Design, synthesis, X-ray crystal structure, and antimicrobial evaluation of novel quinazolinone derivatives containing the 1,2,4-triazole Schiff base moiety and an isopropanol linker

Abstract

A series of novel quinazolinone derivatives (E1-E31) containing the 1,2,4-triazole Schiff base moiety and an isopropanol linker were designed, synthesized and assessed as antimicrobial agents in agriculture. All the target compounds were fully characterized by ¹ H NMR, ¹³ C NMR, and high-resolution mass spectrometry (HRMS). Among them, the structure of compound E12 was further confirmed via single crystal X-ray diffraction method. The experimental results indicated that many compounds displayed good in vitro antibacterial efficacies against the tested phytopathogenic bacteria including Xanthomonas oryzae pv. oryzae (Xoo), Xanthomonas axonopodis pv. citri (Xac), and Ralstonia solanacearum (Rs). For example, compounds E3, E4, E10, E13, and E22 had EC₅₀ (half-maximal effective concentration) values of 55.4, 39.5, 49.5, 53.5, and 57.4 µg/mL against Xoo, respectively, superior to the commercialized bactericide Bismerthiazol (94.5 µg/mL). In addition, the antibacterial efficacies of compounds E10 and E13 against Xac were about two times more effective than control Bismerthiazol, in terms of their EC₅₀ values. Last, the antifungal assays showed that compounds E22 and E30 had the inhibition rates of 52.7% and 54.6% at 50 µg/mL against Gibberella zeae, respectively, higher than the commercialized fungicide Hymexazol (48.4%).

Keywords: 1,2,4-Triazole Schiff base; Antimicrobial effects; Isopropanol; Quinazolinone.