Method for controlling parasitic plants

Abstract

Provided is a technique, such as a technique for controlling parasitic plants, that is useful in the fields of agricultural and horticultural. Parasitic plants are controlled by using a compound capable of having the same or the opposite function as strigolactone, such as an amino acid derivative having a D ring.

Description

How to control parasitic plants

[0001] The present invention relates to a useful technology in the agricultural and horticultural fields, such as a technology for controlling parasitic plants.

[0002] Plants of the Orobanchaceae family (Striga, Orobanche, etc.), Scrophulariaceae (Alectra, etc.), and Convolvulaceae (Cuscuta, etc.) are parasitic plants that adversely affect food production and are a global problem. For example, Striga parasitizes major grains such as sorghum, corn, and rice, while Orobanche parasitizes major vegetables such as tomatoes, potatoes, tobacco, eggplant, and broad beans, causing significant damage. The total damage caused by these parasitic plants in Africa is estimated to be approximately 1 trillion yen. Because the seeds of Striga and Orobanche are very small and Striga can produce approximately 100,000 seeds at a time, control of contaminated soil is extremely difficult. Therefore, there is a need to develop technologies to control Orobanche plants.

[0003] For example, a technique for controlling Orobanchaceae plants is known in which strigolactone or a compound that may have a similar function is used to induce suicide germination in Orobanchaceae plants (Patent Document 1 and Non-Patent Document 1).

[0004] WO2012 / 043813

[0005] Uraguchi et al., (2018) Science, 362, 1301-1305. A femtomolar-range suicide germination stimulant for the parasitic plant Striga hermonthica.

[0006] An object of the present invention is to provide a technique useful in the agricultural and horticultural fields, such as a technique for controlling parasitic plants.

[0007] As a result of extensive research to solve the above problems, the present inventors discovered a group of compounds that may have functions similar to or opposite to those of strigolactone, and completed the present invention.

[0008] That is, the present invention can be exemplified as follows. [1] A composition for controlling parasitic plants, comprising the following components (A), (B), or (C): (A) a compound represented by general formula (I) described below; (B) a compound represented by general formula (II) described below; (C) an amino acid fermentation by-product. In formula (I), X represents an atomic bond or an oxycarbonyl group (OC(=O)), Y represents an oxygen atom (O), a nitrogen atom bonded to a hydrogen atom (NH), or a nitrogen atom bonded to a methyl group (NMe), R1 represents a hydrogen atom (H) or a methyl group, and R2 represents an amino acid, agmatine, guanidine, a structure represented by general formula (R2-1) described below, or a structure represented by general formula (R2-2) described below. In formula (R2-1), n ​​represents an integer of 2 to 5 (i.e., 2, 3, 4, or 5), and in formula (R2-1), R3 and R4 each independently represent a hydrogen atom or an acyl group. In formula (R2-2), a represents an optionally substituted alkylene group having 1 to 4 carbon atoms or an optionally substituted alkenylene group having 2 to 4 carbon atoms, and R5 represents a hydrogen atom (H) or an optionally substituted alkyl group having 1 to 4 carbon atoms. In formula (II), X1 represents an interatomic bond or a methyleneoxy group (CH ２ X2 represents an interatomic bond or a carbonyl group (C(=O)), Y represents an oxygen atom (O) or a nitrogen atom (NH) bonded to a hydrogen atom, R1 represents a hydrogen atom (H) or a methyl group, R2 represents an amino acid, agmatine, guanidine, an aliphatic alcohol, a fatty acid, a structure represented by the general formula (R2-1) or a structure represented by the general formula (R2-2), and b-c represents CH-CH ２or C=CH. [2] The composition, wherein the parasitic plant is controlled by inducing suicide germination or inhibiting germination of the parasitic plant. [3] The composition, wherein the parasitic plant is a plant of the Orobanchaceae family, the Scrophulariaceae family, or the Convolvulaceae family. [4] The composition, wherein the parasitic plant is a plant of the genus Striga, Orobanche, Phelipanche, Alectra, or Cuscuta. [5] The parasitic plant is Striga asiatica, Striga gesnerioides, Striga hermonthica, Striga aspera, Striga asiatica, Striga curviflora, Striga parviflora, Striga angustifolia, Striga latericea, Striga aequinoctialis, Striga angolensis, Striga bilabiate, Striga brachycalyx, Striga chrsantha, Striga dalzielii, Striga elegans, Striga forbesii, Striga gastonii, Striga gracillima, Striga hallaei, Striga hirsuta, Striga junodii, Striga klingii, Striga lepidagathidis, Striga lutea, Striga macrantha, Striga passargei, Striga pinnatifida, Striga primuloides, Striga yemenica, Striga pubiflora, Orobanche ramosa, Orobanche minor, Orobanche crenata, Orobanche cumana, Orobanche foetida, Orobanche aegyptiaca, Orobanche cernua, Phelipanche ramosa, Phelipancheaegyptiaca, Alectra vogelii, Alectra picta, Alectra sessiliflora, Alectra orobanchoides, Alectra fluminensis, Cuscuta australis, Cuscuta campestris, Cuscuta chinensis, Cuscuta indecora, Cuscuta epithymum, Cuscuta epilinum, Cuscuta gronovii, Cuscuta The composition is planiflora, Cuscuta monogyna, Cuscuta pedicellata, Cuscuta palaestina, or Cuscuta rejlexa. [6] The composition, wherein in the component (A), Y is NH and R1 is a methyl group. [7] The composition, wherein the component (A) satisfies any one of the following conditions: (1) X is an atomic bond or an oxycarbonyl group, and R2 is an amino acid bonded through an amino group, agmatine bonded through an amino group, or guanidine bonded through an amino group; (2) X is an atomic bond, and R2 is an amino acid bonded through a carboxyl group; (3) X is an atomic bond, and R2 is an amino acid bonded through a hydroxyl group; (4) X is an atomic bond, and R2 is an amino acid bonded through a thiol group; (5) X is an atomic bond, and R2 is an amino acid bonded through an amide group; (6) X is an atomic bond or an oxycarbonyl group, and R2 is a structure represented by formula (R2-1); (7) X is an atomic bond, and R2 is a structure represented by formula (R2-2). [8] The composition, wherein the component (A) satisfies any one of the following conditions: (1) X is an interatomic bond, Y is NH, R1 is a methyl group, and R2 is an amino acid bonded through an amino group, agmatine bonded through an amino group, guanidine bonded through an amino group, or a structure represented by formula (R2-1); (2) X is an oxycarbonyl group, Y is NH, R1 is a methyl group, and R2 is an amino acid bonded through a carboxyl group or a structure represented by formula (R2-2). [9] The component (B) satisfies any one of the following conditions: (1) X is an interatomic bond, Y is NH, R1 is a methyl group, and R2 is an amino acid bonded through a carboxyl group or a structure represented by formula (R2-2). ２and R1 is H.

[10] The composition, wherein component (B) satisfies any of the following conditions: (1) X1 is an interatomic bond, X2 is a carbonyl group, and R2 is an amino acid bonded via an amino group, agmatine bonded via an amino group, or guanidine bonded via an amino group; (2) X1 is a methyleneoxy group, X2 is an interatomic bond, and R2 is an amino acid bonded via a carboxyl group; (3) X1 is an interatomic bond, X2 is a carbonyl group, and R2 is an aliphatic alcohol; (4) X1 is a methyleneoxy group, X2 is an interatomic bond, and R2 is a fatty acid; (5) X1 is an interatomic bond, X2 is a carbonyl group, and R2 is a structure represented by formula (R2-1); (6) X1 is a methyleneoxy group, X2 is an interatomic bond, and R2 is a structure represented by formula (R2-2); (7) X1 is an interatomic bond, X2 is an interatomic bond, and R2 is a guanidine bonded via an amino group.

[11] The composition, wherein the component (B) satisfies any of the following conditions: (1) X1 is an interatomic bond, X2 is a carbonyl group, Y is NH, and bc is CH—CH ２ , R1 is H, R2 is an amino acid bonded through an amino group, agmatine bonded through an amino group, guanidine bonded through an amino group, or a structure represented by formula (R2-1); (2) X1 is a methyleneoxy group, X2 is an interatomic bond, Y is NH, and bc is CH—CH ２(3) X1 is an interatomic bond, X2 is an interatomic bond, Y is an oxygen atom (O), b-c is C=CH, R1 is a methyl group, and R2 is a guanidine bonded through an amino group.

[12] The composition as described above, except when component (B) is a compound represented by the formulas (Compound 41), (Compound 50), (Compound 52), (Compound 54), (Compound 55), and (Compound 77) described below.

[13] The composition, wherein the component (A) or (B) is selected from the compounds represented by the formulae (Compound 1) to (Compound 20), (Compound 23), (Compound 26) to (Compound 40), (Compound 42) to (Compound 49), (Compound 51), (Compound 53), (Compound 56) to (Compound 76), (Compound 78) to (Compound 80), and (Compound 82) to (Compound 90) described below.

[14] The composition, wherein the component (C) is a fermentation by-product of lysine, tryptophan, threonine, valine, leucine, or isoleucine.

[15] The composition, wherein the component (A), (B), or (C) is used in the form of a liquid containing the component (A), (B), or (C) at a concentration of 10 nM to 10 mM.

[16] A method for controlling parasitic plants, comprising applying the following component (A), (B), or (C) to seeds of a parasitic plant: (A) a compound represented by general formula (I) described below; (B) a compound represented by general formula (II) described below; (C) an amino acid fermentation by-product. In formula (I), X represents an atomic bond or an oxycarbonyl group (OC(═O)), Y represents an oxygen atom (O), a nitrogen atom bonded to a hydrogen atom (NH), or a nitrogen atom bonded to a methyl group (NMe), R1 represents a hydrogen atom (H) or a methyl group, and R2 represents an amino acid, agmatine, guanidine, a structure represented by general formula (R2-1) described below, or a structure represented by general formula (R2-2) described below. In formula (R2-1), n ​​represents an integer of 2 to 5 (i.e., 2, 3, 4, or 5), and in formula (R2-1), R3 and R4 each independently represent a hydrogen atom or an acyl group.In formula (R2-2), a represents an optionally substituted alkylene group having 1 to 4 carbon atoms or an optionally substituted alkenylene group having 2 to 4 carbon atoms, and R5 represents a hydrogen atom (H) or an optionally substituted alkyl group having 1 to 4 carbon atoms. In formula (II), X1 represents an interatomic bond or a methyleneoxy group (CH. ２ X2 represents an interatomic bond or a carbonyl group (C(=O)), Y represents an oxygen atom (O) or a nitrogen atom (NH) bonded to a hydrogen atom, R1 represents a hydrogen atom (H) or a methyl group, R2 represents an amino acid, agmatine, guanidine, an aliphatic alcohol, a fatty acid, a structure represented by the general formula (R2-1) or a structure represented by the general formula (R2-2), and b-c represents CH-CH ２or C═CH.

[17] A method for producing a plant body, the method comprising: inducing suicide germination of a parasitic plant by applying the following component (A), (B), or (C) to seeds of the parasitic plant; cultivating a plant that is a target for parasitism by the parasitic plant after the application; and harvesting the plant body of the target for parasitism by the parasitic plant: (A) a compound represented by general formula (I) described below; (B) a compound represented by general formula (II) described below; (C) an amino acid fermentation by-product. In formula (I), X represents an atomic bond or an oxycarbonyl group (OC(=O)), Y represents an oxygen atom (O), a nitrogen atom bonded to a hydrogen atom (NH), or a nitrogen atom bonded to a methyl group (NMe), R1 represents a hydrogen atom (H) or a methyl group, R2 represents an amino acid, agmatine, guanidine, a structure represented by general formula (R2-1) described below, or a structure represented by general formula (R2-2) described below. In formula (R2-1), n ​​represents an integer of 2 to 5 (i.e., 2, 3, 4, or 5), and in formula (R2-1), R3 and R4 each independently represent a hydrogen atom or an acyl group. In formula (R2-2), a represents an optionally substituted alkylene group having 1 to 4 carbon atoms or an optionally substituted alkenylene group having 2 to 4 carbon atoms, R5 represents a hydrogen atom (H) or an optionally substituted alkyl group having 1 to 4 carbon atoms. In formula (II), X1 represents an interatomic bond or a methyleneoxy group (CH ２ X2 represents an interatomic bond or a carbonyl group (C(=O)), Y represents an oxygen atom (O) or a nitrogen atom (NH) bonded to a hydrogen atom, R1 represents a hydrogen atom (H) or a methyl group, R2 represents an amino acid, agmatine, guanidine, an aliphatic alcohol, a fatty acid, a structure represented by the general formula (R2-1) or a structure represented by the general formula (R2-2), and b-c represents CH-CH ２or C═CH.

[18] A method for producing a plant, the method comprising: cultivating a plant that is to be parasitized by a parasitic plant; inducing germination of the parasitic plant by applying the following component (A), (B), or (C) to seeds of the parasitic plant in the later stage of the cultivation; and harvesting the plant that is to be parasitized by the parasitic plant: (A) a compound represented by general formula (I) described below; (B) a compound represented by general formula (II) described below; (C) an amino acid fermentation by-product. In formula (I), X represents an atomic bond or an oxycarbonyl group (OC(=O)), Y represents an oxygen atom (O), a nitrogen atom bonded to a hydrogen atom (NH), or a nitrogen atom bonded to a methyl group (NMe), R1 represents a hydrogen atom (H) or a methyl group, R2 represents an amino acid, agmatine, guanidine, a structure represented by general formula (R2-1) described below, or a structure represented by general formula (R2-2) described below. In formula (R2-1), n ​​represents an integer of 2 to 5 (i.e., 2, 3, 4, or 5), and in formula (R2-1), R3 and R4 each independently represent a hydrogen atom or an acyl group. In formula (R2-2), a represents an optionally substituted alkylene group having 1 to 4 carbon atoms or an optionally substituted alkenylene group having 2 to 4 carbon atoms, R5 represents a hydrogen atom (H) or an optionally substituted alkyl group having 1 to 4 carbon atoms. In formula (II), X1 represents an interatomic bond or a methyleneoxy group (CH ２ X2 represents an interatomic bond or a carbonyl group (C(=O)), Y represents an oxygen atom (O) or a nitrogen atom (NH) bonded to a hydrogen atom, R1 represents a hydrogen atom (H) or a methyl group, R2 represents an amino acid, agmatine, guanidine, an aliphatic alcohol, a fatty acid, a structure represented by the general formula (R2-1) or a structure represented by the general formula (R2-2), and b-c represents CH-CH ２or C═CH.

[19] A method for producing a plant, the method comprising cultivating a plant that is to be parasitized by a parasitic plant; applying the following component (A), (B), or (C) to seeds of the parasitic plant during the cultivation to suppress germination of the parasitic plant; and harvesting the plant that is to be parasitized by the parasitic plant: (A) a compound represented by general formula (I) described below; (B) a compound represented by general formula (II) described below; (C) an amino acid fermentation by-product. In formula (I), X represents an atomic bond or an oxycarbonyl group (OC(=O)), Y represents an oxygen atom (O), a nitrogen atom bonded to a hydrogen atom (NH), or a nitrogen atom bonded to a methyl group (NMe), R1 represents a hydrogen atom (H) or a methyl group, R2 represents an amino acid, agmatine, guanidine, a structure represented by general formula (R2-1) described below, or a structure represented by general formula (R2-2) described below. In formula (R2-1), n ​​represents an integer of 2 to 5 (i.e., 2, 3, 4, or 5), and in formula (R2-1), R3 and R4 each independently represent a hydrogen atom or an acyl group. In formula (R2-2), a represents an optionally substituted alkylene group having 1 to 4 carbon atoms or an optionally substituted alkenylene group having 2 to 4 carbon atoms, R5 represents a hydrogen atom (H) or an optionally substituted alkyl group having 1 to 4 carbon atoms. In formula (II), X1 represents an interatomic bond or a methyleneoxy group (CH ２ X2 represents an interatomic bond or a carbonyl group (C(=O)), Y represents an oxygen atom (O) or a nitrogen atom (NH) bonded to a hydrogen atom, R1 represents a hydrogen atom (H) or a methyl group, R2 represents an amino acid, agmatine, guanidine, an aliphatic alcohol, a fatty acid, a structure represented by the general formula (R2-1) or a structure represented by the general formula (R2-2), and b-c represents CH-CH ２or C=CH.

[20] The method as mentioned above, wherein the parasitic plant is controlled by inducing suicide germination of the parasitic plant or suppressing germination of the parasitic plant.

[21] The method as mentioned above, wherein the parasitic plant is controlled by the application.

[22] The method as mentioned above, wherein the parasitic plant is a plant of the Orobanchaceae family, the Scrophulariaceae family, or the Convolvulaceae family.

[23] The method as mentioned above, wherein the parasitic plant is a plant of the genus Striga, Orobanche, Phelipanche, Alectra, or Cuscuta.

[24] The parasitic plant is Striga asiatica, Striga gesnerioides, Striga hermonthica, Striga aspera, Striga asiatica, Striga curviflora, Striga parviflora, Striga angustifolia, Striga latericea, Striga aequinoctialis, Striga angolensis, Striga bilabiate, Striga brachycalyx, Striga chrsantha, Striga dalzielii, Striga elegans, Striga forbesii, Striga gastonii, Striga gracillima, Striga hallaei, Striga hirsuta, Striga junodii, Striga klingii, Striga lepidagathidis, Striga lutea, Striga macrantha, Striga passargei, Striga pinnatifida, Striga primuloides, Striga yemenica, Striga pubiflora, Orobanche ramosa, Orobanche minor, Orobanche crenata, Orobanche cumana, Orobanche foetida, Orobanche aegyptiaca, Orobanchecernua, Phelipanche ramosa, Phelipanche aegyptiaca, Alectra vogelii, Alectra picta, Alectra sessiliflora, Alectra orobanchoides, Alectra fluminensis, Cuscuta australis, Cuscuta campestris, Cuscuta chinensis, Cuscuta indecora, Cuscuta epithymum, Cuscuta epilinum, Cuscuta gronovii, Cuscuta planiflora, Cuscuta monogyna, Cuscuta pedicellata, Cuscuta palaestina, or Cuscuta rejlexa.

[25] The method described above, wherein in the component (A), Y is NH and R1 is a methyl group.

[26] The method, wherein component (A) satisfies any of the following conditions: (1) X is an atomic bond or an oxycarbonyl group, and R2 is an amino acid bonded via an amino group, agmatine bonded via an amino group, or guanidine bonded via an amino group; (2) X is an atomic bond and R2 is an amino acid bonded via a carboxyl group; (3) X is an atomic bond and R2 is an amino acid bonded via a hydroxyl group; (4) X is an atomic bond and R2 is an amino acid bonded via a thiol group; (5) X is an atomic bond and R2 is an amino acid bonded via an amide group; (6) X is an atomic bond or an oxycarbonyl group, and R2 is a structure represented by formula (R2-1); (7) X is an atomic bond and R2 is a structure represented by formula (R2-2).

[27] The method, wherein the component (A) satisfies any of the following conditions: (1) X is an interatomic bond, Y is NH, R1 is a methyl group, and R2 is an amino acid bonded through an amino group, agmatine bonded through an amino group, guanidine bonded through an amino group, or a structure represented by formula (R2-1); (2) X is an oxycarbonyl group, Y is NH, R1 is a methyl group, and R2 is an amino acid bonded through a carboxyl group or a structure represented by formula (R2-2).

[28] The component (B) satisfies any of the following conditions: (1) X is an interatomic bond, Y is NH, R1 is a methyl group, and R2 is an amino acid bonded through a carboxyl group or a structure represented by formula (R2-2). ２and R1 is H.

[29] The method, wherein component (B) satisfies any of the following conditions: (1) X1 is an interatomic bond, X2 is a carbonyl group, and R2 is an amino acid bonded via an amino group, agmatine bonded via an amino group, or guanidine bonded via an amino group; (2) X1 is a methyleneoxy group, X2 is an interatomic bond, and R2 is an amino acid bonded via a carboxyl group; (3) X1 is an interatomic bond, X2 is a carbonyl group, and R2 is an aliphatic alcohol; (4) X1 is a methyleneoxy group, X2 is an interatomic bond, and R2 is a fatty acid; (5) X1 is an interatomic bond, X2 is a carbonyl group, and R2 is a structure represented by formula (R2-1); (6) X1 is a methyleneoxy group, X2 is an interatomic bond, and R2 is a structure represented by formula (R2-2); (7) X1 is an atomic bond, X2 is an atomic bond, and R2 is a guanidine bonded via an amino group.

[30] The method, wherein the component (B) satisfies any of the following conditions: (1) X1 is an atomic bond, X2 is a carbonyl group, Y is NH, and bc is CH—CH ２ , R1 is H, R2 is an amino acid bonded through an amino group, agmatine bonded through an amino group, or a structure represented by formula (R2-1); (2) X1 is a methyleneoxy group, X2 is an interatomic bond, Y is NH, and bc is CH—CH ２, R1 is H, and R2 is an amino acid bonded via a carboxyl group, a fatty acid having 2 to 18 carbon atoms, or a structure represented by formula (R2-2); (3) X1 is an atomic bond, X2 is an atomic bond, Y is an oxygen atom (O), b-c is C=CH, R1 is a methyl group, and R2 is guanidine bonded via an amino group.

[31] The method described above, except when component (B) is a compound represented by the formulas (Compound 41), (Compound 50), (Compound 52), (Compound 54), (Compound 55), and (Compound 77) described below.

[32] The method, wherein the component (A) or (B) is selected from the compounds represented by the formulae (Compound 1) to (Compound 20), (Compound 23), (Compound 26) to (Compound 40), (Compound 42) to (Compound 49), (Compound 51), (Compound 53), (Compound 56) to (Compound 76), (Compound 78) to (Compound 80), and (Compound 82) to (Compound 90) described below.

[33] The method, wherein the component (C) is a fermentation by-product of lysine, tryptophan, threonine, valine, leucine, or isoleucine.

[34] The method, wherein the component (A), (B), or (C) is used in the form of a liquid containing the component (A), (B), or (C) at a concentration of 10 nM to 10 mM.

[0009] 1 is a diagram showing the control effect of compound 5 or synthetic strigolactone GR24 on Orobanche minor by inducing suicide germination. 2 is a diagram (photograph) showing the control effect of compound 5 or synthetic strigolactone GR24 on Orobanche minor by inducing suicide germination.

[0010] The present invention will be described in detail below.

[0011] <1> Active ingredient The active ingredient used in the present invention includes the following ingredients (A) to (C): (A) a compound represented by the following general formula (I); (B) a compound represented by the following general formula (II); (C) an amino acid fermentation by-product.

[0012] Component (A) is a compound represented by the following general formula (I). ｎ " and "Rn" (n is a positive integer) may be used interchangeably.

[0013]

[0014] In formula (I), the cyclic structure located on the right side is also referred to as "D ring".

[0015] In formula (I), X represents an interatomic bond or an oxycarbonyl group (OC(=O)). Note that the "oxycarbonyl group" represented by X means that O is bonded to the D ring and C(=O) is bonded to R2.

[0016] In formula (I), Y represents an oxygen atom (O), a nitrogen atom bonded to a hydrogen atom (NH), or a nitrogen atom bonded to a methyl group (NMe).

[0017] In formula (I), R1 represents a hydrogen atom (H) or a methyl group.

[0018] In formula (I), R2 represents an amino acid, agmatine, guanidine, a structure represented by the following general formula (R2-1), or a structure represented by the following general formula (R2-2). In formula (I), R2 may particularly represent an amino acid, agmatine, a structure represented by the following general formula (R2-1), or a structure represented by the following general formula (R2-2).

[0019]

[0020] In formula (R2-1), n ​​represents an integer of 2 to 5 (ie, 2, 3, 4, or 5).

[0021] In formula (R2-1), R3 and R4 each independently represent a hydrogen atom or an acyl group.

[0022]

[0023] In formula (R2-2), a represents an optionally substituted alkylene group having 1 to 4 carbon atoms or an optionally substituted alkenylene group having 2 to 4 carbon atoms.

[0024] In formula (R2-2), R5 represents a hydrogen atom (H) or an optionally substituted alkyl group having 1 to 4 carbon atoms. In particular, R5 in formula (R2-2) may be an optionally substituted alkyl group having 1 to 4 carbon atoms.

[0025] Unless otherwise specified, for component (A), X, Y, n, and R1 through R5 can each be independently selected.

[0026] 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. 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).

[0027] The term "substituted functional group" means that one or more hydrogen atoms constituting the functional group are substituted with a substituent. The term "substituted functional group" is also referred to as "functional group having a substituent." The number of hydrogen atoms substituted with a substituent may be, for example, 1 to 5, 1 to 4, 1 to 3, or 1 to 2. The number of hydrogen atoms substituted with a substituent may specifically be, for example, 1, 2, 3, 4, or 5. The number of hydrogen atoms substituted with a substituent may also be interpreted as the number of substituents possessed by the functional group. When two or more hydrogen atoms are substituted with a substituent, a substituent is independently selected for each hydrogen atom. Examples of hydrogen atoms substituted with a substituent include a hydrogen atom bonded to a carbon atom, a hydrogen atom bonded to a nitrogen atom, and a hydrogen atom bonded to an oxygen atom. The hydrogen atom bonded to a carbon atom may, for example, be a hydrogen atom bonded to a terminal carbon atom, or may not be such a hydrogen atom. A "terminal carbon atom" refers to 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.

[0028] Examples of the substituents of the substituted alkylene group or substituted alkenylene group represented by a include a halogen atom, a hydroxyl group, an amino group, a carboxyl group, an aminocarbonyl group, a mercapto group, an optionally substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted alkoxy group, an optionally substituted alkylamino group, an optionally substituted alkoxycarbonylamino group, an optionally substituted alkoxycarbonyl group, and an optionally substituted alkylthio group. Examples of the substituents of the substituted alkyl group represented by R5 include a halogen atom, a hydroxyl group, an amino group, a carboxyl group, an aminocarbonyl group, a mercapto group, an optionally substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted alkoxy group, an optionally substituted alkylamino group, an optionally substituted alkoxycarbonylamino group, an optionally substituted alkoxycarbonyl group, and an optionally substituted alkylthio group. Examples of the substituent possessed by the functional group constituting the acyl group represented by R3 or R4 (for example, a substituted alkyl group, a substituted cycloalkyl group, a substituted alkenyl group, a substituted aryl group, or a substituted alkoxy group) include a halogen atom, a hydroxyl group, an amino group, a carboxyl group, an aminocarbonyl group, a mercapto group, an optionally substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted alkoxy group, an optionally substituted alkylamino group, an optionally substituted alkoxycarbonylamino group, an optionally substituted alkoxycarbonyl group, and an optionally substituted alkylthio group.

[0029] Substituents possessed by the substituted aryl group in the substituted alkylene group or substituted alkenylene group represented by a include a halogen atom, a hydroxyl group, an amino group, a carboxyl group, and an alkyl group. Substituents possessed by the substituted heteroaryl group in the substituted alkylene group or substituted alkenylene group represented by a include a halogen atom, a hydroxyl group, an amino group, a carboxyl group, and an alkyl group. Substituents possessed by the substituted aryl group in the substituted alkyl group represented by R5 include a halogen atom, a hydroxyl group, an amino group, a carboxyl group, and an alkyl group. Substituents possessed by the substituted heteroaryl group in the substituted alkyl group represented by R5 include a halogen atom, a hydroxyl group, an amino group, a carboxyl group, and an alkyl group. Substituents possessed by the substituted aryl group in the functional group constituting the acyl group represented by R3 or R4 include a halogen atom, a hydroxyl group, an amino group, a carboxyl group, and an alkyl group. Substituents possessed by the substituted heteroaryl group in the functional group constituting the acyl group represented by R3 or R4 include a halogen atom, a hydroxyl group, an amino group, a carboxyl group, and an alkyl group.

[0030] Examples of the substituents on the substituted alkoxy group in the substituted alkylene group or substituted alkenylene group represented by a include a halogen atom, a hydroxyl group, an amino group, a carboxyl group, an aminocarbonyl group, an aryl group, and a heteroaryl group. Examples of the substituents on the substituted alkoxycarbonyl group in the substituted alkylene group or substituted alkenylene group represented by a include a halogen atom, a hydroxyl group, an amino group, a carboxyl group, an aminocarbonyl group, an aryl group, and a heteroaryl group. Examples of the substituents on the substituted alkoxy group in the substituted alkyl group represented by R5 include a halogen atom, a hydroxyl group, an amino group, a carboxyl group, an aminocarbonyl group, an aryl group, and a heteroaryl group. Examples of the substituents on the substituted alkoxycarbonyl group in the substituted alkyl group represented by R5 include a halogen atom, a hydroxyl group, an amino group, a carboxyl group, an aminocarbonyl group, an aryl group, and a heteroaryl group. Examples of the substituents of the substituted alkoxy group in the functional group constituting the acyl group as R3 or R4 include a halogen atom, a hydroxyl group, an amino group, a carboxyl group, an aminocarbonyl group, an aryl group, and a heteroaryl group. Examples of the substituents of the substituted alkoxycarbonyl group in the functional group constituting the acyl group as R3 or R4 include a halogen atom, a hydroxyl group, an amino group, a carboxyl group, an aminocarbonyl group, an aryl group, and a heteroaryl group.

