JP2006298785A - Diamine derivative, its manufacturing method and bactericide having the same as active ingredient - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a novel bactericide which exhibits a broad pest control spectrum against pathogenic bacteria of various crops and solves an urgent problem of resistant bacteria. <P>SOLUTION: The diamine derivative is represented by formula (1) (wherein R1, R2, R5, and R10 are each hydrogen or a substituent such as a 1-6C alkyl group; R3, R4, R6, R7, R8, and R9 are each hydrogen or a substituent such as a 1-6C alkyl group or they are linked with one another to form a carbon-containing 3-6C cycloalkyl group; and Q is an aryl group or a heterocycle), and its manufacturing method is also disclosed, and the bactericide comprises this compound as an active ingredient. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to a novel diamine derivative, a method for producing the same, and a fungicide containing these as active ingredients.

  Disease control plays a major role in crop cultivation, and various fungicides have been developed and used. However, there is not always enough in the bactericidal activity and the harm to useful crops. Also, in recent years, resistant bacteria to drugs have emerged due to heavy use of agricultural and horticultural fungicides, and existing drugs may not exhibit sufficient activity. Furthermore, there is a need for new fungicides that are safe and can control harmful bacteria at low concentrations due to environmental problems. It has been disclosed in WO03008372 that diamine derivatives are useful as pest control agents so far. However, WO03008372 shows control activity only for rice blast, whereas the diamine derivative of the compound of the present invention shows activity against incurable diseases such as plague, downy mildew, and Psium disease, and the structure is also described in the gazette specification. Different from the compound.

International Publication 03/008372 Pamphlet

  An object of the present invention is to provide a new agricultural and horticultural fungicide that exhibits a broad disease control spectrum against pathogenic bacteria of various crops and solves the problem of resistant bacteria that is currently becoming more serious.

  The inventors of the present invention synthesized various diamine derivatives and examined their physiological activities. As a result, the compounds of the present invention have a broad spectrum of disease control, have extremely excellent bactericidal activity, and do no harm to useful crops. As a result, the present invention was completed.

That is, the present invention is as follows.
[1]. Formula (1) (Formula 1)

[In the formula, R1 is an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or a group having 2 to 6 carbon atoms. An alkynyl group, an aryl group, a heterocycle, an arylalkyl group having 1 to 6 carbon atoms in the alkyl group, or a heterocyclic alkyl group having 1 to 6 carbon atoms in the alkyl group; R2, R5 and R10 are each independently Hydrogen atom, alkyl group having 1 to 6 carbon atoms, cycloalkyl group having 3 to 6 carbon atoms, alkenyl group having 2 to 6 carbon atoms, cycloalkenyl group having 3 to 6 carbon atoms, alkynyl group having 2 to 6 carbon atoms , An acyl group, an aryl group, a heterocyclic ring, an arylalkyl group having 1 to 6 carbon atoms in an alkyl group, or a heterocyclic alkyl group having 1 to 6 carbon atoms in an alkyl group, R3 and R4, R6 and R7, And R8 9 each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or 2 carbon atoms. Represents an alkynyl group having 6 carbon atoms, an aryl group, a heterocyclic ring, an arylalkyl group having 1 to 6 carbon atoms in the alkyl group, or a heterocyclic alkyl group having 1 to 6 carbon atoms in the alkyl group, or R3 and R4, R6 and R7, or R8 and R9 may be bonded to each other to form a hydrocarbon ring having 3 to 6 carbon atoms, and Q represents an aryl group or a heterocyclic ring. ] The diamine derivative represented by this.

[2]. A fungicide containing the diamine derivative according to the above [1] as an active ingredient.
[3]. Formula (2) (Formula 2)

[Wherein R 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8, R 9 and R 10 represent the same meaning as [1]. The compound represented by formula (3)

[Wherein Q represents the same meaning as [1], and X represents a leaving group. ] The manufacturing method of the diamine derivative as described in [1] characterized by reacting with the compound represented by this.
[4]. The compound represented by the formula (2) (Chemical formula 2) is converted into the formula (4) (Chemical formula 4).

[Wherein Q represents the same meaning as [1]. ] The manufacturing method of the diamine derivative as described in [1] characterized by reacting with the compound represented by this.
[5]. Formula (5) (Formula 5)

[Wherein R5, R6, R7, R8, R9, R10 and Q represent the same meaning as [1]. The compound represented by formula (6)

[Wherein, R1, R2, R3 and R4 have the same meaning as [1], and X represents a leaving group. ] The manufacturing method of the diamine derivative as described in [1] characterized by reacting with the compound represented by this.
[6]. A compound represented by formula (5) (chemical formula 5)

[Wherein R1, R2, R3 and R4 represent the same meaning as [1]. ] The manufacturing method of the diamine derivative as described in [1] characterized by reacting with the compound represented by this.
[7]. Formula (8) (Formula 8)

[Wherein R 2, R 3, R 4, R 5, R 6, R 7, R 8, R 9, R 10 and Q represent the same meaning as [1]. The compound represented by formula (9)

[Wherein R 1 represents the same meaning as [1], and Y represents a leaving group. ] The manufacturing method of the diamine derivative as described in [1] characterized by reacting with the compound represented by this.
[8]. [1] A method for controlling pests, wherein the diamine derivative according to [1] is used in combination with at least one other fungicide and / or insecticide.

  The diamine derivative according to the present invention is useful as an agricultural fungicide because it has a broad bactericidal spectrum, has extremely excellent bactericidal activity, and has no harmful effect on useful crops. The diamine derivative according to the present invention has a high control effect against tomato blight, potato blight, cucumber downy mildew, grape downy mildew, and rice blast. Moreover, in addition to the above-mentioned diseases, it is effective against Pythium spp. In addition, it has the characteristics of excellent penetration, residual effect, and rain resistance without causing phytotoxicity to crops.

The present invention is described in detail below.
In the diamine derivative represented by the formula (1) and the method for producing the same, examples of typical substituents include, but are not limited to, the following.

  Examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group. These may be substituted with a substituent, and have 3 to 6 carbon atoms. Examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like. These may be substituted with a substituent. Examples of the alkenyl group having 2 to 6 carbon atoms include a vinyl group and a propenyl group. Group, butenyl group, pentenyl group, hexenyl group and the like, which may be substituted by a substituent, and examples of the cycloalkenyl group having 3 to 6 carbon atoms include a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, A cyclohexenyl group and the like, which may be substituted by a substituent, and an alkynyl having 2 to 6 carbon atoms. Examples of the group include an ethynyl group, a propynyl group, a butynyl group, a pentynyl group, and a hexynyl group. These may be substituted with a substituent, and examples of the aryl group include a phenyl group and a naphthyl group. These may be substituted by a substituent. Examples of the heterocycle include furan, thiophene, oxazole, pyrrole, 1H-pyrazole, 3H-pyrazole, imidazole, thiazole, oxazole, isoxazole, isothiazole, [1,2,3 ] Oxadiazole, [1,2,4] oxadiazole, [1,3,4] oxadiazole, furazane, [1,2,3] thiadiazole, [1,2,4] thiadiazole, [1, 2,5] thiadiazole, [1,3,4] thiadiazole, 1H- [1,2,3] triazole, 2H [1,2,3] triazole, 1H- [1,2,4] triazole, 2H- [1,2,4] triazole, 1H-tetrazole, 5H-tetrazole, pyridine, pyran, thiopyran, pyridazine, pyrimidine, pyrazine [1,2,3] triazine, [1,2,4] triazine, [1,3,5] triazine, 2H- [1,2,3] oxadiazine, 2H- [1,2,4] oxadiazine, 2H- [1,2,5] oxadiazine, 2H- [1,2,6] oxadiazine, 4H- [1,2,3] oxadiazine, 4H- [1,2,4] oxadiazine, 4H- [1,2 , 5] oxadiazine, 4H- [1,2,6] oxadiazine, 4H- [1,3,4] oxadiazine, 4H- [1,3,5] oxadiazine, 2H- [1,2,3] thiadia Gin, 2H- [1,2,4] thiadiazine, 2H- [1,2,5] thiadiazine, 2H- [1,2,6] thiadiazine, 4H- [1,2,3] thiadiazine, 4H- [1 , 2,4] thiadiazine, 4H- [1,2,5] thiadiazine, 4H- [1,2,6] thiadiazine, 4H- [1,3,4] thiadiazine, 4H- [1,3,5] thiadiazine 2,3-dihydropyridine, 3,4-dihydropyridine, 1,3-dioxane, 1,4-dioxane, 3,4-dihydro-2H-pyran, 3,6-dihydro-2H-pyran, 3,4-dihydro -2H-thiopyran, 3,6-dihydro-2H-thiopyran, morpholine, chroman, chromene, isobenzofuran, indolizine, indole, 3H-indole, dihydroindole, isoindo 1H-indazole, 2H-indazole, purine, quinoline, isoquinoline, 4H-quinolidine, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, carbazole, acridine, phenazine, phenanthroline, phenothiazine, phenoxazine, indoline, isoindoline, benzofuran, dihydro Benzofuran, benzothiophene, benzo [c] thiophene, benzo [c] isothiazole, benzo [c] isoxazole, dihydrobenzothiophene, benzoxazole, benzisoxazole, benzimidazole, benzothiazole, benzoisothiazole, 1H-benzo Triazole, 2H-benzotriazole, benzo [1,4] dioxane, 2,3-dihydrobenzo [1,4] dioxane, ben [1,3] dioxole, β-carboline, benzo [1,2,5] oxadiazole, benzo [1,2,5] thiadiazole, pteridine, imidazo [1,2-a] pyridine, imidazo [1,2 -A] pyrimidine, pyrazolo [1,5-a] pyrimidine, [1,2,4] triazolo [1,5-a] pyrimidine and the like, which may be substituted with a substituent, and an acyl group Examples thereof include an alkylcarbonyl group such as an acetyl group or an arylcarbonyl group such as a benzoyl group, which may be substituted with a substituent.

