Enantioselective degradation and chiral stability of the herbicide fluazifop-butyl in soil and water

Qi, Yanli; Liu, Donghui; Luo, Mai; Jing, Xu; Wang, Peng; Zhou, Zhiqiang

doi:10.1016/j.chemosphere.2015.12.040

Cited by 38 publications

(29 citation statements)

References 30 publications

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“…Diclofop-methyl exhibited diverse enantioselective behaviors in different biodegradation matrices, with its (-)-enantiomer being degraded faster in soil samples and more slowly in Chinese cabbage samples [128]. The same multiplicity of enantioselective behaviors was observed for fluazifop-butyl, which was enantioselectively biodegraded in soil, though the enantiomer preferentially degraded varied within samples, while its degradation on water samples was non-enantioselective [130].…”

Section: Biodegradation Studies Of Chiral Pesticidesmentioning

confidence: 80%

“…All the works with GC described direct enantioselective methods using cyclodextrin-based CSP, the CSP most often applied in enantioselective analysis of organochlorine compounds [169,170]. Enantioselective LC-MS/MS methods performed direct chiral analysis, mostly using polysaccharide-based CSP [21,123,130,152,153], although the utilization of a cyclodextrin-based CSP was also described [131]. Soil is the major matrix used in pesticides' biodegradation studies, accounting for more than 70% of the works considered in this review, probably because it is the primary environmental compartment with which they are in contact.…”

Section: Biodegradation Studies Of Chiral Pesticidesmentioning

confidence: 99%

“…Generally, all the studies reported enantioselective biodegradation to some extent in the various matrices considered (for instance, algae cultures, agricultural soil, sediment, water, and vegetables) [127][128][129][130]. Diclofop-methyl exhibited diverse enantioselective behaviors in different biodegradation matrices, with its (-)-enantiomer being degraded faster in soil samples and more slowly in Chinese cabbage samples [128].…”

Section: Biodegradation Studies Of Chiral Pesticidesmentioning

confidence: 99%

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Chiral Analysis of Pesticides and Drugs of Environmental Concern: Biodegradation and Enantiomeric Fraction

et al. 2017

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Abstract:The importance of stereochemistry for medicinal chemistry and pharmacology is well recognized and the dissimilar behavior of enantiomers is fully documented. Regarding the environment, the significance is equivalent since enantiomers of chiral organic pollutants can also differ in biodegradation processes and fate, as well as in ecotoxicity. This review comprises designed biodegradation studies of several chiral drugs and pesticides followed by enantioselective analytical methodologies to accurately measure the enantiomeric fraction (EF). The enantioselective monitoring of microcosms and laboratory-scale experiments with different environmental matrices is herein reported. Thus, this review focuses on the importance of evaluating the EF variation during biodegradation studies of chiral pharmaceuticals, drugs of abuse, and agrochemicals and has implications for the understanding of the environmental fate of chiral pollutants.

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Section: Biodegradation Studies Of Chiral Pesticidesmentioning

confidence: 80%

Section: Biodegradation Studies Of Chiral Pesticidesmentioning

confidence: 99%

Section: Biodegradation Studies Of Chiral Pesticidesmentioning

confidence: 99%

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Chiral Analysis of Pesticides and Drugs of Environmental Concern: Biodegradation and Enantiomeric Fraction

et al. 2017

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“…[10][11][12] Qi et al also demonstrated that S-enantiomer degraded faster than R-enantiomer in tomato and cucumber, resulting in a higher residue of the R-enantiomer in the samples. The degradation of fluazifop-butyl is enantioselective in different environments.…”

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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“…In the past few decades, more and more chiral pesticides have been used in agricultural pest control. 6,7 Therefore, a chiral analysis method should be established to precisely evaluate the risks of chiral pesticide enantiomers in environment. 2,3 The identification of enantiomers has attracted much attention due to the fact that one enantiomer probably shows high efficiency with low toxicity and the unwanted enantiomer is toxic to environment with little effect.…”

Section: Introductionmentioning

confidence: 99%

Enantiomeric separation of prothioconazole and prothioconazole‐desthio on chiral stationary phases

Liu

Ding

2019

Chirality

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Prothioconazole is a type of broad-spectrum triazole thione fungicide developed by the Bayer Company. Prothioconazole-desthio is the main metabolite of prothioconazole in the environment. In our study, enantiomeric separation of prothioconazole and prothioconazole-desthio was performed on various chiral stationary phases (CSPs) by high-performance liquid chromatography (HPLC). It was found that polysaccharide CSPs showed better ability than brushing CSPs in enantiomeric separation. The successful chiral separation of prothioconazole could be achieved on self-made Chiralcel OD, commercialized Chiralcel OJ-H and Lux Cellulose-1. Chiralpak IA, Chiralpak IB, Chiralpak IC, Chiralcel OD, Chiralpak AY-H, Chiralpak AZ-H, and Lux Cellulose-1 realized the baseline separation of prothioconazole-desthio enantiomers. Simultaneous enantiomeric separation of prothioconazole and prothioconazole-desthio was performed on Lux Cellulose-1 using acetonitrile (ACN) and water as mobile phase. In most cases, low temperature favored the separation of two compounds. The influence of the mobile phase ratio or type was deeply discussed. We obtained larger Rs and longer analysis time with a smaller proportion of isopropanol (IPA) or ethanol and more water content at the same temperature. The ratio of ACN and water had influences on the outflow orders of prothioconazole-desthio enantiomers. This work provides a new approach for chiral separation of prothioconazole and prothioconazole-desthio with a discussion of chiral separation mechanism on different CSPs.

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Enantioselective degradation and chiral stability of the herbicide fluazifop-butyl in soil and water

Cited by 38 publications

References 30 publications

Chiral Analysis of Pesticides and Drugs of Environmental Concern: Biodegradation and Enantiomeric Fraction

Chiral Analysis of Pesticides and Drugs of Environmental Concern: Biodegradation and Enantiomeric Fraction

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

Enantiomeric separation of prothioconazole and prothioconazole‐desthio on chiral stationary phases

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