WO2020054878A1 - Agent améliorant la tolérance au sel pour plantes - Google Patents

Agent améliorant la tolérance au sel pour plantes Download PDF

Info

Publication number
WO2020054878A1
WO2020054878A1 PCT/JP2019/036863 JP2019036863W WO2020054878A1 WO 2020054878 A1 WO2020054878 A1 WO 2020054878A1 JP 2019036863 W JP2019036863 W JP 2019036863W WO 2020054878 A1 WO2020054878 A1 WO 2020054878A1
Authority
WO
WIPO (PCT)
Prior art keywords
salt
plant
compound
salt tolerance
ring
Prior art date
Application number
PCT/JP2019/036863
Other languages
English (en)
Japanese (ja)
Inventor
一史 川端
世吾 小野
Original Assignee
積水化学工業株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 積水化学工業株式会社 filed Critical 積水化学工業株式会社
Priority to JP2020546245A priority Critical patent/JP7325429B2/ja
Publication of WO2020054878A1 publication Critical patent/WO2020054878A1/fr

Links

Images

Classifications

    • 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
    • A01H1/00—Processes for modifying genotypes ; Plants characterised by associated natural traits
    • A01H1/12—Processes for modifying agronomic input traits, e.g. crop yield
    • A01H1/122—Processes for modifying agronomic input traits, e.g. crop yield for stress resistance, e.g. heavy metal resistance
    • A01H1/1225—Processes for modifying agronomic input traits, e.g. crop yield for stress resistance, e.g. heavy metal resistance for drought, cold or salt resistance
    • 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
    • A01G7/00—Botany in general
    • 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
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • 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
    • 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

