CN109769803A - A kind of pesticide polyelectrolyte nano-micelle and preparation method thereof - Google Patents
A kind of pesticide polyelectrolyte nano-micelle and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a kind of pesticide polyelectrolyte nano-micelles and preparation method thereof.In the pesticide polyelectrolyte nano-micelle, hydrophobic pesticidal is wrapped in the nano-micelle formed by the interaction of charge between Sensor Chip CM 5 and polycationic electrolyte.The hydration partial size of the pesticide polyelectrolyte nano-micelle is 150~300nm；And/or the surface of the pesticide polyelectrolyte nano-micelle has negative charge.Nano carrier material used in the present invention is the good and biodegradable natural polymeric material derivative of biocompatibility, and its is from a wealth of sources, cheap；Preparation method prevents the organic solvent using surfactant and high poison, and composite environmental-friendly requirement has the characteristics that preparation process simply and reaction condition is mild, can pesticidal preparations production technical field with good application prospect；The spherical structure of rule is presented in prepared pesticide polyelectrolyte nano-micelle, disperses stability that is uniform and being able to maintain the long period.
Description
Technical field
The invention belongs to pesticidal preparations production technical field more particularly to a kind of pesticide polyelectrolyte nano-micelle and its systems
Preparation Method.
Background technique
Nano pesticide technology is a branch of nanometer biotechnology, is the nanoscale that pesticide is realized using carrier technique
Contain, realize the technology of the performances such as pesticide is water-soluble, protection and slow control.Because most pesticides do not dissolve in traditional pesticide technology
Water, needs for pesticide to be dissolved in first in application process in organic solvent and then missible oil dosage form is made with convenient in addition surfactant
For spray dispenser.Nano pesticide then utilizes nano material package pesticide to solve the problems, such as that the water of pesticide is insoluble.It does not need to be added with
Solvent and surfactant, it can thus be avoided a large amount of toxic organic solvents and surface-active in slightly solubility Pesticidal products
The use of agent reduces pollution and organic residue of the chemical substance to crops.Simultaneously the fast of pesticide can also be prevented by sustained release
Prompt drop solution and extend and drug effect and improve the bioavilability of pesticide；In addition, nano material can also be by improving pesticide
Blade face attachment, delay and covering performance, reduce and are lost, improve the spray pattern of pesticide；Since nano material used has
Preferable biocompatibility, therefore, nano pesticide can also improve its environmental behaviour and improve its biological safety.
However, existing nano pesticide micella is mainly self-assembly of nanometer by hydrophobe effect using amphiphilic polymers
Micella, main method includes multi-emulsion method, emulsification mechanism and nanoprecipitation method etc., but there are all for these materials and method
More disadvantages, as amphiphilic polymers materials synthesis is relatively complicated, therefore the amphiphilic polymers material price being commercialized is expensive.System
The step of standby micella, is cumbersome and production technology is relative complex, needs multiple programs, means and equipment, higher cost, technique needs
It is further simplified, and often introduces a large amount of organic solvents and auxiliary agent, generation environment pollution and harm limit its scale metaplasia
It produces.Therefore, efficient, easy and nano pesticide of green and preparation method thereof is researched and developed to be of great significance.
Summary of the invention
The object of the present invention is to provide a kind of pesticide polyelectrolyte nano-micelle and preparation method thereof, preparation method letters
Single, without using the big organic solvent of toxicity, composite environmental-friendly requirement, rule is presented in prepared pesticide polyelectrolyte nano-micelle
Spherical structure disperses stability that is uniform and being able to maintain the long period.
Present invention firstly provides a kind of pesticide polyelectrolyte nano-micelle, in the pesticide polyelectrolyte nano-micelle,
Hydrophobic pesticidal is wrapped in the nanometer formed by the interaction of charge between Sensor Chip CM 5 and polycationic electrolyte
In micella.
In above-mentioned pesticide polyelectrolyte nano-micelle, the hydration partial size of the pesticide polyelectrolyte nano-micelle can be
150~300nm.The surface of the pesticide polyelectrolyte nano-micelle has negative charge.
