METHOD OF PROVIDING PLANT WITH STRESS RESISTANCE

Abstract
A method of providing a plant with stress resistance, comprising applying at least one substance (A) to the plant, said at least one substance (A) being selected from the group consisting of a compound represented by Formula (I) and the like and salts thereof. Phytotoxicity of a plant due to agricultural chemicals is reduced by providing the plant with stress resistance. [In Formula (I), R1 to R4 each independently represents a hydrogen atom, —SO3H, —PO3H2, a glycosyl group or —COR11. R11 represents an unsubstituted or substituted C1 to C30 alkyl group or an unsubstituted or substituted C2 to C30 alkenyl group.].
Description
TECHNICAL FIELD

The present invention relates to a method of providing a plant with stress resistance. More specifically, the present invention relates to a method of providing a plant with resistance to biological stress, physical stress or chemical stress which affects the growth of the plant.


BACKGROUND ART

Plants grown at farmlands or ordinary home gardens are always exposed to various biological or non-biological stresses. In general, agricultural crops subjected to breed improvement tend to be less resistant to these stresses. In order to reduce biological stress such as agricultural pests and weeds to maintain a crop yield, agricultural chemicals are used such as fungicides, insecticides and herbicides. However, agricultural chemicals may have insufficient effects, and may cause phytotoxicity when improperly used, and may allow agricultural pests and weeds to develop resistance to the agricultural chemicals, and may pose concerns about safety for environmental life. Meanwhile, the right plant in the right place, breed improvement, irrigation, greenhouse, soil improvement and the like are utilized to respond environmental stress such as temperature, moisture, illuminance, soil pH and salt concentrations. Attempts have been made for conferring stress resistance using a plant growth regulator and the like, but effects have been unsatisfactory. Further, plant viral diseases may cause serious damage to key crops such as cereal crops, vegetables and fruit trees. However, to date, agricultural chemicals have not been found which sufficiently demonstrate practical effects against plant viral diseases.


Meanwhile, Non-patent Literature 1 describes that ascorbic acid is involved in disease resistance, hormone actions and the like, and Non-patent Literature 2 describes that ascorbic acid affects plant aging. However, even when ascorbic acid is externally given to a plant, its physiological effect is very limited because ascorbic acid is present at a high concentration in a plant body. Therefore, there will be almost no practical effect.


Nonetheless, Patent Literature 1 describes that a certain derivative of ascorbic acid demonstrates a preventive and curative effect against a plant virus disease, and proposes to apply it to a plant. Further, Patent Literature 2 discloses a composition comprising an antimicrobic antibiotic such as neomycin sulfate and ascorbic acid, and states that this composition can control a plant disease.


CITATION LIST
Non-patent Literatures



  • Non-patent Literature 1: Vitamins 79 (2): 116-117 (2005)

  • Non-patent Literature 2: The Horticulture Journal, 6 (2): 169-175



Patent Literatures



  • Patent Literature 1: WO 2011/030816 A

  • Patent Literature 2: JP 2001-508808 A



SUMMARY OF THE INVENTION
Problems to be Solved by the Invention

An object of the present invention is to provide a method of providing a plant with resistance to biological stress, physical stress or chemical stress which affects the growth of the plant.


Means for Solving the Problems

As a result of conducting extensive studies to achieve the above object, the present inventors complete the present invention which has the following aspects.


[1] A method of providing a plant with stress resistance, wherein the method comprises applying at least one substance (A) to the plant, said at least one substance (A) being selected from the group consisting of compounds represented by Formula (I), compounds represented by Formula (II) and salts thereof.




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[In Formula (I), R1 to R4 each independently represents a hydrogen atom, —SO3H, —PO3H2, a glycosyl group, or —COR11. R11 represents an unsubstituted or substituted C1 to C30 alkyl group or an unsubstituted or substituted C2 to C30 alkenyl group.]




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[In Formula (II), R5 and R6 each independently represents a hydrogen atom, —SO3H, —PO3H2, a glycosyl group or —COR11. R11 represents an unsubstituted or substituted C1 to C30 alkyl group or an unsubstituted or substituted C2 to C30 alkenyl group.]


[2] The method according to [1], wherein the substance (A) is a compound represented by Formula (I) [provided that R1 to R4 are not each simultaneously a hydrogen atom] or a salt thereof.


[3] The method according to [1], wherein the substance (A) is a compound represented by Formula (I) [provided that at least one of R1 to R4 represents —COR11, and R11 represents an unsubstituted or substituted C12 to C30 alkyl group or an unsubstituted or substituted C12 to C30 alkenyl group.] or a salt thereof.


[4] The method according to [1], wherein the substance (A) is a compound represented by Formula (I) [provided that R1 to R4 each independently represents a hydrogen atom or —COR11, and at least one of R1 to R4 represents —COR11. R11 represents an unsubstituted or substituted C1 to C30 alkyl group or an unsubstituted or substituted C2 to C30 alkenyl group. R11 in at least one of —COR11 represents an unsubstituted or substituted C12 to C30 alkyl group or an unsubstituted or substituted C12 to C30 alkenyl group.] or a salt thereof.


[5] The method according to [1], wherein the substance (A) is a composition comprising a water soluble substance (A1) of those selected from the group consisting of compounds represented by Formula (I), compounds represented by Formula (II) and salts thereof; and a lipid soluble substance (A2) of those selected from the group consisting of compounds represented by Formula (I), compounds represented by Formula (II) and salts thereof.


[6] The method according to any one of [1] to [5], wherein the stress is biological stress due to plant viruses, phytopathogenic bacteria, phytopathogenic filamentous fungi, pests or weeds; or physical or chemical stress due to high temperature, low temperature, high illuminance, low illuminance, excessive humidity, dryness, salt, acidity, agricultural chemicals, chemical substances or heavy metals.


[7] A stress resistance conferring composition for a plant, wherein the composition comprises at least two substances (A) selected from the group consisting of compounds represented by Formula (I), compounds represented by Formula (II) and salts thereof.




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[In Formula (I), R1 to R4 each independently represents a hydrogen atom, —SO3H, —PO3H2, a glycosyl group or —COR11. R11 represents an unsubstituted or substituted C1 to C30 alkyl group or an unsubstituted or substituted C2 to C30 alkenyl group.]




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[In Formula (II), R5 and R6 each independently represents a hydrogen atom, —SO3H, —PO3H2, a glycosyl group or —COR11. R11 represents an unsubstituted or substituted C1 to C30 alkyl group or an unsubstituted or substituted C2 to C30 alkenyl group.]


[8] The composition according to [7], wherein one of the substances (A) is a water soluble substance (A1) of those selected from the group consisting of compounds represented by Formula (I), compounds represented by Formula (II) and salts thereof; and another of the substances (A) is a lipid soluble substance (A2) of those selected from the group consisting of compounds represented by Formula (I), compounds represented by Formula (II) and salts thereof.


[9] A stress resistance conferring composition for a plant, wherein the composition comprises at least one water soluble substance (A1) selected from the group consisting of compounds represented by Formula (Ia), compounds represented by Formula (IIa) and salts thereof; and


at least one lipid soluble substance (A2) selected from the group consisting of compounds represented by Formula (Ib), compounds represented by Formula (IIb) and salts thereof.




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[In Formula (Ia), R1a to R4a each independently represents a hydrogen atom, —SO3H, —PO3H2 or a glycosyl group.]




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[In Formula (IIa), R5a to R6a each independently represents a hydrogen atom, —SO3H, —PO3H2 or a glycosyl group.]




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[In Formula (Ib), R1b to R4b each independently represents a hydrogen atom or —COR11. At least one of R1b to R4b represents —COR11, and R11 represents an unsubstituted or substituted C1 to C30 alkyl group or an unsubstituted or substituted C2 to C30 alkenyl group.]




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[In Formula (IIb), R5b and R6b each independently represents a hydrogen atom or —COR11. At least one of R5b and R6b represents —COR11, and R11 represents an unsubstituted or substituted C1 to C30 alkyl group or an unsubstituted or substituted C2 to C30 alkenyl group.]


[10] A method of reducing phytotoxicity of a plant due to an agricultural chemical, wherein the method comprises providing the plant with stress resistance by the method according to any one of [1] to [6].


[11] The method of reducing phytotoxicity of a plant due to an agricultural chemical according to claim 10, wherein the agricultural chemical comprises at least one selected from the group consisting of fungicides, insecticides, plant growth regulators and herbicides.


Advantageous Effects of the Invention

The method according to the present invention can provide a plant with resistance to biological stress, physical stress or chemical stress which affects the growth of the plant. As a result, for example, phytotoxicity due to agricultural chemicals comprising a substance and the like which may affect a physiological function of a plant can be reduced, and damage due to plant diseases including virus diseases can be reduced. Moreover, even under poor environmental conditions such as high temperature, low temperature, dryness and soil conditions, reduced crop yield, deteriorated quality and the like can be prevented.


EMBODIMENTS FOR CARRYING OUT THE INVENTION

The method of providing a plant with stress resistance according to the present invention comprises applying the substance (A) to a plant.


(Substance (A))

The substance (A) is at least one selected from the group consisting of compounds represented by Formula (I), compounds represented by Formula (II) and salts thereof.


In Formula (I), R1 to R4 each independently represents a hydrogen atom, —SO3H, —PO3H2, a glycosyl group or —COR11.


In Formula (II), R5 and R6 each independently represents a hydrogen atom, —SO3H, —PO3H2, a glycosyl group or —COR11.


The glycosyl group is a sugar residue such as a monosaccharide or a low molecular weight oligosaccharide (which is, specifically, a partial structure of a molecule in which a hemiacetal hydroxy group at a sugar portion is removed to give a connecting position). Examples of monosaccharides include glucose, galactose, fructose, rhamnose and the like, and examples of oligosaccharides include rutinose, vicianose, lactose, maltose, sucrose and the like. Therefore, examples of glycosyl groups include a glucosyl group, a galactosyl group, a fructosyl group, a rhamnosyl group and the like. Further, glycosyl groups include disaccharide groups in which any combination of these groups are connected in the 1-2 linkage, the 1-3 linkage, the 1-4 linkage or the 1-6 linkage.


R11 in —COR11 represents an unsubstituted or substituted C1 to C30 alkyl group or an unsubstituted or substituted C2 to C30 alkenyl group.


As used herein, the term “unsubstituted” means that a corresponding group comprises only a group serving as a mother nucleus. Note that when described only under the name of a group serving as a mother nucleus without a description of “substituted”, it means “unsubstituted” unless otherwise stated.


Meanwhile, the term “substituted” means that any hydrogen atom in a group serving as a mother nucleus is substituted with a group having a structure which is different from or the same as the mother nucleus. Therefore, the term “substituent” is another group substituted on a group serving as a mother nucleus. The number of substituents may be 1, or may be 2 or more. Two or more substituents may be the same, or may be different. For example, a substituted C1 to C30 alkyl group is a group having a structure in which the group serving as a mother nucleus is a C1 to C30 alkyl group, and any hydrogen atom thereof is substituted with a group having a different structure (“substituent”).


A “C1 to C30 alkyl group” in R11 is a saturated hydrocarbon group comprising 1 to 30 carbon atoms. A C1 to C30 alkyl group may be a linear chain, or may be a branched chain. Examples of C1 to C30 alkyl groups include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an i-propyl group, an i-butyl group, an s-butyl group, a t-butyl group, an i-pentyl group, a neopentyl group, a 2-methylbutyl group, a 2,2-dimethylpropyl group, an i-hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group (a myristyl group), a pentadecyl group, a hexadecyl group (a cetyl group, a palmityl group), a heptadecyl group, an octadecyl group (a stearyl group), a nonadecyl group, an icosyl group, a henicosyl group, a triacontyl group and the like.


