JP2024118186A - Fused ring type heteroarylcarboxamide derivative or its salt, and fungicide containing the same as an active ingredient - Google Patents

Abstract

To provide a compound that exhibits superior effect as an agent for agricultural and horticultural use, particularly a microbicide for agricultural and horticultural use.SOLUTION: Provided is a fused heteroarylcarboxamide derivative represented by formula (I), serving as an active ingredient, or a salt thereof, where R1-R9 each represent, for example, a hydrogen atom, a C1-C6 alkyl group or the like, Y represents, for example, a bond, A1 and A2 each represent, for example, phenyl or the like, n and m each represent 0 or 1, where n+m is 1 or 2.SELECTED DRAWING: None

Description

The present invention relates to a fused heteroarylcarboxamide derivative or a salt thereof, and a fungicide containing the same as an active ingredient.

In the agricultural and horticultural fields, various fungicides have been developed and put to practical use for the purpose of controlling various pathogens.
However, conventionally widely used pesticides do not necessarily satisfy the requirements for their effectiveness, spectrum, residual activity, and further for the reduction of application frequency and application amount. In addition, the emergence of pathogenic bacteria that have developed resistance to conventionally widely used pesticides is also a problem. For example, in the cultivation of vegetables, fruit trees, flowers, tea, wheat, rice, and the like, various pathogenic bacteria that have developed resistance to various types of fungicides such as triazoles, imidazoles, pyrimidines, benzimidazoles, dicarboximides, phenylamides, and strobilurins have appeared in various places, and it is becoming more and more difficult to control these resistant pathogenic bacteria every year.
Therefore, there is a constant demand for new pesticides that are sufficiently effective at low doses against various pathogens that have developed resistance to conventional agricultural and horticultural fungicides, and that have little adverse effect on the environment.

Various new fungicides have been proposed to meet these demands, but they do not necessarily meet all of the above demands.

Patent Document 1 discloses the following carboxamide derivatives that have fungicidal activity and contain a phenoxy group (page 183, compound number I-002). However, Patent Document 1 does not disclose any compounds that contain imidazopyridine in the position corresponding to pyridine.

Patent Document 2 discloses an imidazopyridine carboxamide derivative having a phenoxy group (compound number 3 on page 35). However, the compound disclosed in Patent Document 2 is related to medicines such as sedatives, and is a compound in which an aryl group such as a pyridyl group is directly bonded to the nitrogen atom of the carboxamide group, and is not a compound in which the nitrogen atom is bonded at least via a methylene group.

Brochure No. WO2021/224220 CN 114437062

The present invention aims to provide a new substance that is useful for controlling various fungi, and in particular, that is highly effective against various fungi that have developed resistance to conventional fungicides, and that is effective at low doses, thus providing a highly safe substance with reduced problems such as residual toxicity and environmental pollution.

As a result of intensive research aimed at solving the above problems, the present inventors have found that the fused heteroarylcarboxamide derivatives defined by the following formula or salts thereof, and fungicides containing the same as active ingredients, are compounds having properties that can meet the above demands, and have thus completed the present invention.

（式中、
Ｒ¹は、水素、Ｃ₁～Ｃ₆のアルキル基、Ｃ₃～Ｃ₆のシクロアルキル基又はＣ₁～Ｃ₆のアルコキシ基を示し、
Ｒ²及びＲ³は、それぞれ独立に水素原子又はＣ₁～Ｃ₆のアルキル基を示し、Ｒ²及びＲ³は一緒になって、Ｃ₃～Ｃ₆のシクロアルキル基を形成してもよく、
Ｒ⁴及びＲ⁵は、それぞれ独立に水素原子、ハロゲン原子又はＣ₁～Ｃ₆のアルキル基を示し、Ｒ⁴及びＲ⁵は一緒になって、Ｃ₃～Ｃ₆のシクロアルキル基を形成してもよく、
Ｒ⁶は、水素原子、ハロゲン原子、Ｃ₁～Ｃ₆のアルキル基、Ｃ₃～Ｃ₆のシクロアルキル基、Ｃ₁～Ｃ₆のアルコキシ基、Ｃ₁～Ｃ₆のハロアルキル基、Ｃ₁～Ｃ₆のハロアルコキシ基、Ｃ₁～Ｃ₆アルキルチオ基、Ｃ₁～Ｃ₆アルキルスルフィニル基、Ｃ₁～Ｃ₆アルキルスルホニル基、無置換もしくは置換基Ｚ¹を有するフェニル基、又は無置換もしくは置換基Ｚ¹を有する５～１０員環のヘテロアリール基を示し、
Ｒ⁷は、水素原子、ハロゲン原子、シアノ基、Ｃ₁～Ｃ₆のアルキル基、Ｃ₃～Ｃ₆のシクロアルキル基、Ｃ₁～Ｃ₆のアルコキシ基、Ｃ₁～Ｃ₆のハロアルキル基、Ｃ₁～Ｃ₆のハロアルコキシ基、Ｃ₃～Ｃ₆のシクロアルキル基、Ｃ₁～Ｃ₆アルキルチオ基、Ｃ₁～Ｃ₆アルキルスルフィニル基、Ｃ₁～Ｃ₆アルキルスルホニル基、無置換もしくは置換基Ｚ²を有するフェニル基、又は無置換もしくは置換基Ｚ²を有する５～１０員環のヘテロアリール基を示し、
Ｒ⁸は、水素原子、ハロゲン原子、Ｃ₁～Ｃ₆のアルキル基、Ｃ₁～Ｃ₆のアルコキシ基、Ｃ₁～Ｃ₆のハロアルキル基、Ｃ₁～Ｃ₆のハロアルコキシ基、Ｃ₃～Ｃ₆のシクロアルキル基、Ｃ₁～Ｃ₆のアルキルチオ基、Ｃ₁～Ｃ₆のアルキルスルフィル基、Ｃ₁～Ｃ₆のアルキルスルホニル基、無置換もしくは置換基Ｚ³を有するフェニル基、又は無置換もしくは置換基Ｚ³を有する５～１０員環のヘテロアリール基を示し、 That is, the present invention provides a compound represented by the following formula (I):

