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

A kind of derivatization reagent and coumarin technology, which is applied in the design and synthesis of coumarin fluorescent derivative reagents, and the application field in the detection of fipronil, which can solve the complex pre-test treatment of samples, the easy residue of fipronil, and the cost of inspection. Advanced problems, to achieve the effect of low detection limit and quantitative limit, accurate results and good application prospects

Active Publication Date: 2022-03-25
JIANGXI AGRICULTURAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, fipronil is easy to remain, difficult to degrade in nature, and unfavorable to the environment, so it is necessary to detect and control it
[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), the above detection methods have their own advantages and disadvantages, but there are also some shortcomings, such as complex pre-treatment of samples, high inspection costs, need for expensive and sophisticated instruments, and cumbersome operations, etc.

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: Preparation of coumarin-based fluorescent derivatizing reagent L1 (7-(diethylamino)-2-oxo-2H-chromone-3-carboxylic acid) with structure of formula (I)

[0028] (1) Preparation of intermediates with structure of formula (III)

[0029] Dissolve 4-(diethylamino)salicylaldehyde (9.7g, 1.0mmol) and diethyl malonate (16.0g, 2.0mmol) in 150mL of anhydrous ethanol solution, add 10mL of piperidine, and mix them The solution was stirred at 80 °C for 6 h, and the progress of the reaction was detected by TLC. After the reaction was completed, the solution was cooled to room temperature, desolubilized, mixed with silica gel, and purified and separated by column chromatography (eluent: petroleum ether: ethyl acetate = 10:1, v / v) to obtain the structure of formula (III) the intermediate compound. The obtained intermediate was a reddish-brown solid with a yield of 75.8%. The structural representation data is as follows: 1 H NMR(500MHz, DMSO)δ8.54(s,1H),7.62(d,J=9.0Hz,1H)...

Embodiment 2

[0032] Example 2: Establishment of a method for the detection of fipronil by pre-column derivatization of a coumarin-based fluorescent derivatization reagent with the structure of formula (I)

[0033] (1) Preparation of pre-column derivatized products of fipronil

[0034] The pre-column derivatization reaction of fipronil is shown in the following figure:

[0035]

[0036]The coumarin-based fluorescent derivatization reagent L1 (0.47g, 1mmol) and 40mL of dichloromethane were added to a 100mL eggplant-shaped flask, and DMAP (0.19g, 0.85mmol) and EDC (0.19g, 0.5mmol) were sequentially added under stirring at 35°C. And fipronil (0.32 g, 0.4 mmol) was added to the above solution, the reaction was continued, and the reaction progress was detected by TLC. After the reaction was completed, 40 mL of saturated NaOH solution and 20 mL of water were added, extracted with dichloromethane (3×50 mL), the organic phases were combined, dried over anhydrous sodium sulfate, desolubilized, a...

Embodiment 3

[0042] Example 3: Pre-column derivatization of coumarin-based fluorescent derivatization reagents with the structure of formula (I) to detect residual fipronil in eggs

[0043] (1) Extraction and pretreatment of residual fipronil in eggs

[0044] Egg samples: supermarket purchase, random sampling. Extraction: Shell the sample eggs and mix them well with a homogenizer; accurately weigh 5g of egg homogenate (accurate to 0.01g), place it in a 50mL centrifuge tube, add 20mL of chromatographically pure acetonitrile solution; shake and mix by hand for 1min, and then Shake with constant temperature oscillator for 5 min; then add 2 g of sodium chloride and 6 g of anhydrous sodium sulfate to the centrifuge tube, manually shake and mix for 1 min, and centrifuge at 4000 r / min for 10 min; take the supernatant and place it in a 4 °C refrigerator for testing .

[0045] (2) Method and conditions of pre-column fluorescence derivatization reaction of fipronil extract

[0046] The method and...

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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 coumarin-based fluorescent derivative reagent with novel structure and its application in the detection of fipronil. Tests have proved that the coumarin-based fluorescent derivative reagent designed and synthesized by the present invention has strong fluorescence intensity, and the HPLC-FLD method for determining fipronil based on the pre-column derivatization established by the derivative reagent has high sensitivity and low detection limit. and low limit of quantification, good stability and reproducibility, the method is applied to the detection of fipronil residues in eggs, the results are accurate and reliable, and are superior to the currently reported HPLC-MS / MS and GC-MS methods. The coumarin-based fluorescent derivatization reagent designed and synthesized by the present invention has excellent performance, and the pre-column derivatization detection method of fipronil 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 coumarin-based fluorescent derivative reagent and its application in the detection of fipronil. Background technique [0002] In 2017, "poisonous eggs" with excessive fipronil content were successively discovered in the markets of many European countries. This "poisonous egg" incident has spread to many countries and regions around the world. Problem Egg". The "poisoned egg" incident has aroused people's high attention to food safety, and has thus sounded the alarm for the prevention and control of excessive fipronil residues. High-sensitivity and high-accuracy detection technology is the basis for ensuring the smooth progress of high-standard limit monitoring. Therefore, the research on fipronil residue detection has attracted much attention. [0003] Fipronil, Chinese trade name: Ruijinte, is a highly active insecticide with ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/16C09K11/06G01N30/06G01N21/64
CPCC07D311/16C09K11/06G01N30/06G01N21/6428C09K2211/1088
Inventor 尹忠平刘佳彭大勇上官新晨陈继光李冬文张清峰吴少福
Owner JIANGXI AGRICULTURAL UNIVERSITY
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