TW201010989A - Amide compound and use thereof - Google Patents

Abstract

An amide compound of the formula (I): (wherein, R1 represents a hydrogen atom or fluorine atom and R2 represents a C3 to C8 linear alkenyl group orC3 to C8 linear alkynyl group.) has an excellent controlling effect on a plant disease.

Description

201010989 VI. Description of the Invention [Technical Field to Which the Invention Is Applicable] The present invention relates to a guanamine compound and its use for controlling plant diseases. [Prior Art] Some compounds have been developed and used as active ingredients of plant disease control compositions. However, these compounds do not necessarily indicate sufficient plant disease control effects in some cases. SUMMARY OF THE INVENTION The present invention provides a compound having an excellent control effect on plant diseases. The invention is as follows. [1] A guanamine compound of the formula (I):

Wherein 'R1 represents a hydrogen atom or a fluorine atom, and R2 represents a C3-C8 linear alkenyl group or a C3-C8 linear alkynyl group. (hereinafter referred to as the compound of the present invention). [2] A guanamine compound according to [1], wherein Ri is a fluorine atom, and R2 is a C3-C8 linear alkenyl group. [3] A guanamine compound according to [2], wherein R2 is a C5-C7 linear alkenyl group. [4] A guanamine compound according to [2], wherein R2 is 4-pentenyl, 5-hexenyl or 6-heptenyl. [10] The indoleamine compound of [1], wherein R1 is a hydrogen atom, and R2 is a C3-C8 linear alkenyl group. [6] A guanamine compound according to [5], wherein R2 is a C5-C7 linear alkenyl group. [7] A guanamine compound according to [5], wherein R2 is 4-pentenyl, 5-hexyl or 6-heptenyl. [8] The guanamine compound according to [1], wherein R1 is a fluorine atom, and is a C 3 - C 8 linear alkynyl group. [9] A guanamine compound according to [8], wherein R2 is a C5-C7 linear alkynyl group. [10] A guanamine compound according to [8], wherein R2 is 4-pentynyl, 5-hexynyl or 6-heptynyl. [11] A guanamine compound according to [1], wherein R1 is a hydrogen atom, and R2 is a C3-C8 linear alkynyl group. [12] A guanamine compound according to [11], wherein R2 is a C5-C7 linear block group. [13] A guanamine compound according to [11], wherein R2 is 4-pentynyl, 5-hexynyl or 6-heptynyl. [14] A plant disease controlling composition comprising the indoleamine compound and an inert carrier as described in any one of [1] to t13]. (hereinafter referred to as the plant disease control composition of the present invention) [15] - A method for controlling plant diseases, which has an effective amount of the indoleamine compound as described in any one of [13] applied to a plant or soil The steps. (The method for controlling plant diseases according to the present invention) [16] The use of the indoleamine compound according to any one of [1] to [13] for controlling plant diseases in -6 - 201010989. [17] N-(2-Fluoro-3-(2-propenyloxy)phenyl)methyl-benzothiazole-6-carboxyguanamine. [18] N-(2-Fluoro-3-(4-pentenyloxy)phenyl)methyl-benzoxazol-6-carboxyguanamine. [19] N-(2-Fluoro-3-(5-hexenyloxy)phenyl)methyl-benzothiazole-6-carboxyguanamine. φ [20] N-(2-Fluoro-3-(6-heptenyloxy)phenyl)methyl-benzothiazole-6-carboxyguanamine. [21] N-(2-Fluoro-3-(2-pentenyloxy)phenyl)methyl-benzothiazole-6-carboxyguanamine. [22] N-(3-(2-Propoxy)phenyl)methyl-benzothiazole-6-carboxyguanamine. [23] N-(3-(4-pentenyloxy)phenyl)methyl-benzothiazole-6-carboxyindole Amine. Φ [24] N-(3-(5-hexenyloxy)phenyl)methyl-benzothiazole-6-carboxyguanamine. [25] N-(3_(6-heptenyloxy)phenyl)methyl-benzothiazole-6-carboxyindoleamine. [26] N-(3-(2-Butoxy)phenyl)methyl-benzothiazole-6-carboxyindoleamine. [27] N-(3-(2-pentenyloxy)phenyl)methyl-benzothiazole-6-carboxyindoleamine. [28] N-(2-Fluoro-3-(2-propynyloxy)phenyl)methyl-benzothiazole-6- 201010989 Carboxamide. [29] N-(2-Fluoro-3-(4-pentynyloxy)phenyl)methyl-benzothiazole-6-carboxyguanamine. [3 0] N-(2-Fluoro-3-(5-hexynyloxy)phenyl)methyl-benzothiazole-6-carboxyguanamine. [31] N-(2-Fluoro-3-(2-pentynyloxy)phenyl)methyl-benzothiazole-6-carboxyguanamine. [32] N-(3-(2-propynyloxy)phenyl)methyl-benzothiazole-6-carboxyindole amide. [33] N-(3-(4-pentynyloxy)phenyl)methyl-benzothiazole-6-carboxyindoleamine. [34] N-(3-(5-hexynyloxy)phenyl)methyl-benzosoxaconazole-6-carboxyindoleamine. [35] N-(3-(2-butynyloxy)phenyl)methyl-benzothiazole-6-carboxyindoleamine.

[36] N-(3-(2-pentynyloxy)phenyl)methyl-benzothiazole-6-carboxyindole G amine. [37] N-(2-Fluoro-3_(2-butynyloxy)phenyl)methyl-benzothiazole-6-carboxyguanamine. [38] N-(2-Fluoro-3-(7-octenyloxy)phenyl)methyl-benzothiazole-6-carboxyguanamine. [39] N-(3-(7-Octyloxy)phenyl)methyl-benzothiazole-6-carboxyindoleamine. The compounds of the present invention include, for example, the following specific examples. -8- 201010989 R2 in the formula (I) represents a 2-propenylamine compound; R2 in the formula (I) represents a 2-propynylamine derivative; and R2 in the formula (I) represents a C4-C6 a linear alkenyl amidoxime compound; R2 in the formula (I) represents a C4-C6 linear alkynyl amidoxime compound; R1 represents a hydrogen atom and R2 represents a CM-C6 linear alkenyl amidoxime compound; R1 represents a hydrogen atom and R2 represents a decylamine compound of a C4-C6 linear alkynyl group; R1 represents a fluorine atom and R2 represents a decylamine compound of a C4-C6 linear alkenyl group; and R1 represents a fluorine atom and R2 represents a C4-C6 straight An alkynyl group of amidoxime compounds. The C3-C8 linear alkenyl group represented by R2 includes a propenyl group, a linear butenyl group, a linear pentenyl group, a linear hexenyl group, a linear heptenyl group, and a linear octene group. Examples of the propylene group include a 2-propenyl group. Examples of linear butenyl groups include 2-butenyl, and 3-butenyl. Examples of linear pentenyl groups include 2-pentenyl, 3-pentenyl and 4-pentenyl. Examples of linear hexenyl groups include 2-hexenyl, 3-hexenyl, 4-hexenyl and 5-hexenyl. Examples of linear heptenyl groups include 2-heptenyl, 3-heptenyl, 4-heptenyl, 5-heptenyl and 6-heptenyl. Examples of linear octenyl groups include 2-octenyl, 3-octenyl, 4-octenyl, 5-octenyl, 6-octenyl and 7-octenyl. The C3-C8 linear alkynyl group represented by R2 includes a propynyl group, a linear butynyl group, a linear pentynyl group, a linear hexynyl group, a linear heptynyl group, and a linear octynyl group. Examples of propynyl include 2-propynyl. An example package of a linear butynyl group -9 - 201010989 includes 2-butynyl and 3-butynyl. Examples of linear pentynyl groups include 2-pentynyl, 3-pentynyl and 4-pentynyl. Examples of linear hexynyl groups include 2-hexyl, 3-hexyl, 4-hexynyl and 5-hexynyl. Examples of linear heptynyl groups include 2-heptynyl, 3-heptynyl, 4-heptynyl, 5-heptynyl and 6-heptynyl. Examples of linear octynyl groups include 2-octynyl, 3-octynyl, 4-octynyl, 5-octynyl, 6-octynyl and 7-octynyl. A method of producing the compound of the present invention will be described. The compound of the present invention can be produced, for example, by the following (manufacturing method 1) to (manufacturing Q method 3). (Production Method 1) The compound of the present invention can be produced by reacting a compound (Π), a compound (III) or a salt thereof (for example, hydrochloric acid and hydrobromic acid may be mentioned) with a condensing agent.

(wherein R1 and R2 represent the same meaning as described above). The reaction is usually carried out in the presence of a solvent. Examples of the solvent used in the reaction include ethers such as tetrahydrofuran (hereinafter referred to as THF), ethylene glycol dimethyl ether, tertiary butyl methyl ether (hereinafter referred to as MTBE), and the like; aliphatic hydrocarbons such as hexane, Heptane, octane, etc.; aryl-10- 201010989 aromatic hydrocarbons such as toluene, xylene, etc.; halogenated hydrocarbons such as chlorobenzene, etc.; esters such as butyl acetate, ethyl acetate, etc.; Such as acetonitrile and the like; guanamines such as N,N-dimethylformamide (hereinafter referred to as DMF) and the like; sulfoxides such as dimethyl sub-milling (hereinafter referred to as DMSO), etc.; nitrogen-containing aroma Group compounds such as pyridine and the like; and mixtures thereof. Examples of the condensing agent used in the reaction include carbodiimides such as 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (hereinafter referred to as φ is wsc). 1,3-dicyclohexylcarbodiimide or the like, and hexafluorophosphoric acid (benzotriazol-1-yloxy)tris(dimethylamino)scale (hereinafter referred to as BOP reagent). In the reaction, the compound (III) is usually used in an amount of from 0.5 to 3 mol, based on 1 mol of the compound (II), and the proportion of the condensing agent is usually from 1 to 5 mol, based on 1 mol of the compound (II). The reaction temperature of the reaction is usually in the range of -2 (TC to 140 ° C. The reaction time of the reaction is usually in the range of 1 to 24 hours. After the end of the reaction, if the solid is precipitated by adding water to the reaction mixture, the present invention The compound can be isolated by filtration. If solid precipitation does not occur by adding water to the reaction mixture, the compound of the present invention can be obtained by extracting a mixture of the reaction mixture and water with an organic solvent, and drying and concentrating the organic layer. The isolated compound of the present invention can also be further purified by chromatography, recrystallization, etc. (Production Method 2) The compound of the present invention can be obtained by allowing the compound (IV) or its hydrochloride, and -11 - 201010989 The compound (III) or a salt thereof (for example, a hydrochloride and a hydrobromide salt may be mentioned) is produced by reacting in the presence of a base.

Wherein R1 and R2 represent the same meanings as described above. The reaction is usually carried out in the presence of a solvent. Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, MTBE, etc.; aliphatic hydrocarbons such as hexane, heptane, octane, etc.; aromatic hydrocarbons such as toluene, Xylene and the like; halogenated hydrocarbons such as chlorobenzene and the like; esters such as butyl acetate, ethyl acetate and the like; nitriles such as acetonitrile and the like; and mixtures thereof. Examples of the base used in the reaction include base metal carbonates such as sodium carbonate, potassium carbonate and the like; tertiary amines such as triethylamine, diisopropylethylamine and the like; and nitrogen-containing aromatic compounds such as Pyridine, 4-dimethylamino acridine, etc., etc. In the reaction, the compound (ΠΙ) is usually used in an amount of from 0.5 to 3 mol, based on 1 mol of the compound (IV), and the amount of the base is usually from 1 to 5 mol, based on 1 mol of the compound (IV). The reaction temperature of the reaction is usually in the range of -20 ° C to 100 ° C. The reaction time for the reaction is usually in the range of from 〇1 to 24 hours. After the end of the reaction, if the solid is precipitated by adding water to the reaction mixture, the compound of the present invention can be isolated by filtration. If water is added to the reaction mixture by -12-201010989 without solid precipitation, the compound of the present invention can be isolated by extracting a mixture of the reaction mixture and water with an organic solvent, and drying and concentrating the organic layer. The isolated compound of the invention can also be further purified by chromatography, recrystallization, and the like. (Manufacturing method 3)

The compound of the present invention can be produced by reacting the compound (V) and the compound (VI) in the presence of a base.

