Design, Synthesis, and Antifungal Activity of Some Novel Phenylthiazole Derivatives Containing an Acylhydrazone Moiety
Crop fungal diseases pose a serious threat to global crop production and quality. Developing new and efficient fungicides is an important measure to control crop diseases. Phenylthiazole was found to be an excellent antifungal skeleton based on our previous study on the structural optimization and b...
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| Format: | Article |
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MDPI AG
2023-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/20/7084 |
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| author | Yao Tian Jinchao Shi Xiaoqian Deng Tingyu Yu Yong Hu Richa Hu Yufeng Lei Linhua Yu Xiang Zhu Junkai Li |
| author_facet | Yao Tian Jinchao Shi Xiaoqian Deng Tingyu Yu Yong Hu Richa Hu Yufeng Lei Linhua Yu Xiang Zhu Junkai Li |
| author_sort | Yao Tian |
| collection | DOAJ |
| description | Crop fungal diseases pose a serious threat to global crop production and quality. Developing new and efficient fungicides is an important measure to control crop diseases. Phenylthiazole was found to be an excellent antifungal skeleton based on our previous study on the structural optimization and biological activity of the natural product thiasporine A. To find new fungicides, 45 phenylthiazole derivatives containing an acylhydrazone moiety were designed and synthesized by the principle of active substructure splicing. Forty-two of the forty-five compounds are novel, except for compounds <b>E1</b>, <b>E14</b>, and <b>E33</b>. Their structures were structurally characterized by <sup>1</sup>H NMR, <sup>13</sup>C NMR, and HRMS. The antifungal activities of the target compounds against <i>Magnaporthe oryzae Colletotrichum camelliaet</i>, <i>Bipolaris maydis</i>, and <i>Sclerotinia sclerotiorum</i> were evaluated at 25 μg/mL. The bioassay results revealed that most of these compounds exhibited excellent antifungal activities against <i>M. oryzae</i> and <i>C. camelliaet</i> at 25 μg/mL. In particular, compounds <b>E4</b>, <b>E10</b>, <b>E14</b>, <b>E17</b>, <b>E23</b>, <b>E26</b>, and <b>E27</b> showed the inhibition rate of more than 80% against <i>M. oryzae</i>, with EC<sub>50</sub> values of 1.66, 2.01, 2.26, 1.45, 1.50, 1.29, and 2.65 μg/mL, respectively, which were superior to that of the commercial fungicides Isoprothiolane (EC<sub>50</sub> = 3.22 μg/mL) and Phenazine-1-carboxylic acid (EC<sub>50</sub> = 27.87 μg/mL). The preliminary structure–activity relationship (SAR) results suggested that introducing methyl, halogen, or methoxy at the ortho-position of R<sup>1</sup> and the para-position of R<sup>2</sup> can endow the final structure with excellent antifungal activity against <i>M. oryzae</i>. The current results provide useful data for developing phenylthiazole derivatives as new fungicides for controlling rice blast caused by <i>M. oryzae</i>. |
| first_indexed | 2024-03-10T21:01:04Z |
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| publishDate | 2023-10-01 |
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| spelling | doaj.art-da9db23d5d6f4e13a9b0058b8fda758c2023-11-19T17:32:30ZengMDPI AGMolecules1420-30492023-10-012820708410.3390/molecules28207084Design, Synthesis, and Antifungal Activity of Some Novel Phenylthiazole Derivatives Containing an Acylhydrazone MoietyYao Tian0Jinchao Shi1Xiaoqian Deng2Tingyu Yu3Yong Hu4Richa Hu5Yufeng Lei6Linhua Yu7Xiang Zhu8Junkai Li9Engineering Research Center of Ecology and Agricultural Use of Wetland, Ministry of Education, Hubei Key Laboratory of Waterlogging Disaster and Agricultural Use of Wetland, College of Agriculture, Yangtze University, Jingzhou 434025, ChinaEngineering Research Center of Ecology and Agricultural Use of Wetland, Ministry of Education, Hubei Key Laboratory of Waterlogging Disaster and Agricultural Use of Wetland, College of Agriculture, Yangtze University, Jingzhou 434025, ChinaEngineering Research Center of Ecology and Agricultural Use of Wetland, Ministry of Education, Hubei Key Laboratory of Waterlogging Disaster and Agricultural Use of Wetland, College of Agriculture, Yangtze University, Jingzhou 434025, ChinaEngineering Research Center of Ecology and Agricultural Use of Wetland, Ministry of Education, Hubei Key Laboratory of Waterlogging Disaster and Agricultural Use of Wetland, College of Agriculture, Yangtze University, Jingzhou 434025, ChinaEngineering Research Center of Ecology and Agricultural Use of Wetland, Ministry of Education, Hubei Key Laboratory of Waterlogging Disaster and Agricultural Use of Wetland, College of Agriculture, Yangtze University, Jingzhou 434025, ChinaEngineering