In above-mentioned pesticide polyelectrolyte nano-micelle, the Sensor Chip CM 5 can be carboxymethyl-β -1, and the Portugal 3-D- is poly-
Sugar.Carboxymethyl-β -1,3-D- the glucan is the carboxyl methylation derivant from yeast dextran.Carboxymethyl-the β-
The degree of substitution by carboxymethyl of 1,3-D- glucan can be 50%~75%.
The polycationic electrolyte can be chitosan, chitosan hydrochloride, chitosan quaternary ammonium salt, nucleoprotamine sulfuric acid
At least one of salt and cationic polypeptide.
The hydrophobic pesticidal raw medicine can be avermectin, Fluoxastrobin, Prochloraz, propiconazole, paclobutrazol, efficient chlorine cyanogen chrysanthemum
At least one of ester and Cyhalothrin.
In above-mentioned pesticide polyelectrolyte nano-micelle, the Sensor Chip CM 5, the polycationic electrolyte and
The mass ratio of the hydrophobic pesticidal raw medicine can be 2:(0.8~1.2): (0.05~0.1), concretely 2:1:(0.05~
0.1), 2:1:0.05 or 2:1:0.1.
In above-mentioned pesticide polyelectrolyte nano-micelle, the pesticide polyelectrolyte nano-micelle can be made by the following method
It is standby to obtain: the Sensor Chip CM 5, the polycationic electrolyte and the hydrophobic pesticidal raw medicine self assembly in water,
Obtain the pesticide polyelectrolyte nano-micelle.
The specific steps of the method can are as follows: the aqueous solution of the polycationic electrolyte is added dropwise to by the carboxylic first
In the mixed liquor of the solution composition of the aqueous solution of base glucan and the pesticide original medicine, solid product is collected by centrifugation, can be obtained
The pesticide polyelectrolyte nano-micelle.
The mass percentage of the aqueous solution of the polycationic electrolyte can be 0.1~0.2%, concretely
0.1%.
The mass percentage of the aqueous solution of the Sensor Chip CM 5 can be 0.2~0.4%, concretely 0.2%.
The mass percentage of the solution of the pesticide original medicine can be 0.05~0.1%, concretely 0.1%.
Solvent in the solution of the pesticide original medicine is organic solvent that can be miscible with water, such as ethyl alcohol, methanol and acetonitrile
At least one of.
Liquid is stirred during the dropwise addition, the revolving speed of the stirring can be 700~900rpm, concretely
900rpm；Continue to stir after being added dropwise, the time can be 5~20min, concretely 10min.
The revolving speed of the centrifugation can be 8000~13000rmp, concretely 12000rpm；Time is 5~10min, specifically
It can be 10min.
Invention further provides the preparation methods of above-mentioned pesticide polyelectrolyte nano-micelle, include the following steps: institute
Sensor Chip CM 5, the polycationic electrolyte and the hydrophobic pesticidal raw medicine self assembly in water are stated, is obtained described
Pesticide polyelectrolyte nano-micelle.
In above-mentioned preparation method, the specific steps of the method can are as follows: by the water-soluble of the polycationic electrolyte
Drop adds in the mixed liquor by the solution composition of the aqueous solution and the pesticide original medicine of the Sensor Chip CM 5, is collected by centrifugation
The pesticide polyelectrolyte nano-micelle can be obtained in solid product.
The mass percentage of the aqueous solution of the polycationic electrolyte can be 0.1~0.2%, concretely
0.1%.
The mass percentage of the aqueous solution of the Sensor Chip CM 5 can be 0.2~0.4%, concretely 0.2%.
The mass percentage of the solution of the pesticide original medicine can be 0.05~0.1%, concretely 0.1%.The agriculture
Solvent in the solution of medicine raw medicine is organic solvent that can be miscible with water, such as at least one of ethyl alcohol, methanol and acetonitrile.
Liquid is stirred during the dropwise addition, the revolving speed of the stirring can be 700~900rpm, concretely
900rpm；Continue to stir after being added dropwise, the time can be 5~20min, concretely 10min.
The revolving speed of the centrifugation can be 8000~13000rmp, concretely 12000rpm；Time can be 5~10min, tool
Body can be 10min.
