Synthesis and antifungal activity of new salicylic acid derivatives
A simple one-step procedure for synthesis of 1-methoxy-1-oxoalkan-2-yl salicylates and 1-methoxy-1-oxoalkan-2-yl 2-[(1-methoxy-1-oxoalkan-2-yl)oxy]benzoates by reaction of salicylic acid with several methyl 2-bromoalkanoates was developed. The reactions were carried out in N,N-dimethylformamide (DMF...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Sciendo
2017-03-01
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| Series: | Polish Journal of Chemical Technology |
| Subjects: | |
| Online Access: | https://doi.org/10.1515/pjct-2017-0019 |
| _version_ | 1818578651657011200 |
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| author | Wodnicka Alicja Huzar Elżbieta Krawczyk Maria Kwiecień Halina |
| author_facet | Wodnicka Alicja Huzar Elżbieta Krawczyk Maria Kwiecień Halina |
| author_sort | Wodnicka Alicja |
| collection | DOAJ |
| description | A simple one-step procedure for synthesis of 1-methoxy-1-oxoalkan-2-yl salicylates and 1-methoxy-1-oxoalkan-2-yl 2-[(1-methoxy-1-oxoalkan-2-yl)oxy]benzoates by reaction of salicylic acid with several methyl 2-bromoalkanoates was developed. The reactions were carried out in N,N-dimethylformamide (DMF) in the presence of anhydrous potassium carbonate. Conditions for regioselective synthesis of target compounds were established. The developed procedure could be easily applied in the industrial production process. The new salicylic acid derivatives were obtained with satisfactory yields and were characterized by MS and 1H NMR spectra. The fungicidal activity of the prepared compounds was tested in vitro against seven species of plant pathogenic fungi. The best results were observed for 1-methoxy-1-oxoalkan-2-yl salicylates which showed moderate or good activity against Botrytis cinerea and Rhizoctonia solani. |
| first_indexed | 2024-12-16T06:49:12Z |
| format | Article |
| id | doaj.art-174d46238ff54597b3387d7607bbcb1f |
| institution | Directory Open Access Journal |
| issn | 1899-4741 |
| language | English |
| last_indexed | 2024-12-16T06:49:12Z |
| publishDate | 2017-03-01 |
| publisher | Sciendo |
| record_format | Article |
| series | Polish Journal of Chemical Technology |
| spelling | doaj.art-174d46238ff54597b3387d7607bbcb1f2022-12-21T22:40:27ZengSciendoPolish Journal of Chemical Technology1899-47412017-03-0119114314810.1515/pjct-2017-0019pjct-2017-0019Synthesis and antifungal activity of new salicylic acid derivativesWodnicka Alicja0Huzar Elżbieta1Krawczyk Maria2Kwiecień Halina3West Pomeranian University of Technology, Szczecin, Faculty of Chemical Technology and Engineering, Institute of Organic Chemical Technology, al. Piastów 42, 71-065, Szczecin, PolandWest Pomeranian University of Technology, Szczecin, Faculty of Chemical Technology and Engineering, Institute of Organic Chemical Technology, al. Piastów 42, 71-065, Szczecin, PolandInstitute of Industrial Organic Chemistry, Annopol 6, 03-236, Warszawa, PolandWest Pomeranian University of Technology, Szczecin, Faculty of Chemical Technology and Engineering, Institute of Organic Chemical Technology, al. Piastów 42, 71-065, Szczecin, PolandA simple one-step procedure for synthesis of 1-methoxy-1-oxoalkan-2-yl salicylates and 1-methoxy-1-oxoalkan-2-yl 2-[(1-methoxy-1-oxoalkan-2-yl)oxy]benzoates by reaction of salicylic acid with several methyl 2-bromoalkanoates was developed. The reactions were carried out in N,N-dimethylformamide (DMF) in the presence of anhydrous potassium carbonate. Conditions for regioselective synthesis of target compounds were established. The developed procedure could be easily applied in the industrial production process. The new salicylic acid derivatives were obtained with satisfactory yields and were characterized by MS and 1H NMR spectra. The fungicidal activity of the prepared compounds was tested in vitro against seven species of plant pathogenic fungi. The best results were observed for 1-methoxy-1-oxoalkan-2-yl salicylates which showed moderate or good activity against Botrytis cinerea and Rhizoctonia solani.https://doi.org/10.1515/pjct-2017-0019salicylic acidsalicylatesantifungal activity |
| spellingShingle | Wodnicka Alicja Huzar Elżbieta Krawczyk Maria Kwiecień Halina Synthesis and antifungal activity of new salicylic acid derivatives Polish Journal of Chemical Technology salicylic acid salicylates antifungal activity |
| title | Synthesis and antifungal activity of new salicylic acid derivatives |
| title_full | Synthesis and antifungal activity of new salicylic acid derivatives |
| title_fullStr | Synthesis and antifungal activity of new salicylic acid derivatives |
| title_full_unstemmed | Synthesis and antifungal activity of new salicylic acid derivatives |
| title_short | Synthesis and antifungal activity of new salicylic acid derivatives |
| title_sort | synthesis and antifungal activity of new salicylic acid derivatives |
| topic | salicylic acid salicylates antifungal activity |
| url | https://doi.org/10.1515/pjct-2017-0019 |
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