Abstract
A novel mosaic structure Silica@C/Co@ZIF-67 composite was synthesized by successfully embedding Co nanoparticles on the surface of silica spheres with the help of thermoplastic polyethyleneimine by carbon-reduction. The ZIF-67 half-shell layer structure was synthesized by the in-situ growth of ZIF-67 on the surface of silica spheres through the coordination of 2-methylimidazole with Co metal nodes. The composite was used as a magnetic solid-phase extraction adsorbent combined with high performance liquid chromatography-ultraviolet detector (HPLC–UV) for the extraction and determination of benzoylurea insecticides (BUs) in vegetables and tea. Based on the presence of π-π, hydrophobic and hydrogen bonding interactions between Silica@C/Co@ZIF-67 and BUs, the BUs were rapidly captured by the composites resulting in high adsorption performance. Under the optimal extraction parameters, the linear ranges were 0.3–200 µg L−1 for diflubenzuron, 0.6–200 µg L−1 for chlorbenzuron, and 1.0–200 µg L−1 for triflumuron, teflubenzuron, and flufenoxuron, with correlation coefficients (R2) greater than 0.9991. The limits of detection (LODs) of the method were 0.1–0.3 μg L−1, and the relative standard deviations (RSDs) were 1.2–3.0% for intra-day and 2.6–4.6% for inter-day. In the spiked recovery experiments of vegetables and tea, the recoveries of the five kinds of BUs ranged from 75.8 to 112.9%. In addition, after 10 repetitions using Silica@C/Co@ZIF-67, the recoveries of the five kinds of BUs were still as high as 78.4 to 83.9%.
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References
Parven A, Khan MSI, Prodhan MDH, Venkateswarlu K, Megharaj M, Meftaul IM (2021) Human health risk assessment through quantitative screening of insecticide residues in two green beans to ensure food safety. J Food Compost Anal 103:140121. https://doi.org/10.1016/j.jfca.2021.104121
Matsumura F (2010) Studies on the action mechanism of benzoylurea insecticides to inhibit the process of chitin synthesis in insects: a review on the status of research activities in the past, the present and the future prospects. Pestic Biochem Physiol 97:133–139. https://doi.org/10.1016/j.pestbp.2009.10.001
Wang X, Ma R, Hao L, Wu Q, Wang C, Wang Z (2018) Mechanochemical synthesis of covalent organic framework for the efficient extraction of benzoylurea insecticides. J Chromatogr A 1551:1–9. https://doi.org/10.1016/j.chroma.2018.03.053
Wang JJ, Zhang TT, Gong ZG, Gao Y, Wang JD, Zhang Y (2017) Determination of eight benzoylurea insecticides in high-fat foodstuff samples by gel permeation chromatography followed by high-performance liquid chromatography-tandem mass spectrometry. Food Anal Methods 10:3098–3105. https://doi.org/10.1007/s12161-017-0868-4
Capriotti AL, Cavaliere C, La Barbera G, Montone CM, Piovesana S, Laganà A (2019) Recent applications of magnetic solid-phase extraction for sample preparation. Chromatographia 82:1251–1274. https://doi.org/10.1007/s10337-019-03721-0
Sun M, Li C, Feng J, Sun H, Sun M, Feng Y, Ji X, Han S, Feng J (2022) Development of aerogels in solid-phase extraction and microextraction, TrAC. Trends Anal Chem 146:116497. https://doi.org/10.1016/j.trac.2021.116497
Meng Z, Li X, Qiao K, Zeng H, Cui X, Liu Z, Ju Z, Lu R, Gao H, Zhou W (2021) Phosphonium-based deep eutectic solvent coupled with vortex-assisted liquid-liquid microextraction for the determination of benzoylurea insecticides in olive oil. J Sep Sci 44:1529–1536. https://doi.org/10.1002/jssc.202001075
Wang HZ, Wang TT, Hong MX, Wang ZY, Jin XY, Wu H (2023) Direct solidification of switchable-hydrophilicity salicylic acid: a design for the on-site dispersive liquid-liquid microextraction of benzoylurea insecticides in water and honey samples. J Chromatogr A 1688. https://doi.org/10.1016/j.chroma.2022.463710
