Classifications

• • 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
  • A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
  • A01G7/00—Botany in general
  • A01G7/06—Treatment of growing trees or plants, e.g. for preventing decay of wood, for tingeing flowers or wood, for prolonging the life of plants
• • 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

Definitions

• the present invention relates to an agent for improving environmental stress resistance in plants and a method for improving environmental stress resistance.
• ergothioneine is known to be a compound that can affect plant growth.
• Patent Document 1 discloses a fertilizer containing ergothioneine and a culture of a microorganism capable of biosynthesizing ergothioneine.
• Patent Document 2 reports that applying ergothioneine alone to plants promotes plant growth and increases yields.
• Patent Document 3 reports that nitrogenase activity is improved by applying a microbial extract containing ergothioneine as fertilizer.
• Patent Documents 4 and 5 report that applying glycine betaine to plants controls plant stress and related conditions and promotes plant growth.
• Patent Documents 1, 2, and 3 do not state clearly about the effect of improving the environmental stress resistance of plants.
• Patent Documents 4 and 5 also state 2-mercaptohistidine betaine (ergothioneine) in addition to glycine betaine, but there are no examples for ergothioneine, and its effects have not been confirmed.
• one aspect of the present invention aims to provide an environmental stress tolerance enhancer and a method for improving environmental stress tolerance that can effectively improve the environmental stress tolerance of plants.
• one embodiment of the present invention provides an agent for improving environmental stress tolerance for plants, comprising, as an active ingredient, a compound represented by the following formula (I) or a tautomer thereof, or an agriculturally acceptable salt thereof:
• R 1 and R 2 independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms
• R 3 to R 5 independently represent an alkyl group having 1 to 4 carbon atoms
• a method for improving environmental stress resistance in a plant includes treating the plant with the above-mentioned environmental stress resistance improving agent.
• an environmental stress tolerance enhancer and a method for improving environmental stress tolerance that can effectively improve the environmental stress tolerance of plants.
• the environmental stress tolerance improving agent contains, as an active ingredient, a compound represented by the following formula (I) (hereinafter simply referred to as “compound (I)”) or a tautomer, or an agriculturally acceptable salt thereof.
• compound (I) a compound represented by the following formula (I) (hereinafter simply referred to as “compound (I)”) or a tautomer, or an agriculturally acceptable salt thereof.
• R1 and R2 independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
• R3 to R5 independently represent an alkyl group having 1 to 4 carbon atoms.
• the alkyl group may be linear or branched, i.e., methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl.
• At least one of R1 and R2 is preferably a hydrogen atom, and more preferably both are hydrogen atoms.
• R1 and R2 are alkyl groups, they are preferably methyl, ethyl, or propyl, more preferably methyl or ethyl, and even more preferably methyl.
• R3 to R5 are preferably each independently a methyl group, an ethyl group, or a propyl group, more preferably a methyl group or an ethyl group, and even more preferably a methyl group. It is preferable that at least one of R3 to R5 is a methyl group, more preferably at least two of R3 to R5 are methyl groups, and even more preferably all of R3 to R5 are methyl groups.
• the tautomer refers to a tautomer of compound (I).
• Compound (I) has a tautomer when at least one of R 1 and R 2 is a hydrogen atom. More specifically, when R 2 is a hydrogen atom in formula (I), a compound represented by the following formula (II) (hereinafter simply referred to as “compound (II)”) may exist as a tautomer.
• R 1 is a hydrogen atom in formula (I)
• a compound represented by the following formula (III) hereinafter simply referred to as “compound (III)
• compound (II) and compound (III) are collectively referred to simply as "tautomers”.
• R 1 to R 5 are the same as R 1 to R 5 in formula (I).
• a preferred compound as compound (I) or its tautomer is specifically ergothioneine, and more preferably L-(+)-ergothioneine.
• Ergothioneine is also known to be produced by bacteria and fungi. Examples of production methods using such microorganisms include the methods described in Patent Documents JP-A-2012-105618, JP-A-2014-223051, WO2016/104437, WO2016/121285, WO2015/168112, and WO2017/150304.
• ergothioneine cultures containing ergothioneine obtained from these microorganisms may be used as they are, or ergothioneine may be concentrated or purified before use.
• Agriculturally acceptable generally means something that is safe, non-toxic, and not biologically or otherwise undesirable, and is acceptable for use as a pesticide, particularly for use in improving plants' resistance to environmental stresses.
• Agriculturally acceptable salt of compound (I) or its tautomer means an agriculturally acceptable salt as defined above that provides the action and effect of compound (I) or its tautomer.
• Examples of such salts include hydrates, solvates, acid addition salts, salts formed when an acidic proton present in compound (I) or its tautomer is replaced by a metal ion, and salts formed when the acidic proton is coordinated with an organic base or an inorganic base.
• Acid addition salts may be formed with inorganic or organic acids.
• Inorganic acids include hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, and phosphoric acid.
• Organic acids include acetic acid, benzenesulfonic acid, benzoic acid, camphorsulfonic acid, citric acid, ethanesulfonic acid, fumaric acid, glucoheptonic acid, gluconic acid, glutamic acid, glycolic acid, hydroxynaphthoic acid, 2-hydroxyethanesulfonic acid, lactic acid, maleic acid, malic acid, mandelic acid, methanesulfonic acid, muconic acid, 2-naphthalenesulfonic acid, propionic acid, salicylic acid, succinic acid, dibenzoyl-L-tartaric acid, tartaric acid, p-toluenesulfonic acid, trimethylacetic acid, and trifluoroacetic acid.
• Metal ions that can replace the acidic protons present in compound (I) or its tautomers include, for example, alkali metal ions, alkaline earth metal ions, and aluminum ions.
• Organic bases that can coordinate with the acidic protons present in compound (I) or its tautomers include, for example, diethanolamine, ethanolamine, N-methylglucamine, triethanolamine, and tromethamine.
• Inorganic bases include, for example, aluminum hydroxide, calcium hydroxide, potassium hydroxide, sodium carbonate, and sodium hydroxide.
• the environmental stress resistance improving agent according to this embodiment contains compound (I) or a tautomer thereof, or an agriculturally acceptable salt thereof as an active ingredient, and thus plants treated with the agent have improved resistance to environmental stress compared to plants not treated with the agent.
• enhanced resistance to environmental stress refers to the suppression of physiological disorders caused by environmental stress in plants treated with the environmental stress resistance enhancer of this embodiment, compared to plants not treated with the agent.
• an “indicator of suppression of physiological disorders caused by environmental stress” is the environmental stress suppression rate.
• the “environmental stress suppression rate” is the rate at which physiological disorders occurring in a plant after growing for a specified period of time in an environment where environmental stress is applied are suppressed by treating the plant with the environmental stress resistance enhancer according to the embodiment, compared to a plant that is not treated with the agent. For example, if the physiological disorders occurring in a plant not treated with the environmental stress resistance enhancer in an environment where environmental stress is applied are taken as 100%, and the physiological disorders occurring in a plant treated with the agent are taken as 20%, then the environmental stress suppression rate is 80%. With regard to the “environmental stress suppression rate”, “resistance to environmental stress is improved” means that the environmental stress suppression rate is high.
• “Indicators of physiological disorders” include, for example, death, chlorosis (whitening or yellowing), necrosis, and wilting in plants, and death, chlorosis (whitening or yellowing), necrosis, and wilting in leaves, but are not limited to these. Examples include decreases in plant height, root length, number of flowers, number of fruits, and seed yield.
• plant mortality rate is the ratio of the number of plants that have died after growing the plants under specified conditions for a specified period of time to the number of plants tested; for example, if 100 plants are grown under specified conditions for a specified period of time and 80 plants have died, the mortality rate is 80%.
