title: Synthesis, Characterization, and Antifungal Activity of Phenylpyrrole-Substituted Tetramic Acids Bearing Carbonates.
abstract: 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 (13)C-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.
authors.affiliation: Jiangsu Key Laboratory of Pesticide Science, Nanjing Agricultural University, Nanjing 210095, China. 2013111008@njau.edu.cn.|Department of Chemistry, College of Science, Nanjing Agricultural University, Nanjing 210095, China. 2013111008@njau.edu.cn.
authors.forename: Wen-Qin
authors.initials: WQ
authors.lastname: Xu
authors.affiliation: Jiangsu Key Laboratory of Pesticide Science, Nanjing Agricultural University, Nanjing 210095, China. chenmin@njau.edu.cn.|Department of Chemistry, College of Science, Nanjing Agricultural University, Nanjing 210095, China. chenmin@njau.edu.cn.|Key Laboratory of Monitoring and Management of Crop Diseases and Pest Insects, Ministry of Agriculture, Nanjing Agricultural University, Nanjing 210095, China. chenmin@njau.edu.cn.
authors.forename: Min
authors.initials: M
authors.lastname: Chen
authors.affiliation: Jiangsu Key Laboratory of Pesticide Science, Nanjing Agricultural University, Nanjing 210095, China. 2014111008@njau.edu.cn.|Department of Chemistry, College of Science, Nanjing Agricultural University, Nanjing 210095, China. 2014111008@njau.edu.cn.
authors.forename: Kun-Yao
authors.initials: KY
authors.lastname: Wang
authors.affiliation: Jiangsu Key Laboratory of Pesticide Science, Nanjing Agricultural University, Nanjing 210095, China. 2013111010@njau.edu.cn.|Department of Chemistry, College of Science, Nanjing Agricultural University, Nanjing 210095, China. 2013111010@njau.edu.cn.
authors.forename: Zheng-Jiao
authors.initials: ZJ
authors.lastname: Ren
authors.affiliation: Department of Chemistry, College of Science, Nanjing Agricultural University, Nanjing 210095, China. luaimin@njau.edu.cn.|Key Laboratory of Monitoring and Management of Crop Diseases and Pest Insects, Ministry of Agriculture, Nanjing Agricultural University, Nanjing 210095, China. luaimin@njau.edu.cn.
authors.forename: Ai-Min
authors.initials: AM
authors.lastname: Lu
authors.affiliation: Jiangsu Key Laboratory of Pesticide Science, Nanjing Agricultural University, Nanjing 210095, China. ycl@njau.edu.cn.|Department of Chemistry, College of Science, Nanjing Agricultural University, Nanjing 210095, China. ycl@njau.edu.cn.|Key Laboratory of Monitoring and Management of Crop Diseases and Pest Insects, Ministry of Agriculture, Nanjing Agricultural University, Nanjing 210095, China. ycl@njau.edu.cn.
authors.forename: Chun-Long
authors.initials: CL
authors.lastname: Yang
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002254:Carbonates / Q000138:chemical synthesis / Q000737:chemistry; D018360:Crystallography, X-Ray; D005659:Fungicides, Industrial / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005670:Fusarium / Q000187:drug effects; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011760:Pyrrolidinones / Q000138:chemical synthesis / Q000737:chemistry; D013329:Structure-Activity Relationship; D014961:X-Ray Diffraction
chemical_list: D000935:Antifungal Agents; D002254:Carbonates; D005659:Fungicides, Industrial; D011758:Pyrroles; D011760:Pyrrolidinones; C009435:tetramic acid
keywords: antifungal activity; carbonate; crystal structure; pyrrole; synthesis; tetramic acid