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Pyrido [1,2-a] Pyrimidinone Mesoionic Compounds Containing Vanillin Moiety: Design, Synthesis, Antibacterial Activity, and Mechanism.

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Xanthomonas oryzae pv. oryzicola (Xoo) is a plant pathogen responsible for rice bacterial blight disease that remains challenging for prevention and cure. To discover innovative and extremely potent antibacterial agents,… Click to show full abstract

Xanthomonas oryzae pv. oryzicola (Xoo) is a plant pathogen responsible for rice bacterial blight disease that remains challenging for prevention and cure. To discover innovative and extremely potent antibacterial agents, vanillin moiety was introduced to develop a series of novel mesoionic derivatives. Compound 15 demonstrated excellent in vitro antibacterial activity against Xoo, with a 50% effective concentration value (EC50) of 27.5 μg/mL, which was superior to that of the positive control agent thiodiazole copper (97.1 μg/mL) and comparable to that of compound "A11" (17.4 μg/mL). The greenhouse pot experiment also revealed that compound 15 had 38.5% curative and 36.8% protective efficacy against rice bacterial leaf blight in vivo at 100 μg/mL, which was higher than those of thiodiazole copper (31.2 and 32.6%, respectively) and compound "A11" (29.6 and 33.2%, respectively). Compound 15 enhanced the activities of related defense enzymes, increased chlorophyll content, and promoted the resistance of rice to bacterial infection by modulating the photosynthetic pathway. This study provides a basis for the subsequent structural modification and mechanism research of mesoionic derivatives.

Keywords: rice bacterial; antibacterial activity; vanillin moiety; mechanism

Journal Title: Journal of agricultural and food chemistry
Year Published: 2022

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