1-(3-chlorphenyl)-3-(2-chloropyridine-4-yl) urea as well as preparation method and application thereof
By splicing 2,4-dichloropyridine and 3-chlorophenylurea to prepare 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea, the phytotoxicity problem caused by chlorpyrifos was solved, achieving more efficient crop yield increase and safety, and it is suitable for growth regulation of fruits, vegetables and grain crops.
Patent Information
- Application Number
- CN202511747372.5
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-11-26
- Publication Date
- 2026-02-24
AI Technical Summary
Existing plant growth regulators, such as chlorpyrifos, can easily cause phytotoxicity problems such as protruding fruit blossom ends, cracked fruit, and deformed fruit when used improperly, affecting the quality of agricultural products and consumer safety. Moreover, it is difficult to avoid side effects while promoting fruit setting and increasing yield.
Using the principle of active substructure splicing, 2,4-dichloropyridine and 3-chlorophenylurea were spliced to prepare 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea. The target product was generated by interfacial reaction with water as solvent and the reaction conditions were controlled, thereby enhancing the molecular polarity and lipophilicity.
It increases crop yield, enhances stress resistance, reduces pesticide damage such as fruit cracking and fruit blossom end protrusion, exhibits higher safety and efficiency, and promotes fruit expansion and nutrient absorption in target crops.
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Figure CN121554415A_ABST
Abstract
Description
Technical Field
[0001] This invention relates to the field of plant chemical control technology, specifically to a 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea, its preparation method, and its application. Background Technology
[0002] Chlorpyrifos (also known as chlorpyrifos, KT-30) is a phenylurea plant growth regulator with cytokinin activity, its biological activity being 10-100 times higher than that of 6-benzylaminopurine. This agent is widely used in fruit trees, vegetables, grain crops, and medicinal herbs, promoting cell division and elongation, enhancing photosynthesis, promoting the absorption and utilization of water and fertilizer by plants, and regulating the directional transport of nutrients, thereby achieving multiple agronomic effects such as promoting fruit enlargement, increasing crop yield, and improving preservation.
[0003] With the improvement of people's living standards, the market demand for fresh fruits and vegetables continues to grow, and the fruit and vegetable industry has played an important role. To improve the yield and quality of fruits and vegetables, agricultural production often involves applying hormones or similar active substances to the leaves or soil to promote cell growth, enhance the absorption of elements such as nitrogen, phosphorus, and zinc, thereby regulating plant growth and development, increasing fruit set rate, and enhancing crop resistance. Against this backdrop, various compounds with plant growth regulating functions are constantly being developed and put into application.
[0004] However, with the widespread use of plant growth regulators, the quality and safety issues of related agricultural products have become increasingly prominent, seriously affecting the improvement of agricultural quality and efficiency and the healthy development of the industry. Taking chlorpyrifos as an example, as an exogenous phenylurea regulator, it is effective in improving fruit setting rate and increasing fruit size. However, if the concentration, timing, or method of application is incorrect, it can easily lead to phytotoxicity in sensitive crops, such as protruding fruit blossom ends, fruit cracking, and deformities. This not only affects the marketability and economic benefits of the product but also poses consumer safety risks.
[0005] Therefore, there is an urgent need in current agricultural production for an improved plant growth regulator that can effectively avoid side effects such as fruit cracking and deformity while ensuring the promotion of fruit setting and increased yield, so as to meet the market's demand for safe and high-quality fruits and vegetables and promote high-quality and sustainable agricultural development. Summary of the Invention
[0006] To address the aforementioned technical problems, this invention employs the principle of active substructure splicing to effectively splice 2,4-dichloropyridine and 3-chlorophenylurea, thereby obtaining a novel compound with plant growth regulating activity. This compound can increase crop yield and enhance stress resistance, and is safe and effectively prevents phytotoxic deformities such as fruit cracking and protruding fruit blossom ends.
[0007] To achieve the above objectives, the technical solution of the present invention is implemented as follows: A 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea, with the structural formula shown in Formula I: .
[0008] Preferably, the method for preparing the 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea includes the following steps: (1) Add 2,4-dichloropyridine, 3-chlorophenylurea, catalyst and water to the reactor, heat and stir to mix evenly, add sodium carbonate, and continue to heat and stir to react; (2) After the reaction in step (1) is completed, the mixture is cooled, filtered, washed and dried to obtain 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea as shown in Formula I; The reaction equation is shown below: .
[0009] Reaction Mechanism: The -NH-CO-NH2 group in 3-chlorophenylurea undergoes an initial reaction (60℃, 3h) and, under catalytic conditions, initially undergoes nucleophilic aromatic substitution with 2,4-dichloropyridine in water. Water serves as the solvent, providing the reaction medium. The temperature of 60℃ aims to activate the reactants while avoiding excessive hydrolysis.
[0010] Reaction: The nitrogen atom of 3-chlorophenylurea attacks the chlorine atom at position 4 of 2,4-dichloropyridine, generating the target compound of formula I and releasing HCl. The reaction formula is as follows: ; As the reaction proceeds, the solution becomes acidic. To prevent hydrolysis, sodium carbonate is added in batches at this point to provide a stable and continuous alkaline reaction environment, neutralize the byproduct hydrochloric acid, promote the reaction to the right, and enhance the activity of the nucleophile (deprotonation). Heating to 85°C accelerates the completion of the reaction.
[0011] Post-processing removes byproducts (such as inorganic salts) and residual reagents, purifying the product. Washing with saturated sodium bicarbonate solution ensures neutralization of any residual acid and dissolves water-soluble impurities. The solid product is separated by vacuum filtration and dried to remove moisture.
[0012] Preferably, in step (1), the molar ratio of 2,4-dichloropyridine, 3-chlorophenylurea and sodium carbonate is 1-1.2:1:1.2-1.6, and the concentration of 2,4-dichloropyridine in the reaction system is 0.12-0.25 mmol / mL.
[0013] Preferably, the temperature for heating and stirring to achieve uniform mixing in step (1) is 55-65℃, and the time is 2-5h.
[0014] Preferably, in step (1), sodium carbonate is added in 2-3 batches, with an interval of 12-17 minutes between the two batches.
[0015] Preferably, in step (1), the temperature of heating and stirring after adding sodium carbonate is 80-100℃, and the reaction time is 2-5h.
[0016] Preferably, the catalyst in step (1) is one or a combination of polyethylene glycol PEG200, tetrabutylammonium bromide, tetrabutylammonium chloride, tetramethylammonium bromide and benzyltriethylammonium chloride; the molar amount of the catalyst is 1wt% to 5wt% of the raw material 2,4-dichloropyridine.
[0017] The cooling temperature in step (2) is room temperature (10-40℃).
[0018] Preferably, in step (2), the washing is performed using a saturated sodium bicarbonate solution, and the solution is washed 1-2 times until neutral.
[0019] Preferably, the application of 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea in increasing the yield of fruit and vegetable crops includes kiwifruit, watermelon, cantaloupe, cucumber, tomato, pepper, eggplant, navel orange, tangerine, pear, apple and lychee.
[0020] Preferably, the application of 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea in enhancing the fertilizer efficiency of grain crops, wherein the grain crops include rice, wheat, soybean, peanut and potato; wherein the 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea promotes the absorption and utilization of nitrogen fertilizer, phosphorus fertilizer and zinc fertilizer by the grain crops.
