Direct Enantiomeric Separation and Determination of Hexythiazox Enantiomers in Environment and Vegetable by Reverse-Phase High-Performance Liquid Chromatography
Abstract
:1. Introduction
2. Materials and Methods
2.1. Chemicals and Reagents
2.2. Apparatus and Chiral HPLC Analysis
2.3. Method Validation
2.4. Sample Preparation
2.5. Data Analysis
3. Results
3.1. Chiral Separation of Hexythiazox Enantiomers
3.2. Effects of Temperature on Hexythiazox Enantiomers Separation
3.3. Thermodynamic Parameters on Hexythiazox Enantiomers Separation
3.4. Hexythiazox Enantiomers Analysis in Vegetable and Environment
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
Abbreviations
References
- Thwaite, W.G. Resistance to Clofentezine and Hexythiazox in Panonychus-Ulmi from Apples in Australia. Exp. Appl. Acarol. 1991, 11, 73–80. [Google Scholar] [CrossRef]
- Saber, A.N.; Malhat, F.M.; Badawy, H.M.; Barakat, D.A. Dissipation dynamic, residue distribution and processing factor of hexythiazox in strawberry fruits under open field condition. Food Chem. 2016, 196, 1108–1116. [Google Scholar] [CrossRef] [PubMed]
- Ganjisaffar, F.; Perring, T.M. Effects of the miticide hexythiazox on biology of Galendromus flumenis (Acari: Phytoseiidae). Int. J. Acarol. 2016, 43, 169–172. [Google Scholar] [CrossRef]
- Abdourahime, H.; Anastassiadou, M.; Brancato, A.; Brocca, D.; Carrasco Cabrera, L.; De Lentdecker, C.; Ferreira, L.; Greco, L.; Jarrah, S.; Kardassi, D.; et al. Review of the existing maximum residue levels for hexythiazox according to Article 12 of Regulation (EC) No 396/2005. EFSA J. 2019, 17, e05559. [Google Scholar]
- Liu, W.; Gan, J.; Schlenk, D.; Jury, W.A. Enantioselectivity in environmental safety of current chiral insecticides. Proc. Natl. Acad. Sci. USA 2005, 102, 701–706. [Google Scholar] [CrossRef] [Green Version]
- Ye, J.; Wu, J.; Liu, W. Enantioselective separation and analysis of chiral pesticides by high-performance liquid chromatography. TrAC-Trend Anal. Chem. 2009, 28, 1148–1163. [Google Scholar] [CrossRef]
- Ye, J.; Zhao, M.; Liu, J.; Liu, W. Enantioselectivity in environmental risk assessment of modern chiral pesticides. Environ. Pollut. 2010, 158, 2371–2383. [Google Scholar] [CrossRef]
- Jeschke, P. Current status of chirality in agrochemicals. Pest. Manag. Sci. 2018, 74, 2389–2404. [Google Scholar] [CrossRef]
- De Albuquerque, N.C.P.; Carrao, D.B.; Habenschus, M.D.; de Oliveira, A.R.M. Metabolism studies of chiral pesticides: A critical review. J. Pharm. Biomed. Anal. 2018, 147, 89–109. [Google Scholar] [CrossRef]
- Chang, J.; Xu, P.; Li, W.; Li, J.; Wang, H. Enantioselective Elimination and Gonadal Disruption of Lambda-Cyhalothrin on Lizards (Eremias argus). J. Agric. Food Chem. 2019, 67, 2183–2189. [Google Scholar] [CrossRef]