• plant mortality rate "improved resistance to environmental stress” means that plants treated with the environmental stress tolerance improving agent of this embodiment have a lower mortality rate in an environment where environmental stress is applied, compared to plants that have not been treated with the agent.
• leaf mortality is the ratio of the number of leaves that have died after a test plant has been grown for a specified period under specified conditions to the number of leaves of the plant. For example, if a plant has been grown for a specified period under specified conditions and 8 of 10 leaves have died, the leaf mortality is 80%.
• improved resistance to environmental stress means that plants treated with the environmental stress resistance improving agent of this embodiment have a lower mortality rate in an environment where environmental stress is applied, compared to plants that have not been treated with the agent.
• an example of the "leaf bleaching rate” is the ratio of the number of bleached leaves after a test plant is grown for a specified period under specified conditions to the number of leaves of the plant. For example, if a plant grows for a specified period under specified conditions and 8 of 10 leaves are bleached, the leaf bleaching rate is 80%.
• "improved resistance to environmental stress” means that a plant treated with the environmental stress resistance improving agent according to this embodiment has a lower bleaching rate in an environment where environmental stress is applied, compared to a plant not treated with the agent.
• leaf necrosis rate is the ratio of necrotic leaf area of a test plant after the plant is grown for a specified period under specified conditions to the total leaf area of the plant, and as an example, when 80 cm2 of a total leaf area of 100 cm2 is necrotic after the plant is grown for a specified period under specified conditions, the leaf necrosis rate is 80%.
• “leaf necrosis rate” “resistance to environmental stress is improved” means that a plant treated with the environmental stress resistance improver according to this embodiment has a lower necrosis rate under an environment loaded with environmental stress than a plant not treated with the agent.
• leaf wilting rate is the ratio of the number of leaves that have wilted after a test plant has been grown for a specified period under specified conditions to the number of leaves on that plant. For example, if a plant has been grown for a specified period under specified conditions and 8 of 10 leaves have wilted, the leaf wilting rate is 80%.
• improved resistance to environmental stress means that plants treated with the environmental stress resistance improving agent of this embodiment have a lower wilting rate in an environment where environmental stress is applied, compared to plants that have not been treated with the agent.
• “resistance to environmental stress is improved” means that a plant treated with the environmental stress resistance improver of this embodiment has a higher plant height under an environment where environmental stress is applied, compared to a plant not treated with the agent.
• root length means that a plant treated with the environmental stress resistance improver of this embodiment has a longer root length under an environment where environmental stress is applied, compared to a plant not treated with the agent.
• number of flowers means that a plant treated with the environmental stress resistance improver of this embodiment has a larger number of flowers under an environment where environmental stress is applied, compared to a plant not treated with the agent.
• “resistance to environmental stress is improved” means that a plant treated with the environmental stress resistance improver of this embodiment has a larger number of fruits under an environment where environmental stress is applied, compared to a plant not treated with the agent.
• “resistance to environmental stress is improved” means that a plant treated with the environmental stress resistance improving agent according to this embodiment has a higher seed yield under an environment loaded with environmental stress than a plant not treated with the agent.
• a preferred embodiment is an environmental stress resistance enhancer for suppressing withering, chlorosis (whitening or yellowing), necrosis, or wilting of plants or leaves caused by environmental stress.
• environmental stress refers to environmental factors that plants may be subjected to that inhibit normal growth. Examples include high temperature stress, low temperature stress, freezing stress, salt stress, excess nutrient stress, drought stress, excess water stress, ultraviolet stress, low light stress, and high light stress.
• Normal growth here refers to the level of growth when these factors are not present and when not treated with the environmental stress resistance improving agent of this embodiment. Furthermore, normal growth being difficult not only includes cases where growth is difficult, but also cases where the level of growth is poorer than normal growth.
• the environmental stress resistance improver according to this embodiment preferably contains compound (I) or an agriculturally acceptable salt thereof as an active ingredient.
• the environmental stress resistance improver according to this embodiment may contain multiple compounds selected from compound (I) and its tautomers or agriculturally acceptable salts thereof as active ingredients.
• compound (I) and compound (II) or compound (III) may exist in equilibrium.
• the ratio of compound (I) to compound (II) or compound (III) may vary depending on the solvent, temperature, pH, etc.
• the environmental stress tolerance improving agent in the present embodiment generally exhibits an effect of improving environmental stress tolerance in all plants, and examples of applicable plants include the following.
• Gramineae such as rice, wheat, barley, rye, oats, triticale (triticale), corn, sorghum, sugarcane, turfgrass, bentgrass, bermudagrass, fescue and ryegrass;
• Fabaceae such as soybean, peanut, kidney bean, pea, adzuki bean and alfalfa; Convolvulaceae such as sweet potato; Solanaceae such as chili pepper, bell pepper, tomato, eggplant, potato and tobacco;
• Polygonaceae such as buckwheat;
• Asteraceae such as sunflower;
• Araliaceae such as ginseng; Brassicas such as rapeseed, broccoli, Chinese cabbage, turnip, cabbage, arugula, radish and radish; Chenopodiaceae such as sugar beet; Malvaceae
• wild plants, plant cultivars, plants and plant cultivars obtained by conventional biological breeding such as crossbreeding or protoplast fusion, and genetically modified plants and plant cultivars obtained by genetic engineering can be mentioned.
• genetically modified plants and plant cultivars include herbicide-resistant crops, pest-resistant crops incorporating an insecticidal protein-producing gene, disease-resistant crops incorporating a disease-resistance-inducing substance-producing gene, crops with improved taste, crops with improved yield, crops with improved storability, and crops with improved yield.
• Genetically modified plant cultivars approved in each country can be listed in the database of the International Society for Agri-Biotechnology (ISAA).
• AgriSure, AgriSure 3000GT, AgriSure 3122 E-Z Refuge, AgriSure 3122 Refuge Renew AgriSure Artesian 3030A, AgriSure Artesian 3011A, AgriSure Duracade, AgriSure Duracade 5222 E-Z Refuge, AgriSure GT, AgriSure GT/CB/LL, AgriSure RW, AgriSure Viptera 3110, AgriSure Viptera 3111, AgriSure Viptera 3220 E-Z Refuge, AgriSure Viptera 3220 Refuge Renew, BiteGard, Bollgard, Bollgard II, Bollgard II/Roundup Ready, Bollgard 3 XtendFlex Cotton, Bollg ard Cotton, Bollgard/Roundup Ready Cotton, B.t., B.t/BXN Cotton, B.t.
• the environmental stress resistance improver in this embodiment is generally used by mixing the active ingredient compound (I) or a tautomer thereof, or a mixture thereof with a carrier, a surfactant and other formulation auxiliary, and formulating it into various forms such as dusts, granules, powders, wettable powders, water-soluble powders, emulsions, liquids, oils, aerosols, microcapsules, pastes, coatings, fumigants, fumigants and micro-dusting agents.
• Carriers used as formulation adjuvants include solid carriers and liquid carriers.
• Solid carriers are used as powder carriers and granular carriers, and include, for example, minerals such as clay, talc, diatomaceous earth, zeolite, montmorillonite, bentonite, kaolinite, kaolin, pyrophyllite, rosewood, acid clay, activated clay, attapulgite, attapulgus clay, limestone, calcite, marble, vermiculite, perlite, pumice, silica stone, silica sand, sericite (sericite) and pottery stone; synthetic organic substances such as urea; salts such as calcium carbonate, sodium carbonate, magnesium carbonate, sodium sulfate, ammonium sulfate, potassium chloride, hydrated lime and baking soda; amorphous silica (white Examples of suitable carriers include synthetic inorganic substances such as carbon, fumed silica, etc.