[0031] Examples of the substituents of the substituted alkylamino group in the substituted alkylene group or substituted alkenylene group represented by a include a halogen atom, a hydroxyl group, an amino group, a carboxyl group, an aminocarbonyl group, an N-alkyl group, an aryl group, and a heteroaryl group. Examples of the substituents of the substituted alkoxycarbonylamino group in the substituted alkylene group or substituted alkenylene group represented by a include a halogen atom, a hydroxyl group, an amino group, a carboxyl group, an aminocarbonyl group, an N-alkyl group, an aryl group, and a heteroaryl group. Examples of the substituents of the substituted alkylamino group in the substituted alkyl group represented by R5 include a halogen atom, a hydroxyl group, an amino group, a carboxyl group, an aminocarbonyl group, an N-alkyl group, an aryl group, and a heteroaryl group. Examples of the substituents of the substituted alkoxycarbonylamino group in the substituted alkyl group represented by R5 include a halogen atom, a hydroxyl group, an amino group, a carboxyl group, an aminocarbonyl group, an N-alkyl group, an aryl group, and a heteroaryl group. Examples of the substituents of the substituted alkylamino group in the functional group constituting the acyl group as R3 or R4 include a halogen atom, a hydroxyl group, an amino group, a carboxyl group, an aminocarbonyl group, an N-alkyl group, an aryl group, and a heteroaryl group. Examples of the substituents of the substituted alkoxycarbonylamino group in the functional group constituting the acyl group as R3 or R4 include a halogen atom, a hydroxyl group, an amino group, a carboxyl group, an aminocarbonyl group, an N-alkyl group, an aryl group, and a heteroaryl group. The term "N-alkyl group" refers to an alkyl group that substitutes for the hydrogen atom of an amino group.

[0032] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0033] Examples of alkyl groups include alkyl groups having 1 to 12 carbon atoms. Examples of alkyl groups include, in particular, alkyl groups having 1 to 6 carbon atoms. Examples of alkyl groups include, more particularly, alkyl groups having 1 to 4 carbon atoms. The alkyl group may be linear or branched. Examples of alkyl groups having 1 to 6 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, 2,3-dimethylpropyl, and hexyl. Examples of alkyl groups having 1 to 4 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, and tert-butyl. The descriptions of alkyl groups also apply mutatis mutandis to N-alkyl groups.

[0034] The alkylene group may be linear or branched. Examples of the alkylene group having 1 to 4 carbon atoms include a methylene group, an ethylene group, a propylene group, an isopropylene group, a butylene group, an isobutylene group, a sec-butylene group, and a tert-butylene group.

[0035] The alkenylene group may be linear or branched. Examples of the alkenylene group having 2 to 4 carbon atoms include an ethenylene group, a propenylene group, an isopropenylene group, a butenylene group, an isobutenylene group, and a sec-butenylene group.

[0036] Examples of the aryl group include aryl groups having 6 to 14 carbon atoms. Examples of the aryl group particularly include aryl groups having 6 to 10 carbon atoms. Specific examples of the aryl group include a phenyl group, a naphthyl group, and a fluorenyl group.

[0037] The term "heteroaryl group" refers to an aryl group having at least one heteroatom selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom as a ring-constituting atom. Examples of heteroaryl groups include heteroaryl groups having 3 to 14 carbon atoms. Examples of heteroaryl groups include, in particular, heteroaryl groups having 4 to 10 carbon atoms. Examples of heteroaryl groups include, more particularly, heteroaryl groups having 4 to 9 carbon atoms. Specific examples of heteroaryl groups include furanyl groups, pyrrolyl groups, oxazolyl groups, imidazolyl groups, pyrazolyl groups, pyranyl groups, indenyl groups, thiophenyl groups, pyridinyl groups, indolyl groups, and quinolinyl groups. Examples of heteroaryl groups include, in particular, imidazolyl groups and indolyl groups.

[0038] Examples of the alkoxy group include alkoxy groups having 1 to 6 carbon atoms. Examples of the alkoxy group particularly include alkoxy groups having 1 to 4 carbon atoms. The alkoxy group may be linear or branched. Specific examples of the alkoxy group include methoxy, ethoxy, 1-propoxy, 2-propoxy, n-butoxy, i-butoxy, sec-butoxy, tert-butoxy, 1-pentyloxy, 2-pentyloxy, 3-pentyloxy, 2-methyl-1-butyloxy, 3-methyl-1-butyloxy, 2-methyl-2-butyloxy, 3-methyl-2-butyloxy, 2,2-dimethyl-1-propyloxy, 1-hexyloxy, 2-hexyloxy, and 3-hexyloxy. Examples of the alkoxy group particularly include tert-butoxy.

[0039] The optionally substituted alkyl group is an alkyl group or a substituted alkyl group. The alkyl group is as described above. The above descriptions of the alkyl group and its substituent can be applied mutatis mutandis to the alkyl group and the substituent that constitute the substituted alkyl group. For example, examples of the optionally substituted alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, a tert-butyl group, and a benzyl group.

[0040] The optionally substituted alkylene group is an alkylene group or a substituted alkylene group. The alkylene group is as described above. The alkylene group and the substituent constituting the substituted alkylene group can be respectively described mutatis mutandis with respect to the alkylene group and the substituent thereof.

[0041] The optionally substituted alkenylene group is an alkenylene group or a substituted alkenylene group. The alkenylene group is as described above. The alkenylene group and the substituent constituting the substituted alkenylene group can be the same as those described above for the alkenylene group and its substituent.

[0042] The optionally substituted aryl group is an aryl group or a substituted aryl group. The aryl group is as described above. The aryl group and the substituent constituting the substituted aryl group can be respectively described mutatis mutandis with respect to the aryl group and the substituent thereof.

[0043] Specific examples of substituted aryl groups include alkylaryl groups which may be substituted (i.e., alkylaryl groups and substituted alkylaryl groups). The alkyl groups, aryl groups, and substituents constituting the alkylaryl groups or substituted alkylaryl groups are the same as those described above for the alkyl groups, aryl groups, and their substituents. Specific examples of optionally substituted alkylaryl groups include methylphenyl groups (e.g., 2-, 3-, or 4-methylphenyl groups).

[0044] Specific examples of the substituted aryl group include a hydroxyphenyl group (such as a 2-, 3-, or 4-hydroxyphenyl group), a chlorophenyl group (such as a 2-, 3-, or 4-chlorophenyl group), a dichlorophenyl group (such as a 2,5-dichlorophenyl group), a fluorophenyl group (such as a 2-, 3-, or 4-fluorophenyl group), and a 2,3-dihydroxyindenyl group.

[0045] The optionally substituted heteroaryl group is a heteroaryl group or a substituted heteroaryl group. The heteroaryl group is as described above. The heteroaryl group and the substituent constituting the substituted heteroaryl group can be respectively described mutatis mutandis with respect to the heteroaryl group and the substituent thereof.

[0046] The optionally substituted alkoxy group is an alkoxy group or a substituted alkoxy group. The alkoxy group is as described above. The alkoxy group and the substituent constituting the substituted alkoxy group can be respectively described mutatis mutandis with respect to the alkoxy group and the substituent thereof.

[0047] Specific examples of the substituted alkoxy group include optionally substituted arylalkoxy groups (i.e., arylalkoxy groups and substituted arylalkoxy groups). The aryl group, alkoxy group, and substituents constituting the arylalkoxy group or substituted arylalkoxy group can be the same as those described above for the aryl group, alkoxy group, and their substituents. Specific examples of the optionally substituted arylalkoxy group include a phenylmethoxy group.

[0048] Specific examples of the substituted alkoxy group include a hydroxyalkoxy group (such as a hydroxyethoxy group) and a trifluoromethoxy group.

[0049] The optionally substituted alkylamino group is an alkylamino group or a substituted alkylamino group. The above-described description of the alkyl group can be applied mutatis mutandis to the alkyl group constituting the alkylamino group. The above-described description of the alkyl group and its substituent can be applied mutatis mutandis to the alkyl group and substituent constituting the substituted alkylamino group. For example, the number of carbon atoms in the alkyl group (e.g., 1 to 12 or 1 to 6) can be interpreted as the number of carbon atoms in the optionally substituted alkylamino group (excluding the number of carbon atoms in the substituent). Specific examples of the substituted alkylamino group include optionally substituted carboxyalkylamino groups (i.e., carboxyalkylamino groups and substituted carboxyalkylamino groups). The number of carbon atoms in the optionally substituted carboxyalkylamino group (excluding the number of carbon atoms in the substituent) may be, for example, 2 to 13 or 2 to 7. Specific examples of the carboxyalkylamino group include a carboxymethylamino group and a 1-methylcarboxymethylamino group. Specific examples of the substituted carboxyalkylamino group include a carboxyalkylamino group substituted with a hydroxyl group, an amino group, a carboxyl group, a phenyl group, an indolyl group, or an N-methyl group. More specific examples of the substituted carboxyalkylamino group include a 1-(aminobutyl)carboxymethylamino group, a 1-methylcarboxymethylamino group, a 1-(indolylmethyl)carboxymethylamino group, a 1-(carboxymethyl)carboxymethylamino group, a 1-(1-hydroxyethyl)carboxymethylamino group, a 1-(hydroxymethyl)carboxymethylamino group, a 1-isobutylcarboxymethylamino group, a 1-benzylcarboxymethylamino group, and an N-methylcarboxymethylamino group.

[0050] The optionally substituted alkoxycarbonyl group is an alkoxycarbonyl group or a substituted alkoxycarbonyl group. The alkoxy group constituting the alkoxycarbonyl group can be described mutatis mutandis as described above for the alkoxy group. The alkoxy group and the substituent constituting the substituted alkoxycarbonyl group can be described mutatis mutandis as described above for the alkoxy group and the substituent. Specific examples of the optionally substituted alkoxycarbonyl group include an indolylacetylmethoxycarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, an isopropoxycarbonyl group, a butoxycarbonyl group, an isobutoxycarbonyl group, a sec-butoxycarbonyl group, a tert-butoxycarbonyl group (also referred to as Boc), a phenylmethoxycarbonyl group, a 9-fluorenylmethyloxycarbonyl group (also referred to as Fmoc), a 3-methylphenyloxyacetyl group, a 3-chlorophenylmethoxycarbonyl group, a trifluoromethoxycarbonyl group, a 2,5-dichlorobenzoyl group, and a benzyloxycarbonyl group (also referred to as Cbz). Particular examples of the optionally substituted alkoxycarbonyl group include a tert-butoxycarbonyl group, a 9-fluorenylmethyloxycarbonyl group, and a benzyloxycarbonyl group.

[0051] The optionally substituted alkoxycarbonylamino group is an alkoxycarbonylamino group or a substituted alkoxycarbonylamino group. With regard to the alkoxy group (or alkoxycarbonyl group) constituting the alkoxycarbonylamino group, the above-mentioned description of the alkoxy group (or alkoxycarbonyl group) can be applied mutatis mutandis. With regard to the alkoxy group (or alkoxycarbonyl group) and substituents constituting the substituted alkoxycarbonylamino group, the above-mentioned description of the alkoxy group (or alkoxycarbonyl group) and its substituents can be applied mutatis mutandis. Specific examples of the optionally substituted alkoxycarbonylamino group include a tert-butoxycarbonylamino group, a 9-fluorenylmethyloxycarbonylamino group, and a benzyloxycarbonylamino group.

[0052] The optionally substituted alkylthio group is an alkylthio group or a substituted alkylthio group. The alkyl group constituting the alkylthio group can be described mutatis mutandis as described above for the alkyl group. The alkyl group and substituent constituting the substituted alkylthio group can be described mutatis mutandis as described above for the alkyl group and its substituent. A specific example of the optionally substituted alkylthio group is a methylthio group.

[0053] Examples of acyl groups include optionally substituted alkylcarbonyl groups, optionally substituted cycloalkylcarbonyl groups, optionally substituted alkenylcarbonyl groups, optionally substituted arylcarbonyl groups, and optionally substituted alkoxycarbonyl groups. The optionally substituted alkylcarbonyl groups are alkylcarbonyl groups or substituted alkylcarbonyl groups. The optionally substituted cycloalkylcarbonyl groups are cycloalkylcarbonyl groups or substituted cycloalkylcarbonyl groups. The optionally substituted alkenylcarbonyl groups are alkenylcarbonyl groups or substituted alkenylcarbonyl groups. The optionally substituted arylcarbonyl groups are arylcarbonyl groups or substituted arylcarbonyl groups. The optionally substituted alkoxycarbonyl groups are alkoxycarbonyl groups or substituted alkoxycarbonyl groups. The substituents possessed by the functional groups constituting the acyl groups (e.g., substituted alkyl groups, substituted cycloalkyl groups, substituted alkenyl groups, substituted aryl groups, or substituted alkoxy groups) are as described above. The descriptions of the optionally substituted alkyl group, optionally substituted aryl group, and optionally substituted alkoxy group constituting the acyl group can be applied mutatis mutandis to the descriptions of the optionally substituted alkyl group, optionally substituted aryl group, and optionally substituted alkoxy group, respectively. Examples of cycloalkyl groups include cyclic alkyl groups having 3 to 8 carbon atoms. Examples of cycloalkyl groups include, in particular, cyclic alkyl groups having 4 to 6 carbon atoms. Specific examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups. Examples of alkenyl groups include alkenyl groups having 2 to 6 carbon atoms. The alkenyl group may be linear or branched. Specific examples of alkenyl groups include vinyl, allyl, propenyl, butenyl, butadienyl, pentenyl, pentadienyl, hexenyl, and hexadienyl groups. Examples of acyl groups include, in particular, optionally substituted alkylcarbonyl groups and optionally substituted alkoxycarbonyl groups.Specific examples of the acyl group include an acetyl group, a propionyl group, a butyryl group, an isobutyryl group, a valeryl group, an isovaleryl group, a pivaloyl group, a hexanoyl group, an acryloyl group, a methacryloyl group, a crotonoyl group, an isocrotonoyl group, a cyclopropanoyl group, a cyclobutanoyl group, a cyclopentanoyl group, a cyclohexanoyl group, a benzoyl group, and the above-mentioned optionally substituted alkoxycarbonyl groups. Particular examples of the acyl group include an acetyl group, a tert-butoxycarbonyl group, a 9-fluorenylmethyloxycarbonyl group, and a benzyloxycarbonyl group.

[0054] The "amino acid" as R2 means an amino acid bonded to X by an appropriate bond. In addition, when X is an interatomic bond, the "bond between an amino acid and X" in formula (I) is to be read as the "bond between an amino acid and a D ring."

[0055] Examples of the amino acid as R2 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.

[0056] An "amino acid bonded via an amino group" refers to an amino acid bonded to X via the nitrogen atom of the amino group. When an amino acid has two or more amino groups, either of the amino groups may be used for bonding to X. For example, either the α-amino group or the ε-amino group may be used for bonding to X.

[0057] An "amino acid bonded via a carboxyl group" refers to an amino acid bonded to X 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 X. For example, the α-carboxyl group may be used to bond to X, or another carboxyl group may be used to bond to X.

[0058] "Hydroxy-linked amino acid" means an amino acid linked to X through the oxygen atom of the hydroxyl group.

[0059] "Thiol-linked amino acid" means an amino acid linked to X through the sulfur atom of the thiol group.

[0060] "Amino acid bonded through an amide group" means an amino acid bonded to X through the nitrogen atom of the amide group.

[0061] Examples of amino acids include basic amino acids such as lysine, ornithine, arginine, histidine, citrulline, diaminobutanoic acid, and diaminopropanoic 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 known as "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, and sarcosine. Amino acids may or may not have substituents on their amino and / or carboxyl groups. That is, unless otherwise specified, the term "amino acid" encompasses those having substituents on their amino and / or carboxyl groups. That is, the amino acid also includes those having a substituent on the amino group and / or carboxyl group of the above-mentioned amino acid. Examples of the substituent on the amino group in the amino acid include an optionally substituted alkoxycarbonyl group and an optionally substituted alkyl group. That is, the amino group in the amino acid may constitute, for example, an optionally substituted alkoxycarbonylamino group or an optionally substituted alkylamino group. Examples of the substituent on the amino group in the amino acid include, in particular, a tert-butoxycarbonyl group, a 9-fluorenylmethyloxycarbonyl group, and a benzyloxycarbonyl group. Examples of the substituent on the carboxyl group in the amino acid include an optionally substituted alkyl group or an amino group. That is, the carboxyl group in the amino acid may constitute, for example, an optionally substituted alkoxycarbonyl group or aminocarbonyl group. Examples of the substituent on the carboxyl group in the amino acid include, in particular, a methyl group, an ethyl group, a tert-butyl group, and a benzyl group.

[0062] "Agmatine" as R2 means agmatine bound to X by an appropriate bond. In addition, when X is an interatomic bond, the "bond between agmatine and X" in formula (I) shall be read as the "bond between agmatine and the D ring."

[0063] Agmatine as R2 includes agmatine bound at the amino group.

[0064] "Agmatine bound via an amino group" means agmatine bound to X via the nitrogen atom of the amino group. Any of the amino groups of agmatine may be used for binding to X. For example, the amino group of the guanidine moiety may be used for binding to X, or the N-4-amino group may be used for binding to X.

[0065] Agmatine may or may not have a substituent at its amino group. That is, unless otherwise specified, "agmatine" includes those having a substituent at its amino group. The above-mentioned description of the substituent at the amino group of amino acids can be applied mutatis mutandis to the substituent at the amino group of agmatine.

[0066] The "guanidine" as R2 means guanidine bonded to X by an appropriate bond. In addition, when X is an interatomic bond, the "bond between guanidine and X" in formula (I) is to be read as the "bond between guanidine and D ring."

[0067] Guanidine as R2 includes guanidine linked through an amino group.

[0068] "Amino-linked guanidine" means a guanidine linked to X at the nitrogen atom of the amino group.

[0069] Guanidine may or may not have a substituent on its amino group. That is, unless otherwise specified, "guanidine" includes those having a substituent on its amino group. For the substituent on the amino group of guanidine, the description of the substituent on the amino group of the amino acid described above can be applied mutatis mutandis. In addition, an example of the substituent on the amino group of guanidine is an optionally substituted alkylcarbonyl group. For the optionally substituted alkylcarbonyl group as a substituent on the amino group of guanidine, the description of the optionally substituted alkylcarbonyl group as an acyl group described above can be applied mutatis mutandis.

[0070] Specific examples of the structure represented by formula (R2-1) include ethylenediamine, propylenediamine, putrescine, and cadaverine when R3 and R4 are H. Specific examples of the structure represented by formula (R2-1) include ethylenediamine, propylenediamine, putrescine, and cadaverine when R3 and / or R4 are not H, in which the hydrogen atom of the amino group is substituted by R3 and / or R4.

[0071] Specific examples of the structure represented by formula (R2-2) include malonic acid, succinic acid, glutaric acid, adipic acid, fumaric acid, maleic acid, and citric acid, each of which has a hydrogen atom of a carboxyl group substituted with R5.

[0072] In one embodiment, Y may be NH and R1 may be a methyl group.

[0073] In one embodiment, X can be an atomic bond or an oxycarbonyl group, and R can be an amino-linked amino acid, an amino-linked agmatine, or an amino-linked guanidine. In one embodiment, specifically, X can be an atomic bond or an oxycarbonyl group, and R can be an amino-linked amino acid or an amino-linked agmatine.

[0074] In one embodiment, X may be an interatomic bond and R2 may be an amino acid linked through a carboxyl group.

[0075] In one embodiment, X may be an interatomic bond and R2 may be an amino acid linked through a hydroxyl group.

[0076] In one embodiment, X may be an interatomic bond and R2 may be an amino acid linked through a thiol group.

[0077] In one embodiment, X may be an interatomic bond and R2 may be an amino acid linked through an amide group.

[0078] In one embodiment, X may be an atomic bond or an oxycarbonyl group, and R2 may be a structure represented by formula (R2-1).

[0079] In one embodiment, X may be an interatomic bond, and R2 may be a structure represented by formula (R2-2).

[0080] In one embodiment, X may be an atomic bond, R1 may be a methyl group, R2 may be an amino acid linked through an amino group, agmatine linked through an amino group, guanidine linked through an amino group, or a structure represented by formula (R2-1). In one embodiment, particularly, X may be an atomic bond, R1 may be a methyl group, R2 may be an amino acid linked through an amino group, agmatine linked through an amino group, or a structure represented by formula (R2-1).

[0081] In one embodiment, X may be an oxycarbonyl group, R1 may be a methyl group, and R2 may be an amino acid linked via a carboxyl group or a structure represented by formula (R2-2).

[0082] In one embodiment, X may be an atomic bond, Y may be NH, R1 may be a methyl group, R2 may be an amino acid linked through an amino group, agmatine linked through an amino group, guanidine linked through an amino group, or a structure represented by formula (R2-1). In one embodiment, particularly, X may be an atomic bond, Y may be NH, R1 may be a methyl group, R2 may be an amino acid linked through an amino group, agmatine linked through an amino group, or a structure represented by formula (R2-1).

[0083] In one embodiment, X may be an oxycarbonyl group, Y may be NH, R1 may be a methyl group, and R2 may be an amino acid linked via a carboxyl group or a structure represented by formula (R2-2).

[0084] Component (B) is a compound represented by the following general formula (II). ｎ" and "Rn" (n is a positive integer) may be used interchangeably. ｎ " and "Xn" (n is a positive integer) may be used interchangeably.

[0085]

[0086] In formula (II), the cyclic structure located on the right side is also referred to as "D ring".

[0087] In formula (II), X1 represents an atomic bond or a methyleneoxy group (CH ２ The "methyleneoxy group" as X1 represents CH ２ is bonded to ring D, and O is bonded to X2. Note that when X2 is an interatomic bond, the "bond between O and X2" of a methyleneoxy group is to be read as "bond between O and R2."

[0088] In formula (II), X2 represents an atomic bond or a carbonyl group (C(=O)).

[0089] In formula (II), Y represents an oxygen atom (O) or a nitrogen atom (NH) bonded to a hydrogen atom.

[0090] In formula (II), R1 represents a hydrogen atom (H) or a methyl group.

[0091] In formula (II), R2 represents an amino acid, agmatine, guanidine, an aliphatic alcohol, a fatty acid, a structure represented by the above general formula (R2-1), or a structure represented by the above general formula (R2-2).

[0092] In formula (II), bc is CH—CH ２ Or C=CH.

[0093] Unless otherwise specified, for component (B), bc, X1, X2, Y, n, and R1 through R5 can each be independently selected.

[0094] The structure represented by formula (R2-1) and the structure represented by formula (R2-2) are as described above.

[0095] The "amino acid" as R2 in formula (II) means an amino acid bound to X2 via an appropriate bond. Note that the "bond between an amino acid and X2" in formula (II) is to be read as the "bond between an amino acid and X1" when X2 is an interatomic bond. Furthermore, the "bond between an amino acid and X2" in formula (II) is to be read as the "bond between an amino acid and the D ring" when X1 and X2 are interatomic bonds. The description of the "amino acid" as R2 in formula (I) can be applied mutatis mutandis to the "amino acid" as R2 in formula (II).

[0096] "Agmatine" as R2 in formula (II) means agmatine bound to X2 by an appropriate bond. Note that "the bond between agmatine and X2" in formula (II) shall be read as "the bond between agmatine and X1" when X2 is an interatomic bond. Furthermore, "the bond between agmatine and X2" in formula (II) shall be read as "the bond between agmatine and the D ring" when X1 and X2 are interatomic bonds. With regard to "agmatine" as R2 in formula (II), the description of "agmatine" as R2 in formula (I) can be applied mutatis mutandis.

[0097] "Guanidine" as R2 in formula (II) means guanidine bonded to X2 by an appropriate bond. Note that, when X2 is an interatomic bond, the "bond between guanidine and X2" in formula (II) shall be read as "the bond between guanidine and X1." Furthermore, when X1 and X2 are interatomic bonds, the "bond between guanidine and X2" in formula (II) shall be read as "the bond between guanidine and ring D." With regard to "guanidine" as R2 in formula (II), the description of "guanidine" as R2 in formula (I) can be applied mutatis mutandis.

[0098] The "aliphatic alcohol" as R2 in formula (II) means an aliphatic alcohol bonded to X2 via the oxygen atom of a hydroxyl group. Note that the "bond between an aliphatic alcohol and X2" in formula (II) is to be read as the "bond between an aliphatic alcohol and X1" when X2 is an interatomic bond. Furthermore, the "bond between an aliphatic alcohol and X2" in formula (II) is to be read as the "bond between an aliphatic alcohol and a D ring" when X1 and X2 are interatomic bonds.

[0099] The aliphatic alcohol may be a saturated aliphatic alcohol or an unsaturated aliphatic alcohol. The aliphatic alcohol may be linear or branched. Examples of the aliphatic alcohol include aliphatic alcohols having 2 to 26, 2 to 22, or 2 to 18 carbon atoms. Examples of the aliphatic alcohol particularly include aliphatic alcohols having 2 to 18 carbon atoms. Specific examples of the aliphatic alcohol include ethanol, propanol, isopropanol, butanol, isobutanol, sec-butanol, tert-butanol, pentanol, isopentanol, 2,3-dimethylpropanol, hexanol, heptanol, octanol, nonanol, decanol, undecyl alcohol, dodecyl alcohol, tridecyl alcohol, tetradecyl alcohol, pentadecyl alcohol, and hexadecyl alcohol. alcohol, cis-9-hexadecen-1-ol, heptadecyl alcohol, octadecyl alcohol, cis-9-octadecen-1-ol, cis,cis-9,12-octadecadien-1-ol, 9,12,15-octadecanetrien-1-ol, 6,9,12-octadecanetrien-1-ol, nonadecyl alcohol, eicosanol, heneicosanol, docosanol, tetracosanol, and hexacosanol.

[0100] The "fatty acid" as R2 in formula (II) means a fatty acid bonded to X2 via the oxygen atom of the OH of the carboxyl group. Note that the "bond between a fatty acid and X2" in formula (II) is to be read as the "bond between a fatty acid and X1" when X2 is an interatomic bond. Furthermore, the "bond between a fatty acid and X2" in formula (II) is to be read as the "bond between a fatty acid and a D ring" when X1 and X2 are interatomic bonds.

[0101] The fatty acid may be saturated or unsaturated. The fatty acid alcohol may be straight-chain or branched. Fatty acids include fatty acids having 2 to 26, 2 to 22, or 2 to 18 carbon atoms. Fatty acids particularly include fatty acids having 2 to 18 carbon atoms. Specific examples of fatty acids include acetic acid, propionic acid, succinic acid, butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, linoleic acid, α-linolenic acid, γ-linolenic acid, arachidic acid, arachidonic acid, behenic acid, lignoceric acid, nervonic acid, cerotic acid, eicosapentaenoic acid, docosapentaenoic acid, and docosahexaenoic acid.

[0102] In one embodiment, X1 may be an interatomic bond and X2 may be a carbonyl group.

[0103] In one embodiment, X1 may be a methyleneoxy group and X2 may be an interatomic bond.

[0104] In one embodiment, X1 may be an interatomic bond and X2 may be an interatomic bond.

[0105] In one embodiment, X1 may be a methyleneoxy group and X2 may be a carbonyl group.

[0106] In one embodiment, Y is NH and bc is CH—CH ２ , R1 may be H.

[0107] In one embodiment, X1 is an interatomic bond, X2 is a carbonyl group, Y is NH, and bc is CH—CH ２ , R1 may be H.

[0108] In one embodiment, X1 is a methyleneoxy group, X2 is an interatomic bond, Y is NH, and bc is CH—CH ２ , R1 may be H.

[0109] In one embodiment, X1 can be an atomic bond, X2 can be a carbonyl group, and R2 can be an amino-linked amino acid, an amino-linked agmatine, or an amino-linked guanidine. In one embodiment, specifically, X1 can be an atomic bond, X2 can be a carbonyl group, and R2 can be an amino-linked amino acid or an amino-linked agmatine.

[0110] In one embodiment, X1 may be a methyleneoxy group, X2 may be an interatomic bond, and R2 may be an amino acid linked through a carboxyl group.

[0111] In one embodiment, X1 can be an interatomic bond, X2 can be a carbonyl group, and R2 can be an aliphatic alcohol.

[0112] In one embodiment, X1 may be a methyleneoxy group, X2 may be an interatomic bond, and R2 may be a fatty acid.

[0113] In one embodiment, X1 may be an interatomic bond, X2 may be a carbonyl group, and R2 may be a structure represented by formula (R2-1).

[0114] In one embodiment, X1 may be a methyleneoxy group, X2 may be an interatomic bond, and R2 may be a structure represented by formula (R2-2).

[0115] In one embodiment, X1 is an interatomic bond, X2 is a carbonyl group, Y is NH, and bc is CH—CH ２ , R1 is H, and R2 may be an amino acid linked through an amino group, an agmatine linked through an amino group, a guanidine linked through an amino group, or a structure represented by formula (R2-1). In one embodiment, particularly, X1 is an atomic bond, X2 is a carbonyl group, Y is NH, and bc is CH—CH ２ , R1 is H, and R2 may be an amino acid linked through an amino group, agmatine linked through an amino group, or a structure represented by formula (R2-1).

[0116] In one embodiment, X1 is a methyleneoxy group, X2 is an interatomic bond, Y is NH, and bc is CH—CH ２R1 may be H, and R2 may be an amino acid bonded via a carboxyl group, a fatty acid having 2 to 18 carbon atoms, or a structure represented by formula (R2-2).

[0117] In one embodiment, X1 can be an interatomic bond, X2 can be an interatomic bond, and R2 can be guanidine linked through an amino group.

[0118] In one embodiment, X1 can be an interatomic bond, X2 can be an interatomic bond, Y can be an oxygen atom (O), bc can be C=CH, R1 can be a methyl group, and R2 can be a guanidine linked through an amino group.

[0119] Specific examples of X, Y, n, and R1 to R5 of component (A) include X, Y, n, and R1 to R5 of the compounds represented by the formulae (Compound 1) to (Compound 20), (Compound 23), (Compound 26) to (Compound 37), (Compound 80), and (Compound 82) to (Compound 85) described below. That is, specific examples of X, Y, n, and R1 to R5 of component (A) may be selected from X, Y, n, and R1 to R5 of the compounds represented by the formulae (Compound 1) to (Compound 20), (Compound 23), (Compound 26) to (Compound 37), (Compound 80), and (Compound 82) to (Compound 85) described below.

