Studies On Synthesis And Properties Of Pyrazole Acrylonitrile Compounds With Biological Activities

Safe,efficient,economical and environmentally friendly is the development trend of pesticides.Acrylonitrile compounds have high efficiency,low toxicity,no cross-resistance to existing pesticides and environmental compatibility in various characteristics.Pyrazole compounds has became a hot field because of its structural changes,high biological activity,low toxicity,broad-spectrum.Pyrazolyl acrylonitrile compounds which had framework of both pyrazole and acrylonitrile have attracted more and more concern to the majority of researchers.In this paper,novel pyrazolyl acrylonitrile compounds were designed and synthesized by pro-drug theory,analogue synthesis,and sub-structure theory.The details was listed as follow.1.The current situation and the development trend of insecticides were reviewed in this thesis,the recent research progress of pyrazole compounds and pyrazolyl acrylonitrile compounds are also dscribed in detail.2.Cyenopyrafen as the lead compound,a series of 27 novel and unreported Cyenopyrafen derivatives I were designed and synthesized by using pro-drug theory,analogue synthesis,and sub-structure theory.Their structures were showed as follow.2-(4-(tert-butyl)phenyl)-2-cyano-1-(1,3,4-substituent-1H-pyrazol-5-yl)substituted with vinyl acetate3.Synthetic methods of acrylonitrile compounds were studied and the reaction conditions were optimized.Its structures of all target compounds were confirmed by using IR,1H NMR and LC-MS.4.Insecticidal,acaricidal,fungicidal,herbicidal activity of the acrylonitrile compounds were studied.The insecticidal activity bioassay results expressed that compounds I showed excellent acaricidal activity and basically A-level mortality against Tetranychus urticae at a concentration of 500 mg/L.Compounds I showed slightly results from A-level mortality to C-level mortality against Aphis fabae.Compounds I showed poor activity against Mythimna siparata.Fungicidal activity bioassay results showed that the compound I exhibited good control effect against Corn rust and not obvious inhibiting effect against other fungicidal at the measured concentrations.Herbicidal activity bioassay results expressed that pyrazolyl acrylonitrile compounds showed no herbicidal activities completely.5.The structure-activity relationship based on biological activity for the target compounds was discussed.The law which was summarized can provide some theoretical guidance for designing such compounds in the future.