Enantioselective separation and pharmacokinetic dissipation of cyflumetofen in field soil by ultra‐performance convergence chromatography with tandem mass spectrometry

Liu, Na; Dong, Fengxia; Xu, Jun; Liu, Xingang; Chen, Zenglong; Pan, Xinglu; Chen, Xixi; Zheng, Yongquan

doi:10.1002/jssc.201501123

Cited by 27 publications

(20 citation statements)

References 21 publications

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“…Metabolism of the racemic cyflumetofen in spider mites in vivo by hydrolysation of the 2‐methoxyethylester and decarboxylation forming the achiral enol metabolite …”

Section: Acaricidesmentioning

confidence: 99%

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Current status of chirality in agrochemicals

Jeschke

2018

Pest Management Science

153

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The agrochemical industry is searching continuously for new pesticides to develop products that have optimal efficacy, lower application rates in the field, increased selectivity, favourable toxicological and environmental safety, enhanced user friendliness and better economic viability. One strategy by which to achieve these ambitious goals makes use of the unique properties of molecules containing asymmetric centres. In the past, many natural products and their congeners have been a source of inspiration in the design of new active ingredients, and the molecular structures of the resulting compounds have become increasingly complex; some 30% contain fragments with asymmetric centres. However, despite enormous progress in catalytic asymmetric processes over the past decade, few agrochemicals are produced in an enantiomerically pure or enriched form on an industrial scale. Since 2007, ∼ 43% of the 44 products launched (insecticides, acaricides, fungicides, nematicides and herbicides) contain one or more asymmetric centres in the molecule (∼ 47%) and most have been launched as racemic mixtures of enantiomers or diastereomers. This review provides an overview of the current status of chiral agrochemicals launched over the past 10 years and describes the inherently connected challenges of modern agricultural chemistry by managing important aspects resulting from the stereochemistry of these innovative products. © 2018 Society of Chemical Industry.

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“…Metabolism of the racemic cyflumetofen in spider mites in vivo by hydrolysation of the 2‐methoxyethylester and decarboxylation forming the achiral enol metabolite …”

Section: Acaricidesmentioning

confidence: 99%

“…Dissipation of racemic cyflumetofen in field soil was shown to be enantioselective, because the ( αR )‐( + ) ‐ cyflumetofen enantiomer is preferentially degraded (half‐life of ( αR )‐( + ) ‐ and ( αS )‐( − ) ‐ cyflumetofen: 12.2 versus 13.6 days) …”

Section: Acaricidesmentioning

confidence: 99%

Current status of chirality in agrochemicals

Jeschke

2018

Pest Management Science

153

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“…[17][18][19][20] The combination of UPC 2 and MS/MS could further improve the sensitivity of method. The system has been improved on the traditional SFC and can use columns of sub-2 μm fully porous particles to achieve better and faster separation with good repeatability and stability.…”

Section: Introductionmentioning

confidence: 99%

Ultra‐performance convergence chromatography with tandem mass spectrometry‐assisted method for rapid enantioseparation and determination of fluazifop‐butyl in tobacco and soil

et al. 2019

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A quick, green, and sensitive method for chiral separation and determination of fluazifop-butyl enantiomers in tobacco and soil was established by ultraperformance convergence chromatography with tandem mass spectrometry (UPC 2 -MS/MS). The baseline separation was obtained on an ACQUITY UPC 2 Trefoil CEL2 column in 4 minutes with CO 2 and methanol as mobile phase. Column temperature, auto back pressure regulator pressure (ABPR), and modifier solvent were optimized to obtain the best separation efficiency.Under the optimal conditions, the recoveries of both enantiomers were 82.8% to 99.5% with relative standard deviations (RSDs) less than 5.5% at three different concentration levels in two matrices. Good coefficients of determination (R 2 ≥ 0.9976) were achieved over the concentration range of 10 to 500 ng/mL. The limits of detection (LODs) for all enantiomers in the two matrices varied from 1.6 to 2.1 μg/kg, and the limits of quantification (LOQs) did not exceed 7.0 μg/kg. The proposed method was then successfully applied to analyze authentic samples, confirming that it was a green, convenient, and reliable strategy for the analysis of fluazifop-butyl enantiomers in tobacco and soil.

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“…These particles can achieve faster separation by using higher flow than sub-5 m particles. The sensitivity of the method is improved greatly by combining UPC 2 and MS/MS [21][22][23][24].…”

Section: Introductionmentioning

confidence: 99%

An environmentally friendly method for the enantioseparation and determination of benalaxyl in tobacco and soil by ultra‐performance convergence chromatography with tandem mass spectrometry

Yang

Tang

et al. 2018

J of Separation Science

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For the purpose of chiral separation and determination of benalaxyl enantiomers in tobacco and soil, we developed a rapid, green, and sensitive method using ultra-performance convergence chromatography with tandem mass spectrometry. The samples were extracted and purified by the quick, easy, cheap, effective, rugged, and safe method before injection. The baseline separation was obtained on a chiral column in 5 min with carbon dioxide and ethanol as mobile phase. Separation parameters were optimized for the best separation efficiency. Under optimal conditions, the recoveries of both enantiomers were 77.1-98.4% with relative standard deviations <5.0% at spiked level of 0.1, 2.0, and 5.0 mg/kg in two matrices. Good coefficients of determination were achieved over the concentration range of 10-250 ng/mL. The limit of detection and the limit of quantification for all enantiomers ranged from 0.43 to 0.72 μg/kg and from 1.25 to 2.15 μg/kg, respectively. The results show that ultra-performance convergence chromatography with tandem mass spectrometry provides a reliable, green, and rapid method for the separation and determination of benalaxyl enantiomers in tobacco and soil. This method has important theoretical significance for studying the enantioselectivity and bioactivity of benalaxyl in the environment and in organisms.

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Enantioselective separation and pharmacokinetic dissipation of cyflumetofen in field soil by ultra‐performance convergence chromatography with tandem mass spectrometry

Cited by 27 publications

References 21 publications

Current status of chirality in agrochemicals

Current status of chirality in agrochemicals

Ultra‐performance convergence chromatography with tandem mass spectrometry‐assisted method for rapid enantioseparation and determination of fluazifop‐butyl in tobacco and soil

An environmentally friendly method for the enantioseparation and determination of benalaxyl in tobacco and soil by ultra‐performance convergence chromatography with tandem mass spectrometry

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