(Wherein,
R ¹ represents hydrogen, a C ₁ -C ₆ alkyl group, a C ₃ -C ₆ cycloalkyl group, or a C ₁ -C ₆ alkoxy group;
R ² and R ³ each independently represent a hydrogen atom or a C ₁ -C ₆ alkyl group, and R ² and R ³ may together form a C ₃ -C ₆ cycloalkyl group;
^R4 and ^R5 each independently represent a hydrogen atom, a halogen atom, or a _C1 - _C6 alkyl group, and ^R4 and ^R5 may together form a _C3 - _C6 cycloalkyl group;
R ⁶ represents a hydrogen atom, a halogen atom, a C ₁ -C ₆ alkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ haloalkyl group, a C ₁ -C ₆ haloalkoxy group, a C ₁ -C ₆ alkylthio group, a C ₁ -C ₆ alkylsulfinyl group, a C ₁ -C ₆ alkylsulfonyl group, an unsubstituted or substituted phenyl group with Z ¹ , or an unsubstituted or substituted 5- to 10-membered heteroaryl group with Z ¹ ;
R ⁷ represents a hydrogen atom, a halogen atom, a cyano group, a C ₁ -C ₆ alkyl group, a C 3 -C ₆ cycloalkyl group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ haloalkyl group, a C ₁ -C ₆ haloalkoxy group, a C _{3 -C 6} cycloalkyl group, a C ₁ -C ₆ alkylthio group, a C ₁ -C ₆ alkylsulfinyl group, a C ₁ -C ₆ alkylsulfonyl group, an unsubstituted or substituted phenyl group having Z ² , or an unsubstituted or substituted 5- to 10-membered heteroaryl group having Z ² ;
^R8 represents a hydrogen atom, a halogen atom, a _C1 -C6 alkyl group, a C1- _C6 alkoxy group, _{a C1} - _C6 haloalkyl group, a _C1 - _C6 haloalkoxy group, a _C3 - _C6 cycloalkyl group, a _C1 - _C6 alkylthio _group , a _C1 - _C6 alkylsulfyl group, a _C1 - _C6 alkylsulfonyl group, an unsubstituted or substituted phenyl group with ^Z3 , or an unsubstituted or substituted 5-10-membered heteroaryl group with ^Z3 ;

R ⁹ represents a hydrogen atom, a halogen atom, a C ₁ -C ₆ alkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₆ alkoxy group, or a C ₁ -C ₆ haloalkyl group;
n and m are each 0 or 1, but n+m is 1 or 2;
Y represents an oxygen atom or a bond;
^A1 represents a phenyl group, a naphthyl group or a 5- to 10-membered heteroaryl group which may be unsubstituted or substituted with a substituent ^Z4 ;
^A2 represents a phenyl group, a naphthyl group, a phenoxy group, a naphthyloxy group, a 5- to 10-membered heteroaryl group, or a 5- to 10-membered heteroaryloxy group, which may be unsubstituted or substituted by a substituent ^Z5 ;
The substituent Z ¹ represents a halogen atom, a C ₁ -C ₆ alkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₆ alkoxy group, a nitro group, a cyano group, a C ₁ -C ₆ haloalkyl group, or a C ₁ -C ₆ haloalkoxy group, the number of the substituent Z ¹ may be one or more, and when there are two or more substituents, they may be the same or different from each other;
The substituent ^Z2 represents a halogen atom, a _C1 - _C6 alkyl group, a C3- _C6 cycloalkyl group, a _C1 - _C6 alkoxy group, a nitro group _, a cyano group, a _C1 - _C6 haloalkyl group, or a _C1 - _C6 haloalkoxy group, and the number of the substituent ^Z2 may be one or more, and when two or more substituents are present, they may be the same or different from each other;
The substituent ^Z3 represents a halogen atom, a _C1 - _C6 alkyl group, a C3- _C6 cycloalkyl group, a _C1 - _C6 alkoxy group, a nitro group _, a cyano group, a _C1 - _C6 haloalkyl group, or a _C1 - _C6 haloalkoxy group, and the number of the substituent ^Z3 may be one or more, and when two or more substituents are present, they may be the same or different from each other;

The substituent ^Z4 represents a halogen atom, a _C1 - _C6 alkyl group, a C3- _C6 cycloalkyl group, a _C1 - _C6 alkoxy group, a nitro group ^, a cyano group, _{a C1} - _C6 haloalkyl group, or a _C1 - _C6 haloalkoxy group, and may be one or more than one, and when it has two or more substituents, they may be the same or different from each other;
The substituent ^Z5 represents a halogen atom, a _C1 - _C6 alkyl group, a C3- _C6 cycloalkyl group, a _C1 - _C6 alkoxy group, a nitro group, a cyano group, _{a C1} - _C6 haloalkyl group, or a _C1 - _C6 haloalkoxy group, and ^Z5 may be one or more, and when it has two or more substituents, they may be the same or different from each other.
or a salt thereof (hereinafter also referred to as "the compound of the present invention"), and a fungicide containing the same as an active ingredient.
The present invention also relates to a method for producing a fused heteroarylcarboxamide derivative or a salt thereof, which is represented by the following reaction:

（式中、R⁶、R⁷、R⁸、R⁹及びＡ¹は、上記式(I)で定義した通りである）
で表されるカルボン酸誘導体と、
下記式(XVII)、

（式中、R¹、R²、R³、R⁴、R⁵、Ａ²、Ｙ、ｎ及びｍは、上記式(I)で定義したとおりである）
で表されるアミン誘導体とを反応させることを特徴とする製造方法。 The following formula (II):

(wherein R ⁶ , R ⁷ , R ⁸ , R ⁹ and A ¹ are as defined in formula (I) above).
and a carboxylic acid derivative represented by the formula:
The following formula (XVII):

(wherein ^R1 , ^R2 , ^R3 , ^R4 , ^R5 , ^A2 , Y, n and m are as defined in formula (I) above).
and reacting the compound represented by the formula (I) with an amine derivative represented by the formula (I).

The compounds of the present invention show excellent effects against various fungi.

