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Critical Reviews in Analytical Chemistry Publication details, including instructions for authors and subscription information: http://www.tandfonline.com/loi/batc20
Chromatographic methods for analysis of triazine herbicides a
a
b
Hana Hassan Abbas , Abdalla A. Elbashir & Hassan Y. Aboul-Enein a
Chemistry Department, Faculty of Science, University of Khartoum, Khartoum 11115, Sudan b
Pharmaceutical and Medicinal Chemistry Department, Pharmaceutical and Drug Industries Research Division, National Research Centre, Dokki, Cairo, Egypt Accepted author version posted online: 30 Jun 2014.
To cite this article: Hana Hassan Abbas, Abdalla A. Elbashir & Hassan Y. Aboul-Enein (2014): Chromatographic methods for analysis of triazine herbicides, Critical Reviews in Analytical Chemistry, DOI: 10.1080/10408347.2014.927731 To link to this article: http://dx.doi.org/10.1080/10408347.2014.927731
Disclaimer: This is a version of an unedited manuscript that has been accepted for publication. As a service to authors and researchers we are providing this version of the accepted manuscript (AM). Copyediting, typesetting, and review of the resulting proof will be undertaken on this manuscript before final publication of the Version of Record (VoR). During production and pre-press, errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal relate to this version also.
PLEASE SCROLL DOWN FOR ARTICLE Taylor & Francis makes every effort to ensure the accuracy of all the information (the “Content”) contained in the publications on our platform. However, Taylor & Francis, our agents, and our licensors make no representations or warranties whatsoever as to the accuracy, completeness, or suitability for any purpose of the Content. Any opinions and views expressed in this publication are the opinions and views of the authors, and are not the views of or endorsed by Taylor & Francis. The accuracy of the Content should not be relied upon and should be independently verified with primary sources of information. Taylor and Francis shall not be liable for any losses, actions, claims, proceedings, demands, costs, expenses, damages, and other liabilities whatsoever or howsoever caused arising directly or indirectly in connection with, in relation to or arising out of the use of the Content. This article may be used for research, teaching, and private study purposes. Any substantial or systematic reproduction, redistribution, reselling, loan, sub-licensing, systematic supply, or distribution in any form to anyone is expressly forbidden. Terms & Conditions of access and use can be found at http:// www.tandfonline.com/page/terms-and-conditions
ACCEPTED MANUSCRIPT Chromatographic methods for analysis of triazine herbicides Hana Hassan Abbas1, Abdalla A. Elbashir*1, Hassan Y. Aboul-Enein2*
1
Chemistry Department, Faculty of Science, University of Khartoum, Khartoum 11115, Sudan.
2
Pharmaceutical and Medicinal Chemistry Department, Pharmaceutical and Drug Industries
Downloaded by [University of Texas Libraries] at 03:46 05 December 2014
Research Division, National Research Centre, Dokki, Cairo, Egypt
Abstract Gas chromatography (GC) and High Performance Liquid chromatography (HPLC) coupled to different detectors, and in combination with different sample extraction methods are most widely used for analysis of triazine herbicides in different environmental samples. Nowadays, many variations and modifications of extraction and sample preparation methods such as solid phase microextraction (SPME), hollow fiber-liquid phase microextraction (HF-LPME), stir bar sportive extraction (SBSE), headspace-solid phase microextraction (HS-SPME), dispersive liquid-liquid microextraction (DLLME), dispersive liquid-liquid microextraction based on solidification of floating organic droplet (DLLME-SFO), ultrasound-assisted emulsification microextraction (USAEME), and others, have been introduced