Novel Meta-Diamide Derivatives Bearing Triazole: Design, Synthesis and Bioactivity

Abstract In searching for novel insecticide lead, 20 new meta-diamide compounds containing triazole were designed and synthesized regarding Cyproflanilide as lead compound. All the compounds were characterized by ¹H NMR, ¹³C NMR and HR MS. In preliminary bioassay, we found that one of the compounds: N-(cyclopropylmethyl)-N-(5-((2,6-dibromo-4-(perfluoropan-2-yl)phenyl)carbamoyl)-2-(1H-1,2,4-triazol-1-yl)phenyl)-6-(trifluoromethyl) Nicotinamide (16a) showed 93% mortality rate to P. xylostella at 1 mg/L and 100% mortality rate to M. separata at 2 mg/L. It is obviously superior to the known compounds Ⅰa and Ⅰb, and it is equivalent to Cyproflanilide. It is providing important clues for subsequent structure-activity relationship studies. From this, we explored the structure-activity relationship of these compounds. Through comprehensive analysis of their structural characteristics and insecticidal activity data, we found that specific halogen groups and substituents in the compounds have a significant impact on insecticidal activity. This provides important guidance for subsequent structural optimization and activity enhancement.