Synthesis and bioactivities of diamide derivatives containing a phenazine-1-carboxamide scaffold

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-mobile fungicidal molecules to phloem-mobile types.

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“…The PCA-amino acid conjugates 4a – l were synthesized as previously described [ 12 , 15 ]. The synthetic route is described in Scheme 1 .…”

Section: Methodsmentioning

confidence: 99%

“…Then, a solution of oxalyl chloride (15 mmol) in 15 mL CH 2 Cl 2 was slowly added. The reaction was stirred at reflux temperature for 12 h. The mixture was evaporated under vacuum, and the residue is dissolved in 15 ml anhydrous CH 2 Cl 2 , which was used in the next step without purification [ 15 ].…”

Section: Methodsmentioning

confidence: 99%

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

Huang

Zhu

et al. 2018

Molecules

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“…The primary fungicidal activities of 10 PCA-amino acid conjugates were evaluated using an amended agar assay described in our previously published literature. 15,17 Each test compound was first dissolved within a suitable amount of acetone and diluted with water containing 0.1% Tween 80 to 2 mmol L −1 , and 1 mL of each was then added to 9 mL molten (50 ∘ C) sterile potato dextrose agar (PDA the PDA culture and PT represented colony diameter of amended agar plates. All statistical analyses were performed using DPS 7.05 software using analysis of variance at P = 0.05.…”

Section: In Vitro Assays Of Fungicidal Activitiesmentioning

confidence: 99%

“…1) is an important N-containing heterocyclic secondary metabolite, with a wide range of biological activities, isolated from numerous bacterial genera, including Pseudomonas and Streptomycetes. [15][16][17] PCA has been found to be effective against several phytopathogenic fungi, and has been registered in China as the biofungicide 'Shenqinbactin' against rice sheath blight caused by Rhizoctonia solani. 18,19 The synthesis and biosynthesis of PCA and its derivatives have been widely studied and reported in the literature.…”

Section: Introductionmentioning

confidence: 99%

The influence of steric configuration of phenazine‐1‐carboxylic acid‐amino acid conjugates on fungicidal activity and systemicity

Zhu

Hsiang

et al. 2019

Pest Management Science

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BACKGROUND Conjugating an amino acid onto existing fungicidal parent structures has been demonstrated to be an effective way to endow non‐phloem mobile fungicides with phloem mobility. To alter the systemicity of the fungicide PCA (phenazine‐1‐carboxylic acid), 10 amino acids derivatives of this fungicide were designed and synthesized, and their synthesis, characterization, phloem and xylem mobility in Ricinus communis L, and their fungicidal activity in vitro are described. RESULTS The systemicity experiments in Ricinus communis system demonstrated that all conjugates exhibited obvious phloem mobility compared with non‐phloem‐mobile PCA, and the introduction of an L‐amino acid to PCA more greatly enhanced the phloem mobility. The five D‐amino acid conjugates exhibited higher xylem mobility than that of PCA and of each corresponding L‐amino acid conjugate. Most conjugates were found to exhibit moderate in vitro fungicidal activities against six pathogenic fungi, which were lower than that of PCA. The results of the bioassay showed fungicidal activities of PCA‐amino acid conjugates associated not only with different amino acids, but also with their conformation. Conjugation with D‐amino acid contributed to the in vitro fungicidal activities of PCA‐amino acid conjugates. CONCLUSIONS The current research offers a new strategy for enhancing the systemicity of non‐phloem‐mobile fungicides and presents some useful information on the effects of introducing amino acids of different steric configurations on the fungicidal activity, phloem and xylem mobility of the parent fungicide. © 2019 Society of Chemical Industry

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“…All the compounds were tested the herbicidal activities against Echinochloa crus-galli and Brassica napus by the seed germination method [25]. The method of dispensing was equal to that in the experiment of antifungal activities.…”

Section: Determination Of Herbicidal Activitiesmentioning

confidence: 99%

Chemical Constituents from Fraxinus hupehensis and Their Antifungal and Herbicidal Activities

et al. 2020

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The phytochemical investigation of Fraxinus hupehensis led to the isolation and characterization of ten compounds which were identified as fraxin (1), fraxetin (2), esculetin (3), cichoriin (4), euphorbetin (5), kaempferol-3-O-β-rutinoside (6), oleuropein (7), linoleic acid (8), methyl linoleate (9), and β-sitosterol (10). Structures of the isolated constituents were characterized by 1H NMR, 13C NMR and HRMS. All the compounds, except compounds 3 and 4, were isolated for the first time from this plant. Further, this was the first report for the occurrence of compound 5 in the Fraxinus species. Antifungal activity evaluation showed that compound 2 exhibited significant inhibitory effects against Bipolaris maydis, Sclerotium rolfsii, and Alternaria solani with EC50 values of 0.31 ± 0.01 mmol/L, 10.50 ± 0.02 mmol/L, and 0.40 ± 0.02 mmol/L respectively, compared to the positive control, Carbendazim, with its EC50 values of 0.74 ± 0.01 mmol/L, 1.78 ± 0.01 mmol/L and 1.41 ± 0.00 mmol/L. Herbicidal activity tests showed that compounds 8–10 had strong inhibitory effects against the roots of Echinochloa crus-galli with EC50 values of 1.16 ± 0.23 mmol/L, 1.28 ± 0.58 mmol/L and 1.33 ± 0.35 mmol/L respectively, more potently active than that of the positive control, Cyanazine, with its EC50 values of 1.56 ± 0.44 mmol/L. However, none of the compounds proved to be active against the tested bacteria (Erwinia carotovora, Pseudomonas syringae, and Ralstonia solanacearum).

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Synthesis and bioactivities of diamide derivatives containing a phenazine-1-carboxamide scaffold

Cited by 16 publications

References 20 publications

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

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

The influence of steric configuration of phenazine‐1‐carboxylic acid‐amino acid conjugates on fungicidal activity and systemicity

Chemical Constituents from Fraxinus hupehensis and Their Antifungal and Herbicidal Activities

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