[0021] The beneficial effects of this invention are: 1. This invention provides a method for preparing 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea with plant growth regulating activity. The method uses water as a solvent and cleverly utilizes interfacial reaction to obtain the target product. The reaction conditions are mild and the product yield is high. 2. Compared to existing chlorpyrifos, the regulator prepared in this invention introduces an electron-withdrawing Cl at the 3-position of the benzene ring, which enhances the polarity or lipophilicity of the molecule. Moderate lipophilicity helps the compound penetrate biological membranes (such as plant cell membranes), resulting in better rapid action. Compared to existing chlorpyrifos, at the same application rate, it exhibits lower fruit cracking rates, significant fruit expansion effects, and higher yields in target crops such as apples and pears, while demonstrating higher safety. 3. The 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea of the present invention has the effect of promoting the absorption and utilization of nutrients such as nitrogen, phosphorus, potassium and zinc in rice, wheat, soybean, peanut and potato crops. It can be used as an effective ingredient of fertilizer synergist, thereby achieving the effect of increasing yield and income. Detailed Implementation
[0022] The technical solutions in the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those of ordinary skill in the art without creative effort are within the scope of protection of the present invention. Example 1
[0023] This embodiment prepares a 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea. The preparation steps are as follows: In a reaction flask equipped with a stirrer and thermometer, 10 mmol of 2,4-dichloropyridine, 10 mmol of 3-chlorophenylurea, 0.1 mmol of polyethylene glycol PEG200, and 80 ml of water were added. The mixture was heated to 60 °C and stirred for 3 h. Then, 15 mmol of sodium carbonate powder was added in three batches (15 min apart), and the temperature was raised to 85 °C and reacted for 3 h. After the reaction was completed, the mixture was cooled to room temperature, washed twice with saturated sodium bicarbonate solution, filtered directly, and dried at room temperature to obtain compound I with a yield of 98%. The mechanism of aqueous phase catalysis by PEG200 is as follows: PEG200 has good water solubility and can form a homogeneous mixed solvent with water, reducing the surface tension of the reactants 2,4-dichloropyridine and 3-chlorophenylurea. As a co-solvent, PEG200 can improve the solubility of the reactants, making them easier to disperse and contact, thereby promoting the reaction. The molecular structure of PEG200 consists of numerous repeating -O-CH2-CH2- units. In aqueous catalysis, its steric hindrance effect hinders the aggregation of reaction intermediates or products, stabilizes intermediates, and prevents side reactions. The oxygen atom on its ether bond possesses a lone pair of electrons, which can form stable complexes with cations in the aqueous phase, especially with Na+. The long chain of PEG itself is an organophile. This "PEG-Na+-nucleophilic anion" complex acts like a "small boat," transporting the nucleophile from the aqueous phase to the organic phase (i.e., the oil droplet or solid surface containing 2,4-dichloropyridine), thereby catalyzing and promoting the reaction.
[0024] Compound I molecular formula: C 12 H9Cl2N3O
[0025] Mass spectrometry analysis revealed the following elemental composition (%) of this compound: Calculated values: C, 51.09; H, 3.22; N, 14.89; Measured values: C, 51.11; H, 3.20; N, 14.94. The NMR results were as follows: 1H NMR (500MHz, DMSO-d): 9.27(s, 1H, NH), 9.17(s, 1H, NH), 8.12(d, 1H, CH), 7.90(s, 1H, CH), 7.90(s, 1H, CH), 7.46(d, 1H, CH), 7.39(m, 1H, CH), 7.16(d, 1H, CH), 6.81(d, 1H, CH), 6.67(d, 1H, CH).
