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ANALYTICAL AND BIOANALYTICAL CHEMISTRY · 2018 ·Vol. 410 ·期 6 ·1647-1656 · IF 3.307

Synthesis and application of imidazolium-based ionic liquids as extraction solvent for pretreatment of triazole fungicides in water samples

Yang Jiale,Fan Chen,Kong Dandan,Tang Gang,Zhang Wenbing,Dong Hongqiang,Liang You,Wang Deng,Cao Yongsong

Five novel ionic liquids (ILs), 1,3-dibutylimidazolium bromide [BBMIm][Br], 1-pentyl-3-butylimidazolium bromide [BPMIm][Br], 1-hexyl-3-butylimidazolium bromide [BHMIm][Br], 1,1'-(butane-1,4-diyl)bis(3-butylimidazolium) bromide [C 4 (BMIm) 2 ][Br 2 ], and 1,1'-(butane-1,4-diyl)bis(3-methylimidazolium) bromide [C 4 (MIm) 2 ][Br 2 ], were prepared and used in situ to react with bis(trifluoromethane)sulfonamide lithium salt to extract the myclobutanil, tebuconazole, cyproconazole, and prothioconazole from water samples. The results showed that mono-cationic ILs had much better recovery than dicationic ILs, and mono-imidazolium IL bearing butyl groups at N-1 and N-3 sites had the best recovery. When the length of the alkyl substituent group was more than four carbons at N-3 site, the recovery decreased with increase of alkyl chain length of 1-butylimidazolium IL. The extraction efficiency order of triazoles from high to low was [BBMIm][Br], [BPMIm][Br], [BHMIm][Br], [BMIm][Br] (1-butyl-3-methylimidazolium bromide), [C 4 (BMIm) 2 ]Br 2 , [C 4 (MIm) 2 ]Br 2 . An in situ ionic liquid dispersive liquid–liquid microextraction combined with ultrasmall superparamagnetic Fe 3 O 4 was established as a pretreatment method for enrichment of triazole fungicides in water samples by using the synthetic [BBMIm][Br] as the cationic IL and used to detect analytes followed by high-performance liquid chromatography. Under the optimized conditions, the proposed method showed a good linearity within a range of 5–250 μg L −1 , with the determination coefficient ( r 2 ) varying from 0.998 to 0.999. High mean enrichment factors were achieved ranging from 187 to 323, and the recoveries of the target analytes from real water samples at spiking levels of 10.0, 20.0, and 50.0 μg L −1 were between 70.1% and 115.0%. The limits of detection for the analytes were 0.74–1.44 μg L −1 , and the intra-day relative standard deviations varied from 5.23% to 8.65%. The proposed method can be further applied to analyze and monitor pesticides in other related samples. The scheme of the in-situ DLLME method for the determination of triazoles using the imidazolium-based ionic liquids

研究领域: 分析化学 · 环境科学 · 农药检测
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SEPARATION AND PURIFICATION TECHNOLOGY · 2024 · IF 8.1

Separation of ethanol/n-hexane azeotrope by imidazolium ionic liquids: Experimental study and mechanism analysis

Yu Wang,Ruoyu Hu,Wenli Liu,Zhaoyou Zhu,Yinglong Wang,Jingwei Yang,Jianguang Qi,Peizhe Cui

In the process of producing low-carbon alcohols from coal, azeotropic waste containing ethanol and n-hexane is generated. To prevent environmental risks and resource waste from solvent loss, this study selected green solvent ionic liquids (ILs) for their separation. First, we screened five anions with high selectivity based on the conductor-like screening model for realistic solvents (COSMO-RS), and through various quantum chemical calculations, we found that the anions play a significant role in the separation of the two components, with [HSO 4 ] − showing the best separation performance. Second, we predicted the phase equilibrium data for ILs containing [HSO 4 ] − in the azeotropic system, considering practical factors such as price and viscosity, and selected [EMIM][HSO 4 ], [BMIM][HSO 4 ], and [HMIM][HSO 4 ] for experiments. The results indicated that simpler cation side chains enhance the separation capability of the system. Then, a toxicity analysis of the ILs ensured their biocompatibility and feasibility. Finally, we established the extraction distillation process and visualized the interactions between the ILs and the azeotropic system through molecular dynamics simulations. This work provides theoretical guidance for the separation of alcohols and alkanes in the industry.

