Method for preventing insect damage to plants

Abstract

Provided is a technology useful in agricultural and horticultural fields, and includes a technology for preventing insect damage to plants. The present invention prevents insect damage to plants by using a compound represented by general formula (I).

Description

How to prevent insect damage to plants

[0001] The present invention relates to a technique useful in the agricultural and horticultural fields, such as a technique for preventing insect damage to plants.

[0002] According to a United Nations report, the world population is expected to increase by 2 billion people over the next 30 years, reaching 9.7 billion in 2050. The Food and Agriculture Organization of the United Nations has stated that to accommodate this population growth, agricultural production (e.g., production of food, feed, and biofuels) in 2050 will need to increase by more than 50% compared to 2012 (Non-Patent Document 1).

[0003] On the other hand, damage to plants caused by insect pests and other factors has been reported. For example, 26 to 40% of grains are lost to pests, pathogens, weeds, viruses, etc.

[0004] Most insect pest control technologies rely on insecticidal synthetic chemical pesticides, which has repeatedly led to the emergence of pesticide-resistant pests. Therefore, there is a need to develop insect pest control technologies that do not allow the emergence of drug-resistant pests.

[0005] When plants are fed by pests, glutamate leaks out of the damaged cells and converts it into Ca 2+ Activates glutamate receptor GLR3.3 / 3.6, a permeable ion channel, and releases the generated Ca 2+ It has been revealed that the signal propagates rapidly through the vascular bundles, and within minutes, even in distant organs that are not directly fed, the plant resistance hormone jasmonic acid is synthesized, activating systemic defense mechanisms (Non-patent Document 2).

[0006] In addition to glutamic acid, glutamic acid derivatives can also be applied to plants, which can increase Ca levels via glutamate receptors. 2+ It has been reported that this induces a signal that induces insect resistance in the plant (Patent Document 1).

[0007] International Publication No. 2024 / 010005

[0008] FAO, The future of food and agriculture - Trends and challenges, 2017. Toyota, M et al., Glutamate triggers long-distance, calcium-based plant defense signaling. Science. 2018 Sep 14;361(6407):1112-1115.

[0009] An object of the present invention is to provide a useful technology in the agricultural and horticultural fields, such as a technology for preventing insect damage to plants.

[0010] As a result of intensive research conducted by the present inventors to solve the above-mentioned problems, they discovered that various compounds can induce insect resistance without damaging the plant, and that insect resistance is induced not only in the plant to which the compound is applied, but also in plant plants that are present in the vicinity of the applied compound but to which the active ingredient has not been applied, thereby making it possible to prevent insect damage to plants, and thus completed the present invention.

[0011] That is, the present invention can be exemplified as follows: [1] A composition for inducing insect resistance in a plant or for preventing insect damage in a plant, the composition comprising the following component (A): (A) a compound represented by the general formula (I) described below. [In formula (I), R １ represents a hydrogen atom (H), a hydroxyl group, an amino group, an optionally substituted alkyl group, an optionally substituted alkylamino group, an optionally substituted alkoxy group, agmatine, glycerol, glucose, an amino acid, a dipeptide, or a tripeptide; R ２ represents an optionally substituted alkyl group having 7 to 10 carbon atoms or an optionally substituted alkenyl group having 7 to 10 carbon atoms.] [2] R ２ [3] The composition (specifically described in [1] or [2]) above, wherein component (A) is selected from the group consisting of compounds that satisfy any of the following conditions: (1) R １ is a hydroxyl group, R ２is an alkyl group having 7 to 10 carbon atoms; (2) R １ is an alkylamino group substituted with a hydroxyl group, R ２ is an alkyl group having 7 to 10 carbon atoms; (3) R １ is an alkoxy group, R ２ is an alkyl group having 7 to 10 carbon atoms; (4) R １ is an amino acid, R ２ is an alkyl group having 7 to 10 carbon atoms; (5) R １ is an amino acid, R ２ is an alkenyl group having 7 to 10 carbon atoms; and (6) R １ is a dipeptide, R ２ is an alkyl group having 7 to 10 carbon atoms. [4] The composition (specifically described in any of [1] to [3]) in which the component (A) is selected from the group consisting of compounds represented by the formulas (Compound 3) to (Compound 6), (Compound 12) to (Compound 16), (Compound 19), (Compound 20), and (Compound 23) described below. [5] The composition (specifically described in any of [1] to [3]) in which the component (A) is one or both of a mixture represented by the formula (Mixture 1) and a mixture represented by the formula (Mixture 2) described below. [In Formula (Mixture 1), R ２ represents an alkyl group of a residue of a fatty acid derived from coconut oil having 7 to 10 carbon atoms, and mixture 1 is ２ is an alkyl group of a residue of a fatty acid derived from multiple types of palm oil having 7 to 10 carbon atoms.] [In formula (Mixture 2), R ２ represents an alkyl group of a residue of a fatty acid derived from coconut oil having 7 to 10 carbon atoms, and mixture 2 is represented by R ２is an alkyl group of residues of multiple types of palm oil-derived fatty acids having 7 to 10 carbon atoms.] [6] The composition (specifically according to any one of [1] to [5]) above, wherein the insect damage is caused by organisms classified into the order Lepidoptera, Hemiptera, Coleoptera, Diptera, Orthoptera, Thysanoptera, Tylenchida, Collembola, Acarina, or Stylommatophora. [7] The insect pests include those of the following families: Plutellidae, Noctuidae, Pyralidae, Tortricidae, Leafminer, Bone-borer, Gelechiidae, Crambidae, Arctiidae, Lymantriidae, Leafhoppers, Delphacidae, Psyllidae, Aphididae, Aleyrodidae, Scale insects, Miridae, Tingidae, Hemiptera, Lygaeidae, Scarabaeidae, Elateridae, Coccinellidae, Cerambycidae, Chrysomelidae, Curculionidae, Muscidae, Calliphoridae, Sarcophagidae, and The composition (specifically, the composition according to any one of [1] to [6]) is for insect damage caused by organisms classified into the following families: Tephritidae, Tephritidae, Euloidea, Chloropidae, Acrididae, Locustidae, Scytothripidae, Thripidae, Thysanidae, Scytothripidae, Aphelenchoidae, Neotylenchidae, Pyrrhocoridae, Pyrrhocoridae, Tetranychidae, Miteridae, Acaridae, Astigmatidae, Sarcoptidae, Slugidae, or Scytothripidae. [8] The composition (specifically, any one of [1] to [7]) as described above, wherein the plant is a grass family plant, a solanaceae plant, a cucurbit family plant, a legume family plant, a cruciferous family plant, a rose family plant, a moraceae plant, a mallow family plant, a pipal family plant, a lily family plant, a asteraceae plant, an amaranthaceae plant, an ericaceae family plant, a vitiaceae family plant, a citrus family plant, a rubiaceae plant, an oleaceae family plant, a laurel family plant, an Anacardiaceae family plant, a Sapindaceae plant, or a Lamiaceae plant. [9] A method for inducing insect resistance in a plant, the method comprising applying the following component (A) to the plant: (A) a compound represented by the general formula (I) described below. [In formula (I), R １ represents a hydrogen atom (H), a hydroxyl group, an amino group, an optionally substituted alkyl group, an optionally substituted alkylamino group, an optionally substituted alkoxy group, agmatine, glycerol, glucose, an amino acid, a dipeptide, or a tripeptide; R ２represents an optionally substituted alkyl group having 7 to 10 carbon atoms, or an optionally substituted alkenyl group having 7 to 10 carbon atoms.]

[10] A method for preventing insect damage to plants, comprising applying the following component (A) to the plants: (A) a compound represented by the general formula (I) described below. [In formula (I), R １ represents a hydrogen atom (H), a hydroxyl group, an amino group, an optionally substituted alkyl group, an optionally substituted alkylamino group, an optionally substituted alkoxy group, agmatine, glycerol, glucose, an amino acid, a dipeptide, or a tripeptide; R ２ represents an optionally substituted alkyl group having 7 to 10 carbon atoms, or an optionally substituted alkenyl group having 7 to 10 carbon atoms.]

[11] A method for producing a plant, comprising applying the following component (A) to a plant and cultivating the plant: (A) a compound represented by the general formula (I) described below. [In formula (I), R １ represents a hydrogen atom (H), a hydroxyl group, an amino group, an optionally substituted alkyl group, an optionally substituted alkylamino group, an optionally substituted alkoxy group, agmatine, glycerol, glucose, an amino acid, a dipeptide, or a tripeptide; R ２ represents an optionally substituted alkyl group having 7 to 10 carbon atoms or an optionally substituted alkenyl group having 7 to 10 carbon atoms.]

[12] R ２

[13] The method (specifically, any one of [9] to

[12] ) above, wherein the component (A) is selected from the group consisting of compounds that satisfy any of the following conditions: (1) R １ is a hydroxyl group, R ２ is an alkyl group having 7 to 10 carbon atoms; (2) R １ is an alkylamino group substituted with a hydroxyl group, R ２ is an alkyl group having 7 to 10 carbon atoms; (3) R １ is an alkoxy group, R ２ is an alkyl group having 7 to 10 carbon atoms; (4) R１ is an amino acid, R ２ is an alkyl group having 7 to 10 carbon atoms; (5) R １ is an amino acid, R ２ is an alkenyl group having 7 to 10 carbon atoms; and (6) R １ is a dipeptide, R ２ is an alkyl group having 7 to 10 carbon atoms.

[14] The method (specifically described in any of [9] to

[13] ) above, wherein the component (A) is selected from the group consisting of compounds represented by the formulas (Compound 3) to (Compound 6), (Compound 12) to (Compound 16), (Compound 19), (Compound 20), and (Compound 23) described below.

[15] The method (specifically described in any of [9] to

[14] ) above, wherein the component (A) is one or both of a mixture represented by the formula (Mixture 1) and a mixture represented by the formula (Mixture 2) described below. [In Formula (Mixture 1), R ２ represents an alkyl group of a residue of a fatty acid derived from coconut oil having 7 to 10 carbon atoms, and mixture 1 is ２ is an alkyl group of a residue of a fatty acid derived from multiple types of palm oil having 7 to 10 carbon atoms.] [In formula (Mixture 2), R ２ represents an alkyl group of a residue of a fatty acid derived from coconut oil having 7 to 10 carbon atoms, and mixture 2 is represented by R ２is an alkyl group of residues of multiple types of palm oil-derived fatty acids having 7 to 10 carbon atoms.]

[16] The method (specifically according to any of [9] to

[15] ) above, wherein the insect damage is caused by organisms classified into the order Lepidoptera, Hemiptera, Coleoptera, Diptera, Orthoptera, Thysanoptera, Tylenchida, Collembola, Acarina, or Stylommatophora.

[17] The insect pests include those of the following families: Plutellidae, Noctuidae, Pyralidae, Tortricidae, Leafminer, Bone-borer, Gelechiidae, Crambidae, Arctiidae, Lymantriidae, Leafhoppers, Delphacidae, Psyllidae, Aphididae, Aleyrodidae, Scale insects, Miridae, Tingidae, Hemiptera, Lygaeidae, Scarabaeidae, Elateridae, Coccinellidae, Cerambycidae, Chrysomelidae, Curculionidae, Muscidae, Calliphoridae, Sarcophagidae, and The method (specifically, the method according to any one of [9] to

[16] ) is characterized in that the insect damage is caused by an organism classified into the family Tephritidae, Tephritidae, Euloidea, Chloropsoidea, Acrididae, Locustidae, Scytothripsidae, Thripidae, Thripidae, Scytothripsidae, Aphelenchoidae, Neotylenchidae, Pyrrhocoridae, Pyrrhocoridae, Tetranychidae, Miteidae, Acaridae, Astigmatidae, Sarcoptidae, Slugidae, or Scytothripidae.

[18] The method (specifically according to any one of [9] to

[17] ) described above, wherein the plant is a grass family plant, a solanaceae family plant, a cucurbit family plant, a legume family plant, a Brassicaceae family plant, a rose family plant, a mulberry family plant, a mallow family plant, a pipal family plant, a lily family plant, a asteraceae family plant, an amaranthaceae family plant, an Ericaceae family plant, a Vitaceae family plant, a Rutaceae family plant, a Rubiaceae family plant, an Oleaceae family plant, a Lauraceae family plant, an Anacardiaceae family plant, a Sapindaceae family plant, or a Lamiaceae family plant.

[0012] According to the present invention, useful results can be obtained in the agricultural and horticultural fields, such as prevention of insect damage to plants.

[0013] FIG. 1 shows the herbicide damage suppression effect of glutamic acid derivatives on komatsuna seedlings. The vertical axis shows the degree of damage in the Mixture 1-treated or jasmomate-treated plots, with the degree of damage in the sorbitol-treated plot set at 100. The horizontal axis shows the number of days after application of Mixture 1 or jasmomate. FIG. 2 shows the effect of Compound 15 or Mixture 1 on inducing expression of the AtJAZ5 gene in leaves of wild-type Arabidopsis thaliana Columbia-0. FIG. 3 shows the effect of Compound 15 or Mixture 1 on inducing expression of the AtJAZ7 gene in leaves of wild-type Arabidopsis thaliana Columbia-0. FIG. 4 shows the effect of Mixture 1 on inducing herbicide damage on komatsuna seedlings.

[0014] <1> Active ingredient In the present invention, the following ingredient (A) is used: (A) A compound represented by the following general formula (I):

[0015] The above component (A) is also referred to as the "active component."

[0016] Component (A) is a compound represented by the following general formula (I). ｎ " and "Rn" (n is a positive integer) may be used interchangeably.

[0017]

[0018] In formula (I), R １ represents a hydrogen atom (H), a hydroxyl group, an amino group, an optionally substituted alkyl group, an optionally substituted alkylamino group, an optionally substituted alkoxy group, agmatine, glycerol, glucose, an amino acid, a dipeptide, or a tripeptide.

[0019] In formula (I), R ２ represents an optionally substituted alkyl group having 7 to 10 carbon atoms, or an optionally substituted alkenyl group having 7 to 10 carbon atoms.

[0020] In one embodiment, R ２ may be an alkyl group having 7 to 10 carbon atoms.

[0021] In one embodiment, R ２may be an alkenyl group having 7 to 10 carbon atoms.

[0022] In one embodiment, R １ is a hydroxyl group, R ２ may be an alkyl group having 7 to 10 carbon atoms.

[0023] In one embodiment, R １ is an alkylamino group substituted with a hydroxyl group, R ２ may be an alkyl group having 7 to 10 carbon atoms.

[0024] In one embodiment, R １ is an alkoxy group, R ２ may be an alkyl group having 7 to 10 carbon atoms.

[0025] In one embodiment, R １ is an amino acid, R ２ may be an alkyl group having 7 to 10 carbon atoms.

[0026] In one embodiment, R １ is an amino acid, R ２ may be an alkenyl group having 7 to 10 carbon atoms.

[0027] In one embodiment, R １ is a dipeptide, R ２ may be an alkyl group having 7 to 10 carbon atoms.