[0026] The successful preparation of the target product 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea was demonstrated. Example 2
[0027] This embodiment prepares a 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea. The preparation steps are as follows: In a reaction flask equipped with a stirrer and thermometer, 10 mmol of 2,4-dichloropyridine, 10 mmol of 3-chlorophenylurea, 0.1 mmol of tetrabutylammonium bromide and 80 ml of water were added. The mixture was heated to 60 °C and stirred for 5 h. Then, 12 mmol of sodium carbonate powder was added in three batches (12 min apart). The temperature was raised to 85 °C and the mixture was reacted for 5 h. After the reaction was completed, the mixture was cooled to room temperature, washed twice with water in a saturated sodium bicarbonate solution, filtered directly, and dried at 60 °C to obtain compound I with a yield of 98%. Example 3
[0028] This embodiment prepares a 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea. The preparation steps are as follows: In a reaction flask equipped with a stirrer and thermometer, 10 mmol of 2,4-dichloropyridine, 10 mmol of 3-chlorophenylurea, 0.1 mmol of tetramethylammonium bromide and 80 ml of water were added. The mixture was heated to 60 °C and stirred for 5 h. Then, 16 mmol of sodium carbonate powder was added in three batches, and the temperature was raised to 85 °C and reacted for 3 h. After the reaction was completed, the mixture was cooled to room temperature, washed twice with water in a saturated sodium bicarbonate solution, filtered directly, and dried to obtain compound I with a yield of 98%. Example 4
[0029] This embodiment prepares a 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea. The preparation steps are as follows: In a reaction flask equipped with a stirrer and thermometer, 10 mmol of 2,4-dichloropyridine, 10 mmol of 3-chlorophenylurea, 0.1 mmol of benzyltriethylammonium chloride and 80 ml of water were added. The mixture was heated to 60 °C and stirred for 2.5 h. Then, 15 mmol of sodium carbonate powder was added in three batches (with an interval of 15 min between each batch). The temperature was raised to 85 °C and the mixture was reacted for 3 h. After the reaction was completed, the mixture was cooled to room temperature, washed twice with water in a saturated sodium bicarbonate solution, filtered directly, and dried to obtain compound I with a yield of 97%. Example 5
[0030] This embodiment prepares a 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea. The preparation steps are as follows: In a reaction flask equipped with a stirrer and thermometer, 10 mmol of 2,4-dichloropyridine, 10 mmol of 3-chlorophenylurea, 0.5 mmol of tetrabutylammonium bromide and 80 ml of water were added. The mixture was heated to 60 °C and stirred for 5 h. Then, 15 mmol of sodium carbonate powder was added in three batches (15 min apart). The temperature was raised to 85 °C and the mixture was reacted for 2.5 h. After the reaction was completed, the mixture was cooled to room temperature, washed twice with water in a saturated sodium bicarbonate solution, filtered directly, and dried to obtain compound I with a yield of 97%. Example 6
[0031] This embodiment prepares a 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea. The preparation steps are as follows: In a reaction flask equipped with a stirrer and thermometer, 10 mmol of 2,4-dichloropyridine, 10 mmol of 3-chlorophenylurea, 0.3 mmol of tetrabutylammonium bromide and 80 ml of water were added. The mixture was heated to 50 °C and stirred for 5 h. Then, 12 mmol of sodium carbonate powder was added in two batches (17 min apart). The temperature was raised to 90 °C and the mixture was reacted for 5 h. After the reaction was completed, the mixture was cooled to room temperature, washed twice with water in a saturated sodium bicarbonate solution, filtered directly, and dried to obtain compound I with a yield of 95%. Example 7
[0032] This embodiment prepares a 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea. The preparation steps are as follows: In a reaction flask equipped with a stirrer and thermometer, 10 mmol of 2,4-dichloropyridine, 10 mmol of 3-chlorophenylurea, 0.4 mmol of benzyltriethylammonium chloride and 80 ml of water were added. The mixture was heated to 85 °C and stirred for 3 h. Then, 15 mmol of sodium carbonate powder was added in three batches (15 min apart) and reacted at 85 °C for 3 h. After the reaction was completed, the mixture was cooled to room temperature, washed twice with water in a saturated sodium bicarbonate solution, filtered directly, and dried at 45 °C to obtain compound I with a yield of 95%. Example 8