A “C2 to C30 alkenyl group” in R11 is an unsaturated hydrocarbon group comprising 2 to 30 carbon atoms having at least one carbon-carbon double bond. A C2 to C30 alkenyl group may be a linear chain, or may be a branched chain. Examples of C2 to C30 alkenyl groups include a vinyl group, a 1-propenyl group, an isopropenyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 4-pentenyl group, a 1-hexenyl group, a 2-hexenyl group, a 3-hexenyl group, a 4-hexenyl group, a 5-hexenyl group, a 1-heptenyl group, a 6-heptenyl group, a 1-octenyl group, a 7-octenyl group, a 1-methyl-allyl group, a 2-methyl-allyl group, a 1-methyl-2-butenyl group, a 2-methyl-2-butenyl group, an octenyl group, a nonenyl group, a decenyl group, an undecenyl group, a dodecenyl group, a tridecenyl group, a tetradecenyl group, a pentadecenyl group, a hexadecenyl group, a heptadecenyl group, an octadecenyl group, a nonadecenyl group, an icosenyl group, a henicosenyl group, a triacontenyl group and the like.


Examples of groups which can be a “substituent” in the C1 to C30 alkyl group or the C2 to C30 alkenyl group include a hydroxyl group; a mercapto group; an amino group; a nitro group; a halogen atom such as a chlorine atom, a fluorine atom, a bromine atom; an alkoxy group such as a methoxy group, an ethoxy group, an isopropoxy group, an n-propoxy group, an n-butoxy group, an isobutoxy group, an s-butoxy group, a t-butoxy group; an aryloxy group such as a phenoxy group, a 1-naphthyloxy group; a haloalkoxy group such as a fluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, a 2-chloroethoxy group, a 2,2,2-trichloroethoxy group, a 1,1,1,3,3,3-hexafluoro-2-propoxy group; an alkylthio group such as a methylthio group, an ethylthio group; an arylthio group such as a phenylthio group, a 1-naphthylthio group; an alkylamino group such as a methylamino group, a diethylamino group; an arylamino group such as an anilino group, a 1-naphthyl amino group; a cyano group and the like.


Preferably, the above R11 represents an unsubstituted or substituted C8 to C20 alkyl group or an unsubstituted or substituted C8 to C20 alkenyl group.


The substance (A) is preferably a compound represented by Formula (I) or a salt thereof. Further, preferably, R1 to R4 in Formula (I) are not simultaneously hydrogen atoms.


Moreover, the substance (A) is preferably a compound represented by Formula (I) [at least one of R1 to R4 represents —COR11. R11 represents an unsubstituted or substituted C12 to C30 alkyl group or an unsubstituted or substituted C12 to C30 alkenyl group.] or a salt thereof.


Examples of “C12 to C30 alkyl groups” include a dodecyl group, a tridecyl group, a tetradecyl group (a myristyl group), a pentadecyl group, a hexadecyl group (a cetyl group, a palmityl group), a heptadecyl group, an octadecyl group (a stearyl group), a nonadecyl group, an icosyl group, a henicosyl group, a triacontyl group and the like.


Examples of “Substituted C12 to C30 alkyl groups” include a 2-hydroxytridecyl group, a 1-hydroxypentadecyl group, an 11-hydroxyheptadecyl group, a 1-aminoheptadecyl group and the like.


Examples of “C12 to C30 alkenyl groups” include a dodecenyl group, a tridecenyl group, a tetradecenyl group, a pentadecenyl group, a hexadecenyl group, a heptadecenyl group, an octadecenyl group, a nonadecenyl group, an icosenyl group, a henicosenyl group, a triacontenyl group and the like.


Examples of “substituted C12 to C30 alkenyl groups” include a 7-hydroxy-8-pentadecenyl group, a 1-hydroxy-8-heptadecenyl group, a 1-amino-8-heptadecenyl group and the like.


Further, the substance (A) is preferably a compound represented by Formula (I) [R1 to R4 each independently represents a hydrogen atom or —COR11, and at least one of R1 to R4 represents —COR11, and R11 represents an unsubstituted or substituted C1 to C30 alkyl group or an unsubstituted or substituted C2 to C30 alkenyl group, and R11 in at least one of —COR11 represents an unsubstituted or substituted C12 to C30 alkyl group or an unsubstituted or substituted C12 to C30 alkenyl group.] or a salt thereof.


Specific examples of the substance (A) as described above can include ascorbic acid 6-myristate, ascorbic acid 6-palmitate, ascorbic acid 6-stearate, ascorbic acid 2-myristate, ascorbic acid 2-palmitate, ascorbic acid 2-stearate, ascorbic acid 2,6-dimyristate, ascorbic acid 2,6-dipalmitate, ascorbic acid 2,6-distearate and the like.


There is no particular limitation for salts of a compound represented by Formula (I) and salts of a compound represented by Formula (II) as long as they are agriculturally and horticulturally acceptable salts. They can include, for example, an alkali metal salt such as a sodium salt, a potassium salt; an alkaline earth metal salt such as a calcium salt, a magnesium salt and the like.


The substance (A) used for the present invention can be obtained by a known synthesis approach. For example, an esterification reaction of a fatty acid compound with ascorbic acid for introducing —COR11 into any of R1 to R4, an esterification reaction of a phosphoric acid compound with ascorbic acid for introducing —PO3H2 into any of R1 to R4, an esterification reaction of a sulfuric acid compound with ascorbic acid for introducing —SO3H into any of R1 to R4, and other known reactions can be used for synthesis. Further, the substances (A) obtained by the aforementioned synthesis methods can be purified by a known method such as extraction, distillation, chromatography. Moreover, many of the substances (A) used for the present invention are commercially available, and therefore it is also possible to use them.


The structure of the substance (A) can be identified or confirmed by a known analytical means such as an IR spectrum, an NMR spectrum, a mass spectrum, elementary analysis.


The substance (A) may be used alone, but is preferably used in combination of at least two. In a case where a combination of two is used, the substance (A) is preferably a composition comprising a water soluble substance (A1) of those selected from the group consisting of compounds represented by Formula (I), compounds represented by Formula (II) and salts thereof; and a lipid soluble substance (A2) of those selected from the group consisting of compounds represented by Formula (I), compounds represented by Formula (II) and salts thereof because an effect of the substance (A) is synergistically enhanced.


In a case where a combination of two is used, more specifically, the substance (A) is preferably a composition comprising at least one water soluble substance (A1) selected from the group consisting of compounds represented by Formula (Ia), compounds represented by Formula (IIa) and salts thereof; and at least one lipid soluble substance (A2) selected from the group consisting of compounds represented by Formula (Ib), compounds represented by Formula (IIb) and salts thereof.




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[In Formula (Ia), R1a to R4a each independently represents a hydrogen atom, —SO3H, —PO3H2 or a glycosyl group.]




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[In Formula (IIa), R5a to R6a each independently represents a hydrogen atom, —SO3H, —PO3H2 or a glycosyl group.]




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[In Formula (Ib), R1b to R4b each independently represents a hydrogen atom or —COR11. At least one of R1b to R4b represents —COR11, and R11 represents an unsubstituted or substituted C1 to C30 alkyl group or an unsubstituted or substituted C2 to C30 alkenyl group, preferably an unsubstituted or substituted C12 to C30 alkyl group or an unsubstituted or substituted C12 to C30 alkenyl group.]




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[In Formula (IIb), R5b and R6b each independently represents a hydrogen atom or —COR11. At least one of R5b and R6b represents —COR11, and R11 represents an unsubstituted or substituted C1 to C30 alkyl group or an unsubstituted or substituted C2 to C30 alkenyl group, preferably an unsubstituted or substituted C12 to C30 alkyl group or an unsubstituted or substituted C12 to C30 alkenyl group.]


The mass ratio of the lipid soluble substance (A2) to the water soluble substance (A1) is usually from 0.001 to 1000, preferably from 0.1 to 10.


The substance (A) can be prepared into a formulation such as a wettable powder, an emulsifiable concentrate, a water soluble powder, a water dispersible granule, a dust, a tablet and the like. There is no particular limitation for a method of preparing a formulation, and a known preparation method can be used depending on a dosage form.


There is no particular limitation for a method of applying the substance (A) to a plant, and a known application method in the field of agriculture and horticulture can be used. Further, an application method to a plant can be suitably determined depending on the type and the like of a target plant. For example, preferred modes of application can include foliage application, dipping treatment, soil irrigation, seed treatment, water culture medium treatment, smoking treatment, ordinary temperature fogging treatment and the like. The method according to the present invention may be used without limitation by cultivation forms such as soil cultivation and hydroponic cultivation. Further, excellent effects can be achieved even when used in a special environment such as meristem culture. An application amount of the substance (A) according to the present invention can be suitably determined depending on meteorological conditions, formulation forms, application times, application methods, application places, target diseases to be controlled, target crops and the like.


There is no particular limitation for plants to which the method according to the present invention can be employed, and they may be either edible plants or non-edible plants. Examples of the target plants include cereal crops such as rice plant, wheat, corn; legumes such as soybean, azuki bean, peanut; fruit trees such as citrus, apple, pear, grape, peach; vegetables such as tomato, lettuce, cabbage, onion, green onion, bell pepper; pepos such as cucumber, watermelon, melon, pumpkin; root vegetables such as potato, sweet potato, Chinese yam, carrot, radish; crops for processing such as cotton, sugarbeet, hop, sugarcane, rubber tree, coffee, tobacco, tea; grass such as ryegrass, timothy, orchard grass; lawn grasses such as bentgrass, grass, and the like.


The method according to the present invention can provide a plant with stress resistance. Such stresses include biological stress due to plant viruses, phytopathogenic bacteria, phytopathogenic filamentous fungi, agricultural pests, weeds, or microorganisms used as biological agricultural chemicals or arthropods; physical or chemical stress due to high temperature, low temperature, high illuminance, low illuminance, excessive humidity, dryness, salinity, acidity, agricultural chemicals, chemical substances or heavy metals.


There is no particular limitation for plant viruses which may cause stress. For example, preferably, they can include gemini viruses having a single stranded DNA as the genome, cauliflower mosaic virus having double stranded DNA as the genome, tobacco mosaic virus, tomato bushy stunt virus having a single stranded RNA as the genome, rice ragged stunt virus having double stranded RNA as the genome and the like.


There is no particular limitation for phytopathogenic bacteria which may cause stress. For example, they include Burkholderia plantarii, Acidovorax avenae, Burkholderia glumae, Xanthomonas campestris pv. oryzae, Pseudomonas lachrymans, Erwinia carotovora and the like.


There is no particular limitation for phytopathogenic filamentous fungi which may cause stress. For example, they include Pyricularia oryzae, Gibberella fujikuroi, Cochliobolus miyabeanus, Erysiphe graminis f. sp. tritici, Gibberella zeae, Puccinia recondita, Septoria tritici, Leptosphaeria nodorum, Ustilago tritici, Sphaerotheca fuliginea, Pseudoperonospora cubensis, Mycosphaerella melonis, Fusarium oxysporum, Botrytis cinerea, Colletotrichum orbiculare, Cladosporium cucumerinum, Corynespora cassicola, Cladosporium fulvum, Phytophthora infestans and the like.


