Pyrazole amide compounds as well as preparation method application of pyrazole amide compounds

A compound and pyrazole technology, applied in the field of pyrazole amide compounds and their preparation, can solve the problems of high cost of synthesis of brassinolide, many metabolic sites, easy metabolic inactivation and the like, so as to improve the ability of resisting lodging, Easy to prepare, low cost 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] US6667278B2 (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 through 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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  • Pyrazole amide compounds as well as preparation method application of pyrazole amide compounds
  • Pyrazole amide compounds as well as preparation method application of pyrazole amide compounds
  • Pyrazole amide compounds as well as preparation method application of pyrazole amide compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Example 1, 4-(1H-pyrazole-3-amino)-4-oxobutanoic acid methyl ester (R in formula (I) 1 and R 2 is H, R is the synthesis of methyl butyrate)

[0056]

[0057] 1) Synthesis of N-Boc-3-aminopyrazole

[0058]

[0059] In a 100 mL round bottom flask, add 3-aminopyrazole (10 mmol) and di-tert-butyl dicarbonate (Boc) 2 O (14mmol), 15mL tetrahydrofuran (solvent A) was stirred and dissolved, added DMAP (0.6mmol, 6%) in an ice-salt bath and stirred for 2-4 hours, returned to room temperature, concentrated, beaten with ethyl acetate / petroleum ether, and filtered to obtain pure product. The specific method of solvent beating is: to 1g of the initial product to be purified, add the mixed solvent (V 乙酸乙酯 / V 石油醚 =2:1) ​​5mL, stirred at room temperature until the product was completely precipitated, and the pure product was obtained by suction filtration.

[0060] 2) Synthesis of 4-[(N-Boc-pyrazole)-3-amino]-4-oxobutanoic acid methyl ester

[0061]

[0062]In a 100mL ro...

Embodiment 2

[0070] Embodiment 2, the determination of the growth regulation activity of plant

[0071] (1) Hypocotyl elongation activity experiment of Arabidopsis mutant det2-1

[0072] Seeds of the Arabidopsis mutant det2-1 were sterilized with 70% ethanol for 1 min, and 1% sodium hypochlorite for 15 min at the same time, washed with sterile water and sown in 1 / 2MS (0.8% agar, 1% sucrose and compounds with specified concentrations); 4°C refrigerator After vernalization for 3 days, they were transferred to dark conditions and cultured at 22°C for 7 days. After the whole plant was photographed, the length of the hypocotyl was measured by ImageJ software.

[0073] test results

[0074] The test results of all compounds are shown in Tables 2 and 3.

[0075] Table 2 The test results of hypocotyl elongation of control drug Arabidopsis thaliana

[0076]

[0077] Table 3 The elongation test results of hypocotyls in Arabidopsis thaliana

[0078]

[0079] It can be seen from the above Ta...

Embodiment 3

[0080] Embodiment 3, paddy rice blade inclination experiment

[0081] Rice (Nipponbare) seeds use 10% H 2 o 2 Disinfect for 20 minutes, wash with sterile water, germinate in an incubator at 30°C for 3 days, and culture the young shoots under light for 5-6 days, cut off the leaf angle at 28°C and place it in different concentrations of medicinal liquid for 48 hours, measure with a protractor Leaf inclination.

[0082] test results

[0083] The test results of all compounds are shown in Tables 4 and 5 below

[0084] Table 4 Effects of control chemicals on the tilt angle of rice leaves

[0085]

[0086] Table 5 Effects of synthetic compounds on rice leaf tilt angle

[0087]

[0088] It can be seen from the above Tables 4 and 5 that 24-epiBL has a very high activity. At a concentration of 10 μM, the leaf tilt angle reaches 125±9°. However, when Bikinin is at a maximum concentration of 100 μM, its activity is not as good as that of 24-epiBL, which can only reach 75°. ±8...

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Abstract

The invention discloses pyrazole amide compounds as well as a preparation method application of the pyrazole amide compounds. The structural general formula of the pyrazole amide compounds is shown in the formula I (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 pyrazole amide compound and a preparation method and application thereof. 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 ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/40A01N43/56A01P21/00A01P13/00
Inventor 段留生刘少金于春欣胡堂路陶群周于毅李召虎
Owner CHINA AGRI UNIV
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