Phenylpyrimidine compound-containing seed coating agent capable of promoting seed germination rate and seedling rate and application thereof

Abstract

The invention relates to a phenylpyrimidine compound-containing seed coating agent capable of promoting the germination rate and the seedling rate of seeds and application of the phenylpyrimidine compound-containing seed coating agent. According to the phenyl pyrimidine compound shown in the formula (I), related auxiliaries including polyvinyl alcohol serving as a film-forming agent, lauryl sodium sulfate serving as a wetting agent, sodium methylene dinaphthalene sulfonate serving as a dispersing agent and xanthan gum serving as a thickening agent are added and ground to prepare a nanoscale suspension type seed coating agent, and then rice seed coating is conducted, so that the germination rate and the seedling rate of seeds can be increased; the seed consumption is reduced. The core component is 4, 6-dichloro-5-phenyl-2-methylpyrimidine, and the effective mass concentration of the 4, 6-dichloro-5-phenyl-2-methylpyrimidine is 2-4%. The method aims at solving the problems of large seed consumption, poor seedling emergence and irregular seedlings in modes of mechanical seeding, direct seeding and the like of rice in rice planting areas in the middle and lower reaches of the Yangtze River, is beneficial to reducing the seeding quantity and improving the seedling rate, has the advantages of simplicity, convenience and trouble saving, and can save cost and improve efficiency.

Description

Technical Field

[0001] The invention belongs to the fields of pesticides, plant protection and cultivation, and relates to a seed coating agent of phenylpyrimidine compounds capable of improving seed germination rate and seedling rate and application thereof. Background Art

[0002] Machine-seeded rice and direct-seeded rice are important rice production methods in the middle and lower reaches of the Yangtze River. They have the advantages of labor-saving, cost-saving and high efficiency. In recent years, due to factors such as tight rice-wheat rotation and insufficient labor, various rice-wheat light cultivation methods such as machine-seeded direct-seeded rice have been widely used, but they have brought the following problems: (1) Seed vitality problem. Due to the tight rice-wheat rotation time and insufficient labor, field preparation is often not in place, and the flatness and uniformity are poor. During the direct-seeding or machine-seeding stage, the seeds are exposed to adverse conditions such as temperature, moisture, and soil flatness. The germination potential of the seeds often decreases, resulting in insufficient basic seedlings in the early stage of the field, resulting in a small number of ears in the later stage, which ultimately affects the yield; (2) Seedling rate problem. From sowing to germination, seeds are mainly self-sustaining. Although seeds with weak bud potential can germinate, the germination rate and seedling success rate are low, resulting in the seedling population being prone to uneven, uneven, and weak seedlings, which is not conducive to unified field management and affects the quality of the crop population. The above problems have seriously affected the high-yield and high-quality production of rice, and restricted the widespread application of machine-sown direct-seeded rice. In production, in order to ensure the emergence rate and seedling rate of seeds, this problem is often solved by increasing the amount of seeds used. However, if the amount of seeds used is too high, it will cause fierce competition among seedlings for resources such as fertilizer, water, light, and temperature. The group is prone to small and weak seedlings, which are not strong enough, thus affecting the emergence of seedlings, which will have a series of adverse effects on the emergence and mid-to-late growth of machine-sown rice or direct-seeded rice after sowing, and ultimately affect the yield and quality of rice. Therefore, in order to improve the emergence rate and seedling rate, the use of special rice seed coating agents for coating is a new technical approach and measure, which not only improves the emergence rate and seedling rate, but also reduces the amount of seeds used. This direction is currently a hot spot and focus of research on high-yield and stress-resistant cultivation and regulation technology of rice.

[0003] Seed coating agents are compositions containing one or more active ingredients, and they play an important role in seed disinfection, slow-release fertilizers, pest control, improving crop resistance, and reducing environmental pollution. Advanced seed coating agents processed with high-tech technology can evenly adhere to the outer surface of seeds to form a protective film, concentrate the drug power around the seeds, release the drug effect slowly, and are not easily affected by the external environment, making it difficult for pests and diseases to survive around them. They can achieve a good disease prevention and seedling protection effect without other agents, with high utilization efficiency and extended drug efficacy period; the surface of seeds after coating is smooth, which is conducive to mechanical sowing. At the same time, the coating agent can adjust the size of seed particles and improve the efficiency of mechanical sowing.