- Chang, W.; Nie, J.; Yan, Z.; Wang, Y.; Farooq, S. Systemic Stereoselectivity Study of Etoxazole: Stereoselective Bioactivity, Acute Toxicity, and Environmental Behavior in Fruits and Soils. J. Agric. Food Chem. 2019, 67, 6708–6715. [Google Scholar] [CrossRef]
- Chen, Z.; Yao, X.; Dong, F.; Duan, H.; Shao, X.; Chen, X.; Yang, T.; Wang, G.; Zheng, Y. Ecological toxicity reduction of dinotefuran to honeybee: New perspective from an enantiomeric level. Environ. Int. 2019, 130, 104854. [Google Scholar] [CrossRef]
- Tong, Z.; Dong, X.; Yang, S.; Sun, M.; Gao, T.; Duan, J.; Cao, H. Enantioselective effects of the chiral fungicide tetraconazole in wheat: Fungicidal activity and degradation behavior. Environ. Pollut. 2019, 247, 1–8. [Google Scholar] [CrossRef] [PubMed]
- Xu, C.; Sun, X.; Niu, L.; Yang, W.; Tu, W.; Lu, L.; Song, S.; Liu, W. Enantioselective thyroid disruption in zebrafish embryo-larvae via exposure to environmental concentrations of the chloroacetamide herbicide acetochlor. Sci. Total Environ. 2019, 653, 1140–1148. [Google Scholar] [CrossRef] [PubMed]
- Perez-Fernandez, V.; Dominguez-Vega, E.; Chankvetadze, B.; Crego, A.L.; Garcia, M.A.; Marina, M.L. Evaluation of new cellulose-based chiral stationary phases Sepapak-2 and Sepapak-4 for the enantiomeric separation of pesticides by nano liquid chromatography and capillary electrochromatography. J. Chromatogr. A 2012, 1234, 22–31. [Google Scholar] [CrossRef] [PubMed]
- Fox, S.; Strasdeit, H.; Haasmann, S.; Bruckner, H. Gas chromatographic separation of stereoisomers of non-protein amino acids on modified gamma-cyclodextrin stationary phase. J. Chromatogr. A 2015, 1411, 101–109. [Google Scholar] [CrossRef]
- Wang, P.; Jiang, S.; Liu, D.; Zhang, H.; Zhou, Z. Enantiomeric resolution of chiral pesticides by high-performance liquid chromatography. J. Agric. Food Chem. 2006, 54, 1577–1583. [Google Scholar] [CrossRef] [PubMed]
- Tian, Q.; Zhou, Z.Q.; Lv, C.G.; Yang, J.J. Direct enantiomeric separation of chiral pesticides by liquid chromatography on polysaccharide-based chiral stationary phases under reversed phase conditions. Anal. Methods 2012, 4, 2307–2317. [Google Scholar] [CrossRef]
- Tan, Q.; Fan, J.; Gao, R.; He, R.; Wang, T.; Zhang, Y.; Zhang, W. Stereoselective quantification of triticonazole in vegetables by supercritical fluid chromatography. Talanta 2017, 164, 362–367. [Google Scholar] [CrossRef]
- Liu, N.; Dong, F.; Xu, J.; Liu, X.; Chen, Z.; Pan, X.; Chen, X.; Zheng, Y. Enantioselective separation and pharmacokinetic dissipation of cyflumetofen in field soil by ultra-performance convergence chromatography with tandem mass spectrometry. J. Sep. Sci. 2016, 39, 1363–1370. [Google Scholar] [CrossRef]
- Shea, D.; Penmetsa, K.V.; Leidy, R.B. Enantiomeric and isomeric separation of pesticides by cyclodextrin-modified micellar electrokinetic chromatography. J. AOAC Int. 1999, 82, 1550–1561. [Google Scholar] [CrossRef] [Green Version]
