CN108064844A - A kind of cyclodextrin modified graphene-houghite pesticide slow-releasing agent and preparation method thereof - Google Patents
A kind of cyclodextrin modified graphene-houghite pesticide slow-releasing agent and preparation method thereof Download PDFInfo
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- CN108064844A CN108064844A CN201711388920.5A CN201711388920A CN108064844A CN 108064844 A CN108064844 A CN 108064844A CN 201711388920 A CN201711388920 A CN 201711388920A CN 108064844 A CN108064844 A CN 108064844A
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- cyclodextrin
- houghite
- pesticide
- releasing agent
- modified graphene
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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
-
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
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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)
- Medicinal Preparation (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses a kind of cyclodextrin modified graphene houghite pesticide slow-releasing agents, are made again with houghite stripper hybrid reaction by cyclodextrin modified graphene inclusion pesticide.This method makes full use of cyclodextrin to the Inclusion property and graphene of object and the electrostatic interaction of houghite, greatly improves the sustained release performance of hybrid.Drugloading rate is the 3%~50% of the hybrid by percentage to the quality.Hybrid of the present invention has the characteristics that simple preparation process, mild condition, drugloading rate is big, sustained release performance is good, the preparation available for pesticide slow-releasing agent.
Description
Technical field
The present invention relates to a kind of cyclodextrin modified graphene-houghite pesticide slow-releasing agents and preparation method thereof, belong to
New material and pesticide release control technology field.
Background technology
Graphene is developed in recent years a kind of tightly packed into the two of monolayer honeycomb shape lattice structure by carbon atom
Reform material is the elementary cell for building other dimension Carbon Materials.Due to its have unique engineering properties, macroscopic property,
Chemical property and optical property make it have great answer in fields such as electronics, information, the energy, catalysis, material and biological medicines
Use prospect.Due to the reasons in structure of itself, it is easy to be piled into self-assembly, and many advantageous properties of graphene can only be
It can just be showed when being individual layer two-dimensional structure, and designing or introduce the next effective dispersed graphite alkene of new functional molecular prevents its heap
Product brings new function to become an important problem simultaneously.
Cyclodextrin (cyclodextrin, abbreviation CD) is to pass through α-Isosorbide-5-Nitrae glucosides by 6,7 or 8 D- glucopyranose units
Interior hydrophobic, the outer hydrophilic cyclic oligosaccharide that key connection forms, be referred to as α-, β-and gamma-cyclodextrin.Since its is special
" cone cylinder " shape structure, cyclodextrin can form stable master with the various organic and inorganic and biomolecule of Selective recognition and inclusion
The super-molecule assembling body of object inclusion complex or nanostructured.Cyclodextrin is environmentally friendly, good with water solubility, biocompatibility
The characteristics such as good, have become significant subject molecule a kind of in supramolecular chemistry, know in sensing, catalysis, self assembly, molecule
Not, the fields extensive use such as medicament transport.If with cyclodextrin modified graphene, reaching enhancing graphene water solubility and preventing
While its self aggregation, moreover it is possible to which cyclodextrin (Supramolecular Recognition ability and inclusion) and graphene (high-ratio surface and highly conductive) is excellent
Good molecule performance is combined together, and will have extensive use in sensing, electro-catalysis, fluorescence and electronics etc..Guo Yujing etc.
