CN108569997A - One kind is used for the compound and its application method of Plant-induced resistance - Google Patents
One kind is used for the compound and its application method of Plant-induced resistance Download PDFInfo
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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- A01N35/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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Abstract
The invention discloses a kind of compounds and its application method for being used for Plant-induced resistance, and shown in the compound formula such as formula (I), the meaning of wherein R group is shown in specification.Compound disclosed by the invention has good stability and water solubility, and shows excellent induction plant disease-resistant activity, is agriculturally there is good use value.
Description
Technical field
The invention belongs to biological pesticides and plant protection art, and in particular to a kind of compound is in Plant-induced resistance
Using.
Background technology
Induction of resistance is also known as plant immune, refers to plant under the stimulation of the inducible factor of physical chemistry or biology, by swashing
The immune system of living plant itself and the metabolism for adjusting itself, to generate the performance that can resist disease and adverse circumstance.Due to
Have many advantages, such as has a broad antifungal spectrum, it is environmentally friendly safely, be not likely to produce drug resistance, plant immune inducer (also known as plant disease-resistant
Activator) just as the recent studies on hot spot in pesticide developing.
Domestic and international numerous studies show that plant immune inducer has and improve cropper resistance and effective prevention and control crop disease
Harmful ability.American scientist exists within 2006《Nature》It first proposed the concept of plant immune system on magazine.Then, moral
State scientist has found：Plant in nature can identify exempting from for the microorganisms such as bacterium, virus and mould invasion with special
Epidemic disease sensor (immune system).Plant can perceive the presence of pathogen by the immune system of itself, when pathogen infection,
Plant will start the signal path in downstream, induce corresponding Resistant reaction to resist the invasion of pathogen.People utilize plant
This induction immune resistance mechanism of object uses elicitor or exciton exploitation at inducer or immune formulation, and for its function
In the prevention of plant disease.Plant immune inducer is to resistance signal caused by plant through endogenous signal transmitter bigcatkin willow
Acid, jasmonic, ethylene etc. and be transmitted to entire plant, cause host anti-by the regulation and control and expression of a series of disease-resistant related genes
Imperial enzyme system such as phenylalanine lyase, beta-1,3-glucanase, chitinase, peroxidase etc. and disease-resistance substance such as lignin
Mitigate and prevent the generation of disease with the variation of protective plant protecting agent etc. to resist the intrusion and development of pathogen.
Currently, studies have found that there is many compounds induction plant to generate resistance to resist the energy of pathogen infection
Power.Such as salicylic acid (SA), 2,6- dichloro-isonicotinic acids (INA), diazosulfide (BTH) class compound, probenazole (PBZ), β-
Aminobutyric acid (BABA), methyl jasmonate (MeJA), amino-oligosaccharide etc..In addition, Chinese Academy of Agricultural Sciences's plant protection research
First, China anti-viral protein biological pesticide is developed recently --- 6% oligosaccharides catenin wettable powder.Plant
Inducer itself is non-toxic or low-toxic, environmental sound, so being very promising novel biopesticide.But it is traditional
Plant induced resistance agent such as BTH is there are poorly water-soluble, catenin is unstable, it is degradable, influence the problems such as plant growth.
Invention content
It is an object of the invention to according to above-mentioned deficiency in the prior art, provide a kind of novel, efficient plant inducer
Anti-agent can improve rapidly the ability of plant resistant pathogen infection after, while safe and harmless to plant, to environment without dirt
Dye.
The present invention provides a kind of compound for being used for Plant-induced resistance, structure is as shown in logical formula (I)：
In formula above：
R can be indicated：Hydroxyl, C1-C6Alkyl, C2-C6Alkenyl, C2-C6Alkynyl, the wherein alkyl, alkenyl and alkynyl group
Optionally by 1 to 3 independently selected from halogen, C1-C6Alkoxy, C1-C6Alkylthio group, aryl, heteroaryl substituent group take
Generation.R can not be individually for methyl.
Wherein substituent group is represented as optionally being substituted, this means that they can be carried or can be without one
A or multiple same or different substituent groups, such as one to three substituent group.Normally, not more than three are existed simultaneously in this way
Optional substituent group.When a group is represented as substituted, such as alkyl, this includes the part for being other groups
Those of alkyl in group, such as alkylthio group.
Term " halogen " refers to fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine.When halogen is as substituent group, it is substituted
Group can contain one or more same or different halogen atoms, and can for example represent CH2Cl、CHCl2、CCl3、
CH2F、CHF2、CF3、CF3CH2、CH3CF2、CF3CF2Or CCl3CCl2。
Alkyl substituent can be straight chain either branch.Quantity depending on the carbon atom mentioned, alkyl its
Body or part as another substituent group are such as methyl, ethyl, n-propyl, normal-butyl, n-pentyl, n-hexyl and theirs is different
Structure body, such as isopropyl, isobutyl group, sec-butyl, tertiary butyl or isopentyl.