  Examples of the substituent for the alkyl group having 1 to 6 carbon atoms include an alkyl group such as a methyl group, an ethyl group, a propyl group or a butyl group, a cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group or a cyclohexyl group, and trifluoro Halogen-substituted alkyl groups such as methyl group, difluoromethyl group, bromodifluoromethyl group or trifluoroethyl group, alkoxy groups such as methoxy group, ethoxy group, propoxy group or butoxy group, trifluoromethoxy group, difluoromethoxy group or trifluoro Halogen-substituted alkoxy groups such as ethoxy groups, halogen-substituted alkoxy groups such as methylthio groups, ethylthio groups, propylthio groups or butylthio groups, alkylthio groups such as trifluoromethylthio groups, difluoromethylthio groups or trifluoroethylthio groups Alkylsulfinyl groups such as ruthio group, methanesulfinyl group, ethanesulfinyl group, propanesulfinyl group or butanesulfinyl group, halogen-substituted alkylsulfinyl groups such as trifluoromethanesulfinyl group, difluoromethanesulfinyl group or trifluoroethanesulfinyl group, methanesulfonyl group An alkylsulfonyl group such as an ethanesulfonyl group, a propanesulfonyl group or a butanesulfonyl group, a halogen-substituted alkylsulfonyl group such as a trifluoromethanesulfonyl group, a difluoromethanesulfonyl group or a trifluoroethanesulfonyl group, a methylamino group, a phenylaminomethyl group Or an aminomethyl group such as an aminomethyl group, an amide group such as an acetylamino group or a benzoylamino group, An amino group such as an amino group, a phenylaminomethyl group, or an aminomethyl group, an amide group such as an acetylamino group or a benzoylamino group, a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, an acetyl group Or acyl groups, such as a benzoyl group, can be illustrated.

  The number of carbon atoms in the cycloalkyl group having 3 to 6 carbon atoms, the alkenyl group having 2 to 6 carbon atoms, the cycloalkenyl group having 3 to 6 carbon atoms, the alkynyl group having 2 to 6 carbon atoms, the aryl group, the heterocycle, and the alkyl group. Examples of the substituent of the arylalkyl group having 1 to 6 or the heterocyclic alkyl group having 1 to 6 carbon atoms of the alkyl group include alkyl groups such as methyl group, ethyl group, propyl group, and butyl group, cyclopropyl group, and cyclobutyl. Group, cycloalkyl group such as cyclopentyl group or cyclohexyl group, halogen-substituted alkyl group such as trifluoromethyl group, difluoromethyl group, bromodifluoromethyl group or trifluoroethyl group, methoxy group, ethoxy group, propoxy group or butoxy group Alkoxy group, trifluoromethoxy group, difluoromethoxy group or trifluoro Halogen-substituted alkoxy groups such as ethoxy groups, alkylthio groups such as methylthio groups, ethylthio groups, propylthio groups or butylthio groups, halogen-substituted alkylthio groups such as trifluoromethylthio groups, difluoromethylthio groups or trifluoroethylthio groups, methanesulfinyl groups, Alkylsulfinyl groups such as ethanesulfinyl group, propanesulfinyl group or butanesulfinyl group, halogen-substituted alkylsulfinyl groups such as trifluoromethanesulfinyl group, difluoromethanesulfinyl group or trifluoroethanesulfinyl group, methanesulfonyl group, ethanesulfonyl group, propanesulfonyl Group or alkylsulfonyl group such as butanesulfonyl group, trifluoromethanesulfonyl group, difluoromethanesulfonyl group Is a halogen-substituted alkylsulfonyl group such as a trifluoroethanesulfonyl group, an aryl group such as a phenyl group or a naphthyl group, furan, thiophene, oxazole, pyrrole, 1H-pyrazole, 3H-pyrazole, imidazole, thiazole, oxazole, isoxazole, isothiazole , Tetrahydrofuran, pyrazolidine, pyridine, pyran, pyrimidine, pyrazine and the like heterocycle, methylamino group, phenylaminomethyl group, aminomethyl group such as aminomethyl group, acetylamino group, amide group such as benzoylamino group, etc. Can be exemplified by a fluorine atom, a chlorine atom, a halogen atom of a bromine atom or an iodine atom, an acyl group such as an acetyl group or a benzoyl group.

  In the compounds represented by the formulas (3) and (6), the leaving group includes a halogen atom typified by a chlorine atom, an alkoxy group typified by a methoxy group and an ethoxy group, and an aryl typified by a phenoxy group. An acyloxy group represented by an oxy group, an acetyloxy group and a benzoyloxy group, an alkoxycarbonyloxy group represented by a methoxycarbonyloxy group, an arylcarbonyloxy group represented by a phenylcarbonyloxy group, N-hydroxysuccinimide, Examples thereof include 1-hydroxybenzotriazole and imidazole group.

  In the compound represented by the formula (9), examples of the leaving group include a chlorine atom and a fluorine atom, an imidazole group, and a 1H-1,2,4-triazole group.

  The compound of the present invention represented by the formula (1) is a novel compound, and the compound represented by the formula (1) can be produced by the method described in the reaction formula (1) (chemical formula 10).

[Wherein R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 have the same meaning as in formula (2) (Chemical Formula 11), and Q and X represent the formula (3) (Chemical Formula 12) Means the same. ]
In the reaction formula (1), the amine derivative represented by the formula (2) and the salt thereof are mixed with the known carbonyl compound represented by the formula (3) in a solvent-free or solvent-free, base-free or base, trialkylaluminum, etc. By reacting in the presence of a metal reagent, a diamine derivative represented by the formula (1) can be produced.

  Bases used in the reaction represented by the reaction formula (1) include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkaline earth metal hydroxides such as magnesium hydroxide and calcium hydroxide, hydrogen Alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal alcoholates such as sodium methoxide and sodium ethoxide; alkali metal oxides such as sodium oxide; carbonates such as potassium carbonate and sodium carbonate; Phosphate salts such as potassium, trisodium phosphate, dipotassium monohydrogen phosphate, disodium monohydrogen phosphate, acetates such as sodium acetate and potassium acetate, pyridine, 4- (dimethylamino) pyridine, triethylamine, imidazole, diazabicyclone Examples include organic bases such as decene.

  The amount of these bases to be used is not particularly limited, and can be used as a solvent when the above organic bases are used.

  When these bases are used, the solvent used in the reaction includes water, alcohols such as methanol, ethanol, propanol and butanol, halogenated hydrocarbons such as dichloromethane and chloroform, and aromatics such as benzene, toluene and xylene. Hydrocarbons, aliphatic hydrocarbons such as hexane and heptane, dimethylformamide (DMF), dimethylacetamide (DMA), dimethylsulfoxide (DMSO), 1,3-dimethyl-2-imidazolidinone (DMI), 1- Aprotic polar solvents such as methyl-2-pyrrolidone (NMP), ethers such as ethyl ether, isopropyl ether, 1,2-dimethoxyethane (DME), tetrahydrofuran (THF), dioxane, acetonitrile, propionitrile, etc. List nitriles Door can be.

  Examples of the metal reagent used in the reaction represented by the reaction formula (1) include alkylaminomagnesium halide (Bodrux reaction) made from Grignard reagent and alkylamine, lithium aluminum hydride, trimethylaluminum, triethylaluminum, and the like. be able to. The amount of these metal reagents used is not particularly limited.

  When using these metal reagents, the solvents used for the reaction include halogenated hydrocarbons such as dichloromethane and chloroform, aromatic hydrocarbons such as benzene, toluene and xylene, and aliphatic hydrocarbons such as hexane and heptane. And ethers such as ethyl ether, isopropyl ether, 1,2-dimethoxyethane (DME), tetrahydrofuran (THF) and dioxane.

  The reaction temperature and reaction time for the above reaction can be varied over a wide range. In general, the reaction temperature is preferably -78 to 200 ° C, more preferably -78 to 100 ° C, and the reaction time is preferably 0.01 to 50 hours, more preferably 0.1 to 15 hours.

  The equivalent of the carbonyl compound represented by the formula (3) is preferably 1 to 2 equivalents, more preferably 1 to 1.2 equivalents with respect to the amine derivative represented by the formula (2).

  The amine derivative represented by the formula (2) of the reaction formula (1) and a salt thereof can be produced by the method described in the reaction formula (2) (Chemical Formula 11).

[Wherein R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 represent the same meaning as in formula (2) (Chemical Formula 11), and R11 may be a t-butyl group or may be substituted. Represents a benzyl group. ]
In the reaction formula (2), the diamine derivative represented by the formula (2) can be produced by reacting the diamine derivative represented by the formula (10) with an acid or by hydrogenation reaction.

  As the acid in this case, hydrogen chloride, hydrogen bromide, sulfuric acid, nitric acid, acetic acid, trifluoroacetic acid and the like can be used. The amount of these acids used is not particularly limited, and can be used as a solvent.

  The hydrogenation reaction can be carried out in a suitable solvent, in the presence of a catalyst, at normal pressure or under pressure, in a hydrogen atmosphere. Examples of the catalyst include a palladium catalyst such as palladium-carbon, a nickel catalyst such as Raney nickel, a cobalt catalyst, a ruthenium catalyst, a rhodium catalyst, a platinum catalyst, and the like. Examples of the solvent include water, alcohols such as methanol and ethanol, benzene, Aromatic hydrocarbons such as toluene, chain or cyclic ethers such as ether, dioxane and tetrahydrofuran, and esters such as ethyl acetate can be used. The reaction temperature and reaction time for the above reaction can be varied over a wide range. In general, the reaction temperature may be appropriately selected from −20 ° C. to the reflux temperature of the solvent to be used, and the reaction time in the range of several minutes to 96 hours.

  The diamine derivative represented by the formula (10) of the reaction formula (2) and the salt thereof can be produced by the method described in the reaction formula (3) (Chemical Formula 12).

[Wherein R1, R2, R3, R4 and X have the same meaning as in formula (6) (Chemical 15), and R5, R6, R7, R8, R9, R10 and R11 have the same meaning as in formula (10). To express. ]
In the reaction formula (3), the amine derivative represented by the formula (11) and a salt thereof are mixed with a known amino acid derivative represented by the formula (6) in a solvent-free or solvent-free, abasic or base, trialkylaluminum, etc. By reacting in the presence of a metal reagent, a diamine derivative represented by the formula (10) can be produced.

  Moreover, as a base in this case, the thing similar to what is used by the method shown by Reaction formula (1) can be used. The amount of these bases to be used is not particularly limited, and can be used as a solvent when the above organic bases are used.