Here, R1 and R2 represent the same meanings as described above, and L represents a chlorine atom, a bromine atom, an iodine atom, a methyl fluorenyloxy group, a trimethyl methoxy group or a p-toluene sulfonyloxy group. The hydrazine reaction is usually carried out in the presence of a solvent. Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, MTBE, etc.; aromatic hydrocarbons such as toluene, xylene, etc.; halogenated hydrocarbons such as chlorobenzene, etc.; nitriles For example, acetonitrile or the like; guanamine such as DMF, etc.; sub-milling such as DMSO, etc.; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, etc.; water; and mixtures thereof. Examples of the base to be used in the reaction include alkali metal carbonates such as sodium carbonate, potassium carbonate, carbonic acid planing, etc.; alkali metal hydroxides such as sodium hydroxide and the like, and alkali metal hydrides such as sodium hydride and the like. -13- 201010989 In the reaction, the ratio of the compound (VI) is usually from 1 to 10 mol' based on 1 mol of the compound (V), and the ratio is usually from 1 to 5 mol based on 1 mol of the compound ( V) meter. The reaction temperature of the reaction is usually in the range of -20 ° C to 100 ° C. The reaction time for the reaction is usually in the range of 0.1 to 24 hours. After the end of the reaction, if the solid is precipitated by adding water to the reaction mixture, the compound of the present invention can be isolated by filtration. If solid precipitation does not occur by adding water to the reaction mixture, the compound of the present invention can be isolated by extracting a mixture of the reaction mixture and water with an organic solvent, and drying and concentrating the organic layer. The isolated compound of the invention can also be further purified by chromatography, recrystallization, and the like. The compound (V) can be produced, for example, by the following (Synthesis Method 1) or (Synthesis Method 2). (Synthesis Method 1) The compound (V) can be obtained by reacting the compound (11), the compound (VII) or a phosphonium salt thereof (for example, a hydrochloride and a hydrobromide salt) and a condensing agent. Manufacturing.

Wherein 'R denotes the same meaning as described above. The reaction is usually carried out in the presence of a solvent. Examples of the solvent used in the reaction of the-14-201010989 include ethers such as THF, ethylene glycol dimethyl ether, MTBE, etc.; aliphatic hydrocarbons such as hexane, heptane, and octane Alkane or the like; aromatic hydrocarbons such as toluene, xylene, etc.; halogenated hydrocarbons such as chlorobenzene, etc.; esters such as butyl acetate, ethyl acetate, etc.; nitriles such as acetonitrile, etc.; guanamine such as DMF Etc.; sub-milling such as DMSO, etc.; nitrogen-containing aromatic compounds such as pyridine, etc.; and mixtures thereof. Examples of the condensing agent used in the reaction include carbodiimides such as hydrazine WSC, 1,3-dicyclohexylcarbodiimide, and the like, and a BOP reagent. In the reaction, the ratio of the compound (VII) is usually 0.5 to 3 mol, based on 1 mol of the compound (II), and the proportion of the condensing agent is usually 1 to 5 mol, based on 1 mol of the compound (II). . The reaction temperature of the reaction is usually in the range of -2 ° C to 14 (TC. The reaction time of the reaction is usually in the range of 1 to 24 hours. After the end of the reaction, if the solid is precipitated by adding water to the reaction mixture, the compound ( V) can be separated by filtration. If solid precipitation does not occur by adding water to the reaction mixture, the compound (V) can be obtained by extracting a mixture of the reaction mixture and water with an organic solvent, and drying and concentrating the organic layer. Further, the isolated compound (V) can be further purified by chromatography, recrystallization, etc. (Synthesis Method 2) Compound (V) can be obtained by allowing compound (IV) and compound (VII) Or its hydrochloride is produced by reacting in the presence of a base. -15- 201010989

Wherein R1 represents the same meaning as described above. The reaction is usually carried out in the presence of a solvent. Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, MTBE, etc.; aliphatic hydrocarbons such as hexane, heptane, octane, etc.; aromatic hydrocarbons such as toluene, Xylene and the like; halogenated hydrocarbons such as chlorobenzene and the like; esters such as butyl acetate, ethyl acetate and the like; nitriles such as acetonitrile and the like; and mixtures thereof. Examples of the ruthenium used in the reaction include ruthenium metal carbonates such as sodium carbonate, potassium carbonate and the like; tertiary amines such as triethylamine, diisopropylethylamine and the like; and nitrogen-containing aromatic compounds such as Pyridine, dimethylaminopyridine, and the like. In the reaction, the compound (VII) is usually used in an amount of from 0.5 to 1 mol, based on 1 mol of the compound (IV), and the amount of the hydrazine is usually from 1 to 5 mol, based on 1 mol of the compound (IV). . The reaction temperature range of the reaction is usually from -2 ° C to 10 ° C. The reaction time for the reaction is usually in the range of from 〇1 to 24 hours. After the end of the reaction, if the solid is precipitated by adding water to the reaction mixture, the compound (V) can be isolated by filtration. If solid precipitation does not occur by adding water to the reaction mixture, the compound (V) can be isolated by extracting a mixture of the reaction mixture and water with an organic solvent, and drying the organic layer from -16 to 201010989. The isolated compound (V) can also be further purified by chromatography, recrystallization, or the like. The compounds of the invention specifically include the following compounds. N-(2-Fluoro-3-(2-propenyloxy)phenyl)methyl-benzothiazole-6-carboxamide, N-(2-fluoro-3-(2-butoxy)benzene Methyl-benzothiazole-6-carboxamide, φ N-(2-fluoro-3-(3-butoxy)phenyl)methyl-benzothiazole-6-carboxamide, N -(2-fluoro-3-(2-pentenyloxy)phenyl)methyl-benzothiazole-6-carboxamide, N-(2-fluoro-3-(3-pentenyloxy)benzene Methyl-benzothiazole-6-carboxamide, N-(2-fluoro-3-(4-pentenyloxy)phenyl)methyl-benzothiazole-6-carboxamide, Φ N -(2-fluoro-3-(2-hexenyloxy)phenyl)methyl-benzothiazole-6-carboxamide, N-(2-fluoro-3-(3-hexenyloxy)benzene Methyl-benzothiazole-6-carboxamide, N-(2-fluoro-3-(4-hexenyloxy)phenyl)methyl-benzothiazole-6-carboxamide, N- (2-Fluoro-3-(5-hexenyloxy)phenyl)methyl-benzothiazole-6-carboxamide, N-(2-fluoro-3-(2-heptenyloxy)phenyl Methyl-benzothiazole-6-carboxyindole-17- 201010989 Amine, N-(2-fluoro-3-(3-heptenyloxy)phenyl)methyl-benzothiazole-6-carboxamide , N-(2-Fluoro-3-(4-heptenyloxy)phenyl)methyl-benzothiazole-6-carboxamide, N-(2-Fluoro-3 -(5-heptenyloxy)phenyl)methyl-benzothiazole-6-carboxamide, N-(2-fluoro-3-(6-heptenyloxy)phenyl)methyl-benzo Thiazole-6-carboxyindole, N-(2-fluoro-3-(2-octenyloxy)phenyl)methyl-benzothiazole-6-carboxamide, N-(2-fluoro-3 -(3-octenyloxy)phenyl)methyl-benzothiazole-6-carboxamide, N-(2-fluoro-3-(4-octenyloxy)phenyl)methyl-benzo Thiazole-6-carboxamide, N-(2-fluoro-3-(5-octenyloxy)phenyl)methyl-benzothiazole-6-carboxyindole, N-(2-fluoro-3 -(6-octenyloxy)phenyl)methyl-benzothiazole-6-carboxamide, N-(2-fluoro-3-(7-octenyloxy)phenyl)methyl-benzo Thiazole-6-carboxamide, N-(3-(2-propenyloxy)phenyl)methyl-benzothiazole-6-carboxamide, N-(3-(2-butoxy)benzene Methyl-benzothiazole-6-carboxamide, N-(3-(3-butoxy)phenyl)methyl-benzothiazole-6-carboxamide, -18- 201010989 N- (3-(2•pentenyloxy)phenyl)methyl-benzothiazole-6-carboxamide, N-(3-(3-pentenyloxy)phenyl)methyl-benzothiazole- 6-Carboguanamine, N-(3-(4-pentenyloxy)phenyl)methyl-benzothiazole-6-carboxylate Amine, N-(3-(2-hexenyloxy)phenyl)methyl-benzothiazole-6-carboxamide, N-(3-(3-hexenyloxy)phenyl)methyl- Benzothiazole-6-carboxamide, N-(3-(4-hexenyloxy)phenyl)methyl-benzothiazole-6-carboxamide, N-(3-(5-hexeneoxy) Phenyl)methyl-benzothiazole-6-carboxamide, 9 N-(3-(2-heptenyloxy)phenyl)methyl-benzothiazole-6-carboxamide, N- (3-(3-heptenyloxy)phenyl)methyl-benzothiazole-6-carboxamide, N-(3-(4-heptenyloxy)phenyl)methyl-benzothiazole- 6-Carboguanamine, N-(3-(5-heptenyloxy)phenyl)methyl-benzothiazole-6-carboxamide, N-(3-(6-heptenyloxy)phenyl Methyl-benzothiazole-6-carboxamide, N-(3-(2-octenyloxy)phenyl)methyl-benzothiazole-6-carboxamide, N-(3-(3) -octenyloxy)phenyl)methyl-benzothiazole-6-carboxamide, N_(3-(4-octenyloxy)phenyl)methyl-benzothiazole-6-carboxamide, φ Ν-(3·(5-octenyloxy)phenyl)methyl-benzothiazole-6-carboxamide, Ν-(3-(6-octenyloxy)phenyl)methyl-benzo Thiazol-6-carboxyguanamine, Ν-(3-(7-octenyloxy)phenyl)methyl-benzene Thiazole-6-carboxamide, Ν-(2-fluoro-3-(2-propynyloxy)phenyl)methyl-benzothiazole-6-carboxamide, Ν_(2-fluoro-3-( 2-butynyloxy)phenyl)methyl-benzothiazole-6-carboxamide, N_(2-.fluoro-3-(3-butynyloxy)phenyl)methylbenzothiazole- 6-Carboxylimine, -19 - 201010989 N-(2-Fluoro-3-(2-pentynyloxy)phenyl)methyl-benzothiazole-6-carboxamide, N-(2-Fluoro- 3-(3-pentynyloxy)phenyl)methyl-benzothiazole-6-carboxamide, N-(2-fluoro-3-(4-pentynyloxy)phenyl)methyl-benzene And thiazol-6-carboxyguanamine, N-(2-fluoro-3-(2-hexynyloxy)phenyl)methyl-benzothiazole-6-carboxamide, φ N-(2-fluoro- 3-(3-hexynyloxy)phenyl)methyl-benzothiazole-6-carboxamide, N-(2-fluoro-3-(4-hexynyloxy)phenyl)methyl-benzene And thiazol-6-carboxyguanamine, N-(2-fluoro-3-(5-hexynyloxy)phenyl)methyl-benzothiazole-6-carboxamide, N-(2-fluoro-3 -(2-heptynyloxy)phenyl)methyl-benzothiazole-6-carboxamide, Θ N-(2-fluoro-3-(3-heptynyloxy)phenyl)methyl-benzene And spyrazole-6-carboxyguanamine, N-(2-fluoro-3-(4-heptynyloxy)phenyl)methyl-benzothiazole -6-carboxyguanamine, N-(2-fluoro-3-(5-heptynyloxy)phenyl)methyl-benzothiazole-6-carboxamide, N-(2-fluoro-3-() 6-heptynyloxy)phenyl)methyl-benzothiazole-6-carboxamide, -20- 201010989 N-(2-fluoro-3-(2-octynyloxy)phenyl)methyl- Benzothiazole-6-carboxamide, N-(2-fluoro-3-(3-octynyloxy)phenyl)methyl-benzothiazole-6-carboxamide, N-(2-fluoro- 3-(4-octynyloxy)phenyl)methyl-benzothiazole-6-carboxamide, N-(2-fluoro-3-(5-octynyloxy)phenyl)methyl-benzene And thiazol-6-carboxyguanamine, N-(2-fluoro-3-(6-octynyloxy)phenyl)methyl-benzothiazole-6-carboxamide, N-(2-fluoro- 3-(7-octynyloxy)phenyl)methyl-benzothiazole-6-carboxamide, N-(3-(2-propynyloxy)phenyl)methyl-benzothiazole-6 - Carboxylamamine ' N-(3-(2-butynyloxy)phenyl)methyl-benzothiolan-6-carboxamide, N-(3-(3-butynyloxy)phenyl Methyl-benzothiazole-6-carboxamide, #Ν-(3·(2-pentynyloxy)phenyl)methyl-benzothiazole-6-carboxamide, Ν-(3-( 3-pentynyloxy)phenyl)methyl-benzothiazole-6-carboxamide, Ν-(3-(4-pentynyloxy)phenyl Methyl-benzothiazole-6-carboxamide, Ν-(3-(2-hexynyloxy)phenyl)methyl-benzothiazole-6-carboxamide, Ν-(3-(3) -hexynyloxy)phenyl)methyl-benzothiazole-6-carboxamide, Ν-(3-(4-hexynyloxy)phenyl)methyl-benzothiazole-6-carboxyguanamine , Ν-(3-(5-hexynyloxy)phenyl)methyl-benzothiazole-6-carboxamide, Ν-(3-(2-heptynyloxy)phenyl)methyl-benzene And thiazol-6-carboxyguanamine, Ν-(3-(3-heptynyloxy)phenyl)methyl-benzothiazole-6-carboxamide, -21 - 201010989 N-(3-(4- Rf alkynyloxy)phenyl)methyl-benzothiazole-6-carboxamide, N-(3-(5-heptynyloxy)phenyl)methyl-benzothiazole-6-carboxamide N-(3-(6-heptynyloxy)phenyl)methyl-benzothiazole-6-carboxamide, N-(3-(2-octynyloxy)phenyl)methyl-benzo Thiazole-6-carboxamide, N-(3-(3-octynyloxy)phenyl)methyl-benzothiazole-6-carboxamide, N-(3-(4-octynyloxy) Phenyl)methyl-benzothiazole-6-carboxamide, N-(3-(5-octynyloxy)phenyl)methyl-benzothiazole-6-carboxamide, N-(3- (6-octynyloxy)phenyl)methyl-benzothiazole-6-carboxyguanamine and φ N-(3-(7-octynyloxy)phenyl)methylbenzothiazole-6-carboxamide. The plant disease controlling composition of the present invention comprises the compound of the present invention and an inert carrier. Inert carriers include solid carriers, liquid carriers, and gaseous carriers. The plant disease control composition of the present invention is usually prepared into a wettable powder, a powder, and a water dispersible by further adding an auxiliary agent for a blending agent such as a surfactant, a tackifier, a dispersing agent, a stabilizer, or the like. Granules, fluids, granules, dry fluids, emulsions, aqueous liquids, oily solutions, fuming agents, aerosols, microcapsules, and the like. The plant disease control composition of the present invention comprises a compound of the present invention in a weight ratio of usually from 0.1 to 99%, preferably from 0.2 to 90%. Examples of solid carriers include clay (eg, kaolin, diatomaceous earth, synthetic hydrated oxidized sand, Fubasami clay, bentonite, and acid clay), talc, and other inorganic minerals (eg, sericite, quart powder, sulfur powder, activated carbon) Fine powders and granules of calcium carbonate and hydrated vermiculite, and the like, and examples of liquid carriers include water; alcohols (for example, methanol and ethanol), ketones (for example, acetone and methyl ethyl ketone), and aromatics. Hydrocarbons-22- 201010989 (eg, benzene, toluene, xylene, ethylbenzene, and methylnaphthalene), aliphatic hydrocarbons (eg, Zhenghexin, Huanyuan and kerosene), vinegar (eg, acetic acid B) Esters and butyl acetate), nitriles (for example, acetonitrile and isobutyronitrile), ethers (for example, diterpene and diisopropyl ether), guanamines (for example, DMF and dimethylacetamide) ), halogenated hydrocarbons (for example, dichloroethane and trichloroethylene, carbon tetrachloride) and the like. Examples of the surfactant include alkyl sulfate, alkyl sulfonate, alkyl aryl sulfonate, alkyl aryl ether and polyoxyethylenate, polyoxyethylene glycol ether (p〇iyOXyethylene) Glycol ethers), polyvalent alcohol esters, sugar alcohol derivatives, and the like. Examples of other auxiliaries for use in the blend include tackifiers and dispersants, in particular casein, gelatin, polysaccharides (for example, starch, gum arabic, cellulose derivatives and alginic acid), lignin derivatives , bentonite, sugar, synthetic water-soluble polymers (for example, polyvinyl alcohol, polyvinylpyrrolidone and polyacrylic acid), PAP (isopropyl acid phosphate), BHT (2,6-9 di-tertiary 4-methyl-phenol), BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oil, mineral oil, fatty acid Or its esters and so on. The application method of the plant disease controlling composition of the present invention for controlling plant diseases includes, for example, treating plants such as spraying on stems and leaves, treating cultivated soil for plants such as soil treatment, and the like, and treating seeds such as seed disinfection, etc. Wait. The plant disease control composition of the present invention may also be blended with other agents as follows: fungicides, insecticides, acaricides, nematicides, herbicides other than -23-201010989, plant growth regulators, fertilizers Or soil amendments, or used simultaneously with but not mixed. Examples of active ingredients of such other fungicides include: oxazole fungicidal compounds such as propiconazole, prothioconazole, triadimenol, prochloraz, penconazole ), tebuconazole, flusilazole, diniconazole, bromuconazole, epoxiconazole, difenoconazole, cyproconazole, chlorpyrifos (metconazole), triflumizole, tetraconazole, microbutanil, fenbuconazole, hexaconazole, fluquinconazole, carbazole

