Design, Synthesis and Fungicidal Activity of 2-Substituted Phenyl-2-oxo-, 2-Hydroxy- and 2-Acyloxyethylsulfonamides

Wang, Minlong; Peng, Rui; Liu, Caixiu; Du, Yan; Qin, Peiwen; Qi, Zhiqiu; Ji, Mingshan; Li, Xinghai; Cui, Zi‐Ning

doi:10.3390/molecules22050738

Cited by 12 publications

(9 citation statements)

References 29 publications

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“…However, there are currently only four sulfonamide fungicides: flusulfamide, which acts against Plasmodiophora brassicae [19], tolnifanide, which acts against Cladosporium cucumerinum, and cyazofamid and amisulbrom, which act against Oomycetes [20,21]. Therefore, more attention should be paid to sulfonamides in the development of fungicides with improved properties [22][23][24] and the ability to target a wider array of pathogens. Recently, some sulfonamides, such as cycloalkylsulfonamides and benzenesulfonamides, were reported as being able to control Sclerotinia sclerotiorum, Fusarium oxysporum, Thanatephorus cucumeris, and B. cinerea [25,26].…”

Section: Introductionmentioning

confidence: 99%

The Effect of (1S,2R-((3-bromophenethyl)amino)-N-(4-chloro-2-trifluoromethylphenyl) cyclohexane-1-sulfonamide) on Botrytis cinerea through the Membrane Damage Mechanism

et al. 2019

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In recent years, Botrytis cinerea has led to serious yield losses because of its resistance to fungicides. Many sulfonamides with improved properties have been used. (1S,2R-((3-bromophenethyl)amino)-N-(4-chloro-2-trifluoromethylphenyl)cyclohexane-1-sulfonamide) (abbreviation: SYAUP-CN-26) is a new sulfonamide compound that has excellent activity against B. cinerea. This study investigated the effect of SYAUP-CN-26 on electric conductivity, nucleic acids leakage, malondialdehyde (MDA) content, and reducing sugars and membrane structure reduction of B. cinerea. The results showed that the cell membrane permeability of B. cinerea increased with increasing concentrations of SYAUP-CN-26; meanwhile, the sugar content decreased, the malondialdehyde content increased, and relative electric conductivity and nucleic acid substance leakage were observed in the cell after exposure to 19.263 mg/L SYAUP-CN-26 for 24 h. After 48 h of exposure to 1.823 mg/L and 19.263 mg/L SYAUP-CN-26, the cell membranes of B. cinerea mycelia were observed to be damaged under propidium iodide (PI) and transmission electron microscopy (TEM) observations. It is assumed that SYAUP-CN-26 was responsible for the damage of cell membrane. Overall, the results indicate that SYAUP-CN-26 could inhibit the growth of B. cinerea cells by damaging the cell membranes.

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Section: Introductionmentioning

confidence: 99%

The Effect of (1S,2R-((3-bromophenethyl)amino)-N-(4-chloro-2-trifluoromethylphenyl) cyclohexane-1-sulfonamide) on Botrytis cinerea through the Membrane Damage Mechanism

et al. 2019

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“…The compounds to be tested were processed to 5% emulsifiable concentrate (EC) formulations and diluted with water to 500 μg mL −1 . The rest of the procedures were given in ref [ 17 ]. The seedlings were maintained in a greenhouse pot at 24 ± 1 °C and relative humidity above 90%.…”

Section: Methodsmentioning

confidence: 99%

“…The molecular size and charge distribution characteristics of sulfonamide are similar to amide. Additionally, reasonable introduction of sulfonyl can increase metabolic stability of the functional molecule and prolong the duration of action by blocking the metabolic instability site and improve the bioavailability [ 17 ]. Compounds with active sulfonamide and amide substructure may have a new mechanism of action.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and SAR of Novel 2-Glycinamide Cyclohexyl Sulfonamide Derivatives against Botrytis cinerea

et al. 2018

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N-(2-trifluoromethyl-4-chlorophenyl)-2-oxocyclohexyl sulfonamide (chesulfamide) is in the limelight as a novel fungicide, and has fungicidal activity against Botrytis cinerea. For exploring more novel structures, 33 new compounds were synthesized by N-alkylation and acid–amine coupling reactions with chesulfamide as the core moiety, and their structures were characterized and established by 1H-NMR, 13C-NMR, MS, and elemental analysis. The structure of (1R,2S)-2-(2-(N-(4-chloro-2-trifluoromethylphenyl)sulfamoyl)-cyclohexylamino)-N-(2-trifluoromethylphenyl) acetamide (II-19) was defined by X-ray single crystal diffraction. The in vivo and in vitro fungicidal activities against B. cinerea were evaluated. The bioassay results of mycelial growth demonstrated that most compounds exhibited excellent inhibitory activity against B. cinerea at 50 μg mL−1, and 7 compounds showed lower EC50 values than boscalid (EC50 = 4.46 μg mL−1) against B. cinerea (CY-09). In cucumber pot experiment, the inhibitory rates of four compounds (II-4, II-5, II-12, and II-13) against B. cinerea were 90.48, 93.45, 92.86, and 91.07, which were better than cyprodinil (88.69%), the best performing of all controls. In tomato pot experiment, the control efficacy of two analogs (II-8 and II-15) were 87.98 and 87.97% at 200 μg mL−1, which were significantly higher than boscalid (78.10%). Most compounds have an excellent fungicidal effect on B. cinerea, with potential as a lead compound for developing new pesticides.

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“…Thirty-five (35) derivatives of 2-substituted phenyl-2-oxo-, 2-Hydroxy-and 2-Acyloxyethylsulfonamides used in the research are found in literature (Wang et al, 2017). The activities of these compounds were reported in EC50 (mg/L), which were converted to pEC50 (pEC50 = -log1/ EC50).…”

Section: Datamentioning

confidence: 99%

Qsar Study of 2-Substituted Phenyl-2-Oxo-, 2-Hydroxyl- And 2-Acylloxyethylsulfonamides as Fungicides

Isyaku

Uzairu²,

Shallangwa³

2019

J. Eng. Exact Sci.

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An insilico study was carried out on a series of thirty-five (35) sulfonyl-containing compounds for their antifungal activities against Botrytis Cinerea fungi using QSAR techniques. Using Spartan 14 molecular modelling software to draw the molecular structure of the compounds, the DFT/B3LYP/6-31G* quantum method of the software was used in optimizing the drawn compounds. The optimized compounds of the dataset were then underbring into PaDEL-Descriptor software for their molecular descriptors calculation. The calculated PaDel-descriptors were then subjected to data-Pretreatment and later splitted into 70% training set and 30% test set. The model was generated using the training set and the test set for the validation of the model built. Using Genetic Function Algorithm (GFA) the model was developed. Four models were developed in which model 1 was chosen as the optimum model with good statistical parameters; R 2 = 0.954, R 2 adj =0.941, cross validation R 2 / Q 2 cv = 0.888 and R 2 pred = 0.839. The model proposed was found to be stable, robust and showed a good internal and external validation. Other statistical analysis such as mean effect, variance inflation factor (VIF), Williams plot among others were also carried out for the applicability domain of the model. k e y w o r d s QSAR 2-substituted Sulfonamides Fungicides

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Design, Synthesis and Fungicidal Activity of 2-Substituted Phenyl-2-oxo-, 2-Hydroxy- and 2-Acyloxyethylsulfonamides

Cited by 12 publications

References 29 publications

The Effect of (1S,2R-((3-bromophenethyl)amino)-N-(4-chloro-2-trifluoromethylphenyl) cyclohexane-1-sulfonamide) on Botrytis cinerea through the Membrane Damage Mechanism

The Effect of (1S,2R-((3-bromophenethyl)amino)-N-(4-chloro-2-trifluoromethylphenyl) cyclohexane-1-sulfonamide) on Botrytis cinerea through the Membrane Damage Mechanism

Design, Synthesis, and SAR of Novel 2-Glycinamide Cyclohexyl Sulfonamide Derivatives against Botrytis cinerea

Qsar Study of 2-Substituted Phenyl-2-Oxo-, 2-Hydroxyl- And 2-Acylloxyethylsulfonamides as Fungicides

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