Abstract
An efficient, reliable, sensitive, rapid, and environmentally friendly analytical method has been developed for the extraction and determination of aryloxyphenoxypropionate herbicides in aqueous and vegetable samples using ionic liquid-based air-assisted liquid–liquid microextraction coupled with high-performance liquid chromatography-diode array detector. In this method, a few microliters of 1-hexyl-3-methylimidazolium hexafluorophosphate (as an extractant) is transferred into the aqueous solution containing the analytes. Fine droplets of the extractant are formed by repeated aspirating and dispersing of the mixture via a syringe needle. During this period, the analytes are extracted into the ionic liquid and then collected at the bottom of the tube after centrifugation. Under the optimum extraction conditions, the method showed low limits of detection and quantification between 0.16 and 0.31 and 0.52 and 0.99 ng mL−1, respectively. Extraction recoveries and enrichment factors were in the ranges of 76–83 % and 380–415, respectively. The relative standard deviations for the extraction of 1.5 ng mL−1 of each analyte were less than 5.2 % for intra-day (n = 6) and inter-day (n = 4) precisions. Finally, different aqueous and vegetable samples were successfully analyzed using the proposed method, and two analytes were determined in some of them at ng mL−1 level.
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Abbreviations
- AALLME:
-
Air-assisted liquid–liquid microextraction
- AOPP:
-
Aryloxyphenoxypropionate
- DAD:
-
Diode array detector
- DLLME:
-
Dispersive liquid–liquid microextraction
- GC:
-
Gas chromatography
- LLE:
-
Liquid–liquid extraction
- LPME:
-
Liquid-phase microextraction
- MS:
-
Mass spectrometry
- SPE:
-
Solid-phase extraction
- UPLC:
-
Ultra high-performance liquid chromatography
- USAEME:
-
Ultrasound-assisted emulsification microextraction
- VADLLME:
-
Vortex-assisted dispersive liquid–liquid microextraction
References
Bagheri H, Banihashemi S (2015) Sol gel-based silver nanoparticles-doped silica polydiphenylamine nanocomposite for micro-solid-phase extraction. Anal Chim Acta 886:56–65
Bagheri H, Es’haghi A, Es–haghi A (2012) Immersed solvent microextraction of aryloxyphenoxypropionate herbicides from aquatic media. Int J Environ Anal Chem 93:450–460
Bagheri H, Dehghan M, Es’haghi A, Naderi M (2013) A conically fixed position single drop microextraction method for isolation of aryloxyphenoxypropionate herbicides from aquatic media. Anal Methods 5:4846–4851
Bagheri H, Piri-Moghadam H, Asgari S (2014) On-line micro solid-phase extraction of clodinafop propargyl from water, soil and wheat samples using electrospun polyamide nanofibers. Chromatographia 77:723–728
Barfi B, Asghari A, Rajabi M, Sabzalian S (2015) Organic solvent-free air-assisted liquid–liquid microextraction for optimized extraction of illegal azo-based dyes and their main metabolite from spices, cosmetics and human bio-fluid samples in one step. J Chromatogr B 989–999:15–25
Cai X, Liu W, Sheng G (2008) Enantioselective degradation and ecotoxicity of the chiral herbicide diclofop in three freshwater alga cultures. J Agric Food Chem 56:2139–2146
Cai K, Hu D, Lei B, Zhao H, Pan W, Song B (2015) Determination of carbohydrates in tobacco by pressurized liquid extraction combined with a novel ultrasound-assisted dispersive liquid–liquid microextraction method. Anal Chim Acta 882:90–100
Elefsiniotis IS, Liatsos GD, Stamelakis D, Moulakakis A (2007) Case report: mixed cholestatic/hepatocellular liver injury induced by the herbicide quizalofop-p-ethyl. Environ Health Perspect 115:1479–1481
Es-haghi A, Zare M, Piri-Moghadam H, Bagheri H (2015) Resorcinol-formaldehyde xerogel as a micro-solid-phase extraction sorbent for the determination of herbicides in aquatic environmental samples. J Sep Sci 38:2305–2311
Ezoddin M, Majidi B, Abdi K (2015) Ultrasound-assisted supramolecular dispersive liquid–liquid microextraction based on solidification of floating organic drops for preconcentration of palladium in water and road dust samples. J Mol Liq 209:515–519
Farajzadeh MA, Afshar Mogaddam MR (2012) Air-assisted liquid–liquid microextraction method as a novel microextraction technique; application in extraction and preconcentration of phthalate esters in aqueous sample followed by gas chromatography-flame ionization detection. Anal Chim Acta 728:31–38
Farajzadeh MA, Bahram M, Jonsson JÀ (2007) Dispersive liquid–liquid microextraction followed by high-performance liquid chromatography-diode array detection as an efficient and sensitive technique for determination of antioxidants. Anal Chim Acta 591:69
Farajzadeh MA, Marzi Khosroshahi E, Khorram P (2013) Simultaneous derivatization and air-assisted liquid–liquid microextraction of some parabens in personal care products and their determination by GC with flame ionization detection. J Sep Sci 36:3571–3578
Farajzadeh MA, Afshar Mogaddam MR, Gorbanpour H (2014) Development of a new microextraction method based on elevated temperature dispersive liquid–liquid microextraction for determination of triazole pesticides residues in honey by gas chromatography-nitrogen phosphorus detection. J Chromatogr A 1347:8–16
Farajzadeh MA, Afshar Mogaddam MR, Aghanassab M (2016a) Deep eutectic solvent-based dispersive liquid–liquid microextraction. RSC Adv 8:2576–2283
