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Synthesis and bioactivities of Phenazine-1-carboxylic acid derivatives based on the modification of PCA carboxyl group

Zhipeng Xiong  Junfan Niu  Hao Liu  Zhihong Xu  Junkai Li  Qinglai Wu  
【摘要】: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. Most compounds exhibited significant fungicidal activities in vitro. In particular, compound 6 exhibited inhibition effect against Rhizoctonia solani with EC50 values of 4.35 mg/L and compound 3 b exhibited effect against Fusarium graminearum with EC50 values of 8.30 mg/L, compared to the positive control PCA with its EC50 values of 7.88 mg/L(Rhizoctonia solani) and 127.28 mg/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 et.al. And appropriate modifications on carboxyl group of PCA were useful to extend the fungicidal scope.

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