Phenylurea compound, method for preparing same, and use thereof, and composition for promoting crop cell division and method for using same
By preparing and applying phenylurea compounds with a formula IV structure, the limitations of existing cytokinin-based plant growth regulators have been overcome, achieving stable and safe cell division effects, and promoting crop growth, development, and yield improvement.
Patent Information
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- HENAN ZHENGSHI CHEMICAL PRODUCTS CO LTD
- Filing Date
- 2025-05-22
- Publication Date
- 2026-06-04
AI Technical Summary
Existing cytokinin-based plant growth regulators suffer from limitations in availability, unstable efficacy, inconvenience in use, and insufficient safety in practical applications, making it difficult to meet the needs of modern agricultural production.
A phenylurea compound was developed, prepared by addition and substitution reactions, having a phenylurea compound of formula IV, for use in the preparation of formulations and combined with an inert carrier to form a composition that promotes crop cell division, suitable for a variety of crops and plant parts.
This study developed a cytokinin-like substance that is stable, easy to use, and safe. It can promote crop seed germination, cotyledon expansion, leaf greening and yield increase, fruit retention and expansion, and has a significant effect on promoting cell division.
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Figure CN2025096446_04062026_PF_FP_ABST
Abstract
Description
A phenylurea compound, its preparation method and application; a composition for promoting crop cell division and its application method.
[0001] This application claims priority to Chinese Patent Application No. CN202411734748.4, filed on November 28, 2024, entitled "A phenylurea compound and its preparation method and application, a composition for promoting crop cell division and its application method", the entire contents of which are incorporated herein by reference. Technical Field
[0002] This application relates to the field of plant growth regulator technology, and in particular to a phenylurea compound and its preparation method and application, a composition for promoting crop cell division and its application method. Background Technology
[0003] In modern agricultural production, plant growth regulators are increasingly widely used. Cytokinin-based plant growth regulators, such as zeatin, furfurylaminopurine, 6-benzylaminopurine, chlorpyrifos, and thidiazuron, have physiological effects such as promoting cell division and expansion, promoting fruit setting and expansion, and delaying leaf senescence. They can effectively regulate crop growth and development, improving crop yield and quality. However, these traditional plant growth regulators often have certain limitations in practical applications. For example, zeatin, being an endogenous plant cytokinin, is mostly obtained through bio-fermentation, which limits the availability of the finished product. Furfurylaminopurine and benzylaminopurine have mild effects, making them unsuitable for certain applications, such as fruit setting and expansion in zucchini. Chlorpyrifos has poor mobility and is often used by dipping flowers and fruits, which is inconvenient for agricultural operations. Thiidiazuron has high biological activity; low concentrations promote cell division, but high concentrations used as a defoliant raise concerns about safety. Therefore, there is a need to develop a cytokinin-based substance that is stable, easy to use, and safe.
[0004] Application content
[0005] In view of this, the purpose of this application is to provide a phenylurea compound, its preparation method and application, a composition for promoting crop cell division and its application method. The phenylurea compound of this application is a class of cytokinin substances that are stable in effect, easy to use, and safe in action.
[0006] To achieve the above-mentioned objectives, this application provides the following technical solution:
[0007] This application provides a phenylurea compound having the structure shown in Formula IV:
[0008] In Formula IV, R1 is a phenyl or a monosubstituted phenyl, wherein the substituent in the monosubstituted phenyl is -X, C1-C5 alkoxy, C1-C5 alkyl or C1-C5 fluoroalkyl, and X is a halogen; R2 is selected from hydrogen or C1-C10 alkyl.
[0009] Preferably, the substituent is located at the para, ortho, or meta position of the amino group connected to the phenyl group.
[0010] Preferably, X is fluorine, chlorine, or bromine.
[0011] Preferably, R1 is phenyl, p-methylphenyl, p-fluorophenyl, or m-chlorophenyl.
[0012] Preferably, R2 is hydrogen or methyl.
[0013] Preferably, the phenylurea compound has the structure shown in any one of formulas IV-a to IV-e:
[0014] This application also provides a method for preparing the phenylurea compounds described in the above technical solution, comprising the following steps:
[0015] A compound having the structure shown in Formula I, sodium cyanate, and a solvent are mixed and subjected to an addition reaction to obtain an addition product having the structure shown in Formula II;
[0016] The addition product and a compound having the structure shown in Formula III are mixed and subjected to a substitution reaction to obtain the phenylurea compound;
[0017] In Formulas I and II, R1 is a phenyl or a monosubstituted phenyl, wherein the substituent in the monosubstituted phenyl is -X, C1-C5 alkoxy, C1-C5 alkyl or C1-C5 fluoroalkyl, and X is a halogen;
[0018] In Formula III, R2 is selected from hydrogen or C1 to C10 alkyl groups.
[0019] Preferably, the molar ratio of the compound having the structure shown in Formula I to sodium cyanate is 1:1 to 1:100.
[0020] Preferably, the compound having the structure shown in Formula I is aniline, 3-chloroaniline, 4-fluoroaniline, or 4-methylaniline.
[0021] Preferably, the mass ratio of the compound having the structure shown in Formula I to the solvent is 1:1 to 1:100.
[0022] Preferably, the solvent is an organic-water mixture.
