Synthesis, Characterization, and Agricultural Biological Activities of 5-Fluoro-2-hydroxy Butyrophenone

A novel synthetic approach towards 5-fluoro-2-hydroxy butyrophenone is reported. Using 4-fluorophenol as a raw material, the processes of etherification protection, Friedel-Crafts acylation and demethylation provide the target compound under mild conditions. The structure was characterized by the me...

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Main Authors: Fengli Xin, Chunhua Du, Gongjia Lan, Zhuanping Wu
Format: Article
Language:English
Published: Wiley 2013-01-01
Series:Journal of Chemistry
Online Access:http://dx.doi.org/10.1155/2013/895892
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author Fengli Xin
Chunhua Du
Gongjia Lan
Zhuanping Wu
author_facet Fengli Xin
Chunhua Du
Gongjia Lan
Zhuanping Wu
author_sort Fengli Xin
collection DOAJ
description A novel synthetic approach towards 5-fluoro-2-hydroxy butyrophenone is reported. Using 4-fluorophenol as a raw material, the processes of etherification protection, Friedel-Crafts acylation and demethylation provide the target compound under mild conditions. The structure was characterized by the melting point and IR, MS, 1H-NMR, and 13C-NMR spectroscopy. The bioassay results indicate that the target compound exhibits potent antifungal activities against Valsa mali, Coniella dipodiella, and other agricultural plant fungi. The target compound also shows potent herbicidal activities for Lactuca sativa, a dicotyledon, and Echinochloa crus-galli, a monocotyledon. The toxicity regression C50 values of the compound against Valsa mali, Coniothyrium diplodiella, Lactuca sativa seedling, and Echinochloa crusgalli seedling were calculated by SPSS. The Hormesis effect for roots of Echinochloa crusgalli was confirmed.
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publishDate 2013-01-01
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spelling doaj-art-4318865737634ca7bb586e79fb8e5e4b2025-02-03T06:07:59ZengWileyJournal of Chemistry2090-90632090-90712013-01-01201310.1155/2013/895892895892Synthesis, Characterization, and Agricultural Biological Activities of 5-Fluoro-2-hydroxy ButyrophenoneFengli Xin0Chunhua Du1Gongjia Lan2Zhuanping Wu3College of Chemistry & Pharmacy, Qingdao Agricultural University, Research Center of Agricultural Bionic Engineering & Technology of Shandong Province, Qingdao 266109, ChinaCollege of Chemistry & Pharmacy, Qingdao Agricultural University, Research Center of Agricultural Bionic Engineering & Technology of Shandong Province, Qingdao 266109, ChinaCollege of Chemistry & Pharmacy, Qingdao Agricultural University, Research Center of Agricultural Bionic Engineering & Technology of Shandong Province, Qingdao 266109, ChinaCollege of Chemistry & Pharmacy, Qingdao Agricultural University, Research Center of Agricultural Bionic Engineering & Technology of Shandong Province, Qingdao 266109, ChinaA novel synthetic approach towards 5-fluoro-2-hydroxy butyrophenone is reported. Using 4-fluorophenol as a raw material, the processes of etherification protection, Friedel-Crafts acylation and demethylation provide the target compound under mild conditions. The structure was characterized by the melting point and IR, MS, 1H-NMR, and 13C-NMR spectroscopy. The bioassay results indicate that the target compound exhibits potent antifungal activities against Valsa mali, Coniella dipodiella, and other agricultural plant fungi. The target compound also shows potent herbicidal activities for Lactuca sativa, a dicotyledon, and Echinochloa crus-galli, a monocotyledon. The toxicity regression C50 values of the compound against Valsa mali, Coniothyrium diplodiella, Lactuca sativa seedling, and Echinochloa crusgalli seedling were calculated by SPSS. The Hormesis effect for roots of Echinochloa crusgalli was confirmed.http://dx.doi.org/10.1155/2013/895892
spellingShingle Fengli Xin
Chunhua Du
Gongjia Lan
Zhuanping Wu
Synthesis, Characterization, and Agricultural Biological Activities of 5-Fluoro-2-hydroxy Butyrophenone
Journal of Chemistry
title Synthesis, Characterization, and Agricultural Biological Activities of 5-Fluoro-2-hydroxy Butyrophenone
title_full Synthesis, Characterization, and Agricultural Biological Activities of 5-Fluoro-2-hydroxy Butyrophenone
title_fullStr Synthesis, Characterization, and Agricultural Biological Activities of 5-Fluoro-2-hydroxy Butyrophenone
title_full_unstemmed Synthesis, Characterization, and Agricultural Biological Activities of 5-Fluoro-2-hydroxy Butyrophenone
title_short Synthesis, Characterization, and Agricultural Biological Activities of 5-Fluoro-2-hydroxy Butyrophenone
title_sort synthesis characterization and agricultural biological activities of 5 fluoro 2 hydroxy butyrophenone
url http://dx.doi.org/10.1155/2013/895892
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