CN111171086B - Wheat stress-resistant preparation and application thereof - Google Patents
Wheat stress-resistant preparation and application thereof Download PDFInfo
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- CN111171086B CN111171086B CN202010057545.1A CN202010057545A CN111171086B CN 111171086 B CN111171086 B CN 111171086B CN 202010057545 A CN202010057545 A CN 202010057545A CN 111171086 B CN111171086 B CN 111171086B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01C—PLANTING; SOWING; FERTILISING
- A01C1/00—Apparatus, or methods of use thereof, for testing or treating seed, roots, or the like, prior to sowing or planting
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
- A01G7/00—Botany in general
- A01G7/06—Treatment of growing trees or plants, e.g. for preventing decay of wood, for tingeing flowers or wood, for prolonging the life of plants
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
- C08B37/0027—2-Acetamido-2-deoxy-beta-glucans; Derivatives thereof
- C08B37/003—Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A40/00—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production
- Y02A40/10—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in agriculture
Abstract
The invention belongs to the technical field of agricultural preparations, and particularly relates to a wheat drought-resistant preparation and application thereof as a plant growth regulator. The wheat stress-resistant compound is a chitosan aminobutyric acid derivative, and the general formula of the wheat stress-resistant compound is shown as a formula I; the wheat stress-resistant compound is applied to a wheat drought-resistant preparation. The wheat stress-resistant compound is applied to being used as a plant growth regulator. The chitosan-aminobutyric acid compound is prepared into a preparation with the concentration of 1mg/L-1g/L, the effects of drought resistance and the like of wheat are enhanced in a seed soaking, root irrigation or spraying mode, and the chitosan-aminobutyric acid compound has good application potential due to the advantages of easily available raw materials, simple synthesis method, safety, environmental protection, easy degradation, convenient operation, growth promotion effect and the like.
Description
Technical Field
The invention belongs to the technical field of agricultural preparations, and particularly relates to a wheat drought-resistant preparation and application thereof as a plant growth regulator.
Background
Wheat is not only an important grain crop in the world, but also the second major grain crop in China, and the yield of wheat is directly related to the living state of people and is closely related to the development of national economy. In germination, development and growth periods of wheat, the wheat is often stressed by drought, rain and the like, particularly in the germination period and seedling period, the resistance of the small surface is weak, so that large-area non-emergence of seedlings, seedling desiccation and wilting, early leaf recession, damage to a photosynthetic system and other adverse states are easily caused, the growth and development of the wheat in the later period are not facilitated, and the yield is finally influenced.
Disclosure of Invention
The invention aims to overcome the defects of complex proportion, limited action effect and poor environment friendliness of the existing drought-resistant preparation, and provides the drought-resistant wheat preparation which is simple in preparation, novel in structure and environment-friendly and is from natural sources, and the application of the drought-resistant wheat preparation as a plant growth regulator.
In order to achieve the purpose, the invention adopts the technical scheme that:
a wheat stress-resistant compound is a chitosan aminobutyric acid derivative with a general formula shown in formula I,
in the formula I, the raw materials are shown in the specification,
n =1-250; n1 and n2 are both larger than 1.
The preparation method of the wheat stress-resistant compound comprises the following steps: dissolving aminobutyric acid in a buffer solution, uniformly mixing, then adding a condensing agent and a coupling agent, and stirring at room temperature for reacting for 2-4 hours; and then adding chitosan into the reaction solution for reaction, purifying the reaction solution, and freeze-drying to obtain the chitosan aminobutyric acid derivative shown in the formula I.
Adding chitosan into the reaction system, and then stirring for 18-48 hours or reacting for 1-3 hours under the microwave condition; and after the reaction is finished, filling the reaction solution into a dialysis bag, dialyzing with deionized water, and freeze-drying to obtain the chitosan aminobutyric acid derivative shown in the formula I.
The microwave conditions are power: 100-2000W, time: 1-3 hours, temperature: 25-80 ℃.
The amino butyric acid: condensing agent: the molar ratio of the coupling agent is 1 (2-3) to (2-3); condensing agent: the molar ratio of the coupling agent is 1; aminobutyric acid: the molar ratio of the chitosan is (7-200) to 1 according to the polymerization degree of the chitosan; the buffer solution is 0.1mol/L morpholine ethanesulfonic acid water solution with pH = 5.5; the condensing agent is 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride (EDC & HCl); the coupling agent is N-hydroxysuccinimide (NHS), and the aminobutyric acid is gamma-aminobutyric acid or beta-aminobutyric acid.
An application of a wheat stress-resistant compound, and an application of the wheat stress-resistant compound in a wheat drought-resistant preparation.
The wheat seeds or wheat plants are treated by seed soaking, foliage spraying or root irrigation, and the period for treating the plants is a seed germination period and/or a seedling period.
An application of a wheat stress-resistant compound, which is an application of the wheat stress-resistant compound as a plant growth regulator.
A wheat stress-resistant preparation contains the compound.
The preparation is water agent, powder, wettable powder, missible oil, suspending agent or microemulsion.
The stress-resistant wheat preparation is suitable for drought in natural state, nutrient solution simulated drought and other stress environments.
The concentration range of the preparation is 1mg/L-1g/L.
The principle is as follows: the carboxyl of the aminobutyric acid is activated by a condensing agent and a coupling agent and then is subjected to acylation reaction with the amino of chitosan with acetyl removed to form an amido bond, but because the aminobutyric acid also has an amino group, the activated carboxyl in the free aminobutyric acid also reacts with the amino of the aminobutyric acid grafted to the chitosan oligosaccharide, so that the synthesized derivative is a chitosan polyaminobutyric acid derivative. And the experimental time can be shortened by using the microwave reactor.
The invention has the advantages that:
the chitosan-aminobutyric acid derivative has the advantages of novel structure, simple synthesis method, wide raw material source and low cost; the fertilizer acts on wheat in a seed soaking, root irrigation or spraying manner, so that the effects of drought resistance and the like of the wheat are enhanced, and meanwhile, the fertilizer is safe, environment-friendly, easy to degrade, convenient and fast to operate, has the advantages of growth promotion and the like, and has good application potential; the method specifically comprises the following steps:
1. the invention synthesizes a series of novel chitosan-aminobutyric acid derivatives, and has the advantages of novel structure, simple synthesis method, wide raw material source and low cost.
2. The compound of the invention can obviously enhance the drought-resistant activity of wheat, and obviously improves the drought-resistant effect of the components of chitosan (or chitosan oligosaccharide), beta-aminobutyric acid or gamma-aminobutyric acid.
3. The wheat drought-resistant preparation has wide application, convenient implementation and obvious use effect; meanwhile, by adopting the wheat drought-resistant preparation, the emergence rate of wheat seeds is improved, the good growth of the wheat in the seedling stage is ensured, the drought-resistant capability of the wheat is improved, and the yield is further ensured.
Drawings
FIG. 1 is an infrared spectrum of chitosan (chitosan) according to an embodiment of the present invention, wherein the absorption characteristic of the infrared spectrum (cm) is shown -1 ): 3243.18, 2879.09, 1606.56, 1510.03, 1413.54, 1374.05, 1150.94, 1058.14, 1028.52, etc.
FIG. 2 is an infrared spectrum of a chitosan derivative 1 obtained by the method of the present invention (1K-B: 1000Da chitosan and beta-aminobutyric acid derivative), which has characteristic absorption in the infrared (cm) spectrum -1 ): 3273.51, 2874.66, 1634, 1545, 1378, 1148.96, 1062.09, 1026.54, etc.
FIG. 3 is an infrared spectrum of chitosan derivative 2 obtained by the method of the present invention (1K-G: 1000Da chitosan and gamma-aminobutyric acid derivative), wherein the characteristic infrared absorption (cm-1) is as follows: 3273.86, 2872.95, 1632, 1547, 1375.68, 1148.64, 1058.64, 1027.95, etc.
FIG. 4 is an infrared spectrum of chitosan derivative 3 obtained by the method of the present invention (9K-G: 9000Da chitosan and γ -aminobutyric acid derivative), wherein the characteristic infrared absorption (cm-1) is as follows: 3273.95, 2872.95, 1634.14, 1549.43, 1373.64, 1152.73, 1056.59, 1027.95, etc.
FIG. 5 is an infrared spectrum of chitosan derivative 4 obtained by the method of the present invention provided in the example of the present invention (9K-G: 9000Da chitosan and beta-aminobutyric acid derivative), wherein the characteristic absorption in the infrared (cm-1): 3279.10, 2873.28, 1634.14, 1549.43, 1372.13, 1151.49, 1060.87, 1023.44, etc.
Fig. 6 is a liquid nuclear magnetic carbon spectrum of 1K chitosan-poly β -aminobutyric acid (chitosan-BABA), 1K chitosan-poly γ -aminobutyric acid (chitosan-GABA), and chitosan (chitosan) obtained by the method of the present invention according to the embodiment of the present invention.
Detailed Description
The following examples further illustrate embodiments of the present invention, and it should be understood that the embodiments described herein are for purposes of illustration and explanation only and are not intended to limit the invention.
The compound of the invention takes chitosan as a framework (see figure 1), and an amino butyric acid structure is grafted on the 2-amino position of the chitosan.
In the formula I, the compound has the following structure,
n＝1-250。
the process for the preparation of the compounds of formula I according to the invention is described in more detail below, without however restricting the invention to these particular processes.
Example 1:
the preparation method of the chitosan aminobutyric acid derivative comprises the following steps:
dissolving gamma-aminobutyric acid or beta-aminobutyric acid in 0.1mol/L morpholine ethanesulfonic acid aqueous solution with pH =5.5, uniformly mixing, then adding 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride (EDC. HCl) and N-hydroxysuccinimide (NHS), and stirring at room temperature for reacting for 2 hours; adding chitosan into the reaction solution and continuously stirring for 24 hours; and after the reaction is finished, filling the reaction solution into a dialysis bag, dialyzing with deionized water, and freeze-drying to obtain the chitosan aminobutyric acid derivative shown in the formula I.
That is, when beta-aminobutyric acid is added to the derivative 1,
in the formula I, the compound has the following structure,
n =6, n2 being greater than 1.
When gamma-aminobutyric acid is added to the derivative 2,
in the formula I, the raw materials are shown in the specification,
n =6, n1 being greater than 1.
The chitosan has high deacetylation and polymerization degree of 6. The amino butyric acid: EDC & HCl condensing agent: the molar ratio of NHS is 1; aminobutyric acid: the molar ratio of chitosan was 7.
The infrared spectrum shows that: the infrared spectrum of chitosan derivative 1 (FIG. 2) was 1606.56cm in comparison with the infrared spectrum of chitosan (FIG. 1) -1 NH of (2) 2 The characteristic absorption peak disappeared, indicating NH 2 The reaction has occurred; 1634 and 1545cm -1 The C = O absorption peak and the N-H deformation vibration absorption peak indicate the formation of a new amide bond. In conclusion, the synthesis of derivative 1 was successfully demonstrated.
The infrared spectrum shows that: the infrared spectrum of chitosan derivative 2 (FIG. 3) was 1606.56cm in comparison with the infrared spectrum of chitosan (FIG. 1) -1 NH of (2) 2 The characteristic absorption peak disappeared, indicating NH 2 The reaction has occurred; 1632 and 1547cm -1 The C = O absorption peak and the N-H deformation vibration absorption peak indicate that a new amido bond is formed, and the synthesis of the derivative 2 is proved to be successful.
Example 2
The preparation method of the chitosan aminobutyric acid derivative comprises the following steps:
dissolving gamma-aminobutyric acid or beta-aminobutyric acid in 0.1mol/L morpholine ethanesulfonic acid aqueous solution with pH =5.5, uniformly mixing, then adding 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride (EDC. HCl) and N-hydroxysuccinimide (NHS), and stirring at room temperature for reacting for 3 hours; then placing the reaction solution in a microwave reactor for 2 hours at the temperature of 600W and 40 ℃; and after the reaction is finished, filling the reaction solution into a dialysis bag, dialyzing with deionized water, and freeze-drying to obtain the chitosan aminobutyric acid derivative shown in the formula I.
That is, when gamma-aminobutyric acid is added to the derivative 3,
in the formula I, the compound has the following structure,
n =56, n1 being greater than 1.
In the derivative 4, when beta-aminobutyric acid is added,
in the formula I, the raw materials are shown in the specification,
n =56, n2 being greater than 1.
The infrared spectrum shows that: the IR spectrum (FIG. 4) of chitosan derivative 3 was 1606.56cm in comparison with the IR spectrum (FIG. 1) of chitosan -1 NH of (2) 2 The characteristic absorption peak disappeared, indicating NH 2 The reaction has occurred; 1634.14 and 1549.43cm -1 The C = O absorption peak and the N-H deformation vibration absorption peak indicate that a new amido bond is formed, and the synthesis of the derivative 3 is proved to be successful in conclusion.
The chitosan has high deacetylation and the polymerization degree of 56. The amino butyric acid: EDC & HCl condensing agent: the molar ratio of NHS is 1; aminobutyric acid: the molar ratio of chitosan was 60.
Example 3
Weighing 0.0125g of beta-aminobutyric acid (marked as B); weighing 0.0125G of gamma-aminobutyric acid (marked as G); 0.0125g chitooligosaccharide (1K) with molecular weight of 1000 Da; 0.0125g of the chitosan β -aminobutyric acid derivative (1K-B) prepared in example 1 above; 0.0125G of chitosan gamma-aminobutyric acid derivative (1K-G) prepared in example 1; and (3) respectively using water to fix the volume to 25mL to prepare each sample group of the wheat drought-resistant preparation, and simultaneously using deionized water as a blank group.
The wheat seeds are treated by utilizing the sample groups, and the specific experiment is as follows:
the experimental method comprises the following steps:
respectively carrying out seed soaking treatment on the wheat seeds for 8 hours by using the sample group and the blank group; taking out the soaked seeds, placing the seeds on moist gauze, and placing the seeds in a dark place for accelerating germination for 24 hours; selecting full and uniform-grade white exposed seeds with similar growth states, and sowing the seeds in flowerpots filled with soil with corresponding humidity, wherein 50 seeds are planted in each flowerpot, and the seeds are sown under the soil for 3cm; culturing in an illumination incubator under the conditions of 25/20 deg.C (day/night), illumination intensity of 60%, illumination period of 14/10h (day/night), and relative humidity of 65 + -5%; and measuring the related indexes of the wheat seedlings after the wheat grows to two leaves and one heart. The indices mentioned in this example are only partial indices.
Specific relevant indexes are as follows: (1) malondialdehyde (MDA) represents one of the products of lipid peroxidation under drought stress, and the amount of Malondialdehyde (MDA) represents the magnitude of membrane damage; (2) electrolyte leaching rate represents the permeability of the membrane and also represents the degree and stability of damage; (3) the relative water content of the leaves represents the water retaining capacity of the leaves of the wheat seedlings; (4) after the wheat seedlings grow to have two leaves and one core, measuring the root length, the seedling height and the seedling wet weight of the wheat seedlings, drying the wheat seedlings to constant weight by using a 105 ℃ oven, and measuring the dry weight of the seedlings; (see tables 1 and 2)
TABLE 1 influence of drought-resistant preparations of wheat on various indexes of wheat seedling leaves
| Group of | The malondialdehyde content is nmol/g | The leaching rate of electrolyte% | Relative water content of leaf |
| Control | 22.40 | 1.30 | 85.67 |
| Drought | 34.23 | 7.50 | 68.73 |
| B+drought | 27.69 | 4.23 | 71.87 |
| G+drought | 28.29 | 5.88 | 71.56 |
| 1K+drought | 32.78 | 7.44 | 70.47 |
| (1K-B)+drought | 26.55 | 3.89 | 72.31 |
| (1K-G)+drought | 26.95 | 3.99 | 72.19 |
As can be seen from table 1, the malondialdehyde content after drought treatment in each sample group and blank group is significantly increased, the malondialdehyde of wheat seedlings can be significantly reduced after treatment with the stress-resistant preparation derivative of the invention, and the effect is significant compared with that of the raw material, and the damage to plasma membranes is reduced; meanwhile, the electrolyte leaching rate of the drought-treated sample is obviously increased, the electrolyte leaching rate of the wheat seedling can be obviously reduced after the drought-treated sample is treated by an anti-stress preparation, the effect is obvious compared with that of the raw material, and the damage degree of lipid peroxidation on the membrane is further verified from another angle; in addition, the drought in the experiment obviously reduces the water content of the leaves, the water content of the leaves is obviously improved after the treatment of the wheat stress-resistant preparation sample group, and the effect is obvious compared with that of the raw materials.