• plant-based carriers such as wood flour, corn stalks (cobs), walnut shells (nut husks), fruit kernels, rice husks, coconut shells, sawdust, bran, soy flour, powdered cellulose, starch, dextrin, and sugars (lactose, sucrose, etc.); and various polymer carriers such as cross-linked lignin, cationic gels, gelatin that gels when heated or with a polyvalent metal salt, water-soluble polymer gels (agar, etc.), chlorinated polyethylene, chlorinated polypropylene, polyvinyl acetate, polyvinyl chloride, ethylene/vinyl acetate copolymers, and urea/aldehyde resins.
• plant-based carriers such as wood flour, corn stalks (cobs), walnut shells (nut husks), fruit kernels, rice husks, coconut shells, sawdust, bran, soy flour, powdered cellulose, starch, dextri
• Liquid carriers include, for example, aliphatic solvents such as paraffins (normal paraffin, isoparaffin, naphthene); aromatic solvents such as xylene, alkylbenzene, alkylnaphthalene, and solvent naphtha; mixed solvents such as kerosene; machine oils such as refined high-boiling aliphatic hydrocarbons; alcohols such as methanol, ethanol, isopropanol, butanol, and cyclohexanol; polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, hexylene glycol, polyethylene glycol, and polypropylene glycol; polyhydric alcohol derivatives such as propylene glycol ethers; acetone, acetophenone, cyclohexanone, and methylcyclohexanone.
• paraffins normal paraffin, isoparaffin, naphthene
• aromatic solvents such as
• esters such as fatty acid methyl esters (coconut oil fatty acid methyl esters), ethylhexyl lactate, propylene carbonate, and dibasic acid methyl esters (dimethyl succinate, dimethyl glutamate, dimethyl adipate); nitrogen-containing solvents such as N-alkylpyrrolidones and acetonitrile; sulfur-containing solvents such as dimethyl sulfoxide; oils and fats such as coconut oil, soybean oil, and rapeseed oil; amide solvents such as dimethylformamide, N,N-dimethyloctanamide, N,N-dimethyldecanamide, 5-(dimethylamino)-2-methyl-5-oxo-valeric acid methyl ester, and N-acylmorpholine solvents (CAS No. 887947-29-7, etc.); and water.
• esters such as fatty acid methyl esters (coconut oil fatty acid methyl esters), ethylhe
• Surfactants used as formulation adjuvants include nonionic surfactants, anionic surfactants, cationic surfactants, amphoteric surfactants, silicone surfactants, fluorine-based surfactants, and biosurfactants.
• nonionic surfactants include sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, sucrose fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene resin acid esters, polyoxyethylene fatty acid diesters, polyoxyethylene alkyl ethers, polyoxyethylene alkyl phenyl ethers, polyoxyethylene dialkyl phenyl ethers, polyoxyethylene alkyl phenyl ether formalin condensates, polyoxyethylene/polyoxypropylene block polymers, alkyl polyoxyethylene/polyoxypropylene block polymer ethers, alkyl phenyl polyoxyethylene/polyoxypropylene block polymer ethers, polyoxyethylene alkyl amines, polyoxyethylene
• Anionic surfactants include, for example, sulfates such as alkyl sulfate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl phenyl ether sulfate, polyoxyethylene benzyl (or styryl) phenyl (or phenylphenyl) ether sulfate, and polyoxyethylene/polyoxypropylene block polymer sulfate; paraffin (alkane) sulfonate, ⁇ -olefin sulfonate, dialkyl sulfosuccinate, alkylbenzene sulfonate, mono- or dialkylnaphthalene sulfonate, naphthalene sulfonate-formaldehyde condensate, alkyl diphenyl ether disulfonate, lignin sulfonate, polyoxyethylene alkyl ether sulfate ...
• Examples of such compounds include sulfonates such as polyoxyethylene alkyl phenyl ether sulfonate and polyoxyethylene alkyl ether sulfosuccinic acid half ester; carboxylates such as fatty acids, resin acids, polycarboxylic acids, alkyl ether carboxylates, alkenyl succinic acids, N-acyl amino acids, and naphthenic acids; and phosphates such as polyoxyethylene alkyl ether phosphate, polyoxyethylene mono- or dialkyl phenyl ether phosphate, polyoxyethylene benzyl (or styryl) phenyl (or phenyl phenyl) ether phosphate, polyoxyethylene/polyoxypropylene block polymer phosphate, and alkyl phosphate.
• carboxylates such as fatty acids, resin acids, polycarboxylic acids, alkyl ether carboxylates, alkenyl succinic acids, N-acyl amino acids,
• cationic surfactants include salts of amines such as alkylamines and alkylpentamethylpropylenediamines; salts of ammoniums such as alkyltrimethylammonium, methylpolyoxyethylenealkylammonium, alkylpyridinium, mono- or dialkylmethylated ammonium, alkyldimethylbenzalkonium, and benzethonium (octylphenoxyethoxyethyldimethylbenzylammonium).
• amines such as alkylamines and alkylpentamethylpropylenediamines
• salts of ammoniums such as alkyltrimethylammonium, methylpolyoxyethylenealkylammonium, alkylpyridinium, mono- or dialkylmethylated ammonium, alkyldimethylbenzalkonium, and benzethonium (octylphenoxyethoxyethyldimethylbenzylammonium).
• amphoteric surfactants include dialkyldiaminoethyl betaine, alkyldimethylbenzyl betaine, and lecithin (phosphatidylcholine, phosphatidylethanolamine, etc.).
• silicone surfactant is trisiloxane ethoxylate.
• fluorosurfactants include perfluoroalkyl carboxylates, perfluoroalkyl sulfonates, and perfluoroalkyl trimethyl ammonium salts.
• biosurfactants include sophorolipids, rhamnolipids, trehalose lipids, mannosylalditol lipids, cellobiose lipids, glucose lipids, oligosaccharide fatty acid esters, spiculesporic acid, corynomycolic acid, agaritic acid, surfactin, serawettin, viscosin, lykensin, arthrofactin, emulsan, and alasan.
• formulation adjuvants include inorganic salts (sodium, potassium, etc.) used as pH adjusters; water-soluble salts such as table salt; xanthan gum, guar gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymers, acrylic polymers, polyvinyl alcohol, starch derivatives, water-soluble polymers (polysaccharides, etc.), alginic acid and its salts, etc. used as thickeners; metal stearates, sodium tripolyphosphate, sodium hexametaphosphate, etc.
• inorganic salts sodium, potassium, etc.
• water-soluble salts such as table salt
• xanthan gum, guar gum carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymers, acrylic polymers, polyvinyl alcohol, starch derivatives, water-soluble polymers (polysaccharides, etc.), alginic acid and its salts, etc. used as thickeners
• additives include sodium polyphosphate, sodium polyacrylate, sodium lignosulfonate, sodium citrate, sodium gluconate/glucoheptanoate, ethylenediaminetetraacetic acid and its disodium or ammonium salts; pigments and dyes used as colorants; fluorine-based defoamers, silicone-based defoamers, ethylene oxide/propylene oxide copolymers used as defoamers; phenol-based antioxidants, amine-based antioxidants, sulfur-based antioxidants, phosphoric acid-based antioxidants used as antioxidants; salicylic acid-based ultraviolet absorbers, benzophenone-based ultraviolet absorbers used as ultraviolet absorbers; quicklime, magnesium oxide, etc. used as drying agents; and other spreading agents and chemical damage reducers.
• the formulations are either used as is or diluted to a specified concentration with a diluent such as water.
• a diluent such as water.
• concentration of compound (I) is preferably in the range of 0.0001 to 1% by weight. The same applies to tautomers of compound (I).
• compositions are formulated to contain 0.1 to 90% by weight, more preferably 0.2 to 50% by weight, of compound (I) as the active ingredient.
• the amount of compound (I) used is 0.005 to 50 kg, more preferably 0.03 to 30 kg, per hectare of agricultural or horticultural land such as fields, rice paddies, orchards, and greenhouses. The same applies to the tautomers of compound (I).
• concentrations and amounts used vary depending on the formulation, time of use, method of use, location of use, and target plants, and can be increased or decreased without adhering to the above ranges.
• the environmental stress tolerance improver in the present embodiment can be used in combination with other known active ingredients to improve its performance as an environmental stress tolerance improver, or to impart an effect other than the improvement of environmental stress tolerance.
• Other known active ingredients include active ingredients contained in known environmental stress tolerance improvers, known plant growth regulators, fungicides, insecticides, miticides, nematicides, and herbicides.
• Active ingredients of known environmental stress resistance improvers include, for example, seaweed extract, corn extract, microalgae, mycorrhizal fungi, humic acid, fulvic acid, oxidized glutathione, L-proline, glycine betaine, 5-aminolevulinic acid, 2-hexenal, trehalose, silicic acid, nicotinic acid, acetic acid, and ethanol.
• Active ingredients of known plant growth regulators include, for example, aminoethoxyvinylglycine, chlormequat, chlorpropham, cyclanilide, dikeglac, daminozide, ethephon, flurprimidol, flumetralin, forchlorfenuron, gibberellin, mepiquat chloride, methylcyclopropene, benzylaminopurine, paclobutrazol, prohexadione, thidiazuron, tributyl phosphorotrithioate, trinexapac-ethyl, uniconazole, and 1-naphthalene acetate sodium.
