CN108990991A - A kind of preparation method for the nanoparticle containing fluazinam based on poly lactide-glycolide acid - Google Patents
A kind of preparation method for the nanoparticle containing fluazinam based on poly lactide-glycolide acid Download PDFInfo
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- CN108990991A CN108990991A CN201810799325.9A CN201810799325A CN108990991A CN 108990991 A CN108990991 A CN 108990991A CN 201810799325 A CN201810799325 A CN 201810799325A CN 108990991 A CN108990991 A CN 108990991A
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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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
- A01N25/10—Macromolecular compounds
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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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/12—Powders or granules
- A01N25/14—Powders or granules wettable
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- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
A kind of preparation method for the nanoparticle containing fluazinam based on poly lactide-glycolide acid, belongs to nano material agriculture field.It specifically includes: fluazinam Flu and PLGA is dissolved in the methylene chloride as dispersed phase；PVA or SDS are completely dissolved and prepare continuous phase in deionized water；Dispersed phase is poured into SPG film；Then it adjusts pressure and dispersed phase is dispersed in mixing emulsification generation lotion completely in the continuous phase continuously stirred, completely after emulsification, lotion is continued into stirring 24 hours to evaporate the methylene chloride in emulsion droplet, obtained cured fluazinam PLGA microballoon is centrifuged, it is washed with distilled water, then freeze-drying is collected, and obtains Flu-PLGA particle；Product of the invention has good water-soluble and stability, and the sustained release lasting period is long, and preparation method is simple, and repeatability is high.
Description
Technical field
The invention belongs to nano material agriculture fields.The present invention relates to a kind of slow-release nano pesticides to be contained based on PLGA
The preparation method and application of wide-spectrum bactericide fluazinam.
Technical background
Pesticide keeps playing a significant role in grain yield in prevention and treatment pest disaster, but a large amount of pesticides flow into ambient enviroment meeting
Lead to ecosystem destruction and food pollution.Nano controlled-release technology has broad application prospects, and the moisture of pesticide can be improved
Property and its penetrating power in blade surface are dissipated, and reduces the catalytic degradation of the drug due to caused by the environmental factors such as illumination, by
So that drug therefore can be there is sustained release performance with sustained release in the encapsulating of carrier and extends the lasting period of drug.
Poly lactide-glycolide acid (poly (lactic-co-glycolic acid), PLGA) polymer is due to it
Hypotoxicity, biodegradable and sustained release ability and the carrier for being widely used as various active drug molecules, such as small molecule
Compound and nucleotide.Its safety of food and drug administration (FDA) approved has good biology in human body
Degradability and biocompatibility, the application report in pesticide is very few at present.
Fluazinam [fluoro- 2, the 6- dinitro-toluene of the chloro- N- of 3- (the chloro- 5- trifluoromethyl -2- pyridyl group of 3-)-α, α, α-three
Amine] it is a kind of pyridyl amine wide-spectrum bactericide (Fluazinam, Flu), for fungitoxicity based on non-coupled oxidative phosphorylation
Effect prevents and treats the disease as caused by grey grape born of the same parents, to interlink spore genus, Botrytis, Phytophthora, Sclerotinia and black cultivates Pseudomonas bacterium
It is highly effective, but its is not soluble in water, is easier to decompose under light illumination, applies and is subject to certain restrictions in agricultural.
Film emulsifying technology (Shirasu Porous Glass membrane, SPG) be develop in recent years one kind it is novel
Emulsification method has many advantages, such as that emulsification condition mildly consumes little energy, and membrane emulsification can preferably control partial size, reduce partial size
It is distributed and realizes batch production.There is presently no the application reports in the preparation of nano pesticide compound system.
Summary of the invention
A kind of slow-release nano pesticide contains the preparation method of wide-spectrum bactericide fluazinam, including following step based on PLGA
It is rapid:
(1) fluazinam Flu and PLGA are dissolved in the methylene chloride as dispersed phase, fluazinam Flu is in methylene chloride
Concentration be preferably 1-30mg/ml, then more preferable 4mg/ml.
