Results
Title

Synthesis and bioactivities of phenazine-1-carboxylic piperazine derivatives.

Authors

Han, Fei; Yan, Ru; Zhang, Min; Xiang, Zhu; Wu, Qinglai; Li, Junkai

Abstract

Phenazine-1-carboxylic acid (PCA) as a natural product which has significant inhibition effects against many soil-borne fungal phytopathogens in agricultural application and has been registered in China as the fungicide against rice sheath blight. In order to find new higher fungicidal activities lead compounds and develop new eco-friendly agrochemicals, we introduced substructure piperazines which also have high biological activity into PCA, designed and synthesized a series of phenazine-1-carboxylic piperazine derivatives, and their structures were confirmed by 1H NMR and HRMS. Most compounds exhibited certain in vitro fungicidal activities. In particular, Compounds 5r exhibited the activity against all the tested pathogenic fungi, such as Rhizoctonia solani, Alternaria solani, Fusarium oxysporum, Fusarium graminearum, Pyricularia oryzac Cavgra, with the EC50 value of 24.6μM, 42.9μM, 73.7μM, 73.8μM, 34.2μM, respectively, more potent activities than PCA (33.2μM, 81.5μM, 186.5μM, 176.4μM, 37.3μM). This result provided a highly active lead compound for the further structure optimization design.

Subjects

CHINA; PIPERAZINE; RICE sheath blight; RHIZOCTONIA solani; PATHOGENIC fungi; FUSARIUM oxysporum; ALTERNARIA

Publication

Natural Product Research, 2020, Vol 34, Issue 9, p1282

ISSN

1478-6419

Publication type

Academic Journal

DOI

10.1080/14786419.2018.1556656