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DL-beta-amino butyric acid derivative and its preparing method and use

A technology of aminobutyric acid and derivatives, which is applied in the field of aminobutyric acid derivatives, and can solve the problems of low induction activity and large dosage

Inactive Publication Date: 2005-05-18
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The technical problem to be solved by the present invention is: in order to overcome the shortcomings of the existing DL-β-aminobutyric acid derivatives and DL-β-aminobutyric acid inducing plants to produce systemic disease resistance to pathogenic bacteria with low induction activity and large dosage , the present invention provides DL-β-aminobutyric acid derivatives and a preparation method thereof, and they are applied to induce plants to produce systemic disease resistance to pathogenic bacteria with high induction activity and small dosage

Method used

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  • DL-beta-amino butyric acid derivative and its preparing method and use
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  • DL-beta-amino butyric acid derivative and its preparing method and use

Examples

Experimental program
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Effect test

Embodiment 1

[0047] Step 1, the synthesis of 2-methyl-6-hydrouracil:

[0048] Take 43g of crotonic acid (1), 75g of urea, and 150mL of ethylene glycol, heat to 190°C under stirring, keep the temperature at 185°C to 195°C, and reflux for 1 hour. After the reaction is complete, cool the solution and put it in the refrigerator Freeze overnight until a large amount of white solids appear, filter, wash with cold ethanol and a small amount of ice water, dry the white solids obtained, and then recrystallize in ethanol to obtain the product 2-methyl-6-hydrouracil ( 2);

[0049] Step 2, synthesis of DL-β-aminobutyric acid:

[0050] Add 2.56g of 2-methyl-6-hydrouracil (2) into the reaction flask, add 8g of sodium hydroxide and 200mL of water, and heat to reflux for 8 hours under mechanical stirring. After the reaction is completed, the solution is cooled and passed through 50-100 mesh cation exchange resin column, carbon dioxide gas is released at the beginning, rinse with about 800mL of distilled...

Embodiment 2～17

[0058] The 1st~4 steps, with embodiment 1;

[0059] Step 5, except that the aniline in Example 1 is replaced by phenethylamine, o-chloroaniline, m-chloroaniline, 2,4,5-trichloroaniline, m-bromoaniline, p-bromoaniline, o-methylaniline, m-methylaniline, o-methoxyaniline, p-fluoroaniline, 2,3,4-trifluoroaniline, 2-aminothiazole, 2-amino-1,3,5-thiadiazole, 3-amino-5- Except methylpyrazole, 3-amino-5-phenyl-1,2,4-triazole or 3-methylthio-4-cyano-5-aminopyrazole, other are the same as embodiment 1, respectively get Products and their yields are shown in II-1b, II-1c, II-1d, II-1e, II-1f, II-1g, II-1h, II-1i, II-1j, II-1k, II-1l, II-1m, II-1n, II-1o, II-1p, II-1q.

Embodiment 18

[0061] The 1st~4 steps, with embodiment 1;

[0062] The 5th step, the synthesis of 2-N-benzothiazole-3-N-benzyloxycarbonyl-aminobutanamide (II-1r):

[0063]Dissolve 1.5 mmol of 2-aminobenzothiazole in 8 mL of tetrahydrofuran, add 0.23 mL of triethylamine, cool in an ice-water bath, and add 1 mmol of 3-benzyloxycarbonyl-β-aminobutyryl chloride (5) dropwise at 0°C 6mL tetrahydrofuran solution, white insoluble matter was formed, which was triethylamine hydrochloride, monitored by TLC, reacted for 0.5 to 1 hour, filtered, evaporated the solvent under reduced pressure, added 20mL chloroform to dissolve the residue, washed with 1mol / L hydrochloric acid , washed with water, dried with anhydrous sodium sulfate, removed the solvent, separated by vacuum column chromatography to obtain the product or recrystallized with toluene to obtain the product 2-N-benzothiazole-3-N-benzyloxycarbonyl-aminobutyramide (II -1r) 0.23 g, yield 61%.

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Abstract

The present invention relates to DL-beta-amino butyric acid derivative and its preparation process and use. The compound is used as plant disease resistance activating agent in plant guard mechanism to induce plant to produce systemic pathogenic bacteria resistance, and has high inducing activity and small used amount.

Description

technical field [0001] The technical scheme of the present invention relates to derivatives of aminobutyric acid. Background technique [0002] Plant diseases caused by microorganisms, such as powdery mildew, rust, and blight, will seriously affect the growth and development of plants, and will seriously endanger the quality of crop products. In order to deal with plant diseases and insect pests, people have used pesticides for a long time. However, as a result of the use of existing pesticides, although crop pests and diseases were effectively controlled at that time, the pollution and destruction of the ecological environment also made people pay a heavier price. In particular, the pollution caused by HC6 and DDT has exceeded people's expectations. Although they have been out of use for many years, their residues can still be detected in many agricultural products. Therefore, research and exploration of new technologies and new ways of plant protection has always been on...

Claims

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Application Information

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IPC IPC(8): A01N25/22C07C229/12
Inventor 李正名臧洪俊倪长春范志金王素华
Owner NANKAI UNIV
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