Synthesis and bioactivities of Phenazine-1-carboxylic acid derivatives based on the modification of PCA carboxyl group.
Phenazine-1-carboxylic acid (PCA) as a natural product widely exists in microbial metabolites of Pseudomonads and Streptomycetes and has been registered for the fungicide against rice sheath blight in China. To find higher fungicidal activities compounds and study the effects on fungicidal activities after changing the carboxyl group of PCA, we synthesized a series of PCA derivatives by modifying the carboxyl group of PCA and their structures were confirmed by1H NMR and HRMS. Most compounds exhibited significant fungicidal activities in vitro. In particular, compound 6 exhibited inhibition effect against Rhizoctonia solani with EC50values of 4.35mg/L and compound 3b exhibited effect against Fusarium graminearum with EC50values of 8.30mg/L, compared to the positive control PCA with its EC50values of 7.88mg/L (Rhizoctonia solani) and 127.28mg/L (Fusarium graminearum), respectively. The results indicated that the carboxyl group of PCA could be modified to be amide group, acylhydrazine group, ester group, methyl, hydroxymethyl, chloromethyl and ether group etc. And appropriate modifications on carboxyl group of PCA were useful to extend the fungicidal scope.
School of Agricultural, Yangtze University, Jingmi Road 88, Jingzhou 434025, China.
Zhipeng
Z
Xiong
School of Agricultural, Yangtze University, Jingmi Road 88, Jingzhou 434025, China.
Junfan
J
Niu
School of Agricultural, Yangtze University, Jingmi Road 88, Jingzhou 434025, China.
Hao
H
Liu
School of Agricultural, Yangtze University, Jingmi Road 88, Jingzhou 434025, China.
Zhihong
Z
Xu
School of Agricultural, Yangtze University, Jingmi Road 88, Jingzhou 434025, China. Electronic address: junkaili@sina.com.
Junkai
J
Li
School of Agricultural, Yangtze University, Jingmi Road 88, Jingzhou 434025, China. Electronic address: wql106@163.com.
Qinglai
Q
Wu
D005659:Fungicides, Industrial / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity*; D005670:Fusarium / Q000187:drug effects*; D012275:Oryza / Q000382:microbiology; D010619:Phenazines / Q000138:chemical synthesis / Q000737:chemistry / Q000633:toxicity; D010935:Plant Diseases / Q000382:microbiology / Q000517:prevention & control*; D012232:Rhizoctonia / Q000187:drug effects*; D013329:Structure-Activity Relationship; D014908:Triticum / Q000382:microbiology
D005659:Fungicides, Industrial; D010619:Phenazines; C037165:1-phenazinecarboxylic acid
Carboxyl group; Derivatives; Fungicidal activity; Phenazine-1-carboxylic acid; Synthesis