CN103125497A - Fenoxaprop-p-ethyl cyclodextrin inclusion compound and preparation method thereof - Google Patents
Fenoxaprop-p-ethyl cyclodextrin inclusion compound and preparation method thereof Download PDFInfo
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- CN103125497A CN103125497A CN2012105320986A CN201210532098A CN103125497A CN 103125497 A CN103125497 A CN 103125497A CN 2012105320986 A CN2012105320986 A CN 2012105320986A CN 201210532098 A CN201210532098 A CN 201210532098A CN 103125497 A CN103125497 A CN 103125497A
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- cyclodextrin
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Abstract
The invention provides fenoxaprop-p-ethyl cyclodextrin inclusion compound and a preparation method of the fenoxaprop-p-ethyl cyclodextrin inclusion compound. Cyclodextrin or cyclodextrin derivatives are dissolved in water to obtain a solution A, fenoxaprop-p-ethyl is dissolved in organic solvent to obtain a solution B, under the temperature of 5 DEG C to 10 DEG C, the solution B is stirred and slowly dripped into the solution A, after dropwise adding, the solution is stirred continuously under 5 DEG C to 10 DEG C for 24 hours to 48 hours, after stirring is finished, obtained mixture is maintained under 0 DEG C to 4 DEG C for 24 hours to 48 hours then is filtered, filtered-out contents are air dried under room temperature after washing, and the fenoxaprop-p-ethyl cyclodextrin inclusion compound is prepared. The fenoxaprop-p-ethyl cyclodextrin inclusion compound improves the water-solubility of pesticide, and reduces the harm of pesticide to environment without influencing the herbicidal activity of the pesticide.
Description
(1) technical field
The present invention relates to a kind of fenoxapropPethyl cyclodextrin inclusion compound and preparation method thereof.
(2) background technology
FenoxapropPethyl is a kind of aryl phenoxy propionic acid class selectivity, low toxicity herbicide, has interior suction conductivity, mainly in the weeds body suppresses the synthetic of fatty acid, destroys growing point and makes weeds dead.FenoxapropPethyl water-soluble very low, surfactants therefore more commonly used with its composite be that 6.9% emulsifiable concentrate is used, but said preparation wherein contains the disagreeableness surfactant of environment.Be to reduce the pesticidal preparations component to the harm of environment, need to be in pesticidal preparations the friendly material of environment for use, improve simultaneously the water-soluble of agricultural chemicals.
(3) summary of the invention
The inclusion compound that the purpose of this invention is to provide a kind of fenoxapropPethyl and cyclodextrin or cyclodextrine derivatives can improve the water-soluble of fenoxapropPethyl in the situation that do not affect activity of weeding.
The technical solution used in the present invention is:
A kind of fenoxapropPethyl cyclodextrin inclusion compound makes by the following method: cyclodextrin or cyclodextrine derivatives is soluble in water, obtain solution A; FenoxapropPethyl is dissolved in organic solvent, obtains solution B; Under 5 ~ 10 ℃, slowly be added drop-wise in solution A solution B under stirring, continue at after dropwising under 5 ~ 10 ℃ and stir, stirred altogether 24 ~ 48 hours, after stirring is completed, the gained mixture is filtered after placing 24 ~ 48 hours under 0 ~ 4 ℃, leach thing room temperature after washing air-dry, make described fenoxapropPethyl cyclodextrin inclusion compound; Described fenoxapropPethyl is 1:1 ~ 3 with the ratio of the mole dosage of cyclodextrin or cyclodextrine derivatives, and described cyclodextrin or derivatives thereof is one of following: beta-schardinger dextrin-, methyl-β-cyclodextrin, 2-HP-BETA-CD.In this inclusion compound, the inclusion of fenoxapropPethyl and the derivative of cyclodextrin or cyclodextrin is than being 1:1, and namely each fenoxapropPethyl molecule is by a cyclodextrin or cyclodextrine derivatives molecule institute inclusion.
Preferably, described cyclodextrin or derivatives thereof is beta-schardinger dextrin-, and fenoxapropPethyl is 1:1.2 with the ratio of the mole dosage of beta-schardinger dextrin-.
