CN101396021A - Use of hinokitiol metal compound - Google Patents
Use of hinokitiol metal compound Download PDFInfo
- Publication number
- CN101396021A CN101396021A CNA2007101523533A CN200710152353A CN101396021A CN 101396021 A CN101396021 A CN 101396021A CN A2007101523533 A CNA2007101523533 A CN A2007101523533A CN 200710152353 A CN200710152353 A CN 200710152353A CN 101396021 A CN101396021 A CN 101396021A
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- Prior art keywords
- oleyl alcohol
- metal compound
- cypressol
- cypress
- cypress oleyl
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Abstract
The invention provides a Cypress oleic alcoholic metallic compound due to the strong antibiotic activity of the compound against infectious pathogenicbacteria and vegetable pathogenicbacteria. The compound can be applied to blocking the infection of infectious pathogenicbacteria for materials by the bacteriostasis or antibiotic functional characteristic, as well as to the environmental cleaning and disease control in farming industry and agricultural plant disease control, thus expanding the application of the Cypress oleic alcoholic metallic compound.
Description
Technical field
The present invention relates to the purposes of cypressol metal compound, relate in particular to cypressol metal compound and give material and press down/purposes of antibacterial functions characteristic, and the purposes of cypressol metal compound in agricultural plant disease control, the aquaculture depollution of environment.
Background technology
The cypress oleyl alcohol also claims thujaplicin (Hinokitiol), and its molecular formula is C
10H
12O
2, molecular weight is 164.20; Its melting point is 51～52 ℃.The cypress oleyl alcohol obtains its white/faint yellow crystallization by distilling to make with extra care, and has following physicochemical property: be insoluble in water, meet light and easily decompose, and to metal tool corrosivity, easily decompose non-refractory, melt and dissolved back, and special odor is arranged.Though the cypress oleyl alcohol has very strong antibacterial activity for various bacteriums, it can be widely used in fields such as medicine, cosmetics and food fresh-keeping; But since its for light, thermoae weak stability, its utmost point be insoluble in water with and to the extremely strong performances such as corrosivity of metal, the facility that can influence its extensive use is implemented.
As promptly disclosing a kind of manufacture method of cypress oil alcohol composition soluble in water in approved No. 1569370 patent of Japan (manufacture method of water ease of solubility cypress oleyl alcohol), cypress oil alcohol composition with this method manufacturing is the heterogeneity assembly of a kind of organic acid salt and cypress oleyl alcohol, though it easily is dissolved in water, the cypress oleyl alcohol is met the labile unstable characteristic of light and is not improved at all.
In view of this, according to a kind of preparation method that can improve the cypress oil alcoholic compound or the cypress oil alcohol composition of the above-mentioned physicochemical property of cypress oleyl alcohol at all, be the facilitating property of extensive use of cypress oleyl alcohol.On this basis, the purposes of cypressol metal compound can be extended in the material surface processing of filming, and in material, add, press down/the antibacterial functions characteristic and give material, particularly its purposes is extended to control and the purification of aquaculture environment and the control of Animal diseases of agricultural plant disease.
Summary of the invention
Technical problem to be solved by this invention provides cypressol metal compound and adds in material surface is filmed processing, material, give material and press down/the antibacterial functions characteristic, with and in the control of plant disease and the application in the aquaculture depollution of environment and the disease prevention and cure.
For solving the problems of the technologies described above, the present invention records cypressol metal compound by experiment and has antibacterial/antibacterial activity to phytopathogen, in view of the above, proposes the application of cypressol metal compound in control of plant disease.
Preferably, cypressol metal compound comprises: cypress oleyl alcohol-Na, Hinokitiol-K, cypress oleyl alcohol-Ni, Hinokitiol-Ca, cypress oleyl alcohol-Mg, Hinokitiol-Cu, cypress oleyl alcohol-Zn, cypress oleyl alcohol-Ag, cypress oleyl alcohol-Mn, cypress oleyl alcohol-Mo, Hinokitiol-Fe
+ 2Reach-Fe with the cypress oleyl alcohol
+ 3
Preferably, phytopathogen comprises plant pathogenic fungi.
Preferably, phytopathogen comprises plant pathogenetic bacteria.
Preferably, phytopathogen comprises plant pathogeny line insect.
For solving the problems of the technologies described above, the present invention records cypressol metal compound by experiment and has antibacterial/antibacterial activity to the zymad bacterium, and propose cypressol metal compound material antibacterial and antibiotic on application, and the application of cypressol metal compound in the aquaculture depollution of environment and disease prevention and cure.
Preferably, cypressol metal compound is filmed at material surface and is handled and add in material and give material antibacterial and antibacterial characteristics.