There is no particular limitation for pests which may cause stress, and examples of the pests include:


Lepidoptera pests, for example, Spodoptera frugiperda, Leucania, Spodoptera litura, Agrotis ipsilon, Adoxophyes honmai, Homona magnanima, Carposina niponensis Walsingham, Cydia molesta, Phyllocnistis citrella, Caloptilia theivora, Phyllonorycter ringoniella, Lymantria dispar, Euproctis pseudoconspersa, Chilo suppressalis, Cnaphalocrocis medinalis, Ostrinia nubilalis, Hyphantria cunea, Cadra cautella, the genus Heliothis, the genus Helicoverpa, the genus Agrotis, Tinea translucens, Ostrinia furnacalis, Pieris brassicae, Heliothis virescens, Plutella xylostella, cutworm (a kind of Noctuidae) and the like;


Hemiptera pests, for example, Aphidae such as Lipaphis erysimi, Rhopalosiphum padi, Myzus persicaem, Aphis gossypii, Aphis favae; Aleyrodidae such as Trialeurodes vaporariorum, Bemisia tabaci, Bemisia argentifolii; Pyrrhocoroidea, Riptortus clavatus, Nezara antennata, Unaspis yanonensis, Pseudococcus longispinis, Psylla pyricola, Stephanitis nashi, Nilaparvata lugens, Laodelphax straitellus, Sogatella furcifera, Nephotettix cincticeps and the like;


Coleoptera pests, for example, Phyllotreta striolata, Aulacophora femoralis, Leptinotarsa decemlineata, Phaedon cochleariae, Lissorhoptrus oryzophilus, Sitophilus zeamais, Callosobruchus chinensis, Popillia japonica, Anomala rufocuprea, corn rootwarm, the genus Diabrotic, Lasioderma serricorne, Lyctus brunneus, Monochamus alternatus, Anoplophora malasiaca, the genus Agriote, Epilachna vigintioctopunctata, Trogossitidae, Anthonomus grandis and the like;


Orthoptera pests, for example, locust, Locusta migratoria and the like;


Thysanoptera pests, for example, Thrips palmi, Scirtothrips dorsalis, Thrips tabaci, Frankliniella intonsa and the like;


Diptera pests, for example, Dacus cucurbitae, Bactrocera dorsalis, Agromyza oryzae and the like;


Mites, for example, Tetranychidae such as Tetranychus urticae, Tetranychus cinnabarinus, Tetranychus kanzawa, Panonychus citri, Panonychus ulmi, Tenuipalpidae; Aculops pelekassi, Aculus schlechtendali, Polyphagotarsonemus latus, Rhizoglyphus robini and the like.


Among these, agricultural pests for which application are particularly preferred include Aphidoidea, Aleyrodoidea, Thripidae, and Tetranychidae.


There is no particular limitation for weeds which may cause stress, and examples of them include gramineous weeds such as Echinochloa crus-galli, Sorghum bicolor, Setaria faberi Herrm, Setaria viridis, Setaria glauca, Alopecurus aequalis, Digitaria ciliaris, Eleusine indica, Poa annua; Compositae weeds such as Xanthium strumarium, Ambrosia artemisiifolia, Ambrosia trifida, Erigeron annuus, Erigeron philadelphicus, Erigeron canadensis, Conyza sumatrensis, Youngia japonica, Conyza bonariensis, Gnaphalium japonicum, Bidens, Artemisia princeps; Oxalis corniculata, Plantago asiatica, Polygonaceae, Capsella bursa-pastoris, Cardamine flexuosa, Galium aparine Abutilon theophrasti, Hydrocotyle sibthorpioides, Solanum nigrum, Ipomoea hederacea, Amaranthus lividus, Amaranthus viridis, Amaranthus retroflexus, Chenopodium album var. centrorubrum, Chenopodium album, Viola verecunda, Sida spinosa, Trifolium repens, Senna obtusifolia, Scirpus hotarui, Eleocharis acicularis, Cyperus serotinus Rottb, Monochoria vaginalis, Lindernia procumbens, Elatine triandra, Sagittaria pygmaea and the like. Preferably, they include plant parasites such as the genus Striga of Scrophulariaceae and the genus Orobanche of Orobanchaceae, which are parasitic on cereal crops, legumes, eggplant, tomato and the like in Africa, causing significant decrease in crop yields. Further, they include Amaranthus palmeri of Amaranthaceae, Ambrosia artemisiifolia and Erigeron canadensis of Asteraceae, which are glyphosate resistant weeds.


There is no particular limitation for high temperature and low temperature which may cause stress. They include, for example, high temperature injury and low temperature injury which may decrease the growth and quality of rice plant, high temperature injury which may decrease the fruit setting percentage of Solanaceae crops such as tomato, high temperature injury which tends to occur particularly in tunnel cultivation and greenhouse cultivation of lettuce and the like, high temperature injury which may inhibit the growth of turves, freezing and frost damage to tea plant and fruit trees such as citrus and the like.


There is no particular limitation for excessive humidity and dryness which may cause stress. For example, they are the poor growth of crops due to excessive humidity resulting from excessive rain fall, irrigation and poorly drained soil; or the decrease in disease resistance; or the wilt of crops due to dryness resulting from the shortage of rain fall and irrigation, sandy soil and the like.


There is no particular limitation for physical properties of soil which may cause stress. For example, they are growth disorders of crops in salty soil, acidic soil or alkaline soil and the like. Among these, effects on the poor growth in salty soil and acidic soil, in particular, effects on the poor growth of crops which are weak to acidic soil such as spinach, garden pea, fava bean, onion, asparagus, lettuce, burdock are significant, and it is effective for improving the yields and qualities of these crops.


There is no particular limitation for chemical substances which may cause stress, including at least one compound selected from agricultural chemicals such as herbicides, growth regulators, plant hormones, disease resistance inducers, fungicides, insecticides, miticides; fertilizers; surfactants; allelopathy substances produced by other plants which affects crops and the like.


There is no particular limitation for agricultural chemicals which may cause stress, and examples of the chemicals include those described as substances which may affect a physiological function of a plant.


Phytotoxicity which may cause stress is, for example, phytotoxicity when treated at a concentration above the usage standard and when applied to non-intended crops, and in addition, phytotoxicity occurring under high temperature and strong light conditions and the like. Further, the application range of agricultural chemicals can be extended wider than the conventional application range because the present invention controls those phytotoxicitys.


There is no particular limitation for heavy metals which may cause stress, and examples of the heavy metals include iron, zinc, copper, manganese, nickel, cobalt, tin, chromium, lead, cadmium, mercury, arsenic and the like.


Phytotoxicity of a plant due to agricultural chemicals can be reduced by the method according to the present invention. Examples of agricultural chemicals include herbicides; growth regulators; plant hormones; resistance inducers against pathogens; fungicides, insecticides, miticides, repellents, fertilizers, surfactants which may cause phytotoxicity when used at a high concentration; and the like. Among these, preferred is at least one selected from the group consisting of fungicides, insecticides, plant growth regulators and herbicides. Further, the agricultural chemical is preferably a respiratory inhibitor. Furthermore, the agricultural chemical is preferably a strobilurin compound.


Examples of fungicides include those such as captan, folpet, thiuram, dilam, zineb, maneb, mancozeb, propineb, polycarbamate, chlorothalonil, quintozene, captaphore, iprodione, procymidone, fluoroimide, mepronil, flutolanil, pencycuron, oxycarboxin, fosetylaluminium, propamocarb, hexaconazole, imibenconazole, tebuconazole, difenoconazole, prothioconazole, fenbuconazole, diclobutrazol, bitertanol, myclobutanil, flusilazole, hexaconazole, etaconazole, fluotrimazole, triadimefon, triadimenol, flutriafen, penconazole, diniconazole, cyproconazole, fenarimol, triflumizole, prochloraz, imazalil, kresoxim-methyl, trifloxystrobin, azoxystrobin, pyraclostrobin, orysastrobin, pefurazoate, tridemorph, fenpropimorph, trifolin, buthiobate, pyrifenox, anilazine, polyoxin, metalaxyl, oxadixyl, furalaxyl, isoprothiolane, probenazole, pyrrolnitrin, blasticidin S, kasugamycin, validamycin, dihydrostreptomycin sulfate, benomyl, carbendazim, thiophanate-methyl, hymexazol, basic copper chloride, basic copper sulfate, fentinacetate, triphenyltin hydroxide, diethofencarb, chinomethionate, binapacryl, lecithin, sodium bicarbonate, dithianon, dinocap, fenaminosulf, dichlomedin, guazatine, dodine, IBP, edifenphos, mepanipyrim, ferimzone, trichlamid, metasulfocarb, fluazinam, etoquinolak, dimethomorph, pyroquilon, tecloftalam, fthalide, phenazine oxide, thiabendazole, tricyclazole, vincrozoline, cymoxanil, guazatine, propamocarb hydrochloride, oxolinic acid, cyflufenamid, iminoctadine, triazine, fenhexamid, cyazofamid, cyprodinil, carpropamide, boscalid. They also include resistance inducers against a pathogen such as probenazole, tiadinil.


Among these, particularly preferred are strobilurin based fungicides such as kresoxim-methyl, trifloxystrobin, azoxystrobin, pyraclostrobin, orysastrobin.


Herbicides include 2,4-D, MCPA, clomeprop, dicamba, chlorotoluron, diuron, linuron, isouron, fenuron, neburon, simazine, atrazine, simetryn, prometryn, hexazinone, propazine, desmetryn, terbumeton, propanil, bromoxynil, ioxynil, pyridate, chloridazon, bentazone, chlomethoxyfen, bifenox, acifluorfen sodium salt, flumioxazin, thidiazimin, oxadiazon, sulfentrazone, pentoxazone, pyraclonil, pyrazolynate, pyrazoxyfen, benzofenap, mesotrione, isoxaflutole, isoxachlortole, amitrole, aclonifen, diflufenican, benzobicyclon, diclofop-methyl, fluazifop-butyl, alloxydim sodium salt, clethodim, sethoxydim, tralkoxydim, tepraloxydim, bensulfuron-methyl, pyrazosulfuron-ethyl, rimsulfuron, imazosulfuron, prosulfuron, flumetsulam, diclosulam, metosulam, imazapyr, imazaquin, pyrithiobac-sodium salt, bispyribac-sodium salt, pyriminobac-methyl, flucabazone, propoxycarbazone, glyphosate, glyphosate ammonium salt, glufosinate, trifluralin, pendimethalin, benfluralin, prodiamine, propham, dithiopyr, alachlor, metolachlor, pethoxamid, acetochlor, propachlor, dimethenamid, diphenamid, napropamide, mefenacet, fentrazamide, molinate, dimepiperate, cycloate, esprocarb, thiobencarb, thiocarbazil, bensulide, dalapon, asulam, DNOC, dinoseb, flupoxam, traiziflam, quinchlorac, cinmethylin, dazomet, dymron, etobenzanide, oxaziclomefone, pyributicarband the like.


Examples of insecticides include organophosphate based and carbamate based insecticides such as fenthion, fenitrothion, diazinon, chlorpyrifos, ESP, vamidothion, phenthoate, dimethoate, formothion, malathlon, trichlorfon, thiometon, phosmet, dichlorvos, acephate, EPBP, methylparathion, oxydemeton-methyl, ethion, salithion, cyanophos, isoxathion, pyridaphenthion, phosalone, methidathion, sulprofos, chlorfenvinphos, tetrachlorvinphos, dimethylvinphos, propaphos, isofenphos, ethylthiometon, prophenophos, pyraclophos, monocrotophos, azinephosmethyl, aldicarb, methomyl, thiodicarb, carbofuran, carbosulfane, benfuracarb, furathiocarb, propoxur, BPMC, MTMC, MIPC, carbaryl, pirimicarb, ethiofencarb, phenoxycarb, cartap, thiocyclam, bensultap; pyrethroid based insecticides such as permethrin, cypermethrin, deltamethrin, fenvalerate, fenpropathrin, pyrethrin, allethrin, tetramethrin, resmethrin, dimethrin, propathrin, phenothrin, prothrin, fluvalinate, cyfluthrin, cyhalothrin, flucythrinate, etofenprox, cycloprothrin, tralomethrin, silafluofen, acrinathrin; neonicotinoid based insecticides such as imidacloprid, acetamiprid, nitenpyram, thiacloprid, clothianidin, thiamethoxam, dinotefuran, nithiazine; benzoylphenylurea based insecticides such as diflubenzuron, chlorfluazuron, hexaflumuron, triflumuron, flufenoxuron, furcycloxuron, buprofezin, pyriproxifen, methoprene, benzoepin, diafenthiuron, fipronil, nicotine sulfate, rotenone, metaldehyde, acetamiprid, chlorphenapyl, nitenpyram, thiacloprid, clothianidin, thiamethoxam, dinotefuran, indoxacarb, pymetrozine, spinosad, emamectin, pyridalyl, tebufenozide, chromafenozide, methoxyfenozide, tolfenpyrad, flubendiamide, chlorantraniliprole, cyantraniliprole; Nematicides such as fenamiphos, phosthiazate, cadusafos; miticides such as chlorbenzilate, phenisobromolate, dicofol, amitraz, BPPS, benzomate, hexythiazox, fenbutatin-oxide, polynactin, chinomethionate, CPCBS, tetradifon, avermectin, milbemectin, clofentezine, cyhexatin, pyridaben, fenpyroximate, tebufenpyrad, cyenopyrafen, cyflumetofen, pyrimidifen, phenothiocarb, dienochlor, fluacrypyrim, acequinocyl, bifenazate, etoxazole, spirodiclofen, fenazaquin; microorganism-derived formulations such as BT agents; and the like.


