Summary
An antifungal study againstAspergillus niger,A. oryzae,Myrothecium verrucaria, andTrichoderma viride in Yeast Nitrogen Base supplemented with 1%D-glucose and 0.088%L-asparagine was carried out using 8-quinolinol and 3-, 5-, 6-, 7-, 3,6-, and 5,7-chlorinated and brominated-8-quinolinols. Binary mixtures of 3- and 6-halo- and 5- and 7-halo-8-quinolinols were intermolecularly synergistic. MICs of the monohalo synergistic mixtures admixed with a MIC of the corresponding dihalo-8-quinolinols were not synergistic. The dihalo-8-quinolinols with substituents in positions corresponding to those of the synergistic binary mixtures appeared to attack the same sites of action as the binary pairs. The enhanced activities of 3,6- and 5,7-dichloro-8-quinolinols and 3,6- and 5,7-dibromo-8-quinolinols are believed to be due to intramolecular synergism. The greater fungitoxicity of 5-, 6-, and 7-monohalo-8-quinolinols over 8-quinolinol can also be explained as due to intramolecular synergism. 3,6-Dihalo- and 5,7-dihalo-8-quinolinols formed synergistic pairs of compounds.
Zusammenfassung
8-Chinolinol und verschiedene halogenierte 8-Chinolinole wurden auf ihre Fungitoxizität gegenüberAspergillus niger,A. oryzae,Myrothecium verrucaria undTrichoderma viride untersucht. Binäre Mischungen von 3- und 6-Halogen- bzw. 5- und 7-Halogen-8-chinolinol zeigten intermolekularen Synergismus, während bei Mischungen von mono- und dihalogenierten 8-Chinolinolen kein entsprechender Effekt beobachtet werden konnte. Die erhöhte Aktivität von 3,6-und 5,7-Dichlor-8-chinolinol und 3,6- und 5,7-Dibrom-8-chinolinol wird durch intramolekularen Synergismus erklärt, desgleichen die höhere Aktivität monohalogenierter 8-Chinolinole gegenüber 8-Chinolinol. 3,6-Dihalogenierte und 5,7-dihalogenierte 8-Chinolinole bilden synergistische Paare.
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Gershon, H., Gershon, M. Intramolecular synergism, an explanation for the enhanced fungitoxicity of halo-8-quinolinols. Monatsh Chem 126, 1303–1309 (1995). https://doi.org/10.1007/BF00807059
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DOI: https://doi.org/10.1007/BF00807059