[0023] Preferably, the organic matter in the organic-water mixture includes one or more of formic acid, acetic acid, propionic acid, isopropionic acid, butyric acid, N,N-dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, dimethyl ether, acetonitrile, and sulfolane.
[0024] Preferably, the addition reaction is carried out at a temperature of 0–100°C for a time of 1–48 h.
[0025] Preferably, the molar ratio of the addition product to the compound having the structure shown in Formula III is 1:1 to 1:100.
[0026] Preferably, the compound having the structure shown in Formula III is adenine or N9-methyladenine.
[0027] Preferably, the substitution reaction further includes the addition of an aqueous hydrochloric acid solution, wherein the aqueous hydrochloric acid solution has a mass percentage of 1% to 30%.
[0028] Preferably, the mass ratio of the addition product to the hydrochloric acid aqueous solution is 1:1 to 1:100.
[0029] Preferably, the substitution reaction is carried out at a temperature of 0–100°C for a time of 1–48 h.
[0030] This application also provides the application of the phenylurea compounds described in the above technical solutions in the preparation of formulations.
[0031] Preferably, the formulation is used to promote cell division.
[0032] Preferably, the formulation includes a plant growth regulator.
[0033] Preferably, the formulation is a soluble concentrate, a suspension concentrate, a wettable powder, or a water-dispersible granule.
[0034] This application also provides a composition for promoting crop cell division, comprising an active ingredient and an inert carrier, wherein the active ingredient is a phenylurea compound as described in the above-mentioned technical solution.
[0035] Preferably, the active ingredient in the composition has a mass percentage of 1-99%.
[0036] Preferably, the inert carrier includes a carrier that is acceptable in agriculture, forestry, or health.
[0037] Preferably, the composition is applied to a plant, a part of a plant, or a plant site.
[0038] Preferably, the plants include food crops, oil crops, cash crops, vegetable crops, fruit trees, flowers, medicinal plants, and garden crops.
[0039] Preferably, the grain crops include wheat, rice, corn, and potatoes; the oil crops include soybeans, peanuts, rapeseed, or sesame; the cash crops include tea trees, tobacco, cotton, sugarcane, or Sichuan pepper; the vegetable crops include tomatoes, peppers, cucumbers, zucchini, cowpeas, or spinach; the fruit trees include apples, pears, grapes, kiwifruit, mangoes, cherries, or dates; the flowers include roses, Chinese roses, or chrysanthemums; the medicinal plants include yams, Panax notoginseng, ginseng, or wolfberries; and the garden crops include lawns, nurseries, or trees.
[0040] Preferably, the plant part includes plant tissues and organs.
[0041] Preferably, the plant tissues or organs include cotyledons, seeds, leaves, or fruit contact.
[0042] Preferably, the method of use further includes: mixing the composition with other pesticides or other plant growth regulators or using it simultaneously.
[0043] Preferably, the other pesticides include one or more of fungicides, insecticides, and herbicides.
[0044] This application provides a phenylurea compound, and compared with the prior art, the advantages of this application are as follows:
[0045] The phenylurea compounds of this application possess cytokinin-like bioactivity, effectively promoting seed germination, cotyledon expansion, increased chlorophyll content, fruit retention, and fruit enlargement in crops. They exhibit stable effects and are safe for crops. Experimental results show that the phenylurea compounds of this application have cytokinin-like efficacy, effectively promoting seed germination in rice and peanuts, cotyledon expansion in radishes and cucumbers, maintaining green leaves and increasing yield in peanuts, promoting fruit setting and retention in zucchini, and increasing fruit enlargement and sweetness in grapes.
[0046] This application also provides a method for preparing the phenylurea compounds described in the above technical solution. The process of this application is simple, has low operating cost, and high product yield, and can be produced on a large scale. Attached Figure Description
[0047] Figure 1 is a schematic diagram illustrating the principle of preparing phenylurea compounds according to an embodiment of this application;
[0048] Figure 2 shows the growth of cucumber cotyledons. From top to bottom in Figure 2, the values are: blank water, chlorpyrifos-1ppm, chlorpyrifos-10ppm, IV-a 1ppm, and IV-a 10ppm.
[0049] Figure 3 shows the growth of radish cotyledons. From top to bottom in Figure 3, the values are: water blank, chlorpyrifos-1ppm, chlorpyrifos-10ppm, IV-a 1ppm, and IV-a 10ppm.
[0050] Figure 4 shows a photograph of zucchini treated with IV-a whole-plant spraying.
[0051] Figure 5 shows a real photo of zucchini treated with IV-a spraying.
[0052] Figure 6 shows a picture of the deformed melons obtained by thiamethoxam treatment;
[0053] Figure 7 shows a picture of a cucumber treated with chlorpyrifos;
[0054] Figure 8 shows the comparison of fruit size of Shine Muscat fruit treated with whole-plant spraying. From top to bottom in Figure 8, the treatments are: farmer self-prevention, thiamethoxam, IV-c 2ppm, and IV-c 20ppm.