  Moreover, as a metal reagent in this case, the thing similar to what is used by the method shown by Reaction formula (1) can be used. The amount of these metal reagents used is not particularly limited.

  Moreover, as an organic solvent in this case, the thing similar to what is used by the method shown by Reaction formula (1) can be used.

  The usage-amount of the compound represented by Formula (6) is 1-4 equivalent with respect to the amine derivative represented by Formula (11), Preferably it is 1-2 equivalent.

The reaction temperature and reaction time for the above reaction can be varied over a wide range. Generally, the reaction temperature is -20 to 200 ° C, preferably 0 to 100 ° C. The reaction time is 0.01 to 50 hours, preferably 0.1 to 15 hours.
The compound represented by the formula (6) in the reaction formula (3) is obtained by converting the amino acid derivative represented by the formula (7) into thionyl chloride, oxalyl chloride, phosgene, phosphorus oxychloride, phosphorus trichloride, phosphorus pentachloride, odor It can be produced by a conventional method of reacting with thionyl bromide, phosphorus tribromide, diethylaminosulfur trifluoride, 1,1′-carbonylbis-1H-imidazole and the like.

  The compound represented by the formula (6) in the reaction formula (3) is to react the amino acid derivative represented by the formula (7) with alcohols such as methyl alcohol and ethyl alcohol, and phenols such as phenol and nitrophenol. It can also be produced by a conventional method.

  The compound represented by the formula (6) in the reaction formula (3) can be produced by a conventional method in which the amino acid derivative represented by the formula (7) is reacted with chloroformate esters such as methyl chloroformate and phenyl chloroformate. it can.

The compound represented by the formula (6) in the reaction formula (3) can also be produced by a conventional method in which the amino acid derivative represented by the formula (7) is reacted with N-hydroxysuccinimide, 1-hydroxybenzotriazole and the like. it can.
The amine derivative represented by the formula (11) of the reaction formula (3) and its salt are those other than those commercially available, such as Gabriel method, delpin method, reduction of cyano group, amide, imine, oxime, etc. It can be easily produced by a known amine synthesis method or a method described in Tetrahedron Asymmetry, Vol. 11, page 1907 (2000).

  The diamine derivative represented by Formula (10) can also be produced by the method described in Reaction Formula (4) (Chemical Formula 13).

[Wherein, R1, R2, R3 and R4 represent the same meaning as in formula (7) (Chemical Formula 16), and R5, R6, R7, R8, R9, R10 and R11 represent the same meaning as in formula (10). ]
In the reaction formula (4), the amine derivative represented by the formula (11) and a salt thereof are reacted with the known amino acid derivative represented by the formula (7) in the absence of a solvent or in a solvent to obtain a formula (10) The diamine derivative represented can be produced.

  As the condensing agent in this case, N, N′-dicyclohexylcarbodiimide, 1,1′-carbonylbis-1H-imidazole, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide / hydrochloride, 2-chloro-1 , 3-dimethylimidazolium chloride and the like can be used.

  The usage-amount of a condensing agent is 1-3 equivalent with respect to the compound represented by Formula (7), Preferably it is 1-1.5 equivalent.

  Moreover, as an organic solvent in this case, the thing similar to what is used by the method shown by Reaction formula (1) can be used.

  The usage-amount of the carboxylic acid derivative represented by Formula (7) is 1-2 equivalent with respect to the amine derivative represented by Formula (11), Preferably it is 1-1.2 equivalent.

  The reaction temperature and reaction time for the above reaction can be varied over a wide range. Generally, the reaction temperature is -20 to 200 ° C, preferably 0 to 100 ° C. The reaction time is 0.01 to 50 hours, preferably 0.1 to 15 hours.

  The compound represented by the formula (7) in the reaction formula (4) can be produced by a conventional method in which a corresponding amino acid is reacted with a sulfonyl chloride or a sulfonyl halide of a sulfonyl fluoride.

  The compound represented by the formula (7) in the reaction formula (4) usually reacts a corresponding amino acid with a sulfonic anhydride, N-sulfonylimidazolide, N-sulfonyl-1H-1,2,4-triazole. It can be manufactured by the method.

  The compound represented by the formula (3) in the reaction formula (1) is obtained by converting a known carboxylic acid derivative represented by the formula (4) into thionyl chloride, oxalyl chloride, phosgene, phosphorus oxychloride, phosphorus trichloride, pentachloride. It can be produced by a conventional method of reacting with phosphorus, thionyl bromide, phosphorus tribromide, diethylaminosulfur trifluoride, 1,1′-carbonylbis-1H-imidazole or the like.

  The compound represented by the formula (3) of the reaction formula (1) is obtained by combining a known carboxylic acid derivative represented by the formula (4) with alcohols such as methyl alcohol and ethyl alcohol, phenols such as phenol and nitrophenol. It can also be produced by a conventional method of reacting.

  The compound represented by Formula (3) of Reaction Formula (1) is a conventional method in which a known carboxylic acid derivative represented by Formula (4) is reacted with chloroformate esters such as methyl chloroformate and phenyl chloroformate. Can also be manufactured.

  The compound represented by the formula (3) in the reaction formula (1) is prepared by reacting a known carboxylic acid derivative represented by the formula (4) with N-hydroxysuccinimide, 1-hydroxybenzotriazole, or the like. Can also be manufactured.

  The compound of the present invention represented by Formula (1) can also be produced by the method described in Reaction Formula (5) (Chemical Formula 14).

[Wherein R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 have the same meaning as in formula (2) (Chemical Formula 11), and Q is the same as in Formula (3) (Chemical Formula 12). Represents meaning. In the reaction formula (5), the amine derivative represented by the formula (2) and a salt thereof are reacted with the known carboxylic acid derivative represented by the formula (4) in the absence of a solvent or in a solvent to obtain the formula (1). The diamine derivative represented by this can be manufactured.

  As the condensing agent in this case, N, N′-dicyclohexylcarbodiimide, 1,1′-carbonylbis-1H-imidazole, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide / hydrochloride, 2-chloro-1 , 3-dimethylimidazolium chloride and the like can be used.

  The usage-amount of a condensing agent is 1-3 equivalent with respect to the compound represented by Formula (4), Preferably it is 1-1.5 equivalent.

  Moreover, as an organic solvent in this case, the thing similar to what is used by the method shown by Reaction formula (1) can be used.

  The usage-amount of the carboxylic acid derivative represented by Formula (4) is 1-2 equivalent with respect to the amine derivative represented by Formula (2), Preferably it is 1-1.2 equivalent.

  The reaction temperature and reaction time for the above reaction can be varied over a wide range. Generally, the reaction temperature is -20 to 200 ° C, preferably 0 to 100 ° C. The reaction time is 0.01 to 50 hours, preferably 0.1 to 15 hours.

  The compound of this invention represented by Formula (1) can also be manufactured by the method as described in Reaction Formula (6) (Chemical Formula 15).

[Wherein R5, R6, R7, R8, R9, R10 and Q represent the same meaning as in formula (5) (Chemical formula 14), and R1, R2, R3, R4 and X represent the formula (6) (Chemical formula 15). Means the same. ]
In the reaction formula (6), the amine derivative represented by the formula (5) and a salt thereof are converted to a known compound represented by the formula (6) and a metal such as a base or a base and a trialkylaluminum in a solvent or solvent. By reacting in the presence of a reagent, a diamine derivative represented by the formula (1) can be produced.

  Moreover, as a base in this case, the thing similar to what is used by the method shown by Reaction formula (1) can be used. The amount of these bases to be used is not particularly limited, and can be used as a solvent when the above organic bases are used.

  Moreover, as a metal reagent in this case, the thing similar to what is used by the method shown by Reaction formula (1) can be used. The amount of these metal reagents used is not particularly limited.

  Moreover, as an organic solvent in this case, the thing similar to what is used by the method shown by Reaction formula (1) can be used.

  The usage-amount of the compound represented by Formula (6) is 1-4 equivalent with respect to the amine derivative represented by Formula (5), Preferably it is 1-2 equivalent.

  The reaction temperature and reaction time for the above reaction can be varied over a wide range. Generally, the reaction temperature is -20 to 200 ° C, preferably 0 to 100 ° C. The reaction time is 0.01 to 50 hours, preferably 0.1 to 15 hours.

  The compound of this invention represented by Formula (1) can also be manufactured by the method as described in Reaction Formula (7) (Chemical Formula 16).

[Wherein R5, R6, R7, R8, R9, R10 and Q represent the same meaning as in formula (5) (Chemical formula 14), and R1, R2, R3 and R4 are the same as in formula (7) (Chemical formula 16). Represents meaning. ]
In the reaction formula (7), the amine derivative represented by the formula (5) and a salt thereof are reacted with the known carboxylic acid derivative represented by the formula (7) in the absence of a solvent or in a solvent to obtain the formula (1). The diamine derivative represented by these can be manufactured.

  As the condensing agent in this case, N, N′-dicyclohexylcarbodiimide, 1,1′-carbonylbis-1H-imidazole, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide / hydrochloride, 2-chloro-1 , 3-dimethylimidazolium chloride and the like can be used.

  The usage-amount of a condensing agent is 1-3 equivalent with respect to the compound represented by Formula (7), Preferably it is 1-1.5 equivalent.

  Moreover, as an organic solvent in this case, the thing similar to what is used by the method shown by Reaction formula (1) can be used.

  The usage-amount of the carboxylic acid derivative represented by Formula (7) is 1-2 equivalent with respect to the amine derivative represented by Formula (5), Preferably it is 1-1.2 equivalent.

  The reaction temperature and reaction time for the above reaction can be varied over a wide range. Generally, the reaction temperature is -20 to 200 ° C, preferably 0 to 100 ° C. The reaction time is 0.01 to 50 hours, preferably 0.1 to 15 hours.

  The compound of the present invention represented by the formula (1) can also be produced by the method described in the reaction formula (8) (chemical formula 17).

