Design, Synthesis and Bioactivity of Novel Low Bee-Toxicity Compounds Based on Flupyrimin

oleh: Xingxing Lu, Huan Xu, Xiaoming Zhang, Tengda Sun, Yufan Lin, Yongheng Zhang, Honghong Li, Xuesheng Li, Xinling Yang, Hongxia Duan, Yun Ling

Format: Article
Diterbitkan: MDPI AG 2022-09-01

Deskripsi

Neonicotinoids are important insecticides for controlling aphids in agriculture. Growing research suggested that neonicotinoid insecticides are a key factor causing the decline of global pollinator insects, such as bees. Flupyrimin (FLP) is a novel nicotinic insecticide with unique biological properties and no cross-resistance, and is safe for pollinators. Using FLP as the lead compound, a series of novel compounds were designed and synthesized by replacing the amide fragment with a sulfonamideone. Their structures were confirmed by <sup>1</sup>H NMR, <sup>13</sup>C NMR and HRMS spectra. Bioassay results showed that compound <b>2j</b> had good insecticidal activity against <i>Aphis glycines</i> with an LC<sub>50</sub> value of 20.93 mg/L. Meanwhile, compound <b>2j</b> showed significantly lower acute oral and contact toxicity to <i>Apis mellifera</i>. In addition, compound <b>2j</b> interacted well with the protein in insect acetylcholine binding protein (AChBP). The molecular docking on honeybee nicotinic acetylcholine receptor (nAChR) indicated that the sulfonamide group of compound <b>2j</b> did not form a hydrogen bond with Arg173 of the β subunit, which conforms to the reported low bee-toxicity conformation. In general, target compound <b>2j</b> can be regarded as a bee-friendly insecticide candidate.