Plant growth regulator containing alkenyladenine and oxyenyladenine and application of plant growth regulator in crop stress resistance

Abstract

The invention relates to the technical field of growth regulators, and particularly discloses a plant growth regulator containing alkenyladenine and oxyenyladenine and application of the plant growth regulator in crop stress resistance. The plant growth regulator is prepared from 0.000125% of alkenyladenine, 0.000875% of oxyenyladenine, 1 to 10% of surfactant, 0.1 to 0.5% of stabilizer, 2 to 5% of cosolvent, 0.1 to 0.5% of defoaming agent, 0.1 to 0.5% of synergist, 0.01 to 0.1% of pH regulator, 0.01 to 0.05% of preservative and the balance of water. Compared with the prior art, the prepared plant growth regulator is more stable in property and not prone to deterioration and precipitation. By compounding alkenyladenine and oxyenyladenine, cell division is synergistically promoted, cold resistance, drought resistance and other capacities are enhanced, and growth quality improvement, stress resistance and disaster reduction are both considered.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of growth regulators, in particular to a plant growth regulator containing enkanthine and hydroxyenkanthine and its application in crop stress resistance. BACKGROUND

[0002] Enkanthine is a natural cytokinin plant growth regulator in nature, commonly found in plant young root tips, seeds and fruits. Its core function is to promote plant cell division and differentiation, which can not only promote lateral bud germination, induce adventitious root formation and accelerate plant tissue growth, but also delay leaf senescence by inhibiting chlorophyll decomposition, prolonging photosynthesis time, especially suitable for fresh-keeping of vegetables and flowers. In agricultural applications, it has a wide range of applications, which can be used for apple, pear, tomato, rice, wheat and other crops. Spraying during flowering or young fruit stage can reduce physiological fruit drop, using before harvesting of vegetables can extend shelf life, and using during grain filling stage of rice can promote grain filling.

[0003] Hydroxyenkanthine is an artificial cytokinin regulator. Compared with natural enkanthine, it has stronger stability and is not easily decomposed in soil and plant body, and its effective period can be extended by 30-50%. Its core function revolves around cell division, and it has more significant promoting effect on bud differentiation. At the same time, it can enhance the stress resistance of crops such as low temperature and drought, help crops to keep flowers and fruits, promote fruit enlargement, increase single fruit weight, improve sugar and vitamin content of fruits, reduce the proportion of deformed fruits, and improve the quality of crops. It is more focused on application in economic crops such as cotton, tobacco, strawberry, grape and watermelon in agriculture.

[0004] CN106900730A discloses a plant growth regulator composition, the effective component of which is composed of active component A and active component B. The active component A is thidiazuron, and the active component B is selected from a group of purine plant growth regulators, and the purine plant growth regulator contains at least one of furfuryl amino purine, enkanthine and hydroxyenkanthine. The application also provides a preparation method and application of the composition. The test results show that the composition can effectively regulate crop growth, improve the disease and stress resistance of crops, promote the healthy growth of crops, and improve the yield of crops.

[0005] CN108496966A relates to a plant growth regulator composition containing choline chloride and hydroxyenkanthine. In the effective component, the content ratio of choline chloride to hydroxyenkanthine is 0.5-60:0.1-50, and further preferably 1-50:0.5-30. The composition also contains a filler additive, and the weight ratio of the effective component to the filler additive is 1:0.1-15. The composition of the application mainly has the effects of promoting crop growth, enhancing photosynthesis of crops, improving crop yield and quality, etc.

[0006] Enesit and hydroxyenestit not only can regulate plant growth, but also can enhance the stress resistance of crops by maintaining cell viability and stabilizing physiological metabolism as natural cytokinin. Hydroxyenestit focuses on activating stress resistance mechanism and accelerating adversity recovery. The combination of the two can not only make up for the shortcomings of single component in growth regulation, but also make the regulation effect more accurate and the growth state more stable. In terms of growth regulation, it can achieve whole-cycle adaptation of strong seedling stage, stable flowering stage and optimal fruiting stage, and provide more comprehensive protection in stress resistance. The effect is more stable and efficient than using a single component, especially suitable for crops with high yield and quality requirements in frequent adversity. However, the solubility of enesit and hydroxyenestit is generally low, and they are easy to be oxidized. Therefore, the preparation of water agent may be affected by precipitation, which may affect the later use. SUMMARY

[0007] In view of the above defects of the prior art, the technical problem to be solved by the present application is to provide a plant growth regulator containing enesit and hydroxyenestit and its application in crop stress resistance.