[0033] This embodiment prepares a 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea. The preparation steps are as follows: In a reaction flask equipped with a stirrer and thermometer, 10 mmol of 2,4-dichloropyridine, 10 mmol of 3-chlorophenylurea, 0.1 mmol of tetrabutylammonium bromide, 0.1 mmol of benzyltriethylammonium chloride, 0.3 mmol of polyethylene glycol, and 80 ml of water were added. The mixture was heated to 85 °C and stirred for 3 h. Then, 15 mmol of sodium carbonate powder was added in three batches (15 min apart), and the mixture was reacted at 90 °C for 3 h. After the reaction was completed, the mixture was cooled to room temperature, washed twice with water in a saturated sodium bicarbonate solution, filtered directly, and dried to obtain compound I with a yield of 95%. Example 9
[0034] This embodiment prepares a 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea. The preparation steps are as follows: In a reaction flask equipped with a stirrer and thermometer, 10 mmol of 2,4-dichloropyridine, 10 mmol of 3-chlorophenylurea, 0.1 mmol of tetrabutylammonium bromide, 0.1 mmol of benzyltriethylammonium chloride, 0.3 mmol of polyethylene glycol, and 80 ml of water were added. The mixture was heated to 85 °C and stirred for 3 h. Then, 15 mmol of sodium carbonate powder was added in three batches (15 min apart), and the mixture was reacted at 100 °C for 2 h. After the reaction was completed, the mixture was cooled to room temperature, washed twice with water in a saturated sodium bicarbonate solution, filtered directly, and dried to obtain compound I with a yield of 97%. Example 10
[0035] This embodiment prepares a 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea. The preparation steps are as follows: In a reaction flask equipped with a stirrer and thermometer, 10 mmol of 2,4-dichloropyridine, 10 mmol of 3-chlorophenylurea, 0.1 mmol of benzyltriethylammonium chloride and 80 ml of water were added. The mixture was heated to 60 °C and stirred for 2.5 h. Then, 15 mmol of sodium carbonate powder was added in three batches (with an interval of 15 min between each batch). The temperature was raised to 80 °C and the mixture was reacted for 5 h. After the reaction was completed, the mixture was cooled to room temperature, washed twice with water in a saturated sodium bicarbonate solution, filtered directly, and dried to obtain compound I with a yield of 95%. Application Example 1: Fruit Enlargement and Safety Test
[0036] To evaluate the effects of different concentrations of 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea on fruit expansion and safety (fruit cracking rate, single fruit weight, yield) of crops, and to determine the safe and effective application concentration for each crop, a fruit expansion and safety experiment of 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea was conducted. (1) Test target and test conditions
[0037] The following 12 target crops were used in this experiment: Kiwifruit: Golden Red 50 Navel orange: Fukumoto Mandarin Orange: See You Tomorrow Pear: Laiyang Pear Apple: Fuji Lychee: Concubine's Smile Watermelon: 8424 Melon: Honeydew Melon Cucumber: Xinjin Research No. 4 Tomatoes: Provence Chili peppers: Multicolor bell peppers Eggplant: Black and large This experiment targeted a wide variety of crops, so tests were conducted in different locations: kiwifruit, navel oranges, and tangerines were tested in Ya'an City, Sichuan Province; apples and pears were tested in Yantai City, Shandong Province; lychees were tested in Maoming City, Guangdong Province; and watermelons, cantaloupes, cucumbers, tomatoes, peppers, and eggplants were tested in Zhengzhou City, Henan Province. (2) Instruments and equipment and test concentration
[0038] Experimental instruments and materials: sprayer, electronic balance, beaker, graduated cylinder, labels, notebook Test concentrations: Three test concentrations were set for test product compound I, namely 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea, namely 10 mg / L, 20 mg / L and 30 mg / L; Using chlorpyrifos as a positive control, the same experimental concentration was set to compare the experimental results. (3) Test methods and activity evaluation
[0039] Preparation of drug solution: Weigh 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea technical and chlorpyrifos technical, dilute with a small amount of distilled water to the target concentration (10 mg / L, 20 mg / L and 30 mg / L), and stir evenly.