[Wherein R 2, R 3, R 4, R 5, R 6, R 7, R 8, R 9, R 10 and Q represent the same meaning as in formula (8) (Chemical Formula 17), and R 1 and Y represent the formula (9) (Chemical Formula 18) Means the same. ]
In reaction formula (8), the amine derivative represented by formula (8) and a salt thereof are reacted with a known compound represented by formula (9) in the absence of a base or a base in the absence of a solvent or solvent. Thus, a diamine derivative represented by the formula (1) can be produced.
As the base in this case, the same base as that used in the method represented by the reaction formula (1) can be used. The amount of these bases to be used is not particularly limited, and can be used as a solvent when the above organic bases are used.

  Moreover, as an organic solvent in this case, the thing similar to what is used by the method shown by Reaction formula (1) can be used.

  The usage-amount of the compound represented by Formula (9) is 1-4 equivalent with respect to the diamine derivative represented by Formula (8), Preferably it is 1-2 equivalent.

The reaction temperature and reaction time for the above reaction can be varied over a wide range. Generally, the reaction temperature is -20 to 200 ° C, preferably 0 to 100 ° C. The reaction time is 0.01 to 50 hours, preferably 0.1 to 15 hours.
The amine derivative represented by the formula (8) of the reaction formula (8) and a salt thereof can be produced by the method described in the reaction formula (9) (chemical formula 18).

[Wherein R2, R3, R4, R5, R6, R7, R8, R9, R10 and Q represent the same meaning as in formula (8) (Chemical Formula 17), and R12 may be a t-butyl group or may be substituted. Represents a benzyl group. ]
In the reaction formula (9), the diamine derivative represented by the formula (8) can be produced by reacting the diamine derivative represented by the formula (1) with an acid or hydrogenation reaction.

  As the acid in this case, hydrogen chloride, hydrogen bromide, sulfuric acid, nitric acid, acetic acid, trifluoroacetic acid and the like can be used. The amount of these acids used is not particularly limited, and can be used as a solvent.

  As the catalyst for the hydrogenation reaction, the same catalyst as that used in the method represented by the reaction formula (2) can be used.

As the solvent used in the reaction represented by the reaction formula (9), the same solvents as those used in the method represented by the reaction formula (1) can be used.
The reaction temperature and reaction time for the above reaction can be varied over a wide range. In general, the reaction temperature may be appropriately selected from −20 ° C. to the reflux temperature of the solvent to be used, and the reaction time in the range of several minutes to 96 hours.
The compound represented by the formula (9) of the reaction formula (8) is produced by a conventional method in which the corresponding sulfonic acid and its salt are reacted with thionyl chloride, phosgene, phosphorus oxychloride, phosphorus trichloride, phosphorus pentachloride and the like. it can.
The compound represented by the formula (9) of the reaction formula (8) can be produced by a conventional method of chlorinating the corresponding thiol, disulfide, sulfinic acid and the like.
The compound represented by the formula (9) in the reaction formula (8) can be produced by a conventional method in which the corresponding sulfinic acid is reacted with chlorine, copper (II) chloride, or sulfuryl chloride.
The compound represented by the formula (9) of the reaction formula (8) can be produced by a conventional method in which the corresponding sulfonyl chloride is reacted with an alkali fluoride represented by sodium fluoride.
The compound represented by the formula (9) of the reaction formula (8) can be produced by a conventional method in which the corresponding sulfonyl chloride is reacted with imidazole or 1H-1,2,4-triazole.

  The diamine derivative represented by the formula (1) has an asymmetric carbon depending on the type of the substituent, and may exist as an optical isomer, a diastereoisomer, a racemate, and a mixture in any ratio. All isomers of this type as well as mixtures thereof are encompassed by the present invention.

  The agricultural and horticultural fungicides containing the diamine derivative represented by the formula (1) which is the compound of the present invention as an active ingredient are algal fungi (Oomycetes), ascomycetes (Ascomycetes), incomplete fungi (Deuteromycetes), basidiomycetes (Basidiomycetes), fungi belonging to Plasmodiophoromycetes and other pathogenic fungi can be used against a wide variety of plant diseases including the field of vegetables, fruit trees, rice, cereals, flowers, turfgrass. Next, specific disease names (bacteria names) are given as non-limiting examples. For example, rice blast (Pyricularia oryzae), sesame leaf blight (Cochliobolus miyabeanus), blight (Rhizoctonia solani), idiot seedling (Gibberella fujikuroi), seedling blight (Pythium graminicola, etc.), wheat Powdery mildew (Erysiphe graminis f.sp.hordei; f.sp.tritici), leafy leaf disease (Pyrenophora graminea), net leaf disease (Pyrenophora teres), leaf blight (Gibberella zeae), rust disease (Puccinia striiformis) ; P. graminis; P. recondita; P. hordei), snow rot (Typhula sp .; Micronectriella nivalis), naked smut (Ustilago tritici; U. nuda), eye disease (Pseudocercosporella herpotrichoides), cloud disease (Rhynchosporium) secalis), leaf blight (Septoria tritici), blight (Leptosphaeria nodorum), brown snow rot (Pythium iwayamai etc.) caused by Pythium spp.Plasmopara viticola, powdery mildew (Uncinula necator), Black mildew (Elsinoe ampelina), late rot (Glomerella cingulata), rust (Phakopsora ampelopsidis), apple udon Disease (Podosphaera leucotricha), black spot disease (Venturia inaequalis), spotted leaf disease (Alternaria mali), red star disease (Gymnosporangium yamadae), moniliosis (Sclerotinia mali), rot (Valsa mali), pear black spot disease (Alternaria kikuchi) ), Black streak (Venturia nashicola), red streak (Gymnosporangium haraeanum), pear plague (Phytophthora cactorum), peach streak (Sclerotinia cinerea), black streak (Cladosporium carpophilum), phomopsis spoilage (Phomopsis sp. , Plague (Phytophthora sp.), Oyster anthracnose (Gloeosporium kaki), deciduous leaf disease (Cercospora kaki; Mycosphaerella nawae), downy mildew (Pseudoperonospora cubensis), plague (Phytophthora melonis, Phytophthorahythiat) , Powdery mildew (Sphaerotheca fuliginea), anthracnose (Colletotrichum lagenarium), vine blight (Mycosphaerella melonis), tomato plague (Phytophthora infestans), seedling blight (Pythium vezans, Rhizoctonia solani), ring rot (Alternari) a solani), leaf mold (Cladosporium fulvam), root rot (Pythium myriotylum, Pythium dissotocum), eggplant powdery mildew (Erysiphe cichoracoarum), plague (Phytophthora infestans), brown rot (Phytophthora capsici vegetable), Brassicaceae Of black spot (Alternaria japonica), white spot (Cerocosporella barassicae), clubroot (Plasmodiophora brassicae), downy mildew (Peronospora brassicae), white ony mildew (Phytophthora porri), rust (Puccinia allii), soybean Phytophthora megasperma, downy mildew (Peronospora manshurica), purpura (Cercospora kikuchii), black scab (Elsinoe glycines), black spot (Diaporthe phaseololum), common bean anthracnose (Colletotrichum lindemuthianum), peanut black Astringency (Mycosphaerella personatum), brown spot (Cercospora arachidicola), pea powdery mildew (Erysiphe pisi), downy mildew (Peronospora pisi), potato plague (Phytophthora infestans), summer plague (Alternaria sol ani), tea net rot (Exobasidium reticulatum), white scab (Elsinoe leucospila), tobacco scab (Alternaria longipes), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), sugar beet brown spot (Cercospora beticola), downy mildew (Peronospora schachtii), black spot of rose (Diplocarpon rosae), downy mildew (Peronospora sparsa), plague (Phytophthora megasperma), powdery mildew (Sphaerotheca pannosa), chrysanthemum leaf spot ( Septoria chrysanthemi-indici), white rust (Puccinia horiana), plague (Phytophthora cactorum), strawberry powdery mildew (Sphaerotheca humuli), plague (Phytophthora nicotianae), fruit rot (Pythium ultimum), cucumber, tomato, strawberry, Gray mold disease (Botrytis cinerea), sclerotia disease (Sclerotinia sclerotiorum), brown patch disease (Rhizoctonia solani), dollar spot disease (Sclerotinia homoeocarpa), curvularia leaf blight (Curvularia geniculata), rust disease ( Puccinia zoysiae), Helmintosporium leaf blight (Cochiliobolus sp.), Cloud shape disease (Rhynchosporium secalis), Blast disease (Pyricularia oryzae), Blight (Gaeumannomyces graminis), Anthracnose (Colletotrichum graminicola), Snow rot brown Typhula incarnata, Typhula ishikariensis, Snow rot (Sclerotinia borealis), Fairy rings (Marasmius oreades, etc.), Pythium aphanidermatum, etc. Is mentioned.

  The diamine derivatives represented by the formula (1) are, in particular, grape mildew (Plasmopara viticola), cucumber downy mildew (Pseudoperonospora cubensis), potato and tomato fungus (Phytophthora infestans), turf Pythium fungus (Pythium It has a strong bactericidal action on many oomycetes such as aphanidermatum etc., and various plant diseases caused by Plasmopara, Pseudoperonospora, Peronospora, and Pythium pathogens, downy mildew, seedling Excellent control effect against blight, pisium disease, etc.

  Since the diamine derivative represented by the formula (1) has a good compatibility with the plant body at the concentration of the active compound necessary for controlling the phytopathogenic fungus, All chemical treatments, chemical treatments for rootstocks and seeds, soil treatment, etc. are possible.

  The diamine derivative represented by the formula (1), which is the compound of the present invention, can be used in combination with other fungicides, insecticides, herbicides, plant growth regulators, and other agricultural chemicals, soil improvers or fertilizers. In addition, mixed preparations with these are also possible.

  The diamine derivative represented by the formula (1) which is a compound of the present invention may be used as it is, but it is preferably applied in the form of a composition mixed with a carrier containing a solid or liquid diluent. The carrier as used herein means a synthetic or natural inorganic or organic substance formulated to help the active ingredient reach the site to be treated and to facilitate the storage, transport and handling of the active ingredient compound.

  Suitable solid carriers include clays such as montmorillonite, kaolinite and bentonite, diatomaceous earth, white clay, talc, vermiculite, gypsum, calcium carbonate, silica gel, ammonium sulfate and other inorganic substances, soy flour, sawdust, wheat flour, etc. Examples include plant organic substances and urea.