The inventor passes through test of many times, find fenoxapropPethyl by with the effect of cyclodextrin or derivatives thereof generation inclusion, the inclusion complex that forms has not only strengthened the water-soluble of fenoxapropPethyl agricultural chemicals well, and activity of weeding is not had impact substantially, therefore solved well fenoxapropPethyl pesticide water dissolubility problem.
The invention still further relates to a kind of method for preparing described fenoxapropPethyl cyclodextrin inclusion compound, described method is as follows: cyclodextrin or cyclodextrine derivatives is soluble in water, obtain solution A; FenoxapropPethyl is dissolved in organic solvent, obtains solution B; Under 5 ~ 10 ℃, slowly be added drop-wise in solution A solution B under stirring, continue at after dropwising under 5 ~ 10 ℃ and stir, stirred altogether 24 ~ 48 hours, after stirring is completed, the gained mixture is filtered after placing 24 ~ 48 hours under 0 ~ 4 ℃, (purpose of washing is that the fenoxapropPethyl of unnecessary not inclusion is removed through washing to leach thing, the washing solvent for use is the organic solvent of solubilized fenoxapropPethyl, for example acetone, methyl alcohol, ethanol, ethanol or isopropyl alcohol) after room temperature air-dry, make described fenoxapropPethyl cyclodextrin inclusion compound; Described fenoxapropPethyl is 1:1 ~ 3 with the ratio of the mole dosage of cyclodextrin or cyclodextrine derivatives, and described cyclodextrin or derivatives thereof is one of following: beta-schardinger dextrin-, methyl-β-cyclodextrin, 2-HP-BETA-CD; Described organic solvent is one of following: acetone, methyl alcohol, ethanol, ethanol or isopropyl alcohol.
Preferably, described cyclodextrin or derivatives thereof is beta-schardinger dextrin-.
Preferably, described organic solvent is acetone.
Preferably, described fenoxapropPethyl is 1:1.2 with the ratio of the mole dosage of cyclodextrin or cyclodextrine derivatives.
In described solution A, the concentration of cyclodextrin or cyclodextrine derivatives is 0.9 ~ 1.8g/L.
In described solution B, the concentration of fenoxapropPethyl is 10 ~ 500 g/L.
Beneficial effect of the present invention is mainly reflected in: the invention provides a kind of fenoxapropPethyl cyclodextrin inclusion compound, improved the water-soluble of agricultural chemicals, reduce it to the harm of environment, and do not affect its activity of weeding.
(4) description of drawings
Fig. 1 is means of differential scanning calorimetry (DSC) spectrogram of embodiment 2 products;
Fig. 2 is the Fourier transform infrared spectrogram of embodiment 2 products.
(5) embodiment
The present invention is described further below in conjunction with specific embodiment, but protection scope of the present invention is not limited in this:
Embodiment 1:
The beta-schardinger dextrin-(1.135g, 1mmol) that is dried to after constant weight is placed in there-necked flask, adds 70mL distilled water wiring solution-forming; FenoxapropPethyl (253mg, 1mmol) is dissolved in acetone (10mL).Slowly drip the acetone soln of fenoxapropPethyl in cyclodextrin solution, stir while dripping, temperature remains on 10 ℃, and time for adding is 8 hours, stirs after dropwising 16 hours again.After stirring is completed, products therefrom is filtered after placing 36 hours under 0 ~ 4 ℃, leach thing 3 times with the acetone washing, then will leach thing at room temperature air-dry, can obtain fenoxapropPethyl and β-cyclodextrin inclusion complex, product is white powder.
Embodiment 2:
The beta-schardinger dextrin-(1.135g, 1mmol) that is dried to after constant weight is placed in glass mortar, adds 70mL distilled water wiring solution-forming; FenoxapropPethyl (300mg, 1.2mmol) is dissolved in methyl alcohol (15mL).Slowly drip the methanol solution of fenoxapropPethyl in cyclodextrin solution, stir while dripping, temperature remains on 10 ℃, and time for adding is 8 hours, stirs after dropwising 16 hours again.After stirring is completed, products therefrom is filtered after placing 36 hours under 0-4 ℃, leach thing 3 times with methanol wash, then will leach thing at room temperature air-dry, can obtain fenoxapropPethyl and beta-cyclo dextrin included compound, product is white powder.
Prepared inclusion complex characterizes by the following method:
With differential scanning calorimetry (DSC) mensuration fenoxapropPethyl and beta-schardinger dextrin-whether inclusion occurs, result such as accompanying drawing 1.With Fourier transform infrared (FTIR) mensuration fenoxapropPethyl and beta-schardinger dextrin-whether inclusion occurs, result such as accompanying drawing 2.
Fig. 1 shows, in the DSC collection of illustrative plates of fenoxapropPethyl, demonstrates a very sharp-pointed endothermic peak at 358.2 K places, and this endothermic peak corresponds to the fusing point of fenoxapropPethyl.The DSC collection of illustrative plates of beta-schardinger dextrin-is the endothermic peak of a non-constant width between 363-413K, and this may be because the beta-schardinger dextrin-dehydration forms.The DSC collection of illustrative plates of fenoxapropPethyl and beta-schardinger dextrin-mixture is the stack of fenoxapropPethyl and beta-schardinger dextrin-collection of illustrative plates, but demonstrate significantly the characteristic peak of fenoxapropPethyl melting and the characteristic peak of beta-schardinger dextrin-dehydration, this shows in mixed system, and these two kinds of materials do not show obvious interaction.And in the DSC collection of illustrative plates with the sample of the fenoxapropPethyl of preparing and beta-schardinger dextrin-, the endothermic peak of beta-schardinger dextrin-has reduced a lot, simultaneously the fusing point peak of fenoxapropPethyl almost disappears, this explanation fenoxapropPethyl has entered in the cavity of beta-schardinger dextrin-, substituted the part hydrone in the beta-schardinger dextrin-cavity, the dehydration peak of beta-schardinger dextrin-reduces simultaneously.
Fig. 2 shows, in the infrared spectrum of FE and beta-schardinger dextrin-mixture, all can see the characteristic absorption of the fenoxapropPethyl that is diluted, and illustrates stronger interaction does not occur between fenoxapropPethyl and beta-schardinger dextrin-.Differently therewith be, in grinding the sample that fenoxapropPethyl and beta-schardinger dextrin-prepare, the characteristic absorption of β-aromatic rings (1628,1570,1505 and 146 2cm
-1) further diluted, and, the absorption of the carbonyl of fenoxapropPethyl (1736 cm
-1) the basic disappearance, illustrate between FE and cyclodextrin clathration has occured.
Embodiment 3:
The 2-HP-BETA-CD (1.177g, 1mmol) that is dried to after constant weight is placed in there-necked flask, adds 40mL distilled water wiring solution-forming; FenoxapropPethyl (300mg, 1.2mmol) is dissolved in acetone (10mL).Slowly drip the acetone soln of fenoxapropPethyl in cyclodextrin solution, stir while dripping, temperature remains on 10 ℃, and time for adding is 8 hours, stirs after dropwising 16 hours again.After stirring is completed, products therefrom is filtered after placing 36 hours under 0 ~ 4 ℃, leach thing 2 times with the acetone washing, then will leach thing at room temperature air-dry, can obtain fenoxapropPethyl and 2-HP-BETA-CD inclusion complex, product is white powder.
Claims (8)
1. fenoxapropPethyl cyclodextrin inclusion compound makes by the following method: cyclodextrin or cyclodextrine derivatives is soluble in water, obtain solution A; FenoxapropPethyl is dissolved in organic solvent, obtains solution B; Under 5 ~ 10 ℃, slowly be added drop-wise in solution A solution B under stirring, continue at after dropwising under 5 ~ 10 ℃ and stir, stirred altogether 24 ~ 48 hours, after stirring is completed, the gained mixture is filtered after placing 24 ~ 48 hours under 0 ~ 4 ℃, leach thing room temperature after washing air-dry, make described fenoxapropPethyl cyclodextrin inclusion compound; Described fenoxapropPethyl is 1:1 ~ 3 with the ratio of the mole dosage of cyclodextrin or cyclodextrine derivatives, and described cyclodextrin or derivatives thereof is one of following: beta-schardinger dextrin-, methyl-β-cyclodextrin, 2-HP-BETA-CD.
