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

• Published in: Molecules (Basel, Switzerland) Vol. 23; no. 9; p. 2139
• Main Authors: Yu, Linhua, Huang, Di, Zhu, Xiang, Zhang, Min, Yao, Zongli, Wu, Qinglai, Xu, Zhihong, Li, Junkai
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 25.08.2018; MDPI
• Subjects: Acetic acid; amino acid; Amino acids; Amino Acids - chemistry; Aqueous solutions; bioactivities; Carbonyl compounds; Carbonyls; Carboxylic acids; Chemical Phenomena; Chemistry Techniques, Synthetic; Chromatography; Conjugates; Dichloromethane; Drug Design; Esters; Ethyl acetate; Foliage; Fungicides, Industrial - chemistry; Fungicides, Industrial - pharmacology; Glycine; Lithium; Lithium hydroxides; Pesticides; Phenazine; Phenazine-1-carboxylic acid; phenazine-1-carboxylic acid (PCA); Phenazines - chemistry; Phloem; Phloem - chemistry; phloem mobility; Phosgene; Plant growth; Plant growth substances; Polyethylene; Polyethylenes; Recrystallization; Room temperature; Seeds; synthesis; Triethylamine; Vascular diseases; China; synthesis; phenazine-1-carboxylic acid (PCA); phloem mobility; amino acid; bioactivities
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules23092139

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 ⁻ were designed and synthesized via a simple synthetic route. In vitro bioassays results showed that all synthesized compounds ⁻ exhibited certain fungicidal activities against six tested fungi. Compound exhibited relatively good fungicidal activity against , and the EC 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 L. Among them, nine conjugates were found in phloem sap, and L-PCA-Valine 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-mobile fungicidal molecules to phloem-mobile types.