Research shows that cyclodextrin modified graphene hybrid significantly improves the dispersion performance of graphene, to 5 kinds of biomolecule (DOPA
Amine, uric acid, noradrenaline, change tyrosine, biochemical tryptophan) and 3 kinds of drugs (paracetamol, rutin, thioridazine)
It is respectively provided with good recognition capability (Y.J.Guo, S.J.Guo, J.T.Ren, Y.M.Zhai, S.J.Dong, E.K.Wang, ACS
Nano, 2010,4,4001-4010.).They, which also study, shows that the membrane electrode based on cyclodextrin-graphene hybrid is not only shown
Graphene excellent electrical properties are shown, and show the cyclodextrin Supramolecular Recognition ability excellent to fungicide carbendazim
(Y.J.Guo, S.J.Guo, J.Li, E.K.Wang, S.J.Dong, Talanta, 2011,84,60-64.).Open quick etc. establish
With β-CD modification graphene detection anabasine insecticide paichongding electrochemical method (M.Zhang, H.T.Zhao,
X.Yang, A.J.Dong, H.Zhang, J.Wang, G.Y.Liu, X.C.Zhai, Sens.Actuators B：Chem., 2016,
229,190-199.).Cyclodextrin modified graphene hybrid can identify the organic guest molecule of inclusion, however cyclodextrin is located at
Graphene surface, guest molecule is easy to release inclusion in the cavities.How come control guest molecule dischargeIn graphite
Alkene surface loads houghite again can solve the problems, such as this.
Houghite is a kind of typical layered anionic material, it can accommodate various biologies and organic molecule etc. and be formed with
Machine-inorganic functional hybrid.LDH has the characteristics that synthetic method is relatively easy, ion-exchange capacity is high and charge density is high.By
It is negatively charged in graphene surface, and houghite is positively charged, and class neatly can be loaded in graphene surface using electrostatic interaction
Stone.The present invention utilizes cyclodextrin modified graphene inclusion pesticide, loads houghite again in graphene surface and is prepared into pesticide
Sustained release agent discharges so as to fulfill to the control of pesticide.By the end of the report that yet there are no pertinent literature.
The content of the invention
Cyclodextrin modified graphene has good molecule distinguishability to pesticide molecule, however sustained release performance is poor.This
Invention provides a kind of cyclodextrin modified graphene-houghite pesticide slow-releasing agent and preparation method thereof, available for pesticide
Conveying and sustained release.
Cyclodextrin modified graphene-houghite pesticide slow-releasing agent of the present invention, is by cyclodextrin modified graphite
Alkene inclusion pesticide is made again with houghite stripper hybrid reaction.Wherein, the cyclodextrin is non-ionic cyclodextrin；Ring
The graphene of dextrin modification is obtained by graphene oxide and cyclodextrin reaction reduction；The houghite stripper is by class water
Talcum reacts stripping in formamide solvent and obtains.The pesticide for cypermethrin, effective cypermethrin, Cyhalothrin,
One kind in decis, Biphenthrin, drugloading rate are the 3%~50% of sustained release agent by percentage to the quality.
In above-mentioned cyclodextrin modified graphene-houghite pesticide slow-releasing agent：Cyclodextrin is alpha-cyclodextrin, β-ring paste
In essence, gamma-cyclodextrin, methyl-B-cyclodextrin, hydroxyethyl-β-cyclodextrin, hydroxypropyl-β-cyclodextrin, hydroxyl fourth group-beta-cyclodextrin
One kind.
The preparation method of sustained release agent of the present invention, be by cyclodextrin modified graphene elder generation inclusion pesticide, then with class water
Talcum stripper hybrid reaction is made by filtering, washing dry.Wherein concretely comprise the following steps：
(A) weigh graphene oxide by design flow and cyclodextrin is scattered in the water of removing carbon dioxide, ultrasonic 30min, 50
DEG C heating stirring is reacted 2 days；Aforesaid liquid is cooled to room temperature, hydrazine hydrate is measured by design flow and ammonium hydroxide is added thereto, 60
3h is stirred to react at DEG C；By above-mentioned solution high speed centrifugation, centrifugation 3 times is washed with 95% ethyl alcohol, will be deposited in dry at 60 DEG C
To cyclodextrin modified graphene (CD-rGO)；(B) weigh a certain amount of houghite by design flow and be dispersed in formamide solvent
In, ultrasonic 30min, heating stirring is reacted 2 days at 60 DEG C, obtains transparent houghite stripper；(C) weighed by design flow
A certain amount of pesticide is dissolved in N-Methyl pyrrolidone solvent, and a certain amount of CD-rGO is taken to be dispersed in above-mentioned system, ultrasound
30min reacts certain time in 50 DEG C of heating stirrings, adds a certain amount of houghite stripper and reacts 1 day, with 95%
Ethyl alcohol washing centrifugation 3 times, 60 DEG C of dryings obtain hybrid.
Cyclodextrin modified graphene provided by the invention-houghite sustained release agent preparation method makes full use of cyclodextrin pair
Inclusion property and graphene, the electrostatic interaction of houghite therebetween of pesticide, overcome cyclodextrin modified graphene
The shortcomings that sustained release performance is poor realizes pesticide and slowly discharges.The preparation method is with preparation process is simple, drugloading rate is high, structure
Stablize, the features such as sustained release performance is good.
Description of the drawings
Fig. 1 is that the x-ray powder of cyclodextrin modified graphene-houghite pesticide slow-releasing agent prepared by embodiment 1 spreads out
Penetrate (XRD) figure (XRD diagram of sample BC/HECD-rGO/LDH)
Fig. 2 is that the Fourier transformation of cyclodextrin modified graphene-houghite pesticide slow-releasing agent prepared by embodiment 1 is red
External spectrum figure (FTIR) (the FTIR figures of sample BC/HECD-rGO/LDH, HECD-rGO and BC)
Fig. 3 is that cyclodextrin modified graphene-houghite pesticide slow-releasing agent prepared by embodiment 1 is discharged in different pH
Rate diagram (release profiles of the BC/HECD-rGO/LDH in pH=6.8, pH=5.0)
Specific embodiment
Embodiment 1
Step a weighs 1.0g graphene oxides (GO) and is scattered in the 250ml flasks for filling 100ml removing carbon dioxide water,
The 100ml aqueous solutions containing 6g hydroxyethyl cyclodextrins (HECD), ultrasonic 30min are continuously added, 50 DEG C of heating stirrings are reacted 2 days；
Aforesaid liquid is cooled to room temperature, 0.33ml hydrazine hydrates, 1.66ml ammonium hydroxide is separately added into, 3h is stirred to react at 60 DEG C；It will be upper
Solution is stated in 8000 revs/min of high speed centrifugations, precipitation is washed with 95% ethyl alcohol, centrifuged 3 times, will be deposited at 60 DEG C and be dried to obtain
Cyclodextrin modified graphene (being denoted as HECD-rGO).
Step b weighs the addition of 1.0g houghites and fills in the 250ml flasks of 80ml formamides, in 60 DEG C of stirred in water bath
Obtain within 2 days transparent houghite stripper.
Step c weighs 1.0g effective cypermethrins (BC) active compound and is dissolved in the 250ml burnings for filling 45ml N-Methyl pyrrolidones
In bottle, 1.0g HECD-rGO, ultrasonic 30min are continuously added, reacts 8h in 50 DEG C of heating stirrings.Then 80ml class neatlys are added in
Stone stripper, the reaction was continued for 24 hours, is cooled to room temperature.Centrifugation, precipitation are washed with 95% ethyl alcohol, centrifuged 3 times, will be deposited in 60 DEG C
Lower dry 12h, grinding obtain cyclodextrin modified graphene-houghite pesticide slow-releasing agent (being denoted as BC/HECD-rGO/LDH).
It is shown by XRD spectra (Fig. 1), cyclodextrin modified graphene-houghite pesticide slow-releasing agent has graphene
The feature of crystalline structure and houghite.It is further confirmed to contain effective cypermethrin in sustained release agent by FTIR spectrograms (Fig. 2),
Ultraviolet spectrophotometry is used to determine that BC contents is 3.50% in sample.Understand that hybrid exists by sustained release agent elution profiles (Fig. 3)
PH5.0 and 6.8 has good sustained release performance.
Embodiment 2
Step a weighs 1.0g GO and is scattered in the 250ml flasks for filling 100ml removing carbon dioxide water, continuously add containing
The 100ml aqueous solutions of 6g hydroxypropyl cyclodextrins (HPCD), ultrasonic 30min, 50 DEG C of heating stirrings are reacted 2 days；Aforesaid liquid is cold
But room temperature is arrived, 0.33ml hydrazine hydrates, 1.66ml ammonium hydroxide is separately added into, 3h is stirred to react at 60 DEG C；By above-mentioned solution 8000
Rev/min high speed centrifugation, precipitation are washed with 95% ethyl alcohol, centrifuged 3 times, will be deposited at 60 DEG C be dried to obtain it is cyclodextrin modified
Graphene (is denoted as CD-rGO).
Step b prepares houghite stripper with step b in embodiment 1.
Step c weighs 1.0g effective cypermethrin active compounds and is dissolved in the 250ml flasks for filling 45ml N-Methyl pyrrolidones
In, 1.0g CD-rGO, ultrasonic 30min are added in, reacts 8h in 50 DEG C of heating stirrings.Then 160ml houghites are added in remove
Liquid, the reaction was continued for 24 hours, is cooled to room temperature.Centrifugation, precipitation wash centrifugation 3 times with 95% ethyl alcohol, will be deposited at 60 DEG C dry
12h, grinding obtain cyclodextrin modified graphene-houghite sustained release agent.It is determined using ultraviolet spectrophotometry in sample
Effective cypermethrin content is 5.0%.
Embodiment 3
Step a weighs 1.0g GO and is scattered in the 250ml flasks for filling 100ml removing carbon dioxide water, and addition contains
The 100ml aqueous solutions of 6gHPCD, ultrasonic 30min, 50 DEG C of heating stirrings are reacted 2 days；Aforesaid liquid is cooled to room temperature, is added respectively
Enter 0.50ml hydrazine hydrates, 1.66ml ammonium hydroxide, 3h is stirred to react at 60 DEG C；By above-mentioned solution in 8000 revs/min of high speed centrifugations,
Precipitation is washed with 95% ethyl alcohol, centrifuged 3 times, will be deposited in and is dried to obtain cyclodextrin modified graphene at 60 DEG C and (is denoted as HPCD-
rGO)。
Step b prepares houghite stripper with step b in embodiment 1.
Step c weighs 1.0g Cyhalothrin active compounds and is dissolved in the 250ml flasks for filling 45ml N-Methyl pyrrolidones
In, 1.0g HPCD-rGO, ultrasonic 30min are added in, reacts 8h in 50 DEG C of heating stirrings.Then 160ml houghites are added in remove
Liquid, the reaction was continued for 24 hours, is cooled to room temperature.Centrifugation, precipitation wash centrifugation 3 times with 95% ethyl alcohol, will be deposited at 60 DEG C dry
12h, grinding obtain cyclodextrin modified graphene-houghite sustained release agent.It is determined using ultraviolet spectrophotometry in sample
Cyhalothrin content is 3.5%.
Embodiment 4
Step a weighs 1.0g GO and is scattered in the 250ml flasks for filling 100ml removing carbon dioxide water, adds in and contains 4g hydroxyls
The 100ml aqueous solutions of butyl cyclodextrin (HBCD), ultrasonic 30min, 50 DEG C of heating stirrings are reacted 2 days；Aforesaid liquid is cooled to
Room temperature is separately added into 0.33ml hydrazine hydrates, 1.66ml ammonium hydroxide, 3h is stirred to react at 60 DEG C；By above-mentioned solution at 8000 revs/min
Clock high speed centrifugation, precipitation are washed with 95% ethyl alcohol, centrifuged 3 times, and cyclodextrin modified graphite is dried to obtain by being deposited at 60 DEG C
Alkene (is denoted as HBCD-rGO).
Step b prepares houghite stripper with step b in embodiment 1.
Step c weighs 1.0g Biphenthrin active compounds and is dissolved in the 250ml flasks for filling 45ml N-Methyl pyrrolidones, adds
Enter 1.0gHBCD-rGO, ultrasonic 30min, react 8h in 50 DEG C of heating stirrings.Then 160ml houghite strippers are added in, after
Continuous reaction for 24 hours, is cooled to room temperature.Centrifugation, precipitation wash centrifugation 3 times with 95% ethyl alcohol, will be deposited at 60 DEG C dry 12h, grind
Mill obtains cyclodextrin modified graphene-houghite sustained release agent.It is determined using ultraviolet spectrophotometry efficient in sample
Benzene chrysanthemum ester content is 4.5%.
