5,7-dimethyl[1,2,4]triazolo[1,5-c]pyrimidine-2-sulphonyl chloride | 112729-27-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并嘧啶类
• 英文名称: 5,7-dimethyl[1,2,4]triazolo[1,5-c]pyrimidine-2-sulphonyl chloride
• 英文别名: 5,7-Dimethyl[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonyl chloride；5,7-dimethyl-[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonyl chloride
• CAS: 112729-27-8
• 化学式: C₇H₇ClN₄O₂S
• mdl: MFCD19200527
• 分子量: 246.677
• InChiKey: FTNNUZAZQKCNQZ-UHFFFAOYSA-N

物化性质

• 密度：
  1.74±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  85.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,7-dimethyl[1,2,4]triazolo[1,5-c]pyrimidine-2-sulphonyl chloride 、 2,5-二氟苯胺 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 N-(2,5-difluorophenyl)-5,7-dimethyl-[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide
  参考文献：
  名称：

  Syntheses and herbicidal activity of new triazolopyrimidine-2-sulfonamides as acetohydroxyacid synthase inhibitor

  摘要：

  The triazolopyrimidine-2-sulfonanilide, discovered from preparing bioisosteres of the sulfonylurea herbicides, is an important class of acetohydroxyacid synthase (AHAS, EC 4.1.3.18) inhibitors. At least over ten triazolopyrimidine sulfonanilides have been commercialized as herbicides for the control of broadleaf weeds and grass with cereal crop selectivity. Herein, a series of triazolopyrimidine-2-sulfonanilides were designed and synthesized with the aim of discovery of new herbicides with higher activity. The assay results of the inhibition activity of the synthesized compounds against Arabidopsis thatiana AHAS indicated that some compounds showed a little higher activity against flumetsulam (FS), the first commercial triazolopyrimidine-2-sulfonanilide-type herbicide. The k(i) values of two promising compounds 3d and 8h are respectively, 1.61 and 1.29 mu M, while that of FS is 1.85 mu M. Computational simulation results indicated the ester group of compound 3d formed hydrogen bonds with the surrounding residues Arg'198 and Ser653, which accounts for its 11.5-folds higher AHAS inhibition activity than Y6610. Further green house assay showed that compound 3d has comparable herbicidal activity as FS. Even at the concentration of 37.5 g.ai/ha, 3d showed excellent herbicidal activity against Galium aparine, Cerastium arvense, Chenopodium album, Amaranthus retroflexus, and R mu mex acetasa, moderate herbicidal activity against Polygonum humifusum, Cyperus iria, and Eclipta prostrate. The combination of in vitro and in vivo assay indicated that 3d could be regarded as a new potential acetohydroxyacid synthase-inhibiting herbicide candidate for further study. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.015
• 作为产物：
  描述：

  5,7-dimethyl-3H-[1,2,4]triazolo[1,5-c]pyrimidine-2-thione 以 二氯甲烷 、 水 为溶剂， 生成 5,7-dimethyl[1,2,4]triazolo[1,5-c]pyrimidine-2-sulphonyl chloride
  参考文献：
  名称：

  Triazolopyrimidine herbicides

  摘要：

  该发明提供了除草三唑磺胺类化合物，以及它们的制备方法和含有它们的组合物。这些化合物的结构如下：其中Ra代表氢，Rb代表一个基团R³CONHCR²=CR¹-，或者Ra和Rb一起代表一个结构为-C(R³)=N-C(R²)=C(R¹)-或-C(=Y)-N(R⁶)-C(R²)=C(R¹)-的链，其中R¹、R²和R³分别代表氢、羟基、硫醇基、卤素、氰基、氨基、烷基氨基、二烷基氨基，或取代或未取代的烷基、芳基、芳基烷基、烷氧基或烷硫基；Y代表氧或硫，R⁶代表氢或取代或未取代的烷基或芳基；或者R¹和R²一起代表-CH=CH-CH=CH-或-(CH₂)n-，其中n为3、4或5；R⁴代表取代的苯基或取代或未取代的芳基烷基或杂环芳基基团；R⁵代表氢、酰基、羧基、烷氧羰基、烷基磺酰基，或者取代或未取代的烷基、烯基、炔基、芳基或芳基烷基，或者一个结构为的基团，其中Ra和Rb如上定义。