The present invention will be described in detail below.
In the compound of the present invention represented by formula (I), the heteroaryl group may be either a 5- to 10-membered monocyclic or condensed ring, and may have one or more of the same or different ring-constituting heteroatoms. The type of heteroatom is not particularly limited, and examples thereof include a nitrogen atom, an oxygen atom, and a sulfur atom. Suitable examples of the ring constituting the heteroatom include a furyl group, a thienyl group, a thiazolyl group, an isothiazolyl group, a pyrazolyl group, a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a quinolyl group, an isoquinolyl group, a benzoxazolyl group, and a benzotriazolyl group.
Examples of the C1-C6 alkyl group include linear or branched alkyl groups having ₁ to ₆ , preferably 1 to 4, carbon atoms, such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, and isohexyl.
The halogen atom refers to a chlorine atom, a bromine atom, an iodine atom or a fluorine atom.
Suitable examples of the cycloalkyl group formed by combining R ² and R ³ , and R ⁴ and R ⁵ together, include a cyclopropane ring, a cyclobutane ring, a cyclopentane ring, and a cyclohexane ring.
Suitable examples of the C ₃ -C ₆ cycloalkyl group include a cyclopropane group, a cyclobutane group, a cyclopentane group, and a cyclohexane group.
The _C1 -C6 alkoxy group is a group having an oxygen atom between the carbon atoms in the carbon-carbon bond of an alkyl group, and examples thereof include linear or branched alkoxy groups having 1 to ₆ , preferably 1 to 4, carbon atoms, such as a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, a tert-butoxy group, an n-pentyloxy group, or an n-hexyloxy group.

The C ₁ -C ₆ haloalkyl group means an alkyl group in which any carbon atom in the above alkyl group is substituted with a halogen atom, and examples thereof include linear or branched haloalkyl groups having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, substituted with preferably 1 to 9 halogen atoms, such as a fluoromethyl group, a chloromethyl group, a difluoromethyl group, a trifluoromethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, a dichlorofluoromethyl group, a 1-fluoroethyl group, a 2-fluoroethyl group, a 2-chloroethyl group, a 2-bromoethyl group, a 2-iodoethyl group, a 2,2,2-trifluoroethyl group, a 2,2,2-trichloroethyl group, a pentafluoroethyl group, a 2,2-difluoroethyl group, a 1-fluoroisopropyl group, a 3-fluoropropyl group, a 3-chloropropyl group, a 3-bromopropyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a 4-fluorobutyl group, a 4-chlorobutyl group, a nonafluorobutyl group, and the like.

The C ₁ -C 6 haloalkoxy group includes the C ₁ -C ₆ haloalkoxy group described above. and ₆ alkoxy groups in which any carbon atom of the alkoxy group is substituted with a halogen atom, such as a fluoromethoxy group, a dichloromethoxy group, a trichloromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, a chlorodifluoromethoxy group, a bromodifluoromethoxy group, a dichlorofluoromethoxy group, a 1-fluoroethoxy group, a 2-fluoroethoxy group, a 2-chloroethoxy group, a 2-bromoethoxy group, a 2-iodoethoxy group, a 2,2,2-trifluoroethoxy group, a 2,2,2-trichloroethoxy group, a pentafluoroethoxy group, a 1-fluoroisopropoxy group, a 3-fluoropropoxy group, a 3-chloropropoxy group, a 3-bromopropoxy group, a 4-fluorobutoxy group, or a 4-chlorobutoxy group, which is preferably substituted with 1 to 9 halogen atoms, and which have a straight or branched chain haloalkoxy group having 1 to 6 carbon atoms, preferably 1 to 3 carbon atoms.
The _C1 - _C6 alkylthio group is a thio group substituted with the above-mentioned alkyl group, and examples of the _C1 - _C6 alkylthio group include alkylthio groups such as a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group, an n-butylthio group, an s-butylthio group, a t-butylthio group, an n-pentylthio group, and an n-hexylthio group.

The alkylsulfinyl group is a sulfinyl group substituted with the above-mentioned alkyl group, and examples of the _C1 - _C6 alkylsulfinyl group include alkylsulfinyl groups such as methylsulfinyl group, ethylsulfinyl group, n-propylsulfinyl group, isopropylsulfinyl group, n-butylsulfinyl group, s-butylsulfinyl group, t-butylsulfinyl group, n-pentylsulfinyl group, and n-hexylsulfinyl group.
The C ₁ -C ₆ alkylsulfonyl group is a sulfonyl group substituted with the above-mentioned alkyl group, and examples of the C ₁ -C ₆ alkylsulfonyl group include alkylsulfonyl groups such as methylsulfonyl group, ethylsulfonyl group, n-propylsulfonyl group, isopropylsulfonyl group, n-butylsulfonyl group, s-butylsulfonyl group, t-butylsulfonyl group, n-pentylsulfonyl group, and n-hexylsulfonyl group.

Representative methods for producing the fused heteroaryl amide derivative of the present invention represented by formula (I) and its intermediate, the heteroaryl carboxylic acid represented by formula (II), are described below. However, the scope of the present invention is not limited in any way by the production method, and any appropriately modified production method is also included.

[式中、
Ｒ⁶は、水素原子、ハロゲン原子、Ｃ₁～Ｃ₆のアルキル基、Ｃ₃～Ｃ₆のシクロアルキル基、Ｃ₁～Ｃ₆のアルコキシ基、Ｃ₁～Ｃ₆のハロアルキル基、Ｃ₁～Ｃ₆のハロアルコキシ基、Ｃ₁～Ｃ₆アルキルチオ基、Ｃ₁～Ｃ₆アルキルスルフィニル基、Ｃ₁～Ｃ₆アルキルスルホニル基、無置換もしくは置換基Ｚ¹を有するフェニル基、又は無置換もしくは置換基Ｚ¹を有するヘテロアリール基を示し、
Ｒ⁹は、水素原子、ハロゲン原子、Ｃ₁～Ｃ₆のアルキル基、Ｃ₃～Ｃ₆のシクロアルキル基、Ｃ₁～Ｃ₆のアルコキシ基、又はＣ₁～Ｃ₆のハロアルキル基を示し、
R¹⁰は、ハロゲン原子、シアノ基を示し、
R’は、Ｃ₁～Ｃ₆のアルキル基を示し、そして
Halは、ハロゲン原子を示す。] (Reaction Scheme 1)

[Wherein,
R ⁶ represents a hydrogen atom, a halogen atom, a C ₁ -C ₆ alkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ haloalkyl group, a C ₁ -C ₆ haloalkoxy group, a C ₁ -C ₆ alkylthio group, a C ₁ -C ₆ alkylsulfinyl group, a C ₁ -C ₆ alkylsulfonyl group, an unsubstituted or substituted phenyl group with Z ¹ , or an unsubstituted or substituted heteroaryl group with Z ¹ ;
R ⁹ represents a hydrogen atom, a halogen atom, a C ₁ -C ₆ alkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₆ alkoxy group, or a C ₁ -C ₆ haloalkyl group;
R ¹⁰ represents a halogen atom or a cyano group;
R' represents a _C1 - _C6 alkyl group, and
Hal represents a halogen atom.

