A seed coating agent containing a phenylpyrimidine compound for promoting seed germination rate and seedling rate and application thereof

Abstract

The present application relates to a kind of seed dressing containing phenyl pyrimidine compound which can promote seed germination rate and seedling rate and its application.Phenyl pyrimidine compound shown in formula (I) is made into nanoscale suspension type seed dressing after being ground by adding relevant adjuvant including film-forming agent polyvinyl alcohol, wetting agent sodium dodecyl sulfate, dispersing agent methylene bisnaphthalene sulfonic acid sodium and thickening agent xanthan gum, then water rice seed coating is carried out, can improve the germination rate and seedling rate of seed, reduce seed consumption.Core component is 4,6-dichloro-5-phenyl-2-methyl pyrimidine, and its effective mass concentration is 2-4%.The method is aimed at the problem of large seed consumption, poor emergence and uneven seedling in rice planting area in middle and lower reaches of Yangtze River such as rice mechanical sowing and direct seeding, which helps to reduce seeding rate, improve seedling rate, has the advantages of simple and convenient, saves time, can save and increase benefits.

Description

Technical Field

[0001] This invention belongs to the fields of pesticides, plant protection and cultivation, and relates to a seed coating agent of phenylpyrimidine compounds that can improve seed germination rate and seedling rate and its application. Background Technology

[0002] Machine-sown rice and direct-seeded rice are important planting methods for rice production in the middle and lower reaches of the Yangtze River, with advantages of saving labor, reducing costs and increasing efficiency. In recent years, due to factors such as tight rice-wheat intercropping schedules and labor shortages, various simplified rice and wheat cultivation methods such as machine-sown and direct-seeded rice have been widely used, but this has brought about the following problems: (1) Seed viability problem. Due to tight rice-wheat cropping schedules and labor shortages, field preparation is often inadequate, and the flatness and uniformity are weak. Seeds are in adverse environments such as temperature, moisture and soil flatness during direct-seeding or machine-sown stages, and the germination vigor of seeds often declines, resulting in insufficient basic seedlings in the early stage of the field, leading to fewer panicles in the later stage, and ultimately affecting the yield; (2) Seedling establishment rate problem. Seeds mainly rely on autotrophy from sowing to emergence. Although seeds with weak germination vigor can germinate, the emergence rate and seedling establishment rate are low, which makes it easy for seedlings to have uneven, unequal and weak seedlings, which is not conducive to unified field management and affects the quality of the crop population. The aforementioned problems severely impact high-yield and high-quality rice production, hindering the widespread application of mechanized and direct-seeded rice cultivation. In production, to ensure seed germination and seedling establishment rates, this is often addressed by increasing seed quantity. However, excessive seed quantity leads to fierce competition among seedlings for resources such as fertilizer, water, light, and temperature, resulting in small, weak, and insufficiently robust seedlings, thus affecting seedling emergence. This has a series of adverse effects on seedling emergence and mid-to-late-stage growth in both mechanized and direct-seeded rice, ultimately impacting yield and quality. Therefore, using specialized rice seed coating agents to improve germination and seedling establishment rates is a novel technical approach and measure. It increases germination and seedling establishment rates while reducing seed quantity, and this direction is currently a hot topic and focus of research on high-yield and stress-resistant rice cultivation regulation techniques.

[0003] Seed coating agents are compositions containing one or more active ingredients that play an important role in seed disinfection, slow-release fertilizers and pesticides, pest and disease control, improving crop resistance, and reducing environmental pollution. Advanced seed coating agents, processed using high-tech methods, can evenly adhere to the outer surface of the seed, forming a protective film. The pesticide is concentrated around the seed, releasing its effects slowly and is less affected by the external environment, making it difficult for surrounding pests and diseases to survive. This achieves excellent disease prevention and seedling protection without the need for other pesticides, resulting in high utilization efficiency and extended efficacy. The coated seeds have a smooth surface, which is beneficial for mechanical sowing. Furthermore, the coating agent can regulate seed size, improving the efficiency of mechanical sowing.

