Agent for improving environmental stress tolerance of plants and method for improving environmental stress tolerance

Abstract

An agent for improving the environmental stress tolerance of a plant, which contains, as an active ingredient, a compound represented by formula (I) or a tautomer thereof, or an agronomically acceptable salt thereof. (In formula (I), R1 and R2 independently represent a hydrogen atom or an alkyl group having 1-4 carbon atoms, and R3 to R5 independently represent an alkyl group having 1-4 carbon atoms). # imgabs0 #

Description

Technical Field

[0001] The present invention relates to an agent for improving environmental stress tolerance of plants and a method for improving environmental stress tolerance. Background Art

[0002] Environmental stresses such as global warming, drought, and salt damage adversely affect plant survival and thus cause serious damage in agriculture. Removing environmental stress is difficult or requires a lot of cost, and therefore there has been a demand for agents that improve environmental stress tolerance in a wide range of plants.

[0003] Here, ergothioneine is known as a compound that affects the growth of plants.

[0004] Patent Document 1 discloses ergothioneine and a fertilizer containing a culture of a microorganism capable of biosynthesizing ergothioneine.

[0005] Patent Document 2 reports that the growth of plants can be promoted or the yield can be increased by applying thioneine monomer to plants.

[0006] Patent Document 3 reports that a microbial extract containing ergothioneine is used as a fertilizer to increase nitrogenase activity.

[0007] Furthermore, Patent Documents 4 and 5 report that glycine betaine is applied to plants, thereby controlling stress and conditions associated with the plants and promoting growth of the plants.

[0008] Prior art literature

[0009] Patent Literature

[0010] Patent Document 1: Japanese Patent Application Publication No. 2018-130091

[0011] Patent Document 2: Japanese Patent Application No. 2019-128636

[0012] Patent Document 3: European Patent Application Publication No. 3696154

[0013] Patent Document 4: International Publication No. 96 / 14749

[0014] Patent Document 5: International Publication No. 96 / 23413 Summary of the invention

[0015] Problem that the invention aims to solve

[0016] As mentioned above, various medicaments for improving environmental stress tolerance have been developed, but it is still necessary to show an environmental stress tolerance enhancer of more excellent effect. However, in patent documentation 1, patent documentation 2 and patent documentation 3, there is no clear record of the environmental stress tolerance of plant to improve the effect. In patent documentation 4 and patent documentation 5, except glycine betaine, the record of 2-mercaptohistidine betaine (ergothioneine) has also been seen, but there is no embodiment about ergothioneine, and the effect is not confirmed.

[0017] Therefore, an object of one embodiment of the present invention is to achieve an agent for improving environmental stress tolerance and a method for improving environmental stress tolerance that can effectively improve the environmental stress tolerance of plants.

[0018] Technical Solution

[0019] In order to solve the above problems, an agent for improving plant environmental stress tolerance according to one embodiment of the present invention is an agent for improving plant environmental stress tolerance comprising a compound represented by the following formula (I) or its tautomer, or an agronomically acceptable salt thereof as an active ingredient.

[0020] [Chemical formula 1]

[0021]

[0022] (In formula (I), R 1 and R 2 independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R 3 ~R 5 independently represents an alkyl group having 1 to 4 carbon atoms).

[0023] Furthermore, in order to solve the above-mentioned problems, a method for improving environmental stress tolerance of a plant according to one embodiment of the present invention comprises treating the plant with the above-mentioned environmental stress tolerance improving agent.

[0024] Effects of the Invention

[0025] According to one embodiment of the present invention, an environmental stress tolerance improving agent and an environmental stress tolerance improving method that can effectively improve the environmental stress tolerance of a plant can be provided. DETAILED DESCRIPTION

[0026] 〔Environmental stress tolerance enhancer〕

[0027] (Active ingredient)

[0028] The environmental stress tolerance-enhancing agent of the present embodiment 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.

[0029] [Chemical formula 2]

[0030]

[0031] In formula (I), R 1 and R 2 R independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. 3 ~R 5 Each of them independently represents an alkyl group having 1 to 4 carbon atoms.

[0032] The alkyl group may be linear or branched, that is, may be methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl.

[0033] Preferred R 1 and R 2 At least one of them is a hydrogen atom, and more preferably R 1 and R 2 are all hydrogen atoms. 1 and R 2 In the case of an alkyl group, a methyl group, an ethyl group or a propyl group is preferred, a methyl group or an ethyl group is more preferred, and a methyl group is further preferred.

[0034] R 3 ~R 5 Preferably, each is independently methyl, ethyl or propyl, more preferably methyl or ethyl, and further preferably methyl. 3 ~R 5 At least one is methyl, more preferably R 3 ~R 5 At least two are methyl groups, and more preferably R 3 ~R 5 All are methyl.

[0035] "Tautomers thereof" refers to tautomers of compound (I). 1 and R 2 When at least one of the R is a hydrogen atom, there are tautomers. More specifically, in formula (I), 2 When R is a hydrogen atom, the compound represented by the following formula (II) (hereinafter referred to as "compound (II)") may exist as a tautomer. 1 When it is a hydrogen atom, a compound represented by the following formula (III) (hereinafter, simply referred to as "compound (III)") may exist as a tautomer. Hereinafter, compound (II) and compound (III) are collectively referred to as "tautomers".

[0036] [Chemical formula 3]

[0037]

[0038] In formula (II) and (III), R 1 ~R 5 With R in formula (I) 1 ~R 5 same.

[0039] Specifically, a preferred compound as compound (I) or its tautomer is ergothioneine, and more preferably L-(+)-ergothioneine.

[0040] These compounds can use commercial products, and can use technology well known to those skilled in the art, such as by patent documentation: the compound synthesized by the method of recording in Japanese Unexamined Patent Publication No. 2013-506706 or Japanese Unexamined Patent Publication No. 2006-160748. In addition, known thioneine can be produced by bacteria and fungi. As such an output method using microorganisms, for example, patent documentation can be enumerated: the method of recording in Japanese Unexamined Patent Publication No. 2012-105618, Japanese Unexamined Patent Publication No. 2014-223051, WO2016 / 104437, WO2016 / 121285, WO2015 / 168112 and WO2017 / 150304. As thioneine, the culture obtained by these microorganisms, comprising thioneine, can be directly used, thioneine can also be concentrated or purified for use.

[0041] “Agronomically acceptable” generally means that the substance is safe, non-toxic, and not undesirable in biological or other senses, and is acceptable for use as a pesticide, particularly as a pesticide that improves the tolerance of plants to environmental stress.

[0042] The "agronomically acceptable salt" of compound (I) or its tautomer refers to an agronomically acceptable salt as defined above, which is a salt that can obtain the action and effect of compound (I) or its tautomer. Such salts include, for example, hydrates, solvates, acid addition salts, salts formed when the acidic protons (proton acide) present in compound (I) or its tautomers are replaced by metal ions, and salts formed when the acidic protons are coordinated with organic bases or inorganic bases.

[0043] Acid addition salts can be formed with inorganic acids or organic acids. Examples of inorganic acids include hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, and phosphoric acid. Examples of 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-hydroxyethylsulfonic 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.

[0044] Examples of the metal ion that can substitute for the acidic proton present in compound (I) or its tautomer include alkali metal ions, alkaline earth metal ions and aluminum ions.

[0045] Examples of the organic base that can coordinate with the acidic proton present in compound (I) or its tautomer include diethanolamine, ethanolamine, N-methylglucamine, triethanolamine, and tromethamine, etc. Examples of the inorganic base include aluminum hydroxide, calcium hydroxide, potassium hydroxide, sodium carbonate, and sodium hydroxide, etc.

[0046] The environmental stress tolerance improving agent of the present embodiment contains compound (I) or its tautomer, or an agronomically acceptable salt thereof as an active ingredient, whereby the tolerance of treated plants to environmental stress is improved compared to untreated plants.

[0047] The term “enhanced tolerance to environmental stress” as used herein means that physiological diseases caused by environmental stress are suppressed in plants treated with the environmental stress tolerance-enhancing agent of the present embodiment, compared with untreated plants.

[0048] As an "indicator of suppression of physiological diseases caused by environmental stress", for example, the environmental stress suppression rate can be cited. The "environmental stress suppression rate" refers to the ratio of physiological diseases produced in plants after being cultivated for a specified period under an environment with environmental stress, which are suppressed by treatment with an environmental stress tolerance enhancer according to an embodiment, compared with untreated plants. For example, in an environment with environmental stress, if the physiological diseases produced in plants not treated with an environmental stress tolerance enhancer are taken as 100%, and the physiological diseases produced in plants treated with an environmental stress enhancer are 20%, then the environmental stress suppression rate becomes 80%. "Improved tolerance to environmental stress" with respect to the "environmental stress suppression rate" means that the environmental stress suppression rate is high.

[0049] As "indicators of physiological diseases", for example, dieback, chlorosis (albinism or yellowing), necrosis and wilting in plants can be listed. For example, dieback, chlorosis (albinism or yellowing), necrosis and wilting in leaves can be listed, but are not limited to these examples. Examples include a decrease in plant height, root length, number of flowers, number of fruits and seed yield.

[0050] As an example, the "plant withering rate" is the ratio of the number of plants that withered after the plants were cultivated under specified conditions for a specified period to the number of plants tested. As an example, the withering rate is 80% when 80 plants withered after 100 plants were cultivated under specified conditions for a specified period. "Improved tolerance to environmental stress" in relation to the "plant withering rate" means that the withering rate of plants treated with the environmental stress tolerance enhancer of the present embodiment is low in an environment where environmental stress is applied, compared with untreated plants.

[0051] As an example, "leaf withering rate" refers to the ratio of the number of dead leaves of a plant after being cultivated for a specified period under specified conditions to the number of leaves of the plant to be tested. As an example, the leaf withering rate is 80% when 8 out of 10 leaves are withered after the plant is cultivated for a specified period under specified conditions. "Improved tolerance to environmental stress" in relation to "leaf withering rate" means that the plant treated with the environmental stress tolerance enhancer of the present embodiment has a low withering rate under an environment with environmental stress compared to untreated plants.

[0052] As an example, the "leaves whitening rate" refers to the ratio of the number of leaves that have whitened after the plant is cultivated under specified conditions for a specified period to the number of leaves of the plant to be tested. As an example, the leaf whitening rate is 80% when 8 out of 10 leaves are whitened after the plant is cultivated under specified conditions for a specified period. "Improvement of the system to environmental stress" with respect to the "leaves whitening rate" means that the plants treated with the environmental stress tolerance enhancer of the present embodiment have a low whitening rate under an environment with environmental stress compared to untreated plants.

[0053] As an example, "leaf necrosis rate" refers to the ratio of the leaf area that has necrosis to the total leaf area of ​​the plant after the plant is cultivated under specified conditions for a specified period of time. As an example, the total leaf area of ​​the plant is 100 cm after the plant is cultivated under specified conditions for a specified period of time. 2 80cm 2 The necrosis rate of leaves in the case of necrosis was 80%. "Enhanced tolerance to environmental stress" in terms of "leaf necrosis rate" means that the necrosis rate of plants treated with the environmental stress tolerance enhancer of the present embodiment is low under an environment with environmental stress compared to untreated plants.

[0054] As an example, "leaf wilting rate" refers to the ratio of the number of wilted leaves after a plant is cultivated under specified conditions for a specified period to the number of leaves of the plant to be tested. As an example, the wilting rate of leaves when 8 out of 10 leaves wilt after a plant is cultivated under specified conditions for a specified period is 80%. "Improvement of resistance to environmental stress" with respect to "leaf wilting rate" means that the wilting rate of a plant treated with the environmental stress tolerance enhancer of the present embodiment is low in an environment where environmental stress is applied, compared with an untreated plant.