The invention has the following beneficial effects:
(1) present invention utilizes poly- electrolysis using Sensor Chip CM 5 and conventional polycation electrolyte as assembling original part
Matter nano-micelle forms pesticide polyelectrolyte nano-micelle containing suitable for Multiple Pesticides.Nano carrier material used is made a living
The good and biodegradable natural polymeric material derivative of object compatibility, and its is from a wealth of sources, it is cheap.
(2) preparation method of pesticide polyelectrolyte nano-micelle of the present invention prevents having using surfactant and high poison
Solvent, composite environmental-friendly requirement have the characteristics that preparation process is simple and reaction condition is mild, can produce skill in pesticidal preparations
Art field is with good application prospect.
(3) spherical structure of rule is presented in the pesticide polyelectrolyte nano-micelle prepared by the present invention, disperses uniform and energy
The stability being enough maintained for a long time.It is contained and is tested using avermectin and Fluoxastrobin as model pesticide, drugloading rate all may be used
Reach 50% or more.Averagely hydration partial size keeps good dispersibility and stability in 200nm or so.
Detailed description of the invention
Fig. 1 is the shape after transmission electron microscope (TEM) test for the pesticide polyelectrolyte nano-micelle being prepared in embodiment 1
Looks figure.
Fig. 2 is that the aqueous solution for the pesticide polyelectrolyte nano-micelle being prepared in embodiment 1 passes through dynamic light scattering
(DLS) the hydration grain size distribution after testing.
Fig. 3 is that the aqueous solution for the pesticide polyelectrolyte nano-micelle being prepared in embodiment 1 passes through dynamic light scattering
(DLS) the surface Zeta potential distribution map after testing.
Fig. 4 is the shape after transmission electron microscope (TEM) test for the pesticide polyelectrolyte nano-micelle being prepared in embodiment 2
Looks figure.
Fig. 5 is that the aqueous solution for the pesticide polyelectrolyte nano-micelle being prepared in embodiment 2 passes through dynamic light scattering
(DLS) the hydration grain size distribution after testing.
Fig. 6 is that the aqueous solution for the pesticide polyelectrolyte nano-micelle being prepared in embodiment 2 passes through dynamic light scattering
(DLS) the surface zeta potential potential image after testing.
Specific embodiment
Experimental method used in following embodiments is conventional method unless otherwise specified.
The materials, reagents and the like used in the following examples is commercially available unless otherwise specified.
Carboxymethyl-β -1,3-D- glucan, degree of substitution by carboxymethyl 50-75%, Angel Yeast Biotechnology Co., Ltd；
Chitosan hydrochloride, deacetylation >=90%, ZHEJIANG AOXING BIOTECHNOLOGY CO., LTD；
Avermectin, purity > 96%, Hebei Veyong Biochemical Farm Chemical Co., Ltd.；
Fluoxastrobin, purity 95%-98%, Hebei Veyong Biochemical Farm Chemical Co., Ltd..
Using laser particle analyzer (DLS, Britain Malvern, Zetasizer NanoZS) to acquired in following embodiment
Nano-micelle carry out hydration partial size and surface zeta potential current potential tested.Test condition: nano-micelle in aqueous solution dense
Degree is 0.01mg/ml, and 25 DEG C of temperature, optical maser wavelength 633nm, constant temperature 20min, each sample test three times, take before detecting every time
Average value.
Using transmission electron microscope (TEM, U.S. FEI, Tecnai G220S-TWIN, 200KV) to acquired in following embodiment
Nano-micelle carry out shape characteristic observation.Method for making sample: nano-composition is diluted to 0.005mg/ml with deionized water, is taken
10 μ l samples are added drop-wise on the 230 mesh copper mesh for supporting film containing carbon, after freeze-day with constant temperature, with tem observation sample topography.