[0028] Unless otherwise specified, for component (A), R １ and R ２ can be selected independently of each other.

[0029] The term "optionally substituted functional group" refers collectively to substituted and unsubstituted functional groups. For example, the term "optionally substituted alkyl group" refers collectively to substituted and unsubstituted alkyl groups. A substituted functional group is also referred to as a "substituted functional group," and an unsubstituted functional group as an "unsubstituted functional group." For example, a substituted alkyl group is also referred to as a "substituted alkyl group," and an unsubstituted alkyl group is also referred to as an "unsubstituted alkyl group." A "functional group" without reference to substitution refers to an unsubstituted functional group unless otherwise specified. For example, an "alkyl group" without reference to substitution refers to an unsubstituted alkyl group unless otherwise specified. The "carbon number" in an optionally substituted functional group refers to the number of carbon atoms in the unsubstituted functional group (i.e., the number of carbon atoms excluding the carbon atoms of the substituents), regardless of whether or not the functional group is substituted, unless otherwise specified. The description of an unsubstituted functional group can also be applied mutatis mutandis to the portion of a substituted functional group other than the substituents. For example, the description of an unsubstituted alkyl group can also be applied mutatis mutandis to the portion of a substituted alkyl group other than the substituents (i.e., the alkyl group portion).

[0030] "Substituted functional group" means that one or more hydrogen atoms constituting the functional group are substituted with a substituent. "Substituted functional group" can also be referred to as "functional group has a substituent." The number of hydrogen atoms substituted with substituents may be interpreted as the number of substituents the functional group has. When two or more hydrogen atoms are substituted with substituents, a substituent is selected independently for each hydrogen atom. Examples of hydrogen atoms substituted with substituents include hydrogen atoms bonded to carbon atoms, hydrogen atoms bonded to nitrogen atoms, and hydrogen atoms bonded to oxygen atoms. The hydrogen atom bonded to a carbon atom may or may not be, for example, a hydrogen atom bonded to a terminal carbon atom. "Terminal carbon atom" means the carbon atom at the end of a carbon chain. When the carbon chain is branched, the end may be the end of any branch.

[0031] The optionally substituted alkyl group is an alkyl group or a substituted alkyl group. The alkyl group may be linear, branched, or cyclic. R １ Examples of the alkyl group as R include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isopentyl group, a 2,3-dimethylpropyl group, a hexyl group, a heptyl group, an octyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group. ２ Examples of the alkyl group as R include alkyl groups having 7 to 17 carbon atoms. ２ As the alkyl group for R, particularly, an alkyl group having 7 to 10 carbon atoms can be mentioned. Examples of the alkyl group having 7 to 10 carbon atoms include a heptyl group, an octyl group, a nonyl group, a decyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, and a cyclodecyl group. ２ As the alkyl group, more particularly, alkyl groups of the residue of fatty acids derived from coconut oil having 7 to 10 carbon atoms can be mentioned. Examples of alkyl groups of the residue of fatty acids derived from coconut oil having 7 to 10 carbon atoms include heptyl, octyl, nonyl, and decyl groups.

[0032] The optionally substituted alkylamino group is an alkylamino group or a substituted alkylamino group. The alkyl group constituting the alkylamino group may be linear, branched, or cyclic. R １ Examples of the alkyl group constituting the alkylamino group as defined above include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isopentyl group, a 2,3-dimethylpropyl group, a hexyl group, a heptyl group, an octyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

[0033] The optionally substituted alkoxy group is an alkoxy group or a substituted alkoxy group. The alkoxy group may be linear or branched. R １ Examples of the alkoxy group as the alkoxy group include a methoxy group, an ethoxy group, a 1-propoxy group, a 2-propoxy group, an n-butoxy group, an i-butoxy group, a sec-butoxy group, a tert-butoxy group, a 1-pentyloxy group, a 2-pentyloxy group, a 3-pentyloxy group, a 2-methyl-1-butyloxy group, a 3-methyl-1-butyloxy group, a 2-methyl-2-butyloxy group, a 3-methyl-2-butyloxy group, a 2,2-dimethyl-1-propyloxy group, a 1-hexyloxy group, a 2-hexyloxy group, and a 3-hexyloxy group.

[0034] The optionally substituted alkenyl group is an alkenyl group or a substituted alkenyl group. The alkenyl group may be linear, branched, or cyclic. R ２ The alkenyl group represented by R may be an alkenyl group having 7 to 17 carbon atoms. ２ The alkenyl group as the alkyl group particularly includes an alkenyl group having 7 to 10 carbon atoms. Examples of the alkenyl group having 7 to 10 carbon atoms include a heptenyl group, an octenyl group, a nonenyl group, and a decenyl group.

[0035] R １ Examples of the substituent that the substituted alkyl group may have include a halogen atom, a hydroxyl group, an amino group, a guanidino group, a carboxyl group, an aminocarbonyl group, and a mercapto group.

[0036] R １ Examples of the substituent that the substituted alkylamino group has include a halogen atom, a hydroxyl group, an amino group, a guanidino group, a carboxyl group, an aminocarbonyl group, and a mercapto group.

[0037] R １ Examples of the substituent that the substituted alkoxy group has include a halogen atom, a hydroxyl group, an amino group, a guanidino group, a carboxyl group, an aminocarbonyl group, and a mercapto group.

[0038] R ２ Examples of the substituent that the substituted alkyl group may have include a halogen atom, a hydroxyl group, an amino group, a guanidino group, a carboxyl group, an aminocarbonyl group, and a mercapto group.

[0039] R ２ Examples of the substituent that the substituted alkenyl group has include a halogen atom, a hydroxyl group, an amino group, a guanidino group, a carboxyl group, an aminocarbonyl group, and a mercapto group.

[0040] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0041] R １ The "amino acid" as used herein means an amino acid bound to C(=O) in the above general formula (I) by an appropriate bond.

[0042] R １ Examples of the amino acid as R include amino acids bonded through an amino group, amino acids bonded through a carboxyl group, amino acids bonded through a hydroxyl group, amino acids bonded through a thiol group, and amino acids bonded through an amide group. １ Amino acids as such include, in particular, amino acids linked through the amino group.

[0043] An "amino acid bonded via an amino group" refers to an amino acid bonded to C(=O) in formula (I) via the nitrogen atom of the amino group. When an amino acid has two or more amino groups, any of the amino groups may be used to bond to C(=O) in formula (I). For example, the α-amino group may be used to bond to C(=O) in formula (I), and the ε-amino group may be used to bond to C(=O) in formula (I).

[0044] "Amino acid bonded via a carboxyl group" means an amino acid bonded to C(=O) in formula (I) via the oxygen atom of the OH of the carboxyl group. When an amino acid has two or more carboxyl groups, any of the carboxyl groups may be used to bond to C(=O) in formula (I). For example, an α-carboxyl group may be used to bond to C(=O) in formula (I), or another carboxyl group may be used to bond to C(=O) in formula (I).

[0045] "Hydroxyl-linked amino acid" means an amino acid linked to the C(=O) in formula (I) through the oxygen atom of the hydroxyl group.

[0046] "Amino acid bonded through a thiol group" means an amino acid bonded to the C(=O) in formula (I) through the sulfur atom of the thiol group.

[0047] "Amino acid bonded through an amide group" means an amino acid bonded to the C(=O) in formula (I) through the nitrogen atom of the amide group.

[0048] Examples of amino acids include basic amino acids such as lysine, ornithine, arginine, histidine, citrulline, diaminobutanoic acid, diaminopropanoic acid, and diaminopropionic acid, aliphatic amino acids such as isoleucine, alanine, valine, leucine, and glycine, hydroxymonoaminocarboxylic acid amino acids such as threonine and serine, cyclic amino acids (also called "imino acids") such as proline, aromatic amino acids such as phenylalanine, tyrosine, and tryptophan, sulfur-containing amino acids such as cysteine, cystine, and methionine, acidic amino acids such as glutamic acid and aspartic acid, and amino acids having an amide group in the side chain such as glutamine and asparagine. Examples of amino acids also include norvaline, norleucine, α-aminobutyric acid, γ-aminobutyric acid, hydroxyproline, tert-leucine, sarcosine, and β-alanine.

[0049] An amino acid may or may not have a substituent on its amino group and / or carboxyl group. In other words, unless otherwise specified, the term "amino acid" encompasses those having a substituent on its amino group and / or carboxyl group. In other words, amino acids also include those having a substituent on the amino group and / or carboxyl group of the above-mentioned amino acids. Examples of the substituent on the amino group in an amino acid include an optionally substituted alkylcarbonyl group, an optionally substituted alkyl group, etc. In other words, the amino group in an amino acid may be, for example, an optionally substituted alkylcarbonylamino group, an optionally substituted alkylamino group, etc. Examples of the substituent on the amino group in an amino acid include, in particular, an n-nonylcarbonyl group, a methyl group, an ethyl group, a tert-butyl group, etc. Examples of the substituent on the carboxyl group in an amino acid include, for example, an optionally substituted alkyl group, an amino group, etc. In other words, the carboxyl group in an amino acid may be, for example, an optionally substituted alkoxycarbonyl group, an aminocarbonyl group, etc. Examples of the substituent on the carboxyl group in the amino acid include a methyl group, an ethyl group, a tert-butyl group, a benzyl group, and the like.

[0050] Unless otherwise specified, amino acids may be in the D-configuration, the L-configuration, or a combination thereof. The ratio of D-configuration to L-configuration in a combination is not particularly limited. Amino acids may particularly be in the L-configuration. When an amino acid in the D-configuration or the L-configuration is selected, it is sufficient to use the amino acid in the D-configuration or the L-configuration, and this does not preclude the amino acid in the L-configuration or the D-configuration from being used in combination.

[0051] R １ The "dipeptide" as used herein means a dipeptide bonded to C(=O) in the above general formula (I) by an appropriate bond.

[0052] R １Examples of dipeptides as R include dipeptides linked through amino groups, dipeptides linked through carboxyl groups, dipeptides linked through hydroxyl groups, dipeptides linked through thiol groups, and dipeptides linked through amide groups. １ Dipeptides as such include, in particular, dipeptides linked via amino groups.

[0053] A "dipeptide bonded via an amino group" refers to a dipeptide bonded to C(=O) in formula (I) via the nitrogen atom of the amino group. When a dipeptide has two or more amino groups, any of the amino groups may be used to bond to C(=O) in formula (I). For example, the α-amino group may be used to bond to C(=O) in formula (I), and the ε-amino group may be used to bond to C(=O) in formula (I).

[0054] A "dipeptide bonded via a carboxyl group" refers to a dipeptide bonded to C(=O) in formula (I) via the oxygen atom of the OH of the carboxyl group. When a dipeptide has two or more carboxyl groups, any of the carboxyl groups may be used to bond to C(=O) in formula (I). For example, an α-carboxyl group may be used to bond to C(=O) in formula (I), or another carboxyl group may be used to bond to C(=O) in formula (I).

[0055] "Hydroxyl-linked dipeptide" means a dipeptide linked to the C(=O) in formula (I) through the oxygen atom of the hydroxyl group.

[0056] "Thiol-linked dipeptide" means a dipeptide linked to C(=O) in formula (I) through the sulfur atom of the thiol group.

[0057] "Amido-linked dipeptide" means a dipeptide linked to the C(=O) in formula (I) through the nitrogen atom of the amide group.

[0058] The amino acids constituting a dipeptide are described above with respect to amino acids. The two amino acids constituting a dipeptide may be the same or different. Specific examples of dipeptides include Glu-Val, Val-Val, Cys-Gly, Glu-Glu, Glu-Gly, Gly-Gly, Glu-Phe, and Glu-Pro. Dipeptides may or may not have substituents on their amino and / or carboxyl groups. That is, unless otherwise specified, the term "dipeptide" includes those having substituents on their amino and / or carboxyl groups. The same descriptions of the amino and / or carboxyl groups in amino acids described above with respect to the substituents on the amino and / or carboxyl groups in dipeptides are described above with respect to the substituents on the amino and / or carboxyl groups in amino acids.

[0059] R １ The "tripeptide" as used herein means a tripeptide linked to C(=O) in the above general formula (I) by an appropriate bond.

[0060] R １ Examples of tripeptides as R include tripeptides linked through amino groups, tripeptides linked through hydroxyl groups, and tripeptides linked through thiol groups. １ Tripeptides as such include, in particular, tripeptides linked via amino groups.

[0061] The term "a tripeptide bonded via an amino group" refers to a tripeptide bonded to C(=O) in formula (I) via the nitrogen atom of the amino group. When a tripeptide has two or more amino groups, either of the amino groups may be used to bond to C(=O) in formula (I). For example, the α-amino group may be used to bond to C(=O) in formula (I), and the ε-amino group may be used to bond to C(=O) in formula (I).

[0062] By "hydroxyl-linked tripeptide" is meant a tripeptide linked to the C(=O) in formula (I) through the oxygen atom of a hydroxyl group.

[0063] "Thiol-linked tripeptide" means a tripeptide linked to the C(=O) in formula (I) through the sulfur atom of a thiol group.

[0064] The amino acids constituting a tripeptide are described above with respect to amino acids. The three amino acids constituting a tripeptide may be the same or different. Specific examples of tripeptides include Glu-Glu-Val, Glu-Val-Val, Val-Val-Val, Val-Glu-Val, Val-Val-Glu, Glu-Val-Glu, Val-Glu-Glu, Glu-Glu-Glu, Glu-Glu-Glu, Glu-Glu-Gly, Glu-Gly-Gly, Glu-Glu-Phe, and Glu-Glu-Pro. Tripeptides may or may not have substituents on their amino and / or carboxyl groups. In other words, unless otherwise specified, the term "tripeptide" includes those having substituents on their amino and / or carboxyl groups. The same descriptions of the amino and / or carboxyl groups of amino acids described above with respect to the substituents on the amino and / or carboxyl groups of tripeptides are described above with respect to the substituents on the amino and / or carboxyl groups of amino acids.

[0065] R １ and R ２ Specifically, R in the formulas (compound 3) to (compound 6), (compound 12) to (compound 16), (compound 19), (compound 20), and (compound 23) described below are １ and R ２ That is, functional groups corresponding to R １ and R ２ Specifically, for example, R in the formulas (compound 3) to (compound 6), (compound 12) to (compound 16), (compound 19), (compound 20), and (compound 23) described below, respectively. １ and R ２ The functional groups may be selected from those corresponding to:

[0066] When component (A) can form a salt, component (A) may be used in its free form, its salt, or a combination thereof. That is, unless otherwise specified, the term "component (A)" may refer to component (A) in its free form, its salt, or a combination thereof. "Free form" refers to a form in which no salt is formed. The salt is not particularly limited as long as it does not impair the effects of the present invention. For example, salts of acidic groups such as carboxyl groups include ammonium salts, salts with alkali metals such as sodium and potassium, salts with alkaline earth metals such as calcium and magnesium, aluminum salts, zinc salts, salts with organic amines such as triethylamine, ethanolamine, morpholine, pyrrolidine, piperidine, piperazine, and dicyclohexylamine, and salts with basic amino acids such as arginine and lysine. Furthermore, examples of salts of basic groups such as amino groups include salts with inorganic acids such as hydrochloric acid, sulfuric acid, phosphoric acid, nitric acid, and hydrobromic acid, salts with organic carboxylic acids such as acetic acid, citric acid, benzoic acid, maleic acid, fumaric acid, tartaric acid, succinic acid, tannic acid, butyric acid, hybenzic acid, pamoic acid, enanthic acid, decanoic acid, teoclic acid, salicylic acid, lactic acid, oxalic acid, mandelic acid, and malic acid, and salts with organic sulfonic acids such as methanesulfonic acid, benzenesulfonic acid, and p-toluenesulfonic acid. As the salt, one type of salt may be used, or two or more types of salts may be used in combination.

