WO2022196649A1 - Procédé permettant d'induire une résistance chez une plante, agent induisant une résistance chez une plante et biostimulant - Google Patents

Procédé permettant d'induire une résistance chez une plante, agent induisant une résistance chez une plante et biostimulant Download PDF

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WO2022196649A1
WO2022196649A1 PCT/JP2022/011401 JP2022011401W WO2022196649A1 WO 2022196649 A1 WO2022196649 A1 WO 2022196649A1 JP 2022011401 W JP2022011401 W JP 2022011401W WO 2022196649 A1 WO2022196649 A1 WO 2022196649A1
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carbon atoms
linear
resistance
plant
compound
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Japanese (ja)
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和之 平塚
里江子 小倉
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国立大学法人横浜国立大学
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01H—NEW PLANTS OR NON-TRANSGENIC PROCESSES FOR OBTAINING THEM; PLANT REPRODUCTION BY TISSUE CULTURE TECHNIQUES
    • A01H3/00—Processes for modifying phenotypes, e.g. symbiosis with bacteria
    • A01H3/04—Processes for modifying phenotypes, e.g. symbiosis with bacteria by treatment with chemicals
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
    • A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
    • A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P21/00—Plant growth regulators
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides

Definitions

  • the present invention relates to a method for inducing plant resistance, a plant resistance inducer and a biostimulant.
  • Plants are invaded and attacked by various pathogenic microorganisms such as filamentous fungi, bacteria, and viruses. Plants have developed defense mechanisms to combat them. There are various stages in the defense mechanism. First, in the stage before pathogen invasion, pathogen invasion is blocked by physical barriers such as cell walls and stomatal opening and closing of leaves. Even after pathogen invasion, plant cells recognize the pathogen invasion and accumulate polysaccharides at the site of invasion to inhibit the progress of infection. Furthermore, plants have a mechanism that strengthens resistance not only at sites infected with pathogens, but also at non-infected sites by transmitting signals throughout the body from infected sites. Plant hormones and the expression of many genes are involved in this mechanism.
  • FIG. 1 is a diagram illustrating signal transduction pathways involved in plant resistance induction.
  • SAR Systemic Acquired Resistance
  • SA plant hormone salicylic acid
  • live parasitic pathogens are pathogens that take nutrients from living cells. Live parasitic pathogens often take nutrients from plant cells and coexist with plants. Examples of live parasitic pathogens include rice blast fungus and anthracnose fungus.
  • Probenazole (PBZ, trade name Orizemate) has sales of about 10 billion yen per year, even though it has been developed for more than 40 years.
  • PBZ trade name Orizemate
  • resistance inducers or plant activators with SAR-inducing activity such as acibenzolar-S-methyl (ASM), palydamycin A (VMA), benzothiadiazole (BTH), thiazinyl (TDL). ), isotianil, etc. are known.
  • ASM acibenzolar-S-methyl
  • VMA palydamycin A
  • BTH benzothiadiazole
  • TDL thiazinyl
  • isotianil etc.
  • ISR Induced Systemic Resistance
  • JA jasmonic acid
  • JA mainly induces resistance to "saprophytic pathogens” (also called “dead parasites”), which are pathogens that take nutrients from dead cells, and protective responses to "injuries” such as feeding damage by pests.
  • Sud mold is a representative saprophytic pathogen. Botrytis infects almost all plants, and drug-resistant fungi are very likely to develop. However, compounds with SAR-inducing activity have poor control effects against saprophytic pathogens, and existing plant activators such as probenazole are ineffective against saprophytic pathogens such as botrytis.
  • Non-Patent Document 1 a compound that has the activity of inducing the ISR system, it may be used as a new pest control material that is effective against types of diseases that cannot be dealt with by existing SAR system resistance inducers.
  • studies to date have not found any low-molecular-weight compounds having such activity to the extent that they are commercially available. Bestatin is reported to be a compound that specifically activates JA signaling (Non-Patent Document 1).
  • Non-Patent Documents 2-4 Using Arabidopsis thaliana, it has been shown that all of these induce the expression of JA-responsive genes, including PDF1.2 and VSP2, and are effective in suppressing the formation of lesions caused by botrytis.
  • the treatment with hexanoic acid and arachidonic acid has also been observed to inhibit the formation of lesions in tomatoes (Non-Patent Document 5). This indicates that the JA resistance inducer is effective in controlling gray mold.
  • the efficacy of these agents has problems such as the need for high-concentration treatment.
  • the resistance inducer acts on plants and has no bactericidal activity itself, so it is difficult for drug-resistant bacteria to emerge, and it has been attracting attention in recent years as a low-environmental-burden drug.
  • the only resistance inducers currently in practical use are PBZ and ASM that act on the SA signal transduction system, and no resistance inducers that act on the JA/ET signal transduction system have been put to practical use. .
  • Patent Document 1 that acts on the SA signal transduction system
  • Patent Document 2 that acts on the JA signal transduction system
  • the present invention has been made in view of the above circumstances, and an object of the present invention is to provide a plant resistance-inducing method and a plant resistance-inducing agent having excellent plant resistance-inducing activity. Another object of the present invention is to provide a biostimulant.
  • the present inventors have made intensive studies to solve the above problems, and found that it is possible to activate both the SA signal transduction system and the JA/ET signal transduction system. We have found that resistance can be induced, and have completed the present invention. That is, the present invention has the following aspects.
  • a method for inducing plant resistance comprising: applying a plant resistance inducer to the plant to activate the salicylic acid signaling system and the jasmonic acid and/or ethylene signaling system;
  • the active ingredient of the plant resistance inducer is a low-molecular-weight compound, and one of the active ingredients activates the salicylic acid signal transduction system and the jasmonic acid and/or ethylene signal transduction system.
  • Methods for Inducing Plant Resistance [2] The method according to [1] above, wherein the plant resistance inducer contains a compound represented by the following general formula (1) or a salt thereof as an active ingredient.
  • R 1 , R 2 and R 3 are each independently a linear or branched alkyl group having 1 to 4 carbon atoms, a hydroxyl group, a halogen atom, or a linear or branched chain having 2 to 4 carbon atoms represents an alkenyl group
  • R 4 represents a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, or a linear or branched alkenyl group having 2 to 4 carbon atoms
  • R 5 and R 6 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, a linear or branched alkenyl group having 2 to 4 carbon atoms, or represents a halogen atom.
  • n1 represents the number of R 1 and is an integer of 0 to 5, and when n1 is 2 or more, R 1 may be the same or different.
  • n2 represents the number of R 2 and is an integer of 0 to 5, and when n2 is 2 or more, R 2 may be the same or different.
  • n3 represents the number of R 3 and is an integer of 0 to 3. When n3 is 2 or more, R 3 may be the same or different.
  • R 1 , R 2 and R 3 are each independently a linear or branched alkyl group having 1 to 4 carbon atoms, a hydroxyl group, a halogen atom, or a linear or branched chain having 2 to 4 carbon atoms represents an alkenyl group
  • R 4 represents a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, or a linear or branched alkenyl group having 2 to 4 carbon atoms
  • R 5 and R 6 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, a linear or branched alkenyl group having 2 to 4 carbon atoms, or represents a halogen atom.
  • n1 represents the number of R 1 and is an integer of 0 to 5, and when n1 is 2 or more, R 1 may be the same or different.
  • n2 represents the number of R 2 and is an integer of 0 to 5, and when n2 is 2 or more, R 2 may be the same or different.
  • n3 represents the number of R 3 and is an integer of 0 to 3. When n3 is 2 or more, R 3 may be the same or different.
  • R 1 , R 2 and R 3 are each independently a linear or branched alkyl group having 1 to 4 carbon atoms, a hydroxyl group, a halogen atom, or a linear or branched chain having 2 to 4 carbon atoms represents an alkenyl group
  • R 4 represents a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, or a linear or branched alkenyl group having 2 to 4 carbon atoms
  • R 5 and R 6 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, a linear or branched alkenyl group having 2 to 4 carbon atoms, or represents a halogen atom.
  • n1 represents the number of R 1 and is an integer of 0 to 5, and when n1 is 2 or more, R 1 may be the same or different.
  • n2 represents the number of R 2 and is an integer of 0 to 5, and when n2 is 2 or more, R 2 may be the same or different.
  • n3 represents the number of R 3 and is an integer of 0 to 3. When n3 is 2 or more, R 3 may be the same or different.
  • Fig. 4 shows the results of measurement of JA-responsive gene expression by compound X treatment of Arabidopsis thaliana seedlings having VSP1::Fluc.
  • Fig. 3 shows the results of measurement of JA-responsive gene expression by compound X treatment of adult Arabidopsis thaliana plants having VSP1::Fluc.
  • Fig. 3 shows the results of measurement of SA-responsive gene expression by compound X treatment of Arabidopsis thaliana seedlings harboring PR-1a::Fluc.
  • Fig. 4 shows the results of measurement of JA-responsive gene expression by compound X treatment of Arabidopsis thaliana seedlings having VSP1::Fluc.
  • Fig. 3 shows the results of measurement of SA-responsive gene expression by compound X treatment of Arabidopsis thaliana seedlings harboring PR-1a::Fluc.
  • Fig. 4 shows the results of measurement of JA-responsive gene expression by compound X treatment of Arabidopsis thaliana seedlings having V
  • FIG. 4 shows the measurement results of ET-responsive gene expression by compound X treatment of Arabidopsis thaliana seedlings having PDF1.2::Fluc. It is the result of having evaluated the control effect of the compound X with respect to gray mold. It is the result of evaluating the control effect of compound X against anthracnose.
  • Fig. 4 shows the results of measurement of time-course changes in expression of JA-responsive genes in Arabidopsis thaliana seedlings treated with compound X.
  • Fig. 4 shows the results of measurement of time-course changes in expression of SA-responsive genes in Arabidopsis thaliana seedlings treated with compound X.
  • FIG. Fig. 4 shows the results of measurement of changes over time in the expression of JA-responsive genes in adult Arabidopsis thaliana individuals treated with compound X.
  • 2 shows the results of measurement of time-course changes in expression of SA-responsive genes in mature Arabidopsis thaliana individuals treated with compound X.
  • FIG. Fig. 4 shows the results of measurement of changes over time in the expression of ET-responsive genes in Arabidopsis thaliana seedlings treated with compound X.
  • Fig. 4 shows the results of measurement of time-course changes in the expression of ET-responsive genes in mature Arabidopsis thaliana individuals treated with compound X.
