Design, synthesis, crystal structure, insecticidal activity, molecular docking, and QSAR studies of novel N3-substituted imidacloprid derivatives.
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 ((1)H NMR, (13)C 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.
School of Pharmacy, Lanzhou University , Lanzhou 730000, P.R. China.
Mei-Juan
MJ
Wang
Xiao-Bo
XB
Zhao
Dan
D
Wu
Ying-Qian
YQ
Liu
Yan
Y
Zhang
Xiang
X
Nan
Huanxiang
H
Liu
Hai-Tao
HT
Yu
Guan-Fang
GF
Hu
Li-Ting
LT
Yan
D000818:Animals; D001042:Aphids; D006860:Hydrogen Bonding; D007093:Imidazoles / Q000737:chemistry*; D020128:Inhibitory Concentration 50; D007306:Insecticides / Q000737:chemistry*; D016014:Linear Models; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D000073943:Neonicotinoids; D009574:Nitro Compounds / Q000737:chemistry*; D021281:Quantitative Structure-Activity Relationship
D007093:Imidazoles; D007306:Insecticides; D000073943:Neonicotinoids; D009574:Nitro Compounds; C082359:imidacloprid