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

Abstract

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.

Graphical abstract

Keywords:

• Naphthalenesulfonamide
• insecticidal activity
• structure–activity relationship
• molecular docking

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

This work was financially supported by grants from the National Natural Science Foundation of China [21977083] and from the Open Fund of State Key Laboratory of Bioorganic and Natural Products Chemistry [SKLBNPC19248], Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences.