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)

• Published in: Journal of agricultural and food chemistry Vol. 48; no. 8; pp. 3682 - 3688
• Main Authors: Cantín, Ángel, Moya, Pilar, Miranda, Miguel A, Primo, Jaime, Primo-Yúfera, Eduardo
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.08.2000; Amer Chemical Soc
• Subjects: Agriculture; Agriculture, Multidisciplinary; Animals; Antifungal Agents - chemistry; Antifungal Agents - pharmacology; Biological and medical sciences; Chemical control; Chemistry; Chemistry, Applied; Control; Food Science & Technology; Fundamental and applied biological sciences. Psychology; Fungal plant pathogens; Insecta - microbiology; Life Sciences & Biomedicine; Microbial Sensitivity Tests; Molecular Structure; Penicillium - chemistry; Penicillium - physiology; Physical Sciences; Phytopathology. Animal pests. Plant and forest protection; Protozoa. Invertebrates; Pyrroles - chemical synthesis; Pyrroles - pharmacology; Science & Technology; Spectrum Analysis; ORGANIC-SYNTHESIS; JUVENILE HORMONE-ACTIVITY; insecticide; BETA-KETO-ESTERS; beta-ketoamide; STEREOSELECTIVE SYNTHESIS; analogues; ELECTROORGANIC CHEMISTRY; PENICILLIUM-BREVICOMPACTUM; ELECTROCHEMICAL CYCLIZATION; Penicillium brevicompactum; BIOSYNTHESIS; CONFORMATIONAL-ANALYSIS; fungal metabolites; fungicide; REVERSE-TURN PEPTIDOMIMETICS; Ketoamide; Insecticide; Plant pathogen; Metabolite; Insecta; Pyrrole derivatives; Fungi; Heteroptera; Pest; Chemical control; Lygaeidae; Fungi Imperfecti; Chemical synthesis; Thallophyta; Pesticides; Pest and disease control; Natural product; Biological activity; Fungicide; Microbial origin; Arthropoda; Analog; Oncopeltus fasciatus; Invertebrata; Anti juvenile hormone
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf990948g

New 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