CN100475035C - Sterilizing use of asarin for preventing plant disease induced by plant pathogenic bacterium - Google Patents
Sterilizing use of asarin for preventing plant disease induced by plant pathogenic bacterium Download PDFInfo
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- CN100475035C CN100475035C CNB200710017493XA CN200710017493A CN100475035C CN 100475035 C CN100475035 C CN 100475035C CN B200710017493X A CNB200710017493X A CN B200710017493XA CN 200710017493 A CN200710017493 A CN 200710017493A CN 100475035 C CN100475035 C CN 100475035C
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- 201000010099 disease Diseases 0.000 title claims abstract description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 12
- 230000001954 sterilising effect Effects 0.000 title description 2
- 244000000005 bacterial plant pathogen Species 0.000 title 1
- RKFAZBXYICVSKP-AATRIKPKSA-N alpha-asarone Chemical compound COC1=CC(OC)=C(\C=C\C)C=C1OC RKFAZBXYICVSKP-AATRIKPKSA-N 0.000 claims abstract description 79
- 239000004094 surface-active agent Substances 0.000 claims abstract description 15
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- 239000004530 micro-emulsion Substances 0.000 claims abstract description 13
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- 239000003899 bactericide agent Substances 0.000 claims abstract description 11
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
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- 241000193738 Bacillus anthracis Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- 241000606265 Valeriana jatamansi Species 0.000 description 3
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- DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical compound CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000208173 Apiaceae Species 0.000 description 2
- 241000758795 Aristolochiaceae Species 0.000 description 2
- 235000017965 Asarum canadense Nutrition 0.000 description 2
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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- ABUGVBRDFWGJRD-CHOYNLESSA-N [9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-methyloxolan-2-yl]-2-(2,4-dinitrophenyl)sulfanylpurin-6-yl] [hydroxy(phosphonooxy)phosphoryl] hydrogen phosphate Chemical compound O[C@@H]1[C@H](O)[C@@H](C)O[C@H]1N1C2=NC(SC=3C(=CC(=CC=3)[N+]([O-])=O)[N+]([O-])=O)=NC(OP(O)(=O)OP(O)(=O)OP(O)(O)=O)=C2N=C1 ABUGVBRDFWGJRD-CHOYNLESSA-N 0.000 description 2
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 2
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- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 1
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- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
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- 235000010149 Brassica rapa subsp chinensis Nutrition 0.000 description 1
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- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
An application of asarone in preparing the bactericide for preventing and eliminating the diseases of plant caused by pathogenic bacteria of plant is disclosed. Said bactericide in the form of emulsified oil, microemulsion, or wettable powder is prepared from said asarone, solvent, filler and surfactant.
Description
Technical field
The present invention relates to the tool Fungicidal active compound, particularly asarone and as bactericide in the application aspect the controlling plant diseases.
Background technology
Phytopathogen has very big harm to the growth of plant, and all cause tremendous loss to agricultural production every year.The control of plant disease is mainly based on chemical control, because long-term a large amount of use of chemical bactericide causes the pesticide resistance of pathogen to increase year by year, the residue of pesticide in the agricultural product rise, and food security has been caused great threat.Press for efficient, economic, safe bactericide new varieties and be used for the control of plant disease.
Asarone, English name: asaricin, different name: sarisan.Chemical name: 1-pi-allyl-2-methoxyl group-4,5-methylenedioxybenzenes.CAS number: 18607-93-7; Molecular formula: C
11H
12O
3, molecular weight 192.21, molecular structural formula is:
Asarone belongs to plain class (phenylpropanoid) compound of phenylpropyl alcohol, yellowish green oily liquids.More about the medicinal activity of asarone research report, and to it aspect the agricultural chemicals, particularly as the application study of Fungicidal active substance report not also at present.
Asarone is a kind of plant resource active component, and the floristics that contains asarone is more.Except that Jehol Ligusticum Rhizome (Ligusticum sinense O.), fern leaf Jehol Ligusticum Rhizome (Ligusticumpteridophyllum Franch.) root of Umbelliferae (Umbelliferae), Piperaceae (Piperaceae) De Jia Betel (Piper sarmentosumRoxb.) leaf, (Beilschmiedia miersii) leaf of Lauraceae (Lauraceae), the crape flower root of Chinese wild ginger (Asarum crispulatum C.F.Liang) of anisetree bark of Winteraceae (Illiciaceae) (Illicium difengpi K.I.B.et K.I.M.) and Aristolochiaceae (Aristolochiaceae), the cow hoof root of Chinese wild ginger (Asarum delavayiFranch.), in the different long handle root of Chinese wild ginger plants such as (Asiasarum heterotropoides) distribution is arranged all.