Definitions

  • the present invention relates to an agent for improving salt tolerance of a plant, which enables cultivation in a high salt concentration environment, and a method for improving the salt tolerance of a plant by treating the plant with the agent for improving salt tolerance. More specifically, the present invention provides a compound represented by the following formula (I):
  • Ring A represents a benzene ring, a naphthalene ring or a 6-membered nitrogen-containing aromatic heterocyclic ring, each of which may be further substituted;
  • X represents a single bond or NR (wherein, R represents a hydrogen atom or an optionally substituted phenyl group); and n represents 0 or 1. However, when X represents a single bond, n is 1.
  • a salt thereof, or a salt thereof, or a solvate thereof and a method for improving the salt tolerance of a plant by treating the plant with the salt tolerance improving agent.
  • a method for increasing the salt tolerance of a plant there is a method of introducing a gene involved in the salt tolerance mechanism using a genetic recombination technique. For example, there are halophytes that have acquired osmotic resistance by accumulating osmolyte (proline or betaine) in plant cells. It has been reported that the transgenic plant into which the gene for accumulating osmolyte has been introduced has acquired salt tolerance.
  • the intracellular sodium ion concentration in a plant is mainly determined by a non-selective cation channel (NSCC) that controls uptake into cells, and a cell membrane-type Na + that controls extracellular efflux.
  • NSCC non-selective cation channel
  • Patent Literature 1 discloses that in a transformed plant overexpressing the SOS1 gene identified from a salt-tolerant plant, Telungiella halophilia, excretion of sodium ions out of cells is promoted, Is reported to have improved.
  • Patent Literature 2 reports that a transformed plant overexpressing the SOS2 gene, which is a protein kinase constituting the SOS pathway, also has improved salt tolerance.
  • Patent Document 3 discloses that in a transformed plant in which the vacuole-type Na + / H + antiporter (HvNHX1) gene of barley (Hordeum vulgare) is overexpressed, uptake of sodium ions into vacuoles is promoted, and salt tolerance is improved. Is reported to have improved.
  • HvNHX1 vacuole-type Na + / H + antiporter
  • Non-Patent Document 2 discloses that in a transgenic plant in which the HKT gene of Arabidopsis thaliana is overexpressed, the accumulation of sodium ions in roots is increased, the salt concentration of shoots is suppressed, and the whole plant is reduced. It has been reported that salt tolerance has been improved. However, since the crops produced in this way are genetically modified crops, some countries may not be able to cultivate them at agricultural sites due to regulations.
  • the present invention provides a method for improving the salt tolerance of a plant so that cultivation can be performed in a high salt concentration environment without using a genetic recombination technique, and a plant that can be used in the method.
  • An object of the present invention is to provide a salt resistance improver.
  • Ring A represents a benzene ring, a naphthalene ring or a 6-membered nitrogen-containing aromatic heterocyclic ring, each of which may be further substituted;
  • X represents a single bond or NR (wherein, R represents a hydrogen atom or an optionally substituted phenyl group); and n represents 0 or 1. However, when X represents a single bond, n is 1.
  • R represents a hydrogen atom or an optionally substituted phenyl group
  • n represents 0 or 1.
  • n represents 0 or 1.
  • the compound represented by the formula (I) or a salt thereof, or a solvate thereof can improve or improve the salt tolerance of a plant, and have completed the present invention.
  • Ring A represents a benzene ring, a naphthalene ring or a 6-membered nitrogen-containing aromatic heterocyclic ring, each of which may be further substituted;
  • X represents a single bond or NR (wherein, R represents a hydrogen atom or an optionally substituted phenyl group); and n represents 0 or 1. However, when X represents a single bond, n is 1.
  • compound (I) also referred to as “compound (I)” or a salt thereof, or a solvate thereof, a plant salt tolerance improving agent.
  • the plant salt tolerance improving agent containing the compound (I) or a salt thereof or a solvate thereof according to the present invention can improve or improve the salt tolerance of a plant originally having low salt tolerance. Therefore, by treating the plant with the salt tolerance improving agent for the plant, the plant can be cultivated even in an environment where the concentration of sodium chloride is high. Further, according to the present invention, a plant having improved salt tolerance can be produced by treating a plant with the salt tolerance improving agent for the plant.
  • the plant can grow even in a high-concentration NaCl solution by adding a salt tolerance improver.
  • FIG. 1 is a view showing the growth situation after the transformed Arabidopsis thaliana (P35SP-AtPERK13) was treated with each compound of Examples 1 to 4 and then grown for 3 weeks in the presence of a NaCl solution (Example compound 1 was added).
  • Growth photograph in the case, growth photograph when the example compound 2 is added, growth photograph when the example compound 3 is added, growth photograph when the example compound 4 is added, and the case where no example compound is added as a control Growth photo).
  • FIG. 2 is a graph showing leaf weights after growing tomato seeds for 2 weeks in the presence of a NaCl solution after treating each of the tomato seeds with each of the compounds of Examples 1 to 4 and a photograph showing growth conditions (Example compounds as a control).
  • plant salt tolerance improver refers to a compound containing compound (I) or a salt thereof, or a solvate thereof, and improving or improving the salt tolerance of a plant, particularly a plant originally having a low salt tolerance. It is an agent to do. Therefore, the plant treated with the “plant salt tolerance improving agent” of the present invention can be cultivated even in an environment having a high sodium chloride concentration.
  • the “plant salt tolerance improver” may be composed of only the compound (I) or a salt thereof, or a solvate thereof, but may optionally contain other components.
  • the "plant salt tolerance improving agent" of the present invention may be prepared by formulating compound (I) or a salt thereof, or a solvate thereof together with a carrier (inert carrier). Specifically, compound (I) or a salt thereof, or a solvate thereof is mixed with a suitable inert carrier in an appropriate ratio together with an auxiliary, if necessary, and dissolved, suspended or mixed. , Impregnated, adsorbed, adhered, etc. and formulated into appropriate dosage forms, such as suspensions, milk suspensions, emulsions, solutions, wettable powders, wettable powders, granules, powders, tablets, jumbo, etc. It may be used after conversion.
  • the inert carrier that can be blended with the “plant salt tolerance improver” may be any of a solid and a liquid.
  • Solid inert carriers include, for example, plant powders (eg, soybean flour, cereal flour, wood flour, bark flour, saw flour, tobacco stem flour, walnut husk flour, bran, fibrous powder, etc.), crushed synthesis Synthetic polymers such as resins, clays (eg, kaolin, bentonite, acid clay), talcs (eg, talc, pyrophyllite, etc.), silicas (eg, diatomaceous earth, silica sand, mica, etc.), activated carbon, natural minerals (Eg, sulfur powder, pumice, attapulgite, zeolite, etc.), calcined diatomaceous earth, brick crushed material, fly ash, sand, plastic carrier (eg, polyethylene, polypropylene, polyvinylidene chloride, etc.), inorganic mineral powder (eg, carbonic acid) Calcium
  • liquid inert carrier examples include water, alcohols (eg, methanol, ethanol, isopropyl alcohol, butanol, ethylene glycol, etc.) and ketones (eg, acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, etc.).
