2-chloro-5-(((E)-2-(((E)-(2-ethyl-6-methylphenyl)diazenyl)(nitro)methylene)imidazolidin-1-yl)methyl)pyridine | 1335228-61-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-chloro-5-(((E)-2-(((E)-(2-ethyl-6-methylphenyl)diazenyl)(nitro)methylene)imidazolidin-1-yl)methyl)pyridine
• CAS: 1335228-61-9
• 化学式: C₁₉H₂₁ClN₆O₂
• 分子量: 400.868
• InChiKey: QRONPBUGCATMOM-NVGBRHKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  96.02
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  2-甲基-6-乙基苯胺 、 1-(2-chloro-5-pyridylmethyl)-2-nitromethyleneimidazolidine 在 盐酸 、 sodium nitrite 、 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 以71%的产率得到2-chloro-5-(((E)-2-(((E)-(2-ethyl-6-methylphenyl)diazenyl)(nitro)methylene)imidazolidin-1-yl)methyl)pyridine
  参考文献：
  名称：

  Design, Synthesis, Crystal Structure Analysis, and Insecticidal Evaluation of Phenylazoneonicotinoids

  摘要：

  On the basis of research of the proposed modes of action between neonicotinoids and insect nicotinic acetylcholine receptor (nAChR), a series of phenylazoneonicotinoids were designed and synthesized to further promote the pi-pi interaction between molecule and amino acid residues. The target compounds have been identified on the basis of satisfactory analytical and spectral (H-1 NMR, C-13 NMR, HRMS, and X-ray) data. The preliminary results revealed that tiny differences in substitutes resulted in different configurations and great bioactivity variations. Some compounds with electron-donating groups on positions 2 and 6 of the phenyl ring presented higher insecticidal activity than imidacloprid against cowpea aphids (Aphis craccivora). The impressive crystal structure of the excellent insecticidal activity compound 9q clearly proved that the functional electronegative pharmacophore was approximately vertical to the methyleneimidazolidine plane. The differences in the mode of interaction on nAChR of typical compounds 9h and 9q remain unclear.

  DOI：

  10.1021/jf2029708

文献信息

• [EN] AZO HETEROCYCLIC COMPOUND HAVING INSECTICIDAL ACTIVITY, AND PREPARATION AND APPLICATIONS THEREOF<br/>[FR] COMPOSÉ HÉTÉROCYCLIQUE AZO DOTÉ D'UNE ACTIVITÉ INSECTICIDE ET PRÉPARATION ET APPLICATIONS ASSOCIÉES
  申请人：UNIV EAST CHINA SCIENCE & TECH

  公开号：WO2012065568A1

  公开（公告）日：2012-05-24

  An azo heterocyclic compound as indicated in Formula (I), optical isomers and cis-trans isomers thereof, or agriculturally acceptable salts, and agricultural compositions, preparation method, and applications thereof. The present compound and derivatives thereof have insecticidal activity against homopteran pest insects and lepidopteran pest insects.
• Design, Synthesis, Crystal Structure Analysis, and Insecticidal Evaluation of Phenylazoneonicotinoids
  作者：Zhenjun Ye、Shuang Xia、Xusheng Shao、Jiagao Cheng、Xiaoyong Xu、Zhiping Xu、Zhong Li、Xuhong Qian

  DOI：10.1021/jf2029708

  日期：2011.10.12

  On the basis of research of the proposed modes of action between neonicotinoids and insect nicotinic acetylcholine receptor (nAChR), a series of phenylazoneonicotinoids were designed and synthesized to further promote the pi-pi interaction between molecule and amino acid residues. The target compounds have been identified on the basis of satisfactory analytical and spectral (H-1 NMR, C-13 NMR, HRMS, and X-ray) data. The preliminary results revealed that tiny differences in substitutes resulted in different configurations and great bioactivity variations. Some compounds with electron-donating groups on positions 2 and 6 of the phenyl ring presented higher insecticidal activity than imidacloprid against cowpea aphids (Aphis craccivora). The impressive crystal structure of the excellent insecticidal activity compound 9q clearly proved that the functional electronegative pharmacophore was approximately vertical to the methyleneimidazolidine plane. The differences in the mode of interaction on nAChR of typical compounds 9h and 9q remain unclear.