3-amino-8-fluoro-5-methylthio-1,2,4-triazolo[4,3-c]pyrimidine hydrobromide | 219715-46-5

• 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: 3-amino-8-fluoro-5-methylthio-1,2,4-triazolo[4,3-c]pyrimidine hydrobromide
• 英文别名: 3-Amino-8-fluoro-5-methylthio[1,2,4]triazolo[4,3-c]-pyrimidine hydrobromide；8-Fluoro-5-methylsulfanyl-[1,2,4]triazolo[4,3-c]pyrimidin-3-amine;hydrobromide
• CAS: 219715-46-5
• 化学式: BrH*C₆H₆FN₅S
• 分子量: 280.123
• InChiKey: ZSYHZNWXNRMULL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.15
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-amino-8-fluoro-5-methylthio-1,2,4-triazolo[4,3-c]pyrimidine hydrobromide 、 sodium methylate 在 丙烯酸乙酯 作用下， 以 甲醇 为溶剂， 生成 5-methoxy-8-fluoro-[1,2,4]-triazolo[1,5-c]pyrimidin-2-amine
  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
• 作为产物：
  描述：

  2-methylthio-4-hydrazino-5-fluoropyrimidine 、 溴化氰 以 二氯甲烷 、 异丙醇 为溶剂， 以82%的产率得到3-amino-8-fluoro-5-methylthio-1,2,4-triazolo[4,3-c]pyrimidine hydrobromide
  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

• N-( 1,2,4] TRIAZOLOAZINYL)BENZENESULFONAMIDE AND PYRIDINESULFONAMIDE COMPOUNDS AND THEIR USE AS HERBICIDES
  申请人：Dow Agrosciences LLC

  公开号：EP0877745B1

  公开（公告）日：2001-07-25
• [EN] N-([1,2,4] TRIAZOLOAZINYL)BENZENESULFONAMIDE AND PYRIDINESULFONAMIDE COMPOUNDS AND THEIR USE AS HERBICIDES<br/>[FR] COMPOSES DU N-([1,2,4]TRIAZOLOAZINYL)BENZENE-SULFONAMIDE ET DE PYRIDINE-SULFONAMIDE, ET LEUR UTILISATION COMME HERBICIDES
  申请人：DOW AGROSCIENCES LLC

  公开号：WO1998013367A1

  公开（公告）日：1998-04-02

  (EN) N-(Triazoloazinyl)arylsulfonamide compounds, such as 2,6-dimethoxy-N-(8-chloro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)benzenesulfonamide, 2-methoxy-4-(trifluoromethyl)-N-(5,8-di-methoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)pyridine-3-sulfonamide, and 2-methoxy-6-methoxycarbonyl-N-(5,8-dimethoxy[1,2,4]triazolo-[1,5-a]pyridin-2-yl)benzenesulfonamide were prepared from appropriately substituted 2-amino[1,2,4]triazolo[1,5-c]pyrimidine and 2-amino[1,2,4]triazolo[1,5-a]pyridine compounds and appropriately substituted benzenesulfonyl chloride and pyridine-3-sulfonyl chloride compounds. The compounds were found to be useful as herbicides.(FR) Des composés du N-(triazoloazinyl)aryl-sulfonamide, tels que le 2,6-diméthoxy-N-(8-chloro-5-méthoxy[1,2,4]triazolo[1,5-c]pyrimidine-2-yl)benzène-sulfonamide, le 2-méthoxy-4-(trifluorométhyl)-N-(5,8-diméthoxy[1,2,4]triazolo[1,5-c]pyrimidine-2-yl)pyridine-3-sulfonamide et le 2-méthoxy-6-méthoxycarbonyl-N-(5,8-diméthoxy[1,2,4]triazolo[1,5-a]pyridine-2-yl)benzène-sulfonamide, ont été préparés à partir de composés de la 2-amino[1,2,4]triazolo[1,5-c]pyrimidine et de la 2-amino[1,2,4]triazolo[1,5-a]pyridine convenablement substitués et de composés du chlorure de benzène-sulfonyle et du chlorure de pyridine-3-sulfonyle convenablement substitués. Ces composés se sont avérés utiles comme herbicides.
• 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.