Synthesis And Biological Acitivity Of Acrylonitrile And Oxadiazole Derivatives

The discovery of new active structure requires a lot of manpower and funds.The cost of research and development of new drugs based on existing active groups can be greatly reduced.Acrylonitrile Group is a kind of excellent pesticide active structure,and it has been widely used in the field of pesticides,by splicing different groups with the activity of sterilization,insecticide and weeding through the theory of active splicing and electronic arrangement.In this paper,the intermediate ethyl(Z)-3-(4-(tertbutyl)phenyl)-3-cyano-2-hydroxyacrylate containing acrylonitrile structure was synthesized from p-tert-butylphenyl acetonitrile as the raw material,and this intermediate was used for structural splice with a variety of reactive groups.Finally,10 acrylonitrile compounds were obtained.The structure of these compounds were characterized by spectroscopic methods.The structure-activity relationship between the structure and activity of these compounds was explored through biological activity tests.Two compounds E8 and E10 with high insecticidal activity were obtained.Heterocyclic compounds has always been the core of the research of new pesticides.Among them,oxadiazole compounds are favored by pesticide developers due to their antibacterial,insecticidal and herbicidal effects.1,3,4-oxadiazole is the most studied oxadiazole compounds in China,while the latest Tioxazafen developed by Monsanto contains 1,2,4-oxadiazole ring.Tioxazafen has excellent nematicidal activity,different position of the N element on the ring may greatly affect the biological activity of the compound.In this paper,using 2-hydroxy-benzonitril as the starting material,15 compounds containing 1,2,4-oxadiazole ring were synthesized by etherification,cyano addition hydroxyacylation and anhydrocyclization,13 of which have a completely new structure.The structure of these compounds were characterized by spectroscopic methods.The structure-activity relationship between the structure and activity of these compounds was explored through biological activity tests.Four compounds 7a,7k,7m,and 7o with high insecticidal activity and three compounds 7d,7i and 7n with high antibacterial activity were obtained.In this paper,7d,7i and 7n were further formulated into flowable agent,and the bactericidal effect was verified by field efficacy experiments.