CN113402631B - Preparation method and application of alkaline seed coating agent film-forming agent - Google Patents
Preparation method and application of alkaline seed coating agent film-forming agent Download PDFInfo
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- 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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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
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- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
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Abstract
The invention belongs to the technical field of biological pesticide preparation, and particularly relates to a preparation method and application of an alkaline seed coating agent film-forming agent. Sodium carbonate is used as a catalyst, water is used as a medium, and water-soluble maleylation chitosan sodium, namely the alkaline seed coating agent film-forming agent, is prepared at normal temperature. The film forming agent is a modified chitosan derivative, is easy to dissolve in water, has good film forming performance and easy preparation, has a structure different from other chitosan used in seed coating agents at present, and has the original effect of chitosan. And the sodium maleylation chitosan solution is alkalescent, which is beneficial to reducing the soil acidification phenomenon caused by excessive use of nitrogen fertilizer.
Description
The technical field is as follows:
the invention belongs to the technical field of biological pesticide preparation, and particularly relates to a preparation method and application of an alkaline seed coating agent film-forming agent.
Background art:
seed coating agents, as an environmentally friendly pesticide formulation, are increasingly being used for seed treatment of various crops. The film agent is an important component in the seed coating agent, and can effectively fix the seed coating agent on seeds, so that air and a proper amount of moisture can pass through the film agent, the life function of the seeds is maintained, and the normal germination and emergence growth of the seeds are ensured; and the slow release of active ingredients such as pesticides or seed fertilizers can be realized, the lasting period of the pesticides and fertilizers is prolonged, and the growth of seedlings is promoted. Therefore, screening the film forming agent with excellent performance is a key factor for successfully developing the seed coating agent.
Film-forming agents commonly used in seed coating agents are: polysaccharides such as sodium alginate, pectin, chitosan, gum arabic, gelatin, xanthan gum, starch, methyl cellulose, and derivatives thereof, and polymer polymers such as polyvinyl acetate, polyvinyl alcohol, polyethylene glycol, polyacrylic acids, urea resin, and polyvinylidene chloride. The natural polymer film forming agent is non-toxic, stable, environment-friendly, safe, good in biocompatibility, cheap and easy to obtain, but poor in water solubility; the synthesized macromolecular film-forming agent has excellent stability, film-forming property and cohesiveness, but the preparation process has higher difficulty.
Chitin is widely distributed in nature, exists in shells of crustaceans such as shrimps and crabs, epidermis of insects such as mantis and silkworm (pupa), and cell walls of fungi such as mushrooms, is second only to cellulose in storage amount, and is the second largest renewable resource on the earth. Chitosan is obtained by deacetylation of chitin, and is increasingly used as a film-forming agent in a seed coating agent due to abundant sources. However, the chitosan applied in the seed coating agent is insoluble in water, so acetic acid, hydrochloric acid and the like are adopted for dissolving in the preparation process, but the dissolving operation steps are complicated; the obtained chitosan solution is acidic, and the micro-environment of the seeds and the germinated soil is also acidified after coating.
The invention content is as follows:
the invention aims to solve the technical problem that chitosan serving as a film-forming agent in a seed coating agent needs to be dissolved by acetic acid or hydrochloric acid, the solution is acidic, and the acidification effect on soil is easily caused after the application.
In order to solve the problems, the invention provides a novel chitosan film forming agent with good water solubility, namely sodium maleylation chitosan (figure 1). The film forming agent is a modified chitosan derivative, is easy to dissolve in water, has good film forming performance, is easy to prepare, has a structure different from other chitosan (figure 2) used in seed coating agents at present, and has the corresponding effect of chitosan. And the sodium maleylation chitosan solution is alkalescent, which is beneficial to reducing the soil acidification phenomenon caused by excessive use of nitrogen fertilizer.
