2-amino-8-chloro-5-methoxy-1,2,4-triazolo[1,5-c]pyrimidine | 219715-58-9

• 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: 2-amino-8-chloro-5-methoxy-1,2,4-triazolo[1,5-c]pyrimidine
• 英文别名: 2-Amino-8-chloro-5-methoxy[1,2,4]-triazolo[1,5-c]pyrimidine；2-amino-8-chloro-5-methoxy-[1,2,4]triazolo[1,5-c]pyrimidine；2-Amino-8-chloro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine；8-chloro-5-methoxy-[1,2,4]triazolo[1,5-c]pyrimidin-2-amine
• CAS: 219715-58-9
• 化学式: C₆H₆ClN₅O
• 分子量: 199.6
• InChiKey: QYQKVLHYWFIURN-UHFFFAOYSA-N

物化性质

• 熔点：
  >250 °C(Solv: N,N-dimethylformamide (68-12-2))
• 密度：
  1.83±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 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：
  78.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-amino-8-chloro-5-methoxy-1,2,4-triazolo[1,5-c]pyrimidine 在 三甲基氯硅烷 、 sodium iodide 、 三乙胺 作用下， 以 乙醚 为溶剂， 生成 2-(N-Trimethylsilylamino)-8-chloro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine
  参考文献：
  名称：

  N-(\x9b1, 2, 4! triazoloazinyl) benzenesulfonamide and pyridinesulfonamide

  摘要：

  N-(Triazoloazinyl)芳基磺酰胺化合物，例如2,6-二甲氧基-N-(8-氯-5-甲氧基[1,2,4]三唑[1,5-c]嘧啶-2-基)苯磺酰胺，2-甲氧基-4-(三氟甲基)-N-(5,8-二甲氧基[1,2,4]三唑[1,5-c]嘧啶-2-基)吡啶-3-磺酰胺和2-甲氧基-6-甲氧羰基-N-(5,8-二甲氧基[1,2,4]三唑[1,5-a]吡啶-2-基)苯磺酰胺，是由适当取代的2-氨基[1,2,4]三唑[1,5-c]嘧啶和2-氨基[1,2,4]三唑[1,5-a]吡啶化合物以及适当取代的苯磺酰氯和吡啶-3-磺酰氯化合物制备而成。这些化合物被发现可用作除草剂。

  公开号：

  US05858924A1
• 作为产物：
  描述：

  3-Amino-8-chloro-5-methyl-thio[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 2-amino-8-chloro-5-methoxy-1,2,4-triazolo[1,5-c]pyrimidine
  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) thiophenesulfonamide compounds and their use as herbicides
  申请人：——

  公开号：US20020094935A1

  公开（公告）日：2002-07-18

  N-(Triazoloazinyl)thiophenesulfonamide compounds were prepared from appropriately substituted 2-amino[1,2,4]triazolo[1,5-c]pyrimidine, 2-amino[1,2,4]triazolo[1,5-a]pyrimidine and 2-amino[1,2,4]triazolo[1,5-a]pyridine compounds and appropriately substituted thiophenesulfonyl chloride compounds. The compounds were found to be useful as herbicides.

  N-(三唑啉基)噻吩磺胺化合物是从适当取代的2-氨基[1,2,4]三唑[1,5-c]嘧啶、2-氨基[1,2,4]三唑[1,5-a]嘧啶和2-氨基[1,2,4]三唑[1,5-a]吡啶化合物以及适当取代的噻吩磺酰氯化合物制备而成的。这些化合物被发现对除草剂具有用途。
• N- ([1,2,4,] TRIAZOLOAZINYL) THIOPHENESULFONAMIDE COMPOUNDS AND THEIR USE AS HERBICIDES
  申请人：——

  公开号：US20030199393A1

  公开（公告）日：2003-10-23

  N-(Triazolo[1,5-a]pyrimidinyl)thiophene-sulfonamide compounds were prepared from appropriately substituted 2-amino[1,2,4]triazolo[1,5-a]pyrimidine compounds and appropriately substituted thiophene-sulfonyl chloride compounds. The compounds were found to be useful as herbicides.

