEL (90 d) for rats 29 mg/kg b.w. daily. Other Non-teratogenic. Negative in Ames, gene mutation, cytogenetics and micronucleus tests.

Data show a low toxicity risk and low bioaccumulation, except for some species of algae. Birds Acute oral LD50 for bobwhite quail >2000 mg/kg. Dietary LC50 for bobwhite quail >5200 ppm. Fish LC50 (96 h) for bluegill sunfish 2.69, rainbow trout 1.86 mg/l. Daphnia Acute EC50 (48 h) 1.64 mg/l. Algae EbC50 for Selenastrum 4.45 mg/l. Other aquatic spp. EC50 for Lemna gibba 0.029 mg/l. Bees LD50 (oral and contact) >100 mg/bee. Worms LC50 (14 d) for earthworms 732 mg/kg. Other beneficial spp. Low risk to soil microflora.

Low potential for mobility in soil and rapid degradation minimise potential for leaching into groundwater. Carry-over is not expected after application at approved rates. Animals The main metabolite is the same as in soil. Plants The main metabolite is the same as in soil. Soil/Environment Soil DT50 5.4 d; the main metabolite is the corresponding butanoic acid, formed by cleavage of the amide bond; this metabolite is itself rapidly degraded in soil. Koc 852-1793. Stable to hydrolysis at pH 5-9.