  • alcohols eg, methanol, ethanol, isopropyl alcohol, butanol, ethylene glycol, etc.
  • ketones eg, acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, etc.
  • Ethers eg, ethyl ether, dioxane, cellosolve, dipropyl ether, tetrahydrofuran, etc.
  • aliphatic hydrocarbons eg, kerosene, mineral oil, etc.
  • aromatic hydrocarbons eg, benzene, toluene, xylene, sorbent
  • halogenated hydrocarbons eg, dichloroethane, chloroform, carbon tetrachloride, etc.
  • esters eg, ethyl acetate, diisopropyl phthalate, dibutyl phthalate, geo) Chirufutareto etc.
  • nitriles e.g., acetonitrile
  • dimethyl sulfoxide and the like, which can be used in the form of a single, or a mixture of two or more.
  • Examples of the adjuvants that can be added to the “plant salt tolerance improver” include the following. If necessary, they can be used alone or in combination of two or more.
  • a surfactant can be used as an auxiliary agent for emulsifying, dispersing, solubilizing, etc. the compound (I) or a salt thereof, or a solvate thereof.
  • the surfactant for example, polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene higher fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene sorbitan alkylate, polyoxyethylene sorbitan monolaurate, Examples include, but are not limited to, polyoxyethylene sorbitan monooleate, alkylaryl sulfonates, naphthalene sulfonic acid condensates, lignin sulfonates, higher alcohol sulfates, and the like.
  • starch methylcellulose, carboxymethylcellulose, gum arabic, polyvinyl alcohol, pine oil, bran oil, bentonite, lignin for dispersion stabilization, adhesion, binding and the like of compound (I) or a salt thereof or a solvate thereof.
  • Sulfonates and the like can be used as adjuvants.
  • waxes, stearate salts, alkyl phosphate esters and the like can be used as adjuvants.
  • an antifoaming agent for example, silicone oil or the like can be used as an auxiliary agent.
  • the "plant salt tolerance improving agent" of the present invention is used in combination with one or more substances having a biological (non-environmental) stress tolerance improving activity, a substance having an environmental stress tolerance improving activity, a plant growth regulating activity, etc. You can also.
  • Biological stress includes pests, pathogens and the like. Examples of the environmental stress include salt stress, drought stress, osmotic stress, water stress, high temperature stress, low temperature stress, strong light stress, metal stress and the like.
  • the substance having an activity of improving environmental stress resistance is not particularly limited, and a substance known in the art can be appropriately selected and added.
  • the substance having a biological stress tolerance improving activity is not particularly limited, and examples thereof include a substance having an elicitor activity.
  • the elicitor activity is an action that induces the synthesis of an antibacterial substance such as phytoalexin in a plant.
  • an antibacterial substance such as phytoalexin in a plant.
  • various substances unique to plants are known, and may be appropriately selected according to the target plant.
  • exogenous elicita such as chymotrypsin hydrolyzate of casein protein
  • endogenous elicita such as oligogalacturonic acid, hexose, uronic acid, pentose, deoxyhexose, etc.
  • sucrose ester, carboxymethyl cellulose, carrageenan, Fungal hypha decomposed products, seaweed extracts, and the like are preferable, and those that are water-soluble and can be stably supplied are preferable.
  • the substance having a plant growth regulating activity may be appropriately selected depending on the target plant.
  • auxin antagonist such as uniconazole, indolebutyric acid, 1-naphthylacetamide, parachloroform Auxin agents such as phenoxyacetic acid (4-CPA), cytokinins such as forchlorphenuron, gibberellins such as gibberellins, dwarfing agents such as daminogit, transpiration inhibitors such as paraffin, choline agents, etc.
  • Biologically-derived plant growth regulators such as chlorella extract agents, and ethylene agents such as ethephon agents.
  • the compounding ratio of the compound (I) or a salt thereof, or a solvate thereof to the whole plant salt tolerance enhancer is not particularly limited. However, it may be, for example, about 0.01 to about 90% by mass.
  • the target plant for improving the salt tolerance in the present invention is not particularly limited.
  • the PERK13 gene or its homolog gene which is originally known to play a part in the control mechanism of sodium ion concentration, is originally contained in genomic DNA.
  • the plant may be an angiosperm, an gymnosperm, a fern or a moss, a monocotyledon or a dicotyledon.
  • the plant is, for example, a plant of the family Poaceae such as rice, corn, sorghum, wheat, barley, rye, barley, millet; a plant of the family Solanaceae such as tomato, eggplant, paprika, pepper, potato, and tobacco.
  • a cruciferous plant such as Arabidopsis, oilseed rape, rape, Japanese radish, cabbage, purple cabbage, mekabetsu (petit ver), Chinese cabbage, chingensai, kale, watercress, komatsuna, broccoli, cauliflower, turnip, wasabi, mustard, etc .; Cucurbitaceous plants such as squash, pumpkin, melon, watermelon, etc .; Grapeaceous plants such as grape; Rutaceae plants such as lemon, orange, navel orange, grapefruit, mandarin, lime, sudachi, yuzu, shikuwasha, tankan; apple , Cherry, plum, peach, strawberry Rosaceae plants such as loquat, apricot, plum (plum), prunes, almonds, pears, pears, raspberries, blackberries, cassis, cranberries, blueberries; soybeans, kidney beans, peas, broad beans, soybeans, green beans, chickpeas, etc.
  • Leguminous plants such as lotus; lotus plants such as lotus; sesame plants such as sesame; spinach, beet, sugar beet, quinoa, hinyu, amaranthus, celosia etc .; date palm, oil palm, coconut palm Palmaceae plants, such as acai; Acai plants; Musaceae plants, such as banana, bamboo, and manila; Malvaceae plants, such as cotton and okra; Eucalyptus, etc .; Plants of Euphoraceae, etc .; Is mentioned.
  • “treating a plant with a salt tolerance enhancer” means that the salt tolerance enhancer (that is, the compound (I) or a salt thereof, or a solvate thereof) reaches a target plant. . Therefore, for example, an effective amount for inducing salt tolerance in the target plant may be applied to the target plant or the cultivation carrier of the target plant, as it is, or the salt-tolerant improver may be diluted with water or the like as appropriate. Specific examples include application methods such as direct application to a target plant, plant treatment, crop treatment, and soil admixture, and an application method in which a hydroponic solution in hydroponics is treated with a salt tolerance improver.
  • a method of applying the salt tolerance improver of the present invention to a cultivation carrier that is, an application method such as stock plant treatment, crop treatment, soil mixing, hydroponic solution treatment, etc.
  • a cultivation carrier that is, an application method such as stock plant treatment, crop treatment, soil mixing, hydroponic solution treatment, etc.
  • hydroponic liquid treatment in hydroponic cultivation is preferable.
  • the salt resistance improver according to the present invention can be used as a solution dissolved in water, a solvent, or the like.
  • the solution may further contain sodium chloride.
  • the salt tolerance improver according to the present invention can be applied to soil or a hydroponic solution. In order to increase the contact efficiency between the salt tolerance improver and the plant, it is preferable to directly contact at least a part of the plant.
  • the salt tolerance improver according to the present invention may be applied to plant seedlings or to plant roots. Particularly in hydroponic cultivation, when the salt tolerance enhancer is directly sprayed on the cultivation solution, the salt tolerance enhancer is diluted, and it is difficult to apply the salt tolerance enhancer to the plant by the water flow. It is preferred that the salt resistance improver be directly applied to at least a part of the root in order to make the root act.
