Synthesis and Biological Evaluation of New Analogues of the Active Fungal Metabolites N -(2-Methyl-3-oxodecanoyl)-2-pyrroline and N -(2-Methyl-3-oxodec-8-enoyl)-2-pyrroline (II)
2000; American Chemical Society; Volume: 48; Issue: 8 Linguagem: Inglês
10.1021/jf990948g
ISSN1520-5118
AutoresÁngel Cantı́n, Pilar Moya, Miguel A. Miranda, Jaime Primo, Eduardo Primo‐Yúfera,
Tópico(s)Plant and fungal interactions
ResumoNew analogues of the bioactive enamides isolated from P. brevicompactum (2 and 3) have been synthesized to improve the biological activities. Two different structural modifications have been introduced: substitution of the aliphatic side chain present in the natural products (1−4) by other groups frequently found in other active compounds and use of other nitrogen-containing five-membered rings with different degrees of oxidation. In this way, the insecticidal and fungicidal activities have been improved. Thus, compound 9, which posseses a 3-pyrroline ring, exhibited important insecticidal activity against third-instar nymphs of Oncopeltus fasciatus Dallas (100% mortality at 7.5 μg/cm2). Remarkable fungicidal activity was also found, and preliminary structure−activity relationships could be established. Keywords: Penicillium brevicompactum; fungal metabolites; β-ketoamide; analogues; insecticide; fungicide
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