Simultaneous enantioselective determination of isocarbophos and its main metabolite isocarbophos oxon in rice, soil, and water by chiral liquid chromatography and tandem mass spectrometry.

An efficient enantioselective method for the simultaneous determination of isocarbophos and its main metabolite isocarbophos oxon in rice, soil, and water was developed using liquid chromatography with tandem mass spectrometry. The enantioseparation was performed on a Chiralpak AD-3R column at 30°C using gradient elution. Target compounds were extracted from soil and rice using acetonitrile with omission of a clean-up procedure, while a C18 solid-phase extraction column was used for water samples. Quantification was achieved using matrix-matched calibration. The overall mean recoveries for isocarbophos and isocarbophos oxon enantiomers from the five matrices were 89.7-103 and 90.1-98.7%, with relative standard deviations of 2.1-5.4 and 2.5-4.7%, respectively. Moreover, the absolute configurations of isocarbophos oxon enantiomers were determined by liquid chromatography with tandem mass spectrometry through incubation of each isocarbophos enantiomer in soil, the first eluting enantiomer being confirmed as (R)-(-)-isocarbophos oxon. The proposed method was applied to real soil samples and satisfactory results were obtained.

[1]  Z. Y. Li,et al.  Enantioselective Degradation and Chiral Stability of Phenthoate in Soil , 2007, Bulletin of environmental contamination and toxicology.

[2]  Li Wang,et al.  Rapid determination of pesticide residues in herbs using selective pressurized liquid extraction and fast gas chromatography coupled with mass spectrometry. , 2012, Journal of separation science.

[3]  Qi Zhang,et al.  Screening for pesticide residues in oil seeds using solid-phase dispersion extraction and comprehensive two-dimensional gas chromatography time-of-flight mass spectrometry. , 2012, Journal of separation science.

[4]  Zhiqiang Zhou,et al.  Temperature-controlled ultrasound- and vortex-assisted liquid-liquid microextraction combined with GC for the determination of the concentrations of organophosphorus pesticides in beverage samples. , 2013, Journal of separation science.

[5]  Q. Wang,et al.  HPLC-MS/MS enantioseparation of triazole fungicides using polysaccharide-based stationary phases. , 2012, Journal of separation science.

[6]  Jiandong Jiang,et al.  Isolation of an isocarbophos-degrading strain of Arthrobacter sp. scl-2 and identification of the degradation pathway. , 2009, Journal of microbiology and biotechnology.

[7]  S. Broyde,et al.  Absolute configurations of spiroiminodihydantoin and allantoin stereoisomers: comparison of computed and measured electronic circular dichroism spectra. , 2009, Chemical research in toxicology.

[8]  Zhiqiang Zhou,et al.  Low-density solvent-based vortex-assisted surfactant-enhanced emulsification liquid-liquid microextraction and its application. , 2013, Journal of separation science.

[9]  Xiangyun Wang,et al.  Stereoselective determination of famoxadone enantiomers with HPLC-MS/MS and evaluation of their dissipation process in spinach. , 2011, Journal of separation science.

[10]  Peng Wang,et al.  Enantiomeric separation of chiral pesticides by high-performance liquid chromatography on an amylose tris-(S)-1-phenylethylcarbamate chiral stationary phase. , 2006, Journal of separation science.

[11]  D. Ferreira,et al.  Determination of Absolute Configuration of Natural Products: Theoretical Calculation of Electronic Circular Dichroism as a Tool. , 2010, Current organic chemistry.

[12]  Xiangyun Wang,et al.  Residue analysis and degradation studies of fenbuconazole and myclobutanil in strawberry by chiral high-performance liquid chromatography-tandem mass spectrometry. , 2011, Journal of agricultural and food chemistry.

[13]  J. Gan,et al.  Single and joint acute toxicity of isocarbophos enantiomers to Daphnia magna. , 2008, Journal of agricultural and food chemistry.

[14]  Shulin Zhuang,et al.  Enantioselective analysis and degradation studies of isocarbophos in soils by chiral liquid chromatography-tandem mass spectrometry. , 2012, Journal of agricultural and food chemistry.

[15]  Siyi Pan,et al.  Magnetic solid phase extraction based on magnetite/reduced graphene oxide nanoparticles for determination of trace isocarbophos residues in different matrices. , 2014, Journal of chromatography. A.

[16]  Jatinder Kaur Katnoria,et al.  Analytical methods for estimation of organophosphorus pesticide residues in fruits and vegetables: a review. , 2010, Talanta.

[17]  John J. Evans,et al.  High-performance liquid chromatographic separation of the enantiomers of organophosphorus pesticides on polysaccharide chiral stationary phases. , 2001, Journal of chromatography. A.

[18]  Chun Wang,et al.  Determination of some organophosphorus pesticides in water and watermelon samples by microextraction prior to high-performance liquid chromatography. , 2011, Journal of separation science.

[19]  Jianwei Xie,et al.  Contribution of carboxylesterase and cytochrome P450 to the bioactivation and detoxification of isocarbophos and its enantiomers in human liver microsomes. , 2014, Toxicological sciences : an official journal of the Society of Toxicology.

[20]  P. Plaza-Bolaños,et al.  Multiresidue method for the fast determination of pesticides in nutraceutical products (Camellia sinensis) by GC coupled to triple quadrupole MS. , 2014, Journal of separation science.

[21]  Zhixiang Xu,et al.  Simultaneous determination of ten organophosphate pesticide residues in fruits by gas chromatography coupled with magnetic separation. , 2014, Journal of separation science.

[22]  J. Gan,et al.  Chirality of organophosphorus pesticides: analysis and toxicity. , 2010, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[23]  M. Biziuk,et al.  Determination of organophosphorus and organonitrogen pesticides in water samples , 2010 .

[24]  Jiajia Yang,et al.  Direct enantiomeric separation of chiral pesticides by liquid chromatography on polysaccharide-based chiral stationary phases under reversed phase conditions , 2012 .

[25]  Cheng Zhang,et al.  Enantiomeric separation of organophosphorus pesticides by high-performance liquid chromatography, gas chromatography and capillary electrophoresis and their applications to environmental fate and toxicity assays. , 2010, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[26]  Charles S Wong,et al.  Environmental fate processes and biochemical transformations of chiral emerging organic pollutants , 2006, Analytical and bioanalytical chemistry.

[27]  W. Lindner,et al.  Determination of chlorpyrifos metabolites in human urine by reversed-phase/weak anion exchange liquid chromatography-electrospray ionisation-tandem mass spectrometry. , 2005, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[28]  J. Gawroński,et al.  Determination of absolute configuration--an overview related to this special issue. , 2008, Chirality.

[29]  Weiping Liu,et al.  Enantioselective cytotoxicity of isocarbophos is mediated by oxidative stress-induced JNK activation in human hepatocytes. , 2010, Toxicology.