and developed to obtain sensitive and accurate methods for the analysis of these hazardous compounds. In this review, several analytical properties such as linearity, sensitivity, repeatability and accuracy for each developed method were discussed, and excellent results were obtained for the most of developed methods combined with GC and HPLC techniques for the analysis of triazine herbicides. This review gives an overview of recent publications of the application of GC and HPLC for analysis of triazine herbicides residues in various samples. Keywords: Triazines,GC, HPLC, Sample extraction Correspondence to: Professor Hassan Y. Aboul-Enein ;E-mail:[email protected]; Tel.+201003678948; Fax:+202-33370931 and Dr. Abdalla A.Elbashir; E-mail: [email protected]
1
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Abbreviations used: 2D, two-dimensional; CPD, cloud point extraction; DAD, diode array detector; DI-SPME, direct immersion-solid phase microextraction; DLLME, dispersive liquidliquid microextraction; DLLME-SFO, dispersive liquid-liquid microextraction based on solidification of floating organic droplet; DLPME, dynamic liquid phase microextraction DµSPE, dispersive micro solid-phase extraction; DMAE, dynamic microwave-assisted
Downloaded by [University of Texas Libraries] at 03:46 05 December 2014
extraction; DMISPE, dummy molecularly imprinted solid-phase extraction; DoE, design of experiments; ECD, electron capture detector; FID, flame ionization detector; GC, gas chromatography; GC-MS, gas chromatography-mass spectrometry; HF-LPME, hollow fiberliquid phase microextraction; HFLSME, hollow fiber-liquid-solid microextraction; HFMT, hollow fiber membrane tube; HPLC, high performance liquid chromatography; HS-LPME, headspace liquid phase microextraction; HS-SPME, headspace-solid phase microextraction; IL, ionic liquid; LC-ESI MS/MS, liquid chromatography-electrospray ionization tandem mass spectrometry; LIT-MS3, linear ion trap mass spectrometry; LLE, liquid-liquid extraction; LODs, limits of detection; LOQs, limits of quantification; LPME, Liquid phase microextraction; LPMESFO, liquid phase microextraction based on solidification of floating organic drop; LS, liquidsolid procedure; MEPS, microextraction in packed syringe; MIP, molecularly imprinted polymer; MNPs, magnetic nanoparticles; MSPD, matrix solid-phase dispersion; MSPE, magnatic solid phase extraction; MWCNTs, multiwalled carbon nanotubes; NPD, nitrogen phosphorus detector; PLE, Pressurized liquid extraction; r, correlation coefficient; RP, reversed phase; RSD, relative standard deviation; SBSE, stir bar sorptive extraction; SCX, strong cation exchange; SDME, single drop microextraction; SE, Shaking extraction; SIM, selected ion monitoring; SPE, solid phase extraction; SPME, solid phase microextraction; SWNHs, single-walled carbon nanohorns; TD-GC-MS/MS, gas chromatography-triple quadrupole mass spectrometry; TDS, total diet study; TER, terbuthylazine; TOF MS, time-of-flight mass spectrometry; USAEME, ultrasound-assisted emulsification microextraction; USVADLLME, ultrasound vortex assisted dispersive liquid-liquid microextraction; UV, ultraviolet.
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1. Introduction 1.1 Triazine herbicides
Triazine herbicides are one of the families of herbicides that inhibit or disrupt normal growth and
Downloaded by [University of Texas Libraries] at 03:46 05 December 2014
development of plant. They are extensively applied in many fields such as agriculture, industry and urban areas to soil for the control of weeds in many agricultural crops (Peterson et al., 2001).
The main triazine herbicides are derived from s-triazine, a six member heterocycle with symmetrically located atoms in which positions 2, 4 and 6 are substituted. The stereochemical stability of s-triazines is large enough to persist in environmental samples from several months to many years (Lebaron et al., 2008).