[0008] The main reason for the solubility of enesit and hydroxyenestit is determined by the polarity characteristics of its molecular structure. From the chemical structure, both of them belong to purine derivatives, containing a large number of non-polar aromatic rings and alkyl groups in the molecule, while the hydrophilic groups such as amino and hydroxyl are relatively less. According to the principle of similar dissolves similar, the solubility of substances with low polarity in polar solvents such as water is naturally low. The amino group and carbon-carbon double bond on the purine ring in the molecule are active groups that are easy to be oxidized, and will trigger oxidation reaction when encountering oxidizing agent, oxygen, light and other factors. The preparation of aqueous solution not only is easy to be oxidized, but also may occur hydrolysis, and the activity will gradually decrease with time.

[0009] The present application provides a kind of double surfactant, which is obtained by nucleophilic substitution of acyl chloride prepared from acid and cystamine dihydrochloride. It can effectively reduce the surface tension of water, and its unique structure can form more compact micelles to encapsulate enesit and hydroxyenestit. The purine base part has a certain polarity, which can interact with the barrier layer of micelles, i.e. the interface between hydrophilic head group and hydrophobic tail chain, to form a loaded micelle, thereby ensuring the stability and effective dissolution of the components. The encapsulated drugs can also greatly reduce the risk of oxidation and decomposition, thereby further improving the stability.

[0010] In order to achieve the above-mentioned purpose, the present application provides a plant growth regulator containing ene adenine and hydroxy ene adenine, which comprises ene adenine 0.000125%, hydroxy ene adenine 0.000875%, a surfactant 1-10%, a stabilizer 0.1-0.5%, a cosolvent 2-5%, an antifoaming agent 0.1-0.5%, a synergist 0.1-0.5%, a pH regulator 0.01-0.1%, a preservative 0.01-0.05%, and the rest is water.

[0011] Further, the stabilizer is ascorbic acid.

[0012] Further, the cosolvent is ethanol.

[0013] Further, the antifoaming agent is a silicone antifoaming agent.

[0014] Further, the synergist is azone.

[0015] Further, the pH regulator is citric acid.

[0016] Further, the preservative is sodium benzoate.

[0017] The preparation method of the surfactant comprises the following steps: S1, under the catalysis of N,N-dimethylformamide, the acid and the thionyl chloride are stirred at 70-80 DEG C for 1-2 h, and then the excess thionyl chloride is removed by distillation to obtain an acyl chloride; S2, the acyl chloride in step S1 is added into N,N-dimethylformamide to obtain a solution A, cystamine dihydrochloride is added into N,N-dimethylformamide, and then the solution A is added dropwise at 0-5 DEG C, and after the dropwise addition is completed, the temperature is increased to room temperature, and the stirring is continued for 12-24 h, and then the surfactant is obtained by post-treatment.

[0018] Further, the mass ratio of the acid, the thionyl chloride and N,N-dimethylformamide is 1:3-5:0.001-0.005.

[0019] Further, the acid is one of lauric acid, myristic acid, oleic acid or vanillic acid.

[0020] Further, the mass ratio of the acyl chloride and N,N-dimethylformamide is 1:2-3.

[0021] Further, the mass ratio of the cystamine dihydrochloride and N,N-dimethylformamide is 1:15-25.

[0022] Preferably, the preparation method of the surfactant comprises the following steps: S1, the acid is stirred with thionyl chloride under the catalysis of N,N-dimethylformamide, and then the temperature is raised to 70-80 DEG C for 1-2 h, and then excess thionyl chloride is removed by distillation to obtain an acyl chloride; the mass ratio of the acid, thionyl chloride and N,N-dimethylformamide is 1:3-5:0.001-0.005; S2, the acyl chloride is added to N,N-dimethylformamide to obtain solution A, and the mass ratio of the acyl chloride and N,N-dimethylformamide is 1:2-3; cystamine dihydrochloride is added to N,N-dimethylformamide, and the mass ratio of the cystamine dihydrochloride and N,N-dimethylformamide is 1:15-25; solution A is added dropwise at 0-5 DEG C, and then the temperature is raised to room temperature; stirring is continued for 12-24 h; and after stirring is completed, the surfactant is obtained by post-treatment.

