The acaricidal activity of clove (Eugenia caryophyllata) bud oil-derived eugenol and its congeners (acetyleugenol, isoeugenol, and methyleugenol) against adults of Dermatophagoides farinae and Dermatophagoides pteronyssinus was examined using direct contact application and fumigation methods and compared with those of benzyl benzoate and N,N-diethyl-m-toluamide (DEET). Responses varied according to compound, dose, and mite species. On the basis of LD(50) values, the compound most toxic to D. farinae adults was methyleugenol (0.94 microg/cm(2)) followed by isoeugenol (5.17 microg/cm(2)), eugenol (5.47 microg/cm(2)), benzyl benzoate (9.22 microg/cm(2)), and acetyleugenol (14.16 microg/cm(2)). Very low activity was observed with DEET (37.59 microg/cm(2)). Against D. pteronyssinus adults, methyleugenol (0.67 microg/cm(2)) was much more effective than isoeugenol (1.55 microg/cm(2)), eugenol (3.71 microg/cm(2)), acetyleugenol (5.41 microg/cm(2)), and benzyl benzoate (6.59 microg/cm(2)). DEET (17.85 microg/cm(2)) was least toxic. These results indicate that the lipophilicity of the four phenylpropenes plays a crucial role in dust mite toxicity. The typical poisoning symptom of eugenol and its congeners was a similar death symptom of the forelegs extended forward together, leading to death without knockdown, whereas benzyl benzoate and DEET caused death following uncoordinated behavior. In a fumigation test with both mite species, all four phenylpropenes were much more effective in closed containers than in open ones, indicating that the mode of delivery of these compounds was largely due to action in the vapor phase. Eugenol and its congeners merit further study as potential house dust mite control agents or as lead compounds.