CN101036459A - Eugenol micro-emulsion - Google Patents
Eugenol micro-emulsion Download PDFInfo
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Abstract
本发明涉及一种以丁香酚为有效成分的微乳剂及其制备方法。该微乳剂由丁香酚、溶剂、乳化剂、增效助剂、防冻剂和水组成。本发明中丁香酚微乳剂具有高效、低毒、生产成本低，制备工艺简单，生产、储运、使用过程中安全性好，对环境污染小。The invention relates to a microemulsion with eugenol as an active ingredient and a preparation method thereof. The microemulsion consists of eugenol, solvent, emulsifier, builder, antifreeze and water. The eugenol microemulsion in the invention has high efficiency, low toxicity, low production cost, simple preparation process, good safety during production, storage, transportation and use, and little environmental pollution.
Description
Technical field:
The invention belongs to pesticide field, specifically relating to the eugenol is bactericidal microemulsion of fungicide active ingredient preparation and preparation method thereof.
Background technology:
Eugenol (Eugenol) claims Eugenol again, and eugenol, chemical name are 2-methoxyl group-4-chavicol, and structural formula is:
Outward appearance is colourless to faint yellow consistence oily liquids.Blackening is thick glutinous down to put the irradiation of dew air and light.255 ℃ of boiling points, freezing point-9.2～-9.1 ℃, about 104 ℃ of flash-point, 10.3 ℃ of congealing points, relative density 1.0652～1.0664, refractive index 1.5410.Water-soluble hardly, miscible with ethanol, chloroform, ether, oils.Be present in plant clove of myrtaceae (Syzygium aromaticum) volatile oil, calamus (Acorus calamus L.) volatile oil is in the positions such as rutaceae kamuning (Murraya paniculata (L.) Jack.) leaf.In perfume industry, be used as fumet, can replace caryophyllus oil system perfume, the system vanilla.Also can be used as preservative, active oxygen scavenger etc.Pharmaceutically be used for antibiotic, anti-inflammatory, can be used as the analgesic of tooth etc.
The scientific research personnel has made correlative study work: Song Jun (1996) to eugenol and has measured eugenol to dermatophyte, saccharomycetic inhibitory action in recent years; Zhou Jianxin (2000) is that main antipathogenic composition is an eugenol in the object description caryophyllus oil with putrefying bacteria common in the food such as aspergillus flavus, aspergillus fumigatus, staphylococcus aureus etc.; Li Mingyu (2004) has measured eugenol to cariogenic bacteria streptococcus mutans and the synthetic inhibitory action of streptococcus sobrinus polysaccharide, points out that it is as the possibility of preventing and treating the mouth disease medicine; Building prosperity (2006) is the bacteriostatic activity of object research caryophyllus oil with 5 plant species disease funguses such as Chinese cabbage alternaria, rhizoctonia cerealis, points out that its main antipathogenic composition is an eugenol; Sumbul road (2006) research eugenol and DNA interact, and show that it provides possibility as suppressing cardiovascular disease medicine.More than research all rests on laboratory stage.
Though eugenol be from plant isolation identification compound, it is stable to show chemical property, toxicity is low, easily degraded in environment, to human body and Environmental security, meet the developing direction of biopesticide, exploitation has broad application prospects as biopesticide to show it.Existing eugenol all is directly to adopt water or organic solvent extraction from plant, needs to consume a large amount of plant resourceses.
Summary of the invention
The present invention aims to provide the microemulsion that a kind of eugenol active component and other auxiliary agents are formed a kind of environmental protection, efficient, low toxicity, and this formulation and Environmental compatibility are good.
Another object of the present invention provides a kind of preparation method of this microemulsion.
To achieve these goals, carried out system research through eugenol being suppressed the effect of various plants disease fungus, find that eugenol shows higher inhibitory action to frequently seen plants pathogens such as Rhizoctonia solani Kuhn, fusarium graminearum, Phytophthora capsici germ, apple leaf spoting bacteria, botrytis cinerea, Sclerotinia sclerotiorums under isolated condition, under condition of living body, crop pest there is good control efficiency.
Above-mentioned purpose of the present invention realizes by the following technical solutions.
A kind of bactericidal microemulsion that contains eugenol, it is characterized in that, this bactericidal microemulsion contains the raw material of following mass percent: eugenol 5～20% (being preferably 10～20%), solvent 10～15%, emulsifier 10～20%, builder 0.5～2%, antifreezing agent 2～5%, all the other are water, and the summation of above-mentioned raw materials is 100%.