[0004] After checking, it is found that there are currently no similar patents for seed coating agents for improving germination rate and seedling survival rate. In particular, there is a lack of corresponding technologies and methods for improving seed germination potential and increasing germination rate in fields with complex and changeable environments using planting methods such as machine sowing and direct seeding. Summary of the invention

[0005] The object of the invention is to provide a phenylpyrimidine compound that can improve seed germination rate and seedling rate in view of the above-mentioned deficiencies in the prior art.

[0006] Another object of the present invention is to provide the application of the phenylpyrimidine compound.

[0007] Another object of the present invention is to provide a rice seed coating agent.

[0008] The fourth object of the present invention is to provide a method for preparing the rice seed coating agent.

[0009] The fifth object of the present invention is to provide application of the rice seed coating agent.

[0010] The purpose of the present invention can be achieved through the following technical solutions:

[0011] A phenylpyrimidine compound represented by formula (I),

[0012]

[0013] The synthesis steps of the phenylpyrimidine molecular compound 4,6-dichloro-5-phenyl-2-methylpyrimidine are as follows:

[0014]

[0015] Application of the phenylpyrimidine compounds of the present invention in the preparation of rice seed coating preparations.

[0016] The phenylpyrimidine compound of the present invention is used in the preparation of a rice seed coating preparation for improving seed germination rate, seedling rate and promoting dry matter accumulation in the seedling stage.

[0017] A rice seed coating agent is composed of the phenylpyrimidine compound, a film former, a wetting agent, a dispersant, a thickener and purified water. The film former is polyvinyl alcohol, the wetting agent is sodium lauryl sulfate, the dispersant is sodium methylene dinaphthalene sulfonate, and the thickener is xanthan gum.

[0018] As a preferred embodiment of the present invention, the mass ratio of the phenylpyrimidine compound, film-forming agent, wetting agent, dispersant, thickener and pure water is (2-4):(1-2):(1-3):(2-4):(0.2-0.8):100.

[0019] As a further preferred embodiment of the present invention, the rice seed coating agent is prepared by mixing the phenylpyrimidine compound, film-forming agent, wetting agent, dispersant, thickener and purified water, and then grinding the mixture repeatedly to finally form a 2-4% concentration of a phenylpyrimidine compound nano-type stable suspension.

[0020] The preparation method of the rice seed coating agent of the present invention comprises mixing the phenylpyrimidine compound, film-forming agent, wetting agent, dispersant, thickener and purified water, and then grinding them repeatedly to finally form a 2-4% concentration of phenylpyrimidine compound nano-type stable suspension, which is the rice seed coating agent.

[0021] As a preferred embodiment of the present invention, the phenylpyrimidine compound, film-forming agent, wetting agent, dispersant, thickener and purified water are mixed and repeatedly circulated and ground for 100-120 minutes in a grinder, a chiller and a nano sand mill in sequence, and the indoor ambient temperature of all machines is maintained at 20-25 degrees Celsius to finally form a phenylpyrimidine compound nano-type stable suspension with a concentration of 2-4%.

[0022] The rice seed coating agent of the invention is used in improving seed germination rate, seedling rate and promoting dry matter accumulation in seed seedling stage.

[0023] A method for improving seed germination rate, seedling rate and promoting dry matter accumulation in the seedling stage, comprising: using the rice seed coating agent to coat rice seeds with a germination rate of more than 90%, wherein the volume mass ratio of the rice seed coating agent to the rice seeds is 1:40-60 (mL:g), and drying after coating for standby use.

[0024] As a preferred embodiment of the present invention, seeds with a germination rate of more than 90% are selected and dried and then coated normally, and the seed coating agent of the present invention with a concentration of 2% is taken. The machine-sown rice type is coated according to the ratio of the drug seed volume mass ratio of 1:50-60 (mL:g), and the direct-sown rice type is coated according to the ratio of the drug seed volume mass ratio of 1:40-50 (mL:g). The coating can be done manually or mechanically, and the coating concentration is uniform and the thickness is consistent. The coated seeds are sown according to the normal seed amount for the field, and other management methods are the same as those for the field.

