RESUMO
BACKGROUND: To discover more efficient antimicrobial agents in agriculture, a series of new quinazoline derivatives bearing both sulfonate ester and piperidine-4-carboxamide moieties were synthesized and assessed for their antimicrobial effects. RESULTS: All of the target compounds were fully characterized by proton (1 H) nuclear magnetic resonance (NMR), carbon-13 (13 C) NMR, and high-resolution mass spectroscopy (HRMS), and compound III-6 containing a 3-bromophenyl substituent was clearly confirmed via single-crystal X-ray diffraction analysis. The bioassay results indicated that some compounds displayed noticeable inhibitory effects in vitro against Xanthomonas oryzae pv. oryzicola (Xoc). Further measurements of median effective concentration (EC50 ) values showed that compound III-17 bearing a 4-methoxyphenyl group had the best anti-Xoc efficacy (EC50 = 12.4 µg mL-1 ), far better than the commercialized bismerthiazol (77.5 µg mL-1 ). Moreover, this compound also demonstrated good protection and curative activities in vivo against rice bacterial leaf streak caused by Xoc. CONCLUSION: Compound III-17 had a good potential for further development as a new bactericide for controlling Xoc. © 2023 Society of Chemical Industry.
Assuntos
Anti-Infecciosos , Oryza , Xanthomonas , Ésteres/farmacologia , Quinazolinas/farmacologia , Testes de Sensibilidade Microbiana , Anti-Infecciosos/farmacologia , Antibacterianos , Doenças das Plantas/microbiologiaRESUMO
BACKGROUND: To find more effective agricultural antibiotics, a class of new 2-aminothiazole derivatives containing the 4-aminoquinazoline moiety were synthesized and evaluated for their antimicrobial properties against phytopathogenic bacteria and fungi of agricultural importance. RESULTS: All the target compounds were fully characterized by 1 H NMR, 13 C NMR, and high-resolution mass spectrometry. The bioassay results showed that compound F29 with a 2-pyridinyl substituent exhibited an outstanding antibacterial effect against Xanthomonas oryzae pv. oryzicola (Xoc) in vitro, having an half-maximal effective concentration (EC50 ) value as low as 2.0 µg/mL (over 30-fold more effective than the commercialized agrobactericide bismerthiazol, with an EC50 value of 64.3 µg/mL). In addition, compound F8 with a 2-fluorophenyl group demonstrated a good inhibitory activity toward the bacterium Xanthomonas axonopodis pv. citri (Xac), around twofold more active than bismerthiazol in terms of their EC50 values (22.8 versus 71.5 µg/mL). Interestingly, this compound also demonstrated a notable fungicidal effect against Phytophthora parasitica var. nicotianae, with an EC50 value largely comparable with that of the commercialized fungicide carbendazim. Finally, mechanistic studies revealed that compound F29 exerted its antibacterial effects by increasing the permeability of bacterial membranes, reducing the release of extracellular polysaccharides, and triggering morphological changes of bacterial cells. CONCLUSION: Compound F29 has promising potential as a lead compound for developing more efficient bactericides to fight against Xoc. © 2023 Society of Chemical Industry.