  • the seedlings may be brought into contact with the seedlings planted in a hydroponic bed or soil, or may be planted after bringing the salt tolerance improver into contact with at least a part of the roots.
  • the contact time between the salt tolerance improving agent and the plant may be any time as long as the plant can be salified, and can be appropriately adjusted depending on the type and concentration of the salt resistant agent.
  • the lower limit is preferably 1 minute, 10 minutes, 30 minutes, 1 hour, 2 hours, 4 hours, 8 hours, 12 hours, or 24 hours or more.
  • the upper limit is preferably, for example, within 7 days, 5 days, 3 days, 24 hours, 12 hours, 8 hours, 4 hours, 2 hours, or 1 hour.
  • ⁇ ⁇ ⁇ Tomatoes in the early stage of growth are less resistant to environmental stress than grown tomatoes.
  • the processes of rooting and germination are very sensitive to salt concentration.
  • many tomatoes fail to acquire salt tolerance and die due to high salt stress due to high salt stress.
  • it is preferable that the tomato is grown in an environment with a low salt concentration at an early stage of the growth, and after a certain degree of growth, treatment with a salt tolerance improving agent is performed.
  • the term "to a certain extent” refers to a point in time when the seedling has been grown for at least one week, preferably two weeks, more preferably about three weeks after germination.
  • the ratio of tomatoes to which salt tolerance is imparted by the salt tolerance imparting treatment can be significantly increased, and seedlings that can be cultivated in a high salt concentration environment can be efficiently grown.
  • the switching timing is not particularly limited as long as it is within an arbitrary period after the salt resistance imparting, but it is desirable to switch immediately after the salt resistance imparting process.
  • the term “cultivation carrier” means a support for cultivating a plant, and may be any material capable of growing a plant. For example, it contains so-called various soils, seedling raising mats, water and the like.
  • solid cultivation carriers include sand, vermiculite, cotton, paper, diatomaceous earth, agar, gel-like substances, polymer substances, rock wool, glass wool, wood chips, bark, pumice stone, and the like.
  • the liquid cultivation carrier include, for example, various nutrients necessary for plant growth (for example, nitrogen, phosphorus, potassium, calcium, magnesium, sulfur, iron, manganese, copper, molybdenum, boron, aluminum, silicon, and the like).
  • aqueous carriers containing salts as salts can be mentioned as aqueous carriers containing salts as salts.
  • a solution obtained by adding insufficient salts such as sodium chloride to a commercially available liquid fertilizer A solution obtained by diluting a commercially available concentrated liquid fertilizer with seawater instead of water can be used.
  • a solution in which insufficient salts such as phosphorus are appropriately added to seawater can be used.
  • Such a liquid cultivation carrier preferably contains magnesium chloride in addition to sodium chloride, more preferably contains 0.5% by mass or less of magnesium chloride, and 0.1 to 0.5% by mass. More preferably, it contains magnesium chloride.
  • Hydroponic cultivation that can be suitably used in the method for improving or improving salt tolerance of the present invention can be performed by a general hydroponic cultivation method.
  • a general hydroponic cultivation method For example, it may be performed by a flooding type hydroponic method in which a relatively large amount of a cultivation solution is accumulated in a cultivation tank, or may be performed by a thin film hydroponic method in which a culture solution flows down little by little on a flat surface having a gentle slope. Good.
  • the amount of the salt-tolerant used depends on the compounding ratio of compound (I) or a salt thereof or a solvate thereof as an active ingredient, weather conditions, formulation, application time, application method, Depending on the application site, the target plant, etc., it is usually sufficient to appropriately select and apply the compound (I) or a salt thereof, or a solvate thereof from a range of about 0.01 g to about 10 g per are. Preferably, the range is from about 0.1 to about 5 g.
  • the concentration of the compound (I) or a salt thereof, or a solvate thereof is, for example, about 0.01 to about 2000 ⁇ M, preferably about 0.1 to about 2000 ⁇ M. It is about 1000 ⁇ M, more preferably about 1 to about 300 ⁇ M.
  • “improving or improving salt tolerance” means that the plant grows even in an environment having a salt concentration (sodium ion concentration) at which only 10 to 50% of a plant can grow without using a salt tolerance improving agent. It is preferable that the salt tolerance is improved or improved to the extent possible. When no salt tolerance enhancer is used, the plant can grow even under an environment having a sodium ion concentration that allows only 10 to 30% of the plant to grow. It is more preferable that the salt tolerance is improved or improved, and the salt tolerance is increased to such an extent that it can grow even in an environment having a sodium ion concentration such that only 10% or less of a plant can grow without using a salt tolerance enhancer. A state that can be improved or improved is more preferable.
  • the salt tolerance improving agent of the present invention it is possible to cultivate a plant by hydroponic cultivation using a cultivation solution having a high sodium ion concentration or soil cultivation using a soil having a high sodium ion concentration.
  • the hydroponic solution used in the method for improving the salt tolerance of a plant according to the present invention may be a fresh water containing no sodium chloride, a sodium chloride-containing solution, or the like, and may be switched according to the purpose.
  • the concentration when sodium chloride is contained may be 0.1% by mass or more, and can be appropriately adjusted according to the purpose of cultivation, the salt tolerance of the plant to be cultivated, and the like.
  • the cultivation solution used in the present invention preferably has a sodium chloride concentration of 0.5, 1, 1.5, 2, or 2.5% by mass or more, preferably 4, 3.5, 3, 2,.
  • the content is preferably 5 or 2% by mass or less.
  • the method for evaluating the salt tolerance of a plant in the present invention is not particularly limited, but can be performed, for example, by the following means. That is, a plant of interest is prepared by adding a compound (I) or a salt thereof, or a solvate thereof, in a medium or soil to which a salt is added at an appropriate concentration in the presence or absence of the compound (I) or a solvate thereof. By growing under the conditions of the growth temperature and the growth period of the state, and comparing the growth state and the greening state, it is possible to comprehensively evaluate salt tolerance.
  • 6-membered nitrogen-containing aromatic heterocycle refers to a 6-membered nitrogen-containing aromatic ring having 1 to 4 heteroatoms selected from nitrogen, sulfur and oxygen in addition to carbon. Which contains at least one or more nitrogen atoms as ring-constituting atoms.
  • the "6-membered nitrogen-containing aromatic heterocycle” include pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl and the like.
  • halogen atom refers to a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
  • alkyl means a linear or branched monovalent saturated hydrocarbon group.
  • C 1-6 alkyl means a linear or branched monovalent saturated hydrocarbon group having 1 to 6 carbon atoms.
  • Examples of the “C 1-6 alkyl” include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, 4-methylpentyl, hexyl and the like.
