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Published on: June 23, 2019
Synthesis and phytotoxic activity of new pyridones derived from 4-hydroxy-6-methylpyridin-2(1H)-one
Antonio Jacinto Demuner1, Vania Maria Moreira Valente, Luiz Cláudio Almeida Barbosa
1Department of Chemistry, Federal University of Vicosa, Av. P. H. Rolfs, s/n, 36570-000, Vicosa, MG, Brazil. ademuner@ufv.br
Abstract:
Commercial dehydroacetic acid was converted into 4-hydroxy-6-methylpyridin-2(1H)-one (3), which was then condensed with several aliphatic aldehydes to produce seven new title compounds in variable yields (35-92%). Reaction of 3 with alpha,beta-unsaturated aldehydes resulted in the formation of condensed pyran derivatives 4g' and 4h'. A mechanism is proposed to explain the formation of such compounds. The effects of all methylpyridin-2(1H)-one derivatives on the development of the dicotyledonous species Ipomoea grandifolia and Cucumis sativus and the monocotyledonous species Sorghum bicolor were evaluated. At the dose of 6.7 x 10(-8) mol a.i./g substrate the compounds showed some phytotoxic selectivity, being more active against the dicotyledonous species. These compounds can be used as lead structures for the development of more active phytotoxic products.
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