Preferably, cypressol metal compound comprises: cypress oleyl alcohol-Na, Hinokitiol-K, cypress oleyl alcohol-Ni, Hinokitiol-Ca, cypress oleyl alcohol-Mg, Hinokitiol-Cu, cypress oleyl alcohol-Zn, cypress oleyl alcohol-Ag, cypress oleyl alcohol-Mn, cypress oleyl alcohol-Mo, Hinokitiol-Fe
+ 2Reach-Fe with the cypress oleyl alcohol
+ 3
Preferably, the zymad bacterium comprises the Enterococcus faecium and in the Bacillus subtilis bacterium one or more of staphylococcus, enterococcus faecalis, Gram-negative bacteria, the gram-positive bacteria of gram-positive bacteria.
The present invention has stronger antibacterial activity according to cypressol metal compound to contagiosity cause of disease bacterium and phytopathogen, and propose cypressol metal compound and can be applied to material and press down/antibacterial functions characteristic blocking-up zymad bacterium infects, and cypressol metal compound is in aquaculture depollution of environment disease prevention and cure and the application in the agricultural plant disease control, thus the application of having expanded cypressol metal compound.
Embodiment
Because cypressol metal compound has the antibacterial/antibacterial activity to phytopathogen and phytopathogen, and the application of cypressol metal compound in the agricultural plant disease control proposed; And, because cypressol metal compound has the antibacterial/antibacterial activity to zymad bacterium and phytopathogen, be used for the material surface processing of filming and propose cypressol metal compound, or add in material and give material and press down/the antibacterial functions characteristic, thereby blocking-up zymad bacterium is infected; And the application of cypressol metal compound in the aquaculture depollution of environment and animal diseases control.
Describe the above-mentioned application of cypressol metal compound of the present invention in detail below by specific embodiment.
Embodiment 1: cypressol metal compound is to the antibacterial activity test of phytopathogen.
Experiment material:
(1) anti-biotic material can be cypress oleyl alcohol-Na ,-Ni ,-Ca ,-Cu ,-Zn ,-Ag ,-Mn ,-Fe
+ 2And-Fe
+ 3Deng;
(2) test plant pathogen: as shown in table 1;
Table 1
| The pathogen classification | The pathogen title |
| Fungi | The cotton seedling blight bacterium of Root Rot of Wheat germ (Helminthosporium sativum) fusarium graminearum (Gibberella zeae) soybean sclerotinia crown rot bacterium (Sclerotinia sclerotiorum) tomato early blight bacterium (Alternaria solani) (Rhizoctonia solani AG4) cotton-wilt fusarium (Fusarium oxysporum f.sp.vasinfectum) |
| Stem point mould (Phoma) eggplant fusarium (Fusarium solania) Botrytis cinerea bacterium (Botrytis cenerea) Rhizoctonia solani Kuhn verticillium dahliae pseudo-ginseng post spore germ phytophthora sojae kaufmann﹠gerdemann | |
| Bacterium | The blue or green withered bacterium pseudo-ginseng bacterium paddy rice bacterial leaf spot bacterium of tomato |
| Nematode | Soybean Cyst nematode (Heterodera glycines) root-knot nematode (Meloidogyne incognita) sweet potato stem nematode (Ditylenchus dipsaci) |
Experimental technique: with cypress oleyl alcohol-Na is example
(1) to the influence of plant pathogenic fungi
Contain toxic medium method in indoor employing and measure cypress oleyl alcohol-Na activity for the examination bacterial classification.
Preparation PDA medium is got the 100mL medium respectively and is packed in several 250ml triangular flasks high pressure steam sterilization 30min into.
Take by weighing cypress oleyl alcohol-Na respectively, 0,2.5mg, 5.0mg, 7.5mg, 10.0mg, 95% dissolve with ethanol with 0.5mL, join in (below 50 ℃) 100ml PDA medium of low-grade fever, and shake up rapidly that on average to pour 6 diameters into be in the culture dish of 9cm, make the flat board that contains the variable concentrations medicament, only to add ethanol in contrast.In superclean bench, placed 2-3 days.From cultivating the colony edge for the examination bacterial classification of 4-7d, cut-off directly is the bacterium cake of 8mm, and bacterium faces down, and inserts in the plate 3 repetitions.24 ℃ of following constant temperature culture 3-4d (can proper extension according to the growth rate of survey bacterial classification) measure colony diameter with the cross method of scoring.Calculate the EC50 value of medicament, obtain virulence regression equation, and estimate the bacteriostatic activity of medicament.