- Qiu, J.; Dai, S.; Zheng, C.; Yang, S.; Chai, T.; Bie, M. Enantiomeric separation of triazole fungicides with 3-mum and 5-muml particle chiral columns by reverse-phase high-performance liquid chromatography. Chirality 2011, 23, 479–486. [Google Scholar] [CrossRef]
- Rybar, I.; Gora, R.; Hutta, M. Method of fast trace microanalysis of the chiral pesticides epoxiconazole and novaluron in soil samples using off-line flow-through extraction and on-column direct large volume injection in reversed-phase high performance liquid chromatography. J. Sep. Sci. 2007, 30, 3164–3173. [Google Scholar] [CrossRef]
- Zhang, P.; Yu, Q.; He, Y.; Zhu, W.; Zhou, Z.; He, L. Chiral pyrethroid insecticide fenpropathrin and its metabolite: Enantiomeric separation and pharmacokinetic degradation in soils by reverse-phase high-performance liquid chromatography. Anal. Methods 2017, 9, 4439–4446. [Google Scholar] [CrossRef]
- Zhang, P.; Zhu, W.; Qiu, J.; Wang, D.; Wang, X.; Wang, Y.; Zhou, Z. Evaluating the enantioselective degradation and novel metabolites following a single oral dose of metalaxyl in mice. Pestic. Biochem. Physiol. 2014, 116, 32–39. [Google Scholar] [CrossRef] [PubMed]
- Wang, Y.; Xu, L.; Li, D.; Teng, M.; Zhang, R.; Zhou, Z.; Zhu, W. Enantioselective bioaccumulation of hexaconazole and its toxic effects in adult zebrafish (Danio rerio). Chemosphere 2015, 138, 798–805. [Google Scholar] [CrossRef]
- Wang, Y.; Zhu, W.; Qiu, J.; Wang, X.; Zhang, P.; Yan, J.; Zhou, Z. Monitoring tryptophan metabolism after exposure to hexaconazole and the enantioselective metabolism of hexaconazole in rat hepatocytes in vitro. J. Hazard. Mater. 2015, 295, 9–16. [Google Scholar] [CrossRef]
- Liu, C.; Wang, B.; Xu, P.; Liu, T.; Di, S.; Diao, J. Enantioselective determination of triazole fungicide epoxiconazole bioaccumulation in tubifex based on HPLC-MS/MS. J. Agric. Food Chem. 2014, 62, 360–367. [Google Scholar] [CrossRef]
- Wang, P.; Liu, D.; Jiang, S.; Xu, Y.; Gu, X.; Zhou, Z. The chiral resolution of pesticides on amylose-tris(3,5-dimethylphenylcarbamate) CSP by HPLC and the enantiomeric identification by circular dichroism. Chirality 2008, 20, 40–46. [Google Scholar] [CrossRef]
- Zhang, P.; Yu, Q.; He, X.; Qian, K.; Xiao, W.; Xu, Z.; Li, T.; He, L. Enantiomeric separation of type I and type II pyrethroid insecticides with different chiral stationary phases by reversed-phase high-performance liquid chromatography. Chirality 2018, 30, 420–431. [Google Scholar] [CrossRef]
Stationary Phase | Mobile Phase (v/v) | Temperature (°C) | k1 | k2 | α | Rs | Mobile Phase (v/v) | Temperature (°C) | k1 | k2 | α | Rs |
---|---|---|---|---|---|---|---|---|---|---|---|---|
Lux Cellulose-1 | MeOH/H2O 85/15 | 10 | 3.83 | 4.18 | 1.09 | 0.79 | ACN/H2O 60/40 | 10 | 4.77 | 5.05 | 1.06 | 0.73 |