  N-(三唑并[1,5-a]嘧啶基)噻唑磺酰胺化合物是从适当取代的2-氨基[1,2,4]三唑并[1,5-a]嘧啶化合物和适当取代的噻唑磺酰氯化合物制备而成。这些化合物被发现可用作除草剂。
• N-([1,2,4]triazoloazinyl)benzenesulfonamide and pyridinesulfonamide
  申请人：——

  公开号：US06005108A1

  公开（公告）日：1999-12-21

  N-(Triazoloazinyl)arylsulfonamide compounds, such as 2,6-dimethoxy-N-(8-chloro-5-methoxy[1,2,4]-triazolo[1,5-c]pyrimidin-2-yl)b enzenesulfonamide, 2-methoxy-4-(trifluoromethyl)-N-(5,8-dimethoxy[1,2,4]-triazolo[1,5-c]pyrim idin-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.

  N-(三唑并嗪基)芳基磺酰胺化合物，例如2,6-二甲氧基-N-(8-氯-5-甲氧基[1,2,4]-三唑并[1,5-c]嘧啶-2-基)苯磺酰胺，2-甲氧基-4-(三氟甲基)-N-(5,8-二甲氧基[1,2,4]-三唑并[1,5-c]嘧啶-2-基)吡啶-3-磺酰胺和2-甲氧基-6-甲氧羰基-N-(5,8-二甲氧基[1,2,4]三唑并[1,5-a]嘧啶-2-基)苯磺酰胺，是由适当取代的2-氨基[1,2,4]-三唑并[1,5-c]嘧啶和2-氨基[1,2,4]-三唑并[1,5-a]-吡啶化合物以及适当取代的苯磺酰氯和吡啶-3-磺酰氯化合物制备而成。这些化合物被发现可用作除草剂。
• N-[1,2,4]triazoloazinyl) benzenesulfonamide and pyridinesulfonamide compounds and their use as herbicides
  申请人：Dow AgroSciences LLC

  公开号：US06303814B1

  公开（公告）日：2001-10-16

  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-dimethoxy[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 benzene sulfonyl chloride and pyridine-3-sulfonyl chloride compounds. The compounds were found to be useful as herbicides.

  N-(Triazoloazinyl)芳基磺酰胺化合物，例如2,6-二甲氧基-N-(8-氯-5-甲氧基[1,2,4]三唑[1,5-c]嘧啶-2-基)苯磺酰胺，2-甲氧基-4-(三氟甲基)-N-(5,8-二甲氧基[1,2,4]三唑[1,5-c]嘧啶-2-基)吡啶-3-磺酰胺和2-甲氧基-6-甲氧基羰基-N-(5,8-二甲氧基[1,2,4]三唑[1,5-a]吡啶-2-基)苯磺酰胺，是由适当取代的2-氨基[1,2,4]三唑[1,5-c]嘧啶和2-氨基[1,2,4]三唑[1,5-a]吡啶化合物以及适当取代的苯磺酰氯和吡啶-3-磺酰氯化合物制备而成。这些化合物被发现可用作除草剂。
• N-([1,2,4]triazoloazinyl)thiophenesulfonamide compounds and their use as herbicides
  申请人：Dow AgroSciences LLC

  公开号：US06645918B1

  公开（公告）日：2003-11-11

  N-(Triazolo[1,5-a]pyrimidinyl)thiophenesulfonamide compounds were prepared from appropriately substituted 2-amino[1,2,4]triazolo[1,5-a]pyrimidine compounds and appropriately substituted thiophenesulfonyl chloride compounds. The compounds were found to be useful as herbicides.

  从适当取代的2-氨基[1,2,4]三唑并[1,5-a]嘧啶化合物和适当取代的噻吩磺酰氯化合物中制备了N-(三唑并[1,5-a]嘧啶基)噻吩磺酰胺化合物。这些化合物被发现可用作除草剂。