Design, synthesis, and fungicidal activity of novel 1,3,4-oxadiazole derivatives

Yu, Fuqiang; Guan, Aiying; Li, Mengru; Hu, Lan; Li, Xiaowu

doi:10.1016/j.cclet.2018.01.050

Cited by 21 publications

(9 citation statements)

References 17 publications

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“…In our previous work, a series of quinoline derivatives substituted at the 4-position with significant antifungal activity were obtained through structural simplification of quinine alkaloids . Therefore, continuing our efforts on the discovery of fungicidal quinoline compounds for the control of plant diseases and considering that acylhydrazine and oxadiazole moieties, as privileged structures with a broad-range pharmacological potential, − are widely used in pesticidal and medicinal chemistry, here, we introduced acylhydrazine and oxadiazole groups into the 2-position of quinoline ring to synthesize a series of quinoline derivatives and systematically evaluated their in vitro fungicidal activities against four pathogenic fungi. Moreover, the preliminary mechanism of action of the most effective fungicidal candidate against F.…”

Section: Introductionmentioning

confidence: 99%

Design and Discovery of Novel Antifungal Quinoline Derivatives with Acylhydrazide as a Promising Pharmacophore

Yang

et al. 2021

J. Agric. Food Chem.

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Inspired by natural 2-quinolinecarboxylic acid derivatives, a series of quinoline compounds containing acylhydrazine, acylhydrazone, sulfonylhydrazine, oxadiazole, thiadiazole, or triazole moieties were synthesized and evaluated for their fungicidal activity. Most of these compounds exhibited excellent fungicidal activity in vitro. Significantly, compound 2e displayed the superior in vitro antifungal activity against Sclerotinia sclerotiorum, Rhizoctonia solani, Botrytis cinerea, and Fusarium graminearum with the EC 50 values of 0.39, 0.46, 0.19, and 0.18 μg/mL, respectively, and were more potent than those of carbendazim (EC 50 , 0.68, 0.14, >100, and 0.65 μg/mL, respectively). Moreover, compound 2e could inhibit spore germination of F. graminearum. Preliminary mechanistic studies showed that compound 2e could cause abnormal morphology of cell walls and vacuoles, loss of mitochondrion, increases in membrane permeability, and release of cellular contents. These results indicate that compound 2e displayed superior fungicidal activities and could be a potential fungicidal candidate against plant fungal diseases.

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Section: Introductionmentioning

confidence: 99%

Design and Discovery of Novel Antifungal Quinoline Derivatives with Acylhydrazide as a Promising Pharmacophore

Yang

et al. 2021

J. Agric. Food Chem.

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“…Continuing our efforts on fungicidal agent discovery for the control of rice sheath blight and considering that oxadiazole groups are highly efficient pharmacophores, with a particularly fungicidal effect, 18,19 and widely used in drug and pesticide molecular design, here, we synthesized a series of β-carboline oxadiazole derivatives and systematically 20 evaluated their in vitro and in vivo fungicidal activities against R. solani. Moreover, the preliminary mechanism of action of the most effective fungicidal candidate against R. solani was also evaluated.…”

Section: ■ Introductionmentioning

confidence: 99%

Discovery of β-Carboline Oxadiazole Derivatives as Fungicidal Agents against Rice Sheath Blight

Zhang

Jiang

Zhu

et al. 2018

J. Agric. Food Chem.

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A series of β-carboline oxadiazoles were synthesized, and their fungicidal activities and mechanism of action against rice sheath blight caused by Rhizoctonia solani was evaluated. The results showed that all of these compounds exhibited significant in vitro fungicidal activity. Significantly, compound 5i (EC = 4.2 μg/mL) displayed the best efficacy and superior fungicidal activity compared to validamycin A (EC = 197.6 μg/mL). Moreover, the in vivo test also demonstrated that compound 5i could effectively control rice sheath blight and showed higher in vivo protective and curative activities against R. solani than validamycin A. Preliminary mechanism studies revealed that compound 5i caused the loss of mitochondrial membrane potential, reactive oxygen species accumulation, cell membrane destruction, and DNA synthesis interference. These findings indicated that compound 5i displayed superior fungicidal activities against R. solani and could be a potential fungicidal candidate against rice sheath blight.

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“…Compound A was prepared according to the previously reported methods. [26] Briefly, the mixture of ethyl 2-bromopropanoate (11.00, 60.0 mmol), 1-(4-chlorophenyl)-1H-pyrazol-3-ol (9.93 g, 50.0 mmol) and potassium carbonate (5.60 g, 40.0 mmol) in N,N-dimethylformamide (DMF, 100 mL) was stirred at 100 ℃ for about 5 h. After completion of the reaction (TLC), the reaction mixture was filtered. The filtrate was evaporated to remove DMF in vacuum and the residue was dissolved in ethyl acetate (50 mL).…”

Section: Synthesis Of Ethyl 2-((1-(4-chlorophenyl)-1hpyrazol-3-yl)oxymentioning

confidence: 99%

Design, Synthesis and Fungicidal Activity against Rhizoctonia solani of New Phenylpyrazoloxyl Propionic Acid Derivatives

Yu¹,

Guan²,

Sun³

et al. 2019

Chin. J. Org. Chem.

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抑制作用, 其中 2-((1-(4-氯苯基)-1H-吡唑-3-基)氧基)-N-(4-硝基苯基)丙酰胺(17) (EC 50 ＝1.05 mg/L)和 2-((1-(4-氯苯基)-1H-吡唑-3-基)氧基)-N-(吡啶-2-基)丙酰胺(22) (EC 50 ＝1.02 mg/L)对水稻纹枯病菌的杀菌活性与对照药物戊唑醇 (EC 50 ＝1.02 mg/L)相当; 2-((1-(4-氯苯基)-1H-吡唑-3-基)氧基)-N-(3,4-二氯苯基)丙酰胺(20) (EC 50 ＝0.95 mg/L)活性略优于商品化对照药剂戊唑醇(EC 50 ＝1.02 mg/L).

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Design, synthesis, and fungicidal activity of novel 1,3,4-oxadiazole derivatives

Cited by 21 publications

References 17 publications

Design and Discovery of Novel Antifungal Quinoline Derivatives with Acylhydrazide as a Promising Pharmacophore

Design and Discovery of Novel Antifungal Quinoline Derivatives with Acylhydrazide as a Promising Pharmacophore

Discovery of β-Carboline Oxadiazole Derivatives as Fungicidal Agents against Rice Sheath Blight

Design, Synthesis and Fungicidal Activity against Rhizoctonia solani of New Phenylpyrazoloxyl Propionic Acid Derivatives

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