Synthesis And Insecticidal Activities Of Analogues Of Chlorantraniliprole Containing A Difluoromethyl

The difluoromethyl group exhibits strong lipophilic and electron-withdrawing ability. The introduction of difluoromethyl group into organic molecules can modulate biological properties of the target compounds. In the first part of this dissertation, the difluoromethyl group was introduced into the anthranilic diamides derivatives, ten difluoromethyl-containing chlorantraniliprole analogs was synthesized and the insecticidal activities of all of the compounds’were tested. In the second part of this dissertation, the reaction condition of the high bioactive compound Wjjlll4containing difluoromethyl group was optimized. In the third part of this dissertation, an efficient, novel and mild oxidation of benzylic C-H bond was developed.1. The new fluorine-containing anthranilic diamides derivatives were synthesized by introduction of difluoromethyl group. The ten new compounds were confirmed by’ H NMR.12C NMR.19F NMR and HRMS-ESI, and their insecticidal activities were tested. The preliminary results indicated that all the target compounds exhibited obviously activities against armyworm. The YLXA02. YLXA10showed high insecticidal activities and the mortality against armyworm is about90%at lppm.2. The reaction conditions of the synthesis of high bioactive compound(Wjjlll4) was optimized via changing reaction route, reaction temperature, reaction solvent, ratio of starting materials and so on. The yield is increased obviously. Furthermore, results from the mortality against armyworm indicated that the LC50of the compound (Wjjlll4) is0.23ppm.3. The oxidation of benzylic C-H bond is one of the most useful and fundamental transformations. It is a powerful tool to generate high value chemicals from less expensive starting materials. A green and highly efficient protocol for the oxidation of benzylic methylenes to their corresponding ketones with a combination of Oxone and KBr in aqueous acetonitrile is developed. The H20labeling experiment demonstrated that the oxygen introduced into ketone originated from water. A plausible mechanism was also suggested.