Mei L, Si TT, Wang S, Zhu J, Tang H, Liang XJ (2022) TiO2@MOF-919(Fe-Cu) as a sorbent for the extraction of benzoylurea pesticides from irrigation water and fruit juices. Anal Methods 14:3153–3159. https://doi.org/10.1039/d2ay00842d
Mu MY, Zhu SP, Gao YM, Zhang N, Wang YM, Lu MH (2023) Construction of hierarchically porous metal-organic framework HP-UiO-66–30% for sensitive determination of benzoylurea insecticides. Talanta 260. https://doi.org/10.1016/j.talanta.2023.124540
Sun H, Feng J, Feng J, Sun M, Feng Y, Sun M (2022) Carbon aerogels derived from waste paper for pipette-tip solid-phase extraction of triazole fungicides in tomato, apple and pear. Food Chem 395:133633. https://doi.org/10.1016/j.foodchem.2022.133633
Mei M, Huang X, Liao K, Yuan D (2015) Sensitive monitoring of benzoylurea insecticides in water and juice samples treated with multiple monolithic fiber solid-phase microextraction and liquid chromatographic analysis. Anal Chim Acta 860:29–36. https://doi.org/10.1016/j.aca.2014.12.047
Li S, Liu W, Wang Q, Xu M, An Y, Hao L, Wang C, Wu Q, Wang Z (2022) Constructing magnetic covalent organic framework EB-COF@Fe3O4 for sensitive determination of five benzoylurea insecticides. Food Chem 382:132362. https://doi.org/10.1016/j.foodchem.2022.132362
Li X, Lu XF, Liang XJ, Guo Y, Wang LC, Wang S (2022) Extraction of benzoylurea insecticides from tea leaves based on thermoplastic polyethyleneimine embedded magnetic nanoparticle carbon materials. J Chromatogr A 1681. https://doi.org/10.1016/j.chroma.2022.463476
Fan C, Liang XJ (2023) Metal salts assisted thermoplastic polymer NIPAM in-situ carbonization on porous silica microspheres surface. J Porous Mater 30:541–546. https://doi.org/10.1007/s10934-022-01363-6
Hao L, Wei J, Zheng R, Wang C, Wu Q, Wang Z (2017) Magnetic porous carbon derived from Co-doped metal–organic frameworks for the magnetic solid-phase extraction of endocrine disrupting chemicals. J Sep Sci 40:3969–3975. https://doi.org/10.1002/jssc.201700460
Duo H, Wang S, Lu X, Wang L, Liang X, Guo Y (2021) Magnetic mesoporous carbon nanosheets derived from two-dimensional bimetallic metal-organic frameworks for magnetic solid-phase extraction of nitroimidazole antibiotics. J Chromatogr A 1645:462074. https://doi.org/10.1016/j.chroma.2021.462074
Peh SB, Zhao D (2020) 1 - Synthesis and development of metal–organic frameworks. In: Liu J, Ding F (eds) Nanoporous materials for molecule separation and conversion. Elsevier, Singapore, pp 3–43. https://doi.org/10.1016/B978-0-12-818487-5.00001-7
Tian YQ, Cai CX, Ji Y, You XZ, Peng SM, Lee GH (2002) Co-5(im)(10) center dot 2MB (x): a metal-organic open-framework with zeolite-like topology. Angew Chem Int Ed 41:1384–1386. https://doi.org/10.1002/1521-3773(20020415)41:8%3c1384::Aid-anie1384%3e3.0.Co;2-6
Fairen-Jimenez D, Moggach SA, Wharmby MT, Wright PA, Parsons S, Duren T (2011) Opening the gate: framework flexibility in ZIF-8 explored by experiments and simulations. J Am Chem Soc 133:8900–8902. https://doi.org/10.1021/ja202154j
Chen BL, Yang ZX, Zhu YQ, Xia YD (2014) Zeolitic imidazolate framework materials: recent progress in synthesis and applications. J Mater Chem A 2:16811–16831. https://doi.org/10.1039/c4ta02984d
Zhong GH, Liu DX, Zhang JY (2018) The application of ZIF-67 and its derivatives: adsorption, separation, electrochemistry and catalysts. J Mater Chem A 6:1887–1899. https://doi.org/10.1039/c7ta08268a
Selahle SK, Mpupa A, Nomngongo PN (2022) Combination of zeolitic imidazolate framework-67 and magnetic porous porphyrin organic polymer for preconcentration of neonicotinoid insecticides in river water. J Chromatogr A 1661. https://doi.org/10.1016/j.chroma.2021.462685
del Rio M, Turnes Palomino G, Palomino Cabello C (2020) Metal-organic FRAMEWORK@CARBON hybrid magnetic material as an efficient adsorbent for pollutant extraction. ACS Appl Mater Interfaces 12:6419–6425. https://doi.org/10.1021/acsami.9b19722
