High-performance chiral separation of fourteen triazole fungicides by sulfated beta-cyclodextrin-mediated capillary electrophoresis.
In this paper, sulfated beta-cyclodextrin-mediated capillary electrophoresis (CE) is evaluated as a new approach for the chiral separation of triazole-type fungicides. The 14 fungicides investigated were bitertanol, cyproconazole, difenoconazole, diniconazole, flutriafol, hexaconazole, myclobutanil, paclobutrazol, penconazole, propiconazole, tebuconazole, tetraconazole, triadimefon and triadimenol. Under the optimal conditions, excellent enantioseparation was achieved for all the 14 fungicides, including those fungicides containing two chiral centers. To our knowledge, this is the only system to date that offers outstanding enantiodiscrimination towards all triazole-type fungicides. The impact of the molecular structures of the triazole compounds on their migration behavior was studied. Similar to other chemical systems involving host-guest complexation, the interaction between sulfated beta-cyclodextrin and the triazole compounds was found to be affected by a variety of factors, including electrostatic force, hydrogen bonding, steric effect and hydrophobicity. These factors, coupled with the countercurrent electroosmotic flow (EOF), were believed to be the major forces behind the exceptional chiral selectivity.
Wu
Y S
YS
Department of Chemistry, National University of Singapore, Singapore.
Lee
H K
HK
Li
S F
SF
D003505:Cyclodextrins / Q000737:chemistry*; D019075:Electrophoresis, Capillary / Q000379:methods*; D005659:Fungicides, Industrial / Q000737:chemistry / Q000302:isolation & purification*; D013237:Stereoisomerism; D014230:Triazoles / Q000737:chemistry / Q000302:isolation & purification*; D047392:beta-Cyclodextrins
D003505:Cyclodextrins; D005659:Fungicides, Industrial; D014230:Triazoles; D047392:beta-Cyclodextrins; C031215:betadex