研究领域: 化学工程 · 绿色溶剂 · 量子化学计算 · 分子动力学模拟
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Polymers · 2020 ·Vol. 12 ·期 10 ·2171 · IF 3.426

Synthesis of a New Imidazole Amino Acid Ionic Liquid Polymer and Selective Adsorption Performance for Tea Polyphenols

Yingjie Luo,Xiaoxia Huang,Shun Yao,Lincai Peng,Fulin Li,Hang Song

A series of imidazolium ionic liquid monomers with L-Proline anions (ViImCn-L-Pro and (ViIm)2Cn(L-Pro)2) were firstly synthesized, after which new copolymer materials were prepared by polymerization of the ionic liquid monomers with N,N′-methylene diacrylamide (MBA). Polymerization conditions, including the ratio of Ils(ViImCn-L-Pro or (ViIm)2Cn(L-Pro)2) and MBA, solvent, ionic liquids and initiator’s amount, were investigated and found to have an important effect on the adsorption capacity. Polymerization conditions were shown to have more significant impacts on adsorption capacities in the following order: the ratio of Ils and MBA > the amount of initiator > ionic liquids > solvent. The polymers were characterized by IR, EA, SEM, particle size distribution and TG. One of the polymers exhibited the highest selective adsorption capacity of tea polyphenols (521 mg/g). which was significantly higher than other adsorption media. The absorbed tea polyphenols could be desorbed readily with 2% hydrochloric acid methanol solution as eluent. The polymer material could maintain a higher adsorption capacity after four reuses. Based on this polymer, a new method for the efficient separation of tea polyphenols from tea water could be developed.Keywords:ionic liquid polymer;imidazole;amino acid;adsorption;tea polyphenols

研究领域: 化学工程 · 食品科学
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Applied Sciences-Basel · 2020 ·Vol. 10 ·期 3 ·894 · IF 2.474

Study on Degradation of Benzothiazolium-Based Ionic Liquids by UV-H2O2

Jianhui Gu,Huimin Zang,Shun Yao,Xuejiao Wang,Minghui Zhu,Hang Song

Ionic liquids (ILs) are considered to be a new type of solvent due to their low vapor pressure, some unique properties and are expected to be used widely in the following days. Given their water solubility, stable chemical structure, and biological toxicity, ILs probably reach aquatic environments and become long-term pollutants. We studied the fate of benzothiazolium-based ionic liquids catalyzed by UV-H2O2in water. Due to the synergistic effect of UV and H2O2, the degradation efficiency can be significantly improved compared to any of them alone. Fitting results showed that the degradation reaction follows pseudo-first-order kinetics and reaction rate constants with hydroxyl radicals ranging from 0.0005 s−1to 0.0529 s−1. The experimental data showed that satisfactory results can be obtained at a temperature of 45 ℃, an initial concentration of ionic liquid of 0.1 M, and a hydrogen peroxide concentration of 0.1 M. We also explored the effects of chloride ions and pH on degradation reactions. In an appropriate situation, the degradation yield of [C4Bth]PF6could achieve 97% in 60 min and 99% in 90 min. The UV-H2O2combination process could provide an effective technique for the treatment of benzothiazolium-based ionic liquids in wastewater.Keywords:photocatalysis;degradation;benzothiazole ionic liquid;H2O2

研究领域: 环境科学 · 化学工程
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FOOD CHEMISTRY · 2022 · IF 9.231

Carbon aerogels derived from waste paper for pipette-tip solid-phase extraction of triazole fungicides in tomato, apple and pear

Haili Sun,Juanjuan Feng,Jiaqing Feng,Mingxia Sun,Yang Feng,Min Sun

In order to develop environmentally friendly, economical and facile preparation method of carbon aerogels (CAs), the waste printing paper as the raw material was combined with graphene oxide and carboxylic multi-walled carbon nanotubes to produce CAs (ρ = 44 mg cm −3 ). The CAs with different composition were investigated, the addition of graphene oxide led to the reduction of adsorption sites and the reduction of extraction performance. But the carbon nanotubes made CAs have a better pore structure. The CAs as adsorbent were loaded into a pipette-tip for solid-phase extraction of hexaconazole and diniconazole. Coupled with gas chromatography, an analytical method was established under the optimized conditions. The limits of detection were between 0.08 and 0.32 mg kg −1 , the linear ranges were 0.96–200.0 mg kg −1 and 0.24–200.0 mg kg −1 . The relative recoveries were in the range of 81.0–119%. The results indicated that the method had potential application for the determination of triazole fungicides.