[0055] "Enhanced tolerance to environmental stress" with respect to "plant height" as another example means that compared with untreated plants, the plant height of the plant treated with the environmental stress tolerance enhancer of the present embodiment is higher under an environment where environmental stress is applied. In addition, "enhanced tolerance to environmental stress" with respect to "root length" as another example means that compared with untreated plants, the root length of the plant treated with the environmental stress tolerance enhancer of the present embodiment is longer under an environment where environmental stress is applied. In addition, "enhanced tolerance to environmental stress" with respect to "number of flowers" as another example means that compared with untreated plants, the number of flowers of the plant treated with the environmental stress tolerance enhancer of the present embodiment under an environment where environmental stress is applied is large. In addition, "enhanced tolerance to environmental stress" with respect to "number of fruits" as another example means that compared with untreated plants, the number of fruits of the plant treated with the environmental stress tolerance enhancer of the present embodiment under an environment where environmental stress is applied is large. Furthermore, “improved tolerance to environmental stress” with respect to “seed yield” as another example means that the seed yield of plants treated with the environmental stress tolerance improving agent of the present embodiment is greater under an environment where environmental stress is applied than that of untreated plants.

[0056] Among them, a preferred embodiment is an agent for improving environmental stress tolerance for suppressing plant or leaf dieback, chlorosis (albinosis or yellowing), necrosis or wilting caused by environmental stress.

[0057] "Environmental stress" in this specification refers to environmental factors that may hinder normal growth of plants. For example, it can be listed as: high temperature stress, low temperature stress, freezing stress, salt stress, excess nutrient stress, dryness stress, excess water stress, ultraviolet stress, weak light stress and strong light stress.

[0058] It should be noted that these factors are basically conditions that are difficult to cultivate normally when not treated with the environmental stress tolerance enhancer of the present embodiment. Normal cultivation mentioned here refers to the degree of cultivation under the state that these factors are not involved and the environmental stress tolerance enhancer of the present embodiment is not treated. In addition, being difficult to cultivate normally not only includes the situation of cultivating difficulty, but also includes the situation that the degree of cultivation is poor compared with normal cultivation.

[0059] Preferably, the environmental stress tolerance enhancer of the present embodiment comprises compound (I) or its agronomically acceptable salt as an active ingredient. The environmental stress tolerance enhancer of the present embodiment may also comprise a plurality of compounds of compound (I) and its tautomers or their agronomically acceptable salts as an active ingredient.

[0060] Generally, in a solution, 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.

[0061] (Application Target)

[0062] The environmental stress tolerance enhancer in the present embodiment generally exhibits an effect of enhancing tolerance to environmental stress for all plants, and the following can be cited as examples of applicable plants. Wheat families such as rice, wheat, barley, rye, oats, triticosecale, corn, sorghum, sugarcane, grass, herbs, bermudagrass, fescue, and ryegrass; legume families such as soybeans, peanuts, beans, peas, red beans, and alfalfa; Convolvulaceae families such as sweet potatoes; Solanaceae families such as red peppers, bell peppers, tomatoes, eggplants, potatoes, and tobacco; Polygonaceae families such as buckwheat; Compositae families such as sunflowers; Araliaceae families such as ginseng; Cruciferae families such as rapeseed, cauliflower, Chinese cabbage, turnip, cabbage, rocket, radish, and radish; Quinoa families such as beets; Malvaceae families such as cotton; Rubiaceae families such as coffee trees ; Sterculiaceae such as cocoa; Tea such as tea; Cucurbitaceae such as watermelon, melon, cucumber and pumpkin; Liliaceae such as onion, scallion and garlic; Rosaceae such as strawberry, apple, almond, apricot, plum, yellow peach, prune, peach and pear; Apiaceae such as carrot; Taro such as taro; Anacardiaceae such as mango; Bromeliaceae such as pineapple; Papaya such as papaya; Persimmon such as persimmon; Moraceae such as blueberry; Walnut such as pecan; Musaceae such as banana; Oleaceae such as olive; Arecaaceae such as coconut and date; Rutaceae such as tangerine, orange, grapefruit and lemon; Grapes such as grapevine; Flowers and ornamental plants, trees other than fruit trees and other ornamental plants.

[0063] In addition, wild plants, plant cultivars, plants and plant cultivars obtained by existing biological breeding such as cross-breeding or protoplasm fusion, and transgenic plants and plant cultivars obtained by gene manipulation can be listed. As transgenic plants and plant cultivars, for example, herbicide-resistant crops, pest-resistant crops integrated with insecticidal protein production genes, disease-resistant crops integrated with disease resistance inducing substance production genes, taste-improved crops, yield-improved crops, storage-improved crops, and yield-improved crops can be listed. As transgenic plant cultivars recognized in various countries, varieties stored in the database of the International Service for the Acquisition of Agri-biotech Applications (ISAAA) can be listed. Specifically, the following registered trademarks are listed: AgriSure, AgriSure 3000GT, AgriSure3122E-Z Refuge, AgriSure 3122Refuge Renew, AgriSure Artesian 3030A, AgriSureArtesian 3011A, AgriSure Duracade, AgriSure Duracade 5222E-Z Refuge, AgriSureGT, AgriSure GT / CB / LL, AgriSure RW, AgriSure Viptera 3110, AgriSure Viptera 3111, AgriSure Viptera3220E-Z Refuge, AgriSure Viptera 3220Refuge Renew, BiteGard, Bollgard, Bollgard II, Bollgard II / Roundup Ready, Bollgard 3XtendFlex Cotton, Bollgard Cotton, Bollgard / Roundup Ready Cotton, Bt, Bt / BXN Cotton, BtMaize, BtXtra, BXN, BXN Canola, BXN Cotton, Clearfield, DroughtGard, Enlist, Enlist Cotton, Enlist WideStrike 3Cotton, Genuity, Genuity Bollgard II XtendFlex, GenuityIntacta RR2 Pro, Genuity SmartStax, Genuity SmartStax RIB Complete, Genuity VTDouble Pro, Genuity VT Double Pro RIBComplete, Genuity VT Triple Pro, GenuityVT Triple Pro RIB Complete, GlyTol, GlyTol Cotton, Herculex, Herculex 1, HerculexRW, Herculex XTRA, IMI, IMI Canola, InVigor, KnockOut, Liberty Link, Liberty LinkConola, Liberty Link cotton, NatureGard, Newleaf, Nucotn, Optimum, Optimum AcreMax, Optimum AcreMax I, Optimum AcreMax-R, Optimum AcreMax RW, Optimum AcreMax RW-R, Optimum AcreMax Xtra-R, Optimum AcreMax Xtreme-R, Optimum AcreMax Xtreme, Optimum Intrasect, Optimum Intrasect Xtra, Optimum Intrasect Xtreme, OptimumLeptra, Optimum TRIsect, Poast Compatible, Powercore, Powercore Corn, PowercoreCorn Refuge Advanced, Protecta, Roundup Ready, Roundup Ready 2, Roundup ReadyConola, Roundup Ready Cotton, Roundup Ready Xtend, Roundup Ready / YieldGard, RRFlex / Bollgard II, SCS, SmartStax, SmartStax Refuge Advanced, StarLink, Twinlink, VipCot, VipCot Cotton, WideStrike, WideStrike 3, YieldGard, YieldGard Corn Borner, YieldGard Rootworm, YieldGard Plus, and YieldGard VT Triple, etc.

[0064] (Formulation)

[0065] As for the environmental stress tolerance enhancer in this embodiment, the compound (I) or its tautomer or their mixture as the active ingredient is usually mixed with a carrier, a surfactant and other formulation adjuvants, and formulated into various forms such as powders, granules, powder granules, hydrates, aqueous solvents, emulsions, liquids, oils, aerosols, microcapsules, pastes, coatings, fumigants, fumigants and trace dispersers for use.

[0066] Examples of carriers used as formulation adjuvants include solid carriers and liquid carriers. Solid carriers can be used in the form of powder carriers and granular carriers, for example, clay, talc, diatomaceous earth, zeolite, montmorillonite, bentonite, kaolinite, kaolin, pyrophyllite, wax stone, acid clay, activated clay, attapulgite, attapulgite, etc. The carrier materials include minerals such as clay, limestone, calcite, marble, vermiculite, perlite, pumice, silica, silica sand, 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, slaked lime and sodium bicarbonate; synthetic inorganic substances such as amorphous silicon dioxide (white carbon, fumed silica, etc.) and titanium dioxide; plant carriers such as wood powder, corn stalks (cobs), walnut shells (nut skins), fruit cores, rice husks, coconut shells, sawdust, bran, soybean flour, cellulose powder, starch, dextrin and sugars (lactose, sucrose, etc.); various polymer carriers such as cross-linked lignin, cationic gel, gelatin gelled by heating or multivalent metal salts, water-soluble polymer gel (agar, etc.), chlorinated polyethylene, chlorinated polypropylene, polyvinyl acetate, polyvinyl chloride, ethylene / vinyl acetate copolymers and urea / formaldehyde resins.

[0067] Examples of the liquid carrier include: aliphatic solvents such as paraffins (normal paraffins, isoparaffins, cycloparaffins); aromatic solvents such as xylene, alkylbenzenes, alkylnaphthalenes, and solvent naphtha; mixed solvents such as kerosene; motor oils such as purified high-boiling aliphatic hydrocarbons; alcohols such as methanol, ethanol, isopropanol, butanol, and cyclohexanol; polyols such as ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, hexylene glycol, polyethylene glycol, and polypropylene glycol; polyol derivatives such as propylene glycol ethers; acetone, acetophenone, cyclohexanone, methylcyclohexanone And ketones such as γ-butyrolactone; esters such as fatty acid methyl ester (coconut oil fatty acid methyl ester), ethylhexyl lactate, propylene carbonate and dibasic acid methyl ester (dimethyl succinate, dimethyl glutamate, dimethyl adipate); nitrogen-containing solvents such as N-alkyl pyrrolidones 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-pentanoic acid methyl ester and N-acylmorpholine solvents (CAS No.887947-29-7, etc.); water, etc.

[0068] Surfactants used as formulation adjuvants include nonionic surfactants, anionic surfactants, cationic surfactants, amphoteric surfactants, silicone surfactants, fluorine-based surfactants, and biosurfactants. Examples of 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 alkylphenyl ethers, polyoxyethylene dialkylphenyl ethers, polyoxyethylene alkylphenyl ether formalin condensates, polyoxyethylene / polyoxypropylene block polymers, alkyl polyoxyethylene / polyoxypropylene block polymer ethers, alkylphenyl polyoxyethylene / polyoxypropylene block polymer ethers, polyoxyethylene alkylamines, polyoxyethylene fatty acid amides, polyoxyethylene fatty acid diphenyl ethers, polyoxyethylene benzylphenyl (or phenylphenyl) ethers, polyoxyethylene styrylphenyl (or phenylphenyl) ethers, polyoxyethylene castor oils, polyoxyethylene hydrogenated castor oils, and alkylglycosides.

[0069] Examples of the anionic surfactant include sulfates such as alkyl sulfates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkylphenyl ether sulfates, polyoxyethylene benzyl (or styryl) phenyl (or phenylphenyl) ether sulfates, and polyoxyethylene / polyoxypropylene block polymer sulfates; paraffin (alkane) sulfonates, α-olefin sulfonates, dialkyl sulfosuccinates, alkylbenzene sulfonates, monoalkylnaphthalene sulfonates or dialkylnaphthalene sulfonates, naphthalene sulfonate / formalin condensates, alkyl diphenyl ether disulfonates, lignin Sulfonates such as sulfonates, polyoxyethylene alkylphenyl ether sulfonates and polyoxyethylene alkyl ether sulfosuccinic acid half esters; carboxylates such as fatty acids, resin acids, polycarboxylic acids, alkyl ether carboxylates, alkenyl succinic acid, N-acylamino acids and cycloalkanoic acid; phosphates such as polyoxyethylene alkyl ether phosphates, polyoxyethylene monoalkylphenyl ether phosphates or polyoxyethylene dialkylphenyl ether phosphates, polyoxyethylene benzyl (or styryl) phenyl (or phenylphenyl) ether phosphates, polyoxyethylene / polyoxypropylene block polymer phosphates and alkyl phosphates, etc.

[0070] Examples of the cationic surfactant include salts of amines such as alkylamine and alkyl pentamethylpropylenediamine; salts of ammoniums such as alkyltrimethylammonium, methylpolyoxyethylenealkylammonium, alkylpyridinium, monoalkylmethylated ammonium or dialkylmethylated ammonium, alkyldimethylbenzalkonium, and benzethonium (octylphenoxyethoxyethyldimethylbenzylammonium); and the like.