In reaction scheme 1, the compound of formula (IV) can be produced by reacting the carboxylic acid derivative of formula (III) with an alcohol represented by R'OH in the presence of a condensation reagent and a base in an inert solvent, or by reacting the acid derivative of formula (III) with a large excess of R'OH in the presence of an acid. The starting compound (III) is basically a known compound or a compound that is readily available from known compounds to those skilled in the art.
The reaction temperature in the reaction using a condensation reagent is usually in the range of -20°C to the boiling point of the solvent, and the reaction time is usually in the range of 0.2 hours to 24 hours. The alcohol represented by R'OH is usually used in the range of 1 to 5 times the molar amount of the carboxylic acid derivative represented by general formula (III).
Examples of the condensation reagent used in Reaction Scheme 1 include diethyl cyanophosphate (DEPC), carbonyldiimidazole (CDI), 1,3-dicyclohexylcarbodiimide (DCC), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, chlorocarbonates, 2-chloro-1-methylpyridinium iodide, and the like. The amount of the reagent used is usually in the range of 1 to 3 times the molar amount of the acid derivative of general formula (III).

Examples of bases include inorganic bases such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate, and potassium hydrogen carbonate; acetates such as sodium acetate and potassium acetate; metal alkoxides such as potassium t-butoxide, sodium methoxide, and sodium ethoxide; tertiary amines such as triethylamine, diisopropylethylamine, and 1,8-diazabicyclo[5.4.0]undec-7-ene; and nitrogen-containing aromatic compounds such as pyridine and dimethylaminopyridine. The amount of base used is usually in the range of 1 to 10 times the molar amount of the carboxylic acid derivative represented by the general formula (III).

In Reaction Scheme 1, a solvent may or may not be used. Examples of solvents that can be used include chain or cyclic ethers such as dimethyl ether, diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, dioxane, etc.; aromatic hydrocarbons such as benzene, toluene, xylene, etc.; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, etc.; nitriles such as acetonitrile, etc.; esters such as methyl acetate, ethyl acetate, butyl acetate, etc.; and polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, DMSO, 1,3-dimethyl-2-imidazolidinone, etc. These inert solvents can be used alone or in combination of two or more.
When a large excess of R'OH is reacted in the presence of an acid, the reaction temperature is usually within the range of 0°C to the boiling point of the solvent, and the reaction time is usually within the range of 0.2 to 24 hours.
The acid includes sulfuric acid, hydrogen chloride, thionyl chloride, and the like.
After the reaction, the target compound may be isolated from the reaction system containing the target compound by a conventional method, and if necessary, purified by recrystallization, column chromatography, or the like to produce the target compound.

[式中、
Ｒ⁶、Ｒ⁹、R’及びHalは、前記式(IV)で定義したとおりである。
Qは、ハロゲン原子、又はO-A¹を示し、
A¹は、無置換もしくは置換基Ｚ⁴を有する、フェニル基、ナフチル基又は５～１０員環のヘテロアリール基を示し、そして
置換基Ｚ⁴は、ハロゲン原子、Ｃ₁～Ｃ₆のアルキル基、Ｃ₃～Ｃ₆のシクロアルキル基、Ｃ₁～Ｃ₆のアルコキシ基、ニトロ基、シアノ基、Ｃ₁～Ｃ₆のハロアルキル基又はＣ₁～Ｃ₆のハロアルコキシ基を示し、置換基Ｚ⁴は、１つ又は２つ以上であってもよく、２つ以上の置換基を有するときは、互いに同一であっても異なっていてもよい。]
化合物（Ｖ）は、基本的には、公知化合物であるか、当業者において公知の化合物から直ちに入手可能な化合物である。 (Reaction Scheme 2)

[Wherein,
R ⁶ , R ⁹ , R' and Hal are as defined above in formula (IV).
Q represents a halogen atom or OA ¹ ;
A ¹ represents a phenyl group, a naphthyl group, or a 5-10 membered heteroaryl group which is unsubstituted or has a substituent Z ⁴ , and the substituent Z ⁴ represents a halogen atom, a C ₁ -C ₆ alkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₆ alkoxy group, a nitro group, a cyano group, a C ₁ -C ₆ haloalkyl group, or a C ₁ -C ₆ haloalkoxy group, and the number of the substituents Z ⁴ may be one or more, and when two or more substituents are present, they may be the same or different.]
Compound (V) is basically a known compound or a compound readily available from known compounds to those skilled in the art.

The compound represented by the formula (VI) can be produced by reacting an aromatic halogen compound (V) with a cyanating agent in the presence of a palladium compound. The reaction is usually carried out in the presence of a solvent. Examples of the solvent include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol and ethanol, aprotic polar solvents such as N,N-dimethylformamide, N-methylpyrrolidone, and DMSO, and mixtures thereof. Examples of the cyanating agent include zinc cyanide, etc. Examples of the palladium compound include tetrakis(triphenylphosphine)palladium, etc.
In the reaction of Reaction Scheme 2, the cyanating agent is usually used in a ratio of 1 to 5 moles and the palladium compound is usually used in a ratio of 0.01 to 0.5 moles, relative to 1 mole of the compound of Formula (V). The reaction temperature is usually within the range of 50 to 200° C., and the reaction time is usually within the range of 0.5 to 24 hours.
The target compound obtained in each of the above reactions can be easily isolated from the reaction mixture by a commonly used isolation means, such as organic solvent extraction, chromatography, recrystallization, distillation, etc., and can be further purified by a commonly used purification means.

