5-Bromo-2-(3-chloropyridin-2-yl)pyrazole-3-carbonyl isothiocyanate | 1392234-72-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-Bromo-2-(3-chloropyridin-2-yl)pyrazole-3-carbonyl isothiocyanate
• 英文别名: 5-bromo-2-(3-chloropyridin-2-yl)pyrazole-3-carbonyl isothiocyanate
• CAS: 1392234-72-8
• 化学式: C₁₀H₄BrClN₄OS
• 分子量: 343.591
• InChiKey: JYCQVPMNMPPKNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-Bromo-2-(3-chloropyridin-2-yl)pyrazole-3-carbonyl isothiocyanate 在 potassium carbonate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of Novel 3-Chloropyridin-2-yl-Pyrazole Derivatives and their Insecticidal, Fungicidal Activities and QSAR Study

  摘要：

  在我们早期的研究中，报道了一系列含有酰基硫脲连接基（C）的邻氨基苯甲酰胺显示了良好的活性。基于这一研究，设计并合成了从C衍生出的四个系列新型吡啶基吡唑衍生物（D-G）。共合成24个化合物，所有化合物均通过熔点、1H NMR、13C NMR和HRMS进行了表征。生物测定结果表明，化合物5b、5c和6b对东方粘虫（Mythimna separata）在200mg/L下显示出100%的杀虫活性。评估了它们对A. solani、F. graminearum、P. capsici、S. sclerotiorum、B. cinerea和R. solani的杀菌活性，结果显示含有酰基胍连接基的化合物7a-g对B. cinerea显示出良好的抗菌活性，其中7d和7f在50mg/L下对B. cinerea显示出97.5%的抑制活性。为进一步探究基于杀虫活性数据的全面构效关系，进行了比较分子场分析（CoMFA），并获得了统计上可靠且预测能力良好的模型（r2 = 0.972，q2 = 0.604）。

  DOI：

  10.2174/1570180811310060005
• 作为产物：
  描述：

  3-溴-1-(3-氯-2-吡啶)-1H-吡唑-5-羧酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.5h， 生成 5-Bromo-2-(3-chloropyridin-2-yl)pyrazole-3-carbonyl isothiocyanate
  参考文献：
  名称：

  新型含酰基硫脲和酰基脲的邻氨基苯甲酰胺的合成及杀虫活性

  摘要：

  设计并合成了两个系列的含酰基硫脲和酰基脲接头的邻氨基苯甲酰胺，其接头的长度和柔性有所变化，可与已知的邻氨基二酰胺杀虫剂进行比较。总共合成了26种新化合物，所有化合物均通过1 H核磁共振和高分辨率质谱进行了表征。评估了它们对东方粘虫（Mythimna separata），蚊虫幼虫（Culex pipiens pallens）和小菜蛾（Plutella xylostella）的杀虫活性。对东方粘虫的杀幼虫活性表明，在某些结构中引入酰基硫脲可以保留其杀虫活性。15种化合物中的8种（13a – 13e，14a – 14e和15a – 15e）在10 mg / L时表现出100％的杀幼虫活性。然而，酰脲的引入降低了杀虫活性；11种化合物（17a – 17k）中只有3种在200 mg / L时表现出100％的杀幼虫活性。全细胞膜片钳技术表明，化合物13b和绿蒽醌对电压门控钙通道表现出相似的作用。钙成像

  DOI：

  10.1021/jf302446c

文献信息

• Synthesis and Insecticidal Activity of Novel N-Pyridylpyrazole Carbonyl Thioureas
  作者：Baolei Wang、Yi Ma、Lixia Xiong、Zhengming Li

  DOI：10.1002/cjoc.201100386

  日期：2012.4

  series of novel N‐pyridylpyrazole carbonyl thioureas were designed and synthesized. Their structures were characterized by melting points, 1H NMR, IR and elemental analysis or HRMS. The bioassay tests indicated that some of these compounds exhibited moderate insecticidal activity against Mythimna separata Walker and Culex pipiens pallens. Among 17 compounds, 5n and 5p showed 100% larvicidal activity against

  设计并合成了一系列新型的N-吡啶基吡唑羰基硫脲。它们的结构通过熔点，1 H NMR，IR和元素分析或HRMS表征。生物测定结果表明，这些化合物中的一些对粘实蛾和淡色库蚊具有中等的杀虫活性。在17种化合物中，5n和5p在100 mg / L的测试浓度下对Mythimna separata Walker表现出100％的杀幼虫活性。
• [EN] PYRAZOLE FORMYLTHIOUREA DERIVATIVE, PREPARATION METHOD THEREFORE AND USE THEREOF<br/>[FR] DÉRIVÉ DE PYRAZOLE FORMYLTHIOURÉE, SON PROCÉDÉ DE PRÉPARATION ET SON UTILISATION
  申请人：UNIV NANKAI

  公开号：WO2012163095A1

  公开（公告）日：2012-12-06

  一种如式I的吡唑甲酰基硫脲化合物，其制备方法以及应用。式I化合物具有杀虫活性，可以作为农用杀虫剂。
• Synthesis, Insecticidal Activities, and SAR Studies of Novel Pyridylpyrazole Acid Derivatives Based on Amide Bridge Modification of Anthranilic Diamide Insecticides
  作者：Bao-Lei Wang、Hong-Wei Zhu、Yi Ma、Li-Xia Xiong、Yong-Qiang Li、Yu Zhao、Ji-Feng Zhang、You-Wei Chen、Sha Zhou、Zheng-Ming Li