[0067] Furthermore, when component (A) can form a hydrate, component (A) may be used as a non-hydrate, a hydrate, or a combination thereof. That is, the term "component (A)" (e.g., "component (A) in free form" or "salt of component (A)") may encompass both the non-hydrate and the hydrate, unless otherwise specified.

[0068] Component (A) may be in any form, such as an ion, when used.

[0069] As component (A), one kind of component may be used, or two or more kinds of components may be used in combination. When two or more kinds of components are selected as component (A), the "amount" or "concentration" of component (A) may mean the total amount or total concentration of the selected components, unless otherwise specified.

[0070] Component (A) may be a commercially available product or may be obtained by appropriate production. The production method of component (A) is not particularly limited. Component (A) can be produced, for example, by a known method. Specific examples of component (A) include chemical synthesis, enzymatic reaction, fermentation, extraction, or a combination thereof. Component (A) may be purified to a desired degree or not. That is, component (A) may be a purified product, or a material containing component (A). Specific examples of materials containing component (A) include fermentation products such as culture solutions, bacterial cells, and culture supernatants obtained by culturing microorganisms capable of producing component (A), agricultural and aquatic livestock products containing component (A), and processed products thereof. Processed products include materials such as the above-mentioned fermentation products that have been subjected to processes such as concentration, dilution, drying, fractionation, extraction, and purification. As component (A), for example, a material having a component (A) content of 1% (w / w) or more, 5% (w / w) or more, 10% (w / w) or more, 30% (w / w) or more, 50% (w / w) or more, 70% (w / w) or more, 90% (w / w) or more, or 95% (w / w) or more may be used.

[0071] By utilizing the active ingredient, specifically by applying the active ingredient to a plant, for example, insect resistance in the plant may be induced, i.e., the effect of inducing insect resistance in the plant may be obtained. This effect is also referred to as an "insect resistance induction effect." Thus, the active ingredient may be used, for example, to induce insect resistance in a plant. "Insect resistance" may mean resistance to insect damage, and specifically may mean the property of reducing the severity of insect damage. "Inducing insect resistance in a plant" may be used interchangeably with "conferring insect resistance to a plant" or "improving insect resistance in a plant."

[0072] By utilizing an active ingredient, specifically by applying the active ingredient to a plant, for example, pest repellency in the plant may be induced, i.e., an effect of inducing pest repellency in the plant may be obtained. This effect is also referred to as a "pest repellency induction effect." Thus, the active ingredient may be used, for example, to induce pest repellency in the plant. "Pest repellency" may mean repellency against pests, and specifically may mean the property of reducing the arrival, approach, etc. of pests. "Inducing pest repellency in a plant" may be used interchangeably with "imparting pest repellency to a plant" or "improving pest repellency in a plant."

[0073] By utilizing the active ingredient, specifically by applying the active ingredient to a plant, for example, insect damage to the plant may be prevented, that is, an effect of preventing insect damage to the plant may be obtained. This effect is also referred to as an "insect damage prevention effect." Thus, the active ingredient may be used, for example, to prevent insect damage to the plant. In particular, the insect damage prevention effect may be obtained by inducing insect resistance in the plant and / or by inducing pest repellency in the plant. Thus, the insect damage prevention effect may be an example of an insect resistance induction effect and / or a pest repellency induction effect. "Prevention of insect damage" may be used interchangeably with "alleviation of insect damage," "reduction of insect damage," or "control of insect damage."

[0074] By utilizing an active ingredient, specifically by applying the active ingredient to a plant, insect resistance in the plant may be induced, for example, not only in the plant to which the active ingredient has been applied, but also in plant strains that are present in the vicinity of the applied plant and to which the active ingredient has not been applied, i.e., the effect of inducing insect resistance in the plant may be obtained.

[0075] By utilizing an active ingredient, specifically by applying the active ingredient to a plant, for example, pest repellency in the plant may be induced not only in the plant to which the active ingredient has been applied, but also in plant plants that are present in the vicinity of the applied plant and to which the active ingredient has not been applied, i.e., the effect of inducing pest repellency in the plant may be obtained.

[0076] By utilizing an active ingredient, specifically by applying the active ingredient to a plant, for example, insect damage to the plant may be prevented not only in the plant to which the active ingredient has been applied, but also in plant plants that are present in the vicinity of the applied plant and to which the active ingredient has not been applied, i.e., the effect of preventing insect damage to the plant may be obtained.

[0077] By utilizing the active ingredient, specifically by applying the active ingredient to a plant, for example, the cultivation performance of the plant may be improved, i.e., an effect of improving the cultivation performance of the plant may be obtained. This effect is also referred to as a "cultivation performance improving effect." In particular, the cultivation performance improving effect may be obtained by inducing insect resistance in the plant, inducing pest repellency in the plant, and / or preventing insect damage to the plant. Therefore, the cultivation performance improving effect may be an example of an insect resistance inducing effect, a pest repellent effect, and / or an insect damage prevention effect. Specific examples of improvements in plant cultivation performance include improvements in plant yield, plant growth, and plant survival. In particular, improvements in plant cultivation performance include improvements in plant yield.

[0078] By utilizing an active ingredient, specifically by applying the active ingredient to a plant, for example, the quality of the plant may be improved, i.e., an effect of improving the quality of the plant may be obtained. This effect is also referred to as a "quality improvement effect." In particular, the quality improvement effect may be obtained by inducing insect resistance in the plant, inducing pest repellency in the plant, and / or preventing insect damage to the plant. Thus, the quality improvement effect may be an example of an insect resistance induction effect, a pest repellency effect, and / or an insect damage prevention effect.

[0079] "Improved plant quality" means that a characteristic of a plant species is qualitatively and / or quantitatively improved when compared to the same characteristic of a control plant grown under the same conditions without the method of the present invention. Specific examples of improved plant quality include improved plant appearance, improved appearance of the harvested product (e.g., seeds, fruits, leaves, vegetables, etc.), improved organoleptic properties (e.g., taste, aroma, texture, etc.) of the harvested product, improved storage life and / or storage stability of the harvested product, improved processability of the harvested product, more uniform plant growth (e.g., meaning that the plants germinate, flower, and / or fruit simultaneously), and improved food safety of the harvested product.

[0080] The type of plant is not particularly limited as long as it is susceptible to insect damage.

[0081] The plant may be, for example, a woody plant or a herbaceous plant. Examples of the plant include grasses (rice, barley, wheat, corn, sorghum, millet, sugarcane, oats, lawn grass, pearl millet, finger millet, fonio, etc.), solanaceae plants (tomato, bell pepper, eggplant, potato, tobacco, etc.), cucurbits (cucumber, melon, pumpkin, etc.), legumes (pea, soybean, kidney bean, alfalfa, peanut, broad bean, cowpea, lentil, chickpea, clover, groundnut, bambara groundnut, etc.), Brassicaceae plants (radish, Chinese cabbage, cabbage, komatsuna, nanohana, bok choy, Arabidopsis, etc.), Rosaceae plants (strawberry, apple, pear, peach, etc.), and cucurbits. Examples include plants of the family Crotalaceae (such as mulberry), plants of the family Malvaceae (such as cotton), plants of the family Apiaceae (such as carrots, parsley, and celery), plants of the family Liliaceae (such as leeks, onions, and asparagus), plants of the family Asteraceae (such as burdock, sunflower, chrysanthemum, garland chrysanthemum, safflower, and lettuce), plants of the family Amaranthaceae (such as sugar beets), plants of the family Ericaceae (such as blueberries and cranberries), plants of the family Vitaceae (such as grapes), plants of the family Rutaceae (such as Satsuma mandarins, lemons, and yuzu), plants of the family Rubiaceae (such as coffee trees), plants of the family Oleaceae (such as olives), plants of the family Lauraceae (such as avocados), plants of the family Anacardiaceae (such as mangoes and cashew trees), plants of the family Sapindaceae (such as lychees), and plants of the family Lamiaceae (such as coleus).

[0082] The plant may be one type of plant, or two or more types of plants.

[0083] "Insect damage" may refer to damage caused by pests. Insect damage includes feeding damage (i.e., the feeding of plants by pests).

[0084] The type of pest is not particularly limited as long as it can cause insect damage.

[0085] Pests include agricultural pests.

[0086] Specific examples of pests include Lepidoptera (Plutellidae, Noctuidae, Pyralidae, Tortricidae, Leafminers, Boneworms, Gelechiidae, Crambidae, Arctiidae, Lymantriidae, etc.), Hemiptera (Cicadiidae, Delphacidae, Psyllidae, Aphididae, Aleyrodidae, Coccinellidae, Tingidae, Hemiptera, etc.), Coleoptera (Scarabaeidae, Elateridae, Coccinellidae, Cerambycidae, Chrysomelidae, Curculionidae, etc.), Diptera (Muscidae, Blackflies, Examples include organisms classified into the following families: Arthridae, Sarcophagidae, Anthomyiidae, Tephritidae, Euloidea, Chloropidae, etc.), Orthoptera (Acrididae, Locustidae, Sclerotidae, etc.), Thysanoptera (Thysanoptera, Thripidae, Sclerotidae, Sclerotidae, etc.), Tylenchidae (Aphelencoidae, Neotylenchidae, etc.), Collembola (Sclerotidae, Sclerotidae, etc.), Acari (Tetranychidae, Miteridae, Acaridae, Sarcoptidae, etc.), and Stylommatophora (Slugmitidae, Sclerotidae, etc.).

[0087] Specific examples of pests of the order Lepidoptera include the rice stem borer, rice leafroller, skipper butterfly, rice armyworm, armyworm, two-banded nodule, common cutworm, beetle moth, lesser beetle moth, soybean pod moth, bean root moth, turmeric moth, turnip cutworm, potato cutworm, potato leaf moth, white nodule, tobacco budworm, tobacco cotton moth, armyworm moth, beet armyworm, diamondback moth, cabbage white butterfly, large brassicae butterfly, yellow spotted moth, and silver looper moth. Specific examples of pests of the Hemiptera order include the brown planthopper, the whitebacked planthopper, the sparse brown planthopper, the green rice leafhopper, the lightning leafhopper, the red-striped rice bug, the red-bearded green rice bug, the spider bug, the green stink bug, the southern green stink bug, the rice stink bug, the black rice bug, the thorny spotted bug, the large thorny spotted bug, the white-spotted stink bug, the rice-winged long-horned bug, the narrow-horned stink bug, the one-spotted stink bug, the brown marmorated stink bug, the spotted stink bug, the onion aphid, the wheat collar aphid, the corn aphid, and the soybean aphid. Specific examples of pests of the order Coleoptera include the coffee bark beetle, rice water weevil, rice leaf beetle, rice weevil, comb beetle, round beetle, cuprea beetle, cuprea beetle, bean beetle, Japanese beetle, red-billed dung beetle, common lady beetle, two-striped leaf beetle, large 24-spot lady beetle, 24-spot lady beetle, two-striped lady beetle, small beetle, Japanese beetle, striped beetle, cucumber beetle, and striped flea beetle.Specific examples of pests of the order Diptera include the rice brown fly, rice leaf miner, wheat gall midge, seed fly, soybean pod gall midge, soybean stem beetle, bean leaf miner, tomato leaf miner, black-legged leaf miner, and eggplant leaf miner. Specific examples of pests in the Orthoptera order include the rice grasshoppers and the long-winged grasshoppers.Specific examples of pests in the Thripida order include the rice thrips and the southern melon thrips.Specific examples of pests in the Tylenchida order include the root-knot nematode, the root-lesion nematode, and the cyst nematode.Specific examples of pests in the Collembola order include the white springtail and the Matsumoto white springtail.Specific examples of pests in the order Acari include wheat mites, two-spotted spider mites, Kanzawa spider mites, Tyrophagus putrescentiae, and Tarsorrhexis striata.Specific examples of pests in the order Stylommatophora include snails and slugs.

[0088] The pest may be one type of pest, or two or more types of pests.

[0089] The insect resistance induction effect is, for example, 2+ This can be confirmed by using signal transduction as an indicator. That is, when the active ingredient is used, the Ca 2+ It is possible that the active ingredient exerted an insect pest resistance induction effect when signal transduction was enhanced. 2+ "Increased signal transduction" refers to the increase in Ca in plant strains treated with the active ingredient. 2+ Increased signal transduction and / or Ca in plants that have not been treated with active ingredients and are present in the vicinity of the plant. 2+ This means increased signal transduction. 2+ Signal transduction can be confirmed by calcium imaging using, for example, a calcium indicator or a calcium-sensitive fluorescent protein. Specifically, for example, in a transgenic plant modified to express a calcium-sensitive fluorescent protein, calcium imaging can be used to detect calcium. 2+ Signal transduction can be confirmed. Examples of calcium-sensitive fluorescent proteins include Cameleon, TN-XL, GCaMP3, G-GECO, and R-GECO. Detection of signals (e.g., fluorescence) in calcium imaging can be performed using a detector appropriate for the type of signal, such as a fluorescence detector. Specifically, calcium imaging can be performed, for example, by the procedures described in the Examples.

[0090] The insect resistance induction effect can be confirmed, for example, using the expression of insect resistance genes as an indicator. That is, if the expression of an insect resistance gene is increased when the active ingredient is used compared to when the active ingredient is not used, it is possible that the active ingredient has an insect resistance induction effect. Here, "increased expression of an insect resistance gene" refers to increased expression of an insect resistance gene in a plant strain to which the active ingredient has been applied, and / or increased expression of an insect resistance gene in plant strains in the vicinity of the plant to which the active ingredient has not been applied. An example of an insect resistance gene is the AtOPR3 gene. The AtOPR3 gene encodes 12-oxophytodienoic acid reductase, which is involved in jasmonic acid biosynthesis. Increased gene expression can be confirmed, for example, by measuring the transcription level (e.g., mRNA level), translation level (e.g., protein level encoded by the gene), or activity of the protein encoded by the gene. Methods for measuring mRNA level include Northern hybridization and qPCR. Methods for measuring the amount of protein include Western blotting. Methods for measuring protein activity can be appropriately selected depending on various conditions, such as the type of target protein.