[0071] Examples of the amphoteric surfactant include dialkyldiaminoethyl betaine, alkyldimethylbenzyl betaine, and lecithin (phosphatidylcholine, phosphatidylethanolamine, and the like).

[0072] Examples of the silicone-based surfactant include trisiloxane ethoxylate and the like.

[0073] Examples of the fluorinated surfactant include perfluoroalkyl carboxylates, perfluoroalkyl sulfonates, and perfluoroalkyl trimethyl ammonium salts.

[0074] Examples of the biosurfactant include sophorolipids, rhamnolipids, trehalolipids, mannosyl alditol lipids, cellobiose lipids, glucose lipids, fatty acid oligosaccharide esters, penicillic acid, corynomycolic acid, agaritinic acid, surfactin, serrawettin, viscosin, lichenin, actin, emulsan, and arasan.

[0075] Other formulation adjuvants include: inorganic salts (sodium, potassium, etc.) used as pH adjusters; water-soluble salts such as salt; xanthan gum, guar gum, carboxymethyl cellulose, polyvinyl pyrrolidone, carboxyvinyl polymers, acrylic acid polymers, polyvinyl alcohol, starch derivatives, water-soluble polymers (polysaccharides, etc.), alginic acid and its salts, etc. used as thickeners; metal stearate, sodium tripolyphosphate, sodium hexametaphosphate, etc. used as disintegrating and dispersing agents; benzoic acid and its salts, sorbic acid and its salts, propionic acid and its salts, p-hydroxybenzoic acid, methyl p-hydroxybenzoate, 1,2-benzothiazoline-3- Ketones, etc.; sodium polyphosphate, sodium polyacrylate, sodium lignin sulfonate, sodium citrate, sodium gluconic acid / glucose enanthate, ethylenediaminetetraacetic acid and its disodium salt or ammonium salt, etc. used as supplements; pigments, dyes, etc. used as colorants; fluorine-based defoamers, silicone-based defoamers, ethylene oxide / propylene oxide copolymers, etc. used as defoamers; phenol-based antioxidants, amine-based antioxidants, sulfur-based antioxidants, phosphoric acid-based antioxidants, etc. used as antioxidants; salicylic acid-based ultraviolet absorbers, benzophenone-based ultraviolet absorbers, etc. used as ultraviolet absorbers; quicklime, magnesium oxide, etc. used as desiccants; as well as spreading agents and phytotoxicity reducing agents, etc.

[0076] The preparations may be used directly or diluted with a diluent such as water to a predetermined concentration. The concentration of compound (I) when diluted is preferably in the range of 0.0001 to 1% by weight. The same applies to tautomers of compound (I).

[0077] These preparations contain 0.1 to 90% by weight, more preferably 0.2 to 50% by weight of compound (I) as an active ingredient to prepare the preparation. In addition, the use amount of compound (I) is 0.005 to 50 kg, more preferably 0.03 to 30 kg per hectare of agricultural and horticultural land such as dry fields, paddy fields, orchards and greenhouses. The same is true for the tautomers of compound (I). Their use concentration and use amount vary according to dosage form, use period, method of use, use place and target plant, etc., and therefore can be increased or decreased without being restricted to the above-mentioned range.

[0078] (Other active ingredients)

[0079] The environmental stress tolerance enhancer in the present embodiment can also be combined with other known active ingredients to improve the performance of the environmental stress tolerance enhancer and use it, or to give an effect different from the environmental stress tolerance enhancement and use it. As other known active ingredients, known environmental stress tolerance enhancers, known plant growth regulators, fungicides, insecticides, acaricides, nematicides and active ingredients contained in herbicides can be listed.

[0080] Examples of known active ingredients of agents for improving environmental stress tolerance include seaweed extracts, corn extracts, microalgae, mycorrhizae, humic acid, fulvic acid, oxidized glutathione, L-proline, glycine betaine, 5-aminolevulinic acid, 2-hexenal, trehalose, silicic acid, nicotinic acid, acetic acid, and ethanol.

[0081] Examples of known active ingredients of plant growth regulators include aminoethoxyvinylglycine, chlormequat chloride, chlorpropamide, cyprodinil, furanil, diaminobutyric acid, ethephon, flumequat, chlorfenapyr, gibberellin, mepiquat chloride, methylcyclopropene, benzylaminopurine, paclobutrazol, prohexadione, thidiazuron, tributylphosphorotrithioate, trinexapac-ethyl, uniconazole, sodium 1-naphthylacetate, 1-naphthylacetamide, 1-methylcyclopropene, 4-CPA (4-chlorophenoxyacetic acid), MCPB (ethyl 2-methyl-4-chlorophenoxybutyrate), pyralid, indolebutyric acid, indole ester, calcium formate, chlormequat chloride, choline, cyanamide, dichlorprop, isodecanol, sorbitan trioleate, and 1-naphthylacetate. triole), nicosulfuron, cypermethrin, butralin, prohydrojasmon, anisiflupurin and pendimethalin, etc.

[0082] Examples of effective ingredients suitable for use as fungicides include nucleic acid anabolism inhibitors, fungicides acting on the cytoskeleton and motor proteins, respiration inhibitors, amino acid / 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 biopesticides / bioderived pesticides with multiple mechanisms of action.

[0083] Specifically, examples of the nucleic acid anabolic inhibitor include benalaxyl, benalaxyl-M or kiralaxyl, furalaxyl, metalaxyl, metalaxyl-M or mefenoxam, furamide, oxadixyl, bremoxam, dimethoate, pyrimidine, oxadixyl, oxamoxadone, octhilone and oxolinic acid.

[0084] In addition, examples of fungicides that act on the cytoskeleton and motor proteins include benomyl, carbendazim, thiabendazole, thiabendazole, thiabendazole, thiabendazole-methyl, ethidium bromide, ethaconazole, pencycuron, zoxadiazole, fluobenzamide, fluopicolide, cyanooxystrobin, metrafenone, and pyriofenone.

[0085] In addition, examples of respiratory inhibitors include difluanid, fenazaquin, tolfenpyrad, oxadone, benzovindiflupyr, bixafen, boscalid, carboxin, fenuram, flubeneteram, fluindapyr, fluopyram, flutolanil, flubenpyram, fluopyram, indopyram, isopyram, isopyram, pyraclostrobin, pyraclostrobin, oxadone, oxadone, pyraclostrobin, pyraclostrobin, bixafen, flutolanil, thiopyram, thiopyram, oxadone, pyraclostrobin ... astrobin), oxathiapiprolin, fenamidone, enoxabiodinium, flufenoxystrobin, fluoxastrobin, kresoxim-methyl, tolystrobin, fenoxystrobin, tetrazobactam, orysastrobin, picoxystrobin, pyraclostrobin, oxathiapiprolin, pyraclostrobin, pyraclostrobin, pyribencarb, chlorpyrifos, trifloxystrobin, indazolesulfamide, cyazofamid, pyridine, florylpicoxamid, metarylpicoxamid, binacarb, dinocap, fluazinam, meptyldinocap, triphenyltin acetate, triphenyltin chloride, triphenyltin hydroxide, sithiostrobin and pyraclostrobin, etc.

[0086] Examples of the amino acid and protein biosynthesis inhibitors include cyprodinil, myclobutanil, pyrimethanil, blasticidin S, kasugamycin, streptomycin, and oxytetracycline.

[0087] In addition, examples of the signal transduction inhibitor include proquinazid, quinoline, fludioxonil, ethoxyconazole, sclerotinol, fenpiclonil, iprodione, procymidone, and vinclozolin.

[0088] In addition, as inhibitors of lipid biosynthesis or transport / cell membrane structure or function, there can be listed: EDDP, IBP, IPA, dichlorvos, biphenyl, chloroanisole, chloranil (CNA), tetrabendazim, pentachloronitrobenzene (PCNB), tetrachloronitrobenzene (TCNB), methyl tolclofos, iodopropynyl butylcarbamate (iodocarb), cymoxanil, thiophanate-methyl, extracts of Melaleuca alternifolia (tea oil tree), mixtures of plant oils (eugenol, geraniol, thymol), natamycin, fluoxapiprolin and fluthiazolin, etc.

[0089] Examples of the cell membrane sterol biosynthesis inhibitor include pentoconazole, bifenthrin, oxadiazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, eticonazole, fenbuconazole, fluoxytioconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imazalil, imipenem, ipfentrifluconazole, clofoconazole, metconazole, myclobutanil, oxpoconazole, pyraclostrobin, penconazole, prochloraz, propiconazole, prothioconazole, silyfloxacin, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, trichlorfonazole, flufenimol, flufenimol, pyraclostrobin, pyraclostrobin, triamcinol, methyl (2RS)-2-[2-chloro-4-(4-chloro- [phenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propionate, 1-((1H-1,2,4-triazol-1-yl)methyl)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methylcyclopentane-1-ol, 2-((1H-1,2,4-triazol-1-yl)methyl)-3-(4-chlorobenzyl)-2-hydroxy-1-methylcyclopentane-1-carboxylic acid methyl ester, aldimol, dodecacyclic morpholine, fenhexamid, tridecacyclic morpholine, fenpropidin, spiroxamine, fenhexamid, fenpyrazamine, barnyard grass carbendazim, naftifine and terbinafine, etc.

[0090] Examples of the cell wall biosynthesis inhibitor include polyoxin, benthiopyrad (benthiopyrad isopropyl ester), dimethomorph, flumorph, valinomycin, mandipropamid, pyrimorph, and valazin.

[0091] Examples of the melanin biosynthesis inhibitor include pyrochloridone, tricyclazole, cyproconazole, diclofenac, cyanamide, and tolprocarb.

[0092] Resistance inducers for host plants include: acibenzolar-S-methyl, propanthiazol, tiadinil, isothiazol, laminarin, giant knotweed extract, Bacillus mycoides isolate J, cell wall of Saccharomyces cerevisiae LAS117 strain, fosetyl alcohol (fosetyl aluminum, fosetyl potassium, fosetyl sodium), phosphoric acid, phosphates and dichlobentiazox, etc.

[0093] As the multi-site fungicide, there can be mentioned: ferbam, mancozeb, maneb, metiram, propineb, thiram, zinc thiazole, mancozeb, ziram, maneb, dithiazide, dicyanoanthraquinone, dichlofluanid, tolylfluanid, octadine, octadine acetate, octadine benzenesulfonate, copper or various copper salts (for example, basic copper chloride, copper hydroxide, basic copper sulfate, copper sulfate, organic copper (hydroxyquinoline copper), copper nonylphenolsulfonate, DBEDC, etc.), sulfur, captan, captol, folpet, TPN (chlorothalonil), quinoxaline ring system (mite killing manganese), fluoroimide and sulfamethoxam, etc.

[0094] Examples of biopesticides / bio-derived pesticides having multiple mechanisms of action include Bacillus subtilis AFS032321, Bacillus amyloliquefaciens QST713, Bacillus amyloliquefaciens FZB24, Bacillus amyloliquefaciens MBI600, Bacillus amyloliquefaciens D747, Bacillus amyloliquefaciens F727, Gliocladium CR-7, Gliocladium J1446, Pseudomonas chlororaphis AFS009, Streptomyces glaucum K61, Streptomyces lydicus WYEC108, Trichoderma aureum I-1237, Trichoderma aureum LU132, Trichoderma aureum SC1, Trichoderma acanthosporum T34, an extract derived from Citrus amygdalus, and an extract derived from the cotyledons of lupin seedlings.

[0095] Other compounds for fungicide use include chloroinconazide, cintamidine, flumetylsulforim, flutoxazone, cymoxanil, cymoxanil, dipymetitrone, dodine, chloranil, pyrimidine, sulfamethoxam, flutianil, harpin, inorganic salts (bicarbonates (sodium bicarbonate, potassium bicarbonate), potassium carbonate), ipflufenoquin, ipflufenoquin, natural origin, motor oil, organic oil, picarbutrazox, pyridachlometyl, quinofumelin, tebufloquin, chloranil (bactericide), imidazobactam, jinggangmycin, aminopyrifen, and shiitake mycelium extract.