  DOI：10.1021/jf4012467

  日期：2013.6.12

  Anthranilic diamides are one of the most important classes of modern agricultural insecticides. To discover new structure-modified compounds with high activity, series of novel carbonyl thioureas, carbonyl ureas, oxadiazoles, carbonyl thiophosphorylureas, oxadiazole-containing amides, and thiazoline-containing amides were designed through the modification of the amide bridge based on the structure of chlorantraniliprole and were synthesized, and bioassays were carried out. The compounds were characterized and confirmed by melting point, IR, H-1 NMR, and elemental analyses or HRMS. Preliminary bioassays indicated that some compounds exhibited significant insecticidal activities against oriental armyworm, diamondback moth, beet armyworm, corn borer, and mosquito. Among them, trifluoroethoxyl-containing carbonyl thiourea 20a showed best larvicidal activity against oriental armyworm, with LC50 and LC95 values of 0.1812 and 0.7767 mg/L, respectively. Meanwhile, 20c and 20e showed 86 and 57% death rates against diamondback moth at 0.005 mg/L, and the LC50 values of the two compounds were 0.0017 and 0.0023 mg/L, respectively, which were lower than that of the control chlorantraniliprole. The relationship between structure and insecticidal activity was discussed, and the HF calculation results indicated that the carbonyl thiourea moiety plays an important role in the insecticidal activity. The present work demonstrated that the trifluoroethoxyl-containing carbonyl thioureas can be used as lead compounds for further development of novel insecticides.
• Synthesis of Novel 3-Chloropyridin-2-yl-Pyrazole Derivatives and their Insecticidal, Fungicidal Activities and QSAR Study
  作者：Ji-Feng Zhang、Chen Liu、Yi Ma、Bao-Lei Wang、Li-Xia Xiong、Shu-Jing Yu、Zheng-Ming Li

  DOI：10.2174/1570180811310060005

  日期：2013.5.1

  In our early study, a series of anthranilic diamides containing acylthiourea linker (C) was reported to display favorable activities. Based on that research, four series of novel pyridylpyrazole derivatives (D-G) derived from C were designed and synthesized. Totally 24 compounds were synthesized and all the compounds were characterized by melting points, 1H NMR, 13C NMR and HRMS. Bioassay results indicated that compounds 5b, 5c and 6b showed 100 % insecticidal activities against oriental armyworm (Mythimna separata) at 200mg/L. Their fungicidal activities against A. solani, F. graminearum, P. capsici, S. sclerotiorum, B. cinerea and R. solani were evaluated and the results indicated that compounds 7a-g which contained acylguanidine linker showed favourable antibacterial activity against B. cinerea, among which 7d and 7f showed 97.5 % inhibitory activities against B. cinerea at 50mg/L. To further explore the comprehensive structure-activity relationship on the basis of insecticidal activity data, comparative molecular field analysis (CoMFA) was performed, and a statistically reliable model with good predictive power (r2 = 0.972, q2 = 0.604) was achieved.

  在我们早期的研究中，报道了一系列含有酰基硫脲连接基（C）的邻氨基苯甲酰胺显示了良好的活性。基于这一研究，设计并合成了从C衍生出的四个系列新型吡啶基吡唑衍生物（D-G）。共合成24个化合物，所有化合物均通过熔点、1H NMR、13C NMR和HRMS进行了表征。生物测定结果表明，化合物5b、5c和6b对东方粘虫（Mythimna separata）在200mg/L下显示出100%的杀虫活性。评估了它们对A. solani、F. graminearum、P. capsici、S. sclerotiorum、B. cinerea和R. solani的杀菌活性，结果显示含有酰基胍连接基的化合物7a-g对B. cinerea显示出良好的抗菌活性，其中7d和7f在50mg/L下对B. cinerea显示出97.5%的抑制活性。为进一步探究基于杀虫活性数据的全面构效关系，进行了比较分子场分析（CoMFA），并获得了统计上可靠且预测能力良好的模型（r2 = 0.972，q2 = 0.604）。
• Synthesis and Insecticidal Activities of Novel Anthranilic Diamides Containing Acylthiourea and Acylurea
  作者：Ji-Feng Zhang、Jun-Ying Xu、Bao-Lei Wang、Yu-Xin Li、Li-Xia Xiong、Yong-Qiang Li、Yi Ma、Zheng-Ming Li

  DOI：10.1021/jf302446c

  日期：2012.8.8

  xylostella) were evaluated. The larvicidal activities against oriental armyworm indicated that the introduction of acylthiourea into some structures could retain their insecticidal activity; 8 of the 15 compounds (13a–13e, 14a–14e, and 15a–15e) exhibited 100% larvicidal activity at 10 mg/L. However, the introduction of acylurea decreased the insecticidal activity; only 3 of the 11 compounds (17a–17k) exhibited

  设计并合成了两个系列的含酰基硫脲和酰基脲接头的邻氨基苯甲酰胺，其接头的长度和柔性有所变化，可与已知的邻氨基二酰胺杀虫剂进行比较。总共合成了26种新化合物，所有化合物均通过1 H核磁共振和高分辨率质谱进行了表征。评估了它们对东方粘虫（Mythimna separata），蚊虫幼虫（Culex pipiens pallens）和小菜蛾（Plutella xylostella）的杀虫活性。对东方粘虫的杀幼虫活性表明，在某些结构中引入酰基硫脲可以保留其杀虫活性。15种化合物中的8种（13a – 13e，14a – 14e和15a – 15e）在10 mg / L时表现出100％的杀幼虫活性。然而，酰脲的引入降低了杀虫活性；11种化合物（17a – 17k）中只有3种在200 mg / L时表现出100％的杀幼虫活性。全细胞膜片钳技术表明，化合物13b和绿蒽醌对电压门控钙通道表现出相似的作用。钙成像