  公开号：

  EP0244948A3

文献信息

• Syntheses and herbicidal activity of new triazolopyrimidine-2-sulfonamides as acetohydroxyacid synthase inhibitor
  作者：Chao-Nan Chen、Qiong Chen、Yu-Chao Liu、Xiao-Lei Zhu、Cong-Wei Niu、Zhen Xi、Guang-Fu Yang

  DOI：10.1016/j.bmc.2010.06.015

  日期：2010.7

  The triazolopyrimidine-2-sulfonanilide, discovered from preparing bioisosteres of the sulfonylurea herbicides, is an important class of acetohydroxyacid synthase (AHAS, EC 4.1.3.18) inhibitors. At least over ten triazolopyrimidine sulfonanilides have been commercialized as herbicides for the control of broadleaf weeds and grass with cereal crop selectivity. Herein, a series of triazolopyrimidine-2-sulfonanilides were designed and synthesized with the aim of discovery of new herbicides with higher activity. The assay results of the inhibition activity of the synthesized compounds against Arabidopsis thatiana AHAS indicated that some compounds showed a little higher activity against flumetsulam (FS), the first commercial triazolopyrimidine-2-sulfonanilide-type herbicide. The k(i) values of two promising compounds 3d and 8h are respectively, 1.61 and 1.29 mu M, while that of FS is 1.85 mu M. Computational simulation results indicated the ester group of compound 3d formed hydrogen bonds with the surrounding residues Arg'198 and Ser653, which accounts for its 11.5-folds higher AHAS inhibition activity than Y6610. Further green house assay showed that compound 3d has comparable herbicidal activity as FS. Even at the concentration of 37.5 g.ai/ha, 3d showed excellent herbicidal activity against Galium aparine, Cerastium arvense, Chenopodium album, Amaranthus retroflexus, and R mu mex acetasa, moderate herbicidal activity against Polygonum humifusum, Cyperus iria, and Eclipta prostrate. The combination of in vitro and in vivo assay indicated that 3d could be regarded as a new potential acetohydroxyacid synthase-inhibiting herbicide candidate for further study. (C) 2010 Elsevier Ltd. All rights reserved.
• Triazolopyrimidine herbicides
  申请人：SCHERING AGROCHEMICALS LIMITED

  公开号：EP0244948A3

  公开（公告）日：1989-03-15

  The invention provides herbicidal triazolesulphonamides, processes for their preparation and compositions containing them, the compounds being of the formula: and the salts thereof, where Ra represents hydrogen and Rb represents a group R³CONHCR²=CR¹-, or Ra and Rb together represent a chain of formula -C(R³)=N-C(R²)=C(R¹)- or -C(=Y)-N(R⁶)-C(R²)=C(R¹)-, where R¹, R² and R³, which may be the same or different, each represent hydrogen, hydroxy, mercapto, halo, cyano, amino, alkylamino, dialkylamino, or substituted or unsubstituted alkyl, aryl, aralkyl, alkoxy or alkylthio, Y is oxygen or sulphur, and R⁶ is hydrogen or a substituted or unsubstituted alkyl or aryl group; or R¹ and R² together represent -CH=CH-CH=CH- or -(CH₂)n- where n is 3, 4 or 5; R⁴ represents substituted phenyl or a substituted or unsubstituted aralkyl or heteroaryl group; and R⁵ represents hydrogen, acyl, carboxy, lkoxycarbonyl, alkylsulphonyl, or a substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl or aralkyl group, or a group of the formula: where Ra and Rb are as defined hereinbefore.

  该发明提供了除草三唑磺胺类化合物，以及它们的制备方法和含有它们的组合物。这些化合物的结构如下：其中Ra代表氢，Rb代表一个基团R³CONHCR²=CR¹-，或者Ra和Rb一起代表一个结构为-C(R³)=N-C(R²)=C(R¹)-或-C(=Y)-N(R⁶)-C(R²)=C(R¹)-的链，其中R¹、R²和R³分别代表氢、羟基、硫醇基、卤素、氰基、氨基、烷基氨基、二烷基氨基，或取代或未取代的烷基、芳基、芳基烷基、烷氧基或烷硫基；Y代表氧或硫，R⁶代表氢或取代或未取代的烷基或芳基；或者R¹和R²一起代表-CH=CH-CH=CH-或-(CH₂)n-，其中n为3、4或5；R⁴代表取代的苯基或取代或未取代的芳基烷基或杂环芳基基团；R⁵代表氢、酰基、羧基、烷氧羰基、烷基磺酰基，或者取代或未取代的烷基、烯基、炔基、芳基或芳基烷基，或者一个结构为的基团，其中Ra和Rb如上定义。