A series of new sulfone compounds containing the 1,3,4-oxadiazole moiety were designed and synthesized. Their structures were identified by (1)H and (13)C nuclear magnetic resonance and elemental analyses. Antibacterial bioassays indicated that most compounds exhibited promising in vitro antibacterial bioactivities against tobacco bacterial wilt at 200 μg/mL. The relationship between structure and antibacterial activity was also discussed. Among the title compounds, 5'c, 5'h, 5'i, and 5'j could inhibit mycelia growth of Ralstonia solanacearum in vitro by approximately 50% (EC(50)) at 39.8, 60.3, 47.9, and 32.1 μg/mL, respectively. Among them, compound 5'j was identified as the most promising candidate due to its stronger effect than that of Kocide 3000 [Cu(OH)(2)] within the same concentration range. Field trials demonstrated that the control effect of compound 5'j against tobacco bacterial wilt was better than that of the commercial bactericide Saisentong. For the first time, the present work demonstrated that sulfone derivatives containing 1,3,4-oxadiazole can be used to develop potential bactericides for plants.

This study aimed to synthesize some new sulfone derivatives containing a 1,3,4-oxadiazole moiety and investigate their in vitro antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas axonopodis pv. citri (Xac), the pathogens of rice bacterial leaf blight and citrus canker, respectively, by performing turbidimeter tests. Antibacterial bioassay results showed that compound 6d revealed excellent bioactivities against Xoo and Xac, with the 50% effective concentration (EC50) values of 0.17 and 1.98 μg/mL, respectively, compared with thiodiazole copper (121.82 and 77.04 μg/mL, respectively) and bismerthiazol (92.61 and 58.21 μg/mL, respectively). Meanwhile, greenhouse-condition trials indicated that, compared with thiodiazole copper and bismerthiazol, compound 6d more effectively reduced rice bacterial leaf blight.

2-Cyanoacrylate is an important kind of herbicide targeted in photosystem II. Starting from cyano ethyl acetate, the chiral title compounds were synthesized under microwave irradiation, which has the advantages of shorter reaction time, higher yield, and simpler procedure. A half-leaf method was used to determine the inhibition and curative efficacies of the eight chiral products against tobacco mosaic virus in vivo. It was found that chiral compound IIc-R possesses moderate inhibition and curative effect in vivo with rates of 89.1 and 43.1%, respectively. In the MTT test, these new chiral compounds were found to possess weak antiproliferation activities to PC3 and A431 cells.

Catalytic transfer hydrogenation (CTH) reactions are efficient transformation routes to upgrade biobased chemicals. Herein, we report a facile and template-free route to synthesize a series of heterogeneous nitrogen-containing alkyltriphosphonate− metal hybrids with enhancive Lewis acid and base sites, and their catalytic activity in converting biomass-derived carbonyl compounds to corresponding alcohols in 2-propanol. Particularly, a quantitative yield of furfuryl alcohol (FFA) was obtained from furfural (FUR) over organotriphosphate−zirconium hybrid (ZrPN) under mild conditions. The presence of Lewis basic sites adjacent to acid sites with an appropriate base/acid site ratio (1:0.7) in ZrPN significantly improved the yield of FFA. Mechanistic studies for the transformation of FUR to FFA with ZrPN in 2-propanol-d 8 evidently indicate CTH reaction proceeding via a direct intermolecular hydrogen transfer route. It was also found that ZrPN could catalyze isomerization of C 3 −C 6 aldoses to ketoses involving intramolecular hydrogen transfer in water.