CN110037037B - Method for preventing pathogen from infecting plant - Google Patents
Method for preventing pathogen from infecting plant Download PDFInfo
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- CN110037037B CN110037037B CN201910426805.5A CN201910426805A CN110037037B CN 110037037 B CN110037037 B CN 110037037B CN 201910426805 A CN201910426805 A CN 201910426805A CN 110037037 B CN110037037 B CN 110037037B
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
- A01G13/00—Protecting plants
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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Abstract
The application relates to application of a compound shown as a formula I, a stereoisomer thereof, or an agriculturally or forestry chemically acceptable salt thereof or a composition containing the compound shown as the formula I, the stereoisomer thereof, or the agriculturally or forestry chemically acceptable salt thereof in preventing or controlling or treating invasive diseases of plants caused by pathogens. The application also relates to a method of preventing or controlling or treating infestation of plants by a pathogen, and to a method of preventing or controlling or treating an infectious disease of a plant caused by a pathogen.
Description
Technical Field
The application belongs to the technical field of pesticides, relates to a method for preventing or controlling or treating pathogen infection of plants, and also relates to a method for preventing or controlling or treating infectious diseases of plants caused by pathogens.
Background
Phloem parasitic bacteria are harmful bacteria parasitic on plant phloem, and because the bacteria are mainly parasitic on the phloem of the plant, once the bacteria are fixedly planted and propagated on the phloem, phloem tissue necrosis and sieve tube blockage can be caused, the transportation and absorption of plant nutrient substances are influenced, and then the plant is diseased and dead. The germs are easy to be carried and infected by plant hoppers, cicadas and other winged insects, and can also be infected by grafting.
At present, most of devastating plant diseases are found to be related to phloem parasitic bacteria in the world, such as huanglongbing, zebra chip disease, grape golden disease, pear recession disease and the like.
The yellow shoot disease is a devastating disease in the citrus production in the world, is also called yellow shoot disease, yellow blight, blue fruit disease and phloem recession disease, is caused by a phloem bacillus (Candidatus Liberibacter spp.) parasitizing in the phloem of plants, and can infect various rutaceous plants including citrus, poncirus, kumquat, murraya and the like. The damping off disease of Taiwan province is also yellow dragon disease. The Bacterium, i.e., a Bacterium of the genus Bacterium-Like-Organisms (Bacterium-Like-Organisms), has a double membrane, and the wall membrane structure of a pathogen has the characteristics of a wall membrane of a gram-negative Bacterium, and thus may be called a gram-negative Bacterium. The species of Brevibacterium can be classified into Asian (Candidatus Liberibacter asiaticus) African (Candidatus Liberibacter africanus) and American (Candidatus Liberibacter americaus). Currently, there is no effective treatment for huanglongbing, which is distributed in nearly 50 countries and regions of asia, africa, oceania, south america and north america, at home and abroad. 11 citrus production provinces (cities and autonomous regions) in China are seriously affected by the disease, and the healthy development of the citrus industry is severely restricted.
The zebra chip disease is mainly caused by infection of plants by a bacterium which is a phloem parasitic bacterium Candidatus Liberibacter solanaceous of solanaceae, which is a bacterium difficult to culture, and the bacterium can infect solanaceae plants such as potatoes, tomatoes, eggplants, green tomatoes, tree tomatoes and the like and can infect umbelliferae plants such as carrots, celery and the like through grafting or spreading by psyllids, so that the yield and the quality of the crops are seriously influenced. The pathogen is similar to the yellow dragon disease pathogen in classification status, and no effective treatment means exists at present, and the pathogen is also a destructive disease.
The grape golden disease is caused by pathogenic grape golden phytoplasma (Grapevine flavescence potato), the shape of thalli of the grape golden disease is irregular, phloem of a diseased plant exists, the grape golden disease mainly proliferates in a host plant and a mediator leafhopper, the grape golden disease cannot grow on an artificial culture medium until now, the grape golden disease is mainly characterized in that a young shoot has no yield, the flower is usually called to be withered immediately after the flower withering, sometimes, fruit grains shrink and the taste is extremely bitter. The old diseases recur frequently, the plants wither completely, the yield of the diseased trees is reduced by 20-30%, and the whole grape garden is damaged when the disease is serious, so that the grape industry planting area is damaged.
Pear failure disease is mainly caused by Pear failure Phytoplasma (Candidatus Phytoplasma pyri, Pear decline Phytoplasma). The pear decay disease phytoplasma is predominantly filamentous, usually with 3-layer membrane branches, but lacks a rigid cell wall. Pathogenic phytoplasmas have not been cultured successfully in vitro to date. During the growing season, pear failure phytoplasmas proliferate rapidly in phloem sieve tubes, and some pear trees may die within months. The disease is a disease occurring in the growth period of pear trees, the loss can reach 27% in the early stage of the disease, the fruit yield can be reduced by 25% in 7-8 years, and great loss is caused to farmers.
Plant diseases caused by phloem parasitic bacteria, such as huanglongbing, zebra chip disease, grape golden disease, pear recession disease and the like, have strong infectivity, and no effective prevention and control means for the bacteria is available at present. Therefore, the search for compounds that are highly effective in inhibiting and killing phloem parasites is still a major area of research in the field.
Disclosure of Invention
The inventors have unexpectedly found that a compound of formula I, a stereoisomer thereof, or an agriculturally or forestry chemically acceptable salt thereof, can inhibit the growth and reproduction of pathogens parasitic in the phloem of plants, and therefore, the compound of formula I, the stereoisomer thereof, or the agriculturally or forestry chemically acceptable salt thereof, can be used for preventing or controlling or treating pathogen infestation of plants, or for preventing or controlling or treating pathogen-induced invasive diseases of plants, such as huanglongbing, zebra chip disease, grape golden disease, pear decline disease, and the like.
The application relates to application of a compound shown as a formula I, a stereoisomer thereof, or an agriculturally or forestry chemically acceptable salt thereof or a composition containing the compound shown as the formula I, the stereoisomer thereof, or the agriculturally or forestry chemically acceptable salt thereof in preventing or controlling or treating invasive diseases of plants caused by pathogens.