Table 2 effect of wheat drought-resistant agent on wheat seedling biomass.
| Group of | Miao height (cm) | Root length (cm) | Miao Wet weight (g) | Miao Dry weight (g) |
| Control | 33.57 | 28.23 | 0.4424 | 0.0476 |
| Drought | 25.03 | 9.70 | 0.1366 | 0.0210 |
| B+drought | 25.88 | 10.53 | 0.1450 | 0.0219 |
| G+drought | 25.89 | 10.10 | 0.1637 | 0.0221 |
| 1K+drought | 25.29 | 9.77 | 0.1577 | 0.0224 |
| (1K-B)+drought | 27.20 | 13.10 | 0.2052 | 0.0301 |
| (1K-G)+drought | 26.63 | 12.83 | 0.1702 | 0.0250 |
In addition, as can be seen from table 2, the drought stress in the experiment obviously reduces the seedling height, root length, seedling wet weight and seedling dry weight of the wheat seedling, the seedling height, root length, seedling wet weight and seedling dry weight of the wheat are obviously increased after the wheat anti-stress preparation is treated, the effect is obvious compared with that of the raw materials, and the wheat anti-drought preparation can improve the drought stress resistance of the wheat seedling.
Example 4:
weighing 0.0125g of beta-aminobutyric acid (marked as B); weighing 0.0125G of gamma-aminobutyric acid (marked as G); 0.0125g chitooligosaccharide (1K) with molecular weight of 1000 Da; 0.0125g of the chitosan β -aminobutyric acid derivative (1K-B) prepared in example 1 above; 0.0125G of the chitosan gamma-aminobutyric acid derivative (1K-G) prepared in example 1; and (3) respectively using water to fix the volume to 25mL to prepare each sample group of the wheat drought-resistant preparation, and simultaneously using deionized water as a blank group.
The wheat seeds are treated by utilizing the sample groups, and the specific experiment is as follows:
respectively carrying out seed soaking treatment on the wheat seeds for 8 hours by using the sample group and the blank group; taking out the seeds, placing the seeds on moist gauze, and placing the seeds in a dark place for accelerating germination for 24 hours; selecting full, uniform-grade and similar-growth-state lubai seeds, and sowing the seeds in a water culture device containing Hoagland nutrient solution/Hoagland nutrient solution +20% PEG6000, wherein 25 seeds are planted in each pot, and each group comprises 4 bottles; placing in a light incubator for culture under the culture conditions of 25/20 ℃ (day/night), illumination intensity of 60%, illumination cycle of 14/10h (day/night) and relative humidity of 65 +/-5%, and spraying the wheat leaves with the wheat stress-resistant preparation prepared in the embodiment 2 every day after four days of culture; and measuring the related indexes of the wheat seedlings after the wheat grows to two leaves and one heart. The indices mentioned in this example are only partial indices.
Specific relevant indexes are as follows: (1) malondialdehyde (MDA) represents one of the products of lipid peroxidation under drought stress, and the amount of Malondialdehyde (MDA) represents the magnitude of membrane damage; (2) electrolyte leaching rate represents the permeability of the membrane and also represents the degree and stability of damage; (3) the relative water content of leaves represents the capacity of the leaves of the wheat seedlings to retain water; (4) in the experiment, after the wheat seedlings grow to have two leaves and one heart, the seedling height and the seedling wet weight of the wheat seedlings are measured; (see tables 3 and 4).
TABLE 3 influence of wheat stress-resistant preparation on various indexes of wheat seedling leaves
| Group of | The malondialdehyde content is nmol/g | Electrolyte leaching rate% | Relative water content of leaf |
| Control | 5.55 | 1.49 | 85.23 |
| Drought | 9.01 | 12.19 | 69.80 |
| B+drought | 7.28 | 10.68 | 71.63 |
| G+drought | 6.54 | 9.04 | 71.75 |
| 1K+drought | 7.41 | 11.21 | 70.24 |
| (1K-B)+drought | 6.46 | 6.8 | 72.42 |
| (1K-G)+drought | 6.3 | 6.23 | 72.97 |
As can be seen from Table 3, the malonaldehyde content after hypertonic treatment in this experiment is significantly increased, the malonaldehyde production of wheat seedlings can be significantly reduced after treatment with the stress-resistant preparation, and the effect is significant compared with that of the raw material, and the damage to plasma membranes is reduced. Meanwhile, in the experiment, the permeation rate of the electrolyte is obviously increased by the high permeation treatment, the permeation rate of the electrolyte of the wheat seedlings can be obviously reduced after the treatment of the anti-stress preparation, the effect is obvious compared with that of the raw material, and the damage degree of the lipid peroxidation on the membrane is verified from another angle; in addition, the water content of the leaves is obviously reduced by hypertonicity in the experiment, the water content of the leaves is obviously improved after the leaves are treated by the wheat stress-resistant preparation, and the effect is obvious compared with that of the raw materials.
Table 4 effect of wheat stress tolerance preparation on wheat seedling biomass.
