Enantiomeric separation of indoxacarb on an amylose‐based chiral stationary phase and its application in study of indoxacarb degradation in water

Zhang, Yuping; Zhang, Kankan; Song, Baoan; Ling, Hu-Rong; Li, Zhining; Li, Meichuan; Hu, Deyu

doi:10.1002/bmc.3178

Cited by 12 publications

(7 citation statements)

References 17 publications

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“…Individual enantiomers with enantio purity >99.0% were obtained by enantioselective separation of the indoxacarb racemate using semipreparative HPLC . Single crystals of enantiopure S -indoxacarb and enantiopure R -indoxacarb were obtained by recrystallization from dimethyl sulfoxide and ethanol mixture at room temperature.…”

Section: Resultsmentioning

confidence: 99%

“…Indoxacarb powder enriched with the S -enantiomer (2.33S/1R, 97.3% purity) was provided by Yancheng Limin Agrochemical Co., Ltd. (Jiangsu, China). The two indoxacarb enantiomers were prepared by semipreparative high-performance liquid chromatography (HPLC) in our laboratory . HPLC-grade n -hexane and isopropanol (IPA) were purchased from Jiangsu Hanbang Science and Technology Co., Ltd. (Jiangsu, China).…”

Section: Materials and Methodsmentioning

confidence: 99%

“…The two indoxacarb enantiomers were prepared by semipreparative high-performance liquid chromatography (HPLC) in our laboratory. 29 HPLC-grade n-hexane and isopropanol (IPA) were purchased from Jiangsu Hanbang Science and Technology Co., Ltd. (Jiangsu, China). All other chemicals and solvents used were of analytical grade and purchased from commercial sources.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

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Comparative Study of the Selective Degradations of Two Enantiomers in the Racemate and an Enriched Concentration of Indoxacarb in Soils

Zhang

Ling

et al. 2014

J. Agric. Food Chem.

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In this study, selective degradations of the two enantiomers of indoxacarb in the concentrate (2.33S/1R) and racemate (1S/1R) are examined. The absolute configurations of indoxacarb enantiomers were determined using X-ray diffraction. The results showed that in two alkaline soils, the S-(+)-indoxacarb was preferentially degraded in both the concentrate and racemate. In one acid soil, the two enantiomers degraded no-selectivity. In another acid soil and one neutral soil, the R-(-)-indoxacarb was preferentially degraded in both the concentrate and racemate. Indoxacarb enantiomers were configurationally stable in the five soils, and no interconversion was observed during the incubation. Because no significant difference in degradation was observed after samples were sterilized, the observed enantioselectivity may be attributed primarily to microbial activity in soils. The results indicate that the selective degradation behavior was the same for both formulations that were tested.

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Section: Resultsmentioning

confidence: 99%

Section: Materials and Methodsmentioning

confidence: 99%

Section: ■ Materials and Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Comparative Study of the Selective Degradations of Two Enantiomers in the Racemate and an Enriched Concentration of Indoxacarb in Soils

Zhang

Ling

et al. 2014

J. Agric. Food Chem.

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“…For instance, Zhang, Hu, et al () demonstrated that S‐ (+)‐indoxacarb is preferentially degraded in two alkaline soils while R‐ (−)‐indoxacarb is preferentially degraded in acidic soil; Sun et al found that R‐ (−)‐indoxacarb degrades faster in Beijing cabbage, but the opposite result is obtained in the Anhui cabbage (Sun et al, ). Moreover, some reports have proven that S‐ indoxacarb is preferentially degraded over R‐ indoxacarb in cucumber, tomato (Wang et al, ), water (Zhang et al, ), soil (Sun et al, ) and tea (Zhang et al, ). In those reports, the degradation of indoxacarb enantiomers exhibits individual differences, and their half‐lives vary in different matrices.…”

Section: Introductonmentioning

confidence: 99%

Degradation and residues of indoxacarb enantiomers in rice plants, rice hulls and brown rice using enriched S‐indoxacarb formulation and enantiopure formulation

