Compounds containing 1, 4-diazacyclohexane piperazine and uses thereof

Abstract

The invention relates to the technical field of regulation and control of crop seed vigor, in particular to a compound containing 1, 4-diazacyclohexane piperazine and application thereof.The compound containing 1, 4-diazacyclohexane piperazine is of a chemical structure as shown in a general formula (I): # imgabs0. The compound containing 1, 4-diazacyclohexane piperazine can effectively improve the seed vigor, and the activity of the seeds can be effectively improved. The yield and the quality of crops are effectively improved.

Description

Technical Field

[0001] The invention relates to the technical field of regulating crop seed vitality, and in particular to a compound containing 1,4-diazacyclohexanepiperazine and a use thereof. Background Art

[0002] Seed vigor is the potential ability of seeds to germinate, grow and form healthy plants under suitable conditions, and is an important indicator for evaluating seed quality. Factors affecting seed vigor include internal factors, such as seed genetic characteristics, individual development status, and external factors, such as mechanical damage, high temperature and high humidity environment, and storage time. At present, the main way to improve seed vigor is to optimize seed genetic characteristics and storage conditions, thereby improving crop yield and quality.

[0003] However, current methods for optimizing seed genetic characteristics and storage conditions are relatively inefficient and not suitable for large-scale production and application. Summary of the invention

[0004] The object of the present invention is to avoid the deficiencies in the prior art and provide a compound containing 1,4-diazacyclohexanepiperazine and its use. The compound containing 1,4-diazacyclohexanepiperazine can efficiently enhance seed vitality and effectively improve the yield and quality of crops.

[0005] To achieve the above object, the present invention provides the following technical solutions:

[0006] Provided is a compound containing 1,4-diazacyclohexanepiperazine, which has a chemical structure shown by general formula (I):

[0007]

[0008] Also provided is the use of the compound containing 1,4-diazacyclohexanepiperazine in improving the vitality of crop seeds.

[0009] In some embodiments, the seeds are crop seeds.

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

[0011] In some embodiments, the corn is seed stored for more than 1 year.

[0012] Provided is a use of a compound containing 1,4-diazacyclohexanepiperazine in preparing a medicine for improving the vitality of crop seeds.

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

[0014] Provided is a pharmaceutical composition containing the above-mentioned 1,4-diazacyclohexanepiperazine-containing compound as an active ingredient and one or more pharmaceutically acceptable excipients.

[0015] The compound containing 1,4-diazacyclohexanepiperazine of the present invention and the beneficial effects of its use:

[0016] The compound containing 1,4-diazacyclohexanepiperazine of the present invention comprises a basic skeleton and 1,4-diazacyclohexanepiperazine connected to the skeleton. The pyrido[2,3-D]pyrimidine and 4-methoxy-phenyl in the basic skeleton can realize the regulation of ABA (plant hormone abscisic acid) signal pathway, which can then effectively improve the vitality of crop seeds, promote rapid germination of seeds and robust and consistent emergence of seedlings. 1,4-diazacyclohexanepiperazine can coordinate with its skeleton to further improve the vitality of crop seeds. The present invention develops the application of the compound containing 1,4-diazacyclohexanepiperazine in improving seed vitality, which is suitable for large-scale production and application. BRIEF DESCRIPTION OF THE DRAWINGS

[0017] Figure 1 This is a test of the treatment effect of the compound containing 1,4-diazacyclohexanepiperazine in Experimental Example 1 on the germination rate and seedling rate of corn seeds.

[0018] Figure 2 It is a schematic diagram of the basic skeleton of the AZD8055 compound. DETAILED DESCRIPTION

[0019] The preferred embodiments of the present invention will be described in more detail below with reference to the accompanying drawings. Although the preferred embodiments of the present invention are shown in the accompanying drawings, it should be understood that the present invention can be implemented in various forms and should not be limited by the embodiments described herein. On the contrary, these embodiments are provided to make the present invention more thorough and complete, and to fully convey the scope of the present invention to those skilled in the art.

[0020] Example 1

[0021] In order to illustrate the acquisition method of the compound containing 1,4-diazacyclohexanepiperazine of the present invention, the following contents are disclosed:

[0022] like Figure 2 The basic skeleton of the AZD8055 compound shown is the basic skeleton of a compound containing 1,4-diazacyclohexanepiperazine, wherein basic skeleton 1 (pyrido[2,3-D]pyrimidine) and basic skeleton 2 (4-methoxy-phenyl) are the basic structures for achieving mTOR inhibition and thus regulating seed vitality, and on this basic skeleton, 1,4-diazacyclohexanepiperazine is derived at the 3-position of the benzene ring of basic skeleton 2, which can better achieve the improvement of seed vitality.

[0023] In order to illustrate how to synthesize the basic skeleton of AZD8055 compound, the synthesis idea is explained as follows:

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

[0025]

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

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

[0028] Will synthesis

[0029] Will Synthesis of the chemical structure of general formula (I)

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

[0031] Then, R 1 Design is performed to specifically obtain a compound containing 1,4-diazacyclohexanepiperazine:

[0032]

[0033] Effect verification:

[0034] In order to illustrate the effect of the compound containing 1,4-diazacyclohexanepiperazine of the present invention on improving seed vitality, the following experiment was conducted.

[0035] The AZD8055 compound involved in the experimental example 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] Experimental Example The compound containing 1,4-diazacyclohexanepiperazine is:

[0043]

[0044] The AZD8055 compound and the compound containing 1,4-diazacyclohexanepiperazine were used to treat the vitality of different crop seeds, as shown in the following details:

[0045] 1.1 Seed germination experiment: refer to Wang et al. (2010) with slight modifications. Seeds of promoted varieties such as rice, sweet corn, soybean, tomato, cucumber, water spinach, Chinese cabbage and their related stockpiles were used as test objects. Three replicates were set for each material. 50 mature and plump seeds were selected for each replicate and placed in a transparent disposable culture dish with a diameter of 9 cm covered with filter paper. 10 mL of distilled water was added, and then the culture dish was placed in a 28°C constant temperature and light incubator (light 12 h / dark 12 h) for 5 or 7 days. The germination standard was when the embryo broke through the seed coat by 2 mm, and the seedling standard was when the radicle reached the length of the seed and the embryo reached more than half of the length of the seed. The number of seeds that germinated and seedled was counted every 12 hours. The germination rate for 5 consecutive days was counted as the 5-day germination potential (GP), germination index (GI) = ∑ (Gt / Dt) (Dt represents the number of germination days), Gt represents the number of germinated seeds per day corresponding to Dt, and T50 is the time required for the germination rate to reach half (d: day).

[0046] 1.2 Germination experiment with exogenous reagents: For different crops, select the corresponding concentration of reagents from 0μM, 0.2μM, 2μM, 5μM, and 10μM for exogenous treatment. The germination rate of 3-5 days under different concentration conditions and the germination potential for 5 consecutive days are statistically analyzed.

[0047] 1.3 Seedling growth identification experiment:

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

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

[0050] (3) Then pour the seeds into a 50 mL sterile centrifuge tube, add 10 mL of 75% anhydrous ethanol, and wash the seeds on a shaker at 200 rpm for 5 min. Pour off the alcohol 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 in a clean bench and wash the seeds on a shaker at 200 rpm for 15-20 min. Then pour out the sodium hypochlorite in the clean bench and wash with sterile water for 3-5 times.

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

[0053] (6) After most of the seeds have turned white, they are disinfected with alcohol on the surface and opened in a clean bench. Seeds with consistent germination are inoculated onto 1 / 2MS culture medium plates containing reagents of different concentrations. After sealing, they are placed in a 28°C constant temperature and light incubator (12 h light / 12 h dark) for 12 days.

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

[0055] 1.4 Seedling soil culture growth experiment:

[0056] Three replicates were set for each material. Thirty mature and plump seeds were selected for each replicate and placed in a 9-cm diameter transparent disposable culture dish covered with filter paper. 10 mL of distilled water or reagent treatment solution was added, and then the culture dish was placed in a 28°C constant temperature and light incubator (12 h of light / 12 h of darkness) for 3 days. The seeds were then transferred to a pot filled with moist field soil and placed in a 28°C constant temperature and light incubator (12 h of light / 12 h of darkness) for 14 days. During this period, the growth of the seedlings was observed and recorded and photographed.

[0057] Experimental Example 1

[0058] The corn varieties were tested and compared with the AZD8055 treatment. Figure 1 The results showed that the compound containing 1,4-diazacyclohexane piperazine (labeled as YSW-9) was found to have an improved effect on germination rate compared with AZD8055 treatment. At the same time, in the test of direct-seeding soil after treatment, the compound containing 1,4-diazacyclohexane piperazine had a better effect on improving the seedling rate, further indicating that the compound containing 1,4-diazacyclohexane piperazine has a higher effect on improving seed germination rate, and the application of the compound containing 1,4-diazacyclohexane piperazine in improving seed activity was developed.

[0059] The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention. For those skilled in the art, the present invention may have various modifications and variations. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention shall be included in the protection scope of the present invention.

Claims

1. A compound containing 1,4-diazacyclohexanepiperazine, characterized in that: It is a chemical structure shown in general formula (I):

2. Use of the compound containing 1,4-diazacyclohexanepiperazine according to claim 1 in improving the vitality of crop seeds.

3. The use according to claim 2, characterized in that: The seeds are crop seeds.

4. The use according to claim 2, characterized in that: The crop seeds are rice and corn.

5. The use according to claim 2, characterized in that: The corn is seeds stored for more than one year.

6. Use of the compound containing 1,4-diazacyclohexanepiperazine according to claim 1 in the preparation of a medicament for improving the vitality of crop seeds.

7. The drug according to claim 6, characterized in that The drug is administered in the following manner: the drug is mixed with seeds, and the seeds are allowed to germinate and grow.

8. A pharmaceutical composition, characterized in that The invention contains the 1,4-diazacyclohexanepiperazine compound as claimed in claim 1 as an active ingredient and one or more pharmaceutical excipients.

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