农药学学报2021，Vol.23Issue(2)：287-295,9.DOI:10.16801/j.issn.1008-7303.2021.0022
含1,3,4-噻(噁)二唑吩嗪-1-甲酰胺类衍生物的合成与杀菌活性
Design, synthesis and fungicidal activities of phenazine-1-carboxamida conjugates of 1,3,4-thia(oxa)diazole
摘要
Abstract
Phenazine-1-carboxylic acid (PCA), isolated from Pseudomonas, is a very important fungicidal agent. PCA and its derivatives revealed good biological activities in the field of medicine andagrichemicals. In this paper, two series of PCA derivatives containing 1,3,4-thiadiazole and 1,3,4-oxadiazole were designed and synthesized to explore novel fungicidal candidates. Their in vitro and in vivo fungicidal activities were evaluated. The title compounds I8 (X=S, R=2-OCH3) and I22 (X=O, R=2-OCH3) had EC50 vaues of 33.25 μg/mL and 46.52 μg/mL against Fusarium graminearum, respectively, which were about 3-4 times better than of PCA (EC50 = 128.54 μg/mL). In vivo results showed that compounds I8 and I22 gave better bioactivity (inhibitory rates of 58.69％ and 55.37％ at 500 μg/mL, respectively) against F. graminearum than that of PCA (25.14％). Preliminary structure-activity relationship study found that the introduction of electron-donating groups were favored to improving the activity of the derivatives, and the substitution at ortho-position of benzene ring would be favored to fungicidal activity. The substitution position of the same substituent on the benzene ring was in the order of o > p > m according to the bioactivity.These results can be used to guide the further structural modification of these compounds for novel fungicidal agent.关键词
吩嗪-1-甲酸/1,3,4-噻二唑/1,3,4-噁二唑/杀菌活性Key words
phenazine-1-carboxylic acid/1/3/4-thiadiazole/1/3/4-oxadiazole/fungicidal activity分类
化学化工引用本文复制引用
何敏,古景文,李司丞,向绪稳,姜珊,崔紫宁..含1,3,4-噻(噁)二唑吩嗪-1-甲酰胺类衍生物的合成与杀菌活性[J].农药学学报,2021,23(2):287-295,9.基金项目
the National Key Research and Development Program of China(2017YFD0200504) （2017YFD0200504）
the National Natural Science Foundation of China(32072450,31570122) （32072450,31570122）
the International Cooperation Special Project of Guangdong Province(2020A0505100048) （2020A0505100048）
the National Key Project for Basic Research(973 Program,2015CB150600). （973 Program,2015CB150600）