Solvent is ethanol, methyl alcohol, acetone, ethyl acetate or dimethyl sulfoxide (DMSO), preferred alcohol and methyl alcohol.
Emulsifier is selected from two or more mixtures in alkyl polyoxyethylene ether, polyoxyethylene carboxylate, polyoxyethylene nonylphenol ether, phenethyl phenol polyethenoxy ether, triphenyl vinyl phenol polyoxyethylene poly-oxygen propylene aether, alkylbenzenesulfonate, the alkane naphthalene sulfonate.
Builder can be one or both compositions in azone, compound sodium nitrophenolate, Nafusaku, the thiophene ketone.
One or both compositions in the optional spent glycol of antifreezing agent, propane diols, glycerine, polyethylene glycol, the urea.
Water is running water, distilled water or deionized water.
Wherein, eugenol can adopt the eugenol plant crude extract of eugenol (but not contain) of synthetic, can not need to consume a large amount of plant resourceses like this.
Concrete preparation method is:
Microemulsion among the present invention adopts the conventional method preparation: with the former medicinal cosolvent dissolving of eugenol, treat to stir after eugenol fully dissolves, add emulsifier, builder and antifreeze during stirring, after treating above-mentioned system mixing, again water is slowly added in the above-mentioned mixed liquor, stir again freely disperse, homogeneous, transparent, stable weak yellow liquid.The used mixing speed of the present invention is 60 rev/mins～200 rev/mins, and mixing time is 30 minutes～1 hour, and whipping temp is a normal temperature.
The eugenol micro-emulsion that contains provided by the present invention has following beneficial effect: 1, because this formulation is main matrix with water, saved a large amount of organic solvents, environmental pollution is little, uses the back noresidue; 2, nonflammable, storage, transportation safety; 3, production technology is simple, is convenient to preparation, and cost is low; 4, good drug efficacy, many targets action site, pathogen is difficult for developing immunity to drugs.
Embodiment
Reach the field efficacy of medicament of the present invention for a better understanding of the present invention, below the present invention is described in further detail by the following embodiment that finishes according to above technical scheme, but be not limited to these embodiment.
Embodiment 1:
The eugenol micro-emulsion of following different content all adopts this method to make: eugenol dissolves fully with solvent, treat to stir after eugenol fully dissolves, add emulsifier, builder and antifreeze during stirring, after treating above-mentioned system mixing, again water is slowly added in the above-mentioned mixed liquor, can be made into the eugenol micro-emulsion of different content after fully stirring.
(1) eugenol micro-emulsion: eugenol 5%, ethanol 10%, alkyl polyoxyethylene ether and polyoxyethylene nonylphenol ether 20%, azone 2%, ethylene glycol and glycerine 5%, running water complement to 100%.
(2) eugenol micro-emulsion: eugenol 10%, methyl alcohol 15%, polyoxyethylene carboxylate and phenethyl phenol polyethenoxy ether 18%, compound sodium nitrophenolate 0.5%, propane diols 4%, deionized water complement to 100%.
(3) eugenol micro-emulsion: eugenol 15%, acetone 13%, polyoxyethylene nonylphenol ether and phenethyl phenol polyethenoxy ether 10%, thiophene ketone 0.8%, glycerine 3%, distilled water complement to 100%.
(4) eugenol micro-emulsion: eugenol 20%, ethyl acetate 15%, alkylbenzenesulfonate and alkane naphthalene sulfonate 15%, compound sodium nitrophenolate and Nafusaku 2%, polyethylene glycol 2%, running water complement to 100%.
In superincumbent component and the proportioning, solvent can also be selected dimethyl sulfoxide (DMSO) for use except that ethanol, methyl alcohol, acetone, ethyl acetate, but preferred alcohol or methyl alcohol.
Emulsifier is generally selected the mixture of two or more any proportionings in alkyl polyoxyethylene ether, polyoxyethylene carboxylate, polyoxyethylene nonylphenol ether, phenethyl phenol polyethenoxy ether, triphenyl vinyl phenol polyoxyethylene poly-oxygen propylene aether, alkylbenzenesulfonate, the alkane naphthalene sulfonate for use.
Builder is generally selected the composition of one or both any proportionings in azone, compound sodium nitrophenolate, Nafusaku, the thiophene ketone for use.
Antifreezing agent is generally selected the composition of one or both any proportionings in ethylene glycol, propane diols, glycerine, polyethylene glycol, the urea for use.