[0040] Spraying: Spraying should be carried out on windless, sunny mornings (8:00-10:00) or evenings (16:00-18:00); select plots with consistent growth status for spraying treatment, with each treatment covering 1 acre, and divide it into 3 evenly distributed plots. Since the planting, growth and maturity stages of crops are different, spraying should be carried out in the early stage of crop enlargement.
[0041] Crop management: During the fruit expansion period, record crop growth, count the number of fruits set and the number of cracked fruits, and manage water and fertilizer properly.
[0042] Sample collection: Samples were collected when the experimental fruits reached the appropriate maturity for picking. Fifty fruits were randomly picked from each tree for different treatment groups. The weight of a single fruit, the number of fruits, the number of cracked fruits, and the yield per acre for each treatment were measured and recorded. The data were compiled and summarized, and the experimental data are expressed as average values.
[0043] The test results are shown in Table 1-4 below.
[0044] Table 1. Effects of Compound I on the yield of the target fruit crop.
[0045] Table 2. Effects of Compound I on the yield of the target fruit crop.
[0046] Table 3. Effects of Compound I on the yield of target cucurbit vegetables.
[0047] Table 4. Effects of Compound I on the yield of the target vegetable crop.
[0048] This invention uses Compound I prepared in Example 1 to conduct experiments on different target crops at various treatment concentrations. The results are shown in Tables 1-4. As can be seen from Tables 1-4, with the increase of Compound I and chlorpyrifos dosage, the fruit cracking rate of target fruits and vegetables significantly increased, the yield increased, and the average single fruit weight increased. Compared with the chlorpyrifos control agent, Compound I prepared in this invention has a lower fruit cracking rate and a higher yield per acre at the same dosage. In summary, Compound I, as a novel compound with plant growth regulating activity, has a fruit expansion effect on kiwifruit, watermelon, cucumber, tomato, pepper, eggplant, navel orange, mandarin orange, pear, apple, and lychee and is safe without fruit cracking damage, indicating that Compound I of this invention exhibits higher application safety. Application Example 2: Fertilizer Synergy Trial
[0049] To further verify the actual effect of compound I provided by this invention on improving crop fertilizer absorption and utilization, this invention adopts the method of indoor bioassay + field experiment, and combines different application methods such as basal application, foliar spraying, drip irrigation, fertigation and hydroponics to make actual experimental effect evaluation. Test target food crops:
[0050] Wheat, soybeans, peanuts, potatoes Experimental Example 1: Effect of Compound I prepared in this invention on wheat fertilizer absorption and utilization (fertigation) Experimental crop: wheat; Test location: Weihui County, Xinxiang, Henan Province; Experimental treatment: For basal application, 19-19-19 compound fertilizer was selected. Simultaneously, during the wheat jointing stage, 20 kg of compound fertilizer (19-19-19) per mu was applied as topdressing, along with 50 g of zinc sulfate and different amounts of Compound I prepared in Example 1, applied via fertigation. Chlorophyll content was measured 7 days after application. Leaves from the peak growth period were also collected and sent to the Henan Academy of Agricultural Sciences for testing to determine the content of nitrogen, phosphorus, potassium, zinc, and other elements.
[0051] The experimental design for the test reagents is shown in Table 5: Table 5:
[0052] The experimental results are shown in Table 6: (1) Table 6: Effects of each treatment on wheat chlorophyll content and leaf nitrogen, phosphorus, potassium and zinc content;
[0053]
[0054] Table 6 shows that applying compound I of this invention as a fertilizer synergist to wheat significantly promotes the chlorophyll content in wheat leaves. Nitrogen absorption rate increases with fluctuations, then decreases with fluctuations, with an increase rate of 2-19.5%. Phosphorus absorption rate increases with fluctuations and then decreases, with an increase rate of 4-26%. Potassium absorption rate increases with fluctuations, with a potassium absorption promotion rate of 0.4-7.7%. Zinc absorption rate increases by 38.3-51.6%. In summary, an application rate of 20-60 g / mu can significantly increase the content of nitrogen, phosphorus, potassium, zinc, and chlorophyll in wheat leaves.
