2-(cyclohexylcarbamoyl)-5-chloro-N'-((5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene)benzohydrazide | 1228312-53-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(cyclohexylcarbamoyl)-5-chloro-N'-((5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene)benzohydrazide
• 英文别名: 4-chloro-2-N-[(5-chloro-3-methyl-1-phenylpyrazol-4-yl)methylideneamino]-1-N-cyclohexylbenzene-1,2-dicarboxamide
• CAS: 1228312-53-5
• 化学式: C₂₅H₂₅Cl₂N₅O₂
• 分子量: 498.412
• InChiKey: QHESDWVTBUEMIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  88.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氯酞酰亚胺 在 盐酸 、 一水合肼 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2-(cyclohexylcarbamoyl)-5-chloro-N'-((5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene)benzohydrazide
  参考文献：
  名称：

  Design, Synthesis, and Insecticidal Activities of Phthalamides Containing a Hydrazone Substructure

  摘要：

  Fluobendiamide is the first commercialized artificial synthetic insecticide acting on the ryanodine receptor. This new molecule possesses a combination of excellent insecticidal activity and eco-friendly characteristics with a skeleton structure of phthalamide. In this study, we incorporated hydrazone, present in many pesticidal compounds reported during the last two decades, into phthalamide derivatives via Schiff-base condensation and aminolysis to obtain 21 new compounds; these compounds were characterized by proton nuclear magnetic resonance ((1)H NMR), infrared spectroscopy (IR), and high-resolution mass spectrometry (HRMS) or elemental analysis. A preliminary bioassay against peach aphids (Myzus persicae) revealed that the title compounds exhibited good stomach toxicity at 600 mg/L. Twelve new compounds were found to display higher activity than postive control flubendiamide (LC(50) = 184.099 mg/L), however, LC(50) was less than 100 mg/L only for compounds 4e, 4o, 4s, 4t (59-77 mg/L). That is, combinations of a p-fluorophenyl or (methyl)thienyl group at the Ar position with an isopropyl or cyclohexyl group at the R position might improve the lethality of the designed phthalamide derivative. Preliminary results of a bioassay at 600 mg/L against diamondback moth (Plutella xylostella, Linnaeus) showed that only the title compound 4e possessed good larvicidal activity. On comparison of the bioassay results of stomach toxicity and larvicidal activity, it is noteworthy that the compound incorporating phenylpyrazolyl exhibited good larvicidal activity and poor stomach activity.

  DOI：

  10.1021/jf1000919

文献信息

• Design, Synthesis, and Insecticidal Activities of Phthalamides Containing a Hydrazone Substructure
  作者：Ming Liu、Yi Wang、Wei-zi Wangyang、Feng Liu、Yong-liang Cui、You-sheng Duan、Min Wang、Shang-zhong Liu、Chang-hui Rui

  DOI：10.1021/jf1000919

  日期：2010.6.9

  Fluobendiamide is the first commercialized artificial synthetic insecticide acting on the ryanodine receptor. This new molecule possesses a combination of excellent insecticidal activity and eco-friendly characteristics with a skeleton structure of phthalamide. In this study, we incorporated hydrazone, present in many pesticidal compounds reported during the last two decades, into phthalamide derivatives via Schiff-base condensation and aminolysis to obtain 21 new compounds; these compounds were characterized by proton nuclear magnetic resonance ((1)H NMR), infrared spectroscopy (IR), and high-resolution mass spectrometry (HRMS) or elemental analysis. A preliminary bioassay against peach aphids (Myzus persicae) revealed that the title compounds exhibited good stomach toxicity at 600 mg/L. Twelve new compounds were found to display higher activity than postive control flubendiamide (LC(50) = 184.099 mg/L), however, LC(50) was less than 100 mg/L only for compounds 4e, 4o, 4s, 4t (59-77 mg/L). That is, combinations of a p-fluorophenyl or (methyl)thienyl group at the Ar position with an isopropyl or cyclohexyl group at the R position might improve the lethality of the designed phthalamide derivative. Preliminary results of a bioassay at 600 mg/L against diamondback moth (Plutella xylostella, Linnaeus) showed that only the title compound 4e possessed good larvicidal activity. On comparison of the bioassay results of stomach toxicity and larvicidal activity, it is noteworthy that the compound incorporating phenylpyrazolyl exhibited good larvicidal activity and poor stomach activity.