Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2020 May 15;17(10):3453.
doi: 10.3390/ijerph17103453.

Direct Enantiomeric Separation and Determination of Hexythiazox Enantiomers in Environment and Vegetable by Reverse-Phase High-Performance Liquid Chromatography

Ping Zhang  1   2   3 , Sheng Wang  1   2 , Dongmei Shi  1   2 , Yangyang Xu  1   2 , Furong Yang  1   2 , Xile Deng  4 , Yuhan He  1   2 , Lin He  1   2   3
Affiliations

Direct Enantiomeric Separation and Determination of Hexythiazox Enantiomers in Environment and Vegetable by Reverse-Phase High-Performance Liquid Chromatography

Ping Zhang et al. Int J Environ Res Public Health. .

Abstract

In the present study, the direct enantiomeric separation of hexythiazox enantiomers on Lux cellulose-1, Lux cellulose-2, Lux cellulose-3, Lux cellulose-4, Lux amylose-1 and Chirapak IC chiral columns were carefully investigated by reverse-phase high-performance liquid chromatography (RP-HPLC). Acetonitrile/water and methanol/water were used as mobile phase at a flow rate of 0.8 mL·min-1. The effects of chiral stationary phase, temperature, thermodynamic parameters, mobile phase component and mobile phase ratio on hexythiazox enantiomers separation were fully evaluated. Hexythiazox enantiomers received a baseline separation on the Lux cellulose-3 column with a maximum resolution of Rs = 2.09 (methanol/water) and Rs = 2.74 (acetonitrile/water), respectively. Partial separations were achieved on other five chiral columns. Furthermore, Lux amylose-1 and Chirapak IC had no separation ability for hexythiazox enantiomers when methanol/water was used as mobile phase. Temperature study indicated that the capacity factor (k) and resolution factor (Rs) decreased with column temperature increasing from 10 °C to 40 °C. The enthalpy (ΔH) and entropy (ΔS) involved in hexythiazox separation were also calculated and demonstrated the lower temperature contributed to better separation resolution. Moreover, the residue analytical method for hexythiazox enantiomers in the environment (soil and water) and vegetable (cucumber, cabbage and tomato) were also established with reliable accuracy and precision under reverse-phase HPLC condition. Such results provided a baseline separation method for hexythiazox enantiomers under reverse-phase conditions and contributed to an environmental and health risk assessment of hexythiazox at enantiomer level.

Keywords: enantiomeric separation; environment; hexythiazox; residue analysis; vegetable.

PubMed Disclaimer

Conflict of interest statement

The authors declare no conflicts of interest. The funders had no role in the writing of the manuscript and in the decision to publish the results.

Figures

Figure 1
Figure 1
Chemical structure of hexythiazox enantiomers.
Figure 2
Figure 2
Chiral resolution chromatograms of hexythiazox enantiomers on Lux cellulose-1 (A–D), Lux cellulose-2 (E–H), Lux cellulose-3 (I–L), Lux cellulose-4 (M–P), Lux amylose-1 (Q–T) and Chirapak IC (U–X) columns at 20 °C with an ACN/H2O ratio of 90/10 (A,E,I,M,Q,U), 80/20 (B,F,J,N,R,V), 70/30 (C,G,K,O,S,W) and 60/40 (D,H,L,P,T,X), respectively.
Figure 3
Figure 3
Van’t Hoff plots of hexythiazox on (A) Lux Cellulose-1 (acetonitrile/water, 60/40), (B) Lux Cellulose-2 (acetonitrile/water, 70/30), (C) Chirapak IC (acetonitrile/water, 60/40) and (D) Lux amylose-1 (acetonitrile/water, 60/40).
Figure 4
Figure 4
Representative chromatograms of hexythiazox enantiomers on the Lux Cellulose-3 column. (A) Standard solution; (B) extracted from water; (C) extracted from soil; (D) extracted from cucumber; (E) extracted from cabbage; (F) extracted from tomato.
See this image and copyright information in PMC

References

    1. Thwaite W.G. Resistance to Clofentezine and Hexythiazox in Panonychus-Ulmi from Apples in Australia. Exp. Appl. Acarol. 1991;11:73–80. doi: 10.1007/BF01193730. - DOI
    1. 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. doi: 10.1016/j.foodchem.2015.10.052. - DOI - PubMed
    1. Ganjisaffar F., Perring T.M. Effects of the miticide hexythiazox on biology of Galendromus flumenis (Acari: Phytoseiidae) Int. J. Acarol. 2016;43:169–172. doi: 10.1080/01647954.2016.1256348. - DOI
    1. 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. - PMC - PubMed
    1. 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. doi: 10.1073/pnas.0408847102. - DOI - PMC - PubMed

Publication types

MeSH terms

Substances

LinkOut - more resources