N-(2,6-difluorophenyl)-5-methoxy-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide | 1159487-31-6

• 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: N-(2,6-difluorophenyl)-5-methoxy-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide
• 英文别名: Y6610；N-(2,6-difluorophenyl)-5-methoxy-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide
• CAS: 1159487-31-6
• 化学式: C₁₂H₉F₂N₅O₃S
• 分子量: 341.298
• InChiKey: AURRGAZZXRJZGY-UHFFFAOYSA-N

物化性质

• 密度：
  1.69±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  5-methoxy-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl chloride 、 2,6-二氟苯胺 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以5.2 g的产率得到N-(2,6-difluorophenyl)-5-methoxy-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide
  参考文献：
  名称：

  Design and synthesis of N-2,6-difluorophenyl-5-methoxyl-1,2,4-triazolo[1,5-a]-pyrimidine-2-sulfonamide as acetohydroxyacid synthase inhibitor

  摘要：

  Triazolopyrimidine-2-sulfonamide belongs to a herbicide group called acetohydroxyacid synthase inhibitors. With the aim to discover new triazolopyrimidine sulfonanilide compounds with high herbicidal activity and faster degradation rate in soil, the methyl group of Flumetsulam (FS) was modified into a methoxy group to produce a new herbicidal compound, N-2,6-difluorophenyl-5-methoxy-1,2,4-triazolo[1,5-a] pyrimidine-2-sulfonamide (experimental code: Y6610). The enzymatic kinetic results indicated that compound Y6610 and FS have k(i) values of 3.31 x 10 (6) M and 3.60 x 10 (7) M against Arabidopsis thaliana AHAS, respectively. The 10-fold lower enzyme-inhibiting activity of Y6610 was explained rationally by further computational simulations and binding free energy calculations. In addition, compound Y6610 was found to display the same level in vivo post-emergent herbicidal activity as FS against some broad-leaf weeds and good safety to rice, maize, and wheat at the dosages of 75-300g ai/ha. Further determination of the half-lives in soil revealed that the half-life in soil of Y6610 is 3.9 days shorter than that of FS. The experimental results herein showed that compound Y6610 could be regarded as a new potential acetohydroxyacid synthase-inhibiting herbicide candidate for further study. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.03.018

文献信息

• Design and synthesis of N-2,6-difluorophenyl-5-methoxyl-1,2,4-triazolo[1,5-a]-pyrimidine-2-sulfonamide as acetohydroxyacid synthase inhibitor
  作者：Chao-Nan Chen、Li-Li Lv、Feng-Qin Ji、Qiong Chen、Hui Xu、Cong-Wei Niu、Zhen Xi、Guang-Fu Yang

  DOI：10.1016/j.bmc.2009.03.018

  日期：2009.4

  Triazolopyrimidine-2-sulfonamide belongs to a herbicide group called acetohydroxyacid synthase inhibitors. With the aim to discover new triazolopyrimidine sulfonanilide compounds with high herbicidal activity and faster degradation rate in soil, the methyl group of Flumetsulam (FS) was modified into a methoxy group to produce a new herbicidal compound, N-2,6-difluorophenyl-5-methoxy-1,2,4-triazolo[1,5-a] pyrimidine-2-sulfonamide (experimental code: Y6610). The enzymatic kinetic results indicated that compound Y6610 and FS have k(i) values of 3.31 x 10 (6) M and 3.60 x 10 (7) M against Arabidopsis thaliana AHAS, respectively. The 10-fold lower enzyme-inhibiting activity of Y6610 was explained rationally by further computational simulations and binding free energy calculations. In addition, compound Y6610 was found to display the same level in vivo post-emergent herbicidal activity as FS against some broad-leaf weeds and good safety to rice, maize, and wheat at the dosages of 75-300g ai/ha. Further determination of the half-lives in soil revealed that the half-life in soil of Y6610 is 3.9 days shorter than that of FS. The experimental results herein showed that compound Y6610 could be regarded as a new potential acetohydroxyacid synthase-inhibiting herbicide candidate for further study. (C) 2009 Elsevier Ltd. All rights reserved.