Synthesis, Antibacterial Activity, and Mechanisms of Novel 6-Sulfonyl-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole Derivatives

A series of novel 6-sulfonyl-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole derivatives were designed and synthesized. CoMFA models were established to analyze the quantitative structure-activity relationships on the basis of the EC50 values of the compounds. The models were used to design and synthesize compounds 32 and 33 with higher activities. The EC50 values of compound 33 against Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas oryzae pv. oryzicola (Xoc) were 0.59 and 1.63 mg/L, respectively, which were higher than those of thiodiazole copper (90.43 and 97.93 mg/L) and bismerthiazol (68.37 and 75.59 mg/L). Moreover, protective activities of compound 33 against bacterial leaf streak (BLS) and bacterial leaf blight (BLB) were 49.65% and 49.42%, respectively, which were superior to those of thiodiazole copper (44.28% and 41.51%) and bismerthiazol (38.89% and 40.09%). Protective activity of compound 33 against BLS was closely related to the improvement of defense-related enzyme activities, chlorophyll content, and photosynthesis activation. This is consistent with the upregulated expression of defense responses and photosynthesis-related proteins.