  • haloalkyl means a group in which one or more hydrogen atoms in the “alkyl” group have been substituted with halogen. Specifically, for example, trifluoromethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, , 2,3,3-tetrafluoropropyl, 3,3,3-trifluoropropyl, 4,4,4-trifluorobutyl, 5,5,5-trifluoropentyl, 6,6,6-trifluorohexyl And the like. Among them, “halo C 1-3 alkyl” is preferable.
  • C 1-6 alkoxy means a group in which the above “C 1-6 alkyl” group is bonded to an oxygen atom, that is, a linear or branched alkoxy group having 1 to 6 carbon atoms.
  • Examples of the “C 1-6 alkoxy” include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, isopentyloxy, neopentyloxy, hexyloxy and the like.
  • C 1-3 alkoxy is preferable.
  • C 3-8 cycloalkyl means a monovalent group derived from a saturated hydrocarbon ring having 3 to 8 carbon atoms. Further, the C 3-8 cycloalkyl may be crosslinked. Examples of the “C 3-6 cycloalkyl” include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bicyclo [1,1,1] pentane and the like. Among them, “C 3-6 cycloalkyl” is preferable.
  • acyl means a monovalent group formed by removing a hydroxyl group from a carboxy group of a carboxylic acid.
  • acyl preferably, for example, formyl, C 1-6 alkyl-carbonyl (eg, acetyl, propionyl, butyryl, isobutyryl, pentanoyl, hexanoyl, heptanoyl, etc.), halo C 1-6 alkyl-carbonyl (eg, , Trifluoroacetyl, etc.), C 3-8 cycloalkyl-carbonyl (eg, cyclopropylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, etc.), C 6-14 aryl-carbonyl (eg, benzoyl, etc.), C 6-14 aryl C 1-6 alkyl - carbonyl (e.g., benzylcarbonyl, etc.), C
  • C 6-14 aryl means an aromatic hydrocarbon group having 6 to 14 carbon atoms.
  • Examples of the “C 6-14 aryl” include phenyl, naphthyl (eg, 1-naphthyl, 2-naphthyl), acenaphthylenyl, azulenyl, anthryl, phenanthryl and the like.
  • C 6-10 aryl is preferable, and phenyl is particularly preferable.
  • C 1-6 alkylsulfanyl refers to a group in which the above “C 1-6 alkyl” group is bonded to a sulfur atom, that is, a linear or branched alkylsulfanyl group having 1 to 6 carbon atoms. means.
  • C 1-6 alkylsulfanyl includes, for example, methylsulfanyl, ethylsulfanyl, propylsulfanyl, isopropylsulfanyl, butylsulfanyl, isobutylsulfanyl, sec-butylsulfanyl, tert-butylsulfanyl, pentylsulfanyl, isopentylsulfanyl, neopentyl Pentylsulfanyl, 1-ethylpropylsulfanyl, hexylsulfanyl and the like can be mentioned. Among them, “C 1-3 alkylsulfanyl” is preferable.
  • C 1-6 alkylsulfinyl refers to a group in which the above “C 1-6 alkyl” group is bonded to a sulfinyl group, that is, a linear or branched alkylsulfinyl group having 1 to 6 carbon atoms. means.
  • C 1-6 alkylsulfinyl examples include, for example, methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl, tert-butylsulfinyl, pentylsulfinyl, isopentylsulfinyl, neopentyl Pentylsulfinyl, 1-ethylpropylsulfinyl, hexylsulfinyl and the like can be mentioned. Among them, “C 1-3 alkylsulfinyl” is preferable.
  • C 1-6 alkylsulfonyl refers to a group in which the above “C 1-6 alkyl” group is bonded to a sulfonyl group, that is, a linear or branched alkylsulfonyl group having 1 to 6 carbon atoms. means.
  • C 1-6 alkylsulfonyl examples include, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl, tert-butylsulfonyl, pentylsulfonyl, isopentylsulfonyl, neopentyl Pentylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl and the like can be mentioned. Among them, “C 1-3 alkylsulfonyl” is preferable.
  • “optionally substituted amino” includes, for example, C 1-6 alkyl, halo C 1-6 alkyl, C 3-8 cycloalkyl, C 6-14 aryl, C 6-14 aryl C 1-6 alkyl, formyl, C 1-6 alkyl-carbonyl, C 6-14 aryl-carbonyl, C 6-14 aryl C 1-6 alkyl-carbonyl, C 1-6 alkoxy-carbonyl, carbamoyl, mono- or Examples thereof include an amino group optionally having one or two substituents selected from di-C 1-6 alkyl-carbamoyl, C 1-6 alkylsulfonyl and C 6-14 arylsulfonyl.
  • amino which may be substituted, amino, mono- - or di -C 1-6 alkylamino (e.g., methylamino, dimethylamino, ethylamino, diethylamino, propylamino, dibutylamino), a mono - Or di-halo C 1-6 alkylamino (eg, trifluoromethylamino), mono- or di-C 3-8 cycloalkylamino (eg, cyclopropylamino, cyclohexylamino), mono- or di-C 6- 14 arylamino (eg, phenylamino), mono- or di-C 6-14 arylC 1-6 alkylamino (eg, benzylamino, dibenzylamino), formylamino, mono- or di-C 1-6 alkyl - carbonylamino (e.g., acetylamino, propionylamino), mono- - -
  • substituents in ring A or R means unsubstituted or 1-3 substituted.
  • each substituent may be the same or different.
  • substituents include a halogen atom, hydroxy, optionally substituted amino (eg, amino, methylamino, dimethylamino, trifluoromethylamino, acetylamino), carboxy, cyano, nitro, C 1-6 alkyl ( For example, methyl, ethyl, propyl), halo C 1-6 alkyl (for example, trifluoroalkyl), C 3-8 cycloalkyl (for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl), C 1-6 alkoxy (for example, Methoxy, ethoxy), sulfanyl, C 1-6 alkylsulfanyl (eg, methylsulfanyl), C
  • Ring A represents a benzene ring, a naphthalene ring or a 6-membered nitrogen-containing aromatic heterocycle, each of which may be further substituted.
  • Ring A is preferably a benzene ring, a naphthalene ring or a pyrimidine ring, each of which may be further substituted.
  • Examples of the “optionally substituted” substituent in ring A include the groups described above, and more preferably a halogen atom, hydroxy, C 1-6 alkyl (eg, methyl), halo C 1-6 Alkyl (eg, trifluoromethyl), or C 1-6 alkoxy (eg, methoxy).
  • X represents a single bond or NR (wherein, R represents a hydrogen atom or a phenyl group which may be substituted). X is preferably a single bond or NH.
  • R represents a hydrogen atom or a phenyl group which may be substituted
  • X is preferably a single bond or NH.
  • R represents a hydrogen atom or a phenyl group which may be substituted
  • X is preferably a single bond or NH.
  • R represents a hydrogen atom or a phenyl group which may be substituted
  • X is preferably a single bond or NH.
  • R represents a hydrogen atom or a phenyl group which may be substituted
  • X is preferably a single bond or NH.
  • R represents a hydrogen atom or a phenyl group which may be substituted
  • X is preferably a single bond or NH.
  • R represents a hydrogen atom or a phenyl group which may be substitute
  • n 0 or 1. However, when X represents a single bond, n is 1.
  • Suitable compounds (I) include the following compounds.
  • Ring A is a 6-membered nitrogen-containing aromatic heterocyclic ring which may be further substituted;
  • X is NH; and
  • n is 0; Compound (I).
  • Ring A is a pyrimidine ring which may be further substituted; X is NH; and n is 0; Compound (I).
  • Ring A is a benzene ring or a naphthalene ring, each of which may be further substituted; X is a single bond; and n is 1.
  • Compound (I) is a benzene ring or a naphthalene ring, each of which may be further substituted; X is a single bond; and n is 1.
  • Ring A is a naphthalene ring which may be further substituted; X is a single bond; and n is 1.
  • Compound (I) is a naphthalene ring which may be further substituted; X is a single bond; and n is 1.
  • Ring A is a benzene ring which may be further substituted;
  • X is NR (where R represents a phenyl group which may be substituted); and
  • n is 1.
  • compound (I) examples include, for example, naphazoline (Example 1), moxonidine (Example 2), phentolamine (Example 3), trazoline (Example 4), and the like described in the following Examples. And a compound selected from the group consisting of salts.
  • the compound (I) of the present invention can be produced by applying various known production methods utilizing characteristics based on the basic skeleton or the type of the substituent.
  • Known methods include, for example, “ORGANIC FUNCTIONAL GROUP PREPARATIONS”, 2nd edition, ACADEMIC PRESS, INC. 1989, “Comprehensive Organic Transformations”, VCH Publishers Inc. , 1989, and the like.
  • it is effective in production technology to protect the functional group with an appropriate protecting group at the stage of a raw material or an intermediate, or to replace the functional group with a group that can be easily converted to the functional group. It may be.