[0096] Examples of effective ingredients suitable for insecticide use include: acetylcholinesterase (AChE) inhibitors, GABA-agonist chloride channel blockers, sodium channel modulators, nicotinic acetylcholine receptor (nAChR) competitive modulators, nicotinic acetylcholine receptor (nAChR) allosteric modulators, glutamate-agonist chloride channel (GluCl) allosteric modulators, juvenile hormone analogs, other nonspecific (multi-site) inhibitors, chord organ TRPV channel modulators, mite growth inhibitors acting on CHS1, insect midgut membrane disruptors derived from microorganisms, mitochondrial ATP synthase inhibitors, oxidative phosphorylation uncouplers that disrupt proton gradients, nicotinic Acetylcholine receptor (nAChR) channel blockers, chitin biosynthesis inhibitors acting on CHS1, chitin biosynthesis inhibitors (type 1), molting inhibitors (Diptera), ecdysone (molting hormone) receptor agonists, octopamine receptor agonists, mitochondrial electron transport system complex III inhibitors, mitochondrial electron transport system complex I inhibitors (METI), voltage-dependent sodium channel blockers, acetyl CoA carboxylase inhibitors, mitochondrial electron transport system complex IV inhibitors, mitochondrial electron transport system complex II inhibitors, ryanodine receptor modulators, chord organ modulators, GABA-agonist chloride ion channel allosteric modulators and baculovirus, etc.

[0097] Examples of acetylcholinesterase (AChE) inhibitors include alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, NAC (carbaryl), carbofuran, carbosulfan, ethiofencarb, BPMC (fenbutylcarb), fenothiocarb, formetanate, furathiocarb, and fenthiocarb. b), MIPC (isoprocarb), methiocarb, methomyl, MTMC (methoxamyl), oxamyl, pirimicarb, PHC (propoxur), thiodicarb, thiofanox, triazamate, trimetacarb, XMC, MPMC (methoxal), acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, Cadusafos, chlorethoxyphos, CVP, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, CYAP, demeton-S-methyl, diazinon, DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfophos ton), EPN, ethion, ethoprophos, famphur, fenamiphos, MEP (fenthion), MPP (fenthion), fosthiazate, heptenophos, imiciafos, isofenphos, isopropyl O-(methoxyaminothiophos) salicylate), isoxathion, malathion, mecarbam, methamidophos, DMTP (methidathion),mevinphos, monocrotophos, BRP, omethoate, oxydemeton-methyl, parathion, parathion-methyl, PAP, phorate, phosalone, PMP, phosphamidon, phoxim, pirimiphos-methyl, profenofos enofos), propetamphos, prothiofos, pyraclofos, pyridafenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, CVMP, thiometon, triazophos, DEP, and vamidothion.

[0098] Examples of GABA agonist chloride channel blockers include chlordane, endosulfan, dienochlor, ethiprole, fipronil, pyriprole, and nicofluprole.

[0099] Examples of sodium channel modulators include acralthrin, allethrin (acralthrin, d-cis-trans-, d-trans-isomers), bifenthrin, bioallethrin (bioallethrin, S-cyclopentenyl-isomers), bioresmethrin, chloroprallethrin, chlorfenson, cycloprothrin, cyfluthrin (cyfluthrin, β-isomer), cyfluthrin (cyfluthrin, λ-, γ-isomers), chlorfenthrin, Cypermethrin (cypermethrin, α-, β-, θ-, ζ-isomers), cypermethrin [(1R)-trans isomer], deltamethrin, dimefluthrin, ethynethrin [(EZ)-(1R)-isomer], esfenvalerate, ethofenprox, fenpropathrine, fenvalerate, flubrocythrinate, flucythrinate ), flumethrin, fluvalinate (τ-fluvalinate), halfenprox, imiprothrin, kadethrin, metofluthrin, momfluorothrin, ε-metofluthrin, ε-methoxyfluthrin, permethrin, phenothrin [(1R)-trans isomer], prallethrin, profluthrin in), pyrethrin, resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomer], tralomethrin, transfluthrin, DDT, methoxychlor, aldrin, dieldrin and lindane, etc.

[0100] Examples of competitive modulators of nicotinic acetylcholine receptors (nAChR) include acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, nicotine sulfate (nicotine), sulfoxaflor, flupyradifurone, dicloromezine, fenmezoditiaz, and trifluanid.

[0101] Examples of the nicotinic acetylcholine receptor (nAChR) allosteric modulators include spinetoram, spinosad, flupyrimine, and GS-omega / kappa HXTX-Hv1a peptide.

[0102] Examples of the glutamate agonist chloride channel (GluCl) allosteric modulators include abamectin, emamectin-benzoate, lepimectin, and milbemectin.

[0103] Examples of the juvenile hormone analogs include hydroprene, kinoprene, methoprene, fenoxycarb, and pyriproxyfen.

[0104] Other nonspecific (multi-site) inhibitors include methyl bromide, other halogenated alkanes, chloropicrin, sodium aluminum fluoride, sulfuryl fluoride, borax, boric acid, disodium octaborate, sodium metaborate, tartar emetic, dazomethane, metam ammonium, metam sodium, and methyl isothiocyanate.

[0105] Examples of the chord organ TRPV channel modulators include pymetrozine, pyrifluquinazon, and afidopyropen.

[0106] Examples of mite growth inhibitors that act on CHS1 include clofentezine, diflovidazin, hexythiazox, and etoxazole.

[0107] Examples of insect midgut membrane disruptors derived from microorganisms include Bacillus thuringiensis subsp. israelensis, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. tenebrionis, proteins contained in Bt crops (Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Bb, Cry34Ab1 / Cry35Ab1), and Bacillus sphaericus.

[0108] Examples of the mitochondrial ATP synthase inhibitor include diafenthiuron, azolisin, hydroxytricyclohexyltin (cyclohexyltin), fenbutatin, BPPS (propargyl) and fenthion.

[0109] Examples of the oxidative phosphorylation uncoupler that disturbs the proton gradient include chlorfenapyr, DNOC, and sulfluramid.

[0110] Examples of the nicotinic acetylcholine receptor (nAChR) channel blocker include thiosulfuron, cartap hydrochloride, thiocarb, thiophanate-methyl sodium salt, and thiophanate-methyl.

[0111] Examples of the chitin biosynthesis inhibitor that acts on CHS1 include bistrifluan, chlorfenapyr, diflubenzuron, flufenoxuron, flufenoxuron, hexaflumuron, fluazifop, noflubenzuron, nobifluumuron, fluazifop, thiophanate-methyl and tetracycline.

[0112] Examples of chitin biosynthesis inhibitors (type 1) include thiazolinone and the like.

[0113] Examples of molting inhibitors (Diptera insects) include cyromazine and the like.

[0114] Examples of the ecdysone (molting hormone) receptor agonist include chromafenazate, chlorfenapyr, methoxyfenapyr, and tebufenozide.

[0115] Examples of the octopamine receptor agonist include amitraz and the like.

[0116] Examples of the mitochondrial electron transport system complex III inhibitor include hydrazone, acequinoxaline, pyrimidifen, flupyroxystrobin, and bifenazate.

[0117] Examples of the mitochondrial electron transport system complex I inhibitor (METI) include fenazaquin, fenpyrad, pyridaben, pyrimidifen, tebufenpyrad, tolfenpyrad, and rotenone.

[0118] Examples of the voltage-dependent sodium channel blocker include indoxacarb and metaflumizone.

[0119] Examples of the acetyl-CoA carboxylase inhibitor include spirodiclofen, spiromesifen, spiropidion, spidoxamat, spirobudifen, and spirotetramat.

[0120] Examples of the mitochondrial electron transport system complex IV inhibitor include aluminum phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide (calcium cyanide / sodium cyanide), and potassium cyanide.

[0121] Examples of the mitochondrial electron transport system complex II inhibitor include cypermethrin, ethoxifen, cyfluthrin, pyflubumide, and cyclobutrifluram.

[0122] Examples of the ryanodine receptor modulator include chlorantraniliprole, cyantraniliprole, cyclonantraniliprole, flubendiamide, tetraniliprole, fluchlordiniliprole, thiotraniliprole, tetrachlorantraniliprole, cyhalodiamide, and cyproflanilide.

[0123] Examples of the string organ regulator include flonicamid and the like.

[0124] Examples of the GABA agonist chloride ion channel allosteric modulators include bromofenac, fluazifop, and isocycloseram.

[0125] Examples of the baculovirus include Cydia pomonella granulovirus (GV), Thaumatotibia leucotreta granulovirus (GV), Anticarsis gemmatalis MNPV, and Helicoverpa armigera NPV.

[0126] Other insecticides, acaricides and nematicides include: azadirachtin, benzamectin, bromocriptine, quinoxaline ring system (mite), trichlorodiphenyltrichloroethane (Kelson), lime sulfur, mancozeb, trifluoromethylpyrifos, sulfur, acynonapyr, amidoflumet, benzpyrimoxan, fluazaindolizine, flufenoxone, fluhexafon, flupentiofenox, flometoquin, metaldehyde, tyclopyrazoflor, dimpropyridaz, triflumic acid trifluenfuronate, indazapyroxamet, sulfilimine, Burkholderia bacteria, Culex pipiens Wolbachia Zap strain, Nepeta tenuifolia extract, fatty acid monoesters with glycerol or propylene glycol, neem oil, motor oil, rapeseed oil, blended oil, starch, reduced starch saccharide, sodium oleate, ferric phosphate, nemadectin, Beauveria bassiana, Metarhizium anisopliae strain (F52), Paecilomyces fumosorum Apopka strain (97), diatomaceous earth, DCIP (dichloroisopropyl ether), DD (1,3 dichloropropylene), levamisole hydrochloride, morantel tartrate, and tioxazafen, etc.

[0127] Examples of effective ingredients suitable for use as herbicides include acetolactate synthesis (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) inhibitory compounds, phenoxyacetic acid compounds, hydroxyphenylpyruvate dioxygenase (HPPD) inhibitory compounds, and triazine compounds.

[0128] Examples of the acetolactate synthesis (ALS) inhibitor compounds include imazamethabenz and imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, amidosulfuron, azimsulfuron, bensulfuron and bensulfuron-methyl, chlorisulfuron, and chlorisulfuron. muron and chlorimuron-methyl, chlorimuron-ethyl, chlorsulfuron, chlortoluron, cyclosulfamuron, ethametsulfuron and ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flu Flupyrsulfuron-methyl and its salts, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron and its salts, iodosulfuron-methyl and its salts, mesosulfuron, mesosulfuron-methyl, metazosulfuron, mesosulfuron-methyl tsulfuron), metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron,Sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron and its salts, triflusulfuron, triflusulfuron-methyl, tritosulfuron, imazamethabenz-methyl, bispyribac-butyl sodium), cloransulam, cloransulam-methyl, diclosulam, florasulam, flucarbazone and its salts, flumetsulam, metosulam, orthosulfamuron, penoxsulam, pyroxsulam, propoxycarbazone and its salts, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac and its salts, pyroxsulam, thiencarbazone, thiencarbazone-methyl and triafamone, etc.

[0129] Examples of the amino acid compound include bialaphos and salts thereof, glufosinate and salts thereof, glufosinate-ammonium and salts thereof, and glyphosate and salts thereof.

[0130] Examples of the cyclohexanedione compounds include fenthion, butroxydim, clethodim, cloproxydim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, and tralkoxydim.

[0131] Examples of the acetamide compound include naproxamide, dimethachlor, pethoxamid, acetochlor, alachlor, CDAA, butenachlor, delachlor, diethatyl-ethyl, propisochlor, prynachlor, butachlor, dimethenamid, dimethenamid-p, metazachlor, metolachlor, metolachlor, pretilachlor, propachlor, thenylchlor, flufenacet, and mefenacet.

[0132] Examples of the bipyridylium compound include cyperquat, morfamquat, diquat, and paraquat.

[0133] Examples of the allyloxyphenoxypropionic acid compounds include clodinafop, clodinafop-propargyl, clofop, cyhalofop-butyl, diclofop, diclofop-methyl, diclofop-P-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fluazifop, butyl fluazifop, and butyl fluazifop. haloxyfop, haloxyfop-methyl, haloxyfop-P-methyl, isoxapyrifop, metamifop, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-P-ethyl and quizalofop-P-tefuryl, etc.