[0120] Specific examples of b-c, X1, X2, Y, n, and R1 to R5 of component (B) include b-c, X1, X2, Y, n, and R1 to R5 of the compounds represented by the formulae (Compound 1) to (Compound 20), (Compound 23), (Compound 26) to (Compound 80), and (Compound 82) to (Compound 90) described below. That is, specific examples of b-c, X1, X2, Y, n, and R1 to R5 of component (B) may be selected from b-c, X1, X2, Y, n, and R1 to R5 of the compounds represented by the formulae (Compound 1) to (Compound 20), (Compound 23), (Compound 26) to (Compound 80), and (Compound 82) to (Compound 90) described below.

[0121] Specific examples of component (A) or (B) include compounds represented by the formulae (Compound 1) to (Compound 20), (Compound 23), (Compound 26) to (Compound 80), and (Compound 82) to (Compound 90) described below. Specific examples of component (A) or (B) include compounds represented by the formulae (Compound 1) to (Compound 20), (Compound 23), (Compound 26) to (Compound 61), (Compound 65) to (Compound 80), and (Compound 83) to (Compound 90) described below. Specific examples of component (A) or (B) include compounds represented by the formulae (Compound 1) to (Compound 8), (Compound 27) to (Compound 30), (Compound 38) to (Compound 56), and (Compound 66) to (Compound 77) described below. The compounds represented by the formulae (Compound 1) to (Compound 20), (Compound 23), (Compound 26) to (Compound 37), (Compound 80), and (Compound 82) to (Compound 85) may all be examples of component (A) or (B). The compounds represented by the formulae (Compound 38) to (Compound 79) and (Compound 86) to (Compound 90) may all be examples of component (B). In one embodiment, component (A) may exclude the compound represented by formula (Compound 85). In one embodiment, component (B) may exclude the compounds represented by formulae (Compound 41), (Compound 50), (Compound 52), (Compound 54), (Compound 55), (Compound 58), (Compound 65), (Compound 77), (Compound 85), (Compound 86), (Compound 87), and (Compound 90). That is, in one embodiment, specific examples of component (A) or (B) include compounds represented by formulae (Compound 1) to (Compound 20), (Compound 23), (Compound 26) to (Compound 40), (Compound 42) to (Compound 49), (Compound 51), (Compound 53), (Compound 56), (Compound 57), (Compound 59) to (Compound 64), (Compound 66) to (Compound 76), (Compound 78) to (Compound 80), (Compound 82) to (Compound 84), (Compound 88), and (Compound 89). In one embodiment, compounds represented by formulae (Compound 41), (Compound 50), (Compound 52), (Compound 54), (Compound 55), and (Compound 77) may be excluded from component (B).That is, in one embodiment, specific examples of component (A) or (B) include compounds represented by formulae (Compound 1) to (Compound 20), (Compound 23), (Compound 26) to (Compound 40), (Compound 42) to (Compound 49), (Compound 51), (Compound 53), (Compound 56) to (Compound 76), (Compound 78) to (Compound 80), and (Compound 82) to (Compound 90).

[0122] When component (A) or (B) can form a salt, component (A) or (B) 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. Furthermore, the term "component (B)" may refer to component (B) in its free form, its salt, or a combination thereof. 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. 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 formic acid, 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 their halides; and salts with organic sulfonic acids such as methanesulfonic acid, benzenesulfonic acid, and p-toluenesulfonic acid. Examples of halides include heptafluorobutyric acid. As the salt, one type of salt may be used, or two or more types of salts may be used in combination.

[0123] Furthermore, when component (A) or (B) can form a hydrate, component (A) or (B) 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. Furthermore, the term "component (B)" (e.g., "component (B) in free form" or "salt of component (B)") may encompass both the non-hydrate and the hydrate unless otherwise specified.

[0124] Component (A) or (B) may be in any form, such as an ion, when used.

[0125] As component (A) or (B), one substance may be used, or two or more substances may be used in combination. When two or more components are selected as component (A) or (B), the "amount" or "concentration" of component (A) or (B) may mean the total amount or concentration of the selected components, unless otherwise specified.

[0126] Component (A) or (B) may be commercially available or may be obtained by appropriate production. The method for producing component (A) or (B) is not particularly limited. Component (A) or (B) can be produced, for example, by known methods. Specifically, component (A) or (B) can be produced, for example, by chemical synthesis, enzymatic reaction, fermentation, extraction, or a combination thereof. Component (A) or (B) may be purified to a desired degree or not. That is, purified products may be used as component (A) or (B), or materials containing component (A) or (B) may be used. Specific examples of materials containing component (A) or (B) include fermentation products such as culture broth, bacterial cells, and culture supernatant obtained by culturing microorganisms capable of producing component (A) or (B), agricultural, aquatic, and livestock products containing component (A) or (B), and processed products thereof. Examples of processed products include those obtained by subjecting materials such as the above-mentioned fermentation products to treatments such as concentration, dilution, drying, fractionation, extraction, purification, etc. As component (A) or (B), for example, a material having a content of component (A) or (B) 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.

[0127] Component (C) is an amino acid fermentation by-product.

[0128] "Amino acid fermentation by-products" is a general term for the liquid remaining after separating amino acids from an amino acid fermentation broth (also referred to as "amino acid fermentation by-product liquid"), its concentrate, and fractions thereof. The concentrate may be, for example, a liquid (i.e., a concentrated liquid) or a solid (i.e., a dried product). The fraction is not particularly limited as long as it contains a fraction having the function of an active ingredient as described below. The term "fraction of a concentrate" may be used interchangeably with the term "concentrate of a fraction."

[0129] "Amino acid fermentation broth" means a culture broth containing amino acids.

[0130] The amino acids for the amino acid fermentation by-product and the amino acid fermentation liquor include lysine, tryptophan, threonine, valine, leucine, and isoleucine. The amino acids for the amino acid fermentation by-product and the amino acid fermentation liquor may all be L-amino acids. The amino acids separated from the amino acid fermentation liquor may all be free amino acids, salts thereof, or combinations thereof.

[0131] The amino acid fermentation broth can be obtained by culturing a microorganism capable of producing an amino acid.

[0132] The term "microorganism capable of producing an amino acid" may refer to a microorganism capable of producing a target amino acid when cultured in a medium and accumulating the amino acid in the medium to an extent that it can be separated.

[0133] Examples of microorganisms include bacteria. Examples of bacteria include bacteria belonging to the Enterobacteriaceae family and coryneform bacteria. Examples of bacteria belonging to the Enterobacteriaceae family include bacteria of the genus Escherichia, such as Escherichia coli, and bacteria of the genus Pantoea, such as Pantoea ananatis. Examples of coryneform bacteria include bacteria of the genus Corynebacterium, such as Corynebacterium glutamicum.

[0134] Microorganisms capable of producing amino acids may be those that inherently have this ability, or may be those that have been modified to have this ability. Microorganisms capable of producing amino acids can be obtained, for example, by imparting amino acid production ability to a microorganism or by enhancing the amino acid production ability of a microorganism. Imparting or enhancing amino acid production ability (specifically, L-amino acid production ability) can be carried out, for example, by methods that have traditionally been used to breed amino acid-producing bacteria (see Amino Acid Fermentation, Academic Press Center, first published May 30, 1986, pp. 77-100). Methods for imparting or enhancing amino acid production ability (specifically, L-amino acid production ability) are disclosed, for example, in US2018-0282773 and WO2018 / 030507.

[0135] Specific examples of L-amino acid-producing bacteria and methods for imparting or enhancing L-amino acid-producing ability are given below. The properties of L-amino acid-producing bacteria and modifications for imparting or enhancing L-amino acid-producing ability as exemplified below may be used alone or in appropriate combination.

[0136] <L-Threonine-Producing Bacteria> Methods for imparting or enhancing L-threonine-producing ability include, for example, modifying bacteria to enhance the activity of one or more enzymes selected from L-threonine biosynthetic enzymes. Examples of such enzymes include, but are not limited to, aspartokinase III (lysC), aspartate semialdehyde dehydrogenase (asd), aspartokinase I (thrA), homoserine kinase (thrB), threonine synthase (thrC), and aspartate aminotransferase (aspartate transaminase) (aspC). Among these enzymes, enhancing the activity of one or more enzymes selected from aspartokinase III, aspartate semialdehyde dehydrogenase, aspartokinase I, homoserine kinase, aspartate aminotransferase, and threonine synthase is preferred. The L-threonine biosynthetic genes may be introduced into a strain in which threonine degradation is suppressed, such as the E. coli TDH6 strain (JP 2001-346578 A), which is deficient in threonine dehydrogenase activity.

[0137] The activity of L-threonine biosynthetic enzymes is inhibited by the final product, L-threonine. Therefore, to construct an L-threonine-producing bacterium, it is preferable to modify the L-threonine biosynthetic genes so that they are not subject to feedback inhibition by L-threonine. The thrA, thrB, and thrC genes constitute the threonine operon, which forms an attenuator structure. Expression of the threonine operon is inhibited by isoleucine and threonine in the culture medium and is suppressed by attenuation. Enhanced expression of the threonine operon can be achieved by removing the leader sequence or attenuator of the attenuation region (Lynn, SP, Burton, WS, Donohue, TJ, Gould, RM, Gumport, RI, and Gardner, JFJ Mol. Biol. 194:59-69 (1987); WO02 / 26993; WO2005 / 049808; WO2003 / 097839).

[0138] Although a native promoter exists upstream of the threonine operon, this promoter may be replaced with a non-natural promoter (WO98 / 04715). Alternatively, the threonine operon may be constructed so that the genes involved in threonine biosynthesis are expressed under the control of a lambda phage repressor and promoter (EP0593792B). Bacteria engineered to be immune to feedback inhibition by L-threonine can also be obtained by selecting strains resistant to α-amino-β-hydroxyvaleric acid (AHV), an L-threonine analog.

[0139] The threonine operon thus modified to be free from feedback inhibition by L-threonine preferably has an increased expression level in the host by increasing its copy number or by linking it to a strong promoter. The copy number can be increased by introducing a plasmid containing the threonine operon into the host. Alternatively, the copy number can be increased by transferring the threonine operon onto the host genome using a transposon, Mu phage, or the like.

[0140] Methods for imparting or enhancing L-threonine-producing ability also include methods for imparting L-threonine resistance or L-homoserine resistance to a host. Conferring resistance can be achieved, for example, by enhancing the expression of a gene that confers resistance to L-threonine or a gene that confers resistance to L-homoserine. Examples of genes that confer resistance include the rhtA gene (Res. Microbiol. 154:123-135 (2003)), rhtB gene (EP0994190A), rhtC gene (EP1013765A), yfiK gene, and yeaS gene (EP1016710A). For methods of imparting L-threonine resistance to a host, see the methods described in EP0994190A and WO90 / 04636.

[0141] Specific examples of L-threonine-producing bacteria or parent strains for deriving them include E. coli TDH-6 / pVIC40 (VKPM B-3996; U.S. Pat. Nos. 5,175,107 and 5,705,371), E. coli 472T23 / pYN7 (ATCC 98081; U.S. Pat. No. 5,631,157), E. coli NRRL B-21593 (U.S. Pat. No. 5,939,307), E. coli FERM BP-3756 (U.S. Pat. No. 5,474,918), E. coli FERM BP-3519 and FERM BP-3520 (U.S. Pat. No. 5,376,538), E. coli MG442 (Gusyatiner et al., Genetika (in Russian), 14, 947-956 (1978)), E. coli VL643 and VL2055 (EP1149911A), and E. coli VKPM B-5318 (EP0593792B).

[0142] The VKPM B-3996 strain is a strain in which the plasmid pVIC40 has been introduced into the TDH-6 strain. The TDH-6 strain is sucrose-utilizing, lacks the thrC gene, and has a leaky mutation in the ilvA gene. The TDH-6 strain also has a mutation in the rhtA gene that confers resistance to high concentrations of threonine or homoserine. The plasmid pVIC40 is a thrA vector derived from RSF1010, which contains a mutant thrA gene encoding aspartokinase homoserine dehydrogenase I that is resistant to feedback inhibition by threonine and a wild-type thrBC gene. *This strain is a plasmid into which the BC operon has been inserted (U.S. Patent No. 5,705,371). The mutant thrA gene encodes aspartokinase homoserine dehydrogenase I, which is substantially desensitized to threonine feedback inhibition. Strain B-3996 was deposited on November 19, 1987, at the All-Union Scientific Center of Antibiotics (Nagatinskaya Street 3-A, 117105 Moscow, Russia) under accession number RIA 1867. This strain was also deposited on April 7, 1987, at the Russian National Collection of Industrial Microorganisms (VKPM) (FGUP GosNII Genetika, 1 Dorozhny proezd., 1 Moscow 117545, Russia) under accession number VKPM B-3996.

[0143] The VKPM B-5318 strain is non-auxotrophic for isoleucine and harbors the pPRT614 plasmid, in which the regulatory region of the threonine operon in the pVIC40 plasmid has been replaced with a temperature-sensitive lambda phage C1 repressor and PR promoter. VKPM B-5318 was deposited on May 3, 1990, with the Russian National Collection of Industrial Microorganisms (VKPM) (FGUP GosNII Genetika, 1 Dorozhny proezd., 1 Moscow 117545, Russia) under the accession number VKPM B-5318.

[0144] The thrA gene encoding aspartokinase homoserine dehydrogenase I of E. coli has been elucidated (nucleotide positions 337-2799, GenBank accession NC_000913.2, gi: 49175990). The thrA gene is located between the thrL and thrB genes on the chromosome of E. coli K-12. The thrB gene encoding homoserine kinase of Escherichia coli has been elucidated (nucleotide positions 2801-3733, GenBank accession NC_000913.2, gi: 49175990). The thrB gene is located between the thrA and thrC genes on the chromosome of E. coli K-12. The thrC gene encoding threonine synthase in E. coli has been elucidated (nucleotide positions 3734-5020, GenBank accession number NC_000913.2, gi: 49175990). The thrC gene is located between the thrB gene and the yaaX open reading frame on the chromosome of E. coli K-12. The thrA gene contains a mutant thrA gene encoding aspartokinase homoserine dehydrogenase I that is resistant to feedback inhibition by threonine, and the wild-type thrBC gene. * The BC operon can be obtained from the well-known plasmid pVIC40 (US Pat. No. 5,705,371) present in the threonine-producing strain E. coli VKPM B-3996.

[0145] The E. coli rhtA gene is located at 18 min on the E. coli chromosome, close to the glnHPQ operon, which encodes components of the glutamine transport system. The rhtA gene is identical to ORF1 (ybiF gene, nucleotide positions 764-1651, GenBank accession number AAA218541, gi:440181) and is located between the pexB and ompX genes. The expression unit for the protein encoded by ORF1 is called the rhtA gene (rht: resistant to homoserine and threonine). Furthermore, the rhtA23 mutation, which confers resistance to high concentrations of threonine or homoserine, has been found to be a G→A substitution at position -1 relative to the ATG start codon (ABSTRACTS of the 17th International Congress of Biochemistry and Molecular Biology in conjugation with Annual Meeting of the American Society for Biochemistry and Molecular Biology, San Francisco, California, August 24-29, 1997, abstract No. 457, EP1013765A).

[0146] The asd gene of E. coli has already been identified (nucleotide positions 3572511 to 3571408, GenBank accession number NC_000913.1, gi:16131307), and can be obtained by PCR using primers designed based on the nucleotide sequence of the gene (White, TJ et al., Trends Genet., 5, 185 (1989)). The asd genes of other microorganisms can also be obtained in a similar manner.

[0147] The aspC gene of E. coli has also been identified (nucleotide positions 983742 to 984932, GenBank accession number NC_000913.1, gi:16128895), and can be obtained by PCR using primers designed based on the nucleotide sequence of this gene. The aspC genes of other microorganisms can also be obtained in a similar manner.

[0148] Furthermore, examples of coryneform bacteria capable of producing L-threonine include Corynebacterium acetoacidophilum AJ12318 (FERM BP-1172; US Pat. No. 5,188,949).

[0149] <L-lysine-producing bacteria> Examples of methods for imparting or enhancing L-lysine-producing ability include a method of modifying bacteria so that the activity of one or more enzymes selected from L-lysine biosynthetic enzymes is increased. Such enzymes include, but are not limited to, dihydrodipicolinate synthase (dapA), aspartokinase III (lysC), dihydrodipicolinate reductase (dapB), diaminopimelate decarboxylase (lysA), diaminopimelate dehydrogenase (ddh) (U.S. Pat. No. 6,040,160), phosphoenolpyruvate carboxylase (ppc), aspartate semialdehyde dehydrogenase (asd), aspartate aminotransferase (aspartate transaminase), and the like. transaminase (aspC), diaminopimelate epimerase (dapF), tetrahydrodipicolinate succinylase (dapD), succinyl-diaminopimelate deacylase (dapE), and aspartase (aspA) (EP 1253195 A).Among these enzymes, it is preferable to enhance the activity of one or more enzymes selected from dihydrodipicolinate reductase, diaminopimelate decarboxylase, diaminopimelate dehydrogenase, phosphoenolpyruvate carboxylase, aspartate aminotransferase, diaminopimelate epimerase, aspartate semialdehyde dehydrogenase, tetrahydrodipicolinate succinylase, and succinyldiaminopimelate deacylase. Furthermore, in the L-lysine-producing bacterium or a parent strain for deriving it, the expression levels of a gene involved in energy efficiency (cyo) (EP 1170376 A), genes encoding nicotinamide nucleotide transhydrogenase (pntAB) (U.S. Pat. No. 5,830,716), the ybjE gene (WO 2005 / 073390), or a combination thereof may be increased. Since aspartokinase III (lysC) is subject to feedback inhibition by L-lysine, its activity can be enhanced by utilizing a mutant lysC gene encoding aspartokinase III desensitized to feedback inhibition by L-lysine (U.S. Patent No. 5,932,453). Examples of aspartokinase III desensitized to feedback inhibition by L-lysine include aspartokinase III derived from Escherichia coli having one or more of the following mutations: a substitution of isoleucine for methionine at position 318, an aspartic acid for glycine at position 323, or an isoleucine for threonine at position 352 (U.S. Patent Nos. 5,661,012 and 6,040,160). Furthermore, since dihydrodipicolinate synthase (dapA) is subject to feedback inhibition by L-lysine, its activity can be enhanced by utilizing a mutant dapA gene encoding dihydrodipicolinate synthase desensitized to feedback inhibition by L-lysine.An example of a dihydrodipicolinate synthase that is desensitized to feedback inhibition by L-lysine is dihydrodipicolinate synthase derived from Escherichia coli that has a mutation in which the histidine residue at position 118 is substituted with a tyrosine residue (U.S. Pat. No. 6,040,160).

[0150] Another method for imparting or enhancing L-lysine-producing ability is to modify a bacterium so as to reduce the activity of one or more enzymes selected from enzymes that catalyze reactions that branch off from the L-lysine biosynthetic pathway to produce compounds other than L-lysine. Examples of such enzymes include, but are not limited to, homoserine dehydrogenase, lysine decarboxylase (U.S. Pat. No. 5,827,698), and malic enzyme (WO2005 / 010175).

[0151] Furthermore, methods for imparting or enhancing L-lysine-producing ability to coryneform bacteria include, for example, modifying bacteria to enhance the activity of the lysine export system (lysE) (WO 97 / 23597). The lysE gene of Corynebacterium glutamicum ATCC 13032 corresponds to the complementary sequence of the sequence at positions 1329712 to 1330413 in the genome sequence registered in the NCBI database as GenBank accession NC_006958 (VERSION NC_006958.1 GI:62388892). The LysE protein of Corynebacterium glutamicum ATCC13032 is registered as GenBank accession YP_225551 (YP_225551.1 GI:62390149).

[0152] Furthermore, examples of L-lysine-producing bacteria or parent strains for deriving them include mutant strains resistant to L-lysine analogs. L-lysine analogs inhibit the growth of bacteria such as Enterobacteriaceae bacteria and coryneform bacteria, but this inhibition is completely or partially relieved when L-lysine is coexistent in the medium. L-lysine analogs include, but are not limited to, oxalysine, lysine hydroxamate, S-(2-aminoethyl)-L-cysteine ​​(AEC), γ-methyllysine, and α-chlorocaprolactam. Mutant strains resistant to these lysine analogs can be obtained by subjecting bacteria to conventional artificial mutagenesis treatments.

[0153] Specific examples of L-lysine-producing bacteria or parent strains for deriving them include E. coli AJ11442 (FERM BP-1543, NRRL B-12185; U.S. Pat. No. 4,346,170) and E. coli VL611. In these strains, feedback inhibition of aspartokinase by L-lysine is desensitized.

[0154] A specific example of an L-lysine-producing bacterium or a parent strain for deriving it is the E. coli WC196 strain. The WC196 strain was developed by conferring AEC resistance to the W3110 strain, derived from E. coli K-12 (U.S. Patent No. 5,827,698). The WC196 strain was designated E. coli AJ13069 and deposited on December 6, 1994, with the National Institute of Bioscience and Human-Technology, Agency of Industrial Science and Technology (now the Patent Organism Depositary, National Institute of Technology and Evaluation, Japan, 2-5-8 Kazusa Kamatari, Kisarazu City, Chiba Prefecture, Japan, Postal Code: 292-0818, Address: Room 120) under Accession No. FERM P-14690. On September 29, 1995, the deposit was transferred to an international deposit under the Budapest Treaty and assigned Accession No. FERM BP-5252 (U.S. Patent No. 5,827,698).

[0155] Preferred L-lysine-producing bacteria include E. coli WC196ΔcadAΔldc and E. coli WC196ΔcadAΔldc / pCABD2 ( WO 2010 / 061890 ). WC196ΔcadAΔldc is a strain constructed by disrupting the cadA and ldcC genes encoding lysine decarboxylase from the WC196 strain. WC196ΔcadAΔldc / pCABD2 is a strain constructed by introducing the plasmid pCABD2 ( U.S. Patent No. 6,040,160 ), which contains lysine biosynthetic genes, into WC196ΔcadAΔldc. WC196ΔcadAΔldc was designated AJ110692 and deposited internationally on October 7, 2008, at the Patent Organism Depositary of the National Institute of Advanced Industrial Science and Technology (currently the Patent Organism Depositary of the National Institute of Technology and Evaluation, Room 120, 2-5-8 Kazusa Kamatari, Kisarazu City, Chiba Prefecture, Japan, postal code: 292-0818) under accession number FERM BP-11027. pCABD2 contains a mutant dapA gene derived from Escherichia coli that has a mutation (H118Y) that relieves feedback inhibition by L-lysine and encodes dihydrodipicolinate synthase (DDPS), a mutant lysC gene derived from Escherichia coli that has a mutation (T352I) that relieves feedback inhibition by L-lysine and encodes aspartokinase III, a dapB gene derived from Escherichia coli that encodes dihydrodipicolinate reductase, and a ddh gene derived from Brevibacterium lactofermentum that encodes diaminopimelate dehydrogenase.

[0156] Another preferred L-lysine-producing bacterium is the E. coli AJIK01 strain (NITE BP-01520). The AJIK01 strain was designated E. coli AJ111046 and deposited on January 29, 2013, with the Patent Microorganisms Depositary, National Institute of Technology and Evaluation (Postal Code: 292-0818, Address: Room 122, 2-5-8 Kazusa Kamatari, Kisarazu City, Chiba Prefecture, Japan). It was transferred to international deposit under the Budapest Treaty on May 15, 2014, and assigned accession number NITE BP-01520.

[0157] Examples of coryneform bacteria capable of producing L-lysine include AEC-resistant mutants (Corynebacterium glutamicum (Brevibacterium lactofermentum) AJ11082 (NRRL B-11470) strain, etc.; JP-B-56-1914, JP-B-56-1915, JP-B-57-14157, JP-B-57-14158, JP-B-57-30474, JP-B-58-10075, JP-B-59-4993, JP-B-61-35840, JP-B-62-24074, JP-B-62-36673, JP-B-5-11958, JP-B-7-112437, JP-B-59-11458, JP-B-59-12 ... Hei 7-112438); mutant strains that require amino acids such as L-homoserine for growth (JP 48-28078, JP 56-6499); mutant strains that are resistant to AEC and also require amino acids such as L-leucine, L-homoserine, L-proline, L-serine, L-arginine, L-alanine, and L-valine (U.S. Pat. No. 3,708,395, No. 3,825,472); mutants resistant to DL-α-amino-ε-caprolactam, α-amino-lauryllactam, aspartic acid analogs, sulfonamides, quinoids, and N-lauroylleucine; mutants resistant to oxaloacetate decarboxylase inhibitors or respiratory enzyme inhibitors (JP Patent Publication Nos. 50-53588, 50-31093, 52-102498, 53-9394, 53-86089, 53-97); 83, JP-A-55-9759, JP-A-56-32995, JP-A-56-39778, JP-B-53-43591, JP-B-53-1833); mutants requiring inositol or acetate (JP-A-55-9784, JP-A-56-8692); mutants sensitive to fluoropyruvic acid or temperatures above 34°C (JP-A-55-9783, JP-A-53-86090); and mutants resistant to ethylene glycol (U.S. Pat. No. 4,411,997).

[0158] <L-leucine-producing bacteria> Methods for imparting or enhancing L-leucine-producing ability include, for example, modifying bacteria so that the activity of one or more enzymes selected from L-leucine biosynthetic enzymes is increased. Examples of such enzymes include, but are not limited to, enzymes encoded by genes in the leuABCD operon. Furthermore, for example, a mutant leuA gene encoding isopropyl malate synthase that is desensitized to feedback inhibition by L-leucine (U.S. Patent No. 6,403,342) can be suitably used to enhance enzyme activity.

[0159] Specific examples of L-leucine-producing bacteria or parent strains for deriving them include leucine-resistant E. coli strains (e.g., strain 57 (VKPM B-7386; U.S. Pat. No. 6,124,121)), E. coli strains resistant to leucine analogs such as β-2-thienylalanine, 3-hydroxyleucine, 4-azaleucine, and 5,5,5-trifluoroleucine (JP-B-62-34397 and JP-A-8-70879), E. coli strains obtained by the genetic engineering method described in WO96 / 06926, and strains belonging to the genus Escherichia such as E. coli H-9068 (JP-A-8-70879).

[0160] An example of a coryneform bacterium capable of producing L-leucine is Corynebacterium glutamicum (Brevibacterium lactofermentum) AJ3718 (FERM P-2516), which is resistant to 2-thiazolealanine and β-hydroxyleucine and is auxotrophic for isoleucine and methionine.

[0161] <L-Isoleucine-producing bacteria> Methods for imparting or enhancing L-isoleucine-producing ability include, for example, modifying bacteria to increase the activity of one or more enzymes selected from L-isoleucine biosynthetic enzymes, including, but not limited to, threonine deaminase and acetohydroxyacid synthase (JP-A-2-458, EP-0356739A, U.S. Pat. No. 5,998,178).

[0162] Specific examples of L-isoleucine-producing bacteria or parent strains for deriving them include Escherichia bacteria such as mutants resistant to 6-dimethylaminopurine (Japanese Patent Laid-Open No. 5-304969), mutants resistant to isoleucine analogs such as thiaisoleucine and isoleucine hydroxamate, and mutants resistant to isoleucine analogs as well as DL-ethionine and / or arginine hydroxamate (Japanese Patent Laid-Open No. 5-130882).

[0163] Examples of coryneform bacteria capable of producing L-isoleucine include coryneform bacteria in which the brnE gene encoding a branched-chain amino acid excretion protein has been amplified (Japanese Patent Application Laid-Open No. 2001-169788), coryneform bacteria in which L-isoleucine production ability has been imparted by protoplast fusion with an L-lysine-producing bacterium (Japanese Patent Application Laid-Open No. 62-74293), coryneform bacteria in which homoserine dehydrogenase activity has been enhanced (Japanese Patent Application Laid-Open No. 62-91193), threonine hydroxamate-resistant strains (Japanese Patent Application Laid-Open No. 62-195293), α-ketomalone-resistant strains (Japanese Patent Application Laid-Open No. 61-15695), methyllysine-resistant strains (Japanese Patent Application Laid-Open No. 61-15696), and Corynebacterium glutamicum (Brevibacterium flavum) AJ12149 (FERM BP-759; U.S. Pat. No. 4,656,135).

[0164] <L-valine-producing bacteria> Methods for imparting or enhancing L-valine-producing ability include, for example, modifying bacteria to increase the activity of one or more enzymes selected from L-valine biosynthetic enzymes. Such enzymes include, but are not limited to, enzymes encoded by genes in the ilvGMEDA operon and ilvBNC operon. ilvBN encodes acetohydroxyacid synthase, and ilvC encodes isomeroductase (WO 00 / 50624). The ilvGMEDA operon and ilvBNC operon are subject to expression repression (attenuation) by L-valine, L-isoleucine, and / or L-leucine. Therefore, to enhance enzyme activity, it is preferable to remove or modify the region required for attenuation to release the expression repression caused by the resulting L-valine. Furthermore, threonine deaminase encoded by the ilvA gene is an enzyme that catalyzes the deamination reaction from L-threonine to 2-ketobutyric acid, which is the rate-limiting step in the L-isoleucine biosynthesis pathway. Therefore, for L-valine production, it is preferable that the ilvA gene is disrupted or the like to reduce threonine deaminase activity.

[0165] Another method for imparting or enhancing L-valine-producing ability is to modify a bacterium so as to reduce the activity of one or more enzymes selected from enzymes that catalyze reactions that branch off from the L-valine biosynthetic pathway to produce compounds other than L-valine. Examples of such enzymes include, but are not limited to, threonine dehydratase involved in L-leucine synthesis and enzymes involved in D-pantothenic acid synthesis (WO 00 / 50624).

[0166] Specific examples of L-valine-producing bacteria or parent strains for deriving them include E. coli strains modified to overexpress the ilvGMEDA operon (US Pat. No. 5,998,178).