Through retrieving on CNKI, at present domestic still haveing nothing to do in asarone to the inhibiting report of agriculture pathogen,, domestic research to this compound mainly concentrates on Chinese medicine and the pharmacology.And abroad asarone was once had fragmentary report to the inhibition activity of phytopathogen, but do not carry out the data of system research.
Summary of the invention
The objective of the invention is to, provide asarone to be used to prepare the application of control by the bactericide of the microbial plant disease of pathogenic.
The applicant is mixed with the agriculture chemicals fungicide that spraying is used with asarone and solvent, filler and surfactant, and its formulation is missible oil, microemulsion or wetting powder.
The raw material and the percentage by weight thereof of missible oil, microemulsion and wetting powder are respectively:
Wetting powder: asarone 20%～60%, filler or solvent 0～74%, surfactant 1%～25%, the summation of raw material is 100%;
Missible oil: asarone 5%～50%, solvent 40～95%, surfactant 5%～35%, the summation of raw material is 100%;
Microemulsion: asarone 10%～50%, solvent 40～84%, surfactant 1%～20%, the summation of raw material is 100%.
Above-mentioned filler is one or more mixtures in white carbon black, bentonite, diatomite or the filler well known in the art;
Above-mentioned solvent is one or more mixtures in methyl alcohol, ethanol, positive isopropyl alcohol, ethyl acetate, aromatic hydrocarbon or the solvent well known in the art;
Above-mentioned surfactant is one or more a mixture of this area various surfactants commonly used.
Through applicant's further research, preparation form and field control effectiveness test with the agriculture chemicals fungicide of asarone preparation have proved that asarone has good inhibition activity to plant pathogenic fungi.Asarone is as bactericide, and its efficient, low toxicity are suitable for the requirement of plant disease chemical control.
Embodiment
Below the present invention is described in further detail.
The applicant separates having obtained asarone in the fitochemical studies to Ligusticum jeholense (Ligusticum jeholense Nakaiet Kitag).
One, the acquisition of asarone:
Extracting the method that obtains asarone from the plant that contains asarone is specially:
The plant sample drying that will contain asarone is pulverized; At room temperature divide 3 extractions with acetone, for the first time extraction time is 48 hours, for the second time, extraction time is 12h for the third time, merges No. 3 times extract, and concentrated plant extract; With benzinum (30～60 ℃ of boiling ranges) the gained plant extract is extracted; Inspissated oil ether extraction phase obtains concentrate; Concentrate benzinum: chloroform=7: 2 wash-outs; Gains behind the wash-out are used benzinum again: chloroform=1: 1 wash-out obtains asarone at last.
Two, the preparation of asarone bactericide
Asarone and solvent, filler and surfactant are mixed with pesticidal preparations such as missible oil, microemulsion and wetting powder, are used for control by the microbial plant disease of pathogenic.The percentage by weight of each raw material is in the above-mentioned various formulation:
| Formulation | Asarone % | Filler or solvent % | Surfactant % |
| Wetting powder | 20～60 | 0～74 | 1～25 |
| Missible oil | 5～50 | 40～95 | 5～15 |
| Microemulsion | 10～50 | 40～84 | 1～20 |
Used filler is one or more mixtures in the material known altogether of white carbon black, bentonite, diatomite or this area staff in the asarone preparation preparation; Used solvent is one or more mixtures in the material known altogether of methyl alcohol, ethanol, positive isopropyl alcohol, ethyl acetate, aromatic hydrocarbon or this area staff; Used surfactant is one or more a mixture of this area various surfactants commonly used.
EXPERIMENTAL EXAMPLE
One, asarone is to the fungistatic effect of 20 plant species pathogen mycelial growths
Asarone is given birth to survey to the stripped bacteriostasis of 20 plant species pathogens and be the results are shown in Table 1.