[0134] Examples of the carbamate compounds include asulam, carbetamide, desmedipham, chlorprocarb, phenisopham, cycloate, dimepiperate, pebulate, tiocarbazil, vernolate, barban, chlorbufam, chlorpropham, propham, swep, phenmedipham, butylate, EPTC, esprocarb, molinate, orbencarb, prosulfocarb, pyributicarb, benthiocarb, and triallate.

[0135] Examples of the pyridine compound include aminopyralid, clopyralid, diflufenican, dithiopyr, fluridone, fluroxypyr, halauxifen, florpyrauxifen, picloram and its salts, picolinafen, thiazopyr, and triclopyr and its salts.

[0136] Examples of the urea compound include benzothiazole, bromuron, buturon, chlorbromuron, chloroxuron, difenoxuron, dimefuron, ethidimuron, fenuron, fluothiuron, metobenzuron, metobromuron, metoxuron, monolinuron, and metobenzuron. The following are some of the drugs listed in the patent application: CMU), neburon, parafluron, siduron, thiazafluron, chlorotoluron, daimuron, DCMU, fluometuron, isoproturon, linuron, methabenzthiazuron, tebuthiuron, cumyluron, karbutilate and isouron.

[0137] Examples of the dinitroaniline compound include benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, isopropalin, nitrarine, profluralin, oryzalin, pendimethalin, prodiamine, and trifluralin.

[0138] Examples of the protoporphyrinogen oxidase (PPO) inhibitory compound include acifluorfen, aclonifen, azafenidin, bifenox, chlomethoxynil, ethoxyfen, ethoxyfen-ethyl, fomesafen, fluazolate, fluoroglycofen, fluoroglycofen-ethyl, halosafen, lactofen, oxyfluorfen, butafenacil, epyrifenacil, CNP, fluorodifen, CFNP, NIP, oxyfluorfen, chlorpyrifos, thalim), flumipropyn, carfentrazone, carfentrazone-ethyl, cinidon-ethyl, flumiclorac-pentyl, flumioxazin, fluthiacet, fluthiacet-methyl, oxadiargyl, oxadiazon, pentoxazone, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, benzfendizone, profluazol and flufenpyr-ethyl, etc.

[0139] Examples of phenoxyacetic acid compounds include 2,4,5-T, 2,4-D and salts thereof, 2,4-DB and salts thereof, clomeprop, dichlorprop, fenoprop, MCPA and salts thereof, MCPB and salts thereof, MCPP and salts thereof, and mecoprop-P and salts thereof.

[0140] Examples of hydroxyphenylpyruvate dioxygenase (HPPD) inhibitory compounds include benzobicyclon, benzofenap, bicyclopyrone, isoxaflutole, mesotrione, pyrasulfotole, pyrzolate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, topramezone, fenquinotrione, and tolpyralate.

[0141] Examples of the triazine compound include atraton, aziprotryne, chlorazine, cyprazine, desmetryn, dipropetryn, eglinazine-ethyl, ipazine, methoprene, procyazine, proglinazine, prometon, propazine, sebuthylazine, secbumetophenone, and succinimide. n), terbumeton, trietazine, ametryne, atrazine, cyanazine, dimethametryne, hexazinone, indaziflam, metamitron, metribuzin, prometryne, CAT, simetryne, terbuthylazine, terbutryn and triaziflam, etc.

[0142] In addition, other compounds used as herbicides include amicarbazone, ethiozin, isomethiozin, aminocyclopyrachlor, aminotriazole, anilofos, piperophos, beflubutamid, benazolin, benfuresate, bentazone, bromacil, isocil, bromobutyric acid, and chlorpyrifos. Bromobutide, bromofenoxim, bromoxynil, butamifos, DMPA, TCTP (methyl chlorphthalate), cafenstrole, PAC, brompyrazon, chlorthal, clomazone, cumyluron, MDBA and its salts, chloramben, TCBA (2,3,8-TBA), benazolin-ethyl, chlorfequat nac), chlorfenprop, DBN, DCBN, cinmethylin, methiocarb, amitrole, flamprop-M, fosamine, methyldymron, monalide, MSMA, difenzoquat, diflufenzopyr, endothall and its salts, ethofumesate, etobenzanid, benzene fenoxasulfone, fentrazamide, flupoxam, fluorochloridone, flurtamone, indanofan, tridiphane, ioxynil, ipfencarbazone, isoxaben, triaziflam, lenacil, methylarsonic acid, naptalam, flurochloridone,norflurazon, oxaziclomefone, pinoxaden, butyralid, CMMP, propanil, propyzamide, pyridate, pyroxasulfone, promacyl, quinclorac, quinmerac, terbacil, cyclopyrimorate, florpyrazone uxifen-benzyl), lancotrione and its salts, cyclopyranil, bixlozone, tetflupyrolimet, dimesulfazet, dinosam, dinoseb (DNBP), DNOC, telofen, etinofen, medinoterb, disodium methylarsonic acid (DSMA), cacodylic acid, diphenamid , naproanilide, tebutam, bensulide, dalapon, TCA, mefluidide, perfluidone, CAMA, tiafenacil, trifludimoxazin, rimisoxafen, fenpyrazone, dioxopyritrione, cypyrafluone, bipyrazone ), benquitrione, fluchloraminopyr, pyriflubenzoxim, flufenoximacil, iptriazopyrid, flusulfinam, broclozone, indolauxipyr, icafolin, pyraquinate, flupropanate and its salts, and D-limonene, etc.

[0143] [Method for improving environmental stress tolerance of plants]

[0144] The environmental stress tolerance enhancer in the present embodiment can be used in farmland or non-agricultural land such as dry fields, paddy fields, lawns and orchards, for example. In addition, the environmental stress tolerance enhancer in the present embodiment can be used by all fertilization methods, for example, it can be used by the following method: spraying to stems and leaves, mixing into water supply, spraying to soil, injecting into subsoil using an injector, including seed treatment of the treatment of bulbs and tubers, and direct fertilization of plants, etc. Therefore, the environmental stress tolerance enhancement method in the present embodiment includes the step of using the above-mentioned environmental stress tolerance enhancer to apply fertilizer.

[0145] The application by mixing into the water supply is carried out, for example, by supplying water to crops or placing granules into the surface water of paddy fields. In one example, the concentration of the active ingredient in the water supply is 0.5 to 500 mg / L, preferably 1 to 300 mg / L. In addition, the amount of the active ingredient used in the case of placing it into the surface water is, for example, 0.5 to 5000 g, preferably 3 to 3000 g per 10a of paddy fields.

[0146] For application by spraying on stems and leaves or spraying on soil, for example, granules are applied to the planting hole or its periphery when transplanting seedlings, or granules and hydrating agents are applied to seeds, plants or soil around plants. In addition, after spraying on soil, it is sometimes preferable to stir with soil. In the case of spraying on stems and leaves or spraying on the soil surface, the amount of active ingredient used is 100% relative to 1 m 2 The amount for agricultural and horticultural use is, for example, 0.5 to 5000 mg, preferably 3 to 3000 mg.

[0147] In the application by seed treatment, the agent is attached to the seeds by mixing and stirring a hydrating agent, a powder, etc. with the seeds, or by immersing the seeds in a diluted hydrating agent, etc. In addition, seed treatment also includes seed coating treatment. The amount of the active ingredient used in the case of seed treatment is, for example, 0.005 to 10,000 g, preferably 0.05 to 1,000 g, relative to 100 kg of seeds. For seeds treated with agricultural and horticultural agents, they can be used in the same way as ordinary seeds.

[0148] It should be noted that the concentration and amount used vary according to the formulation, use period, method of use, use location and target crop, and therefore can be increased or decreased without being restricted to the above range. As described above, compound (I) and its tautomers show excellent environmental stress tolerance improvement effects on a wide range of plants.

[0149] [Utilization of agents that enhance environmental stress tolerance]

[0150] As described above, the environmental stress tolerance-enhancing agent of the present embodiment exhibits an excellent environmental stress tolerance-enhancing effect in treated plants.

[0151] 〔Summarize〕

[0152] As described above, the agent for improving plant environmental stress tolerance according to the first aspect of the present invention comprises, as an active ingredient, a compound represented by the following formula (I) or a tautomer thereof, or an agronomically acceptable salt thereof.

[0153] [Chemical formula 4]

[0154]

[0155] (In formula (I), R 1 and R 2 independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R 3 ~R 5 independently represents an alkyl group having 1 to 4 carbon atoms).

[0156] Furthermore, with respect to the agent for improving plant environmental stress tolerance according to aspect 2 of the present invention, preferably, in aspect 1, the compound represented by the formula (I) is ergothioneine.

[0157] In addition, with regard to the environmental stress tolerance enhancing agent for plants of scheme 3 of the present invention, it is preferred that, in scheme 1 or 2, tolerance to at least one environmental stress selected from high temperature stress, low temperature stress, freezing stress, salt stress, excess nutrient stress, dryness stress, excess water stress, ultraviolet stress, weak light stress and strong light stress is improved.

[0158] Furthermore, the agent for improving plant environmental stress tolerance according to aspect 4 of the present invention is, in any one of aspects 1 to 3, an agent for improving plant environmental stress tolerance is an agent for improving salt stress tolerance.

[0159] Furthermore, the agent for improving plant environmental stress tolerance according to aspect 5 of the present invention is, in any one of aspects 1 to 3, an agent for improving plant environmental stress tolerance is an agent for improving dryness stress tolerance.

[0160] Furthermore, the agent for improving plant environmental stress tolerance according to aspect 6 of the present invention is, in any one of aspects 1 to 3, an agent for improving plant environmental stress tolerance is an agent for improving high temperature stress tolerance.

[0161] Furthermore, the agent for improving plant environmental stress tolerance according to aspect 7 of the present invention is, in any one of aspects 1 to 3, an agent for improving plant environmental stress tolerance is an agent for improving plant environmental stress tolerance.

[0162] Furthermore, the agent for improving plant environmental stress tolerance according to aspect 8 of the present invention is, in any one of aspects 1 to 3, an agent for improving plant environmental stress tolerance is an agent for improving plant environmental stress tolerance.

[0163] Furthermore, the agent for improving plant environmental stress tolerance according to aspect 9 of the present invention is, in any one of aspects 1 to 3, an agent for improving plant environmental stress tolerance is an agent for improving ultraviolet stress tolerance.

[0164] Furthermore, the agent for improving plant environmental stress tolerance according to aspect 10 of the present invention is, in any one of aspects 1 to 3, an agent for improving plant environmental stress tolerance is an agent for improving strong light stress tolerance.

[0165] Furthermore, the agent for improving plant environmental stress tolerance according to aspect 11 of the present invention is, in any one of aspects 1 to 3, an agent for improving plant environmental stress tolerance is an agent for improving freezing stress tolerance.

[0166] Furthermore, the agent for improving plant environmental stress tolerance according to aspect 12 of the present invention is, in any one of aspects 1 to 3, an agent for improving plant environmental stress tolerance is an agent for improving low temperature stress tolerance.

[0167] Furthermore, a method for improving environmental stress tolerance of a plant according to aspect 13 of the present invention comprises treating the plant with the environmental stress tolerance improving agent according to any one of aspects 1 to 12.

[0168] The following examples are shown to further illustrate the embodiments of the present invention. Of course, the present invention is not limited to the following examples, and it is beyond doubt that various schemes can be adopted for details. Moreover, the present invention is not limited to the above-mentioned embodiments, and various changes can be made within the scope shown in the claims, and the embodiments obtained by appropriately combining the respectively disclosed technical means are also included in the technical scope of the present invention. In addition, all the documents recorded in this specification are cited as references.

[0169] Example

[0170] Hereinafter, L-(+)-ergothioneine is used to show the effect of the environmental stress tolerance improver of the present embodiment.It should be noted that, below, as the compound used for comparison, the glycine betaine as the compound different from the environmental stress tolerance improver of the present embodiment is used.It should be noted that, in the following description, L-(+)-ergothioneine is abbreviated as " EGT " sometimes, and glycine betaine is abbreviated as " GB ".

[0171] [Evaluation Example 1] Comparison of Tolerance Effects on Salt Stress

[0172] L-(+)-ergothioneine (Examples 1-2, Comparative Example 3) and glycine betaine (Comparative Examples 1-2, Comparative Example 4) were prepared to have the concentrations shown in the following Table 1. Commercially available EGT and GB were used, and pure water was used as a solvent.

