Design and synthesis of novel 3-(thiophen-2-yl)-1,5-dihydro-2H-pyrrol-2-one derivatives bearing a hydrazone moiety as potential fungicides

Wang, Xiaobin; Ren, Zhengjiao; Wang, Mengqi; Chen, Min; Lu, Aiming; Si, Weijie; Yang, Chunlong

doi:10.1186/s13065-018-0452-z

Cited by 16 publications

(1 citation statement)

References 30 publications

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“…The antifungal activities of the target compounds were examined at an equivalent concentration of 50 μg/mL using mycelia growth inhibitory rate methods according to the published literature. − Meanwhile, boscalid was tested as the positive control at the same concentration. The in vivo anti- B. cinerea effect of 5a and anti -R. solani effect of 6b were evaluated on tomatoes and rice leaves in fruit and detached leaf assays, where boscalid and validamycin, respectively, served as positive controls.…”

Section: Methodsmentioning

confidence: 99%

Design, Synthesis, Antifungal Activity, and 3D-QASR of Novel Oxime Ether-Containing Coumarin Derivatives as Potential Fungicides

Dai,

Wang,

Teng

et al. 2024

J. Agric. Food Chem.

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Structural modification of natural products is an effective approach for improving antifungal activity and has, therefore, been used extensively in the development of new agrochemical products. In this work, a series of novel coumarin derivatives containing oxime ether structures were designed, synthesized, and evaluated for antifungal activity. Some of the designed compounds exhibited promising antifungal activities against tested fungi, and compounds 4a, 4c, 5a, and 6b had EC 50 values equivalent to those of commercial fungicides. Compound 6b was the most promising candidate fungicide against Rhizoctonia solani (EC 50 = 0.46 μg/mL). In vivo antifungal bioassays suggested that compounds 5a and 6b could serve as novel agricultural antifungals. Furthermore, microscopy demonstrated that compound 6b induced the sprawling growth of hyphae, distorted the outline of cell walls, and reduced mitochondrial numbers. Additionally, the effects of the substituent steric, electrostatic, hydrophobic, and hydrogen-bond fields were elucidated using an accurate and reliable three-dimensional quantitative structure−activity relationship (3D-QSAR) model. The results presented here will guide the discovery of potential novel fungicides for plant disease control in agriculture.

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Section: Methodsmentioning

confidence: 99%

Design, Synthesis, Antifungal Activity, and 3D-QASR of Novel Oxime Ether-Containing Coumarin Derivatives as Potential Fungicides

Dai,

Wang,

Teng

et al. 2024

J. Agric. Food Chem.

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Synthesis of novel pyrrole derivatives from the multicomponent reaction using the new N‐sulfonic acid modified poly (styrene‐diethylenetriamine) as a solid acid catalyst

Abbaspour

Pasha

Tajbakhsh

2022

Applied Organom Chemis

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An efficient acid‐catalyzed synthesis of 1,5‐diaryl‐3‐(arylamino)‐1H‐pyrrol‐2(5H)‐ones is reported using novel N‐sulfonic acid modified poly (styrene‐diethylenetriamine) through three‐component reaction between aldehyde, amine, and ethyl pyruvate in high yields and short times. This heterogeneous solid catalyst is produced by reacting amine‐modified chloromethyl polystyrene with neat chlorosulfonic acid. The structure of the synthesized catalyst was examined with Fourier transform‐infrared spectroscopy (FT‐IR), X‐ray diffraction (XRD), dynamic light scattering (DLS), thermogravimetric analysis (TGA), differential thermal analysis (DTA), scanning electron micrograph (SEM), Brunauer–Emmett–Teller (BET), energy dispersive spectroscopy (EDS), and elemental analyses. The heterogeneous catalyst has many advantages, including an easy work‐up procedure, a high product yield, and the capability to be easily regenerated and reused for at least five cycles without losing its activity.

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2‐Bromo‐2‐chloro‐3‐arylpropanenitriles as C‐3 Synthons for the Synthesis of Functionalized 3‐Aminothiophenes

et al. 2019

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2‐Bromo‐2‐chloro‐3‐arylpropanenitriles can be prepared by Meerwein reaction from 2‐chloroacrylonitrile and various aryldiazonium salts under copper(II) bromide catalysis. They proved to be stable compounds which form 2‐chlorocinnnamonitriles upon treatment with bases. Reaction of the title compounds with substituted thioglycolates gave substituted 3‐aminothiophenes which have not yet been accessible by other routes. Three‐component reactions with the title compound, sodium sulfide and bromonitromethane, chloroacetonitrile, or ethyl 4‐chloroacetoacetate gave 2‐nitro‐ and 2‐cyano‐substituted 3‐aminothiophenes, and thienopyridinediones in high yields and in one single step, respectively.

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Design and synthesis of novel 3-(thiophen-2-yl)-1,5-dihydro-2H-pyrrol-2-one derivatives bearing a hydrazone moiety as potential fungicides

Cited by 16 publications

References 30 publications

Design, Synthesis, Antifungal Activity, and 3D-QASR of Novel Oxime Ether-Containing Coumarin Derivatives as Potential Fungicides

Design, Synthesis, Antifungal Activity, and 3D-QASR of Novel Oxime Ether-Containing Coumarin Derivatives as Potential Fungicides

Synthesis of novel pyrrole derivatives from the multicomponent reaction using the new N‐sulfonic acid modified poly (styrene‐diethylenetriamine) as a solid acid catalyst

2‐Bromo‐2‐chloro‐3‐arylpropanenitriles as C‐3 Synthons for the Synthesis of Functionalized 3‐Aminothiophenes

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