[0091] The insect pest resistance induction effect can be confirmed, for example, using the insect pest prevention effect as an indicator. That is, if the insect pest prevention effect is obtained by the active ingredient, it may be determined that the insect pest resistance induction effect is obtained by the active ingredient.

[0092] The pest repellency induction effect can be confirmed, for example, using the number of approaching pests (e.g., the total number of pests that land on a plant within a certain period of time) as an indicator. That is, if the number of approaching pests (e.g., the total number of pests that land on a plant within a certain period of time) is reduced when the active ingredient is used compared to when the active ingredient is not used, it is possible that the active ingredient has achieved a pest repellency induction effect. Here, "a reduction in the number of approaching pests" means a reduction in the number of approaching pests on the plant to which the active ingredient has been applied, and / or a reduction in the number of approaching pests on plant plants to which the active ingredient has not been applied that are present in the vicinity of the plant.

[0093] The pest repellency induction effect can be confirmed, for example, using the insect damage prevention effect as an indicator. That is, if the insect damage prevention effect is obtained by the active ingredient, it may be determined that the pest repellency induction effect is obtained by the active ingredient.

[0094] The insect damage prevention effect can be confirmed, for example, using the degree of insect damage (e.g., the amount of plant food consumed by pests) as an indicator. That is, if the degree of insect damage to a plant (e.g., the amount of plant food consumed by pests) is reduced when the active ingredient is used compared to when the active ingredient is not used, it can be determined that the active ingredient has achieved an insect damage prevention effect. Here, "reduction in the degree of insect damage" means a reduction in the degree of insect damage in a plant to which the active ingredient has been applied, and / or a reduction in the degree of insect damage in plant plants present in the vicinity of the plant to which the active ingredient has not been applied.

[0095] The insect pest resistance induction effect, pest repellency induction effect, or insect pest prevention effect can be confirmed, for example, using the effect of improving cultivation performance as an indicator. That is, when the cultivation performance improvement effect is obtained by the active ingredient, it may be determined that the insect pest resistance induction effect, pest repellency induction effect, or insect pest prevention effect is obtained by the active ingredient.

[0096] The effect of improving cultivation performance can be confirmed, for example, using plant cultivation performance (e.g., yield, growth, viability, etc.) as an indicator. In other words, if the cultivation performance (e.g., yield, growth, viability, etc.) of a plant is improved when the active ingredient is used compared to when the active ingredient is not used, it can be determined that the active ingredient has an effect of improving cultivation performance. Here, "improvement of plant cultivation performance" means improvement in the cultivation performance of a plant strain to which the active ingredient has been applied, and / or improvement in the cultivation performance of a plant strain present in the vicinity of the plant to which the active ingredient has not been applied.

[0097] The insect pest resistance induction effect, pest repellency induction effect, or insect pest prevention effect can be confirmed, for example, using the quality improvement effect as an indicator. That is, if a quality improvement effect is obtained by an active ingredient, it may be determined that the insect pest resistance induction effect, pest repellency induction effect, or insect pest prevention effect is obtained by the active ingredient.

[0098] The quality improvement effect can be confirmed, for example, using as an indicator the quality of the plant (e.g., the appearance of the plant, the appearance of the harvested product (e.g., seeds, fruits, leaves, vegetables, etc.), the sensory characteristics of the harvested product (e.g., taste, aroma, texture, etc.), the storage period and / or storage stability of the harvested product, the processability of the harvested product, more uniform plant growth (e.g., meaning simultaneous germination, flowering, and / or fruiting of the plant), the food safety of the harvested product, etc.). In other words, it can be determined that a quality improvement effect has been achieved by the active ingredient when the quality of the plant (e.g., the appearance of the plant, the appearance of the harvested product (e.g., seeds, fruits, leaves, vegetables, etc.), the sensory characteristics of the harvested product (e.g., taste, aroma, texture, etc.), the storage period and / or storage stability of the harvested product, the processability of the harvested product, more uniform plant growth (e.g., simultaneous germination, flowering, and / or fruiting of the plant), the food safety of the harvested product, etc.) is improved when the active ingredient is used compared to when the active ingredient is not used. Here, "improving the quality of a plant" means improving the quality of a plant strain to which an active ingredient has been applied, and / or improving the quality of a plant strain that is present in the vicinity of the plant strain to which no active ingredient has been applied.

[0099] <2> Composition of the Present Invention The composition of the present invention is a composition containing an active ingredient (i.e., the above-mentioned component (A)).

[0100] The composition of the present invention can be used by applying it to plants. The use mode of the composition of the present invention will be described in detail in the "Method of the present invention." The composition of the present invention can be used, for example, to achieve the effects exemplified above.

[0101] By utilizing the composition of the present invention, specifically by applying the composition of the present invention to a plant, for example, insect resistance in the plant may be induced, i.e., an insect resistance induction effect may be obtained. Thus, the composition of the present invention may be, for example, a composition for inducing insect resistance in a plant. A composition for inducing insect resistance in a plant is also referred to as an "insect resistance inducer in a plant."

[0102] By utilizing the composition of the present invention, specifically by applying the composition of the present invention to a plant, for example, pest repellency in the plant may be induced, i.e., a pest repellency induction effect may be obtained. Thus, the composition of the present invention may be, for example, a composition for inducing pest repellency in a plant. A composition for inducing pest repellency in a plant is also referred to as a "pest repellency inducer in a plant."

[0103] By utilizing the composition of the present invention, specifically by applying the composition of the present invention to a plant, for example, insect damage to the plant may be prevented, i.e., an insect damage prevention effect may be obtained. Thus, the composition of the present invention may be, for example, a composition for preventing insect damage to plants. A composition for preventing insect damage to plants is also called a "plant insect damage prevention agent." A composition for preventing insect damage to plants may be an example of a composition for inducing insect resistance in plants.

[0104] By utilizing the composition of the present invention, specifically by applying the composition of the present invention to a plant, for example, the plant cultivation performance may be improved, i.e., a cultivation performance improving effect may be obtained. Thus, the composition of the present invention may be, for example, a composition for improving plant cultivation performance. A composition for improving plant cultivation performance is also referred to as a "plant cultivation performance improver." A composition for improving plant cultivation performance may be an example of a composition for inducing insect pest resistance in a plant, a composition for inducing pest repellency in a plant, or a composition for preventing insect pests in a plant.

[0105] By utilizing the composition of the present invention, specifically by applying the composition of the present invention to a plant, for example, the quality of the plant may be improved, i.e., a quality improvement effect may be obtained. Thus, the composition of the present invention may be, for example, a composition for improving plant quality. A composition for improving plant quality is also referred to as a "plant quality improver." A composition for improving plant quality may be an example of a composition for inducing insect pest resistance in a plant, a composition for inducing pest repellency in a plant, or a composition for preventing insect pests in a plant.

[0106] The use of the composition of the present invention as exemplified above may be useful, for example, in the agricultural and horticultural fields. Thus, the composition of the present invention may be used, for example, in the agricultural and horticultural fields. That is, the composition of the present invention may be, for example, an agricultural and horticultural composition. Specifically, the composition of the present invention may be, for example, an agricultural and horticultural composition used in the use of the composition of the present invention as exemplified above.

[0107] The compositions of the present invention may be provided, for example, as pesticides, fertilizers, biostimulants, and the like.

[0108] The composition of the composition of the present invention is not particularly limited as long as the composition of the present invention contains an active ingredient and can achieve the desired effect. The types and amounts of ingredients contained in the composition of the present invention can be appropriately selected depending on various conditions such as the type of target plant, the cultivation method of the target plant, the growth stage of the target plant, the purpose of use of the composition of the present invention, and the mode of use of the composition of the present invention.

[0109] The composition of the present invention may consist of an active ingredient or may contain ingredients other than the active ingredient. Examples of ingredients other than the active ingredient include those commonly used in agricultural chemicals, fertilizers, biostimulants, pharmaceuticals, and other applications. Specific examples of such ingredients include excipients, binders, disintegrants, lubricants, stabilizers, diluents, surfactants, spreaders, pH adjusters, water, alcohol, vitamins, minerals, and other additives. Specific examples of spreaders include Approach (registered trademark) BI (manufactured by Kao Corporation), Mixpower (registered trademark) (manufactured by Syngenta Japan Ltd.), and Squash (manufactured by Maruwa Biochemical Co., Ltd.). The ingredients other than the active ingredient may be a single ingredient, or two or more ingredients may be used. The composition of the present invention may be formulated as appropriate. The dosage form of the composition of the present invention is not particularly limited. The dosage form of the composition of the present invention can be appropriately selected depending on various conditions, such as the mode of use of the composition of the present invention. Examples of dosage forms include liquids, suspensions, powders, tablets, pills, capsules, and pastes.

[0110] The content of the active ingredient in the composition of the present invention is more than 0% (w / w) and not more than 100% (w / w). The content of the active ingredient in the composition of the present invention may be, for example, 20 ppm (w / w) or more, 50 ppm (w / w) or more, 100 ppm (w / w) or more, 200 ppm (w / w) or more, 500 ppm (w / w) or more, 1000 ppm (w / w) or more, 2000 ppm (w / w) or more, 5000 ppm (w / w) or more, 1% (w / w) or more, 2% (w / w) or more, 5% (w / w) or more, 10% (w / w) or more, 20% (w / w) or more, 30% (w / w) or more, 50% (w / w) or more, or 70% (w / w) or more, and may be 100% (w / w) or less, less than 100% (w / w), 99.9% (w / w) or less, 90% (w / w) or less, 70% (w / w) or less. % (w / w) or less, 50 % (w / w) or less, 30 % (w / w) or less, 20 % (w / w) or less, 10 % (w / w) or less, 5 % (w / w) or less, 2 % (w / w) or less, 1 % (w / w) or less, 5000 ppm (w / w) or less, 2000 ppm (w / w) or less, 1000 ppm (w / w) or less, or 500 ppm (w / w) or less, or any compatible combination thereof. The content of the active ingredient in the composition of the present invention may be, specifically, for example, 20 ppm (w / w) to 50 ppm (w / w), 50 ppm (w / w) to 100 ppm (w / w), 100 ppm (w / w) to 1000 ppm (w / w), 1000 ppm (w / w) to 1% (w / w), 1% (w / w) to 10% (w / w), 10% (w / w) to 30% (w / w), 30% (w / w) to 50% (w / w), 50% (w / w) to 70% (w / w), or 70% (w / w) to 99.9% (w / w).Specific examples of the content of the active ingredient in the composition of the present invention include 20 ppm (w / w) to 99.9% (w / w), 100 ppm (w / w) to 99.9% (w / w), 1000 ppm (w / w) to 99.9% (w / w), 1% (w / w) to 99.9% (w / w), 10% (w / w) to 99.9% (w / w), 100 ppm (w / w) to 50% (w / w), 100 ppm (w / w) to 10% (w / w), 100 ppm (w / w) to 1% (w / w), 1000 ppm (w / w) to 50% (w / w), 1000 ppm (w / w) to 10% (w / w), 1000 ppm (w / w) to 1% (w / w), 1 % (w / w) to 50% (w / w), or 1% (w / w) to 10% (w / w).

[0111] The content of the active ingredient in the composition of the present invention may be, for example, 0.1 mM or more, 0.2 mM or more, 0.5 mM or more, 1 mM or more, 2 mM or more, 5 mM or more, 10 mM or more, 20 mM or more, 50 mM or more, 100 mM or more, 200 mM or more, or 500 mM or more, or 1000 mM or less, 500 mM or less, 200 mM or less, 100 mM or less, 50 mM or less, 20 mM or less, 10 mM or less, 5 mM or less, 2 mM or less, or 1 mM or less, or a compatible combination thereof. Specifically, the content of the active ingredient in the composition of the present invention may be, for example, 0.1 to 0.2 mM, 0.2 to 0.5 mM, 0.5 to 1 mM, 1 to 2 mM, 2 to 5 mM, 5 to 10 mM, 10 to 20 mM, 20 to 50 mM, 50 to 100 mM, 100 to 200 mM, 200 to 500 mM, or 500 to 1000 mM. The content of the active ingredient in the composition of the present invention may be, specifically, for example, 0.1 to 1000 mM, 0.5 to 500 mM, or 2 to 200 mM.

[0112] In addition, the content of the active ingredient in the composition of the present invention can be set, for example, so that the concentration of the active ingredient is within a predetermined range when the composition of the present invention is used. The concentration of the active ingredient when the composition of the present invention is used is also referred to as the "use concentration of the active ingredient" or the "application concentration of the active ingredient." The use concentration of the active ingredient may be, in particular, the concentration when the composition of the present invention is used in the form of a liquid.

[0113] The concentration of the active ingredient used is, for example, 0.1 μM or more, 0.2 μM or more, 0.5 μM or more, 1 μM or more, 2 μM or more, 5 μM or more, 10 μM or more, 20 μM or more, 50 μM or more, 0.1 mM or more, 0.2 mM or more, 0.5 mM or more, 1 mM or more, 2 mM or more, 5 mM or more, 10 mM or more, 20 mM or more, 50 mM or more, 100 It may be 1000 mM or less, 200 mM or more, or 500 mM or more, 1000 mM or less, 500 mM or less, 200 mM or less, 100 mM or less, 50 mM or less, 20 mM or less, 10 mM or less, 5 mM or less, 2 mM or less, 1 mM or less, 0.5 mM or less, 0.2 mM or less, 0.1 mM or less, 50 μM or less, 20 μM or less, 10 μM or less, 5 μM or less, 2 μM or less, 1 µM or less, 0.5 µM or less, or 0.2 The concentration of the active ingredient may be, for example, 0.1 to 0.2 μM, 0.2 to 0.5 μM, 0.5 to 1 μM, 1 to 2 μM, 2 to 5 μM, 5 to 10 μM, 10 to 20 μM, 20 to 50 μM, 50 μM to 0.1 mM, 0.1 to 0.2 mM, 0.2 to 0.5 mM, 0.5 to 1 mM, 1 to 2 mM, 2 to 5 mM, 5 to 10 mM, 10 to 20 mM, 20 to 50 mM, 50 to 100 mM, 100 to 200 mM, 200 to 500 mM, or 500 to 1000 mM. The concentration of the active ingredient may be, for example, 0.1 μM to 1000 mM, 0.5 μM to 500 mM, or 2 μM to 200 mM.

[0114] When a material containing an active ingredient is used, the amount of the active ingredient (e.g., content (concentration), amount used, etc.) is calculated based on the amount of the active ingredient itself in the material. When the active ingredient forms a salt or hydrate, the amount of the active ingredient (e.g., content (concentration), amount used, etc.) is calculated based on the mass of the salt or hydrate converted to the mass of an equimolar free form.

[0115] The active ingredient and other ingredients may be mixed together in the composition of the present invention, or may be contained separately in the composition of the present invention, or in any combination thereof.

