6-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-3-methyl-[1,2,4] triazolo[3,4-b][1,3,4]thiadiazole | 1438853-66-7

• 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: 6-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-3-methyl-[1,2,4] triazolo[3,4-b][1,3,4]thiadiazole
• 英文别名: 6-[5-Bromo-2-(3-chloropyridin-2-yl)pyrazol-3-yl]-3-methyl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole；6-[5-bromo-2-(3-chloropyridin-2-yl)pyrazol-3-yl]-3-methyl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole
• CAS: 1438853-66-7
• 化学式: C₁₂H₇BrClN₇S
• 分子量: 396.657
• InChiKey: ZIGVKFGIIHTDIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-肼基-3-氯吡啶 在 dipotassium peroxodisulfate 、 硫酸 、 sodium ethanolate 、 sodium hydroxide 、 三氯氧磷 、 三溴氧磷 作用下， 以 甲醇 、 乙醇 、 水 、 乙腈 为溶剂， 反应 5.0h， 生成 6-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-3-methyl-[1,2,4] triazolo[3,4-b][1,3,4]thiadiazole
  参考文献：
  名称：

  Synthesis, Insecticidal Activities, and SAR Studies of Novel Pyridylpyrazole Acid Derivatives Based on Amide Bridge Modification of Anthranilic Diamide Insecticides

  摘要：

  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.

  DOI：

  10.1021/jf4012467

文献信息

• 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.