Abdelhameed RM, Taha M, Abdel-Gawad H, Mahdy F, Hegazi B (2019) Zeolitic imidazolate frameworks: experimental and molecular simulation studies for efficient capture of pesticides from wastewater. J Environ Chem Eng 7:103499. https://doi.org/10.1016/j.jece.2019.103499
Xian G, Zhang X, Zhu Z, Wu C, Wang Y, Meng Y, Liu Y, Liu Z, Kong L (2023) Polyaniline-coated ZIF-67-derived Co/C nanostructures for efficient electromagnetic wave absorption. ACS Appl Nano Mater 6:8617–8626. https://doi.org/10.1021/acsanm.3c01007
Rezaee S, Shahrokhian S (2019) Facile synthesis of petal-like NiCo/NiO-CoO/nanoporous carbon composite based on mixed-metallic MOFs and their application for electrocatalytic oxidation of methanol. Appl Catal B 244:802–813. https://doi.org/10.1016/j.apcatb.2018.12.013
Rodríguez-Ramos R, Santana-Mayor Á, Socas-Rodríguez B, Herrera-Herrera AV, Rodríguez-Delgado MÁ (2023) Assessment of pesticide residues contamination in cereals and pseudo-cereals marketed in the Canary Islands. Food Chem 400:134089. https://doi.org/10.1016/j.foodchem.2022.134089
Niu M, Li Z, He W, Zhou W, Lu R, Li J, Gao H, Zhang S, Pan C (2020) Attapulgite modified magnetic metal-organic frameworks for magnetic solid phase extraction and determinations of benzoylurea insecticides in tea infusions. Food Chem 317:126425. https://doi.org/10.1016/j.foodchem.2020.126425
Li ZL, Wei YD, Wei JN, Chen KY, He Y, Wang MM (2022) Monodispersed CaCO3@hydroxyapatite/magnetite microspheres for efficient and selective extraction of benzoylurea insecticides in tea beverages samples. J Hazard Mater 433:128754. https://doi.org/10.1016/j.jhazmat.2022.128754
Niu M, Li Z, Zhang S, He W, Li J, Lu R, Gao H, Zeng A, Zhou W (2020) Hybridization of metal-organic frameworks with attapulgite for magnetic solid phase extraction and determination of benzoylurea insecticides in environmental water samples. Microchem J 159. https://doi.org/10.1016/j.microc.2020.105392
Cui X, Wang Y, Shi Y-L, Lu R, Gao H, Zhou W, Huang X (2023) Phenylboronic acid-functionalized magnetic metal-organic framework nanoparticles for magnetic solid phase extraction of five benzoylurea insecticides. J Chromatogr A 1704. https://doi.org/10.1016/j.chroma.2023.464115
Liang X, Ma R, Hao L, Wang C, Wu Q, Wang Z (2018) β-Cyclodextrin polymer@Fe3O4 based magnetic solid-phase extraction coupled with HPLC for the determination of benzoylurea insecticides from honey, tomato, and environmental water samples. J Sep Sci 41:1539–1547. https://doi.org/10.1002/jssc.201701197
Zhang N, Mu M, Zhu S, Gao Y, Lu M (2024) Well-defined Fe3O4@MIL-100(Fe) hollow nanoflower heterostructures for selective dection and monitoring of benzoylurea insecticides from food and water. Food Chem 435:137579. https://doi.org/10.1016/j.foodchem.2023.137579
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The study was supported by the National Natural Science Foundation of China (no. 22206190).
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Xiang Li: experiment, data curation, formal analysis, conceptualization, methodology, software, writing-original draft preparation.
Lili Du: writing- original draft preparation.
Xiaofeng Lu: visualization, investigation.
Shuai Wang: investigation, discussion.
Xiaoxiao Liu: investigation.
Licheng Wang: writing- reviewing and editing, discussion.
Yong Guo: supervision, validation, conceptualization.
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Li, X., Du, L., Lu, X. et al. In situ growth of ZIF-67 to construct core–shell mosaic structural composites for efficient extraction of benzoylurea insecticides. Microchim Acta 191, 90 (2024). https://doi.org/10.1007/s00604-023-06154-7
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DOI: https://doi.org/10.1007/s00604-023-06154-7