  • 2 shows the evaluation results of the antibacterial activity of compound X against gray mold. 2 shows the results of evaluating the antibacterial activity of compound X against anthracnose.
  • Embodiments of the method for inducing plant resistance, the plant resistance inducer, and the biostimulant of the present invention are described below.
  • a method for inducing plant resistance of an embodiment is a method for inducing plant resistance, applying a plant resistance inducer to the plant to activate the salicylic acid signaling system and the jasmonic acid and/or ethylene signaling system;
  • the active ingredient of the plant resistance inducer is a low-molecular-weight compound, and one of the active ingredients activates the salicylic acid signal transduction system and the jasmonic acid and/or ethylene signal transduction system.
  • the plant resistance inducer is classified as "P host plant resistance induction" according to the FRAC: Fungicide Resistance Action Committee classification of drug mechanism of action. This is in sharp contrast to common fungicides (including bactericides) that act on biosynthetic pathways on the pathogen side.
  • the resistance inducer itself has no bactericidal activity. Therefore, there is an advantage that drug-resistant bacteria are less likely to appear.
  • Salicylic acid signaling is the only class of resistance-inducing agents presented above.
  • the plant resistance inducer may be simply referred to as "resistance inducer”.
  • FIG. 1 is a diagram explaining the signal transduction pathways involved in plant resistance induction.
  • the salicylic acid signal transduction system also referred to as "SA system”
  • SA system includes a signal transduction pathway following SA, NPR1 gene expression, and PR1 gene expression.
  • the SA system is capable of inducing resistance to virulent parasites.
  • the jasmonate signal transduction system (also referred to as the "JA system") includes JA, JAR1 gene expression, VSP1 gene expression, and subsequent signal transduction pathways.
  • the JA system is capable of inducing resistance and/or injury responses to dead parasites. Damage responses include pest resistance, drought tolerance, and the like.
  • the ethylene signal transduction system (also referred to as "ET system”) includes a signal transduction pathway following ET, EIN2 gene expression, and PDF1.2 gene expression.
  • the ET system can induce resistance to dead parasites. Since signals from JAR1 also induce PDF1.2 gene expression, jasmonic acid can activate the JA and/or ET system.
  • the application of one active ingredient can activate the SA system and the JA system and/or the ET system, and this finding overturns the conventional concept of resistance induction. It is.
  • ASM and PBZ which are representative resistance inducers that activate only the SA system
  • resistance induction activity equivalent to or greater than that can be exhibited It is presumed that this excellent effect is achieved by a novel mechanism of action that activates the SA system and the JA system and/or the ET system.
  • at least one active ingredient can activate the SA system and the JA system and/or the ET system.
  • the expression of disease resistance can be judged, for example, by any one or more indicators of "1" to "2" below.
  • “1” Using the expression of genes whose expression is induced in the SA system, JA system, or ET system as an index, comparing plants treated with a resistance inducer and untreated plants (control plants), resistance When the expression of the gene is significantly enhanced in the plant treated with the sex-inducing agent, expression of disease resistance can be determined.
  • the expression of genes whose expression is induced in the SA system can be used as an index for the expression of resistance to viable parasitic fungi. Expression of resistance to dead parasite fungi can be indicated by the expression of genes whose expression is induced by the JA system and/or the ET system.
  • Expression of pest resistance in plants can be determined, for example, by any one or more of the following indicators of "3" to "5". Using the expression of genes whose expression is induced in the "3" JA system as an index, the plants treated with the resistance inducer are compared with the untreated plants (control plants), and the resistance inducer is treated. The expression of pest resistance can be judged when the expression of the gene is significantly improved in the plants obtained from the strain. "4" Using the degree of feeding damage on the plant body as an index, the plants treated with the resistance inducer are compared with the untreated plants (control plants). When the state of feeding damage to the plant bodies is improved in the plants that have been treated with insect pests, the development of pest resistance can be determined.
  • the resistance in a plant treated with an inducer Using the inhabitation state of organisms such as pests in the section treated with the resistance inducer as an index, comparing the plants treated with the resistance inducer and the untreated plants (control plants), the resistance In a plant treated with an inducer, development of pest resistance can be judged when the number of living organisms such as pests in the area treated with the resistance inducer is low.
  • the method of the embodiment is excellent in activating the salicylic acid signal transduction system and the jasmonic acid and/or ethylene signal transduction system, and makes plants exhibit excellent resistance.
  • Numerical values representing the extent to which the SA system and the JA system and/or the ET system are activated compared to control plants preferably include the following.
  • the SA system is preferably activated twice or more by using the expression level of the VSP1 gene as an index
  • the JA system is activated by using the expression level of the PR1 gene as an index, as compared with the control plant. It is preferable to activate 2-fold or more, and/or it is preferable to activate the ET system by 2-fold or more using the expression level of the PDF1.2 gene as an index.
  • the activation of the SA system is preferably 2-fold or more, more preferably 2- to 100-fold, further preferably 3- to 60-fold, and particularly preferably 4- to 10-fold.
  • the above activation of the JA system is preferably 2-fold or more, more preferably 2-10 times, and still more preferably 3-8 times.
  • the activation of the ET system is preferably 2-fold or more, more preferably 2- to 150-fold, further preferably 3- to 60-fold, and particularly preferably 4- to 50-fold.
