Novel 1,3,5-thiadiazine-2-thione derivatives containing a hydrazide moiety: Design, synthesis and bioactive evaluation against phytopathogenic fungi in vitro and in vivo

Abstract A series of novel 1,3,5-thiadiazine-2-thione derivatives bearing a hydrazide moiety were designed, synthesized and evaluated for their antifungal activities against Rhizoctonia solani (Rs), Fusarium graminearum (Fg), Botrytis cinerea (Bc) and Colletotrichum capsici (Cc). The in vitro antifungal bioassays indicated that most of title compounds displayed good selectivity and specificity aganist Rs relative to Fg, Bc and Cc. Strikingly, the title compound N '-(4-chlorophenyl)-2-(5-phenyl-6-thioxo-1,3,5-thiadiazinan-3-yl)acethydrazide ( 5b ) obviously inhibited the Rs growth in vitro with the EC 50 value of 0.24 μg/mL, which is approximately 2-folds more effective than the commercialized fungicide carbendazim (0.55 μg/mL). The in vivo anti-Rs effects of title compound 5b were further evaluated on rice leaves with control efficacies of 98.58% at 200 μg/mL and 61.27% at 100 μg/mL. The above researches provide a significant reference for the further structural optimization of 1,3,5-thiadiazine-2-thione derivatives bearing a hydrazide moiety as potential fungicides.