Synthesis And Biological Activity Of Novel Heterocyclic Multithioether

Heterocyclic compounds, especially sulfide-containing heterocyclic compounds, possess the wide range of biological and pharmacological activity, such as anticancer, anti-tumor, anti-oxidation, anti-virus, anti-phlegm disease, antibacterial, etc., and can be widely applied in pharmaceutical, pesticides and industry. Sulfide-containing heterocyclic compounds have become the major tendency in the development of chemical pesticides owing to their flexible architectures and efficient activities.In this work, a series of sulfide-containing heterocyclic compounds were synthesized and biologically activity screening test were carried out, the obtained results are shown as follows.(1) Fifteen novel heterocyclic multithioether were synthesized via hydrazinolysis, salt formation and cyclization with ethyl benzoate and methyl hydrazine as the raw materials. The structures of those compounds were characterized through MS and1H NMR.(2) The synthesis conditions of oxadiazole, thiadiazole and triazole were optimized, and the optimum conditions were obtained by using single factor optimization method. The synthesis conditions were summarized as follows:For benzoyl hydrazine:molar ratio of raw materials benzoylhydrazine:hydrazine hydrate:1:5, reaction time9hours, reaction temperature:110℃. For1,2-diphenyl-5-mercapto-1,3,4-triazole:molar ratio of raw materials benzoylhydrazine: phenylisothiocyanate:1.1:1, reaction time4hours, reaction temperature:80℃;For thio-substituted benzoyl hydrazine salt:molar ratio of benzoylhydrazine and carbon disulfide:1:3, reaction time:14hours, reaction temperature:25℃, potassium hydroxide as catalyst. For thiadiazole compound:molar ratio of2-p-phenyl-5-mercapto-1,3,4-thiadiazole and dibromomethane:2.2:1, reaction time:24hours, reaction temperature:75℃. For oxadiazole compounds:molar radio of2-phenyl-5-mercapto-1,3,4-oxadiazole and dibromobutane:2.2:1, reaction temperature:75℃and reaction time:24hours.(3) The biological activity of the compounds were screened on21kinds of agricultural pathogenic fungi and12kinds of agricultural pathogenic bacteria, and the results suggested that all the compounds had a broad-spectrum of bactericidal activity.