• Effective ingredients suitable for fungicide applications include, for example, nucleic acid synthesis metabolic inhibitors, fungicides acting on the cytoskeleton and motor proteins, respiratory inhibitors, amino acid and protein biosynthesis inhibitors, signal transduction inhibitors, lipid biosynthesis or transport/cell membrane structure or function inhibitors, cell membrane sterol biosynthesis inhibitors, cell wall biosynthesis inhibitors, melanin biosynthesis inhibitors, host plant resistance inducers, multi-site fungicides, and biological pesticides/biologically derived pesticides with multiple modes of action.
• nucleic acid synthesis metabolic inhibitors include benalaxyl, benalaxyl M or chiralaxyl, furalaxyl, metalaxyl, metalaxyl M or mefenoxam, ofurace, oxadixyl, bupirimate, dimethirimol, ethirimol, hydroxyisoxazole, octhilinone, and oxolinic acid.
• Fungicides that act on the cytoskeleton and motor proteins include benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, diethofencarb, ethaboxam, pencycuron, zoxamide, fluopicolide, fluopimomide, fenamacril, metrafenone, and pyriophenone.
• Respiratory inhibitors include diflumetrim, fenazaquin, tolfenpyrad, benodanil, benzobindiflupyr, bixafen, boscalid, carboxin, fenfuram, fluveneteram, fluindapyr, fluopyram, flutolanil, fluxapyroxad, furametpyr, impirfluxam, isofetamide, isoflucipram, isopyrazam, mepronil, oxycarboxin, penflufen, penthiopyrad, pydiflumetofen, pyrapropoin, pyraziflumide, sedaxane, thifluzamide, azoxystrobin, cumoxystrobin, dimoxystrobin, enestrobin, enoxastrobin, famoxadone, and fenamide.
• phenaminestrobin flufenoxystrobin, fluoxastrobin, kresoxim-methyl, mandestrobin, metominostrobin, methyltetraprole, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyroxystrobin, pyribencarb, triclopyricarb, trifloxystrobin, amisulbrom, cyazofamid, fenpicoxamide, florylpicoxamide, methallylpicoxamide, binapacryl, dinocap, fluazinam, meptyldinocap, triphenyltin acetate, triphenyltin chloride, triphenyltin hydroxide, silthiofam, and amethoctrazine.
• amino acid and protein biosynthesis inhibitors include cyprodinil, mepanipyrim, pyrimethanil, blasticidin S, kasugamycin, streptomycin, and oxytetracycline.
• Signal transduction inhibitors include proquinazid, quinoxyfen, fludioxonil, chlozolinate, dimethaclon, fenpiclonil, iprodione, procymidone, and vinclozolin.
• examples of lipid synthesis or transport/cell membrane structure or function inhibitors include edifenphos (EDDP), iprobenfos (IBP), isoprothiolane, pyrazophos, biphenyl, chloroneb, dicloran (CNA), etridiazole, quintozene (PCNB), tecnazene (TCNB), tolclofos-methyl, iodocarb, propamocarb, prothiocarb, tea tree extract, vegetable oil mixture (eugenol, geraniol, thymol), natamycin (pimaricin), fluoxapiproline, and oxathiapiproline.
• EDDP edifenphos
• IBP isoprothiolane
• pyrazophos biphenyl, chloroneb, dicloran (CNA), etridiazole, quintozene (PCNB), tecnazene (TCNB), tol
• Inhibitors of cell membrane sterol biosynthesis include azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, etaconazole, fenbuconazole, fluoxythioconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imazalil, imibenconazole, ipconazole, ipfentrifluconazole, mefentrifluconazole, metconazole, myclobutanil, oxpoconazole, pefurazoate, penconazole, prochloraz, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, triticonazole, fenarimol
• Cell wall biosynthesis inhibitors include polyoxins, benthiavalicarb (benthiavalicarb isopropyl), dimethomorph, flumorph, iprovalicarb, mandipropamide, pyrimorph, and valifenalate.
• Melanin biosynthesis inhibitors include fthalide, pyroquilon, tricyclazole, carpropamid, diclocymet, fenoxanil, and tolprocarb.
• Resistance inducers in the host plant include acibenzolar-S-methyl, probenazole, tiadinil, isotianil, laminarin, Japanese knotweed extract, Bacillus mycoides isolate J, cell wall of Saccharomyces cerevisiae strain LAS117, fosetyl (fosetyl-aluminum, fosetyl potassium, fosetyl sodium), phosphoric acid, phosphate salts, and diclobentiazox.
• Multi-site fungicides include ferbam, mancozeb, maneb, metiram, propineb, thiuram, zinc thiazole, zineb, ziram, ambam, anilazine, dithianon, dichlofluanid, tolylfluanid, guazatine, iminoctadine acetate, iminoctadine albesilate, copper or various copper salts (e.g.
• Biological pesticides/biological pesticides with multiple modes of action include Bacillus subtilis AFS032321 strain, Bacillus amyloliquefaciens QST713 strain, Bacillus amyloliquefaciens FZB24 strain, Bacillus amyloliquefaciens MBI600 strain, Bacillus amyloliquefaciens D747 strain, Bacillus amyloliquefaciens F727 strain, Clonostachys rosea CR-7 strain, and Gliocladium catenaratum J1446 strain, Pseudomonas chlororaphis AFS009 strain, Streptomyces griseoviridis K61 strain, Streptomyces ridix WYEC108 strain, Trichoderma atroviride I-1237 strain, Trichoderma atroviride LU132 strain, Trichoderma atroviride SC1 strain, Trichoderma asperellum T34 strain, Swaingrea glutinosa extract, and extract from
• Other compounds for fungicide use include chlorinconazid, seboctylamin, flumethylsulfolim, flufenoxadiazam, cyflufenamid, cymoxanil, diclomedine, dipimethitron, dodine, fenitropan, ferimzone, flusulfamide, flutianil, harpin, inorganic salts (bicarbonates (sodium bicarbonate, potassium bicarbonate), potassium carbonate), ipflufenoquin, kinoprol, natural product origin, machine oil, organic oil, picarbutrazox, pyridaclomethyl, quinofumelin, tebufloquine, tecloftalam (bactericide), triazoxide, validamycin, aminopyrifen and shiitake mushroom mycelium extract.
• Suitable active ingredients for insecticide applications include, for example, acetylcholinesterase (AChE) inhibitors, GABAergic chloride channel blockers, sodium channel modulators, nicotinic acetylcholine receptor (nAChR) competitive modulators, nicotinic acetylcholine receptor (nAChR) allosteric modulators, glutamatergic chloride channel (GluCl) allosteric modulators, juvenile hormone analogues, other non-specific (multi-site) inhibitors, chordotonal organ TRPV channel modulators, mite growth inhibitors acting on CHS1, microbial-derived insect midgut membrane disruptors, mitochondrial ATP synthase inhibitors, oxidative phosphorylation uncouplers that disrupt the proton gradient, nicotinic acid synthase inhibitors, and nicotinic acid synthase inhibitors.
• AChE acetylcholinesterase
• GABAergic chloride channel blockers sodium channel
• tin acetylcholine receptor (nAChR) channel blockers include tin acetylcholine receptor (nAChR) channel blockers, chitin biosynthesis inhibitors acting on CHS1, chitin biosynthesis inhibitors (type 1), molting inhibitors (Diptera), molting hormone (ecdysone) receptor agonists, octopamine receptor agonists, mitochondrial electron transport complex III inhibitors, mitochondrial electron transport complex I inhibitors (METI), voltage-dependent sodium channel blockers, acetyl CoA carboxylase inhibitors, mitochondrial electron transport complex IV inhibitors, mitochondrial electron transport complex II inhibitors, ryanodine receptor modulators, chordotonal organ modulators, GABA-gated chloride ion channel allosteric modulators, and baculoviruses.
• nAChR tin acetylcholine receptor
• type 1 include tin acetylcholine receptor (nAChR) channel blockers
• Acetylcholinesterase (AChE) inhibitors include alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, NAC (carbaryl), carbofuran, carbosulfan, ethiofencarb, BPMC (fenobucarb), fenothiocarb, formetanate, furathiocarb, MIPC (isoprocarb), methiocarb, methomyl, MTMC (metolcarb), oxamyl, pirimicarb, PHC (propoxycarb), sul), thiodicarb, thiofanox, triazamate, trimethacarb, XMC, MPMC (xylylcarb), acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyphos, CVP (chlorfen
• GABA-gated chloride ion channel blockers include chlordane, benzoepine (endosulfan), dienochlor, ethiprole, fipronil, pyriprol, and nicoflurane.
• Sodium channel modulators include acrinathrin, allethrin (allethrin, d-cis-trans-, d-trans-isomers), bifenthrin, bioallethrin (bioallethrin, S-cyclopentenyl-isomer), bioresmethrin, chloroprallethrin, chlorfenthon, cycloprothrin, cyfluthrin (cyfluthrin, ⁇ -isomer), cyhalothrin (cyhalothrin, ⁇ -, ⁇ -isomers), cypermethrin (cypermethrin, ⁇ -, ⁇ -, ⁇ -, ⁇ -isomers), cyphenothrin [(1R)-trans isomer], deltamethrin, dimefluthrin, empenthrin [(EZ)-(1R)-isomer], esfenvalerate, e
• Nicotinic acetylcholine receptor (nAChR) competitive modulators include acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, nicotine sulfate (nicotine), sulfoxaflor, flupyradifurone, dichloromezothiaz, phenmezodithiaz, and triflumezopyrim.
• Nicotinic acetylcholine receptor (nAChR) allosteric modulators include spinetoram, spinosad, flupirimine and GS-omega/kappa HXTX-Hv1a peptide.
• Glutamate-gated chloride channel (GluCl) allosteric modulators include abamectin, emamectin benzoate, lepimectin, and milbemectin.
