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Picolinamide compounds as well as preparation method application of picolinamide compounds

A technology of compound and pyridine, which is applied in the field of pyridine amide compounds and their preparation, can solve the problems of brassinosteroids such as high synthesis cost, easy metabolism inactivation, and no physiological activity, so as to improve lodging resistance, easy preparation, good control effect

Active Publication Date: 2017-06-13
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no solution to the problems of high synthesis cost of brassinosteroids, many metabolic sites in the body, and easy metabolic inactivation. Therefore, the search for new target receptors for the development of analogues has attracted increasing attention.
[0003] US6667278 (2003) reported that the first class of non-steroidal analogues was imitated according to the structure and unit of BL, and the highly active BM1 (pM level) was obtained by screening, but high concentrations (above nM) showed no physiological activity, and must be combined with IAA (5μM) synergy can play a role

Method used

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  • Picolinamide compounds as well as preparation method application of picolinamide compounds
  • Picolinamide compounds as well as preparation method application of picolinamide compounds
  • Picolinamide compounds as well as preparation method application of picolinamide compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Embodiment 1, the preparation of compound 1a:

[0065] The reaction scheme is shown in the following formula:

[0066]

[0067] In a 100mL round-bottom flask, add 2-amino-5-picoline (10mmol) and succinic anhydride (12mmol), stir and dissolve 15mL tetrahydrofuran (solvent A), heat up and reflux for 2 hours for acylation reaction, cool down after the reaction A solid was precipitated, and the solid was obtained by filtration, and purified by recrystallization from ethanol. The specific method of recrystallization is: add 3 mL of ethanol dropwise to 1 g of the primary product to be recrystallized, heat to reflux until the primary product is completely dissolved, and continue to reflux for 10 minutes, then slowly cool down to precipitate a solid, and filter with suction to obtain a pure product.

Embodiment 2

[0068] Embodiment 2, the preparation of compound 1c:

[0069] The reaction scheme is shown in the following formula:

[0070]

[0071] In a 100mL round-bottomed flask, add 2-amino-5-picoline (10mmol), 3ml (20mmol) triethylamine, 15mL tetrahydrofuran and stir to dissolve, cool to 0°C in an ice-salt bath, and add the prepared solution dropwise at a constant temperature. Monoester succinyl chloride solution in 5ml tetrahydrofuran was added dropwise in 20 minutes; the ice bath was removed, the temperature was slowly raised to room temperature, and the acylation reaction continued for 2-3 hours. The reaction mixture was poured into 150mL ice water, extracted with ethyl acetate (3x 100mL), saturated Washed with brine (3 x 100 mL), dried over anhydrous Na2SO4, concentrated by filtration, and the crude product was purified by recrystallization from ethanol or ethyl acetate. The specific method of recrystallization is: add 3 mL of ethyl acetate dropwise to 1 g of the primary product ...

Embodiment 3

[0072] Embodiment 3, the preparation of compound 1g:

[0073] The reaction scheme is shown in the following formula:

[0074]

[0075] In a 100mL round bottom flask, add 2-amino-5-methylpyridine (10mmol) and 15ml tetrahydrofuran and stir to dissolve, then add 4-(trifluoromethoxy)phenylisocyanate (10mmol), and stir the reaction mixture at room temperature for acyl The reaction was carried out, and the progress of the reaction was detected by TLC. After the reaction, a large amount of solid precipitated out and was concentrated to obtain a crude product, which was purified by recrystallization from ethanol. The specific method of recrystallization is: add 3 mL of ethanol dropwise to 1 g of the primary product to be recrystallized, heat to reflux until the primary product is completely dissolved, and continue to reflux for 10 minutes, then slowly cool down to precipitate a solid, and filter with suction to obtain a pure product.

[0076] According to the same method as above...

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Abstract

The invention discloses picolinamide compounds as well as a preparation method and application of the picolinamide compounds. The structural general formula of the picolinamide compounds is shown in the specification. Relevant biological activity tests find that certain compounds can generate specific brassinolide reaction and are capable of promoting the elongation of hypocotyledonary axis of an arabidopsis mutant det2-1 in the dark, increasing of dip angles of rice leaves, enhancing the salt stress resistance of corns and the like. An individual compound has a very high response value at a lower concentration, is capable of inhibiting the plant height of wheat, delaying the growth and improving the lodging resistance at a high concentration and simultaneously has very good effects of preventing and treating gramineous weeds such as wild oat grass, aegilops tauschii, barnyard grass, setaria viridis and goat grass. The series of the compounds are easily to prepare, low in cost, high in agricultural application and promotion values and worthy of being subsequently deeply researched and developed.

Description

technical field [0001] The invention belongs to the field of plant growth regulators, and relates to a pyridine amide compound and its preparation method and application. Background technique [0002] Brassinolides, also known as brassinolides (BRs), are a class of endogenous plant growth regulators synthesized in plants. It can regulate a variety of enzymes and hormones needed by plants, give full play to the potential and growth advantages of plants, and enhance vitality and drought and waterlogging resistance. In view of the extremely low content of brassinolide etc. in plants (less than 10 -6 ppm) and its excellent physiological activity as a plant hormone in agricultural crops, its synthesis and transformation research has always been favored by scientists from all over the world. However, there is no solution to the problems of high synthesis cost of brassinosteroids, many metabolic sites in the body, and easy metabolic inactivation. Therefore, the exploration of fin...

Claims

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Application Information

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IPC IPC(8): C07D213/75C07D213/74A01N43/40A01P21/00A01P13/00
Inventor 段留生刘少金于春欣胡堂路何彦周于毅李召虎
Owner CHINA AGRI UNIV
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