Research Center of Ecology and Agricultural Use of Wetland, Ministry of Education, Hubei Key Laboratory of Waterlogging Disaster and Agricultural Use of Wetland, College of Agriculture, Yangtze University, Jingzhou 434025, ChinaEngineering Research Center of Ecology and Agricultural Use of Wetland, Ministry of Education, Hubei Key Laboratory of Waterlogging Disaster and Agricultural Use of Wetland, College of Agriculture, Yangtze University, Jingzhou 434025, ChinaEngineering Research Center of Ecology and Agricultural Use of Wetland, Ministry of Education, Hubei Key Laboratory of Waterlogging Disaster and Agricultural Use of Wetland, College of Agriculture, Yangtze University, Jingzhou 434025, ChinaEngineering Research Center of Ecology and Agricultural Use of Wetland, Ministry of Education, Hubei Key Laboratory of Waterlogging Disaster and Agricultural Use of Wetland, College of Agriculture, Yangtze University, Jingzhou 434025, ChinaEngineering Research Center of Ecology and Agricultural Use of Wetland, Ministry of Education, Hubei Key Laboratory of Waterlogging Disaster and Agricultural Use of Wetland, College of Agriculture, Yangtze University, Jingzhou 434025, ChinaCrop fungal diseases pose a serious threat to global crop production and quality. Developing new and efficient fungicides is an important measure to control crop diseases. Phenylthiazole was found to be an excellent antifungal skeleton based on our previous study on the structural optimization and biological activity of the natural product thiasporine A. To find new fungicides, 45 phenylthiazole derivatives containing an acylhydrazone moiety were designed and synthesized by the principle of active substructure splicing. Forty-two of the forty-five compounds are novel, except for compounds <b>E1</b>, <b>E14</b>, and <b>E33</b>. Their structures were structurally characterized by <sup>1</sup>H NMR, <sup>13</sup>C NMR, and HRMS. The antifungal activities of the target compounds against <i>Magnaporthe oryzae Colletotrichum camelliaet</i>, <i>Bipolaris maydis</i>, and <i>Sclerotinia sclerotiorum</i> were evaluated at 25 μg/mL. The bioassay results revealed that most of these compounds exhibited excellent antifungal activities against <i>M. oryzae</i> and <i>C. camelliaet</i> at 25 μg/mL. In particular, compounds <b>E4</b>, <b>E10</b>, <b>E14</b>, <b>E17</b>, <b>E23</b>, <b>E26</b>, and <b>E27</b> showed the inhibition rate of more than 80% against <i>M. oryzae</i>, with EC<sub>50</sub> values of 1.66, 2.01, 2.26, 1.45, 1.50, 1.29, and 2.65 μg/mL, respectively, which were superior to that of the commercial fungicides Isoprothiolane (EC<sub>50</sub> = 3.22 μg/mL) and Phenazine-1-carboxylic acid (EC<sub>50</sub> = 27.87 μg/mL). The preliminary structure–activity relationship (SAR) results suggested that introducing methyl, halogen, or methoxy at the ortho-position of R<sup>1</sup> and the para-position of R<sup>2</sup> can endow the final structure with excellent antifungal activity against <i>M. oryzae</i>. The current results provide useful data for developing phenylthiazole derivatives as new fungicides for controlling rice blast caused by <i>M. oryzae</i>.https://www.mdpi.com/1420-3049/28/20/7084synthesisphenylthiazoleacylhydrazoneantifungal activitystructure–activity relationshiprice blast |
| spellingShingle | Yao Tian Jinchao Shi Xiaoqian Deng Tingyu Yu Yong Hu Richa Hu Yufeng Lei Linhua Yu Xiang Zhu Junkai Li Design, Synthesis, and Antifungal Activity of Some Novel Phenylthiazole Derivatives Containing an Acylhydrazone Moiety Molecules synthesis phenylthiazole acylhydrazone antifungal activity structure–activity relationship rice blast |
| title | Design, Synthesis, and Antifungal Activity of Some Novel Phenylthiazole Derivatives Containing an Acylhydrazone Moiety |
| title_full | Design, Synthesis, and Antifungal Activity of Some Novel Phenylthiazole Derivatives Containing an Acylhydrazone Moiety |
| title_fullStr | Design, Synthesis, and Antifungal Activity of Some Novel Phenylthiazole Derivatives Containing an Acylhydrazone Moiety |
| title_full_unstemmed | Design, Synthesis, and Antifungal Activity of Some Novel Phenylthiazole Derivatives Containing an Acylhydrazone Moiety |
| title_short | Design, Synthesis, and Antifungal Activity of Some Novel Phenylthiazole Derivatives Containing an Acylhydrazone Moiety |
| title_sort | design synthesis and antifungal activity of some novel phenylthiazole derivatives containing an acylhydrazone moiety |
| topic | synthesis phenylthiazole acylhydrazone antifungal activity structure–activity relationship rice blast |
| url | https://www.mdpi.com/1420-3049/28/20/7084 |
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