(2) continuous phase is prepared by the way that PVA or SDS to be completely dissolved in deionized water；PVA or SDS are in deionized water
In concentration be 0.5-2%, it is 0.5% that then the more preferable concentration of PVA, which is the more preferable concentration of 1%, SDS,.
(3) step (1) dispersed phase is poured into SPG film；Then pressure (preferably 100-400kPa) is adjusted by dispersed phase point
It is dispersed in the continuous phase in the step of continuously stirring (2) and emulsification generation lotion completely is mixed, wherein PVA or SDS in lotion
Be (5-20) with the mass ratio of PLGA: 1, then more preferable mass ratio PVA:PLGA be 20:1 and, SDS:PLGA is 10:1 (4)
After step (3) completely emulsification, lotion is continued into stirring 24 hours to evaporate the methylene chloride in emulsion droplet；
(5) cured fluazinam PLGA microballoon is centrifuged after step (4) being evaporated methylene chloride, and then freeze-drying is collected, and is obtained
Flu-PLGA-PVA or Flu-PLGA-SDS particle；The mass ratio of preferred Flu and PLGA is preferably (1-3): 10, more preferably
2:10；
The preparation method of the PLGA load fluazinam, (surface is living in 600-1900nm for Flu-PLGA-PVA size controlling
Property agent PVA) and Flu-PLGA-SDS partial size 300-1100nm (surfactant SDS).
Advantages of the present invention:
Slow-release nano pesticide the particle Flu-PLGA-PVA and Flu-PLGA-SDS of this research preparation have suitable reason
Change property, good water dispersible and stability, the sustained release lasting period is long, and preparation method is simple, and repeatability is high.Since fluazinam is received
The problems such as partial size of rice pesticide is smaller, can solve traditional pesticide water bad dispersibility, and effective rate of utilization is low and environmental pollution, can be with
It is sustained release into fungicide fluazinam on blade, reduces the sprinkling number of pesticide, there is better wetting effect on blade face,
Since the photodissociation that the protective effect of carrier can reduce fluazinam improves the effective rate of utilization of pesticide.
Detailed description of the invention
Fig. 1 is scanning electron microscope image (a) the Flu-PLGA PVA nanoparticle (b) that PLGA contains fluazinam nanoparticle
Flu-PLGA SDS nanoparticle
Fig. 2 is statistical size distribution histogram (a) the Flu-PLGA PVA nanoparticle that PLGA contains fluazinam nanoparticle
Son (b) Flu-PLGA PVA nanoparticle
Fig. 3 be PLGA under ultraviolet light contain fluazinam nanoparticle (surfactant SDS, PVA) light degradation it is bent
Line, using fluazinam marketed drugs as control；
Fig. 4 is that PLGA contains stability diagram picture of the fluazinam nanoparticle under different storage temperatures.
Fig. 5 is that PLGA contains fluazinam nanoparticle in the image of cucumber leaves surface contact angle, with the commercially available medicine of fluazinam
Object is as control Flu-PLGA (SDS) (a) Flu-PLGA NPs (PVA) (b) fluazinam cream preparation (c) deionized water (d)；
Fig. 6 is that PLGA contains bactericidal effect (drug of the fluazinam nanoparticle on day 4 with the 8th day Rhizoctonia solani
The actual concentrations 12.5ug/ml of middle fluazinam), deionized water is negative control, using fluazinam marketed drugs as positive control.
Fig. 7 be various concentration PVA PLGA contain fluazinam nanoparticle Cumulative release profile (PVA concentration 0.5%,
1%, 2%).
Fig. 8 be various concentration SDS PLGA contain fluazinam nanoparticle Cumulative release profile (SDS concentration 0.5%,
1%, 2%).
Specific embodiment
Below with reference to embodiment, the present invention will be further described, but the present invention is not limited to following embodiments.
Embodiment 1:
The fluazinam of a certain amount of 20mg and 100mg PLGA are dissolved in the 5ml methylene chloride as dispersed phase.Passing through will
2g PVA or 1g SDS, which are dissolved completely in 200ml deionized water, prepares continuous phase.By dispersed phase 6ml dissolved with fluazinam and
The dichloromethane solution of PLGA pours into SPG membrane emulsifier.Then pressure 250kPa is adjusted continuously to stir so that dispersed phase to be dispersed in
In the PVA solution (or SDS solution) mixed.After generating enough lotion 200ml (wherein in lotion PLGA and PVA mass ratio
The mass ratio 1:10 of 1:20, PLGA and SDS), lotion is stirred 24 hours to evaporate the methylene chloride in emulsion droplet.It will be cured
The centrifugation of fluazinam PLGA microballoon, is washed with distilled water three times, and then freeze-drying is collected.Preferably the mass ratio of Flu and PLGA is
1:5。
Using the form (Fig. 1) of scanning electron microscope observation nanoparticle, and partial size is detected, size distribution
Histogram is shown in Fig. 2.Result figure 1SEM image shows the spherical shape that nanoparticle is evenly distributed and has smaller size, and Fig. 2 is shown
The average grain diameter of nano particle is about 612.80nmFlu-PLGA NPs (PVA) and 314.13nmFlu-PLGA NPs
(SDS)。
The photodissociation performance of implementation Flu-PLGA nanoparticle and heat-staple measurement (Fig. 3 and Fig. 4).From the residual of fluazinam
Amount assesses the photodissociation behavior of different irradiation times, and commercially available fluazinam preparation is used as and is compareed, and 25 DEG C of room temperature, as a result such as Fig. 3 institute
Show, Flu-PLGA Nano medication has better optical stability compared with fluazinam commercial preparation.Flu-PLGA shown in Fig. 4 receives
Rice drug is only a small amount of at 54 DEG C to decompose in 4 DEG C, 25 DEG C of stabilizations, all has preferable stablize at a temperature of three kinds different
Property.
Using fluazinam commercial preparation and deionized water as positive control, Flu-PLGA nanoparticle is measured in cucumber plant
Contact angle (Fig. 5) on blade: it wins the cucumber plant blade grown at room temperature and that disleaf table is washed with deionized is miscellaneous
Matter is fixed on glass slide after dry, the contact angle dripped with the nanometer medicine on contact angle apparatus measures blade.Flu-PLGA is received
The water dispersion drop of rice drug (1mg/ml, 2ul) is added drop-wise on leaf surface, captures the image of blade surface drop and what is obtained connect
Feeler degree, is averaged for duplicate measurements 6 times, selects deionized water and fluazinam commercial preparation as control.As the result is shown
Flu-PLGA Nano medication has smaller contact angle compared with fluazinam commercial preparation, deionized water, shows that Flu-PLGA receives
Rice drug has better blade face wetability.
The suppression that fungi is grown using Rhizoctonia solani Kuhn (Rhizoctonia solani) as targeting bacterium, measurement Nano medication
Shown in production (Fig. 6) result, Flu-PLGA Nano medication has better fungistatic effect compared with fluazinam commercial preparation.Benefit
With the fungistatic effect of the growth rate method assessment Nano medication of mycelia, the Flu-PLGA (PVA) for being 3.623mg by quality
Flu-PLGA (SDS) Nano medication of 4.310mg is dissolved in 20mlPDA culture medium and gradient dilution preparation is practical containing concentration
For 25ug/ml, the PDA drug containing culture dish of 12.5ug/ml, 6.25ug/ml are beaten and take diameter as the miliary damping-off bacteria cake of 5mm and fall
The drug containing culture dish center of various concentration is set, culture dish is placed in 28 DEG C of incubator and cultivates.It is taken when on day 4 with the 8th day
Each culture dish and measure diameter out, select not the culture dish of drug containing with fluazinam commercial preparation as compareing, preferably actually contain
Flu-PLGA (the PVA, SDS) Nano medication that concentration is 12.5ug/ml has good fungistatic effect.
