Compounds containing 1,4-diazacyclohexanepiperazine and their uses

Abstract

This invention relates to the field of crop seed vigor regulation technology, specifically to compounds containing 1,4-diazacyclohexanepiperazine and their uses. The compounds containing 1,4-diazacyclohexanepiperazine have the chemical structure shown in general formula (I). These compounds can efficiently enhance seed vigor and effectively improve crop yield and quality.

Description

Technical Field

[0001] This invention relates to the field of crop seed vigor regulation technology, specifically to compounds containing 1,4-diazacyclohexanepiperazine and their uses. Background Technology

[0002] Seed vigor is the potential of a seed to germinate, grow, and form a healthy plant under suitable conditions, and it is an important indicator for evaluating seed quality. Factors affecting seed vigor include internal factors, such as seed genetic characteristics and individual development status, and external factors, such as mechanical damage, high temperature and humidity environments, and storage time. Currently, the main approach is to improve seed vigor by optimizing seed genetic characteristics and storage conditions, thereby increasing crop yield and quality.

[0003] However, current methods for optimizing seed genetic characteristics and storage conditions are relatively inefficient and unsuitable for large-scale production and application. Summary of the Invention

[0004] The purpose of this invention is to overcome the shortcomings of the prior art by providing a compound containing 1,4-diazacyclohexanepiperazine and its uses. This compound containing 1,4-diazacyclohexanepiperazine can efficiently enhance seed vigor and effectively improve crop yield and quality.

[0005] To achieve the above objectives, the present invention provides the following technical solution:

[0006] Provided are compounds containing 1,4-diazacyclohexanepiperazine, having the chemical structure shown in general formula (I):

[0007]

[0008] It also provides the use of compounds containing 1,4-diazacyclohexanepiperazine in improving crop seed vigor.

[0009] In some embodiments, the seed is a crop seed.

[0010] In some embodiments, the crop seeds are rice or corn.

[0011] In some implementations, the corn is seed that has been stored for more than one year.

[0012] This provides the use of compounds containing 1,4-diazacyclohexanepiperazine in the preparation of pharmaceuticals for improving crop seed vigor.

[0013] In some embodiments, the drug is administered by mixing the drug with the seeds to allow the seeds to germinate and grow.

[0014] A pharmaceutical composition is provided comprising the above-mentioned compound containing 1,4-diazacyclohexanepiperazine as an active ingredient, and one or more pharmaceutical excipients.

[0015] The beneficial effects of this invention regarding a compound containing 1,4-diazacyclohexanepiperazine and its uses:

[0016] The present invention discloses a compound containing 1,4-diazacyclohexanepiperazine, comprising a basic skeleton and 1,4-diazacyclohexanepiperazine linked to the skeleton. The pyrido[2,3-D]pyrimidine and 4-methoxy-phenyl groups in the basic skeleton regulate the ABA (abscisic acid) signaling pathway, thereby effectively enhancing crop seed vigor, promoting rapid seed germination, and resulting in robust and uniform seedling emergence. The 1,4-diazacyclohexanepiperazine further enhances crop seed vigor in coordination with its skeleton. This invention develops the application of compounds containing 1,4-diazacyclohexanepiperazine in improving seed vigor, suitable for large-scale production and application. Attached Figure Description

[0017] Figure 1 This study investigated the effects of the compound containing 1,4-diazacyclohexanepiperazine in Experiment 1 on the germination rate and seedling rate of maize seeds.

[0018] Figure 2 This is a schematic diagram of the basic skeleton of the AZD8055 compound. Detailed Implementation

[0019] Preferred embodiments of the invention will now be described in more detail with reference to the accompanying drawings. While preferred embodiments of the invention are shown in the drawings, it should be understood that the invention can be implemented in various forms and should not be limited to the embodiments set forth herein. Rather, these embodiments are provided so that the invention will be thorough and complete, and will fully convey the scope of the invention to those skilled in the art.

[0020] Example 1

[0021] To illustrate the method for obtaining compounds containing 1,4-diazacyclohexanepiperazine according to the present invention, the following is disclosed:

[0022] like Figure 2 The basic skeleton of compound AZD8055 shown is the basic skeleton of a compound containing 1,4-diazacyclohexanepiperazine. The basic skeleton 1 (pyrido[2,3-D]pyrimidine) and the basic skeleton 2 (4-methoxy-phenyl) are the basic structures for regulating seed vigor by achieving mTOR inhibition activity. On this basic skeleton, the 3-position derivatization of 1,4-diazacyclohexanepiperazine on the benzene ring of basic skeleton 2 can better enhance seed vigor.

[0023] To illustrate how the basic framework of the AZD8055 compound was synthesized, the synthetic approach is explained below:

[0024] Based on the retrosynthetic method, the analysis is as follows:

[0025]

[0026] Therefore, the method for synthesizing the basic skeleton of the compound AZD8055 shown in general formula (I) includes the following steps:

[0027] 2,6-dichloro-6-carboxypyridine synthesis

[0028] Will synthesis

[0029] Will Chemical structure of general formula (I)

[0030] Those skilled in the art can implement the specific synthetic steps through experimental synthetic methods.

[0031] Subsequently, regarding R 1 The design yielded compounds containing 1,4-diazacyclohexanepiperazine:

[0032]

[0033] Effect verification:

[0034] To illustrate the effect of the compound containing 1,4-diazacyclohexanepiperazine of the present invention on enhancing seed vigor, the following experiments were conducted.

[0035] The AZD8055 compound involved in the experimental examples is:

[0036] Drug Name: AZD-8055

[0037] CAS No.: 1009298-09-2

[0038] Molecular formula: C 25 H 31 N5O4

[0039] Molecular weight: 465.54

[0040] Chemical structure:

[0041]

[0042] The experimental example contains the following compound: 1,4-diazacyclohexanepiperazine

[0043]

[0044] Seed vigor enhancement treatments for different crops were carried out using compound AZD8055 and compounds containing 1,4-diazacyclohexanepiperazine, as detailed below:

[0045] 1.1 Seed germination experiment: The method was slightly modified from Wang et al. (2010). Seeds of popular varieties of rice, sweet corn, soybean, tomato, cucumber, water spinach, and Chinese cabbage, along with their remaining stock, were used as the test subjects. Three replicates were set up for each material. For each replicate, 50 mature and plump seeds were selected and placed in 9cm diameter transparent disposable petri dishes lined with filter paper. 10mL of distilled water was added, and the petri dishes were then placed in a 28℃ constant temperature and light incubator (12h light / 12h darkness) for 5 or 7 days. Germination was defined as the embryo breaking through the seed coat by 2mm, and seedling establishment was defined as the radicle reaching the length of the seed and the embryo reaching more than half the length of the seed. The number of germinated and established seeds was counted every 12 hours. The germination rate over 5 consecutive days is taken as the germination potential (GP) over 5 days. Germination index (GI) = ∑(Gt / Dt) (Dt represents the number of germination days), Gt represents the number of seeds germinated each day corresponding to Dt, and T50 is the time (d: days) required for the germination rate to reach half.

[0046] 1.2 Germination Experiment with Exogenous Reagent Treatment: For different crops, appropriate concentrations of reagents (0 μM, 0.2 μM, 2 μM, 5 μM, and 10 μM) were selected for exogenous treatment. The germination rate was recorded 3-5 days after application under different concentrations, and the germination potential was recorded for 5 consecutive days.

[0047] 1.3 Seedling growth assessment experiment:

[0048] (1) Select 50 mature and plump seeds, gently peel off the husk, and try to avoid damaging the embryo.

[0049] (2) Place the shelled seeds in a 50℃ oven for about 3 days to break dormancy.

[0050] (3) Then pour the seeds into a 50mL sterile centrifuge tube, add 10mL of 75% anhydrous ethanol, wash the seeds with a shaker at 200rpm for 5min, pour out the ethanol in a clean bench (be careful not to drop the seeds), and wash once with sterile water.

[0051] (4) Add 5 mL of 2.5% sodium hypochlorite to the laminar flow hood and wash the seeds with a shaker at 200 rpm for 15-20 min. Then discard the sodium hypochlorite in the laminar flow hood and wash with sterile water 3-5 times.

[0052] (5) In a clean bench, place the washed seeds on sterile filter paper to absorb the moisture. Use tweezers that have been sterilized by high temperature after flaming to carefully pick up the dried seeds and place them on a 1 / 2 MS medium plate. After inoculation, seal the culture dish with sealing film and place it in a dark incubator at 28℃ for 2 days.

[0053] (6) After most of the seeds show white sprouts, disinfect the surface with alcohol and open it in a clean bench. Inoculate the seeds with consistent germination onto 1 / 2MS medium plates containing different concentrations of reagents. After sealing, place them in a 28℃ constant temperature light incubator (12h light / 12h dark) for 12 days.

[0054] (7) Count the length, root length and number of rice seedlings, and take photos.

[0055] 1.4 Seedling growth experiment in soil cultivation:

[0056] Each material was prepared in triplicate. For each replicate, 30 mature, plump seeds were selected and placed in 9cm diameter transparent disposable petri dishes lined with filter paper. 10mL of distilled water or reagent treatment solution was added, and the petri dishes were then placed in a 28℃ constant temperature and light incubator (12h light / 12h dark) for 3 days. Subsequently, the seeds were transferred to pots filled with moist field soil and placed in a 28℃ constant temperature and light incubator (12h light / 12h dark) for 14 days. Seedling growth was observed and photographed during this period.

[0057] Experimental Example 1

[0058] Tests were conducted on maize varieties, comparing them to the AZD8055 treatment. Figure 1 The results showed that a compound containing 1,4-diazacyclohexanepiperazine (labeled YSW-9) exhibited a higher germination rate than the AZD8055 treatment. Furthermore, in tests on directly sown soil after treatment, the compound containing 1,4-diazacyclohexanepiperazine showed a better effect on improving seedling survival rate, further demonstrating that compounds containing 1,4-diazacyclohexanepiperazine have a greater effect on improving seed germination rate, and exploring the application of compounds containing 1,4-diazacyclohexanepiperazine in enhancing seed viability.

[0059] The above description is merely a preferred embodiment of the present invention and is not intended to limit the invention. Various modifications and variations can be made to the present invention by those skilled in the art. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the scope of protection of the present invention.

Claims

1. A compound containing 1,4-diazocyclohexylpiperazine, characterized in that, It is shown in chemical structural formula (I): 。 2. Use of a 1,4-diazabicycloheptane piperazine-containing compound according to claim 1 for increasing the viability of crop seeds; the crop seeds being corn.

3. Use according to claim 2, characterized in that, The corn is seed that has been stored for more than 1 year.

4. Use of a 1,4-diazabicycloheptane piperazine-containing compound according to claim 1 for the preparation of a medicament for increasing the viability of crop seeds; the crop seeds being corn.

5. Use of a 1,4-diazabicycloheptane piperazine-containing compound according to claim 4 for the manufacture of a medicament for increasing the viability of crop seeds, characterized in that, The medicament is administered by mixing the medicament with the seeds and allowing the seeds to germinate and grow.

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