CN100527957C - Chemical activator and its preparation and application - Google Patents
Chemical activator and its preparation and application Download PDFInfo
- Publication number
- CN100527957C CN100527957C CNB2007100657210A CN200710065721A CN100527957C CN 100527957 C CN100527957 C CN 100527957C CN B2007100657210 A CNB2007100657210 A CN B2007100657210A CN 200710065721 A CN200710065721 A CN 200710065721A CN 100527957 C CN100527957 C CN 100527957C
- Authority
- CN
- China
- Prior art keywords
- compound
- preparation
- virus
- acetonyl
- plant
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The chemical activator, 3-acetonyl-3-hydroxyoxindole (AHO), has obvious effect of antagonizing tobacco mosaic virus (TMV). Research shows that AHO acts on the upstream and downstream of plant's salicylic acid path to activate the systemic acquired resistance of plant. As one new kind of chemical activator, AHO may be used in preventing and treating plant diseases caused by plant virus or pathogenic matter.
Description
Affiliated field:
The present invention relates to drug world, more specifically, relate to 3-acetonyl-3-hydroxyl hydroxyindole (3-acetonyl-3-hydroxyoxindole, AHO) bulk drug and preparation thereof, its preparation method, with and prevent and treat in preparation that salicylic acid synthesis accelerant, botanical system resistance activate the application in the preparation in the sick preparation of viroses of plant medicament, resisting tobacco mosaic virus, the plant.
Background technology:
The research of chemical activator is considered to one of important development direction of 21st century novel agrochemical.In recent years, development abroad chemical activator such as INA, BTH and the being used to system that activates economic crops obtain resistance, these chemical activators are synthetic heterocyclic compound, act on the upstream or the downstream of plant salicylate pathway.BTH once obtained the registration listing.But because its toxic and side effect is used to be subjected to bigger restriction.The chemical activator of external report is mainly used in the pathogen of anti-crops at present, seldom reports the effect as Antiphytoviral.
Summary of the invention:
The object of the present invention is to provide the chemical activator that does not have in a kind of prior art, the active ingredient of this chemical activator is 3-acetonyl-3-hydroxyl hydroxyindole.Further, the present invention also aims to provide the preparation method of this chemical activator, and 3-acetonyl-3-hydroxyl hydroxyindole is prevented and treated in preparation, and salicylic acid synthesis accelerant, botanical system resistance activate the application in the preparation in viroses of plant medicament, the sick preparation of resisting tobacco mosaic virus, the plant.
In order to realize above-mentioned purpose of the present invention, the invention provides following technical scheme:
Chemical activator contains 3-acetonyl-3-hydroxyl hydroxyindole and/or acceptable accessories or carrier.
Described chemical activator can further contain disease-resistant fibroin.
The preparation method of described chemical activator, plant is with methyl alcohol-acetone soln refluxing extraction, again through column chromatography for separation, is catalyzer with beta-schardinger dextrin--benzylamine compound in the methanol-water solvent, and isatin and condensation of acetone are after recrystallization prepares compound.
The preparation method of described chemical activator, plant is with 10% acetone-methanol extraction, get medicinal extract after the removal of solvent under reduced pressure, medicinal extract is successively with benzinum, ethyl acetate, chloroform, methyl alcohol, water-soluble separating, its dissolved matter is prepared into corresponding 5 extracting section things through removing after desolvating, and ethyl acetate extraction is partly separated repeatedly by multiple column chromatography and got final product.
Compound 3-acetonyl-3-hydroxyl hydroxyindole is prevented and treated application in the viroses of plant medicament in preparation.
The application of compound 3-acetonyl-3-hydroxyl hydroxyindole in the sick preparation of preparation resisting tobacco mosaic virus.
Compound 3-acetonyl-3-hydroxyl hydroxyindole is the application in the salicylic acid synthesis accelerant in the preparation plant.
The application of compound 3-acetonyl-3-hydroxyl hydroxyindole in preparation botanical system resistance activation preparation.
Chemical activator formulation of the present invention is preferably aqua or microemulsion.