(2) influence that plant pathogenetic bacteria is grown and bred
Cypress oleyl alcohol-Na is joined in King ' the s B medium, make that its concentration is 0,25,50,75,100ppm, fall dull and stereotypedly, place 1-2d.
The preparation bacterial suspension makes its concentration reach 10
7Cfu/ml.Serial dilution then, adjusting its concentration is 10
6Cfu/ml, 10
5Cfu/ml, 10
4Cfu/ml.Get 10 respectively
4The equal suspension 0.1ml of cfu/ml concentration coats on the flat board, and 28 degree are cultivated 2d, the record clump count.
(3) to the influence of plant pathogeny line insect
Cypress oleyl alcohol-Na is dissolved in absolute ethyl alcohol earlier, be diluted to desired concn with sterile water then.With the aqueous solution that contains equivalent ethanol is contrast, puts into each nematode larval 200-300 bar in each concentration cypress oil alcoholic solution respectively, places under the room temperature (20-22C) behind the 2h, measures lethality, and is proofreaied and correct.
Whether dead discriminating can add a 10%NaOH to nematode in treatment fluid, thinks that then nematode is dead if nematode is stiff.Calculate the LD50 of nemic death rate and medicament according to check result.
Experimental result and analysis:
(1) to the bacteriostasis rate of fungi and bacterium
Cypress oleyl alcohol-Na sees also table 2 and table 3 to the bacteriostasis rate analysis of fungi and bacterium.
Table 2 cypress oleyl alcohol-Na is to the bacteriostasis rate analysis of fungi
Table 3 cypress oleyl alcohol-Na is to the bacteriostasis rate analysis of bacterium
The pressing down of Hinokitiol-Cu or cypress oleyl alcohol-Ag/antibacterial effect also will be got well, and minimal inhibitory concentration is 25～75mg/L.
(2) to the toxic effect analysis of nematode
Cypress oleyl alcohol-Na sees also table 4 to the toxic effect analysis of nematode.
Table 4 cypress oleyl alcohol-Na is to the toxic effect analysis of nematode
The toxic effect of Hinokitiol-Fe, Hinokitiol-Cu or cypress oleyl alcohol-Ag also will be got well, and minimal inhibitory concentration is 25～50mg/L.
Embodiment 2: cypressol metal compound is to the antibacterial activity of zymad bacterium
Cypressol metal compound is added in the paint with ultimate density 25 μ g/ml, the medical office appliance of spraying new production, testing equipment, communal facility equipment etc. are given the antibacterial activity coating at material surfaces such as medical device articles for use, communal facility equipment;
Cypressol metal compound (mainly being the colourless or whitening compound of Na, Zn, K, Ca, Mg) is added in the wall covering with ultimate density 120 μ g/ml, spraying hospital body of wall etc., surface of wall is given the antibacterial activity coating;
Cypressol metal compound is dissolved in the spirit solvent with ultimate density 15 μ g/ml, to air-atomizing, air in the sterilizing and purifying hospital;
Cypressol metal compound is added in the cleaning soap (liquid) with ultimate density 10 μ g/ml, and cleaning material is given antibacterial activity and is coated with activity;
More than use example, have and suppress to infect pathogeny bacterium activity, prevent and treat functional effect such as pathogeny bacterium public place infection.Cypressol metal compound is to the staphylococcus of gram-positive bacteria and the growth minimal inhibitory concentration (MIC) of enterococcus faecalis: Hinokitiol-Cu is that 0.75～30 μ g/ml, Hinokitiol-Fe are 0.72～1.35 μ g/ml, and the MIC of cypressol metal compounds such as Na, Zn, K, Ca, Mg is the scope of 26～58 μ g/ml.
Cypressol metal compound is to the Enterococcus faecium of Gram-negative bacteria, gram-positive bacteria and the growth minimal inhibitory concentration (MIC) of Bacillus subtilis bacterium: Hinokitiol-Cu, and-Na ,-Zn ,-K ,-Ca ,-cypressol metal compounds such as Mg are 23～150 μ g/ml scopes.
The antibacterial activity that contagiosity germ in the hospital is had wide region.
Though the present invention discloses as above with preferred embodiment; right its is not in order to limiting the present invention, anyly has the knack of this skill person, without departing from the spirit and scope of the present invention; when can doing a little change and retouching, thus protection scope of the present invention when with aforementioned claims the person of being defined be as the criterion.
Claims (9)
1, according to cypressol metal compound the application of cypressol metal compound in control of plant disease proposed for the antibacterial of phytopathogen and antibacterial functions characteristic.
