Synthesis and phytotoxic activity of new pyridones derived from 4-hydroxy-6-methylpyridin-2(1H)-one.
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.
Demuner
Antonio Jacinto
AJ
Department of Chemistry, Federal University of Vicosa, Av. P. H. Rolfs, s/n, 36570-000, Vicosa, MG, Brazil. ademuner@ufv.br
Valente
Vania Maria Moreira
VM
Barbosa
Luiz Cláudio Almeida
LC
Rathi
Akshat H
AH
Donohoe
Timothy J
TJ
Thompson
Amber L
AL
D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D011728:Pyridones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045868:Sorghum / Q000187:drug effects*; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared
D011728:Pyridones