The relationship between features enabling <scp>SDHI</scp> fungicide binding to the <i>Sc‐Sdh</i> complex and its inhibitory activity against <i>Sclerotinia sclerotiorum</i>

Gao, Yangyang; He, Lifei; Zhu, Jiachen; Cheng, Jiagao; Li, Beixing; Liu, Feng; Mu, Wei

doi:10.1002/ps.5827

Cited by 33 publications

(25 citation statements)

References 45 publications

(79 reference statements)

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“…Sclerotinia sclerotiorum is known to adhere to the host surface and to penetrate the plant cuticle ( Liu et al, 2018 ; Xu et al, 2018 ). This fungal pathogen is able to invade different soybean tissues, such as stem, root, and pod, at different plant growth stages ( Gao et al, 2020 ). It was estimated that the losses produced by S. sclerotiorum in soybean in 1997, 2004, and 2009 were approximately in 953 million, 1.63, and 1.61 billion kg, which correspond to 227, 344, and 560 million dollars, respectively ( Peltier et al, 2012 ).…”

Section: Introductionmentioning

confidence: 99%

Antifungal Mechanism and Efficacy of Kojic Acid for the Control of Sclerotinia sclerotiorum in Soybean

et al. 2022

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Sclerotinia stem rot, which is caused by the fungal pathogen Sclerotinia sclerotiorum, is a soybean disease that results in enormous economic losses worldwide. The control of S. sclerotiorum is a difficult task due to the pathogen’s wide host range and its persistent structures, called sclerotia. In addition, there is lack of soybean cultivars with medium to high levels of resistance to S. sclerotiorum. In this work, kojic acid (KA), a natural bioactive compound commonly used in cosmetic industry, was evaluated for the management of Sclerotinia stem rot. Interestingly, KA showed strong antifungal activity against S. sclerotiorum by inhibiting chitin and melanin syntheses and, subsequently, sclerotia formation. The antifungal activity of KA was not obviously affected by pH, but was reduced in the presence of metal ions. Treatment with KA reduced the content of virulence factor oxalic acid in S. sclerotiorum secretions. Preventive applications of 50 mM KA (7.1 mg/ml) completely inhibited S. sclerotiorum symptoms in soybean; whereas, in curative applications, the combination of KA with prochloraz and carbendazim improved the efficacy of these commercial fungicides. Taken together, the antifungal activity of KA against S. sclerotiorum was studied for the first time, revealing new insights on the potential application of KA for the control of Sclerotinia stem rot in soybean.

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Section: Introductionmentioning

confidence: 99%

Antifungal Mechanism and Efficacy of Kojic Acid for the Control of Sclerotinia sclerotiorum in Soybean

et al. 2022

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“…To study the mechanism of stereoselective fungicidal activity of chiral pesticide pydiflumetofen, docking studies between fungicides and the S. sclerotiorum SDH complex were conducted according to previous research. 29 The primary sequence of S. sclerotiorum SDH is similar to the primary sequences of the porcine SDH complex (PDB: 3SFD), therefore homology modeling was performed by using the crystal structure of the SDH from Sus scrofa as a template. A three-dimensional model of SDH in S. sclerotiorum with high sequence similarity was built based on the aligned sequences by homology modeling using the Prime software homology modeling (Prime, version 4.4; Schrödinger, LLC, New York, NY).…”

Section: Homology Modeling and Molecular Dockingmentioning

confidence: 99%

“…Different factors, including hydrogen bonds, π-π bonds, metal coordination, π-cation interactions, and hydrophobic effects, might result in stereoselective molecular interactions. 39 Gao et al 29 reported that the different SDHI fungicides have varying affinities with the SDH complex of S. sclerotiorum, including two hydrogen bonds and π-π bonds for benzovindiflupyr, three hydrogen bonds for isopyrazam, and two hydrogen bonds for fluxapyroxad. Moreover, the two hydrogen bonds are formed between pydiflumetofen and SDH complex amino acid residues (TRP and TYR).…”

Section: Molecular Interactions Between Pydiflumetofen Enantiomers and Sdhmentioning

confidence: 99%

Evaluation of exploitive potential for higher bioactivity and lower residue risk enantiomer of chiral fungicide pydiflumetofen