[0004] Upon review, there are currently no similar seed coating agent patents for improving germination and seedling survival rates. In particular, there is a lack of corresponding technologies and methods for improving seed vigor and increasing germination rates in fields with complex and variable environments, such as machine sowing and direct seeding. Summary of the Invention

[0005] The purpose of this invention is to address the aforementioned shortcomings of the prior art by providing a phenylpyrimidine compound that can improve seed germination rate and seedling survival rate.

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

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

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

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

[0010] The objective of this invention can be achieved through the following technical solutions:

[0011] The phenylpyrimidine compounds shown in formula (I),

[0012]

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

[0014]

[0015] The application of the phenylpyrimidine compounds described in this invention in the preparation of rice seed coating formulations.

[0016] The application of the phenylpyrimidine compounds described in this invention in the preparation of rice seed coating formulations that improve seed germination rate, seedling rate, and promote the accumulation of dry matter during the seedling stage.

[0017] A rice seed coating agent comprises the aforementioned phenylpyrimidine compound, a film-forming agent, a wetting agent, a dispersant, a thickener, and purified water. The film-forming agent is polyvinyl alcohol, the wetting agent is sodium dodecyl 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 purified 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 formed by repeatedly grinding a mixture of the phenylpyrimidine compound, film-forming agent, wetting agent, dispersant, thickener and purified water to form a 2-4% concentration of phenylpyrimidine compound nanoscale stable suspension.

[0020] The method for preparing the rice seed coating agent of the present invention involves mixing the phenylpyrimidine compound, film-forming agent, wetting agent, dispersant, thickener and purified water, and then repeatedly grinding them to 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 then repeatedly circulated and ground for 100-120 minutes through a grinder, a chiller and a nano-sand mill. The indoor ambient temperature for all machines is maintained at 20-25 degrees Celsius, and finally a 2-4% concentration of phenylpyrimidine compound nano-type stable suspension is formed.

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

[0023] A method for improving seed germination rate, seedling rate, and promoting the accumulation of dry matter during the seedling stage involves coating rice seeds with a germination rate of over 90% using the aforementioned rice seed coating agent. The volume-to-mass ratio of the rice seed coating agent to the rice seeds is 1:40-60 (mL:g). After coating, the seeds are dried for later use.

[0024] As a preferred embodiment of the present invention, seeds with a germination rate of over 90% are selected, dried, and then normally coated. A 2% concentration of the seed coating agent of the present invention is used. For machine-sown rice, the coating ratio is 1:50-60 (mL:g) by volume of the agent; for direct-seeded rice, the coating ratio is 1:40-50 (mL:g). Coating can be done manually or mechanically, ensuring uniform coating concentration and thickness. The coated seeds are then sown at the normal field seed rate, with other management methods the same as in the field.

[0025] Beneficial effects:

[0026] This invention designs and synthesizes phenylpyrimidine compounds with safety, high efficiency, high selectivity, and environmental friendliness through bioelectronic isosterism and active substructure splicing techniques. These compounds are then ground with the addition of relevant adjuvants to form nano-suspension seed coating agents. These agents are then used to coat rice seeds with appropriate ratios of pesticides and seeds, thereby alleviating or eliminating the technical problems of low seed germination vigor and seedling rate, improving the germination rate and seedling rate of rice seeds in the field, reducing seed usage, improving seedling quality, and achieving cost savings and efficiency gains.

[0027] The present invention has the following advantages:

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

[0029] (2) The phenylpyrimidine compound was made into a nano-type rice seed coating agent. The preparation process is simple and convenient.

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

[0031] (4) The use of this phenylpyrimidine compound can solve the problems of low seed germination rate and low seedling emergence rate under simplified cultivation with very low dosage, thereby reducing the amount of seeds used and saving seed costs.

[0032] (5) This nano-type rice seed coating agent is easy to use. It can be used immediately after coating or stored in advance without affecting the seed germination potential and germination rate in the later stage. Attached Figure Description

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

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

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

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

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

[0038] A: Photos of seed germination after coating M17 and Dry-Nurturing Nanny seeds respectively.

[0039] B: Photographs of seed germination after coating of M17 and blank control seeds.

[0040] C:M17 germination rate at different time points after seed coating.

[0041] Indoor germination rate at different time points after D:M17 was used as a seed coating agent

[0042] Figure 6 Seedling survival rate comparison of different treatments

[0043] A: Field photos of seedlings after coating of M17 seeds and the blank control.

