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Trifluralin haptens, as well as preparation method and application thereof

The technology of a hapten and trifluralin, which is applied in the field of immunology, can solve the problems of lack of trifluralin, etc., and achieve the effect of simple and feasible preparation method, high purity and yield, and simple synthesis method

Active Publication Date: 2017-07-07
深圳容金科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is even a lack of trifluralin pesticide residue immunoassay kits in the domestic testing market

Method used

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  • Trifluralin haptens, as well as preparation method and application thereof
  • Trifluralin haptens, as well as preparation method and application thereof
  • Trifluralin haptens, as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Embodiment 1: The synthesis method of trifluralin hapten compound 1c is as follows:

[0043] (1) Ethyl acrylate (3600mg, 36mmol) was dissolved in 30mmol of chloroform, and n-propylamine (3191.94mg, 54mmol) was added in an oil bath and stirred at 40°C for 12h to obtain the ester group-containing secondary amine intermediate 1a.

[0044] (2) Dissolve 1a (239mg, 1.5mmol) in 6ml THF, add NaOH aqueous solution (120mg, 3mmol), stir at room temperature, and perform hydrolysis to obtain 1b after hydrolysis.

[0045] (3) Add 3,5-dinitro-4-chloro-trifluorotoluene (270 mg, 1 mmol) directly to 1b, and stir at room temperature. Use a chromatographic solution with a ratio of n-hexane: ethyl acetate = 2:1 to track the plate. After the reaction is completed, perform acid-base extraction, combine the acid-extracted organic phases, and dry with anhydrous sodium sulfate. Spin-dried at 40°C, and separated on a silica gel plate with a chromatographic solution of n-hexane: ethyl acetate: ac...

Embodiment 2

[0046] Embodiment 2: The synthesis method of trifluralin hapten compound 2c is as follows:

[0047] (1) 2-Pyrrolidone (1000mg, 11mmol) was dissolved in 10ml of DMF, 13.2mmol of NaH (60%) and n-bromopropane (1758.9mg, 14.3mmol) were added, and stirred overnight in an oil bath at 70°C under nitrogen protection. Add 70ml of ethyl acetate to the reaction solution, extract with 50ml of saturated ammonium chloride solution, combine the organic phases, and dry over anhydrous sodium sulfate. Spin-dry at 40°C to obtain the ester group-containing secondary amine intermediate 2a.

[0048] (2) 2a (846mg, 6mmol) was added to 13ml 4N NaOH aqueous solution and stirred in an oil bath at 100°C overnight for hydrolysis to obtain 2b.

[0049] (3) Dissolve 3,5-dinitro-4-chloro-trifluorotoluene (270 mg, 1 mmol) in 6 ml of tetrahydrofuran, add 2b (190.5 mg, 1.5 mmol), and stir at room temperature. Dilute with 30ml of water, add 1M hydrochloric acid to adjust the pH to 2-3, and a precipitate appea...

Embodiment 3

[0050] Embodiment 3: The synthesis method of trifluralin hapten compound 3c is as follows:

[0051] (1) Dissolve valerolactam (2180mg, 20mmol) in 10ml DMF, add 24mmol NaH (60%), n-bromopropane (2950mg, 24mmol), stir in an oil bath at 70°C, and react under nitrogen protection for 4-5 hours. Dilute with 50ml of water, add 1M hydrochloric acid to adjust the pH to 2-3, and a precipitate appears. Extracted twice with ethyl acetate, the amount of ethyl acetate used each time was 50ml, the precipitate was dissolved, washed with 15ml of saturated brine, the organic phases were combined, and dried over anhydrous sodium sulfate. After spin-drying at 40°C, the secondary amine 3a containing an ester group was obtained, and the yield was 55% by weight.

[0052] (2) Add 2.5ml of 37% hydrochloric acid and 2.5ml of water to 3a (846mg, 6mmol), condense and reflux in an oil bath at 100°C for 4-5 hours for hydrolysis, and obtain the hydrolyzate 3b.

[0053] (3) Dissolve 3,5-dinitro-4-chloro-tr...

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Abstract

The invention discloses trifluralin haptens, as well as a preparation method and application thereof. The trifluralin hapten has a structural formula as shown in the specification. The six haptens are specific antibodies which have linker arms derived on amino sites, have active carboxyls, enable a body to generate high titer after being coupled with carrier protein and can be used for identifying common structures of trifluralin pesticide. The hapten compound is simple and convenient in synthesizing method, has relatively high purity, and can be applied to synthesis of antigen systems of animal immune, so that the blank in the technical field of trifluralin immunological detection method in China can be filled, and foundation is laid for further development of trifluralin immunological detection method.

Description

technical field [0001] The invention relates to the technical field of immunology, in particular to trifluralin hapten and its preparation method and application. Background technique [0002] Trifluralin is an important selective pre-emergent dinitroaniline herbicide, which is widely used in crops such as soybeans, barley, vegetables and fruits to control annual grass weeds and some broad-leaved weeds. Grass. Although trifluralin is a low-toxic pesticide, long-term exposure experiments have shown that it can cause damage to the liver and kidneys, and high-dose exposure can cause low fetal weight and height and increase the risk of miscarriage. Due to the widespread use of trifluralin pesticides, its residues are ubiquitous in soil and water, especially in aquatic products (fish, shrimp, crab), which poses a huge hidden danger to the food safety of aquatic products. [0003] In order to avoid the potential harm of trifluralin herbicide, many countries have restricted its u...

Claims

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Application Information

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IPC IPC(8): C07C229/18C07C227/18C07K16/44
CPCC07C229/18C07K16/44
Inventor 穆洪涛李轩陈雪贞贺帆丽刘凤银袁学文
Owner 深圳容金科技有限公司
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