研究领域: 分析化学 · 环境科学
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TOXICOLOGY IN VITRO · 2023 · IF 3.2

Studies on the interaction of five triazole fungicides with human renal transporters in cells

Jing Nie,Jiabei Zhou,Yi Shen,Ruimiao Lin,Haihong Hu,Kui Zeng,Huichang Bi,Min Huang,Lushan Yu,Su Zeng,Jing Miao

The widespread use of triazole fungicides in agricultural production poses a potential risk to human health. This study investigates the interaction of five triazole fungicides, i.e., tebuconazole, triticonazole, hexaconazole, penconazole, and uniconazole with human renal transporters, including OAT1, OAT3, OCT2, OCTN1, OCTN2, MATE1, MATE2-K, MRP2, MDR1, and BCRP, using transgenic cell models. For uptake transporters, triticonazole was the substrate of OAT1 and OAT3 and the inhibitor of OCT2. Tebuconazole and penconazole inhibited OCTN2 (100 μM), while tebuconazole, triticonazole, hexaconazole, penconazole, and uniconazole inhibited MATE1 (100 μM). Tebuconazole and hexaconazole inhibited MATE2-K (100 μM). All five triazole fungicides were not substrates or strong inhibitors of MRP2, MDR1, and BCRP efflux transporters. Penconazole inhibited OCT2 with IC 50  = 1.12 μM. Penconazole and uniconazole inhibited MATE1 with IC 50  = 0.94 μM and 0.87 μM. Tebuconazole and hexaconazole inhibited MATE2-K with IC 50  = 0.96 μM and 1.04 μM, indicating that triazole fungicides may inhibit renal drug transporter activity at low concentrations. Triticonazole was transported by OAT1 and OAT3, and the K m values of triticonazole were 5.81 ± 1.75 and 47.35 ± 14.27, respectively. Tebuconazole and uniconazole were transported by OAT3, and the K m values of tebuconazole and uniconazole were 30.28 ± 7.18 and 87.61 ± 31.70, respectively, which may induce nephrotoxicity.

研究领域: 药理学 · 毒理学 · 分子生物学
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Nanomaterials · 2022 ·Vol. 12 ·期 21 ·3879 · IF 5.719

Encapsulation of Imazalil in HKUST-1 with Versatile Antimicrobial Activity

Hongqiang Dong,Yuke He,Chen Fan,Zhongqiang Zhu,Chunrong Zhang,Xinju Liu,Kun Qian,Tao Tang

Based on high surface areas, adjustable porosity and microbicide activity, metal-organic frameworks (MOFs) HKUST-1 are widely used as drug release carriers for their slow degradation characteristics under slightly acidic conditions. In this work, porous HKUST-1 was reacted rapidly by cholinium salt (as the deprotonation agent and template) in an aqueous solution at room temperature. A novel antimicrobial system based on an imazalil encapsulated metal organic framework (imazalil IL-3@HKUST-1) was established. Imazalil IL-3@HKUST-1 could achieve synergism in inhibiting pathogenic fungi and bacteria. Moreover, six days after treatment, the slow and constant release of imazalil from imazalil IL@HKUST-1 exhibited better sustainability and microbicidal activity than imazalil. We believe that the method may provide a new strategy for related plant diseases caused by bacteria or fungi.Keywords:imazalil;ionic liquid;HKUST-1;antimicrobial activity;safety

研究领域: 植物病理学 · 药物递送系统
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ANALYTICA CHIMICA ACTA · 2020 · IF 5.977

Magnetic solid-phase extraction of triazole fungicides based on magnetic porous carbon prepared by combustion combined with solvothermal method