[0055] Figure 9 shows the comparison of the size of Sunshine Rose berries treated with dipping. From top to bottom in Figure 9, the treatments are: farmer self-treatment, 6-BA, IV-d 20ppm, and IV-d 200ppm. Detailed Implementation
[0056] This application provides a phenylurea compound having the structure shown in Formula IV:
[0057] In Formula IV, R1 is a phenyl or a monosubstituted phenyl, wherein the substituent in the monosubstituted phenyl is -X, C1-C5 alkoxy, C1-C5 alkyl or C1-C5 fluoroalkyl, and X is a halogen; R2 is selected from hydrogen or C1-C10 alkyl.
[0058] In this application, the substituent is preferably located at the para, ortho, or meta position of the amino group connected to the phenyl group.
[0059] In this application, X is preferably fluorine, chlorine, or bromine.
[0060] In this application, R1 is preferably phenyl, p-methylphenyl, p-fluorophenyl, or m-chlorophenyl.
[0061] In this application, R2 is preferably hydrogen or methyl.
[0062] In this application, the phenylurea compound preferably has the structure shown in any one of formulas IV-a to IV-e:
[0063] The phenylurea compounds described in this application have cytokinin-like biological activity and can be used as plant growth regulators.
[0064] This application also provides a method for preparing the phenylurea compounds described in the above technical solution, comprising the following steps:
[0065] A compound having the structure shown in Formula I, sodium cyanate, and a solvent are mixed and subjected to an addition reaction to obtain an addition product having the structure shown in Formula II;
[0066] The addition product and a compound having the structure shown in Formula III were mixed and subjected to a substitution reaction to obtain the phenylurea compound shown.
[0067] In Formulas I and II, R1 is a phenyl or a monosubstituted phenyl, wherein the substituent in the monosubstituted phenyl is -X, C1-C5 alkoxy, C1-C5 alkyl or C1-C5 fluoroalkyl, and X is a halogen;
[0068] In Formula III, R2 is selected from hydrogen or C1 to C10 alkyl groups.
[0069] This application does not have any special restrictions on the source of raw materials; they can be obtained from sources well known to those skilled in the art or from conventional preparation methods.
[0070] Figure 1 is a schematic diagram illustrating the principle of preparing phenylurea compounds according to an embodiment of this application.
[0071] This application involves mixing a compound having the structure shown in Formula I, sodium cyanate, and a solvent to undergo an addition reaction to obtain the addition product, namely Formula II in Figure 1.
[0072] In this application, the molar ratio of the compound having the structure shown in Formula I to sodium cyanate is preferably 1:1 to 1:100, specifically 1:1, 1:10, 1:20, 1:30, 1:40, 1:50, 1:60, 1:70, 1:80, 1:90 or 1:100.
[0073] In this application, the mass ratio of the compound having the structure shown in Formula I to the solvent is preferably 1:1 to 1:100, specifically 1:1, 1:10, 1:20, 1:30, 1:40, 1:50, 1:60, 1:70, 1:80, 1:90 or 1:100.
[0074] In this application, the compound having the structure shown in Formula I is preferably aniline, 3-chloroaniline, 4-fluoroaniline, or 4-methylaniline.
[0075] In this application, the solvent is preferably an organic-water mixture, and the organic in the organic-water mixture preferably includes one or more of formic acid, acetic acid, propionic acid, isopropionic acid, butyric acid, N,N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO), N-methylpyrrolidone, dimethyl ether, acetonitrile, and sulfolane.
[0076] In this application, the temperature of the addition reaction is preferably 0 to 100°C, specifically 0, 10, 20, 30, 40, 50, 60, 70, 80, 90 or 100°C, and the time is preferably 1 to 48 hours, specifically 1, 5, 10, 15, 20, 25, 30, 35, 40 or 48 hours.
[0077] In a specific embodiment of this application, the compound having the structure shown in Formula I, sodium cyanate, and solvent are mixed and heated under stirring to carry out the addition reaction. After the addition reaction is completed, the mixture is allowed to cool naturally to room temperature, stirring is stopped, and then filtered. The resulting filtrate is washed with water and then crystallized with 95 vol% ethanol to obtain the addition product.
[0078] After obtaining the addition product, this application mixes the addition product with a compound having the structure shown in Formula III and performs a substitution reaction to obtain the phenylurea compound.
[0079] In this application, the molar ratio of the addition product to the compound having the structure shown in Formula III is preferably 1:1 to 1:100, specifically 1:1, 1:10, 1:20, 1:30, 1:40, 1:50, 1:60, 1:70, 1:80, 1:90 or 1:100.
[0080] In this application, the compound having the structure shown in Formula III is preferably adenine or N9-methyladenine.
[0081] In this application, the substitution reaction preferably further includes the addition of a solvent, which is preferably an aqueous hydrochloric acid solution, and the mass percentage of the aqueous hydrochloric acid solution is preferably 1% to 30%, specifically 1%, 5%, 10% or 20%.
[0082] In this application, the mass ratio of the addition product to the solvent is preferably 1:1 to 1:100, specifically 1:1, 1:10, 1:20, 1:30, 1:40, 1:50, 1:60, 1:70, 1:80, 1:90 or 1:100.
[0083] In this application, the temperature of the substitution reaction is preferably 0 to 100°C, specifically 0, 10, 20, 30, 40, 50, 60, 70, 80, 90 or 100°C, and the time is preferably 1 to 48 hours, specifically 1, 5, 10, 15, 20, 25, 30, 35, 40 or 48 hours.
