Butroxydim 丁苯草酮

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中文通用名称: 丁苯草酮
英文通用名称: butroxydim (BSI,ISO)
商品名称: Falcon
化学名称: 5-(3-丁酰基-2,4,6-三甲苯基)-2-[1-(乙氧亚胺基]丙基]-3- 羟基-环己-2-烯-1-酮

化学结构类型: 环己烯酮类。
理化性质: 纯品为粉色固体;熔点80.8℃;蒸气压为1×10-6Pa(20℃)。分配系数LogP=1.90(pH7,25℃);水中溶解度为6.9mg/l(20℃);在正常条件下贮存稳定。
毒性: 大鼠急性经口L D50:雌性1635、雄性3476mg/kg;大鼠急性经皮LD50:>2000mg/kg; 本品对兔皮肤无刺激,对兔眼睛有中度刺激。大鼠急性吸入LC50(4小时):>2.99g/l。急性经口LD50(mg/kg):野鸭>2000,鹌鹑1221;鱼毒LC50(96小时,mg/l) :虹鳟>6.9,大翻车鱼8.8。水蚤LC50(48小时):>3.7mg/l。
应用: 阔叶作物苗后用除草剂。
开发公司: 英国捷利康公司开发。


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HRAC A WSSA 1; cyclohexanedione oxime


Common name butroxydim (BSI, pa E-ISO)
IUPAC name 5-(3-butyryl-2,4,6-trimethylphenyl)-2-(1-ethoxyiminopropyl)-3-hydroxycyclohex-2-enone
Chemical Abstracts name 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-[2,4,6-trimethyl-3-(1-oxobutyl)phenyl]-2-cyclohexen-1-one
CAS RN [138164-12-2] Development codes ICIA0500 (ICI)

Mol. wt. 399.5 M.f. C24H33NO4 Form Off-white powdery solid. M.p. 80.8 °C V.p. 1 ´ 10-3 mPa (20 °C) KOW logP = 1.90 (pH 7, 25 °C) Henry 5.79 ´ 10-5 Pa m3 mol-1 (calc.) S.g./density 1.20 (tech., 25 °C) Solubility In water 6.9 mg/l (20 °C). In dichloromethane >500, acetone 450, toluene 480, acetonitrile 380, methanol 90, hexane 30 (all in g/l). Stability Hydrolysis DT50 10.5 d (pH 5), >240 d (pH 7), stable (pH 9) (all 25 °C). pKa 4.36 (23 °C), weak acid

History First sold in 1995. Divested to Crop Care Australasia Pty Ltd in 2002.

Biochemistry Fatty acid synthesis inhibitor, by inhibition of acetyl CoA carboxylase (ACCase). Mode of action Post-emergence herbicide. Uses A post-emergence grass herbicide for use on broad-leaved crops, at 25-75 g/ha. Formulation types WG. Selected products: 'Falcon' (Crop Care)

Residues determined by hplc with u.v. detection, or by hplc-ms.

Oral LD50 for male rats 3476, female rats 1635 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Moderate skin irritant; mild eye irritant (rabbits). Not a skin sensitiser (guinea pigs). Inhalation LC50 (4 h) for rats >2.99 mg/l. NOEL NOAEL (1 y) for dogs 5 mg/kg b.w. daily; NOEL (2 y) for rats 2.5, mice 10 mg/kg b.w. daily (liver tumours only in males at high dose); NOEL developmental for rats 5, rabbits 15 mg/kg b.w. daily. ADI 0.025 mg/kg. Other Genotoxicity negative. Not oncogenic (rats). Toxicity class WHO (a.i.) III EC classification (T; R61| R22| R38| N; R50, R53)

Birds Acute oral LD50 for mallard ducks >2000, bobwhite quail 1221 mg/kg. Sub-acute dietary LC50 (5 d) for mallard ducks >5200, bobwhite quail 5200 mg/kg. Fish LC50 (96 h) for rainbow trout >6.9, bluegill sunfish 8.8 mg/l. Daphnia LC50 (48 h) >3.7 mg/l. Algae EbC50 for Selenastrum capricornutum 0.71 mg/l. Bees LD50 (contact, 24 h) >200 mg/bee. Worms LC50 (14 d) for Eisenia foetida >1000 mg/kg.

Animals In rats, following oral administration, >90% of the dose is excreted within 7 d. Various oxidative transformations of the butyryl chain dominate the metabolic pathway. Neither parent nor metabolites bioaccumulate in tissues. Plants Rapidly metabolised in plants. Soil/Environment Soil Koc 6-1270 (stronger adsorption in low pH soils). Rapid degradation in aerobic soil, lab. DT50 c. 9 d (20 °C, 40% MHC, pH 7.0, 4.09% o.m.); metabolites include 5-(3-butyryl-2,4,6-trimethylphenyl)-3-hydroxy-2-(1-iminopropyl)cyclohex-2-enone, 6-(3-butyryl-2,4,6-trimethylphenyl)-2-ethyl-4,5,6,7-tetrahydro-4-oxo-1,3-benzoxazole, 2-(3-butyryl-2,4,6-trimethylphenyl)glutaric acid and 5-(3-butyryl-2,4,6-trimethylphenyl)-3-hydroxy-2-propionylcyclohex-2-enone.