Thifensulfuron,Thifensulfuron-methyl 噻吩磺隆

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噻吩磺隆

CAS: 79277-67-1
英文名称: Thifensulfuron;Thifensulfuron-methyl
化学名称:3-(4-甲氧基-6-甲基-1,3,5-三嗪-2-基氨基甲酰氨基磺酰基)噻吩-2-甲酸甲酯; Methyl 3-(4-methoxy-6-methyl-1,3,5-triazin-2-ylcarbamoylsulfamoyl)thiophene-2-carboxylate
其他名称:噻黄隆;阔叶散; 宝收,Harmony(Du Pont);DPX-M6316(Du Pont)
分子式:C12H13N5O6S2
分子量:387.4

理化性质:无色固体,熔点186℃,蒸气压17nPa(25℃)。25℃溶解性:水24mg/L(PH4)、260mg/L(PH5)、2.4g/L(PH6),丙酮11.9g/L,乙腈7.3g/L,乙醇0.9g/L,乙酸乙酯2.6g/L,己烷小于0.1g/L,甲醇2.6g/L,二氯甲烷27.5g/L,二甲苯0.2g/L。
毒性LD50(mg/kg):大白鼠急性经口大于5000,野鸭急性经口大于2510,兔急性经皮大于2000。对兔眼睛有轻微刺激作用,但一天后恢复正常。对豚鼠皮肤无刺激作用,也无过敏现象。

作用特点及杀草谱:该品是一种内吸型选择性的苗后除草剂。是侧链氨基酸合成抑制剂,抑制缬氨酸和异亮氨酸的生物合成,从而阻止植物的细胞分裂。该药能迅速被植物根和叶吸收,并传导至分叶组织;以20~30g/ha喷雾,防除小麦天阔叶杂草。以20~40g有效成分/ha(以下同)施用,防除禾谷类作物田中阔叶杂草,如小麦以20~30g/ha喷雾;施用时可加入0.2%~0.5%(体积比)非离子表面活性剂,于作物2叶期至开花期、杂草高度低于10cm、生长旺盛但未开花时期进行芽后施药,持效期一般在30天以内,一个月后对下茬作物无害。对猪殃殃、藜、蓼、马齿苋、婆婆纳、野蒜、芥菜等防效极好;可与甲黄隆混用。

剂型:75%可湿性粉剂、75%干悬浮剂,20%、39%、50%噻吩磺隆·乙草胺,15%苄嘧磺隆·噻吩磺隆,35%噻吩磺隆·乙草胺·莠去津
生产方法:α-氯代丙烯腈与巯基乙酸甲酯在甲醇钠存在下缩合、环合,环合产物经重氮化、氯磺化及氨解,生成3-氨基磺酰基噻吩-2-甲酸甲酯,最后该化合物与3-甲氧基-5-甲基三嗪异氰酸酯反应即得。

1、 丙烯腈在DMF存在下,于10~12℃通氯反应6~7h,得2,3-二氯丙腈;巯基乙酸在浓硫酸存在下,与无水甲醇于室温下反应8h,得巯基乙酸甲酯。
2、将巯基乙酸甲酯、无水甲醇和甲醇钠冷至10~15℃,滴加二氯丙腈和无水甲醇溶液,滴毕于10~15℃继续反应5h,减压蒸出甲醇,残余物冷却后加入冰水,过滤,得3-氨基-2-羧甲基噻吩,产品收率55%,m.p. 58~61℃。
3、将冰醋酸及少许盐酸在泠却下通入二氧化硫,置冰浴中待用。
将3-氨基-2-羧甲基噻吩于0~5℃加入到盐酸、冰醋酸混合液中,搅拌,将亚硝酸钠水溶液慢慢滴入,继续反应30min,于0℃将待用的二氧化硫溶液加入,再加少许氯化亚铜,控制温度自然升至25~30℃,反应10h,将反应液倒入冰水中,过滤、洗涤、干燥,得2-羟甲基-3-磺酰氯噻吩,收率75.7%,m.p.66~68℃。
4、以二氯乙烷为溶剂,将所得的磺酰氯噻吩溶解,冷却至5℃,通入氨气。氨解产物过滤,滤液浓缩处理得产品2-羧甲基-3-磺酰氨基噻吩,收率95%,m.p. 110~114℃。
5、将2-羧甲基-3-磺酰氨基噻吩与3-甲氧基-5-甲基三嗪异氰酸酯反应,制得噻磺隆。

生产情况:美国杜邦公司于1992年在我国登记75%噻吩磺隆可湿性粉剂(商品名称:宝收)用于玉米、小麦田防除阔叶杂草。国内原药生产企业:江苏省农用激素工程技术研究中心;江苏银禾农化有限公司;宣城市群业精细化工研究所;嘉兴金尔太化工有限公司;灌云县光大农化有限公司;江苏瑞东农药有限公司;周口山都丽化工有限公司;南京第一农药集团有限公司;镇江先锋化学有限公司; 江苏腾龙生物药业有限公司;

 

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thifensulfuron-methyl
Herbicide
HRAC B WSSA 2; sulfonylurea

  thifensulfuron-methyl

NOMENCLATURE
thifensulfuron-methyl
Common name thifensulfuron-methyl
IUPAC name methyl 3-(4-methoxy-6-methyl-1,3,5-triazin-2-ylcarbamoylsulfamoyl)thiophen-2-carboxylate
Chemical Abstracts name methyl 3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]-2-thiophenecarboxylate
CAS RN [79277-27-3] Development codes DPX- M6316 (DuPont)

thifensulfuron
Common name thifensulfuron (BSI, ANSI, draft E-ISO); thiameturon* (WSSA former name)
IUPAC name 3-(4-methoxy-6-methyl-1,3,5-triazin-2-ylcarbamoylsulfamoyl)thiophen-2-carboxylic acid
Chemical Abstracts name 3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]-2-thiophenecarboxylic acid
CAS RN [79277-67-1]