In order to achieve the purpose, the invention is realized by the following technical scheme that the preparation method of the alkaline seed coating film-forming agent takes sodium carbonate as a catalyst and water as a medium to prepare water-soluble maleylation chitosan sodium at normal temperature, namely the alkaline seed coating film-forming agent.
Further, the preparation method comprises the following steps:
(1) Adding water and glacial acetic acid into a 100L enamel reaction kettle according to a certain mass ratio, slowly adding chitosan into the kettle under low-speed stirring, and stirring for about 2h to dissolve the chitosan; wherein glacial acetic acid is used as acid regulator to promote chitosan dissolution.
(2) At room temperature, at 20-minute intervals, uniformly and alternately adding weighed sodium carbonate and maleic anhydride which are divided into 6 parts into a high-speed stirring reaction kettle in sequence, and stopping after the high-speed stirring reaction is carried out for a certain time; wherein, sodium carbonate is used as an alkali regulator, and maleic anhydride is used as an acylating agent to participate in the reaction.
(3) Transferring the reaction mixed solution into a 300L dissolving tank, adding 1% (volume/weight percentage) hydrochloric acid while stirring, adjusting the pH value of the solution to 1-2, precipitating the maleoyl chitosan, curing for 1h, performing centrifugal separation, washing the precipitate for 3 times by using dilute hydrochloric acid with the pH value of 2-3, transferring the precipitate into the dissolving tank after dehydrating by a centrifugal machine, adding dilute sodium hydroxide while stirring to dissolve the precipitate into sodium salt, adding acetone to separate out white flocculent precipitate, performing centrifugal separation, and drying the obtained precipitate in the sun or in the air to obtain the target product.
The application of the alkaline seed coating agent film-forming agent is to prepare the multi-effect type composite seed coating agent by taking sodium maleylation chitosan as the film-forming agent, compounding a low-toxicity high-efficiency bactericide, adding an antifreeze agent and other auxiliary agents.
Further, the seed coating agent is prepared by the following steps: 1-5 percent (weight/weight percentage) of the prepared film forming agent is dissolved in a proper amount of water, and then the sterilizing and antifreezing agents with different proportions, the emulsifying agent, the dispersing agent and the warning color with a certain proportion are added according to the requirement; and fully mixing the mixed solution, stirring for 10-15 min by using a magnetic stirrer with the rotating speed of 100-200 r/min, finally supplementing water to 100%, and uniformly stirring by using a vacuum homogenizer to obtain the suspension seed coating agent with different effects.
The invention has the beneficial effects that:
(1) Provides a natural film forming agent with good water solubility and film forming performance, and then compounds a bactericide and an antifreeze to prepare the multi-effect seed coating agent.
(2) The film forming agent has high water solubility, is easy to prepare and is beneficial to the production of seed coating agents.
(3) The film forming agent is alkalescent, which is beneficial to improving the soil acidification degree caused by excessive use of nitrogen fertilizer and improving the germination and growth environment of seeds.
Drawings
FIG. 1 is a structural diagram of sodium maleyl chitosan;
FIG. 2 is a schematic view of chitosan structure;
FIG. 3 is a technical process flow diagram for the preparation of sodium maleyl chitosan;
FIG. 4 is an infrared spectrum of Chitosan (CH) and maleoyl Chitosan (CHM);
FIG. 5 shows the basal rot of wheat stems treated with control;
FIG. 6 shows the wheat stem base rot treated by the seed coating agent of the present invention.
The specific implementation mode is as follows:
in order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention are clearly and completely described below, and it is obvious that the described embodiments are a part of the embodiments of the present invention, but not all of the embodiments. All other embodiments, which can be obtained by a person skilled in the art without making any creative effort based on the embodiments in the present invention, belong to the protection scope of the present invention.