15 | 3.59 | 3.89 | 1.08 | 0.70 | 15 | 4.50 | 4.75 | 1.05 | 0.67 | |||
20 | 3.25 | 3.50 | 1.08 | 0.68 | 20 | 4.34 | 4.56 | 1.05 | 0.66 | |||
25 | 3.00 | 3.20 | 1.07 | 0.66 | 25 | 4.13 | 4.32 | 1.04 | 0.62 | |||
30 | 2.64 | 2.80 | 1.06 | 0.65 | 30 | 3.86 | 4.02 | 1.04 | 0.59 | |||
35 | 2.49 | 2.63 | 1.06 | 0.59 | 35 | 3.72 | 3.85 | 1.04 | 0.54 | |||
40 | 2.30 | 2.39 | 1.04 | 0.44 | 40 | 3.44 | 3.56 | 1.03 | 0.48 | |||
Lux Cellulose-2 | MeOH/H2O 90/10 | 10 | 2.12 | 2.28 | 1.08 | 0.88 | ACN/H2O 70/30 | 10 | 2.90 | 3.05 | 1.05 | 0.72 |
15 | 2.09 | 2.24 | 1.07 | 0.76 | 15 | 2.79 | 2.93 | 1.05 | 0.69 | |||
20 | 1.93 | 2.05 | 1.06 | 0.67 | 20 | 2.65 | 2.76 | 1.04 | 0.63 | |||
25 | 1.78 | 1.88 | 1.06 | 0.63 | 25 | 2.51 | 2.61 | 1.04 | 0.59 | |||
30 | 1.64 | 1.73 | 1.05 | 0.60 | 30 | 2.36 | 2.44 | 1.03 | 0.52 | |||
35 | 1.52 | 1.60 | 1.05 | 0.55 | 35 | 2.22 | 2.29 | 1.03 | 0.51 | |||
40 | 1.41 | 1.47 | 1.04 | 0.52 | 40 | 2.09 | 2.15 | 1.03 | 0.48 | |||
Lux Cellulose-3 | MeOH/H2O 90/10 | 10 | 1.77 | 2.26 | 1.28 | 1.94 | ACN/H2O 60/40 | 10 | 1.31 | 1.76 | 1.35 | 2.49 |
15 | 1.62 | 2.05 | 1.27 | 1.83 | 15 | 1.28 | 1.70 | 1.33 | 2.45 | |||
20 | 1.57 | 1.98 | 1.26 | 1.79 | 20 | 1.23 | 1.62 | 1.32 | 2.28 | |||
25 | 1.46 | 1.83 | 1.25 | 1.77 | 25 | 1.16 | 1.51 | 1.30 | 2.20 | |||
30 | 1.37 | 1.70 | 1.25 | 1.70 | 30 | 1.11 | 1.43 | 1.29 | 2.15 | |||
35 | 1.25 | 1.56 | 1.24 | 1.68 | 35 | 1.05 | 1.34 | 1.27 | 2.01 | |||
40 | 1.16 | 1.43 | 1.23 | 1.61 | 40 | 1.00 | 1.26 | 1.26 | 2.00 | |||
Lux Cellulose-4 | MeOH/H2O 90/10 | 10 | 1.60 | 1.70 | 1.06 | 0.66 | ACN/H2O 70/30 | 10 | 2.18 | 2.32 | 1.06 | 0.76 |
15 | 1.54 | 1.63 | 1.06 | 0.62 | 15 | 2.11 | 2.23 | 1.06 | 0.74 | |||
20 | 1.43 | 1.51 | 1.05 | 0.57 | 20 | 2.04 | 2.15 | 1.05 | 0.73 | |||
25 | 1.32 | 1.38 | 1.05 | 0.54 | 25 | 1.95 | 2.04 | 1.05 | 0.68 | |||
30 | 1.23 | 1.29 | 1.04 | 0.50 | 30 | 1.86 | 1.94 | 1.04 | 0.66 | |||
35 | 1.17 | 1.22 | 1.04 | 0.47 | 35 | 1.72 | 1.79 | 1.04 | 0.61 | |||
40 | 1.08 | 1.11 | 1.03 | 0.42 | 40 | 1.62 | 1.67 | 1.03 | 0.53 | |||
Lux Amylose-1 | - | 10 | - | - | - | - | ACN/H2O 60/40 | 10 | 2.91 | 3.36 | 1.15 | 0.82 |
15 | - | - | - | - | 15 | 2.81 | 3.22 | 1.14 | 0.79 | |||
20 | - | - | - | - | 20 | 2.70 | 3.08 | 1.14 | 0.76 | |||
25 | - | - | - | - | 25 | 2.59 | 2.93 | 1.13 | 0.73 | |||
30 | - | - | - | - | 30 | 2.53 | 2.85 | 1.13 | 0.70 | |||
35 | - | - | - | - | 35 | 2.39 | 2.67 | 1.12 | 0.68 | |||
40 | - | - | - | - | 40 | 2.27 | 2.52 | 1.11 | 0.65 | |||
Chiralpak IC | - | 10 | - | - | - | - | ACN/H2O 60/40 | 10 | 1.71 | 1.84 | 1.07 | 0.72 |
15 | - | - | - | - | 15 | 1.65 | 1.76 | 1.07 | 0.69 | |||
20 | - | - | - | - | 20 | 1.55 | 1.66 | 1.07 | 0.68 | |||
25 | - | - | - | - | 25 | 1.45 | 1.54 | 1.06 | 0.65 | |||
30 | - | - | - | - | 30 | 1.37 | 1.45 | 1.06 | 0.64 | |||