[0173] Three Arabidopsis thaliana (Col-0) were inoculated per well of a 24-well cell culture plate, and 2 mL of a liquid culture medium was prepared by adding 1 wt % sucrose and 0.1 wt % agar powder to MS (Murashige Skoog) medium mixed salts (Fujifilm Wako Pure Chemical Industries, Ltd.).

[0174] In an artificial climate chamber set at room temperature of 22°C, the light period was set to 16 hours and the dark period was set to 8 hours. The light condition was set to a light intensity of 5000 lx in the center under fluorescent light irradiation. On the 4th day after sowing, EGT or GB was added to a prescribed concentration, and 24 hours later, a sodium chloride aqueous solution was added to a final concentration of 100 mM to give salt stress.

[0175] The number of plants that survived on the 10th day after sowing was counted, and the plant dieback rate was evaluated as an indicator of physiological disease. The evaluation results are shown in Table 1. The dieback rate and environmental stress inhibition rate were calculated according to the following formula.

[0176] Death rate (%)

[0177] ={1-(number of surviving plants / number of plants tested)}×100

[0178] Environmental stress inhibition rate (%)

[0179] ={1-(death rate of the area treated with the test compound / death rate of the area without treatment)}×100

[0180] [Table 1]

[0181] Table 1

[0182] Test compound Test compound concentration Salt stress Death rate Environmental stress inhibition rate Example 1 EGT 1mM have 14％ 81％ Example 2 EGT 0.1mM have 39％ 48％ Comparative Example 1 GB 1mM have 75％ 0％ Comparative Example 2 GB 0.1mM have 79％ 0％ Comparative Example 3 EGT 1mM none 0％ - Comparative Example 4 GB 1mM none 0％ - Comparative Example 5 - - have 75％ - Comparative Example 6 - - none 0％ -

[0183] As shown in Table 1, due to salt stress, physiological diseases such as chlorosis were observed in Arabidopsis, and 75% of the Arabidopsis tested died (Comparative Example 5). Even with the treatment with GB, the death caused by salt stress was not suppressed (Comparative Examples 1 and 2). In contrast, by treating with EGT, the death rate became 14% at 1 mM (Example 1) and 39% at 0.1 mM (Example 2), and the death caused by salt stress was suppressed.

[0184] [Evaluation Example 2] Comparison of Tolerance Effects to Dryness Stress

[0185] EGT (Example 3) was prepared so as to have the concentrations described in the following Table 2. A commercially available EGT was used, and pure water was used as a solvent.

[0186] In a plastic pot with a diameter of 60 mm and a height of 55 mm, one individual Arabidopsis thaliana (Col-0) was sown in each pot. A plastic deep dish with a diameter of 160 mm and a height of 28 mm was prepared, and 6 pots were set. As soil, 45 mL of vermiculite, 22.5 mL of granular culture soil (combined horticultural culture soil), and 22.5 mL of vermiculite were added to the pot in sequence.

[0187] In an artificial climate room set at room temperature of 22°C, the light period was set to 16 hours and the dark period was set to 8 hours. The light condition was set to a light intensity of 5000 lx in the center under fluorescent light irradiation. Water was supplied from the bottom and the water level was set to about 5 mm. 50 mL of EGT was added on the 22nd day after sowing, and water supply was stopped for 18 days from 2 days thereafter to give drought stress.

[0188] The number of surviving plants after 18 days of water withdrawal was counted, and the plant dieback rate was evaluated as an indicator of physiological disease. The evaluation results are shown in Table 2. The dieback rate and environmental stress inhibition rate were calculated according to the following formula.

[0189] Death rate (%)

[0190] ={1-(number of surviving plants / number of plants tested)}×100

[0191] Environmental stress inhibition rate (%)

[0192] ={1-(death rate of the area treated with the test compound / death rate of the area without treatment)}×100

[0193] [Table 2]

[0194] Table 2

[0195] Test compound Test compound concentration Dryness stress Death rate Environmental stress inhibition rate Example 3 EGT 1mM have 0％ 100％ Comparative Example 7 - - have 50％ - Comparative Example 8 - - none 0％ -

[0196] As shown in Table 2, physiological diseases such as wilting and necrosis were observed in Arabidopsis due to drought stress, and 50% of the tested Arabidopsis died (Comparative Example 7). On the other hand, all Arabidopsis survived the treatment with EGT (Example 3).

[0197] [Evaluation Example 3] Comparison of Tolerance Effects to Drought Stress

[0198] EGT (Example 4) or GB was prepared so as to have the concentrations described in Table 3 below.

[0199] (Comparative Example 9) Commercially available EGT and GB were used, and pure water was used as a solvent.

[0200] In a plastic pot with a diameter of 60 mm and a height of 55 mm, 90 mL of granular culture soil (combination horticultural culture soil) was added, and one cotton plant (manufactured by Tohoku Corporation) was sown per pot.

[0201] The plants were managed in a greenhouse set at a room temperature of 25° C. 50 mL of EGT or 50 mL of GB were added on the 23rd day after sowing, and water supply was stopped for 4 days starting from 4 days to give drought stress.

[0202] Leaves were collected 4 days after water withdrawal and photographed with a digital camera. Image analysis software WinROOF

[0203] (Mitani Shoji Co., Ltd.) The photographs of the leaves were analyzed to quantify the total leaf area and green leaf area.

[0204] The total leaf area and green leaf area were used to evaluate the leaf necrosis rate after 4 days of water withdrawal. The evaluation results are shown in Table 3. The leaf necrosis rate and environmental stress inhibition rate were calculated according to the following formula.

[0205] Leaf necrosis rate (%)

[0206] ={1-(green leaf area / total leaf area)}×100

[0207] Environmental stress inhibition rate (%)

[0208] ={1-(necrotic rate of leaves in the test compound-treated area / necrotic rate of leaves in the untreated area)}×100 [Table 3]

[0209] Table 3

[0210] Test compound Test compound concentration Dryness stress Leaf necrosis rate Environmental stress inhibition rate Example 4 EGT 0.1mM have 26％ 50％ Comparative Example 9 GB 0.1mM have 68％ 0％ Comparative Example 10 - - have 52％ - Comparative Example 11 - - none 0％ -

[0211] As shown in Table 3, physiological diseases such as wilting, chlorosis, and necrosis were observed in cotton due to drought stress, and 52% of the leaves of the tested cotton were necrotic (Comparative Example 10). Even with the treatment with GB, the necrosis caused by drought stress was not suppressed (Comparative Example 9). In contrast, the necrosis rate caused by drought stress was suppressed to 26% by the treatment with EGT (Example 4).

[0212] [Evaluation Example 4] Comparison of the effect of tolerance to high temperature stress

[0213] EGT (Example 5, Comparative Example 13) or GB (Comparative Example 12, Comparative Example 14) was prepared so as to have the concentrations shown in the following Table 4. Commercially available EGT and GB were used, and pure water was used as a solvent.

[0214] 80 mL of culture soil (manufactured by Hanagokoro Co., Ltd.) was added to a plastic pot with a diameter of 60 mm and a height of 55 mm, and one Arabidopsis thaliana (Col-0) was sown per pot. A plastic deep dish with a diameter of 160 mm and a height of 28 mm was prepared, and four pots were set.

[0215] In an artificial climate room set at room temperature of 22°C, the light period was set to 16 hours and the dark period was set to 8 hours. The light condition was set to a light intensity of 5000 lx in the center under fluorescent light. Water was supplied from the bottom and the water level was set to about 5 mm. On the 41st day after sowing, 50 mL of EGT or 50 mL of GB was added, and one day later, the seeds were exposed to 42°C for 3 hours to give high temperature stress.

[0216] The number of surviving plants after 12 days of high temperature stress was counted, and the plant dieback rate was evaluated as an indicator of physiological disease. The evaluation results are shown in Table 4. The dieback rate and environmental stress inhibition rate were calculated according to the following formula.

[0217] Death rate (%)

[0218] ={1-(number of surviving plants / number of plants tested)}×100

[0219] Environmental stress inhibition rate (%)

[0220] ={1-(death rate of the area treated with the test compound / death rate of the area without treatment)}×100

[0221] [Table 4]

[0222] Table 4

[0223]

[0224]

[0225] As shown in Table 4, due to high temperature stress, physiological diseases such as wilting and necrosis were observed in Arabidopsis, and 75% of the Arabidopsis tested died (Comparative Example 15). Even with the treatment with GB, the death rate caused by high temperature stress was not suppressed (Comparative Example 12). In contrast, by treating with EGT, the death rate caused by high temperature stress was suppressed to 25% (Example 5).

[0226] [Evaluation Example 5] Comparison of Tolerance Effects to Excess Nutrient Stress

[0227] EGT (Example 6) or GB (Comparative Example 17) was prepared so as to have the concentrations described in the following Table 5. Commercially available EGT and GB were used, and pure water was used as a solvent.

[0228] In a plastic pot with a diameter of 60 mm and a height of 55 mm, one individual Arabidopsis thaliana (Col-0) was sown in each pot. A plastic deep dish with a diameter of 160 mm and a height of 28 mm was prepared, and 4 pots were set. As soil, 45 mL of vermiculite, 22.5 mL of granular culture soil (combined horticultural culture soil), and 22.5 mL of vermiculite were added to the pots in sequence.

[0229] In the artificial climate room set at 22 ℃ of room temperature, the photoperiod was set to 16 hours and the dark period was set to 8 hours. The light condition was set to a light intensity of 5000 lx at the center under the irradiation of a fluorescent lamp. The water supply was provided at the bottom, and the water level was set to about 5 mm. On the 61st day after sowing, EGT50 mL or GB50 mL was added, and after 1 day, liquid fertilizer (HYPONeX, Hyponex Japan Co., Ltd.) was diluted 5 times to fertilize, thus giving excessive nutrient stress.

[0230] The number of wilted leaves was evaluated one day after the excess nutrient stress was applied. The evaluation results are shown in Table 5. The leaf wilting rate and environmental stress inhibition rate were calculated according to the following formula.

[0231] Leaf wilting rate (%)

[0232] =(number of wilted leaves / total number of leaves of the tested plants)×100

[0233] Environmental stress inhibition rate (%)

[0234] ={1-(wilting rate of the test compound treated area / wilting rate of the untreated area)}×100

[0235] [Table 5]

[0236] Table 5

[0237] Test compound Test compound concentration Excess nutrient stress Leaf wilting rate Environmental stress inhibition rate Example 6 EGT 0.5mM have 24％ 76％ Comparative Example 17 GB 0.5mM have 89％ 11％ Comparative Example 18 - - have 100％ - Comparative Example 19 - - none 0％ -

[0238] As shown in Table 5, due to excess nutrient stress, a physiological disease of 100% wilting was observed in the leaves of the tested Arabidopsis (Comparative Example 18), and even with the treatment with GB, the wilting rate caused by excess nutrient stress was hardly suppressed (Comparative Example 17). In contrast, the wilting rate of the leaves of Arabidopsis treated with EGT (Example 6) was lower than that of the leaves of Arabidopsis treated with GB, and the wilting of the leaves caused by excess nutrient stress was suppressed.

[0239] [Evaluation Example 6] Comparison of Tolerance Effects to Drought Stress

[0240] EGT (Examples 7 and 8) or GB (Comparative Examples 20 and 21) were prepared so as to have the concentrations described in the following Table 6. Commercially available EGT and GB were used, and pure water was used as a solvent.

[0241] 150 mL of granular culture soil (combined horticultural culture soil) was added to a plastic pot with a side length of 60 mm and a height of 66 mm, and one soybean was sown per pot.

[0242] The plants were managed in a greenhouse set at a room temperature of 25° C. On the 23rd day after sowing, 50 mL of EGT or 50 mL of GB was added, and water supply was stopped for 7 days thereafter to give drought stress.

[0243] The number of dead leaves after 7 days without water was counted, and the leaf death rate was evaluated as an indicator of physiological disease. The evaluation results are shown in Table 6. The leaf death rate and environmental stress inhibition rate were calculated according to the following formula.