  Suitable liquid carriers include aromatic hydrocarbons such as toluene, xylene and cumene, paraffinic hydrocarbons such as kerosene and mineral oil, halogenated hydrocarbons such as carbon tetrachloride, chloroform and dichloroethane, acetone and methyl ethyl ketone. Ketones, ethers such as dioxane, tetrahydrofuran and diethylene glycol dimethyl ether, alcohols such as methanol, ethanol, propanol and ethylene glycol, dimethylformamide, dimethyl sulfoxide and water.

  Further, in order to enhance the efficacy of the diamine derivative represented by the formula (1), which is the compound of the present invention, each of them is used alone or in combination depending on the purpose in consideration of the dosage form, application scene, etc. of the preparation as follows. Can also be used.

  Adjuvants include lignin sulfonates, alkylbenzene sulfonates, alkyl sulfate esters, polyoxyalkylene alkyl sulfates and polyoxyalkylene alkyl phosphates for purposes such as emulsification, dispersion, spreading, wetting, binding and stabilization. Anionic surfactants such as ester salts, polyoxyalkylene alkyl ethers, polyoxyalkylene alkyl aryl ethers, polyoxyalkylene alkyl amines, polyoxyalkylene alkyl amides, polyoxyalkylene alkyl thioethers, polyoxyalkylene fatty acid esters, glycerin fatty acid esters, Nonionic surfactants such as sorbitan fatty acid esters, polyoxyalkylene sorbitan fatty acid esters and polyoxypropylene polyoxyethylene block polymers Calcium stearate, lubricants such as wax, stabilizers such as isopropyl hydroperoxide diene phosphate, other cellulose, carboxymethyl cellulose, casein, gum arabic, and the like. However, these components are not limited to the above.

  The amount of the active ingredient of the diamine derivative represented by the formula (1) which is the compound of the present invention is usually 0.5 to 20% by weight for powders, 5 to 50% by weight for emulsions, and 10 to 90% by weight for wettable powders. In the case of granules, it is 0.1 to 20% by weight and in the case of flowable preparations, it is 10 to 90% by weight. On the other hand, the amount of carrier in each dosage form is usually 60 to 99% by weight for powders, 40 to 95% by weight for emulsions, 10 to 90% by weight for wettable powders, 80 to 99% by weight for granules, and for flowable formulations. 10 to 90% by weight. The amount of the adjuvant is usually 0.1 to 20% by weight for powders, 1 to 20% by weight for emulsions, 0.1 to 20% by weight for wettable powders, 0.1 to 20% by weight for granules, and flowable. In the preparation, it is 0.1 to 20% by weight.

  In order to obtain an additive or synergistic effect on the control of a wide variety of pests occurring in the fields of vegetables, fruit trees, rice, cereals, flowers, turfgrass, the compounds of the present invention and other fungicides and / or insecticides One or more of these may be used in combination.

  As a fungicide that can be used in combination with the diamine derivative represented by the formula (1) which is the compound of the present invention, triazimephone, hexaconazole, propiconazole, ipconazole, prochloraz, triflumizole, tebuconazole, epoxiconazole, difenoconazole , Flusilazole, triadimenol, cyproconazole, metconazole, fluquinconazole, viteltanol, tetraconazole, triticonazole, flutriafor, penconazole, diniconazole, fenbuconazole, bromconazole, imibenconazole, cimeconazole, micro Conazole, microbutanyl, himexazole, imazalyl, furametopil, tifluzamide, etridiazole, oxyspoconazole, oxyspoconazole fuma Azole fungicides such as acid salts, pefrazoate, prothioconazole, pyrimidine fungicides such as pyrifenox, phenarimol, nuarimol, and buprimate Acylalanine fungicides such as thiophanate methyl, thiophanate methyl, benomyl, carbendazim, fuberidazole, thiabendazole and other benzimidazole fungicides, manzeb, propineb, dinebu, methylam, mannebu, dithiocarbamate fungicides such as dilam, thiuram, tetra Organochlorine fungicides such as chloroisophthalonitrile, ethaboxam, oxycarboxin, carboxin, flutolanil, silthiophane, mepronil and other calcines Xamide-type fungicides, dimethomorph, fenpropidine, fenpropimorph, spiroxamine, tridemorph, dodemorph, flumorph, and other morpholine fungicides, azoxystrobin, cresoxime methyl, methinostrobin, orisatrobin, fluoxastrobin, triflixist Robilin-type fungicides such as robin, dimoxystrobin, pyraclostrobin and picoxystrobin, dicarboximide-type fungicides such as iprodione, procymidone, vinclozoline and clozolinate, fursulfamide, dazomet, methylisothiocyanate, chloropicrin, metasulfo Soil disinfectant such as carb, hydroxyisoxazole, hydroxyisoxazole potassium, echromezol, DD, carb, basic copper chloride, basic sulfur Copper disinfectant such as acid copper, nonylphenol sulfonate copper, oxine copper, DBEDC, anhydrous copper sulfate, copper sulfate pentahydrate, cupric hydroxide, inorganic sulfur, hydrated sulfur agent, lime sulfur mixture, zinc sulfate, Inorganic fungicides such as fentine, sodium hydrogen carbonate, potassium hydrogen carbonate, hypochlorite, metallic silver, organophosphorus fungicides such as edifenphos, tolcrofosmethyl, fosetyl, iprobenphos, dinocap, pyrazophos, carpropamide, fusalide, tricyclazole Melanin biosynthesis inhibitors such as pyroxylone, diclocimet, phenoxanil, bactericides such as kasugamycin, validamycin, polyoxins, blasticidin S, teclophthalam, oxytetracycline, mildiomycin, streptomycin, etc., rapeseed oil, etc. Natural product fungicides, Plant activators that induce plant disease resistance such as carbamate fungicides such as nthiavaricarb isopropyl, iprovaricarb, propamocarb, dietofencarb, pyrrolimides such as fluorimide, fludioxanyl, fenpiclonil, probenazole, acibenzoral S methyl, thiazinyl , Cyflufenamide, phenhexamide, quinoxyphene, diflumetrim, metolaphenone, picobenzamide, proquinazide, famoxadone, cyazofamide, phenamidone, zoxamide, boscalid, chlorothalonil, simoxanyl, captan, dithianon, fluazinam, phorazinamide, (RS) -N [2- (1,3-Dimethylbutyl) thiophen-3-yl] -1-methyl-3-trifluoromethyl 1H-pyrazole-4-carboxamide (generic name pending: penthiopyrad), trifolin, oxolinic acid, isoprothiolane, ferimzone, dichromedin, pencyclon, quinomethionate, iminoctazine acetate, iminoctazine albesylate, ambam, polycarbamate, thiadiazine, chloroneb, Examples thereof include organic nickel, guazatine, dodine, quintozene, tolylfluanid, anilazine, nitrotalisopropyl, fenitropan, dichlorane, DPC, dimethylimole, and benzazole.

  Insecticides that can be used in combination with the diamine derivative represented by the formula (1) which is the compound of the present invention include allethrin, tetramethrin, resmethrin, phenothrin, framethrin, permethrin, cypermethrin, deltamethrin, cyhalothrin, cyfluthrin, fenpropatoline, Synthetic pyrethroid insecticides such as tralomethrin, cycloprotorin, flucitrinate, fulvalinate, acrinathrin, teflutrin, bifenthrin, empentrin, beta cyfluthrin, cypermethrin, fenvalerate and the like, and various isomers or pesticide extracts, DDVP, Cyanophos, phenthion, fenitrothion, tetrachlorbinphos, dimethylvinphos, propaphos, methylparathion, temefos, phoxime, acephae , Isofenphos, salicione, DEP, EPN, ethion, mecarbam, pyridafenthione, diazinon, pyrimiphosmethyl, etrimphos, isoxathion, quinalphos, chlorpyrifosmethyl, chlorpyrifos, hosalon, phosmet, methidathion, oxydebrophos, bamidthione, malathion, phentomethone, phentomethionate, dithiophene Organophosphorus insecticides such as ethyl thiomethone, folate, terbufos, profenofos, prothiophos, sulprophos, pyracrofos, monocrotophos, nared, phosthiazete, trichlorfone, etoprophos, kazusafos, chlorfenvinphos, diclofenthion, ethylthiomethone, NAC, MTMC, MIPC, BPMC , XMC, PHC, MPMC, Eth Carbamate insecticides such as fencarb, bendiocarb, pyrimicarb, carbosulfan, benfuracarb, mesomil, oxamyl, aldicarb, thiodicarb, alanib, arylpropyl ether insecticides such as etofenprox and halfenprox, silyl such as silafluophene Insecticidal natural products such as ether compounds, nicotine sulfate, polynactin complex, abamectin, milbemectin, BT agent, cartap, thiocyclam, benzurtap, diflubenzuron, chlorfluazuron, teflubenzuron, triflumuron, flufenoxuron, flucycloxuron, Hexaflumuron, fluazuron, imidacloprid, nitenpyram, acetamiprid, dinotefuran, pymetrozine, fipronil, buprofe Gin, phenoxycarb, pyriproxyfen, methoprene, hydroprene, quinoprene, endosulfan, diafenthiuron, triazuron, tebufenozide, benzoepin, novallon, nobiflumuron, emamectin benzoate, clothianidin, thiacloprid, thiamethoxam, flupirazophos, acephinodiso Etoxazole, fluacrylpyrim, flufenzine, halofenozide, indoxacarb, methoxyphenozide, spirodiclofen, tolfenpyrad, gamma cyhalothrin, ethiprole, amidoflumet, bistrifluron, flonicamid, flubrocis linate, flufenerim, pyridalyl, spinosad, spiromesifen, Silafluophene, cyromazine Insecticides such as lufenuron, esfenvalerate, sodium oleate, potassium oleate, chlorfenapyr, kelsen, azadilactin, carbam, carbam sodium, dicophor, chlorbenzilate, phenisobromolate, tetradiphone, CPCBS, BPPS, quinomethionate Mitricide, such as amitraz, benzomate, hexothiazox, fenbutasin oxide, cyhexatin, dienochlor, clofentedine, pyridaben, fenpyroximate, phenazaquin, tebufenpyrad, pyrimidifen.