[0023] A preparation method of a plant growth regulator containing olefine adenine and hydroxy olefine adenine, comprising the following steps: X1, the cosolvent is stirred with olefine adenine and hydroxy olefine adenine until completely dissolved, a surfactant is added, and then a stabilizer, an antifoaming agent, a synergist and a preservative are sequentially added after uniform stirring to obtain a mixed solution; X2, a small amount of water is used to dissolve a pH regulator, which is added to the mixed solution under stirring to adjust the pH to 5.8-6.2, and finally water is added to obtain the product.

[0024] The application further provides application of the plant growth regulator containing olefine adenine and hydroxy olefine adenine in crop stress resistance.

[0025] The application has the following beneficial effects: 1, the application adopts the combination of olefine adenine and hydroxy olefine adenine, which can not only synergistically promote cell division, flower and fruit preservation and photosynthetic efficiency, realize balanced growth of crops in the whole cycle, but also stabilize cell membranes, activate antioxidant and osmotic regulation systems and enhance cold and drought resistance, and has the effects of growth improvement and stress resistance reduction.

[0026] 2, the application provides a double surfactant which can effectively reduce the surface tension of water, and the unique structure of the double surfactant can form more compact micelles, so that the double surfactant can wrap olefine adenine and hydroxy olefine adenine, thereby achieving good protection and solubilization effects, and the wrapped drugs can greatly reduce the risk of oxidation and decomposition, thereby further improving the stability. DETAILED DESCRIPTION

[0027] The silicone antifoaming agent is of model Tego Airex 902W and is from Wacker.

[0028] Example 1 A preparation method of a plant growth regulator containing olefine adenine and hydroxy olefine adenine, comprising the following steps: X1, 4 parts of ethanol are stirred with 0.000125 parts of alkenyladenine and 0.000875 parts of hydroxyalkenyladenine until completely dissolved, 5 parts of surfactant are added, and after uniform stirring, 0.3 parts of ascorbic acid, 0.2 parts of silicone defoaming agent, 0.3 parts of azone, 0.03 parts of sodium benzoate are added in sequence, and uniform stirring is continued to obtain a mixed solution; X2, 0.08 parts of citric acid are dissolved in 10 parts of water, and then added to the mixed solution under stirring to adjust the pH to 6.0, and finally water is added to make up to 100 parts, and uniform stirring is performed to obtain the product.

[0029] The preparation method of the surfactant comprises the following steps: S1, lauric acid is stirred with thionyl chloride at 75°C for 1.5h under the catalysis of N,N-dimethylformamide, and then excess thionyl chloride is removed by distillation to obtain an acid chloride; wherein the mass ratio of lauric acid, thionyl chloride and N,N-dimethylformamide is 1:4:0.002; S2, the acid chloride in step S1 is added to N,N-dimethylformamide to obtain solution A, and the mass ratio of acid chloride and N,N-dimethylformamide is 1:2.5; cystamine dihydrochloride is added to N,N-dimethylformamide, and the mass ratio of cystamine dihydrochloride and N,N-dimethylformamide is 1:20; solution A is added dropwise at 0°C, and then the temperature is raised to room temperature; stirring is continued for 12h; after stirring is completed, the product is poured into 5 times the volume of ice water, filtered, washed, recrystallized and dried to obtain the surfactant.

[0030] Example 2 It is basically the same as Example 1, the only difference is that lauric acid is replaced by myristic acid.

[0031] Example 3 It is basically the same as Example 1, the only difference is that lauric acid is replaced by oleic acid.

[0032] Example 4 It is basically the same as Example 1, the only difference is that lauric acid is replaced by vanillic acid.

[0033] Comparative Example 1 A preparation method of a plant growth regulator containing alkenyladenine and hydroxyalkenyladenine, comprising the following steps, in parts by weight: X1, 4 parts of ethanol are stirred with 0.000125 parts of alkenyladenine and 0.000875 parts of hydroxyalkenyladenine until completely dissolved, 5 parts of surfactant are added, and after uniform stirring, 0.3 parts of ascorbic acid, 0.2 parts of silicone defoaming agent, 0.3 parts of azone, 0.03 parts of sodium benzoate are added in sequence, and uniform stirring is continued to obtain a mixed solution; X2, 0.08 parts of citric acid is dissolved in 10 parts of water, then added to the mixture under stirring to adjust pH to 6.0, and finally make up with water to 100 parts, and stir well to obtain.