A list of common s-triazines and some of their properties are given in Table 1. The two most common s-triazines analyzed in waters are atrazine and simazine. The chemical common name depends on the substituent in position 2 (or R1 in Table 1), when a –Cl group is contained the names end with –azine, while –SCH3 and –OCH3 end with –tryn and –ton, respectively. The thermodynamical properties also depend on the substitutes, the acidity decreases according the following order -OCH3
Critical Reviews in Analytical Chemistry Publication details, including instructions for authors and subscription information: http://www.tandfonline.com/loi/batc20
Chromatographic methods for analysis of triazine herbicides a
a
b
Hana Hassan Abbas , Abdalla A. Elbashir & Hassan Y. Aboul-Enein a
Chemistry Department, Faculty of Science, University of Khartoum, Khartoum 11115, Sudan b
Pharmaceutical and Medicinal Chemistry Department, Pharmaceutical and Drug Industries Research Division, National Research Centre, Dokki, Cairo, Egypt Accepted author version posted online: 30 Jun 2014.
To cite this article: Hana Hassan Abbas, Abdalla A. Elbashir & Hassan Y. Aboul-Enein (2014): Chromatographic methods for analysis of triazine herbicides, Critical Reviews in Analytical Chemistry, DOI: 10.1080/10408347.2014.927731 To link to this article: http://dx.doi.org/10.1080/10408347.2014.927731
Disclaimer: This is a version of an unedited manuscript that has been accepted for publication. As a service to authors and researchers we are providing this version of the accepted manuscript (AM). Copyediting, typesetting, and review of the resulting proof will be undertaken on this manuscript before final publication of the Version of Record (VoR). During production and pre-press, errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal relate to this version also.
PLEASE SCROLL DOWN FOR ARTICLE Taylor & Francis makes every effort to ensure the accuracy of all the information (the “Content”) contained in the publications on our platform. However, Taylor & Francis, our agents, and our licensors make no representations or warranties whatsoever as to the accuracy, completeness, or suitability for any purpose of the Content. Any opinions and views expressed in this publication are the opinions and views of the authors, and are not the views of or endorsed by Taylor & Francis. The accuracy of the Content should not be relied upon and should be independently verified with primary sources of information. Taylor and Francis shall not be liable for any losses, actions, claims, proceedings, demands, costs, expenses, damages, and other liabilities whatsoever or howsoever caused arising directly or indirectly in connection with, in relation to or arising out of the use of the Content. This article may be used for research, teaching, and private study purposes. Any substantial or systematic reproduction, redistribution, reselling, loan, sub-licensing, systematic supply, or distribution in any form to anyone is expressly forbidden. Terms & Conditions of access and use can be found at http:// www.tandfonline.com/page/terms-and-conditions
ACCEPTED MANUSCRIPT Chromatographic methods for analysis of triazine herbicides Hana Hassan Abbas1, Abdalla A. Elbashir*1, Hassan Y. Aboul-Enein2*
1
Chemistry Department, Faculty of Science, University of Khartoum, Khartoum 11115, Sudan.
2
Pharmaceutical and Medicinal Chemistry Department, Pharmaceutical and Drug Industries
Downloaded by [University of Texas Libraries] at 03:46 05 December 2014
Research Division, National Research Centre, Dokki, Cairo, Egypt
Abstract Gas chromatography (GC) and High Performance Liquid chromatography (HPLC) coupled to different detectors, and in combination with different sample extraction methods are most widely used for analysis of triazine herbicides in different environmental samples. Nowadays, many variations and modifications of extraction and sample preparation methods such as solid phase microextraction (SPME), hollow fiber-liquid phase microextraction (HF-LPME), stir bar sportive extraction (SBSE), headspace-solid phase microextraction (HS-SPME), dispersive liquid-liquid microextraction (DLLME), dispersive liquid-liquid microextraction based on solidification of floating organic droplet (DLLME-SFO), ultrasound-assisted emulsification microextraction (USAEME), and others, have been introduced and developed to obtain sensitive and accurate methods for the analysis of these hazardous compounds. In this review, several analytical properties such as linearity, sensitivity, repeatability and accuracy for each developed method were discussed, and excellent results were obtained for the most of developed methods combined with GC and HPLC techniques for the analysis of triazine herbicides. This review gives an overview of recent publications of the application of GC and HPLC for analysis of triazine herbicides residues in various samples. Keywords: Triazines,GC, HPLC, Sample extraction Correspondence to: Professor Hassan Y. Aboul-Enein ;E-mail:[email protected]; Tel.