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

Qiu, Jing; Dai, Shikun; Zheng, Chuangmu; Yang, Shuming; Chai, Tuanyao; Mei, Bie

doi:10.1002/chir.20950

Cited by 44 publications

(38 citation statements)

References 21 publications

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“…21 Additionally, cyproconazole (5) and bromuconazole (9) also can get good separations by cyclodextrin-modified micellar electrokinetic capillary chromatography. 23 In previous reports, fenbuconazole (10) got very satisfactory separation on CDMPC with R s of 3.96-9.03 using ACN/water and MET/water 14,15 and was significantly better than separation on ACMPC with R s of 0.85. Konwick et al, cyproconazole (5), metconazole (8), and bromuconazole (9) were separated using the Chiralsel-Dex column on gas chromatography with electron capture detector.…”

Section: Effects Of Different Modifiers On Enantioseparationmentioning

confidence: 84%

“…The best resolutions were obtained at 20 C for simeconazole (1), carfentrazone-ethyl (4), cyproconazole (5), and metconazole (8); 30 C for diclobutrazol (2) and nuarimol (3); and 40 C for famoxadone (6) and etaconzole (7). 15,26 Generally, the change of solvent percentage in mobile phase would not change enantiomeric optical rotation signals, but the change of solvent types would lead to reversed signals. 24,25 Elution Order HPLC with ORD is often applied to detect elution orders according to positive (+) or negative (À) optical rotation signals of enantiomers.…”

Section: Effects Of Column Temperature On Enantioseparationmentioning

confidence: 99%

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Direct Enantioseparation of Nitrogen‐heterocyclic Pesticides on Amylose‐tris‐(5‐chloro‐2‐methylphenylcarbamate) by Reversed‐Phase High‐Performance Liquid Chromatography

et al. 2012

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In this study, 11 nitrogen-heterocyclic pesticides were stereoselectively separated on amylose-tris-(5-chloro-2-methylphenylcarbamate) chiral stationary phase, using reversed-phase high-performance liquid chromatography with diode array detector and optical rotation detector at 426 nm. The effects of mobile phase composition and column temperature (5-40 °C) on separation were investigated. When acetonitrile and water were used as mobile phase, satisfactory separations were obtained on amylose-tris-(5-chloro-2-methylphenylcarbamate) for four pesticides with elution orders of (+)/(-)-simeconazole (1), (-)/(+)-nuarimol (3), (-)/(+)-carfentrazone-ethyl (4), and (-)/(+)/(-)/(+)-bromuconazole (9) and part separations for three with elution orders of (-)/(+)-famoxadone (6), (+)/(-)-fenbuconazole (10), and (-)/(+)-triapenthenol (11). Only two chromatographic peaks on diode array detector were obtained for diclobutrazol (2), cyproconazole (5), etaconazole (7), and metconazole (8), although they should have four stereoisomers in theory because of presences of two chiral centers in molecules. The stereoisomeric optical signals of all pesticides did not reverse with temperature changes but would reverse with different solvent types for some pesticides. These results will be useful to prepare and analyze individual enantiomers of chiral pesticides.

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Section: Effects Of Different Modifiers On Enantioseparationmentioning

confidence: 84%

Section: Effects Of Column Temperature On Enantioseparationmentioning

confidence: 99%

Direct Enantioseparation of Nitrogen‐heterocyclic Pesticides on Amylose‐tris‐(5‐chloro‐2‐methylphenylcarbamate) by Reversed‐Phase High‐Performance Liquid Chromatography

et al. 2012

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“…1 A large number of pesticides contain stereogenic centers and are introduced into markets in the form of racemates. 1 A large number of pesticides contain stereogenic centers and are introduced into markets in the form of racemates.…”

