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Design and synthesis of a carbazole-based fluorescent derivative reagent and its application in the detection of fipronil and fipronil metabolites

A derivative reagent, carbazole-based technology, applied in the design and synthesis of carbazole-based fluorescent derivative reagents, the application field of detection of fipronil and fipronil metabolites, can solve the problem of complex pre-treatment of samples and poor sensitivity , high cost of testing, etc., to achieve the effect of fipronil and its metabolites pre-column derivatization detection method with sensitivity, good application prospects, and high sensitivity

Active Publication Date: 2021-06-18
JIANGXI AGRICULTURAL UNIVERSITY
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  • Abstract
  • Description
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Problems solved by technology

[0004] At present, the detection methods of fipronil and its metabolites in food include high performance liquid chromatography (HPLC), high performance liquid chromatography-tandem mass spectrometry (HPLC-MS / MS), gas chromatography (GC) and gas chromatography- Mass spectrometry (GC-MS), these detection methods have their own advantages and disadvantages, and there are still some shortcomings. For example, the method with high detection sensitivity will be accompanied by complicated sample pre-treatment, high inspection cost, expensive and sophisticated instruments, The operation is relatively cumbersome and other shortcomings, while the low-cost, convenient and fast detection method has poor detection sensitivity

Method used

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  • Design and synthesis of a carbazole-based fluorescent derivative reagent and its application in the detection of fipronil and fipronil metabolites
  • Design and synthesis of a carbazole-based fluorescent derivative reagent and its application in the detection of fipronil and fipronil metabolites
  • Design and synthesis of a carbazole-based fluorescent derivative reagent and its application in the detection of fipronil and fipronil metabolites

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1: Carbazole-based fluorescent derivatization reagent L2 (4-(2-(9-ethyl-9H-carbazol-3-yl)-1H-phenanthro[9,10-d] with the structure of formula (I) ]imidazol-1-yl) butanoic acid) preparation

[0035] (1) Preparation of intermediates with formula (Ⅲ) structure

[0036] Weigh 9-ethylcarbazole (5.86g, 30mmol) and dissolve it in 50mL of DMF solution, add phosphorus oxychloride (7mL, 75mmol) dropwise under ice-cooling at 0°C, and complete the dropwise addition within 30min. Then the temperature was raised to 98°C, stirred under reflux, and the progress of the reaction was detected by TLC. After the reaction was finished, cool to room temperature, dilute with 150 mL of water, extract with dichloromethane (3×100 mL), combine the organic phases, dry over anhydrous sodium sulfate, precipitate from the solvent, mix the sample with silica gel, and purify and separate by column chromatography (the eluent is Petroleum ether: ethyl acetate=15:1, v / v), the intermediate compoun...

Embodiment 2

[0043] Example 2: Establishment of a method for detecting fipronil by pre-column derivatization of a carbazole-based fluorescent derivatization reagent with a structure of formula (I)

[0044] (1) Preparation of fipronil pre-column derivatization reaction product

[0045] The pre-column derivatization reaction of fipronil is shown in the figure below:

[0046]

[0047] The fluorescent derivatization reagent L2 (0.16g, 1mmol) and dichloromethane (40mL) were added to a 100mL eggplant-shaped flask, and DMAP (0.12g, 3mmol), DCC (0.23g, 1.5mmol) and fluorine were added sequentially under stirring at 35°C. Chrynil (0.07g, 0.5mmol), continue to stir the reaction, TLC detection of the reaction progress. After the reaction, wash twice with 20mL of saturated brine and once with 20mL of water, extract the water layer with dichloromethane (3×50mL), dry over anhydrous sodium sulfate, remove solvent, and purify and separate by silica gel column chromatography (elution The solvent is n-...

Embodiment 3

[0053] Example 3: Establishment of a method for detecting fipronil metabolites by pre-column derivatization of a carbazole-based fluorescent derivatization reagent with a structure of formula (I)

[0054] (1) Pre-column derivatization reaction of fipronil metabolite (fipronil sulfoxide)

[0055] The main conditions for the pre-column derivatization of fipronil metabolites (fipronil sulfoxide) are as follows: EDC / DMAP is used as a catalytic condensation agent, dichloromethane is used as a solvent, and the molar concentration ratio of fipronil sulfoxide to L2 is 1: 8. Reaction in a water bath at 45°C for 75 minutes, the pre-column derivatization reaction is complete, and the derivative product is N-(3-cyano-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4 -((trifluoromethyl)thio)-1H-pyrazol-5-yl)-4-(2-(9-ethyl-9H-carbazol-3-yl)-1H-phenanthro[9, 10-d] imidazol-1-yl) butanamide (DX1), which has strong fluorescence intensity.

[0056] (2) Pre-column derivatization of fipronil metabol...

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Abstract

The invention relates to the field of food and agricultural safety detection, in particular to the design and synthesis of a carbazole-based fluorescent derivative reagent with novel structure and its application in the detection of fipronil and fipronil metabolites. Tests have proved that the carbazole fluorescent derivatization reagent designed and synthesized by the present invention has strong fluorescence intensity, and the HPLC of fipronil and its metabolite fipronil sulfoxide can be determined based on the pre-column derivatization established by the derivatization reagent. ‑FLD (High Performance Liquid Chromatography‑Fluorescence Detection) method has high sensitivity, low detection limit and quantification limit, good stability and reproducibility. This method is applied to residual fipronil and its metabolite fipronil sulfoxide in eggs The detection results are accurate and reliable, and are superior to the currently reported HPLC-MS / MS and GC-MS methods. The carbazole fluorescent derivatization reagent designed and synthesized by the present invention has excellent performance, and the pre-column derivatization detection method of fipronil and its metabolites based on it is sensitive, reliable and accurate, and has a good application prospect.

Description

technical field [0001] The invention relates to the field of food and agricultural safety detection, in particular to the design and synthesis of a carbazole fluorescent derivative reagent and its application in the detection of fipronil and fipronil metabolites. Background technique [0002] In August 2017, "poisonous eggs" with excessive fipronil content were discovered in the European market, which aroused people's high attention to food safety. In the same year, such "poisonous eggs" also appeared in Hong Kong, China and Taiwan, China. With the development of the incident, the situation became more and more severe. The "poisonous egg" incident spread to the whole world, causing people to panic. This incident sounded the alarm for the prevention and control of excessive fipronil residues. Research has therefore attracted much attention. [0003] Fipronil (English name: fipronil) is a new type of fluorine- and chlorine-containing phenylpyrazole insecticide developed by t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/04C09K11/06G01N30/06G01N21/64
CPCC07D403/04C09K11/06C09K2211/1029C09K2211/1044G01N21/6428G01N30/06
Inventor 尹忠平彭大勇刘佳上官新晨李冬文陈继光蒋艳张清峰
Owner JIANGXI AGRICULTURAL UNIVERSITY
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