35 | - | - | - | - | 35 | 1.29 | 1.36 | 1.05 | 0.62 | |||
40 | - | - | - | - | 40 | 1.24 | 1.30 | 1.05 | 0.55 |
Column | Mobile Phase (v/v) | lnk = −△H/RT + △S/R + lnφ | R2 | △H (KJ mol-1) | △S/R+ lnφ | lnα = −∆∆H/RT + ∆∆S/R | R2 | △△H (KJ mol-1) | △△S (J mol-1) |
---|---|---|---|---|---|---|---|---|---|
Lux Cellulose-1 | MeOH/H2O 85/15 | lnk1 = 1560.1/T−4.1536 | 0.994 | −12.97 | −4.55 | lnα = 132.9/T-0.3805 | 0.962 | −1.10 | −3.16 |
lnk2 = 1693/T−4.5341 | 0.995 | −14.08 | −4.78 | ||||||
ACN/H2O 60/40 | lnk1 = 936.25/T−1.7378 | 0.988 | −7.78 | −0.35 | lnα = 71.652/T-0.1962 | 0.998 | −0.60 | −1.63 | |
lnk2 = 1007.9/T−1.934 | 0.990 | −8.38 | −0.42 | ||||||
Lux Cellulose-2 | MeOH/H2O 90/10 | lnk1 = 1276.6/T−3.7204 | 0.980 | −10.61 | −3.56 | lnα = 90.966/T-0.2477 | 0.996 | −0.76 | −2.06 |
lnk2 = 1367.5/T−3.9682 | 0.982 | −11.37 | −5.55 | ||||||
ACN/H2O 70/30 | lnk1 = 983.82/T−2.3939 | 0.990 | −8.18 | −3.71 | lnα = 71.12/T-0.2006 | 0.995 | −0.59 | −1.67 | |
lnk2 = 1054.9/T−2.5946 | 0.992 | −8.77 | −5.99 | ||||||
Lux Cellulose-3 | MeOH/H2O 90/10 | lnk1 = 1211/T−3.7009 | 0.986 | −10.07 | −5.37 | lnα = 99.749/T-0.1097 | 0.994 | −0.83 | −0.91 |
lnk2 = 1310.8/T−3.8105 | 0.988 | −10.90 | −5.78 | ||||||
ACN/H2O 60/40 | lnk1 = 824.51/T−2.6256 | 0.986 | −6.85 | −1.43 | lnα = 192.8/T-0.3828 | 0.997 | −1.60 | −3.18 | |
lnk2 = 1017.3/T−3.0084 | 0.989 | −8.46 | −1.63 | ||||||
Lux Cellulose-4 | MeOH/H2O 90/10 | lnk1 = 1193.9/T−3.7285 | 0.992 | −9.93 | −6.93 | lnα = 74.735/T-0.2033 | 0.988 | −0.62 | −1.69 |
lnk2 = 1268.7/T−3.9318 | 0.992 | −10.55 | −9.69 | ||||||
ACN/H2O 70/30 | lnk1 = 872.27/T−2.2803 | 0.967 | −7.25 | −1.05 | lnα = 80.151/T-0.2215 | 0.997 | −0.67 | −1.84 | |
lnk2 = 952.42/T−2.5018 | 0.971 | −7.92 | −0.97 | ||||||
Lux Amylose-1 | ACN/H2O 60/40 | lnk1 = 715.75/T−1.4515 | 0.987 | −5.95 | −1.43 | lnα = 113.47/T-0.258 | 0.996 | −0.94 | −2.15 |
lnk2 = 829.22/T−1.7095 | 0.989 | −6.89 | −1.63 | ||||||
Chirapak IC | ACN/H2O 60/40 | lnk1 = 1003.6/T−2.9947 | 0.995 | −8.34 | −1.05 | lnα = 65.454/T-0.1604 | 0.992 | −0.54 | −1.33 |
lnk2 = 1069.1/T-3.1551 | 0.995 | −8.89 | −0.97 |
Compound | Matrix | Spiked Levels (mg∙kg−1 or mg∙L−1) | Intraday a | Interday b | ||||||
---|---|---|---|---|---|---|---|---|---|---|
Day 1 | Day 2 | Day 3 | ||||||||
Recovery (%) | RSD c (%) | Recovery (%) | RSD (%) | Recovery (%) | RSD (%) | Recovery (%) | RSD (%) | |||
E1 | soil | 0.05 | 89.38 | 4.87 | 88.00 | 5.31 | 87.21 | 5.59 | 88.19 | 5.36 |
0.5 | 94.33 | 4.52 | 98.93 | 3.12 | 90.82 | 2.67 | 94.69 | 4.98 | ||
5 | 96.58 | 3.48 | 97.55 | 2.80 | 93.34 | 2.62 | 95.83 | 3.54 | ||
water | 0.05 | 81.40 | 5.91 | 84.91 | 5.34 | 87.76 | 6.14 | 84.69 | 6.58 | |
0.5 | 88.77 | 4.38 | 92.99 | 3.92 | 94.36 | 5.01 | 92.04 | 5.16 | ||
5 | 93.96 | 4.89 | 94.18 | 2.05 | 97.46 | 1.66 | 95.20 | 3.59 | ||
cucumber | 0.05 | 95.94 | 6.29 | 91.75 | 6.68 | 88.75 | 3.87 | 92.15 | 6.63 | |