Embodiment 2:
By 10mg, the fluazinam of 20mg, 30mg are dissolved in the 5ml dichloro as dispersed phase with three parts of 100mg PLGA respectively
In methane.Then, continuous phase is prepared by the way that 2g PVA or 1g SDS to be dissolved completely in 200ml deionized water.Then, will
Dispersed phase pours into SPG membrane emulsifier.Then adjust pressure 250Pa with dispersed phase is dispersed in the PVA solution continuously stirred (or
SDS solution) in；(the mass ratio of the mass ratio 1:20, PLGA and SDS of PLGA and PVA in lotion after generating 200ml lotion
1:10), lotion is stirred 24 hours to evaporate the methylene chloride in emulsion droplet.Finally, by cured fluazinam PLGA microballoon from
The heart is washed with distilled water three times, and then freeze-drying is collected.Different dosages are to the drugloading rate of Flu-PLGA nanoparticle and pattern
Influence is shown in Table 1.Go out the nanoparticle drugloading rate with higher that drug input amount is 20mg as the result is shown and does not generate crystallization point
It is preferable to dissipate property, drugloading rate is 13.8%Flu-PLGA NPs (PVA) and 11.6%Flu-PLGA NPs (SDS).With this dosage
Nano medication carry out sustained release experiment simultaneously using commercially available fluazinam preparation as compare.As a result Flu-PLGA phase as shown in Figure 7
There is better sustained release performance for commercially available medicament.
Influence of the different dosages of table 1 to the drugloading rate and pattern of Flu-PLGA nanoparticle
(a) influence (a) (a) of the PVA concentration to influence (b) the SDS concentration of nanoparticle properties to nanoparticle properties
PVA
(b)SDS
Embodiment 3:
The fluazinam of 20mg and 100mg PLGA are dissolved in the 5ml methylene chloride as dispersed phase.Then, pass through by
1g, 2g, 3gPVA, which are dissolved completely in 200ml deionized water, prepares continuous phase, i.e., PVA concentration is 0.5%, 1%, 1.5%.
Then dispersed phase is poured into SPG membrane emulsifier.Then pressure 250Pa is adjusted so that dispersed phase to be dispersed in the PVA continuously stirred
In solution.After generating 200ml lotion, lotion is stirred 24 hours to evaporate the methylene chloride in emulsion droplet.Finally, will solidification
Fluazinam PLGA microballoon centrifugation, washing, freeze-drying collect.The accumulative release rate of Flu-PLGA nanoparticle is measured (see
15mgFlu-PLGA (PVA, SDS) nano particle uniformly Fig. 8) is suspended in 5ml ethyl alcohol respectively: in the mixed solution of water 1:1,
Suspension is transferred in bag filter, bag filter is sealed in 95ml using ethyl alcohol: burning of the water 1:1 mixed solution as dissolution medium
In cup, 37 DEG C are placed the beaker, is cultivated in the constant-temperature table of 100rpm.It is drawn in specific time interval molten outside 5ml bag filter
Isometric fresh dissolution medium is added in liquid.It is detected by high performance liquid chromatography (HPLC), testing conditions, mobile phase first
Alcohol: water=85:15, sampling volume v=10ul, Detection wavelength 240nm, 30 DEG C of column temperature, retention time about 6min.The result shows that
Emulsifier concentration be 1%PVA prepared by nanoparticle, shown compared with the PVA nanoparticle of other two kinds of concentration compared with
High release rate.
Embodiment 4:
The fluazinam of 20mg and 100mg PLGA are dissolved in the 5ml methylene chloride as dispersed phase.Then, pass through by
1g, 2g, 3gSDS, which are dissolved completely in 200ml ionized water, prepares continuous phase, i.e., SDS concentration is 0.5%, 1%, 1.5%.