Xiaofei Han,Jia Chen,Zhan Li,Kaijun Quan,Hongdeng Qiu

A magnetic porous carbon (Fe 3 O 4 @PC) was successfully fabricated based on combustion combined with solvothermal method , and then used as magnetic solid-phase extraction absorbent for the determination of four triazole fungicides . The porous carbon was fabricated by imperfect combustion of filter paper loaded with zinc nitrate hexahydrate, which possessed extremely abundant pores, high specific surface area (908.05 m 2  g −1 ) and large pore volume . Due to the introduction of solvothermal method used to prepare Fe 3 O 4 @PC, homogeneously distributed magnetic nanoparticles and high saturation magnetization were obtained. Compared with another magnetic porous carbon (Fe 3 O 4 @C), Fe 3 O 4 @PC obviously enhanced enrichment factors and extraction recoveries. Several key parameters influencing extraction efficiency were optimized. The satisfactory enrichment factors, low limits of detection of the method and good linearities were achieved under the optimal conditions. The relative recoveries ranged from 82.8% to 113.2% in three spiked real samples with relative standard deviations lower than 6.2%. The results indicated the great potential of the novel Fe 3 O 4 @PC as adsorbent for the extraction of triazole fungicides from complex real samples.

研究领域: 分析化学 · 环境科学
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ANALYTICAL LETTERS · 2020 · IF 1.467

Enantiomeric Separation of Chiral Triazole Pesticides by a mono-6-(4-Nitrophenyl)-ureido-β-cyclodextrin-Bonded Stationary Phase Using High-Performance Liquid Chromatography

Yazhou Shuang,Zhigang Cao,Tianci Zhang,Laisheng Li

A mono-6-(4-nitrophenyl)-ureido-β-cyclodextrin-bonded chiral stationary phase (NCDSP), containing π-electron withdrawing groups, was prepared by immobilizing a self-prepared mono-6-(4-nitrophenyl)-ureido-β-cyclodextrin ligand onto ordered mesoporous silica gel SBA-15, on which the ligand was synthesized by the reaction of mono-6-amino-β-cyclodextrin with 4-nitrophenylisocyanate. The structure of NCDSP was characterized by infrared spectroscopy, elemental analysis, thermogravimetric analysis and solid nuclear magnetic resonance. The introduction of electron-withdrawing (π-acidic) groups facilitated the separation of the π-electron-rich (π-basic) triazole chiral pesticides. In addition, the ureido group linkage allowed NCDSP to be a hydrogen bond-accepting and -donating chiral station phase and prevented the hydrolysis associated with nitrobenzoate and nitrophenylcarbamate linkages. As a result, the enantioseparations of nine triazole pesticides were achieved using NCDSP. Meanwhile, the chromatographic conditions, such as the pH and the composition of mobile phases, were investigated in detail. Moreover, in a comparative study with a cyclodextrin stationary phase (CDSP), the NCDSP provided higher enantioselectivity. Baseline separations for most of these triazoles on NDCSP were observed in relatively short times from 10 to 20 min. The highest resolution achieved was 2.87. Otherwise, incomplete enantiomeric separation was observed on the CDSP with a maximum resolution of less than 1.18. For the NCDSP, in addition to the inclusion effect, the π-π interaction between the electron-deficient stationary phase and the electron-donating triazoles significantly contributed to the chiral separation. This work reports a simple and convenient method for the preparation of the NCDSP with the rapid separation of chiral triazole pesticides.

CAS / MDL: 108-67-8
研究领域: 分析化学 · 农药科学
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JOURNAL OF COLLOID AND INTERFACE SCIENCE · 2017 · IF 4.233

Study on the influences of two thiazole flavor ingredients on Cu corrosion caused by chloride ion

Shi Mo,Hong Qun Luo,Nian Bing Li

Green corrosion inhibitors are of great benefit to the protection of pipes or tanks in seawater systems. The properties of the corrosion inhibitor such as toxicity and anticorrosion performance are closely related to its molecular structure. Some thiazole derivatives are commonly known as food flavors . The influences of two thiazole flavor ingredients on Cu corrosion in NaCl solution were analyzed in this study, namely, 4-methyl-5-vinylthiazole (MVT) and 5-(2-hydroxyethyl)-4-methylthiazole (HMT). Potentiodynamic polarization and electrochemical impedance spectroscopy measurements were employed to evaluate their anti-corrosion abilities. Theoretical calculations were conducted to investigate their possible adsorption modes. The thiazole ring endows the two compounds with the high inhibition performace. However, with a conjugated system , the ethenyl has a more pronounced contribution to electron donation and adsorption ability on the Cu surface than hydroxyethyl group.

