Targeted Synthesis of Anthranilic Diamides Insecticides Containing Trifluoroethoxyl Phenylpyrazole

• Published in: Chemical research in Chinese universities Vol. 37; no. 3; pp. 655 - 661
• Main Authors: Li, Huangong, Zhao, Yangyang, Sun, Pengwei, Gao, Li, Xiong, Lixia, Yang, Na, Zhou, Sha, Li, Yuxin, Li, Zhengming
• Format: Journal Article
• Language: English
• Published: Changchun Jilin University and The Editorial Department of Chemical Research in Chinese Universities 01.06.2021; Springer Nature B.V
• Subjects: Analytical Chemistry; Biological activity; Calcium compounds; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Hydrogen bonds; Imaging techniques; Inorganic Chemistry; Insecticides; Molecular docking; NMR; Nuclear magnetic resonance; Organic Chemistry; Physical Chemistry; Pyrazole; Synthesis; Mode of the action; Molecular docking; Trifluoroethoxylphenylpyrazole; Anthranilic diamide derivative; Insecticidal bioactivity
• ISSN: 1005-9040; 2210-3171
• DOI: 10.1007/s40242-020-0287-8

A series of novel anthranilic diamides analogues( 9 a– 9 t) containing trifluoroethoxyl pyrazole moiety was designed and synthesized and their insecticidal bioactivities against Mythimna separata (Walker, M. separata ) and Plutellaxylostella ( P. xylostella ) were evaluated. The structures of the title compounds were confirmed by 1 H NMR, 13 C NMR and HRMS. Preliminary insecticidal activities showed that some of the title compounds possessed good to excellent bioactivities towards M. separata and P. xylostella . Compounds 9 c and 9 t exhibited 100% mortality rate against M. separate at 0.2 mg/L. For the P. xylostella , the synthesized compounds( 9 c– 9 e, 9 i and 9 o) showed 70%, 80%, 75 %, 65% and 60% insecticidal activities at 1×10 −6 mg/L, respectively, higher than that of chlorantraniliprole(0). Based on excellent insecticidal activities, the mode of the action was tested by the calcium-imaging technique, the results of which demonstrated that the novel compounds shared the same target with chlorantraniliprole. The binding pose of the most active compound 9 t in RyRs of P. xylostella was predicted by molecular docking, which showed that compound 9 t interacted with the residues Glu140(A) and His147(A) via hydrogen bond.