1-(5-amino-2-bromo-4-fluorophenyl)-4-difluoromethyl-3-methyl-1H-1,2,4-triazol-5-one | 916730-25-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(5-amino-2-bromo-4-fluorophenyl)-4-difluoromethyl-3-methyl-1H-1,2,4-triazol-5-one
• 英文别名: 1-(5-amino-2-bromo-4-fluorophenyl)-4-(difluoromethyl)-3-methyl-1H-1,2,4-triazol-5(4H)-one；2-(5-amino-2-bromo-4-fluorophenyl)-4-(difluoromethyl)-5-methyl-1,2,4-triazol-3-one
• CAS: 916730-25-1
• 化学式: C₁₀H₈BrF₃N₄O
• 分子量: 337.099
• InChiKey: RUVCQZJVPAMGIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  61.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(5-amino-2-bromo-4-fluorophenyl)-4-difluoromethyl-3-methyl-1H-1,2,4-triazol-5-one 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 3.17h， 生成 ethyl {6-bromo-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl]benzothiazol-2-ylthio}acetate
  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：

  2-溴-4-氟苯胺 在 盐酸 、 硫酸 、 叠氮磷酸二苯酯 、 四丁基溴化铵 、 硝酸 、 铁粉 、 氯化铵 、 三乙胺 、 potassium hydroxide 、 sodium nitrite 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 为溶剂， 反应 8.08h， 生成 1-(5-amino-2-bromo-4-fluorophenyl)-4-difluoromethyl-3-methyl-1H-1,2,4-triazol-5-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

• Syntheses and Herbicidal Activities of Novel Triazolinone Derivatives
  作者：Yan-Ping Luo、Li-Li Jiang、Guo-Dong Wang、Qiong Chen、Guang-Fu Yang

  DOI：10.1021/jf703654g

  日期：2008.3.1

  triazolinones 1 displayed much better herbicidal activities than phenylurea-type triazolinones 2. Most fortunately, compound 3, methyl 2-[3-methyl-(2-fluoro-4-chloro-5-ethylsulfonamidephenyl)-4,5-dihydro-5-oxo-1 H-1,2,4-triazol-4-yl]methylenephenyl-2-( E)-methoxyiminoacetate, was found to be the most promising candidate due to its comparable herbicidal activity at 75-150 g of active ingredient/ha with

  原卟啉原氧化酶（Protox，EC 1.3.3.4）已被确定为除草剂最重要的作用靶标之一。为了寻找新型的Protox抑制剂，通过引入三种药效基团，环酰亚胺，苯基脲和（E）-2-甲氧基亚氨基-2-邻甲苯基乙酸甲酯，设计并合成了一系列标题化合物1、2和3，进入三唑啉酮的支架中。生物测定结果表明，所得到的环状酰亚胺型三唑啉酮1具有比苯脲型三唑啉酮2更好的除草活性。最幸运的是，化合物3是甲基2- [3-甲基-（2-氟-4-氯-5-）乙基磺酰胺苯基）-4,5-二氢-5-氧代-1 H-1,2,4-三唑-4-基]亚甲基苯基-2-（E）-甲氧基亚氨基乙酸酯，被发现是最有前途的候选物，因为其在75-150 g活性成分/公顷下的除草活性与商业产品次磺en相当。根据除草谱和作物选择性的测试结果，可以开发出化合物3作为芽后除草剂，用于防治稻田阔叶杂草。
• 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