Synthesis, antifungal activity and in vitro mechanism of novel 1-substituted-5-trifluoromethyl-1H-pyrazole-4-carboxamide derivatives
Inspired by the wide application of amides in plant pathogens, a series of novel 1-substituted-5-trifluoromethyl‑1H‑pyrazole-4-carboxamide derivatives were designed and synthesized. Bioassay results indicated that some target compounds exhibited excellent and broad-spectrum in vitro and certain in v...
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| Format: | Article |
| Language: | English |
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Elsevier
2022-08-01
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| Series: | Arabian Journal of Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535222003033 |
| _version_ | 1818208649248505856 |
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| author | Jingxin Yang Dewen Xie Chengzhi Zhang Cailong Zhao Zhibing Wu Wei Xue |
| author_facet | Jingxin Yang Dewen Xie Chengzhi Zhang Cailong Zhao Zhibing Wu Wei Xue |
| author_sort | Jingxin Yang |
| collection | DOAJ |
| description | Inspired by the wide application of amides in plant pathogens, a series of novel 1-substituted-5-trifluoromethyl‑1H‑pyrazole-4-carboxamide derivatives were designed and synthesized. Bioassay results indicated that some target compounds exhibited excellent and broad-spectrum in vitro and certain in vivo antifungal activities. Among them, the in vitro EC50 values of Y13 against G. zeae, B. dothidea, F. prolifeatum and F. oxysporum were 13.1, 14.4, 13.3 and 21.4 mg/L, respectively. The in vivo protective activity of Y13 against G. zeae at 100 mg/L was 50.65%. SAR analysis revealed that the phenyl on the 1-position of the pyrazole ring was important for this activity. An antifungal mechanism study of Y13 against G. zeae demonstrated that this compound may disrupt the cell membrane of mycelium, thus inhibiting the growth of fungi. These mechanistic study results were inconsistent with those for traditional amides and may provide a novel view for deep study of this series of pyrazole carboxamide derivatives. |
| first_indexed | 2024-12-12T04:48:10Z |
| format | Article |
| id | doaj.art-da0925b915154d35bb7afbaacd539907 |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-12-12T04:48:10Z |
| publishDate | 2022-08-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj.art-da0925b915154d35bb7afbaacd5399072022-12-22T00:37:33ZengElsevierArabian Journal of Chemistry1878-53522022-08-01158103987Synthesis, antifungal activity and in vitro mechanism of novel 1-substituted-5-trifluoromethyl-1H-pyrazole-4-carboxamide derivativesJingxin Yang0Dewen Xie1Chengzhi Zhang2Cailong Zhao3Zhibing Wu4Wei Xue5State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang 550025, ChinaState Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang 550025, ChinaState Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang 550025, ChinaState Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang 550025, ChinaCorresponding authors.; State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang 550025, ChinaCorresponding authors.; State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang 550025, ChinaInspired by the wide application of amides in plant pathogens, a series of novel 1-substituted-5-trifluoromethyl‑1H‑pyrazole-4-carboxamide derivatives were designed and synthesized. Bioassay results indicated that some target compounds exhibited excellent and broad-spectrum in vitro and certain in vivo antifungal activities. Among them, the in vitro EC50 values of Y13 against G. zeae, B. dothidea, F. prolifeatum and F. oxysporum were 13.1, 14.4, 13.3 and 21.4 mg/L, respectively. The in vivo protective activity of Y13 against G. zeae at 100 mg/L was 50.65%. SAR analysis revealed that the phenyl on the 1-position of the pyrazole ring was important for this activity. An antifungal mechanism study of Y13 against G. zeae demonstrated that this compound may disrupt the cell membrane of mycelium, thus inhibiting the growth of fungi. These mechanistic study results were inconsistent with those for traditional amides and may provide a novel view for deep study of this series of pyrazole carboxamide derivatives.http://www.sciencedirect.com/science/article/pii/S1878535222003033Pyrazole carboxamidesMolecular designFungicidal activityMolecular dockingSAR analysisAntifungal mechanism |
| spellingShingle | Jingxin Yang Dewen Xie Chengzhi Zhang Cailong Zhao Zhibing Wu Wei Xue Synthesis, antifungal activity and in vitro mechanism of novel 1-substituted-5-trifluoromethyl-1H-pyrazole-4-carboxamide derivatives Arabian Journal of Chemistry Pyrazole carboxamides Molecular design Fungicidal activity Molecular docking SAR analysis Antifungal mechanism |
| title | Synthesis, antifungal activity and in vitro mechanism of novel 1-substituted-5-trifluoromethyl-1H-pyrazole-4-carboxamide derivatives |
| title_full | Synthesis, antifungal activity and in vitro mechanism of novel 1-substituted-5-trifluoromethyl-1H-pyrazole-4-carboxamide derivatives |
| title_fullStr | Synthesis, antifungal activity and in vitro mechanism of novel 1-substituted-5-trifluoromethyl-1H-pyrazole-4-carboxamide derivatives |
| title_full_unstemmed | Synthesis, antifungal activity and in vitro mechanism of novel 1-substituted-5-trifluoromethyl-1H-pyrazole-4-carboxamide derivatives |
| title_short | Synthesis, antifungal activity and in vitro mechanism of novel 1-substituted-5-trifluoromethyl-1H-pyrazole-4-carboxamide derivatives |
| title_sort | synthesis antifungal activity and in vitro mechanism of novel 1 substituted 5 trifluoromethyl 1h pyrazole 4 carboxamide derivatives |
| topic | Pyrazole carboxamides Molecular design Fungicidal activity Molecular docking SAR analysis Antifungal mechanism |
| url | http://www.sciencedirect.com/science/article/pii/S1878535222003033 |
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