The application also relates to a method for preventing or controlling or treating infestation of plants by a pathogen, which comprises treating the pathogen, its habitat or the plant to be protected from pathogen attack, propagation material of the plant, the soil, an organic substrate, an area, a substance or a space with an effective amount of at least one compound of the formula I, its stereoisomers, or an agriculturally or forestry chemically acceptable salt thereof.
The present application also relates to a method for preventing or controlling or treating an infectious disease of a plant caused by a pathogenic agent, comprising applying an effective amount of at least one compound represented by formula I, a stereoisomer thereof, or an agriculturally or forestry chemically acceptable salt thereof to the plant, propagation material thereof, fruit thereof, or soil, organic substrate, area or space in which it grows.
The present application also relates to a method for preventing or controlling or treating infestation of plants by a pathogen, comprising treating the pathogen, its habitat or the plant to be protected from pathogen attack, propagation material of the plant, soil, organic substrate, area, substance or space with a composition comprising an effective amount of at least one compound of formula I, a stereoisomer thereof, or an agriculturally or forestry chemically acceptable salt thereof.
The present application also relates to a method for preventing or controlling or treating an infectious disease of a plant caused by a pathogen, comprising: applying a composition comprising an effective amount of at least one compound of formula I, a stereoisomer thereof, or an agriculturally or forestry chemically acceptable salt thereof, to the plant, propagation material thereof, fruit thereof, or soil, organic substrate, area or space in which it is grown.
In certain embodiments, the pathogens described herein are pathogens that are parasitic in the phloem of a plant, such as bacteria that are parasitic in the phloem of a plant (e.g., Phytoplasma (Phytoplasma), phloem (Candidatus Liberibacter spp)).
In certain embodiments, the pathogen described herein is a mycobacterium asian species (Candidatus Liberibacter asiaticus), a mycobacterium african species (Candidatus Liberibacter africanus), a mycobacterium americana species (Candidatus Liberibacter americanus), a Candidatus Liberibacter solanacearum, a grape yellow Phytoplasma (grape yellow mosaic virus do Phytoplasma), or a pear failure Phytoplasma (Candidatus Phytoplasma pyri).
In certain embodiments, the infectious disease caused by a pathogen described herein is huanglongbing, zebra fingi, grapevine or pear failure.
In certain embodiments, the plant described herein is a solanaceous plant (e.g., potato, tomato, eggplant, green tomato, tamato, etc.), an umbelliferae plant (e.g., carrot, celery, etc.), a rutaceae plant (e.g., citrus, poncirus, kumquat, murraya, etc.), a vitiidae plant (e.g., grape), or a rosaceous plant (e.g., pear).
In certain embodiments, the compositions described herein further comprise an adjuvant.
The structural formula of the compound shown in the formula I is shown as follows,
wherein R is1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14Each independently selected from: hydrogen, fluorine, chlorine, bromine, iodine, C1-8Alkyl radical, C1-8Alkoxy, nitro, hydroxyl, cyano, amino.
In certain embodiments, R in the compound of formula I1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14Each independently selected from: hydrogen, fluorine, chlorine, bromine, iodine, C1-6Alkyl radical, C1-6Alkoxy, nitro, hydroxyl, cyano, amino.
In certain embodiments, R in the compound of formula I1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14Each independently selected from: hydrogen, fluorine, chlorine, bromine, iodine, C1-4Alkyl radical, C1-4Alkoxy, nitro, hydroxyl, cyano, amino.
In certain embodiments, R in the compound of formula I1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14Each independently selected from: hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, methoxy, ethoxy, n-propoxy, isopropyloxy, n-butyloxy, isobutyloxy, sec-butyloxy, tert-butyloxy, n-pentyloxy, n-hexyloxy, nitro, hydroxyl, cyano or amino.
In certain embodiments, R in the compound of formula I1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14Each independently selected from: hydrogen, fluorine, chlorine, bromine, hydroxyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropyloxy, n-butyloxy, isobutyloxy, sec-butyloxy, tert-butyloxy.
In certain embodiments, R in the compound of formula I1、R2、R3、R4、R5Each independently selected from: hydrogen, fluoro, chloro, bromo, hydroxy, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, n-propoxy and isopropyloxy;
R6、R7、R8、R9each independently selected from: hydrogen, fluoro, chloro, bromo, hydroxy, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, n-propoxy and isopropyloxy;
R10、R11、R12、R13、R14each independently selected from: hydrogen, fluorine, chlorine, bromine, hydroxyl, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, n-propoxy and isopropyloxy.
In certain embodiments, R in the compound of formula I1、R2、R3、R4、R5Each independently selected from: hydrogen, fluorine, chlorineBromine and hydroxyl;
R6、R7、R8、R9each independently selected from: hydrogen, fluoro, chloro, bromo, methyl and methoxy;
R10、R11、R12、R13、R14each independently selected from: hydrogen, fluorine, chlorine, bromine and hydroxyl.
In certain embodiments, R in the compound of formula I1Is hydrogen, bromine or chlorine; r2Is hydrogen or bromine; r3Is hydrogen, bromine or hydroxy; r4Is hydrogen, fluorine, chlorine or bromine; r5Is hydrogen or chlorine; r6Is hydrogen; r7Is hydrogen, bromine, methyl or methoxy; r8Is hydrogen or chlorine; r9Is hydrogen, methyl or methoxy; r10Is hydrogen or chlorine; r11Is hydrogen, chlorine, fluorine or bromine; r12Is hydrogen, chlorine or hydroxyl; r13Is hydrogen, chlorine or bromine; r14Is hydrogen, chlorine or bromine.
In certain embodiments, the compound of formula I is selected from:
the various terms and phrases used herein have the ordinary meaning as is known to those skilled in the art and, to the extent that they do not conform to known meanings, they do not conform to the meaning of the present invention.
The term "C" as used in this application1-8Alkyl "means a straight or branched chain alkyl group having 1 to 8 carbon atoms, such as 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms, e.g. C1-6Alkyl radical, C1-4An alkyl group. Specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl.
The term "C" as used in this application1-8Alkoxy "means C as defined above1-8Radicals obtained by linking carbon atoms of alkyl radicals to oxygen atoms, e.g. "C1-6Alkoxy group "," C1-4Alkoxy ", specific examples include, but are not limited to, methoxy, ethoxy, propoxy, or the like.