[0244] Leaf death rate (%)

[0245] = (number of dead leaves / total number of leaves of the tested plants) × 100

[0246] Environmental stress inhibition rate (%)

[0247] ={1-(leaves withering rate in the area treated with the test compound / leaves withering rate in the area not treated)}×100

[0248] [Table 6]

[0249] Table 6

[0250] Test compound Test compound concentration Dryness stress Leaf death rate Environmental stress inhibition rate Example 7 EGT 1mM have 38％ 39％ Example 8 EGT 0.1mM have 55％ 11％ Comparative Example 20 GB 1mM have 62％ 0％ Comparative Example 21 GB 0.1mM have 71％ 0％ Comparative Example 22 - - have 62％ - Comparative Example 23 - - none 0％ -

[0251] As shown in Table 6, physiological diseases such as leaf wilting and necrosis were observed in soybeans due to drought stress, and 62% of the leaves of the tested soybeans died (Comparative Example 22). Even with the treatment with GB, the death rate caused by drought stress was not suppressed (Comparative Examples 20 and 21). In contrast, by treating with EGT, the death rate caused by drought stress was suppressed to 55% at 0.1 mM (Example 8) and to 38% at 1.0 mM (Example 7).

[0252] [Evaluation Example 7] Comparison of Tolerance Effects to Drought Stress

[0253] EGT (Example 9) or GB was prepared so as to have the concentrations described in Table 7 below.

[0254] (Comparative Example 24) Commercially available EGT and GB were used, and pure water was used as a solvent.

[0255] 1 kg of granular culture soil (combined garden culture soil) was added to a plastic pot having a diameter of 135 mm and a height of 110 mm, and 5 radishes (water radishes) were sown per pot.

[0256] The plants were managed in a greenhouse set at 25°C. On the 22nd day after sowing, 50 mL of EGT or 50 mL of GB was added, and water supply was stopped for 7 days. Then, the plants were cultivated under water supply for 7 days, and water supply was stopped again for 7 days to give drought stress.

[0257] The number of dead leaves of the radish subjected to drought stress was counted, and the leaf death rate was evaluated as an indicator of physiological disease. The evaluation results are shown in Table 7. The leaf death rate and environmental stress inhibition rate were calculated according to the following formula.

[0258] Leaf death rate (%)

[0259] = (number of dead leaves / total number of leaves of the tested plants) × 100

[0260] Environmental stress inhibition rate (%)

[0261] ={1-(leaves withering rate of the test compound treated area / leaves withering rate of the untreated area)}×100 [Table 7]

[0262] Table 7

[0263] Test compound Test compound concentration Dryness stress Leaf death rate Environmental stress inhibition rate Example 9 EGT 0.5mM have 17％ 71％ Comparative Example 24 GB 0.5mM have 73％ 0％ Comparative Example 25 - - have 59％ - Comparative Example 26 - - none 0％ -

[0264] As shown in Table 7, physiological diseases such as leaf wilting and necrosis were observed in radish due to drought stress, and 59% of the leaves of the tested radish died (Comparative Example 25). Even with the treatment with GB, the death rate due to drought stress was not suppressed (Comparative Example 24). On the other hand, the death rate due to drought stress was suppressed to 17% by the treatment with EGT (Example 9).

[0265] [Evaluation Example 8] Comparison of Tolerance Effects to Drought Stress

[0266] EGT (Example 10) or GB was prepared so as to have the concentrations described in Table 8 below.

[0267] (Comparative Example 27) Commercially available EGT and GB were used, and pure water was used as a solvent.

[0268] 1 L of seedling culture soil (manufactured by TAKII Seedlings) was added to a plastic pot with a diameter of 135 mm and a height of 110 mm, and a lawn of 100 mm square Zoysia japonica (Korean grass) was laid in each pot.

[0269] The plants were managed in a greenhouse set at 25°C. About one month after the lawn was laid, 12.5 mL of EGT or 12.5 mL of GB was added, and water supply was stopped for 7 days. Then, after cultivation under water supply for 7 days, water supply was stopped again for 7 days to give drought stress.

[0270] The number of dead leaves of Zoysia japonica subjected to drought stress was counted, and the leaf death rate was evaluated as an indicator of physiological disease. The evaluation results are shown in Table 8. The leaf death rate and environmental stress inhibition rate were calculated according to the following formula.

[0271] Leaf death rate (%)

[0272] = (number of dead leaves / total number of leaves of the tested plants) × 100

[0273] Environmental stress inhibition rate (%)

[0274] ={1-(leaves withering rate of the test compound treated area / leaves withering rate of the untreated area)}×100 [Table 8]

[0275] Table 8

[0276] Test compound Test compound concentration Dryness stress Leaf death rate Environmental stress inhibition rate Example 10 EGT 0.1mM have 35％ 65％ Comparative Example 27 GB 0.1mM have 100％ 0％ Comparative Example 28 - have 100％ - Comparative Example 29 - 0％ -

[0277] As shown in Table 8, physiological diseases such as necrosis were observed in Zoysia japonica due to drought stress, and 100% of the leaves of the tested Zoysia japonica died (Comparative Example 28). Even with the treatment with GB, the death rate caused by drought stress was not suppressed (Comparative Example 27). In contrast, the death rate caused by drought stress was suppressed to 35% by the treatment with EGT (Example 10).

[0278] [Evaluation Example 9] Comparison of Tolerance Effects to Excess Water Stress

[0279] EGT (Example 11, Comparative Example 31) or GB (Comparative Examples 30, 32) were prepared to have the concentrations shown in the following Table 9. Commercially available EGT and GB were used, and pure water was used as a solvent.

[0280] 5 mL of pure water was added to a 9 cm petri dish covered with filter paper, and 12 rapeseed seeds were sown in each petri dish. The culture was managed in an artificial climate room set at room temperature of 22°C, with a light period of 16 hours and a dark period of 8 hours. The light condition was set to a light intensity of 5000 lx in the center under fluorescent light irradiation.

[0281] On the 6th day after sowing, pure water in the culture dish was drained, and 5 mL of EGT or 5 mL of GB was added to the culture dish. One day later, 50 mL of pure water was added to the culture dish to give excess water stress.

[0282] The number of surviving plants 19 days after the excess water stress was applied was counted, and the plant dieback rate was evaluated as an indicator of physiological disease. The evaluation results are shown in Table 9. The dieback rate and environmental stress inhibition rate were calculated according to the following formula.

[0283] Death rate (%)

[0284] ={1-(number of surviving plants / number of plants tested)}×100

[0285] Environmental stress inhibition rate (%)

[0286] ={1-(death rate of the area treated with the test compound / death rate of the area without treatment)}×100

[0287] [Table 9]

[0288] Table 9

[0289] Test compound Test compound concentration Excess water stress Death rate Environmental stress inhibition rate Embodiment 11 EGT 0.1mM have 25％ 58％ Comparative Example 30 GB 0.1mM have 60％ 0％ Comparative Example 31 EGT 0.1mM none 0％ - Comparative Example 32 GB 0.1mM none 0％ - Comparative Example 33 - - have 60％ - Comparative Example 34 - - none 0％ -

[0290] As shown in Table 9, due to excess water stress, physiological diseases such as chlorosis were observed in rapeseed, and 60% of the rapeseed tested died (Comparative Example 33). Even with the treatment with GB, the death rate caused by excess water stress was not suppressed (Comparative Example 30). In contrast, by treating with EGT, the death rate caused by excess water stress was suppressed to 25% (Example 11).

[0291] [Evaluation Example 10] Comparison of the effect of resistance to ultraviolet stress

[0292] EGT (Examples 12, 13, Comparative Examples 37, 38) or GB (Comparative Examples 35, 36, 39, 40) were prepared to have the concentrations shown in the following Table 10. Commercially available EGT and GB were used, and pure water was used as a solvent.

[0293] 5 mL of pure water was added to a 9 cm petri dish covered with filter paper, and 10 wheat seeds were sown in each petri dish. The culture was managed in an artificial climate room set at a room temperature of 22°C, with a light period of 16 hours and a dark period of 8 hours. The light condition was set to a light intensity of 5000 lx in the center under fluorescent light irradiation.

[0294] On the 7th day after sowing, the pure water in the culture dish was drained and 5 mL of EGT was added to the culture dish.

[0295] One day later, the ultraviolet radiation intensity was set to 550 μW / cm under the irradiation of an ultraviolet lamp (manufactured by Toshiba Corporation, GL-15) with a wavelength of 254 nm. -2 , exposed for 1 hour, thereby giving ultraviolet stress.

[0296] The number of dead leaves was counted 6 days after the ultraviolet stress was applied, and the leaf death rate was evaluated as an indicator of physiological disease. The evaluation results are shown in Table 10. The leaf death rate and environmental stress inhibition rate were calculated according to the following formula.

[0297] Leaf death rate (%)

[0298] = (number of dead leaves / total number of leaves of the tested plants) × 100

[0299] Environmental stress inhibition rate (%)

[0300] ={1-(leaves withering rate of the test compound treated area / leaves withering rate of the untreated area)}×100 [Table 10]

[0301] Table 10

[0302] Test compound Test compound concentration UV stress Leaf death rate Environmental stress inhibition rate Example 12 EGT 1mM have 23％ 57％ Embodiment 13 EGT 0.1mM have 34％ 36％ Comparative Example 35 GB 1mM have 44％ 17％ Comparative Example 36 GB 0.1mM have 50％ 6％ Comparative Example 37 EGT 1mM none 0％ - Comparative Example 38 EGT 0.1mM none 1％ - Comparative Example 39 GB 1mM none 0％ - Comparative Example 40 GB 0.1mM none 5％ - Comparative Example 41 - - have 53％ - Comparative Example 42 - - none 0％ -

[0303] As shown in Table 10, due to ultraviolet stress, physiological diseases such as chlorosis were observed in wheat, and 53% of the wheat leaves tested died (Comparative Example 41). Even with GB treatment, the death rate caused by ultraviolet stress was almost not suppressed (Comparative Examples 35 and 36). In contrast, the death rate of wheat treated with EGT was lower than that of wheat treated with GB, and the death rate caused by ultraviolet stress was suppressed to 34% at 0.1 mM (Example 13) and to 23% at 1.0 mM (Example 12).

[0304] [Evaluation Example 11] Comparison of the effect of resistance to ultraviolet stress

[0305] EGT (Examples 14, 15, Comparative Examples 45, 46) or GB (Comparative Examples 43, 44, 47, 48) were prepared to have the concentrations shown in the following Table 11. Commercially available EGT and GB were used, and pure water was used as a solvent.

[0306] Zoysia japonica (Korean grass) cut into 50 mm squares was placed in a petri dish and managed in a greenhouse set at room temperature of 25°C. The plant height was trimmed to a length of 10 mm. 10 mL of EGT or 10 mL of GB was added to each petri dish, and after one day, the ultraviolet radiation intensity of the ultraviolet light with a wavelength of 254 nm was set to 525 μW / cm under the irradiation of an ultraviolet lamp (manufactured by Toshiba, GL-15). -2 , exposed for 1 hour, thereby giving ultraviolet stress.

[0307] The number of dead leaves was counted 7 days after the ultraviolet stress was applied, and the leaf death rate was evaluated as an indicator of physiological disease. The evaluation results are shown in Table 11. The leaf death rate and environmental stress inhibition rate were calculated according to the following formula.

[0308] Leaf death rate (%)

[0309] = (number of dead leaves / total number of leaves of the tested plants) × 100

[0310] Environmental stress inhibition rate (%)

[0311] ={1-(leaves withering rate of the test compound treated area / leaves withering rate of the untreated area)}×100 [Table 11]

[0312] Table 11

[0313] Test compound Test compound concentration UV stress Leaf death rate Environmental stress inhibition rate Embodiment 14 EGT 1mM have 6％ 90％ Embodiment 15 EGT 0.1mM have 13％ 79％ Comparative Example 43 GB 1mM have 59％ 6％ Comparative Example 44 GB 0.1mM have 54％ 14％ Comparative Example 45 EGT 1mM none 0％ - Comparative Example 46 EGT 0.1mM none 2％ - Comparative Example 47 GB 1mM none 0％ - Comparative Example 48 GB 0.1mM none 2％ - Comparative Example 49 - - have 63％ - Comparative Example 50 - - none 0％ -

[0314] As shown in Table 11, due to ultraviolet stress, physiological diseases such as chlorosis were observed in Zoysia japonica, and 63% of the leaves of the tested Zoysia japonica died (Comparative Example 49). Even with GB treatment, the death rate caused by ultraviolet stress was almost not suppressed (Comparative Examples 43 and 44). In contrast, Zoysia japonica treated with EGT had a lower death rate than Zoysia japonica treated with GB, and the death rate caused by ultraviolet stress was suppressed to 13% at 0.1 mM (Example 15) and to 6% at 1.0 mM (Example 14).