[式中、Ｒ⁶、Ｒ⁹、Ｒ¹⁰、R’、A¹及びHalは、前記式 (IV)、（Ｖ）及び(VI)で定義した通りである。]
前記式（IX）で表される化合物は、前記式（VII）で表される化合物と、前記式(VIII)で表される化合物とを、塩基の存在下又は不存在下に、不活性溶媒中で反応させることにより製造することができる。化合物（VII）は、基本的には、公知の化合物であるか、又は当業者において公知の化合物から直ちに入手可能な化合物である。
前記式(VIII)で表される化合物は、市販品であってもよく、周知の方法に従った別の化合物の転化又は誘導体化によって得てもよい。 (Reaction Scheme 3)

[In the formula, R ⁶ , R ⁹ , R ¹⁰ , R′, A ¹ and Hal are as defined in formulas (IV), (V) and (VI).]
The compound represented by the formula (IX) can be produced by reacting the compound represented by the formula (VII) with the compound represented by the formula (VIII) in an inert solvent in the presence or absence of a base. Compound (VII) is basically a known compound or a compound readily available from known compounds to those skilled in the art.
The compounds of formula (VIII) may be commercially available or may be obtained by conversion or derivatization of other compounds according to well-known methods.

As the solvent used in the reaction between the compound of formula (VII) and the compound of formula A ¹ -OH, a wide variety of known solvents can be used as long as they are inert to the reaction. Examples of such solvents include aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane, and heptane, aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene, and xylene, halogenated hydrocarbon solvents such as methylene chloride, 1,2-dichloroethane, and chloroform, ether solvents such as diethyl ether, tetrahydrofuran, and 1,4-dioxane, ester solvents such as methyl acetate and ethyl acetate, ketone solvents such as acetone and methyl ethyl ketone, amide solvents such as N,N-dimethylformamide, nitrile solvents such as acetonitrile and propionitrile, and aprotic polar solvents such as N-methylpyrrolidone and N,N'-dimethylimidazolinone. These solvents can be used alone or in combination of two or more as necessary.

The base used in the reaction between the compound of formula (VII) and the compound of formula (VIII) may be a known inorganic base or organic base. Examples of inorganic bases include alkali metal carbonates such as sodium carbonate, potassium carbonate, and sodium bicarbonate, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, and alkali metal hydrides such as sodium hydride and potassium hydride. Examples of organic bases include alkali metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium t-butoxide, and amines such as triethylamine and pyridine. These bases may be used alone or in combination of two or more.
Such a base can be used in an amount of usually 1 to 100 equivalents, preferably 1 to 2 equivalents, relative to the compound represented by the formula (VIII).

The ratio of the compound of the formula (VII) to the compound of the formula (VIII) is more preferably 1 to 1.2 moles of the compound (VIII) relative to the compound (VII).
The reaction can usually be carried out within a temperature range from -78°C to the boiling point of the solvent used, and is preferably carried out at 0°C to 100°C.
The reaction time varies depending on the reaction temperature etc. and cannot be generalized, but the reaction is usually completed within about 0.5 to 24 hours.
The target compound obtained in each of the above reactions can be easily isolated from the reaction mixture by a commonly used isolation means, such as organic solvent extraction, chromatography, recrystallization, distillation, etc., and can be further purified by a commonly used purification means.

[式中、Ｒ⁶、Ｒ⁹、R’、及びA₁は、前記式(IX)で定義されている通りである。]
化合物（Ｘ）は、基本的には、公知の化合物であるか、又は当業者において公知の化合物から直ちに入手可能な化合物である。
前記式（XI)で表される化合物は、前記式(X)の化合物と接触還元触媒とを水素雰囲気下で反応させることにより製造することができる。該反応は、通常溶媒の存在下で行われる。溶媒としては、例えば、テトラヒドロフランや、エチレングリコールジメチルエーテル、tert-ブチルメチルエーテル、1，4-ジオキサン等のエーテル類、ヘキサンや、ヘプタン、オクタン等の脂肪族炭化水素類、トルエン、キシレン等の芳香族炭化水素類、メタノールや、エタノール等のアルコール類、Ｎ，Ｎ－ジメチルホルムアミドや、Ｎ－メチルピロリドン、DMSO等の非プロトン性極性溶媒、及びこれらの混合物が挙げられる。 (Reaction Scheme 4)

[In the formula, R ⁶ , R ⁹ , R′, and A ₁ are as defined in formula (IX).]
The compound (X) is basically a known compound or a compound that is readily available to those skilled in the art from known compounds.
The compound represented by formula (XI) can be produced by reacting the compound represented by formula (X) with a catalytic reduction catalyst under a hydrogen atmosphere. The reaction is usually carried out in the presence of a solvent. Examples of the solvent include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol and ethanol, aprotic polar solvents such as N,N-dimethylformamide, N-methylpyrrolidone, and DMSO, and mixtures thereof.

Examples of the catalytic reduction catalyst include palladium-activated carbon, platinum oxide, and palladium hydroxide.
In the reaction of Reaction Scheme 4, the catalytic reduction catalyst is usually used in a ratio of 0.01 to 0.5 moles per mole of the compound of formula (X). The reaction temperature is usually within the range of 0°C to the boiling point of the solvent, and is preferably room temperature to 100°C. The reaction time is usually within the range of 0.5 to 24 hours.
The target compound obtained in each of the above reactions can be easily isolated from the reaction mixture by a commonly used isolation means, such as organic solvent extraction, chromatography, recrystallization, distillation, etc., and can be further purified by a commonly used purification means.

