Imazosulfuron 唑吡嘧磺隆，咪唑磺隆

中文通用名称: 唑吡嘧磺隆
英文通用名称: imazosulfuron （BSI,ISO）
商品名称: Takeoff、Sibatito
试验代号: TH-913
化学名称:
1-(2-氯咪唑[1,2a]吡啶- 3 -基磺酰基)-3-(4,6-二甲氧基嘧啶-2-基)脲
1-(2-chloroimidazo[1,2a]pyridin-3-ylsulfonyl)-3-(4,6-dimethoxypyrimidin-2-yl)urea
CA主题索引名及CAS登录号:
2-chloro-N-[[(4,6-dimethoxypyrimidinyl)amino]carbonyl]imidazo[1,2a]pyridine-3-sulfonamide
[122548-33-8]

化学结构类型: 磺酰脲类
理化性质: 纯品为颗粒状固体；熔点183~184℃(分解)；密度1.574(25℃)；蒸气压为4.5×10-8Pa(25℃)。分配系数 LogP＝0.049。溶解度为（25℃，mg/l） ：水中6.75 (pH 5.1)，6 7 (pH6.1)，308 (pH 7.0)；乙腈2500；乙酸乙酯2200；丙酮4800；二氯甲烷12900；二甲苯400。电离常数pKa 4.0。

毒性:
大(小)鼠急性经口LD50：>5000mg/kg；兔急性经皮LD50：>2000mg/kg； 本品对兔眼睛和皮肤无刺激。大鼠急性吸入LC50(4小时)：2.4mg/l。野鸭急性经口LD50：>2250mg/kg；野鸭LC50：>5620mg/kg；鱼毒LC50(48小时)：鲤鱼>10mg/l；对水蚤 LC50(3小时)：>40mg/l。Ames试验呈阴性。

制剂:
0.3％颗粒剂。混剂有Batl 8.8％颗粒剂：0.3％唑吡嘧磺隆、5.0％杀草隆、3.5％苯噻草胺；Gosign 12.3％颗粒剂： 0.3％唑吡嘧磺隆、7.0％禾草畏、5.0％杀草隆；Hayate7.0％颗粒剂：0.3％唑吡嘧磺隆、5.0％杀草隆、0.2％敌草索、1.5％丙草胺；Award 41.2％胶悬剂：0.3％唑吡嘧磺隆、27.5％杀草隆、12.0％稗草畏。

作用机理: 乙酰乳酸合成酶(ALS)的抑制剂，即通过根部吸收唑吡嘧磺隆，然后输送到整株植物中，对支链氨基酸的生物合成的关键酶乙酰乳酸合成酶有强烈的抑制作用。唑吡嘧磺隆抑制杂草尖芽生长，阻止根部和幼苗的生长发育，从而使全株死亡。
适宜作物: 水稻和草坪
安全性: 由于唑吡嘧磺隆在水稻中可迅速代谢为无活性物质，因此即使水稻植株吸收一定量的唑吡嘧磺隆，也不会对水稻产生任何药害，对水稻安全。在各种气候条件下，该药剂对水稻均十分安全，故可在任何地区使用。
防除对象: 唑吡嘧磺隆可防除稻田大多数一年生与多年生阔叶杂草如牛毛毡、慈菇、莎草、泽泻、眼子菜、水芹等具有很好的活性。它亦能防除恶性杂草如野荸荠、野慈姑等。
使用方法: 唑吡嘧磺隆是一种可苗前和苗后使用的、阔叶杂草除草剂，其持效期为40~50天。水稻田使用剂量为75~100克有效成分/公顷，草坪中使用剂量为500~1000克有效成分/公顷。
合成方法:
唑吡嘧磺隆的合成方法较多，最可行的方法如下：以2-氨基吡啶为起始原料，首先与氯乙酸反应，再经氯化、氯磺化、胺化，然后与氯甲酸苯酯反应，最后与二甲氧基嘧啶胺缩合即得目的物。反应式为：

主要原料与中间体: 2-氨基吡啶、氯乙酸或溴乙酸、氯磺酸、三氯氧磷、氯甲酸苯酯反应、4,6-二甲氧基嘧啶-2-胺
分析方法: HPLC
开发公司: 日本武田制药公司。

imazosulfuron
Herbicide
HRAC B WSSA 2; sulfonylurea

NOMENCLATURE
Common name imazosulfuron (BSI, pa E-ISO)
IUPAC name 1-(2-chloroimidazo[1,2-a]pyridin-3-ylsulfonyl)-3-(4,6-dimethoxypyrimidin-2-yl)urea
Chemical Abstracts name 2-chloro-N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]imidazo[1,2-a]pyridine-3-sulfonamide
CAS RN [122548-33-8] Development codes TH-913