Farajzadeh MA, Mohebbi A, Feriduni B (2016b) Development of continuous dispersive liquid-liquid microextraction performed in home-made device for extraction and preconcentration of aryloxyphenoxy-propionate herbicides from aqueous samples followed by gas chromatography-flame ionization detection. Anal Chim Acta 920:1–9
Gong A, Zhu X (2015) Dispersive solvent-free ultrasound-assisted ionic liquid dispersive liquid–liquid microextraction coupled with HPLC for determination of ulipristal acetate. Talanta 131:603–608
Guan W, Zhang H (2012) Determination and study on residue and dissipation of benazolin-ethyl and quizalofop-p-ethyl in rape and soil. Int J Environ Anal Chem 93:679–691
Hu L, Zhang P, Shan W, Wang X, Li S, Zhou W, Gao H (2015) In situ metathesis reaction combined with liquid-phase microextraction based on the solidification of sedimentary ionic liquids for the determination of pyrethroid insecticides in water samples. Talanta 144:98–104
Ju S, Deng J, Cheng J, **ao N, Huang K, Hu C, Zhao H, **e J, Zhan X (2015) Determination of leucomalachite green, leucocrystal violet and their chromic forms using excitation-emission matrix fluorescence coupled with second-order calibration after dispersive liquid–liquid microextraction. Food Chem 185:479–487
Li S, Gao P, Zhang J, Li Y, Peng B, Gao H, Zhou W (2012) Sequential dispersive liquid-liquid microextraction for the determination of aryloxyphenoxy-propionate herbicides in water. J Sep Sci 35:3389–3395
Liu Y, He M, Chen B, Hu B (2015) Simultaneous speciation of inorganic arsenic, selenium and tellurium in environmental water samples by dispersive liquid–liquid microextraction combined with electrothermal vaporization inductively coupled plasma-mass spectrometry. Talanta 142:213–320
Lucini L, Molinari GP (2011) Detection of the herbicide fenoxaprop-p-ethyl, its agronomic safener isoxadifen ethyl and their metabolites residue in rice. Qual Assur Saf Crops Foods 3:63–68
Luo M, Liu D, Zhao L, Han J, Liang Y, Wang P, Zhou Z (2014) A novel magnetic ionic liquid modified carbon nanotube for the simultaneous determination of aryloxyphenoxy-propionate herbicides and their metabolites in water. Anal Chim Acta 852:88–96
Rezaee M, Assadi Y, Hosseini MRM, Aghaee E, Ahmadi F, Berijani S (2006) Determination of organic compounds in water using dispersive liquid–liquid microextraction. J Chromatogr A 1116:1–9
Tuzen M, Pekiner OZ (2015) Ultrasound-assisted ionic liquid dispersive liquid–liquid microextraction combined with graphite furnace atomic absorption spectrometric for selenium speciation in foods and beverages. Food Chem 188:619–624
Wu H, Li G, Liu S, Hu N, Geng D, Chen G, Sun Z, Zhao X, **a L, You J (2016) Monitoring the contents of six steroidal and phenolic endocrine disrupting chemicals in chicken, fish and aquaculture pond water samples using pre-column derivatization and dispersive liquid–liquid microextraction with the aid of experimental design methodology. Food Chem 192:98–106
Xue J, Chen X, Jiang W, Liu F, Li H (2015) Rapid and sensitive analysis of nine fungicide residues in chrysanthemum by matrix extraction-vortex-assisted dispersive liquid–liquid microextraction. J Chromatogr B 975:9–17
Yan Y, Chen X, Hu S, Bai X (2014) Applications of liquid-phase microextraction techniques in natural product analysis: a review. J Chromatogr A 1368:1–17
Yang M, ** X, Wu X, Lu R, Zhou W, Zhang S, Gao H (2015) Vortex-assisted magnetic β-cyclodextrin/attapulgite-linked ionic liquid dispersive liquid–liquid microextraction coupled with high-performance liquid chromatography for the fast determination of four fungicides in water samples. J Chromatogr A 1381:37–47
You X, **ng Z, Liu F, Zhang X (2015) Air-assisted liquid–liquid microextraction by solidifying the floating organic droplets for the rapid determination of seven fungicide residues in juice samples. Anal Chim Acta 874:54–60
Zhan GÖ, Zden SÖ, Alpertunga B (2005) Determination of commonly used herbicides in surface water using solid-phase extraction and dual-column HPLC-DAD. J Environ Sci Health, Part B 40:827–840
Zhang Y, Lee HK (2012) Determination of ultraviolet filters in water samples by vortex-assisted dispersive liquid–liquid microextraction followed by gas chromatography-mass spectrometry. J Chromatogr A 1249:25–31
Acknowledgments
Authors are grateful to Research Council of the University of Tabriz for financial support.
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Mir Ali Farajzadeh has received research grants from University of Tabriz.
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Mir Ali Farajzadeh declares that he has no conflict of interest. Mahdi Bamorowat declares that he has no conflict of interest. Mohammad Reza Afshar Mogaddam declares that he has no conflict of interest.
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Farajzadeh, M.A., Bamorowat, M. & Afshar Mogaddam, M.R. Ionic Liquid-Based Air-Assisted Liquid–Liquid Microextraction for the Extraction and Preconcentration of Aryloxyphenoxypropionate Herbicides from Aqueous and Vegetable Samples Followed by HPLC-DAD. Food Anal. Methods 10, 749–758 (2017). https://doi.org/10.1007/s12161-016-0637-9
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DOI: https://doi.org/10.1007/s12161-016-0637-9