[0167] Furthermore, L-valine-producing bacteria or parent strains for deriving them also include strains having a mutation in aminoacyl-tRNA synthetase (U.S. Pat. No. 5,658,766). An example of such a strain is E. coli VL1970, which has a mutation in the ileS gene encoding isoleucine-tRNA synthetase. E. coli VL1970 was deposited on June 24, 1988, with the Russian National Collection of Industrial Microorganisms (VKPM) (FGUP GosNII Genetika, 1 Dorozhny proezd., 1 Moscow 117545, Russia) under accession number VKPM B-4411. Furthermore, L-valine-producing bacteria or parent strains for deriving them also include strains that require lipoic acid for growth and / or that can tolerate H. + and mutant strains lacking -ATPase (WO96 / 06926).

[0168] L-valine-producing bacteria or parent strains for deriving them also include strains resistant to amino acid analogs, etc. Examples of such strains include coryneform bacterial strains that are L-isoleucine and L-methionine auxotrophic, resistant to D-ribose, purine ribonucleosides, or pyrimidine ribonucleosides, and capable of producing L-valine (FERM P-1841, FERM P-29) (JP 53-025034), coryneform bacterial strains that are resistant to polyketoides (FERM P-1763, FERM P-1764) (JP 06-065314), and coryneform bacterial strains that are resistant to L-valine in a medium containing acetate as the sole carbon source and sensitive to pyruvate analogs (e.g., fluoropyruvic acid) in a medium containing glucose as the sole carbon source (FERM BP-3006, FERM BP-3007) (JP Patent No. 3006929).

[0169] <L-tryptophan-producing bacteria> Methods for imparting or enhancing L-tryptophan-producing ability include, for example, modifying bacteria so that the activity of one or more enzymes selected from L-tryptophan biosynthetic enzymes is increased.

[0170] L-tryptophan biosynthetic enzymes include, but are not limited to, 3-deoxy-D-arabinoheptulosonate-7-phosphate synthase (aroG), 3-dehydroquinate synthase (aroB), shikimate dehydrogenase (aroE), shikimate kinase (aroL), 5-enolpyruvylshikimate-3-phosphate synthase (aroA), and chorismate synthase (aroC), which are biosynthetic enzymes common to aromatic amino acids (EP 763127B). Expression of the genes encoding these enzymes is controlled by the tyrosine repressor (tyrR), and the activity of these enzymes may be enhanced by deleting the tyrR gene (EP 763127B).

[0171] L-tryptophan biosynthetic enzymes include, but are not limited to, anthranilate synthase (trpE), tryptophan synthase (trpAB), and phosphoglycerate dehydrogenase (serA). For example, L-tryptophan production ability can be imparted or enhanced by introducing DNA containing the tryptophan operon. Tryptophan synthase consists of α and β subunits encoded by the trpA and trpB genes, respectively. Since anthranilate synthase is subject to feedback inhibition by L-tryptophan, its activity can be enhanced by using a gene encoding the enzyme with a mutation introduced that relieves the feedback inhibition. Since phosphoglycerate dehydrogenase is subject to feedback inhibition by L-serine, its activity can be enhanced by using a gene encoding the enzyme with a mutation introduced that relieves the feedback inhibition. Furthermore, L-tryptophan-producing ability may be imparted or enhanced by increasing the expression of an operon (ace operon) consisting of malate synthase (aceB), isocitrate lyase (aceA), and isocitrate dehydrogenase kinase / phosphatase (aceK) (WO2005 / 103275).

[0172] L-tryptophan-producing bacteria may be modified to reduce biosynthesis of aromatic amino acids other than L-tryptophan. Furthermore, L-tryptophan-producing bacteria may be modified to enhance uptake systems for by-products. Examples of by-products include aromatic amino acids other than L-tryptophan. Examples of genes encoding by-product uptake systems include the pheP gene encoding the L-phenylalanine uptake system and the tyrP gene encoding the L-tyrosine uptake system (EP1484410).

[0173] Specific examples of L-tryptophan-producing bacteria or parent strains for deriving them include E. coli JP4735 / pMU3028 (DSM10122) and JP6015 / pMU91 (DSM10123) carrying a mutant trpS gene encoding a partially inactivated tryptophanyl-tRNA synthetase (U.S. Pat. No. 5,756,345), E. coli SV164 carrying a trpE allele encoding an anthranilate synthase that is not subject to feedback inhibition by tryptophan, E. coli SV164 (pGH5) carrying a serA allele encoding a phosphoglycerate dehydrogenase that is not subject to feedback inhibition by serine and a trpE allele encoding an anthranilate synthase that is not subject to feedback inhibition by tryptophan (U.S. Pat. No. 6,180,373), and a strain into which a tryptophan operon containing a trpE allele encoding an anthranilate synthase that is not subject to feedback inhibition by tryptophan has been introduced (Japanese Patent Application Laid-Open No. 57-71397, Examples of such strains include those described in JP 62-244382 A1 and U.S. Pat. No. 4,371,614 A1, tryptophanase-deficient E. coli AGX17(pGX44) (NRRL B-12263) and AGX6(pGX50)aroP (NRRL B-12264) (U.S. Pat. No. 4,371,614 A1), E. coli AGX17 / pGX50,pACKG4-pps (WO 9708333 and U.S. Pat. No. 6,319,696 A1) that have increased phosphoenolpyruvate-producing ability, and strains belonging to the genus Escherichia that have increased activity of the protein encoded by the yedA gene or yddG gene (U.S. Pat. No. 2003-0148473 A1 and U.S. Pat. No. 2003-0157667 A1).

[0174] Examples of coryneform bacteria capable of producing L-tryptophan include sulfaguanidine-resistant Corynebacterium glutamicum AJ12118 (FERM BP-478) (Japanese Patent No. 1681002), a strain into which a tryptophan operon has been introduced (Japanese Patent Laid-Open No. 63-240794), and a strain into which a gene encoding shikimate kinase derived from a coryneform bacterium has been introduced (Japanese Patent No. 1994749).

[0175] The culture conditions for the amino acid-producing microorganisms are not particularly limited as long as the microorganisms can grow and produce the target amino acid. The culture can be carried out under, for example, normal conditions used for culturing microorganisms such as bacteria. The culture conditions may be appropriately set depending on various conditions such as the type of microorganism used.

[0176] The medium used for culturing a microorganism capable of producing an amino acid is not particularly limited, as long as the microorganism can grow and the target amino acid can be produced. For example, a conventional medium used for culturing microorganisms such as bacteria can be used as the medium. For example, a medium containing a carbon source, a nitrogen source, a phosphate source, a sulfur source, and components selected from various other organic and inorganic components as needed can be used as the medium. The types and concentrations of the medium components can be appropriately determined depending on various conditions, such as the type of microorganism used.

[0177] Specific examples of carbon sources include sugars such as glucose, fructose, galactose, xylose, arabinose, sucrose, lactose, cellobiose, blackstrap molasses, starch hydrolysates, and biomass hydrolysates, organic acids such as acetic acid, fumaric acid, citric acid, and succinic acid, alcohols such as glycerol, crude glycerol, and ethanol, and fatty acids. As the carbon source, one type of carbon source may be used, or two or more types of carbon sources may be used in combination.

[0178] Specific examples of the nitrogen source include ammonium salts such as ammonium sulfate, ammonium chloride, and ammonium phosphate, organic nitrogen sources such as peptone, casamino acids, yeast extract, malt extract, meat extract, corn steep liquor, and soy protein hydrolysate, ammonia, and urea. As the nitrogen source, one type of nitrogen source may be used, or two or more types of nitrogen sources may be used in combination.

[0179] Specific examples of the phosphate source include phosphate salts such as potassium dihydrogen phosphate and dipotassium hydrogen phosphate, and phosphate polymers such as pyrophosphate. As the phosphate source, one type of phosphate source may be used, or two or more types of phosphate sources may be used in combination.

[0180] Specific examples of sulfur sources include inorganic sulfur compounds such as sulfates, thiosulfates, and sulfites, and sulfur-containing amino acids such as cysteine, cystine, and glutathione. As the sulfur source, one type of sulfur source may be used, or two or more types of sulfur sources may be used in combination.

[0181] Specific examples of other various organic components and inorganic components include inorganic salts such as sodium chloride and potassium chloride; trace metals such as iron, manganese, magnesium, and calcium; vitamins such as vitamin B1, vitamin B2, vitamin B6, nicotinic acid, nicotinamide, and vitamin B12; amino acids; nucleic acids; and organic components containing these, such as peptone, casamino acids, yeast extract, malt extract, meat extract, corn steep liquor, and soy protein hydrolysate. As other various organic components and inorganic components, one type of component may be used, or two or more types of components may be used in combination.

[0182] Cultivation may be carried out by liquid culture (i.e., in a liquid medium). Cultivation may be carried out, for example, under aerobic conditions. "Aerobic conditions" in the case of liquid culture means that the dissolved oxygen concentration in the liquid medium is 0.33 ppm or higher, which is the detection limit using an oxygen membrane electrode, and preferably 1.5 ppm or higher. The oxygen concentration may be controlled, for example, to 5-50%, preferably about 10%, of the saturated oxygen concentration. Specifically, cultivation under aerobic conditions may be carried out, for example, by aerobic culture, shaking culture, agitation culture, or a combination thereof. The pH of the medium may be, for example, 3-10, preferably 4.0-9.5. The pH of the medium can be adjusted as needed during cultivation. The pH of the medium can be adjusted using various alkaline or acidic substances, such as ammonia gas, ammonia water, sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, magnesium carbonate, sodium hydroxide, calcium hydroxide, or magnesium hydroxide. The culture temperature may be, for example, 20 to 40°C, preferably 25 to 37°C. The culture period may be, for example, 10 to 120 hours. The culture may be carried out, for example, by batch culture, fed-batch culture, continuous culture, or a combination thereof. The culture may also be divided into a pre-culture and a main culture. For example, the pre-culture may be carried out on a solid medium such as an agar medium, and the main culture may be carried out in a liquid medium. The culture may be continued, for example, until the carbon source in the medium is consumed or until the activity of the microorganism capable of producing amino acids is lost.

[0183] By culturing a microorganism capable of producing amino acids in this manner, amino acids accumulate in the medium, thereby obtaining an amino acid fermentation broth.

[0184] Amino acids can be separated from the amino acid fermentation broth by known techniques used for separating and purifying compounds. Examples of such techniques include the ion exchange resin method (Nagai, H. et al., Separation Science and Technology, 39(16), 3691-3710), precipitation, membrane separation (JP-A-9-164323, JP-A-9-173792), and crystallization (WO2008 / 078448, WO2008 / 078646). These techniques can be used alone or in appropriate combination. Furthermore, when amino acids precipitate in the medium, they can be separated from the amino acid fermentation broth by solid-liquid separation techniques such as centrifugation or filtration.

[0185] By separating the amino acids from the amino acid fermentation liquor in this manner, an amino acid fermentation by-product liquor is obtained as a by-product.

[0186] Concentration or fractionation of the amino acid fermentation by-product liquid can be carried out, for example, by a conventional method. Methods for concentrating the amino acid fermentation by-product liquid include vacuum concentration, freeze-drying, and spray-drying. Methods for fractionating the amino acid fermentation by-product liquid include the techniques used for separating and purifying the compounds exemplified above.

[0187] The active ingredient may have a function similar to that of strigolactone. Thus, by using the active ingredient, for example, an effect based on the function similar to that of strigolactone may be obtained. In other words, by using the active ingredient, for example, an effect similar to that obtained by using strigolactone may be obtained.

[0188] Examples of functions similar to those of strigolactone include the function of inducing germination of parasitic plants, the function of inhibiting plant branching, and the function of inducing hyphal branching of mycorrhizal fungi. The active ingredient may have, for example, one or more (e.g., all) of the functions similar to those of strigolactone listed above. The active ingredient may, for example, have at least the function of inducing germination of parasitic plants. The terms "germination of parasitic plants" and "germination of seeds of parasitic plants" may be used interchangeably. For example, compounds represented by the formulas (Compound 1) to (Compound 3), (Compound 5) to (Compound 14), (Compound 16) to (Compound 20), (Compound 23), (Compound 26) to (Compound 35), (Compound 37), (Compound 38), (Compound 40), (Compound 53), (Compound 60), (Compound 72), (Compound 83), (Compound 88), and (Compound 89) described below may have the function of inducing germination of parasitic plants. Furthermore, for example, compounds represented by the formulae (Compound 1) to (Compound 3), (Compound 5) to (Compound 8), (Compound 27) to (Compound 30), (Compound 38), (Compound 40), (Compound 53), and (Compound 72) described below can have the function of inducing germination of parasitic plants.

[0189] Furthermore, unlike strigolactone, the active ingredient may have the function of suppressing the germination of parasitic plants. For example, compounds represented by the formulae (Compound 4), (Compound 15), (Compound 36), (Compound 39), (Compounds 42) to (Compound 49), (Compound 51), (Compound 56), (Compound 57), (Compound 59), (Compound 61), (Compound 63), (Compounds 66) to (Compound 71), (Compounds 73) to (Compound 76), (Compounds 78) to (Compound 80), and (Compound 84) described below may have the function of suppressing the germination of parasitic plants. For example, compounds represented by the formulae (Compound 4), (Compound 39), (Compounds 42) to (Compound 49), (Compound 51), (Compound 56), (Compounds 66) to (Compound 71), and (Compounds 73) to (Compound 76) described below may have the function of suppressing the germination of parasitic plants.

[0190] In one aspect, the use of an active ingredient, specifically application of the active ingredient to seeds of a parasitic plant, may induce or inhibit germination of the parasitic plant, i.e., an effect of inducing or inhibiting germination of the parasitic plant may be obtained. The effect of inducing germination of a parasitic plant may also be referred to as a "germination-inducing effect." The effect of inhibiting germination of a parasitic plant may also be referred to as a "germination-inhibiting effect." Induced germination of a parasitic plant may include suicidal germination of the parasitic plant. "Suicidal germination of a parasitic plant" may refer to germination of a parasitic plant in an environment where a target plant for the parasitic plant is not present. A target plant for the parasitic plant may also be referred to as a "target plant for parasitism." A parasitic plant that has undergone suicide germination may be unable to parasitize the target plant and may therefore die. Furthermore, inhibiting germination of a parasitic plant may prevent the growth of the parasitic plant and its infestation of the target plant. Therefore, for example, parasitic plants may be controlled by inducing suicide germination of parasitic plants or by suppressing germination of parasitic plants, i.e., an effect of controlling parasitic plants may be obtained. The effect of controlling parasitic plants is also referred to as a "parasitic plant control effect." The parasitic plant control effect may be an example of a germination induction effect or a germination suppression effect. By inducing suicide germination of parasitic plants, suppressing germination of parasitic plants, or controlling parasitic plants, for example, the cultivation performance of the parasitic target plant may be improved, i.e., an effect of improving the cultivation performance of the parasitic target plant may be obtained. The effect of improving the cultivation performance of the parasitic target plant is also referred to as a "parasitic target plant cultivation performance improvement effect." The effect of improving the cultivation performance of the parasitic target plant may be an example of a germination induction effect, a germination suppression effect, or a parasitic plant control effect. Examples of improving the cultivation performance of the parasitized target plant include improving the yield of the parasitized target plant, improving the growth of the parasitized target plant, and improving the survival rate of the parasitized target plant. Examples of improving the cultivation performance of the parasitized target plant include improving the yield of the parasitized target plant in particular. Examples of improving the plant yield include improving the yield of the entire plant body and improving the yield of parts of the plant body such as leaves, roots, fruits, and seeds.

[0191] Parasitic plants include root parasitic plants. Parasitic plants also include plants whose germination is induced by strigolactone. Specific examples of parasitic plants include plants of the Orobanchaceae family, Scrophulariaceae family, and Convolvulaceae family. Orobanchaceae plants include plants of the genus Striga, Orobanche, and Phelipanche. Orobanchaceae plants particularly include plants of the genus Striga and Orobanche. Plants of the Striga genus include Striga asiatica, Striga gesnerioides, Striga hermonthica, Striga aspera, Striga asiatica, Striga curviflora, Striga parviflora, Striga angustifolia, Striga latericea, Striga aequinoctialis, Striga angolensis, Striga bilabiate, Striga brachycalyx, Striga chrsantha, Striga dalzielii, Striga elegans, Striga forbesii, Striga gastonii, Striga gracillima, Striga hallaei, Striga hirsuta, Striga junodii, Striga klingii, Striga lepidagathidis, Striga lutea, Striga macrantha, Striga passargei, Striga pinnatifida, Striga Examples of plants in the genus Orobanche include Orobanche ramosa, Orobanche minor, Orobanche crenata, Orobanche cumana, Orobanche foetida, Orobanche aegyptiaca, and Orobanche cernua.Examples of plants in the Phelipanchi genus include Phelipanche ramosa and Phelipanche aegyptiaca. Examples of plants in the Scrophulariaceae family include Alectra genus. Examples of plants in the Alectra genus include Alectra vogelii, Alectra picta, Alectra sessiliflora, Alectra orobanchoides, and Alectra fluminensis. Examples of plants in the Convolvulaceae family include Cuscuta genus. Examples of plants in the Cuscuta genus include Cuscuta australis, Cuscuta campestris, Cuscuta chinensis, Cuscuta indecora, Cuscuta epithymum, Cuscuta epilinum, Cuscuta gronovii, Cuscuta planiflora, Cuscuta monogyna, Cuscuta pedicellata, Cuscuta palaestina, and Cuscuta rejlexa. If the classification of a parasitic plant is changed, the parasitic plant may be treated as belonging to either or both of the classifications before and after the change. However, if the classification of a parasitic plant is changed, the parasitic plant will be treated as belonging to both the classifications before and after the change unless otherwise specified. For example, Orobanche ramosa L. is currently classified as Phelipanche ramosa (L.) Pomel, but unless otherwise specified, Orobanche ramosa L. will be treated as belonging to both the Orobanche and Phelipanche genera, and as belonging to both Orobanche ramosa and Phelipanche ramosa. The parasitic plant may be one species, or two or more species.

[0192] The type of parasitic target plant is not particularly limited as long as it is a target for the parasitic plant to parasitize. The parasitic target plant may be, for example, a woody plant or a herbaceous plant. Parasitic plants include grasses (rice, barley, wheat, corn, sorghum, millet, sugarcane, oats, lawn grass, pearl millet, finger millet, fonio, etc.), solanaceae (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.), cruciferous plants (radish, Chinese cabbage, cabbage, komatsuna, nanohana, bok choy, Arabidopsis, etc.), and roses (strawberry, apple, pear, peach, etc.). , Moraceae plants (such as mulberry), Malvaceae plants (such as cotton), Apiaceae plants (such as carrots, parsley, and celery), Liliaceae plants (such as leeks, onions, and asparagus), Asteraceae plants (such as burdock, sunflower, chrysanthemum, garland chrysanthemum, safflower, and lettuce), Amaranthaceae plants (such as sugar beets), Ericaceae plants (such as blueberries and cranberries), Vitaceae plants (such as grapes), Rutaceae plants (such as Satsuma mandarins, lemons, and yuzu), Rubiaceae plants (such as coffee trees), Oleaceae plants (such as olives), Lauraceae plants (such as avocados), Anacardiaceae plants (such as mangoes and cashew trees), Sapindaceae plants (such as lychees), and Lamiaceae plants (such as coleus). The target plant may be one species of plant, or two or more species of plants.

[0193] The germination-inducing effect or germination-inhibiting effect can be confirmed, for example, using the germination of parasitic plants as an indicator. That is, if the germination of parasitic plants is promoted when the active ingredient is used compared to when the active ingredient is not used, it can be determined that the germination of parasitic plants has been induced by the active ingredient. Promotion of germination of parasitic plants can be measured, for example, as an increase in the germination rate or the germination speed of parasitic plants. The germination rate of parasitic plants can be measured, for example, by the procedures described in the Examples. Furthermore, if the germination of parasitic plants is inhibited when the active ingredient is used compared to when the active ingredient is not used, it can be determined that the germination of parasitic plants has been inhibited by the active ingredient. Inhibition of germination of parasitic plants can be measured, for example, as a decrease in the germination rate or the germination speed of parasitic plants. Note that inhibition of germination also includes cases where no germination is observed at all.

[0194] The germination-inducing effect or germination-inhibiting effect can also be confirmed, for example, by confirming the parasitic plant control effect. The parasitic plant control effect can be confirmed, for example, using the growth, survival, or parasitism of the parasitic plant as an indicator. That is, if the growth, survival, or parasitism of the parasitic plant is reduced when the active ingredient is used compared to when the active ingredient is not used, it can be determined that the parasitic plant has been controlled by the active ingredient.

[0195] The germination-inducing effect or germination-inhibiting effect can also be confirmed, for example, by confirming the effect of improving the cultivation performance of the parasitized target plant. The effect of improving the cultivation performance of the parasitized target plant can be confirmed, for example, using the cultivation performance of the parasitized target plant as an indicator. That is, if the cultivation performance (e.g., yield, growth, or survival) of the parasitized target 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 improved the cultivation performance of the parasitized target plant.

[0196] In one embodiment, the use of an active ingredient, specifically the application of the active ingredient to a plant, may suppress the branching of the plant, i.e., an effect of suppressing the branching of the plant may be obtained. The effect of suppressing the branching of the plant is also referred to as a "branching suppressing effect." A plant whose branching is suppressed by an active ingredient is also referred to as a "target plant." Examples of plant branching include branches of the above-ground parts of the plant. Suppressing the branching of the target plant may, for example, improve the cultivation performance of the target plant, i.e., an effect of improving the cultivation performance of the target plant may be obtained. The effect of improving the cultivation performance of the target plant is also referred to as an "effect of improving the cultivation performance of the target plant." The effect of improving the cultivation performance of the target plant may be an example of a branching suppressing effect. Examples of improvements in the cultivation performance of the target plant include improvements in the yield, growth, and survival of the target plant. Examples of improvements in the cultivation performance of the target plant include improvements in the yield of the target plant.

[0197] The type of plant to be cultivated is not particularly limited as long as its branching is inhibited by the active ingredient. The description of the parasitic target plant described above can be applied mutatis mutandis to the plant to be cultivated. For example, the plant to be cultivated includes the plants exemplified as the parasitic target plant.

[0198] The branching-inhibiting effect can be confirmed, for example, using the branching of the target plant as an indicator. That is, if the branching of the target plant is inhibited when the active ingredient is used compared to when the active ingredient is not used, it can be determined that the active ingredient has inhibited the branching of the target plant. The inhibition of branching of the target plant can be measured, for example, as a decrease in the number of branches per individual target plant.

[0199] The branching-inhibiting effect can also be confirmed, for example, by confirming the effect of improving the cultivation performance of the target plant. The effect of improving the cultivation performance of the target plant can be confirmed, for example, using the cultivation performance of the target plant as an indicator. That is, if the cultivation performance (e.g., yield, growth, or viability) of the target 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 improved the cultivation performance of the target plant.

[0200] Furthermore, in one aspect, the use of an active ingredient, specifically application of the active ingredient to a mycorrhizal fungus, may induce hyphal branching of the mycorrhizal fungus, i.e., an effect of inducing hyphal branching of the mycorrhizal fungus may be obtained. The effect of inducing hyphal branching of the mycorrhizal fungus is also referred to as a "hyphal branching induction effect." A plant that is a target for symbiosis with a mycorrhizal fungus is also referred to as a "target symbiosis plant." Inducing hyphal branching of the mycorrhizal fungus may, for example, improve the cultivation performance of the target symbiosis plant, i.e., an effect of improving the cultivation performance of the target symbiosis plant may be obtained. The effect of improving the cultivation performance of the target symbiosis plant is also referred to as an "effect of improving the cultivation performance of the target symbiosis plant." The effect of improving the cultivation performance of the target symbiosis plant may be an example of a hyphal branching induction effect. Examples of improvements in the cultivation performance of the target symbiosis plant include improving the yield, growth, and survival of the target symbiosis plant. An example of an improvement in the cultivation performance of the symbiotic target plant is an improvement in the yield of the symbiotic target plant.

[0201] Mycorrhizal fungi include arbuscular mycorrhizal fungi, which include fungi of the phylum Glomeromycota.

[0202] The type of symbiotic target plant is not particularly limited as long as it is a symbiotic target for the mycorrhizal fungus. Regarding the symbiotic target plant, for example, the description of the parasitic target plant described above can be applied mutatis mutandis. For example, the symbiotic target plant includes the plants exemplified as parasitic target plants.

[0203] The hyphal branching induction effect can be confirmed, for example, using mycorrhizal fungal hyphal branching as an indicator. That is, if mycorrhizal fungal hyphal branching is promoted when the active ingredient is used compared to when the active ingredient is not used, it can be determined that the active ingredient has induced mycorrhizal fungal hyphal branching. Promotion of mycorrhizal fungal hyphal branching can be measured, for example, as the production of hyphae with finely branched tips, as observed when the mycorrhizal fungus reaches the vicinity of the roots of the target plant.

[0204] The branching-inhibiting effect can also be confirmed, for example, by confirming the effect of improving the cultivation performance of the target plant. The effect of improving the cultivation performance of the target plant can be confirmed, for example, using the cultivation performance of the target plant as an indicator. That is, if the cultivation performance (e.g., yield, growth, or viability) of the target 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 improved the cultivation performance of the target plant.

[0205] Furthermore, strigolactone-like functions can be measured using the binding activity of an active ingredient to a strigolactone receptor. Examples of strigolactone receptors include the Arabidopsis strigolactone receptor D14 (DWARF14) protein, the rice strigolactone receptor D14, the Striga strigolactone receptor HTL (HYPOSENSITIVE TO LIGHT), the Orobanche strigolactone receptor D14 protein, and the D14 and HTL / KAI2 (HYPOSENSITIVE TO LIGHT / KARRIKIN INSENSITIVE2) proteins of other parasitic plants. Thus, if binding activity between an active ingredient and a strigolactone receptor is observed, it can be determined that the active ingredient has a strigolactone-like function (i.e., the use of the active ingredient produces effects based on the same function as strigolactone). The binding activity of an active ingredient to a strigolactone receptor can be measured, for example, by measuring the inhibition by the active ingredient of the binding between Yoshimulactone Green (YLG), a fluorescent probe-labeled synthetic strigolactone, and D14. The inhibition of the binding between Yoshimulactone Green (YLG) and D14 by the active ingredient can be measured, for example, by the procedures described in the Examples.

[0206] <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), (B), or (C)).

[0207] The composition of the present invention can be used by applying it to targets such as seeds of parasitic plants, cultivated plants, and mycorrhizal fungi. The use of the composition of the present invention is 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.

[0208] In one embodiment, the germination of a parasitic plant may be induced or inhibited by using the composition of the present invention, specifically by applying the composition of the present invention to seeds of a parasitic plant. That is, the composition of the present invention may be, for example, a composition for inducing germination of a parasitic plant or a composition for inhibiting germination of a parasitic plant. A composition for inducing germination of a parasitic plant may be, for example, a composition for inducing suicide germination of a parasitic plant. For example, a parasitic plant may be controlled by inducing suicide germination of a parasitic plant or by inhibiting germination of a parasitic plant. That is, the composition of the present invention may be, for example, a composition for controlling a parasitic plant. A composition for controlling a parasitic plant may be an example of a composition for inducing germination of a parasitic plant or a composition for inhibiting germination of a parasitic plant. Inducing suicide germination of a parasitic plant, inhibiting germination of a parasitic plant, or controlling a parasitic plant may improve the cultivation performance of the parasitic target plant, for example. Thus, the composition of the present invention may be used, for example, in cultivating a parasitic target plant. That is, the composition of the present invention may be, for example, a composition for cultivating a parasitic target plant, such as a composition for improving the cultivation performance of a parasitic target plant. A composition for cultivating a parasitic target plant, such as a composition for improving the cultivation performance of a parasitic target plant, may be an example of a composition for inducing germination of a parasitic plant, a composition for inhibiting germination of a parasitic plant, or a composition for controlling a parasitic plant. The composition for inducing germination of a parasitic plant, the composition for inhibiting germination of a parasitic plant, the composition for controlling a parasitic plant, and the composition for improving the cultivation performance of a parasitic target plant are also referred to as a "parasitic plant germination inducer," a "parasitic plant germination inhibitor," a "parasitic plant control agent," and an "agent for improving the cultivation performance of a parasitic target plant," respectively.

[0209] In one embodiment, the use of the composition of the present invention, specifically the application of the composition of the present invention to a target plant for cultivation, may suppress branching of the plant. That is, the composition of the present invention may be, for example, a composition for suppressing branching of a target plant for cultivation. Suppressing branching of a target plant for cultivation may, for example, improve the cultivation performance of the target plant for cultivation. Thus, the composition of the present invention may be used, for example, in cultivating a target plant for cultivation. That is, the composition of the present invention may be, for example, a composition for cultivating a target plant for cultivation, such as a composition for improving the cultivation performance of a target plant for cultivation. A composition for cultivating a target plant for cultivation, such as a composition for improving the cultivation performance of a target plant for cultivation, may be an example of a composition for suppressing branching of a target plant for cultivation. The composition for suppressing branching of a target plant for cultivation and the composition for improving the cultivation performance of a target plant for cultivation are also referred to as a "branching inhibitor for a target plant for cultivation" and a "cultivation performance improver for a target plant for cultivation," respectively.

