Chlorsulfuron 氯磺隆

氯磺隆

基本信息
英文通用名：chlorsulfuron
其他名称：绿黄隆、克lean、Opx-4189
CAS号：64902-72-3
分子式：C12H12ClN5O4S
分子量：357.77 氯磺隆
化学性质：纯品为白色结晶，无臭味。m.p.174～178℃，192℃分解，蒸气压6.133×10-4Pa (25℃)。在有机溶剂中溶解度：二氯甲烷102g/L，丙酮57g/L，甲醇14g/L，甲苯3g/L，己烷10mg/L；25℃时在水中溶解度：100～125mg/L (pH=4.1), 27.9g/L (pH=7)。酸性条件下不稳定，pH值5.7～7时水解半衰期为4～8周，pH值4时为1周。干燥条件下，30d内在植物表面光分解30%,土壤表面光分解15%。在土壤中半衰期为4～6周。

毒性
雄性大鼠急性经口LD50为5545mg/kg，雌性为6293mg/kg；兔急性经皮LD50>3400mg/kg。对眼睛有轻微刺激，对皮肤无刺激。以500mg/kg剂量饲喂大鼠90d，未发现病变。大鼠2年饲养试验作用剂量为100mg/kg，小鼠为500mg/kg。动物试验未见致畸、致癌、致突变作用。虹鳟鱼LC50>250mg/kg(96h)，鹌鹑LC50>5000mg/kg饲料（8d)。

剂型
80%可湿性粉剂，20%、75%干胶悬剂。

用途
内吸、超高效磺酰脲类除草剂。药剂被杂草叶面或根系吸收后，可传导到植株全身，通过抑制乙酰乳酸酶的活性，阻碍支链氨基酸、缬氨酸和亮氨酸的合成，从而使细胞分裂停止，植株失绿，枯萎而死。用于防除禾谷作物田的阔叶杂草及禾本科杂草，如藜、蓼、苋、猪殃殃、苘麻、田旋花、田蓟、荞麦蔓、母菊，以及狗尾草、黑麦草、早熟禾、小根蒜等。对野燕麦、龙葵效果不佳。芽前或芽后早期使用，一般在秋季作物播后芽前或春季杂草芽后施药，更宜芽后叶面处理。用0.15～0.6g有效成分/100m2 ，对水喷雾。与绿麦隆、异丙隆混用效果良好。对后茬敏感的作物有玉米、油菜等，药量超过0.6g对后茬水稻也略有影响。绿黄隆是1978年美国杜邦公司开发的磺酰脲类新型除草剂，1981年将其商品化，它是低毒广谱的麦田选择性除草剂，其突出的特点是具有超高活性。
使用方法：杂草芽前或芽后都可使用，芽后叶面喷雾效果更好。一般秋季作物播后芽前或春季杂草后施药。每亩用有效成分1-2克，对水喷雾。

注意事项
氯磺隆高效且残效期长，使用量要严格控制，不能随意加大，以免对后茬作物产生不良影响。

chlorsulfuron
Herbicide
HRAC B WSSA 2; sulfonylurea

NOMENCLATURE
Common name chlorsulfuron (BSI, draft E-ISO, (m) draft F-ISO, ANSI, WSSA)
IUPAC name 1-(2-chlorophenylsulfonyl)-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea
Chemical Abstracts name 2-chloro-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]benzenesulfonamide
CAS RN [64902-72-3] EEC no. 265-268-5 Development codes DPX 4189 (DuPont); W4189

PHYSICAL CHEMISTRY
Mol. wt. 357.8 M.f. C12H12ClN5O4S Form White crystalline solid. M.p. 170-173 °C (purity 98%) V.p. 3 ´ 10-6 mPa (25 ºC, Knudsen gas effusion) KOW logP = -0.99 (pH 7) Henry 5 ´ 10-10 (pH 5); 3.5 ´ 10-11 (pH 7); 3.2 ´ 10-12 (pH 9) (all Pa m3 mol-1, calc.) S.g./density 1.48 Solubility In water 590 (pH 5), 31800 (pH 7) (both mg/l, 25 ºC). In dichloromethane 1.4, acetone 4, methanol 15, toluene 3, hexane <0.01 (all in g/l, 25 ºC). Stability Stable to light when dry. Decomposes at 192 ºC. In aqueous solutions, DT50 23 d (pH 5, 25 ºC); >31 d (pH 7 and above). Hydrolysis is also promoted by polar organic solvents such as methanol and acetone. pKa 3.4