[式中、Ｒ⁶、Ｒ⁹、Ｒ‘、及びA¹ は、前記式(XI)を示し、
Ｒ⁸は、水素原子、ハロゲン原子、Ｃ₁～Ｃ₆のアルキル基、Ｃ₁～Ｃ₆のハロアルキル基、Ｃ₃～Ｃ₆のシクロアルキル基、無置換もしくは置換基Ｚ³を有するフェニル基、又は無置換もしくは置換基Ｚ³を有する５～１０員環のヘテロアリール基を示し、そして
R¹¹は、ヒドロキシ基、ハロゲン原子又はＣ₁～Ｃ₆のアルコキシ基を示す。 ]
化合物（ＸＩ）は、基本的には、公知の化合物であるか、又は当業者において公知の化合物より直ちに入手可能な化合物である。 (Reaction Scheme 5)

[In the formula, R ⁶ , R ⁹ , R′, and A ¹ represent the formula (XI),
^R8 represents a hydrogen atom, a halogen atom, a _C1 - _C6 alkyl group, a _C1 - _C6 haloalkyl group, a _C3 - _C6 cycloalkyl group, an unsubstituted or substituted phenyl group having ^Z3 , or an unsubstituted or substituted 5- to 10-membered heteroaryl group having ^Z3 ;
R ¹¹ represents a hydroxy group, a halogen atom, or a C ₁ -C ₆ alkoxy group.
Compound (XI) is essentially a known compound or a compound readily available to those skilled in the art from known compounds.

The compound represented by the formula (XIV) can be produced by reacting the compound represented by the formula (XI) with the compound represented by the formula (XII) or the compound represented by the formula (XIII) in an inert solvent in the presence or absence of a base.
The reaction temperature in this reaction is usually in the range of -20°C to 120°C, preferably 20°C to 100°C, and the reaction time is usually in the range of 0.2 hours to 24 hours, preferably 0.5 hours to 5 hours. The compounds of the formula (XII) and the formula (XIII) are usually used in the range of 1 to 5 times by mol, preferably 1 to 2 times by mol, based on the compound of the formula (XI).

Examples of bases include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, and potassium hydrogen carbonate; acetates such as sodium acetate and potassium acetate; metal alkoxides such as potassium t-butoxide, sodium methoxide, and sodium ethoxide; tertiary amines such as triethylamine, diisopropylethylamine, and 1,8-diazabicyclo[5.4.0]undec-7-ene; and nitrogen-containing aromatic compounds such as pyridine and dimethylaminopyridine. The amount of base used is usually 1 to 10 times the molar amount of the aromatic methaneamine compound (XI), and preferably 1 to 2 times the molar amount.

This reaction may or may not require the use of a solvent, but any solvent that does not significantly inhibit this reaction may be used. Examples of the solvent that can be used include chain or cyclic ethers such as dimethyl ether, diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, dioxane, etc.; aromatic hydrocarbons such as benzene, toluene, xylene, etc.; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, etc.; nitriles such as acetonitrile; esters such as methyl acetate, ethyl acetate, butyl acetate, etc.; and polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, DMSO, 1,3-dimethyl-2-imidazolidinone, etc. These inert solvents may be used alone or in combination of two or more.
After the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and if necessary, purified by recrystallization, column chromatography, or the like to produce the target product.

[式中、Ｒ⁶、Ｒ⁸、Ｒ⁹、Ｒ‘及びA¹ は、前記式(XIV)の定義の通りである。]
前記式(XV)で表される化合物は、前記式(XIV)の化合物と、脱水剤とを不活性溶媒中で反応させることにより製造することができる。
この反応における反応温度は、通常-２０℃～２００℃、好ましくは２０℃～１２０℃の範囲で、反応時間は、通常０．２時間～２４時間、好ましくは０．５時間～５時間の範囲で行なわれる。脱水剤は、前記式(XIV)の化合物に対して、通常１～１０倍モル、好ましくは１～５倍モルの範囲で使用される。 (Reaction Scheme 6)

[In the formula, R ⁶ , R ⁸ , R ⁹ , R′, and A ¹ are as defined in formula (XIV).]
The compound represented by the formula (XV) can be produced by reacting the compound represented by the formula (XIV) with a dehydrating agent in an inert solvent.
The reaction temperature in this reaction is usually in the range of -20°C to 200°C, preferably 20°C to 120°C, and the reaction time is usually in the range of 0.2 hours to 24 hours, preferably 0.5 hours to 5 hours. The dehydrating agent is usually used in the range of 1 to 10 times by mol, preferably 1 to 5 times by mol, based on the compound of formula (XIV).

Examples of inert solvents include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, tert-butyl methyl ether, 1,4-dioxane, etc., aliphatic hydrocarbons such as hexane, heptane, octane, etc., aromatic hydrocarbons such as toluene, xylene, etc., alcohols such as methanol, ethanol, etc., aprotic polar solvents such as N,N-dimethylformamide, N-methylpyrrolidone, DMSO, etc., and mixtures thereof. Examples of dehydrating agents include phosphoryl chloride, trifluoromethanesulfonic anhydride, etc.
After the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and if necessary, purified by recrystallization, column chromatography, or the like to produce the target product.

[式中、Ｒ⁶、Ｒ⁸、Ｒ⁹、Ｒ‘、Ｘ及びA¹は、前記式(XV)を示し、Ｒ⁷は、ハロゲン原子を示す。]
前記式(XVI)で表される化合物は、前記式(XV)の化合物と、ハロゲン化剤とを不活性溶媒中で反応させることにより製造することができる。
ハロゲン化剤としては、例えば、N-クロロスクシンイミドや、N-ブロモスクシンイミド、塩化スルフリル等が挙げられる。 (Reaction Scheme 7)

[In the formula, R ⁶ , R ⁸ , R ⁹ , R′, X and A ¹ represent the formula (XV), and R ⁷ represents a halogen atom.]
The compound represented by the formula (XVI) can be produced by reacting the compound represented by the formula (XV) with a halogenating agent in an inert solvent.
Examples of the halogenating agent include N-chlorosuccinimide, N-bromosuccinimide, and sulfuryl chloride.

Examples of the inert solvent include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, tert-butyl methyl ether, 1,4-dioxane, etc.; aliphatic hydrocarbons such as hexane, heptane, octane, etc.; aromatic hydrocarbons such as toluene, xylene, etc.; alcohols such as methanol, ethanol, etc.; aprotic polar solvents such as N,N-dimethylformamide, N-methylpyrrolidone, DMSO, etc.; and mixtures thereof.
The reaction temperature in this reaction is usually in the range of -20°C to 200°C, preferably 20°C to 120°C, and the reaction time is usually in the range of 0.2 hours to 24 hours, preferably 0.5 hours to 5 hours. The halogenating agent is usually used in the range of 1 to 20 times by mol, preferably 1 to 10 times by mol, based on the compound of formula (XV).
After the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and if necessary, the target product can be produced by purifying the product by recrystallization, column chromatography, or the like.