Example (b): preparation of film forming agent-sodium maleylation chitosan and field test for preventing and treating wheat stem basal rot
1. Preparation of film-forming agent-sodium maleochitosan:
weighing 20g of chitosan, putting the chitosan into a 1000ml three-neck flask provided with a stirrer, adding a proper amount of water and glacial acetic acid, and stirring for about 2 hours to dissolve the chitosan. Weighing the sodium carbonate and the acylating agent maleic anhydride with the experimental amount, evenly dividing into six parts, alternately adding the two parts at room temperature, quickly stirring after the addition, and continuously reacting for 1 hour. After the reaction is stopped, pouring the reactant into a 1000ml beaker, adding 1% hydrochloric acid while stirring, adjusting the pH value of the solution to 1-2, precipitating the maleoyl chitosan, curing for 1h, performing centrifugal separation, washing the precipitate for 3 times by using dilute hydrochloric acid with the pH value of 2-3, transferring the precipitate into a dissolving tank after the precipitate is dehydrated by a centrifugal machine, adding dilute sodium hydroxide while stirring to precipitate sodium salt to be dissolved, then adding acetone to precipitate white flocculent precipitate, performing centrifugal separation, and drying or airing the obtained precipitate to obtain the film-forming agent, namely the maleoyl chitosan sodium.
1.1 Structure and characterization of sodium maleoyl chitosan:
comparing the infrared spectra (FIG. 4) of Chitosan (CH) and Ma Laike glycan (CHM), the presence of a primary amine bending vibration peak δ NH at 1650cm-1 in chitosan, an amide stretching vibration peak υ NH at 3100cm-1 in maleyl chitosan, an amide stretching vibration peak υ C = O at 1620cm-1 and an amide bending vibration peak δ NH at 1550cm-1, indicating that N-acylation at the amino group at C2 position was performed; the expansion vibration peak upsilon C = O of ester appears at 1720cm-1 position in the maleoyl chitosan, which indicates that O-acylation is carried out on hydroxyl at C3 and C6 positions.
1.2 Water solubility:
the sodium maleylated chitosan prepared by the present invention and chitosan purchased from the market, each 2g, were taken and added with 50ml of water respectively, stirred for 5 minutes, and the results show: the sodium maleylation chitosan is completely dissolved, and the common chitosan is insoluble in water. Another published patent CN109809865a shows: the acylated chitosan used as the film agent is insoluble in water and needs to be dissolved by acetic acid; in other disclosed seed coating patents, chitosan used as a film-forming agent is insoluble in water and needs to be dissolved by acetic acid or hydrochloric acid for use, which is not described herein.
1.3 determination of pH value of the film-forming agent:
the pH value of the film-forming agent is measured according to the method of GB/T1601-93, the pH value is 7.5-8.5, and the film-forming agent is alkalescent.
1.4 measurement of film formation time:
coating seeds of corn, wheat, mung bean and Chinese cabbage with the seed coating agent compounded by the maleyl chitosan, pouring the uniformly coated seeds on a clean paper surface, observing the surface of the paper surface, and recording the film forming time until the solidified film is not sticky. After 3 times of repeated tests, the measured film forming time is between 4.5 and 7.0min (see table 1), and the film forming time is far lower than 20min specified in the related standard of the seed coating agent, which indicates that the maleoyl chitosan has good film forming property.
TABLE 1 film Forming time for seed coating with sodium maleoyl Chitosan Complex seed coating
| Repetition of | Corn seed | Wheat seeds | Mung bean seeds | Chinese cabbage seeds |
| 1 | 5.5 | 6.5 | 5.5 | 4.5 |
| 2 | 6.0 | 6.5 | 6.0 | 4.5 |
| 3 | 5.5 | 7.0 | 6.0 | 5.0 |
1.5 measurement of film formation uniformity:
dripping the sodium maleyl chitosan on a glass slide, casting, drying and forming a film, and then soaking in water for 0.5h to completely scrape off a film from the glass slide. This indicates that the uniformity and integrity of the film formation are good.
