Determination of the Optical Purity of Fungicides of the Triazole Series

Shapovalova, E. N.; Шпигун, О. А.; Nesterova, L. M.; Belov, M. Yu.

doi:10.1023/b:janc.0000018969.54931.5a

Cited by 15 publications

(14 citation statements)

References 5 publications

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“…The relationship between absolute configurations and optical rotations of the tebuconazole enantiomers were already reported in previous study. 9 Correspondingly, the first eluted enantiomer was (2)-R-tebuconazole, while the second one was (1)-S-tebuconazole in our study. Representative chromatograms of (A) extract from blank soil 3, (B) extract from soil 3 fortified with rac-tebuconazole (1 lg/g), (C) extract from soil 3 after 160-days incubation with rac-tebuconazole, (D) extract from untreated cabbage, (E) extract from cabbage fortified with rac-tebuconazole (1 lg/g), (F) extract from cabbage at 28 days after treatment with rac-tebuconazole, (G) extract from untreated cucumber fruit, (H) extract from cucumber fruit fortified with rac-tebuconazole (0.1 lg/g), and (I) extract from cucumber fruit at 7 days after treatment with rac-tebuconazole.…”

Section: Results and Disscussion Identification Elution Order Of Tebusupporting

confidence: 66%

“…Its absolute configuration was already confirmed with left-optical (2) rotation of Renantiomer and right-optical (1) rotation of S-enantiomer. 9 Tebuconazole was marketed as the racemic product, although the fungicidal activity of the (2)-R-enantiomer is greater than (1)-S-enantiomer. 10 A great number of methods have been reported for achiral analysis and residue determinations of tebuconazole in various matrixes.…”

Section: Introductionmentioning

confidence: 99%

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Enantioselective degradation of tebuconazole in cabbage, cucumber, and soils

Wang¹,

Wang²,

Zhang³

et al. 2011

Chirality

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The enantioselective degradation of tebuconazole has been investigated to elucidate the behaviors in agricultural soils, cabbage, and cucumber fruit. Rac-tebuconazole was fortified into three types of agricultural soils and sprayed foliage of cabbage and cucumber, respectively. The degradation kinetics, enantiomer fraction and enantiomeric selectivity were determined by reverse-phase high-performance liquid chromatography (HPLC) and liquid chromatography-mass spectrometry/mass spectrometry (LC-MS/MS) on a Lux amylose-2 chiral column. The process of the degradation of tebuconazole enantiomers followed first-order kinetic in the test soils and vegetables. It has been shown that the degradation of tebuconazole was enantioselective. The results indicated that the (+)-S-tebuconazole showed a faster degradation in cabbage, while the (-)-R-tebuconazole dissipated faster than (+)-S-form in cucumber fruit and the test soils.

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Section: Results and Disscussion Identification Elution Order Of Tebusupporting

confidence: 66%

Section: Introductionmentioning

confidence: 99%

Enantioselective degradation of tebuconazole in cabbage, cucumber, and soils

Wang¹,

Wang²,

Zhang³

et al. 2011

Chirality

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“…The polar carbamate groups of CDMPC were thought as the main chiral recognition regions because those can physically interact with the analytes through hydrogen bonding with NH groups and dipole–dipole interactions with CO groups. Phenylcarbamate contribute to chiral recognition not only by the direct interaction with enantiomers, but also by maintaining the highly organized structure of CSP through intermolecular hydrogen bonds 9, 11. In this study, the chiral recognition process may be the joint interactions including hydrogen bonding between OH on hexaconazole ( 1 ) , flutriafol ( 2 ) , diniconazole ( 3 ) , and NH on CSP; dipole–dipole between CO on triadimefon ( 9 ), CN on myclobutanil ( 7 ) , fenbuconazole ( 8 ) and CO on CSP; π‐π interaction between aromatic rings of triazole fungicides and phenyl groups of the CSP.…”

Section: Resultsmentioning

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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“…It is observed that the elution order of tebuconazole was (1)-tebuconazole, (À)-tebuconazole. Furthermore, the relationships between absolute configurations and ORs of the two tebuconazole enantiomers were determined by the previous research work [16]. Therefore, the first eluted enantiomer was (1)-S-tebuconazole, while the second was (À)-R-tebuconazole in this study.…”

Section: Elution Order Determination Of Tebuconazole Enantiomersmentioning

confidence: 82%

“…Tebuconazole has an asymmetrically substituted C atom and consists of a pair of enantiomers. Its absolute configuration was already confirmed with leftoptical (À) rotation of R-enantiomer and right-optical (1) rotation of S-enantiomer [16]. However, this fungicide is commonly marketed and administered as a racemic product, although the fungicidal activity of the (À)-R-enantiomer is greater than (1)-S-enantiomer [17].…”

Section: Introductionmentioning

confidence: 99%

Enantioselective determination of triazole fungicide tebuconazole in vegetables, fruits, soil and water by chiral liquid chromatography/tandem mass spectrometry

Dong

Liu

et al. 2011

J of Separation Science

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A novel and sensitive method was developed for the determination of tebuconazole enantioselectively using reversed-phase LC-MS/MS. The separation and determination were performed using on an amylose-based chiral stationary phase, a Lux 3u Amylose-2 column (150 mm×2.0 mm), under isocratic conditions at 0.3 mL/min flow rate. A series of chiral stationary phases were investigated and the effect of mobile phase composition on the enantioseparation was discussed. Parameters including the matrix effect, linearity, precision, accuracy and stability were evaluated. Under optimal conditions, the overall mean recoveries for two enantiomers from the soil, tomato, cucumber, pear and apple samples were 79.3-101.1% with 2.8-11.5% intra-day relative standard deviations (RSDs) and 4.1-8.6% inter-day RSDs at 5, 25 and 50 μg/kg levels; the mean enantiomer recoveries from the water samples were 89.6-101.9% with 3.3-10.2% intra-day RSDs and 5.1-7.7% inter-day RSDs at 0.25, 0.5 and 2.5 μg/kg levels. The limits of detection (LODs) for all enantiomers in tomato, cucumber, pear, apple, soil and water were less than 0.6 μg/kg, whereas the limit of quantification (LOQ) did not exceed 2.0 μg/kg. The results indicate that this proposed method is convenient and reliable for the enantioselective determination of tebuconazole enantiomers in foods and environment samples.

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Determination of the Optical Purity of Fungicides of the Triazole Series

Cited by 15 publications

References 5 publications

Enantioselective degradation of tebuconazole in cabbage, cucumber, and soils

Enantioselective degradation of tebuconazole in cabbage, cucumber, and soils

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

Enantioselective determination of triazole fungicide tebuconazole in vegetables, fruits, soil and water by chiral liquid chromatography/tandem mass spectrometry

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