  • Examples of such a functional group include an amino group, a hydroxyl group, a carboxyl group, and the like.
  • W. Greene and P.M. G. FIG. Wuts, "Protective Groups in Organic Synthesis (3rd edition, 1999)" includes a protecting group, which may be appropriately selected and used according to these reaction conditions. According to such a method, a desired compound can be obtained by introducing the substituent and carrying out the reaction, and then removing the protective group or converting it to a desired group, if necessary.
  • ring A is as defined above, and P represents a protecting group such as an acyl group (eg, formyl, acetyl, propionyl, butyryl, etc.))
  • P represents a protecting group such as an acyl group (eg, formyl, acetyl, propionyl, butyryl, etc.)
  • Step 1 is a step of producing compound (3) by reacting compound (1) with compound (2) in the presence of phosphorus oxychloride (POCl 3 ).
  • This step can be carried out using an excess amount of phosphorus oxychloride as a reactant / solvent, and can also be carried out in the presence of phosphorus oxychloride in a solvent that does not affect the reaction.
  • the amount of phosphorus oxychloride to be used is generally 1.0 to 100 mol, preferably 2.0 to 50 mol, more preferably 5.0 to 50 mol, per 1 mol of compound (1).
  • the amount of compound (2) to be used is generally 1.0 to 10 mol, preferably 1.1 to 3 mol, more preferably 1.1 to 2 mol, per 1 mol of compound (1).
  • This reaction is preferably performed in an excessive amount of phosphorus oxychloride, but can be performed in a solvent that does not affect the reaction.
  • the reaction solvent for example, diethyl ether, tetrahydrofuran (hereinafter abbreviated as THF), 1,2-dimethoxyethane, dichloromethane, chloroform, toluene, a mixed solvent thereof, or the like can be used, and preferably, dichloromethane is used. It is.
  • the reaction temperature can usually be arbitrarily selected from 20 ° C to 106 ° C, and is preferably from 50 ° C to 100 ° C.
  • the reaction time is usually about 1 to 70 hours.
  • Step 2 This step is a step of producing a compound (I) by removing the protecting group P from the compound (3).
  • This step can be performed in a solvent that does not affect the reaction.
  • Conditions for deprotection of the protecting group P include, for example, T.I. W. Greene and P.M. G. FIG. Wuts, "Protective Groups in Organic Synthesis (3rd edition, 1999)" may be used by appropriately selecting the deprotection conditions.
  • (Production method B) (Production method of compound (I-3) and compound (I-4))
  • R 1 represents an alkyl group (eg, methyl, ethyl, etc.)
  • Step 3 is a step of producing a compound (5) by reacting the compound (4) with a cyanoacetate.
  • This step can be performed in the presence of a base and a metal catalyst in a solvent that does not affect the reaction.
  • the base used is not particularly limited, but is preferably potassium carbonate, sodium carbonate, cesium carbonate or sodium hydride.
  • the metal catalyst to be used include a monovalent copper catalyst and the like, and among them, copper iodide is preferable.
  • the amount of the cyanoacetate to be used is generally 1.0 to 10 mol, preferably 1.0 to 3.0 mol, per 1 mol of compound (4).
  • the amount of the base to be used is generally 1.0 to 10 mol, preferably 1.0 to 3.0 mol, per 1 mol of compound (4).
  • the amount of the metal catalyst to be used is generally 0.001 to 1.0 mol, preferably 0.01 to 0.5 mol, more preferably 0.05 to 0.2 mol, per 1 mol of compound (1). It is.
  • reaction can be carried out in a solvent that does not affect the reaction.
  • the reaction solvent is not particularly limited, but is preferably dimethyl sulfoxide, 1,4-dioxane or hexamethylphosphoric triamide.
  • the reaction temperature is usually from 70 ° C to 170 ° C, preferably from 90 ° C to 140 ° C.
  • the reaction time is usually about 0.5 to 12 hours.
  • Step 4 is a step of producing a compound (6) by a hydrolysis reaction of the compound (5) under acidic conditions or basic conditions, followed by a decarboxylation reaction. This step can also be carried out by heating in a mixed solvent of dimethyl sulfoxide and water in the presence of lithium chloride or sodium chloride.
  • the acid used is not particularly limited, but concentrated sulfuric acid is preferred.
  • the base used is not particularly limited, but potassium hydroxide or sodium hydroxide is preferable.
  • the reaction solvent is not particularly limited, but preferably, under acidic conditions, ethyl acetate and a 50% acetic acid aqueous solution are used. It is a mixed solvent, and is a mixed solvent of ethanol and water under basic conditions.
  • the reaction temperature is usually from 60 ° C to 100 ° C, preferably from 80 ° C to 90 ° C.
  • the reaction time is usually about 8 to 60 hours.
  • the amount of lithium chloride or sodium chloride used is as follows: 5) Usually 0.5 to 10 mol, preferably 1.0 to 5.0 mol, per 1 mol.
  • the reaction temperature is usually from 60 ° C to 180 ° C, preferably from 80 ° C to 160 ° C.
  • the reaction time is usually about 4 to 60 hours.
  • Step 5 is a step of producing a compound (I) by reacting the compound (6) with ethylenediamine under heating conditions.
  • This step can be performed in the presence of a catalytic amount of thioacetamide in ethylenediamine or in a solvent that does not affect the reaction.
  • the amount of thioacetamide to be used is generally 0.01 to 0.2 mol, preferably 0.01 to 0.1 mol, per 1 mol of compound (6).
  • the amount of ethylenediamine to be used is generally 1.0 to 100 mol, preferably 1.2 to 20 mol, per 1 mol of compound (6).
  • This reaction is preferably carried out using an excess amount of ethylenediamine as a reaction solvent, but can also be carried out in a solvent that does not affect the reaction.
  • a reaction solvent is ethanol.
  • the reaction temperature is generally from 60 ° C to 170 ° C, preferably from 70 ° C to 140 ° C.
  • the reaction time is usually about 0.5 to 24 hours.
  • rings A and R are as defined above, and Y is a halogen atom (fluorine atom, chlorine atom, bromine atom, iodine atom) or an alkylsulfonyloxy group optionally substituted with a halogen atom (for example, leaving groups such as methanesulfonyloxy, ethanesulfonyloxy, propanesulfonyloxy, trifluoromethanesulfonyloxy, and arylsulfonyloxy groups (for example, phenylsulfonyloxy, tolylsulfonyloxy, etc.) are shown.)
  • Step 6 In this step, after reacting compound (7) and compound (8) under heating conditions, water and an organic solvent are added to stop the reaction, the aqueous layer is cooled, and the compound is crystallized.
  • the amount of compound (8) to be used is generally 1.0 to 2 mol, preferably 1.0 to 1.2 mol, per 1 mol of compound (7).
  • This reaction is preferably performed without a solvent.
  • the reaction temperature is usually 100 ° C to 180 ° C, preferably 150 ° C, and the crystallization temperature is usually -10 ° C to 10 ° C, preferably -10 ° C to 0 ° C. is there.
  • the reaction time is usually about 4 to 24 hours.
  • the salt of compound (I) can be converted into a basic salt or an acidic salt by reacting with a base or an acid according to a known method.
  • the solvate of compound (I) or a salt thereof can be produced by performing crystallization or the like after mixing with a solvent according to a known method.
  • the salt of compound (I) indicates a basic salt or an acidic salt of compound (I).
  • the “basic salt” of the compound (I) of the present invention includes, for example, alkali metal salts such as sodium salt, potassium salt and lithium salt; alkaline earth metal salts such as magnesium salt and calcium salt; N-methyl Organic base salts such as morpholine salt, triethylamine salt, tributylamine salt, diisopropylethylamine salt, dicyclohexylamine salt, N-methylpiperidine salt, pyridine salt, 4-pyrrolidinopyridine salt, picoline salt; glycine salt, lysine salt, arginine Examples include salts, amino acids such as ornithine, glutamate and aspartate, and are preferably alkali metal salts (eg, sodium salt).
