Design, Synthesis, and Antifungal Activity of Novel Chalcone Derivatives Containing a Piperazine Fragment

Zhou, Qing; Tang, Xuemei; Chen, Shuai; Zhan, Wenliang; Hu, Die; Zhou, Ran; Sun, Nan; Wu, Yongjun; Xue, Wei

doi:10.1021/acs.jafc.1c05933

Cited by 51 publications

(34 citation statements)

References 30 publications

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“…The protective and curative effects of compound 4y against R. solani were also assessed using the potted rice method. , An appropriate amount of compound 4y or control agents in 200 μL of DMSO was mixed with the solution containing distilled water (50 mL) and Tween-20 (500 μL). For the experiment of curative effects, after inoculation with R.…”

Section: Methodsmentioning

confidence: 99%

Discovery of Novel Quinazoline-2-Aminothiazole Hybrids Containing a 4-Piperidinylamide Linker as Potential Fungicides against the Phytopathogenic Fungus Rhizoctonia solani

Ding

Lin

et al. 2022

J. Agric. Food Chem.

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A total of 29 novel quinazoline-2-aminothiazole hybrids containing a 4-piperidinylamide linker were designed, synthesized, and evaluated for their anti-microbial properties against phytopathogenic fungi and bacteria of agricultural importance. The anti-fungal assays indicated that some of the target compounds exhibited excellent inhibitory effects in vitro against Rhizoctonia solani. For example, 11 compounds within this series (including 4a, 4g, 4h, 4j, 4o, 4s, 4t, 4u, 4v, 4y, and 4b′) were found to possess EC50 values (effective concentration for 50% activity) ranging from 0.42 to 2.05 μg/mL against this pathogen. In particular, compound 4y with a 2-chloro-6-fluorophenyl substituent displayed a potent anti-R. solani efficacy with EC50 = 0.42 μg/mL, nearly threefold more effective than the commercialized fungicide Chlorothalonil (EC50 = 1.20 μg/mL) and also slightly superior to the other fungicide Carbendazim (EC50 = 0.53 μg/mL). Moreover, compound 4y could efficiently inhibit the growth of R. solani in vivo on the potted rice plants, displaying an impressive protection efficacy of 82.3% at 200 μg/mL, better than those of the fungicides Carbendazim (69.8%) and Chlorothalonil (48.9%). Finally, the mechanistic studies showed that compound 4y exerted its anti-fungal effects by altering the mycelial morphology, increasing the cell membrane permeability, and destroying the cell membrane integrity. On the other hand, some compounds demonstrated good anti-bacterial effects in vitro against Xanthomonas oryzae pv. oryzae (Xoo). Overall, the presented results implied that 4-piperidinylamide-bridged quinazoline-2-aminothiazole hybrids held the promise of acting as lead compounds for developing more efficient fungicides to control R. solani.

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Section: Methodsmentioning

confidence: 99%

Discovery of Novel Quinazoline-2-Aminothiazole Hybrids Containing a 4-Piperidinylamide Linker as Potential Fungicides against the Phytopathogenic Fungus Rhizoctonia solani

Ding

Lin

et al. 2022

J. Agric. Food Chem.

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“…We performed turbidimetry tests to evaluate the in vitro antibacterial activity of compounds E1 – E24 against five bacteria. − …”

Section: Methodsmentioning

confidence: 99%

“…32−34 2.In Vitro Antifungal Activity. The compounds E1−E24 against 10 fungi were determined by the mycelium growth rate test 34. 2.In Vivo Antiviral Activity.…”

mentioning

confidence: 99%

Design, Synthesis, and Biological Evaluation of Novel 1,4-Pentadien-3-one Derivatives Containing a Sulfonamide Moiety