PHYSICAL CHEMISTRY
thifensulfuron-methyl
Mol. wt. 387.4 M.f. C12H13N5O6S2 Form Off-white solid with no odour. M.p. 176 ºC; (tech. 171.1 ºC) V.p. 1.7 ´ 10-5 mPa (25 ºC, Knudsen method) KOW logP = 1.06 (pH 5), 0.02 (pH 7), 0.0079 (pH 9) Henry 9.7 ´ 10-16 Pa m3 mol-1 (pH 7, 25 ºC) S.g./density 1.580 Solubility In water 223 (pH 5), 2240 (pH 7), 8830 (pH 9) (all in mg/l, 25 ºC). In hexane <0.1, o-xylene 0.212, ethyl acetate 3.3, methanol 2.8, acetonitrile 7.7, acetone 10.3, dichloromethane 23.8 (all in g/l, 25 ºC). Stability Aqueous hydrolysis DT50 4-6 (pH 5), 180 (pH 7), 90 (pH 9) (all in days). pKa 4.0 (25 ºC)

thifensulfuron
Mol. wt. 373.4 M.f. C11H11N5O6S2

COMMERCIALISATION
History Herbicidal activity of thifensulfuron-methyl reported by R. M. Ambach et al. (Proc. North Cent. Weed Control Conf., 1985, 39, 1220). Introduced by E. I. du Pont de Nemours and Co.; first approval in 1988. Manufacturers DuPont; Fengle

APPLICATIONS
thifensulfuron-methyl
Biochemistry Affects sensitive weeds through inhibition of the enzyme acetolactate synthase (ALS). Inhibition of ALS leads to the rapid cessation of cell division and subsequent growth processes in plants. Mode of action Post-emergence, selective herbicide acting primarily through foliar uptake with little or no soil activity Uses Selective control of a wide range of annual weeds in cereals, maize and pasture. Phytotoxicity Treated cereals may experience a temporary inhibition of growth and colour changes in the leaves, but these have no ultimate effect on the yield. Formulation types TB; WG. Selected products: 'Harmony' (DuPont); 'Pinnacle' (DuPont); mixtures: 'Canvas' (+ tribenuron-methyl+ metsulfuron-methyl) (DuPont)

OTHER PRODUCTS
thifensulfuron-methyl
'Prospect' (DuPont); 'Refine' (DuPont) mixtures: 'Basis' (+ rimsulfuron) (DuPont); 'Calibre' (+ tribenuron-methyl) (DuPont); 'Concert' (+ chlorimuron-ethyl) (DuPont); 'Grid' (+ rimsulfuron) (DuPont); 'Harmony Express' (+ carfentrazone-ethyl) (DuPont); 'Harmony Extra' (+ tribenuron-methyl) (DuPont); 'Harmony M' (+ metsulfuron-methyl) (DuPont); 'Lexus Millenium' (+ flupyrsulfuron-methyl-sodium) (DuPont); 'Millenium' (+ flupyrsulfuron-methyl-sodium) (DuPont); 'Reliance' (+ chlorimuron-ethyl) (DuPont); 'Scoop' (+ metsulfuron-methyl) (DuPont); 'Synchrony STS' (+ chlorimuron-ethyl) (DuPont) Discontinued products: 'Crackshot' * (Cyanamid) mixtures: 'DP 928' * (+ metsulfuron-methyl) (DuPont); 'DUK 110' * (+ tribenuron-methyl) (DuPont)

ANALYSIS
Product and residue analysis by hplc/ms/ms (Handbook of Residue Analytical Methods, pp 400-410).

MAMMALIAN TOXICOLOGY
thifensulfuron-methyl
Oral Acute oral LD50 for rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits >2000 mg/kg. Non-irritating to skin or eyes. Not a skin sensitiser. Inhalation LC50 (4 h) for rats >7.9 mg/l air. NOEL NOAEL (90 d) for rats 100 mg/kg diet; (2 y) for rats 500 mg/kg diet. NOAEL in reproduction (2 generation) in rats 2500 mg/kg diet; teratogenicity in rats 200 mg/kg daily. ADI 0.26 mg/kg. Other Non-mutagenic in the Ames and three other mutagenicity tests. Toxicity class WHO (a.i.) U; EPA (formulation) IV (TB, WG)

ECOTOXICOLOGY
thifensulfuron-methyl
Birds Acute oral LD50 for mallard ducks >2510 mg/kg. Dietary LC50 (8 d) for mallard ducks and Japanese quail >5620 mg/kg diet. Fish LC50 (96 h) for rainbow trout 410, bluegill sunfish 520 mg/l. Daphnia LC50 (48 h) 970 mg/l. Algae NOEC (120 h) for green algae 15.7 mg/l. Bees Non-toxic to bees. LD50 (48 h, topical) >12.5 mg/bee. Worms LC50 >2000 mg/kg.

ENVIRONMENTAL FATE
Animals In mammals, following oral administration of thifensulfuron-methyl, 70-75% of the unchanged material is excreted in the urine and faeces. The primary degradation mechanism involves hydrolysis of the methoxycarbonyl group, O-demethylation of the heterocyclic ring, and hydrolysis of the sulfonylurea group. Plants In field-grown wheat and corn, residues dissipate rapidly, involving cleavage of the urea bridge and metabolism of the methoxy group on the triazine ring and hydrolysis of the methyl ester group on the thiophene ring. Soil/Environment Thifensulfuron-methyl degrades rapidly in soil by microbial degradation, chemical hydrolysis and photoylsis; DT50 <1 to 7 days, DT90 <1 to 50 days.