• Juvenile hormone mimetics include hydroprene, kinoprene, methoprene, fenoxycarb and pyriproxyfen.
• non-specific (multi-site) inhibitors include methyl bromide, other alkyl halides, chloropicrin, sodium aluminum fluoride, sulfuryl fluoride, borax, boric acid, disodium octaborate, sodium metaborate, tartar emetic, dazomet, carbam (metam ammonium salt), metam sodium salt, and methyl isothiocyanate (methyl isothiocyanate).
• Chodontoid TRPV channel modulators include pymetrozine, pyrifluquinazone, and afidopiropen.
• Mite growth inhibitors that act on CHS1 include clofentezine, diflobidazine, hexythiazox, and etoxazole.
• Microbial-derived insect midgut membrane disrupting agents include Bacillus thuringiensis subsp. israelensis, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki, and Bacillus thuringiensis subsp. These include proteins contained in B. tenebrionis, B.t. crops (Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Bb, Cry34Ab1/Cry35Ab1), and Bacillus sphaericus.
• Mitochondrial ATP synthase inhibitors include diafenthiuron, azocyclotin, tricyclohexyltin hydroxide (cyhexatin), fenbutatin oxide, BPPS (propargite), and tetradifon.
• Oxidative phosphorylation uncouplers that disrupt the proton gradient include chlorfenapyr, DNOC, and sulfluramide.
• Nicotinic acetylcholine receptor (nAChR) channel blockers include bensultap, cartap hydrochloride, thiocyclam, thiosultap sodium salt, and monosultap.
• Chitin biosynthesis inhibitors that act on CHS1 include bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, and triflumuron.
• Examples of chitin biosynthesis inhibitors include buprofezin.
• molting inhibitors include cyromazine.
• Ecdysone receptor agonists include chromafenozide, halofenozide, methoxyfenozide, and tebufenozide.
• octopamine receptor agonists examples include amitraz.
• Mitochondrial complex III electron transport inhibitors include hydramethylnon, acequinocyl, fluacrypyrim, flupiroxystrobin, and bifenazate.
• Mitochondrial electron transport complex I inhibitors include fenazaquin, fenpyroximate, pyridaben, pyrimidifen, tebufenpyrad, tolfenpyrad, and delis (rotenone).
• Examples of voltage-dependent sodium channel blockers include indoxacarb and metaflumizone.
• Acetyl CoA carboxylase inhibitors include spirodiclofen, spiromesifen, spiropydione, spidoxamat, spirobudifen, and spirotetramat.
• mitochondrial electron transport chain complex IV inhibitors examples include aluminum phosphide, calcium phosphide, hydrogen phosphide, zinc phosphide, hydrocyanic acid (calcium cyanide, sodium cyanide), and potassium cyanide.
• mitochondrial electron transport complex II inhibitors examples include cyenopyrafen, sietopyrafen, cyflumetofen, piflubumid, and cyclobutrifluram.
• Ryanodine receptor modulators include chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide, tetraniliprole, fluchlordiniliprole, thioantraniliprole, tetrachlorantraniliprole, cyhalodiamide, and ciproflanilide.
• chordotonal organ modulators examples include flonicamide.
• GABA-gated chloride ion channel allosteric modulators include broflanilide, fluxamethamide, and isocycloceram.
• Baculoviruses include the codling moth Cydia pomonella GV, the false codling moth Thaumatotibia leucotreta GV, the velvet bean caterpillar Anticarsis gemmatalis MNPV, and the cotton bollworm Helicoverpa armigera NPV.
• insecticides include azadirachtin, benzomate (benzoximate), phenisobromorate (bromopropylate), quinoxalines (quinomethionate), kelthane (dicofol), lime sulfur, mancozeb, pyridalyl, sulfur, acinonapyr, amidoflumet, benzpyrimoxane, fluazaindolizine, fluensulfone, fluhexafon, flupentiofenox, flometoquin, metaldehyde, cyclopyrazoflor, zinypropylidaz, trifluenfuronate, indazapiroxamet, sulfiflumin, burkholder.
• Bacillus subtilis Wolbachia pipientis (Zap)
• Atractylodes macrocarpa extract fatty acid monoesters with glycerin or propanediol
• neem oil machine oil, rapeseed oil, blended oil
• Metarhizium anisopria strain F52
• Paecilomyces fumosoroseus apopka strain 97
• diatomaceous earth DCIP (dichlorodiisopropyl ether), D-D (1,3 dichloropropene), levamisole hydrochloride, morantel tartrate, and thioxazafen.
• Effective ingredients suitable for herbicide applications include, for example, acetolactate synthase (ALS) inhibitor compounds, amino acid compounds, cyclohexanedione compounds, acetamide compounds, bipyridylium compounds, allyloxyphenoxypropionic acid compounds, carbamate compounds, pyridine compounds, urea compounds, dinitroaniline compounds, protoporphyrinogen oxidase (PPO) inhibitor compounds, phenoxyacetic acid compounds, hydroxyphenylpyruvate dioxygenase enzyme (HPPD) inhibitor compounds, and triazine compounds.
• ALS acetolactate synthase
• PPO protoporphyrinogen oxidase
• HPPD hydroxyphenylpyruvate dioxygenase enzyme
• Acetolactate synthesis (ALS) inhibitor compounds include imazamethabenz and imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, amidosulfuron, azimsulfuron, bensulfuron and bensulfuron-methyl, chlorimuron and chlorimuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron and ethametsulfuron-methyl, ethametsulfuron-ethyl, ethametsulfuron ...
• Toxicsulfuron Flazasulfuron, Flucetosulfuron, Flupyrsulfuron, Flupyrsulfuron-methyl and its salts, Foramsulfuron, Halosulfuron, Halosulfuron-methyl, Imazosulfuron, Iodosulfuron and its salts, Iodosulfuron-methyl and its salts, Mesosulfuron, Mesosulfuron-methyl, Metazosulfuron, Metsulfuron, Metsulfuron-methyl, Nicosulfuron, Oxasulfuron, Primisulfuron, Primisulfuron Examples include furon methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosulfuron ethyl, rimsulfuron, sulfometuron, sulfometuron methyl, sulfosulfuron, thifensulfuron, thifensulfuron methyl,
• Amino acid compounds include bialaphos and its salts, glufosinate and its salts, glufosinate P and its salts, and glyphosate and its salts.
• Cyclohexanedione compounds include alloxydim, butroxydim, clethodim, cloproxydim, cycloxydim, propoxydim, sethoxydim, tepraloxydim, and tralkoxydim.
• Acetamide compounds include napropamide, dimethachlor, petoxamide, acetochlor, alachlor, allidochlor (CDAA), butenachlor, delacrol, diethylethyl, propisochlor, pirinachlor, butachlor, dimethenamid, dimethenamid P, metazachlor, metolachlor, S-metolachlor, pretilachlor, propachlor, thenylchlor, flufenacet, and mefenacet.
• Bipyridylium compounds include cyperquat, morphamquat, diquat, and paraquat.
• Allyloxyphenoxypropionic acid compounds include clodinafop, clodinafop propargyl, clofop, cyhalofop butyl, diclofop, diclofop methyl, diclofop P methyl, fenoxaprop, fenoxaprop ethyl, fenoxaprop P ethyl, fluazifop, fluazifop butyl, fluazifop P butyl, haloxyfop, haloxyfop methyl, haloxyfop P methyl, isoxapyripop, metamifop, propaquizafop, quizalofop, quizalofop ethyl, quizalofop P ethyl and quizalofop P tefuryl.
• Carbamate compounds include asuram, carbetamide, desmedipham, chlorprocarb, phenisopham, cycloate, dimepiperate, pebulate, thiocarbazil, vernalate, barban, chlorbufam, chlorpropham, propham, swep, phenmedipham, butyrate, EPTC, esprocarb, molinate, orbencarb, prosulfocarb, pyributicarb, thiobencarb (benthiocarb), and triallate.
• Pyridine compounds include aminopyralid, clopyralid, diflufenican, dithiopyr, fluridone, fluroxypyr, haloxifene, florpyrauxifene, picloram and its salts, picolinafen, thiazopyr, and triclopyr and its salts.
• Urea compounds include benzthiazolone, bromuron, buturon, chlorbromuron, chloroxuron, difenoxuron, dimefuron, ethidimuron, fenuron, fluothiuron, metobenzuron, metobromuron, metoxuron, monolinuron, monuron (CMU), nebulon, parafluron, siduron, thiazafluron, chlorotoluron, dymuron, diuron (DCMU), fluometuron, isoproturon, linuron, methabenzthiazuron, tebuthiuron, cumyluron, carbutilate, and isouron.
• Dinitroaniline compounds include benfluralin (beslodin), butralin, dinitramine, ethalfluralin, fluchloralin, isopropaline, nitralin, profluralin, oryzalin, pendimethalin, prodiamine, and trifluralin.
• Protoporphyrinogen oxidase (PPO) inhibitors include acifluorfen, aclonifen, azafenidin, bifenox, clomethoxynil, ethoxyfene, ethoxyfene ethyl, fomesafen, fluazolate, fluoroglycofen, fluoroglycofen ethyl, halosafen, lactofen, oxyfluorfen, butafenacil, epirifenacil, chlornitrofen (CNP), fluorodifen, fluoronitrofen (CFNP), nitrofen (NIP), oxyflufen, chlorphthalim, flumipropine, carfentrazone, carfentrazone ethyl, cinidon ethyl, flumiclorac pentyl, flumioxazin, fluthiacet, fluthiacet methyl, oxadiargyl, ox
• Phenoxyacetic acid compounds include 2,4,5-T, 2,4-D and their salts, 2,4-DB and their salts, clomeprop, dichlorprop, fenoprop, MCPA and its salts, MCPB and its salts, mecoprop (MCPP) and its salts, and mecoprop P and its salts.
• HPPD inhibitor compounds include benzobicyclon, benzofenap, bicyclopyrone, isoxaflutole, mesotrione, pyrasulfotole, pyrazolinate (pyrazolate), pyrazoxyfene, sulcotrione, tefuryltrione, tembotrione, topramezone, fenquinotrione, and tolpyralate.
