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.
To evaluate the effect of simplifying the beta-ketoamide system present in active isolated metabolites from Penicillium brevicompactum (2 and 3) on the activity, new analogues with a monocarbonylic amide functionality have been obtained. In this way, the insecticidal and fungicidal activities have been improved in relation to the natural products taken as lead molecules. Thus, two of the synthetic analogues (5a and 5b) showed very important insecticidal activities against third-instar nymphs of Oncopeltus fasciatus Dallas, with acute LD(50) values of 3.0 and 1.5 microg/cm(2), respectively. Moreover, some analogues showed good levels of fungicidal activity against a wide range of commercially important and taxonomically diverse fungi; remarkably, compound 7c has proved to be highly active against Colletotrichum gloesporoides and Colletotrichum coccodes, with ED(50) values of 2.04 and 11.7 microg/mL, respectively.
Moya
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Instituto de Tecnología Química UPV-CSIC and Departamento de Química, Universidad Politécnica de Valencia, 46022 Valencia, Spain.
Cantín
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A
Miranda
M A
MA
Primo
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J
Primo-Yúfera
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E
D000818:Animals; D020231:Colletotrichum / Q000187:drug effects; D005659:Fungicides, Industrial / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D007313:Insecta; D007306:Insecticides / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D007928:Lethal Dose 50; D008826:Microbial Sensitivity Tests; D010407:Penicillium / Q000378:metabolism*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D005659:Fungicides, Industrial; D007306:Insecticides; C412904:N-(2-methyl-3-oxodec-8-enoyl)-2-pyrroline; C412903:N-(2-methyl-3-oxodecanoyl)-2-pyrroline; D011758:Pyrroles