The term "amino" as used in the present application refers to NH2-。
The term "agriculturally or forestry chemically acceptable salt" as used herein means a salt of a compound of the present application that is acceptable in agricultural or forestry chemistry and has the desired pharmacological activity of the parent compound. Such salts include: acid addition salts with inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, and the like, or with organic acids; such as acetic acid, propionic acid, hexanoic acid, cyclopentanepropionic acid, glycolic acid, pyruvic acid, lactic acid, malonic acid, succinic acid, malic acid, maleic acid, fumaric acid, tartaric acid, citric acid, benzoic acid, cinnamic acid, mandelic acid, methanesulfonic acid, ethanesulfonic acid, benzenesulfonic acid, naphthalenesulfonic acid, camphorsulfonic acid, glucoheptonic acid, gluconic acid, glutamic acid, hydroxynaphthoic acid, salicylic acid, stearic acid, muconic acid, and the like.
The term "effective amount" as used herein denotes an amount sufficient to control harmful pathogens without causing significant damage to the treated plant or plant propagation material. The amount may vary within wide limits and depends on various factors such as the pathogenic species to be controlled, the plant or plant propagation material being treated, the climatic conditions, the mode of application and the particular compound used.
The term "adjuvant" as used in the present application is to be understood as a generic term for the various auxiliary substances used in the processing and application of pesticide dosage forms, which are mixed or combined with the active substances to achieve better application, in particular to plants or plant propagation material.
Common adjuvants include solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, solubilizers, permeation enhancers, protective colloids, adhesives, thickeners, humectants, antifreeze agents, defoamers, colorants, tackifiers, and binders.
Suitable solvents and liquid carriers include water and organic solvents, such as mineral oil fractions, e.g. kerosene, diesel; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, such as toluene, paraffins, tetrahydronaphthalene, alkylated naphthalenes; alcohols, such as ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, such as cyclohexanone; esters, such as lactate, carbonate, fatty acid ester, γ -butyrolactone; a fatty acid; a phosphonate ester; amines; amides, such as N-methylpyrrolidone, fatty acid dimethylamide; and mixtures thereof.
Suitable solid carriers or fillers include mineral earths, for example silicates, silica gels, talc, kaolin, limestone, lime, chalk, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium oxide; polysaccharides, such as cellulose, starch; fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, such as cereal flour, bark flour, wood flour and nut shell flour, and mixtures thereof.
Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, and mixtures thereof. Such surfactants may be used as emulsifiers, dispersants, solubilizers, wetting agents, penetration enhancers, protective colloids, or adjuvants.
Suitable anionic surfactants are alkali metal, alkaline earth metal or ammonium salts of sulfonic acids, sulfuric acids, phosphoric acids, carboxylic acids and mixtures thereof. Examples of sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignosulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl-and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, sulfates of ethoxylated alkylphenols, sulfates of alcohols, sulfates of ethoxylated alcohols or sulfates of fatty acid esters. An example of a phosphate is a phosphate ester. Examples of carboxylates are alkyl carboxylates and also carboxylated alcohol or alkylphenol ethoxylates.
Suitable cationic surfactants include quaternary surfactants, such as quaternary ammonium compounds having 1 or 2 hydrophobic groups, or salts of long chain primary amines.
Suitable nonionic surfactants include alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates include compounds of alkoxylated alcohols, alkylphenols, amines, amides, arylphenols, fatty acids, or fatty acid esters. Examples of N-substituted fatty acid amides include fatty acid glucamides or fatty acid alkanolamides. Examples of esters include fatty acid esters, glycerides or monoglycerides. Examples of sugar-based surfactants include sorbitan, ethoxylated sorbitan, sucrose and glucose esters or alkyl polyglucosides. Examples of polymeric surfactants include homopolymers or copolymers of vinyl pyrrolidone, vinyl alcohol, or vinyl acetate.
Suitable amphoteric surfactants include alkyl betaines and imidazolines.
Suitable thickeners include polysaccharides (e.g. xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates and silicates.
Suitable antifreeze agents include ethylene glycol, propylene glycol, urea and glycerol.
Suitable antifoams include polysiloxanes, long chain alcohols and fatty acid salts.
Suitable colorants (e.g., red, blue or green colored) include pigments of low water solubility and water-soluble dyes. Specific examples include inorganic colorants (e.g., iron oxide, titanium oxide, iron hexacyanoferrate) and organic colorants (e.g., alizarin colorants, azo colorants, and phthalocyanine colorants).
Suitable tackifiers or adhesives include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylates, biological or synthetic waxes and cellulose ethers.
The compounds of formula I, stereoisomers thereof, or agriculturally or forestry chemically acceptable salts or compositions thereof described herein may be used on their own or in the form of formulations depending on their respective physical and/or chemical properties. The preparation can be in the form of missible oil, suspending agent, wettable powder, granule, water agent, poison bait, mother liquor, mother powder, aerosol, ready-to-use solution, powder, oil-in-water emulsion, water-in-oil emulsion, oil agent, foaming agent, paste and the like.
When the pathogens, their habitat or the plants to be protected from the pathogen, propagation material of plants, soil, organic substrate, area, substance or space are treated with the compounds of the formula I, their stereoisomers, or their agriculturally or forestry chemically acceptable salts or compositions described herein, the treatment can be carried out using conventional treatment methods, for example dipping, spraying, atomizing, irrigating, evaporating, dusting, fogging, broadcasting, foaming, painting, spreading, irrigating, drip irrigating, infusing, etc. For propagation material (but not for seeds) it is also performed by dry seed treatment, wet seed treatment, slurry treatment, encrustation treatment, application of one or more coatings, etc. The active substances can also be applied by the ultra-low method or the active substance preparation or the active substance itself can be injected into the soil or organic matrix. For example, the compounds of formula I, stereoisomers thereof, or agriculturally or forestry chemically acceptable salts or compositions thereof described herein may be applied by spraying onto the foliage of a plant, or by infusion into the trunk.
