State Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, China.
J Agric Food Chem. 2024 Oct 23;72(42):23118-23130. doi: 10.1021/acs.jafc.4c04369. Epub 2024 Oct 14.
Mesoionic structures have become important advancements in recent agrochemical design. However, their potential beyond serving as excellent insecticides remains unexplored with limited reports available. Herein, a series of imidazo[1,2-]pyridine mesoionics were developed by structurally incorporating sulfonyl piperazine moieties into imidazo[1,2-]pyridines. Many of the obtained derivatives demonstrated bioactivity against tomato spotted wilt virus (TSWV) in bioassays. In particular, compound , identified via three-dimensional quantitative structure activity relation models, displayed encouraging protective performance (half-maximal effect concentration = 252 μg/mL) compared to the positive controls ningnanmycin (332 μg/mL) and vanisulfane (523 μg/mL). Through defense enzyme assays, real-time quantitative polymerase chain reaction, and proteomics analysis, was identified as a plant immunomodulator that promotes defense enzyme activity and the mediates oxidative phosphorylation pathway, enabling plants to resist TSWV. We expect this study to help expand the possibilities of mesoionic compounds.
中杂环结构在最近的农用化学品设计中取得了重要进展。然而，除了作为优秀的杀虫剂之外，它们的潜力尚未得到探索，因为可用的报告有限。在此，通过将磺酰基哌嗪部分结构并入咪唑并[1,2-a]吡啶中，开发了一系列咪唑并[1,2-a]吡啶中杂环。获得的许多衍生物在生物测定中对番茄斑点萎蔫病毒（TSWV）表现出生物活性。特别是，通过三维定量构效关系模型鉴定的化合物 ，与阳性对照宁南霉素（332μg/mL）和 vanisulfane（523μg/mL）相比，显示出令人鼓舞的保护性能（半数最大效应浓度=252μg/mL）。通过防御酶测定、实时定量聚合酶链反应和蛋白质组学分析， 被鉴定为一种植物免疫调节剂，可促进防御酶活性并介导氧化磷酸化途径，使植物能够抵抗 TSWV。我们希望这项研究有助于扩大中杂环化合物的可能性。
