3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide | 1438853-57-6

• 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: 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide
• 英文别名: Des-[N-(4-chloro-2-methyl-6[((methylamino)carboyl))phenyl]] Chlorantraniliprole；5-bromo-2-(3-chloropyridin-2-yl)pyrazole-3-carboxamide
• CAS: 1438853-57-6
• 化学式: C₉H₆BrClN₄O
• 分子量: 301.53
• InChiKey: ALGLHCFROQVWRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 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：
  73.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 N-((3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)methyl)-4-(tert-butyl)benzamide
  参考文献：
  名称：

  N-吡啶基吡唑并-5-甲基胺及其衍生物的设计，合成和杀虫活性评估

  摘要：

  在寻找新型杀虫剂时，设计并合成了一系列N-吡啶基吡唑并5-甲基胺及其衍生物。中得到的22的目标化合物，生物测定法表明，一些目标化合物的表现出良好的杀虫活性对小菜蛾（小菜蛾）和草地贪夜蛾（草地夜蛾）。特别是，化合物9j表现出对小菜蛾的最佳杀虫活性，LC 50值为22.11 mg / L，化合物9q对S. frugiperda的杀虫活性最好。100 mg / L时死亡率为73.99％。结构-活性关系（SAR）分析表明，R 1处的4-CF 3与N-吡啶基吡唑通过酰胺键连接可以增强目标化合物的杀虫活性。这项研究为进一步设计和优化N-吡啶基吡唑衍生物提供了有价值的线索。

  DOI：

  10.1002/jhet.4136
• 作为产物：
  描述：

  2-肼基-3-氯吡啶 在 dipotassium peroxodisulfate 、 lithium hydroxide monohydrate 、 硫酸 、 sodium ethanolate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三溴氧磷 作用下， 以 四氢呋喃 、 乙醇 、 水 、 乙腈 为溶剂， 反应 2.0h， 生成 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide
  参考文献：
  名称：

  N-吡啶基吡唑并-5-甲基胺及其衍生物的设计，合成和杀虫活性评估

  摘要：

  在寻找新型杀虫剂时，设计并合成了一系列N-吡啶基吡唑并5-甲基胺及其衍生物。中得到的22的目标化合物，生物测定法表明，一些目标化合物的表现出良好的杀虫活性对小菜蛾（小菜蛾）和草地贪夜蛾（草地夜蛾）。特别是，化合物9j表现出对小菜蛾的最佳杀虫活性，LC 50值为22.11 mg / L，化合物9q对S. frugiperda的杀虫活性最好。100 mg / L时死亡率为73.99％。结构-活性关系（SAR）分析表明，R 1处的4-CF 3与N-吡啶基吡唑通过酰胺键连接可以增强目标化合物的杀虫活性。这项研究为进一步设计和优化N-吡啶基吡唑衍生物提供了有价值的线索。

  DOI：

  10.1002/jhet.4136

文献信息

• 一种含脲桥的苯甲酰胺类衍生物及其制备方法与应用
  申请人：浙江工业大学

  公开号：CN106336395A

  公开（公告）日：2017-01-18

  本发明提供了一种含脲桥的苯甲酰胺类衍生物及其制备方法与应用，该含脲桥的苯甲酰胺类衍生物即3‑溴‑N‑((2‑胺基甲酰基苯基)胺基甲酰基)‑1‑(3‑氯吡啶‑2‑基)‑1H‑吡唑‑5‑甲酰胺衍生物在200～100μg/mL浓度下本发明得到的有些化合物对东方粘虫有一定的抑制率，化合物I‑3、化合物I‑5、化合物I‑6和化合物I‑10在200ppm其抑制率分别达到100％、80％，当浓度为100ppm时，化合物I‑3的抑制率仍有60％。本发明所述化合物为具有杀虫活性的新化合物，为新农药的研发提供了基础。
• 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.
• Zhu, Yong; Zhao, Wen; Han, Liang, Journal of the Chemical Society of Pakistan, 2017, vol. 39, # 3, p. 464 - 470
  作者：Zhu, Yong、Zhao, Wen、Han, Liang、Dong, Wei-Li、Liu, Xing-Hai

  DOI：——

  日期：——
• COMPOSITION COMPRISING A BIOLOGICAL CONTROL AGENT AND AN INSECTICIDE
  申请人：Bayer CropScience AG

  公开号：EP2925143A2

  公开（公告）日：2015-10-07
• [EN] COMPOSITION COMPRISING A BIOLOGICAL CONTROL AGENT AND AN INSECTICIDE<br/>[FR] COMPOSITION COMPRENANT UN AGENT DE LUTTE BIOLOGIQUE ET UN INSECTICIDE
  申请人：BAYER CROPSCIENCE AG

  公开号：WO2014086750A2

  公开（公告）日：2014-06-12

  The present invention relates to a composition comprising at least one biological control agent selected from the group consisting of Paecilomyces lilacinus strain 251 (AGAL No. 89/030550) and Coniothyrium minitons CON/M/91-08 (DSM 9660) and/or a mutant of these strains having all the identifying characteristics of the respective strain, and/or at least one metabolite produced by the respective strain that exhibits activity against nematodes, insects and/or phytopathogens, and at least one insecticide (I) selected from the group consisting of GABA-gated chloride channel antagonists and chloride channel activators in a synergistically effective amount. Furthermore, the present invention relates to a kit of parts comprising said composition and the use of said composition.