• Triazine compounds include atraton, aziprothrin, chlorazine, cyprazine, desmetryn, dipropetryn, eglinadine ethyl, ipazine, metoprothrin, procyazine, progliadine, prometon, propazine, sebutylazine, secbumeton, terbumeton, trietazine, ametryn, atrazine, cyanazine, dimethamethryn, hexazinone, indaziflam, metamitron, metribuzin, prometryn, simazine (CAT), simetryn, terbuthylazine, terbutryn, and triaziflam.
• Triazine compounds include atraton, aziprothrin, chlorazine, cyprazine, desmetryn, dipropetryn, eglinadine ethyl, ipazine, metoprothrin, procy
• herbicides include amicarbazone, ethiozin, isomethiozin, aminocyclopyrachlor, aminotriazole, anilofos, piperophos, beflubutamid, benazolin, benfuresate, bentazon, bromacil, isocyl, bromobutide, bromofenoxime, bromoxynil, butamiphos, DMPA, TCTP (chlorthal dimethyl), cafenstrole, chloridazon (PAC), brompyrazone, chlorthal, clomazone, cumyluron, dicamba (MDBA) and its salts, chloramben, TCBA (2,3,8-TBA), benazolin ether, Chil, chlorfenac, chlorfenprop, dichlobenil (DBN), chlorthiamid (DCBN), cinmethylin, methiozolin, amitrole, flamprop M, fosamine, methyldymron, monalid, MSMA
• the environmental stress tolerance improver in this embodiment can be used in, for example, cultivated land or non-cultivated land such as fields, paddy fields, lawns, and orchards.
• the environmental stress tolerance improver in this embodiment can be used by any fertilization method, for example, foliage spraying, mixing into water supply, soil spraying, injection into subsoil using an injector, seed treatment including treatment of bulbs and tubers, and direct fertilization of plants. Therefore, the method for improving environmental stress tolerance in this embodiment includes a procedure of fertilizing using the above-mentioned environmental stress tolerance improver.
• Application by mixing into water supply is carried out, for example, by administering granules to the water supplied to crops or to the water on the surface of a paddy field.
• the concentration of the active ingredient in the water supply is 0.5 to 500 mg/L, preferably 1 to 300 mg/L.
• the amount of active ingredient used when administered to the water on the surface of a paddy field is, for example, 0.5 to 5000 g, preferably 3 to 3000 g per 10 ares of paddy field.
• foliage spray or soil spraying can be carried out, for example, by treating the planting hole or its surroundings when transplanting seedlings, or by treating the seeds, plants, or the soil surrounding the plants with granules and wettable powders. In some cases, it may be preferable to mix the soil with the product after spraying.
• the amount of active ingredient used when spraying foliage or on the soil surface is, for example, 0.5 to 5000 mg, preferably 3 to 3000 mg per m2 of agricultural or horticultural land.
• the agent is attached to the seeds by mixing and stirring the wettable powder or dust with the seeds, or by immersing the seeds in a diluted wettable powder.
• Seed treatment also includes seed coating treatment.
• the amount of active ingredient used in seed treatment is, for example, 0.005 to 10,000 g, preferably 0.05 to 1,000 g, per 100 kg of seeds. Seeds treated with agricultural and horticultural agents can be used in the same way as normal seeds.
• concentration and amount used may vary depending on the formulation, time of use, method of use, location of use, target crop, etc., and may be increased or decreased without being bound by the above range.
• compound (I) and its tautomers exhibit excellent effects of improving environmental stress resistance in a wide range of plants.
• the environmental stress tolerance improving agent in the present embodiment exhibits an excellent effect of improving environmental stress tolerance in a treated plant.
• the agent for improving environmental stress tolerance of a plant according to embodiment 1 of the present invention contains, as an active ingredient, a compound represented by the following formula (I) or a tautomer thereof, or an agriculturally acceptable salt thereof.
• R 1 and R 2 independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms
• R 3 to R 5 independently represent an alkyl group having 1 to 4 carbon atoms
• the compound represented by formula (I) is preferably ergothioneine.
• the plant environmental stress resistance enhancer of aspect 3 according to the present invention preferably enhances resistance to at least one environmental stress selected from high temperature stress, low temperature stress, freezing stress, salt stress, excess nutrient stress, drought stress, excess water stress, ultraviolet stress, low light stress, and high light stress.
• the plant environmental stress tolerance improver of aspect 4 according to the present invention is any one of aspects 1 to 3, in which the environmental stress tolerance improver is a salt stress tolerance improver.
• plant environmental stress resistance improver of aspect 5 is an agent for improving drought stress resistance in any one of aspects 1 to 3.
• the plant environmental stress resistance improver of aspect 6 of the present invention is any one of aspects 1 to 3, in which the environmental stress resistance improver is a high temperature stress resistance improver.
• the plant environmental stress resistance improver of aspect 7 according to the present invention is an agent for improving environmental stress resistance in any one of aspects 1 to 3, wherein the agent is an agent for improving resistance to excess nutrient stress.
• plant environmental stress resistance improver of aspect 8 of the present invention is an agent for improving excess water stress resistance in any one of aspects 1 to 3.
• the plant environmental stress resistance improver of aspect 9 according to the present invention is any one of aspects 1 to 3, in which the environmental stress resistance improver is an ultraviolet stress resistance improver.
• the plant environmental stress resistance improver of aspect 10 according to the present invention is any one of aspects 1 to 3, in which the environmental stress resistance improver is a strong light stress resistance improver.
• the plant environmental stress resistance improver of aspect 11 of the present invention is any one of aspects 1 to 3, in which the environmental stress resistance improver is a freezing stress resistance improver.
• plant environmental stress resistance improver of aspect 12 of the present invention is an agent for improving low-temperature stress resistance in any one of aspects 1 to 3.
• the method for improving environmental stress resistance of a plant according to aspect 13 of the present invention includes treating a plant with an environmental stress resistance improver according to any one of aspects 1 to 12.
• L-(+)-ergothioneine L-(+)-ergothioneine
• glycine betaine which is a different compound from the environmental stress resistance improver according to this embodiment, will be used as a comparative compound.
• EGT L-(+)-ergothioneine
• GB glycine betaine
• Arabidopsis thaliana (Col-0) was seeded at three plants per well in a 24-well cell culture plate. 2 mL of liquid medium was placed per well, containing 1% by weight sucrose and 0.1% by weight agar powder in Murashige and Skoog medium mixed salts (Fujifilm Wako Pure Chemical Industries, Ltd.).
• the artificial climate chamber was set at a room temperature of 22°C, with a light period of 16 hours and a dark period of 8 hours. Light conditions were set to a light intensity of 5000 lx at the center under fluorescent light. Four days after sowing, EGT or GB was added to the designated concentration, and 24 hours later, a sodium chloride solution was added to a final concentration of 100 mM to impart salt stress.
• Mortality rate (%) ⁇ 1 - (number of surviving plants/number of plants tested) ⁇ x 100
• Environmental stress suppression rate (%) ⁇ 1 - (mortality rate in test compound-treated area/mortality rate in untreated area) ⁇ x 100
• Arabidopsis thaliana (Col-0) was sown in plastic pots measuring 60 mm in diameter and 55 mm in height, with one plant per pot. Six pots were placed in a deep plastic dish measuring 160 mm in diameter and 28 mm in height. As soil, 45 mL of vermiculite, 22.5 mL of granular culture soil (Kumiai horticultural culture soil), and 22.5 mL of vermiculite were placed in the pots, in that order.
• the artificial climate chamber was set at a room temperature of 22°C, with a light period of 16 hours and a dark period of 8 hours. Light conditions were set to a light intensity of 5000 lx at the center under fluorescent light. Water was supplied from the bottom, with the water level set to approximately 5 mm. 22 days after sowing, 50 mL of EGT was added, and drought stress was applied by stopping water supply from two days later for 18 days.
• the number of surviving plants 18 days after the water supply was cut off was counted, and the mortality rate of the plants was evaluated as an index of physiological disorders. The evaluation results are shown in Table 2.
• the mortality rate and the environmental stress inhibition rate were calculated according to the following formulas.
• Mortality rate (%) ⁇ 1 - (number of surviving plants/number of plants tested) ⁇ x 100