Claims (4)
1. a kind of cyclodextrin modified graphene-houghite pesticide slow-releasing agent is by cyclodextrin modified graphene inclusion agriculture
Medicine is made again with houghite stripper hybrid reaction.Its cyclodextrin is non-ionic cyclodextrin；Cyclodextrin modified stone
Black alkene is obtained by graphene oxide and cyclodextrin reaction reduction；The houghite stripper is in formamide by houghite
Middle reaction, which is removed, to be obtained.
2. pesticide slow-releasing agent according to claim 1, it is characterized in that：Cyclodextrin is alpha-cyclodextrin, beta-cyclodextrin, γ-ring
One kind in dextrin, methyl-B-cyclodextrin, hydroxyethyl-β-cyclodextrin, hydroxypropyl-β-cyclodextrin, hydroxyl fourth group-beta-cyclodextrin.
3. pesticide slow-releasing agent according to claim 1, it is characterized in that：Pesticide is cypermethrin, effective cypermethrin, trifluoro
One kind in cypermethrin, decis, Biphenthrin, pesticide concentration by percentage to the quality for the sustained release agent 3%~
50%.
4. the preparation method of pesticide slow-releasing agent according to claim 1, step are：(A) oxidation stone is weighed by design flow
Black alkene and cyclodextrin are scattered in the water of removing carbon dioxide, ultrasonic 30min, and 50 DEG C of heating stirrings are reacted 2 days；Aforesaid liquid is cold
But room temperature is arrived, hydrazine hydrate is measured by design flow and ammonium hydroxide is added thereto, 3h is stirred to react at 60 DEG C；By above-mentioned solution at a high speed from
The heart washs centrifugation 3 times with 95% ethyl alcohol, will be deposited at 60 DEG C and be dried to obtain cyclodextrin modified graphene (CD-rGO)；(B)
A certain amount of houghite is weighed by design flow to be dispersed in formamide solvent, ultrasonic 30min, heating stirring is reacted at 60 DEG C
2 days, obtain transparent houghite stripper；(C) weigh a certain amount of pesticide by design flow to be dissolved in N-Methyl pyrrolidone, take
A certain amount of CD-rGO is dispersed in above-mentioned system, ultrasonic 30min, is reacted certain time in 50 DEG C of heating stirrings, is added one
Quantitative houghite stripper reacts 1 day, washs centrifugation 3 times with 95% ethyl alcohol, 60 DEG C of dryings obtain pesticide slow-releasing agent.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110663683A (en) * | 2019-10-30 | 2020-01-10 | 淄博职业学院 | Slow-release type weeding and sterilizing double-effect pesticide and preparation method thereof |
| CN111642515A (en) * | 2020-06-01 | 2020-09-11 | 南京师范大学 | Cyhalothrin nano slow-release pesticide preparation and preparation method thereof |
| CN114404647A (en) * | 2021-12-30 | 2022-04-29 | 振德医疗用品股份有限公司 | High-viscosity slow-release antibacterial water-resistant silicon-containing ostomy care composition and preparation method thereof |
-
2017
- 2017-12-18 CN CN201711388920.5A patent/CN108064844A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110663683A (en) * | 2019-10-30 | 2020-01-10 | 淄博职业学院 | Slow-release type weeding and sterilizing double-effect pesticide and preparation method thereof |
| CN110663683B (en) * | 2019-10-30 | 2021-06-22 | 淄博职业学院 | Slow-release type weeding and sterilizing double-effect pesticide and preparation method thereof |
| CN111642515A (en) * | 2020-06-01 | 2020-09-11 | 南京师范大学 | Cyhalothrin nano slow-release pesticide preparation and preparation method thereof |
| CN114404647A (en) * | 2021-12-30 | 2022-04-29 | 振德医疗用品股份有限公司 | High-viscosity slow-release antibacterial water-resistant silicon-containing ostomy care composition and preparation method thereof |
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Application publication date: 20180525 |