Synthesis And Biological Activity Of Benzophenonehydrazone Derivatives Containing Semicarbazone Structure

Metaflumizone (BAS320I) is a new compound belonging to semicarbazone class ofbroad-spectrum pectrum pesticides within the suction,its name(IUAC):(E+Z)-2-[2-(4-cyanophenyl)-1-(3-trifluoromethylphenyl)ethylidene]-N-[4-(Trifluoromethoxy)phenyl]-hydrazine carbonyl oxamide.In this thesis,using Metaflumizone as a lead compound,wedesigned and synthesised 166 derivatives.All compound were confirmed by 1H NMRand MS,and the primary study of structure-activity relationship have done.1. we combined metaflumizone and benzophenone structural similarity, focusing on theabolition methylene structure of methylene diphenyl ketone, combined with previouslydeveloped benzophenone hydrazone, design with semicarbazone of benzophenonehydrazone structure of new compounds using split activing structural synthesis methodand similar synthesis method.2. A series of aryl isocyanate were synthesized using Aryl amine, Triphosgene. Thismethod is safer than carbonyl chloride and diphosgene,and mild reaction conditions,easy to operate experiments.3.A series of 4-halogenated-N-alkyl-N'-alkyl sulfonamide benzophenonehydrazonewere synthesized using 4-nitrobenzoyl chloride, halogenatebenzene, methanesulfonylchloride, hydrazine hydrate,et al, as starting materials, by Friedel-Crafts reaction, alkyl sulfonyl chloride, alkylationand addition-elimination reaction. 4. 4-halogenated-N-alkyl-N'-alkyl sulfonamide benzophenonehydrazone was treatedwith various phenylisocyanates to give novel benzophenonehydrazone derivativescontaining semicarbazone structure. The structures of the products were characterizedby 1H NMR and MS.5.The bioassay result showed that:Metaflumizone derivatives have great insecticidalactivity, especially for Lepidoptera.At the concentration of 100mg/L, ZJ3966, ZJ 3967,ZJ 3969-3971 and others exhibited more than 80% mortality of Spodoptera litura; At theconcentration of 100mg/L,ZJ4207-4221, ZJ4227 and others exhibited more than 80%mortality of Diamondback moth. So they have great potential commercial applications.