Microemulsion physicochemical property and stability in this invention:
Outward appearance: light yellow transparent liquid.There are not visible suspension and precipitation.
Emulsifying dispersivity: eugenol micro-emulsion can be rapidly, be dispersed in the water naturally, is transparent homogeneous phase solution.
Ageing stability: seasoning is stable under the normal temperature.
Cold storage stability test:
Get 20mL 20% eugenol micro-emulsion and put into tool plug test tube, in the refrigerator of (0 ± 1) ℃ behind the storage 14d, that the preparation outward appearance keeps is transparent, do not have precipitation and layering is separated out, do not had in crystallization, the mobile and equal no change of emulsifiability.
The heat storage stability test:
Test 20ml 20% eugenol micro-emulsion seals in ampoule and is placed on (54 ± 2) ℃ constant temperature after 14 days, does not have muddiness, layering, crystallization, preparation outward appearance homogeneous phase transparent.
Adopt the content of active ingredient eugenol in the high-efficient liquid phase chromatogram technique analysis preparation.The average resolution ratio of 20% eugenol micro-emulsion is 1.38%.The result shows that heat storage stability is good.
Test examples 1: measure the inhibition activity of eugenol to the frequently seen plants disease fungus
1, for the examination bacterial classification
Fusarium moniliforme (Fusarium moniliforme), rice blast fungus (pyricutaria oryzae), Rhizoctonia solani Kuhn ((Rhizoctonia solani), rhizoctonia cerealis (Rhizotonia cerealis), fusarium graminearum (Fusarium graminearum), apple leaf spoting bacteria (Rhizoctonia solani), ring rot of apple bacterium (Macrophoma kuwatsukai), botrytis cinerea (Botryris cinerea), Sclerotinia sclerotiorum (Sclerotinia sclerotiorum), sugar beet leaf spot bacteria (Cecospora beticola), the wet bubble of mushroom germ (Mycogone pemiciosa), Phytophthora capsici germ (Phytophora capsici), tobacco brown spot pathogen (Altermaria alternata) and garlic purple plague purpura germ (Stemphylium vesicarium) provide with detection research institute by academy of agricultural sciences, Jiangsu Province food quality safety.
2, test method
Adopt the mycelial growth rate method to measure the inhibition activity of eugenol:, to go out to beat cut-off at colony edge and directly be the bacterium dish of 0.5cm with each bacterial strain activation to each pathogen.Access contains the PDA culture medium flat plate central authorities of eugenol series final concentration (0,12.5,25,50,100,200 μ g/mL), places to cultivate 3～5d under 25 ℃ of constant incubator dark conditions, measures colony diameter, calculates concentration and virulence regression equation in the inhibition.
Table 1 eugenol is to the inhibitory action of different plant pathogenic fungis
| Phytopathogen pathogen | Virulence regression equation (Toxic regression equation) | Concentration Ec in the inhibition 50/(μg/mL) | Correlation coefficient (R) |
| Fusarium moniliforme | Y＝2.2199x+0.6079 | 95.17 | 0.9781 |
| Rice blast fungus | Y＝2.0923x+1.9298 | 29.33 | 0.9765 |
| Rhizoctonia solani Kuhn | Y＝2.4437x+0.5390 | 66.91 | 0.9739 |
| Rhizoctonia cerealis | Y＝1.7380x+2.4070 | 31.04 | 0.9812 |
| Fusarium graminearum | Y＝2.5205x-0.0612 | 101.87 | 0.9825 |
| The apple leaf spoting bacteria | Y＝1.8537x+1.4994 | 77.34 | 0.9825 |
| The ring rot of apple bacterium | Y＝2.6068x+0.2729 | 65.07 | 0.9701 |
| Botrytis cinerea | Y＝2.2566x+0.9120 | 64.80 | 0.9877 |
| Sclerotinia sclerotiorum | Y＝1.9056x+1.9482 | 39.94 | 0.9990 |
| Sugar beet leaf spot bacteria | Y＝2.1272x+1.2231 | 59.63 | 0.9887 |
| The wet bubble of mushroom germ | Y＝2.2561x+1.2338 | 46.70 | 0.9875 |
| The Phytophthora capsici germ | Y＝4.1630x-4.3882 | 179.95 | 0.9628 |
| Tobacco brown spot pathogen | Y＝4.3230x-3.5878 | 96.94 | 0.9754 |
| Garlic purple plague purpura germ | Y＝1.6481x+1.5347 | 126.66 | 0.9581 |
Test examples 2: the field control effectiveness test of eugenol micro-emulsion
Eugenol micro-emulsion control powdery mildew of strawberry field trial (testing program is according to " pesticide field efficacy medicine test criterion (two) " design):
One, experimental scheme and arrangement
1, for studying thing and controlling object.
