Imidacloprid hapten, complete antigen and synthesis and application of imidacloprid hapten and complete antigen

A complete antigen, imidacloprid technology, applied in the direction of animal/human protein, serum albumin, ovalbumin, etc., can solve the problems of endangering the environment or human health, entering the soil or human body, complex reaction conditions, etc., to save synthesis costs, The synthesis method is simple and efficient, and the effect of efficient and accurate detection

Inactive Publication Date: 2022-01-28
信达安检测技术(天津)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, pesticides containing imidacloprid have been registered for use in more than 120 countries around the world. The scope of application involves more than 60 kinds of crops such as grain, vegetables, fruit trees, and tea. On the one hand, it has a certain impact on the environment. On the other hand, there are a lot of residues in the plant itself, and these residues will eventually enter the soil or the human body, endangering the environment or human health.
[0004] At present, in order to study the relevant mechanism of imidacloprid antigen that can cause an immune response in animals, most experimenters have certain limitations in the method of preparing imidacloprid hapten and imidacloprid complete antigen. For example, the invention patent with application publication number CN109917126A discloses an imidacloprid hapten The preparation method, the invention patent with application publication number CN107805241A discloses a preparation method of imidacloprid hapten and complete antigen, and the preparation methods of the two invention patents for preparing imidacloprid hapten and complete antigen have long reaction time and complicated reaction conditions, involving Oil bath heating, multiple extractions, column loading and other steps, so the present invention relates to a new imidacloprid hapten, complete antigen and related synthesis methods, which can be applied to immunoassay technology and avoid the above limitations

Method used

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  • Imidacloprid hapten, complete antigen and synthesis and application of imidacloprid hapten and complete antigen
  • Imidacloprid hapten, complete antigen and synthesis and application of imidacloprid hapten and complete antigen
  • Imidacloprid hapten, complete antigen and synthesis and application of imidacloprid hapten and complete antigen

Examples

Experimental program
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Effect test

preparation example Construction

[0050] The synthetic method of this imidacloprid hapten comprises the steps:

[0051] S1. Preparation of imidacloprid intermediate

[0052] Dissolving imidacloprid in DMF, adding sodium hydride and tert-butyl halocarboxylate, obtains the tert-butyl carboxylate intermediate of imidacloprid N substitution, wherein, the molar ratio of imidacloprid, sodium hydride and tert-butyl halocarboxylate is 1:1-1.1:1-3;

[0053] S2. Preparation of imidacloprid hapten

[0054] Under acidic conditions and deprotection reagent environment, imidacloprid N-substituted tert-butyl carboxylate intermediate undergoes de-tert-butyl reaction to obtain imidacloprid hapten, and the deprotection reagent is hydrochloric acid, trifluorohydrochloric acid, hydrobromic acid One, the imidacloprid hapten is imidacloprid hapten derivative 2-[3-[(6-chloropyridyl-3-yl)methyl]-2-nitroimidazolin-1-yl]acetic acid, 3-[3-[(6-chloropyridyl-3-yl)methyl]-2-nitroimidazolin-1-yl]propanoic acid, 4-[3-[(6-chloropyridyl- 3...

Embodiment 1

[0071] The imidacloprid hapten synthesized in this example is 2-[3-[(6-chloropyridyl-3-yl)methyl]-2-nitroimidazolin-1-yl]acetic acid (hapten 1).

[0072] This embodiment relates to a kind of imidacloprid hapten and its synthesis method:

[0073] S1. Preparation of imidacloprid intermediate

[0074] Weigh 5g of imidacloprid and dissolve it in 20ml of DMF, stir, add 0.469g of sodium hydride (60% in mineral oil) in batches, stir at room temperature for 30min, add 7.6344g of tert-butyl bromoacetate dropwise, and stir the reaction Overnight, the reaction solution was slowly poured into 150 ml of ice-saturated saturated ammonium chloride solution, extracted three times with 150 ml of tertiary methyl ether, the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain a crude intermediate;

[0075] S2. Preparation of imidacloprid hapten

[0076] Weigh 0.2g of the intermediate obtained in step S1, slowly add 5...

Embodiment 2

[0080] The imidacloprid hapten synthesized in this example is 3-[3-[(6-chloropyridyl-3-yl)methyl]-2-nitroimidazolin-1-yl]propionic acid (hapten 2) .

[0081] This embodiment relates to a kind of imidacloprid hapten and its synthesis method:

[0082] S1. Preparation of imidacloprid intermediate

[0083] Weigh 5g of imidacloprid and dissolve it in 20ml of DMF, stir well, add 0.469g of sodium hydride (60% in mineral oil) in batches, stir at room temperature for 30min, drop in 8.183g of tert-butyl bromopropionate, and react Stir overnight, slowly pour the reaction solution into 150ml of ice-saturated saturated ammonium chloride solution, extract 3 times with 150ml of tertiary methyl ether, combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, and concentrate in vacuo to obtain the crude product of the target product the intermediate;

[0084] S2. Preparation of imidacloprid hapten

[0085] Weigh 0.2g of the intermediate obtained in step S1, ...

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Abstract

The invention provides an imidacloprid hapten, a complete antigen and synthesis and application of the imidacloprid hapten and the complete antigen. The invention relates to the imidacloprid hapten and the synthesis method thereof; the synthesis method of the imidacloprid hapten is simple and efficient; and compared with the prior art, the synthesis method can save the synthesis cost of the imidacloprid hapten and improve the synthesis efficiency of the imidacloprid hapten. The invention also relates to the imidacloprid complete antigen and two synthesis methods thereof. The imidacloprid complete antigen basically retains the characteristic structure of imidacloprid.

Description

technical field [0001] The invention relates to an imidacloprid hapten and a complete antigen and its synthesis and application, belonging to the technical field of imidacloprid hapten and complete antigen. Background technique [0002] Imidacloprid (IMI) is a nitromethylene systemic insecticide, which belongs to the chlorinated nicotinyl insecticides, also known as neonicotinoid insecticides, with broad-spectrum, high efficiency, low toxicity, low Residue and other characteristics, it has multiple effects such as contact killing, stomach poisoning and systemic absorption. After the pests are exposed to the pesticide, the normal conduction of their central nervous system is blocked, causing them to be paralyzed and dead. It can be mainly used to control pests with piercing-sucking mouthparts, and the pests are not easy to develop resistance. [0003] At present, pesticides containing imidacloprid have been registered for use in more than 120 countries around the world. The ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/06C07K14/765C07K14/77C07K14/795C07K16/44G01N33/53
CPCC07D401/06C07K14/765C07K14/77C07K14/795C07K16/44G01N33/5308G01N2430/10
Inventor 冯艳武许翠华郭志远王永旭郭志雄葛怀娜于兴华
Owner 信达安检测技术(天津)有限公司
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