[0116] <3> Method of the Present Invention The method of the present invention is a method comprising applying an active ingredient (i.e., the above-mentioned component (A)) to a plant. The method of the present invention can be carried out, for example, to obtain the effects exemplified above.

[0117] By carrying out the method of the present invention, specifically by applying the active ingredient to a plant, for example, insect resistance in the plant may be induced, i.e., an insect resistance induction effect may be obtained. Thus, the method of the present invention may be, for example, a method for inducing insect resistance in a plant.

[0118] By carrying out the method of the present invention, specifically by applying the active ingredient to a plant, for example, pest repellency in the plant may be induced, i.e., a pest repellency induction effect may be obtained. Thus, the method of the present invention may be, for example, a method for inducing pest repellency in a plant.

[0119] By carrying out the method of the present invention, specifically by applying the active ingredient to a plant, for example, insect damage to the plant may be prevented, i.e., an insect damage prevention effect may be obtained. Thus, the method of the present invention may be, for example, a method for preventing insect damage to a plant. The method for preventing insect damage to a plant may be an example of a method for inducing insect resistance in a plant.

[0120] By carrying out the method of the present invention, specifically by applying an active ingredient to a plant, for example, the cultivation performance of the plant may be improved, i.e., a cultivation performance improving effect may be obtained. Thus, the method of the present invention may be, for example, a method for improving the cultivation performance of a plant. The method for improving the cultivation performance of a plant may be an example of a method for inducing insect resistance in a plant, a method for inducing pest repellency in a plant, or a method for preventing insect damage in a plant.

[0121] By carrying out the method of the present invention, specifically by applying an active ingredient to a plant, for example, the quality of the plant may be improved, i.e., a quality improvement effect may be obtained. Thus, the method of the present invention may be, for example, a method for improving the quality of a plant. The method for improving the quality of a plant may be an example of a method for inducing insect resistance in a plant, a method for inducing pest repellency in a plant, or a method for preventing insect damage in a plant.

[0122] The active ingredient can be applied to plants, for example, using the composition of the present invention (i.e., by applying the composition of the present invention). That is, one embodiment of the method of the present invention may be, for example, a method comprising applying the composition of the present invention to plants. "Applying an active ingredient to plants" also encompasses applying the composition of the present invention to plants. The composition of the present invention can be applied to plants, for example, directly or after being diluted, dispersed, or dissolved in a liquid such as water, physiological saline, buffer, alcohol, or DMSO. That is, the composition of the present invention can be applied to plants, for example, after adjusting the concentration to obtain the active ingredient use concentration as exemplified above. The composition of the present invention can be applied to plants, particularly in liquid form. The composition of the present invention can be used alone or in combination with other ingredients. The same description of the other ingredients other than the active ingredient in the description of the composition of the present invention applies mutatis mutandis. That is, the composition of the present invention can be used in combination with additives such as a spreading agent.

[0123] The application method of the composition of the present invention is not particularly limited as long as the desired effect is obtained. The application method of the composition of the present invention can be appropriately selected depending on various conditions, such as the type of pest, the type of plant, the plant cultivation method, the plant growth stage, and the intended use of the composition of the present invention. The composition of the present invention can be applied to plants using the usual methods for applying pesticides, fertilizers, biostimulants, etc. to plants. The composition of the present invention may be applied to the plant itself, to the medium in which the plant is cultivated, or a combination thereof. "Applying an active ingredient to a plant" is not limited to applying the composition of the present invention to the plant itself, but also includes applying the composition of the present invention to the medium in which the plant is cultivated. The medium in which the plant is cultivated is also referred to as a "growth medium" or "growth system." The growth medium can be appropriately selected depending on various conditions, such as the type of plant and the cultivation method. The plant cultivation method is not particularly limited. Plant cultivation can be carried out, for example, using the same method as a usual plant cultivation method, except for applying the composition of the present invention. Plant cultivation methods include soil culture, hydroponics, and nutrient solution soil culture. Hydroponics include hydroponics and solid medium culture. Hydroponics include nutrient film technique (NFT) and deep flow technique (DFT). That is, the medium (growth medium) in which plants are grown includes soil, hydroponic culture solution, and solid medium. Application to the plant itself includes spraying or coating the plant, and immersion of the plant. The composition of the present invention may be applied to the entire plant or to a part of the plant. For example, when the growth medium is a plant, the composition of the present invention may be applied to the entire plant or to a part of the plant. The composition of the present invention may be applied to, for example, the entire above-ground part of the plant. Examples of parts of the plant include leaves, stems, trunks, roots, flowers, fruits, and seeds. Examples of parts of the plant include leaves, in particular. When the composition of the present invention is applied to leaves, the composition of the present invention may be applied to only one or both of the upper and lower surfaces of the leaves. Specific examples of application to plants include foliar spraying and root dipping.Application to the growth medium includes spraying, irrigation, and mixing into the growth medium. Specifically, for example, the composition of the present invention may be applied (e.g., sprayed) to the growth medium through an irrigation tube. Application to the growth medium may be carried out so that the active ingredient reaches a position where it can act on the plant. For example, application to the medium in which the plant is grown may be carried out so that the active ingredient reaches the root zone of the plant.

[0124] The application timing of the composition of the present invention is not particularly limited as long as the desired effect is obtained. The application timing of the composition of the present invention can be appropriately selected depending on various conditions, such as the type of pest, the type of plant, the plant cultivation method, the plant growth stage, and the intended use of the composition of the present invention. When the composition of the present invention is applied to a growth medium, the growth medium may or may not already contain a plant. The desired effect may be obtained in the plant by applying the composition of the present invention to the plant itself or by applying the composition of the present invention to a growth medium already containing a plant. Furthermore, the desired effect may be obtained in plants that may exist in the growth medium in the future by applying the composition of the present invention to a growth medium without a plant. Examples of plants that may exist in the growth medium in the future include plants that will be transferred to the growth medium from outside in the future and plants that will be generated in the growth medium in the future. The composition of the present invention may be applied only once, or may be applied twice or more times. The composition of the present invention may be applied intermittently or continuously.

[0125] The application amount of the composition of the present invention is not particularly limited as long as the desired effect can be obtained.The application amount of the composition of the present invention can be appropriately selected depending on various conditions such as the type of pest, the type of plant, the plant cultivation method, the growth stage of the plant, the purpose of use of the composition of the present invention, and the application method and application time of the composition of the present invention.

[0126] The application rate of the composition of the present invention is, for example, 100 L / ha or more, 200 L / ha or more, 500 L / ha or more, 1000 L / ha or more, 1500 L / ha or more, 2000 L / ha or more, 3000 L / ha or more, 4000 L / ha or more, as the application rate of the composition of the present invention in liquid form (for example, the composition of the present invention in liquid form containing the active ingredient at the use concentration as exemplified above). or more than 100,000 L / ha, or more than 150,000 L / ha, or more than 200,000 L / ha, or more than 300,000 L / ha, or more than 500,000 L / ha, or more than 70,000 L / ha, or more than 100,000 L / ha, or more than 150,000 L / ha, or more than 200,000 L / ha, or more than 300,000 L / ha, or more than 500,000 L / ha, or more than 7 It may be 50,000 L / hectare or more, 1,000,000 L / hectare or less, 750,000 L / hectare or less, 500,000 L / hectare or less, 300,000 L / hectare or less, 200,000 L / hectare or less, 150,000 L / hectare or less, 100,000 L / hectare or less, 70,000 L / hectare or less, 50,000 L / hectare or less, 30,000 L The water flow rate may be 10,000 L / hectare or less, 10,000 L / hectare or less, 9000 L / hectare or less, 8000 L / hectare or less, 7000 L / hectare or less, 6000 L / hectare or less, 5000 L / hectare or less, 4000 L / hectare or less, 3000 L / hectare or less, 2000 L / hectare or less, or 1500 L / hectare or less, or any compatible combination thereof.The application rate of the composition of the present invention is, for example, 100 L / ha to 1500 L / ha, 1500 L / ha to 5000 L / ha, 5000 L / ha to 10,000 L / ha, 10,000 L / ha to 30,000 L / ha, 30 L / ha to 40,000 L / ha, 40 L / ha to 50,000 L / ha, 50 L / ha to 60,000 L / ha, 60 L / ha to 80,000 L / ha, 80 L / ha to 100,000 L / ha, 90 L / ha to 150,000 L / ha, 100 L / ha to 20,000 L / ha, 150 L / ha to 20,000 L / ha, 150 L / ha to 30,000 L / ha, 150 L / ha to 5000 L / ha, 150 L / ha to 5000 L / ha, 150 L / ha to 20, ... The capacity may be from 1,000 L / hectare to 50,000 L / hectare, from 50,000 L / hectare to 100,000 L / hectare, from 100,000 L / hectare to 150,000 L / hectare, from 150,000 L / hectare to 200,000 L / hectare, from 200,000 L / hectare to 500,000 L / hectare, or from 500,000 L / hectare to 10,000,000 L / hectare. Specific examples of the application rate of the composition of the present invention include, for example, a liquid composition of the present invention (for example, a liquid composition of the present invention containing the active ingredient at a use concentration such as those exemplified above) of 100 L / ha to 1,000,000 L / ha, 200 L / ha to 1,000,000 L / ha, 500 L / ha to 1,000,000 L / ha, 1000 L / ha to 750,000 L / ha, 10,000 L / ha to 750,000 L / ha, or 100,000 L / ha to 750,000 L / ha.

[0127] Furthermore, the application rate of the composition of the present invention can be determined taking into consideration not only the application area (two-dimensional factors) but also three-dimensional factors. That is, the application rate of the composition of the present invention can be determined, for example, depending on the height of the plants to which the composition of the present invention is applied (e.g., sprayed). Specifically, the application rate of the composition of the present invention in liquid form (e.g., a liquid composition of the present invention containing the active ingredient at a use concentration as exemplified above) for plants from ground level to knee height may be 1,000 L / ha to 750,000 L / ha, 1,000 L / ha to 30,000 L / ha, 1,000 L / ha to 5,000 L / ha, or 1,000 L / ha to 1,500 L / ha. Specifically, the application rate of the composition of the present invention may be, for example, as the application rate of the composition of the present invention in liquid form (for example, the composition of the present invention in liquid form containing the active ingredient at the use concentration as exemplified above), for plants of knee height to human height, 1500 L / ha to 750,000 L / ha, 1500 L / ha to 70,000 L / ha, 1500 L / ha to 10,000 L / ha, or 1500 L / ha to 3000 L / ha. Specifically, the application rate of the composition of the present invention may be, for example, as the application rate of the composition of the present invention in liquid form (for example, a liquid composition of the present invention containing the active ingredient at a use concentration as exemplified above), for plants having a height of a human to 2 meters, from 3,000 L / ha to 750,000 L / ha, from 3,000 L / ha to 100,000 L / ha, from 3,000 L / ha to 30,000 L / ha, or from 3,000 L / ha to 5,000 L / ha. Specifically, the application rate of the composition of the present invention may be, for example, as the application rate of the composition of the present invention in liquid form (for example, a composition of the present invention in liquid form containing the active ingredient at the use concentration as exemplified above), for plants of 2 meters or more, 5,000 L / ha to 750,000 L / ha, 5,000 L / ha to 150,000 L / ha, 5,000 L / ha to 30,000 L / ha, or 5,000 L / ha to 7,000 L / ha.

[0128] When the composition of the present invention is applied to a growing medium (for example, by irrigation to the ground surface), the application rate of the composition of the present invention may be, for example, 250,000 L / ha to 750,000 L / ha as the application rate of the composition of the present invention in liquid form (for example, the composition of the present invention in liquid form containing the active ingredient at the use concentration as exemplified above).

[0129] The composition of the present invention can be applied only once, or can be applied in multiple portions.The composition of the present invention can be applied in multiple portions, for example, two or more, three or more, five or more, or ten or more portions.When the composition of the present invention is applied in multiple portions, "application amount of the composition of the present invention" means the total application amount of the composition of the present invention by applying multiple portions.

[0130] The application amount of the composition of the present invention can be set, for example, so that the application amount of the active ingredient falls within a predetermined range.

[0131] The application rate of the active ingredient may be, for example, 1 mmol / ha or more, 2 mmol / ha or more, 5 mmol / ha or more, 10 mmol / ha or more, 20 mmol / ha or more, 50 mmol / ha or more, 100 mmol / ha or more, 200 mmol / ha or more, 500 mmol / ha or more, 1 mol / ha or more, 2 mol / ha or more, 5 mol / ha or more, 10 mol / ha or more, 20 mol / ha or more, 50 mol / ha or more, 100 mol / ha or more, 200 mol / ha or more, 500 mol / ha or more, 1,000 mol / ha or more, 2,000 mol / ha or more, 5,000 mol / hectare or more, 10,000 mol / hectare or more, 20,000 mol / hectare or more, 50,000 mol / hectare or more, 100,000 mol / hectare or more, 150,000 mol / hectare or more, or 200,000 mol / hectare or more, and may be 250,000 mol / hectare or less, 200,000 mol / hectare or less, 150,000 mol / hectare or less, 100,000 mol / hectare or less, 50,000 mol / hectare or less, 20,000 mol / hectare or less, 10,000 mol / hectare or less, 5,000 mol / hectare or less, 2,000 mol / hectare or less, 1,000 mol / hectare or less, 500 mol / hectare or less, 200 mol / hectare or less, 100 mol / hectare or less, 50 mol / hectare or less, 20 mol / hectare or less, 10 mol / hectare or less, 5 mol / hectare or less, 2 mol / hectare or less, 1 mol / hectare or less, 500 mmol / hectare or less, 200 mmol / hectare or less, 100 mmol / hectare or less, 50 mmol / hectare or less, 20 mmol / hectare or less, 10 mmol / hectare or less, 5 mmol / hectare or less, or 2 mmol / hectare or less, or any compatible combination thereof.Specific examples of the application rate of the active ingredient include 1 mmol / ha to 2 mmol / ha, 2 mmol / ha to 5 mmol / ha, 5 mmol / ha to 10 mmol / ha, 10 mmol / ha to 20 mmol / ha, 20 mmol / ha to 50 mmol / ha, 50 mmol / ha to 100 mmol / ha, 100 mmol / ha to 200 mmol / ha, 200 mmol / ha to 500 mmol / ha, 500 mmol / ha to 1 mol / ha, 1 mol / ha to 2 mol / ha, 2 mol / ha to 5 mol / ha, 5 mol / ha to 10 mol / ha, and 10 mol / ha to 20 mol / hectare, 20 mol / hectare to 50 mol / hectare, 50 mol / hectare to 100 mol / hectare, 100 mol / hectare to 200 mol / hectare, 200 mol / hectare to 500 mol / hectare, 500 mol / hectare to 1,000 mol / hectare, 1,000 mol / hectare to 2,000 mol / hectare, 2,000 mol / hectare to 5,000 mol / hectare, 5,000 mol / hectare to 10,000 mol / hectare, 10,000 mol / hectare to 20,000 mol / hectare, 20,000 mol / hectare to 50,000 mol / hectare, 50,000 mol / hectare to 100,000 mol / hectare, 100,000 mol / hectare to 150,000 mol / hectare, 150,000 mol / hectare to 200,000 mol / hectare, or 200,000 mol / hectare to 250,000 mol / hectare. When the composition of the present invention is applied in multiple applications, the "application amount of the active ingredient" refers to the total application amount of the active ingredient over the multiple applications.