[0210] In one embodiment, the use of the composition of the present invention, specifically the application of the composition of the present invention to mycorrhizal fungi, may induce hyphal branching of mycorrhizal fungi. That is, the composition of the present invention may be, for example, a composition for inducing hyphal branching of mycorrhizal fungi. Inducing hyphal branching of mycorrhizal fungi may, for example, improve the cultivation performance of a target symbiotic plant. Thus, the composition of the present invention may be used, for example, in cultivating a target symbiotic plant. That is, the composition of the present invention may be, for example, a composition for cultivating a target symbiotic plant, such as a composition for improving the cultivation performance of a target symbiotic plant. A composition for cultivating a target symbiotic plant, such as a composition for improving the cultivation performance of a target symbiotic plant, may be an example of a composition for inducing hyphal branching of mycorrhizal fungi. The composition for inducing hyphal branching of mycorrhizal fungi and the composition for improving the cultivation performance of a target symbiotic plant are also referred to as a "mycorrhizal fungal hyphal branching inducer" and a "target symbiotic plant cultivation performance improver," respectively.

[0211] 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.

[0212] The composition of the present invention may be provided, for example, as a pesticide. The composition of the present invention may also be provided, for example, as a fertilizer.

[0213] 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.

[0214] 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 ingredients commonly used in agricultural chemicals, fertilizers, pharmaceuticals, etc. Specific examples of such ingredients include excipients, binders, disintegrants, lubricants, stabilizers, diluents, surfactants, spreaders, pH adjusters, and additives such as water, alcohol, vitamins, and minerals. Specific examples of spreaders include Approach BI TM (Kao Corporation), Mix Power TM (Syngenta Japan Ltd.), Squash TM (Maruwa Biochemical Co., Ltd.). As the component other than the active ingredient, one component may be used, or two or more components 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 selected as appropriate 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.

[0215] The content of the active ingredient in the composition of the present invention is more than 0% (w / w) and less than 100% (w / w). The content of the active ingredient in the composition of the present invention may be, for example, 0.0005% (w / w) or more, 0.001% (w / w) or more, 0.002% (w / w) or more, 0.005% (w / w) or more, 0.01% (w / w) or more, 0.02% (w / w) or more, 0.05% (w / w) or more, 0.1% (w / w) or more, 0.2% (w / w) or more, 0.5% (w / w) or more, 1% (w / w) or more, 2% (w / w) or more, 5% (w / w) or more, or 10% (w / w) or more. % (w / w) or less, 99.9% (w / w) or less, 70% (w / w) or less, 50% (w / w) or less, 30% (w / w) or less, 20% (w / w) or less, 15% (w / w) or less, 10% (w / w) or less, 5% (w / w) or less, 2% (w / w) or less, 1% (w / w) or less, 0.5% (w / w) or less, 0.2% (w / w) or less, 0.1% (w / w) or less, 0.05% (w / w) or less, or 0.02% (w / w) or less, or any compatible combination thereof. The content of the active ingredient in the composition of the present invention may be, for example, 10 nM or more, 20 nM or more, 50 nM or more, 100 nM or more, 200 nM or more, 500 nM 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, 100 μM or more, or 200 μM or more, or 1 M 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. When the composition of the present invention contains two or more active ingredients, the contents of those two or more active ingredients in the composition of the present invention may be set independently or in total within the range of the content of the active ingredients in the composition of the present invention exemplified above (provided that the total content of those two or more active ingredients in the composition of the present invention is 100% (w / w) or less). In addition, when the composition of the present invention contains two or more active ingredients, the "content of the active ingredients in the composition of the present invention" means the total content of those two or more active ingredients in the composition of the present invention, unless otherwise specified.

[0216] 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.

[0217] The concentration of the active ingredient used may be, for example, 1 nM or more, 2 nM or more, 5 nM or more, 10 nM or more, 20 nM or more, 50 nM or more, 100 nM or more, 200 nM or more, 500 nM 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, 100 μM or more, 200 μM or more, 500 μM or more, or 1 mM or more, or 10 mM or less, 5 mM or less, 2 mM or less, 1 mM or less, 500 μM or less, 200 μM or less, 100 μM 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, 500 nM or less, 200 nM or less, or 100 nM or less, or a compatible combination thereof. The concentration of the active ingredient used may be, for example, 1 nM to 10 nM, 10 nM to 100 nM, 100 nM to 1 μM, 1 μM to 10 μM, 10 μM to 100 μM, 100 μM to 1 mM, or 1 mM to 10 mM. The concentration of the active ingredient used may be, for example, 1 nM to 1 mM, 10 nM to 10 mM, 10 nM to 1 mM, 10 nM to 100 μM, 100 nM to 10 mM, 100 nM to 1 mM, 100 nM to 100 μM, 1 μM to 10 mM, 1 μM to 1 mM, 1 μM to 100 μM, 10 μM to 10 mM, 10 μM to 1 mM, 10 μM to 100 μM, 100 μM to 10 mM, or 100 μM to 1 mM. When two or more active ingredients are used, the use concentrations of those two or more active ingredients may be set independently or in total within the range of the use concentrations of the active ingredients exemplified above. When two or more active ingredients are used, the "use concentration of the active ingredients" means the total use concentration of those two or more active ingredients unless otherwise specified.

[0218] When a material containing an active ingredient is used, the amount of the active ingredient (e.g., content (concentration) or amount used) 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) or amount used) is calculated based on the mass of the salt or hydrate converted to the equimolar mass of the free form. When the active ingredient is ingredient (C), the amount of the active ingredient (e.g., content (concentration) or amount used) is calculated based on the dry weight of ingredient (C).

[0219] 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.

[0220] <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), (B), or (C)) to a target such as a parasitic plant seed, a target plant to be cultivated, or a mycorrhizal fungus. The method of the present invention can be carried out, for example, to obtain the effects exemplified above.

[0221] In one aspect, by carrying out the method of the present invention, specifically by applying an active ingredient to seeds of a parasitic plant, germination of the parasitic plant may be induced or suppressed. That is, the method of the present invention may be, for example, a method for inducing or suppressing germination of a parasitic plant. The method for inducing germination of a parasitic plant may be, for example, a method for inducing suicide germination of a parasitic plant. Inducing or suppressing suicide germination of a parasitic plant may, for example, control the parasitic plant. That is, the method of the present invention may be, for example, a method for controlling a parasitic plant. The method for controlling a parasitic plant may be an example of a method for inducing or suppressing germination of a parasitic plant. Inducing suicide germination of a parasitic plant, suppressing germination of a parasitic plant, or controlling a parasitic plant may, for example, improve the cultivation performance of the parasitic target plant. Thus, the method of the present invention may be used, for example, in cultivating a parasitic target plant. That is, the method of the present invention may be, for example, a method for cultivating a parasitic target plant, such as a method for improving the cultivation performance of a parasitic target plant. A method for cultivating a parasitic target plant, such as a method for improving the cultivation performance of a parasitic target plant, may be an example of a method for inducing germination of a parasitic plant, a method for suppressing germination of a parasitic plant, or a method for controlling a parasitic plant.

[0222] Furthermore, in one aspect, branching of a target plant may be suppressed by carrying out the method of the present invention, specifically by applying an active ingredient to the target plant. That is, the method of the present invention may be, for example, a method for suppressing branching of a target plant. Suppressing branching of a target plant may, for example, improve the cultivation performance of the target plant. Thus, the method of the present invention may be used, for example, in cultivating a target plant. That is, the method of the present invention may be, for example, a method for cultivating a target plant, such as a method for improving the cultivation performance of a target plant. A method for cultivating a target plant, such as a method for improving the cultivation performance of a target plant, may be an example of a method for suppressing branching of a target plant.

[0223] Furthermore, in one aspect, hyphal branching of mycorrhizal fungi may be induced by carrying out the method of the present invention, specifically by applying an active ingredient to mycorrhizal fungi. That is, the method of the present invention may be, for example, a method for inducing hyphal branching of mycorrhizal fungi. Inducing hyphal branching of mycorrhizal fungi may, for example, improve the symbiotic target plant. Thus, the method of the present invention may be used, for example, for cultivating a symbiotic target plant. That is, the method of the present invention may be, for example, a method for cultivating a symbiotic target plant, such as a method for improving the cultivation performance of a symbiotic target plant. A method for cultivating a symbiotic target plant, such as a method for improving the cultivation performance of a symbiotic target plant, may be an example of a method for inducing hyphal branching of a mycorrhizal fungus.

[0224] 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.

[0225] 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 target object, the growth method of the target object, the growth stage of the target object, and the intended use of the composition of the present invention. The composition of the present invention can be applied to the target object in the usual manner, for example, by applying a pesticide or fertilizer to plant seeds, plants, or mycorrhizal fungi. The composition of the present invention may be applied to the target object itself, such as parasitic plant seeds, cultivated plants, or mycorrhizal fungi, or to the medium in which the target object is grown, or to a combination thereof. The medium in which the target object is grown 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 target object and the growth method of the target object. Examples of growth of the target object include germination of parasitic plants, cultivation of cultivated plants, and growth of mycorrhizal fungi. The growth method of the target object is not particularly limited. The growth of the target object can be carried out, for example, by the same method as a conventional method for growing the target object, except for the application of the composition of the present invention. Examples of cultivation methods for plants, such as target plants, include soil culture, nutrient solution culture, and nutrient solution soil culture. Examples of nutrient solution culture include hydroponics and solid medium culture. Examples of hydroponics include the nutrient film technique (NFT) and the deep flow technique (DFT). That is, examples of growth media in which plants, such as target plants, are grown include soil, hydroponic culture solution, and solid medium. The growth of other target objects, such as parasitic plant germination and mycorrhizal fungi growth, can also be carried out in the same medium in which plants, such as target plants, are grown. Therefore, the above-mentioned descriptions of the medium in which plants, such as target plants, are grown, can be applied mutatis mutandis to the medium in which other target objects, such as parasitic plant germination and mycorrhizal fungi growth, are grown. That is, media for the germination of parasitic plants and the growth of other targets, such as mycorrhizal fungi, include the media exemplified as media for cultivating plants. Note that the media for the germination of parasitic plants can also be the media for cultivating target plants. Furthermore, the media for the growth of mycorrhizal fungi can also be the media for cultivating target plants.Application to the target object itself includes spraying, painting, and immersion of the target object. The composition of the present invention may be applied to the entire target object or to a portion of the target object. For example, when the target object is a plant, the composition of the present invention may be applied to the entire plant body or to a portion of the plant body. The composition of the present invention may be applied to, for example, the entire above-ground part of the plant body. Examples of parts of the plant body include leaves, stems, trunks, roots, and fruits. 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 immersion. Application to growth media include spraying, irrigation, and mixing of the growth media. Specifically, the composition of the present invention may be applied (e.g., sprayed) to the growth media through an irrigation tube. Application to the growth media may be carried out so that the active ingredient reaches a position where it can act on the target object. For example, application to the medium in which the plants are grown may be carried out so that the active ingredients reach the root zone of the plants.

[0226] 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 target object, the growth method of the target object, the growth stage of the target object, 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 target object may or may not already be present in the growth medium. The desired effect may be obtained in the target object by applying the composition of the present invention to the target object itself or by applying the composition of the present invention to a growth medium in which the target object already exists. Furthermore, the desired effect may be obtained in an object that may exist in the growth medium in the future by applying the composition of the present invention to a growth medium in which the target object does not exist. Examples of objects that may exist in the growth medium in the future include objects that will be transferred to the growth medium from outside in the future and objects 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.

[0227] For example, when the compositions of the present invention are used to induce or inhibit the germination of parasitic plants, the compositions of the present invention may be applied before the emergence of the parasitic plants.

[0228] Specifically, for example, when the composition of the present invention is used to induce suicidal germination of a parasitic plant (e.g., to control a parasitic plant by inducing suicidal germination), the composition of the present invention may be applied before the parasitic plant germinates so that the germination of the parasitic plant is induced during a period when the target plant is not present in the growth medium. That is, for example, when the composition of the present invention is used to induce suicidal germination of a parasitic plant (e.g., to control a parasitic plant by inducing suicidal germination), the composition of the present invention may be applied before the parasitic plant germinates and at a time when the target plant is not present in the growth medium. The period or time when the target plant is not present in the growth medium includes a period or time before planting seeds or seedlings of the target plant in the growth medium. When cultivating a parasitized target plant after inducing suicidal germination of a parasitic plant or after controlling a parasitic plant, for example, seeds or seedlings of the parasitized target plant may be planted, the parasitized target plant may germinate, and / or the parasitized target plant may be grown after inducing suicidal germination of a parasitic plant or after controlling a parasitic plant.

[0229] Specifically, for example, when the composition of the present invention is used to induce germination of a parasitic plant (e.g., to control a parasitic plant by inducing germination), the composition of the present invention may be applied before the germination of the parasitic plant so that the germination of the parasitic plant is induced during a period when the productivity of the parasitic target plant is not affected by parasitism by the parasitic plant. By inducing germination of the parasitic plant during a period when the productivity of the parasitic target plant is not affected by parasitism by the parasitic plant, the parasitic plant may parasitize the parasitic target plant during the same period. Examples of periods during which the productivity of the parasitic target plant is not affected by parasitism by the parasitic plant include the later period of cultivation of the parasitic target plant, i.e., the later period of the cultivation season of the parasitic target plant. The "later period of growth of the parasitic target plant" may mean, for example, the period after the parasitic target plant has grown sufficiently. Furthermore, "the later stage of growth of the parasitized target plant" may mean, for example, a period after 50% or more, 60% or more, 70% or more, 80% or more, 90% or more, or 95% or more of the entire cultivation period of the parasitized target plant has elapsed. "The entire cultivation period of the parasitized target plant" may mean the period from planting seeds or seedlings of the parasitized target plant to completion of cultivation of the parasitized target plant (e.g., harvesting of the plant body). At this time, the composition of the present invention may be applied (e.g., sprayed) to the growth medium, for example, through an irrigation tube. After germination and infestation of the parasitized plant, but before the parasitized plant matures and produces seeds, the parasitized plant may be removed from the growth medium. For example, the parasitized plant may be collected (e.g., harvested) from the growth medium together with the parasitized target plant.

[0230] Specifically, for example, when the composition of the present invention is used to suppress the germination of a parasitic plant (e.g., to control a parasitic plant by suppressing germination), the composition of the present invention may be applied before the germination of the parasitic plant so that the germination of the parasitic plant is suppressed while the target plant is present in the growth medium. That is, for example, when the composition of the present invention is used to suppress the germination of a parasitic plant (e.g., to control a parasitic plant by suppressing germination), the composition of the present invention may be applied before the germination of the parasitic plant and at a time when the target plant is not present in the growth medium or when the target plant is present in the growth medium. That is, by applying the composition of the present invention in advance at a time when the target plant is not present in the growth medium, the germination of the parasitic plant may be suppressed while the target plant is present in the growth medium thereafter. Furthermore, by applying the composition of the present invention at a time when the target plant is present in the growth medium, the germination of the parasitic plant may be suppressed while the target plant is present in the growth medium. When the compositions of the present invention are used to inhibit the germination of parasitic plants (e.g., to control parasitic plants by inhibiting germination), the compositions of the present invention may be applied, for example, particularly when the target plant is present in the growth medium, including a period or time after the target plant germinates and a period or time after the seedlings of the target plant are planted in the growth medium.

[0231] By applying the composition of the present invention to parasitic plant seeds or to a growth medium in which parasitic plant seeds are already present, it may be possible to induce germination (e.g., suicide germination) of the parasitic plant, inhibit germination of the parasitic plant, control parasitic plants emerging from the seeds, and / or improve the cultivation performance of plants that are parasitic targets of parasitic plants emerging from the seeds. Furthermore, by applying the composition of the present invention to a growth medium in which no parasitic plant seeds are present, it may be possible to induce germination (e.g., suicide germination) of parasitic plants that may be present in the growth medium in the future, inhibit germination of parasitic plants that may be present in the growth medium in the future, control parasitic plants emerging from the seeds, and / or improve the cultivation performance of plants that are parasitic targets of parasitic plants emerging from the seeds. That is, the compositions of the present invention may be used, for example, to control parasitic plants in growing media that are already contaminated with parasitic plant seeds, or may be used prophylactically to control parasitic plants in growing media that may be contaminated with parasitic plant seeds in the future.

[0232] For example, when the composition of the present invention is used to suppress branching in cultivated plants, the composition of the present invention may be applied before branching of the cultivated plants has progressed. Specifically, when the composition of the present invention is used to limit branching of cultivated plants to a desired level, the composition of the present invention may be applied before branching of the cultivated plants has progressed to the desired level.

[0233] For example, when the composition of the present invention is used to induce hyphal branching of mycorrhizal fungi, the composition of the present invention may be applied before hyphal branching of the mycorrhizal fungi is complete, or, for example, the composition of the present invention may be applied after hyphal branching of the mycorrhizal fungi is complete to further promote hyphal branching.

[0234] 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 target object, the growth method of the target object, the growth stage of the target object, 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.

[0235] 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. 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 such as those exemplified above) may be, for example, 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. Furthermore, the application rate of the composition of the present invention can be determined taking into consideration not only the application area (a two-dimensional element) but also three-dimensional elements. That is, the application rate of the composition of the present invention can be set, 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, for example, as the application rate of the composition of the present invention in liquid form (e.g., the composition of the present invention in liquid form containing the active ingredient at the use concentration exemplified above), for plants from the ground surface 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. The application rate of the composition of the present invention may be, for example, 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 for plants of 2 meters or more when the composition of the present invention is in liquid form (e.g., a liquid composition of the present invention containing the active ingredient at a use concentration as exemplified above). When the composition of the present invention is applied to a growing medium (e.g., 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 when the composition of the present invention is in liquid form (e.g., a liquid composition of the present invention containing the active ingredient at a use concentration as exemplified above). The composition of the present invention may be applied once or in multiple applications. The composition of the present invention may be applied, for example, in two or more applications, three or more applications, five or more applications, or ten or more applications. When the composition of the present invention is applied in multiple applications, the term "application amount of the composition of the present invention" refers to the total application amount of the composition of the present invention in multiple applications.

[0236] 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.

[0237] The application rate of the active ingredient is, for example, 1 μmol / hectare or more, 10 μmol / hectare or more, 20 μmol / hectare or more, 50 μmol / hectare or more, 100 μmol / hectare or more, 200 μmol / hectare or more, 500 μmol / hectare or more, 1 mmol / hectare or more, 2 mmol / hectare or more, 5 mmol / hectare or more, 10 mmol / hectare or more, 20 mmol / hectare or more, 50 mmol / hectare or more. or more, 100 mmol / hectare or more, 200 mmol / hectare or more, 500 mmol / hectare or more, 1 mol / hectare or more, 2 mol / hectare or more, 5 mol / hectare or more, 10 mol / hectare or more, 20 mol / hectare or more, 50 mol / hectare or more, 100 mol / hectare or more, 300 mol / hectare or more, 500 mol / hectare or more, 1000 mol / hectare or more, or 15 The concentration may be 2500 mol / hectare or more, 1500 mol / hectare or less, 1000 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 The concentration may be tar 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, 2 mmol / hectare or less, 1 mmol / hectare or less, 500 μmol / hectare or less, 200 μmol / hectare or less, or 100 μmol / hectare or less, or any compatible combination thereof.The application rate of the active ingredient may be, for example, 1 μmol / ha to 100 μmol / ha, 10 μmol / ha to 1 mmol / ha, 1 mmol / ha to 10 mmol / ha, 10 mmol / ha to 100 mmol / ha, 100 mmol / ha to 1 mol / ha, 1 mol / ha to 10 mol / ha, 10 mol / ha to 100 mol / ha, 100 mol / ha to 500 mol / ha, 500 mol / ha to 1000 mol / ha, 1000 mol / ha to 1500 mol / ha, or 1500 mol / ha to 2500 mol / ha. When the composition of the present invention is applied in multiple applications, the "application amount of the active ingredient" means the total application amount of the active ingredient in multiple applications.

[0238] 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.

[0239] 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), (B), or (C)) to a target object such as a parasitic plant seed, a target plant to be cultivated, or a mycorrhizal fungus, and cultivating the plant. The combination of the target object and the plant to be produced can be selected appropriately. Examples of combinations of the target object and the plant to be produced include a combination of a parasitic plant seed and a target parasitic plant, a target plant to be cultivated and a target plant to be cultivated (meaning that the target plant to which the active ingredient has been applied is cultivated), and a combination of a mycorrhizal fungus and a symbiotic target plant. The method for cultivating the plant to be produced is not particularly limited. The cultivation of the plant to be produced can be carried out, for example, by the same method as a conventional method for cultivating plants, except for applying the active ingredient to the target object. The plant cultivation method is as described above. The application of the active ingredient and cultivation of the plant to be produced may be carried out, for example, so as to obtain the desired effect of the application of the active ingredient. For example, the application of the active ingredient may be carried out during cultivation of the plant to be produced, or the cultivation of the plant to be produced may be carried out after the application of the active ingredient. Specifically, for example, cultivation of the parasitic target plant may be carried out after inducing suicide germination of the parasitic plant, after suppressing germination of the parasitic plant, or after controlling the parasitic plant. That is, one embodiment of the method of the present invention may be, for example, a method for producing a parasitic target plant (specifically, a plant body of a parasitic target plant), comprising applying an active ingredient (i.e., the above-mentioned component (A), (B), or (C)) to the seeds of the parasitic plant to induce suicide germination of the parasitic plant, suppress germination of the parasitic plant, or control the parasitic plant; and cultivating the parasitic target plant after the application (specifically, after inducing suicide germination of the parasitic plant, after suppressing germination of the parasitic plant, or after controlling the parasitic plant).Furthermore, one embodiment of the method of the present invention may be a method for producing a parasitized target plant (specifically, a plant body of a parasitized target plant), comprising, for example, cultivating the parasitized target plant; and applying an active ingredient (i.e., the above-mentioned component (A), (B), or (C)) to the seeds of the parasitized plant during the cultivation, thereby suppressing germination of the parasitized plant. The plant (specifically, the plant body) can be harvested as appropriate. That is, the method of the present invention may further comprise harvesting the plant (specifically, the 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, the plant body) to be harvested may be the whole plant body or a part of the plant body. Examples of the part of the plant body include leaves, stems, trunks, roots, and fruits.

[0240] <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 germination (e.g., suicide germination) of a parasitic plant, suppressing germination of a parasitic plant, controlling a parasitic plant, suppressing branching of a cultivated plant, inducing hyphal branching of a mycorrhizal fungus, or improving the cultivation performance of a plant (e.g., a parasitic target plant, a cultivated target plant, or a symbiotic target plant), or the use of the active ingredient in the manufacture of a composition for inducing germination (e.g., suicide germination) of a parasitic plant, suppressing germination of a parasitic plant, controlling a parasitic plant, suppressing branching of a cultivated plant, inducing hyphal branching of a mycorrhizal fungus, or improving the cultivation performance of a plant (e.g., a parasitic target plant, a cultivated target plant, or a symbiotic target plant).

[0241] The present invention also discloses active ingredients for use in the above-mentioned applications. That is, the present invention discloses active ingredients for use in, for example, inducing germination (e.g., suicide germination) of parasitic plants, suppressing germination of parasitic plants, controlling parasitic plants, suppressing branching of cultivated plants, inducing hyphal branching of mycorrhizal fungi, or improving the cultivation performance of plants (e.g., parasitic target plants, cultivated target plants, or symbiotic target plants), and active ingredients for use in producing compositions for inducing germination (e.g., suicide germination) of parasitic plants, suppressing germination of parasitic plants, controlling parasitic plants, suppressing branching of cultivated plants, inducing hyphal branching of mycorrhizal fungi, or improving the cultivation performance of plants (e.g., parasitic target plants, cultivated target plants, or symbiotic target plants).

[0242] The present invention will now be described in more detail with reference to the following non-limiting examples.

[0243] Synthesis Example Compounds 1 to 90 were obtained by the following method. The structures of Compounds 1 to 90 are shown in the following formulas (Compound 1) to (Compound 90), respectively.

[0244] Synthesis example 1 N α Pyridine (0.2 mL) was added to a chloroform solution (5 mL) of -Boc-Lys-OMe·AcOH·nH2O (0·AcOH) (296 mg, 0.87 mmol, as monohydrate) and stirred at 0°C for 5 minutes. After stirring, a chloroform solution (5 mL) of triphosgene (266 mg, 0.99 mmol) was added and the mixture was stirred for an additional 2 hours. 0.1 N hydrochloric acid was added to the reaction mixture, followed by partition extraction with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated to dryness under reduced pressure. The resulting residue was dissolved in chloroform (2 mL) without purification, and 5-hydroxy-3-methyl-2,5-dihydrofuran-2-one (115 mg, 1.01 mmol) and triethylamine (0.15 mL, 1.08 mmol) were added. The mixture was stirred at room temperature for 5 hours. Chloroform was added to the reaction mixture, which was then partition washed with 0.1 N hydrochloric acid. The organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated to dryness under reduced pressure, and the resulting residue was purified by reverse-phase HPLC (linear gradient of water-acetonitrile) to obtain Compound 1. Yield: 13%; ESI MS m / z: 423.1 (M+Na). +; 1 H NMR (400 MHz, CD3OD) δ 7.09 (1H, t, J=1.6 Hz), 6.85 (1H, t, J=1.6 Hz), 4.11 (1H, dd, J=4.8, 8.8 Hz), 3.73 (3H, s), 3.16 (2H, t, J=6.8 Hz), 1.94 (3H, s), 1.79 (1H, m), 1.67 (1H, m), 1.58-1.52 (2H, m), 1.46 (11H, brs).

[0245]

[0246] Synthesis Example 2: Compound 1 (23 mg, 0.057 mmol) was dissolved in formic acid (0.1 mL) and stirred at room temperature for 18 hours. The reaction mixture was concentrated to dryness under reduced pressure to obtain compound 2 as a formate salt. Yield: 99%; ESI MS m / z: 301.0 (M+H). + ; 1 H NMR (400 MHz, CD3OD)δ9.26 (1H, s), 7.09 (1H, t, J=1.6 Hz), 6.85 (1H, t, J=1.6 Hz), 4.06 (1H, t, J=6.4 Hz), 3.86 (3H, s), 3.25-3.12 (2H, m), 1.99-1.89 (5H, m), 1.62-1.43 (4H, m).

[0247]

[0248] Synthesis example 3 N ε Compound 3 was obtained from -Boc-lysine t-butyl ester and 5-hydroxy-3-methyl-2,5-dihydrofuran-2-one in the same manner as in the preparation of Compound 1. Yield: 20%. 1 H NMR (400 MHz, CD3OD)δ7.11 (1H, m), 6.85 (1H, m), 4.06 (1H, m), 3.07-3.03 (2H, m), 1.95 (3H, d, J=0.8 Hz), 1.81 (1H, m), 1.69 (1H, m), 1.49-1.44 (22H, m)

[0249]

[0250] Synthesis Example 4 Compound 4 was obtained from Compound 3 in the same manner as in Compound 2. Yield: 99%; ESI MS m / z: 287.0 (M+H) + ; 1 H NMR (400 MHz, D2O)δ7.08 (0.5H, d, J=1.6 Hz), 7.05 (0.5H, d, J=2.0 Hz), 6.76 (0.5H, t, J=1.6 Hz), 6.74 (0.5H, t, J=1.6 Hz), 3.95 (1H, m), 2.91 (2H, t, J=7.6 Hz), 1.85 (3H, s), 1.76 (1H, m), 1.68-1.58 (3H, m), 1.39-1.33 (2H, m).

[0251]

[0252] Synthesis Example 5: Carbodiimidazole (CDI) (80 mg, 0.49 mmol) was dissolved in THF (3 mL), and 5-hydroxy-3-methyl-2,5-dihydrofuran-2-one (59 mg, 0.52 mmol) was added. The mixture was stirred at room temperature for 5 hours. Phenylalanine t-butyl ester hydrochloride (125 mg, 0.49 mmol) was added to the reaction mixture, followed by triethylamine (0.08 mL, 0.57 mmol) under ice cooling. The mixture was stirred at room temperature for an additional 1 hour. Ethyl acetate was added to the reaction mixture, followed by distribution washing with 0.1N hydrochloric acid. The organic layer was dehydrated and dried over anhydrous sodium sulfate and then concentrated to dryness under reduced pressure. The residue was purified by reverse-phase HPLC (water containing 0.1% formic acid - acetonitrile) to obtain compound 5. Yield: 35%; ESI MS m / z: 384.1 (M+Na). + ; 1 H NMR (400 MHz, CD3OD)δ7.33-7.22 (5H, m), 7.09 (0.5H, s), 7.05 (0.5H, s), 6.81 (0.5H, brs), 6.78 (0.5H, brs), 4.34 (1H, m), 2.96 (1H, m), 2.11 (1H, m), 1.44 (4H, s), 1.41 (5H, m).

[0253]

[0254] Synthesis Example 6: Compound 6 was obtained using leucine t-butyl ester hydrochloride and 5-hydroxy-3-methyl-2,5-dihydrofuran-2-one as starting materials in the same manner as in the preparation of Compound 5. Yield: 21%; ESI MS m / z: 350.0 (M+Na). + ; 1 H NMR (400 MHz, CD3OD)δ7.11 (1H, m), 6.85 (1H, m), 4.12 (1H, m), 1.95 (3H, s), 1.73 (1H, m), 1.60-1.56 (2H, m), 1.49 (9H, s), 0.99-0.94 (6H, m).

[0255]

[0256] Synthesis Example 7: Compound 7 was obtained using mono N-Boc-propylenediamine as a starting material in the same manner as in the synthesis of Compound 1. Yield: 40%; ESI MS m / z: 337.1 (M+Na). + ; 1 H NMR (400 MHz, CD3OD)δ7.09 (1H, t, J=1.6 Hz), 6.85 (1H, t, J=1.6 Hz), 3.19 (2H, t, J=6.8 Hz), 3.10 (2H, t, J=6.8 Hz), 1.94 (3H, s), 1.71-1.64 (2H, m), 1.45 (9H, s).

[0257]

[0258] Synthesis Example 8 Compound 8 was obtained as a formate salt from Compound 7 in the same manner as in Compound 2. Yield: 99%; ESI MS m / z: 215.0 (M+H) + ; 1H NMR (400 MHz, CD3OD)δ8.34 (1H, s), 7.10 (1H, t, J=1.6 Hz), 6.85 (1H, t, J=1.6 Hz), 3.30-3.23 (2H, m), 3.00 (2H, t, J=7.6 Hz), 1.949 (3H, s), 1.945-1.88 (2H, m).

