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Direct Enantioseparation of Nitrogen‐heterocyclic Pesticides on Amylose‐tris‐(5‐chloro‐2‐methylphenylcarbamate) by Reversed‐Phase High‐Performance Liquid Chromatography
Author(s) -
Yang Wenwen,
Qiu Jing,
Chen Tianjin,
Yang Shuming,
Hou Shicong
Publication year - 2012
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22092
Subject(s) - chemistry , acetonitrile , chromatography detector , enantiomer , chromatography , chirality (physics) , elution , phase (matter) , high performance liquid chromatography , tris , pesticide , organic chemistry , biochemistry , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , agronomy , biology , quark
In this study, 11 nitrogen‐heterocyclic pesticides were stereoselectively separated on amylose‐tris‐(5‐chloro‐2‐methylphenylcarbamate) chiral stationary phase, using reversed‐phase high‐performance liquid chromatography with diode array detector and optical rotation detector at 426 nm. The effects of mobile phase composition and column temperature (5–40 °C) on separation were investigated. When acetonitrile and water were used as mobile phase, satisfactory separations were obtained on amylose‐tris‐(5‐chloro‐2‐methylphenylcarbamate) for four pesticides with elution orders of (+)/(−)‐simeconazole (1) , (−)/(+)‐nuarimol (3) , (−)/(+)‐carfentrazone‐ethyl (4) , and (−)/(+)/(−)/(+)‐bromuconazole (9) and part separations for three with elution orders of (−)/(+)‐famoxadone (6) , (+)/(−)‐fenbuconazole (10) , and (−)/(+)‐triapenthenol (11) . Only two chromatographic peaks on diode array detector were obtained for diclobutrazol (2) , cyproconazole (5) , etaconazole (7) , and metconazole (8) , although they should have four stereoisomers in theory because of presences of two chiral centers in molecules. The stereoisomeric optical signals of all pesticides did not reverse with temperature changes but would reverse with different solvent types for some pesticides. These results will be useful to prepare and analyze individual enantiomers of chiral pesticides. Chirality 24:1031–1036, 2012 . © 2012 Wiley Periodicals, Inc.