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.
The fastest and most effective way to control pests is to use pesticides. However, with the accumulation of pesticide resistance and the difficulties of rapidly producing new pesticides, it is of great significance to create new pesticides through new synthetic methods. In this study, we report a computer-aided drug design (CADD)-assisted method to obtain two lead sulfonamides by homology modeling and virtual screening. On this basis, the lead compounds were synthesized from p-chlorocresol by four steps of esterification, sulfonation, sulfonamidation, and amidation. Further, 71 derivatives were synthesized by optimizing the lead compounds, and their insecticidal activities against Mythimna separata were evaluated by the leaf-dipping method. Notably, seven sulfonamides (5a, 5g, 5h, 5m, 6b, 6g, and 6m) with excellent insecticidal activity were obtained, and the possible binding modes between receptors and active groups in sulfonamides were verified by structure–activity relationship and docking simulation, which provided theoretical support for the subsequent development of these novel candidate insecticides.
Oomycetes are one type of the most highly destructive of the diseases that cause damage to some important crop plants, such as potato late blight, cucumber downy mildew, and grape downy mildew. As main approach of the ongoing search for new botanical fungicide from plant, the secondary metabolites of D. aspersa were investigated. Through efficient bioassay-guided isolation, two new (1 and 2) and 12 known compounds (3 - 14) were isolated, and their structures were determined via extensive NMR, HR-ESI-MS, and IR. They were isolated from this genus for the first time except for compounds 11 and 12. The biological properties of 1 - 14 were evaluated against Pseudoperonospora cubensis and Phytophthora infestans. Compounds 1 - 8 showed potent antifungal activity in vitro. Additionally, compound 3 has preferable control effect on cucumber downy mildew, showing dual effect of protection and treatment in vivo.
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