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In this study, 18 novel thiochroman-4-one derivatives incorporating oxime ether and 1,3,4-oxadiazole thioether moieties were synthesized and their structures analyzed by  1 H NMR,  13 C NMR, and HRMS. Their  in vitro  antibacterial activities against  Xanthomonas oryzae  pv . oryzae  ( Xoo ) and  Xanthomonas axonopodis  pv . citri  ( Xac ) as well as antifungal activities against  Botrytis cinerea  ( B. cinerea ),  Verticillium dahliae  ( V. dahliae ), and  Fusarium oxysporum  ( F. oxysporum ) were determined. Bioassay results showed that compound 6-chloro-2-(5-(methylthio)-1,3,4-oxadiazol-2-yl)thiochroman-4-one  O -methyl oxime ( 7a ) was found to be the most active against  Xoo  and  Xac , with the median effective concentration values (EC 50 ) of 17 and 28 μg/mL, respectively, which were even better than those of Bismerthiazol and Thiodiazole copper. Meanwhile, compound 2-(5-(ethylthio)-1,3,4-oxadiazol-2-yl)-6-methylthiochroman-4-one  O -methyl oxime ( 7j ) showed better  in vitro  antifungal activity against  B. cinerea , with the inhibition rate of 79%, than that of Carbendazim. As far as we know, this paper is the first report on the synthesis and antibacterial and antifungal activities of this series of novel thiochroman-4-one derivatives incorporating oxime ether and 1,3,4-oxadiazole thioether moieties.

phosphorus, sulfur, and silicon and the related elements

Synthesis and antibacterial and antifungal activities of novel thiochroman-4-one derivatives incorporating oxime ether and 1,3,4-oxadiazole thioether moieties