[0034] Comparative Example 2 A preparation method of a plant growth regulator containing enadenotucide and hydroxyenadenutucide, comprising the following steps, in parts by weight: X1, 4 parts of ethanol is stirred with 0.000125 parts of enadenutucide and 0.000875 parts of hydroxyenadenutucide until completely dissolved, 5 parts of Tween 80 is added, and then 0.3 parts of ascorbic acid, 0.2 parts of silicone antifoam, 0.3 parts of azone, and 0.03 parts of sodium benzoate are added in sequence under stirring to obtain a mixture; X2, 0.08 parts of citric acid is dissolved in 10 parts of water, then added to the mixture under stirring to adjust pH to 6.0, and finally make up with water to 100 parts, and stir well to obtain.

[0035] Test Example 1 The plant growth regulators prepared in the examples and comparative examples are used as test objects to carry out efficacy tests in wheat fields. The planting specification of the test field is 150,000 plants per mu, and the total test area is 50 mu 2 and is divided into test plots, each treatment is set with 4 repetitions, the plots are arranged randomly, and guard rows are set between the plots to avoid mutual interference. The test treatment is as follows: 1 time of spraying treatment is carried out at each of the wheat green-up and jointing stages, the dosage is 40 mL per mu, the water spraying amount per mu is 30 kg, and the physiological and biochemical indexes of wheat are determined regularly after treatment. After the wheat matures, five-point sampling method is used to sample each plot, 10 wheat plants are selected from each point, and the indexes such as plant height, 1 m 2 effective ear number, thousand-grain weight, and plot yield are investigated and determined. All index calculations are performed in accordance with the "Guidelines for Pesticide Field Efficacy Tests".

[0036] Table 1

[0037] As can be seen from Table 1, the plant growth regulator prepared in the examples can effectively increase the yield of wheat, because enadenotucide can promote plant cell division and differentiation, and hydroxyenadenotucide can enhance the stress resistance of crops such as low temperature and drought, so that the wheat grows well and the yield is obviously improved. Compared with the control examples, the effect of the plant growth regulator of the examples is obviously better, which may be because control example 1 does not add a surfactant, and control example 2 uses non-ionic surfactant Tween 80, while the gemini surfactant prepared in the examples can more effectively reduce the surface tension of water than the general non-ionic surfactant, and its unique structure can form a more compact micelle to wrap enadenotucide and hydroxyenadenotucide. The purine base part has a certain polarity and can interact with the barrier layer of the micelle, that is, the junction region of the hydrophilic head group and the hydrophobic tail chain, to form a loaded micelle, which is beneficial to the stability and dissolution of the active ingredients, so that the active ingredients can better play a role.

[0038] In example 4, the surfactant is prepared using vanillic acid, and the aromatic ring of the purine base and the benzene ring of vanillic acid may produce π-π stacking effect, and the wrapping and solubilization effect is stronger. In addition, the phenolic hydroxyl and methoxyl of vanillic acid together with the amide bond provide more hydrogen bond sites for the purine base of the drug, forming a strong multiple anchoring effect. The O-H bond on the phenolic hydroxyl of vanillic acid is relatively weak, and when free radicals exist in the system, it can quickly provide a hydrogen atom to the free radicals, so that the highly active free radicals are converted into stable molecules, and a stable phenoxyl radical is formed. The generated phenoxyl radical becomes very stable due to the large π bond conjugated system of the benzene ring and the electron-donating effect of the ortho methoxyl group. This stability prevents it from continuing to take hydrogen from other molecules to initiate a chain reaction, thereby interrupting the chain transfer of oxidation and protecting the easily oxidized active ingredients. This may be the reason why the yield-increasing effect of example 4 is the most significant.

[0039] Compared with examples 1 and 2, the hydrophobic chain of example 3 is longer and the hydrophobic effect is stronger, which can better drive the wrapping of the hydrophobic part of the drug, and the solubilization and stabilization effect of the drug is improved, so the regulation performance is better.

