Novel Camphor Sulfonohydrazide and Sulfonamide Derivatives as Potential Succinate Dehydrogenase Inhibitors against Phytopathogenic Fungi/Oomycetes

Yang, Zihui; Sun, Xuebao; Jin, Daojun; Qiu, Yigui; Chen, Linlin; Sun, Lu; Gu, Wen

doi:10.1021/acs.jafc.2c05628

Cited by 11 publications

(10 citation statements)

References 50 publications

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“…The antifungal activity of curcumol and its derivatives against five fungi was assayed by mycelium growth rate method as literature reported [26] . ( Supporting Information )…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Antifungal Activity of Curcumol Derivatives

Gao

Jin

Jian

et al. 2023

Chemistry & Biodiversity

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To discover novel and effective antifungal candidates, a series of new curcumol derivatives were designed, synthesized, and evaluated their antifungal activity against five phytopathogenic fungi by the mycelium growth rate method. Derivatives c4, c22 and c23 exhibited excellent antifungal activity against Phomopsis sp. with EC50 values of 3.06, 3.07, and 3.16 μM, respectively. Specifically, compound c4 exhibited the strongest antifungal activity against Phomopsis sp., which was 44 times that of pyrimethanil (EC50=134.37 μM). The results of scanning electron microscopy (SEM) and transmission electron microscopy (TEM) indicated that compound c4 could cause cell senescence and death of Phomopsis sp. by changing the normal hyphal morphology and disrupting the normal metabolism of hyphal cells. Moreover, compound c4 showed excellent curative effect against Phomopsis sp. on kiwifruit. These findings confirmed that compound c4 has great potential as a potent antifungal agent.

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“…The antifungal activity of curcumol and its derivatives against five fungi was assayed by mycelium growth rate method as literature reported [26] . ( Supporting Information )…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Antifungal Activity of Curcumol Derivatives

Gao

Jin

Jian

et al. 2023

Chemistry & Biodiversity

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“…The crystal structure of SDH (respiratory complex II) was acquired from the Protein Data Bank (PDB code 2FBW). , The molecular docking studies were performed using the CDOCKER protocol for the receptor–ligand interaction section of Discovery Studio 2021 software.…”

Section: Methodsmentioning

confidence: 99%

Discovery of Pyrazole-5-yl-amide Derivatives Containing Cinnamamide Structural Fragments as Potential Succinate Dehydrogenase Inhibitors

Cheng,

Xu,

Cui

et al. 2023

J. Agric. Food Chem.

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To promote the development of novel agricultural succinate dehydrogenase inhibitor (SDHI) fungicides, we introduced cinnamamide and nicotinamide structural fragments into the structure of pyrazol-5-yl-amide by carbon chain extension and scaffold hopping, respectively, and synthesized a series of derivatives. The results of the biological activity assays indicated that most of the target compounds exhibited varying degrees of inhibitory activity against the tested fungi. Notably, compounds G22, G28, G34, G38, and G39 exhibited excellent in vitro antifungal activities against Valsa mali with EC 50 values of 0.48, 0.86, 0.57, 0.73, and 0.87 mg/L, respectively, and this result was significantly more potent than boscalid (EC 50 = 2.80 mg/L) and closer to the specialty control drug tebuconazole (EC 50 = 0.30 mg/L). Compounds G22 and G34 also exhibited excellent in vivo protective and curative effects against V. mali at 40 mg/L. The SEM and TEM observations indicated that compounds G22 and G34 may affect normal V. mali mycelial morphology as well as the cellular ultrastructure. Molecular docking analysis results indicated that G22 and boscalid possessed a similar binding mode to that of SDH, and detailed SDH inhibition assays validated the feasibility of the designed compounds as potential SDH inhibitors. Compounds G22 and G3 were selected for theoretical calculations, and the terminal carboxylic acid group of this series of compounds may be a key region influencing the antifungal activity. Furthermore, toxicity tests on Apis mellifera l. revealed that compounds G22 and G34 exhibited low toxicity to A. mellifera l. populations. The above results demonstrated that these series of pyrazole-5-yl-amide derivatives are promising for development as potential low-risk drug-resistance agricultural SDHI fungicides.

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“…[29][30][31] Further understanding of the antimicrobial mechanism of compound C17 against Phomopsis sp. was obtained through the effect of extracellular polysaccharides (EPS) produced by Phomopsis sp., [32][33] alteration of Phomopsis sp. cell membrane permeability, [34][35] scanning electron microscopy (SEM) observations, [36] transmission electron microscopy (TEM) observations [37] and leakage of cytoplasmic content.…”

Section: Fungimentioning

confidence: 99%

Synthesis and Antifungal Activity of 2‐(2‐Benzoxazolyl)‐1‐arylethanone and 2‐(2‐Benzoxazolyl)‐1‐alkylethanone Derivatives

Che,

Jin,

Sun

et al. 2023

Chemistry & Biodiversity

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To discover more effective antifungal candidates, 33 benzoxazole derivatives, were designed, synthesized, and evaluated for their antifungal activity against seven phytopathogenic fungi by the mycelium growth rate method. Among 33 benzoxazole derivatives had thirteen derivatives no reported, and new derivatives C17 exhibited good inhibitory activity against Phomopsis sp. with EC50 values of 3.26 μM. Structure–activity relationship (SAR) of these derivatives analysis indicated that the substituent played a key role in antifungal activity in ortho‐, meta‐ and para‐ substituted acetophenones. The preliminary mechanistic exploration demonstrated that C17 might exert its antifungal activity by targeting the mycelia cell membrane, which was verified by the observed changes in mycelial morphology, the formation of extracellular polysaccharides, cellular contents, cell membrane permeability and integrity, among other effects. Furthermore, C17 had potent curative effect against Phomopsis sp. in vivo, which indicated that C17 may be as a novelty potent antifungal agent.

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Novel Camphor Sulfonohydrazide and Sulfonamide Derivatives as Potential Succinate Dehydrogenase Inhibitors against Phytopathogenic Fungi/Oomycetes

Cited by 11 publications

References 50 publications

Synthesis and Antifungal Activity of Curcumol Derivatives

Synthesis and Antifungal Activity of Curcumol Derivatives

Discovery of Pyrazole-5-yl-amide Derivatives Containing Cinnamamide Structural Fragments as Potential Succinate Dehydrogenase Inhibitors

Synthesis and Antifungal Activity of 2‐(2‐Benzoxazolyl)‐1‐arylethanone and 2‐(2‐Benzoxazolyl)‐1‐alkylethanone Derivatives

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