Among these, particularly preferred are neonicotinoid based insecticides such as imidacloprid, acetamiprid, nitenpyram, thiacloprid, clothianidin, thiamethoxam, dinotefuran, nithiazine; and insecticides or miticides which have respiratory inhibition effects such as chlorphenapyl, pymetrozine, pyridaben, fenpyroximate, tolfenpyrad, tebufenpyrad, cyenopyrafen, cyflumetofen, fluacrypyrim, acequinocyl, fenazaquin.


Examples of plant hormones include gibberellins (for example, gibberellin A3, gibberellin A4, gibberellin A7 and the like), auxins (for example, 2,4-D, IAA, NAA and the like), cytokinins (for example, kinetin, benzyladenine and the like), abscisic acid, jasmone acids, brassinosteroids, strigolactones, salicylic acid and the like.


As plant growth regulators, in addition to the aforementioned plant hormones, mentioned are hymexazol, uniconazole, trinexapac, daminozide, cyanamide and the like.


Examples of fertilizers include nitrogenous fertilizers, phosphatic fertilizers, potash fertilizers, calcareous fertilizers, magnesium fertilizers, silicate fertilizers, trace element fertilizers, animal matter fertilizers, plant matter fertilizers and the like. When the concentration of a water soluble component of a fertilizer is too high, fertilizer disorders such as withering and death of root and leaf may be caused to a plant. Further, when a certain type of a fertilizer such as ammonium sulfate is used in a large amount, the growth of a plant may be compromised through soil acidification.


A surfactant is used as an auxiliary component of an agrochemical formulation, as an active component of some insecticides or miticides, or as a spreader. Examples of surfactants include nonionic surfactants such alkylphenyl ether in which polyoxyethylene is added, alkyl ether in which polyoxyethylene is added, higher fatty acid ester in which polyoxyethylene is added, sorbitan higher fatty acid ester in which polyoxyethylene is added, tristyrylphenyl ether in which polyoxyethylene added; anionic surfactants such as a sulfuric ester salt of alkylphenyl ether in which polyoxyethylene is added, alkylbenzene sulfonate, a sulfuric ester salt of higher alcohol, alkylnaphthalenesulfonate, polycarboxylate, lignin sulfonate, a formaldehyde condensate of alkylnaphthalenesulfonate, a copolymer of isobutylene-maleic anhydride; cationic surfactants such as alkyltrimethylammonium chloride, methyl.polyoxyethylene.alkylammonium chloride, alkyl.N-methylpyridium bromide, mono- or di-alkylmethylated ammonium chloride, alkylpentamethylpropylenediamine dichloride, alkyldimethylbenzalkonium chloride, benzethonium chloride; amphoteric surfactants such as dialkyldiaminoethylbetaine, alkyldimethylbenzylbetaine, dialkyldiaminoethylglycine, alkyldimethylbenzylglycine; and the like.







EXAMPLES

The present invention will be described in detail with reference to Examples, but the scope of the present invention shall not be limited by these.


Various substances (A) were synthesized by esterifying, glycosylating or oxidizing ascorbic acid, isoascorbic acid or dehydroascorbic acid by a known reaction. Some of the substances (A) synthesized are shown in Tables 1 and 2. R1 to R4 in Table 1 correspond to R1 to R4 in Formula (I). R5 and R6 in Table 2 correspond to R5 and R6 in Formula (II).


[Table 1]