Wang

Zhang

et al. 2021

Pest Management Science

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BACKGROUND: Pydiflumetofen, as a new succinate dehydrogenase inhibitor (SDHI) chiral fungicide, has been used in crop production because of its broad-spectrum and high-efficiency antifungal activity. However, little is known about pydiflumetofen at the chiral level. The stereoselective bioactivity and degradation of pydiflumetofen enantiomers were therefore investigated. RESULTS: Pydiflumetofen presented effective bioactivity against the eight tested phytopathogens, and its enantiomers showed significant differences in activity. The bioactivity of R-pydiflumetofen was 9.0-958.8 times higher than that of the S enantiomer. Treatment with R-pydiflumetofen increased the cell membrane permeability of Sclerotinia sclerotiorum and decreased exopolysaccharide and oxalic acid production more than treatment with S-pydiflumetofen. Furthermore, R-pydflumetofen exhibited better inhibitory activity against the succinate dehydrogenase enzyme of S. sclerotiorum than S-pydiflumetofen by 584-fold. According to homology modeling and molecular docking studies, the binding affinities of the R and S enantiomers were −7.0 and −5.3 kcal mol −1 , respectively. Additionally, the degradation half-lives of Sand R-pydiflumetofen in three vegetables (cucumber, eggplant, and cowpea) under field conditions were 2.56-3.12 days and 2.48-2.76 days, respectively, which reveals that R-pydiflumetofen degrades faster than S-pydiflumetofen.CONCLUSION: Based on the results obtained, R-pydiflumetofen not only exhibited a higher bactericidal activity, but also posed fewer residual risks in the environment. The mechanism of the stereoselective bioactivity was correlated with the stereoselective inhibition activity of the target enzyme and affected the cell membrane permeability and the production of exopolysaccharide and oxalic acid. This research could provide a foundation for the systematic evaluation of pydiflumetofen from an enantiomeric view.

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“…Pyrazole carboxamide derivatives showed a broad spectrum of antifungal activities as the succinate dehydrogenase inhibitor (SDHI), − and some of them reached the market in the past decade, such as penthiopyrad, penflufen, sedaxane, bixafen, fluxapyroxad, and pydiflumetofen (Scheme A). , Despite the remarkable effectiveness of commercial SDHI fungicides to agricultural production and food security in the past decade, invasive fungal diseases continue to cause global agricultural production reduction because these commercial SDHI fungicides possess similar structural skeletons, which may easily lead to drug resistance with continuous drug therapy. − Novel pharmacophores should be urgently explored to avoid SDH-based fungi cross-resistance.…”

Section: Introductionmentioning

confidence: 99%

Discovery of Novel Pyrazole Carboxylate Derivatives Containing Thiazole as Potential Fungicides

Xia

Cheng

Liu

et al. 2021

J. Agric. Food Chem.

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Inspired by commercially established fluxapyroxad as the lead compound of novel efficient antifungal ingredients, novel pyrazole carboxylate derivatives containing a flexible thiazole backbone were successfully designed, synthesized, and detected for their in vitro and in vivo biological activities against eight agricultural fungi. The antifungal bioassay results showed that compound 24 revealed excellent bioactivities against Botrytis cinerea and Sclerotinia sclerotiorum, with median effective concentrations (EC 50 ) of 0.40 and 3.54 mg/L, respectively. Compound 15 revealed remarkable antifungal activity against Valsa mali, with an EC 50 value of 0.32 mg/L. For in vivo fungicide control against B. cinerea and V. mali, compounds 3 and 24 at 25 mg/L, respectively, displayed prominent efficacy on cherry tomatoes and apple branches. Molecular docking results demonstrated that compound 15 could form an interaction with several crucial residues of succinate dehydrogenase (SDH), and the in vitro enzyme assay indicated that the target compound 15 displayed an inhibitory effect toward SDH, with an IC 50 value of 82.26 μM. The experimental results indicated that phenyl pyrazole carboxylate derivatives displayed a weak antifungal property and low activity compared to the other title substituent pyrazole carboxylate derivatives. Compounds 3, 15, and 24 are promising antifungal candidates worthy of further fungicide development due to their prominent effectiveness.

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The relationship between features enabling SDHI fungicide binding to the Sc‐Sdh complex and its inhibitory activity against Sclerotinia sclerotiorum

Cited by 33 publications

References 45 publications

Antifungal Mechanism and Efficacy of Kojic Acid for the Control of Sclerotinia sclerotiorum in Soybean

Antifungal Mechanism and Efficacy of Kojic Acid for the Control of Sclerotinia sclerotiorum in Soybean

Evaluation of exploitive potential for higher bioactivity and lower residue risk enantiomer of chiral fungicide pydiflumetofen

Discovery of Novel Pyrazole Carboxylate Derivatives Containing Thiazole as Potential Fungicides

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