Butachlor 丁草胺

丁草胺

英文通用名：Butachlor
又名：灭草特、去草胺。
CAS号：23184-66-9
分子式：C17H26ClNO2
分子量：311.86
化学名称：2-氯-N-(2,6-二乙基苯基)-N-(丁氧甲基)乙酰胺
主要剂型：60%乳油，5%颗粒剂。

理化性质
丁草胺为琥珀色液体，沸点为196℃（66.7kPa）。难溶于水，可与丙酮、苯、乙醇、乙酸乙酯、己烷混溶。275℃分解，在pH 7～10稳定，对紫外光稳定。

药剂特性
丁草胺为酰胺类选择性内吸传导除草剂。纯品为淡黄色油状液体，具有微芳香味。难溶于水，易溶于多种有机溶剂。在常温及中性、弱碱性条件下化学性质稳定。强酸条件下会加速其分解，在土壤中可被降解。对人畜低毒，对皮肤、眼睛有刺激作用，对鱼类高毒。丁草胺主要通过杂草的幼芽吸收，而后传导全株而起作用。芽前和苗期均可使用。植物吸收丁草胺后，在体内抑制和破坏蛋白酶，影响蛋白质的形成，抑制杂草幼芽和幼根正常生长发育，从而使杂草死亡。在粘壤土及有机质含量较高的土壤上使用，药剂可被土壤胶体吸收，不易被淋溶，特效期可达1-2个月。

主要用途
选择性芽前除草剂。主要用于直播或移栽水稻田防除的一年生禾本科杂草及某些阔叶杂草。对小麦、大麦、甜菜、棉花、花生和白菜作物也有选择性。有效剂量为每公顷1.0-4.5kg（有效成分）。一般是作芽前土壤表面处理，水田苗后也可应用，是水稻田除草剂的重要品种。

防除对象
在旱田应用需在土壤润湿的条件下施药。可防除稗草、马唐草、狗尾草、牛毛草、鸭舌草、节节草、异型沙草等一年生禾本科杂草和某些双子叶杂草。适用于白菜类、豆菜、萝卜类、甘蓝类、茄果类、菠菜等菜田除草。

使用方法
（l）菜豆、豇豆、小白菜、茴香、育苗甘蓝、菠菜等直播菜田除草，于播种前亩用60%乳油100毫升，兑水40－50公斤，均匀喷雾畦面，然后播种。
（2）花椰菜、甘蓝、茄子、甜（辣）椒、西红柿等移栽田，于定植前亩用60%乳油150克，兑水50公斤，均匀喷雾处理土壤。

注意事项
（l）本品对出土前杂草防效较好，大草防效差，应尽量在播种定植前施药。
（2）土壤有一定湿度时使用丁草胺效果好。旱田应在施药前浇水或喷水，以提高药效。
（3）瓜类和茄果类蔬菜的播种期，使用本品有一定的药害，应用时应慎重。
（4）本品主要杀除单子叶杂草，对大部分阔叶杂草无效或药效不大。菜田阔叶杂草较多的地块，可考虑改用其他除草剂。
（5）喷药要力求均匀，防止局部用药过多造成药害，或漏喷现象。

butachlor
Herbicide
HRAC K3 WSSA 15; chloroacetamide

NOMENCLATURE
Common name butachlor (BSI, draft E-ISO, (m) draft F-ISO, ANSI, WSSA, JMAF); no name (France)
IUPAC name N-butoxymethyl-2-chloro-2',6'-diethylacetanilide
Chemical Abstracts name N-(butoxymethyl)-2-chloro-N-(2,6-diethylphenyl)acetamide
CAS RN [23184-66-9] Development codes CP 53 619 (Monsanto)

PHYSICAL CHEMISTRY
Composition ³93.5% pure. Mol. wt. 311.9 M.f. C17H26ClNO2 Form Light yellow to purple liquid with a faint, sweet odour. M.p. -2.8 °C to 1.7 °C B.p. 156 ºC/0.5 mmHg V.p. 2.4 ´ 10-1 mPa (25 °C) Henry 3.74 ´ 10-3 Pa m3 mol-1 (calc.) S.g./density 1.076 (25 ºC) Solubility In water 20 mg/l (20 ºC). Soluble in most organic solvents, including diethyl ether, acetone, benzene, ethanol, ethyl acetate, and hexane. Stability Decomposes at ³165 ºC. Stable to u.v. light. Stable indefinitely £45 °C. F.p. >135 °C (Tag closed cup) Other properties Viscosity 37 cP (25 °C)