TABLE 1





Compound #
R1
R2
R3
R4



















1
H
H
H
H


2
SO3H
H
H
H


3
PO3H2
H
H
H


4
glucosyl
H
H
H


5
mannosyl
H
H
H


6
galactosyl
H
H
H


7
COCH3
H
H
H


8
COC3H7-i
H
H
H


9
COC17H35-n
H
H
H


10
COC16H33-n
H
H
H


11
COC18H37-n
H
H
H


12
CO(CH2)7CH═CHC6H13-n
H
H
H


13
COCH═CH2
H
H
H


14
COCH2CH═CH2
H
H
H


15
H
SO3H
H
H


16
H
PO3H2
H
H


17
H
glucosyl
H
H


18
H
mannosyl
H
H


19
H
galactosyl
H
H


20
H
COCH3
H
H


21
H
COC3H7-i
H
H


22
H
COC17H35-n
H
H


23
H
COC16H33-n
H
H


24
H
COC18H37-n
H
H


25
H
CO(CH2)7CH═CHC6H13-n
H
H


26
H
COCH═CH2
H
H


27
H
COCH2CH═CH2
H
H


28
H
H
SO3H
H


29
H
H
PO3H2
H


30
H
H
glucosyl
H


31
H
H
mannosyl
H


32
H
H
galactosyl
H


33
H
H
COCH3
H


34
H
H
COC3H7-i
H


35
H
H
COC17H35-n
H


36
H
H
COC16H33-n
H


37
H
H
COC18H37-n
H


38
H
H
CO(CH2)7CH═CHC6H13-n
H


39
H
H
COCH═CH2
H


40
H
H
COCH2CH═CH2
H


41
H
H
H
SO3H


42
H
H
H
PO3H2


43
H
H
H
glucosyl


44
H
H
H
mannosyl


45
H
H
H
galactosyl


46
H
H
H
COCH3


47
H
H
H
COC3H7-i


48
H
H
H
COC17H35-n


49
H
H
H
COC16H33-n


50
H
H
H
COC18H37-n


51
H
H
H
CO(CH2)7CH═CHC6H13-n


52
H
H
H
COCH═CH2


53
H
H
H
COCH2CH═CH2


54
SO3H
SO3H
H
H


55
SO3H
PO3H2
H
H


56
SO3H
glucosyl
H
H


57
SO3H
mannosyl
H
H


58
SO3H
galactosyl
H
H


59
SO3H
COCH3
H
H


60
SO3H
COC3H7-i
H
H


61
SO3H
COC17H35-n
H
H


62
SO3H
COC16H33-n
H
H


63
SO3H
COC18H37-n
H
H


64
SO3H
CO(CH2)7CH═CHC6H13-n
H
H


65
SO3H
COCH═CH2
H
H


66
SO3H
COCH2CH═CH2
H
H


67
SO3H
SO3H
H
H


68
SO3H
PO3H2
H
H


69
SO3H
glucosyl
H
H


70
SO3H
mannosyl
H
H


71
SO3H
galactosyl
H
H


72
SO3H
COCH3
H
H


73
SO3H
COC3H7-i
H
H


74
SO3H
COC17H35-n
H
H


75
SO3H
COC16H33-n
H
H


76
SO3H
COC18H37-n
H
H


77
SO3H
CO(CH2)7CH═CHC6H13-n
H
H


78
SO3H
COCH═CH2
H
H


79
SO3H
COCH2CH═CH2
H
H


80
glucosyl
SO3H
H
H


81
glucosyl
PO3H2
H
H


82
glucosyl
glucosyl
H
H


83
glucosyl
mannosyl
H
H


84
glucosyl
galactosyl
H
H


85
glucosyl
COCH3
H
H


86
glucosyl
COC3H7-i
H
H


87
glucosyl
COC17H35-n
H
H


88
glucosyl
COC16H33-n
H
H


89
glucosyl
COC18H37-n
H
H


90
glucosyl
CO(CH2)7CH═CHC6H13-n
H
H


91
glucosyl
COCH═CH2
H
H


92
glucosyl
COCH2CH═CH2
H
H


93
COC16H33
SO3H
H
H


94
COC16H33
PO3H2
H
H


95
COC16H33
glucosyl
H
H


96
COC16H33
mannosyl
H
H


97
COC16H33
galactosyl
H
H


98
COC16H33
COCH3
H
H


99
COC16H33
COC3H7-i
H
H


100
COC16H33
COC17H35-n
H
H


101
COC16H33
COC16H33-n
H
H


102
COC16H33
COC18H37-n
H
H


103
COC16H33
CO(CH2)7CH═CHC6H13-n
H
H


104
COC16H33
COCH═CH2
H
H


105
COC16H33
COCH2CH═CH2
H
H


106
CO(CH2)7CH═CHC6H13
SO3H
H
H


107
CO(CH2)7CH═CHC6H13
PO3H2
H
H


108
CO(CH2)7CH═CHC6H13
glucosyl
H
H


109
CO(CH2)7CH═CHC6H13
mannosyl
H
H


110
CO(CH2)7CH═CHC6H13
galactosyl
H
H


111
CO(CH2)7CH═CHC6H13
COCH3
H
H


112
CO(CH2)7CH═CHC6H13
COC3H7-i
H
H


113
CO(CH2)7CH═CHC6H13
COC17H35-n
H
H


114
CO(CH2)7CH═CHC6H13
COC16H33-n
H
H


115
CO(CH2)7CH═CHC6H13
COC18H37-n
H
H


116
CO(CH2)7CH═CHC6H13
CO(CH2)7CH═CHC6H13-n
H
H


117
CO(CH2)7CH═CHC6H13
COCH═CH2
H
H


118
CO(CH2)7CH═CHC6H13
COCH2CH═CH2
H
H


119
SO3H
H
SO3H
H


120
SO3H
H
PO3H2
H


121
SO3H
H
glucosyl
H


122
SO3H
H
mannosyl
H


123
SO3H
H
galactosyl
H


124
SO3H
H
COCH3
H


125
SO3H
H
COC3H7-i
H


126
SO3H
H
COC17H35-n
H


127
SO3H
H
COC16H33-n
H


128
SO3H
H
COC18H37-n
H


129
SO3H
H
CO(CH2)7CH═CHC6H13-n
H


130
SO3H
H
COCH═CH2
H


131
SO3H
H
COCH2CH═CH2
H


132
PO3H2
H
SO3H
H


133
PO3H2
H
PO3H2
H


134
PO3H2
H
glucosyl
H


135
PO3H2
H
mannosyl
H


136
PO3H2
H
galactosyl
H


137
PO3H2
H
COCH3
H


138
PO3H2
H
COC3H7-i
H


139
PO3H2
H
COC17H35-n
H


140
PO3H2
H
COC16H33-n
H


141
PO3H2
H
COC18H37-n
H


142
PO3H2
H
CO(CH2)7CH═CHC6H13-n
H


143
PO3H2
H
COCH═CH2
H


144
PO3H2
H
COCH2CH═CH2
H


145
glucosyl
H
SO3H
H


146
glucosyl
H
PO3H2
H


147
glucosyl
H
glucosyl
H


148
glucosyl
H
mannosyl
H


149
glucosyl
H
galactosyl
H


150
glucosyl
H
COCH3
H


151
glucosyl
H
COC3H7-i
H


152
glucosyl
H
COC17H35-n
H


153
glucosyl
H
COC16H33-n
H


154
glucosyl
H
COC18H37-n
H


155
glucosyl
H
CO(CH2)7CH═CHC6H13-n
H


156
glucosyl
H
COCH═CH2
H


157
glucosyl
H
COCH2CH═CH2
H


158
COC16H33-n
H
SO3H
H


159
COC16H33-n
H
PO3H2
H


160
COC16H33-n
H
glucosyl
H


161
COC16H33-n
H
mannosyl
H


162
COC16H33-n
H
galactosyl
H


163
COC16H33-n
H
COCH3
H


164
COC16H33-n
H
COC3H7-i
H


165
COC16H33-n
H
COC17H35-n
H


166
COC16H33-n
H
COC16H33-n
H


167
COC16H33-n
H
COC18H37-n
H


168
COC16H33-n
H
CO(CH2)7CH═CHC6H13-n
H


169
COC16H33-n
H
COCH═CH2
H


170
COC16H33-n
H
COCH2CH═CH2
H


171
CO(CH2)7CH═CHC6H13-n
H
SO3H
H


172
CO(CH2)7CH═CHC6H13-n
H
PO3H2
H


173
CO(CH2)7CH═CHC6H13-n
H
glucosyl
H


174
CO(CH2)7CH═CHC6H13-n
H
mannosyl
H


175
CO(CH2)7CH═CHC6H13-n
H
galactosyl
H


176
CO(CH2)7CH═CHC6H13-n
H
COCH3
H


177
CO(CH2)7CH═CHC6H13-n
H
COC3H7-i
H


178
CO(CH2)7CH═CHC6H13-n
H
COC17H35-n
H


179
CO(CH2)7CH═CHC6H13-n
H
COC16H33-n
H


180
CO(CH2)7CH═CHC6H13-n
H
COC18H37-n
H


181
CO(CH2)7CH═CHC6H13-n
H
CO(CH2)7CH═CHC6H13-n
H


182
CO(CH2)7CH═CHC6H13-n
H
COCH═CH2
H


183
CO(CH2)7CH═CHC6H13-n
H
COCH2CH═CH2
H


184
SO3H
H
H
SO3H


185
SO3H
H
H
PO3H2


186
SO3H
H
H
glucosyl


187
SO3H
H
H
mannosyl


188
SO3H
H
H
galactosyl


189
SO3H
H
H
COCH3


190
SO3H
H
H
COC3H7-i


191
SO3H
H
H
COC17H35-n


192
SO3H
H
H
COC16H33-n


193
SO3H
H
H
COC18H37-n


194
SO3H
H
H
CO(CH2)7CH═CHC6H13-n


195
SO3H
H
H
COCH═CH2


196
SO3H
H
H
COCH2CH═CH2


197
PO3H2
H
H
SO3H


198
PO3H2
H
H
PO3H2


199
PO3H2
H
H
glucosyl


200
PO3H2
H
H
mannosyl


201
PO3H2
H
H
galactosyl


202
PO3H2
H
H
COCH3


203
PO3H2
H
H
COC3H7-i


204
PO3H2
H
H
COC17H35-n


205
PO3H2
H
H
COC16H33-n


206
PO3H2
H
H
COC18H37-n


207
PO3H2
H
H
CO(CH2)7CH═CHC6H13-n


208
PO3H2
H
H
COCH═CH2


209
PO3H2
H
H
COCH2CH═CH2


210
glucosyl
H
H
SO3H


211
glucosyl
H
H
PO3H2


212
glucosyl
H
H
glucosyl


213
glucosyl
H
H
mannosyl


214
glucosyl
H
H
galactosyl


215
glucosyl
H
H
COCH3


216
glucosyl
H
H
COC3H7-i


217
glucosyl
H
H
COC17H35-n


218
glucosyl
H
H
COC16H33-n


219
glucosyl
H
H
COC18H37-n


220
glucosyl
H
H
CO(CH2)7CH═CHC6H13-n


221
glucosyl
H
H
COCH═CH2


222
glucosyl
H
H
COCH2CH═CH2


223
COC16H33-n
H
H
SO3H


224
COC16H33-n
H
H
PO3H2


225
COC16H33-n
H
H
glucosyl


226
COC16H33-n
H
H
mannosyl


227
COC16H33-n
H
H
galactosyl


228
COC16H33-n
H
H
COCH3


229
COC16H33-n
H
H
COC3H7-i


230
COC16H33-n
H
H
COC17H35-n


231
COC16H33-n
H
H
COC16H33-n


232
COC16H33-n
H
H
COC18H37-n


233
COC16H33-n
H
H
CO(CH2)7CH═CHC6H13-n


234
COC16H33-n
H
H
COCH═CH2


235
COC16H33-n
H
H
COCH2CH═CH2


236
CO(CH2)7CH═CHC6H13-n
H
H
SO3H


237
CO(CH2)7CH═CHC6H13-n
H
H
PO3H2


238
CO(CH2)7CH═CHC6H13-n
H
H
glucosyl


239
CO(CH2)7CH═CHC6H13-n
H
H
mannosyl


240
CO(CH2)7CH═CHC6H13-n
H
H
galactosyl


241
CO(CH2)7CH═CHC6H13-n
H
H
COCH3


242
CO(CH2)7CH═CHC6H13-n
H
H
COC3H7-i


243
CO(CH2)7CH═CHC6H13-n
H
H
COC17H35-n


244
CO(CH2)7CH═CHC6H13-n
H
H
COC16H33-n


245
CO(CH2)7CH═CHC6H13-n
H
H
COC18H37-n


246
CO(CH2)7CH═CHC6H13-n
H
H
CO(CH2)7CH═CHC6H13-n


247
CO(CH2)7CH═CHC6H13-n
H
H
COCH═CH2


248
CO(CH2)7CH═CHC6H13-n
H
H
COCH2CH═CH2


249
SO3H
SO3H
SO3H
H


250
SO3H
SO3H
PO3H2
H


251
SO3H
SO3H
glucosyl
H


252
SO3H
SO3H
mannosyl
H


253
SO3H
SO3H
galactosyl
H


254
SO3H
SO3H
COCH3
H


255
SO3H
SO3H
COC3H7-i
H


256
SO3H
SO3H
COC17H35-n
H


257
SO3H
SO3H
COC16H33-n
H


258
SO3H
SO3H
COC18H37-n
H


259
SO3H
SO3H
CO(CH2)7CH═CHC6H13-n
H


260
SO3H
SO3H
COCH═CH2
H


261
SO3H
SO3H
COCH2CH═CH2
H


262
PO3H2
PO3H2
SO3H
H


263
PO3H2
PO3H2
PO3H2
H


264
PO3H2
PO3H2
glucosyl
H


265
PO3H2
PO3H2
mannosyl
H


266
PO3H2
PO3H2
galactosyl
H


267
PO3H2
PO3H2
COCH3
H


268
PO3H2
PO3H2
COC3H7-i
H


269
PO3H2
PO3H2
COC17H35-n
H


270
PO3H2
PO3H2
COC16H33-n
H


271
PO3H2
PO3H2
COC18H37-n
H


272
PO3H2
PO3H2
CO(CH2)7CH═CHC6H13-n
H


273
PO3H2
PO3H2
COCH═CH2
H


274
PO3H2
PO3H2
COCH2CH═CH2
H


275
glucosyl
glucosyl
SO3H
H


276
glucosyl
glucosyl
PO3H2
H


277
glucosyl
glucosyl
glucosyl
H


278
glucosyl
glucosyl
mannosyl
H


279
glucosyl
glucosyl
galactosyl
H


280
glucosyl
glucosyl
COCH3
H


281
glucosyl
glucosyl
COC3H7-i
H


282
glucosyl
glucosyl
COC17H35-n
H


283
glucosyl
glucosyl
COC16H33-n
H


284
glucosyl
glucosyl
COC18H37-n
H


285
glucosyl
glucosyl
CO(CH2)7CH═CHC6H13-n
H


286
glucosyl
glucosyl
COCH═CH2
H


287
glucosyl
glucosyl
COCH2CH═CH2
H


288
COC16H33-n
COC16H33-n
SO3H
H


289
COC16H33-n
COC16H33-n
PO3H2
H


290
COC16H33-n
COC16H33-n
glucosyl
H


291
COC16H33-n
COC16H33-n
mannosyl
H


292
COC16H33-n
COC16H33-n
galactosyl
H


293
COC16H33-n
COC16H33-n
COCH3
H


294
COC16H33-n
COC16H33-n
COC3H7-i
H


295
COC16H33-n
COC16H33-n
COC17H35-n
H


296
COC16H33-n
COC16H33-n
COC16H33-n
H


297
COC16H33-n
COC16H33-n
COC18H37-n
H


298
COC16H33-n
COC16H33-n
CO(CH2)7CH═CHC6H13-n
H


299
COC16H33-n
COC16H33-n
COCH═CH2
H


300
COC16H33-n
COC16H33-n
COCH2CH═CH2
H


301
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
SO3H
H


302
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
PO3H2
H


303
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
glucosyl
H


304
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
mannosyl
H


305
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
galactosyl
H


306
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
COCH3
H


307
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
COC3H7-i
H


308
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
COC17H35-n
H


309
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
COC16H33-n
H


310
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
COC18H37-n
H


311
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
H


312
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
COCH═CH2
H


313
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
COCH2CH═CH2
H


314
SO3H
SO3H
H
SO3H


315
SO3H
SO3H
H
PO3H2


316
SO3H
SO3H
H
glucosyl


317
SO3H
SO3H
H
mannosyl


318
SO3H
SO3H
H
galactosyl


319
SO3H
SO3H
H
COCH3


320
SO3H
SO3H
H
COC3H7-i


321
SO3H
SO3H
H
COC17H35-n


322
SO3H
SO3H
H
COC16H33-n


323
SO3H
SO3H
H
COC18H37-n


324
SO3H
SO3H
H
CO(CH2)7CH═CHC6H13-n


325
SO3H
SO3H
H
COCH═CH2


326
SO3H
SO3H
H
COCH2CH═CH2


327
PO3H2
PO3H2
H
SO3H


328
PO3H2
PO3H2
H
PO3H2


329
PO3H2
PO3H2
H
glucosyl


330
PO3H2
PO3H2
H
mannosyl


331
PO3H2
PO3H2
H
galactosyl


332
PO3H2
PO3H2
H
COCH3


333
PO3H2
PO3H2
H
COC3H7-i


334
PO3H2
PO3H2
H
COC17H35-n


335
PO3H2
PO3H2
H
COC16H33-n


336
PO3H2
PO3H2
H
COC18H37-n


337
PO3H2
PO3H2
H
CO(CH2)7CH═CHC6H13-n


338
PO3H2
PO3H2
H
COCH═CH2


339
PO3H2
PO3H2
H
COCH2CH═CH2


340
glucosyl
glucosyl
H
SO3H


341
glucosyl
glucosyl
H
PO3H2


342
glucosyl
glucosyl
H
glucosyl


343
glucosyl
glucosyl
H
mannosyl


344
glucosyl
glucosyl
H
galactosyl


345
glucosyl
glucosyl
H
COCH3


346
glucosyl
glucosyl
H
COC3H7-i


347
glucosyl
glucosyl
H
COC17H35-n


348
glucosyl
glucosyl
H
COC16H33-n


349
glucosyl
glucosyl
H
COC18H37-n


350
glucosyl
glucosyl
