Design, Synthesis, Phloem Mobility, and Bioactivities of a Series of Phenazine-1-Carboxylic Acid-Amino Acid Conjugates

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Linhua YuJunkai Li

Abstract

Developing fungicides with phloem mobility that can be applied to leaves to control root or vascular pathogens has long been desirable. To achieve this goal, an efficient and economical strategy involves introducing an amino acid into the existing highly active parent pesticide molecule. Hence, 12 L-phenazine-1-carboxylic acid (PCA)-amino acid conjugates 4a⁻l were designed and synthesized via a simple synthetic route. In vitro bioassays results showed that all synthesized compounds 4a⁻l exhibited certain fungicidal activities against six tested fungi. Compound 4c exhibited relatively good fungicidal activity against Rhizoctonia solani, and the EC50 value was 0.084 ± 0.006 mmol/L. The phloem mobility experiments revealed that introducing an amino acid to PCA could effectively endow PCA with phloem mobility in R. communis L. Among them, nine conjugates were found in phloem sap, and L-PCA-Valine 4d exhibited the highest phloem mobility. Analysis results from the prediction of the Kleier model indicated that an active carrier-mediated mechanism may be involved in L-PCA-amino acid conjugates-a result that needs to be confirmed and complemented with further tests. The current research provides useful data for modifying non-phloem-mob...Continue Reading

References

Aug 29, 1997·Biochimica Et Biophysica Acta·J F CholletJ L Bonnemain
Nov 10, 2004·Pest Management Science·Jean-François CholletJean-Louis Bonnemain
Aug 1, 1996·Journal of Experimental Botany·F C Hsu, D A Kleier
Oct 28, 2011·Journal of Agricultural and Food Chemistry·Wen YangMeng-Ling Lu
May 17, 2012·Journal of Agricultural and Food Chemistry·Han-Xiang WuHan-Hong Xu
Apr 17, 2013·Journal of Agricultural and Food Chemistry·Jian-Guo YuanHan-Hong Xu
May 2, 2014·Journal of Agricultural and Food Chemistry·Pei-Wen QinHan-Hong Xu
Jun 12, 2014·Journal of Agricultural and Food Chemistry·Zhiwei LeiHanhong Xu
Oct 27, 2016·Bioorganic & Medicinal Chemistry Letters·Junfan NiuJunkai Li
Mar 23, 2017·Bioorganic & Medicinal Chemistry Letters·Zhipeng XiongQinglai Wu
Dec 1, 2017·Pesticide Biochemistry and Physiology·Junfan NiuJunkai Li
Mar 31, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Qingqing ShengHanhong Xu

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Methods Mentioned

BETA
PCA
column chromatography
NMR

Software Mentioned

DPS

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