Table 1 asarone is to the inhibitory action measurement result (72h) of 20 kinds of pathogen mycelial growths
| For the examination bacterial classification | Inhibiting rate (%) |
| Deuteromycotina | |
| Cotton-wilt fusarium Fusarium oxysporium f.sp.vasinfectum | 89.5 |
| Verticillium dahliae Verticillium dahliae | 97.4 |
| Cucumber fusarium axysporum Fusarium oxysporum f.sp.cucumerinum | 43.2 |
| Botrytis cinerea Botrytis cirerea | 100.0 |
| Rhizoctonia cerealis Rhizoctonia cerealis | 100.0 |
| Tomato early blight bacterium Alternaria solani | 77.8 |
| Black spot of cabbage bacterium Alternaria oleracea | 100.0 |
| Chinese cabbage alternaria Alternaria brassicae | 31.0 |
| Tobacco brown spot pathogen Alternaria alternate | 0.0 |
| Root rotof flax bacterium Bipolaris sorokiniana | 0.0 |
| Rice blast fungus Pyricularia oryzae | 0.0 |
| Ascomycotina | |
| Fusarium graminearum Fusarium graminearum | 99.4 |
| Apple anthrax bacteria Glomerella cingulata | 61.1 |
| Sclerotinia sclerotiorum Sclerotinia sclerotiorum | 0.0 |
| Gaeumannomyces graminis Geaumannomyces graminis | 100.0 |
| Dry rot of apple bacterium Botryosphaeria berengeriana de Not | 60.0 |
| Cucumber sclerotiorum Sclerotinia sclerotiorum | 100.0 |
| Wheat snow mold bacterium Gerlachia nivalis Gams and Mull | 35.3 |
| Basidiomycotina | |
| Rhizoctonia solani Kuhn Thanatephorus cucumeris | 100.0 |
| Mastigomycotina | |
| Phytophthora capsici germ Phytophthora capsici | 100.0 |
Annotate: three repetitions are established in each processing in the test, and data are the mean value of three repetitions in the table, down together; The confession examination concentration of asarone is 100mg/L.
As can be known from Table 1, asarone all has certain inhibitory action to 16 kinds of pathogens in 20 kinds of pathogens of Deuteromycotina, Ascomycotina, Basidiomycotina, Mastigomycotina when 100mg/L.Wherein withered to cotton, cotton is yellow to wither, tomato early the inhibiting rates of 12 kinds of pathogens such as epidemic disease all more than 60%; To Phytophthora capsici germ, cucumber sclerotiorum, rhizoctonia cerealis, botrytis cinerea, Rhizoctonia solani Kuhn, gaeumannomyces graminis, the former bacterium inhibiting rate of black spot of cabbage up to 100%.
Two, asarone is to 7 kinds of pathogen mycelial growth inhibitory action toxicity test results
System measurement asarone to Phytophthora capsici germ, cucumber sclerotiorum, rhizoctonia cerealis, botrytis cinerea, Rhizoctonia solani Kuhn, gaeumannomyces graminis, 7 kinds of inhibiting virulence of pathogen mycelia of black spot of cabbage bacterium, the results are shown in Table 2.
Table 2 asarone is to 7 kinds of pathogen mycelial growth inhibitory action toxicity test results (72h)
| For examination bacterial classification Pathogenic fungi | Virulence curve Regression equation of fungieidal activity | Correlation coefficient r Regression coefficient | EC 50(mg/L) | 95% confidence limit 95%CL |
| Phytophthora capsici germ P.capsici | Y＝2.8784+1.6095X | 0.9638 | 58.0917 | 45.841～73.617 |
| Cucumber sclerotiorum S.sclerotiorum | Y＝2.2846+1.8220X | 0.9980 | 30.9280 | 38.134～64.351 |
| Rhizoctonia cerealis R..cerealis | Y＝4.1136+0.9495X | 0.9839 | 37.7185 | 21.579～65.928 |
| Botrytis cinerea B.cirerea | Y＝-2.5463+2.6791X | 0.9826 | 70.6609 | 63.043～79.200 |
| Rhizoctonia solani Kuhn T.cucumeris | Y＝0.2200+1.9891X | 0.9317 | 34.6906 | 18.574～64.790 |
| Gaeumannomyces graminis G..graminis | Y＝2.1283+1.8407X | 0.9930 | 63.2608 | 43.750～91.473 |
| Black spot of cabbage bacterium A.oleracea | Y＝0.2491+2.8452X | 0.9954 | 40.2228 | 21.347～75.789 |
As shown in Table 2, asarone all has good inhibitory effect, the EC of 72h to cucumber sclerotiorum, Rhizoctonia solani Kuhn, rhizoctonia cerealis, black spot of cabbage bacterium, Phytophthora capsici germ, gaeumannomyces graminis, 7 kinds of pathogens of tomato gray mould
50Be respectively 30.9280mg/L, 34.6906mg/L, 37.7185mg/L, 40.2228mg/L, 58.0917mg/L, 63.2608mg/L, 70.6609mg/L.
Three, asarone is to the measurement result of 4 kinds of pathogen spore germination inhibitory action virulence
Measured the influence (table 3) of asarone to 4 kinds of pathogen spore germinations.
