Green Design, Synthesis, and Molecular Docking Study of Novel Quinoxaline Derivatives with Insecticidal Potential against Aphis craccivora.

Abstract

An efficient and environmentally friendly method was established for designing novel 3-amino-1,4-dihydroquinoxaline-2-carbonitrile (1) via the reaction of bromomalononitrile and benzene-1,2-diamine under microwave irradiation in an excellent yield (93%). This targeted amino derivative was utilized for the construction of a series of Schiff bases (8–13). A new series of thiazolidinone derivatives (15–20) were synthesized in high yields (89–96%) via treatment of thioglycolic acid with Schiff bases (8–13) under microwave irradiation in high yields (89–96%). Moreover, new pyrimidine derivatives (26–30 and 35–38) were prepared by treatment of compound 1 with arylidenes (21–25) and/or alkylidenemalononitriles (31–34) using piperidine as a basic catalyst under microwave conditions. Based on elemental analyses and spectral data, the structures of the new assembled compounds were determined. The newly synthesized quinoxaline derivatives were screened and studied as an insecticidal agent against Aphis craccivora. The obtained results indicate that compound 16 is the most toxicological agent against nymphs of cowpea aphids (Aphis craccivora) compared to the other synthesized pyrimidine and thiazolidinone derivatives. The molecular docking study of the new quinoxaline derivatives registered that compound 16 had the highest binding score (−10.54 kcal/mol) and the thiazolidinone moiety formed hydrogen bonds with Trp143.