Discovery of Novel Isoxazoline Compounds that Incorporate a para-Diamide Moiety as Potential Insecticidal Agents against Fall Armyworm (Spodoptera frugiperda)

• Published in: Journal of agricultural and food chemistry 2023-04, Vol.71 (14), p.5516-5524
• Main Authors: Jiang, Biaobiao, Li, Fangyi, Feng, Di, Wei, Wenchao, Luo, Yuqin, He, Siqi, Dong, Yawen, Hu, Deyu
• Format: Article
• Language: English
• Subjects: Agricultural and Environmental Chemistry; Animals; Diamide - chemistry; Insecta; Insecticides - chemistry; Isoxazoles - chemistry; Molecular Docking Simulation; Spodoptera
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/acs.jafc.3c00351

Spodoptera frugiperda is a major migratory agricultural pest, which seriously impedes agricultural production around the world. To discover potent compounds against S. frugiperda, a number of novel isoxazoline derivatives were designed and synthesized and created on account of the identified lead compound F32 (4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methyl-N-(3-propionamidophenyl)­benzamide). Based on the three-dimensional quantitative structure–activity relationship of those compounds, the compound G22 (N-(4-acetamidophenyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzamide) was developed. A bioassay showed that G22 is highly lethal to S. frugiperda (LC50 = 1.57 mg/L), a more effective control than insecticides fipronil (LC50 = 78.8 mg/L) and chlorantraniliprole (LC50 = 1.60 mg/L). Field trials were also implemented to identify candidate agents. Furthermore, from the insect γ-aminobutyric acid (GABA) enzyme-linked immunosorbent assay, it is obvious that G22 could up-regulate the expression of GABA of insects, which showed a similar result to fipronil. The analysis of molecular docking exhibited that the hydrophobic effect and hydrogen bonds play key roles in the combination between G22 with GABA receptors. This study provides a potent isoxazoline candidate compound for the S. frugiperda control.