When treating leaves with a compound of formula I, a stereoisomer thereof, or an agriculturally or forestry chemically acceptable salt or composition thereof as described herein, the active substance may generally be applied in a dose of from 10g to 1000 kg/ha. The dose may be lower if a tree trunk infusion is possible. In the case of seed treatment, the dose of active substance applied can generally be between 0.1g and 10kg per 100kg of seed. It should be clearly understood that the dosages specified above are given as illustrative examples of the invention. The person skilled in the art knows how to adjust the applied dose depending on the nature of the crop to be treated.
The term "propagation material" as used herein shall be understood to mean the reproductive parts of a plant which may be used in the propagation of the plant, including seeds, plants, seedlings (including test-tube plantlets), fruits, rootstocks, scions, cuttings, leaves, sprouts, tubers, bulbs, corms, pollen, plant culture material (including transgenic plants) and the like.
As used herein, the concentration unit "M" means mol/L, mM means mmol/L, and μ M means μmol/L.
In the present application, the term "about" is to be understood within ± 10%, ± 9%, ± 8%, ± 7%, ± 6%, ± 5%, ± 4%, ± 3%, ± 2%, ± 1%, ± 0.5%, ± 0.1%, ± 0.05% or ± 0.01% of the specified numerical value.
The invention has the beneficial technical effects
The compound shown in the formula I, the stereoisomer thereof or the agriculturally or forestry chemically acceptable salt thereof can inhibit the growth and reproduction of pathogens parasitizing in plant phloem, can be used for preventing or controlling or treating the pathogens, particularly the pathogens parasitizing in the plant phloem, such as bacteria parasitizing in the plant phloem (such as Phytoplasma and phloem), infecting plants, and can also be used for preventing or controlling or treating invasive diseases of plants caused by the pathogens, such as yellow dragon disease, zebra chip disease, grape golden disease, pear recession disease and the like.
Detailed Description
Embodiments of the present invention will be described in detail below with reference to examples, but those skilled in the art will appreciate that the following examples are only illustrative of the present invention and should not be construed as limiting the scope of the present invention. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products commercially available.
Compounds 1-10 used in the following examples were all purchased from Shanghai ceramic Biotechnology Ltd.
Example 1: antibacterial experiment for papaya endophyte
1.1 Experimental Equipment and reagents
1.1.1 Experimental Equipment
A microplate reader (BioTek), an ultra-clean bench (Suzhou purification equipment Co., Ltd.), a sterilization pot (Sanyo), a pH meter (METTLER TOLEDO), a thermostat (MJX-250B-Z) and the like.
1.1.2 Experimental reagents
Alpha-ketoglutaric acid (Sigma), N-carbamoylmethyl ethanesulfonic acid (Sigma), TMN-FH insect culture medium (Sigma), fetal bovine serum (Gibco), papaya endophytes (Liberibacter crescens BT-1, Shanghai Bao Tibet organisms), and the like.
1.2 Experimental procedures:
1.2.1 preparation of the culture Medium
The formulation method is shown in Table 1.
TABLE 1 preparation of BM7 culture Medium
1.2.2 antimicrobial experiments
As the phloem parasitic bacteria can not be artificially cultured in vitro so far, the phloem parasitic bacteria can not be used for screening in vitro antibacterial drugs, and the method with higher international acceptance at present is to screen in vitro antibacterial drugs by using the phloem parasitic bacteria similar bacteria, namely pawpaw endophyte (Liberibacter crescens BT-1).
The experiment adopts papaya endophyte to carry out in vitro antibacterial experiment. The experimental method comprises the following steps: 190 μ L of compounds (e.g., drug water insoluble, DMSO solubilization by adding appropriate amount, but DMSO final concentration does not exceed 1%) diluted in BM7 medium at various concentrations were added to 96-well plates at a concentration of about 2 x 10 per well610 mul/mL of recovered pawpaw endophyte, the final concentration of the drug compound in the experimental system is 100.0mg/mL, 10.0mg/mL, 1.0mg/mL, 0.1mg/mL,0.01mg/mL, 0.001mg/mL, 0.0001mg/mL, 0.00001mg/mL, and final concentration of bacteria of about 1 x 105Per well. In the experiment, a control group was set up simultaneously, and the control group had 190. mu.L of BM7 medium and a concentration of about 2X 10610 mu L of recovered pawpaw endophyte per mL. The 96-well plate was then incubated at 28.5 ℃ for 120 hours, and OD at 600nm was measured using a microplate reader.
The antibacterial rate of the drug was calculated according to the following formula:
percent antibacterial activity ═ ODControl group-ODAdministration set)/ODControl group*100％
1.3 results of the experiment
The results of the antibacterial experiments are shown in table 2.
TABLE 2 results of the antibacterial experiments
1.4 conclusion of the experiment
From the above-mentioned antibacterial test results, it was found that the compounds 1, 4, 6 and 9 had 100% of antibacterial effect at a final concentration of 0.0001mg/ml or more (including 0.0001mg/ml), and the compounds 2, 3, 5, 7, 8 and 10 had 100% of antibacterial effect at a final concentration of 0.001mg/ml or more (including 0.001 mg/ml).
Example 2: antibacterial experiment for xanthomonas in-vitro leaves
2.1 Experimental Equipment and reagents
2.1.1 Experimental Equipment
Real-time fluorescent quantitative PCR instruments (Roche), centrifuges (Beckman), super clean benches (Suzhou purification), sterilization pots (Sanyo), ultramicro nucleic acid protein analyzers (Thermo), and the like.
2.1.2 Experimental reagents
CTAB-Triton DNA extract, proteinase K (10mg/mL), 1M Dithiothreitol (DTT), Tris-phenol-chloroform-isoamyl alcohol mixture (wherein the volume ratio of Tris-phenol, chloroform and isoamyl alcohol is 25:24:1), chloroform-isoamyl alcohol mixture (wherein the volume ratio of chloroform and isoamyl alcohol is 24:1), 3M sodium acetate, isopropanol, 75% ethanol, 10 XPCR Buffer, 10mmol dNTPs, 5 u/. mu.l rTaq and the like, wherein the above reagents are all purchased from TaKaRa.