The present invention relates to the compound 3-acetonyl shown in the chemical formula (1)-3-hydroxyl hydroxyindole:
The present invention is based on the botanical system of finding and study newtype and obtain the resistance chemical activator, screening active ingredients and the antiviral Study on Mechanism of reactive compound by resisting tobacco mosaic virus, found 3-acetonyl-3-hydroxyl hydroxyindole (3-acetonyl-3-hydroxyoxindole, AHO) (1) has the effect of obvious suppression tobacco mosaic virus (TMV), study on mechanism shows, compound (1) has the effect that significant inducing plant system obtains resistance.Be different from other synthetic chemical activator, compound (1) both can act on the upstream of plant salicylate pathway, can act on the downstream of salicylate pathway again, and this compound has easy preparation, characteristics that toxicity is low, can be used as novel chemical activator and be widely used in antiviral, the anti-microbial pathogen of economic crops, become new biopesticide.
Embodiment:
Further illustrate essentiality content of the present invention with embodiments of the invention below, but do not limit the present invention with this:
Embodiment 1:
3-acetonyl-3-hydroxyl hydroxyindole (3-acetonyl-3-hydroxyoxindole, AHO) preparation of (1):
(1) 17 kilograms of usefulness 10% acetone-methanol extraction of dry weight plant acanthaceous indigo (Strobilanthesis cusia) herb, after the removal of solvent under reduced pressure, get medicinal extract, get small part medicinal extract, successively with benzinum, ethyl acetate, chloroform, methyl alcohol, water-soluble separating, its dissolved matter dissolves the solution that is made into 10mg/ml concentration through being prepared into corresponding 5 extracting section things except that after desolvating with DMSO, measures the anti-TMV activity of each several part respectively with ELISA.Ethyl acetate extract separates by multiple column chromatography method repeatedly as active principle, obtains single anti-TMV reactive compound 3-acetonyl-3-hydroxyl hydroxyindole (3-acetonyl-3-hydroxyoxindole, AHO) (1) 17 milligram.
The hydrogen spectrum of table 1 compound (1) and carbon spectrum data
3-acetonyl-3-hydroxyl hydroxyindole (3-acetonyl-3-hydroxyoxindole, AHO) (1)
Be colourless needle, mp 115-117 ℃ (chloroform-methanol), molecular weight are 205, its molecular formula C
11H
11NO
3, optical activity is zero, shows that it is a racemic modification.Its chemical constitution is proved by the X-single crystal diffraction.
The main spectral data of compound (1) is as follows:
UV
λ ETO20nm(logλ)：286(4.23)；EIMS(m/z，％)：205(M
+，57)，187(12)，177(6)，172(14)，162(100)，148(86)，120(84)，92.IRv
max KBrcm
-1：3369，3321(OH)，1760(C＝O)。Hydrogen spectrum and carbon spectrum data see Table 1.
(2) by isatin be the method for feedstock production: 1 gram beta-schardinger dextrin-is dissolved in 100 ml waters, adds 100 ml methanol again.The benzylamine of 1.5 equivalents is added drop-wise in the solution reactant liquor backflow 2-3 hour.Removal of solvent under reduced pressure, residue is washed till no benzylamine smell with methyl alcohol, and the beta-schardinger dextrin-of the white powder that obtains-benzylamine compound is as catalysts.
The commercially available isatin (isatin) of 1 gram is dissolved in water (100 milliliters) and the methyl alcohol (100 milliliters), the acetone that adds 3 equivalents, beta-schardinger dextrin-with 5%-benzylamine compound at room temperature reacted 20 minutes after adding reactant liquor, question response liquid becomes light yellow back cessation reaction by redness, removal of solvent under reduced pressure, the residue dissolve with methanol with the methanol-water recrystallization, obtains the colourless acicular crystal of product.Yield 80%.
Embodiment 2:
The inhibiting rate test that compound (1) duplicates TMV under different dispenser conditions:
For the mechanism of action of the anti-TMV that inquires into compound (1), the present invention has designed three kinds of reagent methods: A) connect virus after the first dispenser, B) connect virus back dispenser, C) medicine and viral combined inoculation earlier.It is 100,200,300,400 that medicine divides 5 concentration, 500nM.Application method: connect virus after the first dispenser, or to connect the dispenser of virus back earlier all be foliage application, medicine and viral combined inoculation be the compound of variable concentrations with after TMV mixes, placement was inoculated in 15 minutes then under 37 ℃ of conditions.Detection method: withered spot detects, Electronic Speculum detects, enzyme linked immunosorbent detection (ELISA) detects.Experimental result shows, connects virus back dispenser and medicine earlier, these two kinds of reagent modes of viral combined inoculation are very low to the inhibiting rate of virus, and connects virus after the first dispenser, to the inhibiting rate of virus all 80% or more as show.This has just hinted that compound (1) is not to directly act on virus but system's acquisition resistance (table 2) of inducing plant.