(triticonazole), bitertanol, imazalil, flutriafol, simeconazole, or ipconazole; a cyclic amine fungicidal compound such as fenfluz ( Fenpropimorph), tridemorph, or fenpropidin; benzimidazole fungicidal compounds such as carbendazim, benomyl, thiabendazole, or methylpoly Thiophanate-methyl; procymidone; cyprodinil; pyrimethanil; diethofencarb; thiuram; fiuazinain, wande (mancozeb): iprodione; vinclozolin, tetrachloroisophthalonitrile-24- 201010989 (chlorothalonil); captan; capprine (m ep anipyrim), seed dressing Fenpiclonil; fludioxonil; dichlofluanid; folpet; kresoxim-methyl; azoxystrobin; trifloxystrobin; Fluoxastrobin; steep oxygen bacteria vinegar (pi Coxystrobin); pyraclostrobin; dimoxystrobin; pyribencarb; metomycin (metominostrobin); enestroburin; spiroxamine; quinoxyfen; Fenhex amid; famoxadone; fenamidone; zoxamide; etaboxam; amisulbrom; propidium zinc Iprovalicarb); benthiavalicarb; cyazofamid; mandipropamid; boscalid; Pj± penthiopyrad; metrafenone Fluopyram; bixafen; cyflufenamid; proquinazid; oressastrobin; furametpyr; thifluzamide ; mepronil; fluolanil; flusulfamide; fluopicolide; metalaxyl ;; kiralaxyl; fosetyl; Cymoxanil); pencycuron: tolclofos-methyl ; carpropamid; diclocymet; fenoxanil; tricyclazole; pyroquilon; culling fever-25- 201010989 (probenazole); Isodinil; tiadinil: tebufroquin; diclomezine; kasugamycin; ferimzone; fthalide; (validamycin); hydroxyisoxazole; dioctyloctylamine acetate (iminoctadin-acetate); isoprothiolane; oxo丨inic acid; oxytetracycline; streptomycin; Isopyrazam; BAF-14182; flutianil; analytical copper oxide; copper (II) hydroxide; basic copper sulfate; organic copper; Examples of active ingredients of insecticides include the following compounds = (1) organophosphorus compounds acephate, phosphating, butathiofos, cadusafos, chlorethoxyfos, chlorfenvinphos ), chlorpyrifos, chlorpyrifos-methyl, cyanophos: CYAP, diazinon, DCIP (dichlorodiisopropyl ether), depletion of phosphorus (dichlofenthion): ECP Dichlorvos: DDVP, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, benefit Etrimfos, fenthion: MPP' fenitrothion: MEP, fosthiazate, formothion, phosphine, isofenphos, plusfusone (isoxathion), marathion (maathion), mesulfenfos, methadinion: DMTP, monocrotophos, naled: BRP, oxydeprofos: ESP, balason-26- 201010989 (parathion), Yubi Phosalone, phosmet: PMP, pirimiphos-methyl, pyridafenthion, quinalphos, phenthoate: PAP, profenofos ), propaphos, prothiofos, pyraclorfos, salithion, sulprofos, tebupirimfos, temephos, kill Tetrachlorvinphos, terbufos 'thiometon ' trichlorphon : DEP, vamidothion, phorate, cadusafos, etc.; (2) urethane compound alanycarb, bendiocarb, benfuracarb, BPMC, carbaryl, carbofuran, carbosulfan ), cloethocarb, ethiofencarb, fenobucarb, fenothiocarb, fenoxycarb, furathiocarb, isoprocarb (isoprocarb) : MIPC, treatment of pest control Metocarb), metomyl, metiocarb, NAC, oxamyl, pirimicarb, propoxur: PHC 'XMC, thiodicarb , xylylcarb, aldicarb, etc.; (3) synthetic pyrethroid compounds -27- 201010989 aninin (acrinathrin), arrhenone (allethrin), befunning (b enfluthrin , β_cyfluthrin, bifenthrin, cycloprothrin, cyprofen, cyhalothrin, cypermethrin, deltamethrin , esfenvalerate, ethofenprox, fenpropathrin, fenvalerate, flucythrinate, flufenoprox, flumethrin, fuhuali Fluvalinate, halfenprox, imiprothrin, p.ermethrin, prallethrin, pyrethrins, resmethrin, σ- Sigma-cypermethrin Afluofen), tefluthrin, trolomethrin, transfluthrin, tetramethrin, phenothrin, cyphenothrin, alpha-race Alpha-cypermethrin, zeta-cypermethrin, lambda-cyhalothrin, furamethrin, tau-f.luvalinate , 2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl (EZ)-(IRS, 3RS; IRS, 3SR)-2,2-dimethyl-3-propan- 1-alkenylcyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4-methylbenzyl (EZ)-(IRS, 3RS; 1RS, 3SR)-2,2-dimethyl- 3-prop-1-enylcyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl (1RS, 3RS; 1RS, 3SR)-2,2 - dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate, etc.; •28- 201010989 (4) Neretic toxin compound cartap, free speed (bensultap), sulfur Thiocyclam, monosultap, bisultap, etc.; (5) new nicotine compounds imidacloprid, nitenpyram, aceta Miprid) thiamethoxam, thiacloprid, dinotefuran, clothianidin, etc.; (6) Benzamidine urea compound chlorfluazuron, double three Bistrifluron, diafenthiuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron hexaflumuron, lufenlong Lufenuron), novaluron, noviflumuron, teflubenzuron, triflumuron, triazlon, etc.; (7) phenylpyrazole compound acetaminophen (acetoprole) ), ethiprole, fipronil 'vaniliprole, pyriprole 'pyrafluprole, etc.; (8) Bt toxin insecticide derived from fresh spores of Bacillus thuringiensis, Crystalline toxin produced by S. cerevisiae, and mixtures thereof; (9) Hydrazine compound -29- 201010989 Chromofenozide, halofenozide, methoxyfenozide, tebufenoz Ide), etc.; (1) organochlorine compounds Aldrin, dieldrin, dienochlor, endosulfan, methoxychlor, etc.

(1) natural insecticides, mechanical oils and nicotine sulfates; and (12) other pesticides

Avermectin-B, bromopropylate, buprofezin, chlorphenapyr, cyromazine, DD (l,3-dichloropropene) ), emamectin- benzoate, fenazaquin, flupyrazofos, hydroprene, metoprene, indoxacarb, worm Ketone (metoxadiazone), milbemy cin-A, pymetrozine, pyridalyl, pyriproxyfen, spinosad, sulfluramid , tolfenpyrad, triazamate, flubendiamide, lepimectin, arsenic acid, benclothiaz, calcium cyanamide, calcium polysulfide, chlordane, DDT, DSP, Flufenerim, flonicamid, flurimfen, formetanate, metam-ammonium, metam-sodium, bromide, -30- 201010989 nidinotefuran, oily acid, Protrifenbute, spironolactone (spiro) Mesifen), sulfur, metaflumizone, spirotetramat, pyrifluquinazone, spinetoram, and chlorantraniliprole and cyantraniliprole. Examples of active ingredients of acaricides include acequinocyl _, amitraz, benzoximate, bifenaate, bromopropyl ate, and diarrhea (chinomethionat), chlorobenzilate, PCBS (chlorfenson), clofentezine, cyflumetofen, kelthane (dicofol), According to etoxazole, fenbutatin oxide, fenothiocarb, fenpyroximate, fluacrypyrim, fluproxyfen, hexythiazox 'propagite · · · BPPS, polynactins, pyridaben, Pyrimidifen, tebufenpyrad, tetradifon, spirodiclofen, snail Examples of active ingredients of spiromesifen, spirotetramat, amidoflumet, and cyenopyrafen ° nematicides include DCIP, fosthiazate, levamisol hydrochloride, methyl isoform Thiocyanate ; Molang obtained tartrate (moraltel tartarate), and imicyafos. The method for controlling plant diseases of the present invention has the step of applying an effective amount of the compound of the present invention to plants or soil. The control method of the present invention is usually carried out by applying the plant disease control composition of the present invention to plants or soil by -31 - 201010989. In the method for controlling plant diseases of the present invention, the amount of the plant disease controlling composition of the present invention varies depending on weather conditions, a modulation form, an application period, an application method, an application position, a target disease, a target crop, and the like, and the present invention The compound of the present invention is usually contained in the plant disease controlling composition in an amount of from 1 to 500 g (preferably from 2 to 200 g) / 1 000 m2. Emulsions, wettable powders, fluids and the like are usually diluted with water before application, and @ In this case, the concentration of the compound of the present invention after dilution is usually from 0.0005 to 2% by weight, preferably 〇.〇〇. 5 to 1% by weight, while powders, granules and the like are usually used without being diluted. In the treatment of the seed, the compound of the present invention in the plant disease controlling composition of the present invention is usually contained in an amount of from 0.001 to 100 g', preferably from 0.01 to 50 g, based on 1 kg of the seed. The plant disease control composition of the present invention can be used as a control composition for plant diseases of agricultural land such as fields, rice fields, peats, orchards, and the like. The plant disease controlling composition of the present invention can prevent or prevent plant diseases caused by plant diseases used in cultivating the crop land of the "grass" "crop". Crops: corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybeans, peanuts, artemisia, beets, rapeseed, sunflower, sugar cane, tobacco, etc.; vegetables: eggplant vegetables (eggplant, tomato, sweet) Pepper, pepper, potato, etc.), melon vegetables (cucumber, pumpkin, winter squash, watermelon, cantaloupe, etc.), cruciferous vegetables (Japanese small carrots, white phthalocyanine, horseradish, stalk cabbage, Chinese cabbage) Vegetables, mustard, broccoli, broccoli, etc.), chrysanthemum vegetables (burdock, chrysanthemum, artichoke, lettuce, etc. -32- 201010989, etc.), liliaceae vegetables (onions, onions, garlic, and reeds), ammiaceous vegetables ( Carrots, incense, axe, European radish, etc.), leeks (spinach, swiss, etc.), mint vegetables (perilla, mint, basil, etc.), strawberries, sweet potatoes, Japanese yam, oysters, etc. , flower; foliage plant; fruit: mineral fruit (mineral fruit, pear, Japanese pear, papaya, medlar, etc.), stone fleshy fruits (peach, plum (pium), nectarine, Prunus mume, cherries, almonds, plums, etc.), citrus fruits (citrus, orange, lemon, rime, grapefruit, etc.), nuts (nuts) (chessnuts, walnuts, hazelnuts, almonds, pistachios) , cashew nuts, Australian walnut nuts, etc.), berries (blueberries, cranberries, blackberries, raspberries, etc.), grapes, persimmons, olives, alfalfa, bananas, coffee, date palms, coconuts, etc., non-fruit trees Other trees: tea, mulberry, flowering plants, street trees (ash, birch, hawthorn, eucalyptus, ginkgo, lilac, maple, eucalyptus, aspen, jude, maple, plane tree, dragonfly Trees 'Thuja, fir, hemlock, juniper, pinus, spruce, and yew) and so on. The aforementioned "Crops" include crops that have been rendered resistant by typical breeding or genetic engineering techniques: HPPD inhibitors such as isoxaflutole, ALS inhibitors such as imazethapyr ( Imazethapyr) or thifensulfuron-methyl, an EPSP synthase inhibitor, a branamine synthase inhibitor, and a herbicide such as bromoxynil. -33- 201010989 Examples of "crops" that are resistant by typical breeding methods include Clearfield (registered trademark) canola, which is resistant to imidazolinone herbicides such as imazethapyr, and weed suppression to sulfonamide ALS An agent such as thifensulfuron-methyl is resistant to STS yellow S. In addition, examples of "crops" that are resistant by genetic recombination include maize varieties that are resistant to glyphosate or g 1 u f 〇 s i n a t e. Such corn varieties have been marketed under the product names such as "RoundupReady (registered trademark) " and "LibertyLink (registered trademark)" _ The aforementioned "crop" includes genetically engineered crops produced using this genetic recombination technique, It can, for example, synthesize selective toxins known in the genus Bacillus. Examples of toxins expressed in such genetically engineered crops include insecticides derived from Bacillus cereus or Bacillus popilliae. Protein; δ-endotoxin derived from S. serrata such as CrylAb, Cry 1 Ac ' Cry 1 F ' Cry 1 F a2, Cry2Ab, Cry3A, Cry3Bbl or Cry9C; insecticidal proteins such as VIP1, VIP2, VIP3, or VIP3A; Insecticidal protein from nematodes; toxins produced by animals such as scorpion toxin, spider toxin, bee toxin, or specific insect neurotoxin; filamentous toxin; plant lectin; lectin; protease inhibitor such as trypsin inhibition Agent, serine protease inhibitor, patatin, cystatin, or papain inhibition Ribosome-inactivating proteins (RIP) such as lysine, corn-RIP, acacia, luffin, saporin, or briodin; steroid metabolism enzymes such as 3-hydroxyl Steroid oxidase, hull steroid-UDP-glucoside-34- 201010989 ecdyster 〇id - UDP - g 1 uc 〇sy 1 transferase , or cholesterol oxidase; ecdysone inhibitor; hmg-coa reductase Ion channel inhibitors such as sodium channel inhibitors or calcium channel inhibitors; vasopressin esterase; diuretic hormone receptor; purine synthase; biphenylmethyl synthase; chitinase; and polyglucose. Toxins expressed in isogenic crops include: δ-endotoxin proteins such as CrylAb, CrylAc, CrylF, CrylFa2, φ Cry2Ab, Cry3A, Cry3Bbl or Cry9C and insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A; Deleted toxins; and modified toxins. These mixed toxins are produced using genetic recombination techniques and thus new combinations of different regions of the protein. Remove some CrylAb known to contain the amino acid sequence of a partial deletion of the toxin. Modified toxin-based one or more amino acid substitutions generated by the action of the native toxin. Examples of such toxins and recombinant plants capable of synthesizing such toxins are described in EP-A-0 3 74 753, WO 93/07278, WO 95/34656, EP-A-0 427 529, EP-A-45 1 878, W Ο 0 3 / 0 5 2 0 7 3 and so on. The toxins contained in these recombinant plants enable plants to provide resistance to insect pests particularly belonging to Coleoptera, Diptera and Lepidoptera. Further, genetically recombinant plants comprising one or more insecticidal pest resistance gene groups and exhibiting one or more toxins are known, and some of these genetically recombinant plants are commercially available. Examples of such genetically modified plants include YieldGard (registered trademark) (a variant of maize expressing CrylAb toxin), -35- 201010989

YieldGard Rootworm (registered trademark) (a maize variety showing Cry3Bbl toxin), YieldGard Plus (registered trademark) (a maize variety showing CrylAb and Cry3Bbl toxin), Herculex I (registered trademark) (expressing phosphinotricine N-acetoxytransferase (PAT) For maize varieties resistant to CrylFa2 toxin and gluphosinate, NuCOTN33B (a cotton variety showing Cry 1 Ac toxin), Bollgard I (registered trademark) (a cotton variant showing CrylAc toxin), Bollgard II ( Registered trademark) (expressing cotton varieties of CrylAc and Cry2Ab toxins), _ VIPCOT (registered trademark) (presenting cotton varieties of VIP toxins), NewLeaf (registered trademark) (potato varieties expressing Cry3A toxin), NatureGard (registered trademark) , Agrisure (registered trademark), GT Advantage (GA21 glyphosate resistant), Agrisure (registered trademark), CB Advantage (Btll corn glutinous (CB) characteristics), and Protecta (registered trademark). The aforementioned "crop" also includes crops produced using genetic engineering techniques.

It produces a selective anti-pathogenic substance. G PR proteins and the like are known as such anti-pathogenic substances (PRPs, EP_A-0 392 225). The production of such anti-pathogenic substances and genetically modified crops is described in ΕΡ-Α-0 392 225, WO 95/3 3 8 1 8 , ΕΡ-Α-0 353 191 and the like. Examples of such anti-pathogenic substances expressed in genetically modified crops include: ion channel inhibitors such as sodium channel inhibitors or calcium channel inhibitors (KP1, KP4 and KP6 toxins are known, etc., which are Produced); purine synthase; biphenylmethyl synthase; chitinase; polydextrose-36-201010989 enzyme; PR protein; and anti-pathogenic substances produced by microorganisms such as peptide antibiotics, antibiotics with heterocycles A protein factor associated with plant disease resistance (which is referred to as the plant disease resistance gene and is described in WO 03/000906). As a plant disease which can be controlled by the compound of the present invention, for example, a plant disease caused by a filamentous fungus is mentioned. More specific examples include, but are not limited to, the following diseases. The method for controlling a plant disease according to the present invention is usually carried out by using the plant disease controlling composition of the present invention in accordance with the above method for applying the plant disease controlling composition of the present invention. Rice-growing plants: Magnaporthe grisea, Cochliobolus miyabeanus, Rhizoctonia solani, Gibberella fujikuroi, S cl erophthor a macrospor a); wheat, barley and oats: Erysiphe graminis, Fusarium graminearum, F_ avenacerum, F_ culmorum, Fusarium oxysporum Microdochium nivale), Puccinia striiformis, P. graminis, P. recondite, R. hordei, Typhula sp. , Ustilago tritici, Wheat smut (U. nuda), Tilletia caries, Pseudocercosporella herpotrichoides, Rhynchosporium secalis, leaves Blight (Septoria tritici) 'Bright wheat blight -37- 201010989 (Leptosphaeria nodorum), Pyren〇phora teres Drechsler, small Gaeumannomyces graminis, Pyrenophora tritici-repentis; Citrus: Diaporthe citri, Elsinoe fawcetti, Penicillium digitatum , mandarin orange peony (Ρ· italicum); apple · wilting (Monilinia mali), apple black husk (Valsa ceratosperma), apple powdery mildew (Podosphaera leucotricha), brick bacillus apple disease prototype _ ( Alternaria alternata apple pathotype), Venturia inaequalis, Glomerella cingulata; Pear: Venturia nashicola, V_ pirina, Rhizoctonia chinensis pear prototype (Alternaria alternata Japanese pear pathotype), Gymnosporangium haraeanum; peach: Monilinia fructicola, Cladosporium carpophilum, Phomopsis sp.; grape: black pox (Elsinoe ampelina), grape Late rot (Glomerella @ cingulata) Phytophthora (Uncinula necator) rust (Phakopsora) Ampelopsidis), Guignardia bidwellii, Plasmopara viticola; persimmon: Gloeosporium kaki, Cercospora kaki, My cosphaerell a nawae; Gourds Colletotrichum lagenarium, Sphaerotheca fuliginea, Mycosphaerella melonis, Fusarium oxysporum, Phytophthora spp. (Pseudoperonospora -38- 201010989 cubensis), Phytophthora sp. ), Pythium sp.; before: Alternaria solani, Cladosporium fulvum, Phytophthora infestans; anterior: Phomopsis vexans ), Erysiphe cichoracearum; Brassica family Alternaria japonica, Cercosporella brassicae, Plasmodiophora parasitica, Brassica Peronospora parasitica; bacteria: amaranth rust (Puccinia allii); large : Ce_rcospora kikuchii, Elsinoe glycines, Diaporthe phaseolorum var. sojae, Asian soybean rust (Phakopsora pachyrhizi); Sensitive bean: Colletotrichum lindemthianum; Peanut: Arachis chinensis Cercospora personata), Cercospora arachidicola, Sclerotium rolfsii; Pea: Erysiphe pisi; Potato: Alternaria, Phytophthora infestans, Verticillium Verticillium albo-atrum, V. dahliae, V. nigrescens; strawberry: Sphaerotheca humuli; tea crop: Excasidium Reticulatum), Elsinoe leucospila, Pestalotiopsis sp., Colletotrichum theae-sinensis; Su grass: Alternaria longipes, Erysiphe cichoracearum, C ο 11 etotri Chum t ab a cum, Phytophthora infestans -39- 201010989 (Peronospora tab.acina), tobacco Pathogen (Phytophthora nicotianae); beet: leaf spot (Cercospora beticola), amaranth leaf spot fungus (Thanatephorus cucumeris), species of fungus (Aphanomyces sochlioides); Rose: black spot (Diplocarpon

Rosaae), Sphaerotheca pannosa; Chrysanthemum: Septoria chrysanthemi-indici, Puccinia horiana; Botrytis cinerea, Botrytis cinerea Byssoidea), B. squamosa, Botrytis alii; various crops: gray bacterium, sclerotinia sclerotiorum; radish: Alternaria brassicicola; Grassland: Sclerotinia homeocarpa, Rhizoctonia so.lani; and banana: Mycosphaerella fijiensis, Mycosphaerella musicola. [Examples] Examples of the production examples, formulation examples and test examples of the present invention are shown below. Production Example 1 0.26 g of carbonic acid planer was added to 0.20 g of N-(2-fluoro-3-hydroxyphenyl)methyl-benzothiazole-6-carboxamide, 0.10 g of 3-bromo-1-propene and 5 In a mixture of ml DMF, and the mixture was stirred at room temperature for 4 hours. Water was added to the reaction mixture, and the resulting solid was collected by filtration. The solid was washed successively with -40-201010989 aqueous sodium hydroxide solution, water and hexane to give 0.22 g of N-(2-fluoro-3-(2-propenyloxy)phenyl)methyl-benzothiazole-6. Carboxylamidine (hereinafter referred to as Compound (1) of the present invention). The compound of the invention (1)

H-NMR (CDC13) 6: 9.11 (1Η, s), 8.48 (1H, s), 8.16 (1H, d, J = 8.5 Hz), 7.88 (1H, d, J = 8.5 Hz), 7.06-7.02 ( (2H, d, J = 17.4 Hz), 5.32 , d, J = 5.1 Hz), 4.61 (2H, d, J = 5.1 Hz). Manufacturing Example 2 Add 0.26 g of carbonic acid to 0_20 g of N-(2-fluoro-3-hydroxyphenyl) ® methyl a mixture of benzothiazole-6-carboxamide, 0.13 g of 5-bromo-1-pentene and 5 ml of DMF, and the mixture was stirred at room temperature for 4 hours. Water was added to the reaction mixture, and the resulting solid was collected by filtration. The solid was washed successively with aqueous sodium hydroxide solution, water and hexane to give 0.23 g of N-(2-fluoro-3-(4-pentenyloxy)phenyl)methyl-benzothiazole-6-carboxyindole. Amine (hereinafter referred to as compound (2) of the present invention).