• Environmental stress suppression rate (%) ⁇ 1 - (mortality rate in test compound-treated area/mortality rate in untreated area) ⁇ x 100
• the plants were kept in a greenhouse with a room temperature of 25°C. 23 days after sowing, 50 mL of EGT or 50 mL of GB was added, and 4 days later, water supply was stopped for 4 days to cause drought stress.
• Leaf necrosis rate 4 days after the water supply was cut off was evaluated using the total leaf area and green leaf area. The evaluation results are shown in Table 3.
• the leaf necrosis rate and the environmental stress inhibition rate were calculated according to the following formulas.
• Leaf necrosis rate (%) ⁇ 1 - (green leaf area/total leaf area) ⁇ x 100
• Environmental stress suppression rate (%) ⁇ 1 - (leaf necrosis rate in the test compound-treated group/leaf necrosis rate in the untreated group) ⁇ x 100
• the artificial climate chamber was set at a room temperature of 22°C, with a light period of 16 hours and a dark period of 8 hours. Light conditions were set so that the light intensity was 5000 lx at the center under fluorescent light irradiation. Water was supplied from the bottom, with the water level set to approximately 5 mm. 41 days after sowing, 50 mL of EGT or 50 mL of GB was added, and one day later, the plants were exposed to a 42°C environment for 3 hours to cause high temperature stress.
• the number of surviving plants 12 days after the application of high temperature stress was counted, and the plant mortality rate was evaluated as an index of physiological disorder.
• the evaluation results are shown in Table 4.
• the mortality rate and environmental stress suppression rate were calculated according to the following formulas.
• Mortality rate (%) ⁇ 1 - (number of surviving plants/number of plants tested) ⁇ x 100
• Environmental stress suppression rate (%) ⁇ 1 - (mortality rate in test compound-treated area/mortality rate in untreated area) ⁇ x 100
• Arabidopsis thaliana (Col-0) was sown in plastic pots measuring 60 mm in diameter and 55 mm in height, with one plant per pot. A deep plastic dish measuring 160 mm in diameter and 28 mm in height was prepared and four pots were placed in it. As soil, 45 mL of vermiculite, 22.5 mL of granular culture soil (Kumiai horticultural culture soil), and 22.5 mL of vermiculite were placed in the pots, in that order.
• the artificial climate chamber was set at a room temperature of 22°C, with a light period of 16 hours and a dark period of 8 hours. Light conditions were set so that the light intensity was 5000 lx at the center under fluorescent light irradiation. Water was supplied from the bottom, with the water level set to approximately 5 mm. 61 days after sowing, 50 mL of EGT or 50 mL of GB was added, and one day later, liquid fertilizer (HYPONEX, manufactured by Hyponex Japan) was applied at a 5-fold dilution to provide excess nutrient stress.
• liquid fertilizer (HYPONEX, manufactured by Hyponex Japan) was applied at a 5-fold dilution to provide excess nutrient stress.
• Leaf wilting rate (%) (number of wilted leaves/total number of leaves on the tested plant) x 100
• Environmental stress suppression rate (%) ⁇ 1 - (Wilting rate of test compound-treated group/Wilting rate of untreated group) ⁇ x 100
• the plants were kept in a greenhouse with a room temperature set at 25°C. 23 days after sowing, 50 mL of EGT or 50 mL of GB was added, and then water supply was stopped for 7 days to cause drought stress.
• Leaf mortality rate (%) (number of dead leaves/total number of leaves on the tested plant) x 100
• Environmental stress suppression rate (%) ⁇ 1 - (leaf mortality rate in test compound-treated area/leaf mortality rate in untreated area) ⁇ x 100
• the plants were kept in a greenhouse with a room temperature of 25°C. 22 days after sowing, 50 mL of EGT or 50 mL of GB was added, after which water supply was stopped for 7 days. After that, the plants were grown under water supply for 7 days, and then water supply was stopped again for another 7 days to apply drought stress.
• Leaf mortality rate (%) (number of dead leaves/total number of leaves on the tested plant) x 100
• Environmental stress suppression rate (%) ⁇ 1 - (leaf mortality rate in test compound-treated area/leaf mortality rate in untreated area) ⁇ x 100
• nursery soil (Takii Seeds) was placed in plastic pots measuring 135mm in diameter and 110mm in height, and 100mm square pieces of turfgrass (Korean grass) were planted per pot.
• the plants were kept in a greenhouse with a room temperature of 25°C. Approximately one month after turfing, 12.5mL of EGT or 12.5mL of GB was added, and then watering was stopped for seven days. After that, the plants were grown with water for seven days, and then watering was stopped for another seven days to apply drought stress.
• Leaf mortality rate (%) (number of dead leaves/total number of leaves on the tested plant) x 100
• Environmental stress suppression rate (%) ⁇ 1 - (leaf mortality rate in test compound-treated area/leaf mortality rate in untreated area) ⁇ x 100
• the number of surviving plants 19 days after the application of excess water stress was counted, and the mortality rate of the plants was evaluated as an index of physiological disorders.
• the evaluation results are shown in Table 9.
• the mortality rate and the environmental stress suppression rate were calculated according to the following formulas.
• Mortality rate (%) ⁇ 1 - (number of surviving plants/number of plants tested) ⁇ x 100
• Environmental stress suppression rate (%) ⁇ 1 - (mortality rate in test compound-treated area/mortality rate in untreated area) ⁇ x 100
• the pure water in the petri dishes was removed, and then 5 mL of EGT or 5 mL of GB was added to the petri dishes.
• the dishes were exposed to ultraviolet light stress for 1 hour under irradiation with an ultraviolet lamp (Toshiba Corporation, GL-15) set so that the ultraviolet radiation intensity at a wavelength of 254 nm was 550 ⁇ W/cm -2 .
• Leaf mortality rate (%) (number of dead leaves/total number of leaves on the tested plant) x 100
• Environmental stress suppression rate (%) ⁇ 1 - (leaf mortality rate in test compound-treated area/leaf mortality rate in untreated area) ⁇ x 100
• UV stress caused physiological disorders such as chlorosis in wheat, with 53% of the test wheat leaves dying (Comparative Example 41), and treatment with GB did little to suppress the mortality rate due to UV stress (Comparative Examples 35 and 36).
• wheat treated with EGT had a lower mortality rate than wheat treated with GB, with the mortality rate due to UV stress suppressed to 34% at 0.1 mM (Example 13) and 23% at 1.0 mM (Example 12).
• Lawn grass (Korean lawn grass) cut into 50 mm squares was placed on a petri dish and managed in a greenhouse set at a room temperature of 25° C. The grass was trimmed to a length of 10 mm. 10 mL of EGT or 10 mL of GB was added per petri dish, and one day later, the plants were exposed to ultraviolet light stress for 1 hour under irradiation with an ultraviolet lamp (Toshiba Corporation, GL-15) set so that the ultraviolet radiation intensity at a wavelength of 254 nm was 525 ⁇ W/cm ⁇ 2 .
• an ultraviolet lamp Toshiba Corporation, GL-15
• Leaf mortality rate (%) (number of dead leaves/total number of leaves on the tested plant) x 100
• Environmental stress suppression rate (%) ⁇ 1 - (leaf mortality rate in test compound-treated area/leaf mortality rate in untreated area) ⁇ x 100
• the plants were kept in an artificial climate chamber set at a room temperature of 22°C, with a light period of 16 hours and a dark period of 8 hours.
• the light conditions were set to a light intensity of 5000 lx at the center under fluorescent light irradiation. 43 days after sowing, 12.5 mL of EGT or 12.5 mL of GB was added, and one day later, the plants were exposed to LED light (Esbaybulbs) with a light intensity of 2000 ⁇ mol/m -2 /sec for 24 hours to apply strong light stress.
• LED light Esbaybulbs
• Leaf whitening rate (%) (number of bleached leaves/total number of leaves on the tested plant) x 100
• Environmental stress suppression rate (%) ⁇ 1 - (chlorosis rate of leaves in test compound-treated area/chlorosis rate of leaves in untreated area) ⁇ x 100
• the pure water was removed from the petri dishes, and 5 mL of EGT or 5 mL of GB was added to the dishes. 14 days later, the dishes were exposed to a -20°C environment for 20 minutes, and one day later, the dishes were exposed to a -20°C environment for 20 minutes to induce freezing stress.
• the pure water was removed from the petri dishes, and 5 mL of EGT or 5 mL of GB was added to the dishes.
• the dishes were exposed to a -20°C environment for 20 minutes to induce freezing stress.
• the pure water was removed from the petri dishes, and 1 mL of EGT or 1 mL of GB was added to the dishes. 24 hours later, the dishes were exposed to a 4°C environment for 48 hours to induce low temperature stress.
• Leaf wilting rate (%) (number of wilted leaves/total number of leaves on the tested plant) x 100
• Environmental stress suppression rate (%) ⁇ 1 - (leaf wilting rate in test compound-treated group/leaf wilting rate in untreated group) ⁇ x 100