[0025] Beneficial effects:

[0026] The present invention designs and synthesizes phenylpyrimidine compounds with the characteristics of safety, high efficiency, high selectivity and environmental friendliness through technical approaches such as bioisostere and active substructure splicing. The compounds are ground by adding relevant auxiliary agents to prepare nano-suspension seed coating agents, and then the rice seeds are coated with a suitable drug-seed ratio, thereby alleviating or eliminating the technical difficulties of low seed germination potential and seedling rate, improving the germination rate and seedling rate of rice seeds in the field, reducing the amount of seeds used, improving the quality of seedlings, saving costs and increasing efficiency.

[0027] The present invention has the following advantages:

[0028] (1) The synthesis process of the phenylpyrimidine compound is simple and has high yield.

[0029] (2) The phenylpyrimidine compound is made into a nano-type rice seed coating agent, which has a simple preparation process and is easy to operate.

[0030] (3) The phenylpyrimidine compound is safe and efficient and can enhance the activity of various physiological enzymes in the metabolic process of seeds.

[0031] (4) The extremely low dosage of the phenylpyrimidine compound can solve the problem of low seed germination rate and low seedling emergence rate under light and simple cultivation, reduce the amount of seeds used, and save seed costs.

[0032] (5) The nano-type rice seed coating agent is easy to use and can be used immediately after packaging, or it can be coated in advance and stored for later use without affecting the germination potential and germination rate of seeds in the later stage. BRIEF DESCRIPTION OF THE DRAWINGS

[0033] Figure 1 Electron micrograph of 4,6-dichloro-5-phenyl-2-methylpyrimidine

[0034] Figure 2 4,6-Dichloro-5-phenyl-2-methylpyrimidine H spectrum

[0035] Figure 3 4,6-Dichloro-5-phenyl-2-methylpyrimidine C spectrum

[0036] Figure 4 Thermal ellipsoid diagram of single crystal of 4,6-dichloro-5-phenyl-2-methylpyrimidine

[0037] Figure 5 Seed germination rate after M17 was used as seed coating agent

[0038] A: Photo of the germination of M17 and Hanyu Baonan seeds after being coated

[0039] B: Photo of germination of seeds of M17 and blank control after coating

[0040] C: Germination rate in the field at different time points after M17 was used as seed coating agent

[0041] D: Germination rate at different time points in the room after M17 was used as seed coating agent

[0042] Figure 6 Comparison of seedling rates under different treatments

[0043] A: Photo of seedlings of M17 and blank control after coating in the field

[0044] B: Photos of indoor seed seedlings of M17 and blank control after coating

[0045] C: Seedling rate of field seeds after coating with M17 as seed coating agent

[0046] D: Seedling rate of indoor seeds after coating with M17 as seed coating agent

[0047] Figure 7 Plant height at 12 and 20 days after germination

[0048] A: Photo of plant height of M17 after coating at 12 days

[0049] B: Photo of plant height of M17 at 20 days after coating

[0050] C: Plant height data of M17 after coating

[0051] Figure 8 Dry matter weight per plant at seedling stage

[0052] A: Photo of the material after M17 coating

[0053] B: Dry weight of stems, leaves and roots after coating with M17 DETAILED DESCRIPTION

[0054] The main equipment involved in the following embodiments are electric lifting basket grinder (model: LZLM-3L, produced by Changzhou Lezu Machinery Technology Co., Ltd.), chiller (model: ZP, produced by Changzhou Lezu Machinery Technology Co., Ltd.), nano sand mill (model: LZNSM-0.3L, produced by Changzhou Lezu Machinery Technology Co., Ltd.). In specific production, they are not limited to the above equipment, and can be similar models from the same manufacturer, or similar equipment from different manufacturers that can achieve the same function.

[0055] Example 1

[0056]

[0057] Sodium glycolate solution was prepared with metallic sodium (3.586 g, 0.156 mol) and purified anhydrous ethanol (200 mL), and acetamidine hydrochloride (7.650 g, 0.0809 mol) and diethyl phenylmalonate (18.910 g, 0.0800 mol) were added and refluxed at 90°C for 4 h; after the reaction was completed and cooled to room temperature, the solvent was distilled off under reduced pressure, the crude sodium salt was added to 1 L of distilled water to dissolve, and concentrated hydrochloric acid was added to the solution to precipitate 4,6-dihydroxy-5-phenyl-2-methylpyrimidine. After separation of the precipitate, it was washed with distilled water and dried under vacuum at 80°C for 6 h. Phosphorus oxychloride (100 mL) was then added. Heat at 100°C for 48 h, treat the excess phosphorus oxychloride with 2 L of ice cubes, and then add dichloromethane to extract (30 mL × 3), combine the organic phase, dry with anhydrous MgSO4, filter, and finally distill under reduced pressure. The crude product was purified by column chromatography (V 乙酸乙酯 :V 石油醚 =1:2), a white crystalline solid was obtained, the product mass was 9.193g, and the yield was 48.1%. ( Figure 1 ).

