Antifungal properties of n-alkoxyacetic acids and their methyl esters

Article abstract of DOI:10.1002/jps.2600680125

Eleven n-alkoxyacetic acids and their methyl esters, in which the alkyl group was C₁-C₉, C₁₁, or C₁₃, were tested against Aspergillus niger, Trichoderma viride, and Myrothecium verrucaria in Sabouraud dextrose agar at pH 4.0 and 5.6. Toxicity to Candida albicans, Trichophyton mentagrophytes, and Mucor mucedo was determined in the same medium at pH 5.6 and 7.0 in the absence and presence of 10% beef serum. The fungitoxicity of the acids was influenced by chain length, pH of the medium, and absence or presence of adsorbents. The toxicity of the esters was influenced primarily by chain length and to a lesser extent by the medium pH and the presence of beef serum. The order of activity of the n-alkoxyacetic acids was according to the number of linear atoms in the chain: 11>12>10>9>8>7>6>14>16. T. mentagrophytes was the organism most strongly affected by these compounds, with the esters being slightly more active than the acids. Compared to other fatty acid analogs, the order of fungitoxicity, on a weight basis, was 2-alkynoic acids >2-alkenoic acids > alkanoic acids > 2-bromoalkanoic acid > 2-fluoroalkanoic acids > n-alkoxyacetic acids.