Landscapes

• Life Sciences & Earth Sciences (AREA)
• Wood Science & Technology (AREA)
• Engineering & Computer Science (AREA)
• Environmental Sciences (AREA)
• Plant Pathology (AREA)
• Zoology (AREA)
• Pest Control & Pesticides (AREA)
• Botany (AREA)
• Forests & Forestry (AREA)
• Ecology (AREA)
• Biodiversity & Conservation Biology (AREA)
• General Health & Medical Sciences (AREA)
• Dentistry (AREA)
• Health & Medical Sciences (AREA)
• Agronomy & Crop Science (AREA)
• Chemical & Material Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Cultivation Of Plants (AREA)
• Fertilizers (AREA)

Priority Applications (7)

Applications Claiming Priority (2)

Publications (1)

Family

ID=90477964

Family Applications (1)

Country Status (8)

Cited By (3)

Citations (17)

Family Cites Families (2)

• 2023
  • 2023-09-25 AR ARP230102540A patent/AR130564A1/es unknown
  • 2023-09-26 CN CN202380061929.2A patent/CN119947585A/zh active Pending
  • 2023-09-26 US US19/113,746 patent/US20260101897A1/en active Pending
  • 2023-09-26 KR KR1020257009331A patent/KR20250051108A/ko active Pending
  • 2023-09-26 JP JP2024549406A patent/JP7748574B2/ja active Active
  • 2023-09-26 EP EP23872312.6A patent/EP4595752A4/en active Pending
  • 2023-09-26 WO PCT/JP2023/034858 patent/WO2024071089A1/ja not_active Ceased
  • 2023-09-26 AU AU2023354193A patent/AU2023354193A1/en active Pending
• 2025
  • 2025-08-20 JP JP2025137328A patent/JP2025169401A/ja active Pending

Patent Citations (17)

Non-Patent Citations (3)

Also Published As

Similar Documents

Legal Events