[0132] The above-mentioned description of the application mode of the composition of the present invention can be applied mutatis mutandis to any other case in which an active ingredient is applied to a plant. That is, the active ingredient may be applied to a plant, for example, at a use concentration such as those exemplified above. Also, the active ingredient may be applied to a plant, for example, at an application rate of the active ingredient such as those exemplified above. Also, the active ingredient may be prepared as a composition, such as a liquid composition, containing the active ingredient and applied to a plant. The description of the composition of the present invention can be applied mutatis mutandis to a composition containing an active ingredient. The active ingredient can be applied to a plant, particularly in the form of a liquid. That is, the active ingredient may be specifically prepared as a liquid composition containing the active ingredient at a use concentration such as those exemplified above and applied to a plant. Also, the active ingredient may be used in combination with other ingredients, such as a spreading agent.

[0133] Note that a plant (specifically, a plant body) can be obtained by cultivating a plant using the method of the present invention. Therefore, one embodiment of the method of the present invention may be a method for producing a plant (specifically, a plant body). More specifically, one embodiment of the method of the present invention may be a method for producing a plant (specifically, a plant body) that includes applying an active ingredient (i.e., the above-mentioned component (A)) to a plant and cultivating the plant. The plant cultivation can be carried out, for example, by the same method as a conventional method for cultivating a plant, except for applying the active ingredient to the plant. The plant cultivation method is as described above. The application of the active ingredient and the cultivation of the plant may be carried out, for example, so as to obtain the desired effect of the application of the active ingredient. For example, the active ingredient may be applied during the cultivation of the plant, or the cultivation of the plant may be carried out after the application of the active ingredient. The application of the active ingredient may be carried out, in particular, during the cultivation of the plant. Specifically, for example, by applying an active ingredient to a plant and cultivating the plant, an effect of inducing insect resistance, an effect of inducing pest repellency, an effect of preventing insect damage, an effect of improving cultivation performance, and / or an effect of improving quality may be obtained, thereby efficiently producing a plant (specifically, a plant body). The plant (specifically, a plant body) may be harvested as appropriate. That is, the method of the present invention may further include harvesting the plant (specifically, a plant body). "Harvesting" may be used interchangeably with "recovery." "Harvesting or recovering a plant" may be used interchangeably with "harvesting or recovering a plant body." The plant (specifically, a plant body) to be harvested may be the whole plant body or a part of the plant body. Examples of parts of the plant body include leaves, stems, trunks, roots, flowers, fruits, and seeds.

[0134] <4> Use of Active Ingredient The present invention also discloses the use of the active ingredient in the above-exemplified applications. That is, the present invention discloses, for example, the use of the active ingredient for inducing insect resistance in plants, inducing pest repellency in plants, preventing insect damage in plants, improving plant cultivation performance, and / or improving plant quality, and the use of the active ingredient in the production of a composition for inducing insect resistance in plants, inducing pest repellency in plants, preventing insect damage in plants, improving plant cultivation performance, and / or improving plant quality.

[0135] The present invention also discloses active ingredients for use in the above-exemplified applications. That is, the present invention discloses active ingredients for use, for example, in inducing insect resistance in plants, inducing pest repellency in plants, preventing insect damage in plants, improving plant cultivation performance, and / or improving plant quality, and active ingredients for use in producing compositions for inducing insect resistance in plants, inducing pest repellency in plants, preventing insect damage in plants, improving plant cultivation performance, and / or improving plant quality.

[0136] Synthesis Example Compounds 1 to 23 and Mixture 2 were obtained by the following methods. The structures of Compounds 1 to 23 and the structures of the compounds contained in Mixture 2 are shown in the following formulas (Compound 1) to (Compound 23) and (Mixture 2), respectively.

[0137] (Synthesis Example 1) Synthesis of Compound 1 Glutamic acid (325 mg, 2.21 mmol) was dissolved in 2N aqueous sodium hydroxide solution (4 mL), and isopropanol (2 mL) was added. Then, under ice cooling, hexanoyl chloride (400 μL, 2.00 mmol) was added dropwise in small portions. After stirring at the same temperature for 1 hour, 2N hydrochloric acid (5 mL) was added to the reaction solution. Water was further added, and the mixture was subjected to distribution washing with n-hexane. The aqueous layer was subjected to distribution extraction with ethyl acetate, and the organic layer was dehydrated and dried over anhydrous sodium sulfate and then concentrated to dryness under reduced pressure to obtain Compound 1. Yield 32%; ESI MS m / z 246.0 (M+H)+; 1H NMR (400 MHz, CD3OD)δ4.33 (1H, dd, J=4.8, 9.2 Hz), 2.32-2.28 (2H, m), 2.20-2.06 (3H, m), 1.84 (1H, m), 1.53-1.51 (2H, m), 1.25-1.22 (4H, m), 0.82 (3H, t, J=6.8 Hz).

[0138]

[0139] (Synthesis Example 2) Synthesis of Compound 2 (Step 1) Synthesis of Intermediate 1 HOAt (144 mg, 1.06 mmol) and WSC·HCl (202 mg, 1.05 mmol) were added to a solution of heptanoic acid (135 mg, 1.04 mmol) in acetonitrile (10 mL), and the mixture was stirred at room temperature for 1 hour. To the reaction solution, glutamic acid dimethyl ester hydrochloride (225 mg, 1.06 mmol) and then triethylamine (150 μL, 1.08 mmol) were added, and the mixture was stirred for an additional 3 hours. After the reaction solution was concentrated under reduced pressure, ethyl acetate was added, and the mixture was partitioned and washed sequentially with 10% aqueous citric acid and saturated aqueous sodium bicarbonate. The organic layer was dehydrated and dried over anhydrous sodium sulfate, then concentrated to dryness under reduced pressure to obtain Intermediate 1. Yield 81%; ESI MS m / z 288.1 (M+H)+; 1H NMR (400 MHz, CDCl3)δ6.16 (1H, brd, J=7.6 Hz), 4.66 (1H, m), 3.77 (3H, s), 3.70 (3H, s), 2.42 (1H, m), 2.25-2.21 (3H, m), 2.02 (1H, m), 1.66-1.61 (3H, m), 1.36-1.29 (6H, m), 0.90 (3H, t, J=6.8 Hz).

[0140]

[0141] (Step 2) Synthesis of Compound 2 To a methanol solution (2 mL) of intermediate 1 (285 mg, 0.99 mmol), 2N aqueous sodium hydroxide solution (1.5 mL) was added and stirred at room temperature for 2 hours. 2N hydrochloric acid and then water were added to the reaction solution, followed by partition extraction with ethyl acetate. The organic layer was dehydrated and dried over anhydrous sodium sulfate, and then concentrated to dryness under reduced pressure to obtain Compound 2. Yield 81%; ESI MS m / z 260.1 (M+H)+; 1H NMR (400 MHz, CD3OD)δ4.34 (1H, dd, J=4.8, 9.2 Hz), 2.32-2.28 (2H, m), 2.17-2.05 (3H, m), 1.85 (1H, m), 1.54-1.50 (2H, m), 1.27-1.19 (6H, m), 0.81 (3H, t, J=6.8 Hz).

[0142]

[0143] (Synthesis Example 3) Synthesis of Compound 3 Compound 3 was obtained using glutamic acid and octanoyl chloride as starting materials in the same manner as in "Synthesis of Compound 1" in Synthesis Example 1. Yield: 71%; ESI MS m / z 274.1 (M+H)+; H NMR (400 MHz, CDOD) δ 4.45 (H, dd, J = 4.8, 9.2 Hz), 2.44-2.40 (2H, m), 2.26 (2H, t, J = 7.6 Hz), 2.21 (H, m), 1.96 (H, m), 1.66-1.62 (2H, m), 1.38-1.32 (8H, m), 0.92 (3H, t, J = 6.8 Hz).

[0144]

[0145] (Synthesis Example 4) Synthesis of Compound 4 Compound 4 was obtained using glutamic acid and decanoyl chloride as starting materials in the same manner as in "Synthesis of Compound 1" in Synthesis Example 1. Yield: 76%; ESI MS m / z 302.1 (M+H)+; H NMR (400 MHz, CDOD) δ 4.45 (H, dd, J = 4.8, 9.2 Hz), 2.44-2.40 (2H, m), 2.26 (2H, t, J = 7.6 Hz), 2.19 (H, m), 1.96 (H, m), 1.66-1.62 (2H, m), 1.37-1.31 (12H, m), 0.92 (3H, t, J = 6.8 Hz).

[0146]

[0147] (Synthesis Example 5) Synthesis of Compound 5 (Step 1) Synthesis of Intermediate 2 Intermediate 2 was obtained using undecanoic acid and glutamic acid dimethyl ester hydrochloride as starting materials in the same manner as in "Synthesis of Intermediate 1" in Synthesis Example 2. Yield 68%; ESI MS m / z 344.2 (M+H)+; 1H NMR (400 MHz, CDCl3)δ6.16 (1H, brd, J=8.0 Hz), 4.66 (1H, m), 3.77 (3H, s), 3.70 (3H, s), 2.41 (1H, m), 2.26-2.21 (3H, m), 2.03 (1H, m), 1.66-1.63 (3H, m), 1.32-1.28 (14H, m), 0.90 (3H, t, J=6.8 Hz).

[0148]

[0149] (Step 2) Synthesis of Compound 5 Compound 5 was obtained using Intermediate 2 as a starting material in the same manner as in "Synthesis of Compound 2" in Synthesis Example 2. Yield: 65%; ESI MS m / z 316.1 (M+H)+; H NMR (400 MHz, CDOD) δ 4.33 (H, dd, J = 4.8, 9.2 Hz), 2.30 (H, t, J = 7.6 Hz), 2.16-2.06 (H, m), 1.83 (H, m), 1.54-1.50 (H, m), 1.27-1.19 (H, m), 0.80 (H, t, J = 6.8 Hz).

[0150]

[0151] Synthesis Example 6 Synthesis of Compound 12 Compound 12 was synthesized using glutamic acid dimethyl ester hydrochloride and decanoyl chloride as starting materials in the same manner as in "Synthesis of Compound 1" in Synthesis Example 1. Yield 76%; ESI MS m / z 330.2 (M+H)+; 1H NMR (400 MHz, CD3OD)δ4.46 (1H, dd, J=5.2, 9.2 Hz), 3.73 (3H, s), 3.68 (3H, s), 2.44 (2H, t, J=7.6 Hz), 2.25 (2H, t, J=7.6 Hz), 2.18 (1H, m), 1.95 (1H, m), 1.65-1.61 (2H, m), 1.35-1.31 (12H, m), 0.92 (3H, t, J=7.2 Hz).

[0152]

[0153] (Synthesis Example 7) Synthesis of Compound 13 Compound 13 was synthesized using glutamine and decanoyl chloride as starting materials in the same manner as in "Synthesis of Compound 1" in Synthesis Example 1. Yield: 34%; ESI MS m / z 301.1 (M+H)+; H NMR (400 MHz, CDOD) δ 4.40 (H, dd, J = 4.8, 9.2 Hz), 2.35-2.14 (5H, m), 1.96 (H, m), 1.66-1.62 (2H, m), 1.36-1.31 (12H, m), 0.92 (H, t, J = 6.8 Hz).

[0154]

[0155] Synthesis Example 8: Synthesis of Compound 14: Decanoyl chloride (0.1 mL, 0.49 mmol) was added dropwise to a solution of acetonitrile (2 mL) containing water (0.4 mL) under ice cooling. After stirring at the same temperature for 1 hour, ethyl acetate was added to the reaction mixture. The organic layer was partitioned and washed with 1N hydrochloric acid and saturated aqueous sodium bicarbonate, dehydrated over anhydrous sodium sulfate, and then concentrated to dryness under reduced pressure. The resulting residue was purified by reverse-phase HPLC to obtain Compound 14. Yield: 92%; 1H NMR (400 MHz, CDCl3) δ 2.29 (2H, t, J = 7.6 Hz), 1.64-1.60 (2H, m), 1.35-1.32 (12H, m), 0.92 (3H, t, J = 6.8 Hz).

[0156]

[0157] (Synthesis Example 9) Synthesis of Compound 15 Using methanol and decanoyl chloride as starting materials, compound 15 was obtained by the same method as in "Synthesis of Compound 14" in Synthesis Example 8. Yield 92%; H NMR (400 MHz, CDOD) δ 3.67 (3H, s), 2.33 (2H, t, J = 7.6 Hz), 1.64-1.61 (2H, m), 1.32-1.24 (12H, m), 0.92 (3H, t, J = 6.8 Hz).

[0158]

[0159] (Synthesis Example 10) Synthesis of Compound 17 Compound 17 was synthesized using sarcosine and decanoyl chloride as starting materials in the same manner as in "Synthesis of Compound 1" in Synthesis Example 1. Yield: 91%; ESI MS m / z 244.1 (M+H)+; H NMR (400 MHz, CDOD) δ 4.18 (0.65H, s), 4.11 (1.35H, s), 3.13 (2H, s), 2.96 (1H, s), 2.44 (1.35H, t, J=7.6 Hz), 2.31 (0.65H, t, J=7.6 Hz), 1.65-1.60 (2H, m), 1.38-1.31 (12H, m), 0.94-0.90 (3H, m).

[0160]

[0161] (Synthesis Example 11) Synthesis of Compound 18 (Step 1) Synthesis of Intermediate 3 Intermediate 3 was obtained using trans-2-decenoic acid and glutamic acid dimethyl ester hydrochloride as starting materials in the same manner as in "Synthesis of Intermediate 1" in Synthesis Example 2. Yield 90%; ESI MS m / z 328.1 (M+H)+; 1H NMR (400 MHz, CDCl3)δ6.83 (1H, m), 6.41 (1H, d, J=7.6 Hz), 5.81 (1H, d, J=15.2 Hz), 4.68 (1H, m), 3.73 (3H, s), 3.64 (3H, s), 2.45-2.33 (2H, m), 2.22-2.12 (3H, m), 2.01 (1H, m), 1.43-1.38 (2H, m), 1.28-1.24 (8H, m), 0.85 (3H, t, J=6.8 Hz).

[0162]

[0163] (Step 2) Synthesis of Compound 18 Compound 18 was obtained using Intermediate 3 as a starting material in the same manner as in "Synthesis of Compound 2" in Synthesis Example 2. Yield: 97%; ESI MS m / z 300.1 (M+H)+; H NMR (400 MHz, CDOD) δ 6.83 (1H, m), 6.02 (1H, d, J = 15.6 Hz), 4.52 (1H, dd, J = 4.8, 8.8 Hz), 2.45-2.40 (2H, m), 2.26-2.19 (3H, m), 1.99 (1H, m), 1.51-1.48 (2H, m), 1.39-1.32 (8H, m), 0.92 (3H, t, J = 6.8 Hz).

[0164]

[0165] (Synthesis Example 12) Synthesis of Compound 19 (Step 1) Synthesis of Intermediate 4 Intermediate 4 was obtained using 9-decenoic acid and glutamic acid dimethyl ester hydrochloride as starting materials in the same manner as in "Synthesis of Intermediate 1" in Synthesis Example 2. Yield 89%; ESI MS m / z 328.1 (M+H)+; 1H NMR (400 MHz, CDCl3)δ6.37 (1H, d, J=7.6 Hz), 5.76 (1H, m), 4.97-4.87 (2H, m), 4.60 (1H, m), 3.71 (3H, s), 3.64 (3H, s), 2.44-2.28 (2H, m), 2.20-2.14 (3H, m), 2.02-1.93 (3H, m), 1.61-1.57 (2H, m), 1.35-1.27 (8H, m).

[0166]

[0167] (Step 2) Synthesis of Compound 19 Compound 19 was obtained using Intermediate 4 as the starting material in the same manner as in "Synthesis of Compound 2" in Synthesis Example 2. Yield: 92%; ESI MS m / z 300.1 (M+H)+; H NMR (400 MHz, CDOD) δ 5.82 (1H, m), 5.02-4.91 (2H, m), 4.45 (1H, dd, J=5.2, 9.2 Hz), 2.44-2.40 (2H, m), 2.30-2.15 (3H, m), 2.09-2.03 (2H, m), 1.96 (1H, m), 1.66-1.62 (2H, m), 1.43-1.32 (8H, m).

[0168]

[0169] Synthesis Example 13 Synthesis of Compound 20 Compound 20 was synthesized using γ-glutamylvaline and decanoyl chloride as starting materials in the same manner as in “Synthesis of Compound 1” in Synthesis Example 1. Yield 24%; ESI MS m / z 401.2 (M+H)+; 1H NMR (400 MHz, CD3OD)δ4.40 (1H, dd, J=4.8, 9.2 Hz), 4.35 (1H, d, J=5.6 Hz), 2.43-2.39 (2H, m), 2.29-2.16 (4H, m), 1.98 (1H, m), 1.66-1.62 (2H, m), 1.36-1.32 (12H, m), 0.994 (3H, d, J=6.8 Hz), 0.986 (3H, d, J=7.2 Hz), 0.92 (3H, t, J=6.8 Hz).

[0170]

[0171] (Synthesis Example 14) Synthesis of Compound 21 (Step 1) Synthesis of Intermediate 5 Using 3-phenylpropionic acid and glutamic acid dimethyl ester hydrochloride as starting materials, intermediate 5 was obtained by the same method as in "Synthesis of Intermediate 1" in Synthesis Example 2. Yield: 85%; ESI MS m / z 308.1 (M+H)+; 1H NMR (400 MHz, CDCl3) δ 7.32-7.21 (5H, m), 6.13 (1H, brd, J=7.6 Hz), 4.63 (1H, m), 3.75 (3H, s), 3.69 (3H, s), 3.01-2.96 (2H, m), 2.62-2.50 (2H, m), 2.36-2.14 (3H, m), 1.96 (1H, m).

[0172]

[0173] (Step 2) Synthesis of Compound 21 Compound 21 was obtained using Intermediate 5 as a starting material in the same manner as in "Synthesis of Compound 2" in Synthesis Example 2. Yield: 93%; ESI MS m / z 280.0 (M+H)+; H NMR (400 MHz, CDOD)δ 7.30-7.16 (5H, m), 4.43 (1H, dd, J=4.8, 13.2 Hz), 2.96-2.92 (2H, m), 2.58-2.54 (2H, m), 2.29-2.25 (2H, m), 2.14 (1H, m), 1.88 (1H, m).

[0174]

[0175] (Synthesis Example 15) Synthesis of Compound 22 (Step 1) Synthesis of Intermediate 6 Intermediate 6 was obtained using 8-methylnonanoic acid and glutamic acid dimethyl ester hydrochloride as starting materials in the same manner as in "Synthesis of Intermediate 1" in Synthesis Example 2. Yield 83%; ESI MS m / z 330.2 (M+H)+; 1H NMR (400 MHz, CDCl3)δ6.31 (1H, brd, J=7.6 Hz), 4.62 (1H, m), 3.73 (3H, s), 3.66 (3H, s), 2.42-2.35 (2H, m), 2.22-2.18 (3H, m), 1.99 (1H, m), 1.63-1.57 (2H, m), 1.49 (1H, m), 1.30-1.23 (6H, m), 1.14-1.11 (2H, m), 0.84 (6H, d, J=6.8 Hz).

[0176]

[0177] (Step 2) Synthesis of Compound 22 Compound 22 was obtained from Intermediate 6 by the same method as in "Synthesis of Compound 2" in Synthesis Example 2. Yield: 97%; ESI MS m / z 302.1 (M+H)+; H NMR (400 MHz, CDOD)δ 4.33 (H, dd, J = 5.2, 13.2 Hz), 2.32-2.28 (2H, m), 2.15 (2H, t, J = 7.6 Hz), 2.07 (H, m), 1.84 (H, m), 1.54-1.40 (3H, m), 1.25-1.19 (6H, m), 1.11-1.08 (2H, m), 0.78 (6H, d, J = 6.4 Hz).

[0178]

[0179] (Synthesis Example 16) Synthesis of Compound 23 Compound 23 was obtained using ethanolamine and decanoyl chloride as starting materials in the same manner as in "Synthesis of Compound 1" in Synthesis Example 1. Yield: 96%; ESI MS m / z 216.1 (M+H)+; H NMR (400 MHz, CDOD) δ 3.60 (H, t, J = 5.6 Hz), 3.31-3.29 (2H, m), 2.21 (2H, t, J = 7.6 Hz), 1.64-1.60 (2H, m), 1.35-1.32 (12H, m), 0.92 (3H, t, J = 6.8 Hz).

[0180]

[0181] (Synthesis Example 17) Synthesis of Mixture 2 Mixture 2 was obtained using threonine and coconut oil-derived fatty acid chloride as raw materials in the same manner as in "Synthesis of Compound 1" in Synthesis Example 1.

[0182]

[0183] In the formula (mixture 2), R ２ represents the alkyl group of the residue of a fatty acid derived from coconut oil, and mixture 2 is ２ is a mixture containing compounds in which each of the alkyl groups of the residues of fatty acids derived from multiple types of coconut oil having different carbon numbers (for example, linear alkyl groups having 7, 9 to 11, etc. carbon atoms).

[0184] (Other) Obtaining Compounds 6-11 and 16, and Mixtures 1 and 3 Compounds 6-11 and Mixtures 1 and 3 were purchased from Ajinomoto Co., Inc. Compound 7 is commercially available under the trade name Amisoft® MS-11, compound 8 is commercially available under the trade name Amisoft® MK-11, compound 9 is commercially available under the trade name Amisoft® GS-11P, compound 10 is commercially available under the trade name Amisoft® HS-11P, mix 1 is commercially available under the trade name Amisoft® CS-22, and mix 3 is commercially available under the trade name Amirite® ET-CS-12 (all manufactured by Ajinomoto Co., Inc.). Mixture 3 is a mixture containing a compound represented by the following formula (Mixture 1) and a compound represented by the formula (Mixture 2) described below. Compound 16 was purchased from Tokyo Chemical Industry Co., Ltd. Compound 16 is commercially available under the trade name Decanal (manufactured by Tokyo Chemical Industry Co., Ltd.).

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193] In the formula (mixture 1), R ２ represents the alkyl group of the residue of a fatty acid derived from coconut oil, and Mixture 1 is ２ is a mixture containing compounds in which each of the alkyl groups of the residues of fatty acids derived from multiple types of coconut oil having different carbon numbers (for example, linear alkyl groups having 7, 9 to 11, etc. carbon atoms).

[0194] The present invention will now be described in more detail with reference to the following non-limiting examples.

[0195] (Example 1) Effects of various compounds on Ca in Arabidopsis thaliana 2+ In this example, the Ca induced by contact of Compounds 1 to 23 or Mixtures 1 to 3 with the glutamate receptor of Arabidopsis thaliana was measured. 2+ signal, Ca 2+ The calcium-sensitive fluorescent protein GCaMP3 was introduced into Arabidopsis thaliana recombinant p35S::GCaMP3, and the intracellular calcium levels were visualized by fluorescence. 2+ Changes in the concentration of GCaMP3 were detected as fluorescence intensity, and the Ca concentration in the test plant and surrounding plants was measured. 2+ Signal transduction was analyzed in real time.

[0196] Ca 2+ A real-time imaging assay of the signal was carried out as follows.

[0197] The plant material used was a 2-week-old Arabidopsis thaliana recombinant p35S::GCaMP3 grown on sterile agar medium [1× MS salts, 1% (w / v) sucrose, 0.01% (w / v) myoinositol, 0.05% (w / v) MES, and 0.4% (w / v) gellan gum; pH 5.8 adjusted with KOH]. The plant was placed under a fluorescence microscope SMZ25 (Nikon Solutions Corporation), and 3 μL of compound solution was applied to the junction of the base of the first leaf blade with the petiole. The Ca2+ produced was measured. 2+Signals were evaluated by real-time microscopic imaging using ORCA-Flash 4.0 V2 (Hamamatsu Photonics). Compounds 1–23, mixtures 1–3, and the negative control were each diluted to 100 mM using a dilution medium [1× MS salts, 1% (w / v) sucrose, 0.01% (w / v) myoinositol, and 0.05% (w / v) MES; pH 5.8 adjusted with KOH]. However, because compounds 12–20 have low solubility in water, they were each prepared using the same dilution medium containing 50% DMSO. Some compound solutions were also prepared at multiple concentrations to explore the optimal concentration range. Ca was used as a negative control. 2+ Sorbitol, which does not produce a signal, was used. When each compound was applied to the plant material, no operations that would cause injury to the plant material (for example, cutting the leaves of the plant material) were performed. Ca was also detected in surrounding plants that were not physically in contact with the plant to which the compound or mixture was applied. 2+ Compounds for which a signal was observed were classified as Ca 2+ It was determined to be a signal-inducing compound.

[0198] The results are shown in Tables 1 and 2. In Tables 1 and 2, "Ca 2+ Regarding the "signal" item, the Ca signal was measured in the test plant. 2+ Compounds for which a signal was observed are marked with a "○" and those for which a signal was observed are marked with a "○" 2+ Compounds that did not produce a signal were evaluated as "×." For the "transmissibility" item, compounds that did not produce a signal were evaluated as "×." 2+ Compounds for which signals were observed are marked with a circle. 2+ Compounds for which no signal was observed were rated "X".

[0199]

[0200]

[0201] As can be seen from Tables 1 and 2, when compounds 3 to 6, 12 to 16, 19, 20, and 23, and mixtures 1 to 3 were applied at 100 mM, Ca levels in the test plants and surrounding plants were significantly reduced. 2+Compounds 3 and 4 were applied at 50 mM, compound 6 at 1, 10, and 200 mM, compound 15 at 1, 5, 10, 25, 50, 75, and 2,340 mM, and mixture 1 at 0.5, 1, 10, 200, and 330 mM, and both compounds 3 and 4 induced Ca signaling in the test plants and surrounding plants. 2+ In particular, mixtures 1 and 2 induced a strong Ca signal. 2+ The application of compounds 3-6, 12-16, 19, 20, and 23, and mixtures 1-3 significantly increased Ca levels in the test plants and surrounding plants. 2+ Since the signal transduction was increased, it was suggested that these compounds have an insect pest resistance-inducing effect in the test plants and in the surrounding plants. ２ is an alkyl group having 2 carbon atoms (i.e., an ethyl group), and the hydrogen atom of the ethyl group is substituted with a phenyl group. Mixture 1 is a mixture of acyl glutamates having different numbers of carbon atoms, and R ２ The main component is acyl glutamate (compound 3) with seven carbon atoms, ２ Mixture 2 contains acyl glutamates (compounds 4 to 6) with carbon chains of 9 to 11. Mixture 2 is a mixture of acyl threonine salts with different carbon numbers, and Mixture 3 is a mixture of acyl glutamates and acyl threonine salts with different carbon numbers.

[0202] (Example 2) Effect of glutamic acid derivatives on the induction of insect resistance in practical crops In this example, the effect of Ca 2+Compound 1, which demonstrated a signal induction effect, was evaluated for its insect resistance induction effect in the leaves of food crops. Sorbitol was used as a negative control, and jasmomate solution (the active ingredient is prohydrojasmone; a typical damaging plant hormone), the only commercially available pest repellent that induces insect resistance, was used as a positive control. The test was conducted with 10 plants per test plot (2 planters, 5 plants per planter, no replicates), with the planters spaced at least 50 cm apart in each test plot.

[0203] The plant material used was komatsuna seedlings grown in a planter one month after sowing, and the test organisms were second- to third-instar early larvae of the common cutworm (Spodoptera litura). Mixture 1 was prepared using a 100 mM solution in distilled water. 100 mM sorbitol was used as the negative control. The positive control was prepared using a jasmomate solution diluted 500-fold (0.4 mM prohydrojasmone), the normally recommended application concentration, in distilled water. Mixture 1, the negative control, or the positive control was sprayed evenly over the entire plant in sufficient volume (approximately 30 mL) using a small hand sprayer. The plant material was not injured during spraying (e.g., by cutting the leaves).

[0204] One day after application, eight second- to third-instar Spodoptera litura larvae (80 larvae total per plot) were placed individually on each leaf. Surveys were conducted one day after application (just before release, for phytotoxicity surveys only), four days after application (three days after release), eight days after application (seven days after release), and 11 days after application (ten days after release). The surveys consisted of damage surveys and phytotoxicity surveys. Damage (feeding damage) on all plants in each plot was assessed using five levels: none, minimal, slight, medium, and heavy. The damage level was calculated using the following criteria: "none": no feeding damage observed; "minimal": slight feeding damage observed; "light": feeding damage on less than 10% of the leaf area; "medium": feeding damage on 11-30% of the leaf area; and "heavy": feeding damage on more than 31% of the leaf area. The damage level was calculated using the following formula:

[0205] Damage level = (number of plants with "light" damage + number of plants with "medium" damage x 3 + number of plants with "heavy" damage x 5) / (number of plants surveyed x 5) x 100

[0206] The phytotoxicity survey was carried out by visually observing the stems and leaves after spraying to determine whether or not symptoms of phytotoxicity were present, with a four-point scale.

[0207] The results are shown in Figure 1. The jasmomate-treated plot suffered the same degree of damage as the sorbitol-treated plot, meaning that jasmomate was not found to have any effect on inducing insect resistance. The Mixture 1-treated plot suffered less damage than the sorbitol-treated and jasmomate-treated plots, demonstrating its insect resistance induction effect. Furthermore, no phytotoxicity was observed in the Mixture 1-treated plot.