Alkenyl group may be at the form of linear chain or branched chain, and can be (as appropriate) have these alkenyl parts
(E)-or (Z)-configuration.Example is vinyl and allyl.These alkenyl groups are preferably C2-C6, more preferably C2-C4And
And most preferably C2-C3Alkenyl group.
Alkynyl substituted base may be at the form of linear chain or branched chain.Example is acetenyl and propargyl.These alkynyl groups
Preferably C2-C6, more preferably C2-C4And most preferably C2-C3Alkynyl group.
Alkoxy refers to that-OR bases, wherein R are alkyl for example as defined above.Alkoxy base includes but does not limit to
In methoxyl group, ethyoxyl, 1- methyl ethoxies, propoxyl group, butoxy, 1- methyl propoxyl group and 2- methyl propoxyl group.
Alkylthio group refers to that-SR bases, wherein R are alkyl for example as defined above.Alkylthio radicals include but do not limit to
In methyl mercapto, ethylmercapto group, 1- methylethylthios, rosickyite base, butylthio, 1- methyl-props sulfenyl and 2- methyl-prop sulfenyls.
Represented hydroxy-OH groups
Aryl group is aromatic ring (either individually or as the part of a more macoradical, such as aryloxy group, aryl-alkyl)
Form, they may be at single, double or tricyclic form.The example of such ring includes phenyl, naphthalene, anthryl, indenyl or phenanthrene
Base.Preferred aryl group is phenyl and naphthalene, and phenyl is most preferred.It is considered substituted in aryl moiety,
The aryl moiety is preferably replaced by one to four substituent group, is most preferably replaced by one to three substituent group.
Heteroaryl groups (either individually or as the part of a more macoradical, such as heteroaryloxy, heteroaryl-alkyl)
It is aromatic ring system, these systems include at least one hetero atom and by single ring or the ring of two or more thick sums
Composition.Preferably, monocycle will include up to three hetero atoms and bicyclic system includes up to four hetero atoms, these hetero atoms
Nitrogen, oxygen and sulphur will be preferably chosen from.The example of monocyclic groups include pyridyl group, pyridazinyl, pyrimidine radicals, pyrazinyl, pyrrole radicals,
Pyrazolyl, imidazole radicals, triazolyl (for example, [1,2,4] triazolyl), furyl, thiophenyl, oxazolyl, isoxazolyl, oxadiazoles
Base, thiazolyl, isothiazolyl and thiadiazolyl group.The example of bicyclic radicals includes purine radicals, quinolyl, cinnoline base, quinoxaline
Base, indyl, indazolyl, benzimidazolyl, aisaa benzothiophenyl and benzothiazolyl.The heteroaryl groups of monocycle are preferred
, pyridyl group is most preferred.Be considered substituted in heteroaryl moieties, the heteroaryl moieties preferably by one to
Four substituent group substitutions, are most preferably replaced by one to three substituent group.
The presence of one or more possible asymmetric carbon atoms indicates these changes in the compound with chemical formula (I)
Closing object can exist in the form of optics isomeric forms, that is, enantiomter or diastereoisomer.Chemical formula (I) is intended to wrap
Include the possible isomeric forms of all that and their mixture.
Compound with chemical formula (I) can also be solely mixedly as inducer in plant inducer impedance
It is applied in property.
Immunity energy of the crops to the plant disease caused by fungi, bacterium and virus can be improved in compound of the present invention
Power.
Induction of resistance objective crop of the present invention is preferably tobacco, tomato, rice, potato, corn, banana, flower
Raw, soybean, more preferably tobacco, tomato, rice, potato, banana, most preferably tomato and banana.
The present invention can be used for preventing the plant disease caused by fungi, bacterium and virus.These diseases include by plant
Tobacco mosaic disease caused by virus, pepper virus disease, Virus Diseases of Rice, tomato virus disease, Virus Diseases of Sweet Potato, potato virus disease
With melon virosis and maize dwarf mosaic；The cucumber bacterial angular leaf spot caused by bacterium, cucumber marginal leaf blight, cucumber leaf are withered
Disease, bacterial wilt of tomato, canker of tomato, tomato shot hole, pepper ralstonia solanacearum, bacterial spot of pepper, capsicum soft rot, the soft corruption of Chinese cabbage
Disease, Seed detection, potato bacterial wilt, bacterial soft rot of potato, bacterial ring rot o potato, eggplant bacterial wilt and banana blight；
By fungus-caused cucumber anthracnose, grape rust, downy mildew of garpe, corn stalk rot disease, rice blast, powdery mildew, wheat
Smut, cucumber downy mildew, potato wilt etc..
Most preferably controlling disease is tobacco mosaic disease, tomato wilt, banana blight, cotton verticillium wilt, rice rice blast
Disease, potato bacterial wilt, potato wilt, downy mildew of garpe, corn stalk rot disease.
The method of administration of compound or composition of the present invention is preferably foliage-spray and root trickle irrigation.Foliage-spray is
Refer to, formula (I) compound is sprayed on Plant aboveground position such as with water, the face of blade or back side, stem and branch.Root trickle irrigation is
Refer to, formula (I) compound is added in drip irrigation appliance and imposes on plant root with water droplet.
Another object of the present invention is to provide a kind of inducer composition that can be used for inducing plant disease-resistant, this composition packet
Containing compound defined in the logical formula (I) of at least one.
The composition be preferably 3,4- dihydroxy -3- methyl -2 pentanone, salicylic acid (SA), gaultherolin (MeJA),
Jasmonic (JA), methyl jasmonate (MeJA), 2,6- dichloro-isonicotinic acids (INA), diazosulfide (BTH), probenazole (PBZ),
It is one or more in beta-aminobutyric acid (BABA), amino-oligosaccharide.
Logical formula (I) compound of the present invention is as inducer active constituent in use, amount ranges are 0.5g to 500g/
hm2, optimal usage amount is 5g to 100g/hm2。
The principle of the present invention：Plant in nature can identify the microorganisms such as bacterium, virus and mould with special
The immunosensor (immune system) of invasion.Plant can perceive the presence of pathogen by the immune system of itself, work as cause of disease
When bacterium is infected, plant will start the signal path in downstream, induce corresponding Resistant reaction to resist the invasion of pathogen.This
Invention utilizes this induction immune resistance mechanism of plant, induced activation plant immune system, the resistance signal of generation, resistance signal
It is transmitted to entire plant by salicylic acid, jasmonic/ethylene the signaling pathways of disease resistance, by a series of disease-resistant related genes
Regulation and control and expression cause host defense enzyme system such as phenylalanine lyase, beta-1,3-glucanase, chitinase, peroxidase
Deng and the variation of disease-resistance substance such as lignin and protective plant protecting agent etc. mitigate and prevent disease to resist the intrusion and development of pathogen
Generation.
The preferably following structural formula compound of the present invention is as specific embodiment controlling plant diseases：
The advantageous effect that the present invention obtains：
Compound provided by the present invention can quickly excite plant disease-resistant related gene expression, induce plant disease resistance-related protein
Synthesis improves resistance of the plant to pathogen.During experiment indoors and field use, it can significantly inhibit Tobacco mosaic
The generation of disease, tomato wilt, banana blight, rice blast and cotton verticillium wilt.
Description of the drawings
Fig. 1 B-4-a, B-4-b and Mix processing arabidopsis induce disease-resistant related gene PR-2, PR-3, PDF1.2 and VSP
Expression
Arabidopsis PAL, POD and beta-1,3 glucanase enzymatic activity after Fig. 2 B-4-a, B-4-b and SA are handled
Arabidopsis is to pathogen DC3000 disease resisting effects after Fig. 3 B-4-a, B-4-b, Mix and BTH processing
DC3000 contents in Arabidopsis leaf after Fig. 4 B-4-a, B-4-b, Mix and BTH processing
Inhibiting rate of the arabidopsis to DC3000 after Fig. 5 B-4-a, B-4-b, Mix and BTH processing
Specific embodiment
The above of the present invention is described in further detail by the following examples, but this should not be interpreted as to this
The range for inventing above-mentioned theme is only limitted to embodiment below, and all technologies realized based on the above of the present invention belong to this hair
Bright range.
Prepare embodiment：
1. prepared by compound B-4:Its reaction step is as follows：
By the phenylboric acid of 12mmol, two (triphenylphosphine) palladium chlorides of 0.2mmol and the potassium phosphate of 12mmol are added
In the toluene solution of 50mL, nitrogen protection.The toluene solution of 10mmol crotonyl chlorides is slowly added dropwise, it is small to be warming up to 80 DEG C of reactions 4
When.After reaction, it is cooled to room temperature, filters, column chromatography obtains compound 1.50g, yield 90%.
First step product 10.8mmol is dissolved in the in the mixed solvent of THF and water, the N- methyl-N- oxygen of 11.8mmol is added
Change morpholine and the osmium tetroxide solution 0.5mL of 1M, is stirred overnight at room temperature.After reaction, the thio sulphur of the saturation of 50mL is added
Acid sodium solution stirs 1 hour.Dichloromethane extracts.Hand-type column preparative separation obtains the compound B-4-a and B-4- of two kinds of configurations
b。
2, prepared by compound B-5:Its reaction step is as follows：
By the 3- pyridine boronic acids of 20mmol, the potassium phosphate of two (triphenylphosphine) palladium chlorides and 20mmol of 0.12mmol
It is added in the toluene solution of 80mL, nitrogen protection.The toluene solution of 17mmol crotonyl chlorides is slowly added dropwise, is warming up to 80 DEG C of reactions
8 hours.After reaction, it is cooled to room temperature, filters, column chromatography obtains compound 2.2g, yield 81%.
First step product 13.7mmol is dissolved in the in the mixed solvent of THF and water, the N- methyl-N- oxidations of 15mmol are added
The osmium tetroxide solution 0.8mL of morpholine and 1M, is stirred overnight at room temperature.After reaction, the thiosulfuric acid of the saturation of 60mL is added
Sodium solution stirs 1 hour.Dichloromethane extracts.Hand-type column preparative separation obtains the compound B-5-a and B-5-b of two kinds of configurations.
Application Example
Embodiment 1 improves the expression of disease-resistant related gene
The mixture M ix for preparing 100 μM of concentration B-4-a, B-4-b and B-4-a and B-4-b respectively, chooses 6-7 weeks size
The inducer prepared is uniformly sprayed at arabidopsis surface by arabidopsis spray-on process, if clear water is control, is sampled afterwards for 24 hours, liquid nitrogen
Quick-frozen, then blade total serum IgE is extracted in grinding.The extraction of arabidopsis total serum IgE is according to kit E.Z.N.A.TMPlant RNA
The method extracting that Kit (OMEGA) is provided.Arabidopsis total serum IgE passes through iScript after removing genomic DNA with DNase ITM
Reverse Transcription (Bio-Rad) reverse transcription is cDNA.1ul reverse transcription products are taken to be quantitative fluorescent PCR (SYBR
), Green.Bio-Rad use PCR instrument model CFX96 (Bio-Rad Laboratories, Hercules, CA,
USA).PCR step is 95 DEG C, 15s；95 DEG C, 10s and 60 DEG C, 30s carries out 40 cycles.AtActin is as internal reference (F:5-
AGTGGTCGTACAACCGGTATTGT-3 ', R:5′-GATGGCATGAGGAAGAGAGAAAC-3′).With induction of resistance dependency basis
Because special primer is PCR (AtPDF1.2 genes F:5 '-TTTGCTGCTTTCGACGCAC-3 ', R:5′-
CGCAAACCCCTGACCATG-3′；AtVSP genes F:5 '-TCAGTGACCGTTGGAAGTTGTG-3 ', R:5-
GTTCGAACCATTAGGCTTCAATATG-3′；AtPR-2 genes F:5 '-AGCTTAGCCTCACCACCAATGT-3 ', R:5′-
CCGATTTGTCCAGCTGTGTG-3′；AtPR-3 genes F:5 '-GGCCAGACTTCCCATGAAAC-3 ', R:5′-
CTTGAAACAGTAGCCCCATGAA-3′).After RT-qPCR is expanded, according to the Ct values of each sample with 2-ΔΔCTMethod calculates base
Because of expression value.
The results are shown in Figure 1 PDF1.2 and VSP is in jasmonic/ethylene the signaling pathways of disease resistance two mark bases
Cause, PR-1PR-2 are two very important genes in salicylic acid the signaling pathways of disease resistance.The present invention respectively use B-4-a,
B-4-b and Mix processing arabidopsis has detected the expression of above-mentioned 4 induction of resistance related genes afterwards for 24 hours, wherein after B-4-a processing
Arabidopsis plant PDF1.2, VSP, PR-2 and PR-3 expression quantity be respectively compare 1.95,3.87,5.09 and 2.87 times,
The expression quantity of B-4-b treated Arabidopsis plant PDF1.2, VSP, PR-2 and PR-3 be respectively 6.01 compareed, 7.05,
2.02 and 0.30 times, the expression quantity of Mix treated Arabidopsis plant PDF1.2, VSP, PR-2 and PR-3 is respectively to compare
5.03,1.01,3.99 and 1.68 times.It can be seen that B-4-a, B-4-b and Mix have activated plant immune system well, cause
The expression of disease-resistant related gene.
Embodiment 2 improves resistance-related enzymes enzyme activity
1. arabidopsis induction early period is handled
100 μM of concentration B-4-a, B-4-b and salicylic acid (SA) are prepared, takes 12 basin well-growns and the quasi- south of growing way always
Mustard, is uniformly sprayed on plant leaf tow sides respectively, and 3 repetitions are arranged in every group of 3 plants of processing.After processing, suitable and identical
Under conditions of culture 48h after, carry out enzyme assay experiment.
2. enzyme solution extracts
Each processing takes 0.5g tender leafs grinds in liquid nitrogen respectively, is transferred in 2ml centrifuge tubes, and 1.5ml phosphoric acid is added
Potassium buffer solution (pH=7) is fully homogenized, centrifuges 15min under the conditions of 12000rpm, 4 DEG C, supernatant is taken to be extracted as thick enzyme
Liquid.
3. enzyme assay
Peroxidase (POD)：Reaction solution is that 1.425ml 0.1mol/L, PH7.0 phosphate buffers (include
10uL40mmol/L H2O2, 25ul 200mmol/L guaiacol) and 25uL enzyme solutions, measure at room temperature measured under 470nm it is every
The variation of minute OD.POD enzyme activities=Δ OD470mg-1(pr)·min-1, 3 parallel groups measure, are averaged respectively.
Phenylalanine lyase (PAL)：Reaction solution is 0.95mL 100mmol/L, pH8.5Tris-HCL buffer solution, 0.5ml
15mmol/LL- phenylalanines and 0.5ml enzyme solutions react 15min in 30 DEG C of water-baths, and the hydrochloric acid that 100ml 6mol/L are added is whole
It only reacts, OD values is surveyed under 290nm wavelength, 3 parallel groups are measured, are averaged respectively.Provide to increase in 1h 0.01 as PAL's
One enzyme activity unit.
Beta-1,3-glucanase：The laminarin of 10mg/ml is dissolved in the acetate buffer of 0.05mol/L, pH5.0 first
In liquid, 50ul or more mixed liquors, 50ul enzyme solutions and 1.5ml DNS reagents are taken, 1h is kept the temperature in 37 DEG C, appropriate concentrated hydrochloric acid is added and terminates
Reaction measures OD values under 530nm, with the enzyme amount of generation reduced sugar 1nmol per minute for 1 enzyme activity unit.
4. interpretation of result：
1,3 dextranase of PAL, POD and β-is plant disease-resistant relevant enzyme, as shown in Fig. 2, after B-4-a, B-4-b processing
Arabidopsis leaf in the activity of PAL, POD and beta-1,3 glucanase have promotion compared with clear water compares.Wherein, at B-4-a
The enzymatic activity of PAL and POD is suitable with positive control SA effects in Arabidopsis leaf after reason, β -1, and the activity of 3 dextranases is high
In positive control SA.
Embodiment 3 induces disease resistance of the arabidopsis to DC3000
Respectively with mixture M ix, BTH and clear water processing arabidopsis of 100 μM of B-4-a, B-4-b, B-4-a and B-4-b
For 24 hours, bacterium DC3000 is then met, while setting one and meeting MgSO4As a contrast.Arabidopsis leaf incidence is observed after 3 days.
The disease-resistant situation of arabidopsis handles (such as Fig. 3 significantly lower than clear water after B-4-a, B-4-b, Mix and BTH processing
It is shown), meet MgSO4Blade do not fall ill and illustrate that this experiment is reliable.
The blade of morbidity is shredded, is ground, coated plate, incubator counts clump count after growing 2 days, and it is right after drug-treated to calculate
The inhibition of pathogen DC3000.
As shown in Figure 4 and Figure 5, the tablet of B-4-a, B-4-b, Mix, BTH and clear water processing, clump count every square centimeter point
Not Wei 24,16,36,11,50, relative to CK, the control effect of positive control BTH is best, and inhibiting rate reaches 78%.B-4-a、B-
Secondly, inhibiting rate is respectively 51.33%, 68% and 28% to the control effect of 4-b and Mix.
Resistance of 4 evoking tobacco of embodiment to tobacco mosaic virus (TMV) (TMV)
Weighed respectively on a ten thousandth balance B-1, B-2, B-3, B-4-a, B-4-b, B-5-a, B-5-b, B-6, B-7, B-8,
B-9, B10 and B-11, with clear water by above-mentioned medicament compound concentration be 1000 μM, 100 μM and 10 μM three concentration gradients.Choose 4
The liquid prepared is uniformly sprayed at tobacco blade face by the tobacco seedlings spray-on process of Zhou great little, if clear water is control.After spraying 48 hours,
It is rubbed using half leaf method and is inoculated with TMV.Occur apparent withered spot after 3d, record withered spot number in time, calculates inhibiting rate.
Inhibiting rate calculation formula is as follows:
Inhibiting rate (%)=(control withered spot number one handles withered spot number)/control withered spot number × 100
1 tobacco mosaic virus (TMV) Induced resistant effect of table
Preferred compound shows good inhibitory activity, especially B-3, B- to tobacco TMV viruses as can be seen from Table 1
4-b, B-6 and B-7, its, suppression that B-7 show suitable with positive control BTH effects to the inhibiting rate of TMV under 100 μM of concentration
System activity has been higher than BTH.Wherein optimal compound B-7 reaches the inhibiting rate of tobacco TMV viruses under 100 μM of concentration
82.09% better than commercialization inducer BTH.
Indoor biometrics of the embodiment 5 to rice blast
It is no loadtransformer number for examination rice varieties.100 μM of B-1, B-2, B-3, B-6, BTH are prepared respectively, it is equal with foliar spray method
It is even to be sprayed on the consistent potting rice seedling of 2 leaf, 1 heart stage growing way, clear water is separately set as blank control.Chemicals treatment is inoculated with rice blast after 2 days
Germ, magnaporthe grisea spore suspension concentration are 3.2 × 108Cfu/L, spray inoculation, per basin inoculum concentration 5mL.It is protected in inoculation for 24 hours
Dark condition is demonstrate,proved, for 24 hours rear illumination: dark=12h: 12h；Often handle 20 plants of rice seedlings, 3 repetitions.5~7d investigation hair after inoculation
State of an illness condition, and calculate disease index and control effect.Disease index and control effect calculate by the following method.
Disease index (%)=∑ (morbidity numbers at different levels × opposite value of series) × 100/ investigation total number of sheets × highest represents grade
Number
Control effect=(control group disease index-processing group disease index)/control group disease index × 100%
Grade scale：
Rice blast grade scale：
0 grade：It is disease-free；
1 grade：The brown point of only small needle point size；
2 grades：Larger brown point；
3 grades：Small and circle so that slightly long brown downright bad greyness, diameter l~2mm；
4 grades：Typical rice blast scab or ellipse, long 1~2cm, are normally limited between 2 veins, lesion area deficiency blade face
Long-pending 20%；
5 grades：Typical rice blast scab, injured area are less than 10%；
6 grades：Typical rice blast scab, injured area are 10%~25%；
7 grades：Typical rice blast scab, injured area are 26%~50%；
8 grades：Typical rice blast scab, injured area are 51%~75%；
9 grades：Whole blades are dead.
The experiment of 2 rice rice blast fungus indoor pot of table is raw to survey result
Indoor biometrics of the embodiment 6 to banana blight
It is Brazilian any of several broadleaf plants for examination banana variety, strains tested is Fusarium oxysporum Cuba specialized form.200 μM of B-7 are prepared respectively
With the 1 of SA, JA, INA, BABA, PBZ, BTH and amino-oligosaccharide:1 composition is uniformly sprayed on growing way one with foliar spray method
In the potting banana seedlings of cause, clear water is separately set as blank control.Chemicals treatment is inoculated with Fusarium oxysporum spore after 2 days in banana root
Suspension, spore suspension a concentration of 1 × 108Cfu/L often handles 20 plants of banana seedlings, 3 repetitions per basin inoculum concentration 5mL.It connects
5~7d investigates incidence after kind.
Calculation formula：
Diseased plant rate=diseased plant number/investigation sum × 100%；
Control effect=(control group diseased plant rate-processing group diseased plant rate)/control group diseased plant rate × 100%
Table 3 is to banana blight indoor biometrics result
Field efficacy of the embodiment 7 to tomato wilt
1. experiment condition
Experiment is located at the open country tomato field in the Xinjiang townshiies Bole Belling craze for Japanese pop culture Mo Dun, area 1105m2, soil property is wattenshlick field,
Fertility level is medium, experimental field plants tomato for many years, and tomato wilt occurs heavier.Tomato (drawing 118 in red pool) is in May, 2016
It sows within 18th, transplanting on June 20, seeding row spacing is 40cm × 40cm, 1930 plants/667m of density2.Per plot area 25m2, random area
Group arrangement.
2. experimental design
Test process dosage is effective content, if B-1, B-6, B-7, B-7+BTH (in mass ratio 1：1 mixing) and more bacterium
5 processing of spirit, dosage 75g/hm2, compared with clear water, 3 repetitions.Respectively at June 27, July 7, July 17, sit
Fruiting period August uses DX-9A knapsack hand sprayer spray pesticides on the 2nd, and spraying is uniform, water consumption 750L/hm2。
3. result counts
7d, 14d investigate whole plant incidences in each cell after the 4th dispenser, and calculate disease according to following formula
Strain rate and control effect.
Calculation formula：
Diseased plant rate=diseased plant number/investigation sum × 100%；
Control effect=(control group diseased plant rate-processing group diseased plant rate)/control group diseased plant rate × 100%
Table 4 is to tomato wilt control effect
8 trickle irrigation method of embodiment prevents cotton verticillium wilt
1. experiment condition
Experiment carries out in Xinjiang Bole's Belling townshiies craze for Japanese pop culture Mo Dun cotton field.The cotton field is 5 years old cottons of continuous plant cotton
Field, cotton verticillium wilt over the years occur serious and comparatively uniform.It is western general No. 559 for examination cotton variety, on April 20th, 2016
It is sowed by the way of covered rearing with plastic film, line-spacing 0.83m, spacing in the rows 0.25m, 47880 plants/hm of planting density2.It is experimental field native
Earth is sand, middle fertility (content of organic matter 2.8%).
2. experimental design
Experiment sets B-3, B-6 and B-7 and 3 processing, and concentration for the treatment of 100mg/L will be tested using with water pesticide application technology
Medicament is dissolved in the water tower of dropper device, and cotton root, the long 6m of hillslope processes, width 5m, 4 repetitions, each cell are imposed on water droplet
Between set protection 3 row of row.June 12 carried out the 1st dispenser, after 10d (July 21) carry out the 2nd dispenser.Each cell is except at medicament
Reason factor is different outer, other cultivation management measures are consistent.Other management measures of cotton are routinely produced with crop field.
3. result counts
In cotton verticillium wilt onset peak period (August 12), 5 point sampling of diagonal line, every selection 6 are all made of per cell
Strain, according to domestic cotton verticillium wilt unified section standard, records diseased plant numbers at different levels, and the state of an illness of cotton verticillium wilt is calculated according to formula
Index and control effect.
Grade scale：
0 grade of healthy tree
1 grade of diseased plant blade has 25% or less aobvious symptom, and faint yellow irregular scab is generated between blade master pulse.
2 grades of diseased plant blades have 26% to 50% aobvious symptom, the color of scab to mostly become yellow and yellowish-brown, blade
Edge has volume withered.
3 grades of diseased plant blades have 51% or more aobvious symptom, and the most digital display yellowish-brown of scab, blade edge volume is withered, there is a small number of leaves
Piece withers and falls.
4 grades of diseased plant leaf abscissions are dead at light stalk and plant, occur acute wilting death symptom sometimes.
Calculation formula：
Diseased plant rate=diseased plant number/investigation sum × 100%；
Disease index=Σ (sick grade strain number × represents series) × 100/ investigation sum × highest represent grade
Control effect=(control group disease index-processing group disease index)/control group disease index × 100%
The different inducer processing of table 5 are to cotton verticillium wilt control effect
Field efficacy of the embodiment 9 to potato wilt
Experiment is carried out in Zengcheng City of Guangdong Province, is gram new No. 1 for examination Potato Cultivars.Experiment sets 5 processing B-1, B-2,
B-3, B-10 and B-11, concentration for the treatment of are 100mg/L, if clear water processing is control each 3 repetitions of processing.Cell is random
District's groups arrange, plot area 21.6m2(long 6m × wide 3.6m) plants 6 rows per cell, often 20 nest of row (line-spacing 60cm × nest spacing
30cm), totally 18 cells.It sprays 1 time every 7d, sprays 3 times, taken using 5 points of cell diagonal line after third time dispenser 7d altogether
Sample method distinguishes Investigate incidence, diseased plant rank, disease index and relative control effect, calculates disease index and control effect.
Calculation formula：
Incidence=morbidity strain number/investigation sum × 100%；
Control effect=(control group incidence-processing group incidence)/control group incidence × 100%
The different inducer processing of table 6 are to potato wilt control effect
Field efficacy of the embodiment 10 to the late blight of potato
Experiment is carried out in Zengcheng City of Guangdong Province, is gram new No. 1 for examination Potato Cultivars.Experiment sets 5 processing B-1, B-2,
B-3, B-10 and B-11, concentration for the treatment of are 100mg/L, if clear water processing is control each 3 repetitions of processing.It is sprayed every 7d
Medicine 1 time sprays 3 times altogether, using 5 point sampling of cell diagonal line difference Investigate incidence, diseased plant grade after third time dispenser 7d
Not, disease index and relative control effect calculate disease index and control effect.
Late blight of potato severity Scaling standard：
0 grade, disease-free spot；
1 grade, lesion area accounts for 5% or less entire leaf area；
3 grades, lesion area accounts for the 6%~10% of entire leaf area；
5 grades, lesion area accounts for the 11%~20% of entire leaf area；
7 grades, lesion area accounts for the 21%~50% of entire leaf area；
9 grades, lesion area accounts for 50% or more of entire leaf area.
Calculation formula：
Disease index=Σ (at different levels disease the numbers of sheets × represents series) × 100/ investigation sum × highest represent grade
Control effect=(control group disease index-processing group disease index)/control group disease index × 100%
The different inducer processing of table 7 are to late blight of potato control effect
Field efficacy of the embodiment 11 to downy mildew of garpe
Experiment is carried out in Zengcheng City of Guangdong Province, is triennial " cold fragrant honey " for examination grapevine seedling, and thing row is to double-walled hedge frame
Formula, frame high 1.6m, spacing in the rows 50cm.Experiment sets 6 processing B-1, B-2, B-3, B-6, B10 and B-11, and concentration for the treatment of is
100mg/L, if clear water processing is control each 3 repetitions of processing.It sprays 1 time, sprays altogether 3 times, in third time dispenser every 7d
Using 5 point sampling of cell diagonal line difference Investigate incidence, diseased plant rank, disease index and relative control effect after 7d, disease is calculated
Feelings index and control effect.
Disease scale standard
0 grade：Full leaf disease-free spot；
1 grade：Lesion area accounts for 5% or less the blade gross area；
2 grades：Lesion area accounts for the blade gross area 6%~25%；
3 grades：Lesion area accounts for the blade gross area 26%~50%；
4 grades：Lesion area accounts for the blade gross area 51%~75%；
5 grades：Lesion area accounts for 75% or more the blade gross area
Calculation formula：
Diseased plant rate=diseased plant number/investigation sum × 100%；
Disease index=Σ (sick grade strain number × represents series) × 100/ investigation sum × highest represent grade
Control effect=(control group disease index-processing group disease index)/control group disease index × 100%
The different inducer processing of table 8 are to downy mildew of garpe control effect
Field efficacy of the embodiment 12 to corn stalk rot disease
Experiment is carried out in Zengcheng City of Guangdong Province, is Zheng Dan 958 for examination corn variety.Experiment sets 8 processing B-1, B-2, B-
3, B-6, B-7, B8, B10 and B11, concentration for the treatment of are 100mg/L, if clear water processing is control each 3 repetitions of processing.Often
Every 7d spray 1 time, spray altogether 3 times, after third time dispenser 7d using 5 point sampling of cell diagonal line difference Investigate incidence,
Diseased plant rank, disease index and relative control effect calculate disease index and control effect.
Calculation formula：
Diseased plant rate=diseased plant number/investigation sum × 100%；
Control effect=(control group diseased plant rate-processing group diseased plant rate)/control group diseased plant rate × 100%
The different inducer processing of table 9 are to corn stalk rot disease control effect
Embodiment above describes the basic principles and main features and advantage of the present invention, and the technical staff of the industry should
Understand, the present invention is not limited to the above embodiments, and the above embodiments and description only describe the originals of the present invention
Reason, under the range for not departing from the principle of the invention, various changes and improvements may be made to the invention, these changes and improvements are each fallen within
In the scope of protection of the invention.
Claims (10)
1. one kind is used for the compound of Plant-induced resistance, shown in compound formula such as formula (I)；
R can be indicated：C1-C6Alkyl, C2-C6Alkenyl, C2-C6Alkynyl, the wherein alkyl, alkenyl and alkynyl group are optionally
By 1 to 3 independently selected from hydroxyl, halogen, C1-C6Alkoxy, C1-C6Alkylthio group, aryl, heteroaryl, aryloxy group and heteroaryl
The substituent group of oxygroup replaces, and R can not stand alone as methyl, and the above compound includes its all stereoisomer.
2. according to the compound of claim 1, wherein R is preferably C1-C4Alkyl, C2-C4Alkenyl, C2-C4Alkynyl, the wherein alkane
Base, alkenyl and alkynyl group can be optionally by 1 to 3 independently selected from hydroxyl, F, Cl, Br, C1-C4Alkoxy, C1-C4
Alkylthio group, phenyl, phenoxy group, pyridyl group, pyridazinyl, pyrimidine radicals, pyrazinyl, pyrrole radicals, pyrazolyl, imidazole radicals, triazolyl (example
Such as, [1,2,4] triazolyl), furyl, thiophenyl, oxazolyl, isoxazolyl, oxadiazolyls, thiazolyl, isothiazolyl, thiophene two
Oxazolyl, purine radicals, quinolyl, cinnoline base, quinoxalinyl, indyl, indazolyl, benzimidazolyl, aisaa benzothiophenyl and benzene
Benzothiazolyl substituent group replaces.
3. according to the compound of claim 2, wherein R is preferably ethyl group, vinyl, acetenyl, wherein the alkyl, alkenyl with
And alkynyl group can be optionally by 1 to 3 independently selected from hydroxyl, F, Cl, methoxyl group, methyl mercapto, phenyl, phenoxy group, benzene
The substituent groups such as sulfenyl, pyridyl group, benzothiazolyl replace.
4. according to the compound of claim 3, preferably with lower structure：
5. a kind of Plant-induced resistance composition, it is characterized in that Claims 1-4 compound as defined in any one is as plant
Inducer and salicylic acid (SA), gaultherolin (MeJA), jasmonic (JA), methyl jasmonate (MeJA), the different cigarette of 2,6- dichloros
Sour (INA), diazosulfide (BTH), probenazole (PBZ), beta-aminobutyric acid (BABA), amino-oligosaccharide form interaction combination
Object.
6. compound described in Claims 1-4, it is characterized in that solely or being mixedly used as inducer in Plant-induced resistance
Using.
7. the application described in claim 6, it is characterized in that improving crops to the plant disease caused by fungi, bacterium and virus
Immunocompetence.
8. claim 1 to 5 compound or composition, it is characterised in that be as inducer active ingredient amount ranges
0.5g to 500g/hm2。
9. it is a kind of induction plant disease-resistant method, this method include by compound or composition defined in claim 1 to 5 with
Suitable mode is applied to blade face, stem, branch or the root of plant, and activated plant immune system is resisted pathogenic microorganism and entered
It invades.
10. suitable method described in claim 9 includes sprinkling, is smeared and the agriculturally common insecticide-applying way such as trickle irrigation.
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| CN110463702B (en) * | 2019-08-30 | 2021-03-26 | 沈阳农业大学 | Application of hydroxyketone compound or preparation containing hydroxyketone compound in promoting plant root growth |
| CN110734921A (en) * | 2019-10-29 | 2020-01-31 | 吉林大学 | Detection method of kinds of anthracnose bacteria Colletotrichum siamense of tea trees |
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