H
CO(CH2)7CH═CHC6H13-n


351
glucosyl
glucosyl
H
COCH═CH2


352
glucosyl
glucosyl
H
COCH2CH═CH2


353
COC16H33-n
COC16H33-n
H
SO3H


354
COC16H33-n
COC16H33-n
H
PO3H2


355
COC16H33-n
COC16H33-n
H
glucosyl


356
COC16H33-n
COC16H33-n
H
mannosyl


357
COC16H33-n
COC16H33-n
H
galactosyl


358
COC16H33-n
COC16H33-n
H
COCH3


359
COC16H33-n
COC16H33-n
H
COC3H7-i


360
COC16H33-n
COC16H33-n
H
COC17H35-n


361
COC16H33-n
COC16H33-n
H
COC16H33-n


362
COC16H33-n
COC16H33-n
H
COC18H37-n


363
COC16H33-n
COC16H33-n
H
CO(CH2)7CH═CHC6H13-n


364
COC16H33-n
COC16H33-n
H
COCH═CH2


365
COC16H33-n
COC16H33-n
H
COCH2CH═CH2


366
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
H
SO3H


367
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
H
PO3H2


368
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
H
glucosyl


369
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
H
mannosyl


370
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
H
galactosyl


371
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
H
COCH3


372
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
H
COC3H7-i


373
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
H
COC17H35-n


374
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
H
COC16H33-n


375
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
H
COC18H37-n


376
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
H
CO(CH2)7CH═CHC6H13-n


377
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
H
COCH═CH2


378
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
H
COCH2CH═CH2


379
SO3H
SO3H
SO3H
SO3H


380
SO3H
SO3H
SO3H
PO3H2


381
SO3H
SO3H
SO3H
glucosyl


382
SO3H
SO3H
SO3H
mannosyl


383
SO3H
SO3H
SO3H
galactosyl


384
SO3H
SO3H
SO3H
COCH3


385
SO3H
SO3H
SO3H
COC3H7-i


386
SO3H
SO3H
SO3H
COC17H35-n


387
SO3H
SO3H
SO3H
COC16H33-n


388
SO3H
SO3H
SO3H
COC18H37-n


389
SO3H
SO3H
SO3H
CO(CH2)7CH═CHC6H13-n


390
SO3H
SO3H
SO3H
COCH═CH2


391
SO3H
SO3H
SO3H
COCH2CH═CH2


392
PO3H2
PO3H2
PO3H2
SO3H


393
PO3H2
PO3H2
PO3H2
PO3H2


394
PO3H2
PO3H2
PO3H2
glucosyl


395
PO3H2
PO3H2
PO3H2
mannosyl


396
PO3H2
PO3H2
PO3H2
galactosyl


397
PO3H2
PO3H2
PO3H2
COCH3


398
PO3H2
PO3H2
PO3H2
COC3H7-i


399
PO3H2
PO3H2
PO3H2
COC17H35-n


400
PO3H2
PO3H2
PO3H2
COC16H33-n


401
PO3H2
PO3H2
PO3H2
COC18H37-n


402
PO3H2
PO3H2
PO3H2
CO(CH2)7CH═CHC6H13-n


403
PO3H2
PO3H2
PO3H2
COCH═CH2


404
PO3H2
PO3H2
PO3H2
COCH2CH═CH2


405
glucosyl
glucosyl
glucosyl
SO3H


406
glucosyl
glucosyl
glucosyl
PO3H2


407
glucosyl
glucosyl
glucosyl
glucosyl


408
glucosyl
glucosyl
glucosyl
mannosyl


409
glucosyl
glucosyl
glucosyl
galactosyl


410
glucosyl
glucosyl
glucosyl
COCH3


411
glucosyl
glucosyl
glucosyl
COC3H7-i


412
glucosyl
glucosyl
glucosyl
COC17H35-n


413
glucosyl
glucosyl
glucosyl
COC16H33-n


414
glucosyl
glucosyl
glucosyl
COC18H37-n


415
glucosyl
glucosyl
glucosyl
CO(CH2)7CH═CHC6H13-n


416
glucosyl
glucosyl
glucosyl
COCH═CH2


417
glucosyl
glucosyl
glucosyl
COCH2CH═CH2


418
COC16H33-n
COC16H33-n
COC16H33-n
SO3H


419
COC16H33-n
COC16H33-n
COC16H33-n
PO3H2


420
COC16H33-n
COC16H33-n
COC16H33-n
glucosyl


421
COC16H33-n
COC16H33-n
COC16H33-n
mannosyl


422
COC16H33-n
COC16H33-n
COC16H33-n
galactosyl


423
COC16H33-n
COC16H33-n
COC16H33-n
COCH3


424
COC16H33-n
COC16H33-n
COC16H33-n
COC3H7-i


425
COC16H33-n
COC16H33-n
COC16H33-n
COC17H35-n


426
COC16H33-n
COC16H33-n
COC16H33-n
COC16H33-n


427
COC16H33-n
COC16H33-n
COC16H33-n
COC18H37-n


428
COC16H33-n
COC16H33-n
COC16H33-n
CO(CH2)7CH═CHC6H13-n


429
COC16H33-n
COC16H33-n
COC16H33-n
COCH═CH2


430
COC16H33-n
COC16H33-n
COC16H33-n
COCH2CH═CH2


431
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
SO3H


432
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
PO3H2


433
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
glucosyl


434
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
mannosyl


435
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
galactosyl


436
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
COCH3


437
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
COC3H7-i


438
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
COC17H35-n


439
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
COC16H33-n


440
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
COC18H37-n


441
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n


442
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
COCH═CH2


443
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n
COCH2CH═CH2


















TABLE 2





Compound #
R5
R6







444
H
H


445
SO3H
H


446
PO3H2
H


447
glucosyl
H


448
mannosyl
H


449
galactosyl
H


450
COCH3
H


451
COC3H7-i
H


452
COC17H35-n
H


453
COC16H33-n
H


454
COC18H37-n
H


455
CO(CH2)7CH═CHC6H13-n
H


456
COCH═CH2
H


457
COCH2CH═CH2
H


458
H
SO3H


459
H
PO3H2


460
H
glucosyl


461
H
mannosyl


462
H
galactosyl


463
H
COCH3


464
H
COC3H7-i


465
H
COC17H35-n


466
H
COC16H33-n


467
H
COC18H37-n


468
H
CO(CH2)7CH═CHC6H13-n


469
H
COCH═CH2


470
H
COCH2CH═CH2


471
SO3H
SO3H


472
SO3H
PO3H2


473
SO3H
glucosyl


474
SO3H
mannosyl


475
SO3H
galactosyl


476
SO3H
COCH3


477
SO3H
COC3H7-i


478
SO3H
COC17H35-n


479
SO3H
COC16H33-n


480
SO3H
COC18H37-n


481
SO3H
CO(CH2)7CH═CHC6H13-n


482
SO3H
COCH═CH2


483
SO3H
COCH2CH═CH2


484
PO3H2
SO3H


485
PO3H2
PO3H2


486
PO3H2
glucosyl


487
PO3H2
mannosyl


488
PO3H2
galactosyl


489
PO3H2
COCH3


490
PO3H2
COC3H7-i


491
PO3H2
COC17H35-n


492
PO3H2
COC16H33-n


493
PO3H2
COC18H37-n


494
PO3H2
CO(CH2)7CH═CHC6H13-n


495
PO3H2
COCH═CH2


496
PO3H2
COCH2CH═CH2


497
glucosyl
SO3H


498
glucosyl
PO3H2


499
glucosyl
glucosyl


500
glucosyl
mannosyl


501
glucosyl
galactosyl


502
glucosyl
COCH3


503
glucosyl
COC3H7-i


504
glucosyl
COC17H35-n


505
glucosyl
COC16H33-n


506
glucosyl
COC18H37-n


507
glucosyl
CO(CH2)7CH═CHC6H13-n


508
glucosyl
COCH═CH2


509
glucosyl
COCH2CH═CH2


510
COC16H33-n
SO3H


511
COC16H33-n
PO3H2


512
COC16H33-n
glucosyl


513
COC16H33-n
mannosyl


514
COC16H33-n
galactosyl


515
COC16H33-n
COCH3


516
COC16H33-n
COC3H7-i


517
COC16H33-n
COC17H35-n


518
COC16H33-n
COC16H33-n


519
COC16H33-n
COC18H37-n


520
COC16H33-n
CO(CH2)7CH═CHC6H13-n


521
COC16H33-n
COCH═CH2


522
COC16H33-n
COCH2CH═CH2


523
CO(CH2)7CH═CHC6H13-n
SO3H


524
CO(CH2)7CH═CHC6H13-n
PO3H2


525
CO(CH2)7CH═CHC6H13-n
glucosyl


526
CO(CH2)7CH═CHC6H13-n
mannosyl


527
CO(CH2)7CH═CHC6H13-n
galactosyl


528
CO(CH2)7CH═CHC6H13-n
COCH3


529
CO(CH2)7CH═CHC6H13-n
COC3H7-i


530
CO(CH2)7CH═CHC6H13-n
COC17H35-n


531
CO(CH2)7CH═CHC6H13-n
COC16H33-n


532
CO(CH2)7CH═CHC6H13-n
COC18H37-n


533
CO(CH2)7CH═CHC6H13-n
CO(CH2)7CH═CHC6H13-n


534
CO(CH2)7CH═CHC6H13-n
COCH═CH2


535
CO(CH2)7CH═CHC6H13-n
COCH2CH═CH2









Next, some examples of the formulations according to the present invention are shown. There is no particular limitation for mixing prescriptions for the formulations, and they are widely modifiable. The parts in the formulations of Examples represent parts by weight.


Formulation Example 1
Wettable Powder


















Substance (A)
20 parts



White carbon
20 parts



Diatomaceous earth
52 parts



Sodium alkyl sulfate
 8 parts











The above materials are uniformly mixed, and finely ground to obtain a wettable powder.


Formulation Example 2
Emulsifiable Concentrate


















Substance (A)
20 parts



Xylene
55 parts



Dimethylformamide
15 parts



Polyoxyethylene phenyl ether
10 parts











The above materials are mixed, and dissolved to obtain an emulsion.


Formulation Example 3
Granular formulation


















Substance (A)
10 parts



Talc
37 parts



Clay
36 parts



Bentonite
10 parts



Sodium alkyl sulfate
 7 parts











The above materials are uniformly mixed, finely ground, and then granulated to obtain a granular formulation.


Formulation Example 4
Flowable Formulation



















Substance (A)
10
parts



Polyoxyethylene aryl phenyl ether
2
parts



Dialkyl sulfosuccinate sodium salt
0.5
part



Glycerin
5
parts



Xanthan gum
0.3
part



Water
82.2
parts











The above materials are mixed and wet ground to obtain a flowable formulation.


Formulation Example 5
Water Dispersible Granule


















Substance (A)
30 parts



Inorganic carrier
70 parts











The above materials are uniformly mixed, finely ground, and then granulated to obtain a water dispersible granule.


Test Example 1
Evaluation Test for Relief Effects of High Temperature Injury on Tomato

N,N-dimethylformamide based solutions were prepared according to the formulations shown in Table 3 to give chemical solutions for the tests.


Tomato (breed: Momotaro) grown up to the 2.5 leaf stage in a greenhouse was prepared.


The above chemical solution was sprayed to the stem and leaf parts of the above tomato nursery plants in a sufficient amount, and then air dried. They were allowed to grow at 30° C. for 2 days under conditions of 16 hours under a daylight condition and 8 hours under a dark condition. Then, they were allowed to grow for 6 days under conditions of 16 hours under a daylight condition at 40° C. and 8 hours under a dark condition at 30° C.


Subsequently, a degree of leaf browning and growth inhibition were observed to investigate states of high temperature injury.


Disorders were evaluated by 11 levels of disorder indices from 0 (no disorders) to 10 (withering to death).


High temperature injury relief percentages as compared with a region treated with solvent DMF only (Chemical solution 3) were computed by the following formula.





High temperature injury relief percentage=((disorder index of region treated with solvent only)−(disorder index of each treatment region))/(disorder index of region treated with solvent only)×100


The results are shown in Table 3.











TABLE 3









Chemical solution













1
2
3
















Substance(A) [Conc. ppm]
800
0
0



ascorbyl palmitate



Agric. chemical [Conc. ppm]
0
40
0



Pyraclostrobin



relief percents of high-
57
35
0



temperature injury (%)










Test Example 2
Evaluation Test for Relief Effects of High Temperature Injury on Cherry Tomato

Cherry tomato (breed; Regina, 5 reprications) grown in a greenhouse was prepared.


On August 24 at the first inflorescence anthesis, 0.15% of 4-chlorophenoxyacetic acid was sprayed, and a water dispersible granule of 30% ascorbyl palmitate in an amount described in Table 4 was further applied at the plant foot at intervals of seven days. All fruits were harvested on September 28, and the color of a fruit (classified into red and green), the weight of a fruit, and the number of fruits were investigated to calculate the weight per fruit and the percentage of red fruits (%).


