Study On Synthesis And Insecticidal Activity Of Novel Oxadiazine Compounds

In the 21^th century, pesticide must have the characteristics of high effect, safety, low cost and environmentally-friend. Oxadiazine insecticide indoxcarb as a new type of sodium channel blocker combined a favorable environmental profile with high activity, excellent selectivity, low residue, safe, no cross-resistance. The study on synthesis and bioactivity of oxadiazines has been a hot point in agrochemical research.The latest research development of insecticides and oxadizine insecticides were reviewed in this thesis, the involvement of discovery, varieties and mechanism of the oxadiazine insecticides were introduced in detail. Introducing the optimized bioactive groups, such as carbamate, benzoxazinone and benzoxazolone, to oxadiazin ring of the lead compound indoxacarb, 41 novle compounds have been synthesized by anologue synthesis designing principles such as pro-drug、sub-structure linkage and bioisosterism. According to their structures, these compounds can be divided into four series as followings:（1） methyl 7-chloro-2-（methyl（substitutedphenoxycarbonyl）carbam-oyl）-2,3,4a,5-tetrahydroindeno[1,2-e][1,3,4]oxadiazine-4a-carboxylateâ… :（2） 4a-methyl 2-substitutedphenyl 7-chloro-4a,5-dihydroindeno [１,2-e] [1,3,4] oxadiazine-2,4a（3H）-dicarboxylateâ…¡:（3） methyl 7-chloro-2-（7-fluoro-2,4-disubstituted-3-oxo-3,4-dihydro -2H-benzo[b][1,4]oxazin-6-ylcarbamoyl）-2,3,4a,5-tetrahydroindeno[1,2-e ][1,3,4]oxadiazine-4a-carboxylateâ…¢: （4） methyl 7-chloro-2-（substituted aromatic phenyl carbamoyl）-2,3,4a,5-tetrahydroindeno[1,2-e][1,3,4]oxadiazine-4a-carboxylateâ…£:Synthesis methods for each intermediates and target compounds were studied, and the structures of the prepared compounds were confirmed by ¹H NMR, LC/MS and IR.All of target compounds have been tested. Compoundsâ…¢andâ…£exhibited different extent of insecticidal efficacy, for example,â…¢a、Ⅲd、Ⅲe、Ⅳg andâ…£h exhibited A insecticidal activity（ 100% mortality rate） against Mythimna separate. To our surprise, some of target comounds show promising fungicidal activity, such as compoundsâ…¡i andâ…£f exhibit A fungicidal activity against Erysiphe graminis; compoundsâ…£g andâ…£h also have B fungicidal activity against Erysiphe graminis.