[0259]

[0260] Synthesis Example 9: Compound 9 was obtained using mono N-Boc-cadaverione and 5-hydroxy-3-methyl-2,5-dihydrofuran-2-one as starting materials in the same manner as for Compound 5. Yield: 19%; ESI MS m / z: 365.1 (M+Na). + ; 1 H NMR (400 MHz, CDCl3)δ6.87 (2H, m), 5.06 (1H, brs), 4.57 (1H, brs), 3.25-3.20 (2H, m), 3.14-3.09 (2H, m), 1.97 (3H, s), 1.58-1.48 (4H, m), 1.43 (9H, s), 1.39-1.33 (2H, m).

[0261]

[0262] Synthesis Example 10: Compound 10 was obtained as a formate salt from Compound 9 in the same manner as in Compound 2. Yield: 99%; ESI MS m / z: 243.0 (M+H) + ; 1 H NMR (400 MHz, CD3OD)δ8.51 (1H, s), 7.09 (1H, d, J=1.6 Hz), 6.84 (1H, t, J=1.6 Hz), 3.23-3.14 (2H, m), 2.94 (2H, t, J=7.6 Hz), 1.94 (3H, s), 1.72-1.68 (2H, m), 1.61-1.55 (2H, m), 1.48-1.42 (2H, m).

[0263]

[0264] Synthesis Example 11 Compound 9 (2.5 mg, 0.0073 mmol) was dissolved in heptafluorobutyric acid (0.1 mL) and stirred at room temperature for 18 hours. The mixture was concentrated to dryness under reduced pressure to obtain compound 10 as a heptafluorobutyrate salt. Yield: 99%. 1 H NMR (400 MHz, CD3OD)δ7.09 (1H, d, J=1.6 Hz), 6.85 (1H, t, J=1.6 Hz), 3.25-3.13 (2H, m), 2.94 (2H, t, J=7.6 Hz), 1.94 (3H, s), 1.72-1.68 (2H, m), 1.61-1.56 (2H, m), 1.48-1.42 (2H, m).

[0265] Synthesis Example 12: To a THF solution (15 mL) of compound 10 (formate) (264 mg), triethylamine (0.15 mL) was added and stirred at room temperature for 5 minutes. N,N',N''-tri-Boc-guanidine (327 mg) was added to the reaction solution, and the mixture was further stirred at room temperature for 2 days. After concentrating the reaction solution under reduced pressure, ethyl acetate was added and the mixture was subjected to distribution washing with 1N hydrochloric acid. The organic layer was dehydrated and dried over anhydrous sodium sulfate, and then concentrated to dryness under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane / ethyl acetate) to obtain compound 11. Yield 35%; ESI MS m / z 485.3 (M+H) + ; 1 H NMR (400 MHz, CD3OD)δ7.08 (1H, t, J=1.6 Hz), 6.85 (1H, t, J=1.6 Hz), 3.39-3.36 (2H, m), 3.20-3.16 (2H, m), 1.94 (3H, s), 1.66-1.38 (24H, m).

[0266]

[0267] Synthesis Example 13: Compound 12 was obtained as a formate salt from Compound 11 in the same manner as in Compound 2. Yield: 99%; ESI MS m / z 285 (M+H) + ; 1H NMR (400 MHz, CD3OD)δ8.38 (1H, s), 7.10 (1H, t, J=1.6 Hz), 6.84 (1H, t, J=1.6 Hz), 3.21-3.15 (4H, m), 1.94 (3H, s), 1.65-1.56 (4H, m), 1.46-1.40 (4H, m).

[0268]

[0269] Synthesis Example 14: Compound 12 was obtained as a heptafluorobutyrate salt from Compound 11 in the same manner as in Compound 9. Yield: 99%. 1 H NMR (400 MHz, CD3OD)δ7.09 (1H, s), 6.84 (1H, d, J=1.6 Hz),3.24-3.13 (4H, m), 1.94 (3H, s), 1.66-1.55 (4H, m), 1.45-1.40 (2H, m).

[0270] Synthesis Example 15: Compound 13 was obtained using GABA ethyl ester and 5-hydroxy-3-methyl-2,5-dihydrofuran-2-one as starting materials in the same manner as for Compound 5. Yield: 14%; ESI MS m / z: 272.0 (M+H). + ; 1 H NMR (400 MHz, CD3OD)δ7.09 (1H, t, J=1.6 Hz), 6.85 (1H, t, J=1.6 Hz), 4.14 (2H, q, J=7.2 Hz), 3.20 (2H, t, J=7.2 Hz), 2.38 (2H, t, J=7.2 Hz), 1.94 (3H, s), 1.86-1.79 (2H, m), 1.27 (3H, t, J=7.2 Hz).

[0271]

[0272] Synthesis Example 16: Compound 14 was synthesized using GABA t-butyl ester and 5-hydroxy-3-methyl-2,5-dihydrofuran-2-one as starting materials in the same manner as for Compound 5. Yield: 20%; ESI MS: 322.0 (M+Na). + ; 1H NMR (400 MHz, CD3OD)δ7.09 (1H, t, J=1.6 Hz), 6.85 (1H, t, J=1.6 Hz), 3.20-3.17 (2H, m), 2.29 (2H, t, J=7.6 Hz), 1.94 (3H, s), 1.82-1.75 (2H, m), 1.47 (9H, s).

[0273]

[0274] Synthesis Example 17 Compound 15 was obtained from Compound 14 in the same manner as in Compound 2. Yield: 73%; ESI MS: 244.0 (M+H) + ; 1 H NMR (400 MHz, CD3OD)δ7.09 (1H, t, J=1.6 Hz), 6.85 (1H, t, J=1.6 Hz), 3.23-3.19 (2H, m), 2.36 (2H, t, J=7.6 Hz), 1.94 (3H, s), 1.86-1.79 (2H, m).

[0275]

[0276] Synthesis Example 18: Compound 16 was obtained using L-homoserine lactone hydrochloride and 5-hydroxy-3-methyl-2,5-dihydrofuran-2-one as starting materials in the same manner as for Compound 5. Yield: 7%; ESI MS m / z: 263.9 (M+Na). + ; 1 H NMR (400 MHz, CD3OD)δ7.12 (1H, m), 6.87 (1H, m), 4.52 (0.5H, m), 4.33 (1.5H, m), 4.29 (1H, m), 2.60 (1H, m), 2.33 (1H, m), 1.95 (3H, s).

[0277]

[0278] Synthesis Example 19: Compound 17 was obtained using D-homoserine lactone hydrochloride and 5-hydroxy-3-methyl-2,5-dihydrofuran-2-one as starting materials in the same manner as for Compound 5. Yield: 19%; ESI MS m / z: 263.9 (M+Na). + ;1 H NMR (400 MHz, CD3OD)δ7.11 (1H, m), 6.87 (1H, m), 4.61-4.56 (1.5H, m), 4.51-4.42 (1.5H, m), 4.32 (1H, m), 2.59 (1H, m), 2.33 (1H, m), 1.95 (3H, s).

[0279]

[0280] Synthesis Example 20: Compound 18 was obtained using proline benzyl ester hydrochloride and 5-hydroxy-3-methyl-2,5-dihydrofuran-2-one as starting materials in the same manner as for Compound 5. Yield: 16%; ESI MS m / z: 368.0 (M+Na). + ; 1 H NMR (400 MHz, CD3OD)δ7.42-7.34 (4H, m), 7.12 (0.7H, t, J=1.6 Hz), 7.05 (0.3H, t, J=1.6 Hz), 6.84 (1H, m), 6.70 (0.7H, t, J=1.6 Hz), 6.48 (0.3H, t, J=1.6 Hz), 5.27-5.02 (1.7H, m), 5.03 (0.3H, d, J=11.6 Hz), 4.42 (1H, m), 3.61-3.49 (2H, m), 2.32 (1H, m), 2.07-1.86 (6H, m).

[0281]

[0282] Synthesis Example 21: Compound 19 was obtained using phenylalanine methyl ester hydrochloride and 5-hydroxy-3-methyl-2,5-dihydrofuran-2-one as starting materials in the same manner as for Compound 5. Yield: 22%; ESI MS m / z: 342.0 (M+Na). + ; 1H NMR (400 MHz, CD3OD)δ7.32-7.22 (5H, m), 7.08 (0.5H, s), 7.03 (0.5H, t, J=1.6 Hz), 6.79 (0.5H, s), 6.76 (0.5H, s), 4.48 (1H, m), 3.74 (1.5H, s), 3.72 (1.5H, s), 3.18 (1H, m), 2.97 (1H, m), 1.94 (1.5H, s), 1.93 (1.5H, s).

[0283]

[0284] Synthesis Example 22: Compound 20 was obtained using phenylalanine ethyl ester hydrochloride and 5-hydroxy-3-methyl-2,5-dihydrofuran-2-one as starting materials in the same manner as for Compound 5. Yield: 15%; ESI MS m / z: 356.0 (M+Na). + ; 1 H NMR (400 MHz, CD3OD)δ7.32-7.22 (5H, m), 7.08 (0.5H, s), 7.04 (0.5H, t, J=1.6 Hz), 6.78 (0.5H, d, J=1.2 Hz), 6.76 (0.5H, d, J=1.6 Hz), 4.45 (1H, m), 4.21-4.13 (2H, m), 3.17 (1H, m), 2.98 (1H, m), 1.94 (1.5H, s), 1.93 (1.5H, s), 1.26-1.20 (3H, m).

[0285]

[0286] Synthesis Example 23 (Step 1) Synthesis of Compound 21 HOAt (132 mg, 0.97 mmol) and WSC·HCl (190 mg, 0.99 mmol) were added to a solution of N-Cbz-leucine (259 mg, 0.95 mmol) in acetonitrile (10 mL), and the mixture was stirred at room temperature for 1 hour. Leucine t-butyl ester hydrochloride (235 mg, 1.05 mmol) and triethylamine (0.16 mL, 1.15 mmol) were added to the reaction mixture, and the mixture was stirred at room temperature for an additional 3 hours. The reaction mixture was concentrated under reduced pressure, and ethyl acetate was added. The mixture was then 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, and then concentrated to dryness under reduced pressure to obtain Compound 21. Yield: 93%; ESI MS m / z: 457.2 (M+Na). + ; 1 H NMR (400 MHz, CD3OD) δ 7.39-7.30 (5H, m), 5.12 (1H, d, J=12.0 Hz), 5.09 (1H, d, J=12.0 Hz), 4.35 (1H, dd, J=6.0, 8.8 Hz), 4.22 (1H, m), 1.73 (4H, m), 1.62-1.54 (4H, m), 1.47 (9H, s), 0.99-0.91 (12H, m).

[0287]

[0288] (Step 2) Synthesis of Compound 22: To a solution of compound 21 (370 mg, 0.85 mmol) in ethanol (10 mL), 5% palladium on carbon (54 mg) was added and stirred under a hydrogen atmosphere at room temperature for 18 hours. The reaction mixture was filtered, and the filtrate was concentrated to dryness under reduced pressure to give compound 22. Yield: 88%; ESI MS m / z: 301.2 (M+H). + ; 1H NMR (400 MHz, CD3OD)δ4.37 (1H, t, J=6.8 Hz), 3.40 (1H, dd, J=6.0, 8.0 Hz), 1.79-1.71 (2H, m), 1.63-1.56 (3H, m), 1.48 (9H, s), 1.39 (1H, m), 1.00-0.94 (12H, m).

[0289]

[0290] (Step 3) Synthesis of Compound 23 Compound 23 was obtained from Compound 22 and 5-hydroxy-3-methyl-2,5-dihydrofuran-2-one in the same manner as in the synthesis of Compound 5. Yield: 17%; ESI MS m / z: 463.2 (M+Na). + ; 1 H NMR (400 MHz, CD3OD)δ7.10 (1H, m), 6.84 (1H, m), 4.34 (1H, m), 4.25 (1H, m), 1.95 (3H, s), 1.76-1.71 (2H, m), 1.64-1.58 (4H, m), 1.47 (9H, s), 1.00-0.93 (12H, m).

[0291]

[0292] Synthesis Example 24 (Step 1) Synthesis of Compound 24 Compound 24 was obtained using phenylalanine methyl ester hydrochloride and N-Cbz-proline as starting materials in the same manner as for Compound 21. Yield: 94%; ESI MS m / z: 411.1 (M+H) + ; 1H NMR (400 MHz, CD3OD)δ7.39-7.15 (10H, m), 5.14 (2H, brs), 5.06 (1H, d, J=12.4 Hz), 4.99 (1H, d, J=12.4 Hz), 4.68 (1H, m), 4.29 (1H, m), 3.69 (1.5H, s), 3.65 (1.5H, s), 3.53-3.45 (2H, m), 3.16-3.07 (1.5H, m), 2.92 (0.5H, dd, J=4.8, 14.0 Hz), 2.18 (1H, m), 1.85-1.80 (3H, m).

[0293]

[0294] (Step 2) Synthesis of Compound 25 Compound 25 was obtained from compound 24 in the same manner as for compound 22. Yield: 95%; ESI MS m / z: 277.0 (M+H) + ; 1 H NMR (400 MHz, CD3OD)δ7.31-7.18 (5H, m), 4.72 (1H, dd, J=5.2, 8.8 Hz), 3.74 (3H, s), 3.63 (1H, dd, J=5.2, 9.2 Hz), 3.21 (1H, dd, J=5.2, 14.0 Hz), 3.02 (1H, dd, J=8.8, 14.0 Hz), 2.90-2.84 (2H, m), 2.06 (1H, m), 1.69-1.57 (3H, m).

[0295]

[0296] (Step 3) Synthesis of Compound 26 Compound 26 was obtained from Compound 25 and 5-hydroxy-3-methyl-2,5-dihydrofuran-2-one in the same manner as in the synthesis of Compound 5. Yield: 20%; ESI MS m / z: 417.1 (M+H). + ; 1H NMR (400 MHz, CD3OD)δ7.33-7.06 (6H, m), 7.06-6.77 (1H, m), 4.82 (0.5H, m),4.71 (0.5H, m), 4.35 (0.5H, m), 4.25 (0.5H, m), 3.74 (1.5H, s), 3.70 (1.5H, s), 3.58-3.45 (2H, m), 3.24-2.99 (2H, m), 2.17 (1H, m), 1.97-1.72 (6H, m).

[0297]

[0298] Synthesis Example 25: Compound 27 was obtained using N-Boc-phenylalanine and 5-hydroxy-3-methyl-2,5-dihydrofuran-2-one as starting materials in the same manner as for Compound 21. Yield: 88%; ESI MS m / z: 384.1 (M+Na). + ; 1 H NMR (400 MHz, CD3OD)δ7.19-7.10 (4H, m), 7.03-6.95 (1H, m), 6.83-6.72 (2H, m), 4.29 (1H, m), 3.00 (1H, m), 2.86 (1H, m), 1.82 (0.6H, s), 1.81 (0.4H, s), 1.28 (9H, s).

[0299]

[0300] Synthesis Example 26: Compound 28 was obtained using N-Boc-leucine and 5-hydroxy-3-methyl-2,5-dihydrofuran-2-one as starting materials in the same manner as for Compound 21. Yield: 91%; ESI MS m / z: 350.1 (M+Na). + ; 1H NMR (400 MHz, CD3OD)δ7.03 (0.5H, t, J=1.6 Hz), 7.00 (0.5H, t, J=1.6 Hz), 6.82 (1H, t, J=1.6 Hz), 6.79 (0.5H, d, J=1.6 Hz), 4.09 (1H, m), 1.84 (3H, d, J=1.6 Hz), 1.62 (1H, m), 1.52-1.43 (2H, m), 1.34 (9H, s), 0.86-0.81 (6H, m).

[0301]

[0302] Synthesis example 27 N α -,N ε Compound 29 was obtained using 2-diBoc-lysine and 5-hydroxy-3-methyl-2,5-dihydrofuran-2-one in the same manner as for Compound 21. Yield: 92%; ESI MS m / z: 465.2 (M+Na). + ; 1 H NMR (400 MHz, CD3OD)δ4.01 (1H, m), 2.95-2.92 (2H, m), 1.95 (3H, d, J=0.8 Hz). 1.87 (1H, m), 1.71 (1H, m), 1.49-1.44 (22H, m).

[0303]

[0304] Synthesis Example 28: Compound 30 was obtained using succinic acid mono-t-butyl ester and 5-hydroxy-3-methyl-2,5-dihydrofuran-2-one as starting materials in the same manner as for Compound 21. Yield: 87%; ESI MS m / z: 293.1 (M+Na). + ; 1 H NMR (400 MHz, CD3OD)δ7.12 (1H, t, J=1.6 Hz), 6.92 (1H, t, J=1.6 Hz), 2.67-2.65 (2H, m), 2.59-2.56 (2H, m), 1.86 (3H, s), 1.46 (9H, s).

[0305]

[0306] Synthesis Example 29: Compound 31 was obtained using N-Boc-tryptophan and 5-hydroxy-3-methyl-2,5-dihydrofuran-2-one as starting materials in the same manner as for Compound 21. Yield: 95%; ESI MS m / z: 423.1 (M+Na). + ; 1 H NMR (400 MHz, CD3OD)δ7.41 (1H, m), 7.24 (1H, m), 7.02-6.90 (3H, m), 6.82 (0.33H, t, J=1.6 Hz), 6.73 (0.67H, m), 6.56 (0.67H, t, J=1.6 Hz), 6.32 (0.33H, d, J=2.4 Hz), 4.36 (1H, m), 3.18-3.02 (2H, m), 1.79 (1H, s), 1.72 (2H, s), 1.30 (3H, s), 1.28 (6H, s).

[0307]

[0308] Synthesis Example 30: Compound 32 was obtained using N-Boc-methionine and 5-hydroxy-3-methyl-2,5-dihydrofuran-2-one as starting materials in the same manner as for Compound 21. Yield: 99%; ESI MS m / z: 377.0 (M+MeOH). + ; 1 H NMR (400 MHz, CD3OD)δ7.02 (1H, m), 6.82 (1H, t, J=1.6 Hz), 4.24 (0.5H, m), 4.04 (0.5H, m), 2.53-2.39 (2H, m), 2.08-1.74 (8H, m), 1.34 (9H, s).

[0309]

[0310] Synthesis Example 31: Compound 33 was obtained using N-Boc-aspartic acid β-methyl ester and 5-hydroxy-3-methyl-2,5-dihydrofuran-2-one as starting materials in the same manner as for Compound 21. Yield: 87%; ESI MS m / z: 366.0 (M+Na). + ; 1H NMR (400 MHz, CD3OD)δ7.00 (1H, m), 6.80 (1H, t, J=1.6 Hz), 4.47 (1H, m), 3.59 (3H, s), 2.84-2.67 (2H, m), 1.84 (3H, s), 1.34 (9H, s).

[0311]

[0312] Synthesis Example 32 τ-Benzyl-N α Compound 34 was obtained from -Boc-histidine and 5-hydroxy-3-methyl-2,5-dihydrofuran-2-one in the same manner as for Compound 21. Yield: 21%; ESI MS m / z: 442.2 (M+H). + ; 1 H NMR (400 MHz, CD3OD)δ7.57 (0.5H, m), 7.54 (0.5H, s), 7.27-7.20 (3H, m), 7.15-7.13 (2H, m), 6.96 (0.5H, d, J=1.6 Hz), 6.84-6.69 (3H, m), 5.06 (1H, s), 5.05 (1H, s), 4.30 (1H, m), 2.91-2.81 (2H, m), 1.83 (1.5H, s), 1.81 (1.5H, s), 1.292 (4.5H, s) 1.288 (4.5H, s).

[0313]

[0314] Synthesis example 33 τ-Cbz-N α Compound 35 was obtained from -Boc-histidine and 5-hydroxy-3-methyl-2,5-dihydrofuran-2-one in the same manner as for Compound 21. Yield: 68%; ESI MS m / z: 486.2 (M+H). + ; 1H NMR (400 MHz, CD3OD)δ 8.08 (1H, m), 7.38 (1H, m), 7.30-7.22 (5H, m), 6.96 (1H, m), 6.77 (1H, t, J=1.6 Hz), 5.33 (1.2H, s), 5.05 (0.8H, s), 4.36 (1H, m), 2.97-2.80 (2H, m), 1.81 (3H, s), 1.28 (5.4H, s), 1.27 (3.6H, s).

[0315]

[0316] Synthesis Example 34: 5-Hydroxy-3-methyl-2,5-dihydrofuran-2-one (114 mg, 1.00 mmol) and glutaric anhydride (114 mg, 1.00 mmol) were dissolved in acetonitrile (2 mL), and triethylamine (0.15 mL, 1.08 mmol) was added. The mixture was stirred at room temperature for 2 hours. The solvent and excess reagents were evaporated to dryness under reduced pressure to give compound 36 as a triethylamine salt. Yield: 99%; ESI MS m / z: 250.9 (M+Na). + ; 1 H NMR (400 MHz, CDCl3)δ11.36 (1H, br), 6.94 (1H, d, J=1.6 Hz), 6.88 (1H, t, J=1.6 Hz), 3.11 (2H, q, J=7.2 Hz), 2.48 (2H, t, J=7.2 Hz), 2.38 (2H, t, J=7.2 Hz), 2.05-1.91 (5H, m), 1.27 (3H, t, J=7.2 Hz).

[0317]

[0318] Synthesis Example 35: Compound 37 was obtained using N-Boc-phenylalanine and 5-hydroxy-2,5-dihydrofuran-2-one as starting materials in the same manner as for Compound 21. Yield: 40%; ESI MS m / z: 370.0 (M+Na). + ; 1H NMR (400 MHz, CD3OD)δ7.53 (0.5H, dd, J=1.2, 5.6 Hz), 7.37-7.23 (4.5H, m), 7.05 (0.5H, s), 6.99 (0.5H, t, J=1.2 Hz), 6.38 (1H, t, J=1.2 Hz), 4.42 (1H, m), 3.13 (1H, m), 2.98 (1H, m), 1.40 (9H, s).

[0319]

[0320] Synthesis Example 36: L-pyroglutamic acid and N ε Compound 38 was obtained using -Boc-lysine t-butyl ester hydrochloride as a starting material in the same manner as for Compound 21. Yield: 85%; ESI MS m / z: 414.2 (M+H). + ; 1 H NMR (400 MHz, CD3OD)δ4.28-4.24 (2H, m), 3.05 (2H, t, J=6.8 Hz), 2.54-2.27 (5H, m), 2.15 (1H, m), 1.86-1.83 (2H, m), 1.76-1.68 (2H, m), 1.49 (9H, s), 1.45 (9H, s).

[0321]

[0322] Synthesis Example 37: Compound 38 (150 mg, 0.36 mmol) was dissolved in a 4N solution of hydrochloric acid in dioxane (2 mL) and stirred at room temperature for 18 hours. The mixture was concentrated to dryness under reduced pressure to give compound 39 as a hydrochloride salt. Yield: 99%. 1 H NMR (400 MHz, D2O)δ4.30-4.26 (2H, m), 2.88 (2H, t, J=8.0 Hz), 2.43 (1H, m), 2.33-2.28 (2H, m), 1.97 (1H, m), 1.83 (1H, m), 1.70 (1H, m), 1.61-1.54 (2H, m), 1.39-1.30 (2H, m).

[0323]

[0324] Synthesis example 38 N α Compound 40 was obtained from -Cbz-lysine benzyl ester and L-pyroglutamic acid in the same manner as for compound 21. Yield: 96%; ESI MS m / z: 482.2 (M+H). + ; 1 H NMR (400 MHz, CD3OD)δ7.37-7.30 (10H, m), 5.21-5.06 (4H, m), 4.23 (1H, dd, J=4.8, 8.8 Hz), 4.12 (1H, dd, J=4.8, 8.8 Hz), 3.19-3.16 (2H, m), 2.46-2.34 (2H, m), 2.27 (1H, m), 2.01 (1H, m), 1.84 (1H, m), 1.70 (1H, m), 1.57-1.47 (2H, m), 1.43-1.36 (2H, m).

[0325]

[0326] Synthesis Example 39: Compound 41 was obtained from compound 40 in the same manner as in compound 22. Yield: 92%. 1 H NMR (400 MHz, D2O)δ4.19 (1H, dd, J=5.2, 8.8 Hz), 3.60 (1H, t, J=6.0 Hz), 3.17-3.12 (2H, m), 2.49-2.30 (3H, m), 1.96 (1H, m), 1.77-1.73 (2H, m), 1.49-1.45 (2H, m), 1.32-1.28 (2H, m).

[0327]

[0328] Synthesis example 40 N α Compound 42 was obtained from -Cbz-lysine benzyl ester and D-pyroglutamic acid in the same manner as for Compound 21. Yield: 72%; ESI MS m / z: 482.2 (M+H). + ; 1H NMR (400 MHz, CD3OD)δ7.36-7.29 (10H, m), 5.20-5.06 (4H, m), 4.25 (1H, t, J=4.4 Hz), 4.12 (1H, dd, J=4.8, 8.8 Hz), 3.19-3.15 (2H, m), 2.41-2.34 (2H, m), 2.26 (1H, m), 2.01 (1H, m), 1.83 (1H, m), 1.70 (1H, m), 1.56-1.44 (2H, m), 1.42-1.34 (2H, m).

[0329]

[0330] Synthesis Example 41: Compound 43 was obtained from Compound 42 in the same manner as in Compound 41. Yield: 86%; ESI MS m / z: 258.1 (M+H) + ; 1 H NMR (400 MHz, D2O)δ4.19 (1H, dd, J=5.2, 8.8 Hz), 3.63 (1H, dd, J=6.0, 6.4 Hz), 3.17-3.13 (2H, m), 2.47-2.30 (3H, m), 1.96 (1H, m), 1.84-1.70 (2H, m), 1.51-1.44 (2H, m), 1.38-1.23 (2H, m).

[0331]

[0332] Synthesis Example 42: Compound 44 was obtained using leucine t-butyl ester hydrochloride and D-pyroglutamic acid as starting materials in the same manner as for Compound 21. Yield: 74%; ESI MS m / z: 299.1 (M+H) + ; 1 H NMR (400 MHz, CD3OD)δ4.35 (1H, dd, J=6.4, 8.8 Hz), 4.24 (1H, dd, J=4.8, 8.4 Hz), 2.54-2.28 (3H, m), 2.09 (1H, m), 1.70 (1H, m), 1.66-1.61 (2H, m), 0.99 (3H, d, J=6.4 Hz), 0.94 (3H, d, J=6.4 Hz).

[0333]

[0334] Synthesis Example 43: Compound 45 was obtained using phenylalanine t-butyl ester hydrochloride and D-pyroglutamic acid as starting materials in the same manner as for Compound 21. Yield: 89%; ESI MS m / z: 377.1 (M+HCO). - ; 1 H NMR (400 MHz, CD3OD)δ7.33-7.22 (5H, m), 4.64 (1H, dd, J=6.0, 9.2 Hz), 4.16 (1H, dd, J=4.8, 8.4 Hz), 3.18 (1h, dd, J=6.0, 13.6 Hz), 2.97 (1H, dd, J=9.2, 13.6 Hz), 2.34-2.21 (3H, m), 1.77 (1H, m), 1.44 (9H, s).

[0335]

[0336] Synthesis example 44 N α Compound 46 was obtained from -Cbz-lysine benzyl ester benzenesulfonate and (R)-(-)-5-oxotetrahydrofuran-2-carboxylic acid in the same manner as for Compound 21. Yield: 91%; ESI MS m / z: 483.2 (M+H). + ; 1 H NMR (400 MHz, CD3OD)δ7.38-7.30 (10H, m), 5.20 (1H, d, J=13.4 Hz), 5.15 (1H, d, J=13.4 Hz), 5.10 (2H, s), 3.21 (2H, t, J=6.8 Hz), 2.57-2.54 (3H, m), 2.23-2.14 (2H, m), 1.85 (1H, m), 1.71 (1H, m), 1.59-1.47 (2H, m), 1.43-1.35 (2H, m).

[0337]

[0338] Synthesis example 45 N εCompound 47 was obtained from -Cbz-lysine benzyl ester hydrochloride and D-pyroglutamic acid in the same manner as for Compound 21. Yield: 64%; ESI MS m / z: 482.2 (M+H). + ; 1 H NMR (400 MHz, CD3OD)δ7.41-7.30 (10H, m), 5.19 (1H, d, J=12.0 Hz), 5.16 (1H, d, J=12.0 Hz), 5.07 (2H, s), 4.45 (1H, dd, J=4.8, 9.2 Hz), 4.22 (1H, d, J=4.8, 8.8 Hz), 3.12-3.08 (2H, m), 2.47-2.20 (4H, m), 2.02 (1H, m), 1.89 (1H, m), 1.76 (1H, m), 1.52-1.46 (2H, m), 1.42-1.36 (2H, m).

[0339]

[0340] Synthesis Example 46: Compound 48 was obtained from compound 44 in the same manner as in compound 39. Yield: 99%; ESI MS m / z 243.1 (M+H) + ; 1 H NMR (400 MHz, CD3OD)δ6.34 (1H, d, J=8.0 Hz), 4.48 (1H, m), 4.25 (1H, dd, J=4.8, 8.8 Hz), 2.53-2.40 (2H, m), 2.31 (1H, m), 2.10 (1H, m), 1.71-1.67 (3H, m), 1.00 (3H, d, J=6.0 Hz), 0.96 (3H, d, J=6.0 Hz).