The results are shown in Table 4.












TABLE 4







Substance(A)
no



ascorbyl palmitate
treatment



















dosage(g/stock)
0.5
0.1












yield
Total weight of fruits(g)
342
304
262



Total number of fruits
33
32
38



weight per fruit(g/fruit)
10.4
9.5
6.9



vs. no treatment region(%)
151
138
100


color
Number of red fruits
29
19
16


of
Number of green fruits
4
13
22


fruit
Percents of red fruits(%)
88
59
42



vs. no treatment region(%)
209
141
100









Test Example 3
Evaluation Test for Relief Effects of Low Temperature Injury on Cucumber

N,N-dimethylformamide based solutions were prepared according to the formulations shown in Tables 5 to give chemical solutions for the tests.


Cucumber nursery plants (breed: Sagamihanjiro) grown up to the 1.5 leaf stage in a greenhouse was prepared.


The above chemical solution was sprayed to the stem and leaf parts of the above cucumber nursery plants in a sufficient amount, and then air dried. They were allowed to grow at 25° C. for 2 days under conditions of 16 hours under a daylight condition and 8 hours under a dark condition. Then, they were allowed to grow for 9 days under conditions of 16 hours under a daylight condition at 10° C. and 8 hours under a dark condition at 7° C.


Subsequently, a degree of leaf browning and outgrowth inhibition were observed to investigate states of low temperature injury.


Disorders were evaluated by 11 levels of disorder indices from 0 (no disorders) to 10 (withering to death).


Low temperature injury relief percentages as compared with a region treated with solvent DMF only (Chemical solution 3) were computed by the following formula.





Low temperature injury relief percentage=((disorder index of region treated with solvent only)−(disorder index of each treated region))/(disorder index of region treated with solvent only)×100


The results are shown in Table 5.











TABLE 5









Chemical solution











1
2
3
















Substance(A)[Conc. ppm]
800
0
0



ascorbyl palmitate



Agric. chemical[Conc. ppm]
0
40
0



Pyraclostrobin



relief percents of low-
25
19
0



temperature injury(%)










Test Example 4
Evaluation Test for Relief Effects of Low Temperature Injury on Eggplant

Eggplant (breed: Senryo 2 gou, 3 reprications) grown up to the 4 to 6 leaf stage in a greenhouse was prepared.


A water dispersible granule of 30% ascorbyl palmitate and pyraclostrobin dissolved to 40% with N,N-dimethylformamide were diluted with tap water to a concentration described in Table 6, and the diluted solution was sprayed over the whole nursery plants in a sufficient amount. After air dried, they were allowed to grow for 1 day under conditions of 16 hours under a daylight condition at 18° C. and 8 hours under a dark condition at 13° C., and then allowed to grow under conditions of 16 hours under a daylight condition at 13° C. and 8 hours under a dark condition at 8° C. A degree of disorder was investigated at the elapsed time of 15 days after the spray treatment.


Disorders were evaluated by 4 levels of disorder indices of 0 (no color change), 1 (discolored up to ¼ of the whole), 2 (discolored up to ½ of the whole), 3 (discolored at ½ or more of the whole) with reference to the area of a discolored portion in an expanded leaf after treatment.





Injury relief percentage=((disorder index of untreated region)−(disorder index of each treated region))/(disorder index of untreated region)×100


The results are shown in Table 6.











TABLE 6









Chemical solution











4
5
3
















Substance(A)[Conc. ppm]
1000
0
0



ascorbyl palmitate



Agric. chemical[Conc. ppm]
0
50
0



Pyraclostrobin



relief percents of low-
13.0
13.0
0.0



temperature injury(%)










Test Example 5
Evaluation Test for Relief Effects of Low Temperature Injury on Tomato

Tomato (breed: Reiyo, 4 reprications) grown up to the 3.5 leaf stage in a greenhouse was prepared.


A water dispersible granule of 30% ascorbyl palmitate and pyraclostrobin dissolved to 40% with N,N-dimethylformamide were diluted with tap water to a concentration described in Table 7, and the diluted solution was sprayed over the whole nursery plants in a sufficient amount. After air dried, they were transferred to the outside of the greenhouse at an average temperature of 0.5° C. during night to investigate a degree of low temperature injury on the next morning.


Disorders were evaluated by 5 levels of disorder indices of 0 (no disorder) to 4 (complete withering). From this, disorder relief percentages were computed by the following formula.





Low temperature injury relief percentage=(disorder index of untreated region)−(disorder index of each treatment region)/(disorder index of untreated region)×100


The results are shown in Table 7.











TABLE 7









Chemical solution











6
5
3
















Substance(A)[Conc. ppm]
500
0
0



ascorbyl palmitate



Agric. chemical[Conc. ppm]
0
50
0



Pyraclostrobin



relief percents of low-
100
25
0



temperature injury(%)










Test Example 6
Evaluation Test for Relief Effects of High Temperature Injury on Eustoma grandiflorum


Eustoma grandiflorum (breed: King of Snow) grown at a temperature of 22° C. and 16 hours under dark condition in a cell tray in the room was prepared. When an appropriately half were sprouted after seeding, a water dispersible granule of 30% ascorbyl palmitate was diluted with distilled water to a predetermined concentration, and the diluted solution was sprayed on the whole nursery plants in a sufficient amount. Subsequently, spraying by the same method was performed two times a week for the total of 10 times including the first application. Meanwhile, they were transferred to under conditions of 16 hours under a daylight condition at 35° C. and 8 hours under a dark condition at 15° C. at the expansion stage of a pair of true leaves 3 weeks after seeding, and allowed to grow for 2 weeks. Further, they were transferred to in a glass greenhouse and allowed to grow. Then naturalization was performed upon the expansion stage of two pairs of true leaves 8 week after seeding, and continuously allowed to grow in the greenhouse. Subsequently, the number of those bloomed out of the bolting plants was investigated.


The results are shown in Table 8.












TABLE 8









Chemical solution











7
8















Substance(A)[Conc. ppm]
600
0



ascorbyl palmitate



Number of bolting plants
16
14



Number of bloomed plants
12
5



Percents of bloomed plants(%)
75.0
35.7










Test Example 7
Evaluation Test for Relief Effects of Strong Light Injury on Tomato

Tomato (breed: Reiryo, 2 reprications) grown up to the two leaf stage in a greenhouse was prepared.


A water dispersible granule of 30% of ascorbyl palmitate and pyraclostrobin dissolved to 40% N,N-dimethylformamide were diluted with tap water to each of the concentrations described in Table 9, and the diluted solution was sprayed over the whole nursery plants in a sufficient amount. After air dried, they were exposed to strong light under summer blazing sun. A degree of disorder was investigated at the elapsed time of 4 days after the spraying.


For disorder, a degree of necrosis due to light effects was evaluated by 11 levels of disorder indices from 0 (no necrosis) to 10 (withering to death). From this, disorder relief percentages were computed by the following formula.





Injury relief percentage=((disorder index of untreated region)−(disorder index of each treated region))/(disorder index of untreated region)×100


The results are shown in Table 9.











TABLE 9









Chemical solution











4
5
3
















Substance(A)[Conc. ppm]
1000
0
0



ascorbyl palmitate



Agric. chemical[Conc. ppm]
0
50
0



Pyraclostrobin



relief percents of
50
40
0



strong light injury (%)










Test Example 8
Evaluation Test for Relief Effects of Phytotoxicity on Tomato

N,N-dimethylformamide based solutions were prepared according to the formulations shown in Table 10 to give chemical solutions for the tests.


Tomato nursery plants (breed: Momotaro) grown up to the 4 leaf stage in a greenhouse were prepared.


The above chemical solution was sprayed to the stem and leaf parts of the above tomato nursery plants in an amount of liquid dropping, and then air dried. They were allowed to grow for 7 days under the average temperature and humidity conditions on March in Japan.


Subsequently, phytotoxicity such as a degree of leaf browning and outgrowth inhibition was investigated.


Phytotoxicity was evaluated by 11 levels of phytotoxicity indices of 0 (with no disorder) to 10 (withering to death).


Chemical poisoning injury relief percentages as compared with a region treated with solvent DMF only were computed by the following formula.





Chemical poisoning injury relief percentage=(phytotoxicity index of region treated with solvent only)−(phytotoxicity index of each treated region))/(phytotoxicity index of region treated with solvent only)×100


The results are shown in Table 10.











TABLE 10









Chemical solution
















9
10
11
12
13
14
15
16



















Substance (A) [Conc. ppm]
800
800
0
0
800
800
0
0


ascorbyl palmitate


Agric. chemical [Conc. ppm]


Fluazinam
200
100
200
100
0
0
0
0


Azoxystrobin
0
0
0
0
200
100
200
100


phytotoxicity index
4
2
6
6
4
3
6
5


relief percents
33
67
0
0
33
40
0
0


of phytotoxicity (%)









Test Example 9
Test for Green Color Maintenance Effects (Relief of High Temperature Injury) on Wheat

Wheat (breed, Norin No. 61, 15 plants/m2/region, 2 reprications) grown in the field was used. A water dispersible granule of 30% ascorbyl palmitate in an amount described in Table 11 was applied to the plant foot 4 times at intervals of seven days from the next day of the ear emergence day in August. The leaf color index of top 4 to 5 leaves of each plant in a treatment region was investigated on September 6 to evaluate maintenance effects of leaf color as compared with that in the untreated region.


Leaf color was evaluated by 4 levels of leaf color indices of 1 (discolored at ¼ or less of the whole), 2 (discolored at ½ or less of the whole) and 3 (discolored at ¾ or more of the whole). From this, the mean leaf color index, and green color maintenance effects were computed by the following formula.





Green color maintenance effect=(leaf color index of untreated region)−(leaf color index of each treatment region))/(leaf color index of untreated region)×100


The results are shown in Table 11.












TABLE 11







Substance(A)
no



ascorbyl palmitate
treatment


















appl. amount (g/m2)
1.5



mean leaf color index
1.5
2.0


Green color maintenance effect(%)
25.0
0.0









Test Example 10
Evaluation Test for Relief Effects of Submergence Disorder on Cucumber

Cucumber (breed: Sagamihanjirohushinari, 2 reprications) grown up to the two leaf stage in a greenhouse was prepared.


A water dispersible granule of 30% ascorbyl palmitate and pyraclostrobin adjusted to 40% with N,N-dimethylformamide were diluted with tap water to a predetermined concentration, and the diluted solution was sprayed in a sufficient amount. They were subjected to flood conditions up to immediately below the cotyledon from 2 days after the spray treatment, and the raw weights of an above ground part and a root part of cucumber were each measured at the elapsed time of 11 days after the spray treatment. From this, injury relief percentages were computed by the following formula.





Flood injury relief percentage=((raw weight of each treatment region)−(raw weight of untreated region))/(raw weight of untreated region)×100


The results are shown in Table 12.











TABLE 12









Chemical solution











4
5
3
















Substance(A)[Conc. ppm]
1000
0
0



ascorbyl palmitate



Agric. Chemical[Conc. ppm]
0
50
0



Pyraclostrobin



relief percents of flood
31.9
61.7
0.0



injury in aerial part(%)



relief percents of flood
41.5
39.0
0.0



injury in root(%)










Test Example 11
Evaluation Test for Relief Effects of Flood Injury on Soybean

Soybean (breed: Enrei, 2 reprications) grown up to the two leaf stage in a greenhouse was prepared.


A water dispersible granule of 30% ascorbyl palmitate and pyraclostrobin adjusted to 40% with N,N-dimethylformamide were diluted with tap water to a predetermined concentration, and the diluted solution was sprayed in a sufficient amount. They were subjected to flood conditions up to immediately below the cotyledon from 2 days after the spray treatment, and the raw weights of an above ground part and a root part of soybean were each measured at the elapsed time of 11 days after the spray treatment. From this, injury relief percentages were computed by the following formula.