  • VSP1, PR1, and PDF1.2 genes correspond to genes (homologs) corresponding to the respective genes of the plant to which the resistance inducer is to be used.
  • VSP1 gene examples include genes encoding proteins selected from the group consisting of the following (a1) to (c1).
  • (a1) a protein having the amino acid sequence represented by SEQ ID NO: 1;
  • amino acid sequence represented by SEQ ID NO: 1 is the amino acid sequence of Arabidopsis VSP1 (AT5G24780.1).
  • Examples of the PR1 gene include genes encoding proteins selected from the group consisting of the following (a2) to (c2).
  • (a2) a protein having the amino acid sequence represented by SEQ ID NO: 2;
  • a protein (c2) that has an amino acid sequence that has a sequence identity of 80% or more with the amino acid sequence represented by SEQ ID NO: 2 and that induces resistance in plants
  • amino acid sequence represented by SEQ ID NO: 2 is the amino acid sequence of Arabidopsis PR1 (AT2G14610.1).
  • Examples of the PDF1.2 gene include genes encoding proteins selected from the group consisting of the following (a3) to (c3).
  • (a3) a protein having the amino acid sequence represented by SEQ ID NO: 3;
  • a protein (c3) that has an amino acid sequence that has a sequence identity of 80% or more with the amino acid sequence represented by SEQ ID NO: 3 and that induces resistance in plants
  • amino acid sequence represented by SEQ ID NO: 3 is the amino acid sequence of Arabidopsis PDF1.2 (AT5G44420.1).
  • the "1 to several" bases may be, for example, 1 to 30, 1 to 20, 1 to 10, 1 to 5, or 1 to 3 bases.
  • Said sequence identity may be 80% or more, but less than 100%, for example, 85% or more, 90% or more, 95% or more, or 98% or more.
  • Sequence identity between amino acid sequences can be calculated using known sequence alignment algorithms such as BLAST (Basic Local Alignment Search Tool) and blastp.
  • the plant resistance inducer used in the method of the embodiment is a low-molecular-weight compound, and preferred plant resistance inducers are described in detail below.
  • the term "low-molecular-weight compound” refers to a compound having a molecular weight of 10,000 or less.
  • the method of applying the plant resistance inducer also includes various methods exemplified below as the method of contacting the plant with the plant resistance inducer.
  • a resistance inducer is used to activate the JA system and/or the ET system to induce a wide range of resistance, including resistance to live parasites and dead parasites. can.
  • it has no antibacterial activity against bacteria including live parasites and dead parasites, and can be implemented as a production method with less environmental load, in which damage to environmental microorganisms is reduced.
  • plant resistance inducers can be exemplified as plant resistance inducers used in the method of the embodiment.
  • the plant resistance inducer of the embodiment contains a compound represented by the following general formula (1) or a salt thereof as an active ingredient.
  • R 1 , R 2 and R 3 are each independently a linear or branched alkyl group having 1 to 4 carbon atoms, a hydroxyl group, a halogen atom, or a linear or branched chain having 2 to 4 carbon atoms represents an alkenyl group
  • R 4 represents a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, or a linear or branched alkenyl group having 2 to 4 carbon atoms
  • R 5 and R 6 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, a linear or branched alkenyl group having 2 to 4 carbon atoms, or represents a halogen atom.
  • n1 represents the number of R 1 and is an integer of 0 to 5, and when n1 is 2 or more, R 1 may be the same or different.
  • n2 represents the number of R 2 and is an integer of 0 to 5, and when n2 is 2 or more, R 2 may be the same or different.
  • n3 represents the number of R 3 and is an integer of 0 to 3. When n3 is 2 or more, R 3 may be the same or different.
  • Examples of the linear or branched alkyl group having 1 to 4 carbon atoms for R 1 , R 2 , R 3 , R 4 , R 5 and R 6 include methyl group, ethyl group, n-propyl group and isopropyl group. group, n-butyl group, isobutyl group, sec-butyl group and tert-butyl group.
  • the linear or branched alkenyl group having 2 to 4 carbon atoms of R 1 , R 2 , R 3 , R 4 , R 5 and R 6 preferably has 2 to 3 carbon atoms.
  • Examples of the alkenyl group include ethenyl group (vinyl group) and 2-propenyl group (allyl group).
  • the halogen atoms of R 1 , R 2 , R 3 , R 5 and R 6 are elements belonging to group 17 in the periodic table, such as F, Cl, Br, and I.
  • R 1 , R 2 , R 3 , n1, n2 and n3 are the same as in the general formula (1). ]
  • R 1 , R 2 and R 3 each independently represents a linear or branched alkyl group having 1 to 4 carbon atoms. you can
  • the compound represented by the general formula (1) may be a salt, and the salt is preferably an agriculturally acceptable salt, and depending on the type of substituent, forms an acid addition salt or a salt with a base. sometimes.
  • inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, phosphoric acid, formic acid, acetic acid, propionic acid, oxalic acid, malonic acid, succinic acid, fumaric acid, maleic acid , lactic acid, malic acid, mandelic acid, tartaric acid, dibenzoyltartaric acid, ditoluoyltartaric acid, citric acid, methanesulfonic acid, ethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, aspartic acid, glutamic acid, and other organic acids.
  • Salts salts with inorganic bases such as sodium, potassium, magnesium, calcium and aluminum, salts with organic bases such as methylamine, ethylamine, ethanolamine, lysine and ornithine, salts and ammonium salts of various amino acids and amino acid derivatives such as acetylleucine, etc.
  • Inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, phosphoric acid, formic acid, acetic acid, propionic acid, oxalic acid, malonic acid, succinic acid, fumaric acid, maleic acid, Acid addition salts with organic acids such as lactic acid, malic acid, mandelic acid, tartaric acid, dibenzoyltartaric acid, ditoluoyltartaric acid, citric acid, methanesulfonic acid, ethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, aspartic acid, glutamic acid, etc. is preferred.
  • the active ingredient also includes various hydrates, solvates, and crystal polymorphs of the compound of general formula (1) and salts thereof. Active ingredients also include compounds labeled with various radioactive or non-radioactive isotopes.
  • the compounds of the general formula (1) and salts thereof can be used as the compounds of the general formula (1) and salts thereof.
  • the compounds of the general formula (1) and salts thereof can be produced by applying known synthetic methods to various known compounds by utilizing the characteristics based on the basic structure or the type of substituents. can. In this case, depending on the type of functional group, it may be effective from the viewpoint of production technology to replace the functional group with an appropriate protective group well known to those skilled in the art in the stages from raw materials to intermediates.
  • Plant resistance induction as used herein includes inducing, enhancing, promoting and maintaining disease resistance or pest resistance of plants. Since the plant resistance inducer of the embodiment induces disease resistance, it can also be provided as a plant disease control agent. Since the plant resistance inducer of the embodiment induces pest resistance, it can also be provided as an pest control agent.
  • Inducing, enhancing, and promoting disease resistance or pest resistance of plants means comparing plants treated with the resistance inducer of the embodiment and plants not treated, It means that expression of plant resistance or pest resistance is significantly improved in plants treated with a plant resistance inducer.
  • To maintain the disease resistance or pest resistance of plants is to compare plants treated with the plant resistance inducer of the embodiment and plants that are not treated, and the plant resistance inducer of the embodiment is treated. It means that the expression of plant resistance or pest resistance is significantly prolonged in the plants that have been treated.
  • the SA system, JA system and/or ET system involved in plant resistance induction can be activated. It has been demonstrated in Examples described later that the resistance-inducing agents of the embodiments exhibit resistance-inducing activity equal to or higher than that of the existing resistance-inducing agents ASM and PBZ. This excellent effect is presumed to be achieved by a novel mechanism of action involved in signal transduction. According to the resistance inducer of the embodiment, one active ingredient can activate the SA system and the JA system and/or the ET system.
  • the type of plant to which the resistance inducer is applied is particularly a plant that can acquire resistance by inducing the SAR (i.e., SA system) and ISR (i.e., JA system and/or ET system). It is not limited and may be a land plant or an aquatic plant. As land plants, angiosperms or gymnosperms are suitable, and they may be herbaceous plants or woody plants.
  • Angiosperms include the family Rosaceae, Rutaceae, Grapes, Asteraceae, Orchids, Liliaceae, Legumes, Poaceae, Rubiaceae, Euphorbiaceae, Cyperaceae, Umbelliferae, Labiatae, Cucurbitaceae, Solanaceae, and cruciferous are more preferred, and cruciferous are even more preferred.
  • An onion can be exemplified as the plant belonging to the Liliaceae family.
  • a soybean can be exemplified as the leguminous plant.
  • a carrot can be exemplified as the plant belonging to the Umbelliferae family.
  • Examples of the Poaceae plants include rice, corn, wheat, and wheat.
  • Examples of the Cucurbitaceae plants include melons, watermelons, winter melons, cucumbers, and pumpkins.
  • Examples of the plants belonging to the family Solanaceae include tobacco, tomato, potato, eggplant, green pepper, and the like.
  • Examples of the plants of the cruciferous family include shepherd's purse, rapeseed, cabbage, kale, Chinese cabbage, turnip, Japanese radish, wasabi, and mustard.
  • Tomatoes, tobacco, cucumbers, shepherd's purses, and rapeseeds are examples of preferred plants for which the resistance-inducing agents of the embodiments are used.
  • the resistance inducer of the embodiment may be provided in the form of powders, tablets, granules, fine granules, etc. by mixing with agriculturally acceptable carriers, fillers, etc., if necessary. Alternatively, they can be mixed with agriculturally acceptable solvents, surfactants, emulsifiers, dispersants and the like to form formulations such as emulsions, liquids, suspensions, wettable powders, aqueous solutions and oils.
  • the solvent for dissolving the resistance inducer may be appropriately selected according to the resistance inducer and the type of plant.
  • examples include sulfoxide compounds such as dimethylsulfoxide (DMSO); Hydrophilic solvents such as amide compounds such as N-dimethylacetamide (DMAc) and N-methylpyrrolidone (NMP) are preferred examples.
  • the resistance inducer of the embodiment may be provided in a dosage form that is used in combination with other agricultural and horticultural agents.
  • the resistance inducers of the embodiments and other JA resistance inducers such as bestatin, hexanoic acid, arachidonic acid, and N-acylamide may be provided in dosage forms such as mixtures and combination preparations.
  • the resistance inducer of the embodiment and other SA-based resistance inducers such as probenazole and acibenzolar-S-methyl may be provided in a dosage form such as a mixture or combination preparation.
