Design, Synthesis And Biological Activity Study Of Ferrocenyl Dimethomorph And N-Amino-Maleic Imide Derivatives

Recent years, Carboxylic acid amide (CAA) chemicals are widely used in agriculture as a kind of novel systemic fungicide for their satisfied activity against plant disease caused by oomycete pathogens. At the same time, ferrocene with its unique structure, properties and pharmacological activities have attracted more and more attention to drug researchers. In order to get CAA fungicide of higher biological activity, ferrocenyl were introduced into the skeleton of Dimethomorph instead of phenyl. We synthesized a series of CAA compounds I containing ferrocenyl.Scientists extracted several natural compounds from Lindera species of Lauraceae such as Linderone and Methyllinderone, and studies have shown that they have certain chitin synthase inhibitory activity, but these natural structure can not meet th requirements of drugability. We introduced the substructures of maleic imide and acyl hydrazone into the natural compounds skeleton by substructure linking method and synthesized a series compounds II to get fungicides and insecticides beneficial to environment and human safety.The target compounds were characterized by 1H NMR、19F NMR、13C NMR and HRMS, and their biological activity were tested by mycelial growth rate method with 14 kinds of plant pathogens. The test results show that All of the series Ⅰ compounds have certain inhibitory activity on the measured strains; series Ⅱ compounds have better inhibitory activity, compounds Ⅱ-4 with 3,4-dichloro maleimide structure showed significantly higher activity than that of Ⅱ-1 with maleimide compounds, Ⅱ-3 compounds containing tetrachloro phthalic acid amine showed lower activity. At a concentration of 50ppm, the inhibitory activity of almost all Ⅱ-4 compounds were higher than the natural compounds Linderone and Methyllinderone against strains tested, especially for Rhizoctonia cerealis and Physalospora piricola. Insecticidal activity test aganist Mythimna separata and Culex pipiens pallens to Ⅱ series compounds showed Ⅱ-1 compounds have higher killing activity against Culex pipiens pallens...