  • acid salt of the compound (I) of the present invention
  • hydrohalides such as hydrofluoride, hydrochloride, hydrobromide, hydroiodide, nitrate, perchlorate
  • Inorganic salts such as acid salts, sulfates and phosphates
  • alkanesulfonates such as methanesulfonate, trifluoromethanesulfonate and ethanesulfonate, benzenesulfonate and p-toluenesulfonate.
  • Organic salts such as arylsulfonate, acetate, malate, fumarate, succinate, citrate, ascorbate, tartrate, oxalate and maleate; glycine salts;
  • Examples include amino acid salts such as lysine salt, arginine salt, ornithine salt, glutamate, and aspartate, and are preferably hydrohalides (eg, hydrochloride).
  • the solvate of the compound (I) or a salt thereof is a compound in which a solvent molecule is coordinated with the compound (I) or a salt thereof.
  • the compound (I) of the present invention or a salt thereof or a solvate thereof produced by the above-mentioned method can be obtained by a known method such as extraction, precipitation, distillation, chromatography, fractional recrystallization, recrystallization and the like. Can be separated and purified. Further, the chemical structure of the compound (I) of the present invention or a salt thereof, or a solvate thereof is represented by 1 H-NMR, 13 C-NMR, HPLC, high-resolution liquid chromatography / mass spectrometry (LC-MS / MS). ) Can be identified using conventional instrumental analysis methods.
  • Examples of the compound (I) or a salt thereof used in Test Example 1 below which are commercially available products, include nafazoline hydrochloride (Example 1; manufactured by Tokyo Chemical Industry Co., Ltd.) and moxonidine (Example 2). Sigma-Aldrich), phentolamine hydrochloride (Example 3; Fujifilm Wako Pure Chemical Industries, Ltd.), and tolazoline hydrochloride (Example 4; Fujifilm Wako Pure Chemical Industries, Ltd.) were used as they were.
  • Test Example 1 transformed Arabidopsis thaliana (P35SP-AtPERK13) into which the PERK13 gene had been introduced was used as a plant to which the test compound was administered.
  • the PERK13 gene is known to be involved in the control of sodium ion influx into plants, and it is possible to evaluate the salt tolerance of a test compound in more detail by using a plant into which the gene has been introduced. Become. Here, it is suggested that compounds having salt tolerance are involved in PERK13.
  • the translated region of the Arabidopsis PERK13 gene was cloned and introduced into pBigs, an overexpression vector (pBigs: AtPERK13). This was introduced into Agrobacterium strain GV3101. (Selection of transformants) Arabidopsis thaliana grown for 6 weeks was infected with Agrobacterium by the floral dip method. Thereafter, the infected plants were cultivated for 8 weeks and the seeds were harvested. The obtained seeds were sown on an MS medium (Murashige and Skoog medium, Sigma-Aldrich) containing a selection marker, kanamycin (manufactured by Fuji Film Wako Pure Chemical Industries, Ltd.), and a transformant was selected.
  • MS medium Merashige and Skoog medium, Sigma-Aldrich
  • NaCl solution aqueous sodium chloride solution (hereinafter referred to as NaCl solution) 200 ⁇ L (final concentration: 200 mM) of a 1 M NaCl solution was added to the wells cultured for 2 days after the addition of each of the compounds of Examples 1 to 4 and DMSO (control sample). After the addition, the petri dish was wrapped with parafilm after addition in order to suppress the volatilization of water due to long-term culture, and cultured for 16 hours in the light period at about 22 ° C. for about 2 to 3 weeks.
  • NaCl solution aqueous sodium chloride solution
  • a pot containing a sucrose-containing MS medium (agar medium obtained by adding 0.5% (w / v) sucrose to an MS medium) was prepared in a container containing sterilized water. The bottom surface was immersed in sterile water, but the top surface was not soaked. The above seeds were sown on these pots and grown in an incubator at 25 ° C. for 16 hours in the light period and 8 hours in the dark period for 10 to 14 days.
  • Test Example 2 Three days after the addition of each of the compounds of Examples 1 to 4 and DMSO (control sample), sterilized water soaked in the bottom of the pot was sterilized so that the final concentration of sodium chloride was 1.5% by mass. A 5M aqueous sodium chloride solution and liquid fertilizer (Hyponica A and B solutions were diluted 500-fold) were added. One week later, a sterilized 5M aqueous sodium chloride solution was added so that the final concentration of sodium chloride was 3.0% by mass. Thereafter, the pot was cultured for 14 days. The weight of the cultivated tomato leaves was measured, and a significant difference test was performed. In addition, the results of Test Example 2 were evaluated as growth evaluation values obtained by integrating the degree of growth and greening, based on the five-level evaluation criteria of Test Example 1.
  • FIG. 2 and Table 3 show the results. According to the graph of FIG. 2, it was confirmed that the weight of the leaves of the compound-added groups of Examples 1 to 4 was significantly higher than that of the control sample. Further, according to the photograph of FIG. 2, good growth and greening were observed in all of the compound-added groups of Examples 1 to 4, but in the control, the leaves were withered and the growth was stopped. In addition, according to Table 3, it was confirmed that the growth evaluation values of the compound-added groups of Examples 1 to 4 significantly increased as compared with the control samples. From these results, it was confirmed that the addition of compound (I) of the present invention or a salt thereof significantly improved the salt tolerance of tomato.
  • a pot containing a sucrose-containing MS medium (agar medium obtained by adding 0.5% (w / v) sucrose to an MS medium) was prepared in a container containing sterilized water. The bottom surface was immersed in sterile water, but the top surface was not soaked. The above seeds were sown on these pots and grown in an incubator at 25 ° C. for 16 hours in the light period and 8 hours in the dark period for 10 to 14 days.
  • the amount of chlorophyll was measured by a chlorophyll meter (SPAD-502plus, manufactured by Konica Minolta).
  • the results of Test Example 3 were evaluated as growth evaluation values obtained by integrating the degree of growth and greening, based on the five-level evaluation criteria of Test Example 1.
  • Table 4 shows the results. According to Table 4, the ratio of the number of surviving leaves (survival rate) and the growth evaluation value of the compound-added groups of Examples 1 to 4 can be significantly increased as compared with the control sample. confirmed.
  • the plant salt tolerance improving agent containing the compound (I) or a salt thereof or a solvate thereof according to the present invention can improve or improve the salt tolerance of a plant originally having low salt tolerance.
  • ADVANTAGE OF THE INVENTION According to this invention, the salt tolerance improving agent which can cultivate a plant even under the environment where sodium chloride concentration is high can be provided. Further, according to the present invention, a plant having improved salt tolerance can be produced by treating a plant with the salt tolerance improving agent for the plant.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Environmental Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Botany (AREA)
  • Plant Pathology (AREA)
  • Zoology (AREA)
  • Pest Control & Pesticides (AREA)
  • Developmental Biology & Embryology (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Genetics & Genomics (AREA)
  • Wood Science & Technology (AREA)
  • Ecology (AREA)
  • Biodiversity & Conservation Biology (AREA)
  • Forests & Forestry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Breeding Of Plants And Reproduction By Means Of Culturing (AREA)

