The direct chiral separations of fungicide enantiomers on amylopectin based chiral stationary phase by HPLC

Wang, Peng; Liu, Donghui; Jiang, Shuren; Gu, Xu; Zhou, Zhiqiang

doi:10.1002/chir.20353

Cited by 24 publications

(10 citation statements)

References 18 publications

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“…[56][57][58] Recently, enantiomeric separation and quantification of various chiral pesticides by highperformance liquid chromatography and capillary electrophoresis have been reported by various researchers. [59][60][61][62][63][64][65][66][67][68][69][70][71][72][73][74][75] The general advantages of ICP-MS detection for chiral pesticide determinations in complex environmental samples have been reported. 76) Scientists determined the S and R isomers of metolachlor (3) in water by enantioselective enzyme immunoassay.…”

Section: Chiral Separationsmentioning

confidence: 99%

Chiral pesticides

Sekhon

2009

Journal of Pesticide Science

108

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The enantiomers of chiral pesticides are often metabolized at different rates. In agriculture, the preferred chiral form of a pesticide is more effective at lower application rates or more specific toward a targeted pest. Other advantages of chiral pure pesticides include greater environmental safety, reduced cost, greater specificity and extended patent life. Recent progress in optical resolution, asymmetric synthesis and biocatalysis of chiral pesticides has been described. Techniques to separate enantiomers with chiral HPLC and GC columns, electrophoresis and mass spectrometry have been reported. Chiral chase is actively pursuing asymmetric hydrogenation for the manufacture of a pure single-enantiomer pesticide. Enantioselectivity occurs in pesticidal activities toward target organisms as well as non-targeted organisms. There is a need to characterize both enantiomers of chiral pesticides in order to have an accurate understanding of their distribution and fate in the environment. Enantiomeric analysis can be useful in this aim and this is an important consideration in the risk assessment of pesticides. Use of only the target-active enantiomer of pesticides should be encouraged as it will reduce the pollutant load, provided it has no adverse impact on non-target organisms.

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Section: Chiral Separationsmentioning

confidence: 99%

Chiral pesticides

Sekhon

2009

Journal of Pesticide Science

108

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“…However, so far as we know, enantioselective determination of tebuconazole enantiomers in environmental and food matrices is currently not available. In the past, the vast majority enantioseparation methods of tebuconazole were performed by chiral HPLC with UV detection [27][28][29][30][31][32][33][34]. Moreover, the chiral separation of tebuconazole was also employed by GC-MS technique equipped with a BGB 172 chiral column; however, the two enantiomers were only partially separated [35].…”

Section: Introductionmentioning

confidence: 99%

Enantioselective determination of triazole fungicide tebuconazole in vegetables, fruits, soil and water by chiral liquid chromatography/tandem mass spectrometry

Dong

Liu

et al. 2011

J of Separation Science

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A novel and sensitive method was developed for the determination of tebuconazole enantioselectively using reversed-phase LC-MS/MS. The separation and determination were performed using on an amylose-based chiral stationary phase, a Lux 3u Amylose-2 column (150 mm×2.0 mm), under isocratic conditions at 0.3 mL/min flow rate. A series of chiral stationary phases were investigated and the effect of mobile phase composition on the enantioseparation was discussed. Parameters including the matrix effect, linearity, precision, accuracy and stability were evaluated. Under optimal conditions, the overall mean recoveries for two enantiomers from the soil, tomato, cucumber, pear and apple samples were 79.3-101.1% with 2.8-11.5% intra-day relative standard deviations (RSDs) and 4.1-8.6% inter-day RSDs at 5, 25 and 50 μg/kg levels; the mean enantiomer recoveries from the water samples were 89.6-101.9% with 3.3-10.2% intra-day RSDs and 5.1-7.7% inter-day RSDs at 0.25, 0.5 and 2.5 μg/kg levels. The limits of detection (LODs) for all enantiomers in tomato, cucumber, pear, apple, soil and water were less than 0.6 μg/kg, whereas the limit of quantification (LOQ) did not exceed 2.0 μg/kg. The results indicate that this proposed method is convenient and reliable for the enantioselective determination of tebuconazole enantiomers in foods and environment samples.

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“…In previous studies, tebuconazole enantiomers were always separated by polysaccharide CSPs. 3,15,16 In this study, amylose-2 column was used to separate tebuconazole enantiomers. Amylose-2 column is a new type polysaccharide columns based on amylose-tris(5-chlorine-2-methylphenylcarbamate).…”

Section: Introductionmentioning

confidence: 99%

Enantioselective degradation of tebuconazole in cabbage, cucumber, and soils

Wang¹,

Wang²,

Zhang³

et al. 2011

Chirality

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The enantioselective degradation of tebuconazole has been investigated to elucidate the behaviors in agricultural soils, cabbage, and cucumber fruit. Rac-tebuconazole was fortified into three types of agricultural soils and sprayed foliage of cabbage and cucumber, respectively. The degradation kinetics, enantiomer fraction and enantiomeric selectivity were determined by reverse-phase high-performance liquid chromatography (HPLC) and liquid chromatography-mass spectrometry/mass spectrometry (LC-MS/MS) on a Lux amylose-2 chiral column. The process of the degradation of tebuconazole enantiomers followed first-order kinetic in the test soils and vegetables. It has been shown that the degradation of tebuconazole was enantioselective. The results indicated that the (+)-S-tebuconazole showed a faster degradation in cabbage, while the (-)-R-tebuconazole dissipated faster than (+)-S-form in cucumber fruit and the test soils.

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The direct chiral separations of fungicide enantiomers on amylopectin based chiral stationary phase by HPLC

Cited by 24 publications

References 18 publications

Chiral pesticides

Chiral pesticides

Enantioselective determination of triazole fungicide tebuconazole in vegetables, fruits, soil and water by chiral liquid chromatography/tandem mass spectrometry

Enantioselective degradation of tebuconazole in cabbage, cucumber, and soils

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