Design, synthesis, crystal structure, insecticidal activity, molecular docking, and QSAR studies of novel N3-substituted imidacloprid derivatives

Mei Juan Wang, Xiao Bo Zhao, Dan Wu, Ying Qian Liu, Yan Zhang, Xiang Nan, Huanxiang Liu, Hai Tao Yu, Guan Fang Hu, Li Ting Yan

Research output: Contribution to journalArticlepeer-review

28 Citations (Scopus)

Abstract

Three novel series of N3-substituted imidacloprid derivatives were designed and synthesized, and their structures were identified on the basis of satisfactory analytical and spectral (1H NMR, 13C NMR, MS, elemental analysis, and X-ray) data. Preliminary bioassays indicated that all of the derivatives exhibited significant insecticidal activities against Aphis craccivora, with LC50 values ranging from 0.00895 to 0.49947 mmol/L, and the insecticidal activities of some of them were comparable to those of the control imidacloprid. Some key structural features related to their insecticidal activities were identified, and the binding modes between target compounds and nAChR model were also further explored by molecular docking. By comparing the interaction features of imidacloprid and compound 26 with highest insecticidal activity, the origin of the high insecticidal activity of compound 26 was identified. On the basis of the conformations generated by molecular docking, a satisfactory 2D-QSAR model with six selected descriptors was built using genetic algorithm-multiple linear regression (GA-MLR) method. The analysis of the built model showed the molecular size, shape, and the ability to form hydrogen bond were important for insecticidal potency. The information obtained in the study will be very helpful for the design of new derivatives with high insecticidal activities.

Original languageEnglish
Pages (from-to)5429-5442
Number of pages14
JournalJournal of Agricultural and Food Chemistry
Volume62
Issue number24
DOIs
Publication statusPublished - 18 Jun 2014
Externally publishedYes

Keywords

  • QSAR
  • X-ray diffraction
  • insecticidal activity
  • molecular docking
  • synthesis

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