[式中、Ｒ⁶、Ｒ⁸、Ｒ⁹、Ｒ‘、及びA₁は、前記式(XIV)で規定される通りであり、Ｒ⁷は、水素原子又はハロゲン原子を示す。]
前記式(II)で表される化合物は、前記式(XVI)の化合物を、不活性溶媒中で、酸又は塩基で処理することにより製造することができる。
不活性溶媒としては、例えば、テトラヒドロフランや、エチレングリコールジメチルエーテル、tert-ブチルメチルエーテル、１，４-ジオキサン等のエーテル類、ヘキサンや、ヘプタン、オクタン等の脂肪族炭化水素類、トルエンや、キシレン等の芳香族炭化水素類、メタノールや、エタノール等のアルコール類、Ｎ，Ｎ－ジメチルホルムアミドや、Ｎ－メチルピロリドン、DMSO等の非プロトン性極性溶媒、更には、水を例示することができ、これらの不活性溶媒は、単独で又は２種以上混合して使用することができる。
酸としては、例えば、塩酸や、酢酸等が挙げられる。
塩基としては、例えば、水酸化ナトリウムや、水酸化リチウム、水酸化カリウム等が挙げられる。
この反応における反応温度は、通常-２０℃～２００℃、好ましくは２０℃～１２０℃の範囲で、反応時間は、通常０．２時間～２４時間、好ましくは０．５時間～５時間の範囲で行なわれる。酸又は塩基は、前記式(XVI)の化合物に対して通常１～２０倍モル、好ましくは１～１０倍モルの範囲で使用される。
反応後、目的物は、当該目的物を含む反応系から常法により単離すれば良く、必要に応じて、再結晶化や、カラムクロマトグラフィー等で精製することにより目的物を製造することができる。 (Reaction Scheme 8)

[In the formula, R ⁶ , R ⁸ , R ⁹ , R′, and A ₁ are as defined in the formula (XIV), and R ⁷ represents a hydrogen atom or a halogen atom.]
The compound represented by the formula (II) can be produced by treating the compound represented by the formula (XVI) with an acid or a base in an inert solvent.
Examples of the inert solvent include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, tert-butyl methyl ether, 1,4-dioxane, etc.; aliphatic hydrocarbons such as hexane, heptane, octane, etc.; aromatic hydrocarbons such as toluene, xylene, etc.; alcohols such as methanol, ethanol, etc.; aprotic polar solvents such as N,N-dimethylformamide, N-methylpyrrolidone, DMSO, etc.; and water. These inert solvents can be used alone or in combination of two or more kinds.
The acid includes, for example, hydrochloric acid, acetic acid, and the like.
Examples of the base include sodium hydroxide, lithium hydroxide, and potassium hydroxide.
The reaction temperature in this reaction is usually in the range of -20°C to 200°C, preferably 20°C to 120°C, and the reaction time is usually in the range of 0.2 hours to 24 hours, preferably 0.5 hours to 5 hours. The acid or base is usually used in the range of 1 to 20 times by mol, preferably 1 to 10 times by mol, based on the compound of formula (XVI).
After the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and, if necessary, the target product can be produced by purifying the product by recrystallization, column chromatography, or the like.

[式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ｒ⁶、Ｒ⁷、Ｒ⁸、Ｒ⁹、Ｙ、A¹、A²、ｎ及びｍは、前記式(II)及び先に説明された式（XVII）で規定される通りである。] (Reaction Scheme 9)

[In the formula, ^R1 , ^R2 , ^R3 , ^R4 , ^R5 , ^R6 , ^R7 , ^R8 , ^R9 , Y, ^A1 , ^A2 , n and m are as defined in the formula (II) and the formula (XVII) described above.]

The heteroarylcarboxamide derivative of the present invention represented by general formula (I) can be produced by reacting the compound represented by formula (II) with the amine derivative represented by formula (XVII) in the presence of a condensing agent and a base in an inert solvent, or by converting the compound of formula (II) into an acid halide and then reacting it with the amine derivative represented by formula (XVII) in the presence of a base in an inert solvent.
The amine derivative represented by formula (XVII) may be a commercially available product or may be obtained by the method described in WO2015/007626.
The reaction temperature in the reaction using a condensation reagent is usually in the range of -20°C to 120°C, and the reaction time is usually in the range of 0.2 hours to 24 hours. The amine derivative represented by the formula (XVII) is usually used in the range of 1 to 5 times the molar amount of the compound of the formula (II).
Examples of the condensation reagent used in this reaction include diethyl cyanophosphate (DEPC), carbonyldiimidazole (CDI), 1,3-dicyclohexylcarbodiimide (DCC), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, chlorocarbonates, 2-chloro-1-methylpyridinium iodide, and the like. The amount of the reagent used is usually in the range of 1 to 3 times the molar amount of the heteroaryl carboxylic acid derivative represented by the general formula (II).

Examples of the base include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, and potassium hydrogen carbonate; acetates such as sodium acetate and potassium acetate; metal alkoxides such as potassium t-butoxide, sodium methoxide, and sodium ethoxide; tertiary amines such as triethylamine, diisopropylethylamine, and 1,8-diazabicyclo[5.4.0]undec-7-ene; and nitrogen-containing aromatic compounds such as pyridine and dimethylaminopyridine. The amount of the base used is usually 1 to 10 times the molar amount of the compound of formula (II).
The reaction for converting to an acid halide is usually carried out at a temperature in the range of -20°C to 120°C for a reaction time in the range of 0.2 to 24 hours.
Examples of the acid halogenating agent used for converting to an acid halide include thionyl chloride and oxalyl chloride.
In this reaction, an inert solvent may or may not be used, but any inert solvent that does not significantly inhibit this reaction may be used. Examples of inert solvents that can be used include chain or cyclic ethers such as dimethyl ether, diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, dioxane, etc.; aromatic hydrocarbons such as benzene, toluene, xylene, etc.; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, etc.; nitriles such as acetonitrile; esters such as methyl acetate, ethyl acetate, butyl acetate, etc.; and polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, DMSO, 1,3-dimethyl-2-imidazolidinone, pyridine, etc. These inert solvents can be used alone or in combination of two or more.