Inventive Compound (2) 〇 F

-41 - 201010989 'H-NMR (CDC13) δ: 1.90-1.97 (2H, m), 2.23-2.29 (2H, m), 4.03-4.06 (2H, m), 4.74 (2H, d, J = 5.3 Hz ), 5.00-5.10 (2H, m), 5.82-5.89 (1H, m), 6.62 (1H, s), 6.90-6.95 (1 H, m), 6.98-7.06 (2H, m), 7.87-7.89 ( 1H, m), 8.16 (1H, d, J = 8.5 Hz), 8.48 (1H, s), 9.11 (1H, s). Production Example 3 0.26 g of carbonic acid planer was added to 0.20 g of N-(2-fluoro A mixture of -3-hydroxyphenyl)indolemethyl-benzothiazole-6-carboxamide, 0.14 g of 6-bromo-1-hexene and 5 ml of DMF, and the mixture was stirred at room temperature for 4 hours. Water was added to the reaction mixture, and the resulting solid was collected by filtration. The solid was washed successively with aqueous sodium hydroxide solution, water and hexane to give 0.22 g of bis(2-fluoro-3-(5-hexenyloxy)phenyl)methyl-benzothiazole-6-carboxyindole. Amine (hereinafter referred to as compound (3) of the present invention). Inventive compound (3)

*H-NMR (CDCI3) δ: 1.56-1.63 (2Η, m), 1.81-1.88 (2H, m), 2.11-2.17 (2H, m), 4.04 (2H, t, J = 6.4 Hz), 4.74 ( 2H, d, J = 5.8 Hz), 4.96-5.07 (2H, m), 5.78-5.88 ( 1 H, m), 6.59 (1H, s), 6.92 (1H, td, J = 8.0, 1.9 Hz), 6.98-7.06 (2H, m), 7.88 (1H, dd, J = 8.5, 1.7 Hz), 8.16 (1H, d, J = 8.7 Hz), 8.48 (1H, d, J = 1.4 Hz), 9.11 (1H , s). -42 - 201010989 Manufacturing Example 4

〇·26 g of carbonic acid was absolutely added to 0.20 g of N-(2-fluoro-3-hydroxyphenyl)methyl-benzothiazole-6-carboxamide, 0.15 g of 7-bromo-1-heptene and 5 In a mixture of ml DMF, and the mixture was stirred at room temperature for 4 hours. Water was added to the reaction mixture, and the resulting solid was collected by filtration. The solid was washed successively with aqueous sodium hydroxide solution, water and hexane to give 0.24 g of (2-fluoro-3-(6-heptenyloxy)phenyl)methyl-benzothiazole-6-carboxyindole. Amine (hereinafter referred to as compound (4) of the present invention). The compound of the invention (4)

F ^^L/OCH2CH2CH2CH2CH2CH=CH2

U JH-NMR (CDC13) δ: 1.47- 1.50 (4Η, m), 1.80- 1.87 (2Η, m), 2.07-2.12 (2H, m), 4.03 (2H, t, J = 6.5 Hz), 4.74 ( 2H, Ref, J = 5.8 Hz), 4.93 -5.04 (2H, m), 5.77-5.87 ( 1 H, m), 6.60 (1H, s), 6.90-6.94 (1 H, m), 6.98-7.06 (2H, m), 7.88 (1H, dd, J = 8.5, 1.7 Hz), 8.16 (1H, d, J = 8.5 Hz), 8.48 (1H, d, J = 1.4 Hz), 9.11 (1H, s) Manufacturing example 5

0.23 g of potassium carbonate was added to 0.30 g of N-(2-fluoro-3-hydroxyphenyl)methyl-benzothiazole-6-carboxamide, 0.16 g of 1-bromo-2-pentene and 5 ml of DMF. The mixture was stirred and the mixture was stirred at room temperature for 6 hours. Water was added to the mixture -43-201010989, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, then dried over magnesium sulfate and evaporated. The obtained residue was subjected to silica gel chromatography to obtain 0.24 g of N-(2-fluoro-3-(2-pentenyloxy)phenyl)methyl-benzothiazole-6-carboxamide (hereinafter referred to as Is a compound of the invention (5)) 〇 a compound of the invention (5)

'H-NMR (CDC13) δ: 1.02 (3.0H, td, J = 7.5, 1.4 Hz), 2.08-2.19 (2.OH, m), 4.54 (1.0H, d, J = 5.8 Hz), 4.66 ( 1.0H, d, J = 5.3 Hz), 4.74 (2.OH, d, J = 5.8 Hz), 5.62-5.75 (1.5H, m), 5.87-5.94 (0.5H, m), 6.62 (1.0H, s), 6.91-7.06 (3.OH, m), 7.87 (1.0H, dd, J = 8.5, 1.7 Hz), 8.15 (1.0H, d, J = 8.5 Hz), 8.47 (1.0H, d, J = 1.4 Hz), 9.11 (1.OH, s). Production Example 6 0.28 g of cesium carbonate was added to 0.20 g of N-(3-hydroxyphenyl)methyl-benzothiazole-6-carboxamide, 0.11 g. A mixture of 3-bromo-1-propene and 3 ml of DMF was added, and the mixture was stirred at room temperature for 7 hours. Water and a sodium hydroxide aqueous solution were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated. The obtained residue was subjected to silica gel chromatography to obtain 0.18 g of N-(3-201010989 (2-propenyloxy)phenyl)methyl-benzothiazole-6-carboxamide (hereinafter referred to as the compound of the present invention). (6)). Inventive compound (6) Ο

^-NMR (CDC13) δ: 4.51-4.54 (2Η, m), 4.65 (2H, d, J o =5.6 Hz), 5.26-5.30 ( 1 H, m), 5.38-5.43 ( 1 H, m), 5.99-6.09 (1H, m), 6.62 (1H, s), 6.86 (1H, dd, J = 8.2, 1.9 Hz), 6.94-6.96 (2H, m), 7.27 (1H, t, J = 7.8 Hz) , 7.89 (1H, dd, J = 8.6, 1.6 Hz), 8.15 (1H, d, J = 8.5 Hz), 8.49 (1H, d, J = 1.7 Hz), 9.10 (1H, s). Manufacturing Example 7 0.45 g of cesium carbonate was added to a mixture of 0.30 g of N-(3-hydroxyphenyl)methyl-benzene β-thiazole-6-carboxamide, 0.19 g of 5-bromo-1-pentene and 5 ml of DMF, and The mixture was stirred at room temperature for 6 hours. Water and a sodium hydroxide aqueous solution were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated. The residue obtained was concentrated, and the resulting solid was washed with hexane to give 0.11 g of N-(3-(4-pentenyloxy)phenyl)methyl-benzothiazole-6-carboxamide. (hereinafter referred to as the compound (7) of the present invention). The compound of the invention (7) -45- 201010989

.◦ch2ch2ch2ch=ch2 !H-NMR (CDC13) δ: 1.85- 1.92 (2H, m), 2.21-2.26 (2H, in), 3.97 (2H, t, J = 6.4 Hz), 4.66 (2H, d, J = 5.6 Hz), 4.98-5.01 (1H, m), 5.03-5.09 ( 1 H, m), 5.80- 5.90 ( 1 H, m), 6.46 (1H, s), 6.85 (1H, dd, J = 8.0, 2.2 Hz), 6.92-6.96 (2H, m), 7.26-7.30 ( 1 H, m), 7.89 (1H, dd, J = 8.6, 1.8 Hz), ❿ 8.17 (1H, d, J = 8.5 Hz) ), 8.51 (1H, d, J = 1.4 Hz), 9.12 (1H, s). Production Example 8 0.45 g of carbonic acid was absolutely added to 0.30 g of N-(3-hydroxyphenyl)methyl-benzothiazole-6 a mixture of carboxyguanamine, 0.21 g of 6-bromo-1-hexene and 5 ml of DMF, and the mixture was stirred at room temperature for 6 hours. Water and a sodium hydroxide aqueous solution were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated. The residue obtained was concentrated, and the resulting solid was washed with hexane to give 0.14 g of N-(3-(5-hexenyloxy)phenyl)methyl-benzothiazole-6-carboxamide. (hereinafter referred to as the compound (8) of the present invention). Inventive compound (8)

-46- 201010989 W-NMR (CDC13) δ: 1.5 3 - 1.60 (2H, m), 1.76- 1.83 (2H, m), 2.09-2.15 (2H, m), 3.97 (2H, t, J - 6.4 Hz ), 4.66 (2H, d, J = 5.8 Hz), 4.95-4.98 (1 H, m), 5.00-5.06 (2H, m), 5.77-5.87 (1 H, m), 6.46 (1H, s), 6.84 (1H, dd, J = 8.1, 2.1 Hz), 6.92-6.96 (2H, m), 7.26-7.30 (1 H, m), 7.88 (1H, dd, J = 8.6, 1.8 Hz), 8.17 (1H , d, J = 8.7 Hz), 8.51 (1H, d, J = 1.4 Hz), 9.12 (1H, s). Reference Example 9 0.26 g of carbonic acid planer was added to 0.20 g of N-(3-hydroxyphenyl) A mixture of methyl-benzothiazole-6-carboxyguanamine, 0.16 g of 7-bromo-1-heptene and 5 ml of DMF was added, and the mixture was stirred at room temperature for 4 hours. Water was added to the reaction mixture, and the resulting solid was collected by filtration. The solid was washed successively with sodium hydroxide aqueous hydrazine, water and hexane to give 0.12 g of N-(3-(6-heptenyloxy)phenyl)methyl-benzothiazole-6-carboxamide ( Hereinafter referred to as the compound β (9)) of the present invention. The compound of the invention (9 ) Ο

'H-NMR (CDC13) δ: 9.11 (1Η, s), 8.50 (1H, d, J = 1.7 Hz), 8.16 (1H, d, J = 8.5 Hz), 7.88 (1H, dd, J = 8.5, 1.7 Hz), 7.27 (1H, t, J = 7.9 Hz), 6.95-6.91 (2H, m), 6.84 (1H, dd, J = 8.3, 2.4 Hz), 6.50 (1H, s), 5.86-5.76 ( 1H, m), 5.00 -47- 201010989 (1H, dq, J = 17.1, 1.7 Hz), 4.94 (1H, dd, J = 10.2, 2.0 Hz), 4.66 (2H, d, J = 5.6 Hz), 3.95 (2H, t, J = 6.5 Hz), 2.08 (2H, d, J = 6.8 Hz), 1.82- 1.75 (2H, m), 1.52-1.42 (4H, m). Manufacturing Example 10 0.28 g of carbonic acid planing To a mixture of 0.20 g of N-(3-hydroxyphenyl)methyl-benzothiazole-6-carboxamide, 0.12 g of 1-bromo-2-butene and 5 ml of DMF, and the mixture was stirred at room temperature 4 hour. Water was added to the reaction mixture and the resulting solid was collected by filtration. The solid was washed successively with aqueous sodium hydroxide solution, water and hexane to give 0.23 g of N-(3-(2-butoxy)phenyl)methyl-benzothiazole-6-carboxamide (hereinafter referred to as It is the compound (10)) of the present invention. Inventive Compound (10)

