Synthetic Research Of N-acyl Cyclic Urea And Ionic Compounds With Potential Agrochemical Activity

The using of agrochemicals plays a key role in solving the world food problem. Acyl urea agrochemicals (chlorfluazuron, flufenoxuron, novaluron and so on) once became hotspot in the area of agrochemical research, because of high selectivity to non-target living creature, high surroundings safety, low concentration and quick degradation that traditional agrochemicals can't compare to. Heterocyclic compounds present diversity in structure changes. What's more, heterocyclic compounds are easy degradation in nature and friendly to environment. Now, heterocyclic compounds' patents have taken up nearly90%in the new application of agrochemical patents. N-heterocyclic compounds with high efficiency, low toxicity and environment friendly characteristics have obtained more attention from agrochemical researchers. Considering that acyl urea derivatives and N-heterocyclic compounds have high agrochemical activities and ionic compounds have exclusive designability, novel N-acyl cyclic urea derivatives having several agrochemical activity centers and dual functional acyl cyclic urea nitrogenium ionic compounds were designed and synthesized so as to seek high agrochemical activities' compounds and pharmacophores. Agrochemical activities of ionic compounds were tested.This thesis mainly includes the following three sections.The first section was about synthesis and characterization of novel N-acyl cyclic urea derivatives. In the presence of triethylamine(Et3N), twelve novel N-acyl cyclic urea derivatives were prepared in the yields of35-95%by the reactions of1-((6-chloropyridin-3-yl)methyl)imidazolidin-2-one with various acyl chlorides(aliphatic substituted acyl chlorides, halogenated acyl chlorides, aromatic substituted acyl chlorides and N-heterocyclic substituted acyl chlorides). The synthesized new compounds were characterized by IR,1H NMR spectroscopy,13C NMR spectroscopy, HRMS and elemental analysis. At the same time the optimizing conditions of N-acylation were investigated.The second section was about synthesis and characterization of N-acy1cyclic urea derivatives containing a-tertiary amine. Eleven N-acyl cyclic urea derivatives containing a-tertiary amine were synthesized by the nucleophilic substitution reaction of1-(2-haloacetyl)-3-((6-chloropyridin-3-yl)methyl)imidazolidin-2-one with various secondary amines(azole, hetercyclic secondary amines, aliphatic substituted secondary amines and aromatic substituted secondary amines) in the yields of49-86%. The synthesized compounds were characterized by IR,1H NMR spectroscopy,13C NMR spectroscopy, HRMS and elemental analysis.The third section was about synthesis and characterization of ionic agrochemicals.1-(2-haloacetyl)-3-((6-chloropyridin-3-yl)methyl)imidazolidin-2-one react with N-methyl(butyl) imidazole, N-methyl(butyl) benzimidazole, pyridine,2-methylpyridine, triphenylphosphine and benzothiazole respectively to give eight acyl cyclic urea nitrogenium ionic compounds in high yields. Some ionic compounds' agrochemical activities have been tested, and it shows that3-(2-(3-((6-chloropyridin-3-yl)methyl)-2-oxoimidazolidin-1-yl)-2-oxoethyl)benzo[d]t hiazol-3-ium bromide(7h) has the highest activity in anti-tetranychus cinnabarinus. Salicylic acid,2,6-dihydroxybenzoic acid and pyrazole acid have agrochemical activities and can be used as the intermediates of agrochemicals. Eight dual functional acyl cyclic urea nitrogenium ionic compounds with salicylate,2,6-dihydroxybenzoate and pyrazolate were prepared by ion exchange reaction. The agrochemical activities of dual functional acyl cyclic urea nitrogenium ionic compounds are testing. The synthesized compounds were characterized by1H NMR spectroscopy,13C NMR spectroscopy, mass spectroscopy and IR.