Table 2, compound (1) are to the inhibiting rate of TMV
Embodiment 3:
Under best reagent condition, the influence that the compound of variable concentrations (1) is bred TMV:
The compound of variable concentrations (1) evenly is sprayed on the host of system tobacco K326 blade, inoculates TMV then, inoculates the propagation that detects virus after three days with ELISA.The result shows that along with the increase of compound concentration, the content of virus reduces gradually, when compound concentrations is 500nM (125 μ g/ml), has detected less than virus (table 3).
Table 3, ELISA method (ELISA) are measured plant virus
The negative contrast of CK-, the positive contrast of CK+, positive greater than positive control, negative less than 2 times negative control.
Embodiment 4:
Compound (1) forms the influence of symptom on the cigarette seedling to virus:
After vigorous, the healthy cigarette seedling of growing is handled with the compound (1) of 70 μ g/ml, inoculation TMV (10 μ g/ml), the symptom that the inoculation back was observed the cigarette seedling on the 3rd day, the result shows, connect virus behind the compound 1 processing cigarette seedling with 70 μ g/ml, the cigarette seedling does not show any flower leaf paresthesia, and Electronic Speculum, ELISA detect less than virus; But serious floral leaf then appears in contrast.
Embodiment 5:
The influence that compound (1) is bred TMV:
After vigorous, the healthy cigarette seedling of growing is handled with the compound (1) of 70 μ g/ml, inoculation TMV (10 μ g/ml), the different time sampling of inoculation back, under Electronic Speculum, observe the propagation of TMV, the result shows that the diamond dust frictional inoculation method makes a large amount of viruses enter mesophyll cell, inoculate back second day virus quantity and obviously reduce, inoculation back the 3rd has not observed virus under the Electronic Speculum everyday.
Embodiment 6:
Execute the antivirus action of compound (1) outward:
Mechanism of action for the anti-TMV that studies compound (1), the present invention utilizes withered spot host method further to verify the anti-TMV activity of compound (1), the result shows that tobacco of handling with compound (1) and the tobacco that does not add processing are relatively, the former is obviously much smaller than the tobacco of not handling by quantity and size that TMV infects the withered spot that forms, and can obviously suppress duplicating of TMV.
Embodiment 7:
Execute the influence of compound (1) at home and abroad tobacco to salicylic acid (SA) accumulation and PR-1 expression:
In plant, the raising of SA level and PR-1 gene expression is often followed in the reaction of inducing anti-disease poison.The raising of SA level and PR-1 gene expression is the key that the formation system obtains resistance.Experimental result shows, executes the obvious raising that compound (1) can cause SA level and PR-1 gene expression outward, and is directly proportional with the concentration of compound (1), shows that compound can pass through the defense response of the accumulation inducing plant of SA to TMV.
Embodiment 8
Compound in tobacco (1) is to the active influence of phenylalnine ammonialyase in the tobacco (PAL):
In plant, phenylalnine ammonialyase is the key of synthetic SA.Experimental result proves, executes the activity that compound (1) can obviously improve phenylalnine ammonialyase outward, and promptly compound (1) may be the raising that causes the SA level by the activity that activates phenylalnine ammonialyase.
Embodiment 9:
Execute the influence that compound (1) changes protein group in the tobacco outward:
In order to study the mechanism of action of compound (1) activated plant defense response, the present invention utilized the two-phase electrophoretic analysis with compound (1) handle with the tobacco of handling without compound (1) in the difference of protein group.The result shows, the point of total protein has 2,735 ± 56 to be mated in the tobacco of handling with compound (1).Point without total protein in the tobacco of compound treatment has 2,520 ± 73 to be mated.The protein spots variance analysis is the result show, nearly 45 protein spots change under the condition that compound exists, and there wherein have 20 albumen to change to be relevant with compound 7.Identified 8 points (table 4) with MALDI-MS, comprised two ribosome inactivating proteins, other 6 albumen can be induced by SA equally.Certified have (tables 4) such as SIPK2, SIP19, MAPK1, MAPK2, NTMEK2.Pointed out the defense response of the anti-TMV of plant that compound induces to depend on the SA approach.