[0084] In a specific embodiment of this application, the addition product is dissolved in a 10% hydrochloric acid aqueous solution, the compound having the structure shown in Formula III is added, the substitution reaction is carried out under reflux, a large amount of solid is precipitated, after the substitution reaction is completed, the mixture is naturally cooled to room temperature, filtered, the obtained filter solid is washed with water and dried to obtain the phenylurea compound.
[0085] This application also provides the application of the phenylurea compounds described in the above technical solutions in the preparation of formulations.
[0086] In this application, the formulation is preferably used to promote cell division as a plant growth regulator.
[0087] In this application, the formulation is preferably a soluble agent, a suspension agent, a wettable powder, or a water-dispersible granule.
[0088] The phenylurea compounds of this application are preferably used in their unaltered form.
[0089] In this application, the phenylurea compounds are preferably used in conjunction with carriers and excipients in the field of pharmaceutical formulation.
[0090] The compositions of this application can be administered in the form of a formulation.
[0091] This application also provides a composition for promoting crop cell division, comprising an active ingredient and an inert carrier, wherein the active ingredient is a phenylurea compound as described in the above-mentioned technical solution.
[0092] In this application, the mass percentage of the active ingredient in the composition is preferably 1% to 99%, specifically 1%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, or 99%.
[0093] In this application, the carrier preferably includes an agricultural, forestry, or sanitary acceptable carrier.
[0094] This application also provides a method for using the composition described in the above technical solution, wherein the composition is applied to a plant, a part of a plant, or a plant site.
[0095] In this application, the plants preferably include food crops, oil crops, cash crops, vegetable crops, fruit trees, flowers, medicinal plants, and garden crops; the food crops preferably include wheat, rice, corn, or potatoes; the oil crops preferably include soybeans, peanuts, rapeseed, or sesame; the cash crops preferably include tea trees, tobacco, cotton, sugarcane, or Sichuan pepper; the vegetable crops preferably include tomatoes, peppers, cucumbers, zucchini, cowpeas, or spinach; the fruit trees preferably include apples, pears, grapes, kiwifruit, mangoes, cherries, or dates; the flowers preferably include roses, Chinese roses, or chrysanthemums; the medicinal plants preferably include yams, Panax notoginseng, ginseng, or wolfberries; and the garden crops preferably include lawns, nurseries, or trees.
[0096] In this application, the plant part is preferably a plant tissue or organ, more preferably a cotyledon, seed, leaf, or fruit contact.
[0097] This application preferably involves diluting the phenylurea compound and applying it to plant tissues and organs in an effective amount, specifically:
[0098] Soaking rice seeds in 0.1–1 mg / L of effective amount or treating peanut seeds with 10–100 mg / kg of effective amount can promote seed germination.
[0099] Soaking radish and cucumber cotyledons in an effective dose of 1–10 mg / L promotes an increase in cotyledon weight and leaf area.
[0100] Foliar spraying at an effective concentration of 5–20 mg / L can promote greening of peanut leaves and increase yield.
[0101] Spraying the whole plant with an effective dose of 2–20 mg / L or dipping the fruit with an effective dose of 20–200 mg / L can regulate the growth and development of zucchini and grape fruits and promote fruit retention and expansion.
[0102] In this application, the method of use preferably further includes: mixing or using the composition with other pesticides and other plant growth regulators simultaneously.
[0103] In this application, the other pesticides preferably include fungicides, insecticides, and herbicides.
[0104] This application does not specifically limit the types of other pesticides and other plant growth regulators mentioned, and any types and sources known to those skilled in the art can be used.
[0105] The technical solutions of this application will be clearly and completely described below with reference to the embodiments therein. Obviously, the described embodiments are only a part of the embodiments of this application, and not all of them. All other embodiments obtained by those skilled in the art based on the embodiments of this application without creative effort are within the scope of protection of this application.
[0106] In the examples, CK refers to the blank control group.
[0107] Example 1
[0108] The reaction principle for preparing 1-phenyl-3-(9H-purine-6-amino)urea (compound IV-a) is shown in the following equation:
[0109] 93.13 g (1 mol) of aniline was dissolved in 600 mL of glacial acetic acid, and 300 mL of distilled water was added. The mixture was heated to 60 °C with stirring, and 71.5 g (1.1 mol) of NaNCO was added. The reaction was maintained at this temperature for 12 h. The reaction solution was then cooled to 30 °C and allowed to stand for 4 h. The mixture was filtered, and the solid was washed with water. The wet solid was crystallized with three times its weight of ethanol to obtain 90.0 g of intermediate II, with a purity of 98% and a yield of 66%.
[0110] 90.0 g (0.66 mol) of intermediate II was dissolved in 500 mL of 10 wt% HCl solution. 107.0 g (0.792 mol) of adenine (a compound having the structure shown in Formula III) was added with stirring. The mixture was heated to reflux for 20 h, during which a light brown solid continuously precipitated. After the reaction was complete, the temperature was lowered to 30 °C, and the mixture was filtered. The filtrate was washed with a small amount of water and dried to give 126.0 g of product IV-a, with a purity of 97% and a yield of 75.1%.
[0111] Example 2
[0112] Preparation of 1-(9H-purine-6-amino)-3-(p-tolyl)urea (compound IV-b):
[0113] Except for replacing aniline with an equimolar amount of 4-methylaniline, all other steps were the same as in Example 1, and product IV-b was prepared, with the following structural formula:
[0114] Example 3
[0115] Preparation of 1-(2-chlorophenyl)-3-(9H-purine-6-amino)urea (compound IV-c):
[0116] Except for replacing aniline with an equimolar amount of 3-chloroaniline, the remaining steps are the same as in Example 1, and the product IV-c is prepared with the following structural formula:
[0117] Example 4
[0118] Preparation of 1-(4-fluorophenyl)-3-(9H-purine-6-amino)urea (compound IV-d):
[0119] Except for replacing aniline with an equimolar amount of 4-fluoroaniline, all other steps were the same as in Example 1, and product IV-d was prepared, with the following structural formula:
[0120] Example 5
[0121] Preparation of 1-(2-fluorophenyl)-3-(9H-purine-6-amino)urea (compound IV-e):
[0122] Except for replacing adenine with an equimolar amount of N9-methyladenine, all other steps were the same as in Example 1, and product IV-e was prepared, with the following structural formula:
[0123] Table 1 shows the NMR data of the phenylurea compounds obtained in the examples.
[0124] Table 1. NMR data of phenylurea compounds obtained in the examples.
[0125] Example 6
[0126] 5 wt% soluble concentrate (SL)
[0127] Table 2 shows the formulation for 5 wt% soluble concentrate (SL).
[0128] Table 2 Formulation (wt%) of soluble solvent (SL)
[0129] The phenylurea compounds were processed using conventional soluble solvent processing techniques: feeding, stirring and dissolving, and mixing, to obtain soluble solvents of IV-a, IV-b, IV-c, IV-d, and IV-e in equal amounts. The dilution stability was determined according to GB / T 1603, the pH value was determined according to GB / T 1601, and the low temperature and heat storage stability were determined according to GB / T 19137. After all indicators were qualified, the products were labeled as P1, P2, P3, P4, and P5 respectively.
[0130] Example 7
[0131] 25wt% suspension concentrate (SC).
[0132] Table 3 shows the formulation of 25 wt% suspension concentrate (SC).
[0133] Table 3 Formulation (wt%) of 25wt% Suspension Concentrate (SC)
[0134] Phenylene urea compounds were processed using conventional suspension concentrate manufacturing processes: mixing, shearing, and milling to obtain IV-a, IV-b, IV-c, IV-d, and IV-e suspension concentrates with equal contents. The suspension rate was determined according to GB / T 14825, the pH value was determined according to GB / T 1601, the pourability was determined according to GB / T 31737, the persistent foaming property was determined according to GB / T 28137, and a wet sieve test was conducted according to GB / T 16150. Products meeting all the required standards were labeled as D1, D2, D3, D4, and D5.
[0135] Test case
[0136] Experimental Example 1: Seed Germination Experiment
[0137] Experimental crops: rice, peanuts
[0138] Test date: March 2024
[0139] Experimental location: Bioassay Laboratory, Henan Provincial Crop Chemical Control Technology Research Center
[0140] Test reagents: D1-D5 were used as test reagents (effective ingredient concentrations of 0.1 and 1 ppm for seed soaking; effective ingredient concentrations of 10 mg / kg and 100 mg / kg of seeds for seed dressing). Commercially available 2% benzylaminopurine (6-BA) soluble concentrate (produced by Zhengzhou Zhengshi Chemical Products Co., Ltd.) was set as the control reagent (effective ingredient concentrations of 1 and 10 ppm for seed soaking; effective ingredient concentrations of 10 mg / kg and 100 mg / kg of seeds for seed dressing). Water was set as the blank control.
[0141] Test method:
[0142] The specific method for the rice seed soaking experiment was as follows: Before soaking, the rice seeds were disinfected with sodium hypochlorite and then cleaned. The rice seeds were then soaked in each of the chemical solutions for 36 hours. After soaking, they were rinsed with clean water at least four times to remove any residual chemicals. The rice seeds were then evenly spread in petri dishes, with 40 seeds per dish, and each group was repeated three times. 20 mL of water was added to each petri dish, and the dishes were placed on a light-controlled culture rack with a 12-hour light / dark cycle. During the culture period, the germination of the rice was observed daily, and water was replenished as needed.
[0143] The specific method for the peanut seed dressing experiment is as follows: 25wt% thiamethoxam FS, a commercially available peanut seed dressing agent, was used to dress the seeds at a ratio of 700g:100kg of seeds. The experimental agent and control agent of this application were added together during the seed dressing process. After the seeds were evenly dressed, they were sown in seedling trays with 200 seeds per treatment. After covering with soil, the trays were placed in an artificial sunlight cultivation room for routine cultivation.
[0144] Survey methods: Germination potential of rice was measured on the 3rd day after application of pesticide, and germination rate was measured on the 5th day; germination rate of peanuts was measured on the 10th and 15th days after application of pesticide.
[0145] The results are shown in Tables 4-5. It can be seen that both the phenylurea compounds of this application and the control agent can promote seed germination and improve germination potential and germination rate. Among them, compounds IV-a and IV-c showed the best performance in rice, significantly improving germination potential and final germination rate, both superior to the control agent. In peanuts, the germination rate and germination rate were affected by the seed dressing agent alone. However, the phenylurea compounds of this application, combined with the seed dressing agent, effectively improved the germination rate of peanut seeds, with all treatments superior to the control agent.