[0058] By nuclear magnetic resonance spectroscopy ( 1 H NMR, 13 C NMR) was used to verify the structure of 4,6-dichloro-5-phenyl-2-methylpyrimidine. Figure 2 It can be seen from the hydrogen spectrum that the single signal peak of the compound at 2.66ppm is attributed to the hydrogen on the methyl group of the compound, the signal peak at 7.33-7.46ppm is attributed to the two hydrogens at the ortho position on the benzene ring, and the signal peak at 7.51ppm is attributed to the three hydrogens at the meta-para position on the benzene ring of the compound; Figure 3 It can be seen from the carbon spectrum that the appearance of characteristic peaks of the compound at 167.21, 160.11, 135.15, 130.25, 129.45, 129.27, 128.84, and 25.04 ppm indicates that the compound contains a benzene ring and a pyrimidine skeleton.

[0059] NMR data: 1 H NMR (400MHz, DMSO-d6) δ7.51 (ddd, J=9.9, 6.2, 3.3Hz, 3H), 7.46–7.33 (m, 2H), 2.66 (s, 1H). 13 C NMR (101MHz, DMSO-d6) δ167.21(s), 160.11(s), 135.15(s), 130.25(s), 129.45(s), 129.27(s), 128.84(s), 25.04(s).

[0060] The phenylpyrimidine compound was dissolved in a dichloromethane / n-hexane mixed solvent and slowly evaporated at low temperature to obtain the corresponding crystal. The single crystal structure of the 4,6-dichloro-5-phenyl-2-methylpyrimidine molecule was determined by X-ray single crystal diffraction ( Figure 4 ) The structural information of the molecule was determined. (Color code: C, gray; N, yellow; Cl, ​​green)

[0061] Example 2

[0062] 2.00 g of the 4,6-dichloro-5-phenyl-2-methylpyrimidine product prepared in Example 1 was added with an appropriate amount of auxiliary agents, including: 1.00 g of polyvinyl alcohol (purity Mw 9000-10000, 80% hydrolysis, produced by Shanghai McLean Biochemical Technology Co., Ltd.), a wetting agent 1.00 g of sodium dodecyl sulfate (purity 92.5-100%, produced by Shanghai McLean Biochemical Technology Co., Ltd.), a dispersant 2.00 g of sodium methylene dinaphthalene sulfonate (purity 95%, produced by Shanghai McLean Biochemical Technology Co., Ltd.) and a thickener 0.20 g of xanthan gum (USP grade, Shanghai The mixture was prepared by mixing with purified water to make it 100 mL, and then the mixture was ground repeatedly for 100 minutes in an electric lifting blue grinder (model: LZLM-3L, produced by Changzhou Lezu Machinery Technology Co., Ltd.), a water chiller (model: ZP, produced by Changzhou Lezu Machinery Technology Co., Ltd.), and a nano sand mill (model: LZNSM-0.3L, produced by Changzhou Lezu Machinery Technology Co., Ltd.). The indoor ambient temperature of all machines was maintained at 22°C, and a stable suspension of 4,6-dichloro-5-phenyl-2-methylpyrimidine with a concentration of 2% was finally formed.

[0063] Example 3

[0064] (1) Seed coating

[0065] Select the rice variety Yangxiangyu 200 with a seed germination rate of more than 90%, take 50 mL of the above-mentioned pyrimidine stable suspension seed coating agent, 2000 g of seeds, and direct-seeded rice type, and evenly coat them manually at a drug-seed ratio of 1:40 (mL:g), and then dry them for use.

[0066] (2) Field sowing

[0067] The coated seeds are sown at the normal field seed rate of 15 catties / mu.

[0068] (3) Field management

[0069] After sowing, the field management is the same as normal fields. The specific field survey data and analysis are as follows:

[0070] ① Improve the germination rate of seeds

[0071] After 5 days of germination, the germination rate of the phenylpyrimidine compound (marked as M17 in the following chart) treated as a seed dressing agent was higher than that of the control (CK1 is a dry nurse and CK2 is a blank control) both in the field and indoors. On the 10th day outdoors, the germination rate of M17 was 93.2%, exceeding the two controls of 88.1% and 86.5%, reaching a significant difference level; on the 10th day indoors, the germination rate of M17 was 97.2%, exceeding the two controls of 93.4% and 93.1%, reaching a significant difference level ( Figure 5 ).