Section: Introductionmentioning

confidence: 99%

Direct Enantioseparation of Nitrogen‐Heterocyclic Pesticides on Cellulose‐Based Chiral Column by High‐Performance Liquid Chromatography

et al. 2014

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The enantiomeric separation of eight pesticides including bitertanol (), diclobutrazol (), fenbuconazole (), triticonazole (), imazalil (), triapenthenol (), ancymidol (), and carfentrazone-ethyl () was achieved, using normal-phase high-performance liquid chromatography on two cellulosed-based chiral columns. The effects of isopropanol composition from 2% to 30% in the mobile phase and column temperature from 5 to 40 °C were investigated. Satisfactory resolutions were obtained for bitertanol (), triticonazole (), imazalil () with the (+)-enantiomer eluted first and fenbuconazole () with the (-)-enantiomer eluted first on Lux Cellulose-2 and Lux Cellulose-3. (+)-Enantiomers of diclobutrazol () and triapenthenol () were first eluted on Lux Cellulose-2. (-)-Carfentrazone-ethyl () were eluted first on Lux Cellulose-2 and Lux Cellulose-3 with incomplete separation. Reversed elution orders were obtained for ancymidol (7). (+)-Ancymidol was first eluted on Lux Cellulose-2 while on Lux Cellulose-3 (-)-ancymidol was first eluted. The results of the elution order at different column temperatures suggested that column temperature did not affect the optical signals of the enantiomers. These results will be helpful to prepare and analyze individual enantiomers of chiral pesticides.

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“…According to Qiu's et al (2011), the first peak eluted was S-( À )-diniconazole and the second was R-( þ)-diniconazole as shown in Fig. 1.…”

Section: Methods Validationmentioning

confidence: 98%

Enantioseletive bioaccumulation and metabolization of diniconazole in earthworms (Eiseniafetida) in an artificial soil

Wang

Chen

Guo

et al. 2014

Ecotoxicology and Environmental Safety

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a b s t r a c tDegradation and enantioselective bioaccumulation of diniconazole in earthworms (Eiseniafetida) in artificial soil was investigated using liquid chromatography-tandem mass spectrometry (LC-MS/MS) method under laboratory condition. Three exposure concentrations (1 mg/kg, 10 mg/kg and 25 mg/kg) of diniconazole in soil (dry weight) to earthworms were used. The uptake kinetics fitted the first-order kinetics well. The bioaccumulation factors (BAF) of R, S isomers were 6.6046 and 8.5115 in 25 mg/kg dose exposure, 2.6409 and 2.9835 in 10 mg/kg dose exposure, 1.7784 and 2.0437 in 1 mg/kg dose exposure, respectively. Bioaccumulation of diniconazole in earthworm tissues was enantioselective with a preferential accumulation of S-diniconazole and the enantiomer fractions were about 0.45-0.50 in all three level dose exposures. In addition, it was obvious that both R-diniconazole and S-diniconazole had bioaccumulation effect in earthworm. Diniconazole was metabolized to 1,2,4-triazole, (E)-3-(1H-1,2, 4-triazol-1-yl) acrylaldehyde, (E, S)-4-(2, 4-dichlorophenyl)-2, 2-dimethyl-5-(1H-1,2,4-triazol-1-yl)pent-4-ene-1,3-diol, and (E)-4-(2, 4-dichlorophenyl)-3-hydroxy-2,2-dimethyl-5-(1H-1,2,4-triazol-1-yl) pent-4-enoic acid in earthworms; the metabolites of 1,2,4-triazole and (E)-3-(1H-1,2,4-triazol-1-yl)acrylaldehyde could be detected in soil as well.

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

Cited by 44 publications

References 21 publications

Direct Enantioseparation of Nitrogen‐heterocyclic Pesticides on Amylose‐tris‐(5‐chloro‐2‐methylphenylcarbamate) by Reversed‐Phase High‐Performance Liquid Chromatography

Direct Enantioseparation of Nitrogen‐heterocyclic Pesticides on Amylose‐tris‐(5‐chloro‐2‐methylphenylcarbamate) by Reversed‐Phase High‐Performance Liquid Chromatography

Direct Enantioseparation of Nitrogen‐Heterocyclic Pesticides on Cellulose‐Based Chiral Column by High‐Performance Liquid Chromatography

Enantioseletive bioaccumulation and metabolization of diniconazole in earthworms (Eiseniafetida) in an artificial soil

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