1-(6-bromo-2-mercaptobenzothiazol-5-yl)-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one | 916730-24-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 1-(6-bromo-2-mercaptobenzothiazol-5-yl)-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
• 英文别名: 1-(6-bromo-2-mercaptobenzo[d]thiazol-5-yl)-4-(difluoromethyl)-3-methyl-1H-1,2,4-triazol-5(4H)-one；2-(6-bromo-2-sulfanylidene-3H-1,3-benzothiazol-5-yl)-4-(difluoromethyl)-5-methyl-1,2,4-triazol-3-one
• CAS: 916730-24-0
• 化学式: C₁₁H₇BrF₂N₄OS₂
• 分子量: 393.236
• InChiKey: PGGGDDIRZXJQGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(6-bromo-2-mercaptobenzothiazol-5-yl)-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 0.17h， 以80%的产率得到1-[2-(allylthio)-6-bromobenzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
  参考文献：
  名称：

  Design and synthesis of 1-(benzothiazol-5-yl)-1H-1,2,4-triazol-5-ones as protoporphyrinogen oxidase inhibitors

  摘要：

  Protoporphyrinogen oxidase (PPO, E.C. 1.3.3.4) is the action target for several structurally diverse herbicides. A series of novel 4-(difluoromethyl)-1-(6-halo-2-substituted-benzothiazol-5-yl)-3-methyl-1H-1,2,4-triazol-5(4H)-ones 2a-z were designed and synthesized via the ring-closure of two ortho-substituents. The in vitro bioassay results indicated that the 26 newly synthesized compounds exhibited good PPO inhibition effects with K-i values ranging from 0.06 to 17.79 mu M. Compound 2e, ethyl 2-{[5-(4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-6-fluorobenzo-thiazol-2-yl]thio}acetate, was the most potent inhibitor with K-i value of 0.06 mu M against mtPPO, comparable to (K-i = 0.03 mu M) sulfentrazone. Further green house assays showed that compound 2f (K-i = 0.24 mu M, mtPPO), ethyl 2-{[5-(4(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-6-fluorobenzothiazol-2-yl]thio}propanoate, showed the most promising post-emergence herbicidal activity with broad spectrum even at concentrations as low as 37.5 g ai/ha. Soybean exhibited tolerance to compound 2f at the dosages of 150 g ai/ha, whereas they are susceptible to sulfentrazone even at 75 g ai/ha. Thus, compound 2f might be a potential candidate as a new herbicide for soybean fields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.056
• 作为产物：
  描述：

  1-(2-bromo-4-fluorophenyl)-3-methyl-1H-1,2,4-triazol-5(4H)-one 在 硫酸 、 四丁基溴化铵 、 硝酸 、 铁粉 、 氯化铵 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 1-(6-bromo-2-mercaptobenzothiazol-5-yl)-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
  参考文献：
  名称：

  Design and synthesis of 1-(benzothiazol-5-yl)-1H-1,2,4-triazol-5-ones as protoporphyrinogen oxidase inhibitors

  摘要：

  Protoporphyrinogen oxidase (PPO, E.C. 1.3.3.4) is the action target for several structurally diverse herbicides. A series of novel 4-(difluoromethyl)-1-(6-halo-2-substituted-benzothiazol-5-yl)-3-methyl-1H-1,2,4-triazol-5(4H)-ones 2a-z were designed and synthesized via the ring-closure of two ortho-substituents. The in vitro bioassay results indicated that the 26 newly synthesized compounds exhibited good PPO inhibition effects with K-i values ranging from 0.06 to 17.79 mu M. Compound 2e, ethyl 2-{[5-(4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-6-fluorobenzo-thiazol-2-yl]thio}acetate, was the most potent inhibitor with K-i value of 0.06 mu M against mtPPO, comparable to (K-i = 0.03 mu M) sulfentrazone. Further green house assays showed that compound 2f (K-i = 0.24 mu M, mtPPO), ethyl 2-{[5-(4(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-6-fluorobenzothiazol-2-yl]thio}propanoate, showed the most promising post-emergence herbicidal activity with broad spectrum even at concentrations as low as 37.5 g ai/ha. Soybean exhibited tolerance to compound 2f at the dosages of 150 g ai/ha, whereas they are susceptible to sulfentrazone even at 75 g ai/ha. Thus, compound 2f might be a potential candidate as a new herbicide for soybean fields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.056

文献信息

• SYNTHESIS AND HERBICIDAL ACTIVITY OF 1- (2-SUBSTITUTED BENZO[d]THIAZOL-5-YL)- 1H-1,2,4-TRIAZOL-5(4H)- ONE DERIVATIVES
  申请人：YANG Guangfu

  公开号：US20090143229A1

  公开（公告）日：2009-06-04

  Synthesis and herbicidal activity of novel 1-(2-substituted benzo[d]thiazol-5-yl)-1H-1,2,4-triazol-5(4H)-one derivatives. Using a dose of 300 gai./h, the compounds of the invention possess significant herbicidal activity for Echinochloa crusgalli, Digiatria sanguinalis, Setaria viridis, Brassica juncea, Amaranthus retroflexus and Chenopodium album.

  合成和除草活性的新型1-(2-取代苯并[d]噻唑-5-基)-1H-1,2,4-三唑-5(4H)-酮衍生物。使用300 gai./h的剂量，本发明的化合物对稗草、血茅草、绿色狗尾草、芥菜、反枝苋和藜麦具有显著的除草活性。
• Synthesis and herbicidal activity of 1- (2-substituted benzo[d]thiazol-5-yl)-1H-1,2,4-triazol-5(4H)- one derivatives
  申请人：Huazhong Normal University

  公开号：US07666890B2

  公开（公告）日：2010-02-23

  Synthesis and herbicidal activity of novel 1-(2-substituted benzo[d]thiazol-5-yl)-1H-1,2,4-triazol-5(4H)-one derivatives. Using a dose of 300 gai./h, the compounds of the invention possess significant herbicidal activity for Echinochloa crusgalli, Digiatria sanguinalis, Setaria viridis, Brassica juncea, Amaranthus retroflexus and Chenopodium album.

  合成和除草活性的新型1-(2-取代苯并[d]噻唑-5-基)-1H-1,2,4-三唑-5(4H)-酮衍生物。在300克/公顷的剂量下，本发明的化合物对稗草、血竭草、狗尾草、芥菜、反枝苋和藜麦具有显著的除草活性。
• US7666890B2
  申请人：——

  公开号：US7666890B2

  公开（公告）日：2010-02-23