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Synthesis, Characterization, and Antifungal Activity of Phenylpyrrole-Substituted Tetramic Acids Bearing Carbonates

by Wen-Qin Xu 1,2, Min Chen 1,2,3, Kun-Yao Wang 1,2, Zheng-Jiao Ren 1,2, Ai-Min Lu 2,3 and Chun-Long Yang 1,2,3,*
1
Jiangsu Key Laboratory of Pesticide Science, Nanjing Agricultural University, Nanjing 210095, China
2
Department of Chemistry, College of Science, Nanjing Agricultural University, Nanjing 210095, China
3
Key Laboratory of Monitoring and Management of Crop Diseases and Pest Insects, Ministry of Agriculture, Nanjing Agricultural University, Nanjing 210095, China
*
Author to whom correspondence should be addressed.
Academic Editor: Maria Emília de Sousa
Molecules 2016, 21(3), 355; https://doi.org/10.3390/molecules21030355
Received: 3 February 2016 / Revised: 8 March 2016 / Accepted: 8 March 2016 / Published: 21 March 2016
(This article belongs to the Section Organic Chemistry)
For the aim of discovering new fungicide, a series of phenylpyrrole-substituted tetramic acid derivatives bearing carbonates 6a–q were designed and synthesized via 4-(2,4-dioxopyrrolidin-3-ylidene)-4-(phenylamino)butanoic acids 4a–k and the cyclized products 1′,3,4,5′-tetrahydro-[2,3′-bipyrrolylidene]-2′,4′,5(1H)-triones 5a–k. The compounds were characterized using IR, 1H- and 13C-NMR spectroscopy, mass spectrometry (EI-MS), and elemental analysis. The structure of 6b was confirmed by X-ray diffraction crystallography. The title compounds 6a–q were bioassayed in vitro against the phytopathogenic fungi Fusarium graminearum, Botrytis cinerea and Rhizoctonia solani at a concentration of 100 μg/mL, respectively. Most compounds displayed good inhibitory activity. View Full-Text
Keywords: tetramic acid; pyrrole; carbonate; synthesis; crystal structure; antifungal activity tetramic acid; pyrrole; carbonate; synthesis; crystal structure; antifungal activity
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Xu, W.-Q.; Chen, M.; Wang, K.-Y.; Ren, Z.-J.; Lu, A.-M.; Yang, C.-L. Synthesis, Characterization, and Antifungal Activity of Phenylpyrrole-Substituted Tetramic Acids Bearing Carbonates. Molecules 2016, 21, 355.

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