Embodiment 1 prepares pesticide polyelectrolyte nano-micelle
Pesticide polyelectrolyte nano-micelle is prepared in accordance with the following steps:
(a) preparation of carboxymethyl-β -1,3-D- dextran solution: the carboxymethyl-β -1,3-D- glucan for weighing 40mg is molten
Then solution is sufficiently stirred in the deionized water of 20ml, by ultrasound so that being completely dissolved, obtain 0.2wt% mass percentage and contain
Carboxymethyl-β -1,3-D- the glucan aqueous solution of amount；
(b) preparation of chitosan hydrochloride solution: the chitosan hydrochloride for weighing 20mg is dissolved in the deionized water of 20ml
In, it is then sufficiently stirred, by ultrasound so that being completely dissolved, obtains the polycation electrolyte of 0.1wt% mass percentage
Aqueous solution；
(c) preparation of the pesticide solution: the avermectin for weighing 10mg is dissolved in 10ml methanol, is then sufficiently stirred, and is led to
Ultrasound is crossed so that being completely dissolved, obtains the abamectin solution of 0.1wt% mass percentage；
(d) at room temperature, carboxymethyl-β -1, the 3-D- glucan for the avermectin methanol solution of 1ml being added to 20ml is molten
It in liquid, and is uniformly mixed, is configured to the homogeneous phase solution of 21ml.
(e) the 20ml chitosan hydrochloride aqueous solution of above-mentioned preparation is slowly added dropwise in above-mentioned (d) with 5ml syringe
It in homogeneous phase solution, is added dropwise on one side, solution is slowly stirred with the speed of 900rpm on one side, until being added dropwise, continue to stir
10min, the solution of available appearance transparent and blueing light are centrifuged 10min with 12000rpm, obtain centrifugation product, are used in combination
Deionized water washes away the avermectin of unentrapped, obtains pesticide polyelectrolyte nano-micelle.
The above-mentioned pesticide polyelectrolyte nano-micelle being prepared is dispersed in water again, to obtain containing Avermectin
The aqueous solution of the polyelectrolyte nano-micelle of element.Use high performance liquid chromatography determine avermectin contain efficiency for
58.2%.
The transmission electron microscope photo for the pesticide polyelectrolyte nano-micelle that the present embodiment is prepared is as shown in Figure 1, from the figure
As can be seen that the dry state partial size of pesticide polyelectrolyte nano-micelle is 200nm or so.
Hydration grain size distribution such as Fig. 2 institute of the light scattering for the pesticide polyelectrolyte nano-micelle that the present embodiment is prepared
Show, from this figure, it can be seen that the hydration partial size of pesticide polyelectrolyte nano-micelle is 195.5nm, polydispersity coefficient 0.234.
Zeta potential distribution map such as Fig. 3 institute of the light scattering for the pesticide polyelectrolyte nano-micelle that the present embodiment is prepared
Showing, the pesticide polyelectrolyte nano-micelle surface obtained as can be seen from this figure has a negative charge, and average Zeta potential is-
36.3mV。
Embodiment 2 prepares pesticide polyelectrolyte nano-micelle
Pesticide polyelectrolyte nano-micelle is prepared in accordance with the following steps
(a) preparation of carboxymethyl-β -1,3-D- dextran solution: preparation method is the same as (a) in embodiment 1；
(b) preparation of chitosan hydrochloride solution: preparation method is the same as (b) in embodiment 1；
(c) preparation of the pesticide solution: the Fluoxastrobin for weighing 10mg is dissolved in 10ml methanol, is then sufficiently stirred, is passed through
For ultrasound so that being completely dissolved, preparation obtains the Fluoxastrobin methanol solution of 0.1wt% mass percentage；
(d) at room temperature, the Fluoxastrobin methanol solution of 2ml is added to carboxymethyl-β -1, the 3-D- dextran solution of 20ml
In, and be uniformly mixed, it is configured to the homogeneous phase solution of 22ml.
(e) the chitosan hydrochloride aqueous solution of the above-mentioned preparation of 20ml is slowly added dropwise in above-mentioned (d) with 5ml syringe
In homogeneous phase solution, and solution 10min is slowly stirred with the speed of 900rpm, after being added dropwise, available appearance transparent it is general
The solution of blue light is centrifuged 10min with 12000rpm, obtains centrifugation product, and the Fluoxastrobin of unentrapped is washed with deionized water,
Obtain pesticide polyelectrolyte nano-micelle.
Again it disperses the above-mentioned pesticide polyelectrolyte nano-micelle being prepared in aqueous solution, to obtain containing phonetic
The aqueous solution of the polyelectrolyte nano-micelle of bacterium ester.Use high performance liquid chromatography determine Fluoxastrobin contain efficiency for
53.1%.
