Molecules 2009, 14(12), 4973-4986; doi:10.3390/molecules14124973
Article

Synthesis and Phytotoxic Activity of New Pyridones Derived from 4-Hydroxy-6-Methylpyridin-2(1H)-one

Antonio Jacinto Demuner 1 email, Vania Maria Moreira Valente 1 email, Luiz Cláudio Almeida Barbosa 1,2,* email, Akshat Rathi 2 email, Timothy J. Donohoe 2 email and Amber L. Thompson 2 email
1 Department of Chemistry, Federal University of Vicosa, Av. P. H. Rolfs, s/n, 36570-000, Vicosa, MG, Brazil 2 Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK
* Author to whom correspondence should be addressed.
Received: 5 November 2009; in revised form: 24 November 2009 / Accepted: 30 November 2009 / Published: 1 December 2009
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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 α,β-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 × 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.
Keywords: pyridine; x-ray; phytotoxicity; weeds; herbicides

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MDPI and ACS Style

Jacinto Demuner, A.; Moreira Valente, V.M.; Almeida Barbosa, L.C.; Rathi, A.; Donohoe, T.J.; Thompson, A.L. Synthesis and Phytotoxic Activity of New Pyridones Derived from 4-Hydroxy-6-Methylpyridin-2(1H)-one. Molecules 2009, 14, 4973-4986.

AMA Style

Jacinto Demuner A, Moreira Valente VM, Almeida Barbosa LC, Rathi A, Donohoe TJ, Thompson AL. Synthesis and Phytotoxic Activity of New Pyridones Derived from 4-Hydroxy-6-Methylpyridin-2(1H)-one. Molecules. 2009; 14(12):4973-4986.

Chicago/Turabian Style

Jacinto Demuner, Antonio; Moreira Valente, Vania Maria; Almeida Barbosa, Luiz Cláudio; Rathi, Akshat; Donohoe, Timothy J.; Thompson, Amber L. 2009. "Synthesis and Phytotoxic Activity of New Pyridones Derived from 4-Hydroxy-6-Methylpyridin-2(1H)-one." Molecules 14, no. 12: 4973-4986.

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