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Dimethomorph hapten, and preparation method and application thereof

The technology of dimethomorph and mesomorpholine is applied in the field of dimorpholine hapten and its preparation, which can solve the problems of many pretreatment steps, low recovery rate and the like, and achieves simple synthesis method, fast detection method, high yield effect

Active Publication Date: 2020-05-12
NATIONAL MARINE ENVIRONMENTAL MONITORING CENTRE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At home and abroad, the detection method for dimethomorph mainly adopts gas chromatography. Gas chromatography is accurate, reliable and has high sensitivity, but there are many pretreatment steps and the recovery rate is low.

Method used

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  • Dimethomorph hapten, and preparation method and application thereof
  • Dimethomorph hapten, and preparation method and application thereof
  • Dimethomorph hapten, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Embodiment 1: the synthesis of dimethomorph hapten

[0038] Step 1) p-nitrobenzoyl chloride 50.0g (purchased from Shanghai McLean Biochemical Technology Co., Ltd., article number N814650), with absolute ethanol as solvent, p-nitrobenzoyl chloride: chlorobenzene: aluminum trichloride (purchased from Shanghai McLean Biochemical Technology Co., Ltd., product number A822326) with a molar ratio of 1:2.5:1.5, a reaction temperature of 75° C., and a reaction time of 1.5 h. The reaction solution became viscous, reddish brown, stopped the reaction, poured into 2M sulfuric acid aqueous solution for treatment, suction filtered and washed with water, added the filter cake into dilute sodium hydroxide solution, heated and stirred, washed with water until neutral, and dried to obtain a yellow crude product. After dissolving in 95% ethanol, filtering and recrystallizing, 46.1 g of white solid, product 1, was obtained, with a yield of 92.2%.

[0039] Step 2) Dissolve 29.5 g of triethy...

Embodiment 2

[0043] Example 2: Identification of dimethomorph haptens

[0044] Samples of product 3, product 4, and product 5 in Example 1 were sent to Beijing Zhongke Huiren Technology Co., Ltd. for NMR identification. The specific results are as follows:

[0045] Get the product 3 structure of above-mentioned embodiment 1 and be characterized as:

[0046] 1 H NMR: δ6.16 (1H, s), 6.99 (2H, ddd, J = 8.0, 1.3, 0.6Hz), 7.38 (2H, ddd, J = 8.5, 1.5, 0.5Hz), 7.50-7.61 (4H, 7.53(ddd,J=8.0,1.5,0.6Hz),7.58(ddd,J=8.5,1.6,0.5Hz)).

[0047] Get the product 4 structure of above-mentioned embodiment 1 and be characterized as:

[0048] 1 H NMR: δ3.51-3.67 (8H, 3.59 (ddd, J = 15.2, 10.2, 3.2Hz), 3.62 (ddd, J = 12.2, 3.2, 2.4Hz)), 6.35 (1H, s), 6.82 (2H ,ddd,J=8.4,1.2,0.5Hz),7.31-7.40(4H,7.34

[0049] ddd,J=8.4,1.9,0.5Hz),7.37(ddd,J=8.4,1.4,0.5Hz)),7.57(2H,ddd,J=8.4,1.7,0.5Hz).

[0050] Get the product 5 structure of above-mentioned embodiment 1 and be characterized as:

[0051] 1 H NMR: δ3.51-3....

Embodiment 3

[0052] Example 3: Dimethomorph antigen

[0053] Step 1) Dissolve 50 mg of dimethomorph hapten with dilute hydrochloric acid, add dropwise 1.5% sodium nitrite solution, and keep stirring under ice bath. After the solution turned blue-black, stop adding the sodium nitrite solution and continue the reaction for 15 minutes.

[0054] Step 2) One portion was added dropwise to bovine serum albumin solution (pH 8.3, 0.2M carbonate buffer solution) (purchased from sigma company, product number 5479) with a concentration of 20 mg / mL, and the other portion was added dropwise to 10 mg / mL In mL ovalbumin solution (purchased from sigma, product number A5503) (pH 8.3, 0.2M carbonate buffer solution), stir, adjust the pH to 10, react at 2-8°C for 3h, and use 0.01M PBS Dialyze for 3 days, aliquot and store at -20°C.

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Abstract

The invention relates to the technical field of biology, and discloses a dimethomorph hapten, and a preparation method and an application thereof. The dimethomorph hapten reserves the chemical structure of dimethomorph to the greatest extent, a nitrogen-containing group capable of being coupled with proteins is introduced through chemical synthesis, the synthesis method is simple, and the productpurity and yield are high; and the hapten is used as a raw material to prepare an antigen system suitable for animal immunization, and a prepared monoclonal antibody has good specificity, affinity and antibody titer, and can be used for preparing an enzyme linked immunosorbent assay kit, and the kit has the advantages of low detection cost, and fast, efficient and accurate detection method, and is suitable for on-site monitoring of dimethomorph residues in vegetables and fruits and screening of a large number of samples.

Description

technical field [0001] The invention belongs to the field of biotechnology, and in particular relates to a dimethomorph hapten and its preparation method and application. Background technique [0002] Dimethomorph is a derivative of cinnamic acid compounds. It was first reported in France in 1988 for the prevention and treatment of grape downy mildew and potato and tomato late blight. It is a new control of downy mildew pathogenic fungi It is a high-efficiency systemic fungicide for diseases, and has high activity against benzamide fungicide-resistant and sensitive strains. In practical applications, dimethomorph is another effective method for preventing and treating oomycete diseases after metalaxyl. It is an ideal fungicide, especially suitable for the control of drug resistance in fields where benzamide fungicide-resistant pathogenic individuals are dominant. [0003] However, long-term laboratory research has found that dimethomorph can cause cancer and gene mutations ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/185C07K14/765C07K14/77C07K16/44G01N33/577
CPCC07D295/185C07K14/765C07K14/77C07K16/44G01N33/577G01N2430/00
Inventor 王睿睿
Owner NATIONAL MARINE ENVIRONMENTAL MONITORING CENTRE
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