Enantioselective behaviors of cis-epoxiconazole in vegetables-soil-earthworms system by liquid chromatography-quadrupole-time-of-flight mass spectrometry

Qi, Peipei; Di, Shanshan; Cang, Tao; Yang, Xiao; Wang, Xiangyun; Wang, Zhiwei; Hao, X. Q.; Zhao, Huiyu; Wang, Xinquan

doi:10.1016/j.scitotenv.2019.136039

Cited by 14 publications

(5 citation statements)

References 26 publications

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“…In SnE, the concentrations of trans (+)-1 R ,3 R- and trans (−)-1 S ,3 S -tetramethrin (Figure A) in earthworms were faster accumulated to maximum levels of 6.7 mg/kg on the 1st day and 45.9 mg/kg on the 2nd day, respectively, and then greatly decreased to 0.44 and 0.42 mg/kg on the 21st day. The accumulation and degradation tendencies were consistent with the report of Qi et al, who showed that the cis -epoxiconazole in earthworms also quickly reached the highest concentration on the first day and then decreased slowly until the end of exposure time. However, in SaE (Figure B), the maximum accumulation concentrations of 32.9 mg/kg for trans (+)-1 R ,3 R- tetramethrin and 79.3 mg/kg for trans (−)-1 S ,3 S -tetramethrin in earthworms were observed on the 2nd day and then sharply decreased to a lower level on 21st day.…”

Section: Resultssupporting

confidence: 91%

Systematic Stereoselectivity Evaluations of Tetramethrin Enantiomers: Stereoselective Cytotoxicity, Metabolism, and Environmental Fate in Earthworms, Soils, Vegetables, and Fruits

Wang²,

Guo³

et al. 2022

J. Agric. Food Chem.

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Tetramethrin is a widely applied type I chiral pyrethroid insecticide that exists as a mixture of four isomers. In the present study, its stereoselective cytotoxicity, bioaccumulation, degradation, and metabolism were investigated for the first time at the enantiomeric level in detail by using a sensitive chiral high-performance liquid chromatography−tandem mass spectroscopy (HPLC-MS/MS) method. Results showed that among rac-tetramethrin and its four enantiomers, the trans (+)-1R,3R-tetramethrin had the strongest inhibition effect on the PC12 cells. In the earthworm exposure trial, the concentration of trans (−)-1S,3Stetramethrin was 0.94−8.92 times in earthworms (cultivated in natural soil) and 1.67−5.01 times (cultivated in artificial soil) higher than trans (+)-1R,3R-tetramethrin, respectively. In the greenhouse experiment, the trans (+)-1R,3R-tetramethrin and cis (+)-1R,3Stetramethrin were preferentially degraded. Furthermore, for rat liver microsome in vitro incubation, the maximum metabolism rate of cis (−)-1S,3R-tetramethrin was 1.50 times higher than its antipodes. Altogether, the aim of this study was to provide a scientific and reasonable reference for the possibility of developing a single enantiomer to replace the application of rac-tetramethrin, which could possess better bioactivity and lower ecotoxicity, and thus permit more reliable and accurate environmental monitoring and risk assessment.

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Section: Resultssupporting

confidence: 91%

Systematic Stereoselectivity Evaluations of Tetramethrin Enantiomers: Stereoselective Cytotoxicity, Metabolism, and Environmental Fate in Earthworms, Soils, Vegetables, and Fruits

Wang²,

Guo³

et al. 2022

J. Agric. Food Chem.

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“…So, monomers 1 and 2 were S -diniconazole and R -diniconazole, respectively. Similarly, Qi et al reported that the values of (+)-cis-epoxiconazole and 2 R , 3 S -cis-epoxiconazole were positive in the wavelength range of 200–250 nm …”

Section: Results and Discussionmentioning

confidence: 84%

“…Similarly, Qi et al reported that the values of (+)-cis-epoxiconazole and 2R, 3S-cis-epoxiconazole were positive in the wavelength range of 200−250 nm. 28 3.2. Chiral Separation of Diniconazole Enantiomers.…”

Section: Resultsmentioning

confidence: 99%

Enantioselective Dissipation, Residue, and Risk Assessment of Diniconazole Enantiomers in Four Kinds of Fruits

Teng

Wang

et al. 2021

J. Agric. Food Chem.

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Chiral diniconazole is a widely used triazole fungicide, while its enantioselective behaviors in fruits have not been reported. In this article, the absolute configuration was confirmed. A fast supercritical fluid chromatography-tandem mass spectrometry (SFC-MS/MS) method was developed for the chiral separation and enantioselective study of diniconazole in four kinds of fruits. The residual concentrations gradually decreased with time in four kinds of fruits after applying diniconazole. The dissipation half-lives of R-diniconazole and S-diniconazole were in the range of 5.3–7.9 and 2.5–7.1 days respectively, and S-diniconazole was degraded preferentially. The residue concentrations were lower than the EU’s MRL (0.01 mg/kg) on the 40th (harvest time), 30th, and 10th day in pear, jujube, and apple, respectively. But, in peach, residue concentrations were still higher than the MRL after 60 days and the ratio of R/S was 2.2. These results could be helpful for the reasonable use and risk assessment of chiral diniconazole.

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“…Therefore, this could cause relative enrichment of trans (+)-2S,4S-and cis (−)-2S,4R-PRO in E. fetida. Our results were consistent with the report of Qi et al, 45 who had proved that the concentration of cis-epoxiconazole in earthworms could quickly reach the maximum concentration on the first day and then decreased to a lower level by the end of exposure time. The above results also showed that the stereoselectivity of PRO in SnE is more significant than that in SaE, and trans (+)-2S,4S-and cis (−)-2S,4R-PRO were relatively enriched in E. fetida.…”

Section: Stereoselective Cytotoxic Effects Of Pro On Neuronal and Lun...mentioning

confidence: 99%

Comprehensive Stereoselectivity Assessment of Toxicokinetics, Tissue Distribution, Cytotoxicity, and Environmental Fate of Chiral Pesticide Propiconazole

Ma,

Xin,

Zhao

et al. 2023

J. Agric. Food Chem.

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Enantioselective behaviors of cis-epoxiconazole in vegetables-soil-earthworms system by liquid chromatography-quadrupole-time-of-flight mass spectrometry

Cited by 14 publications

References 26 publications

Systematic Stereoselectivity Evaluations of Tetramethrin Enantiomers: Stereoselective Cytotoxicity, Metabolism, and Environmental Fate in Earthworms, Soils, Vegetables, and Fruits

Systematic Stereoselectivity Evaluations of Tetramethrin Enantiomers: Stereoselective Cytotoxicity, Metabolism, and Environmental Fate in Earthworms, Soils, Vegetables, and Fruits

Enantioselective Dissipation, Residue, and Risk Assessment of Diniconazole Enantiomers in Four Kinds of Fruits

Comprehensive Stereoselectivity Assessment of Toxicokinetics, Tissue Distribution, Cytotoxicity, and Environmental Fate of Chiral Pesticide Propiconazole

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