^-NMR (CDC13) 6: 9.12 (1Η, s), 8.50 (1H, s), 8.16 (1H, d, J = 8.5 Hz), 7.89 (1H, d, J = 8.5 Hz), 7.27 (1H, t, J = 7.8 Hz), 6.95 (2H, d, J = 12.3 Hz), 6.86 (1H, dd, J = 7.8, 2.3 Hz), 6.54 (1H, s), 5.90-5.82 ( 1 H, m) , 5.75-5.69 (1H, m), 4.66 (2H, d, J = 5.6 Hz), 4.46 (2H, d, J = 5.8 Hz), 1.74 (3H, d, J = 6.0 Hz). Manufacturing Example 11 48 - 201010989 Add 0.28 g of carbonic acid planing to a mixture of 0.20 g of N-(3-hydroxyphenyl)methyl-benzothiazole-6-carboxamide, 0.14 g of 1-bromo-2-pentene and 5 ml of DMF And the mixture was stirred at room temperature for 4 hours. Water was added to the reaction mixture, and the resulting solid was collected by filtration. The solid was washed successively with aqueous sodium hydroxide solution, water and hexane to obtain 0.18 g of N-(3-(2-pentenyloxy)phenyl)methyl-benzothiazole-6-carboxamide (hereinafter referred to as Is the compound (11)) of the present invention. Reference

The compound of the present invention (1 1) 〇

OCH2CH=CHCH2CH3 !H-NMR (CDC13) 6: 9.12 (1H? d, J = 0.7 Hz), 8.50 (1H, s), 8.17 (1H, d, J = 8.5 Hz), 7.89 (1H, d, J = 8.5 Hz), 7.30-7.24 ( 1 H, m), 6.96-6.94 (2H, m), 6.86 (1H, dd, J -8.0, 2.4 Hz), 6.49 ( 1 H, s), 5.9 2 - 5 · 6 0 ( 2 H,m ), 4 · 6 7 - 4.4 8 (4H, m), 2.18-2.06 (2H, m), 1.01 (3H, t, J = 7.5 Hz). Manufacturing Example 12

0.28 g of carbonic acid was added to 0.20 g of N-(2-fluoro-3-hydroxyphenyl)methyl-benzothiazole-6-carboxamide, 0.10 g of 3-bromo-1-propyne and 5 ml of DMF. The mixture was stirred and the mixture was stirred at room temperature for 4 hours. Water was added to the reaction mixture, and the resulting solid was collected by filtration. The solid was washed successively with aqueous sodium hydroxide solution, water and hexane to give 0.17 g of N-(2-fluoro-3-(2-propynyloxy)phenyl)methyl-benzothiazole-6-carboxyindole. Amine (hereinafter referred to as the present invention - 49 - 201010989 Compound (12)). Inventive Compound (12)

F ^X.och2c=ch

U 1H-NMR (CDCI3) δ: 9.12 (1Η, s), 8.48 (1H, s), 8.16 (1H, d, J = 8.7 Hz), 7.88 (1H, d, J = 8.5 Hz), 7.08-7.07 φ (3H, m), 6.65 (1H, s), 4.78 (2H, d, J = 2.4 Hz), 4.74 (2H, d, J = 5.8 Hz), 2.55 (1H, t, J = 2.4 Hz). Production Example 13 0.11 g of 5-chloro-1-pentyne was added to 0.25 g of N-(2-fluoro-3-hydroxyphenyl)methyl-benzothiazole-6-carboxamide, about 10 mg of sodium iodide In a mixture of 36 mg of 55% sodium hydride (in oil) and 4 ml of DMF, and the mixture was stirred at 80 ° C for 2 hours, followed by stirring at 100 ° C for 2 hours. The reaction mixture was allowed to cool to about room temperature. Water and aqueous sodium hydroxide solution were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated. The residue obtained was subjected to silica gel chromatography to obtain 0.22 g of N-(2-fluoro-3-(4-pentynyloxy)phenyl)methyl-benzothiazole-6-carboxamide (hereinafter referred to as Is the compound (13)) of the present invention. The compound of the invention (13) -50- 201010989

Och2ch2ch2c=ch JH-NMR (CDC13) δ: 1.98 (1H, t, J = 2.7 Hz), 2.01-2.08 (2H, m), 2.45 (2H, td, J = 6.9, 2.6 Hz), 4.15 (2H, t, J = 6.1 Hz), 4.74 (2H, d, J = 5.4 Hz), 6.58 (1H, s), 6.93-7.07 (3H, m), 7.88 (1H, dd, J = 8.5, 1.7 Hz), 8.16 (1H, d, ❹ J - 8.5 Hz), 8.48 (1H, d, J = 1.5 Hz), 9.11 (1H, s). Manufacturing example 1 4 Add 0.13 g of 6-chloro-1-hexyne to 0.25 g N-(2-Fluoro-3-hydroxyphenyl)methyl-benzothiazole-6-carboxamide, about 10 mg sodium iodide, 36 mg 55% sodium hydride (in oil) and 4 ml DMF The mixture was stirred for 2 hours and then stirred at 100 ° C for 2 hours. The reaction mixture was allowed to cool to about room temperature. Water and aqueous sodium hydroxide solution were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated. The residue obtained was subjected to silica gel chromatography to obtain 23 g of N-(2-fluoro-3-(5-hexynyloxy)phenyl)methyl-benzothiazole-6-carboxamide ( Hereinafter referred to as the compound (14) of the present invention.

Inventive Compound (14) Ο F

-51 - 201010989 *H-NMR (CDC13) δ: 1.71.1.78 (2H, m), 1.92-1.99 (3H, m), 2.29 (2H, td, J = 7.〇, 2.6 Hz), 4.06 (2H ,t, J = 6.2 Hz), 4.73 (2H, d, J = 5.6 Hz), 6.63 (1H, s), 6.90-6.94 (1H, m), 6.98-7.06 (2H, m), 7 88 ( 1 H, dd, J = 8.5, 1.5 Hz), 8.15 (1H, d, J = 8.5 Hz), 8.47 (1H, d, J = 1.0 Hz), 9.11 (1H, s). Manufacturing Example 15

Add 0.23 g of potassium carbonate to 〇25 g n-(2-fluoro-3-hydroxyphenyl)methyl-benzothiazole-6-carboxamide, 016 g 丨bromo-2-pentyne and 4 ml DMF The mixture was stirred and the mixture was stirred at room temperature for 6 hours. Water was added to the reaction mixture' and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, then dried over magnesium sulfate and evaporated. The residue obtained was subjected to silica gel chromatography to obtain 0.23 g of Ν-(2-fluoro-3-(2-pentynyloxy)phenyl)methyl-benzothiazole-6-carboxyguanamine (hereinafter referred to as Is a compound of the invention (15)) 〇 a compound of the invention (15)

Ο F

!H-NMR (CDCI3) δ: 1.12 (3Η, t, J = 7.4 Hz), 2.19-2.26 (2H, m), 4.74-4.75 (4H, m), 6.59 (1H, s), 7.06-7.07 ( 3H, m), 7.88 (1H, dd, J = 8.5, 1.7 Hz), 8.16 (1H, d, J = 8.5 Hz), 8.48 (1H, d, J = 1.7 Hz), 9.11 (1H, s). 201010989 Manufacturing Example 1 6 0.28 g of carbonic acid planer was added to 0.20 g of N-(3-hydroxyphenylmethyl)-benzothiazole-6-carboxamide, 0.11 g of 3-bromo-abpropan and 5 ml of DMF. The mixture was stirred and the mixture was stirred at room temperature for 4 hours. Water and a sodium hydroxide aqueous solution were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated. # The residue obtained was subjected to silica gel chromatography to obtain 0.17 g of N-(3-(2-propynyloxy)phenyl)methyl-benzothiazole-6-carboxamide (hereinafter referred to as the present invention). Compound (16)). Inventive compound (16) Ο

j-NMR (CDC13) δ: 9.12 (1H, s), 8.51 (1H, d, J = 1.7 Hz), 8.17 (1H, d, J = 8.5 Hz), 7.89 (1H, dd, J = 8.5, 1.7 Hz), 7.31 (1H, t, J = 8.0 Hz), 7.03-7.00 (2H, m), 6.95-6.92 (1H, m), 6.50 (1H, s), 4.70 (2H, d, J = 2.4 Hz), 4.68 (2H, d, J = 5.6 Hz), 2.51 (1H, t, J = 2.4 Hz). Manufacturing Example 17 Add 0.14 g of 5-chloro-1-pentyne to 0.30 g of N-(3- a mixture of hydroxyphenyl)methyl-benzothiazole-6-carboxamide, about 10 mg sodium iodide, 5 1 mg of 55% sodium hydride (in oil) and 5 ml DMF, and the mixture is at 80 - 53 - 201010989. (: stirring for 2 hours, followed by stirring at 100 ° C for 2 hours. The reaction mixture was allowed to cool to about room temperature. Water and aqueous sodium hydroxide solution were added to the reaction mixture, and the mixture was extracted with ethyl acetate. It was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to give 0.20 g of N-(3-(4-pentynyloxy)phenyl)methyl- Benzothiazole-6-carboxyguanamine (hereinafter referred to as the compound (17) of the present invention). The present compound (17) Ο <ΝϊΧ η^〇γ • H-NMR (CDC13) δ: 1.95-2.03 (3H, m), 2.41 (2H, td, J = 7.0, 2.7 Hz), 4.08 (2H, t, J = 6.0 Hz), 4.67 (2H, d, J = 5.6 Hz), 6.45 (1H, s), 6.86 ( 1H, dd, J = 8.2, 2.4 Hz), 6.93 -6.97 (2H, m), 7.26-7.30 (1 H, m), 7.89 (1H, dd, J = 8.5, 1.7 Hz), 8.17 (1H, d , J = 8.5 Hz), 8.51 (1H, d, J = 1.7 Hz), 9.12 ( 1 H, s). 〇Production Example 18 Add 0.16 g of 6-chloro-1-hexyne to 0.30 g of N-(3 a mixture of -hydroxyphenyl)methyl-benzopyrazine-6-anthraquinone, about 10 mg of sodium arachidate, 51 mg of 55% sodium hydride (in oil) and 5 ml of DMF, and The mixture was stirred at 80 ° C for 2 hours' and then at 100 ° C for 2 hours. The reaction mixture was allowed to cool to about room temperature. Water and aqueous sodium hydroxide were added to the mixture, and the mixture was extracted with ethyl acetate. The layer was washed with brine brine - 54 - 201010989) then dried over magnesium sulfate and evaporated. The obtained residue was subjected to silica gel chromatography to obtain 0.28 g of N-(3-(5-hexynyloxy)phenylmethyl-benzothiazole-6-carboxamide (hereinafter referred to as the compound of the present invention ( 18)). Compounds of the invention (1 8)

OCH2CH2CH2CH2CeCH O 'H-NMR (CDC13) δ: 1.68- 1.76 (2H, m), 1.8 8- 1.95 (2H, m), 1.96 (1H, t, J = 2.7 Hz), 2.27 (2H, td, J = 7.0, 2.5 Hz), 3.99 (2H, t, J = 6.3 Hz), 4.66 (2H, d, J = 5.6 Hz), 6.46 (1H, s), 6.84 (1H, dd, J = 8.1, 2.3 Hz) , 6.92-6.96 (2H, m), 7.26-7.30 ( 1 H, m), 7.89 (1H, dd, J = 8.7, 1.7 Hz), 8.17 (1H, d, J = 8.7 Hz), 8.51 (1H, d, J = 1.7 Hz), 9.12 (1H, s). ® Manufacturing Example 19 0.28 g of carbonic acid was added to 0.20 g of N-(3-hydroxyphenyl)methyl-benzothiazole-6-carboxamide, A mixture of 0.12 g of 1-bromo-2-butyne and 5 ml of DMF was added and the mixture was stirred at room temperature for 4 hours. Water was added to the reaction mixture, and the resulting solid was collected by filtration. The solid was washed successively with aqueous sodium hydroxide solution, water and hexane to give N-(3-(2-butynyloxy)phenyl)methyl-benzothiazole-6-carboxamide. (hereinafter referred to as the compound (19) of the present invention). The present invention (19) -55- 201010989 ο

Och2c 三cch3 NMR (CDC13)S: 9.12 (1H, s), 8.51 (1H, s), 8.17 (1H, d, J - 8.5 Hz), 7.89 (1H, d, J = 8.7 Hz), 7.31- 7.24 (1H, m), 7.00-6.91 (3H, m), 6.48 (1H, s), 4.68-4.65 (4H, m), 1. .83 (3H, d, J = 1.4 Hz). Manufacturing example 2 0 0.28 g of carbonic acid planer was added to a mixture of 0.20 g of N-(3-hydroxyphenyl)methyl-benzoxazol-6-carboxamide, 0.13 g of 1-bromo-2-pentyne and 5 ml of DMF.