[0315] [Evaluation Example 12] Comparison of Tolerance Effects to Strong Light Stress

[0316] EGT (Example 16) or GB (Comparative Example 51) was prepared so as to have the concentrations described in the following Table 12. Commercially available EGT and GB were used, and pure water was used as a solvent.

[0317] 90 mL of culture soil (manufactured by Hanagokoro Co., Ltd.) was placed in a plastic pot having a diameter of 60 mm and a height of 55 mm, and four Arabidopsis thaliana (Col-0) were sown per pot.

[0318] The plants were maintained in an artificial climate chamber set at 22°C, with a light period of 16 hours and a dark period of 8 hours. The light condition was set to a light intensity of 5000 lx in the center under fluorescent light. 12.5 mL of EGT or 12.5 mL of GB was added on the 43rd day after sowing, and one day later, the light intensity was set to 2000 μmol / m under LED light (Esbaybulbs). -2 / sec, exposed for 24 hours, thereby giving strong light stress.

[0319] The number of albinized leaves of Arabidopsis thaliana subjected to strong light stress was counted, and the leaf albinism rate was evaluated as an indicator of physiological disease. The evaluation results are shown in Table 12. The leaf albinism rate and environmental stress inhibition rate were calculated according to the following formula.

[0320] Leaf bleaching rate (%)

[0321] = (number of whitened leaves / total number of leaves of the tested plants) × 100

[0322] Environmental stress inhibition rate (%) = {1-(leaves albinism rate in the test compound treated area / leaves albinism rate in the untreated area)} × 100 [Table 12]

[0323] Table 12

[0324] Test compound Test compound concentration Strong light stress Leaf bleaching rate Environmental stress inhibition rate Example 16 EGT 0.1mM have 8％ 78％ Comparative Example 51 GB 0.1mM have 40％ 0％ Comparative Example 52 - - have 37％ - Comparative Example 53 - - none 0％ -

[0325] As shown in Table 12, due to strong light stress, physiological diseases such as chlorosis were observed in Arabidopsis, and 37% of the leaves of the tested Arabidopsis turned white (Comparative Example 52). Even with the treatment with GB, the leaf whitening caused by strong light stress was not suppressed (Comparative Example 51). In contrast, by treating with EGT, the leaf whitening rate caused by strong light stress was suppressed to 8% (Example 16).

[0326] [Evaluation Example 13] Comparison of the effect of tolerance to freezing stress

[0327] EGT (Example 17, Comparative Example 55) or GB (Comparative Examples 54 and 56) were prepared so as to have the concentrations described in the following Table 13. Commercially available EGT and GB were used, and pure water was used as a solvent.

[0328] 5 mL of pure water was added to a 9 cm petri dish covered with filter paper, and 10 broccoli seeds were sown in each petri dish. The culture was managed in an artificial climate room set at room temperature of 22°C, with a light period of 16 hours and a dark period of 8 hours. The light condition was set to a light intensity of 5000 lx in the center under fluorescent light irradiation.

[0329] On the 6th day after sowing, pure water in the culture dish was removed and 5 mL of EGT or GB was added to the culture dish. After 14 days, the culture dishes were exposed to -20°C for 20 minutes and after 1 day, the culture dishes were exposed to -20°C for 20 minutes to give freezing stress.

[0330] The number of plants that survived 24 hours after freezing stress was counted, and the plant dieback rate was evaluated as an indicator of physiological disease. The evaluation results are shown in Table 13. The dieback rate and environmental stress inhibition rate were calculated according to the following formula.

[0331] Death rate (%)

[0332] ={1-(number of surviving plants / number of plants tested)}×100

[0333] Environmental stress inhibition rate (%)

[0334] ={1-(death rate of the area treated with the test compound / death rate of the area without treatment)}×100

[0335] [Table 13]

[0336] Table 13

[0337] Test compound Test compound concentration Freezing stress Death rate Environmental stress inhibition rate Embodiment 17 EGT 0.1mM have 38％ 56％ Comparative Example 54 GB 0.1mM have 100％ 0％ Comparative Example 55 EGT 0.1mM none 0％ - Comparative Example 56 GB 0.1mM none 0％ - Comparative Example 57 - - have 86％ - Comparative Example 58 - - none 0％ -

[0338] As shown in Table 13, physiological diseases such as stem breakage and necrosis were observed in cauliflower due to freezing stress, and 86% of the broccoli tested died (Comparative Example 57). Even with the treatment with GB, the death rate caused by freezing stress was not suppressed (Comparative Example 54). In contrast, the death rate caused by freezing stress was suppressed to 38% by the treatment with EGT (Example 17).

[0339] [Evaluation Example 14] Comparison of the effect of tolerance to freezing stress

[0340] EGT (Example 18, Comparative Example 60) or GB (Comparative Examples 59, 61) were prepared so as to have the concentrations described in the following Table 14. Commercially available EGT and GB were used, and pure water was used as a solvent.

[0341] 5 mL of pure water was added to a 9 cm petri dish covered with filter paper, and 10 strawberry (wild strawberry) seeds were sown in each petri dish. The culture was managed in an artificial climate room set at room temperature of 22°C, with a light period of 16 hours and a dark period of 8 hours. The light condition was set to a light intensity of 5000 lx in the center under fluorescent light irradiation.

[0342] On the 15th day after sowing, pure water in the culture dish was drained, and 5 mL of EGT or 5 mL of GB was added to the culture dish. Nine days later, the culture dishes were exposed to -20°C for 20 minutes to give freezing stress.

[0343] The number of surviving plants 3 days after freezing stress was counted, and the plant dieback rate was evaluated as an indicator of physiological disease. The evaluation results are shown in Table 14. The dieback rate and environmental stress inhibition rate were calculated according to the following formula.

[0344] Death rate (%)

[0345] ={1-(number of surviving plants / number of plants tested)}×100

[0346] Environmental stress inhibition rate (%)

[0347] ={1-(death rate of the area treated with the test compound / death rate of the area without treatment)}×100

[0348] [Table 14]

[0349] Table 14

[0350] Test compound Test compound concentration Freezing stress Death rate Environmental stress inhibition rate Embodiment 18 EGT 0.1mM have 29％ 54％ Comparative Example 59 GB 0.1mM have 63％ 0％ Comparative Example 60 EGT 0.1mM none 0％ - Comparative Example 61 GB 0.1mM none 0％ - Comparative Example 62 - - have 63％ - Comparative Example 63 - - none 0％ -

[0351] As shown in Table 14, physiological diseases such as necrosis were observed in strawberries due to freezing stress, and 63% of the tested strawberries died (Comparative Example 62). Even with GB treatment, the death rate caused by freezing stress was not suppressed (Comparative Example 59). In contrast, the death rate caused by freezing stress was suppressed to 29% by treatment with EGT (Example 18).

[0352] [Evaluation Example 15] Comparison of the effect of tolerance to low temperature stress

[0353] EGT (Examples 19, 20, Comparative Examples 66, 67) or GB (Comparative Examples 64, 65, 68, 69) were prepared to have the concentrations shown in the following Table 15. Commercially available EGT and GB were used, and pure water was used as a solvent.

[0354] 1 mL of pure water was added to a 3.5 cm petri dish covered with filter paper, and 5 rocket seeds were sown in each petri dish. The culture was managed in an artificial climate room set at room temperature of 22°C, with a light period of 16 hours and a dark period of 8 hours. The light condition was set to a light intensity of 5000 lx in the center under fluorescent light irradiation.

[0355] On the 4th day after sowing, pure water in the culture dish was drained, and 1 mL of EGT or 1 mL of GB was added to the culture dish. 24 hours later, the dishes were exposed to a 4°C environment for 48 hours to give low temperature stress.

[0356] The number of wilted leaves of rocket 3 days after low temperature stress was applied was evaluated. The evaluation results are shown in Table 15. The leaf wilting rate and environmental stress inhibition rate were calculated according to the following formula.

[0357] Leaf wilting rate (%)

[0358] =(number of wilted leaves / total number of leaves of the tested plants)×100

[0359] Environmental stress inhibition rate (%)

[0360] ={1-(wilting rate of leaves in the test compound-treated area / wilting rate of leaves in the untreated area)}×100 [Table 15]

[0361] Table 15

[0362] Test compound Test compound concentration Low temperature stress Leaf wilting rate Environmental stress inhibition rate Embodiment 19 EGT 1mM have 0％ 100％ Embodiment 20 EGT 0.1mM have 0％ 100％ Comparative Example 64 GB 1mM have 60％ 10％ Comparative Example 65 GB 0.1mM have 60％ 10％ Comparative Example 66 EGT 1mM none 0％ - Comparative Example 67 EGT 0.1mM none 0％ - Comparative Example 68 GB 1mM none 0％ - Comparative Example 69 GB 0.1mM none 0％ - Comparative Example 70 - - have 67％ - Comparative Example 71 - - none 0％ -

[0363] As shown in Table 15, due to low temperature stress, physiological diseases such as 67% wilting were observed in the leaves of the tested rocket (Comparative Example 70), and even when GB was used for treatment, the wilting rate of leaves caused by low temperature stress was almost not suppressed (Comparative Examples 64 and 65). In contrast, by treating with EGT, the wilting rate of leaves caused by low temperature stress was suppressed to 0% (Examples 19 and 20).

Claims

1. A plant environmental stress tolerance enhancer, comprising a compound represented by the following formula (I) or its tautomer, or an agronomically acceptable salt thereof as an active ingredient, [Chemical formula 1] In formula (I), R 1 and R 2 independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R 3 ~R 5 Each of them independently represents an alkyl group having 1 to 4 carbon atoms.

2. The environmental stress tolerance enhancing agent according to claim 1, wherein The compound shown in the formula (I) is ergothioneine.

3. The environmental stress tolerance enhancing agent according to claim 1, wherein The environmental stress tolerance enhancing agent enhances tolerance to at least one environmental stress selected from high temperature stress, low temperature stress, freezing stress, salt stress, excess nutrient stress, dryness stress, excess water stress, ultraviolet stress, weak light stress and strong light stress.

4. The environmental stress tolerance enhancing agent according to claim 1, wherein The environmental stress tolerance enhancing agent is a salt stress tolerance enhancing agent.

5. The environmental stress tolerance enhancing agent according to claim 1, wherein The environmental stress tolerance enhancing agent is a desiccation stress tolerance enhancing agent.

6. The environmental stress tolerance enhancing agent according to claim 1, wherein The environmental stress tolerance enhancing agent is a high temperature stress tolerance enhancing agent.

7. The environmental stress tolerance enhancing agent according to claim 1, wherein The environmental stress tolerance enhancing agent is an excess nutrient stress tolerance enhancing agent.

8. The environmental stress tolerance enhancing agent according to claim 1, wherein The environmental stress tolerance enhancing agent is an excess water stress tolerance enhancing agent.

9. The environmental stress tolerance enhancing agent according to claim 1, wherein The environmental stress tolerance enhancing agent is an ultraviolet stress tolerance enhancing agent.

10. The environmental stress tolerance enhancing agent according to claim 1, wherein The environmental stress tolerance enhancing agent is a strong light stress tolerance enhancing agent.

11. The environmental stress tolerance enhancing agent according to claim 1, wherein The environmental stress tolerance enhancing agent is a freezing stress tolerance enhancing agent.

12. The environmental stress tolerance enhancing agent according to claim 1, wherein The environmental stress tolerance enhancing agent is a low temperature stress tolerance enhancing agent. 13 . A method for improving environmental stress tolerance of a plant, comprising treating the plant with the environmental stress tolerance improving agent according to any one of claims 1 to 12.

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