Novel Meta-Diamide Compounds Containing Sulfide Derivatives Were Designed and Synthesized as Potential Pesticides

菜蛾 黑豆蚜 亚砜 化学 硫化物 立体化学 铅化合物 质子核磁共振 组合化学 有机化学 生物 生物化学 幼虫 植物 有害生物分析 同翅目 蚜虫科 体外
作者
Jingwen Wu,Shuaihui Dang,Yan Zhang,Sha Zhou
出处
期刊:Molecules [MDPI AG]
卷期号:29 (6): 1337-1337
标识
DOI:10.3390/molecules29061337
摘要

The meta-diamide (m-diamide) insecticide, Broflanilide, was characterized by its high efficiency, low toxicity and lack of cross-resistance with traditional GABA receptors. In accordance with the principles of drug molecular design, easily derivable sulfur with diverse bioactivities was introduced while leading with the parent Broflanilide. Twelve novel m-diamide target compounds containing sulfide derivatives were synthesized through exploration guided by the literature. Their structures were confirmed by melting points, 1H NMR, 13C NMR and HRMS. Insecticidal activity assessments revealed that most target compounds A–D exhibited 100% lethality against Plutella xylostella (P. xylostella) and Aphis craccivora Koch (A. craccivora) at 500 mg·L−1. Notably, for P. xylostella, compounds C-2, C-3, C-4 and D-2 demonstrated 60.00–100.00% insecticidal activity even at a concentration as low as 0.625 mg·L−1. As determined by structure–activity relationship (SAR) analysis, compounds with R1 = CH3 and R2 = Br (B-1, C-2 and D-2) and sulfoxide compound C-3 contained 100.00% lethality against A. craccivora at 500 mg·L−1, surpassing the lethality when leading with the parent Broflanilide in terms of efficacy. Consequently, it can be inferred that the sulfoxide compound (C-3) requires further investigation as a potential active molecule for new insecticides. These explorations provide valuable references for future research on the synthesis and insecticidal activities of sulfide-containing m-diamide compounds.
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