Novel 1,3,4-oxadiazole thioether and sulfone derivatives bearing a flexible N-heterocyclic moiety: Synthesis, characterization, and anti-microorganism activity
In the search for more efficient and versatile anti-phytopathogen agents, a series of new 1,3,4-oxadiazole thioether/sulfone analogues bearing a flexible N-containing heterocyclic pattern were elaborately prepared, and their bioactivities against plant pathogenic microorganisms were systematically e...
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| Format: | Article |
| Language: | English |
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Elsevier
2023-02-01
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| Series: | Arabian Journal of Chemistry |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S187853522200795X |
| _version_ | 1797952742914785280 |
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| author | Fang Wang Bin-Xin Yang Tai-Hong Zhang Qing-Qing Tao Xiang Zhou Pei-Yi Wang Song Yang |
| author_facet | Fang Wang Bin-Xin Yang Tai-Hong Zhang Qing-Qing Tao Xiang Zhou Pei-Yi Wang Song Yang |
| author_sort | Fang Wang |
| collection | DOAJ |
| description | In the search for more efficient and versatile anti-phytopathogen agents, a series of new 1,3,4-oxadiazole thioether/sulfone analogues bearing a flexible N-containing heterocyclic pattern were elaborately prepared, and their bioactivities against plant pathogenic microorganisms were systematically evaluated. Bioassay screening results demonstrated that compounds 32 and 33 significantly inhibited the growth of Xanthomonas oryzae pv. oryzae (Xoo) in vitro (32, EC50 = 5.17 mg L−1; 33, EC50 = 1.19 mg L−1), which were significantly surpass commercial bismerthiazol (BT) and thiodiazole copper (TC). Meanwhile, pot experiments confirmed the prospective applications of compound 33 in managing rice bacterial leaf blight and its good safety toward rice plants. Further studies showed that compound 33 interfered with the formation of bacterial biofilms and inhibited bacterial virulence factors. Furthermore, an in vitro antifungal bioassay showed that compound 32 possessed remarkable growth inhibitory activity against Sclerotinia sclerotiorum (S.s., EC50 = 22.16 mg L−1) and Verticillium dahlia (V.d. EC50 = 32.78 mg L−1). These results all confirmed that the designed 1,3,4-oxadiazole compounds displayed potential for managing plant microbial diseases through targeting dihydrolipoamide S-succinyltransferase (DLST). |
| first_indexed | 2024-04-10T22:52:10Z |
| format | Article |
| id | doaj.art-08c994ca27b04b1fa34e34d4142e60f8 |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-04-10T22:52:10Z |
| publishDate | 2023-02-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj.art-08c994ca27b04b1fa34e34d4142e60f82023-01-15T04:21:39ZengElsevierArabian Journal of Chemistry1878-53522023-02-01162104479Novel 1,3,4-oxadiazole thioether and sulfone derivatives bearing a flexible N-heterocyclic moiety: Synthesis, characterization, and anti-microorganism activityFang Wang0Bin-Xin Yang1Tai-Hong Zhang2Qing-Qing Tao3Xiang Zhou4Pei-Yi Wang5Song Yang6State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R and 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 and 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 and 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 and 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 and 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 and 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 and D of Fine Chemicals of Guizhou University, Guiyang 550025, ChinaIn the search for more efficient and versatile anti-phytopathogen agents, a series of new 1,3,4-oxadiazole thioether/sulfone analogues bearing a flexible N-containing heterocyclic pattern were elaborately prepared, and their bioactivities against plant pathogenic microorganisms were systematically evaluated. Bioassay screening results demonstrated that compounds 32 and 33 significantly inhibited the growth of Xanthomonas oryzae pv. oryzae (Xoo) in vitro (32, EC50 = 5.17 mg L−1; 33, EC50 = 1.19 mg L−1), which were significantly surpass commercial bismerthiazol (BT) and thiodiazole copper (TC). Meanwhile, pot experiments confirmed the prospective applications of compound 33 in managing rice bacterial leaf blight and its good safety toward rice plants. Further studies showed that compound 33 interfered with the formation of bacterial biofilms and inhibited bacterial virulence factors. Furthermore, an in vitro antifungal bioassay showed that compound 32 possessed remarkable growth inhibitory activity against Sclerotinia sclerotiorum (S.s., EC50 = 22.16 mg L−1) and Verticillium dahlia (V.d. EC50 = 32.78 mg L−1). These results all confirmed that the designed 1,3,4-oxadiazole compounds displayed potential for managing plant microbial diseases through targeting dihydrolipoamide S-succinyltransferase (DLST).http://www.sciencedirect.com/science/article/pii/S187853522200795X1, 3, 4-oxadiazole derivativesThioether derivativesSulfone derivativesAntibacterial activity |
| spellingShingle | Fang Wang Bin-Xin Yang Tai-Hong Zhang Qing-Qing Tao Xiang Zhou Pei-Yi Wang Song Yang Novel 1,3,4-oxadiazole thioether and sulfone derivatives bearing a flexible N-heterocyclic moiety: Synthesis, characterization, and anti-microorganism activity Arabian Journal of Chemistry 1, 3, 4-oxadiazole derivatives Thioether derivatives Sulfone derivatives Antibacterial activity |
| title | Novel 1,3,4-oxadiazole thioether and sulfone derivatives bearing a flexible N-heterocyclic moiety: Synthesis, characterization, and anti-microorganism activity |
| title_full | Novel 1,3,4-oxadiazole thioether and sulfone derivatives bearing a flexible N-heterocyclic moiety: Synthesis, characterization, and anti-microorganism activity |
| title_fullStr | Novel 1,3,4-oxadiazole thioether and sulfone derivatives bearing a flexible N-heterocyclic moiety: Synthesis, characterization, and anti-microorganism activity |
| title_full_unstemmed | Novel 1,3,4-oxadiazole thioether and sulfone derivatives bearing a flexible N-heterocyclic moiety: Synthesis, characterization, and anti-microorganism activity |
| title_short | Novel 1,3,4-oxadiazole thioether and sulfone derivatives bearing a flexible N-heterocyclic moiety: Synthesis, characterization, and anti-microorganism activity |
| title_sort | novel 1 3 4 oxadiazole thioether and sulfone derivatives bearing a flexible n heterocyclic moiety synthesis characterization and anti microorganism activity |
| topic | 1, 3, 4-oxadiazole derivatives Thioether derivatives Sulfone derivatives Antibacterial activity |
| url | http://www.sciencedirect.com/science/article/pii/S187853522200795X |
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