2. fenoxapropPethyl cyclodextrin inclusion compound as claimed in claim 1, is characterized in that described cyclodextrin or derivatives thereof is beta-schardinger dextrin-, and fenoxapropPethyl is 1:1.2 with the ratio of the mole dosage of beta-schardinger dextrin-.
3. one kind prepares the method for fenoxapropPethyl cyclodextrin inclusion compound as claimed in claim 1, and described method is as follows: cyclodextrin or cyclodextrine derivatives is soluble in water, obtain solution A; FenoxapropPethyl is dissolved in organic solvent, obtains solution B; Under 5 ~ 10 ℃, slowly be added drop-wise in solution A solution B under stirring, continue at after dropwising under 5 ~ 10 ℃ and stir, stirred altogether 24 ~ 48 hours, after stirring is completed, the gained mixture is filtered after placing 24 ~ 48 hours under 0 ~ 4 ℃, leach thing room temperature after washing air-dry, make described fenoxapropPethyl cyclodextrin inclusion compound; Described fenoxapropPethyl is 1:1 ~ 3 with the ratio of the mole dosage of cyclodextrin or cyclodextrine derivatives, and described cyclodextrin or derivatives thereof is one of following: beta-schardinger dextrin-, methyl-β-cyclodextrin, 2-HP-BETA-CD; Described organic solvent is one of following: acetone, methyl alcohol, ethanol, ethanol or isopropyl alcohol.
4. method as claimed in claim 3, is characterized in that described cyclodextrin or derivatives thereof is beta-schardinger dextrin-.
5. method as described in claim 3 or 4, is characterized in that described organic solvent is acetone.
6. method as described in claim 3 or 4, is characterized in that described fenoxapropPethyl and the ratio of the mole dosage of cyclodextrin or cyclodextrine derivatives are 1:1.2.
7. method as described in claim 3 or 4 is characterized in that the concentration of cyclodextrin in described solution A or cyclodextrine derivatives is 0.9 ~ 1.8g/L.
8. method as described in claim 3 or 4, the concentration that it is characterized in that fenoxapropPethyl in described solution B is 10 ~ 500 g/L.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106614649A (en) * | 2016-12-02 | 2017-05-10 | 华东理工大学 | Cyclodextrin inclusion compound of cycloxaprid and preparation of wettable powder of cyclodextrin inclusion compound |
| CN109924209A (en) * | 2019-04-12 | 2019-06-25 | 东北农业大学 | A kind of diuron herbicide cyclodextrin inclusion compound and preparation method thereof |
| CN112911934A (en) * | 2018-10-24 | 2021-06-04 | 阿达玛马克西姆有限公司 | Use of cyclodextrins as agrochemical delivery systems |
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| CN102742581A (en) * | 2012-07-20 | 2012-10-24 | 陕西省微生物研究所 | Preparation method of natamycin-hydroxypropyl-beta-cyclodextrin inclusion complex |
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| CN101401572A (en) * | 2008-09-05 | 2009-04-08 | 河北科技大学 | Cyclodextrin of sethoxydim, or its hydrophilic derivant clathrate compound, and method of preparing the same |
| CN102742581A (en) * | 2012-07-20 | 2012-10-24 | 陕西省微生物研究所 | Preparation method of natamycin-hydroxypropyl-beta-cyclodextrin inclusion complex |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106614649A (en) * | 2016-12-02 | 2017-05-10 | 华东理工大学 | Cyclodextrin inclusion compound of cycloxaprid and preparation of wettable powder of cyclodextrin inclusion compound |
| CN106614649B (en) * | 2016-12-02 | 2019-02-15 | 华东理工大学 | A kind of preparation of the cyclodextrin inclusion compound and its wettable powder of cycloxaprid |
| CN112911934A (en) * | 2018-10-24 | 2021-06-04 | 阿达玛马克西姆有限公司 | Use of cyclodextrins as agrochemical delivery systems |
| CN109924209A (en) * | 2019-04-12 | 2019-06-25 | 东北农业大学 | A kind of diuron herbicide cyclodextrin inclusion compound and preparation method thereof |
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Application publication date: 20130605 |