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

[0045] C:M17, when used as a seed dressing agent, resulted in a high seed germination rate in the field.

[0046] D:M17, when used as a seed coating agent, resulted in a high indoor seed germination rate.

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

[0048] A: Plant height photo of M17 12 days after coating

[0049] B: Plant height of M17 20 days after coating

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

[0051] Figure 8 Dry matter weight per seedling

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

[0053] B: Dry weight of stems, leaves and roots after M17 coating Detailed Implementation

[0054] The main equipment involved in the following embodiments is an electric lifting basket grinder (model: LZLM-3L, manufactured by Changzhou Lezu Machinery Technology Co., Ltd.), a chiller (model: ZP, manufactured by Changzhou Lezu Machinery Technology Co., Ltd.), and a nano sand mill (model: LZNSM-0.3L, manufactured by Changzhou Lezu Machinery Technology Co., Ltd.). In actual production, it is not limited to the above-mentioned equipment. It 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 using metallic sodium (3.586 g, 0.156 mol) and purified anhydrous ethanol (200 mL). Ethamidinium hydrochloride (7.650 g, 0.0809 mol) and diethyl phenylmalonate (18.910 g, 0.0800 mol) were added, and the mixture was 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 dissolved in 1 L of distilled water, and concentrated hydrochloric acid was added to precipitate 4,6-dihydroxy-5-phenyl-2-methylpyrimidine. The precipitate was separated, washed with distilled water, and dried under vacuum at 80 °C for 6 h. Phosphorus oxychloride (100 mL) was then added. The mixture was heated at 100 °C for 48 h, and excess phosphorus oxychloride was treated with 2 L of ice. Dichloromethane was then added for extraction (30 mL × 3). The organic phase was combined, dried over anhydrous MgSO4, filtered, and finally distilled under reduced pressure. The crude product was purified by column chromatography (V... 乙酸乙酯 :V 石油醚 =1:2), yielding a white crystalline solid with a product weight of 9.193 g and a yield of 48.1%. Figure 1 ).

[0058] Through nuclear magnetic resonance spectroscopy ( 1 H NMR, 13 The structure of 4,6-dichloro-5-phenyl-2-methylpyrimidine was verified by C10 NMR. Figure 2 The 1H NMR spectrum shows that the singlet signal peak at 2.66 ppm is attributed to the hydrogen atom on the methyl group, the signal peaks at 7.33-7.46 ppm are attributed to the two adjacent hydrogen atoms on the benzene ring, and the signal peak at 7.51 ppm is attributed to the three meta- and para-position hydrogen atoms on the benzene ring. Figure 3 The carbon spectrum shows that the compound contains characteristic peaks at 167.21, 160.11, 135.15, 130.25, 129.45, 129.27, 128.84, and 25.04 ppm, indicating the presence of a benzene ring and a pyrimidine skeleton in the compound.

[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 crystals. 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 molecular structure information has been determined. (Color codes: C, gray; N, yellow; Cl, ​​green)

[0061] Example 2

[0062] Add 2.00g of the 4,6-dichloro-5-phenyl-2-methylpyrimidine product prepared in Example 1 to an appropriate amount of additives, including: 1.00g of polyvinyl alcohol (purity Mw9000-10000, 80% hydrolyzed, produced by Shanghai Maclean Biochemical Technology Co., Ltd.) as a film-forming agent, 1.00g of sodium dodecyl sulfate (purity 92.5-100%, produced by Shanghai Maclean Biochemical Technology Co., Ltd.) as a wetting agent, 2.00g of sodium methylene dinaphthalene sulfonate (purity 95%, produced by Shanghai Maclean Biochemical Technology Co., Ltd.) as a dispersant, and 0.20g of xanthan gum (USP grade, above...) as a thickener. The mixture was produced by Haimaclin Biochemical Technology Co., Ltd. Finally, purified water was added to 100mL. The mixture was then repeatedly circulated and ground for 100 minutes in sequence using an electric lifting basket mill (model: LZLM-3L, produced by Changzhou Lezu Machinery Technology Co., Ltd.), a 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 ambient temperature of all machines was maintained at 22℃, ultimately forming a stable suspension of 4,6-dichloro-5-phenyl-2-methylpyrimidine with a concentration of 2%.

