Novel boron‐containing anthranilic diamide derivatives: design, synthesis, and exploration of the action mode against lepidopteran insects
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2025
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| author | Weibin Xie Peizhuo Li Jinmin Peng Yue Chen Jieyin Liu Xiaochen Wang Zhiguang Yuchi Liangnian He Yuxin Li |
| author_facet | Weibin Xie Peizhuo Li Jinmin Peng Yue Chen Jieyin Liu Xiaochen Wang Zhiguang Yuchi Liangnian He Yuxin Li Weibin Xie Peizhuo Li Jinmin Peng Yue Chen Jieyin Liu Xiaochen Wang Zhiguang Yuchi Liangnian He Yuxin Li |
| collection | Wiley Open Access |
| contents | Novel boron‐containing anthranilic diamide derivatives: design, synthesis, and exploration of the action mode against lepidopteran insects Weibin Xie Peizhuo Li Jinmin Peng Yue Chen Jieyin Liu Xiaochen Wang Zhiguang Yuchi Liangnian He Yuxin Li Pest Management Science AbstractBACKGROUNDDiamide insecticides targeting insect ryanodine receptors (RyRs) have demonstrated exceptional efficacy against lepidopteran insects while exhibiting low toxicity to non‐target organisms. However, their widespread use over the past decade has led to the rapid development of pest resistance, diminishing their long‐term effectiveness. Boron, an essential micronutrient for plant growth, has attracted attention in drug design, owing to its unique chemical properties.RESULTSTo develop new insecticides with novel mechanisms for effective lepidopteran insect control, 19 boron‐containing anthranilic diamide derivatives were designed and synthesized based on the scaffold of chlorantraniliprole (CHL), using active fragment splicing and virtual screening strategies. The structures of the target compounds were confirmed using proton (1H) nuclear magnetic resonance (NMR), carbon‐13 (13C) NMR, fluorine‐19 (19F) NMR, and high‐resolution mass spectrometry (HRMS). Preliminary bioassays revealed that most compounds exhibited good‐to‐excellent insecticidal activity against Mythimna separata and Spodoptera frugiperda. Among them, compound 5b showed remarkable activity against M. separata (60% mortality at 0.1 mg/L), outperforming CHL (40%) at the same concentration. Calcium imaging technique, time‐lapse [Ca2+]ER measurements, and transcriptomic analyses indicated that RyRs may serve as primary targets of compound 5b. Molecular docking further predicted the mode of binding of 5b within the RyRs protein.CONCLUSIONThe boron‐containing anthranilic diamide derivatives are promising candidates for developing next‐generation insecticides, offering valuable insights into overcoming lepidopteran pest resistance. © 2025 Society of Chemical Industry. 10.1002/ps.8979 http://onlinelibrary.wiley.com/termsAndConditions#vor |
| doi_str_mv | 10.1002/ps.8979 |
| format | Artículo Open Access |
| id | wiley_oa_10_1002_ps_8979 |
| institution | Wiley Open Access |
| license_str_mv | http://onlinelibrary.wiley.com/termsAndConditions#vor |
| publishDate | 2025 |
| publisher | Wiley |
| record_format | wiley_oa |
| spellingShingle | Novel boron‐containing anthranilic diamide derivatives: design, synthesis, and exploration of the action mode against lepidopteran insects Weibin Xie Peizhuo Li Jinmin Peng Yue Chen Jieyin Liu Xiaochen Wang Zhiguang Yuchi Liangnian He Yuxin Li Pest Management Science Novel boron‐containing anthranilic diamide derivatives: design, synthesis, and exploration of the action mode against lepidopteran insects Weibin Xie Peizhuo Li Jinmin Peng Yue Chen Jieyin Liu Xiaochen Wang Zhiguang Yuchi Liangnian He Yuxin Li Pest Management Science AbstractBACKGROUNDDiamide insecticides targeting insect ryanodine receptors (RyRs) have demonstrated exceptional efficacy against lepidopteran insects while exhibiting low toxicity to non‐target organisms. However, their widespread use over the past decade has led to the rapid development of pest resistance, diminishing their long‐term effectiveness. Boron, an essential micronutrient for plant growth, has attracted attention in drug design, owing to its unique chemical properties.RESULTSTo develop new insecticides with novel mechanisms for effective lepidopteran insect control, 19 boron‐containing anthranilic diamide derivatives were designed and synthesized based on the scaffold of chlorantraniliprole (CHL), using active fragment splicing and virtual screening strategies. The structures of the target compounds were confirmed using proton (1H) nuclear magnetic resonance (NMR), carbon‐13 (13C) NMR, fluorine‐19 (19F) NMR, and high‐resolution mass spectrometry (HRMS). Preliminary bioassays revealed that most compounds exhibited good‐to‐excellent insecticidal activity against Mythimna separata and Spodoptera frugiperda. Among them, compound 5b showed remarkable activity against M. separata (60% mortality at 0.1 mg/L), outperforming CHL (40%) at the same concentration. Calcium imaging technique, time‐lapse [Ca2+]ER measurements, and transcriptomic analyses indicated that RyRs may serve as primary targets of compound 5b. Molecular docking further predicted the mode of binding of 5b within the RyRs protein.CONCLUSIONThe boron‐containing anthranilic diamide derivatives are promising candidates for developing next‐generation insecticides, offering valuable insights into overcoming lepidopteran pest resistance. © 2025 Society of Chemical Industry. 10.1002/ps.8979 http://onlinelibrary.wiley.com/termsAndConditions#vor |
| title | Novel boron‐containing anthranilic diamide derivatives: design, synthesis, and exploration of the action mode against lepidopteran insects |
| topic | Pest Management Science |
| url | https://scijournals.onlinelibrary.wiley.com/doi/10.1002/ps.8979 |