Structure–toxicity relationships and enhanced acaricidal efficacy of phenylacetonitrile and nitrile derivatives against four mite species
摘要
The essential oil extracted from Lepidium meyenii roots exhibited notable acaricidal efficacy against Dermatophagoides farinae, D. pteronyssinus, Dermanyssus gallinae, and Tyrophagus putrescentiae. The toxicity of the oil, as determined by the fumigant method, was 166, 132, and 13.4 times greater than that of diethyltoluamide against D. farinae, D. pteronyssinus, and T. putrescentiae, respectively. In the contact method, the essential oil showed toxicity levels 2.8, 2.3, and 0.9 times greater than those of diethyltoluamide for the same species. Phenylacetonitrile (72.76%) was identified as the major active component, followed by ethyl linoleic acid (13.52%) and ethyl palmitic acid (7.92%). Phenylacetonitrile was isolated from L. meyenii oil and characterized using spectroscopic techniques. Structure–toxicity relationship analysis revealed that 3-methoxyphenylacetonitrile exhibited the highest fumigant activity, with LD50 values up to 348 times lower than those of diethyltoluamide and permethrin. In contrast, 3-methylphenylacetonitrile showed superior efficacy against D. gallinae in the fumigant (LD50, 7.97 μg·cm−3) and contact (LD50, 9.78 μg·cm−2) methods. This study underscores phenylacetonitrile and nitrile derivatives as promising eco-friendly alternatives to synthetic acaricides due to their high efficacy and low human toxicity. Functional group modifications, particularly methoxy substitutions, significantly enhanced acaricidal activity, likely due to increased electron-donating effects that improve the binding affinity to target proteins. Methyl-substituted derivatives demonstrated moderate activity, attributed to their hydrophobic interactions facilitating exoskeletal penetration. These findings suggest that phenylacetonitrile and its derivatives have strong potential as natural acaricides for managing mite species while minimizing environmental impact. Further study is necessary to explore mechanisms of action and enhance formulations for commercial application.