[0146] Table 4. Effects of different pesticide treatments on rice seed germination.
[0147] Table 5. Effects of different combinations of seed dressing agents on peanut seed germination.
[0148] Experimental Example 2: Cotyledon Expansion Experiment
[0149] Experimental crops: Radish, Cucumber
[0150] Test date: May 2024
[0151] Experimental location: Bioassay Laboratory, Henan Provincial Crop Chemical Control Technology Research Center
[0152] Test reagents: P1-P5 were used as test reagents (active ingredient concentrations of 1 and 10 ppm), and commercially available 0.1% chlorpyrifos soluble concentrate (produced by Zhengzhou Zhengshi Chemical Products Co., Ltd.) was set as the control reagent (active ingredient concentrations of 1 and 10 ppm). Water was set as the blank control.
[0153] Experimental Method: Radish and cucumber seeds were disinfected, washed, and then cultured in a germination box at room temperature in the dark. Before the cotyledons fully expanded, the hypocotyl was removed, and the small cotyledons from each pair were cut off. Cotyledons of uniform size were selected for testing. 5 mL of the reagent solution and 5 mL of purified water were added to petri dishes lined with filter paper, while 10 mL of purified water was added to the blank control. Ten pre-weighed cotyledons were evenly spread in each dish. Five replicates were set up for each treatment, and the plants were cultured under 12 hours of light and 12 hours of darkness.
[0154] Investigation method: After 3 days of cultivation, the cotyledons were removed, and the surface moisture was absorbed with filter paper. The mass of the cotyledons in each dish was immediately weighed using a balance. The increase in cotyledon weight for each treatment was calculated and the average increase in weight was recorded.
[0155] Cytokinins can promote cell separation and expansion, and have the effect of promoting the enlargement of cotyledons in radishes and cucumbers. The cotyledon expansion method is a commonly used method for determining the bioactivity of cytokinins. The results are shown in Table 6 and Figures 2-3. Figure 2 shows the growth of cucumber cotyledons, with the following concentrations from top to bottom: water blank, chlorpyrifos-1 ppm, chlorpyrifos-10 ppm, IV-a 1 ppm, and IV-a 10 ppm. Figure 3 shows the growth of radish cotyledons, with the following concentrations from top to bottom: water blank, chlorpyrifos-1 ppm, chlorpyrifos-10 ppm, IV-a 1 ppm, and IV-a 10 ppm. The compound provided in this application can promote the increase of cotyledon weight and leaf area under this method, exhibiting cytokinin-like bioactivity. Among them, compound IV-a showed the best performance, with all concentrations being superior to the control agent chlorpyrifos in radish and cucumber cotyledons.
[0156] Table 6. Cotyledon growth under different treatments
[0157] Experiment Example 3: Peanut Premature Aging Prevention and Yield Increase Experiment
[0158] Experimental crop: peanut
[0159] Trial period: July-September 2024
[0160] Test location: Dingliu Village, Zhongmu County, Henan Province
[0161] Test reagents: P1-P5 were used as test reagents (active ingredient concentration of 5 and 20 ppm for spraying), and commercially available 2% benzylaminopurine soluble concentrate (produced by Zhengzhou Zhengshi Chemical Products Co., Ltd.) was set as the control reagent (active ingredient of 20 ppm). Water was set as the blank control.
[0162] Experimental method: Peanut fields with uniform growth were selected and randomly divided into plots. Each plot was covered with 4 rows of peanuts, and a protective row of one row width was set between different plots. Each treatment area was 30m. 2 Make sure to label each treatment area; dilute the test agent twice with water, and use a backpack electric sprayer to spray the leaves of each treatment area evenly. Apply the pesticide at the beginning of flowering, and the amount of pesticide solution per mu is 30L / mu.
[0163] Survey indicators: Chlorophyll content (SPAD) was measured 7 days after application and at harvest. Yield, number of fruits and weight of single fruit were measured at harvest.
[0164] Table 7 shows the effects of each treatment on peanut chlorophyll content, yield, and quality. It can be seen that the phenylurea compounds and the conventional regulator 6-benzylaminopurine treatment in this application have a certain promoting effect on peanut yield. Combined with the data on chlorophyll content and peanut number, the increase in yield is mainly based on the increase in chlorophyll content in the leaves, which in turn promotes the accumulation of photosynthetic products, which is conducive to promoting early and abundant pegging, and provides a foundation for early and abundant fruiting and increased yield in the later stage.
[0165] Table 7. Effects of each treatment on peanut chlorophyll content, yield, and quality.
[0166] Experiment Example 4: Fruit Setting and Retention Experiment of Zucchini
[0167] Experimental crop: Zucchini
[0168] Test date: April 2024
[0169] Test location: Huaiyang, Henan
[0170] Test agents: P1-P5 were used as test agents (2 ppm for whole plant spraying and 20 ppm for flower spraying). Commercially available 0.1% thiamethoxam soluble concentrate and 0.1% chlorpyrifos soluble concentrate (both produced by Zhengzhou Zhengshi Chemical Products Co., Ltd.) were set as control agents (2 ppm for whole plant spraying of thiamethoxam and 20 ppm for flower spraying of chlorpyrifos).
[0171] Experimental method: Select plots of land with uniform growth, and randomly divide them into areas, with each plot being 30m in size. 2 Thirty female flowers were selected, fixed, and labeled for each treatment. For whole-plant spraying: after the zucchini began to flower, the P1-P5 test agent and thiamethoxam control agent were diluted with water to a 2 ppm solution and sprayed onto the entire plant once a week, with 1 L of solution per plot. For flower spraying: on the day the zucchini began to flower, before 10:00 AM, the P1-P5 test agent and chlorpyrifos control agent were diluted with water to a 20 ppm solution and sprayed onto the flowers once using a small spray bottle.
[0172] Survey indicators: Observe and record the fruit setting situation weekly, and count the total number of fruits set and the fruit retention rate after 30 days.
[0173] Figure 4 shows a picture of zucchini treated with IV-a whole-plant spraying, Figure 5 shows a picture of zucchini treated with IV-a flower spraying, Figure 6 shows a picture of deformed melons obtained by thiamethoxam treatment, and Figure 7 shows a picture of melons that have failed to retain fruit after treatment with chlorpyrifos, indicating that fruit retention has failed.
[0174] Table 8 shows the effects of each treatment on fruit setting and fruit retention in zucchini. It can be seen that the phenylurea compounds used in this application, whether sprayed on the flowers or the entire plant, can promote fruit setting in zucchini, achieving a fruit retention rate of over 90%. In contrast, the control treatment with chlorpyrifos showed a low fruit retention rate, failing to meet agricultural application requirements. While thiamethoxam achieved a fruit retention rate close to 90%, it carried a risk of producing deformed fruits, causing economic losses for farmers.
[0175] Table 8. Effects of each treatment on fruit setting and fruit retention in zucchini.
[0176] Experiment Example 5: Grape Fruit Enlargement and Sweetening Experiment
[0177] Experimental crop: Grape - Shine Muscat
[0178] Trial period: May-September 2024
[0179] Test location: Xingyang, Henan
[0180] Test agents: For whole-plant spraying, agents D1-D5 were used as test agents (active ingredient concentrations of 2 ppm and 20 ppm), with a commercially available 0.1% thiabendazole soluble concentrate as the control agent (active ingredient concentration of 4 ppm). For fruit dipping treatment, agents P1-P5 were used as test agents (active ingredient concentrations of 20 ppm and 200 ppm), with a commercially available 2% benzyl gibberellic acid soluble concentrate (produced by Zhengzhou Zhengshi Chemical Products Co., Ltd.) as the control agent (active ingredient concentration of 200 ppm). Simultaneously, a farmer self-control plan – a farmer's routine application plan (active ingredients: chlorpyrifos 3 ppm + thiabendazole 2 ppm) – was established. All plans included the addition of 20 ppm of commercially available gibberellic acid for spraying or fruit dipping.
[0181] Experimental method: Three Shine Muscat grapevines were planted in each plot, and five bunches of fruit were randomly selected from each plant and labeled. Fifteen days after the grapevines finished flowering, each treatment was sprayed or dipped in the fruit once.
[0182] Survey indicators: Fruit diameter was measured 7 and 15 days after application of pesticides; single fruit weight and sweetness were measured at harvest. Sweetness was evaluated based on the base sugar content of the fruit bunch (consistent with the harvest standard; a base sugar content >15 was the harvest standard).
[0183] Figure 8 shows the comparison of fruit size of Shine Muscat grapes treated with whole-plant spraying. From top to bottom in Figure 8, the treatments are: Farmer Self-Prevention, Thiabenzodone, IV-c 2ppm, and IV-c 20ppm. Figure 9 shows the comparison of fruit size of Shine Muscat grapes treated with fruit dipping. From top to bottom in Figure 9, the treatments are: Farmer Self-Prevention, 6-BA, IV-d 20ppm, and IV-d 200ppm.
[0184] Table 9 shows the effects of each treatment on the fruit growth of Shine Muscat grapes. As can be seen from Figures 8-9 and Table 9, the phenylurea compounds of this application, whether sprayed or dipped on Shine Muscat grapes, promote fruit development, effectively increase fruit diameter, and do not affect the growth period or have any adverse effects on sweetness and harvest. Among them, the dipping treatment resulted in a faster overall fruit expansion rate.
[0185] Table 9. Effects of each treatment on the fruit growth of Sun Rose.
[0186] The above description is merely a preferred embodiment of this application and does not constitute any limitation on this application. It should be noted that those skilled in the art can make various improvements and modifications without departing from the principles of this application, and these improvements and modifications should also be considered within the scope of protection of this application.
Claims
1. A phenylurea compound, characterized in that, It has the structure shown in Formula IV: In Formula IV, R1 is a phenyl or a monosubstituted phenyl, wherein the substituent in the monosubstituted phenyl is -X, C1-C5 alkoxy, C1-C5 alkyl or C1-C5 fluoroalkyl, and X is a halogen; R2 is selected from hydrogen or C1-C10 alkyl.
2. The phenylurea compound according to claim 1, characterized in that, The substituent is located at the para, ortho, or meta position of the amino group attached to the phenyl group.