Table 3 asarone is to the inhibitory action toxicity test result (12h) of 4 kinds of pathogen spore germinations
| For examination bacterial classification Pathogenic fungi | Virulence curve Regression equation of fungicidal activity | Correlation coefficient r Regression coefficient | EC 50(mg/L) | 95% confidence limit 95%CL |
| Apple anthrax bacteria G.cingulate | Y＝1.1782+2.3397X | 0.9805 | 43.0003 | 38.041～48.606 |
| Exserohilum turcicum E.turcicum | Y＝1.2904+1.9827X | 0.9920 | 74.2928 | 64.346～85.777 |
| Cladosporium leaf and fruit mould of tomato bacterium F.fulva | Y＝2.5330+1.5485X | 0.9897 | 39.1881 | 32.646～47.041 |
| Cucumber anthracnose C.lagenarium | Y＝1.5025+1.8062X | 0.9925 | 86.3728 | 74.340～100.353 |
Asarone all has good inhibitory effect to the spore germination of cladosporium leaf and fruit mould of tomato bacterium, apple anthrax bacteria, Exserohilum turcicum, cucumber anthracnose, its EC
50Be respectively 39.1881mg/L, 43.0003mg/L, 74.2928mg/L, 86.3728mg/L.
Four, the preparation of asarone bactericide
Need to prove that the embodiment that below provides only is preferable example, the invention is not restricted to these embodiment, all can access satisfactory bactericide within the scope of the invention.
The preparation of embodiment 1:25% asarone wetting powder.In cone-type mixer, add the white carbon black 40kg of filler, the bentonite 25kg that are crushed to about 200 orders, the 25kg asarone is sprayed in the blender by high pressure nozzle, mix; Add again and draw back powder 7.5kg, saponin 2.5kg, fully mixed, can make 25% asarone wetting powder 100kg.The water dispersible of preparation, dilution stability, cold and hot storage stability meet the commercially available agricultural chemical preparation and must ask.
The preparation of embodiment 2:55% asarone wetting powder.White carbon black 30kg adds in the cone-type mixer with filler, by high pressure nozzle the 55kg asarone is sprayed in the blender, fully mixes; Add sodium lignin sulfonate 10kg again, ethoxylated dodecyl alcohol 5kg fully mixes, and can make 55% asarone wetting powder.The water dispersible of preparation, dilution stability, cold and hot storage stability meet the commercially available agricultural chemical preparation and must ask.
The preparation of embodiment 3:5% asarone missible oil.With the 5kg asarone, be dissolved in 80kg methyl alcohol and styrene acid APEO 15kg, join in the 200L reactor, under 40～50 ℃ of temperature, stirred 0.5 hour, promptly make 100kg 5% asarone emulsifiable concentrate.The water dispersible of emulsifiable concentrate, dilution stability, cold and hot storage stability meet the commercially available agricultural chemical preparation and must ask.
The preparation of embodiment 4:50% asarone emulsifiable concentrate.In the 200L reactor, with the 50kg asarone, be dissolved in the 35kg ethyl acetate, add styrene acid APEO 5kg again, octyl phenol polyoxy ethyl ether 10kg stirred 0.5 hour under 40～50 ℃ of temperature, promptly made 100kg50% asarone emulsifiable concentrate.The water dispersible of emulsifiable concentrate, dilution stability, cold and hot storage stability meet the commercially available agricultural chemical preparation and must ask.
The preparation of embodiment 5:10% asarone microemulsion.Take by weighing the former medicine 10kg of asarone, be dissolved in the 15kg isopropyl alcohol, add the 10kg calcium dodecyl benzene sulfonate again, 10kg octyl phenol polyoxy ethyl ether, mixed under high-speed stirred, be heated to about 40 ℃; Drip deionized water 55kg under the high-speed stirred, the rate of addition of control water remains on about 40 ℃ temperature; Water droplet adds and finishes, and is warming up to 50 ℃, stirs 1 hour, makes 10% asarone microemulsion 100kg.Stability of formulation, outward appearance etc. meet the requirement of commodity preparation.
The preparation of embodiment 6:20% asarone microemulsion.Take by weighing the former medicine 20kg of asarone, be dissolved in the 30kg ethyl acetate, add the 15kg calcium dodecyl benzene sulfonate again, 5kg styrene acid APEO, mixed under high-speed stirred, be heated to about 40 ℃; Drip deionized water 30kg under the high-speed stirred, the rate of addition of control water remains on about 40 ℃ temperature; Water droplet adds and finishes, and is warming up to 50 ℃, stirs 1 hour, makes 20% asarone microemulsion 100kg.Stability of formulation, outward appearance etc. meet the requirement of commodity preparation.