[0341]

[0342] Synthesis Example 47: Compound 49 was obtained from Compound 45 in the same manner as in Compound 39. Yield: 99%; ESI MS m / z: 277.1 (M+H) + ; 1H NMR (400 MHz, CD3OD)δ7.32-7.21 (5H, m), 4.76 (1H, dd, J=4.8, 9.6 Hz), 4.15 (1H, dd, J=4.8, 8.4 Hz), 3.30 (1H, dd, J=4.4, 10.0 Hz), 2.97 (1H, dd, J=9.6, 10.0 Hz), 3.32-2.19 (3H, m), 1.71 (1H, m).

[0343]

[0344] Synthesis Example 48: Compound 50 was obtained using D-phenylalanine t-butyl ester hydrochloride and D-pyroglutamic acid as starting materials in the same manner as for Compound 21. Yield: 85%; ESI MS m / z: 377.1 (M+HCO). - ; 1 H NMR (400 MHz, CD3OD)δ7.32-7.24 (5H, m), 4.61 (1H, dd, J=6.0, 8.8 Hz), 4.17 (1H, dd, J=4.4, 8.8 Hz), 3.17 (1H, dd, J=6.0, 12.0 Hz), 3.00 (1H, dd, J=8.8, 12.0 Hz), 2.42 (1H, m), 2.30-2.24 (2H, m), 1.96 (1H, m), 1.44 (9H, s).

[0345]

[0346] Synthesis Example 49: Compound 51 was obtained using phenylalanine t-butyl ester hydrochloride and L-pyroglutamic acid as starting materials in the same manner as for Compound 21. Yield: 80%; ESI MS m / z: 377.1 (M+HCO). - ; 1H NMR (400 MHz, CD3OD)δ7.32-7.24 (5H, m), 4.61 (1H, dd, J=6.0, 8.8 Hz), 4.17 (1H, dd, J=4.4, 8.4 Hz), 3.17 (1H, dd, J=6.0, 14.0 Hz), 3.00 (1H, dd, J=8.8, 14.0 Hz), 2.42 (1H, m), 2.30-2.24 (2H, m), 1.97 (1H, m), 1.44 (9H, s).

[0347]

[0348] Synthesis Example 50: Compound 52 was obtained using D-phenylalanine t-butyl ester hydrochloride and L-pyroglutamic acid as starting materials in the same manner as for Compound 21. Yield: 89%; ESI MS m / z: 377.0 (M+HCO). - ; 1 H NMR (400 MHz, CD3OD)δ7.33-7.22 (5H, m), 4.64 (1H, dd, J=6.0, 9.2 Hz), 4.16 (1H, dd, J=4.8, 8.4 Hz), 3.18 (1H, dd, J=6.0, 14.0 Hz), 2.97 (1H, dd, J=9.2, 14.0 Hz), 2.34-2.21 (3H, m), 1.76 (1H, m), 1.44 (9H, s).

[0349]

[0350] Synthesis Example 51: Compound 53 was obtained using leucyl-leucine t-butyl ester hydrochloride and D-pyroglutamic acid as starting materials in the same manner as for Compound 21. Yield: 70%; ESI MS m / z: 456.2 (M+HCO). - ; 1H NMR (400 MHz, CD3OD)δ4.48 (1H, dd, J=6.8, 8.0 Hz), 4.33 (1H, dd, J=6.8, 8.4 Hz), 4.24 (1H, dd, J=4.8, 8.8 Hz), 2.52-2.28 (3H, m), 2.06 (1H, m), 1.78-1.67 (2H, m), 1.65-1.58 (4H, m), 1.48 (9H, s), 1.00 (3H, d, J=6.8 Hz), 0.98 (3H, d, J=6.8 Hz), 0.97 (3H, d, J=6.4 Hz), 0.92 (3H, d, J=6.4 Hz).

[0351]

[0352] Synthesis Example 52: Compound 54 was obtained using sarcosine t-butyl ester and D-pyroglutamic acid as starting materials in the same manner as for Compound 21. Yield: 17%; ESI MS m / z: 513.3 (2M+H). + ; 1 H NMR (400 MHz, CD3OD)δ4.77 (0.7H, dd, J=4.0, 8.8 Hz), 4.59 (0.3H, dd, J=4.4, 8.4 Hz), 4.27 (0.3H, d, J=18.4 Hz), 4.19 (0.7H, d, J=16.8 Hz), 4.12 (0.7H, d, J=18.4 Hz), 3.90 (0.3H, d, J=16.8 Hz), 3.14 (2.1H, s), 2.97 (0.9H, s), 2.57 (1H, m), 2.44-2.30 (2H, m), 2.09 (1H, m), 1.52 (2.7H, s), 1.49 (6.3H, s).

[0353]

[0354] Synthesis Example 53: Compound 55 was obtained using proline t-butyl ester and D-pyroglutamic acid as starting materials in the same manner as for Compound 21. Yield: 12%; ESI MS m / z: 565.3 (2M+H). + ; 1H NMR (400 MHz, CD3OD)δ4.67 (0.25H, dd, J=2.4, 8.8 Hz), 4.60 (0.75H, dd, J=4.4, 8.8 Hz), 4.40 (0.25H, t, J=4.0 Hz), 4.34 (0.75H, dd, J=4.4, 8.8 Hz), 3.76 (1H, m), 3.60 (1H, m), 2.57-2.21 (4H, m), 2.12-1.93 (4H, m), 1.52 (2.25H, s), 1.48 (6.75H, s).

[0355]

[0356] Synthesis Example 54: Compound 56 was obtained from Compound 53 in the same manner as for Compound 39. Yield: 99%; ESI MS m / z: 356.1 (M+H) + ; 1 H NMR (400 MHz, CD3OD)δ4.50-4.43 (2H, m), 4.25 (1H, dd, J=4.4, 8.4 Hz), 2.52-2.28 (3H, m), 2.06 (1H, m), 1.80-1.70 (2H, m), 1.68-1.62 (4H, m), 1.00-0.93 (12H, m).

[0357]

[0358] Synthesis Example 55: Compound 57 was obtained using mono N-Boc-cadaverine and D-pyroglutamic acid as starting materials in the same manner as for Compound 21. Yield: 27%; ESI MS m / z: 314.1 (M+H) + ; 1 H NMR (400 MHz, CD3OD)δ4.17 (1H, m), 3.24-3.20 (2H, m), 3.06 (2H, t, J=6.8 Hz), 2.50-2.28 (3H, m), 2.07 (1H, m), 1.58-1.34 (15H, m).

[0359]

[0360] Synthesis Example 56: Compound 58 was obtained from Compound 57 in the same manner as Compound 39. Yield: 99%; ESI MS m / z: 214.0 (M+H) + ; 1 H NMR (400 MHz, CD3OD)δ4.27 (1H, dd, J=4.8, 8.4 Hz), 3.25 (2H, t, J=6.8 Hz), 2.98-2.94 (2H, m), 2.53-2.32 (3H, m), 2.08 (1H, m), 1.74-1.70 (2H, m), 1.62-1.58 (2H, m), 1.48-1.42 (2H, m).

[0361]

[0362] Synthesis Example 57: Compound 59 was obtained using GABA ethyl ester hydrochloride and D-pyroglutamic acid as starting materials in the same manner as for Compound 21. Yield: 33%; ESI MS m / z: 243.0 (M+H) + ; 1 H NMR (400 MHz, CD3OD)δ4.05-4.00 (3H, m), 3.21-3.12 (2H, m), 2.40-2.16 (5H, m), 1.94 (1H, m), 1,75-1.68 (2H, m), 1.15 (3H, t, J=6.8 Hz).

[0363]

[0364] Synthesis Example 58: Compound 59 (75 mg, 0.31 mmol) was dissolved in ethanol (2 mL), and 1N aqueous sodium hydroxide solution (0.5 mL) was added, followed by stirring at room temperature for 2 hours. After adding water (3 mL), the reaction mixture was filtered with Amberlite FPC3500 (H + The resulting non-adsorbed fraction was concentrated to dryness to give Compound 60. Yield: 90%. 1 H NMR (400 MHz, D2O)δ4.20 (1H, dd, J=5.2, 9.2 Hz), 3.20-3.16 (2H, m), 2.47-2.28 (3H, m), 1.97 (1H, m), 1.76-1.69 (2H, m).

[0365]

[0366] Synthesis Example 59: Compound 61 was obtained using serine methyl ester hydrochloride and D-pyroglutamic acid as starting materials in the same manner as for Compound 21. Yield: 57%; ESI MS m / z: 231.0 (M+H). + ; 1 H NMR (400 MHz, CD3OD)δ4.56 (1H, dd, J=4.0, 9.2 Hz), 4.36 (1H, dd, J=4.8, 8.8 Hz), 3.94 (1H, dd, J=5.2, 11.2 Hz), 3.85 (1H, dd, J=4.0, 11.2 Hz), 3.77 (3H, s), 2.54-2.36 (4H, m), 2.24-2.13 (2H, m).

[0367]

[0368] Synthesis Example 60: Compound 62 was obtained using L-homoserine lactone hydrochloride and N-Boc-L-pyroglutamic acid as starting materials in the same manner as for Compound 21. Yield: 26%; ESI MS m / z: 357.0 (M+HCO2 - ) - ; 1 H NMR (400 MHz, CDCl3)δ7.54 (1H, d, J=8.0 Hz), 4.62 (1H, dd, J=4.4, 9.2 Hz), 4.41 (1H, m), 4.25 (1H, m), 2.75-2.60 (2H, m), 2.50-2.35 (3H, m), 2.17 (1H, m).

[0369]

[0370] Synthesis Example 61: Compound 63 was obtained from Compound 62 in the same manner as Compound 39. Yield: 99%; ESI MS m / z: 213.0 (M+H) + ; 1H NMR (400 MHz, CD3OD)δ4.67 (1H, dd, J=8.8, 11.2 Hz), 4.49 (1H, dd, J=2.0, 8.8 Hz), 4.45-4.25 (2H, m), 2.60-2.30 (5H, m), 2.16 (1H, m).

[0371]

[0372] Synthesis Example 62: Compound 64 was obtained using D-homoserine lactone hydrochloride and N-Boc-L-pyroglutamic acid as starting materials in the same manner as in Compound 21. Yield: 20%; ESI MS m / z: 357.0 (M+HCO2 - ) - ; 1 H NMR (400 MHz, CD3OD)δ4.66-4.58 (2H, m), 4.48 (1H, m), 4.33 (1H, m), 2.67-2.56 (2H, m), 2.52-2.31 (3H, m), 2.00 (1H, m), 1.52 (9H, s).

[0373]

[0374] Synthesis Example 63: Compound 65 was obtained from Compound 64 in the same manner as in Compound 39. Yield: 99%; ESI MS m / z: 212.9 (M+H) + ; 1 H NMR (400 MHz, CD3OD)δ4.55 (1H, dd, J=8.8, 10.8 Hz), 4.38 (1H, dd, J=1.6, 9.2 Hz), 4.34-4.12 (2H, m), 2.45-2.21 (5H, m), 2.01 (1H, m).

[0375]

[0376] Synthesis Example 64: D-pyroglutamic acid (30 mg, 0.023 mmol) was added with n-butanol (0.5 mL) and 4N hydrochloric acid in dioxane (0.5 mL), and the mixture was stirred at room temperature for 4 days. The solvent and excess reagents were removed under reduced pressure to give compound 66 as a colorless oil. Yield: 99%; ESI MS m / z: 186.1 (M+H).+ ; 1 H NMR (400 MHz, CDCl3)δ6.70 (1H, brs), 4.25 (1H, m), 4.16 (2H, m), 2.52-2.34 (3H, m), 2.20 (1H, m), 1.66-1.60 (2H, m), 1.41-1.35 (2H, m), 0.94 (3H, t, J=7.2 Hz).

[0377]

[0378] Synthesis Example 65: Compound 67 was obtained as a colorless oil using D-pyroglutamic acid and n-hexanol as starting materials in the same manner as for Compound 66. ESI MS m / z 214.1 (M+H) + ; 1 H NMR (400 MHz, CDCl3)δ4.26 (1H, m), 4.16-4.15 (2H, m), 2.49 (1H, m), 2.42-2.36 (2H, m), 2.23 (1H, m), 1.68-1.62 (2H, m), 1.37-1.29 (6H, m), 0.90 (3H, t, J=6.8 Hz).

[0379]

[0380] Synthesis Example 66: Compound 68 was obtained using D-pyroglutamic acid and n-dodecanol as starting materials in the same manner as Compound 66. ESI MS m / z 595.5 (2M+H) + ; 1 H NMR (400 MHz, CDCl3)δ4.30 (1H, dd, J=4.4, 8.4 Hz), 4.18 (2H, t, J=6.4 Hz), 2.57-2.29 (3H, m), 2.16 (1H, m), 1.71-1.65 (2H, m), 1.52 (1H, m), 1.37-1.22 (17H, m), 0.92 (3H, t, J=6.8 Hz).

[0381]

[0382] Synthesis Example 67: Compound 69 was obtained using D-pyroglutamic acid and geraniol as starting materials in the same manner as for Compound 21. Yield: 78%; ESI MS m / z: 266.1 (M+H) + ; 1 H NMR (400 MHz, CD3OD)δ5.39 (1H, m), 5.11 (1H, m), 4.71 (2H, d, J=6.8 Hz), 4.29 (1H, dd, J=4.8, 8.8 Hz), 2.50 (1H, m), 2.42-2.28 (2H, m), 2.19-2.06 (5H, m), 1.75 (3H, d, J=1.6 Hz), 1.69 (3H, d, J=1.6 Hz), 1.63 (3H, d, J=1.6 Hz).

[0383]

[0384] Synthesis Example 68: Compound 70 was obtained using nerol and D-pyroglutamic acid as starting materials in the same manner as for Compound 21. Yield: 95%; ESI MS m / z: 266.1 (M+H) + ; 1 H NMR (400 MHz, CD3OD)δ5.39 (1H, m), 5.14 (1H, m), 4.68 (2H, dd, J=0.8, 6.8 Hz), 4.29 (1H, dd, J=4.8, 8.8 Hz), 2.50 (1H, m), 2.42-2.28 (2H, m), 2.20-2.10 (5H, m), 1.79 (3H, d, J=1.2 Hz), 1.70 (3H, d, J=1.2 Hz), 1.64 (3H, d, J=1.2 Hz).

[0385]

[0386] Synthesis Example 69: Compound 71 was obtained using phenethyl alcohol and D-pyroglutamic acid as starting materials in the same manner as for Compound 21. Yield: 54%; m / z: 234.1 (M+H). + ; 1H NMR (400 MHz, CD3OD)δ7.33-7.21 (5H, m), 4.45-4.37 (2H, m), 4.25 (1H, dd, J=4.0, 8.8 Hz), 3.01-2.97 (2H, m), 2.55 (1H, m), 2.43 (1H, m), 2.28-2.24 (2H, m), 2.05-1.99 (2H, m).

[0387]

[0388] Synthesis Example 70: Compound 72 was obtained using indoleacetic acid and (S)-pyroglutaminol as starting materials in the same manner as for Compound 21. Yield: 72%; ESI MS m / z 273.1 (M+H) + ; 1 H NMR (400 MHz, CD3OD)δ7.42 (1H, d, J=7.6 Hz), 7.24 (1H, d, J=8.4 Hz), 7.05 (1H, s), 7.00 (1H, m), 6.92 (1H, m), 4.03 (1H, dd, J=4.0, 11.6 Hz), 3.89 (1H, dd, J=2.0, 11.6 Hz), 3.72 (1H, m), 3.69 (2H, s), 2.07-1.98 (3H, m), 1.60 (1H, m).

[0389]

[0390] Synthesis Example 71: Compound 73 was obtained using indoleacetic acid and (R)-pyroglutaminol as starting materials in the same manner as for Compound 21. Yield: 65%; ESI MS m / z 273.1 (M+H) + ; 1H NMR (400 MHz, CD3OD)δ7.54 (1H, dd, J=1.2, 8.0 Hz), 7.36 (1H, d, J=8.0 Hz), 7.18 (1H, s), 7.12 (1H, m), 7.04 (1H, m), 4.16 (1H, dd, J=4.0, 11.6 Hz), 4.02 (1H, dd, J=5.2, 11.6 Hz), 3.86 (1H, m), 3.85 (2H, s), 2.20-2.11 (3H, m), 1.73 (1H, m).

[0391]

[0392] Synthesis Example 72: Compound 74 was obtained using n-octanoic acid and (R)-pyroglutaminol as starting materials in the same manner as for Compound 21. Yield: 89%; ESI MS m / z: 242.1 (M+H). + ; 1 H NMR (400 MHz, CD3OD)δ4.19 (1H, dd, J=4.0, 11.2 Hz), 4.03-3.92 (2H, m), 2.45-2.26 (5H, m), 1.91 (1H, m), 1.65-1.62 (2H, m), 1.37-1.31 (8H, m), 0.92 (3H, t, J=6.8 Hz).

[0393]

[0394] Synthesis Example 73: Compound 75 was obtained using lauric acid and (R)-pyroglutaminol as starting materials in the same manner as for Compound 21. Yield: 95%; m / z: 595.5 (2M+H). + ; 1 H NMR (400 MHz, CD3OD)δ4.19 (1H, dd, J=4.0, 11.2 Hz), 4.03-3.94 (2H, m), 2.40-2.27 (5H, m), 1.91 (1H, m), 1.65-1.62 (2H, m), 1.37-1.31 (16H, m), 0.92 (3H, t, J=6.8 Hz).

[0395]

[0396] Synthesis Example 74: Compound 76 was obtained using N-Boc-phenylalanine and (R)-pyroglutaminol as starting materials in the same manner as for Compound 21. Yield: 87%; ESI MS m / z 385.2 (M+Na). + ; 1 H NMR (400 MHz, CD3OD)δ7.33-7.22 (5H, m), 4.38 (1H, dd, J=6.0, 8.8 Hz), 4.10-4.08 (2H, m), 3.88 (1H, m), 3.12 (1H, dd, J=6.0, 13.6 Hz), 2.95 (1H, dd, J=8.8, 13.6 Hz), 2.45-2.18 (3H, m), 1.84 (1H, m), 1.41 (9H, s).

[0397]

[0398] Synthesis Example 75: Compound 77 (hydrochloride) was obtained using Compound 42 as a starting material in the same manner as Compound 39. Yield: 99%; ESI MS m / z 263.1 (M+H) + ; 1 H NMR (400 MHz, CD3OD)δ7.37-7.19 (5H, m), 4.43 (1H, t, J=6.8 Hz), 4.26 (1H, dd, J=3.6, 11.2 Hz), 4.06 (1H, dd, J=6.0, 11.2 Hz), 3.90 (1H, m), 3.26-3.16 (2H, m), 2.33-2.28 (2H, m), 2.24-1.76 (2H, m), .

[0399]

[0400] Synthesis Example 76: Compound 78 was obtained using succinic acid semi-t-butyl ester and (R)-pyroglutaminol as starting materials in the same manner as for Compound 21. Yield: 78%; ESI MS m / z: 294.1 (M+Na). + ; 1H NMR (400 MHz, CD3OD)δ4.17 (1H, dd, J=4.0, 11.2 Hz), 4.06 (1H, dd, J=6.0, 11.2 Hz), 3.95 (1H, m), 2.64-2.54 (4H, m), 2.46-2.26 (3H, m), 1.91 (1H, m), 1.46 (9H, s).

[0401]

[0402] Synthesis Example 77: Compound 79 was obtained using N-Boc-GABA and (R)-pyroglutaminol as starting materials in the same manner as for Compound 21. Yield: 57%; ESI MS m / z: 301.0 (M+H). + ; 1 H NMR (400 MHz, CD3OD)δ4.18 (1H, dd, J=3.6, 10.8 Hz), 4.05-3.94 (2H, m), 3.11-3.08 (2H, m), 2.43-2.29 (5H, m), 1.90 (1H, m), 1.82-1.75 (2H, m), 1.45 (9H, s).

[0403]

[0404] Synthesis Example 78: To a THF solution (2 mL) of 5-hydroxy-3-methyl-2,5-dihydrofuran-2-one (35 mg, 0.31 mmol) and N-Boc-glutamine methyl ester (77 mg, 0.30 mmol), concentrated sulfuric acid (0.05 mL) was added and stirred at room temperature for 2 days. Ethyl acetate was added to the reaction solution, and the mixture was partitioned and washed with water. The organic layer was dehydrated and dried over anhydrous sodium sulfate and then concentrated to dryness under reduced pressure. The resulting residue was purified by reverse-phase HPLC (water / acetonitrile) to give compound 80. Yield: 4%; ESI MS m / z: 379.0 (M+Na). + ; 1H NMR (400 MHz, CD3OD) δ7.04 (1H, t, J=1.6 Hz), 6.55 (1H, dd, J=1.6 Hz), 4.15 (1H, m), 3.74 (3H, s), 2.37 (2H, t, J=7.2 Hz), 2.16 (1H, m), 1.94-1.91 (4H, m), 1.459 (4.5H, s), 1.457 (4.5H, s).

[0405]

[0406] Synthesis Example 79 (Step 1) Synthesis of Compound 81 Compound 81 was obtained using octanoic acid and N,N'-di-Boc-guanidine as starting materials in the same manner as for Compound 21. Yield: 66%; ESI MS m / z: 386.2 (M+H) + ; 1 H NMR (400 MHz, CDCl3)δ2.51 (1H, br), 2.32 (1H, t, J=7.2 Hz), 1.69-1.61 (2H, m), 1.50 (9H, s), 1.49 (9H, s), 1.34-1.26 (8H, m), 0.90-0.86 (3H, m).

[0407]

[0408] (Step 2) Synthesis of Compound 82. A 60% dispersion of sodium hydride in mineral oil (26 mg, 1.08 mmol) was dispersed in DMF (1 mL) and stirred at room temperature for 5 minutes. A DMF solution (1 mL) of compound 81 (240 mg, 0.62 mmol) was added and stirred at room temperature for 5 minutes. A DMF solution (1 mL) of 5-bromo-3-methyl-2,5-dihydrofuran-2-one (110 mg, 0.62 mmol) was added to the reaction mixture and stirred at room temperature for 4 hours. Ethyl acetate was added to the reaction mixture, followed by distribution washing with 0.1N hydrochloric acid. The organic layer was concentrated to dryness under reduced pressure and purified using Sep-Pack silica gel (n-hexane / ethyl acetate) to obtain compound 82. Yield: 16%; ESI MS m / z: 482.3 (M+H). + ; 1H NMR (400 MHz, CDCl3)δ6.19 (1H, d, J=7.6 Hz), 5.12 (1H, dd, J=7.6, 11.2 Hz Hz), 3.08-2.94 (2H, m), 1.70-1.61 (2H, m), 1.54 (9H, s), 1.52 (9H, s), 1.50 (3H, s), 1.33-1.27 (8H, m), 0.89 (3H, t, J=6.8 Hz).

[0409]

[0410] (Step 3) Synthesis of Compound 83 Compound 83 was obtained from compound 82 in the same manner as compound 2. Yield: 99%; ESI MS m / z: 282.0 (M+H) + ; 1 H NMR (400 MHz, CDCl3)δ5.38 (1H, brs), 4.67 (1H, brs), 2.82 (1H, m), 2.64 (1H, m), 2.49 (1H, m), 2.30 (1H, m), 1.66-1.61 (3H, m), 1.30-1.26 (8H, m), 0.89-0.86 (3H, m).

[0411]

[0412] Synthesis Example 80: Compound 84 was obtained in the same manner as for Compound 80 using N,N',N''-tri-Boc-guanidine and 5-hydroxy-3-methyl-2,5-dihydrofuran-2-one as starting materials. Yield: 87%. 1 H NMR (400 MHz, CD3OD)δ6.99 (1H, t, J=1.6 Hz), 6.05 (1H, brs), 1.91 (3H, t, J=1.6 Hz), 1.54 (18H, s), 1.46 (9H, s).

[0413]

[0414] Synthesis Example 81: Compound 85 (formate) was obtained from Compound 84 in the same manner as in Compound 2. Yield: 99%. 1H NMR (400 MHz, CD3OD)δ8.53 (1H, s),7.03 (1H, t, J=1.6 Hz), 6.46 (1H, t, J=1.6 Hz), 1.93 (3H, t, J=1.6 Hz).

[0415]

[0416] Synthesis Example 82: Compound 86 was obtained using N-Boc-glutamic acid-γ-t-butyl ester and L-homoserine lactone hydrochloride as starting materials in the same manner as for Compound 21. Yield: 83%; ESI MS m / z: 409.1 (M+Na). + ; 1 H NMR (400 MHz, CD3OD)δ4.63 (1H, dd, J=9.2, 11.2 Hz), 4.45 (1H, dd, J=5.6, 8.8 Hz), 4.33 (1H, m), 3.99 (1H, m), 2.57 (1H, m), 2.38-2.23 (3H, m), 2.11 (1H, m), 1.89 (1H, m), 1.49 (9H, s), 1.46 (9H, s).

[0417]

[0418] Synthesis Example 83: Compound 87 was obtained as a hydrochloride salt from Compound 86 in the same manner as for Compound 39. Yield: 99%; ESI MS m / z: 230.9 (M+H) + ; 1 H NMR (400 MHz,D2O)δ4.62 (1H, dd, J=9.2, 10.8 Hz), 4.51 (1H, m), 4.34 (1H, m), 4.05 (1H, t, J=6.4 Hz), 2.61-2.50 (3H, m), 2.35-2.16 (3H, m).

[0419]

[0420] Synthesis Example 84: Compound 88 was obtained using N-Boc-glutamic acid-γ-t-butyl ester and D-homoserine lactone hydrochloride as starting materials in the same manner as for Compound 21. Yield: 89%; ESI MS m / z: 409.1 (M+Na). +; 1 H NMR (400 MHz, CD3OD)δ4.60 (1H, dd, J=9.6, 11.2 Hz), 4.47 (1H, m), 4.32 (1H, m), 4.00 (1H, m), 2.56 (1H, m), 2.38-2.27 (3H, m), 2.11 (1H, m), 1.91 (1H, m), 1.49 (9H, s), 1.46 (9H, s).

[0421]

[0422] Synthesis Example 85: Compound 89 was obtained as a hydrochloride salt from Compound 88 in the same manner as in Compound 39. Yield: 99%; ESI MS m / z: 231.0 (M+H) + ; 1 H NMR (400 MHz,D2O)δ4.58 (1H, dd, J=9.2, 11.2 Hz), 4.47 (1H, m), 4.30 (1H, m), 3.98 (1H, t, J=6.4 Hz), 2.54-2.45 (3H, m), 2.29-2.10 (3H, m).

[0423]

[0424] Synthesis Example 86: Compound 90 was obtained from Compound 5 in the same manner as Compound 22. Yield: 68%; ESI MS m / z: 386.1 (M+Na) + ; 1 H NMR (400 MHz, CD3OD)δ7.32-7.23 (5H, m), 6.45 (1H, m), 4.33 (1H, m), 3.14-2.92 (2H, m), 2.80-2.72 (2H, m), 1.90 (1H, m), 1.48 (2H, s), 1.43 (3.5H, s), 1.41 (3.5H, s), 1.34 (2H, d, J=6.8 Hz), 1.13 (0.4H, d, J=7.2 Hz), 0.93 (0.6H, d, J=7.2 Hz).

[0425]

[0426] Example 1: Binding activity of various compounds to the Arabidopsis strigolactone receptor D14 protein. In this example, the binding activity of compounds 1-20, 23, 26-61, 65-80, and 83-90 to the Arabidopsis strigolactone receptor D14 protein was analyzed by measuring the degree of inhibition of binding between D14 and Yoshimulactone Green (YLG), a synthetic strigolactone labeled with a fluorescent probe. YLG is a compound that emits green fluorescence upon binding to the strigolactone receptor. D14 has the activity of hydrolyzing strigolactone. When YLG is bound in place of strigolactone, the D-ring moiety of YLG is cleaved from the fluorescent probe, resulting in fluorescence. However, the coexistence of a compound with strigolactone activity inhibits the binding of YLG to D14, resulting in a decrease in fluorescence intensity. By measuring the degree of inhibition, it is possible to measure the degree to which compounds with strigolactone activity bind to the receptor (Reference 1: Tsuchiya et al., (2015) Science, 349, 864-868. Parasitic Plants. Probing strigolactone receptors in Striga hermonthica with fluorescence.).

[0427] The D14 receptor-YLG in vitro assay was performed according to reference 1. One μg of purified D14 protein expressed in Escherichia coli was added to a buffer (100 mM HEPES, 150 mM NaCl, pH 7.0) in a total volume of 100 μL. Measurements were performed using a COSTAR black 96-well plate with a SpectraMax M2 (Molecular Devices). YLG fluorescence was excited at 480 nm and measured at 520 nm. The test compounds were added to the reaction mixture at final concentrations of 100 μM–1000 μM, with YLG at a final concentration of 1 μM. The degree of inhibition obtained using the test compounds was calculated relative to the degree of inhibition obtained using the synthetic strigolactone GR24 at the same concentration, which was set to 100%.

[0428] The results are shown in Tables 1 to 6.

[0429] In the table, "D14 inhibition" indicates the binding activity of each compound to D14. Compounds with a relative inhibition rate of 80% or less are marked with a (+) and others with a (-). Some compounds inhibited the binding of YLG to D14, i.e., they exhibited binding activity to D14. Compound 10 exhibited a (+) "D14 inhibition" for both formate and heptafluorobutyrate. Compound 12 exhibited a (+) "D14 inhibition" for both formate and heptafluorobutyrate.