  When the diamine derivative represented by the formula (1) which is the compound of the present invention and one or more other fungicides and / or insecticides are used in combination, the compound of the present invention and other fungicides and / or insecticides The compound of the present invention may be used as a mixed composition, or other fungicides and / or insecticides may be mixed and used at the time of agrochemical treatment.

  In the following, this description will be described in more detail with reference to examples and test examples.

N- [1- (S)-[[(Benzofuran-2-carbonyl) amino] methyl] -2-methylpropyl] 3-methyl-2- (S)-[(butanesulfonyl) amino] butyric acid amide (Compound No. 4)
N- [1- (S)-[[(Benzofuran-2-carbonyl) amino] methyl] -2-methylpropyl 3-methyl-2- (S) -aminobutyric acid amide (0.46 g, 1.34 mmol) Triethylamine (0.41 g, 4.02 mmol) was added to a dichloromethane solution (10 ml), butanesulfonyl chloride (0.25 g, 1.61 mmol) was added under ice cooling, and the mixture was stirred at room temperature for 5 hours and left overnight. . The reaction solution was washed successively with 5% aqueous citric acid solution, saturated aqueous sodium hydrogen carbonate solution and water, and dried over anhydrous magnesium sulfate. After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was washed with diisopropyl ether to obtain 0.50 g of the desired product as a white solid (yield 80%).

N- [1- (S)-[[(Benzofuran-2-carbonyl) amino] methyl] -2-methylpropyl] 3-methyl-2- (S)-[(benzylsulfonyl) amino] butyric acid amide (Compound No. 7)
N- [1- (S)-[[(Benzofuran-2-carbonyl) amino] methyl] -2-methylpropyl 3-methyl-2- (S) -aminobutyric acid amide (0.46 g, 1.34 mmol) Triethylamine (0.41 g, 4.02 mmol) was added to a dichloromethane solution (10 ml), benzylsulfonyl chloride (0.31 g, 1.61 mmol) was added under ice-cooling, and the mixture was stirred at room temperature for 5 hours and left overnight. . The reaction solution was washed successively with 5% aqueous citric acid solution, saturated aqueous sodium hydrogen carbonate solution and water, and dried over anhydrous magnesium sulfate. After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was washed with diisopropyl ether to obtain 0.27 g of the desired product as a white solid (yield 40%).

N- [1- (S)-[[(Benzofuran-2-carbonyl) amino] methyl] -2-methylpropyl] 3-methyl-2- (S)-[(2-chloroethanesulfonyl) amino] butyric acid amide ( Compound No. 9)
N- [1- (S)-[[(Benzofuran-2-carbonyl) amino] methyl] -2-methylpropyl 3-methyl-2- (S) -aminobutyric acid amide (0.46 g, 1.34 mmol) Triethylamine (0.41 g, 4.02 mmol) was added to a dichloromethane solution (10 ml), 2-chloroethanesulfonyl chloride (0.26 g, 1.61 mmol) was added under ice cooling, and the mixture was stirred at room temperature for 5 hours, then overnight. I left it alone. The reaction solution was washed successively with 5% aqueous citric acid solution, saturated aqueous sodium hydrogen carbonate solution and water, and dried over anhydrous magnesium sulfate. After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was washed with diisopropyl ether to obtain 0.47 g of the desired product as a white solid (yield 74%).

N- [1- (S)-[[(Benzofuran-2-carbonyl) amino] methyl] -2-methylpropyl] 3-methyl-2- (S)-[N-methyl- (1-methylethanesulfonyl) Amino] butyric acid amide (Compound No. 50)
To a dichloromethane solution (50 ml) of benzofuran-2-carboxylic acid (1.73 g, 10.68 mmol), 1,1′-carbonylbis-1H-imidazole (1.76 g, 10.68 mmol) was added at room temperature. Stir for 1 hour. N- [1- (S) -aminomethyl-2-methylpropyl] 2- (S)-[N-methyl- (1-methylethanesulfonyl) amino] -3-methylbutyric acid amide (3.27 g) was added to the reaction solution. , 10.17 mmol) and stirred at room temperature for 5 hours. The reaction mixture was washed successively with 5% aqueous citric acid solution, saturated brine, 2N aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous magnesium sulfate. After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was washed with a mixed solution of diisopropyl ether and n-hexane to obtain 3.68 g of the desired product as a white solid (yield 74%).

N- [1- (S)-[[(6-Chloropyridine-2-carbonyl) amino] methyl] -2-methylpropyl] 2-[(1-butanesulfonyl) amino] acetamide (Compound No. 62)
2-[(1-butanesulfonyl) amino] acetic acid (0.36 g, 1.83 mmol), N- [2- (S) -amino-3-methylbutyl] 6-chloropyridine-2-carboxylic acid amide (0. 40 g, 1.66 mmol), N-hydroxysuccinimide (0.20 g, 1.99 mmol), dicyclohexylcarbodiimide (0.41 g, 1.99 mmol) in dichloromethane solution (50 ml) and triethylamine (0.33 g, 3.32 mmol). ) At room temperature and stirred overnight at room temperature. The resulting precipitate of dicyclohexylurea was filtered and then concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 4: 1). The obtained crude product was washed with diisopropyl ether to obtain 0.57 g of the desired product as a white semi-solid (yield 82%).

[Reference Example 1]
N- [3-methyl-2- (S)-[(1,1-dimethylethyloxycarbonyl) amino] butyl] benzofuran-2-carboxylic acid amide benzofuran-2-carboxylic acid (10.0 g, 61.7 mmol) 1,1′-carbonylbis-1H-imidazole (10.5 g, 64.8 mmol) was added to a dichloromethane solution (150 ml) under ice cooling, and the mixture was stirred at room temperature for 2 hours. N- [1- (S)-(Aminomethyl) -2-methylpropyl] carbamic acid 1,1-dimethylethyl ester (13.1 g, 64.8 mmol) was added to the reaction solution, and the mixture was stirred for 5 hours overnight. I left it alone. The reaction solution was washed successively with water, 5% aqueous citric acid solution, water, saturated aqueous sodium hydrogen carbonate solution and water, and then the organic layer was dried over anhydrous magnesium sulfate. After the inorganic salt was filtered off, the crude product obtained by concentration under reduced pressure was recrystallized using diisopropyl ether to obtain 17.7 g of the desired product as a white solid (yield 83%).

[Reference Example 2]
N- [2- (S) -amino-3-methylbutyl] benzofuran-2-carboxylic acid amide N- [3-methyl-2- (S)-[(1,1-dimethylethyloxycarbonyl) amino] butyl] Benzofuran-2-carboxylic acid amide (17.7 g, 51.0 mmol) was dissolved in ethyl acetate (30 ml), 4N hydrogen chloride / ethyl acetate solution (137 ml) was added, and the mixture was stirred at room temperature for 6 hours and left overnight. The precipitated salt was dissolved in water and washed with ethyl acetate, and then adjusted to pH 14 by adding 20% aqueous sodium hydroxide solution to the aqueous layer. Ethyl acetate was added to the aqueous layer for extraction, and then the organic layer was dried over anhydrous magnesium sulfate. The inorganic salt was filtered off and concentrated under reduced pressure to obtain 12.4 g of the desired product as an oily substance (yield 99%).

[Reference Example 3]
N- [1- (S)-[[(Benzofuran-2-carbonyl) amino] methyl] -2-methylpropyl] 3-methyl-2- (S)-[(1,1-dimethylethyloxycarbonyl) amino ] Butyric acid amide 3-methyl-2- (S)-[(1-methylethyloxycarbonyl) amino] butyric acid (15.2 g, 70.2 mmol) in 1,1′-carbonylbis-1H in dichloromethane solution (150 ml) -Imidazole (11.4 g, 70.2 mmol) was added under ice cooling, and the mixture was stirred at room temperature for 3 hours. N- [2- (S) -amino-3-methylbutyl] benzofuran-2-carboxylic acid amide (13.3 g, 54.0 mmol) was added to the reaction solution, and the mixture was stirred for 5 hours and left overnight. The reaction solution was washed successively with water, 5% aqueous citric acid solution, water, saturated aqueous sodium hydrogen carbonate solution and water, and then the organic layer was dried over anhydrous magnesium sulfate. After the inorganic salt was filtered off, the crude product obtained by concentration under reduced pressure was recrystallized using diisopropyl ether to obtain 19.5 g of the desired product as a white solid (yield 81%).

[Reference Example 4]
N- [1- (S)-[[(Benzofuran-2-carbonyl) amino] methyl] -2-methylpropyl 3-methyl-2- (S) -aminobutyric acid amide N- [1- (S)-[ [(Benzofuran-2-carbonyl) amino] methyl] -2-methylpropyl] 3-methyl-2- (S)-[(1,1-dimethylethyloxycarbonyl) amino] butyric acid amide (19.5 g, 43. 8 mmol) was dissolved in ethyl acetate (30 ml), 4N hydrogen chloride / ethyl acetate solution (117 ml) was added, and the mixture was stirred at room temperature for 6 hours and left overnight. The reaction solution was washed with water and ethyl acetate, and adjusted to pH 14 by adding 20% aqueous sodium hydroxide solution to the aqueous layer. After extraction by adding dichloromethane to the aqueous layer, the organic layer was dried over anhydrous magnesium sulfate. The inorganic salt was filtered off and concentrated under reduced pressure to obtain 12.6 g of the desired product as a white solid (yield 83%).

  The compounds represented by formula (1) that can be produced in the same manner as in Examples 1 to 5 are shown in Table 1 (Table 1-1 to Table 1-5). Some of the physical property values are shown in Table 2 (Table 2-1 to Table 2-2). In Table 1, Me is a methyl group, Et is an ethyl group, nPr is a normal propyl group, iPr is an isopropyl group, nBu is a normal butyl group, iBu is an isobutyl group, and sBu is a secondary group. A butyl group, Bn represents a benzyl group, ClCH2 represents a chloromethyl group, ClCH2CH2 represents a 2-chloroethyl group, ClCH2CH2CH2 represents a 3-chloropropyl group, and p-ClPh represents a para-chlorophenyl group.

  The diamine derivative represented by the formula (1) has an asymmetric carbon depending on the type of the substituent, and may exist as an optical isomer, a diastereoisomer, a racemate, and a mixture in any ratio.

