Synthesis, insecticidal activity, and in silico study of novel carboxamide compounds containing benzoxazole moiety

• Published in: Research on chemical intermediates Vol. 50; no. 4; pp. 1809 - 1825
• Main Authors: Shi, Jian-Jun, Li, Wei-Wei, Tan, Cheng-Xia, Hu, Dong-Song, Xu, Tian-Ming, Liu, Xing-Hai
• Format: Journal Article
• Language: English
• Published: Dordrecht Springer Netherlands 01.04.2024; Springer Nature; Springer Nature B.V
• Subjects: Aminophenol; Catalysis; Chemistry; Chemistry and Materials Science; Chemistry, Multidisciplinary; Inorganic Chemistry; Molecular docking; NMR; Nuclear magnetic resonance; Pests; Physical Chemistry; Physical Sciences; Science & Technology; Carboxamide; Docking; Synthesis; Insecticidal activity; Benzoxazole; DESIGN; MODE; META-DIAMIDE COMPOUNDS; DERIVATIVES
• ISSN: 0922-6168; 1568-5675
• DOI: 10.1007/s11164-024-05230-8

A series of novel carboxamide compounds containing benzoxazole motif was synthesized through multiple steps, including electrophilic substitution, cyclization, reduction and amide formation. These processes utilized ortho-aminophenol and heptafluoro-2-iodopropane as starting materials. The structures of these compounds ( 4a – 4r ) were characterized by 1 H NMR, 13 C NMR, and HRMS. Bioassay results revealed that most of these compounds exhibited significant insecticidal activity against Mythimna separata at 500 mg/L. Among them, compound 6-chloro- N -(4-methoxy-3-(6-(perfluoropropan-2-yl)benzo[ d ]oxazol-2-yl)phenyl)- N -methylnicotinamide ( 4r ) possessed the highest activity, even at 4 mg/L. Molecular docking predicted the binding modes of 4r . These novel carboxamide compounds containing benzoxazole motifs offer valuable insights for designing insecticidal compounds targeting GABA receptors, aiming to control lepidopteran pests effectively.