2,6-dichloro-N-(8-fluoro-5-methoxy-1,2,4-triazolo[1,5-c]pyrimidin-2-yl)benzenesulfonamide | 219713-12-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,6-dichloro-N-(8-fluoro-5-methoxy-1,2,4-triazolo[1,5-c]pyrimidin-2-yl)benzenesulfonamide
• 英文别名: 2,6-dichloro-N-(8-fluoro-5-methoxy-[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)benzenesulfonamide
• CAS: 219713-12-9
• 化学式: C₁₂H₈Cl₂FN₅O₃S
• 分子量: 392.198
• InChiKey: HESLQFPDPPOTQS-UHFFFAOYSA-N

物化性质

• 熔点：
  211-212 °C
• 密度：
  1.804±0.14 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 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：
  8

反应信息

• 作为产物：
  描述：

  2,6-二氯苯磺酰氯 、 5-methoxy-8-fluoro-[1,2,4]-triazolo[1,5-c]pyrimidin-2-amine 在 吡啶 、 二甲基亚砜 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以50%的产率得到2,6-dichloro-N-(8-fluoro-5-methoxy-1,2,4-triazolo[1,5-c]pyrimidin-2-yl)benzenesulfonamide
  参考文献：
  名称：

  Penoxsulam—Structure–activity relationships of triazolopyrimidine sulfonamides

  摘要：

  The discovery of the sulfonamide herbicides, which inhibit the enzyme acetolactate synthase (ALS), has resulted in many investigations to exploit their herbicidal activity. One area which proved particularly productive was the N-aryltriazolo[1,5-c]pyrimidine sulfonamides, providing three commercial herbicides, cloransulam-methyl, diclosulam and florasulam. Additional structure-activity investigations by reversing the sulfonamide linkage resulted in the discovery of triazolopyrimidine sulfonamides with cereal crop selectivity and high levels of grass and broadleaf weed control. Research efforts to exploit these high levels of weed activity ultimately led to the discovery of penoxsulam, a new herbicide developed for grass, sedge and broadleaf weed control in rice. Synthetic efforts and structure-activity relationships leading to the discovery of penoxsulam will be discussed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.010

文献信息

• Penoxsulam—Structure–activity relationships of triazolopyrimidine sulfonamides
  作者：Timothy C. Johnson、Timothy P. Martin、Richard K. Mann、Mark A. Pobanz

  DOI：10.1016/j.bmc.2009.02.010

  日期：2009.6

  The discovery of the sulfonamide herbicides, which inhibit the enzyme acetolactate synthase (ALS), has resulted in many investigations to exploit their herbicidal activity. One area which proved particularly productive was the N-aryltriazolo[1,5-c]pyrimidine sulfonamides, providing three commercial herbicides, cloransulam-methyl, diclosulam and florasulam. Additional structure-activity investigations by reversing the sulfonamide linkage resulted in the discovery of triazolopyrimidine sulfonamides with cereal crop selectivity and high levels of grass and broadleaf weed control. Research efforts to exploit these high levels of weed activity ultimately led to the discovery of penoxsulam, a new herbicide developed for grass, sedge and broadleaf weed control in rice. Synthetic efforts and structure-activity relationships leading to the discovery of penoxsulam will be discussed. (C) 2009 Elsevier Ltd. All rights reserved.