  • Pathogens to be protected by the use of the resistance inducers of the embodiments are not particularly limited, but pathogens that induce SAR or ISR or can be protected by SAR or ISR induction are preferred. Alternatively, it is preferably a pathogen that causes induction of SAR or ISR and can be protected by induction of SAR or ISR. From such a point of view, pathogens to be protected by the resistance inducer of the embodiment are live parasitic pathogens (also simply referred to as "live parasites"), or saprophytic pathogens (also referred to as "dead parasites”) It is more preferable to be live parasitic pathogens (also simply referred to as "live parasites"), or saprophytic pathogens (also referred to as "dead parasites”) It is more preferable to be live parasitic pathogens (also simply referred to as "live parasites"), or saprophytic pathogens (also referred to as "dead parasites”) It is more preferable to be live parasit
  • Live parasitic fungi include various live parasitic phytopathogenic filamentous fungi [Colletotrichum higginsianum, Puccinia graminis, Erysiphe graminis, Ustilago maydis), rice blast fungi (Magnaporthe grisea, etc.)], various live parasitic plant pathogenic bacteria, various plant viruses, and the like.
  • bacteria of the genus Colletotrichum can be preferably exemplified as pathogens to be protected by the use of the resistance-inducing agents of the embodiments.
  • Dead parasites include Botrytis cinerea, Colletotrichum atramentarium, Colletotrichum lagenarium, Phytophthora infestans, and Gaeumannomyces graminis. , Erwinia carotovora, Diplocarpon rosae, Valsa ceratosperma, Cryphonectria parasitica, Claviceps purpurea, Alternaria alternata, Brown spot ( Mycosphaerella pinodes), Cochliobolus miyabeanus, Stemphylium lycopersici, Sclerotinia sclerotiorum, Monilinia sp., Passalora fulva, Cucumber vine (Fusarium oxysporum f.
  • Alternaria alternata of the genus Alternaria and Botrytis cinerea of the genus Botrytis can be exemplified as representative dead parasites.
  • pathogens to be protected by the use of the resistance-inducing agent of the embodiment include dead-parasitic fungi of the genus Alternaria, dead-parasites of Botrytis cinerea, Botrytis byssoidea, Botrytis squamosa, Botrytis allii, and the like.
  • dead-parasitic fungi of the genus Alternaria dead-parasites of Botrytis cinerea
  • Botrytis byssoidea Botrytis squamosa
  • Botrytis allii and the like.
  • the genus Botrytis can be preferably exemplified, and the genus Botrytis is more preferred.
  • Alternaria alternata of the genus Alternaria and Botrytis cinerea of the genus Botrytis can be exemplified as suitable targets for use, and Botrytis cinerea and cucumber Botrytis cinerea can be exemplified as particularly suitable targets for use.
  • Dead matter parasites also include saprophytic pathogens that are conditionally saprophytic due to the surrounding environment.
  • the organisms such as pests to be controlled by using the resistance inducer of the embodiment are not particularly limited.
  • the ISR system induces a protective response against "injuries" such as feeding damage by pests. Therefore, the resistance inducer of the embodiment can be applied as a control agent to a wide variety of organisms such as insect pests, such as plant-eating insects and mites.
  • Organisms such as pests to be controlled by the use of the resistance inducer of the embodiment include coleopteran pests such as callosobruchus chinensis, diamondback moth (Plutella xylostella), lepidopteran pests such as Pieris rapae. Diptera pests such as Musca domestica and Dacus cucurbitae, Nezara antennata Hemiptera pests, Frankliniella occidentalis and other thrips pests, Locusta migratoria etc.
  • Orthoptera pests cockroach pests such as Blattella germanica, acarina pests such as Dermatophagoides farinae, and various agricultural pests such as nematodes such as Meloidogyne incognita.
  • Forest tree pests include Coleoptera pests, Platypus quercivorus and other Platypus quercivorus pests, Bark beetle pests such as Tomicus piniperda, and Mochamus alternatus. and Mochamus pests to which M. saltuaris and the like belong can be exemplified.
  • the present invention provides a method for inducing resistance, comprising contacting a plant to be applied with a compound represented by the general formula (1) or a salt thereof.
  • the present invention provides, as one embodiment, a compound represented by the general formula (1) or a salt thereof for inducing plant resistance.
  • the present invention provides, as one embodiment, use of the compound represented by the general formula (1) or a salt thereof for inducing plant resistance.
  • the present invention provides, as one embodiment, use of the compound represented by the general formula (1) or a salt thereof for producing a resistance inducer.
  • a resistance-inducing agent can induce resistance in a plant to which it is applied by bringing an effective amount into contact with the plant.
  • the method of applying the resistance inducer the method of bringing an effective amount into contact with the plant may be the same as in the case of known inducers.
  • a method of mixing, a method of irrigating the soil, a method of applying or spraying a resistance inducer solution in which a resistance inducer is dissolved, a method of growing a plant in the resistance inducer solution, resistance to hydroponic solutions For example, a method of mixing a sex inducer can be exemplified.
  • a method of contacting plant roots with an effective amount of the resistance inducer is preferable, and examples include a treatment method of applying the resistance inducer to the soil for cultivating the plant or to the hydroponic solution for cultivating the plant, and irrigation treatment. is preferred.
  • the part of the plant to be treated or administered with the resistance inducer is not particularly limited.