PHYSICAL CHEMISTRY
Mol. wt. 412.8 M.f. C14H13ClN6O5S Form Crystalline powder. M.p. 183-184 ºC (decomp.) V.p. 4.5 ´ 10-5 mPa (25 ºC) KOW logP = 0.049 (pH 7, 25 ºC) S.g./density 1.574 g/ml (25.5 ºC) Solubility In water 6.75 (pH 5.1), 67 (pH 6.1), 308 (pH 7.0) (all in mg/l, 25 ºC). In acetonitrile 2500, ethyl acetate 2200, acetone 4800, dichloromethane 12 900, xylene 400 (all in mg/l, 25 °C). pKa 4.0

COMMERCIALISATION
History Development rights licensed to Takeda Chemical Industries Ltd (now Sumitomo Chemical Takeda Agro Company Ltd) by Urania Chemicals GmbH (now Spiess-Urania) in 1994. Manufacturers Sumitomo Chemical Takeda

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 Absorbed by plants mainly through the roots and translocated throughout the plant. Inhibits shoot growth and retards root development. Uses Controls most annual (excluding Echinochloa oryzicola) and perennial broad-leaved weeds and sedges in paddy rice (75-95 g/ha) and turf (500-1000 g/ha). Formulation types GR; SC. Selected products: 'Sibatito' (Sumitomo Chemical Takeda); 'Takeoff' (Sumitomo Chemical Takeda)

OTHER PRODUCTS
'Kocis' (Sumitomo Chemical Takeda, Sipcam Inagra); 'Longet' (Sumitomo Chemical Takeda) mixtures: 'Award' (+ pyributicarb+ daimuron) (Sumitomo Chemical Takeda); 'Crush' (+ cafenstrole+ daimuron) (Sumitomo Chemical Takeda); 'Gosign' (+ daimuron+ esprocarb) (Sumitomo Chemical Takeda); 'Hayate' (+ pretilachlor+ daimuron+ dimethametryn) (Sumitomo Chemical Takeda); 'Batl' (+ mefenacet+ daimuron) (Nihon Bayer, Sumitomo Chemical Takeda); 'Donichi' (+ daimuron+ fentrazamide) (Bayer CropScience, Sumitomo Chemical Takeda, SDS Biotech KK); 'Kikkubai' (+ daimuron+ etobenzanid) (Hodogaya, Sumitomo Chemical Takeda, SDS Biotech KK); 'Leading' (+ fentrazamide) (Nihon Bayer); 'Sheriff' (+ pretilachlor+ cyhalofop-butyl+ dimethametryn) (Otsuka, Sumitomo Chemical Takeda); 'The-One' (+ pentoxazone+ daimuron) (Kaken, Sumitomo Chemical Takeda)

ANALYSIS
Product and residue analysis by hplc. Methods for sulfonylurea residues in crops, soil and water reviewed (A. C. Barefoot et al., Proc. Br. Crop Prot. Conf. - Weeds, 1995, 2, 707).

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats and mice >5000 mg/kg. Skin and eye Acute percutaneous LD50 for male and female rats >2000 mg/kg. Not irritant to eyes and skin (rabbits); not a skin sensitiser (guinea pigs). Inhalation LC50 (4 h) for rats >2.4 mg/l air. NOEL (2 y) for male rats 106.1, female rats 132.46 mg/kg b.w. daily; (1 y) for male and female dogs 75 mg/kg b.w. daily. Not oncogenic in rats and mice. Not teratogenic in rats and rabbits. Other No mutagenic effects in Ames, DNA-repair and chromosomal aberration tests.

ECOTOXICOLOGY
Birds Acute oral LD50 for bobwhite quail and mallard ducks 2250 mg/kg. Dietary LC50 (5 d) for bobwhite quail and mallard ducks >5620 ppm. Fish LC50 (96 h) for carp 250 mg/l. Daphnia EC50 (48 h) >100 mg/l. Bees LD50 (48 h) (oral) 48.2 mg/bee; (contact) 66.5 mg/bee.