The chiral resolution of pesticides on amylose‐tris(3,5‐dimethylphenylcarbamate) CSP by HPLC and the enantiomeric identification by circular dichroism

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

doi:10.1002/chir.20486

Cited by 21 publications

(17 citation statements)

References 18 publications

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“…As a result, the r ‐MX was the more retained enantiomer compared with the s ‐MX. The elution orders are in good agreement with our experimental results, and the energetic difference is comparable with the experimental data (Table 1) 42.…”

Section: Resultssupporting

confidence: 89%

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Computational study of enantioseparation by amylose tris(3,5‐dimethylphenylcarbamate)‐based chiral stationary phase

Li¹,

Liu²,

Wang³

et al. 2010

J of Separation Science

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The mechanism of chiral separation on amylose tris(3,5-dimethylphenylcarbamate) is studied with docking simulations of enantiomers by molecular dynamics. All-atom models of amylose tris(3,5-dimethylphenylcarbamate) on the modified silica gel surface were constructed for the docking simulations of metalaxyl and benalaxyl. The elution orders and energetic differences were also predicted based on the intermolecular interactions, which were in agreement with the experimental results. The radial distribution function was employed to analyze the structural features of the enantiomer-chiral stationary phase complex and used to elucidate the mechanism of chiral separation. The separation of metalaxyl and benalaxyl is mainly controlled by the hydrogen bond. And the binding sites had slight differences for the pair of enantiomers, but obvious differences between different chemicals.

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Section: Resultssupporting

confidence: 89%

“…The more retained enantiomer that has lower interaction energy is s ‐BX. The predicted elution orders and the energetic differences were in agreement with the experimental results (Table 1) 42.…”

Section: Resultssupporting

confidence: 85%

Computational study of enantioseparation by amylose tris(3,5‐dimethylphenylcarbamate)‐based chiral stationary phase

Li¹,

Liu²,

Wang³

et al. 2010

J of Separation Science

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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

109

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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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“…The commonly used chiral separation methods are high‐performance liquid chromatography (HPLC), gas chromatography (GC), capillary electrophoresis (CE), and supercritical fluid chromatography (SFC). Among the many types of chiral separation methods, HPLC based on chiral stationary phases is used widely because of the powerful separation ability for both analytical and preparation purposes . A number of chiral stationary phases (CSPs) for HPLC have been prepared, such as Pirkle model CSP, the polysaccharide‐based CSPs, the macrocyclic antibiotics‐based CSPs, and the cyclodextrin‐based CSPs.…”

Section: Introductionmentioning

confidence: 99%

“…Among the various CSPs, the polysaccharide‐based CSPs are seen as versatile and useful for the separation of enantiomers . Many chiral pesticide enantiomers had been successfully separated by HPLC on polysaccharide chiral phase, such as cellulose‐tris(3,5‐dimethylphenylcarbamate), amylase‐tris(3,5‐dimethylphenylcarbamate) . It is important to develop enantiomeric residue analysis methods of chiral pesticides.…”

Section: Introductionmentioning

confidence: 99%

The Chiral Separation and Enantioselective Degradation of the Chiral Herbicide Napropamide

Liu

Sun

et al. 2014

Chirality

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The chiral pesticide enantiomers often have different toxic effects and environmental behaviors, which suggests that the risk assessments should be on an enantiomeric level. In this work, the chiral separation of the napropamide enantiomers and the stereoselective degradation in tomato, cucumber, rape, cabbage, and soil were investigated. Napropamide enantiomers could be separated absolutely by high-performance liquid chromatography (HPLC) using a Chiralpak IC column with a resolution factor of 11.75 under the optimized condition. Solid phase extraction (SPE) was used for cleanup of the enantiomers in the vegetable samples. The residue analysis method was validated. Good linearities (R(2) = 0.9997) and recoveries (71.43% -97.64%) were obtained. The limits of detection (LOD) were 0.05 mg/kg in soil and 0.20 mg/kg in vegetables. The results of degradation showed that napropamide dissipated rapidly in vegetables with half-lives of only 1.13-2.21 days, but much more slowly in soil, with a half-life of 11.95 d. Slight stereoselective degradation of the two enantiomers was only observed in cabbage, with enantiomeric fraction (EF) = 0.46, and there was no enantioselectivity in the other vegetables. The degradation of napropamide in the five matrixes was fast, and there was no enantioselectivity.

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The chiral resolution of pesticides on amylose‐tris(3,5‐dimethylphenylcarbamate) CSP by HPLC and the enantiomeric identification by circular dichroism

Cited by 21 publications

References 18 publications

Computational study of enantioseparation by amylose tris(3,5‐dimethylphenylcarbamate)‐based chiral stationary phase

Computational study of enantioseparation by amylose tris(3,5‐dimethylphenylcarbamate)‐based chiral stationary phase

Chiral pesticides

The Chiral Separation and Enantioselective Degradation of the Chiral Herbicide Napropamide

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