1.6 determination of influence of film-forming agent on seed germination:
according to GB/T3543.4-1995, the germination test is carried out by using the coated corn, wheat and Chinese cabbage seeds, and the effect of the seed coating agent on seed germination is tested. As can be seen from table 2: no matter the content of the film forming agent is 1.0 percent or 5.0 percent, the germination rates and the germination potentials of the coated wheat, corn and Chinese cabbage seeds are equivalent to those of the control seeds, which shows that the film forming agent has no influence on the germination of the seeds.
TABLE 2 influence of the coating on the seed germination vigor and germination rate
2. Seed coating preparation:
weighing 2g of prepared sodium maleochitosan, adding 20ml of water, stirring and dissolving for later use; 2ml of pentanol azole, 3ml of prothioconazole, 16ml of prochloraz, 8ml of azoxystrobin and 2ml of 1, 2-propylene glycol are respectively measured and mixed, and then stirred for 10min to 15min by a magnetic stirrer with the rotating speed of 100r/min to 200r/min for later use; then 0.5ml of sorbitan fatty acid ester, 0.5ml of PEG2000 (polyethylene glycol 2000) and 0.3ml of alkaline rose essence are respectively measured, after mixing, a magnetic stirrer with the rotating speed of 100 r/min-200 r/min is used for stirring for 10 min-15 min, then the prepared components are mixed, finally water is supplemented to 100ml, and a vacuum homogenizer is used for stirring uniformly to obtain 100ml of suspension seed coating agent.
3. Seed coating:
diluting the seed coating agent prepared in the step 2 by using 100ml of the seed coating agent with water, coating 50kg of wheat seeds, and airing (drying) for later use.
4. And (3) field test design:
4.1 test treatment: the test was carried out with reference to GB/T17980.108-2004. There are 4 treatments in total: (1) the seed coated by the seed coating agent of the invention, (2) the seed coated by the commercial 3 percent difenoconazole suspension seed coating agent, (3) the seed coated by the commercial 50 percent thiophanate-methyl suspension seed coating agent, and (4) the seed not coated are used as the contrast. Each treatment was repeated 3 times for 12 cells, 20m per cell 2 The seeding rate is 10kg/667m2, and the seeding is carried out according to the local normal seeding time.
4.2 disease investigation: in the wheat filling period, randomly taking 5 points in each cell, taking 20 plants in each point, digging out the plants with roots, keeping the root system complete, taking back samples, and carrying out stem base rot grading investigation indoors according to the grading standard: stage 0: the whole plant has no browning symptom; level 1: root deformation; and 3, stage: the first stem node of the overground part has the phenomenon of browning and rotting; and 5, stage: the second stem node of the overground part has browning and rotting phenomena; and 7, stage: the lesion spots exceed the second stem nodes but have no white spikes; and 9, stage: the lesion spots are beyond the second stalk node and have white spikes.
4.3 investigation of effects: the results show (table 3): the control effects of 3 percent of difenoconazole and 50 percent of thiophanate-methyl are respectively 23.9 percent and 29.5 percent, the white spike rate is respectively 9.7 percent and 8.6 percent, the disease indexes are respectively 38.9 and 36.3, and both the disease indexes and the white spike rate are remarkably lower than those of a control; the seed coating agent of the invention has the control effect of 46.3 percent, the white spike rate of 5.2 percent and the disease index of 24.3, and the disease index and the white spike rate are obviously lower than those of the two seed coating agents. Therefore, the seed coating agent of the invention has the best effect.
Table 3: control effect of different seed coating agents on wheat stem basal rot
| Treatment of | Index of disease condition | Control effect (%) | Percentage of white spike (%) |
| 1. The seed coating agent coating of the invention | 24.3aA | 46.3 | 5.2aA |
| 2. 3% Difenoconazole coating | 38.9bA | 23.9 | 9.7bA |
| 3. 50% thiophanate-methyl coating | 36.3bA | 29.5 | 8.6bA |
| 4. Control (without coating) | 56.1cB | — | 17.6cB |
Claims (2)
1. The preparation method of the alkaline seed coating film-forming agent is characterized by comprising the following steps: sodium carbonate is used as a catalyst, water is used as a medium, and water-soluble maleylation chitosan sodium, namely an alkaline seed coating agent film-forming agent, is prepared at normal temperature; the film forming agent is alkalescent, which is beneficial to improving the soil acidification degree caused by excessive use of nitrogen fertilizer and improving the germination and growth environment of seeds;
the preparation method of the alkaline seed coating agent film-forming agent comprises the following steps:
(1) Adding water and glacial acetic acid into a reaction kettle, slowly adding chitosan into the kettle under low-speed stirring, and stirring to dissolve the chitosan;
(2) Uniformly and alternately adding sodium carbonate and maleic anhydride into a high-speed stirring reaction kettle in sequence, and stopping the high-speed stirring reaction after a certain time;
(3) Transferring the reaction mixed solution into a dissolving tank, adding hydrochloric acid while stirring, precipitating and separating out the maleoyl chitosan, and performing first centrifugal separation after curing; washing the precipitate with dilute hydrochloric acid, dewatering with a centrifuge, transferring into a dissolving tank, adding dilute sodium hydroxide under stirring to dissolve the precipitate into sodium salt, adding acetone to separate out white flocculent precipitate, centrifuging for the second time, and sun drying or air drying the obtained precipitate to obtain the target product;
during primary centrifugal separation, adding hydrochloric acid with the volume mass concentration of 1% while stirring, adjusting the pH value of the solution to 1-2, precipitating and separating out the maleoyl chitosan, curing for 1h, and then carrying out centrifugal separation;
during the second centrifugal separation, the precipitate is washed for 3 times by dilute hydrochloric acid with the pH value of 2-3 and then is dehydrated by a centrifugal machine;
in the step (2), sodium carbonate and maleic anhydride which are weighed and divided into 6 equal parts are uniformly and alternately added into a high-speed stirring reaction kettle in sequence at intervals of 20 minutes, and the reaction is stopped after the high-speed stirring reaction kettle is stirred at a high speed for a certain time;
the application of the film forming agent of the alkaline seed coating agent takes the sodium maleylation chitosan as the film forming agent, compounds a low-toxicity high-efficiency bactericide, adds an antifreeze agent and other additives to prepare the multi-effect type composite seed coating agent.
2. A method for preparing the seed coating agent of claim 1, which is characterized by comprising the following steps: dissolving the prepared film forming agent in 1-5 wt% water, and adding different proportions of sterilizing and antifreezing agents, and a certain proportion of emulsifier, dispersant and warning color according to the requirement; and fully mixing the mixed solution, stirring for 10-15 min by using a magnetic stirrer with the rotating speed of 100-200 r/min, finally supplementing water to 100%, and uniformly stirring by using a vacuum homogenizer to obtain the suspension seed coating agent with different effects.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1253732A (en) * | 1998-11-14 | 2000-05-24 | 青岛利中甲壳质公司 | Natural marine fruit vegetable coating fresh-keeping agent |
| CN104558442A (en) * | 2014-12-25 | 2015-04-29 | 青岛文创科技有限公司 | Method for synthesizing chitosan cross-linked polymaleic anhydride super absorbent resin |
| WO2018042311A1 (en) * | 2016-08-29 | 2018-03-08 | Swasti Agro & Bioproducts Pvt Ltd. | Chitosan derivative formulations for plant growth, and building disease resistance |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1253732A (en) * | 1998-11-14 | 2000-05-24 | 青岛利中甲壳质公司 | Natural marine fruit vegetable coating fresh-keeping agent |
| CN104558442A (en) * | 2014-12-25 | 2015-04-29 | 青岛文创科技有限公司 | Method for synthesizing chitosan cross-linked polymaleic anhydride super absorbent resin |
| WO2018042311A1 (en) * | 2016-08-29 | 2018-03-08 | Swasti Agro & Bioproducts Pvt Ltd. | Chitosan derivative formulations for plant growth, and building disease resistance |
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