Design, synthesis and insecticidal activity of novel m-diamides containing sulfide, sulfoxide and sulfone
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Graphical Abstract
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Abstract
With the emergence and widespread use of new insecticides in the market, the resistance of pests to insecticides has increased. To develop efficient, low toxicity, and environmentally friendly green ecological insecticides to address the threat of pest resistance, this work adopts the method of active substructures splicing and uses cyproflanilide as the lead compound to design and synthesize 18 novel meta-diamide compounds containing thioether, sulfoxide, and sulfone. All compounds were characterized by 1H NMR and HRMS and some representative compounds were selected for 13C NMR characterization to further confirm their structures. Most target compounds exhibited excellent insecticidal activity against brown Nilaparvata lugens, especially 12d at 100 mg/L showing 87.32% activity against brown N. lugens. At the same time, some compounds also showed good activity against Tetranychus cinnabarinus, among which 10f showed 100.00% activity against T. cinnabarinus at a concentration of 10 mg/L and 7.63% activity against T. cinnabarinus at 1 mg/L. Based on the bioassay activity, preliminary structure-activity relationships were also discussed, which will provide a theoretical basis for the further development of meta-diamide insecticides.
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