Enantiomeric separation of indoxacarb on an amylose-based chiral stationary phase and its application in study of indoxacarb degradation in water

Direct semipreparative enantioseparation of indoxacarb was performed on a semipreparative Chiralpak IA column using normal-phase high-performance liquid chromatography (HPLC) with n-hexane-isopropanol-ethyl acetate (70:20:10) mixture as mobile phase. Degradation of indoxacarb (2.33S+1R) and its two enantiopure isoforms in three aqueous buffer solutions and four water samples collected from natural water sources was then elucidated by HPLC analysis on Chiralpak IA column. Degradation of all three indoxacarbs complied with first-order kinetics and demonstrated linearity with regression coefficients R-2>0.88. Indoxacarb (2.33S+1R) underwent enantioselective degradation in river water, rain water, and buffer solution of pH7.0. Enantiopure S-(+)-indoxacarb and R-(-)-indoxacarb were both found to be configurationally stable in water. Copyright (c) 2014 John Wiley & Sons, Ltd.