[0072] ② Improve the seedling rate

[0073] After a complete germination cycle, the investigation showed that after the 12th and 20th days of seed germination, the germination had basically stabilized. On the 12th day in the field, the seedling rate after M17 treatment was 95.1%, which was 89.4% higher than the control, reaching a significant difference; on the 12th day in the room, the seedling rate after M17 treatment was 98.1%, which was 93.2% higher than the control, reaching a significant difference. The results showed that the seedling rate of seeds treated with M17 in the field and indoors was higher than that of the control ( Figure 6 ).

[0074] ③No effect on plant height

[0075] like Figure 7 As shown, the investigation showed that after the seeds germinated for 12 days and 20 days, the plant heights of M17 treated as seed coating agents were 14.8 cm and 21.2 cm, respectively, which were similar to the control (14.2 cm, 21.3 cm). There was no significant difference between the two, indicating that there was no effect on the agronomic trait of plant height.

[0076] ④ Promote the accumulation of dry matter in the seedling stage

[0077] Depend on Figure 8 It can be seen that the dry matter weight of the material treated with M17 as a seed dressing agent (stem and leaf dry matter weight 1.606g, root 0.375g) exceeded that of the control (stem and leaf dry matter weight 1.308g, root 0.234g), and the difference reached a significant level, indicating that the substance has the function of promoting material transport.

Claims

1. A phenylpyrimidine compound represented by formula (I), 2. Use of the phenylpyrimidine compound as claimed in claim 1 in the preparation of a rice seed coating preparation.

3. Use of the phenylpyrimidine compound of claim 1 in the preparation of a rice seed coating preparation for improving seed germination rate, seedling rate, and promoting dry matter accumulation in the seedling stage.

4. A rice seed coating agent, characterized in that: The invention is composed of the phenylpyrimidine compound according to claim 1, a film-forming agent, a wetting agent, a dispersant, a thickener and purified water, wherein the film-forming agent is polyvinyl alcohol, the wetting agent is sodium lauryl sulfate, the dispersant is sodium methylene dinaphthalene sulfonate, and the thickener is xanthan gum.

5. The rice seed coating agent according to claim 4, characterized in that: The mass ratio of the phenylpyrimidine compound, film-forming agent, wetting agent, dispersant, thickener and pure water is (2-4): (1-2): (1-3): (2-4): (0.2-0.8):

100.

6. The rice seed coating agent according to claim 4, characterized in that: The rice seed coating agent is prepared by mixing the phenylpyrimidine compound, film-forming agent, wetting agent, dispersant, thickener and purified water, and then grinding them repeatedly to finally form a phenylpyrimidine compound nano-type stable suspension with a concentration of 2-4%.

7. The method for preparing the rice seed coating agent according to any one of claims 4 to 6, characterized in that: The phenylpyrimidine compound, film-forming agent, wetting agent, dispersant, thickener and purified water are mixed and then repeatedly circulated and ground to finally form a 2-4% concentration of phenylpyrimidine compound nano-type stable suspension, which is the rice seed coating agent.

8. The preparation method according to claim 7, characterized in that: The phenylpyrimidine compound, film-forming agent, wetting agent, dispersant, thickener and purified water are mixed, and then repeatedly circulated and ground for 100-120 minutes by a grinder, a water chiller and a nano sand mill in sequence. The indoor ambient temperature of all machines is maintained at 20-25° C., and finally a phenylpyrimidine compound nano-type stable suspension with a concentration of 2-4% is formed.

9. Use of the rice seed coating agent according to any one of claims 4 to 6 in improving seed germination rate, seedling rate, and promoting dry matter accumulation in the seedling stage.

10. A method for improving seed germination rate, seedling rate, and promoting dry matter accumulation in the seedling stage, characterized in that: The rice seed coating agent according to any one of claims 4 to 6 is used to coat rice seeds with a germination rate of more than 90%, wherein the volume mass ratio of the rice seed coating agent to the rice seeds is 1:40 to 50 (mL:g), and the rice seeds are dried after coating for later use.

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