CAS / MDL: 137-00-8 1759-28-0
研究领域: 材料科学 · 电化学
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Thoracic Cancer · 2023 ·Vol. 14 ·期 33 ·3331-3341 · IF 2.9

Evaluation of the inhibitory effect of azoles on pharmacokinetics of lenvatinib in rats both in vivo and in vitro by UPLC-MS/MS

Mengming Xia,Xueyi Song,Zebei Lu,Yu Wang,Quan Zhou,Peiwu Geng,Shuanghu Wang,Yunfang Zhou,Qingjun Wu,Aixia Han

Background Lenvatinib is a multitargeted tyrosine kinase inhibitor used in the treatment of a variety of solid tumors. This study aims to investigate the potential pharmacokinetic interactions between lenvatinib and various azoles (ketoconazole, voriconazole, isavuconazole and posaconazole) when orally administered to rats. Methods A total of 30 Sprague–Dawley rats were randomly allocated into five groups and administered 20 mg/kg of ketoconazole, voriconazole, isavuconazole and 30 mg/kg of posaconazole and 0.5% CMC-Na, through gavage for a duration of 7 days prior to the commencement of the experiment. On the final day, the rats were given 10 mg/kg of lenvatinib. The blood concentration of lenvatinib was determined using UPLC-MS–MS. In vitro lenvatinib were incubated with azoles and rat liver microsomes (RLMs) or human liver microsomes (HLMs). Molecular docking was lastly used to examine the binding strength of the enzymes and ligands with Autodock Vina. Results AUC and C max of lenvatinib significantly increased with each of the azoles ( p < 0.05), whereas CLz/F decreased 0.83-flod, 0.41-fold ( p < 0.05) and 0.72-fold ( p < 0.01) in voriconazole, isavuconazole and ketoconazole in rats. The IC50 of lenvatinib with the azoles were 0.237, 1.300, 0.355 and 2.403 μM in RLMs and 0.160, 1.933, 3.622 and 1.831 μM in HLMs. Molecular docking analysis suggested that azoles exhibited a strong binding ability towards the target enzymes. Conclusion It is imperative to acknowledge the potential drug–drug interactions mediated by CYP3A4 between azoles and lenvatinib, as these interactions hold significant implications for their clinical utilization.

研究领域: 药理学 · 临床医学 · 分子生物学
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Frontiers in Microbiology · 2025 · IF 4.5

Baicalein combined with azoles against fungi in vitro

Mengmin Liang,Qingwen Hu,Junhao Yu,Heng Zhang,Sijie Liu,Jiangrong Huang,Yi Sun

Background: Invasive fungal infections (IFIs) constitute a significant health challenge, particularly among immunocompromised individuals, characterized by a high prevalence and associated mortality rates. The synergistic administration of Baicalein (BE) with azole antifungal agents could potentially herald a novel therapeutic paradigm.Materials and methods: 54 Aspergillus strains and 23 strains of dematiaceous fungi were selected. The standard M38-A2 microbroth dilution method was used to test the minimum inhibitory concentration (MIC) and the fractional inhibitory concentration index (FICI) of fungi when BE combined with itraconazole (ITC), voriconazole (VRC), posaconazole (POS) and Isavuconazole (ISV).Results: BE shows synergistic effects with POS and ITC, with 89.61% and 25.97% of fungal strains. The BE/POS regimen exerted synergistic effects in 87.04% of Aspergillus and an impressive 95.65% of dematiaceous fungi. In comparison, the BE/ITC combination showed significantly lower synergy, affecting 33.33% of Aspergillus and a mere 8.70% of dematiaceous strains. Antagonistic interactions were sporadically observed with BE in combination with ITC, VRC, POS and ISV. Within the azole class, the BE/POS pairing stood out for its frequent synergistic activity, in contrast to the absence of such effects when BE was paired with VRC or ISV. Highlighting the potential of BE/POS as a notably effective antifungal strategy.Conclusion: In vitro, BE/POS combination emerged as the most effective antifungal strategy, exhibiting synergistic effects in the majority of Aspergillus and dematiaceous fungi strains, whereas BE/ITC showed significantly less synergy, and BE with VRC or ISV displayed no synergistic activity.

研究领域: 医学 · 微生物学 · 药理学
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