Chemical Research in Chinese Universities ›› 2024, Vol. 40 ›› Issue (1): 96-108.doi: 10.1007/s40242-023-3218-7

• Articles • Previous Articles     Next Articles

Discovery of Novel Anthranilic Diamide Derivatives Bearing Sulfoximine Group as Potent Insecticide Candidates

ZHANG Hongyuan1,2, PENG Jinmin1,2, ZHONG Yuanhan1,2, CHEN Yue1,2, WANG Qing4, Haditullah HADIATULLAH4, XIE Weibin1,2, XIONG Lixia1,2, YUCHI Zhiguang4, LIU Jingbo3, LI Yuxin1,2   

  1. 1. State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, P. R. China;
    2. Nankai University & Cangzhou Bohai New Area Institute of Green Chemical Engineering, Cangzhou 062550, P. R., China;
    3. College of Horticulture and Landscape Architecture, Tianjin Agricultural University, Tianjin 300392, P. R. China;
    4. Tianjin Key Laboratory for Modern Drug Delivery and High-efficiency, Collaborative Innovation Center of Chemical Science and Engineering, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. China
  • Received:2023-09-18 Online:2024-02-01 Published:2024-01-24
  • Contact: LI Yuxin, LIU Jingbo, YUCHI Zhiguang;;
  • Supported by:
    This work was supported by Nankai University Cangzhou Bohai New Area Green Chemical Research Institute (NCC) Fund, the National Natural Science Foundation of China (Nos. 31972287, 32022073), the National Key Research and Development Program of China (No. 2022YFE0108400), and the Scientific Project of Tianjin Municipal Education Commission, China (No. 2022KJ026).

Abstract: The fall armyworm, Spodoptera frugiperda (S. frugiperda), represents the most resistant insect species and poses serious threat to grain yield. Chlorantraniliprole (CHL), which targets the ryanodine receptors (RyRs) in insects, has demonstrated the efficacy in controlling S. frugiperda. Nevertheless, this has led to emerging resistance in several countries. To counter this resistance, a viable approach involves the development of novel compounds that bind against RyRs via distinct binding sites or modes. In this study, a series of 22 novel anthranilic diamide derivatives was designed and synthesized, and their insecticidal activities were evaluated. Most of these derivatives showed moderate to good insecticidal activity against S. frugiperda and Mythimna separata. Time-lapse fluorescence measurements of endoplasmic reticulum luminal calcium revealed that most derivatives elicited cellular responses similar as CHL when assessed on HEK293 cells expressing S. frugiperda ryanodine receptors (SfRyRs). The mode of action of compound 13a was studied and verified on the isolated neurons by calcium imaging technique. Finally, molecular docking analysis was employed to predict the binding mechanism of compound 13a against SfRyRs. Overall, these novel diamide derivatives hold promise as a valuable resource for guiding the future design of insecticidal compounds targeting RyRs.

Key words: Anthranilic diamide derivative, Sulfoximine, Spodoptera frugiperda, Mode of action, Molecular docking