Synthesis and insecticidal activities of 4-(propargyloxy) benzenesulfonamide derivatives.

A series of 4-(propargyloxy) benzenesulfonamide derivatives with different substituents on the benzene ring were synthesized and evaluated for their insecticidal activity. Some of the compounds showed good insecticidal activity against Mythimna separata, and the LC50 value of the most active compound B2.5 was 0.235 mg/ml. Ultrastructural changes in the midgut epithelial cells of Mythimna separata were observed using transmission electron microscopy, and severe structural damage was found in microvilli, mitochondria and rough endoplasmic reticulum. It indicates that the possible site of action of these benzenesulfonamides is the cytoplasmic membrane and endomembrane system of the midgut epithelial cells. The above provides a basis for the development of novel insecticidal active compounds with a novel mechanism of action.

Design, synthesis, and insecticidal activities of propargyloxy-naphthalene-sulfonamide derivatives.

In our previous studies, a kind of novel benzenesulfonamides was found to be a candidate insecticidal compounds. It was shown that propargyloxy and sulfonamide groups are pharmacodynamic groups. One hundred and twenty-six (126) naphthalenesulfonamides derivatives with propargyloxy functionality were designed and synthesized, and their insecticidal activities were determined. Some of them showed outstanding activity, with LC50 values as low as 0.202 mg ml-1, much lower than that of the positive control celangulin V (23.9 mg ml-1). In addition, the structure-activity relationships were discussed, and molecular docking was used to verify the binding mode of the compound and the target receptor.