Five, field experiment EXPERIMENTAL EXAMPLE
With the reactive compound asarone that the present invention relates to, use compounding method of preparation of the present invention, be mixed with 15% microemulsion, 20% emulsifiable concentrate and 30% wetting powder, carried out the test of pesticide effectiveness of control graw mold of tomato in the land for growing field crops, clear water is contrast, and the control efficiency behind the variable concentrations medicine liquid spray sees Table 4～5.The efficacy survey method is taked parallel lines 2 row samplings, and the incidence of the above fruit of every row investigation 1.5cm is by the generation classification of following grade scale to the fruit gray mold.Calculate control efficiency according to disease index, the significance of difference between each is handled with the analysis of DMRT method.Under the pot experiment condition, carried out the test of control wheat powdery mildew with 50% asarone EC simultaneously.
In experiment,,, all can reach desirable effect by technical scheme preparation of the present invention for various preparations, filler or the solvent of asarone composition, the percentage by weight of surfactant.
1, asarone control wheat powdery mildew results from pot experiment test
Measuring protective effect and the therapeutic action (table 4) of asarone to wheat powdery mildew, the result shows: behind the 7d, asarone is more effective than therapeutic action to the protective effect of wheat white powder.In protective effect, along with the rising of concentration, control efficiency is also high more, and supplying under the examination concentration of 1000mg/L, its preventive effect can reach 68.64%, a little less than the drug effect of contrast medicament triadimefon in 100mg (a.i.)/L dosage processing.Asarone is not obvious to the therapeutic action of wheat white powder, and control efficiency is relatively poor.
Table 4 asarone is to the control efficiency (7d) of wheat powdery mildew
Annotate: adopt DMRT that result of the test is carried out statistical analysis, be meant on α=0.05 level with the different letters in ordered series of numbers mark back to be remarkable difference; Down together.
2, various asarone preparations are to the control efficiency of botrytis cinerea
Measured the control efficiency of the various preparations of asarone, the results are shown in Table 5 graw mold of tomato.
The various asarone preparations of table 5 are to the preventive effect of graw mold of tomato
As known from Table 5, the various preparation forms of asarone are to the better control efficiency of the equal tool of graw mold of tomato, and when being 1000mg/L for amount of reagent, the 14d control efficiency is higher than 80% behind the medicine.
Claims (7)
1. asarone is used to prepare the application of control by the bactericide of the microbial plant disease of pathogenic, and described phytopathogen is botrytis cinerea (Botrytis cirerea) or wheat powdery mildew (Erysiphe graminis).
2. application as claimed in claim 1 is characterized in that, the chemical name of described asarone is 1-pi-allyl-2-methoxyl group-4,5-methylenedioxybenzenes, molecular formula: C
11H
12O
3, molecular weight 192.21, its chemical structural formula is:
And asarone is mixed with missible oil, microemulsion or wetting powder.
3. application as claimed in claim 2 is characterized in that, the raw material of described missible oil and percentage by weight thereof are: asarone 5%～50%, and solvent 40～95%, surfactant 5%～15%, the summation of raw material is 100%.
4. application as claimed in claim 2 is characterized in that, the raw material of described microemulsion and percentage by weight thereof are: asarone 10%～50%, and solvent 40～84%, surfactant 1%～20%, the summation of raw material is 100%.
5. application as claimed in claim 2 is characterized in that, the raw material of described wetting powder and percentage by weight thereof are: asarone 20%～60%, and filler 0～74%, surfactant 1%～25%, the summation of raw material is 100%;
6. as claim 3 or 4 described application, it is characterized in that described solvent is one or more mixtures in methyl alcohol, ethanol, positive isopropyl alcohol, ethyl acetate, the aromatic hydrocarbon.
7. application as claimed in claim 5 is characterized in that, described filler is one or more mixtures in white carbon black, bentonite or the diatomite.
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| CN108142443B (en) * | 2017-12-13 | 2020-07-03 | 中央民族大学 | Asarum sieboldii extract and application thereof as plant antibacterial |
| CN109042745A (en) * | 2018-09-13 | 2018-12-21 | 湖州三零科技有限公司 | Green prevention and control bacterium solution for graw mold of tomato |
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Non-Patent Citations (2)
| Title |
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| Isolation of the antifungal compounds falcarindiol and sarisanfrom Heteromorpha trifoliata. M. Villegas et al.Planta medica,Vol.54 No.1. 1988 |
| Isolation of the antifungal compounds falcarindiol and sarisanfrom Heteromorpha trifoliata. M. Villegas et al.Planta medica,Vol.54 No.1. 1988 * |
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