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

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英文篇名：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 作者：Xiaobin ; Wang ; Xincan ; Fu ; Min ; Chen ; An ; Wang ; Jinghua ; Yan ; Yudong ; Mei ; Mengqi ; Wang ; Chunlong ; Yang 英文作者：Xiaobin Wang;Xincan Fu;Min Chen;An Wang;Jinghua Yan;Yudong Mei;Mengqi Wang;Chunlong Yang;Jiangsu Key Laboratory of Pesticide Science,Nanjing Agricultural University;Department of Chemistry,College of Sciences,Nanjing Agricultural University; 英文关键词：1,3,5-Thiadiazine-2-thione;;Hydrazide;;Crop protection;;Antifungal activity;;Rhizoctonia solani 中文刊名：FXKB 英文刊名：中国化学快报(英文版) 机构：Jiangsu Key Laboratory of Pesticide Science,Nanjing Agricultural University;Department of Chemistry,College of Sciences,Nanjing Agricultural University; 出版日期：2019-07-15 出版单位：Chinese Chemical Letters 年：2019 期：v.30 基金：the grants from the National Natural Science Foundation of China (No. 31772209);; the Fundamental Research Funds for the Central Universities of China (No. KYTZ201604) 语种：英文; 页：FXKB201907015 页数：4 CN：07 ISSN：11-2710/O6 分类号：77-80

摘要

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(5 b)obviously inhibited the Rs growth in vitro with the EC_(50) value of0.24μg/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 5 b 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.
        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(5 b)obviously inhibited the Rs growth in vitro with the EC_(50) value of0.24μg/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 5 b 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.

引文

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