Zhou

Zhu

et al. 2022

J. Agric. Food Chem.

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Novel 1,4-pentadien-3-one derivatives containing a sulfonamide moiety were synthesized, and their antifungal, antibacterial, and antiviral activities were verified. These compounds exhibited better activity against five bacteria, with EC 50 values ranging from 9.6 to 60.1 μg/mL, prominently, which are superior to those of the commercial agent. A great amount of compounds had excellent fungicidal activity in vitro at 100 μg/mL. Strikingly, compound E6 exhibited moderate activity against Phytophthora litchii than azoxystrobin, with the EC 50 value of compound E6 (0.5 μg/mL) drawing near azoxystrobin (0.3 μg/mL). Furthermore, compound E17 had a marked impact on in vivo anti-tobacco mosaic virus, according to the data of microscale thermophoresis, with a K d value of the intermolecular binding force of 0.002 ± 0.001 μM, which was better than the commercial agent of ningnanmycin (K d = 0.121 ± 0.031 μM). In addition, the results of these studies suggest that the use of active splicing can improve the biological activity of natural compounds and provide further complement to the development of novel pesticides.

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“…Rice sheath blight (RSB) caused by Rhizoctonia solani is one of the most destructive diseases of rice (Oryza sativa) in the world . RSB occurs in the entire growth period of rice, mainly damaging leaf sheaths and leaves . RSB has a strong epidemic and a wide range of infection, which can even reduce rice production by 50% in China …”

Section: Introductionmentioning

confidence: 99%

Anti-Fungal Activity of Moutan cortex Extracts against Rice Sheath Blight (Rhizoctonia solani) and Its Action on the Pathogen’s Cell Membrane

Zhao

Wang

et al. 2022

ACS Omega

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Rice sheath blight (RSB) caused by Rhizoctonia solani is one of the most destructive diseases of rice (Oryza sativa). Although chemical fungicides are the most important control methods, their long-term unreasonable application has brought about problems such as environmental pollution, food risks, and non-target poisoning. Therefore, considering the extraction of fungistatic substances from plants may be an alternative in the future. In this study, we found that the Moutan cortex ethanol extract has excellent antifungal activity against R. solani, with a 100% inhibition rate at 1000 μg/mL, which aroused our great exploration interest. In-depth exploration found that the antifungal active ingredients of M. cortex were mainly concentrated in the petroleum ether extract of the M. cortex ethanol extract, which still maintained a 100% inhibition rate with 250 μg/mL, and its effective medium concentration (EC 50 ) was 145.33 μg/mL against R. solani. Through the measurement of extracellular relative conductivity and OD 260 , the petroleum ether extract induced leakage of intracellular electrolytes and nucleic acids, indicating that the cell membrane was ruined. Therefore, we preliminarily determined that the cell membrane may be the target of the petroleum ether extract. Moreover, we found that petroleum ether extract reduced the content of ergosterol, a component of the cell membrane, which may be one of the reasons for the cell membrane destruction. Furthermore, the increase of MDA content would lead to membrane lipid peroxidation, further aggravating membrane damage, resulting in increased membrane permeability. Also, the destruction of the cell membrane was observed by the phenomenon of the mycelium being transparent and broken. In conclusion, this is the first report of the M. cortex petroleum ether extract exhibiting excellent antifungal activity against R. solani. The effect of the M. cortex petroleum ether extract on R. solani may be on the cell membrane, inducing the disorder of intracellular substances and metabolism, which may be one of the antifungal mechanisms against R. solani.

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Design, Synthesis, and Antifungal Activity of Novel Chalcone Derivatives Containing a Piperazine Fragment

Cited by 51 publications

References 30 publications

Discovery of Novel Quinazoline-2-Aminothiazole Hybrids Containing a 4-Piperidinylamide Linker as Potential Fungicides against the Phytopathogenic Fungus Rhizoctonia solani

Discovery of Novel Quinazoline-2-Aminothiazole Hybrids Containing a 4-Piperidinylamide Linker as Potential Fungicides against the Phytopathogenic Fungus Rhizoctonia solani

Design, Synthesis, and Biological Evaluation of Novel 1,4-Pentadien-3-one Derivatives Containing a Sulfonamide Moiety

Anti-Fungal Activity of Moutan cortex Extracts against Rice Sheath Blight (Rhizoctonia solani) and Its Action on the Pathogen’s Cell Membrane

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