<Formulation examples and test examples>
Next, formulation examples and bactericidal activity test examples of the bactericide according to the present invention are shown. In the following description, “parts” means “parts by weight” or “% by weight”.

[Formulation Example 1] (Dust)
2 parts of Compound No. 1 and 98 parts of clay were mixed and ground uniformly to obtain a powder containing 2% of active ingredient.

[Formulation Example 2] (Wetting agent)
Compound No. 7 (10 parts), kaolin (70 parts), white carbon (18 parts) and alkylbenzenesulfonate calcium (2 parts) were uniformly mixed and pulverized to obtain a wettable powder containing 10% active ingredient in the form of fine powder of uniform composition. It was.

[Formulation Example 3] (Wetting agent)
Compound No. 3 (20 parts), alkylbenzenesulfonate calcium (3 parts), polyoxyethylene nonylphenyl ether (5 parts) and clay (72 parts) were uniformly mixed and pulverized, and contained 20% active ingredient in the form of fine powder of uniform composition. A wettable powder was obtained.

[Formulation Example 4] (Wetting agent)
50 parts of the compound of Compound No. 4, 1 part of sodium lignin sulfonate, 5 parts of white carbon and 44 parts of diatomaceous earth were mixed and ground to obtain a wettable powder containing 50% of the active ingredient.

[Formulation Example 5] (Flowable agent)
A flowable agent containing 5 parts of an active ingredient by wet-grinding 5 parts of a compound of Compound No. 3, 7 parts of propylene glycol, 4 parts of sodium lignin sulfonate, 2 parts of dioctyl sulfosuccinate sodium salt, and 82 parts of water with a sand grinder. Obtained.

[Formulation Example 6] (Flowable)
A flowable agent containing 10 parts of an active ingredient by wet-grinding 10 parts of Compound No. 4, 7 parts of propylene glycol, 2 parts of sodium lignin sulfonate, 2 parts of dioctyl sulfosuccinate sodium salt, and 79 parts of water with a sand grinder Got.

[Formulation Example 7] (Flowable agent)
Sand for 25 parts of Compound No. 10, 5 parts of propylene glycol, 5 parts of polyoxyethylene oleate, 5 parts of polyoxyethylene diallyl ether sulfate, 0.2 part of silicon-based antifoaming agent, and 59.8 parts of water The powder was wet pulverized with a grinder to obtain a flowable agent having an active ingredient of 25%.

[Formulation Example 8] (Dust)
Compound 3 of Compound No. 4, 2 parts of fusaride, 20 parts of diatomaceous earth, 30 parts of white clay and 45 parts of talc were uniformly ground and mixed to obtain 100 parts of a powder.

[Formulation Example 9] (Wetting agent)
10 parts of the compound of Compound No. 11, 20 parts of ferrimzone, 1 part of sodium lignin sulfonate, 2 parts of sodium alkylbenzene sulfonate and 67 parts of diatomaceous earth were uniformly ground and mixed to obtain 100 parts of a wettable powder.

[Formulation Example 10] (Wetting agent)
10 parts of the compound of Compound No. 3, 50 parts of basic copper chloride, 5 parts of sodium lauryl phosphate, 5 parts of sodium alkylnaphthalene sulfonate and 30 parts of talc were uniformly ground and mixed to obtain 100 parts of a wettable powder.

[Formulation Example 11] (Wetting agent)
Compound 10 of Compound No. 2, 50 parts of Manzeb, 5 parts of sodium lignin sulfonate, 5 parts of sodium alkylnaphthalene sulfonate, 5 parts of white carbon and 25 parts of diatomaceous earth are uniformly ground and mixed to obtain 100 parts of wettable powder. It was.

[Formulation Example 12] (Wetting agent)
Compound 10 of Compound No. 8, 50 parts of chlorothalonilno, 5 parts of sodium lignin sulfonate, 5 parts of sodium alkylnaphthalene sulfonate, 5 parts of white carbon and 25 parts of diatomaceous earth are uniformly pulverized and mixed. Obtained.

[Formulation Example 13] (Wetting agent)
Compound 10 of Compound No. 10, 40 parts of folpette, 5 parts of sodium lignin sulfonate, 5 parts of sodium alkylnaphthalene sulfonate, 5 parts of white carbon and 35 parts of diatomaceous earth are uniformly pulverized and mixed. Obtained.

[Formulation Example 14] (Flowable agent)
Compound No. 4 (10 parts), Simoxanyl (10 parts), Carboxymethyl cellulose (3 parts), Lignin sulfonate sodium (2 parts), Dioctyl sulfosuccinate sodium salt (1 part) and water (74 parts) were wet-ground with a sand grinder to obtain 100 parts of a flowable agent. It was.

[Formulation Example 15] (Flowable agent)
Compound No. 3 (10 parts), metalaxyl (10 parts), carboxymethyl cellulose (3 parts), lignin sodium sulfonate (2 parts), dioctyl sulfosuccinate sodium salt (1 part) and water (74 parts) were wet-ground with a sand grinder to obtain 100 parts of a flowable agent. It was.

[Formulation Example 16] (Flowable agent)
Compound No. 8 (10 parts), dimethomorph (10 parts), carboxymethyl cellulose (3 parts), lignin sulfonate sodium (2 parts), dioctyl sulfosuccinate sodium salt (1 part) and water (74 parts) were wet-ground with a sand grinder to obtain 100 parts of a flowable agent. It was.

[Formulation Example 17] (Emulsion)
Compound No. 9 (10 parts), imidacloprid (10 parts), cyclohexane (10 parts), xylene (50 parts) and sorbol (Toho Chemicals Surfactant) (20 parts) were uniformly dissolved and mixed to obtain 100 parts of an emulsion.

  Next, the effect of the fungicide of the present invention will be specifically described with reference to test examples. The comparative drug used was a compound described as an agricultural and horticultural fungicide in the specification of WO 03008372, and was prepared in the same manner as the test compound.

Comparative compound

[Test Example 1] Control effect against tomato plague Tomato seedlings in which a compound dissolved in acetone is diluted with water to 250 ppm and four leaves are developed (variety: one in the world, one in a 7.5 cm diameter vinyl pot) 10 mL per pot was sprayed. After air drying, it was transferred to a wet chamber (12 hours light-dark cycle) at 18 ° C. and sprayed with a zoospore suspension of Phytophthora infestans. Four days after inoculation, the diseased area ratio of four leaflets was investigated and evaluated according to the following criteria A to C. The disease area ratio in the untreated area at the time of the survey was 60% or more. The results are summarized in Table 3 (Table 3).

A: Disease area rate less than 5% B: Disease area rate 5% to less than 50% C: Disease area rate 50% or more

[Test Example 2] Control effect against cucumber downy mildew Cucumber seedlings (variety: Sagami Hanjiro, diameter 7.5 cm vinyl) in which the compound dissolved in acetone was diluted with water to 250 ppm and the first leaf was developed. 10 mL per 1 pot was sprayed on 2 pots). After air-drying, it was transferred to a moist chamber installed in a greenhouse, and sprayed with a zoosporangium suspension of Pseudoperonospora cubensis. Seven days after the inoculation, the disease area ratio of the true leaves was investigated and evaluated according to the following criteria A to C. The disease area ratio in the untreated area at the time of the survey was 60 to 80%. The results are summarized in Table 4 (Table 4).

A: Disease area rate less than 5% B: Disease area rate 5% to less than 50% C: Disease area rate 50% or more

[Experiment 3] Grape seedling (variety: Cabernet Sauvignon) grown in a 1 / 2000a pot was cut out to produce a leaf disk having a diameter of 32 mm. The compound dissolved in acetone was diluted with water to 250 ppm, and the leaf disk was immersed for 3 hours. After taking out from the drug solution and air-drying, spray inoculated with a zoosporangium suspension of Plasmopara viticola. The cells were cultured at 18 ° C. for 12 hours with a light / dark light cycle, and the diseased area ratio of leaf discs was investigated 10 days after inoculation, and evaluated according to the following criteria A to C. The disease area ratio in the untreated area at the time of the survey was 60 to 70%. The results are summarized in Table 5 (Table 5).

A: Disease area rate less than 5% B: Disease area rate 5% to less than 50% C: Disease area rate 50% or more

[Test Example 4] Inhibition of hyphal elongation against Pythium sp. After cooling potato dextrose agar medium (hereinafter referred to as PDA) to 40 ° C., a compound dissolved in acetone was added to 100 ppm, and 15 mL was poured into a 9 cm diameter petri dish and cooled. Hardened. The hyphal tip of Pythium aphanidermatum previously grown on PDA was punched out with a 6 mm diameter cork borer and transplanted to a drug-containing PDA with the flora facing down. After culturing in a dark place at 25 ° C. for 24 hours, the hyphal elongation diameter was measured and evaluated according to the following criteria A to C. The results are summarized in Table 6 (Table 6).