The transmission electron microscope photo such as Fig. 4 for the pesticide polyelectrolyte nano-micelle that the present embodiment is prepared shows, can from the figure
To find out, the dry state partial size of pesticide polyelectrolyte nano-micelle is 200nm or so.
The pesticide polyelectrolyte nano-micelle that the present embodiment is prepared light scattering grain size distribution as shown in figure 5,
From this figure, it can be seen that the hydration partial size of pesticide polyelectrolyte nano-micelle is 182.9nm, polydispersity coefficient 0.147.
Zeta potential distribution map such as Fig. 6 institute of the light scattering for the pesticide polyelectrolyte nano-micelle that the present embodiment is prepared
Showing, the pesticide polyelectrolyte nano-micelle surface obtained as can be seen from this figure has a negative charge, and average Zeta potential is-
45.5mV。
Claims (10)
1. a kind of pesticide polyelectrolyte nano-micelle, it is characterised in that: in the pesticide polyelectrolyte nano-micelle, hydrophobicity agriculture
Pack is rolled in the nano-micelle formed by the interaction of charge between Sensor Chip CM 5 and polycationic electrolyte.
2. pesticide polyelectrolyte nano-micelle according to claim 1, it is characterised in that: the pesticide polyelectrolyte nanometer
The hydration partial size of micella is 150~300nm；And/or
The surface of the pesticide polyelectrolyte nano-micelle has negative charge.
3. pesticide polyelectrolyte nano-micelle according to claim 1 or 2, it is characterised in that: the Sensor Chip CM 5
For carboxymethyl-β -1,3-D- glucan；And/or
The degree of substitution by carboxymethyl of the carboxymethyl-β -1,3-D- glucan is 50%~75%.
4. pesticide polyelectrolyte nano-micelle according to any one of claim 1-3, it is characterised in that: it is described it is poly- sun from
Sub- property electrolyte is in chitosan, chitosan hydrochloride, chitosan quaternary ammonium salt, protamine sulfate and cationic polypeptide
It is at least one.
5. pesticide polyelectrolyte nano-micelle described in any one of -4 according to claim 1, it is characterised in that: the hydrophobicity
Pesticide original medicine is in avermectin, Fluoxastrobin, Prochloraz, propiconazole, paclobutrazol, effective cypermethrin and Cyhalothrin
It is at least one.
6. pesticide polyelectrolyte nano-micelle according to any one of claims 1-5, it is characterised in that: the carboxymethyl
The mass ratio of glucan, the polycationic electrolyte and the hydrophobic pesticidal raw medicine is 2:(0.8~1.2): (0.05~
0.1)。
7. the preparation method of pesticide polyelectrolyte nano-micelle of any of claims 1-6, includes the following steps: institute
Sensor Chip CM 5, the polycationic electrolyte and the hydrophobic pesticidal raw medicine self assembly in water are stated, is obtained described
Pesticide polyelectrolyte nano-micelle.
8. according to the method described in claim 7, it is characterized by: the specific steps of the method are as follows: by the polycation
Property electrolyte aqueous solution be added dropwise to by the mixed of the solution composition of the aqueous solution and the pesticide original medicine of the Sensor Chip CM 5
It closes in liquid, solid product is collected by centrifugation, the pesticide polyelectrolyte nano-micelle can be obtained.
9. according to the method described in claim 8, it is characterized by: the quality hundred of the aqueous solution of the polycationic electrolyte
Dividing content is 0.1~0.2%；And/or
The mass percentage of the aqueous solution of the Sensor Chip CM 5 is 0.2~0.4%；And/or
The mass percentage of the solution of the pesticide original medicine is 0.05~0.1%；Solvent in the solution of the pesticide original medicine
For organic solvent that can be miscible with water.
10. method according to claim 8 or claim 9, it is characterised in that: it is stirred liquid during the dropwise addition, it is described to stir
The revolving speed mixed is 700~900rpm；Continue to stir after being added dropwise, the time is 5~20min；And/or
The revolving speed of the centrifugation is 8000~13000rmp, and the time is 5~10min.
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| WO2021093271A1 (en) * | 2019-11-12 | 2021-05-20 | 南京华洲药业有限公司 | Beta cypermethrin nano aqueous agent, preparation method therefor and use thereof |
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