For studying thing: strawberry, kind are Feng Xiang.
Controlling object: powdery mildew of strawberry, pathogen are Sphaerotheca pannosa.
2, reagent agent
Test medicine:
20% eugenol micro-emulsion, the Jiangsu Province Agriculture Science Institute development.
The contrast medicament:
900 times of 70% mancozeb wettable powders, commercially available, Shanghai China safe agricultural chemicals Co., Ltd produces.
3, sub-district design
The selection in test plot: this test is located at Jiangsu Province Agriculture Science Institute gardening research institute test booth base.
5 chemicals treatment are established in test: 20% eugenol micro-emulsion, 200,300,400 μ g/mL, 900 times of 70% mancozeb wettable powders, blank.Sub-district area 15m
2, 4 repetitions, the minizone adopts completely random district group to arrange, respectively at executing the secondary medicine on February 28th, 2007, March 6, the dispenser artificial knapsack sprayer of workers and peasants-16 type, every 667m
2Amount of liquid medicine is 60kg.
4, investigation method
5 samplings of every sub-district diagonal, every five strain.3 representational compound leaves are got in every strain, account for the classification of whole vanelets area percentage with every leaf spot lesion area on the compound leaf.
Grade scale is:
0 grade: no scab;
1 grade: lesion area accounts for whole leaf area below 5%;
3 grades: lesion area accounts for whole leaf area 6%～15%;
5 grades: lesion area accounts for whole leaf area 16%～25%;
7 grades: lesion area accounts for whole leaf area 26%～50%;
9 grades: lesion area accounts for whole leaf area more than 50%.
5, control time and number of times
This test is investigated 3 times altogether, investigation state of an illness radix before the 1st dispenser on February 28, and the 2nd inferior to investigation on March 6 drug effect in mid-term, and March 12 was 6d investigation preventive effect in latter stage behind the last medicine.All look into disease index during each the investigation, calculate preventive effect.
6, drug effect computational methods
CK
0The disease of not dispenser check plot refers to before the spray medicine.CK
1The disease of not dispenser check plot refers to behind the spray medicine.
Pt
0The disease in spray medicine pre-treatment district refers to.Pt
1The disease of spray medicine post processing zone refers to.
Two, result of the test:
Table 2 20% eugenol micro-emulsion control powdery mildew of strawberry field control effectiveness test is the Nanjing as a result
| Handle | Disease refers to radix before the medicine | 6d behind the 1st medicine | 6d behind the 2nd medicine | ||
| Disease refers to | Preventive effect (% | Disease refers to) | Preventive effect (%) | ||
| 20% eugenol micro-emulsion, 200 μ g/mL, 20% eugenol micro-emulsion, 300 μ g/mL, 20% eugenol micro-emulsion, 400 μ g/mL 900 times of CK of 70% mancozeb wettable powder (clear water) | 71.04 58.89 54.07 85.19 72.22 | 17.84 7.41 6.67 19.63 84.44 | 78.52 89.24 89.45 80.29 / | 21.55 9.26 6.3 30.0 91.85 | 76.15c 87.64b 90.84a 72.31c / |
Annotate: different 0.05 significance level that reaches of different lowercase alphabet differentials.
*Be the mean value of 4 repetitions.
Eugenol micro-emulsion is prevented and treated cladosporium leaf and fruit mould of tomato field trial (testing program is according to " pesticide field efficacy medicine test criterion (two) " design):
One, experimental scheme and arrangement
1, for studying thing and controlling object.
For studying thing: tomato, kind are precious big by 903.
Controlling object: cladosporium leaf and fruit mould of tomato, pathogen are Fulvia fulva (Cooke) Ciferri.
2, reagent agent
Test medicine:
5% eugenol micro-emulsion, the Jiangsu Province Agriculture Science Institute development.
The contrast medicament:
1000 times of the clean wetting powders of 52% leaf mold, commercially available, Hebei is praised peak biotechnology Co., Ltd and is produced.
3, sub-district design
The selection in test plot: this test is located at Anhui Province and south, county town one peasant household's tomato planting booth.