  • all the leaves, stems and roots of the plant body may be sprayed, or only some leaves, some stems and some roots may be sprayed.
  • the secondary metabolites produced at the sprayed site spread to the required site of the plant body, and resistance can be acquired even at the non-sprayed site.
  • Resistance can also be acquired by infiltrating plants from the root system by soil treatment, immersion treatment, irrigation treatment, or the like.
  • the amount of resistance inducer used can be adjusted as appropriate according to the resistance inducer and the type of plant.
  • the amount of the active ingredient used per time is 1 to 20 kg/10a, 1 to 10 kg/10a, 1 to 1.3 kg. /10a and can be used once a year, or multiple times as needed, during the period between plant germination and harvest. When used more than once, it is preferable to use 2 to 6 times a year and 1 to 3 times a month.
  • the concentration of the compound represented by the general formula (1) or a salt thereof contained in the solution of the resistance inducer is , preferably 0.1 to 500 ⁇ M, preferably 1 to 500 ⁇ M, preferably 1 to 300 ⁇ M, more preferably 1 to 100 ⁇ M, more preferably 1 to 10 ⁇ M, more preferably 1 to 5 ⁇ M, and in another aspect 10 to 50 ⁇ M. preferable.
  • the amount of a solution of a resistance inducer with a concentration of 0.1 to 500 ⁇ M or 1 to 500 ⁇ M is 1 to 1000 ⁇ L per leaf, and the plant is germinated and harvested. , can be used once a year, or multiple times as needed. When used more than once, it is preferable to use 2 to 6 times a year and 1 to 3 times a month.
  • the concentration of is preferably 0.1 to 500 ⁇ M, preferably 1 to 500 ⁇ M, more preferably 1 to 300 ⁇ M, more preferably 1 to 100 ⁇ M, more preferably 1 to 10 ⁇ M, further preferably 1 to 5 ⁇ M. 10-50 ⁇ M is preferred.
  • the amount of the resistance inducer solution having a concentration of 0.1 to 500 ⁇ M or 1 to 500 ⁇ M is 1 to 1000 ⁇ L per plant body, and the period from germination to harvesting of the plant. Can be used moderately, once a year, or multiple times as needed. When used more than once, it is preferable to use 2 to 6 times a year and 1 to 3 times a month.
  • the timing of using the resistance inducer can be any time during plant sowing, transplanting, or fixed planting. In addition, it can be applied at any stage of growth such as seeds, germinations, juveniles and mature individuals. For example, it may be applied 1 to 3 times from 20 days after germination to 14 days before harvest.
  • the resistance inducers of the embodiments may be used in combination with other agricultural and horticultural agents.
  • the resistance inducer and other agricultural and horticultural agents may be used simultaneously or separately.
  • the resistance inducers of the embodiments may be used in combination with other JA resistance inducers such as bestatin, hexanoic acid, arachidonic acid, and N-acylamide.
  • the resistance inducers of the embodiments may be used in combination with other SAR resistance inducers such as probenazole and acibenzolar-S-methyl.
  • the resistance inducer may be brought into contact with the plant body after the pest outbreak or the onset of the plant disease.
  • the resistance inducer may be used preventively, and the plant body may be contacted with the resistance inducer before the outbreak of pests or the onset of plant diseases.
  • the resistance inducer of the embodiment is capable of inducing good resistance by treating the active ingredient at a low concentration compared to conventional JA resistance inducers.
  • the SA system, JA system and/or ET system involved in plant resistance induction can be activated.
  • the resistance inducer of the embodiment can be suitably used for the method of inducing plant resistance described in the above embodiments.
  • a biostimulant of an embodiment contains a compound represented by the following general formula (1) or a salt thereof as an active ingredient.
  • R 1 , R 2 and R 3 are each independently a linear or branched alkyl group having 1 to 4 carbon atoms, a hydroxyl group, a halogen atom, or a linear or branched chain having 2 to 4 carbon atoms represents an alkenyl group
  • R 4 represents a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, or a linear or branched alkenyl group having 2 to 4 carbon atoms
  • R 5 and R 6 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, a linear or branched alkenyl group having 2 to 4 carbon atoms, or represents a halogen atom.
  • n1 represents the number of R 1 and is an integer of 0 to 5, and when n1 is 2 or more, R 1 may be the same or different.
  • n2 represents the number of R 2 and is an integer of 0 to 5, and when n2 is 2 or more, R 2 may be the same or different.
  • n3 represents the number of R 3 and is an integer of 0 to 3. When n3 is 2 or more, R 3 may be the same or different.
  • biostimulant refers to a substance that, when applied to a plant, has the effect of improving the production and/or accumulation of secondary metabolites in the plant.
  • the compound represented by the general formula (1) or a salt thereof contributes to the activation of multiple plant hormone synthesis pathways. That is, according to the compound represented by the general formula (1) or a salt thereof, biosynthetic pathways are activated over a wide range, and synthesis of various secondary metabolites can be improved.
  • Secondary metabolites include alkaloids and terpenoids, and these secondary metabolites can be used as active ingredients in herbal medicines and herbal medicines.
  • biostimulant of the embodiment for example, by applying to raw material plants of herbal medicines or herbal medicines, it is possible to improve the production and / or accumulation of the active ingredient that is the secondary metabolite of interest.