As can be seen from Table 4, in the experiment, the drought stress obviously reduces the seedling height and the seedling wet weight of the wheat seedlings, the seedling height and the seedling wet weight of the wheat are obviously increased after the wheat anti-stress preparation is treated, the effect is obvious compared with that of the raw materials, and the wheat anti-drought preparation can improve the drought stress resistance of the wheat seedlings.
Example 5:
weighing 0.0125g of beta-aminobutyric acid (marked as B); weighing 0.0125G of gamma-aminobutyric acid (marked as G); 0.0125g of chitooligosaccharide (9K) with a molecular weight of 9000 Da; 0.0125g of chitosan- β -aminobutyric acid derivative (9K-B) prepared in example 2 above; 0.0125G of the chitosan gamma-aminobutyric acid derivative (9K-G) prepared in the above example 2; and (3) respectively using water to fix the volume to 25mL to prepare each sample group of the wheat drought-resistant preparation, and simultaneously using deionized water as a blank group.
The wheat seeds are treated by utilizing the sample groups, and the specific experiment is as follows:
respectively carrying out seed soaking treatment on the wheat seeds for 8 hours by using the sample group and the blank group; taking out the seeds, placing the seeds on moist gauze, and placing the seeds in a dark place for accelerating germination for 24 hours; selecting full and uniform-grade white exposed seeds with similar growth states, and sowing the seeds in flowerpots filled with soil with corresponding humidity, wherein 50 seeds are planted in each flowerpot, and the seeds are sown under the soil for 3cm; culturing in an illumination incubator under the conditions of 25/20 deg.C (day/night), illumination intensity of 60%, illumination period of 14/10h (day/night), and relative humidity of 65 + -5%; and measuring the related indexes of the wheat seedlings after the wheat grows to two leaves and one heart. The indices mentioned in this example are only partial indices.
Specific relevant indexes are as follows: (1) malondialdehyde (MDA) represents one of the products of lipid peroxidation under drought stress, and the amount of Malondialdehyde (MDA) represents the magnitude of membrane damage; (2) electrolyte leaching rate represents the permeability of the membrane and also represents the degree and stability of damage; (3) the relative water content of leaves represents the capacity of the leaves of the wheat seedlings to retain water; (4) in the experiment, after the wheat seedlings grow to have two leaves and one heart, the seedling height and the seedling wet weight of the wheat seedlings are measured; (see tables 5 and 6).
TABLE 5 influence of wheat stress-resistant preparation on various indexes of wheat seedling leaves
| Group of | The malondialdehyde content is nmol/g | The leaching rate of electrolyte% | Relative water content of leaf |
| Control | 22.34 | 1.30 | 86.32 |
| Drought | 34.32 | 7.48 | 67.41 |
| B+drought | 27.71 | 4.25 | 71.86 |
| G+drought | 32.80 | 5.86 | 70.12 |
| 9K+drought | 29.3 | 5.19 | 70.50 |
| (9K-B)+drought | 27.11 | 4.11 | 72.27 |
| (9K-G)+drought | 27.32 | 4.13 | 72.22 |
As can be seen from Table 5, in the experiment, the content of malondialdehyde after drought treatment is obviously increased, the malondialdehyde of wheat seedlings can be obviously reduced after the treatment of the stress-resistant preparation, the effect is obvious compared with that of raw materials, and the damage to plasma membranes is reduced. In the experiment, the permeation rate of electrolyte is obviously increased by drought treatment, the permeation rate of electrolyte of wheat seedlings can be obviously reduced after the drought treatment is carried out by an anti-adversity preparation, the effect is obvious compared with that of raw materials, and the damage degree of lipid peroxidation to the membrane is verified from another angle. In addition, the drought in the experiment obviously reduces the water content of the leaves, the water content of the leaves is obviously improved after the leaves are treated by the wheat stress-resistant preparation, and the effect is obvious compared with that of the raw materials.