Abstract

L'objectif de la présente invention est de fournir un agent améliorant la tolérance au sel pour des plantes, pour permettre la culture dans un environnement à concentration en sel élevée. La présente invention concerne un agent améliorant la tolérance au sel pour des plantes qui contient un composé représenté par la formule (I) [la signification des éléments présents dans la formule sont indiqués dans la description] ou un sel de celui-ci, ou un solvate du composé ou du sel.
PCT/JP2019/036863 2018-09-14 2019-09-12 Agent améliorant la tolérance au sel pour plantes WO2020054878A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2020546245A JP7325429B2 (ja) 2018-09-14 2019-09-12 植物の耐塩性向上剤

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2018-172179 2018-09-14
JP2018172179 2018-09-14

Publications (1)

Publication Number Publication Date
WO2020054878A1 true WO2020054878A1 (fr) 2020-03-19

Family

ID=69776555

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2019/036863 WO2020054878A1 (fr) 2018-09-14 2019-09-12 Agent améliorant la tolérance au sel pour plantes

Country Status (2)

Country Link
JP (1) JP7325429B2 (fr)
WO (1) WO2020054878A1 (fr)

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS51106739A (en) * 1975-03-12 1976-09-21 Takeda Chemical Industries Ltd Satsuchu satsudanizai
WO2006059782A1 (fr) * 2004-11-30 2006-06-08 Riken Préparation visant à renforcer la tolérance des plantes face au stress environnemental
JP2008540441A (ja) * 2005-05-03 2008-11-20 バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト 殺虫性の置換されたアミノアルキル複素環式及びヘテロアリール誘導体
CN104388538A (zh) * 2014-11-18 2015-03-04 中国人民解放军第三军医大学 一种组蛋白去乙酰化酶抑制剂的筛选方法
JP2016069380A (ja) * 2014-09-29 2016-05-09 国立研究開発法人理化学研究所 植物の耐塩性向上剤
JP2017128564A (ja) * 2016-01-18 2017-07-27 国立研究開発法人理化学研究所 植物の耐塩性向上剤
JP2018052893A (ja) * 2016-09-30 2018-04-05 国立研究開発法人理化学研究所 植物の耐塩性向上剤
WO2018147440A1 (fr) * 2017-02-10 2018-08-16 株式会社 メニコン Agent d'induction de résistance végétale à un stress de pression osmotique, et procédé d'atténuation de stress de sécheresse

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS51106739A (en) * 1975-03-12 1976-09-21 Takeda Chemical Industries Ltd Satsuchu satsudanizai
WO2006059782A1 (fr) * 2004-11-30 2006-06-08 Riken Préparation visant à renforcer la tolérance des plantes face au stress environnemental
JP2008540441A (ja) * 2005-05-03 2008-11-20 バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト 殺虫性の置換されたアミノアルキル複素環式及びヘテロアリール誘導体
JP2016069380A (ja) * 2014-09-29 2016-05-09 国立研究開発法人理化学研究所 植物の耐塩性向上剤
CN104388538A (zh) * 2014-11-18 2015-03-04 中国人民解放军第三军医大学 一种组蛋白去乙酰化酶抑制剂的筛选方法
JP2017128564A (ja) * 2016-01-18 2017-07-27 国立研究開発法人理化学研究所 植物の耐塩性向上剤
JP2018052893A (ja) * 2016-09-30 2018-04-05 国立研究開発法人理化学研究所 植物の耐塩性向上剤
WO2018147440A1 (fr) * 2017-02-10 2018-08-16 株式会社 メニコン Agent d'induction de résistance végétale à un stress de pression osmotique, et procédé d'atténuation de stress de sécheresse

Also Published As

Publication number Publication date
JP7325429B2 (ja) 2023-08-14
JPWO2020054878A1 (ja) 2021-09-16

Similar Documents

Publication Publication Date Title
JP2013531688A (ja) ２，５−ジケトピペラジン誘導体を活性成分として含む農業用薬剤
UA127503C2 (uk) Оксадіазоли, призначені для використання у контролі фітопатогенних грибів
WO2009095098A2 (fr) Utilisation de benzothiadiazoles
CN106749080B (zh) 高抗逆性的植物生长调节剂及其制法和用途
KR20200131841A (ko) 식물 생장 조절제 화합물
US5211738A (en) Adenine derivatives and their use as a plant growth regulator
KR20180038463A (ko) 식물 생장 조절제 화합물
JP5915982B2 (ja) イミダゾール誘導体
CN109956904B (zh) 吡唑酰胺类化合物及其应用和杀菌剂
WO2020054878A1 (fr) Agent améliorant la tolérance au sel pour plantes
CN108059613B (zh) 一种吡唑酰胺类化合物及应用
JP6842082B2 (ja) 植物成長調整剤
CN106749044B (zh) 增强植物抗逆性的aba类似物
AU595269B2 (en) Plant growth promotion
JP5366474B2 (ja) Ｄ−アロースを有効成分とする植物のジベレリンシグナル経路抑制剤およびその利用
JP6902748B2 (ja) 植物成長調整剤
WO2018008717A1 (fr) Régulateur de croissance des plantes
JP7325124B2 (ja) ジャスモン酸内生促進剤及びジャスモン酸内生促進方法
JP5205924B2 (ja) 細胞が有する植物由来のサイトカイニン受容体からの細胞内信号伝達を阻害する活性を有する薬剤
RU2683535C1 (ru) Способ повышения урожайности томатов
JP5082474B2 (ja) 新規なキナゾリン誘導体
JPS63303973A (ja) トリアゾール化合物、該化合物の製法及び該化合物を含有する植物生長調整剤並びに該化合物を用いた植物生長調整法
US4718936A (en) 6-(3-thienylmethylamino)-purine, its preparation and its use
KR0146504B1 (ko) 아졸아미드 유도체
WO2019026575A1 (fr) Régulateur de période de floraison, composition agrochimique, et procédé pour réguler la période de floraison d'une plante

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 19861125

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2020546245

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 19861125

Country of ref document: EP

Kind code of ref document: A1