[0063] Example 3

[0064] (1) Seed coating

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

[0066] (2) Field sowing

[0067] After coating, the seeds are sown at the normal field seed rate of 15 catties / mu.

[0068] (3) Field management

[0069] Post-sowing field management is the same as for normal fields. Specific field survey data and analysis are as follows:

[0070] ① Improve seed germination rate

[0071] Five days after germination, the phenylpyrimidine compound (marked as M17 in the following chart) used as a seed dressing agent showed higher germination rates than the controls (CK1 was a dry-land nursery and CK2 was a blank control) in both the field and indoors. Outdoors, on day 10, the germination rate of M17 treatment was 93.2%, exceeding the two controls' 88.1% and 86.5%, respectively, reaching a significant difference. Indoors, on day 10, the germination rate of M17 treatment was 97.2%, exceeding the two controls' 93.4% and 93.1%, respectively, reaching a significant difference. Figure 5 ).

[0072] ② Improve seedling survival rate

[0073] After a complete germination cycle, the survey showed that germination had basically stabilized on days 12 and 20. In the field, the seedling emergence rate after M17 treatment was 95.1% on day 12, exceeding the control's 89.4% (significant difference). In the indoor environment, the seedling emergence rate after M17 treatment was 98.1% on day 12, exceeding the control's 93.2% (significant difference). These results indicate that the seedling emergence rate after M17 treatment was higher than the control in both the field and indoor environments. Figure 6 ).

[0074] ③ No effect on plant height

[0075] like Figure 7 As shown, the survey indicated that on the 12th and 20th day after seed germination, the plant heights of plants treated with M17 as a seed dressing agent were 14.8 cm and 21.2 cm, respectively, which were similar to the control (14.2 cm and 21.3 cm). There was no significant difference between the two, indicating that it had no effect on the agronomic trait of plant height.

[0076] ④ Promote the accumulation of dry matter weight in seeds and seedlings.

[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 (1.606 g for stems and leaves and 0.375 g for roots) exceeded that of the control (1.308 g for stems and leaves and 0.234 g for roots), and the difference was significant, indicating that the substance has the function of promoting substance translocation.

Claims

1. The application of the phenylpyrimidine compounds shown in formula (I) in the preparation of rice seed coating formulations, .

2. The application according to claim 1, characterized in that, The application of the phenylpyrimidine compound of formula (I) as described in claim 1 in the preparation of rice seed coating formulations that improve seed germination rate, seedling rate and promote the accumulation of dry matter during the seedling stage.

3. The application of rice seed coating agents containing phenylpyrimidine compounds of formula (I) in improving seed germination rate, seedling rate, and promoting the accumulation of dry matter during the seedling stage, characterized in that, The rice seed coating agent is composed of a phenylpyrimidine compound as shown in formula (I), a film-forming agent, a wetting agent, a dispersant, a thickener, and purified water. The film-forming agent is polyvinyl alcohol, the wetting agent is sodium dodecyl sulfate, the dispersant is sodium methylene dinaphthalene sulfonate, and the thickener is xanthan gum. The structure of the phenylpyrimidine compound as shown in formula (I) is as follows: .

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

100.

5. The application according to claim 3, characterized in that, The rice seed coating agent is made by mixing the phenylpyrimidine compound, film-forming agent, wetting agent, dispersant, thickener and purified water, and then repeatedly grinding them to form a 2-4% concentration of phenylpyrimidine compound nano-sized stable suspension.

6. A method for improving seed germination rate, seedling survival rate, and promoting the accumulation of dry matter during the seedling stage, characterized in that, Rice seeds with a germination rate of over 90% are coated with a rice seed coating agent. The volume-to-mass ratio of the rice seed coating agent to the rice seeds is 1:40-50 (mL:g). After coating, the seeds are dried for later use. The rice seed coating agent consists of a phenylpyrimidine compound as shown in formula (I), a film-forming agent, a wetting agent, a dispersant, a thickener, and purified water. The film-forming agent is polyvinyl alcohol, the wetting agent is sodium dodecyl sulfate, the dispersant is sodium methylene dinaphthalene sulfonate, and the thickener is xanthan gum. The structure of the phenylpyrimidine compound as shown in formula (I) is as follows: .

Images