Acaricidal constituents isolated from Sinapis alba L. seeds and structure-activity relationships.
Allyl isothiocyanate (AITC) and phenethyl isothiocyanate (PEITC) were isolated from Sinapis alba L. seeds and their effects against Dermatophagoides farinae and D. pteronyssinus were evaluated using the impregnated fabric disk method. The LD 50 values of their compounds and derivatives were then compared with those of a commercial acaricide, benzyl benzoate. On the basis of the LD 50 values against D. farinae, PEITC (0.21 microg/cm(2)) was the most toxic, followed by benzyl isothiocyanate (0.55 microg/cm(2)), phenyl isothiocyanate (1.09 microg/cm(2)), butyl isothiocyanate (1.24 microg/cm(2)), and AITC (1.36 microg/cm(2)); acetyl isothiocyanate (195.01 microg/cm(2)) was the least toxic. In addition, the acaricidal effects of AITC and PEITC against D. farinae were 7.4- and 47.8-fold greater than those of benzyl benzoate, respectively. Against D. pteronyssinus, PEITC was the most toxic (0.19 microg/cm(2)), followed by benzyl isothiocyanate (0.77 microg/cm(2)), phenyl isothiocyanate (1.37 microg/cm(2)), butyl isothiocyanate (1.50 microg/cm(2)), and AITC (2.88 microg/cm(2)); acetyl isothiocyanate (168.82 microg/cm(2)) was the least toxic. AITC and PEITC were 3.3- and 50.4-fold more active than benzyl benzoate against D. pteronyssinus, respectively. Taken together, these findings indicate that AITC, PEITC, and partial derivatives may be useful as preventive agents against dust mites. In addition, these results indicate that structure-activity is related to the aromatic structure, the number of carbon atoms, and the compounds hydrophobicity.
Department of Agricultural Chemistry and Institute of Agricultural Science & Technology, College of Agriculture & Life Science, Chonbuk National University, Chonju 561-756, South Korea.
Jeong-Hyeon
JH
Lim
Hyung-Wook
HW
Kim
Ju-Hyun
JH
Jeon
Hoi-Seon
HS
Lee
D000818:Animals; D040001:Dermatophagoides farinae / Q000187:drug effects*; D007306:Insecticides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D017879:Isothiocyanates / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D012639:Seeds / Q000737:chemistry*; D031226:Sinapis / Q000737:chemistry*; D013329:Structure-Activity Relationship
D007306:Insecticides; D017879:Isothiocyanates; D010936:Plant Extracts; C037152:isothiocyanic acid