COMMERCIALISATION
History Herbicide reported by P. G. Jensen (Weed Control, 1980, 21st, 24). Introduced in USA in 1982, by E. I. du Pont de Nemours Co. Patents US 4127405 Manufacturers DuPont; Sharda

APPLICATIONS
Biochemistry Branched chain amino acid synthesis (ALS or AHAS) inhibitor. Acts by inhibiting biosynthesis of the essential amino acids valine and isoleucine, hence stopping cell division and plant growth. Selectivity derives from rapid metabolism in the crop. Metabolic basis of selectivity in sulfonylureas reviewed (M. K. Koeppe & H. M. Brown, Agro-Food-Industry, 6, 9-14 (1995)). Mode of action Selective systemic herbicide, absorbed by the foliage and roots, with rapid translocation acropetally and basipetally. Uses Control of most broad-leaved weeds and some annual grasses in wheat, barley, oats, rye, triticale, flax, and on non-crop land. Applied pre-emergence, early post-emergence, pre-plant, or early post-plant incorporated, at 9-35 g/ha in crops, 140 g/ha in non-crop situations. Phytotoxicity Phytotoxic to many broad-leaved crops, particularly sugar beet and brassicas. Formulation types WG. Selected products: 'Glean' (DuPont); 'Telar' (USA) (DuPont); 'Granonet' (Agrimix); 'Lasher' (Sanonda)

OTHER PRODUCTS
'Pilargreen' (Pilarquim); 'Press' (AgroSan); 'Uron' (Probelte) mixtures: 'Finesse' (+ metsulfuron-methyl) (DuPont); 'Valinate' (+ linuron) (DuPont)

ANALYSIS
Product analysis by rplc with u.v. detection (CIPAC Handbook, 1998, H, 89; R. V. Slates & M. W. Watson, Anal. Methods Pestic. Plant Growth Regul., 1988, 16, 53). Residues determined by hplc (idem, ibid.; E. W. Zahnow, J. Agric. Food Chem., 1982, 30, 854) and by immunoassay (Kelly et al.,ibid.,1985, 33, 962). Methods for sulfonylurea residues in crops, soil and water reviewed (A. C. Barefoot et al., Proc. Br. Crop Prot. Conf. - Weeds, 1995, 2, 707; C. R. Powley, in, Handbook of Residue Analytical Methods).

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for male rats 5545, female rats 6293 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits 3400 mg/kg. Mild eye irritant; non-irritating and non-sensitising to skin. Inhalation LC50 (4 h) for rats >5.9 mg/l air. NOEL (2 y) for rats 100, mice 500 mg/kg diet; (1 y) for dogs 2000 mg/kg diet. ADI 0.05 mg/kg. Other No oncogenic, mutagenic or teratogenic activity detected in standard tests. Acute i.p. LD50 for rats 1450 mg/kg. Toxicity class WHO (a.i.) U; EPA (formulation) IV (75 WG) EC classification N; R50, R53

ECOTOXICOLOGY
Birds Acute oral LD50 for mallard ducks and bobwhite quail >5000 mg/kg. Dietary LC50 (8 d) for mallard ducks and bobwhite quail >5000 mg/kg diet. Fish LC50 (96 h) for rainbow trout >250, bluegill sunfish >300 mg/l. LC50 for fathead minnow >300, catfish >50, sheepshead minnow >980 mg/l. Daphnia EC50 (48 h) >112 mg/l. Algae EC50 50 mg/l. Bees LD50 (contact) >100 mg/bee. Worms LC50 >2000 mg/kg.

ENVIRONMENTAL FATE
Soil/Environment In soil, degradation and deactivation is through biotic (microbial) and abiotic (hydrolysis) processes, followed by complete degradation to low-molecular-weight compounds through continuing soil microbial processes. Rate of hydrolysis is increased at lower pH. Average half-life under growing-season conditions is c. 4-6 weeks. Koc 40 (pH 7).