2. Academic Validation
  3. Design, Synthesis, and Insecticidal Activities of Novel N-Alkoxyalkyl Meta-Diamides as Potential GABAR Antagonists

Design, Synthesis, and Insecticidal Activities of Novel N-Alkoxyalkyl Meta-Diamides as Potential GABAR Antagonists

  • J Agric Food Chem. 2025 Jul 16;73(28):17446-17457. doi: 10.1021/acs.jafc.5c03018.
Sha Zhou 1 2,  Hao Shen 2 3,  Hua-Long Wu 2,  Bao-Hua Zhang 2,  Tian-Hao Zhou 4,  Xiao-Mu Qiao 1,  Jing Yuan 1,  Ya-Qin Jiang 1,  Ming Liu 5,  An-Liang Chen 1,  Xin-Liang Shen 2,  Jie Chen 1
Affiliations

Affiliations

  • 1 Collaborative Innovation Center of Green Pesticide, National Joint Engineering Laboratory of Biopesticide Preparation, National Key Laboratory for Development and Utilization of Forest Food Resources, School of Forestry and Biotechnology, Zhejiang A&F University, Hangzhou, Zhejiang 311300, China.
  • 2 Zhejiang Udragon Bioscience Co. Ltd, Jiaxing, Zhejiang 314300, China.
  • 3 State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), College of Chemistry, Nankai University, Tianjin 300071, China.
  • 4 Ministry of Agriculture Key Laboratory of Molecular Biology of Crop Pathogens and Insects, Institute of Insect Sciences, Zhejiang University, Hangzhou 310058, China.
  • 5 School of Pharmacy, Binzhou Medical University, Yantai, Shandong 264003, China.
PMID: 40615356 DOI: 10.1021/acs.jafc.5c03018
Abstract

N-alkyl meta-diamides (Ia-If) and N-alkoxyalkyl meta-diamides (IIa-IIIe) were designed and synthesized by using the intermediate derivatization method. Their insecticidal activities were systematically evaluated against resistant Plutella xylostella. Interestingly, the insecticidal activity of compounds IIa-IIIe against resistant P. xylostella showed remarkable consistency with that against sensitive strains of P. xylostella, Spodoptera frugiperda, and Chilo suppressalis. Rapid bioassay results on sensitive P. xylostella revealed outstanding efficacy, particularly for compound IId, which demonstrated mortality rates of 60% and 100% at a concentration of 0.1 μg·mL-1 after 12 and 24 h of exposure, respectively, significantly outperforming broflanilide. To investigate the molecular mechanism of compound IId, comparative bioactivity assays using both wild-type (w1118) and mutant (RdlG335M) Drosophila were conducted, conclusively demonstrating that RdlG335 serves as a critical binding site for compound IId. These findings provide significant insights for the strategic design of meta-diamide compounds, offering a promising approach for managing resistant pest populations.

Keywords

GABAR; broflanilide; insecticidal activity; resistant P. xylostella; trioxyflanilide.

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