Table 6 effect of wheat stress tolerance on wheat seedling biomass.
| Group of | Miao height (cm) | Root length (cm) | Miao Wet weight (g) | Miao gan weight (g) |
| Control | 33.57 | 28.23 | 0.4424 | 0.0476 |
| Drought | 25.03 | 9.70 | 0.1366 | 0.0197 |
| B+drought | 25.88 | 10.53 | 0.1450 | 0.0219 |
| G+drought | 25.89 | 10.10 | 0.1637 | 0.0217 |
| 9K+drought | 25.29 | 9.65 | 0.1668 | 0.0227 |
| (9K-B)+drought | 27.20 | 12.15 | 0.1727 | 0.0234 |
| (9K-G)+drought | 26.63 | 12.05 | 0.1773 | 0.0248 |
As can be seen from Table 6, in the experiment, the drought stress obviously reduces the seedling height, root length, seedling wet weight and seedling dry weight of wheat seedlings, the seedling height, root length, seedling wet weight and seedling dry weight of wheat are obviously increased after the wheat anti-stress preparation is treated, the effect is obvious compared with that of the raw materials, and the wheat anti-drought preparation can improve the drought stress resistance of the wheat seedlings.
Claims (7)
1. A wheat stress-resistant compound is characterized in that: the wheat stress-resistant compound is a chitosan aminobutyric acid derivative, the general formula of which is shown as formula I,
the preparation method of the wheat stress-resistant compound comprises the following steps:
dissolving aminobutyric acid in a buffer solution, uniformly mixing, adding a condensing agent and a coupling agent, and stirring at room temperature for reacting for 2-4 hours; adding chitosan into the reaction solution for reaction, purifying the reaction solution, and freeze-drying to obtain a chitosan aminobutyric acid derivative shown in the formula I; adding chitosan into the reaction system, and then stirring for 18-48 hours or reacting for 1-3 hours under the microwave condition; after the reaction is finished, filling the reaction solution into a dialysis bag, dialyzing with deionized water, and freeze-drying to obtain the chitosan aminobutyric acid derivative shown in the formula I;
the microwave conditions are power: 100-2000W, time: 1-3 hours, temperature: 25-80 ℃;
the amino butyric acid: condensing agent: the molar ratio of the coupling agent is 1 (2-3) to (2-3); condensing agent: the molar ratio of the coupling agent is 1; aminobutyric acid: the molar ratio of the chitosan is (7-200) to 1 according to the polymerization degree of the chitosan; the buffer solution is 0.1mol/L morpholine ethanesulfonic acid water solution with pH = 5.5; the condensing agent is 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride (EDC. HCl); the coupling agent is N-hydroxysuccinimide (NHS); the aminobutyric acid is gamma-aminobutyric acid or beta-aminobutyric acid.
2. A process for the preparation of a wheat stress-resistant compound according to claim 1, characterized in that:
dissolving aminobutyric acid in a buffer solution, uniformly mixing, adding a condensing agent and a coupling agent, and stirring at room temperature for reacting for 2-4 hours; adding chitosan into the reaction solution for reaction, purifying the reaction solution, and freeze-drying to obtain a chitosan aminobutyric acid derivative shown in the formula I;
adding chitosan into the reaction system, and then stirring for 18-48 hours or reacting for 1-3 hours under the microwave condition; after the reaction is finished, filling the reaction solution into a dialysis bag, dialyzing with deionized water, and freeze-drying to obtain the chitosan aminobutyric acid derivative shown in the formula I;
the microwave conditions are power: 100-2000W, time: 1-3 hours, temperature: 25-80 ℃;
the amino butyric acid: condensing agent: the molar ratio of the coupling agent is 1 (2-3) to (2-3); condensing agent: the molar ratio of the coupling agent is 1; aminobutyric acid: the molar ratio of the chitosan is (7-200) to 1 according to the polymerization degree of the chitosan; the buffer solution is 0.1mol/L morpholine ethanesulfonic acid water solution with pH = 5.5; the condensing agent is 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride (EDC.HCl); the coupling agent is N-hydroxysuccinimide (NHS); the aminobutyric acid is gamma-aminobutyric acid or beta-aminobutyric acid.
3. The use of a wheat stress-resistant compound as defined in claim 1, wherein: the wheat stress-resistant compound is applied to a wheat drought-resistant preparation.
4. The use of a wheat stress-resistant compound according to claim 3, characterized in that: the wheat seeds or wheat plants are treated by seed soaking, foliage spraying or root irrigation, and the period for treating the plants is a seed germination period and/or a seedling period.
5. The use of a wheat stress-resistant compound as defined in claim 1, wherein: the wheat stress-resistant compound is applied to being used as a plant growth regulator.
6. A wheat stress-resistant preparation is characterized in that: the formulation comprising a compound of claim 1.
7. The wheat stress-relief preparation according to claim 6, wherein: the preparation is water agent, powder, missible oil, suspending agent or microemulsion.
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