Synthesis And Insecticidal Activities Of Anthranilic Diamides Derivatives

In recent years, research about new pesticides of anthranilic diamides derivatives is developed very quickly. The representative drug pesticide is chlorantraniliprole which is used around the world and favored by the agriculture industry and pesticide researchers.DuPont used the flubendiamide as a lead compound to synthesize a new class of pesticides called anthranilic diamides. Through the research between structural modification and structure-activity relationship from about2000candidate compounds. DuPont found the chlorantraniliprole. It showed high insecticidal activities at very low concentrations and had similar insecticidal mechanism with ryanodine and flubendiamide. Moreover, it had quick effects on lepidopteran pests while non-toxic or less toxic on non-target insects and livestock. Thereby, chlorantraniliprole had security selectivity. Target pests had continued parasites contraction, vomiting and other symptoms when the drug combined ryanodine receptor and then regulated calcium channel.Currently, many researchers use Chlorantraniliprole as a lead compound in order to design and synthesize pesticides with higher insecticidal activities and security selectivity according to the principle of me-too, molecular emission and similar synthesis. We also used Chlorantraniliprole as a lead compound to synthesize new compounds through structure modification and optimization. And we focused on the amide group, which was modified by new amide groups connecting alkyl, cyano. heterocyclic, alkoxy and so on. For example, the chiral amine, amine with two nitrogen atoms and amine with some substituent groups on the nitrogen atoms were selected. About23compounds were synthesized and the reaction route was optimized. In order to adapt to industrial production, we optimized the reaction conditions and post-processing. Interestingly, silica gel, diatomaceous earth and activated carbon were used through post-processing. Dichloromethane (DCM). tetrahydrofuran (THF), acetone, pyridine, and water mixed systems could be solvents. Although both dichloromethane (DCM) and tetrahydrofuran (THF) could be solvents in most cases, we only selected dichloromethane (DCM) for the purpose of post-processing as much as possible.Compounds were identified and analytical methods were set though analytical tools such as NMR, MS and HPLC. We also summarized the special group map features. The insecticidal activities were tested on Diamondback Moths and Oriental Armyworm to establish a structure-activity relationship. Then set up a library of compounds and the foundation for future drug design. These compounds had high insecticidal activities while lower activities than chlorantraniliprole. This result reflected the right design ideas and promoted the development of the match of drug molecules and receptors through computer...