Design, synthesis and biological activity of hydroxybenzoic acid ester conjugates of phenazine-1-carboxylic acid View Full Text


Ontology type: schema:ScholarlyArticle      Open Access: True


Article Info

DATE

2018-12

AUTHORS

Xiang Zhu, Linhua Yu, Min Zhang, Zhihong Xu, Zongli Yao, Qinglai Wu, Xiaoying Du, Junkai Li

ABSTRACT

We prepared 16 novel hydroxybenzoic acid ester conjugates of phenazine-1-carboxylic acid (PCA) and investigated their biological activity. Most of the synthesized conjugates displayed some level of fungicidal activities in vitro against five phytopathogenic fungi. Nine conjugates 5b, 5c, 5d, 5e, 5h, 5i, 5m, 5n and 5o (EC50 between 3.2 μg/mL and 14.1 μg/mL) were more active than PCA (EC50 18.6 μg/mL) against Rhizoctonia solani. Especially conjugate 5c showed the higher fungicidal activity against Rhizoctonia solani which is 6.5-fold than PCA. And the results of the bioassay indicated that the fungicidal activity of conjugates was associated with their LogP, and the optimal LogP values of the more potent fungicidal activities within these conjugates ranged from 4.42 to 5.08. The systemic acquired resistance induced by PCA-SA ester conjugate 5c against rice sheath blight disease in rice seedlings was evaluated. The results revealed that PCA-SA ester conjugate 5c retained the resistance induction activity of SA against rice sheath blight. More... »

PAGES

111

Identifiers

URI

http://scigraph.springernature.com/pub.10.1186/s13065-018-0478-2

DOI

http://dx.doi.org/10.1186/s13065-018-0478-2

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https://app.dimensions.ai/details/publication/pub.1107973325

PUBMED

https://www.ncbi.nlm.nih.gov/pubmed/30386935


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36 schema:description We prepared 16 novel hydroxybenzoic acid ester conjugates of phenazine-1-carboxylic acid (PCA) and investigated their biological activity. Most of the synthesized conjugates displayed some level of fungicidal activities in vitro against five phytopathogenic fungi. Nine conjugates 5b, 5c, 5d, 5e, 5h, 5i, 5m, 5n and 5o (EC<sub>50</sub> between 3.2 μg/mL and 14.1 μg/mL) were more active than PCA (EC<sub>50</sub> 18.6 μg/mL) against Rhizoctonia solani. Especially conjugate 5c showed the higher fungicidal activity against Rhizoctonia solani which is 6.5-fold than PCA. And the results of the bioassay indicated that the fungicidal activity of conjugates was associated with their LogP, and the optimal LogP values of the more potent fungicidal activities within these conjugates ranged from 4.42 to 5.08. The systemic acquired resistance induced by PCA-SA ester conjugate 5c against rice sheath blight disease in rice seedlings was evaluated. The results revealed that PCA-SA ester conjugate 5c retained the resistance induction activity of SA against rice sheath blight.
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