Shi

Gui

Zhao

et al. 2018

Biomedical Chromatography

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A chiral liquid chromatography-tandem high resolution mass spectroscopic method was developed for the analysis of indoxacarb enantiomers in rice plants, rice hulls and brown rice. Chiral separation of two enantiomers was carried out on a Superchiral S-OD column maintained at 20°C and eluted with 0.3 mL/min methanol. Samples were extracted by acetonitrile solution with ultrasound and cleansed by dispersive solid-phase extraction of 50 mg of primary secondary amine and 50 mg of C . This method was successfully used to study the degradation and residues of two enantiomers with enriched S-indoxacarb (2.33S/1R) and pure S-indoxacarb in rice plants. The half-lives of R-indoxacarb and S-indoxacarb were 4.20-4.33 and 3.45-3.57 days in rice plants during the degradation of enriched S-indoxacarb in Guizhou and Hunan, respectively, whereas the half-lives of pure S-indoxacarb were 2.68 and 3.69 days in Guizhou and Hunan, respectively. The results indicated that preferential S-indoxacarb degradation occurred and that enantiomeric transformation was absent in the total experiment periods of pure S-indoxacarb in rice plants. The final residue concentrations of indoxacarb enantiomers in brown rice were significantly less than those in rice plants and rice hulls in the same rice field after applying indoxacarb SC and indoxacarb EC.

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“…They have been detected in municipal sewage effluent and various environmental samples such as surface water, marine, soil, sediment and aquatic biota in many countries. The occurrence of synthetic musks in environmental samples could negatively affect the health of the ecosystem and humans, owing to persistent, chronic exposure of aquatic organisms [ 7 , 8 , 9 , 10 , 11 ].…”

Section: Introductionmentioning

confidence: 99%

Enantioselective Determination of Polycyclic Musks in River and Wastewater by GC/MS/MS

Lee

Gopalan

2016

IJERPH

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The separation of chiral compounds is an interesting and challenging topic in analytical chemistry, especially in environmental fields. Enantioselective degradation or bioaccumulation has been observed for several chiral pollutants. Polycyclic musks are chiral and are widely used as fragrances in a variety of personal care products such as soaps, shampoos, cosmetics and perfumes. In this study, the gas chromatographic separation of chiral polycyclic musks, 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclo-penta-γ-2-benzopyrane (HHCB), 7-acetyl-1,1,3,4,4,6-hexamethyl-1,2,3,4-tetra-hydronaphthalene (AHTN), 6-acetyl-1,1,2,3,3,5-hexamethylindane (AHDI), 5-acetyl-1,1,2,6-tetramethyl-3-iso-propylindane (ATII), and 6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone (DPMI) was achieved on modified cyclodextrin stationary phase (heptakis (2,3-di-O-methyl-6-O-tert-butyl-dimethylsilyl-β-CD in DV-1701)). Separation techniques are coupled to tandem mass spectrometry (MS-MS), as it provides the sensitivity and selectivity needed. River and wastewaters (influents and effluents of wastewater treatment plants (WWTPs)) in the Nakdong River were investigated with regard to the concentrations and the enantiomeric ratios of polycyclic musks. HHCB was most frequently detected in river and wastewaters, and an enantiomeric enrichment was observed in the effluents of one of the investigated wastewater treatment plants (WWTPs). We reported the contamination of river and wastewaters in Korea by chiral polycyclic musks. The results of this investigation suggest that enantioselective transformation may occur during wastewater treatment.

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Enantiomeric separation of indoxacarb on an amylose‐based chiral stationary phase and its application in study of indoxacarb degradation in water

Cited by 12 publications

References 17 publications

Comparative Study of the Selective Degradations of Two Enantiomers in the Racemate and an Enriched Concentration of Indoxacarb in Soils

Comparative Study of the Selective Degradations of Two Enantiomers in the Racemate and an Enriched Concentration of Indoxacarb in Soils

Degradation and residues of indoxacarb enantiomers in rice plants, rice hulls and brown rice using enriched S‐indoxacarb formulation and enantiopure formulation

Enantioselective Determination of Polycyclic Musks in River and Wastewater by GC/MS/MS

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