[0040] Test Example 2 The plant growth regulators prepared in the examples and the control examples were subjected to accelerated stability test, and the prepared water agent was placed at 35°C and 75% humidity for 60 days to observe whether precipitation or other phenomena occurred.

[0041] Table 2

[0042] The solubility of eno-adenine and hydroxy-eno-adenine is poor, and the amino group and carbon-carbon double bond on the purine ring in the molecule are active groups that are easily oxidized, and will trigger oxidation reaction when encountering oxidizing agents, oxygen, light, etc. When prepared into an aqueous solution, not only is it easy to oxidize, but hydrolysis can also occur, and the activity will gradually decrease over time. When stored at high temperatures, the two components will slowly oxidize and hydrolyze, and after oxidation, they will become purine oxides, and after hydrolysis, they will generate small-molecule organic compounds with broken structures. These products are more difficult to dissolve in water than the original components, and thus, precipitates can be clearly seen.

[0043] Compared with the control example, the aqueous solution prepared in the example is more stable, which indicates that the surfactant prepared in the application can play a good protective and solubilizing effect, and the drug wrapped can greatly reduce the risk of oxidation and decomposition, thereby further improving the stability.

[0044] The preferred embodiments of the application are described in detail above. It should be understood that those of ordinary skill in the art can make many modifications and changes without creative labor based on the concept of the application. Therefore, any technical solutions obtained by logical analysis, reasoning or limited experiments based on the prior art within the concept of the application should be within the protection scope determined by the claims.

Claims

1. A plant growth regulator containing enyl adenine and hydroxyenyl adenine, characterized in that, It includes 0.000125% adenine and 0.000875% hydroxyadenine, 1-10% surfactant, 0.1-0.5% stabilizer, 2-5% solubilizer, 0.1-0.5% defoamer, 0.1-0.5% synergist, 0.01-0.1% pH adjuster, 0.01-0.05% preservative, and the balance is water.

2. The plant growth regulator containing enyl adenine and hydroxyenyl adenine as described in claim 1, characterized in that, The stabilizer is ascorbic acid.

3. The plant growth regulator containing enyl adenine and hydroxyenyl adenine as described in claim 1, characterized in that, The co-solvent is ethanol.

4. The plant growth regulator containing enyl adenine and hydroxyenyl adenine as described in claim 1, characterized in that, The defoamer is an organosilicone defoamer.

5. The plant growth regulator containing enyl adenine and hydroxyenyl adenine as described in claim 1, characterized in that, The synergist is azone.

6. The plant growth regulator containing enyl adenine and hydroxyenyl adenine as described in claim 1, characterized in that, The pH adjuster is citric acid.

7. The plant growth regulator containing enyl adenine and hydroxyenyl adenine as described in claim 1, characterized in that, The preservative is sodium benzoate.

8. The plant growth regulator containing enyl adenine and hydroxyenyl adenine as described in claim 1, characterized in that, The method for preparing the surfactant includes the following steps: S1. The acid and thionyl chloride are heated to 70-80℃ and stirred for 1-2 hours under the catalysis of N,N-dimethylformamide. After removing the excess thionyl chloride by distillation, the acyl chloride is obtained. S2. Add the acyl chloride from step S1 to N,N-dimethylformamide to obtain solution A. Add cystamine dihydrochloride to N,N-dimethylformamide and add it dropwise to solution A at 0-5°C. After the addition is complete, raise the temperature to room temperature and continue stirring for 12-24 hours. After stirring, the surfactant is obtained through post-treatment.

9. A method for preparing a plant growth regulator containing enyl adenine and hydroxyenyl adenine as described in any one of claims 1-8, characterized in that, Includes the following steps: X1. Stir the cosolvent with adenine and hydroxyadenine until completely dissolved, add the surfactant, continue stirring until homogeneous, then add the stabilizer, defoamer, synergist and preservative in sequence, and stir until homogeneous to obtain a mixture; X2. Dissolve the pH adjuster in a small amount of water, add it to the mixture while stirring, adjust the pH to 5.8-6.2, and finally add water and stir well.

10. The application of the plant growth regulator containing enyl adenine and hydroxyenyl adenine as described in any one of claims 1-8 in crop stress resistance.

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