  • raw material plants include, but are not limited to, plants such as licorice, ginseng, ginger, and cinnamon.
  • the method of use and dosage form of the biostimulant are the same as those described for the plant resistance inducer above, so a detailed description will be omitted.
  • biostimulants of the embodiments may be provided in dosage forms such as to be used in combination with other agricultural and horticultural agents.
  • the biostimulants of the embodiments and other known compounds having biostimulant effects may be provided in a dosage form such as a combination drug or a combination preparation.
  • biostimulants of embodiments may be used in combination with other agricultural and horticultural agents.
  • Biostimulants and other agricultural and horticultural agents may be used simultaneously or separately.
  • the biostimulants of the embodiments may be used in combination with other known compounds having biostimulant effects.
  • the biostimulants of the embodiments have the effect of improving the production and/or accumulation of secondary metabolites.
  • the expression of biostimulant effects in plants can be determined, for example, by the following indicators. Using the amount of secondary metabolites produced in the plant body as an index, comparing the plant treated with the biostimulant of the embodiment and the plant not treated, the biostimulant of the embodiment is treated The expression of the biostimulant effect can be judged when the amount of the secondary metabolite produced by the plant body is significantly increased in the plant obtained by the treatment.
  • the present invention provides a method for promoting the production of secondary metabolites, comprising contacting a plant with a biostimulant containing the compound represented by the general formula (1) or a salt thereof as an active ingredient.
  • a biostimulant containing the compound represented by the general formula (1) or a salt thereof as an active ingredient offer.
  • Such a method can be exemplified by the same method as described in the method of bringing the plant resistance inducer into contact with the plant, and thus the description thereof is omitted.
  • the present invention provides a method for producing a secondary metabolite, comprising contacting a plant to which the compound represented by the general formula (1) or a salt thereof is applied.
  • the present invention provides a method for improving the production of secondary metabolites, comprising contacting a plant to which the compound represented by the general formula (1) or a salt thereof is applied.
  • VSP1 Vegetable Storage Protein 1
  • the plasmid was introduced into Arabidopsis thaliana via Agrobacterium tumefaciens LBA4404 to obtain transformed Arabidopsis thaliana VSP1::Fluc harboring VSP1::Fluc. Seeds of this transformed Arabidopsis thaliana were sown in a multiwell plate and germinated in an aqueous luciferin solution.
  • DMSO dimethyl sulfoxide
  • a solid medium in which compound X was mixed with MS medium to a concentration of 50 ⁇ M, or a solid medium in which only DMSO was mixed in place of compound X with MS medium was prepared.
  • Time-lapse observation of VSP1 activity was performed in the same manner as above from 24 to 168 hours after replanting, with the time immediately after replanting set to 0 hours.
  • Botrytis is a dead parasite fungus.
  • the results are shown in Figure 5.
  • the graph shows the maximum lesion diameter 72 hours after inoculation. Only when compound X was treated by irrigation, a high inhibitory effect on Botrytis was observed.
  • Anthracnose is a living parasite.
  • the results are shown in Figure 6.
  • the graph shows the maximum lesion diameter 144 hours after inoculation.
  • Compound X exhibited an inhibitory effect similar to or superior to that of ASM, a representative resistance inducer, and was shown to exert an excellent effect in inhibiting the infection and proliferation of Bacillus anthracis.
  • treatment with compound X was carried out by replanting Arabidopsis thaliana in a solid medium in which compound X was mixed with MS medium in the same manner as above, and immediately after replanting was defined as 0 hours of treatment.
  • VSP1 showed an induction pattern in which the expression increased from 48 hours after compound X treatment, reached a peak at 96 hours, and then decreased in activity.
  • PR1 was highly expressed 144 hours after treatment.
  • compound X has such a JA-SA induction pattern, it is thought that it exerted an excellent control effect against both botrytis and anthracnose.
  • FIG. 9A The results are shown in Figures 9A-B.
  • the graph in FIG. 9A is for young seedlings, and the graph in FIG. 9B is for mature individuals.
  • PDF1. 2 was confirmed to be highly expressed 144 hours after compound X treatment. Therefore, it was suggested that compound X is activating the ET system in the late stage.
  • compound X activates not only the JA system but also the SA system and ET system, and is effective against both botrytis (dead parasite) and anthracnose (live parasite). exhibited a clear resistance to This indicates that compound X can induce resistance to a wide range of pathogens. Compound X was able to effectively induce resistance even when applied at low concentrations.
  • compound X is equal to or greater than that of ASM and PBZ, which are representative resistance inducers, and it has been shown to be extremely effective and useful as a resistance inducer.

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Abstract

La présente invention concerne un procédé permettant d'induire une résistance chez une plante, ledit procédé consistant à appliquer un agent inducteur de résistance chez une plante à la plante et ainsi qu'à activer la voie de signalisation de l'acide salicylique (voie SA) et des voies de signalisation de l'acide jasmonique et/ou de l'éthylène (voie JA et/ou voie ET), le principe actif de l'agent induisant la résistance chez une plante étant un composé de faible poids moléculaire et ce seul principe actif activant la voie de SA et les voies de JA et/ou de ET.
PCT/JP2022/011401 2021-03-19 2022-03-14 Procédé permettant d'induire une résistance chez une plante, agent induisant une résistance chez une plante et biostimulant WO2022196649A1 (fr)

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Citations (3)

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