Then, dispersed phase is poured into SPG membrane emulsifier.Then pressure 250Pa is adjusted to continuously stir so that dispersed phase to be dispersed in
In SDS solution.After the lotion for generating enough 200ml, lotion is stirred 24 hours to evaporate the methylene chloride in emulsion droplet.Most
Afterwards, cured fluazinam PLGA microballoon is centrifuged, washing, freeze-drying is collected.Respectively by 15mgFlu-PLGA (PVA, SDS) nanometer
Grain is uniformly suspended in 5ml ethyl alcohol: in the mixed solution of water 1:1, suspension being transferred in bag filter, bag filter is sealed in
95ml is using ethyl alcohol: water 1:1 mixed solution is as in the beaker of dissolution medium.37 DEG C are placed the beaker, the constant-temperature table of 100rpm
Middle culture.Solution outside 5ml bag filter is drawn in specific time interval and adds isometric fresh dissolution medium.By efficient
Liquid chromatography (HPLC) measures, testing conditions, mobile phase methanol: water=85:15, sampling volume v=10ul, detects wave
Long 240nm, 30 DEG C of column temperature, retention time about 6min.The result shows that concentration is nanoparticle prepared by 0.5%SDS, with
The SDS nanoparticle of other two kinds of concentration is compared and shows higher release rate.
Claims (8)
1. the preparation method that a kind of slow-release nano pesticide contains wide-spectrum bactericide fluazinam based on PLGA, which is characterized in that packet
Include following steps:
(1) fluazinam Flu and PLGA are dissolved in the methylene chloride as dispersed phase；
(2) continuous phase is prepared by the way that PVA or SDS to be completely dissolved in deionized water；
(3) step (1) dispersed phase is poured into SPG film；Then it adjusts pressure and dispersed phase is dispersed in the step of continuously stirring (2)
In continuous phase in be mixed completely emulsification generate lotion；
(4) after step (3) completely emulsification, lotion is continued into stirring 24 hours to evaporate the methylene chloride in emulsion droplet；
(5) cured fluazinam PLGA microballoon is centrifuged after step (4) being evaporated methylene chloride, and then freeze-drying is collected, and obtains Flu-
PLGA-PVA or Flu-PLGA-SDS particle.
2. the preparation that a kind of slow-release nano pesticide described in accordance with the claim 1 contains wide-spectrum bactericide fluazinam based on PLGA
Method, which is characterized in that it is 100-400kPa that step (3), which adjusts pressure,.
3. the preparation that a kind of slow-release nano pesticide described in accordance with the claim 1 contains wide-spectrum bactericide fluazinam based on PLGA
Method, which is characterized in that the concentration of step (1) fluazinam Flu in methylene chloride is preferably 1-30mg/ml, then more preferably
4mg/ml。
4. the preparation that a kind of slow-release nano pesticide described in accordance with the claim 1 contains wide-spectrum bactericide fluazinam based on PLGA
Method, which is characterized in that the concentration of step (2) PVA or SDS in deionized water is 0.5%-2%, and then PVA is more preferably dense
It is 0.5% that degree, which is the more preferable concentration of 1%, SDS,.
5. the preparation that a kind of slow-release nano pesticide described in accordance with the claim 1 contains wide-spectrum bactericide fluazinam based on PLGA
Method, which is characterized in that wherein the mass ratio of PVA or SDS and PLGA is (5-20) to step (3) in lotion: 1, then more preferably
Mass ratio PVA:PLGA is 20:1 and SDS:PLGA 10:1.
6. the preparation that a kind of slow-release nano pesticide described in accordance with the claim 1 contains wide-spectrum bactericide fluazinam based on PLGA
Method, which is characterized in that the mass ratio of Flu and PLGA is preferably (1-3): 10, more preferable 2:10.
7. the preparation that a kind of slow-release nano pesticide described in accordance with the claim 1 contains wide-spectrum bactericide fluazinam based on PLGA
Method, which is characterized in that Flu-PLGA-PVA size controlling is in 600-1900nm, Flu-PLGA-SDS partial size 300-1100nm.
8. the slow-release nano pesticide being prepared according to the described in any item methods of claim 1-7 is based on PLGA and contains wide spectrum
Fungicide fluazinam.
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| CN201810799325.9A CN108990991A (en) | 2018-07-19 | 2018-07-19 | A kind of preparation method for the nanoparticle containing fluazinam based on poly lactide-glycolide acid |
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