2, according to the described application of claim 1, it is characterized in that described cypressol metal compound comprises: cypress oleyl alcohol-Na, Hinokitiol-K, cypress oleyl alcohol-Ni, Hinokitiol-Ca, cypress oleyl alcohol-Mg, Hinokitiol-Cu, cypress oleyl alcohol-Zn, cypress oleyl alcohol-Ag, cypress oleyl alcohol-Mn, cypress oleyl alcohol-Mo, Hinokitiol-Fe
+ 2Reach-Fe with the cypress oleyl alcohol
+ 3
3, according to claim 1 or 2 described application, it is characterized in that described phytopathogen comprises plant pathogenic fungi.
4, according to claim 1 or 2 described application, it is characterized in that described phytopathogen comprises plant pathogenetic bacteria.
5, according to claim 1 or 2 described application, it is characterized in that described phytopathogen comprises plant pathogeny line insect.
6, according to cypressol metal compound to the antibacterial of zymad bacterium and antibacterial functions characteristic propose cypressol metal compound material antibacterial and antibiotic on application, and the application of cypressol metal compound in the aquaculture depollution of environment and disease prevention and cure.
According to the described application of claim 6, it is characterized in that 7, cypressol metal compound is filmed at material surface and handled and add and give material antibacterial and antibacterial characteristics in material.
8, according to claim 6 or 7 described application, it is characterized in that described cypressol metal compound comprises: cypress oleyl alcohol-Na, Hinokitiol-K, cypress oleyl alcohol-Ni, Hinokitiol-Ca, cypress oleyl alcohol-Mg, Hinokitiol-Cu, cypress oleyl alcohol-Zn, cypress oleyl alcohol-Ag, cypress oleyl alcohol-Mn, cypress oleyl alcohol-Mo, Hinokitiol-Fe
+ 2Reach-Fe with the cypress oleyl alcohol
+ 3
9, according to the described application of claim 6, it is characterized in that described zymad bacterium comprises the Enterococcus faecium and in the Bacillus subtilis bacterium one or more of staphylococcus, enterococcus faecalis, Gram-negative bacteria, the gram-positive bacteria of gram-positive bacteria.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2007101523533A CN101396021A (en) | 2007-09-28 | 2007-09-28 | Use of hinokitiol metal compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2007101523533A CN101396021A (en) | 2007-09-28 | 2007-09-28 | Use of hinokitiol metal compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101396021A true CN101396021A (en) | 2009-04-01 |
Family
ID=40515076
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2007101523533A Pending CN101396021A (en) | 2007-09-28 | 2007-09-28 | Use of hinokitiol metal compound |
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| Country | Link |
|---|---|
| CN (1) | CN101396021A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103755561A (en) * | 2014-01-10 | 2014-04-30 | 广州英赛特生物技术有限公司 | Beta-chamaecyparis phenolic ester or salt and application thereof in preparation of animal feed additive |
| WO2015103806A1 (en) * | 2014-01-10 | 2015-07-16 | 广州英赛特生物技术有限公司 | 2-hydroxyl-4-n-propyl-1-tropone ester or salt and application thereof in preparing antibacterial agent for animals and growth promoter for feed |
| WO2022247696A1 (en) * | 2021-05-28 | 2022-12-01 | 中国科学院上海药物研究所 | Co-crystal of hinokitiol and tert-butylhydroquinone, preparation method therefor, and use thereof |
-
2007
- 2007-09-28 CN CNA2007101523533A patent/CN101396021A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103755561A (en) * | 2014-01-10 | 2014-04-30 | 广州英赛特生物技术有限公司 | Beta-chamaecyparis phenolic ester or salt and application thereof in preparation of animal feed additive |
| WO2015103806A1 (en) * | 2014-01-10 | 2015-07-16 | 广州英赛特生物技术有限公司 | 2-hydroxyl-4-n-propyl-1-tropone ester or salt and application thereof in preparing antibacterial agent for animals and growth promoter for feed |
| CN103755561B (en) * | 2014-01-10 | 2015-12-09 | 广州英赛特生物技术有限公司 | β-Japan cypress phenolic ester or salt and preparing the application in animal feedstuff additive |
| US9938230B2 (en) | 2014-01-10 | 2018-04-10 | Guangzhou Insighter Biotechnology Co., Ltd. | Esters or salts of 2-hydroxy-4-propylcyclohepta-2,4,6-trienone and application thereof in preparation of animal antibacterial agents and growth promoters used in feed |
| WO2022247696A1 (en) * | 2021-05-28 | 2022-12-01 | 中国科学院上海药物研究所 | Co-crystal of hinokitiol and tert-butylhydroquinone, preparation method therefor, and use thereof |
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Open date: 20090401 |