The evaluation of table 4, protein site
| The albumen numbering | The gene pool sequence number | Molecular weight (kDa) | The PI value | Identification of Fusion Protein |
| 1 | AAF67262 | 35 | 7.0 | SIPK2(42KD) |
| 2 | AAQ75123 | 40 | 7.5 | SIP19 |
| 3 | Q39021 | 42 | 6.5 | MAPK1 |
| 7 | BAA24079 | 39 | 7.64 | MAPK2 |
| 20 | AAB58396 | 45 | 5.53 | SIPK |
| 11 | AAH34151 | 20 | 9.0 | CIP2 |
| 17 | 1PUU A | 30 | 65 | lectinIII |
| 13 | AAL91666 | 25 | 7.5 | cofilin |
Embodiment 10:
The 1% microemulsion control tobacco virus field test results of compound (1):
Tobacco virus is one of main disease of China tobacco, average attack rate is about 10%, serious field piece reaches more than 50%, in order to probe into the effective agent of preventing and treating virus disease, the present invention is according to medicine inspecting institute of the Ministry of Agriculture " pesticide field efficacy medicine test criterion ", carry out 1% solution control tobacco virus field control effectiveness test, for determining the best field using dosage of chemical control tobacco virus, the test medicament provides data to influence and medicament drug effect, the safe and rational practical technique of crop and non-target beneficial organism.Trial crops: tobacco; Controlling object: tobacco virus;
Reagent agent:
Application method and water consumption (liter/hectare): adopt the method for spray pesticide, water consumption is 750 liters/hectare.
Result of the test:
Suitable dispenser period and consumption:, think that bactericide 1% solution provided by the present invention has good control efficiency to tobacco virus according to above result of the test.Dispenser for the first time should be when tobacco virus be just sent out, and sick leaf rate is no more than 5%, continuous use 3 times, 7 days medication interval time.Using amount of formulation to be 15000.00g/hm
2(effective ingredient consumption 150.00g/hm
2) time, (amount of formulation is 535.00g/hm to its control efficiency with contrast medicament 10% Ningnan toxin soluble powder
2, effective ingredient consumption 53.50g/hm
2) and 20% virus of A wetting powder (amount of formulation is 3000.oog/hm
2, effective ingredient consumption 600.00g/hm
2) quite.Therefore recommending using dosage is amount of formulation 15000g/hm
2(effective ingredient consumption 150g/hm
2) more than, this agricultural chemicals by registration after, can large tracts of land promote the use of control in tobacco virus.
Using method: spraying
Safety: do not find in the process of the test crop and non-target beneficial organism are produced harmful effect, safer.
Claims (4)
1, chemical activator contains 3-acetonyl-3-hydroxyl hydroxyindole and acceptable accessories or carrier.
2, the application of compound 3-acetonyl-3-hydroxyl hydroxyindole in the sick preparation of preparation resisting tobacco mosaic virus.
3, compound 3-acetonyl-3-hydroxyl hydroxyindole application in the salicylic acid synthesis accelerant in the preparation tobacco plant.
