Triasulfuron 醚苯磺隆

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醚苯磺隆

CAS NO:82097-50-5
英文名称:Triasulfuron
化学名称:1-[2-(2-氯乙烷基)苯基磺酰基]-3-(4-甲氧基-6-甲基-1,3,5-三嗪-2-基)脲;2-(2-chloroethoxy)-n-(((4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino)carbonyl)benzenesulfonamide
其他名称:农家乐
分子式: C14H16ClN5O5S
分子量: 401.83

理化性质:本品为无色晶体, 熔点186oC, 蒸汽压100fpa(20oC). 溶解性(20oC):水1.5g/L(PH=7), 微溶于丙酮,二氯甲烷,环己酮,甲醇,正辛醇180mg/L,二甲苯166mg/L,微溶于一般有机溶剂.Kow0.11(PH7).亚氨基呈酸性,Pka4.5
稳定性:低于熔点部分分解,水解DT50 2h(PH3),288h(PH9),108h(PH10)
毒性:大鼠急性经口 LD50>5000mg/kg,大鼠急性经皮LD50>2000mg/kg,对兔皮肤稍有刺激作用,但对眼睛无刺激作用。大鼠饲喂的无作用剂量为200mg/kg饲料。虹鳟鱼LC50大于100mg/L。
作用特点及杀草谱:本品属磺酰脲类除草剂,选择性内吸除草剂,是侧链氨基酸合成抑制剂,通过根和叶吸收,并迅速传输到分生组织。苗前苗后用于小粒禾谷类作物如小麦、大麦等,可防除一年生阔叶杂草和某些禾本科杂草,如播娘蒿、荠菜、藜、麦瓶草、猪殃殃、三色堇、碎米荠、地肤、蓼、扁蓄、早熟禾等。使用量为5-15g/ha。本品可与绿麦隆或异丙隆混用,春季施药,对阔叶杂草以及禾本科杂草和双子叶杂草防效尤佳。此外,该除草剂还可与溴苯腈或2甲4氯混用。特殊地区在植前拌土或芽前施用。

剂型:2 0%,75%WDG,75%WP、

生产方法:邻氯乙氧基苯磺酰胺,与光气反应制成相应的异氰酸酯,再与2-氨基-4-甲氧基-6-甲基均三嗪反应,即制得醚苯黄隆。

生产情况:瑞士汽巴嘉基公司开发生产。江苏瑞东农药有限公司;金华市金龙化工有限公司;常州市荣祥生物化学研究所;武汉嘉凯隆科技发展有限公司;江苏省农用激素工程技术研究中心有限公司;浙江泰达作物科技有限公司(100t/a);沈阳丰收农药有限公司;江苏常隆化工有限公司;捷马化工股份有限公司(浙江龙游农药厂)

其他:2002年行政保护期满。

 

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triasulfuron
Herbicide
HRAC B WSSA 2; sulfonylurea

  triasulfuron

NOMENCLATURE
Common name triasulfuron (BSI, draft E-ISO, (m) draft F-ISO)
IUPAC name 1-[2-(2-chloroethoxy)phenylsulfonyl]-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea
Chemical Abstracts name 2-(2-chloroethoxy)-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]benzenesulfonamide
CAS RN [82097-50-5] Development codes CGA 131 036 (Ciba-Geigy)

PHYSICAL CHEMISTRY
Mol. wt. 401.8 M.f. C14H16ClN5O5S Form Fine white powder. M.p. 178.1 °C (decomp.) V.p. <2 ´ 10-3 mPa (25 ºC) (OECD 104) KOW logP = 1.1 (pH 5.0), -0.59 (pH 6.9), -1.8 (pH 9.0) (25 ºC) Henry <8 ´ 10-5 Pa m3 mol-1 (calc.) S.g./density 1.5 g/cm3 Solubility In water 32 (pH 5), 815 (pH 7), 13 500 (pH 8.4) (all in mg/l, 25 ºC). In acetone 14, dichloromethane 36, ethyl acetate 4.3 (all in g/l, 25 ºC). In ethanol 420, n-octanol 130, n-hexane 0.04, toluene 300 (all in mg/l, 25 ºC). Stability Stable for more than 2 years under normal storage conditions. Partial decomposition below the melting point. On hydrolysis, DT50 8.2 h (pH 1), 3.1 y (pH 7), 4.7 h (pH 10). pKa 4.64 (20 ºC)