3. The phenylurea compound according to claim 1, characterized in that, X is fluorine, chlorine, or bromine.
4. The phenylurea compound according to claim 1, characterized in that, R1 is phenyl, p-methylphenyl, p-fluorophenyl, or m-chlorophenyl.
5. The phenylurea compound according to claim 1, characterized in that, R2 is hydrogen or methyl.
6. The phenylurea compound according to claim 1, characterized in that, It has the structure shown in any one of the formulas IV-a to IV-e:
7. The method for preparing the phenylurea compound according to any one of claims 1 to 6, characterized in that, Includes the following steps: A compound having the structure shown in Formula I, sodium cyanate, and a solvent are mixed and subjected to an addition reaction to obtain an addition product having the structure shown in Formula II; The addition product and a compound having the structure shown in Formula III are mixed and subjected to a substitution reaction to obtain the phenylurea compound; In Formulas I and II, R1 is a phenyl or a monosubstituted phenyl, wherein the substituent in the monosubstituted phenyl is -X, C1-C5 alkoxy, C1-C5 alkyl or C1-C5 fluoroalkyl, and X is a halogen; In Formula III, R2 is selected from hydrogen or C1 to C10 alkyl groups.
8. The preparation method according to claim 7, characterized in that, The molar ratio of the compound having the structure shown in Formula I to sodium cyanate is 1:1 to 1:
100.
9. The preparation method according to claim 7 or 8, characterized in that, The compound having the structure shown in Formula I is aniline, 3-chloroaniline, 4-fluoroaniline, or 4-methylaniline.
10. The preparation method according to claim 7, characterized in that, The mass ratio of the compound having the structure shown in Formula I to the solvent is 1:1 to 1:
100.
11. The preparation method according to claim 7 or 10, characterized in that, The solvent is an organic-water mixture.
12. The preparation method according to claim 11, characterized in that, The organic matter in the organic-water mixture includes one or more of formic acid, acetic acid, propionic acid, isopropionic acid, butyric acid, N,N-dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, dimethyl ether, acetonitrile, and sulfolane.
13. The preparation method according to claim 7 or 8, characterized in that, The addition reaction is carried out at a temperature of 0–100°C for a time of 1–48 h.
14. The preparation method according to claim 7, characterized in that, The molar ratio of the addition product to the compound having the structure shown in Formula III is 1:1 to 1:
100.
15. The preparation method according to claim 7 or 14, characterized in that, The compound having the structure shown in Formula III is adenine or N9-methyladenine.
16. The preparation method according to claim 7, characterized in that, The substitution reaction also includes the addition of an aqueous hydrochloric acid solution, wherein the aqueous hydrochloric acid solution has a mass percentage of 1% to 30%.
17. The preparation method according to claim 16, characterized in that, The mass ratio of the addition product to the hydrochloric acid aqueous solution is 1:1 to 1:
100.
18. The preparation method according to claim 7 or 14, characterized in that, The substitution reaction is carried out at a temperature of 0–100°C for a time of 1–48 h.
19. The use of the phenylurea compound according to any one of claims 1 to 6 in the preparation of formulations.
20. The application according to claim 19, characterized in that, The formulation is used to promote cell division.
21. The application according to claim 19, characterized in that, The formulation includes plant growth regulators.
22. The application according to claim 19, characterized in that, The formulation is a soluble concentrate, a suspension concentrate, a wettable powder, or a water-dispersible granule.
23. A composition that promotes crop cell division, characterized in that, It includes an active ingredient and an inert carrier, wherein the active ingredient is a phenylurea compound as described in any one of claims 1 to 6.
24. The composition for promoting crop cell division according to claim 23, characterized in that, The composition contains 1-99% by mass of the active ingredient.
25. The composition for promoting crop cell division according to claim 23, characterized in that, The inert carrier includes carriers that are acceptable in agriculture, forestry, or health.
26. The method of using the composition according to any one of claims 23 to 25, characterized in that, The composition is applied to a plant, a part of a plant, or a plant site.
27. The method of use according to claim 26, characterized in that, The plants mentioned include food crops, oil crops, cash crops, vegetable crops, fruit trees, flowers, medicinal plants, and garden crops.
28. The method of use according to claim 27, characterized in that, The grain crops include wheat, rice, corn, and potatoes; the oil crops include soybeans, peanuts, rapeseed, or sesame; the cash crops include tea trees, tobacco, cotton, sugarcane, or Sichuan pepper; the vegetable crops include tomatoes, peppers, cucumbers, zucchini, cowpeas, or spinach; the fruit trees include apples, pears, grapes, kiwifruit, mangoes, cherries, or dates; the flowers include roses, Chinese roses, or chrysanthemums; the medicinal plants include yams, Panax notoginseng, ginseng, or wolfberries; and the garden crops include lawns, nurseries, or trees.
29. The method of use according to claim 26, characterized in that, The plant parts mentioned include plant tissues and organs.
30. The method of use according to claim 29, characterized in that, The plant tissues and organs include cotyledons, seeds, leaves, or fruit contact.
31. The method of use according to claim 26, characterized in that, The method of use also includes: mixing the composition with other pesticides or other plant growth regulators or using it simultaneously.
32. The method of use according to claim 31, characterized in that, The other pesticides include one or more of fungicides, insecticides, and herbicides.