Back to Search
Start Over
Design, Synthesis, Crystal Structure, Insecticidal Activity, Molecular Docking, and QSAR Studies of Novel N3-Substituted Imidacloprid Derivatives
- Source :
- Journal of Agricultural and Food Chemistry. 62:5429-5442
- Publication Year :
- 2014
- Publisher :
- American Chemical Society (ACS), 2014.
-
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 ((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.
- Subjects :
- Insecticides
Quantitative structure–activity relationship
Magnetic Resonance Spectroscopy
Molecular Structure
Stereochemistry
Hydrogen bond
Imidazoles
Quantitative Structure-Activity Relationship
Hydrogen Bonding
General Chemistry
Nuclear magnetic resonance spectroscopy
Crystal structure
Carbon-13 NMR
Nitro Compounds
Inhibitory Concentration 50
Neonicotinoids
chemistry.chemical_compound
chemistry
Imidacloprid
Aphids
Linear Models
Proton NMR
Animals
Molecule
General Agricultural and Biological Sciences
Subjects
Details
- ISSN :
- 15205118 and 00218561
- Volume :
- 62
- Database :
- OpenAIRE
- Journal :
- Journal of Agricultural and Food Chemistry
- Accession number :
- edsair.doi.dedup.....feb1372726355bba4f60cc2e73031533