Novel quinazolin-4(3H)-one derivatives containing a 1,3,4-oxadiazole thioether moiety as potential bactericides and fungicides: Design, synthesis, characterization and 3D-QSAR analysis

Publication date: Available online 5 August 2019Source: Journal of Saudi Chemical SocietyAuthor(s): Xiaobin Wang, Haoran Hu, Xu Zhao, Min Chen, Tingting Zhang, Chunwen Geng, Yudong Mei, Aimin Lu, Chunlong YangAbstractA series of quinazolin-4(3H)-one derivatives containing a 1,3,4-oxadiazole thioether moiety were designed, synthesized and evaluated for their biological activities against phytopathogenic microorganisms. Antimicrobial bioassays in vitro indicated that most of the target compounds exhibited more significant antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo) than the agricultural bactericide thiadiazole-copper. A comparative molecular similarity index analysis (CoMSIA) model with cross-validated q2 and non-cross-validated r2 values of 0.561 and 0.882 was generated to investigate the structure-activity relationships of title compounds against Xoo. Title compound 6w, which was rationally designed under the guidance of obtained CoMSIA model, exhibited the excellent anti-Xoo effect in vitro with an EC50 value of 29.10 μg/mL, which is approximately 3-folds more effective than thiadiazole-copper (113.93 μg/mL). In addition, compound 6i demonstrated the impressive antifungal effects against Rhizoctonia solani (Rs) and Fusarium graminearum (Fg) in vitro, with the corresponding EC50 values of 11.01 μg/mL and 36.00 μg/mL, which is obviously better than the agricultual fungicide hymexazol (76.74 μg/mL and 56.19 μg/mL, respectively). The above research...
Source: Journal of Saudi Chemical Society - Category: Chemistry Source Type: research