[0055] Experimental Example 2: Effect of Compound I prepared in this invention on the absorption and utilization of peanut fertilizer (foliar spraying) Experimental crop: peanut; Test location: Weihui County, Xinxiang, Henan Province; Experimental treatment: Using 0.5% urea + 0.5% potassium dihydrogen phosphate + 0.1% boron + 0.005% ammonium molybdate as the base fertilizer, and compound I prepared in Example 4 at different concentrations, the mixture was sprayed on the leaves at the initial flowering stage. Seven days after the treatment, the chlorophyll content was measured, the number of peanut peggings was recorded, and functional leaves during the peak growth period were collected and sent to the Henan Academy of Agricultural Sciences for testing to determine the nitrogen, phosphorus, potassium, boron, and molybdenum contents.
[0056] The experimental design for the test reagents is shown in Table 7: Table 7:
[0057] The experimental results are shown in Table 8: (1) Table 8: Effects of each treatment on nitrogen, phosphorus, potassium, boron and molybdenum in peanut leaves, as well as chlorophyll content and number of peggings in peanut leaves;
[0058]
[0059] In this invention, compound I prepared in Example 4 was used to conduct spraying experiments on various treatment groups at different concentrations. The results in Table 8 show that compound I, as a fertilizer enhancer, not only promoted the chlorophyll content of peanuts to varying degrees, but also promoted early pegging of peanuts, thus promoting increased yield in the later stages of peanut production. In addition, the investigation on the absorption and utilization of nitrogen, phosphorus, potassium, boron, and molybdenum in peanut leaves showed that compound I could significantly increase the content of nitrogen, phosphorus, potassium, boron, and molybdenum in peanut leaves during the peak growth period. The increase in the content of these elements is beneficial to promoting early and abundant pegging of peanuts and providing a nutritional basis for increased yield in the later stages. The best absorption and promotion rate of fertilizer effect in peanuts was achieved when the application rate was 40-60 g / mu.
[0060] Experimental Example 3: Effect of Compound I prepared in this invention on the absorption and utilization of soybean fertilizer (fertigation) Experimental crop: soybean; Test location: Weihui County, Xinxiang, Henan Province; Experimental treatment: For basal application, 19-19-19 compound fertilizer was selected. Simultaneously, during the soybean flowering period, 15 kg of compound fertilizer (19-19-19) per mu (approximately 0.067 hectares) was applied as topdressing, along with 20 kg of zinc sulfate and compounds prepared in different concentrations as described in Example 1, applied via fertigation. Chlorophyll content was measured 7 days after application, and leaves were collected and sent to the Henan Academy of Agricultural Sciences for testing to determine the content of nitrogen, phosphorus, potassium, zinc, and other elements.
[0061] The experimental design for the test reagents is shown in Table 9: Table 9:
[0062] The experimental results are shown in Table 10: (1) Table 10: Effects of each treatment on the chlorophyll content and the content of nitrogen, phosphorus, potassium and zinc in soybean leaves;
[0063]
[0064] As shown in Table 10, the application of Compound I of this invention as a fertilizer enhancer significantly increased the content of nitrogen, phosphorus, potassium, zinc, and chlorophyll in soybean leaves. With increasing application rate of Compound I per acre, the chlorophyll content in soybean leaves continued to increase. However, the content of nitrogen, phosphorus, potassium, and zinc in soybean leaves initially increased and then decreased. The optimal overall fertilizer effect was achieved with an application rate of 60g per acre; further increases in application rate resulted in a decrease in the tested nutrient levels.