[0430] Example 2: Germination-inducing activity of various compounds in Orobanche minor. In this example, the germination-inducing activity of compounds 1-20, 23, 26-61, 65-80, and 83-90 in Orobanche minor was analyzed by measuring germination rates. Orobanche minor seeds were used, which parasitize white clover native to Japan. The experiment was performed using a slightly modified version of the method described in Reference 2 (Uraguchi et al., (2018) Science, 362, 1301-1305. A femtomolar-range suicide germination stimulant for the parasitic plant Striga hermonthica.). Dried Orobanche minor seeds were placed in a 1.5 mL tube (50 μL volume), and 100 μL of chloroform was added and stirred to remove the wax layer from the seed coat. The chloroform was then removed by evaporating for at least 3 hours in a fume hood. The seeds were then sterilized by adding 1 mL of approximately 1% sodium hypochlorite, washed three times with sterile water, transferred to a petri dish, and conditioned by incubation at 22°C for 7–10 days in the dark. The solution containing the seeds was then dispensed into 96-well plates (30 μL aliquots) and an equal volume of compound solution was added. The test compounds were added to final concentrations ranging from 100 nM to 10 μM. After incubation at 22°C for 1 week after addition of the treatment solution, the germination rate was assessed by counting the number of germinated seeds under a stereomicroscope. The germination rates obtained using various compounds were calculated relative to the germination rate obtained using the same concentration of synthetic strigolactone GR24, which was set at 100%.

[0431] The results are shown in Tables 1 to 6.

[0432] In the table, "Germination" indicates the germination inducer activity of each compound, with compounds with a relative germination rate of 5% or higher being marked (+) and others marked (-). Several compounds exhibited germination inducer activity for Orobanche minor. Compound 10 had a "Germination" of (+) for both the formate and heptafluorobutyrate salts. Compound 12 had a "Germination" of (+) for both the formate and heptafluorobutyrate salts.

[0433] In the table, "Function" indicates the predicted function of each compound. Compounds with a (+) sign for "Germination" were determined to have a germination-inducing function. Compounds with a (+) sign for "D14 inhibition" and a (-) sign for "Germination" were determined to have a germination-suppressing function.

[0434] In the table, "D ring" in the "D ring portion" column represents a structure represented by the following formula (ID).

[0435]

[0436]

[0437]

[0438]

[0439]

[0440]

[0441]

[0442] Example 3: Control effect of compound 5 or synthetic strigolactone GR24 on Orobanche minor by inducing suicide germination In this example, the parasitic plant control activity of compound 5 was analyzed by measuring the suicide germination activity of the parasitic plant Orobanche minor.

[0443] Suicide germination tests of Orobanche minor were conducted according to reference 2 (Uraguchi et al., (2018) Science, 362, 1301-1305). Plastic pots (52.5 mm diameter at the top, 35 mm diameter at the bottom, 85 mm deep, with holes in the bottom) were filled with 0.52 L of dry soil (a mixture of equal parts of combined potting soil and vermiculite) to a depth of 2 cm. A 2-cm layer of soil containing 5 mg of Orobanche minor was then added. The pots were watered from the bottom and conditioned at 21°C for 14 days. Subsequently, 120 mL of 1 nM or 10 nM Compound 5 (DMSO concentration 0.0001%), 10 nM GR24 (DMSO concentration 0.0001%), or 0.0001% DMSO was applied to the soil surface and incubated for an additional 14 days. Ten white clover seeds were then sown per pot and thinned to three plants. During cultivation, the plants were watered from the bottom every two to three days and 0.1% Hyponex was added once a week. R The plants were fertilized with 6-10-5% NPK fertilizer and grown at 21°C for approximately three months under long-day conditions. The number of Orobanche minor that emerged was counted on the 98th day. The pots were then dismantled and the number of Tubercles and Orobanche minor that had infested the roots was counted.

[0444] The results are shown in Figures 1 and 2. In the figures, "p" indicates the results of Dunnett's multiple test, and "*" indicates that there was a significant difference at the 5% level in Dunnett's multiple test. In the figures, "◯" indicates the average value.

[0445] Example 4: Germination inducer activity of Compound 1 on Orobanche ramosa L. In this example, the germination inducer activity of Compound 1 on Orobanche ramosa L. was analyzed by measuring the germination rate. Orobanche ramosa L. is a parasitic plant that infects tomatoes and is currently classified as Phelipanche ramosa (L.) Pomel. Orobanche ramosa L. seeds were used from a species that infests tomatoes in Portugal. Dried seeds of Orobanche ramosa L. were conditioned in water for one week in a dark, humid environment at 20-26°C. Two mL of the test compounds were added to Petri dishes to achieve final concentrations of 1 μM, 100 nM (Compound 1), or 0.34 μM (GR24). After incubation for one week in a dark, humid environment at 20-26°C, the germination rate was assessed by counting the number of germinated seeds under a stereomicroscope.

[0446] The results are shown in Table 7. In the table, "Germination" indicates the germination-inducing activity of Compound 1, and a (+) was given when the relative value of the germination rate was 4% or more. Compound 1 exhibited germination-inducing activity for Orobanche ramosa L.

[0447]

[0448] According to the present invention, useful results can be obtained in the agricultural and horticultural fields, such as controlling parasitic plants.

Claims

1. A composition for controlling parasitic plants, A composition containing the following ingredients (A), (B), or (C): (A) Compounds represented by the following general formula (I); (B) Compounds represented by the following general formula (II); (C) By-product of amino acid fermentation. 【Chemistry 1】 In formula (I), X represents an interatomic bond or an oxycarbonyl group (OC (=O)), Y represents an oxygen atom (O), a nitrogen atom bonded to a hydrogen atom (NH), or a nitrogen atom bonded to a methyl group (NMe). R1 represents a hydrogen atom (H) or a methyl group. R2 represents an amino acid, agmatine, guanidine, a structure represented by the following general formula (R2-1), or a structure represented by the following general formula (R2-2). 【Chemistry 2】 In formula (R2-1), n represents an integer between 2 and 5 (i.e., 2, 3, 4, or 5), In formula (R2-1), R3 and R4 each independently represent a hydrogen atom or an acyl group. 【Transformation 3】 In formula (R2-2), a represents an alkylene group having 1 to 4 carbon atoms that may be substituted, or an alkenylene group having 2 to 4 carbon atoms that may be substituted. R5 represents a hydrogen atom (H) or an optionally substituted C1-C4 alkyl group. 【Chemistry 4】 In formula (II), X1 is an interatomic bond or a methylene oxy group (CH ２ O) represents, X2 represents an interatomic bond or a carbonyl group (C (=O)), Y represents a nitrogen atom (NH) bonded to an oxygen atom (O) or a hydrogen atom. R1 represents a hydrogen atom (H) or a methyl group. R2 represents an amino acid, agmatine, guanidine, aliphatic alcohol, fatty acid, a structure represented by the general formula (R2-1), or a structure represented by the general formula (R2-2). b-c is CH-CH ２ Alternatively, C = CH.

2. The composition according to claim 1, wherein the parasitic plant is controlled by inducing suicide germination of the parasitic plant or by suppressing the germination of the parasitic plant.

3. The composition according to claim 1 or 2, wherein the parasitic plant is a plant of the Orobanchaceae family, a plant of the Scrophulariaceae family, or a plant of the Convolvulaceae family.

4. The aforementioned parasitic plants include plants of the genus Striga, plants of the genus Orobanche, and The composition according to any one of claims 1 to 3, wherein the plant is a plant of the genus Phelipanche, Alectra, or Cuscuta.

5. The above parasitic plants are Striga asiatica, Striga gesnerioides, Striga hermonthica, Striga aspera, Striga asiatica, Striga curviflora, Striga parviflora, Striga angustifolia, Striga latericea, Striga aequinoctialis, Striga angolensis, Striga bilabiate, Striga brachycalyx, Striga chrsantha, Striga dalzielii, Striga elegans, Striga forbesii, Striga gastonii, Striga gracillima, Striga hallaei, Striga hirsuta, Striga junodii, Striga klingii, Striga lepidagathidis, Striga lutea, Striga macrantha, Striga passargei, Striga pinnatifida, Striga primuloides, Striga yemenica, Striga pubiflora, Orobanche ramosa, Orobanche minor, Orobanche crenata, Orobanche cumana, Orobanche foetida, Orobanche aegyptiaca, Orobanche cernua, Phelipanche ramosa, Phelipanche aegyptiaca, Alectra vogelii, Alectra picta, Alectra sessiliflora, Alectra orobanchoides, Alectra fluminensis, Cuscuta australis, Cuscuta campestris, Cuscuta chinensis, Cuscuta indecora, Cuscuta epithymum, Cuscuta epilinum, Cuscuta gronovii, Cuscuta planiflora, Cuscuta monogyna, Cuscuta pedicellata, CuscutaThe composition according to any one of claims 1 to 4, wherein the composition is palaestina or Cuscuta rejlexa.

6. The composition according to any one of claims 1 to 5, wherein, with respect to component (A), Y is NH and R1 is a methyl group.

7. The composition according to any one of claims 1 to 6, wherein the above component (A) satisfies any of the following conditions: (1) X is an interatomic bond or an oxycarbonyl group, and R2 is an amino acid linked by an amino group, agmatine linked by an amino group, or guanidine linked by an amino group; (2) X is an amino acid bonded by an interatomic bond, and R2 is an amino acid bonded by a carboxyl group; (3) X is an amino acid bonded by an interatomic bond, and R2 is an amino acid bonded by a hydroxyl group; (4) X is an amino acid bonded by an interatomic bond, and R2 is an amino acid bonded by a thiol group; (5) X is an amino acid bonded by an interatomic bond, and R2 is an amino acid bonded by an amide group; (6) X is an interatomic bond or an oxycarbonyl group, and R2 is a structure represented by formula (R2-1); (7) X is an interatomic bond, and R2 is a structure represented by formula (R2-2).

8. The composition according to any one of claims 1 to 7, wherein the above component (A) satisfies any of the following conditions: (1) X is an interatomic bond, Y is NH, R1 is a methyl group, and R2 is an amino acid linked by an amino group, agmatine linked by an amino group, guanidine linked by an amino group, or a structure represented by formula (R2-1); (2) X is an amino acid bonded by an oxycarbonyl group, Y is NH, R1 is a methyl group, and R2 is a carboxyl group, or a structure represented by formula (R2-2).

9. For the aforementioned component (B), Y is NH and b-c is CH-CH ２ The composition according to any one of claims 1 to 8, wherein R1 is H.

10. The composition according to any one of claims 1 to 9, wherein the above component (B) satisfies any of the following conditions: (1) X1 is an interatomic bond, X2 is a carbonyl group, and R2 is an amino acid linked by an amino group, agmatine linked by an amino group, or guanidine linked by an amino group; (2) X1 is an amino acid linked by a methylene oxy group, X2 by an interatomic bond, and R2 by a carboxyl group; (3) X1 is an interatomic bond, X2 is a carbonyl group, and R2 is an aliphatic alcohol; (4) X1 is a methylene oxy group, X2 is an interatomic bond, and R2 is a fatty acid; (5) X1 is an interatomic bond, X2 is a carbonyl group, and R2 is a structure represented by formula (R2-1); (6) X1 is a methylene oxy group, X2 is an interatomic bond, and R2 is a structure represented by formula (R2-2); (7) X1 is an interatomic bond, X2 is an interatomic bond, and R2 is a guanidine bonded by an amino group.

11. The composition according to any one of claims 1 to 10, wherein the above component (B) satisfies any of the following conditions: (1) X1 is an interatomic bond, X2 is a carbonyl group, Y is NH, and b-c is CH-CH ２ R1 is H, and R2 is an amino acid linked by an amino group, agmatine linked by an amino group, guanidine linked by an amino group, or a structure represented by formula (R2-1); (2) X1 is a methylene oxy group, X2 is an interatomic bond, Y is NH, and b-c is CH-CH ２ R1 is an amino acid bonded by H, R2 by a carboxyl group, a fatty acid having 2 to 18 carbon atoms, or a structure represented by formula (R2-2); (3) X1 is guanidine bonded by an interatomic bond, X2 is guanidine bonded by an interatomic bond, Y is an oxygen atom (O), b-c is C=CH, R1 is a methyl group, and R2 is an amino group.

12. The composition according to any one of claims 1 to 11, except that the component (B) is a compound represented by the following formulas (compound 41), (compound 50), (compound 52), (compound 54), (compound 55), and (compound 77). 【Transformation 5】 【Transformation 6】 【Transformation 7】 【Transformation 8】 【Chemistry 9】 【Chemistry 10】

13. The composition according to any one of claims 1 to 12, wherein component (A) or (B) is selected from compounds represented by the following formulas: (compound 1) to (compound 20), (compound 23), (compound 26) to (compound 40), (compound 42) to (compound 49), (compound 51), (compound 53), (compound 56) to (compound 76), (compound 78) to (compound 80), and (compound 82) to (compound 90). 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 [Chemistry 18] 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemistry 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 【Chemistry 27】 【Chemistry 28】 【Chemistry 29】 【Transformation 30】 【Chemistry 31】 【Chemistry 32】 【Transformation 33】 【Transformation 34】 【Chemistry 35】 【Transformation 36】 【Chemistry 37】 【Transformation 38】 【Chemistry 39】 【Chemistry 40】 【Chemistry 41】 【Chemistry 42】 【Chemistry 43】 【Chemistry 44】 【Chemistry 45】 【Chemistry 46】 【Chemistry 47】 【Chemistry 48】 【Chemistry 49】 [Transformation 50] 【Chemistry 51】 【Chemistry 52】 【Chemistry 53】 【Chemistry 54】 【Transformation 55】 【Transformation 56】 【Chemistry 57】 【Transformation 58】 【Chemistry 59】 【Transformation 60】 【Chemistry 61】 【Transformation 62】 【Transformation 63】 【Chemistry 64】 【Transformation 65】 【Chemical Formula 66】 【Transformation 67】 【Transformation 68】 【Transformation 69】 【Transformation 70】 【Chemistry 71】 【Chemistry 72】 【Transformation 73】 【Chemistry 74】 【Chemistry 75】 【Transformation 76】 【Chemical 77】 【Transformation 78】 【Chemistry 79】 【Chemistry 80】 【Chemistry 81】 【Chemistry 82】 【Chemistry 83】 【Chemical 84】 【Chemical 85】 【Chemical 86】 【Chemistry 87】 【Chemical 88】 【Chemistry 89】

14. The composition according to any one of claims 1 to 13, wherein the component (C) is a fermentation by-product of lysine, tryptophan, threonine, valine, leucine, or isoleucine.

15. The composition according to any one of claims 1 to 14, used in the form of a liquid containing component (A), (B), or (C) at a concentration of 10 nM to 10 mM.

16. A method for controlling parasitic plants, A method comprising applying the following components (A), (B), or (C) to the seeds of a parasitic plant: (A) Compounds represented by the following general formula (I); (B) Compounds represented by the following general formula (II); (C) By-product of amino acid fermentation. 【Chemistry 90】 In formula (I), X represents an interatomic bond or an oxycarbonyl group (OC (=O)), Y represents an oxygen atom (O), a nitrogen atom bonded to a hydrogen atom (NH), or a nitrogen atom bonded to a methyl group (NMe). R1 represents a hydrogen atom (H) or a methyl group. R2 represents an amino acid, agmatine, guanidine, a structure represented by the following general formula (R2-1), or a structure represented by the following general formula (R2-2). 【Chemistry 91】 In formula (R2-1), n represents an integer between 2 and 5 (i.e., 2, 3, 4, or 5), In formula (R2-1), R3 and R4 each independently represent a hydrogen atom or an acyl group. 【Chemistry 92】 In formula (R2-2), a represents an alkylene group having 1 to 4 carbon atoms that may be substituted, or an alkenylene group having 2 to 4 carbon atoms that may be substituted. R5 represents a hydrogen atom (H) or an optionally substituted C1-C4 alkyl group. 【Chemistry 93】 In formula (II), X1 is an interatomic bond or a methylene oxy group (CH ２ O) represents, X2 represents an interatomic bond or a carbonyl group (C (=O)), Y represents a nitrogen atom (NH) bonded to an oxygen atom (O) or a hydrogen atom. R1 represents a hydrogen atom (H) or a methyl group. R2 represents an amino acid, agmatine, guanidine, aliphatic alcohol, fatty acid, a structure represented by the general formula (R2-1), or a structure represented by the general formula (R2-2). b-c is CH-CH ２ Alternatively, C = CH.

17. A method for producing plant bodies, Applying the following components (A), (B), or (C) to the seeds of a parasitic plant induces suicide germination of the said parasitic plant; Cultivating the plants that the parasitic plants will host after the application of the aforementioned treatment; and A method comprising harvesting the plant body of the host plant of the parasitic plant: (A) Compounds represented by the following general formula (I); (B) Compounds represented by the following general formula (II); (C) By-product of amino acid fermentation. 【Chemical 94】 In formula (I), X represents an interatomic bond or an oxycarbonyl group (OC (=O)), Y represents an oxygen atom (O), a nitrogen atom bonded to a hydrogen atom (NH), or a nitrogen atom bonded to a methyl group (NMe). R1 represents a hydrogen atom (H) or a methyl group. R2 represents an amino acid, agmatine, guanidine, a structure represented by the following general formula (R2-1), or a structure represented by the following general formula (R2-2). 【Chemical 95】 In formula (R2-1), n represents an integer between 2 and 5 (i.e., 2, 3, 4, or 5), In formula (R2-1), R3 and R4 each independently represent a hydrogen atom or an acyl group. 【Chemistry 96】 In formula (R2-2), a represents an alkylene group having 1 to 4 carbon atoms that may be substituted, or an alkenylene group having 2 to 4 carbon atoms that may be substituted. R5 represents a hydrogen atom (H) or an optionally substituted C1-C4 alkyl group. 【Chemistry 97】 In formula (II), X1 is an interatomic bond or a methylene oxy group (CH ２ O) represents, X2 represents an interatomic bond or a carbonyl group (C (=O)), Y represents a nitrogen atom (NH) bonded to an oxygen atom (O) or a hydrogen atom. R1 represents a hydrogen atom (H) or a methyl group. R2 represents an amino acid, agmatine, guanidine, aliphatic alcohol, fatty acid, a structure represented by the general formula (R2-1), or a structure represented by the general formula (R2-2). b-c represents CH-CH ２ or C=CH.

18. A method for producing plant bodies, The cultivation of plants that parasitize other plants; Inducing germination of the parasitic plant by applying the following components (A), (B), or (C) to the seeds of the parasitic plant during the later stages of cultivation; and A method comprising harvesting the plant body of the host plant of the parasitic plant: (A) Compounds represented by the following general formula (I); (B) Compounds represented by the following general formula (II); (C) By-product of amino acid fermentation. 【Chem.98】 In formula (I), X represents an interatomic bond or an oxycarbonyl group (OC (=O)), Y represents an oxygen atom (O), a nitrogen atom bonded to a hydrogen atom (NH), or a nitrogen atom bonded to a methyl group (NMe). R1 represents a hydrogen atom (H) or a methyl group. R2 represents an amino acid, agmatine, guanidine, a structure represented by the following general formula (R2-1), or a structure represented by the following general formula (R2-2). 【Chem.99】 In formula (R2-1), n represents an integer between 2 and 5 (i.e., 2, 3, 4, or 5), In formula (R2-1), R3 and R4 each independently represent a hydrogen atom or an acyl group. 【Chemistry 100】 In formula (R2-2), a represents an alkylene group having 1 to 4 carbon atoms that may be substituted, or an alkenylene group having 2 to 4 carbon atoms that may be substituted. R5 represents a hydrogen atom (H) or an optionally substituted C1-C4 alkyl group. 【Chemistry 101】 In formula (II), X1 is an interatomic bond or a methylene oxy group (CH ２ O) represents, X2 represents an interatomic bond or a carbonyl group (C (=O)), Y represents a nitrogen atom (NH) bonded to an oxygen atom (O) or a hydrogen atom. R1 represents a hydrogen atom (H) or a methyl group. R2 represents an amino acid, agmatine, guanidine, aliphatic alcohol, fatty acid, a structure represented by the general formula (R2-1), or a structure represented by the general formula (R2-2). b-c is CH-CH ２ Alternatively, C = CH.

19. A method for producing plant bodies, The cultivation of plants that parasitize other plants; By applying the following components (A), (B), or (C) to the seeds of the parasitic plant during the aforementioned cultivation, the germination of the parasitic plant can be suppressed; and A method comprising harvesting the plant body of the host plant of the parasitic plant: (A) Compounds represented by the following general formula (I); (B) Compounds represented by the following general formula (II); (C) By-product of amino acid fermentation. 【Chemical Engineering 102】 In formula (I), X represents an interatomic bond or an oxycarbonyl group (OC (=O)), Y represents an oxygen atom (O), a nitrogen atom bonded to a hydrogen atom (NH), or a nitrogen atom bonded to a methyl group (NMe). R1 represents a hydrogen atom (H) or a methyl group. R2 represents an amino acid, agmatine, guanidine, a structure represented by the following general formula (R2-1), or a structure represented by the following general formula (R2-2). 【Chemistry 103】 In formula (R2-1), n represents an integer between 2 and 5 (i.e., 2, 3, 4, or 5), In formula (R2-1), R3 and R4 each independently represent a hydrogen atom or an acyl group. 【Chemical 104】 In formula (R2-2), a represents an alkylene group having 1 to 4 carbon atoms that may be substituted, or an alkenylene group having 2 to 4 carbon atoms that may be substituted. R5 represents a hydrogen atom (H) or an optionally substituted C1-C4 alkyl group. 【Chemistry 105】 In formula (II), X1 is an interatomic bond or a methylene oxy group (CH ２ O) represents, X2 represents an interatomic bond or a carbonyl group (C (=O)), Y represents a nitrogen atom (NH) bonded to an oxygen atom (O) or a hydrogen atom. R1 represents a hydrogen atom (H) or a methyl group. R2 represents an amino acid, agmatine, guanidine, aliphatic alcohol, fatty acid, a structure represented by the general formula (R2-1), or a structure represented by the general formula (R2-2). b-c is CH-CH ２ Alternatively, C = CH.

20. The method according to claim 16, wherein the parasitic plant is controlled by inducing suicide germination of the parasitic plant or by suppressing the germination of the parasitic plant.

21. The method according to any one of claims 17 to 19, wherein the parasitic plant is controlled by the application described above.

22. Claims 16 to 21, wherein the parasitic plant is a plant of the Orobanchaceae family, a plant of the Scrophulariaceae family, or a plant of the Convolvulaceae family. The method described in item 1.

23. The aforementioned parasitic plants include plants of the genus Striga, plants of the genus Orobanche, and The method according to any one of claims 16 to 22, wherein the plant is a plant of the genus Phelipanche, Alectra, or Cuscuta.

24. The above parasitic plants are Striga asiatica, Striga gesnerioides, Striga hermonthica, Striga aspera, Striga asiatica, Striga curviflora, Striga parviflora, Striga angustifolia, Striga latericea, Striga aequinoctialis, Striga angolensis, Striga bilabiate, Striga brachycalyx, Striga chrsantha, Striga dalzielii, Striga elegans, Striga forbesii, Striga gastonii, Striga gracillima, Striga hallaei, Striga hirsuta, Striga junodii, Striga klingii, Striga lepidagathidis, Striga lutea, Striga macrantha, Striga passargei, Striga pinnatifida, Striga primuloides, Striga yemenica, Striga pubiflora, Orobanche ramosa, Orobanche minor, Orobanche crenata, Orobanche cumana, Orobanche foetida, Orobanche aegyptiaca, Orobanche cernua, Phelipanche ramosa, Phelipanche aegyptiaca, Alectra vogelii, Alectra picta, Alectra sessiliflora, Alectra orobanchoides, Alectra fluminensis, Cuscuta australis, Cuscuta campestris, Cuscuta chinensis, Cuscuta indecora, Cuscuta epithymum, Cuscuta epilinum, Cuscuta gronovii, Cuscuta planiflora, Cuscuta monogyna, Cuscuta pedicellata, CuscutaThe method according to any one of claims 16 to 23, wherein the material is palaestina or Cuscuta rejlexa.

25. The method according to any one of claims 16 to 24, wherein, for the component (A), Y is NH and R1 is a methyl group.

26. The method according to any one of claims 16 to 25, wherein the above component (A) satisfies any of the following conditions: (1) X is an interatomic bond or an oxycarbonyl group, and R2 is an amino acid linked by an amino group, agmatine linked by an amino group, or guanidine linked by an amino group; (2) X is an amino acid bonded by an interatomic bond, and R2 is an amino acid bonded by a carboxyl group; (3) X is an amino acid bonded by an interatomic bond, and R2 is an amino acid bonded by a hydroxyl group; (4) X is an amino acid bonded by an interatomic bond, and R2 is an amino acid bonded by a thiol group; (5) X is an amino acid bonded by an interatomic bond, and R2 is an amino acid bonded by an amide group; (6) X is an interatomic bond or an oxycarbonyl group, and R2 is a structure represented by formula (R2-1); (7) X is an interatomic bond, and R2 is a structure represented by formula (R2-2).

27. The method according to any one of claims 16 to 26, wherein the above component (A) satisfies any of the following conditions: (1) X is an interatomic bond, Y is NH, R1 is a methyl group, and R2 is an amino acid linked by an amino group, agmatine linked by an amino group, guanidine linked by an amino group, or a structure represented by formula (R2-1); (2) X is an amino acid bonded by an oxycarbonyl group, Y is NH, R1 is a methyl group, and R2 is a carboxyl group, or a structure represented by formula (R2-2).

28. For the aforementioned component (B), Y is NH and b-c is CH-CH ２ The method according to any one of claims 16 to 27, wherein R1 is H.

29. The method according to any one of claims 16 to 28, wherein the above component (B) satisfies any of the following conditions: (1) X1 is an interatomic bond, X2 is a carbonyl group, and R2 is an amino acid linked by an amino group, agmatine linked by an amino group, or guanidine linked by an amino group; (2) X1 is an amino acid linked by a methylene oxy group, X2 by an interatomic bond, and R2 by a carboxyl group; (3) X1 is an interatomic bond, X2 is a carbonyl group, and R2 is an aliphatic alcohol; (4) X1 is a methylene oxy group, X2 is an interatomic bond, and R2 is a fatty acid; (5) X1 is an interatomic bond, X2 is a carbonyl group, and R2 is a structure represented by formula (R2-1); (6) X1 is a methylene oxy group, X2 is an interatomic bond, and R2 is a structure represented by formula (R2-2); (7) X1 is an interatomic bond, X2 is an interatomic bond, and R2 is a guanidine bonded by an amino group.

30. The method according to any one of claims 16 to 29, wherein the above component (B) satisfies any of the following conditions: (1) X1 is an interatomic bond, X2 is a carbonyl group, Y is NH, and b-c is CH-CH ２ R1 is H, R2 is an amino acid linked by an amino group, agmatine linked by an amino group, or a structure represented by formula (R2-1); (2) X1 is a methylene oxy group, X2 is an interatomic bond, Y is NH, and b-c is CH-CH ２ R1 is an amino acid bonded by an H group, R2 is an amino acid bonded by a carboxyl group, or a fatty acid with 2 to 18 carbon atoms, or The structure is represented by equation (R2-2); (3) X1 is guanidine bonded by an interatomic bond, X2 is guanidine bonded by an interatomic bond, Y is an oxygen atom (O), b-c is C=CH, R1 is a methyl group, and R2 is an amino group.

31. The method according to any one of claims 16 to 30, except that the component (B) is a compound represented by the following formulas (compound 41), (compound 50), (compound 52), (compound 54), (compound 55), and (compound 77). 【Chemistry 106】 【Chemistry 107】 【Chemistry 108】 【Chemistry 109】 【Chemical 110】 【Chemistry 111】

32. The method according to any one of claims 16 to 31, wherein component (A) or (B) is selected from compounds represented by the following formulas: (compound 1) to (compound 20), (compound 23), (compound 26) to (compound 40), (compound 42) to (compound 49), (compound 51), (compound 53), (compound 56) to (compound 76), (compound 78) to (compound 80), and (compound 82) to (compound 90). 【Chemistry 112】 【Chemistry 113】 【Chemical 114】 【Chemical 115】 【Chemistry 116】 【Chemistry 117】 【Chemistry 118】 【Chemical 119】 【Chemical 120】 【Chemistry 121】 【Chemistry 122】 【Chemical 123】 【Chemistry 124】 【Chemistry 125】 【Chemistry 126】 【Chemistry 127】 【Chemistry 128】 【Chemistry 129】 【Chemistry 130】 【Chemistry 131】 【Chemistry 132】 【Chemistry 133】 【Chemistry 134】 【Chemistry 135】 【Transformation 136】 【Chemistry 137】 【Chemistry 138】 【Chemistry 139】 [Chemistry 140] 【Chemistry 141】 【Chemistry 142】 【Chemistry 143】 【Chemistry 144】 【Chemistry 145】 【Chemistry 146】 【Chemistry 147】 【Chemistry 148】 【Chemistry 149】 [Chemical 150] 【Chemistry 151】 【Chemistry 152】 【Chemistry 153】 【Chemistry 154】 【Chemistry 155】 【Chemistry 156】 【Chemistry 157】 【Chemistry 158】 【Chemistry 159】 [Chemical 160] 【Chemistry 161】 【Chemistry 162】 【Chemistry 163】 【Chemistry 164】 【Chemistry 165】 【Chemistry 166】 【Chemistry 167】 【Chemical 168】 【Chemistry 169】 【Chemistry 170】 【Chemistry 171】 【Chemistry 172】 【Chemistry 173】 【Chemistry 174】 【Chemistry 175】 【Chemistry 176】 【Chemistry 177】 【Chemistry 178】 【Chemistry 179】 【Chemistry 180】 【Chemistry 181】 【Chemistry 182】 【Chemistry 183】 【Chemistry 184】 【Chemistry 185】 【Chemistry 186】 【Chemistry 187】 【Chemical 188】 【Chemical 189】 【Chemistry 190】

33. The method according to any one of claims 16 to 32, wherein the component (C) is a fermentation by-product of lysine, tryptophan, threonine, valine, leucine, or isoleucine.

34. The method according to any one of claims 16 to 33, wherein the component (A), (B), or (C) is used in the form of a liquid containing the component (A), (B), or (C) at a concentration of 10 nM to 10 mM.

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