Use este identificador para citar ou linkar para este item: https://locus.ufv.br//handle/123456789/14606
Tipo: Artigo
Título: Synthesis of new phytogrowth-inhibitory substituted Aryl-p-Benzoquinones
Autor(es): Barbosa, Luiz Cláudio de Almeida
Alvarenga, Elson Santiago de
Demuner, Antônio Jacinto
Virtuoso, Luciano Sindra
Silva, Antônio Alberto
Abstract: Reaction of [(2-alkyloxy)methyl]-1,4-dimethoxybenzene 10 (alkyl=butyl, hexyl, decyl, tridecyl, tetradecyl, hexadecyl, and octadecyl) with ceric ammonium nitrate in order to produce p-benzoquinones (=cyclohexa-2,5-diene-1,4-diones) afforded 5-[(alkyloxy)methyl]-2-(4-formyl-2,5-dimethoxyphenyl)benzo-1,4-quinones 12a-12g in yields that varied from 46 to 97%, accompanied by 2-[(alkyloxy)methyl]benzo-1,4-quinones 11a-11g in only small quantities (< or =5%). These quinones resemble the natural phytotoxic compound sorgoleone, found in Sorghum bicolor. This reaction exemplifies a general procedure for the synthesis of novel aryl-substituted p-benzoquinones. The selective effects of compounds 12a-12g, at the concentration of 5.5 ppm, on the growth of Cucumis sativus, Sorghum bicolor, Euphorbia heterophylla, and Ipomoea grandifolia were evaluated. All compounds caused some inhibition upon the aerial parts and root growth of the tested plants. The most active compound, 2-(4-formyl-2,5-dimethoxyphenyl)-5-[(tridecyloxy)methyl]-benzo-1,4-quinone (12d), caused between 3 and 18%, and 12 and 29% inhibition on the roots and aerial parts development of Cucumis sativus and Sorghum bicolor, respectively, and between 77 and 85%, and 34 and 52% inhibition on the roots and aerial parts growth of Euphorbia heterophylla and Ipomoea grandifolia, respectively.
Palavras-chave: Phytogrowth-inhibitory
Aryl-p-benzoquinones
Editor: Chemistry & Biodiversity
Tipo de Acesso: Open Access
URI: http://dx.doi.org/10.1002/cbdv.200690059
http://www.locus.ufv.br/handle/123456789/14606
Data do documento: 23-Mai-2006
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