5 chemicals treatment are established in test: 5% eugenol micro-emulsion, 300 μ g/mL, 400 μ g/mL, 500 μ g/mL, 1000 times of the clean wetting powders of 52% leaf mold, blank.Sub-district area 15m
2, 4 repetitions, the minizone adopts completely random district group to arrange, respectively at executing the secondary medicine on April 5 (their early stage) in 2007, April 11, the dispenser artificial knapsack sprayer of workers and peasants-16 type, every 667m
2Amount of liquid medicine is 60kg.
4, investigation method
3 samplings in every sub-district, every 5 strain.Every strain branch upper, middle and lower part is got a representational compound leaf, accounts for the classification of whole vanelets area percentage with every vanelets lesion area on the compound leaf.
Grade scale is:
0 grade: no scab;
1 grade: lesion area accounts for whole leaf area below 5%;
3 grades: lesion area accounts for whole leaf area 6%～10%;
5 grades: lesion area accounts for whole leaf area 11%～20%;
7 grades: lesion area accounts for whole leaf area 21%～50%;
9 grades: lesion area accounts for whole leaf area more than 50%.
5, control time and number of times
This test is investigated 2 times altogether, investigation state of an illness radix before the 1st dispenser on April 5, and April 18 i.e. 7d efficacy survey in latter stage behind 2 medicines.
6, drug effect computational methods
CK
0The disease of not dispenser check plot refers to before the spray medicine.CK
1The disease of not dispenser check plot refers to behind the spray medicine.
Pt
0The disease in spray medicine pre-treatment district refers to.Pt
1The disease of spray medicine post processing zone refers to.
Table 3 5% eugenol micro-emulsion is prevented and treated cladosporium leaf and fruit mould of tomato field control effectiveness test Anhui and county as a result
| Handle | Disease refers to radix before the medicine | 7d behind the 2nd medicine | |
| Disease refers to | Preventive effect (%) | ||
| 5% eugenol micro-emulsion, 300 μ g/mL, 5% eugenol micro-emulsion, 400 μ g/mL, 5% eugenol micro-emulsion 500 μ g/mL, 52% leaf mold, 900 times of CK of clean wetting powder (clear water) | 31.90 18.52 17.04 13.33 12.59 | 14.10 7.41 5.56 4.44 16.30 | 65.86c 69.10b 74.80a 76.75a / |
Annotate: different 0.05 significance level that reaches of different lowercase alphabet differentials.
*Be the mean value of 4 repetitions.
Claims (9)
1, a kind of eugenol micro-emulsion, the mass percent that it is characterized in that this each component of microemulsion is: eugenol 5～20%, solvent 10～15%, emulsifier 10～20%, builder 0.5～2%, antifreezing agent 2～5%, all the other are water, and the summation of above-mentioned raw materials is 100%.
2, eugenol micro-emulsion according to claim 1, the percentage by weight that it is characterized in that eugenol is 10～20%.
3, eugenol micro-emulsion according to claim 1 is characterized in that described solvent is ethanol, methyl alcohol, acetone, ethyl acetate or dimethyl sulfoxide (DMSO).
4, eugenol micro-emulsion according to claim 1 is characterized in that described solvent is ethanol or methyl alcohol.
5, eugenol micro-emulsion according to claim 1 is characterized in that described emulsifier is selected from two or more mixtures in alkyl polyoxyethylene ether, polyoxyethylene carboxylate, polyoxyethylene nonylphenol ether, phenethyl phenol polyethenoxy ether, triphenyl vinyl phenol polyoxyethylene poly-oxygen propylene aether, alkylbenzenesulfonate, the alkane naphthalene sulfonate.
6, eugenol micro-emulsion according to claim 1 is characterized in that described builder is one or both compositions in azone, compound sodium nitrophenolate, Nafusaku, the thiophene ketone.
7, eugenol micro-emulsion according to claim 1 is characterized in that described antifreezing agent selects one or both compositions in ethylene glycol, propane diols, glycerine, polyethylene glycol, the urea for use.
8, eugenol micro-emulsion according to claim 1 is characterized in that described water is running water, distilled water or deionized water.
9, a kind of preparation method of eugenol micro-emulsion, it is characterized in that the former medicinal solvent of eugenol is dissolved fully, treat to stir after eugenol fully dissolves, add emulsifier, builder and antifreezing agent during stirring, after treating above-mentioned system mixing, again water is slowly added in the above-mentioned mixed liquor, can be made into eugenol micro-emulsion after fully stirring.
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