4, the application of compound 3-acetonyl-3-hydroxyl hydroxyindole in preparation tobacco plant system resistance activation preparation.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2007100657210A CN100527957C (en) | 2007-03-19 | 2007-03-19 | Chemical activator and its preparation and application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2007100657210A CN100527957C (en) | 2007-03-19 | 2007-03-19 | Chemical activator and its preparation and application |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101019533A CN101019533A (en) | 2007-08-22 |
| CN100527957C true CN100527957C (en) | 2009-08-19 |
Family
ID=38707465
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2007100657210A Active CN100527957C (en) | 2007-03-19 | 2007-03-19 | Chemical activator and its preparation and application |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN100527957C (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101979379A (en) * | 2010-09-30 | 2011-02-23 | 中国科学院昆明植物研究所 | Method for preparing 3-acetonyl-3-hydroxy oxindole (AHO) |
| CN106718887B (en) * | 2016-11-30 | 2018-12-14 | 云南省农业科学院生物技术与种质资源研究所 | A kind of method of fast eliminating Potyvirus |
| CN112616855A (en) * | 2021-01-21 | 2021-04-09 | 贵州大学 | Plant virus disease immunizing agent |
| CN115843807B (en) * | 2023-03-02 | 2023-04-28 | 云南省农业科学院生物技术与种质资源研究所 | Application of swertia herb flavin compound |
| CN116076512B (en) * | 2023-03-16 | 2023-06-02 | 云南省农业科学院生物技术与种质资源研究所 | Application of isoorientin compound |
-
2007
- 2007-03-19 CN CNB2007100657210A patent/CN100527957C/en active Active
Non-Patent Citations (2)
| Title |
|---|
| Analytical studies on biologically active compounds. Part II.separation and quantitation of mixtures of isatin derivatives forapplication to metabolism studies. Ali, Shahina et al.Pakistan journal of scientific and industrial research,Vol.38 No.8. 1995 * |
| Synthesis of Potential Anticonvulsants: Condensation ofIsatins with Acetone and Related Ketones. POPP. F. D. et al.Journal of Pharmaceutical Sciences,Vol.69 No.10. 1980 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101019533A (en) | 2007-08-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104557709B (en) | Pyrazol acid amide compounds containing diphenyl ether and application thereof and composition pesticide | |
| CN101851356B (en) | Shitake mushroom extract and application thereof | |
| US20060228428A1 (en) | A composition for preventing plant diseases resulted from infection of plant pathogens and a method for preparing the same | |
| CN100527957C (en) | Chemical activator and its preparation and application | |
| Bora et al. | Microbial antagonists and botanicals mediated disease management in tea, Camellia sinensis (L.) O. Kuntze: An overview | |
| Ma et al. | Insecticidal activity of camptothecin against Nilaparvata lugens, Brevicoryne brassicae, and Chilo suppressalis | |
| CN101129455A (en) | Sophora extractive and method of preparing the same and application of the same | |
| CN102718731B (en) | 4 /5-methyl-1, 2, 3-thiadiazole formic acid derivative and preparation method thereof | |
| CN102626078B (en) | Ultra-low-volume liquid for preventing and treating plant viral diseases and transmitting media | |
| CN105211083B (en) | A kind of application of Cyclic dipeptides Cyclo (L Ile L Pro) | |
| Ballio et al. | Occurrence of fusicoccin in plant tissues infected by Fusicoccum amygdali del | |
| US20180092954A1 (en) | Erodium crassifolium l'her plant extracts and uses thereof | |
| CN104365598B (en) | Caffeic acid and the application of Arrcostab in bacterial wilt control thereof | |
| CN103788074B (en) | The Synthesis and applications of radix aconiti agrestis crude extract and effective constituent | |
| CN111109258A (en) | Composition containing Vanilothiopsis ether and antiviral agent and application thereof | |
| CN114794115B (en) | Application of Penicillium poland extract in preparing herbicide | |
| Sotelo et al. | Gossypol content on leaves and seeds from some wild Malvaceae species. | |
| CN104206392A (en) | Complex resistance inducer for prevention of tobacco plant virus and fungal disease, and preparation method and application thereof | |
| CN109122727A (en) | Application of colletotrichum gloeosporioides BWH-1 in preparation of herbicide | |
| WO2018214641A1 (en) | Use of agrimonia pilosa extract in preparation of drug for removing plant virus in tomato plants | |
| CN107771866A (en) | A kind of crowndaisy chrysanthemum bacteriostatic activity monomer and its application method | |
| CN106668012A (en) | Application of nitrogenous heterocycle containing aromatic ester compounds to preparation of medicament for resisting Coxsaekievirus B3 type | |
| Frye et al. | Extraction, identification, and quantification of harmala alkaloids in three species of Passiflora | |
| CN105061412A (en) | Fluorine-containing N-furoamide compound and application thereof | |
| CN101401590B (en) | Uses of protopine total alkaloids in agricultural pesticide |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |