R-ureide compounds and uses thereof

Abstract

The invention relates to the technical field of regulation and control of crop seed vigor, in particular to an R-ureide compound and application thereof. The R-ureide compound has a chemical structure as shown in a general formula (I): # imgabs0 #, R is alkyl, and the R-ureide compound can efficiently improve the seed activity and promote the rapid germination of seeds by acting on the internal genetic mechanism of the seeds.

Description

Technical Field

[0001] The invention relates to the technical field of regulating and controlling the vitality of crop seeds, and in particular to an R-urea compound and a use thereof. Background Art

[0002] Seed vigor is an important indicator of seed sowing quality and a major component of seed value. Seed vigor is a complex comprehensive trait, which is manifested in rapid seed germination, stress-resistant germination, and rapid seedling establishment. Seed vigor combines seed germination rate, emergence rate, seedling growth potential, plant resistance, and production potential. It is the ability of seeds to germinate and form new plants in a suitable environment. At present, in order to improve the vitality of rice varieties, the main method is to explore the genes related to seed vigor and analyze their genetic regulation mechanisms. No effective drugs have been found to improve seed vigor. Summary of the invention

[0003] The purpose of the present invention is to avoid the shortcomings of the prior art and provide an R-ureide compound and its use. The R-ureide compound can effectively improve seed vitality and promote rapid seed germination by acting on the genetic mechanism inside the seed.

[0004] To achieve the above object, the present invention provides the following technical solutions:

[0005] Provided is an R-urea compound having a chemical structure shown in general formula (I):

[0006]

[0007] R is an alkyl group.

[0008] Provided is the use of the R-urea compound in improving the vitality of crop seeds.

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

[0010] In some embodiments, the crop seed is corn.

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

[0012] Provided is the use of the R-urea compound 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 R-urea compound as an active ingredient and one or more pharmaceutically acceptable excipients.

[0015] Beneficial effects of an R-urea compound and its use of the present invention:

[0016] The R-ureide compound of the present invention contains pyrido [2,3-D] pyrimidine and 4-methoxy-phenyl in the skeleton, which can achieve the regulation of ABA (plant hormone abscisic acid) signal pathway, which in turn can effectively enhance the vitality of crop seeds, promote rapid germination of seeds and robust and consistent emergence of seedlings, and the R-ureide can coordinate with its skeleton to further enhance the vitality of crop seeds. The application of R-urea in improving seed vitality has been developed, which is suitable for large-scale production and application. BRIEF DESCRIPTION OF THE DRAWINGS

[0017] Figure 1 This is a test of the improvement effect of the R-ureide compound in Experimental Example 1 on the germination rate of seeds of different rice varieties.

[0018] Figure 2 This is a test of the treatment effect of the R-ureide compound of Experimental Example 2 on the germination rate and seedling rate of corn seeds.

[0019] Figure 3 It is a schematic diagram of the basic skeleton of the AZD8055 compound. DETAILED DESCRIPTION

[0020] 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.

[0021] Example 1

[0022] To illustrate the method for obtaining the R-urea compound of the present invention, the following contents are disclosed:

[0023] like Figure 3 The basic skeleton of the AZD8055 compound shown in the figure, wherein basic skeleton 1 (pyrido [2,3-D] pyrimidine) and basic skeleton 2 (4-methoxy-phenyl) are the basic structures for achieving mTOR inhibition activity and thus regulating seed activity, and on this basic skeleton, N-methyl-2-hydroxyethylamine is derived at the 3-position of the benzene ring of basic skeleton 2, which can better achieve the effect of AZD8055 compound in enhancing seed activity.

[0024] In order to illustrate how to synthesize the basic skeleton of AZD8055 compound, the synthesis idea is explained as follows:

[0025] Based on the retrosynthetic method, the analysis is as follows:

[0026]

[0027] Therefore, the synthesis method of the basic skeleton of the AZD8055 compound shown in general formula (I) comprises the following steps:

[0028] 2,6-Dichloro-6-carboxypyridine synthesis Will synthesis Will Synthesis of the chemical structure of general formula (I)

[0029]

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

[0031] Then, R 1 The design is specifically based on R-urea compounds:

[0032]

[0033] Effect verification:

[0034] In order to illustrate the effect of the R-urea compound of the present invention on improving seed vitality, the following experiment was conducted. The AZD8055 compound involved in the experimental example is:

[0035] Drug name: AZD-8055

[0036] CAS No.:1009298-09-2

[0037] Molecular formula: C 25 H 31 N5O4

[0038] Molecular weight: 465.54

[0039] Chemical Structure:

[0040]

[0041] The R-urea compound of the experimental example is:

[0042]

[0043] AZD8055 compound and its R-urea compound were used to improve the vitality of different crop seeds. The details are as follows:

[0044] 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).

[0045] 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.

[0046] 1.3 Seedling growth identification experiment:

[0047] (1) Select 50 mature and plump seeds and gently peel off the husks, trying to avoid damaging the embryo.

[0048] (2) Place the shelled seeds in a 50°C oven for about 3 days to break dormancy.

[0049] (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.

[0050] (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.

[0051] (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.

[0052] (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.

[0053] (7) Count the length of rice seedlings, root length and number of roots, and record and take photos.

[0054] 1.4 Seedling soil culture growth experiment:

[0055] 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.

[0056] Experimental Example 1

[0057] The japonica rice variety Zhonghua 11 and the indica rice varieties Nayou 51 and Shengyou 6126 were tested. The results showed that compared with the AZD8055 treatment, Figure 1 The results showed that the R-urea compound (labeled as YSW-14) had a higher effect of improving the seed germination rate, which showed that the application of the R-urea compound in improving seed vitality was developed.

[0058] Experimental Example 2

[0059] Tests were carried out on maize varieties such as Figure 2 As shown, it was found that the R-ureide compound (labeled as YSW-14) showed different degrees of improvement in germination rate compared with the AZD8055 treatment. At the same time, in the test of direct seeding soil after treatment, the R-ureide compound had a better effect on improving the seedling establishment rate.

[0060] 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. R-ureide compound, characterized in that It is a chemical structure shown in general formula (I): ， R is an alkyl group.

2. Use of the R-ureide compound according to claim 1 in improving the vigor 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 corn.

5. The use according to claim 4, characterized in that: The corn is seeds stored for more than one year.

6. Use of the R-ureide compound 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 R-urea compound according to claim 1 as an active ingredient and one or more pharmaceutical excipients.

Images