And the mixture was stirred at room temperature for 4 hours. Water was added to the reaction mixture, and the resulting solid was collected by filtration. The solid was washed successively with aqueous sodium hydroxide solution, water and hexane to give 0.21 g of N-(3-(2-pentynyloxy)phenyl)methyl-benzothiazole-6-carboxamide (hereinafter referred to as It is the compound (20)) of the present invention.

Inventive compound (20) Ο

^^^.OCH2C=CCH2CH3 *H-NMR (CDC13) δ: 9.12 (1Η, s), 8.50 (1H, d, J = 1.7

Hz), 8.16 (1H, d, J - 8.5 Hz), 7.89 (1H, dd, J = 8.6, 1.8

Hz), 7.29 (1H, t, J = 8.2 Hz), 6.99 (2H, d, J = 6.8 Hz),

6.92 (1H, dd, J = 8.0, 2.2 Hz), 6.50 (1H, s), 4.67 (4H, t, J -56- 201010989 =2.3 Hz), 2.21 (2H, tdd, J = 9.9, 5.0, 2.5 Hz), 1.11 (3H, t, J = 7.5 Hz). Manufacturing Example 2 1

Add 21 g of potassium carbonate to 0.30 g of N-(2-fluoro-3-hydroxyphenyl)methyl-benzothiazole-6-carboxamide, 0.16 g of bromo-2-butyne and 5 ml of DMF The mixture was stirred and the mixture was stirred at room temperature for 8 hours. Water was added to the reaction φ mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, then dried over magnesium sulfate and evaporated. The obtained residue was subjected to silica gel chromatography to obtain 0.26 g of N-(2-fluoro-3-(2-butynyloxy)phenyl)methyl-benzothiazole-6-carboxamide (hereinafter referred to as Is the compound (21)) of the present invention. Inventive Compound (21)

^-NMR (CDC13) 5: 1.85 (3H, t, J = 2.3 Hz), 4.72-4.75 (4H, m), 6.58 (1H, s), 7.05-7.07 (3H, m), 7.88 (1H, dd , J = 8.5, 1.7 Hz), 8.16 (1H, d, J = 8.5 Hz), 8.48 (1H, d, J = 1.7 Hz), 9.11 (1H, s). Manufacturing Example 22 0.20 g N-(2 -Fluoro-3-hydroxyphenyl)methyl-benzothiazole-6-carboxamide, 0.25 g 8-bromo-1-octene, 0.43 g carbonate planer and 3 ml DMF mix -57- 201010989, and mixtures Stir at room temperature for 1 hour. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with brine, then dried over anhydrous magnesium sulfate and evaporated. The residue obtained was subjected to silica gel chromatography to obtain 0.16 g of N-(2-fluoro-3-(7-octenyloxy)phenyl)methyl-benzothiazole-6-carboxamide (hereinafter referred to as Is the compound (22)) of the present invention. Inventive Compound (22) Ο

F

5-^^^N^^V^OCH2CH2CH2CH2CH2CH2CH=CH2 Η Ν- !H-NMR (CDC13) δ: 1.32- 1.52 (6H, m), 1.76-1.84 (2H, m), 2.02-2.08 (2H, m ), 3.99 (2H, t, J = 6.5 Hz), 4.70 (2H, d, J = 5.6 Hz), 4.91-5.03 (2H, m), 5.75-5.86 ( 1 H, m), 6.8 5 -6.90 ( 1 H, m), 6.92-7.02 (2H, m), 7.11-7.16 (1H, m), 7.88 (1H, d, J = 8.5 Hz), 8.07 (1H, d, J = 8.5 Hz), 8.44 ( 1H, s), 9.06 (1H, s). © Manufacturing Example 23 0.20 g of N-3-(hydroxyphenyl)methyl-benzothiazole-6-carboxamide, 0.27 g of 8-bromo-1-octyl The olefin, 0.46 g of carbonic acid planer and 3 ml of DMF were mixed, and the mixture was stirred at room temperature for 2 hours. Water was added to the reaction mixture' and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with brine, dried over anhydrous magnesium sulfate The residue obtained was subjected to silica gel chromatography to obtain 0.13 g of N-(3-(7-octenyloxy)benzene-58-201010989)methyl-benzothiazole-6-carboxamide (hereinafter referred to as Is the compound (23)) of the present invention. Inventive compound (23) Ο

Ki/\^^〇CH2CH2CH2CH2CH2CH2CH=CH2 'H-NMR (CDC13) δ: 1.35- 1.50 (6H, m), 1.74-1.81 (2H, φ m), 2.02-2.08 (2H, m), 3.95 (2H, t, J = 6.5 Hz), 4.65 (2H, d, J = 5.6 Hz), 4.91-5.02 (2H, m), 5.75-5.86 (1 H, m), 6.58-6.62 (1 H, m), 6.82 -6.85 (1 H, m), 6.91 (1H, s), 6.94 (1H, d, J = 7.6 Hz), 7.25-7.29 (1H, m), 7.89 (1H, dd, J = 8.5, 2.0 Hz) , 8.16 (1H, d, J = 8.5 Hz), 8.51 (1H, d, J = 1.7 Hz), 9.11 (1 H, s). Next, the manufacture of the intermediate of the compound of the present invention will be shown with reference to the production examples. . Reference Production Example 1 A mixture of 20 g of 3-hydroxybenzaldehyde, 200 ml of 2-propanol, 16 g of pyridine and 15 g of hydroxylamine hydrochloride was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with 5% hydrochloric acid, water and brine, and dried over magnesium sulfate and concentrated under reduced pressure to afford 26 g of 3-hydroxybenzaldehyde. A mixture of 25 g of 3-hydroxybenzaldehyde oxime, 1.3 g of 5% palladium on carbon and 300 ml of B-59-201010989 alcohol was stirred at room temperature under a hydrogen atmosphere of about 1 atm for 3 hours. The reaction mixture was filtered through Celite (registered trademark). The filtrate was concentrated under reduced pressure. The resulting residue was mixed at 〇 ° C, 200 ml of acetonitrile and 28 g of concentrated hydrochloric acid, and the resulting solid was collected by filtration. The solid was washed with acetonitrile and dried under reduced pressure to give 20 g of 3-hydroxybenzylamine hydrochloride. 3-hydroxybenzylamine hydrochloride. H3N CI-

!H-NMR (DMSO-d6) δ: 3.89 (2H, q, J = 5.6 Hz), 6.79-6.82 (1H, m), 6.88-6.91 (2H, m), 7.18 (1H, t, J = 7.7 Hz), 8.51 (3H, s), 9.72 (1H, s). Reference Production Example 2 4.5 g of 2-fluoro-3-methoxybenzyl alcohol, 2.9 ml of methanesulfonium chloride and 50 ml of THF were mixed, and the mixture was 〇°c stir. 6.0 ml of triethylamine ® was added to the mixture' and the mixture was stirred at 0X for 30 minutes, followed by stirring at room temperature for 2 hours. Ethyl acetate was added to the reaction mixture, and the mixture was filtered through Celite (registered trademark). Water was added to the filtrate' and the mixture was extracted with ethyl acetate. The organic layer was washed sequentially with water and saturated brine and dried over magnesium sulfate, and then concentrated under reduced pressure to afford 6.9 g of (2-fluoro-3-methoxyphenyl)methyl methanesulfonate. (2-fluoro-3-methoxyphenyl)methyl methanesulfonate -60- 201010989

Och3 ^-NMR (CDC13) δ: 3.00 (3H, s), 3.91 (3H, s), 5.30 (2H, s), 6.96-7.14 (3H, m). Reference Production Example 3 6.7 g methanesulfonic acid ( 2_Fluoro-3-methoxyphenyl)methyl ester, 5.3 g of potassium sulfinamide and 60 ml of DMF were mixed' and the mixture was stirred at 70 ° C for 4 hours. Thereafter, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, diluted hydrochloric acid and brine, and dried over magnesium sulfate. The residue obtained was washed with hexane to give 5.8 g of N-(2-fluoro-3-methoxyphenyl)methylimine. N-(2-fluoro-3-methoxyphenyl)methyl quinone imine

*H-NMR (CDCI3) δ: 3.87 (3Η, s), 4.94 (2H, s), 6.86-6.90 (2H, m), 6.98 -7.02 ( 1 H, m), 7.73 (2H, dd, J = 5.4, 3.0 Hz), 7.86 (2H, dd, J = 5.4, 3.0 Hz). Reference Production Example 4 1.63 g of hydrazine monohydrate was added dropwise to 7·7 g of N-(2-fluoro-3-methoxy A mixture of phenyl)methylimine and 30 ml of ethanol, and the mixture -61 - 201010989 was heated to reflux for 4 hours. After that, the reaction mixture was cooled to room temperature. Water was added to the reaction mixture, and the mixture was concentrated under reduced pressure. Dilute hydrochloric acid was added to the residue, and the mixture was filtered. Ethyl acetate was added to the obtained filtrate, and a 15% aqueous sodium hydroxide solution was added to the aqueous layer until the enthalpy was reached. This liquid is separated into 2 layers. Concentrated hydrochloric acid was added to the organic layer, and the mixture was concentrated under reduced pressure to give 4.5 g of 2-fluoro-3-methoxybenzylamine hydrochloride.

2-fluoro-3-methoxybenzylamine hydrochloride

^-NMR (DMSO-d6) δ: 3.85 (3Η, s), 4.03 (2H, q, J = 5.3 Hz), 7.13-7.23 (3H, m), 8.60 (3H, br s). Reference Manufacturing Example 5 24 ml of pyridine was added dropwise to a mixed solution of 1 5.4 g of 2-fluoro-3-methoxybenzaldehyde, @30 ml of THF and 3 ml of water, and under ice cooling, 13.8 g of hydroxylamine hydrochloride was added. salt. The mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure until the total volume was about half. Water was added to the mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with dilute hydrochloric acid and brine, and dried over magnesium sulfate, and then concentrated under reduced pressure to give 16 g of 2-fluoro-3-methoxybenzaldehyde oxime. 2-fluoro-3-methoxybenzaldehyde oxime -62- 201010989

HON

OCH3 ^-NMR (CDCI3) δ: 3.90 (3H, s), 6.96-7.00 ( 1 H, m), 7.03-7.12 (1H, m), 7.30-7.3 3 ( 1 H, m), 7.64-7.78 ( 1 H, m), 8.39 (1H, s). • Reference Manufacturing Example 6 12.8 g of 2-fluoro-3-methoxybenzaldehyde oxime was added to 2.4 g of 10% palladium on carbon, 8.3 ml of 10N hydrochloric acid and 200 In a mixture of ml ethanol, and the mixture was stirred at room temperature under a hydrogen atmosphere of about 1 atm for 3 hours. The reaction mixture was filtered through a solution of Celite (registered trademark). The filtrate was concentrated under reduced pressure to give 8.2 g of 2-fluoro-3-methoxybenzylamine hydrochloride. Reference Production Example 7 10 A mixed solution of 10 g of 2-fluoro-3-methoxybenzaldehyde and 80 ml of ethanol was added to 1.8 g of 10% palladium carbon, 1 ml of water, 6.5 ml of 10N hydrochloric acid and 50 ml of ethanol. The mixture was then added with 5.4 g of hydroxylamine hydrochloride. The mixture was stirred at room temperature for 2 hours. This mixture was stirred at room temperature under a hydrogen atmosphere of about 1 atm for 3 hours. The reaction mixture was passed through a solution of Celite (registered trademark), and the filtrate was concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with chloroform. A 15% aqueous solution of sodium hydroxide was added until the pH of the obtained aqueous layer reached 11 and it was extracted with chloroform. The organic layer was dried over potassium carbonate and then concentrated under reduced pressure to yield s. 2-fluoro-3-methoxybenzylamine

H2N

3 !H-NMR (CDC13) δ: 1.55 (2Η, br s), 3.89 (3H, s), 3.90 (2H, br s), 6.86-6.91 (2H, m), 7.02-7.06 ( 1 H, m Reference Production Example 8 15 ml of 48% hydrobromic acid was added to 4 g of 2-fluoro-3-methoxybenzylamine hydrochloride, and the mixture was heated under reflux for 5 hours. The reaction mixture which was cooled to about room temperature was concentrated under reduced pressure to give 4.0 g of 2-fluoro-3-hydroxybenzamine hydrobromide. 2-fluoro-3-hydroxybenzylamine hydrobromide