[0065] Experimental Example 4: Effect of Compound I prepared in this invention on potato fertilizer absorption and utilization (foliar spraying) Experimental crop: Potato; Test location: Weihui County, Xinxiang, Henan Province; Experimental treatment: Using 0.5% urea + 0.5% potassium dihydrogen phosphate + 0.1% boron + 0.005% ammonium molybdate as the base fertilizer, compound I prepared in Example 4 at different concentrations was applied as a foliar spray during the vegetative growth stage. The chlorophyll content was measured 7 days after application, and leaves from the peak growth stage were collected and sent to the Henan Academy of Agricultural Sciences for testing to determine the nitrogen, phosphorus, potassium, boron, and molybdenum contents.
[0066] The experimental design for the test reagents is shown in Table 11: Table 11:
[0067] The experimental results are shown in Table 12: (1) Table 12: Effects of each treatment on nitrogen, phosphorus, potassium, boron and molybdenum in potato leaves and chlorophyll content in peanut leaves;
[0068]
[0069] This invention uses compound I prepared in Example 4 to conduct spraying experiments on potatoes at various treatment concentrations. The results in Table 13 show that compound I, as a fertilizer synergist, not only promotes the chlorophyll content of potatoes to varying degrees, but also promotes the increase of potato yield in the later stages. In addition, it shows that compound I has a significant promoting effect on the content of nitrogen, phosphorus, potassium, boron and molybdenum in potato leaves. The increase of the content of the above elements reaches the optimal level when the application rate is 40-60 g / mu. These elements provide the nutritional basis for the increase of potato yield in the later stages.
[0070] The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the protection scope of the present invention.
Claims
1. A 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea, characterized in that, It has the structure shown in Equation I: 。 2. The method for preparing 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea according to claim 1, characterized in that: Includes the following steps: (1) Add 2,4-dichloropyridine, 3-chlorophenylurea, catalyst and water to the reactor, heat and stir to mix evenly, add sodium carbonate, and continue to heat and stir to react; (2) After the reaction in step (1) is completed, the mixture is cooled, filtered, washed and dried to obtain 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea as shown in Formula I; The reaction equation is shown below: 。 3. The method for preparing 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea according to claim 2, characterized in that: In step (1), the molar ratio of 2,4-dichloropyridine, 3-chlorophenylurea and sodium carbonate is 1-1.2:1:1.2-1.6, the concentration of 2,4-dichloropyridine in the reaction system is 0.12-0.25 mmol / mL, and the amount of catalyst is 1 wt% to 5 wt% of 2,4-dichloropyridine.
4. The method for preparing 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea according to claim 2, characterized in that: In step (1), the temperature for heating and stirring to achieve uniform mixing is 55-65℃, and the time is 2-5h.
5. The method for preparing 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea according to claim 2, characterized in that: In step (1), sodium carbonate is added in 2-3 batches, with an interval of 12-17 minutes between the two batches.
6. The method for preparing 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea according to claim 2, characterized in that: In step (1), after adding sodium carbonate, the temperature of the heating and stirring reaction is 80-100℃, and the reaction time is 2-5h.
7. The method for preparing 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea according to claim 2, characterized in that: The catalyst in step (2) is one or a combination of polyethylene glycol PEG200, tetrabutylammonium bromide, tetrabutylammonium chloride, tetramethylammonium bromide and benzyltriethylammonium chloride.
8. The method for preparing 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea according to claim 2, characterized in that: In step (2), the washing is performed using a saturated sodium bicarbonate solution, and the solution is washed 1-2 times until neutral.
9. The application of 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea according to claim 1 in increasing fruit yield in fruit and vegetable crops, characterized in that: The fruits and vegetables used in this application include kiwifruit, watermelon, cantaloupe, cucumber, tomato, pepper, eggplant, navel orange, tangerine, pear, apple, and lychee.
10. The application of 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea according to claim 1 in enhancing the fertilizer efficacy of grain crops, characterized in that: The grain crops include rice, wheat, soybeans, peanuts, and potatoes; the 1-(3-chlorophenyl)-3-(2-chloropyridin-4-yl)urea promotes the absorption and utilization of nitrogen, phosphorus, and zinc fertilizers by the grain crops.