Enantiomeric separation of chiral pesticides by high performance liquid chromatography on cellulose tris‐3,5‐dimethyl carbamate stationary phase under reversed phase conditions

Qin, Tian; Lv, Chenyan; Wang, Peng; Ren, Liping; Qiu, Jing; Li, Li; Zhou, Zhiqiang

doi:10.1002/jssc.200600255

Cited by 37 publications

(27 citation statements)

References 44 publications

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“…Thereinto HPLC with chiral stationary phases (CSP) is a most popular method for enantioseparation. For example, good separation were obtained for hexaconazole ( 1 ) , flutriafol ( 2 ) , diniconazole ( 3 ) , triadimefon ( 9 ) on Chiralcel OD with CSP of CDMPC (cellulose‐ tris ‐(3,5‐dimethylphenylcarbamate),10, 11 epoxiconazole ( 5 ) on microcrystalline cellulose triacetate,13 hexaconazole ( 1 ) on ( S , S )‐Whelk O1 column,14 on NP‐HPLC with a mixture of hexane and different polar additives as the eluent, and epoxiconazole ( 5 ) on CDMPC on RP‐HPLC with acetonitrile (ACN) or methanol (MET) and water as mobile phase 12…”

Section: Introductionmentioning

confidence: 99%

Enantiomeric separation of triazole fungicides with 3‐μm and 5‐μml particle chiral columns by reverse‐phase high‐performance liquid chromatography

et al. 2011

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This study used chiral columns packed with 3-μm and 5-μm particles to comparatively separate enantiomers of 9 triazole fungicides, and Lux Cellulose-1 columns with chiral stationary phase of cellulose-tris-(3,5-dimethylphenylcarbamate) were used on reverse-phase high-performance liquid chromatography with flow rates of 0.3 and 1.0 mL min(-1) for 3-μm and 5-μm columns, respectively. The (+)-enantiomers of hexaconazole (1), tetraconazole (4), myclobutanil (7), fenbuconazole (8) and the (-)-enantiomers of flutriafol (2), diniconazole (3), epoxiconazole (5), penconazole (6), triadimefon (9) were firstly eluted from both columns, the elution orders identified with an optical rotation detector didn't change with variety of column particles and mobile phases (acetronitrile/water and methanol/water). The plots of natural logarithms of the selectivity factors (ln α) for all fungicides except penconazole (6) versus the inverse of temperature (1/T) were linear in range of 5-40°C. The thermodynamic parameters (ΔH°, ΔS°, ΔΔH° and ΔΔS°) were calculated using Van't Hoff equations to understand the thermosynamic driving forces for enantioseparation. This work will be very helpful to obtain good enantiomeric separation and establish more efficient analytical method for triazole fungicides. Chirality, 2011. © 2011 Wiley-Liss, Inc.

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Section: Introductionmentioning

confidence: 99%

Enantiomeric separation of triazole fungicides with 3‐μm and 5‐μml particle chiral columns by reverse‐phase high‐performance liquid chromatography

et al. 2011

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“…Pregabalin and omeprazole are both among drugs in which only their S isomer is active . The R form of mandelic acid acts as a key intermediate in the production of semisynthetic penicillins and cephalosporins, and diclofop‐methyl is an organochlorine herbicide for which its R enantiomer shows significantly greater herbicidal activity .…”

Section: Resultsmentioning

confidence: 99%

Preparation and evaluation of a deoxycholic‐calix[4]arene hybrid‐type receptor as a chiral stationary phase for HPLC

Yaghoubnejad

Heydar

Ahmadi

et al. 2018

J of Separation Science

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We report the synthesis and enantioseparation characteristics of two novel covalently immobilized deoxycholic acid derivatives as chiral stationary phases for high-performance liquid chromatography. In the structure of the first stationary phase, the 3-position of deoxycholic acid is substituted with a 3,5-dinitrophenylcarbamoyl group and the second one has an additional calix[4]arene attached to the carboxylic group of the deoxycholic acid. The chromatographic performance of the stationary phases was evaluated with enantioseparation of N-(3,5-dinitrobenzoyl)-dl-leucine, N-(3,5-dinitrobenzoyl)-dl-valine, omeprazole, diclofop-methyl, dl-mandelic acid and (RS)-pregabalin. Comparison of the performance characteristics of the prepared chiral stationary phases provided evidence for the active involvement of the calix[4]arene unit in the chiral recognition process. Both stationary phases are chemically bonded to the silica and can be used in both normal-phase and reversed-phase modes.

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“…S2 and S3). As in the published procedures, the S ‐fipronil in the acetonitrile/water mobile phase elutes first on a column cellulose tri‐3,5‐dimethylphenyl carbamate chiral stationary phase. The first eluted enantiomer was S ‐fipronil, and the second eluted enantiomer was R ‐fipronil.…”

Section: Methodsmentioning

confidence: 99%

Enantioselective bioaccumulation and toxic effects of fipronil in the earthworm Eisenia foetida following soil exposure

Fang

Gao

et al. 2014

Pest Management Science

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BACKGROUND: Enantiomers of chiral pesticides often have different bioactivity, toxicity and environmental behaviours. Fipronil has been used in racemate for agricultural purposes against soil insects, leading to increased inputs into soil environments and complex biota exposures. To understand the potential risk associated with fipronil enantiomer exposure, subchronic toxicity and bioaccumulation tests with earthworms (Eisenia foetida) in fipronil-spiked soils were evaluated under laboratory conditions. RESULTS: Enantioselective toxicity was measured in E. foetida biomass after 28 days of subchronic exposure, with increased toxicity from racemate and S-fipronil compared with R-fipronil. The bioaccumulation of fipronil in earthworm tissues was also enantioselective, with a preferential accumulation of S-fipronil, and the enantiomer fraction was approximately 0.56-0.60. During soil exposure, fipronil was transformed primarily into fipronil sulfide, sulfone and amide, and E. foetida rapidly accumulated fipronil and sulfone.CONCLUSION: This work demonstrates the enantioselective subchronic toxicity and bioaccumulation of enantiomers of fipronil in E. foetida. The earthworm tissues exhibited a relative enrichment of fipronil and fipronil sulfone, and these compounds might biomagnify (with a biota-to-soil accumulation factor of ≥1.0 kg OC kg −1 lip ), allowing for the possible trophic transfer and/or bioaccumulation of all these chemicals if earthworms were consumed by predator organisms.

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Enantiomeric separation of chiral pesticides by high performance liquid chromatography on cellulose tris‐3,5‐dimethyl carbamate stationary phase under reversed phase conditions

Cited by 37 publications

References 44 publications

Enantiomeric separation of triazole fungicides with 3‐μm and 5‐μml particle chiral columns by reverse‐phase high‐performance liquid chromatography

Enantiomeric separation of triazole fungicides with 3‐μm and 5‐μml particle chiral columns by reverse‐phase high‐performance liquid chromatography

Preparation and evaluation of a deoxycholic‐calix[4]arene hybrid‐type receptor as a chiral stationary phase for HPLC

Enantioselective bioaccumulation and toxic effects of fipronil in the earthworm Eisenia foetida following soil exposure

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