A: Inhibition rate for the no-drug group 95% or more B: Inhibition rate for the no-drug group 50-95% C: Inhibition rate for the no-drug group 50%

Claims (13)

Formula (1) (Formula 1)

[In the formula, R1 is an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or a group having 2 to 6 carbon atoms. An alkynyl group, an aryl group, a heterocycle, an arylalkyl group having 1 to 6 carbon atoms in the alkyl group, or a heterocyclic alkyl group having 1 to 6 carbon atoms in the alkyl group; R2, R5 and R10 are each independently Hydrogen atom, alkyl group having 1 to 6 carbon atoms, cycloalkyl group having 3 to 6 carbon atoms, alkenyl group having 2 to 6 carbon atoms, cycloalkenyl group having 3 to 6 carbon atoms, alkynyl group having 2 to 6 carbon atoms , An acyl group, an aryl group, a heterocyclic ring, an arylalkyl group having 1 to 6 carbon atoms in an alkyl group, or a heterocyclic alkyl group having 1 to 6 carbon atoms in an alkyl group, R3 and R4, R6 and R7, And R8 9 each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or 2 carbon atoms. Represents an alkynyl group having 6 carbon atoms, an aryl group, a heterocyclic ring, an arylalkyl group having 1 to 6 carbon atoms in the alkyl group, or a heterocyclic alkyl group having 1 to 6 carbon atoms in the alkyl group, or R3 and R4, R6 and R7, or R8 and R9 may be bonded to each other to form a hydrocarbon ring having 3 to 6 carbon atoms, and Q represents an aryl group or a heterocyclic ring. ] The diamine derivative represented by this.   At least one of R3, R4, R6, R7, R8 and R9 is an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, and an alkyl group having 3 to 6 carbon atoms. A cycloalkenyl group, an alkynyl group having 2 to 6 carbon atoms, an aryl group, a heterocyclic ring, an arylalkyl group having 1 to 6 carbon atoms in an alkyl group, or a heterocyclic alkyl group having 1 to 6 carbon atoms in an alkyl group is represented. The diamine derivative according to claim 1.   The diamine derivative according to claim 2, wherein R10 is a hydrogen atom.   The diamine derivative according to claim 3, wherein R2 and R5 are hydrogen atoms.   A fungicide containing the diamine derivative according to any one of claims 1 to 4 as an active ingredient.   An agricultural and horticultural fungicide containing the diamine derivative according to any one of claims 1 to 4 as an active ingredient. Formula (2) (Formula 2)

[Wherein R 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8, R 9 and R 10 represent the same meaning as in claim 1. The compound represented by formula (3)

[Wherein Q represents the same meaning as in claim 1, and X represents a leaving group. The method for producing a diamine derivative according to any one of claims 1 to 4, wherein the compound is reacted with a compound represented by the formula: The compound represented by the formula (2) (Chemical formula 2) is converted into the formula (4) (Chemical formula 4).

[Wherein Q represents the same meaning as in claim 1. The method for producing a diamine derivative according to any one of claims 1 to 4, wherein the compound is reacted with a compound represented by the formula: Formula (5) (Formula 5)

[Wherein, R5, R6, R7, R8, R9, R10 and Q represent the same meaning as in claim 1.] The compound represented by formula (6)

[Wherein R1, R2, R3 and R4 represent the same meaning as in claim 1, and X represents a leaving group. The method for producing a diamine derivative according to any one of claims 1 to 4, wherein the compound is reacted with a compound represented by the formula: A compound represented by formula (5) (chemical formula 5)

[Wherein R1, R2, R3 and R4 represent the same meaning as in claim 1.] The method for producing a diamine derivative according to any one of claims 1 to 4, wherein the compound is reacted with a compound represented by the formula: Formula (8) (Formula 8)

[Wherein R 2, R 3, R 4, R 5, R 6, R 7, R 8, R 9, R 10 and Q represent the same meaning as in claim 1. The compound represented by formula (9)

[Wherein R 1 represents the same meaning as in claim 1 and Y represents a leaving group. The method for producing a diamine derivative according to any one of claims 1 to 4, wherein the compound is reacted with a compound represented by the formula:   A pest control composition containing the diamine derivative according to any one of claims 1 to 4 and at least one other fungicide and / or insecticide.   Other fungicides and / or insecticides are triadimethone, hexaconazole, propiconazole, ipconazole, prochloraz, triflumizole, tebuconazole, epoxiconazole, difenoconazole, flusilazole, triadimenol, cyproconazole, metconazole, fluconazole Quinconazole, Vitertanol, Tetraconazole, Triticonazole, Frutriafor, Penconazole, Diniconazole, Fenbuconazole, Bromuconazole, Imibenconazole, Cimeconazole, Microconazole, Microbutanyl, Himexazole, Imazaryl, Framethopil, Tifluzamide, Etridiazole , Oxyspoconazole, oxyspoconazole fumarate, pefrazoate, prothioconazole, etc. Agents, pyrimidine fungicides such as pyriphenox, phenarimol, nuarimol, and bupirimate, anilinopyrimidine fungicides such as mepanipyrim, cyprodinyl, pyrimethanil, acylalanine fungicides such as metalaxyl, oxadixyl, benalaxyl, thiophanate methyl, thiophanate methyl, and benomyl Benzimidazole fungicides such as carbendazim, fuberidazole, thiabendazole, dithiocarbamate fungicides such as manzeb, propineb, dineb, methyle, manneb, dilam, thiuram, organochlorine fungicides such as tetrachloroisophthalonitrile, ethaboxam , Carboxamide fungicides such as oxycarboxylin, carboxin, flutolanil, silthiophane, mepronil, dimethomorph, phenpropidin, phen Morpholine fungicides such as ropimorph, spiroxamine, tridemorph, dodemorph, and fullmorph, azoxystrobin, cresoximemethyl, methminostrobin, orisatrobin, floxastrobin, trifloxystrobin, dimoxystrobin, pyraclostrobin, picoxy Strobilurin fungicides such as strobin, dicarboximide fungicides such as iprodione, procymidone, vinclozoline, clozolinate, fursulfamide, dazomet, methylisothiocyanate, chloropicrin, metasulfocarb, hydroxyisoxazole, hydroxyisoxazole potassium, Soil fungicides such as echromesole, DD, carb, basic copper chloride, basic copper sulfate, copper nonylphenol sulfonate, oxine copper, DBEDC , Copper disinfectant such as anhydrous copper sulfate, copper sulfate pentahydrate, cupric hydroxide, inorganic sulfur, hydrated sulfur agent, lime sulfur mixture, zinc sulfate, fentine, sodium bicarbonate, potassium bicarbonate, hypochlorous acid Inorganic fungicides such as chlorate and metallic silver, organophosphorus fungicides such as edifenphos, tolcrofosmethyl, fosetyl, iprobenphos, dinocap, pyrazophos, melanin biosynthesis inhibition such as carpropamide, fusalide, tricyclazole, pyroxylone, diclocimet, phenoxanil Antibiotic bactericides, kasugamycin, validamycin, polyoxins, blasticidin S, teclophthalam, oxytetracycline, mildiomycin, streptomycin and other antibiotic fungicides, rapeseed oil and other natural fungicides, bench-avaricarb isopropyl, iprovaricarb , Propamo Carbamate fungicides such as rubu and dietofencarb, pyrrole fungicides such as fluorimide, fludioxanyl and fenpiclonyl, plant activators that induce plant disease resistance such as probenazole, acibenzoral S methyl, thiazinyl, cyflufenamide, fenhexamide, quinoxyphene , Diflumetrim, Metraphenone, Picobenzamide, Proquinazide, Famoxadone, Ciazofamide, Phenamidone, Zoxamide, Boscalid, Chlorothalonil, Simoxanyl, Captan, Dithianon, Fluazinam, Folpet, Diclofluanid, (RS) -N- [2- (1,3- Dimethylbutyl) thiophen-3-yl] -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide (generic name pending: pen (Opirad), trifolin, oxolinic acid, isoprothiolane, ferrimzone, dichromedin, pencyclon, quinomethionate, iminoctazine acetate, iminoctadine albecate, ambam, polycarbamate, thiadiazine, chloroneb, organonickel, guazatine, dodine, quintozene, tolylfluanid, Bactericides such as anilazine, nitrotal isopropyl, fenitropan, dichlorane, DPC, dimethymol, bench azole, allethrin, tetramethrin, resmethrin, phenothrin, framethrin, permethrin, cypermethrin, deltamethrin, cyhalothrin, cyfluthrin, fenpropatoline, tralomethrin, cyclo Protorin, flucitrinate, fulvalinate, acrinatrin, tefluthrin, Synthetic pyrethroid insecticides such as phenthrin, empentrin, beta cyfluthrin, cypermethrin, fenvalerate, and various isomers or pesticide extracts, DDVP, cyanophos, fenthion, fenitrothion, tetrachlorbinphos, dimethylvinphos, propofos, Methyl parathion, temefos, phoxime, acephate, isofenphos, salicione, DEP, EPN, ethion, mecarbam, pyridafenthion, diazinon, pyrimiphosmethyl, etrimphos, isoxathion, quinalphos, chlorpyrifosmethyl, chlorpyrifos, hosalon, phosmet, methidathione mididefothion , Dimethoate, formothione, thiomethone, ethylthiomethone Organophosphate insecticides such as folate, terbufos, profenofos, prothiophos, sulphophos, pyracrofos, monocrotophos, nared, fothiazeto, trichlorfone, etoprofos, kazusafos, chlorfenvinphos, diclofenthion, ethylthiomethone, NAC, MTMC, MIPC, BPMC, Carbamate insecticides such as XMC, PHC, MPMC, etiophencarb, bendiocarb, pyrimicarb, carbosulfan, benfuracarb, mesomil, oxamyl, aldicarb, thiodicarb, alanib, and arylpropyl ether insecticides such as etofenprox and halfenprox Agents, silyl ether compounds such as silafluophene, nicotine sulfate, polynactin complex, abamectin, milbemecti Insecticidal natural products such as BT agents, cartap, thiocyclam, benzultap, diflubenzuron, chlorfluazuron, teflubenzuron, triflumuron, flufenoxuron, flucycloxuron, hexaflumuron, fluazuron, imidacloprid, nitenpyram, acetamiprid, dinotefuran, Pymetrozine, fipronil, buprofezin, phenoxycarb, pyriproxyfen, metoprene, hydroprene, quinoprene, endosulfan, diafenthiuron, triazuron, tebufenozide, benzoepin, novallon, nobiflumuron, emamectin benzoate, clothianidin, thiacloprid, thiamethoxam, flupiroxam Bifenazate, Chromafenozide, Etoxazole, Fu Acripyrim, flufenzine, halofenozide, indoxacarb, methoxyphenozide, spirodiclofen, tolfenpyrad, gamma cyhalothrin, etiprole, amidoflumet, bistrifluron, flonicamid, flubrosphosphate, flufenerim, pyridalyl, spinosad, spiromesifen, silafluophene, Insecticides such as cyromazine, lufenuron, esfenvalerate, sodium oleate, potassium oleate, chlorfenapyr, kelsen, azadirachtin, carbam, sodium carbam, dicophor, chlorbenzilate, phenisobromolate, tetradiphone, CPCBS, BPPS , Quinomethionate, amitraz, benzomate, hexithiazox, fenbutasine oxide, cyhexatin, die The pest control composition according to claim 12, which is one or more compounds selected from acaricides such as nochlor, clofentezin, pyridaben, fenpyroximate, phenazaquin, tebufenpyrad, and pyrimidifen.