Cis-pairs Of Aromatic Neonicotinoid Compounds Synthesis, Structure, Biological Activity And Molecular Docking Studies

In order to find and screen lead compounds according the development requirements of the 21st century neonicotinoid pesticide, we started with commercial pesticides nitenpyram, through Mannich reaction, and prepared by introducing an aromatic ring into nitenpyram and forming a tetrahydropyrimidine ring fixed cis-Configuration. We designed and synthesized 26 neonicotinoid compoundsⅠa～Ⅰd,Ⅱe-Ⅱz which had not been reported. All these target compounds were confirmed by IR, 1H NMR, MS, and elementary analysis. Their physic-chemical properties, spectrum properties, reaction conditions and synthetic methods were discussed as well. The structure of target compoundsⅠa～Ⅰd,Ⅱe～Ⅱz were as follows: The preliminary biological activities tests of target compounds (Ⅰ), (Ⅱ) were finished in Zhejiang Chemical Industry Research Institute, Branch of National Pesticide R&D South Center. And we also commissioned National Center for Drug Screening to test the acetylcholine activity in some high pesticide activities. The LC50 tests of some compounds were finished by Shanghai Academy of Agricultural Sciences. The German Bayer CropScience Company helped us to test the insecticidal activity to variety pest in different conditions and the pest resistant strains. The results showed that:most of the compounds had 100% death rate in 100 mg/L to the rice brown planthopper(Nilaparvata legen) and alfalfa aphid(Aphis medicagini) obviously kill, some of which still had shown 100% death rate in the 20 mg/L to the rice brown planthopper(Nilaparvata legen) and alfalfa aphid(Aphis medicagini). It had shown its excellent potential for further development and research. To further explore the structure and activity relationships, the compounds Id,Ⅱh, Ilk andⅡn were obtained and tested by single crystal X-ray single crystal diffraction. On the base of preliminary analysis of compounds Id,Ⅱh, Ilk andⅡn crystal structure characteristics, the compounds were docking simulation by AutoDock 4.0 for the initial explanation of its mechanism.