Flood injury relief percentage=((raw weight of each treatment region)−(raw weight of untreated region))/(raw weight of untreated region)×100


The results are shown in Table 13.











TABLE 13









Chemical solution











4
5
3
















Substance(A)[Conc. ppm]
1000
0
0



ascorbyl palmitate



Agric. Chemical[Conc. ppm]
0
50
0



Pyraclostrobin



relief percents of flood
2.8
0.0
0.0



injury in aerial part(%)



relief percents of flood
20.4
3.2
0.0



injury in root(%)










Test Example 12
Evaluation Test for Relief Effects of Acidity Problem on Cucumber

Cucumber (breed: Sagamihanjirohushinari, 2 reprications) hydroponically grown up to the two leaf stage in a 100 ml flask was prepared.


A water dispersible granule of 30% ascorbic acid palmitate and pyraclostrobin adjusted to 40% with N,N-dimethylformamide were diluted with tap water to a predetermined concentration, and the diluted solution was sprayed over the whole nursery plants in a sufficient amount. The water culture medium was adjusted to pH 4 with 1 N hydrochloric acid at the elapsed time of 2 days after the spray treatment, and the above cucumber was continuously allowed to grow hydroponically. Leaf stage of the cucumber was investigated 17 days after the spray treatment. From this, disorder relief percentages were computed by the following formula.





Acidity problem relief percentage=((leaf stage of each treatment region)−(leaf stage of untreated region))/(leaf stage of untreated region)×100


The results are shown in Table 14.











TABLE 14









Chemical solution











4
5
3
















Substance(A)[Conc. ppm]
1000
0
0



ascorbyl palmitate



Agric. Chemical[Conc. ppm]
0
50
0



Pyraclostrobin



relief percents of acidity
15.6
15.6
0.0



problem(%)










Test Example 13
Evaluation Test for Relief Effects of Acidity Problem on Soybean

Soybean (breed: Enrei, 2 reprications) hydroponically grown up to the two leaf stage in a 100 ml flask was prepared.


A water dispersible granule of 30% ascorbyl palmitate and pyraclostrobin dissolved to 40% with N,N-dimethylformamide were diluted with tap water to a predetermined concentration, and the diluted solution was sprayed over the whole nursery plants in a sufficient amount. The water culture medium was adjusted to pH 4 with 1 N hydrochloric acid at the elapsed time of 2 days after the spray treatment, and the above soybean was continuously allowed to grow hydroponically. Disorder in the soybean was investigated at the elapsed time of 11 days after the spray treatment.


For disorder, a degree of necrosis was evaluated by 11 levels of disorder indices from 0 (no necrosis) to 10 (withering to death). From this, problem relief percentages were computed by the following formula.





Acidity problem relief percentage=((disorder index of untreated region)−(disorder index of each treated region))/(disorder index of untreated region)×100


The results are shown in Table 15.











TABLE 15









Chemical solution











4
5
3
















Substance(A)[Conc. ppm]
1000
0
0



ascorbyl palmitate



Agric. Chemical[Conc. ppm]
0
50
0



Pyraclostrobin



relief percents of acidity
43.8
12.5
0.0



problem(%)










Test Example 14
Evaluation Test for Relief Effects of Salt Injury on Cucumber

Cucumber (breed: Sagamihanjirohushinari, 2 reprications) hydroponically grown up to the two leaf stage in a greenhouse was prepared.


A water dispersible granule of 30% ascorbic acid palmitate and pyraclostrobin adjusted to 40% with N,N-dimethylformamide were diluted with tap water to a predetermined concentration, and the diluted solution was sprayed over the whole nursery plants in a sufficient amount. After air dried, they were cultivated with normal irrigation in a greenhouse. Then, the irrigation conditions were changed to 0.1% aqueous sodium chloride solution in 2 cm depth from 2 days after the spraying, and cultivated up to 11 days after the spray treatment. Then the raw weights of an aerial part and a root part were each measured. From this, injury relief percentages were computed by the following formula.





Salt injury relief percentage=((raw weight of each treatment region)−(raw weight of untreated region))/(raw weight of untreated region)×100


The results are shown in Table 16.











TABLE 16









Chemical solution











4
5
3
















Substance(A)[Conc. ppm]
1000
0
0



ascorbyl palmitate



Agric. Chemical[Conc. ppm]
0
50
0



Pyraclostrobin



relief percents of salt
8.8
45.6
0.0



injury in aerial part(%)



relief percents of salt
16.0
20.0
0.0



injury in root(%)










Test Example 15
Evaluation Test for Relief Effects of Salt Injury on Soybean

Soybean (breed: Enrei, 2 reprications) hydroponically grown up to the two leaf stage in a greenhouse was prepared.


A water dispersible granule of 30% ascorbic acid palmitate and pyraclostrobin adjusted to 40% with N,N-dimethylformamide were diluted with tap water to a predetermined concentration, and the diluted solution was sprayed over the whole nursery plants in a sufficient amount. After air dried, they were cultivated with normal irrigation in a greenhouse. Then, the irrigation conditions were changed to 0.1% aqueous sodium chloride solution in 2 cm depth from 2 days after the spraying, and cultivated up to 11 days after the spray treatment. Then the raw weights of an aerial part and a root part were each measured. From this, injury relief percentages were computed by the following formula.





Salt injury relief percentage=((raw weight of each treatment region)−(raw weight of untreated region))/(raw weight of untreated region)×100


The results are shown in Table 17.











TABLE 17









Chemical solution











4
5
3
















Substance(A)[Conc. ppm]
1000
0
0



ascorbyl palmitate



Agric. Chemical[Conc. ppm]
0
50
0



Pyraclostrobin



relief percents of salt
20.4
3.2
0.0



injury in aerial part(%)



relief percents of salt
22.2
2.5
0.0



injury in root(%)










Test Example 16
Test for Symptom Relief Effects Against Tomato Yellow Leaf Curl Virus Disease

N,N-dimethylformamide based solutions were prepared according to the formulations shown in Table 18 to give chemical liquids for the tests.


Tomato nursery plants (breed: Momotaro) grown up to the 8 leaf stage in a greenhouse were prepared.


Tomato nursery plants suffering from tomato yellow leaf curl virus (TYLCV) were used as inoculation sources.


A diseased plant was obliquely cut in round slices at the stem, and graft-inoculated to a tomato nursery plant. In order to prevent dryness, parafilm was wrapped around the grafted portion for protection.


After the graft inoculation, the above chemical solution was sprayed on the stem and leaf part of the tomato nursery plant in a sufficient amount. Then, the above chemical solution was sprayed 3 times at intervals of about one week in a sufficient amount. Symptoms of tomato yellow leaf curl disease were investigated at an elapsed time of 25 days.


Symptoms were evaluated by 5 levels of onset indices of 0 (with no onset) to 4 (fulminant).


Onset inhibition percentages as compared with a region treated with solvent DMF only (Chemical solution 3) were computed by the following formula.





Onset inhibition percentage=(onset index of region treated with solvent only)−(onset index of each treatment region))/(onset index of region treated with solvent only)×100


Further, the expectation values of onset inhibition percentages were computed based on the Colby's equation.


The Colby's equation is E=M+N−MN/100. In the equation, E represents the expectation value of an onset inhibition percentage (%), and M represents an onset inhibition percentage (%) calculated from measurements when the substance (A1) is used alone, and N represent an onset inhibition percentage (%) calculated from measurements when the substance (A2) is used alone. The results are shown in Table 18.











TABLE 18









Chemical solution













17
4
6
18
3
















Substance(A1)[Conc. ppm]
500
0
0
500
0


Ascorbyl glucoside


Substance(A2)[Conc. ppm]
500
1000
500
0
0


ascorbyl palmitate


Onset percentage(%)
10
20
30
40
50


Onset inhibition
80
60
40
20
0


percentage(%)


Expectation value(%)
52
60
40
20
0









Test Example 17
Tests for Relief Effects of Disease Stress on Rice Plant

Nursery plants of rice (breed: Koshihikari, 10 reprications) were prepared. A water dispersible granule of 30% ascorbyl palmitate and pyraclostrobin adjusted to 5% with N,N-dimethylformamide were diluted with tap water to a predetermined concentration, and these were sprayed over the whole nursery plants in a sufficient amount, and then air dried. They were inoculated with Pyricularia oryzae on the next day. The number of rice blast spots was investigated at the elapsed time of 11 days after the inoculation. From this, preventive values were computed by the following formula.





Preventive value=((number of lesion spots in untreated region)−(number of lesion spots in each treated region))/(number of lesion spots in untreated region)×100


The results are shown in Table 19.


[Table 19]











TABLE 19









Chemical solution











19
20
3
















Substance(A)[Conc. ppm]
50
0
0



ascorbyl palmitate



Agric. Chemical[Conc. ppm]
0
5
0



Pyraclostrobin



Number of lesion spots
30
10
33



Preventive value(%)
9
70
0









Claims
  • 1. A method of providing a plant with stress resistance, wherein the method comprises applying at least one substance (A) to the plant, said at least one substance (A) being selected from the group consisting of compounds represented by Formula (I):
  • 2. The method according to claim 1, wherein the substance (A) is a compound represented by Formula (I) provided that R1 to R4 are not each simultaneously a hydrogen atom, or a salt thereof.
  • 3. The method according to claim 1, wherein the substance (A) is a compound represented by Formula (I) provided that at least one of R1 to R4 represents —COR11, and R11 represents an unsubstituted or substituted C12 to C30 alkyl group or an unsubstituted or substituted C12 to C30 alkenyl group, or a salt thereof.
  • 4. The method according to claim 1, wherein the substance (A) is a compound represented by Formula (I) provided that R1 to R4 each independently represents a hydrogen atom or —COR11, and at least one of R1 to R4 represents —COR11. R11 represents an unsubstituted or substituted C1 to C30 alkyl group or an unsubstituted or substituted C2 to C30 alkenyl group. R11 in at least one of —COR11 represents an unsubstituted or substituted C12 to C30 alkyl group or an unsubstituted or substituted C12 to C30 alkenyl group, or a salt thereof.
  • 5. The method according to claim 1, wherein the substance (A) is a composition comprising a water soluble substance (A1) of those selected from the group consisting of compounds represented by Formula (I), compounds represented by Formula (II) and salts thereof; and a lipid soluble substance (A2) of those selected from the group consisting of compounds represented by Formula (I), compounds represented by Formula (II) and salts thereof.
  • 6. The method according to claim 1, wherein the stress is at least one of biological stress due to plant viruses, phytopathogenic bacteria, phytopathogenic filamentous fungi, agricultural pests or weeds; or physical or chemical stress due to high temperature, low temperature, high illuminance, low illuminance, excessive humidity, dryness, salt, acidity, agricultural chemicals, chemical substances or heavy metals.
  • 7. A stress resistance conferring composition for a plant, wherein the composition comprises at least two substances (A) selected from the group consisting of compounds represented by Formula (I):
  • 8. The composition according to claim 7, wherein one of the substances (A) is a water soluble substance (A1) of those selected from the group consisting of compounds represented by Formula (I), compounds represented by Formula (II) and salts thereof; and another of the substances (A) is a lipid soluble substance (A2) of those selected from the group consisting of compounds represented by Formula (I), compounds represented by Formula (II) and salts thereof.
  • 9. A stress resistance conferring composition for a plant, wherein the composition comprises at least one water soluble substance (A1) selected from the group consisting of compounds represented by Formula (Ia):
  • 10. A method of reducing phytotoxicity of a plant due to an agricultural chemical, wherein the method comprises providing the plant with stress resistance by the method according to claim 1.
  • 11. The method of reducing phytotoxicity of a plant due to an agricultural chemical according to claim 10, wherein the agricultural chemical comprises at least one selected from the group consisting of fungicides, insecticides, plant growth regulators and herbicides.
Priority Claims (1)
Number Date Country Kind
JP 2012-161898 Jul 2012 JP national
PCT Information
Filing Document Filing Date Country Kind
PCT/JP2013/004430 7/19/2013 WO 00