H2N HBr ^-NMR (DMSO-d6) δ: 4.04 (2H, q, J = 5.5 Hz), 6.90-6.94 (1H, m), 6.97-7.06 (2H, m), 8.23 (3H, br s), 10.05 (1 H, br s). Reference Production Example 9 7.4 g of 2-fluoro-3-hydroxybenzidine hydrobromide, 12.0 g of BOP reagent and 1 1.0 g of triethylamine were added to 5.0 g of benzothiazole- A mixture of 6-carboxylic acid and 50 ml of DMF, and the mixture was stirred at room temperature for 30 minutes. Water was added to 201010989 to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated. The residue thus obtained was subjected to silica gel chromatography to obtain 9.0 g of N-(2-fluoro-3-hydroxyphenyl)methyl-benzothiazole-6-carboxamide. N-(2-fluoro-3-hydroxyphenyl)methyl-benzothiazole-6-carboxyguanamine

Ο F

!H-NMR (DMSO-d6) δ: 9.78 (1Η, s), 9.54 (1H, s), 9.13 (1H, t, J = 5.7 Hz), 8.70 (1H, d, J = 1.7 Hz), 8.16 (1H, d, J = 8.5 Hz), 8.05 (1H, dd, J = 8.5, 1.7 Hz), 6.93 (1H, t, J = 7.8 Hz), 6.87-6.77 (2H, m), 4.53 (2H, d, J = 5.6 Hz). Refer to Manufacturing Example 1 〇® at 〇 ° C, add 14 g of WSC to lig benzothiazole-6-carboxylic acid, 15 g of 3-hydroxybenzylamine hydrobromide, 20 ml of pyridine and In a mixture of 150 ml of DMF, and the mixture was stirred at room temperature for 1 hour. Water was added to the reaction mixture, and the solvent was distilled off under reduced pressure. Water was added to the residue, and the resulting solid was collected by filtration. The solid was washed with water and hexane, and dried under reduced pressure. 16 g of N-(3-hydroxyphenyl)methyl-benzothiazole-6-carboxamide was obtained. N-(3-hydroxyphenyl)methyl-benzothiazole-6-carboxyguanamine -65- 201010989

: 〇Λ *H-NMR (DMSO-d6) δ: 4.45 (2H, d, J = 5.9 Hz), 6.64 (1H, dd, J = 7.2, 1.6 Hz), 6.76-6.77 (2H, m), 7.12 (1H, t, J = 8.0 Hz), 8.06 (1H, dd, J = 8.5, 1.7 Hz), 8.17 (1H, d, J = 8.5 Hz), 8.71 (1H, d, J = 1.7 Hz), 9.15 (1H, t, J = 5.9 Hz), 9.33 (1H, s), 9.54 (1H, s). Next, an example of the formulation is shown below. The number of parts is expressed by weight. Formulation Example 1 honing and thoroughly mixing 50 parts of one of the compounds (i) to (23) of the present invention, 3 parts of calcium lignosulfonate, 2 parts of magnesium lauryl sulfate, and 45 parts of Synthetic hydrated oxidized sand to obtain a wettable powder. Formulation Example 2 φ 20 parts of one of the compounds (1) to (23) of the present invention and 1.5 parts of sorbitan trioleate and 2 8.5 parts An aqueous solution containing 2 parts of polyvinyl alcohol is mixed, and the mixture is finely honed by wet honing, followed by adding 40 parts of an aqueous solution containing 0.05 parts of celestial gum and 1 part of aluminum magnesium silicate, and additionally 10 parts of propylene glycol was added and stirred to obtain a fluid. Formulation Example 3 - 66 - 201010989 Two parts of the compound (1) to (23) of the present invention, 88 parts of kaolin clay and 1 part by weight of talc were honed and thoroughly mixed to obtain a powder. Formulation Example 4 5 parts of one of the compounds (1) to (23) of the present invention, 14 parts of polyoxyethylene styrene phenyl ether, 6 parts of calcium dodecylbenzene sulfonate and 75 parts were thoroughly mixed. The xylene is obtained as an emulsion. Formulation Example 5 honing and thoroughly mixing 2 parts of the compounds (1) to (23) of the present invention, 1 part of synthetic hydrated cerium oxide, 2 parts of calcium lignosulfonate, 30 parts of bentonite and 65 The kaolin is then added with water, and the mixture is thoroughly kneaded, granulated and dried to obtain granules. Formulation Example 6 Φ mixing and finely honing 10 parts of one of the compounds (1) to (2 3) of the present invention by wet honing, 50 parts of polyoxyethylene alkyl ether ammonium sulfate, 3 5 parts of white carbon and 5 parts of water were obtained to obtain a preparation. Next, test examples will show that the compounds of the present invention are useful for controlling plant diseases. The control effect was evaluated by visually observing the area of the disease spot of the target plant in the study, and comparing the area of the disease spot of the plant treated with the compound of the present invention with the area of the disease spot of the untreated plant. N-(2-methoxyphenyl)methyl-benzothiazole--67-201010989 6-carboxamide (the compound of the following formula (A). Hereinafter referred to as comparative compound (A)) was used together in the test. As a control group.

Test Example 1 A plastic pot was stuffed with sandy loam soil, planted with cucumber (plant variety; Sagarni Hanjiro), and grown in the greenhouse for 12 days. The compounds (2), (3), φ (5), (7), (13), (14), (15) and (17) of the present invention are prepared according to Formulation Example 6, and the mixture is diluted with water to make the active ingredient The concentration is 500 ppm. This diluted liquid is sprayed on the stems and leaves so as to adhere sufficiently to the leaf surface of the cucumber. After spraying, the plants were air-dried, and a PDA medium containing spores of Botrytis cinerea was placed on the leaf surface of the cucumber. After inoculation, it was exposed to humid conditions at 12 °C for 5 days, and then the disease spot area was examined. As a result, the disease plaque of the plants treated with the compounds (2), (3), (5), (7), (13), (14), (15) and (17) of the present invention was untreated. The disease area of the plant is 10% or less. Test Example 2 A plastic pot was stuffed with sandy loam soil, planted with cucumber (plant variety; Sagami Hanjiro), and grown in the greenhouse for 12 days. The compounds (1) to (21) and the comparative compound (A) of the present invention were prepared in accordance with Formulation Example 6, and the mixture was diluted with water so that the concentration of the active ingredient was 500 ppm. This diluted liquid is sprayed on the stems and leaves so as to adhere sufficiently to the leaf surface of the cucumber. After spraying -68-201010989, the plants were air-dried > and the PDA medium containing the hyphae of Sclerotinia sclerotiorum was placed on the leaf surface of the cucumber. After inoculation, it was exposed to humid conditions at 18 °C for 4 days, and then the disease spot area was examined. As a result, the disease spot area of the plants treated with the compounds (1) to (21) of the present invention was 10% or less of the disease spot area of the untreated plants. The disease spot area of the plant treated with the comparative compound (A) was 76 to 100% of the disease spot area of the untreated plant. β Test Example 3 Plastic pots were used to soil the soil, planted in rice (plant variety; Nihonbare), and grown in the greenhouse for 12 days. The compounds (1), (5) to (7), (12) to (16) and (21) of the present invention were prepared according to Formulation Example 6, and the blend was diluted with water so that the concentration of the active ingredient was 500 ppm. This diluted liquid is sprayed on the stems and leaves so as to adhere sufficiently to the leaf surface of the rice. After spraying, the plants were air-dried and pots with leaves affected by rice heat bacteria β (Magnaporthe grisea) were placed around the sprayed plants. All rice plants were placed in humid conditions only at night, and the disease spot area was examined 5 days after inoculation. As a result, the disease spot area of the plants treated with the compounds (1), (5) to (7), (12) to (16) and (2 1) of the present invention is 10% of the disease spot area of the untreated plants. Or less. Industrial Applicability The compound of the present invention is useful as an active ingredient in a plant disease control composition because the compound has a plant disease control effect. -69-

Claims (1)

201010989 VII. Application for Patent Park 1 - The amine compound of formula (I), Wherein R1 represents a hydrogen atom or a fluorine atom, and R2 represents a C3-C8 direct bond or a C3-C8 linear alkynyl group. 2. The indoleamine compound of claim 1, wherein Rlg is a fluorine atom, and R2 is a C3-C8 linear alkenyl group. _ 3. The indoleamine compound of claim 2, wherein R2 is a C5-C7 linear alkenyl group. 4 'A guanamine compound as claimed in claim 2, wherein r2 is 4-pentenyl, 5-hexenyl or 6-heptenyl. 5. The indoleamine compound of claim 1, wherein Ri is a hydrogen atom and R2 is a C3-C8 linear alkenyl group. 6. The indoleamine compound of claim 5, wherein R2 is a C5-C7 linear alkenyl group.瘳 7. The indoleamine compound of claim 5, wherein R2 is 4-pentenyl, 5-hexenyl or 6-heptenyl. 8. The indoleamine compound of claim 1, wherein R1 is a fluorine atom, and R2 is a C3-C8 linear alkynyl group. 9. The indoleamine compound of claim 8, wherein R2 is a C5-C7 linear alkynyl group. 10. The indoleamine compound of claim 8, wherein R2 is 4-pentynyl, 5-hexynyl or 6-heptynyl. -70-201010989 11. The indoleamine compound of claim 1, wherein R1 is a hydrogen atom and R2 is a C3-C8 linear alkynyl group. 12. The indoleamine compound of claim 11, wherein R2 is a C5-C7 linear alkynyl group. The indoleamine compound of claim 11, wherein R2 is 4-pentynyl, 5-hexyl or 6-heptynyl. A plant disease control composition comprising a guanamine compound and an inert carrier as in the first aspect of the patent application. 15. A method of controlling a disease of a plant having the step of applying an effective amount of a guanamine compound as in claim 1 of the patent application to a plant or soil. 16. Use of a guanamine compound as claimed in claim 1 for the control of plant diseases. 17. N-(2-Fluoro-3-(2-propenyloxy)phenyl)methyl-benzothiazole-6-carboxamide. © 1 8. N-(2-Fluoro-3-(4-pentenyloxy)phenyl)methyl-benzothiazole-6-carboxyguanamine. 19. An N-(2-fluoro-3-(5-hexenyloxy)phenyl)methyl-benzothiazole-6-carboxamide. 20. An N-(2-fluoro-3-(6-heptenyloxy)phenyl)methyl-benzothiazole-6-carboxamide. 21-N-(2-Fluoro-3-(2-pentenyloxy)phenyl)methyl-benzothiazole-6-carboxamide. 22--N-(3-(2-propenyloxy)phenyl)methyl-benzothiazole-6-carboxy-71 - 201010989 Amidoxime. 23. N-(3-(4-pentenyloxy)phenyl)methyl-benzothiazole-6-carboxamide. 24. N-(3-(5-hexenyloxy)phenyl)methyl-benzothiazole-6-carboxamide. 25. N-(3-(6-heptenyloxy)phenyl)methyl-benzothiazole-6-carboxamide. 26. N-(3-(2-butoxy)phenyl)methyl-benzothiazole-6-carboxyindole. 27--N-(3-(2-pentenyloxy)phenyl)methyl-benzothiazole-6-carboxyguanamine. 28. N-(2-Fluoro-3-(2-propynyloxy)phenyl)methyl-benzothiazole-6-carboxamide. 29. N-(2-Fluoro-3-(4-pentynyloxy)phenyl)methyl-benzothiazole-6-carboxamide. 30. N-(2-Fluoro-3-(5-hexynyloxy)phenyl)methyl-benzothiazole·6-carboxamide. 31. N-(2-Fluoro-3-(2-pentynyloxy)phenyl)methyl-benzothiazole-6-carboxamide. 32. N-(3-(2-propynyloxy)phenyl)methyl-benzothiazole-6-carboxamide. 33. N-(3-(4-pentynyloxy)phenyl)methyl-benzothiazole-6-carboxamide. 34. N-(3-(5-hexynyloxy)phenyl)methyl-benzothiazole-6-carboxy-72- 201010989 decylamine. 35. N-(3-(2-butynyloxy)phenyl)methyl-benzothiazole-6-carboxamide. 36. N-(3-(2-pentynyloxy)phenyl)methyl-benzothiazole-6-carboxamide. 37. N-(2-Fluoro-3-(2-butynyloxy)phenyl)methyl-benzothiazole-6-carboxamide. Φ 38. —N-(2-Fluoro-3-(7-octenyloxy)phenyl)methyl-benzothiazole-6-decylamine. 39. N-(3-(7-octenyloxy)phenyl)methyl-benzothiazole-6-carboxyguanamine. -73- 201010989 IV. Designated representative circle: (1) The designated representative circle of this case is: None (2), the symbol of the representative circle is simple: No 201010989 V. If there is a chemical formula in this case, please reveal the best indication Chemical formula of the invention: Formula (I) N