[0208] (Example 3) Evaluation of the effect of various compounds on the induction of insect resistance gene expression In this example, the Ca 2+ Compound 15 and Mixture 1, which showed a signal induction effect, were evaluated by qPCR to determine whether they induced the expression of insect resistance genes in plant leaves. Sorbitol was used as a negative control, and monosodium glutamate (MSG) was used as a positive control.

[0209] The AtJAZ5 and AtJAZ7 genes, which encode jasmonate azimuth domain (JAZ) family proteins involved in jasmonate signaling, were selected as insect resistance genes. The AtJAZ5 and AtJAZ7 proteins are regulators of defense responses in plants against insect and pathogen attack. The UBQ10 gene was selected as an internal control. Wild-type Arabidopsis Columbia-0 (Col-0) was used as the plant material.

[0210] Col-0 was incubated for 4 days on sterile agar medium [1 / 2× MS salts, 2% (w / v) sucrose, 0.05% (w / v) MES, 0.001% (v / v) vitamin solution, and 0.5% (w / v) gellan gum; pH 5.7 adjusted with KOH]. 4.5 mL of sterile liquid medium [1 / 2× MS salts, 2% (w / v) sucrose, 0.05% (w / v) MES, 0.001% (v / v) vitamin solution; pH 5.8 adjusted with KOH] and 4.5 μL of 10% (v / v) riboflavin were added to each well of a 6-well plate. After 4 days of incubation, four Col-0 plants were transplanted into each well with tweezers, taking care not to damage the plants, and then incubated overnight. Compound 15 and Mixture 1 were then added at a final concentration of 10 mM. After 48 hours, all four individuals from each well were harvested and frozen in liquid nitrogen. Total RNA was then extracted from 50–200 mg of frozen leaves using the Maxwell® RSC Plant RNA Kit (Promega) according to the manufacturer's instructions. Single-stranded cDNA was prepared using the extracted total RNA as a template and ReverTra Ace® qPCR RT Master Mix (Toyobo Co., Ltd.). A 10 μL reaction system was prepared by adding 100 ng of single-stranded cDNA equivalent to total RNA and primers at a final concentration of 250 nM to Fast SYBR Green Master Mix (Thermo Fisher Scientific). qPCR was performed using QuantStudio® 3 and QuantStudio® Design & Analysis Desktop Software (appliedbiosystems) under the following conditions: 95°C for 20 seconds; 95°C for 1 second, 60°C for 20 seconds, 40 cycles. Primers of SEQ ID NOs: 1 and 2 were used to evaluate the AtJAZ5 gene, primers of SEQ ID NOs: 3 and 4 were used to evaluate the AtJAZ7 gene, and primers of SEQ ID NOs: 5 and 6 were used to evaluate the UBQ10 gene.The relative expression levels of the AtJAZ5 and AtJAZ7 genes to the expression level of the UBQ10 gene (internal standard) were calculated using the ΔΔCt method. The experiment was repeated three times, and the average was calculated.

[0211] The relative expression levels of the AtJAZ5 gene and the AtJAZ7 gene are shown in Figure 2 and Figure 3, respectively. For both genes, Compound 15 and Mixture 1 showed expression-inducing effects equal to or greater than those of MSG.

[0212] (Example 4) Insect resistance induction effect of Mixture 1 in practical crops In this example, in Example 1, Ca 2+ Mixture 1, which was found to have signal induction activity, was evaluated in the leaves of food crops to see if it had the effect of inducing insect resistance.

[0213] The plant material used was komatsuna seedlings grown in a planter one and a half months after sowing, and the test organisms were early third-instar larvae of the common cutworm (Spodoptera Litura). Mixture 1 was prepared as a 100 mM solution using distilled water as the solvent (Mixture 1 solution). One plant was used in each test plot, and 10 test plots were set up, each for Mixture 1 treatment and Mixture 1 untreated.

[0214] A single leaf was harvested from each komatsuna seedling and a cork borer was used to create a 3 cm diameter leaf disk (a total of 10 leaf disks per plant). The leaf disks from the Mixture 1 treatment were immersed in Mixture 1 solution for 10 seconds, after which excess solution was removed and the disks were air-dried in a fume hood. One leaf disk each from the Mixture 1 treatment and Mixture 1 untreated sections was placed leaf-side up on a 9 cm diameter Petri dish lined with agar medium or moistened filter paper. One hour after placement, five Spodoptera litura larvae were released into the dish and maintained in an incubator (set at 25°C, 60% RH, 16L-8D).

[0215] Forty-eight hours after release, the degree of damage to each leaf disk was assessed and divided into five categories: none, slight, medium, heavy, and severe. The degree of damage was calculated. For plots where differences in the degree of damage were observed, the area of ​​damage was calculated using image analysis software (Image J). Damage was classified as "none," meaning no damage at all; "light," meaning damage to less than 25% of the leaf area; "medium," meaning damage to 26-50% of the leaf area; "heavy," meaning damage to 51-75% of the leaf area; and "severe," meaning damage to more than 76% of the leaf area. The degree of damage was calculated using the following formula:

[0216] Damage level = (number of leaves with "light" damage level + number of leaves with "medium" damage level x 2 + number of leaves with "heavy" damage level x 3 + number of leaves with "severe" damage level x 4) / (number of leaves surveyed x 4) x 100

[0217] The results are shown in Figure 3. The damage level in the Mixture 1-treated plot was clearly lower than in the Mixture 1-untreated plot, demonstrating the effect of inducing insect resistance.

[0218] According to the present invention, useful results can be obtained in the agricultural and horticultural fields, such as preventing insect damage to plants.

Claims

1. A composition for inducing insect resistance in plants or for preventing insect damage in plants, comprising the following component (A): (A) a compound represented by the following general formula (I): [In formula (I), R １ represents a hydrogen atom (H), a hydroxyl group, an amino group, an optionally substituted alkyl group, an optionally substituted alkylamino group, an optionally substituted alkoxy group, agmatine, glycerol, glucose, an amino acid, a dipeptide, or a tripeptide; R ２ represents an optionally substituted alkyl group having 7 to 10 carbon atoms, or an optionally substituted alkenyl group having 7 to 10 carbon atoms.

2. R ２ The composition according to claim 1, wherein is an alkyl group having 7 to 10 carbon atoms or an alkenyl group having 7 to 10 carbon atoms.

3. The composition according to claim 1, wherein the component (A) is selected from the group consisting of compounds that satisfy any of the following conditions: (1) R １ is a hydroxyl group, R ２ is an alkyl group having 7 to 10 carbon atoms; (2) R １ is an alkylamino group substituted with a hydroxyl group, R ２ is an alkyl group having 7 to 10 carbon atoms; (3) R １ is an alkoxy group, R ２ is an alkyl group having 7 to 10 carbon atoms; (4) R １ is an amino acid, R ２ is an alkyl group having 7 to 10 carbon atoms; (5) R １ is an amino acid, R ２ is an alkenyl group having 7 to 10 carbon atoms; and (6) R １ is a dipeptide, R ２ is an alkyl group having 7 to 10 carbon atoms.

4. The composition according to claim 1, wherein component (A) is selected from the group consisting of compounds represented by the following formulas (Compound 3) to (Compound 6), (Compound 12) to (Compound 16), (Compound 19), (Compound 20), and (Compound 23):

5. The composition according to claim 1, wherein component (A) is one or both of a mixture represented by the following formula (Mixture 1) and a mixture represented by the following formula (Mixture 2). [In formula (mixture 1), R ２ represents an alkyl group of a residue of a fatty acid derived from coconut oil having 7 to 10 carbon atoms, and mixture 1 is ２ is an alkyl group of a residue of a fatty acid derived from multiple types of palm oil having 7 to 10 carbon atoms.] [In formula (mixture 2), R ２ represents an alkyl group of a residue of a fatty acid derived from coconut oil having 7 to 10 carbon atoms, and mixture 2 is represented by R ２ is an alkyl group of a residue of a fatty acid derived from multiple types of palm oil having 7 to 10 carbon atoms.] 6. The composition according to claim 1, wherein the insect pest is caused by an organism classified in the order Lepidoptera, Hemiptera, Coleoptera, Diptera, Orthoptera, Thysanoptera, Tylenchida, Collembola, Acarina, or Stylommatophora.

7. The insect pest is one of the following families: Plutellidae, Noctuidae, Pyralidae, Tortricidae, Leafminer, Boneworm, Gelechiidae, Crambidae, Arctiidae, Lymantriidae, Leafhoppers, Delphacidae, Psyllidae, Aphididae, Aleyrodidae, Coccinellidae, Tingidae, Hemiptera, Lygaeidae, Scarabaeidae, Elateridae, Coccinellidae, Cerambycidae, Chrysomelidae, Curculionidae, Muscidae, and Calliphoridae.

2. The composition of claim 1, wherein the insect pest is caused by an organism classified in the following families: Sarcophagidae, Anthomyiidae, Tephritidae, Euloidea, Chloropidae, Acrididae, Locustidae, Scyllidae, Thripidae, Thripidae, Thripidae, Aphelenchoidae, Neotylenchidae, Pyrrhocoridae, Pyrrhocoridae, Tetranychidae, Miteidae, Astigmatidae, Sarcoptidae, Slugidae, or Scyllidae.

8. The composition according to any one of claims 1 to 7, wherein the plant is a grass, a solanaceae, a cucurbit, a legume, a cruciferous, a rose, a mulberry, a mallow, a pipal, a lily, a aster, a amaranth, a rhododendron, a vitiaceae, a citrus, a rubiaceae, a oleaceae, a laurel, a anacardiaceae, a Sapindaceae, or a mint family plant.

9. A method for inducing insect resistance in a plant, comprising applying the following component (A) to the plant: (A) a compound represented by the following general formula (I): [In formula (I), R １ represents a hydrogen atom (H), a hydroxyl group, an amino group, an optionally substituted alkyl group, an optionally substituted alkylamino group, an optionally substituted alkoxy group, agmatine, glycerol, glucose, an amino acid, a dipeptide, or a tripeptide; R ２ represents an optionally substituted alkyl group having 7 to 10 carbon atoms, or an optionally substituted alkenyl group having 7 to 10 carbon atoms.

10. A method for preventing insect damage to plants, comprising applying the following component (A) to the plant: (A) a compound represented by the following general formula (I): [In formula (I), R １ represents a hydrogen atom (H), a hydroxyl group, an amino group, an optionally substituted alkyl group, an optionally substituted alkylamino group, an optionally substituted alkoxy group, agmatine, glycerol, glucose, an amino acid, a dipeptide, or a tripeptide; R ２ represents an optionally substituted alkyl group having 7 to 10 carbon atoms, or an optionally substituted alkenyl group having 7 to 10 carbon atoms.

11. A method for producing a plant, comprising applying the following component (A) to a plant and cultivating the plant: (A) a compound represented by the following general formula (I): [In formula (I), R １ represents a hydrogen atom (H), a hydroxyl group, an amino group, an optionally substituted alkyl group, an optionally substituted alkylamino group, an optionally substituted alkoxy group, agmatine, glycerol, glucose, an amino acid, a dipeptide, or a tripeptide; R ２ represents an optionally substituted alkyl group having 7 to 10 carbon atoms, or an optionally substituted alkenyl group having 7 to 10 carbon atoms.

12. R ２ The method according to any one of claims 9 to 11, wherein is an alkyl group having 7 to 10 carbon atoms or an alkenyl group having 7 to 10 carbon atoms.

13. The method according to any one of claims 9 to 11, wherein the component (A) is selected from the group consisting of compounds that satisfy any of the following conditions: (1) R １ is a hydroxyl group, R ２ is an alkyl group having 7 to 10 carbon atoms; (2) R １ is an alkylamino group substituted with a hydroxyl group, R ２ is an alkyl group having 7 to 10 carbon atoms; (3) R １ is an alkoxy group, R ２ is an alkyl group having 7 to 10 carbon atoms; (4) R １ is an amino acid, R ２ is an alkyl group having 7 to 10 carbon atoms; (5) R １ is an amino acid, R ２ is an alkenyl group having 7 to 10 carbon atoms; and (6) R １ is a dipeptide, R ２ is an alkyl group having 7 to 10 carbon atoms.

14. The method according to any one of claims 9 to 11, wherein component (A) is selected from the group consisting of compounds represented by the following formulas (Compound 3) to (Compound 6), (Compound 12) to (Compound 16), (Compound 19), (Compound 20), and (Compound 23):

15. The method according to any one of claims 9 to 11, wherein component (A) is one or both of a mixture represented by the following formula (Mixture 1) and a mixture represented by the following formula (Mixture 2): [In formula (mixture 1), R ２ represents an alkyl group of a residue of a fatty acid derived from coconut oil having 7 to 10 carbon atoms, and mixture 1 is ２ is an alkyl group of a residue of a fatty acid derived from multiple types of palm oil having 7 to 10 carbon atoms.] [In formula (mixture 2), R ２ represents an alkyl group of a residue of a fatty acid derived from coconut oil having 7 to 10 carbon atoms, and mixture 2 is represented by R ２ is an alkyl group of a residue of a fatty acid derived from multiple types of palm oil having 7 to 10 carbon atoms.] 16. The method according to any one of claims 9 to 11, wherein the insect damage is caused by organisms classified into the order Lepidoptera, Hemiptera, Coleoptera, Diptera, Orthoptera, Thysanoptera, Tylenchida, Collembola, Acarina, or Stylommatophora.

17. The insect pest is one of the following: Plutellidae, Noctuidae, Pyralidae, Tortricidae, Leafminer, Boneworm, Gelechiidae, Crambidae, Arctiidae, Lymantriidae, Leafhoppers, Delphacidae, Psyllidae, Aphididae, Aleyrodidae, Coccinellidae, Tingidae, Hemiptera, Lygaeidae, Scarabaeidae, Elateridae, Coccinellidae, Cerambycidae, Chrysomelidae, Curculionidae, Muscidae, Calliphoridae, and Flesh Bugs The method according to any one of claims 9 to 11, wherein the insect damage is caused by an organism classified into the following families: Ectogonidae, Anthomyiidae, Tephritidae, Euloidea, Chloropsoidea, Acrididae, Locustidae, Scytothripidae, Thripidae, Thripidae, Thripidae, Thripidae, Aphelencoidae, Neotylenchidae, Pyrrhocoridae, Pyrrhocoridae, Tetranychidae, Miteidae, Acaridae, Astigmatidae, Sarcoptidae, Slugidae, or Scytothripidae.

18. The method according to any one of claims 9 to 11, wherein the plant is a grass, a solanaceae, a cucurbit, a legume, a cruciferous plant, a rose, a mulberry, a mallow, a pipal, a lily, a aster, a amaranth, an ericaceae, a citrus, a rubiaceae, an oleaceae, a laurel, a saccharine, a sycamore, a sapindaceae, or a mint family plant.

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