COMMERCIALISATION
History Herbicide reported by J. Amrein & H. R. Gerber (Proc. 1985 Br. Crop Prot. Conf. - Weeds, 1, 55). Introduced by Ciba-Geigy AG (now Syngenta AG). Patents US 4514212; EP 44808 Manufacturers Syngenta

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 herbicide, absorbed by the leaves and roots, and rapidly translocated to meristems. Uses Control of broad-leaved weeds pre- and post-emergence in wheat, barley and triticale, at 5-10 g/ha. Formulation types WG. Selected products: mixtures: 'Lintur' (+ dicamba-sodium) (Syngenta); 'Satis' (+ fluoroglycofen-ethyl) (Syngenta)

OTHER PRODUCTS
'Amber' (Syngenta); 'Lo-Gran' (Syngenta) mixtures: 'Dicuran Forte' (+ chlorotoluron) (Syngenta); 'Fuego' (+ dicamba) (dicamba as diglycolamine salt) (Syngenta); 'Keos' (+ isoproturon) (Syngenta); 'Logran B-Power' (+ butafenacil) (Syngenta); 'Logran extra' (+ terbutryn) (Syngenta); 'Rave' (+ dicamba-sodium) (Syngenta); 'Teal' (+ bromoxynil+ ioxynil) (Syngenta); 'Tricuran' (+ chlorotoluron+ terbutryn) (Syngenta); 'Zoom' (+ dicamba-sodium) (Syngenta)

ANALYSIS
Analysis by glc or by hplc with u.v. detection. Methods for sulfonylurea residues in crops, soil and water reviewed (A. C. Barefoot et al., Proc. Br. Crop Prot. Conf. - Weeds, 1995, 2, 707). Details from Syngenta.

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats and mice >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Mild skin irritant; non-irritating to eyes (rabbits). Non-sensitising to skin (guinea pigs). Inhalation LC50 (4 h) for rats >5.18 mg/l air. NOEL (2 y) for rats 32.1 mg/kg b.w. daily, for mice 1.2 mg/kg b.w. daily; (1 y) for dogs 33 mg/kg b.w. daily. ADI 0.012 mg/kg b.w. Toxicity class WHO (a.i.) U; EPA (formulation) IV EC classification N; R50, R53

ECOTOXICOLOGY
Birds Acute oral LD50 for quail and ducks >2150 mg/kg. Fish LC50 (96 h) for rainbow trout, carp, catfish, sheepshead minnow and bluegill sunfish >100 mg/l. Daphnia LC50 (96 h) >100 mg/l. Algae EC50 (5-14 d) for Selenastrum 0.035, Scenedesmus 0.77, Anabaena 1.7, Navicula >100 mg/l. Other aquatic spp. EC50 (48 h) for Quahog clam 56 mg/l. Bees Non-toxic to honeybees. LD50 (acute and contact) >100 mg/bee. Worms LC50 (14 d) for earthworms >1000 mg/kg soil.

ENVIRONMENTAL FATE
Animals Mainly excreted in the urine in unchanged form. Plants In wheat, metabolism is by hydroxylation (para to the sulfonyl urea bridge), followed by conjugation of various hydroxy metabolites with glucose. DT50 in forage c. 3 days. In straw and grain, no residues were detectable at harvest time. Soil/Environment The degradation behaviour in soil is determined by the soil type, pH, and especially temperature and moisture content. Field studies with silty loam, clay loam and sandy loam showed a median DT50 19 d, depending on soil type.