+201003678948; Fax:+202-33370931 and Dr. Abdalla A.Elbashir; E-mail: [email protected]
1
ACCEPTED MANUSCRIPT
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Abbreviations used: 2D, two-dimensional; CPD, cloud point extraction; DAD, diode array detector; DI-SPME, direct immersion-solid phase microextraction; DLLME, dispersive liquidliquid microextraction; DLLME-SFO, dispersive liquid-liquid microextraction based on solidification of floating organic droplet; DLPME, dynamic liquid phase microextraction DµSPE, dispersive micro solid-phase extraction; DMAE, dynamic microwave-assisted
Downloaded by [University of Texas Libraries] at 03:46 05 December 2014
extraction; DMISPE, dummy molecularly imprinted solid-phase extraction; DoE, design of experiments; ECD, electron capture detector; FID, flame ionization detector; GC, gas chromatography; GC-MS, gas chromatography-mass spectrometry; HF-LPME, hollow fiberliquid phase microextraction; HFLSME, hollow fiber-liquid-solid microextraction; HFMT, hollow fiber membrane tube; HPLC, high performance liquid chromatography; HS-LPME, headspace liquid phase microextraction; HS-SPME, headspace-solid phase microextraction; IL, ionic liquid; LC-ESI MS/MS, liquid chromatography-electrospray ionization tandem mass spectrometry; LIT-MS3, linear ion trap mass spectrometry; LLE, liquid-liquid extraction; LODs, limits of detection; LOQs, limits of quantification; LPME, Liquid phase microextraction; LPMESFO, liquid phase microextraction based on solidification of floating organic drop; LS, liquidsolid procedure; MEPS, microextraction in packed syringe; MIP, molecularly imprinted polymer; MNPs, magnetic nanoparticles; MSPD, matrix solid-phase dispersion; MSPE, magnatic solid phase extraction; MWCNTs, multiwalled carbon nanotubes; NPD, nitrogen phosphorus detector; PLE, Pressurized liquid extraction; r, correlation coefficient; RP, reversed phase; RSD, relative standard deviation; SBSE, stir bar sorptive extraction; SCX, strong cation exchange; SDME, single drop microextraction; SE, Shaking extraction; SIM, selected ion monitoring; SPE, solid phase extraction; SPME, solid phase microextraction; SWNHs, single-walled carbon nanohorns; TD-GC-MS/MS, gas chromatography-triple quadrupole mass spectrometry; TDS, total diet study; TER, terbuthylazine; TOF MS, time-of-flight mass spectrometry; USAEME, ultrasound-assisted emulsification microextraction; USVADLLME, ultrasound vortex assisted dispersive liquid-liquid microextraction; UV, ultraviolet.
2
ACCEPTED MANUSCRIPT
ACCEPTED MANUSCRIPT
1. Introduction 1.1 Triazine herbicides
Triazine herbicides are one of the families of herbicides that inhibit or disrupt normal growth and
Downloaded by [University of Texas Libraries] at 03:46 05 December 2014
development of plant. They are extensively applied in many fields such as agriculture, industry and urban areas to soil for the control of weeds in many agricultural crops (Peterson et al., 2001).
The main triazine herbicides are derived from s-triazine, a six member heterocycle with symmetrically located atoms in which positions 2, 4 and 6 are substituted. The stereochemical stability of s-triazines is large enough to persist in environmental samples from several months to many years (Lebaron et al., 2008).
A list of common s-triazines and some of their properties are given in Table 1. The two most common s-triazines analyzed in waters are atrazine and simazine. The chemical common name depends on the substituent in position 2 (or R1 in Table 1), when a –Cl group is contained the names end with –azine, while –SCH3 and –OCH3 end with –tryn and –ton, respectively. The thermodynamical properties also depend on the substitutes, the acidity decreases according the following order -OCH3