0.5 | 93.31 | 5.13 | 92.49 | 3.63 | 95.79 | 5.33 | 93.86 | 5.00 | ||
5 | 97.50 | 2.20 | 96.49 | 3.63 | 96.74 | 3.26 | 96.91 | 3.12 | ||
tomato | 0.05 | 89.65 | 5.21 | 90.54 | 4.01 | 89.30 | 3.80 | 89.83 | 4.42 | |
0.5 | 96.94 | 6.00 | 96.27 | 1.93 | 98.71 | 4.30 | 97.31 | 4.54 | ||
5 | 97.36 | 3.78 | 96.56 | 2.94 | 97.51 | 1.98 | 97.14 | 3.02 | ||
cabbage | 0.05 | 90.36 | 4.76 | 89.39 | 4.22 | 91.65 | 3.85 | 90.47 | 4.41 | |
0.5 | 97.43 | 3.00 | 96.06 | 1.93 | 99.84 | 3.90 | 97.78 | 3.47 | ||
5 | 98.79 | 3.77 | 97.71 | 3.19 | 98.88 | 2.01 | 98.46 | 3.13 | ||
E2 | soil | 0.05 | 91.38 | 5.45 | 88.84 | 6.38 | 89.09 | 5.54 | 89.77 | 5.94 |
0.5 | 95.17 | 4.75 | 93.41 | 3.30 | 93.16 | 2.15 | 93.91 | 3.71 | ||
5 | 97.29 | 3.60 | 99.12 | 3.42 | 95.72 | 1.69 | 97.38 | 3.36 | ||
water | 0.05 | 86.54 | 5.62 | 89.10 | 6.91 | 87.61 | 6.01 | 87.75 | 6.33 | |
0.5 | 91.21 | 2.31 | 96.71 | 3.49 | 99.44 | 5.54 | 95.79 | 5.44 | ||
5 | 95.07 | 4.27 | 93.90 | 2.90 | 97.15 | 2.21 | 95.37 | 3.52 | ||
cucumber | 0.05 | 96.18 | 6.58 | 97.10 | 3.25 | 92.06 | 5.46 | 95.11 | 5.75 | |
0.5 | 94.55 | 2.67 | 94.64 | 1.65 | 93.86 | 4.02 | 94.35 | 2.96 | ||
5 | 96.28 | 2.65 | 98.92 | 4.15 | 97.49 | 2.86 | 97.56 | 3.49 | ||
tomato | 0.05 | 89.57 | 3.08 | 89.16 | 6.44 | 91.84 | 2.06 | 90.19 | 4.45 | |
0.5 | 100.46 | 4.89 | 98.84 | 3.79 | 102.48 | 5.71 | 100.60 | 5.10 | ||
5 | 97.25 | 3.32 | 97.07 | 3.52 | 97.36 | 2.88 | 97.23 | 3.25 | ||
cabbage | 0.05 | 94.86 | 2.93 | 94.50 | 4.05 | 92.78 | 3.98 | 94.05 | 3.81 | |
0.5 | 97.60 | 4.66 | 95.67 | 3.70 | 101.50 | 2.95 | 98.26 | 4.54 | ||
5 | 101.39 | 3.12 | 96.39 | 4.22 | 99.27 | 1.47 | 99.02 | 3.75 |
© 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
Share and Cite
Zhang, P.; Wang, S.; Shi, D.; Xu, Y.; Yang, F.; Deng, X.; He, Y.; He, L. Direct Enantiomeric Separation and Determination of Hexythiazox Enantiomers in Environment and Vegetable by Reverse-Phase High-Performance Liquid Chromatography. Int. J. Environ. Res. Public Health 2020, 17, 3453. https://doi.org/10.3390/ijerph17103453
Zhang P, Wang S, Shi D, Xu Y, Yang F, Deng X, He Y, He L. Direct Enantiomeric Separation and Determination of Hexythiazox Enantiomers in Environment and Vegetable by Reverse-Phase High-Performance Liquid Chromatography. International Journal of Environmental Research and Public Health. 2020; 17(10):3453. https://doi.org/10.3390/ijerph17103453
Chicago/Turabian StyleZhang, Ping, Sheng Wang, Dongmei Shi, Yangyang Xu, Furong Yang, Xile Deng, Yuhan He, and Lin He. 2020. "Direct Enantiomeric Separation and Determination of Hexythiazox Enantiomers in Environment and Vegetable by Reverse-Phase High-Performance Liquid Chromatography" International Journal of Environmental Research and Public Health 17, no. 10: 3453. https://doi.org/10.3390/ijerph17103453