2.2 Experimental methods
2.2.1 leaf harvesting and administration
Since the phloem parasitic bacteria can not be cultured in vitro, fresh citrus leaves which are 100% of those with liberobacter asiaticum detected by PCR are collected for drug sterilization effect experiments. In the experiment, the administration group and the blank control group are set simultaneously. The specific administration mode is that after the leaves with bacteria are ground by liquid nitrogen, the leaves with bacteria are weighed and distributed into ep tubes (50 mg/tube), then 1mL of deionized water prepared compounds with different concentrations 1-10 (for example, the drugs are insoluble in water, and DMSO can be added in a proper amount to assist dissolution, but the DMSO final concentration is not more than 1%) are added into each ep tube, the ep tube is soaked for 72 hours, an equal volume of deionized water is added into a blank control group, and 6 final concentration gradients of each compound in an administration group are respectively set to be 10.0mg/mL, 1.0mg/mL, 0.1mg/mL, 0.01mg/mL, 0.001mg/mL and 0.0001 mg/mL.
2.2.2 nucleic acid extraction and PCR detection
Extracting the DNA of the Huanglongbing disease pathogen from the leaves of the drug according to a CTAB method, and analyzing the nucleic acid purity of the extracted DNA by an ultramicro nucleic acid protein analyzer (the specific DNA extraction method and the purity analysis method can be found in reference to Sympho, Zhengtang spring, Liangdeyang and Quguan syndrome, a simple and efficient method for extracting pure DNA of various plants, plant research, 2015, Vol.35, Issue (3):457-461, DOI:10.7525/j.issn.1673-5102.2015.03.021), performing gene detection by using a real-time fluorescence quantitative PCR instrument after the quality is qualified, and recording the corresponding CT value. The CT value is the cycle number when the amplification curve reaches a threshold value, the higher the bacterium content in the sample is, the lower the corresponding CT value is, and when the CT value is more than 35, the sample is considered to be basically free of the bacterium.
2.3 results of the experiment
The results are shown in Table 3.
TABLE 3 antibacterial test results on Xanthomonas in vitro leaves
2.4 conclusion of the experiment
The experimental results in table 3 show that the CT mean values of the compounds 1, 4, 6 and 9 at final concentrations of 0.001mg/mL or more (including 0.001mg/mL) are >35, which indicates that the compounds at final concentrations of 0.001mg/mL or more (including 0.001mg/mL) have the effect of completely killing the xanthomonas campestris in the excised leaf; the mean CT value of the compounds 2, 3, 5, 7, 8 and 10 is more than 35 when the final concentration is more than 0.01mg/mL (including 0.01mg/mL), which shows that the compounds have the effect of completely killing the yellow dragon disease germs in the leaves in vitro when the final concentration is more than 0.01mg/mL (including 0.01 mg/mL).
Example 3: antibacterial experiment for citrus greening disease
Experimental methods
210 suspected yellow dragon disease infected diseased trees are selected in stone town Hubancun citrus farms in Anyuan county of Ganzhou city in Jiangxi province in 2018, and yellow dragon disease detection is carried out, and the results show that: the incidence rate of the huanglongbing is 100 percent. The method comprises the steps of randomly selecting diseased trees infected with huanglongbing to carry out drug antibacterial tests, inputting drug aqueous solutions with different concentrations (namely aqueous solutions of compounds 1-10, such as drug water insoluble, and adding a proper amount of DMSO for assisting dissolution, wherein the final concentration of DMSO is not more than 1%) into 10 diseased trees of each test group by adopting a trunk infusion method, randomly selecting 10 diseased trees as controls (inputting clear water), starting from 5 months and 1 day, applying the drugs once at the beginning of each month, applying 500mL of the drugs each time, and carrying out an experimental period of 120 days (4 times of drug administration in total). Collecting citrus leaves before each administration, extracting DNA of the yellow shoot pathogens and carrying out PCR detection (the DNA extraction method and the PCR detection method are the same as 2.2.2 in the embodiment 2), and recording corresponding CT values.
Results of the experiment
The results are shown in Table 4.
TABLE 4 antimicrobial test results on Citrus huanglongbing
Remarking: indicates a very significant difference of P <0.01 compared to day 0.
Conclusion of the experiment
The experimental results in table 4 show that compounds 1 to 10 exhibited significant antibacterial effects 60 days after administration at concentrations of 0.001mg/mL and 1.0mg/mL, with compound 1, 4, 6, and 9 at a concentration of 0.001mg/mL showing substantially no occurrence of huanglongbing bacteria in citrus trees 120 days after administration and compound 1 to 10 at a concentration of 1.0mg/mL showing substantially no occurrence of huanglongbing bacteria in citrus trees 120 days after administration, as the administration time was extended. Therefore, the series of compounds have obvious effect of resisting the yellow dragon disease germs.
Example 4: antibacterial experiment for zebra chip disease germs in-vitro leaves
4.1 Experimental Equipment and reagents
4.1.1 Experimental Equipment
Real-time fluorescent quantitative PCR instruments (Roche), centrifuges (Beckman), super clean benches (Suzhou purification), sterilization pots (Sanyo), ultramicro nucleic acid protein analyzers (Thermo), and the like.
4.1.2 Experimental reagents
CTAB-Triton DNA extract, proteinase K (10mg/mL), 1M DTT, a Tris-phenol-chloroform-isoamyl alcohol mixture (wherein the volume ratio of Tris-phenol, chloroform and isoamyl alcohol is 25:24:1), a chloroform-isoamyl alcohol mixture (wherein the volume ratio of chloroform and isoamyl alcohol is 24:1), 3M NaAC, isopropanol, 75% ethanol, 10 XPCR Buffer, 10mmol dNTPs, 5 u/. mu.l rTaq and the like, wherein the above reagents are all purchased from TaKaRa.
4.2 Experimental procedures
4.2.1 leaf harvesting and administration
Since the zebra-sickness germs can not be cultured in vitro, fresh potato leaves which are detected to be 100% with the zebra-sickness germs by PCR are collected to carry out a drug sterilization effect experiment. In the experiment, the administration group and the blank control group are set simultaneously. The specific administration mode is that the bacterial-carrying leaf is ground by liquid nitrogen, weighed and subpackaged into ep tubes (50 mg/tube), then 1mL of deionized water prepared compounds with different concentrations 1-10 (if the drug is water-insoluble, the DMSO can be added in a proper amount to assist dissolution, but the final concentration of the DMSO does not exceed 1%) is added into each ep tube, the drugs are soaked for 72 hours, and the blank control group is added with the deionized water with the same volume. Each compound in the administration group was set to 3 final concentration gradients of 0.01mg/mL, 0.001mg/mL, and 0.0001mg/mL, respectively.
