Butralin 仲丁灵 双丁乐灵

双丁乐灵

CAS号：33629-47-9
英文名称：butralin
化学名称：N-仲丁基-4-叔丁基-2，6-二硝基苯胺；4-(1,1-dimethylethyl)-N-(1-methylpropyl)-2,6-dinitrobenzenamine
其他名称：地乐胺；仲丁灵，丁乐灵，比达宁;硝苯胺灵；止芽素；Amchem 70-25；Amchem A-280
分子式：C14H21N3O4
分子量：295.3

理化性质：略带芳香味的黄橙色晶体。熔点60～61℃，沸点134～136℃（66.5Pa），闪点36℃，蒸气压1.7mPa(25℃)。溶解情况：水1mg/L(24℃)，丁酮9.55kg/kg，丙酮4.48kg/kg，二甲苯3.88kg/kg，苯2.7kg/kg，四氯化碳1.46kg/kg(24～26℃)。

毒性LD50（mg/kg）：大白鼠急性经口12600，大白鼠急性经皮10200。对皮肤、眼睛无刺激作用。鱼毒LC50(48h,mg/L)：鲶鱼4.2，虹鳟3.4。

作用特点及杀草谱：地乐胺是一种二硝基苯胺类选择性、触杀型、芽前土壤处理低毒除草剂。药剂通过杂草幼芽吸收，在体内抑制分生组织的细胞分裂，抑制幼芽、幼根生长而导致杂草死亡。播前用除草剂，也可用于烟草腋芽的抑制。主要适用于大豆、棉花、豌豆、水稻、玉米、向日葵、马铃薯、西瓜、黄瓜、甜菜、花生、苜蓿等作物田，防除稗草、马唐、狗尾草、牛筋草、野燕麦等一年生禾本科杂草和藜、苋、马齿苋等小粒种子阔叶杂草以及大豆菟丝子。西红柿、青椒、茄子田除草，每亩用48％乳油200—250毫升对水，对地表喷雾，混土后再移栽。大豆、菜豆、豌豆、胡萝卜苗香田除草，每亩用48％乳油200—250毫升对水，在播种前对土壤表面喷雾。大白菜、育苗韭菜田除草，每亩用48％乳油150一250毫升，在播种后出苗前对水喷雾。花生田除草，每亩用48％乳油150一200毫升，在播种前对水喷雾并混土。

剂型：48％乳油，36%乳油

生产方法：苯酚与硝酸在醋酸溶液中硝化反应，生成2，6-二硝基酚，进而丁基化，制成2，6-二硝基-4-丁基酚，然后用氯化剂氯化，制得2，6-二硝基-4-叔丁基氯苯。1g仲丁胺滴加到50ml甲苯和2，6-二硝基-4-叔丁基氯苯的回流混合物中，滴闭，混合物回流8小时后，冷却制室温，滤去胺的盐酸盐，减压蒸馏除去甲苯和未反应的胺，物料溶解在热乙醇中，冷却重结晶，得到N-仲丁基-4-叔丁基-2，6-二硝基苯胺。

生产情况：澳大利亚纽发姆有限公司；济南绿邦化工有限公司供应；江苏省百灵农化有限责任公司；江西盾牌化工有限责任公司（江西省临川农药厂）；张掖市大弓农化有限公司（1000t/a）, 山东侨昌化学有限公司; 山东滨农科技有限公司；华阳科技（800t/a ）

butralin
Herbicide, plant growth regulator
HRAC K1 WSSA 3; dinitroaniline

NOMENCLATURE
Common name butralin (BSI, E-ISO, ANSI, WSSA); butraline ((f) F-ISO); no name (Eire, Japan)
IUPAC name N-sec-butyl-4-tert-butyl-2,6-dinitroaniline
Chemical Abstracts name 4-(1,1-dimethylethyl)-N-(1-methylpropyl)-2,6-dinitrobenzenamine
CAS RN [33629-47-9] EEC no. 251-607-4 Development codes Amchem 70-25; Amchem A-820

PHYSICAL CHEMISTRY
Composition Tech. is ³98% (without xylene). Mol. wt. 295.3 M.f. C14H21N3O4 Form Yellow-orange crystals with a slightly aromatic odour. M.p. 61 ºC; (tech., 59 °C) B.p. 134-136 ºC/0.5 mmHg V.p. 0.77 mPa (25 ºC) KOW logP = 4.93 (23? °C) Henry 7.58 ´ 10-1 Pa m3 mol-1 (calc.) S.g./density 1.063 (25 °C) Solubility In water 0.3 mg/l (25 ºC). In ethanol 73, methanol 98, hexane 300 (g/l, 25-26 °C); in dichloroethane 146, benzene 270, acetone 448 (g/100 ml, 24 °C). Stability Decomposes at 265 ºC. Hydrolytically and photochemically stable. Concentrates are stable on storage under dry conditions >3 y, but should not be stored <-5 ºC or allowed to freeze.

COMMERCIALISATION
History Herbicide reported by S. R. McLane et al. (Proc. South. Weed Sci. Soc., 1971, 24, 58). Introduced by Amchem Products Inc. (now Bayer CropScience) and later acquired by CFPI (now Nufarm SA). Patents US 3672866 Manufacturers Nufarm SA

APPLICATIONS
Biochemistry Microtubule assembly inhibitor. Mode of action Selective herbicide, absorbed by germinating seedlings, with slow translocation acropetally. Also acts as a growth regulator, suppressing the growth of shoots, branches, and suckers. Uses Pre-emergence control of annual broad-leaved weeds and grasses in cotton, soya beans, rice, barley, beans, alliums, vines, ornamentals, and orchards of fruit and nut trees; used at 1.12-3.4 kg/ha (depending on soil type). Also used to control suckers on tobacco, at 125 mg/plant. Formulation types EC. Compatibility Incompatible with strong oxidising agents. Selected products: 'Tabamex Plus' (Nufarm SA); mixtures: 'Tamex AG' (+ n-decanol) (Bayer CropScience, Nufarm SA)

OTHER PRODUCTS
'Amex 820' (Nufarm SA); 'Tabamex' (Nufarm SA); 'Tamex 3' (Bayer CropScience); 'Tobago' (Nufarm SA) mixtures: 'Stifle' (+ maleic hydrazide potassium salt) (Crompton); 'Yellow Ribbon' (+ n-decanol) (SDS Biotech KK, Nufarm Ltd) Discontinued products mixtures: 'Linamex' * (+ linuron) (Nufarm SA, Zeneca)

ANALYSIS
Product analysis by glc using an internal standard.

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for male rats 1170, female rats 1049 mg/kg (tech.). Skin and eye Acute percutaneous LD50 (tech.) for rabbits ³2000 mg/kg. Slightly irritating to skin, moderately irritating to eyes (rabbits). Not a skin sensitiser (Magnusson & Kligman and Buehler tests). Inhalation LC50 for rats >9.35 mg/l air. NOEL (2 y) for rats 500 ppm (20-30 mg/kg daily). Toxicity class WHO (a.i.) U; EPA (formulation) IV EC classification (Xn; R22, R63)

ECOTOXICOLOGY
Birds Acute oral LD50 for bobwhite quail >2250, Japanese quail >>5000 mg/kg. Dietary LC50 (8 d) for bobwhite quail and mallard ducks >10 000 mg/kg diet. Fish LC50 (96 h) for bluegill sunfish 1.0, rainbow trout 0.37 mg/l. Daphnia EC50 (48 h) 0.12 mg/l. Algae EC50 (5 d) for Selenastrum capricornutum 0.12 mg/l. Bees LD50 (oral) 95 mg/bee; (contact) 100 mg/bee. Other beneficial spp. Not toxic to soil microflora at usual application rate. Application at 2-10 ´ recommended rate did not significantly alter microbial population.

ENVIRONMENTAL FATE
Animals Extensively metabolised and excreted in urine and faeces. Metabolised in the rat by the primary metabolic processes of N-dealkylation, oxidation and nitro reduction, and by secondary processes of N-acetyl and glucuronic acid conjugation. The majority (85%) of applied butralin was excreted in the urine within 48 h. None was in the organs after 72 h. Butralin is ultimately metabolised to CO2. Soil/Environment In soil, microbial degradation occurs, with formation of the corresponding aniline, ring splitting and evolution of CO2 (P. C. Kearney et al., J. Agric. Food Chem., 1974, 22, 856). Moderately persistent and relatively immobile in terrestrial environments; field dissipation DT50 >3 weeks (10-72.6 d); in water <10% hydrolysed in 30 days. In terrestrial environments, the main routes of butralin dissipation appear to be dependent on microbial degradation. Strongly adsorbed and not leached; lysimeter studies show little migration of butralin beyond the top 6 cm.