COMMERCIALISATION
History Herbicide reported by D. D. Baird & R. P. Upchurch (Proc. South. Weed Control Conf., 23rd, 1970, p. 101). Introduced by Monsanto Co. Patents US 3442945; US 3547620 Manufacturers Agrochem; Comlets; Crystal; Hindustan; Krishi Rasayan; Monsanto; Rallis; RPG; Sinon

APPLICATIONS
Biochemistry Inhibits cell division by blocking protein synthesis; more recent research suggests chloroacetamides may inhibit synthesis of very long chain fatty acids (J. Schmalfuss et al., Abstr. Meeting WSSA, Toronto, 40, 117-118, 2000; P. Böger, Abstr. III Int. Weed Control Congr., Brazil 2000). Mode of action Selective systemic herbicide, absorbed primarily by the germinating shoots, and secondarily by the roots, with translocation throughout the plant, giving higher concentrations in vegetative parts than in reproductive parts. Uses Used pre-emergence for the control of annual grasses and certain broad-leaved weeds in rice, both seeded and transplanted. It shows selectivity in barley, cotton, peanuts, sugar beet, wheat and several brassica crops. Effective rates range from 1.0-4.5 kg/ha. Activity is dependent on water availability such as rainfall following treatment, overhead irrigation or applications to standing water as in rice culture. Phytotoxicity Non-phytotoxic to rice, cotton, barley, wheat, peanuts, sugar beet, and some brassicas. Formulation types EC; GR. Selected products: 'Direk' (Monsanto); 'Machete' (Monsanto); 'Ban Weed' (Crop Health); 'Beta' (Devidayal); 'Butataf' (Rallis); 'Dhanuchlor' (Dhanuka); 'Farmachlor' (Sanonda); 'Hiltaklor' (Hindustan); 'Rasayanchlor' (Krishi Rasayan); 'Trapp' (RPG); 'Vibuta' (Vipesco); 'Wiper' (Nagarjuna Agrichem); mixtures: 'Advance' (+ propanil) (Monsanto); 'Rogue' (+ 2,4-D) (Monsanto)

OTHER PRODUCTS
'Butamach' (BEC); 'Butanox' (Crystal); 'Pilarsete' (Pilarquim); 'Revyone' (Agrochem) mixtures: 'Challenge' (+ propanil) (Monsanto); 'Arkace' (+ quinoclamine) (Agro-Kanesho); 'Bandito' (+ propanil) (Crystal); 'Sable' (+ propanil) (Proficol); 'Sakidori' (+ pentoxazone) (Kaken, Kumiai); 'Vitanyl' (+ propanil) (Vipesco) Discontinued products: 'Butanex' * (Makhteshim-Agan) mixtures: 'Delcut' * (+ oxadiazon) (Hokko); 'Kusakarin' * (+ pyrazolynate) (Hokko, Sankyo)

ANALYSIS
Product analysis by glc with FID (AOAC Methods, 17th Ed., 986.04; CIPAC Handbook, 1988, D, 17) or by i.r. spectrometry. Residues determined by glc. In drinking water, by glc with NPD (AOAC Methods, 17th Ed., 991.07). Details available from Monsanto Co.

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats 2000, mice 4747, rabbits >5010 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits >13 000 mg/kg. Moderate skin irritant; practically non-irritating to eyes (rabbits). Contact sensitisation reactions observed in guinea pigs. Inhalation LC50 (4 h) for rats >3.34 mg/l air. NOEL For rats 100 mg/kg diet (ppm), for mice 50 mg/kg diet (ppm), for dogs 5 mg/kg b.w. daily. Other Oncogenic in rats but not in mice. For detailed toxicology data, please contact Monsanto. Toxicity class WHO (a.i.) U; EPA (formulation) III

ECOTOXICOLOGY
Birds Acute oral LD50 for mallard ducks >4640 mg/kg. Dietary LC50 (5 d) for mallard ducks >10 000, bobwhite quail 6597 mg/kg diet. Fish LC50 (96 h) for rainbow trout 0.52, bluegill sunfish 0.44, carp 0.32, channel catfish 0.10-0.14, fathead minnow 0.31 mg/l. Daphnia LC50 (48 h) 2.4 mg/l. Other aquatic spp. LC50 (96 h) for crayfish 26 mg/l. Bees LD50 (contact) >100 mg/bee.

ENVIRONMENTAL FATE
Animals Metabolised to water-soluble metabolites and excreted. Plants Rapidly metabolised in plants to water-soluble metabolites, leading eventually to mineralisation. Soil/Environment In soil, degradation is principally by microbial activity (Y.-L. Chen and T.-C. Wu, Nippon Noyaku Gakkaishi, 1978, 3, 411). Persists for c. 6-10 weeks. Converted in soil or water to water-soluble derivatives, with a slow evolution of CO2.