4.2.2 nucleic acid extraction and PCR detection
Extracting the DNA of the zebra plague pathogenic bacteria from the dosed leaves according to a CTAB method, and analyzing the nucleic acid purity of the extracted DNA by an ultramicro nucleic acid protein analyzer (the specific DNA extraction method and the purity analysis method can be seen as reference: Dinghao, Zhengtang spring, Liangdeyang, Quguan syndrome, a simple and efficient method for extracting the pure DNA of various plants, plant research, 2015, Vol.35, Issue (3):457-461, DOI:10.7525/j.issn.1673-5102.2015.03.021), performing gene detection by using a real-time fluorescence quantitative PCR instrument after the quality is qualified, and recording the corresponding CT value.
4.3 results of the experiment
The results are shown in Table 5.
TABLE 5 antibacterial test results for Zebra stripe disease germ in vitro leaves
4.4 conclusion of the experiment
As can be seen from the antibacterial experiment results in Table 5, compared with the blank control group, the compounds 1-10 have certain antibacterial effect at the final concentration of 0.0001mg/mL, and the CT value mean value of the compounds is more than 35 at the final concentration of more than 0.001mg/mL (including 0.001mg/mL), which indicates that the compounds have the effect of completely killing the zebra chip disease germs in the in-vitro leaves at the concentration of more than 0.001mg/mL (including 0.001 mg/mL).
Example 5: antibacterial experiment for botrytis cinerea in-vitro leaves
5.1 Experimental Equipment and reagents
5.1.1 Experimental Equipment
The same as in example 2.
5.1.2 Experimental reagents
The same as in example 2.
5.2 Experimental procedures
5.2.1 leaf harvesting and administration
Since the grape golden disease germs can not be cultured in vitro, fresh grape leaves which are 100% tested by PCR and carry the grape golden disease germs are collected to carry out the drug sterilization effect experiment. In the experiment, the administration group and the blank control group are set simultaneously. The specific administration mode is that the bacterial-carrying leaf is ground by liquid nitrogen, the ground bacterial-carrying leaf is weighed and distributed into ep tubes (50 mg/tube), then 1mL of deionized water is added into each ep tube to prepare compounds with different concentrations of 1-10 (if the drug is water-insoluble, the DMSO can be added in a proper amount to assist dissolution, but the final concentration of the DMSO does not exceed 1%), the mixture is soaked for 72 hours, and the same volume of deionized water is added into a blank control group. Each compound in the administration group was set to 3 final concentration gradients of 0.1mg/mL, 0.001mg/mL, and 0.0001mg/mL, respectively.
5.2.2 nucleic acid extraction PCR detection
Extracting the DNA of the botrytis cinerea according to a CTAB method, and performing nucleic acid purity analysis on the extracted DNA by an ultramicro nucleic acid protein analyzer (the specific DNA extraction method and the purity analysis method can be found in reference to: Dinghao, Zhengtang spring, Liangdeyang, Quguan syndrome, a simple and efficient method for extracting pure DNA of various plants, plant research, 2015, Vol.35, Issue (3):457-461, DOI:10.7525/j.issn.1673-5102.2015.03.021), performing gene detection by using a real-time fluorescence quantitative PCR instrument after the quality is qualified, and recording the corresponding CT value.
5.3 results of the experiment
The results are shown in Table 6.
TABLE 6 antibacterial test results for Vibrio aurantiaca in vitro leaves
5.4 conclusion of the experiment
The experimental results in table 6 show that, compared with the blank control group, the compounds 1 to 10 have a certain antibacterial effect at the final concentration of 0.0001mg/ml, and the average value of the CT values of the compounds is more than 35 at the final concentration of more than 0.001mg/ml (including 0.001mg/ml), which indicates that the compounds have the effect of completely killing the golden grape disease germs in the leaves in vitro at the concentration of more than 0.001mg/ml (including 0.001 mg/ml).
Example 6: antibacterial experiment for pear retrogradation disease germs in-vitro leaves
6.1 Experimental Equipment and reagents
6.1.1 Experimental Equipment
The same as in example 2.
6.1.2 Experimental reagents
The same as in example 2.
6.2 Experimental procedures
6.2.1 leaf harvesting and administration
Because the pear recession disease germs can not be cultured in vitro, fresh pear tree leaves which are detected to be 100% with the pear recession disease germs through PCR are collected to carry out a drug sterilization effect experiment. In the experiment, the administration group and the blank control group are set simultaneously. The specific administration mode is that the bacterial-carrying leaf is ground by liquid nitrogen, the ground bacterial-carrying leaf is weighed and distributed into ep tubes (50 mg/tube), then 1mL of deionized water is added into each ep tube to prepare compounds with different concentrations of 1-10 (if the drug is water-insoluble, the DMSO can be added in a proper amount to assist dissolution, but the final concentration of the DMSO does not exceed 1%), the mixture is soaked for 72 hours, and the same volume of deionized water is added into a blank control group. Each compound in the administration group was set to 3 final concentration gradients of 0.1mg/mL, 0.001mg/mL, and 0.0001mg/mL, respectively.
6.2.2 nucleic acid extraction PCR detection
Extracting DNA of pear recession disease pathogenic bacteria from dosed leaves according to a CTAB method, and performing nucleic acid purity analysis on the extracted DNA by using an ultramicro nucleic acid protein analyzer (the specific DNA extraction method and the purity analysis method can be found in reference to: Dinghao, Zhengtang spring, Liangdeyang, Quguan syndrome, a simple and efficient method for extracting pure DNA of various plants, plant research, 2015, Vol.35, Issue (3):457-461, DOI:10.7525/j.issn.1673-5102.2015.03.021), performing gene detection by using a real-time fluorescence quantitative PCR instrument after the quality is qualified, and recording a corresponding CT value.
6.3 results of the experiment
The results are shown in Table 7.
TABLE 7 antibacterial test results for Pyricularia piricola in vitro leaves
6.4 conclusion of the experiment
As can be seen from the detection results in Table 7, compared with a blank control group, the compounds 1-10 have a certain antibacterial effect at a final concentration of 0.001mg/ml, and the CT value mean value of the compounds is more than 35 at a final concentration of more than 0.01mg/ml (including 0.01mg/ml), which indicates that the compounds have the effect of completely killing pear recession disease germs in-vitro leaves at a concentration of more than 0.01mg/ml (including 0.01 mg/ml).
Finally, it should be noted that: the above examples are only intended to illustrate the technical solutions of the present disclosure and not to limit the same; although the present disclosure has been described in detail with reference to preferred embodiments, those skilled in the art will appreciate that: modifications to the specific embodiments of the disclosure or equivalent substitutions for parts of the technical features may still be made; all of which are intended to be encompassed within the scope of the claims of this disclosure without departing from the spirit of the claims of this disclosure.
Claims (35)
1. The use of a compound of formula I or an agriculturally or forestry chemically acceptable salt thereof or a composition comprising a compound of formula I or an agriculturally or forestry chemically acceptable salt thereof for preventing or controlling or treating infectious diseases of plants caused by a pathogenic agent,
wherein R is1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14Each independently selected from: hydrogen, fluorine, chlorine, bromine, iodine, C1-8Alkyl radical, C1-8Alkoxy, nitro, hydroxyl, cyano, amino,
the pathogen is a bacterium parasitizing at the phloem of the plant.
2. The use according to claim 1, wherein the pathogen is a plant genus of Phytoplasma (Phytoplasta) or the genus of the genus Candidatus Liberibacter spp.
3. The use of claim 1, wherein the pathogen is a mycobacterium species asia (Candidatus Liberibacter asiaticus), a mycobacterium african (Candidatus Liberibacter africanus), a mycobacterium america (Candidatus Liberibacter americanus), a Candidatus Liberibacter solanacearum, a grape yellow Phytoplasma (grape yellow pigment multiple Phytoplasma), or a pear failure Phytoplasma (Candidatus Phytoplasma pyri).
4. The use of claim 1, wherein the infectious disease caused by a pathogen is huanglongbing, zebra chip disease, grape golden disease or pear failure.
5. The use according to claim 1, wherein the plant is a solanaceous plant, an umbelliferae plant, a rutaceae plant, a vitiaceae plant or a rosaceae plant.
6. Use according to claim 5, characterized by one or more of the following i) to v):
i) the plant of Solanaceae is potato, tomato, eggplant, green tomato or tree tomato;
ii) the Umbelliferae plant is carrot or celery;
iii) the Rutaceae plant is Citrus, Poncirus or Murraya;
iv) the Vitaceae plant is grape;
v) the Rosaceae plant is a pear.
7. The use according to claim 1, wherein the composition further comprises an adjuvant.
8. A method for preventing or controlling or treating infestation of plants by a pathogen, which comprises treating the pathogen, its habitat or the area, substance or space to be protected from attack by the pathogen with an effective amount of at least one compound of the formula I or an agriculturally or forestry chemically acceptable salt thereof,
wherein R is1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14Each independently selected from: hydrogen, fluorine, chlorine, bromine, iodine, C1-8Alkyl radical, C1-8Alkoxy, nitro, hydroxyl, cyano, amino,
the pathogen is a bacterium parasitizing at the phloem of the plant.
9. The method of claim 8, wherein the substance is a plant, plant propagation material, soil or organic substrate.
10. A method for preventing or controlling or treating infectious diseases of plants caused by pathogens, comprising applying to the plants, propagation material thereof, fruits thereof or the soil, organic substrate, area or space in which they grow, an effective amount of at least one compound of formula I or an agriculturally or forestry chemically acceptable salt thereof,
wherein R is1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14Each independently selected from: hydrogen, fluorine, chlorine, bromine, iodine, C1-8Alkyl radical, C1-8Alkoxy, nitro, hydroxyl, cyano, amino,
the pathogen is a bacterium parasitizing at the phloem of the plant.
11. A method for preventing or controlling or treating infestation of plants by a pathogen, which comprises treating the pathogen, its habitat or the area, substance or space to be protected from attack by the pathogen with a composition comprising an effective amount of at least one compound of formula I or an agriculturally or forestry chemically acceptable salt thereof,
wherein R is1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14Each independently selected from: hydrogen, fluorine, chlorine, bromine, iodine, C1-8Alkyl radical, C1-8Alkoxy, nitro, hydroxyl, cyano, amino,
the pathogen is a bacterium parasitizing at the phloem of the plant.
12. The method of claim 11, wherein the substance is a plant, plant propagation material, soil or organic substrate.
13. A method of preventing or controlling or treating an infectious disease in a plant caused by a pathogen, comprising: applying a composition comprising an effective amount of at least one compound of formula I or an agriculturally or forestry chemically acceptable salt thereof to the plant, to propagation material of the plant, to a fruit of the plant, to soil in which the plant is growing, to an organic substrate in which the plant is growing, to an area in which the plant is growing or to a space in which the plant is growing,
wherein R is1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14Each independently selected from: hydrogen, fluorine, chlorine, bromine, iodine, C1-8Alkyl radical, C1-8Alkoxy, nitro, hydroxyl, cyano, amino,
the pathogen is a bacterium parasitizing at the phloem of the plant.
14. The method of claim 11 or 13, wherein the composition further comprises an adjuvant.
15. The method of any one of claims 8-13, wherein the pathogen is a Phytoplasma (Phytoplasma) or a phloem bacterium (Candidatus Liberibacter spp.) that is parasitic in the phloem of a plant.
16. The method of any one of claims 8-13, wherein the pathogen is a mycobacterium species asia (Candidatus Liberibacter asiaticus), a mycobacterium african (Candidatus Liberibacter africanus), a mycobacterium americana (Candidatus Liberibacter americanus), a candida Liberibacter solanacearum, a grape yellow gold Phytoplasma (grape yellow pigment) or a pear failure Phytoplasma (Candidatus Phytoplasma pyri).
17. The method of any one of claims 8-13, wherein the plant is a solanaceous plant, an umbelliferae plant, a rutaceae plant, a vitiaceae plant, or a rosaceous plant.
18. The method of claim 17, characterized by one or more of the following i) to v):
i) the plant of Solanaceae is potato, tomato, eggplant, green tomato or tree tomato;
ii) the Umbelliferae plant is carrot or celery;
iii) the Rutaceae plant is Citrus, Poncirus or Murraya;
iv) the Vitaceae plant is grape;
v) the Rosaceae plant is a pear.
19. The method of any one of claims 10 or 13, wherein the invasive disease caused by a pathogen is huanglongbing, zebra chip disease, grape golden disease, or pear failure.
20. The use of any one of claims 1 to 7, wherein R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14Each independently selected from: hydrogen, fluorine, chlorine, bromine, iodine, C1-6Alkyl radical, C1-6Alkoxy, nitro, hydroxyl, cyano, amino.
21. The use of claim 20, wherein R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14Each independently selected from: hydrogen, fluorine, chlorine, bromine, iodine, C1-4Alkyl radical, C1-4Alkoxy, nitro, hydroxyl, cyano, amino.
22. The use of any one of claims 1 to 7, wherein R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14Each independently selected from: hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, methoxy, ethoxy, n-propoxy, isopropyloxy, n-butyloxy, isobutyloxy, sec-butyloxy, tert-butyloxy, n-pentyloxy, n-hexyloxy, nitro, hydroxyl, cyano or amino.
23. The use of claim 22, wherein R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14Each independently selected from: hydrogen, fluorine, chlorine, bromine, hydroxyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropyloxy, n-butyloxy, isobutyloxy, sec-butyloxy, tert-butyloxy.
24. The use of any one of claims 1 to 7, wherein R1、R2、R3、R4、R5Each independently selected from: hydrogen, fluoro, chloro, bromo, hydroxy, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, n-propoxy and isopropyloxy;
R6、R7、R8、R9each independently selected from: hydrogen, fluoro, chloro, bromo, hydroxy, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, n-propoxy and isopropyloxy;
R10、R11、R12、R13、R14each independently selected from: hydrogen, fluorine, chlorine, bromine, hydroxyl, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, n-propoxy and isopropyloxy.
25. The use of any one of claims 1 to 7, wherein R1、R2、R3、R4、R5Each independently selected from: hydrogen, fluorine, chlorine, bromine and hydroxyl;
R6、R7、R8、R9each independently selected from: hydrogen, fluoro, chloro, bromo, methyl and methoxy;
R10、R11、R12、R13、R14each independently selected from: hydrogen, fluorine, chlorine, bromine and hydroxyl.
26. The use of any one of claims 1 to 7, wherein R1Is hydrogen, bromine or chlorine; r2Is hydrogen or bromine; r3Is hydrogen, bromine or hydroxy; r4Is hydrogen, fluorine, chlorine or bromine; r5Is hydrogen or chlorine; r6Is hydrogen; r7Is hydrogen, bromine, methyl or methoxy; r8Is hydrogen or chlorine; r9Is hydrogen, methyl or methoxy; r10Is hydrogen or chlorine; r11Is hydrogen, chlorine, fluorine or bromine; r12Is hydrogen, chlorine or hydroxyl; r13Is hydrogen, chlorine or bromine; r14Is hydrogen, chlorine or bromine.
27. The use according to any one of claims 1 to 7, wherein the compound of formula I is selected from:
28. the method of any one of claims 8-13, wherein R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14Each independently selected from: hydrogen, fluorine, chlorine, bromine, iodine, C1-6Alkyl radical, C1-6Alkoxy, nitro, hydroxyl, cyano, amino.
29. The method of claim 28, wherein R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14Each independently selected from: hydrogen, fluorine, chlorine, bromine, iodine, C1-4Alkyl radical, C1-4Alkoxy, nitro, hydroxyl, cyano, amino.
30. The method of any one of claims 8-13, wherein R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14Each independently selected from: hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, methoxy, ethoxy, n-propoxy, isopropyloxy, n-butyloxy, isobutyloxy, sec-butyloxy, tert-butyloxy, n-pentyloxy, n-hexyloxy, nitro, hydroxyl, cyano or amino.
31. The method of claim 30, wherein R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14Each independently selected from: hydrogen, fluorine, chlorine, bromine, hydroxyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropyloxy, n-butyloxy, isobutyloxy, sec-butyloxy, tert-butyloxy.
32. The method of any one of claims 8-13, wherein R1、R2、R3、R4、R5Each independently selected from: hydrogen, fluoro, chloro, bromo, hydroxy, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, n-propoxy and isopropyloxy;
R6、R7、R8、R9each independently selected from: hydrogen, fluoro, chloro, bromo, hydroxy, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, n-propoxy and isopropyloxy;
R10、R11、R12、R13、R14each independently selected from: hydrogen, fluorine, chlorine, bromine, hydroxyl, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, n-propoxy and isopropyloxy.
33. The method of any one of claims 8-13, wherein R1、R2、R3、R4、R5Each independently selected from: hydrogen, fluorine, chlorine, bromine and hydroxyl;
R6、R7、R8、R9each independently selected from: hydrogen, fluoro, chloro, bromo, methyl and methoxy;
R10、R11、R12、R13、R14each independently selected from: hydrogen, fluorine, chlorine, bromine and hydroxylAnd (4) a base.
34. The method of any one of claims 8-13, wherein R1Is hydrogen, bromine or chlorine; r2Is hydrogen or bromine; r3Is hydrogen, bromine or hydroxy; r4Is hydrogen, fluorine, chlorine or bromine; r5Is hydrogen or chlorine; r6Is hydrogen; r7Is hydrogen, bromine, methyl or methoxy; r8Is hydrogen or chlorine; r9Is hydrogen, methyl or methoxy; r10Is hydrogen or chlorine; r11Is hydrogen, chlorine, fluorine or bromine; r12Is hydrogen, chlorine or hydroxyl; r13Is hydrogen, chlorine or bromine; r14Is hydrogen, chlorine or bromine.
35. The method of any one of claims 8-13, wherein the compound of formula I is selected from the group consisting of:
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| CN106034894A (en) * | 2016-05-30 | 2016-10-26 | 广东省农业科学院植物保护研究所 | Method for protecting and restoring germplasm of citrus-Hunglongbing-infected citrus according to two-step method |
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