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 EC 50 values of the compounds. The models were used to design and synthesize compounds 32 and 33 with higher activities. The EC 50 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.

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BACKGROUNDThe rice bacterial leaf blight (BLB) is one of the most serious bacterial diseases caused by Xanthomonas oryzae pv. oryzae (Xoo), which can cause yield loss of rice up to 50%. The three‐dimensional quantitative structure–activity relationship (3D‐QSAR) is an important auxiliary method to find potential high‐efficient pesticides active structures.RESULTSA series of novel 1,3,4‐oxadiazole compounds were designed and synthesized based on the 3D‐QSAR model, and their antibacterial activities in vitro against Xoo were evaluated. The results indicated that all the target compounds showed excellent in vitro antibacterial activities. For example, the compounds 6, 12, 13, 20, 21, and 23 exhibited excellent antibacterial activities against Xoo, with half‐maximal effective concentration (EC50) values of 0.24, 0.31, 0.36, 0.29, 0.19, and 0.31 mg/L, respectively, which were superior to the antibacterial agents thiodiazole copper (127.44 mg/L) and bismerthiazol (91.08 mg/L). Meanwhile, compound 21 showed good antibacterial activity in vivo against BLB, with curative and protective activities of 46.7% and 56.4%, respectively, which were superior to thiodiazole copper (28.5% and 32.5%) and bismerthiazol (37.6% and 38.4%). Compound 21 can significantly reduce the extracellular polysaccharides production of Xoo, increase the permeability of the cell membranes, and also can cause cell surface wrinkles, deformation and dryness.CONCLUSIONThe 3D‐QSAR model can be used to find sulfone compounds containing a 1,3,4‐oxadiazole moiety with higher antibacterial activity, and compound 21 can be used as a potential antibacterial agent in the future. © 2020 Society of Chemical Industry

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The applications of mesoionic compounds and their analogues as agents against plant viruses remain unexplored. This was the first evaluation of the antiviral activities of mesoionic compounds on this issue. Our study involved the design and synthesis of a series of novel imidazo­[1,2-a]­pyridine mesoionic compounds containing a sulfonamide moiety and the assessment of their antiviral activities against potato virus Y (PVY). Compound A33 was assessed on the basis of three-dimensional quantitative structure–activity relationship (3D-QSAR) model analysis and displayed good curative, protective, and inactivating activity effects against PVY at 500 mg/L, up to 51.0, 62.0, and 82.1%, respectively, which were higher than those of commercial ningnanmycin (NNM, at 47.2, 50.1, and 81.4%). Significantly, defensive enzyme activities and proteomics results showed that compound A33 could enhance the defense response by activating the activity of defense enzymes, inducing the glycolysis/gluconeogenesis pathway of tobacco to resist PVY infection. Therefore, our study indicates that compound A33 could be applied as a potential viral inhibitor.

Bacterial leaf blight (BLB) and bacterial leaf streak (BLS) are two serious bacterial diseases caused by Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas oryzae pv. oryzicola (Xoc), respectively. However, the control of these diseases by conventional pesticides remains challenging due to development of resistances. We aimed to address this pending problem and developed a series of novel pyrimidine sulfonamide derivatives. Structurally, title compounds bear a unique oxyacetal group, which has a proven immune-activating effect. Compound E35 designed based on the 3D-QSAR model was demonstrated as the optimal in vitro activity against Xoo and Xoc, with EC50 values of 26.7 and 30.8 mg/L, respectively, which were higher than the positive controls bismerthiazol (29.9 and 32.7 mg/L) and thiodiazole copper (30.5 and 36.4 mg/L). On the prevention level, the biological activity test showed compound E35 had superior protective activity (43.7%) on BLS to thiodiazole copper (32.1%). The defense enzymes and proteomics results suggested that compound E35 could be a versatile candidate as it improved plant’s resistance to disease.

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