Examples of the base include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, and potassium hydrogen carbonate; acetates such as sodium acetate and potassium acetate; metal alkoxides such as potassium t-butoxide, sodium methoxide, and sodium ethoxide; tertiary amines such as triethylamine, diisopropylethylamine, and 1,8-diazabicyclo[5.4.0]undec-7-ene; and nitrogen-containing aromatic compounds such as pyridine and dimethylaminopyridine. The amount of the base used is usually in the range of 1 to 10 times the molar amount of the compound of formula (II).
After the reaction, the target compound may be isolated from the reaction system containing the target compound by a conventional method, and if necessary, purified by recrystallization, column chromatography, or the like to produce the target compound.

The agricultural and horticultural fungicide of the present invention contains the compound of the present invention represented by formula (I) or a salt thereof as an active ingredient. The compound of the present invention can be used alone or in the form of a mixture thereof.
Suitable salts of the compound represented by formula (I) of the present invention include inorganic acid salts such as hydrochlorides, sulfates, nitrates, and phosphates, as well as acetates, fumarates, maleates, oxalates, methanesulfonates, benzenesulfonates, and p-toluenesulfonates.
The amount of the compound of the present invention or a salt thereof (hereinafter collectively referred to as "the compound of the present invention") contained in the agricultural and horticultural fungicide of the present invention is generally 0.1 to 99.9% by mass, preferably 0.2 to 80% by mass, based on the total mass of the formulation.

The agricultural and horticultural fungicide of the present invention can be mixed or used in combination with one or more other fungicides, insecticides, acaricides, repellents, synergists, or plant growth regulators, together with the compound of formula (I) of the present invention, if necessary. The mixture thus obtained has a broad spectrum of activity.

In the agricultural and horticultural fungicide of the present invention, examples of other fungicides (common names) that can be mixed or used in combination with the compound of the present invention include, for example, the following, but the other fungicides that can be mixed or used in combination are not necessarily limited to these.

Specific examples of the active compounds include, for example, D-D (1,3-dichloropropene), acibenzolar-S-methyl, aldimorph, ametoctradin, amisulbrom, andoprim, anilazine, azaconazole, azoxystrobin, basic copper sulfate, benodanil, benomyl, benthiavalicarb-isopropyl, benthiazole, bitertanol, bixafen, blasticidin S, boscalid, bromuconazole, calcium carbonate, buthiobate, lime sulfur, etc. polysulfide), captafol, captan, carbendazim, carboxin, carpropamid, chinomethionat, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate, DBEDC (complex of bis(ethylenediamine)copper-bis-(dodecylbenzenesulfonic acid)), copper hydroxide, copper nonylphenol sulfonate, basic copper chloride oxychloride), cyazofamid, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, dazomet, diclobutrazol, dichlofluanid, dichloclone, diclocymet, diclomezine, diethofencarb, difenoconazole, diflumetrim torim), dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dithane-stainless, dithianon, dodine, echlomezole, edifenphos, enestrobin, epoxiconazole, etaconazole, ethaboxam, extract from mushroom, famoxadone, fenamidone, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenoxanil,

Fenpiclonil, fenpropidin, fenpyrazamine, ferimzone, fluazinam, flumetover, flumorph, fluopicolide, fluopyram, fluoroimide, fluotrimazole, fluoxastrobin, fluquinconazole, flusulfamide, flutolanil, fluxapyroxadil, uxapyroxad, folpet, fosetyl aluminum (fosetyl-AL), fthalide, fuberidazole, fludioxonil, flusilazole, flutianil, flutriafol, furametpyr, fluconazole, guazatine, hexaconazole, hydroxyisoxazole, hymexazol, imazalil, imazalil sulfate, imibenconazole, iminoctadine acetate, iminoctadine-DBS,

Ipconazole, IBP (iprobenfos), iprodione, iprovalicarb, isofetamide, isoprothiolane, isopyrazam, isotianil, kasugamycin, kresoxim-methyl, mancozeb, mandipropamid, maneb, manzeb, mepanipyrim, mepronil, metalaxyl, metam-ammonium, metam-sodium, metconazole, methasulfocarb, methyl bromide bromide, methylisothiocyanate, metominostrobin, metrafenone, mildiomycin, myclobutanil, nickel dimethyldithiocarbamate, nuarimol, orysastrobin, oxadixyl, oxathiapiprolin, oxine-copper, oxolinic acid, oxpoconazole fumarate fumarate, oxycarboxin, oxytetracycline, pebulate, pefurazoate, penconazole, pencycuron, penflufen, penthiopyrad, picarbutrazox, picoxystrobin, piperalin, polycarbamate, polyoxin-B, polyoxins, potassium hydrogen carbonate, probenazole, prochloraz, procymidone, propamocarb, propiconazole, propineb, proquinazid,

Prothioconazole, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyrazophos, pyribencarb, pyridinitril, pyrifenox, pyrimethanil, pyriophenone, pyroquilon, quinoxyfen, quintozene, sedaxane, silver, simeconazole, sodium hydrogen carbonate, sodium hypochlorite hypochlorite, spiroxamine, streptomycin, sulfur, tebufloquin, tebuconazole, tecloftalam, terbinafine, tetraconazole, thiabendazole, thiadiazin, thifluzamide, thiophanate, thiophanate-methyl, thiram, tiadinil, tolclofos-methyl yl), tolprocarb, tolylfluanid, triadimefon, triadimenol, triclopyricarb, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, uniconazole-P, validamycin (-A), vinclozolin, zarilamid, zinc sulfate sulfate), zineb, ziram, zoxamide, quinohumerin, mefentrifluconazole, ipfentrifluconazole, dichlobenthiazox, fenpicoxamid, isoflucipram, fluindapyr, inpyrfluxam, aminopyrifen Examples include aminopyrifen, pyrapropoyne, pyridachlomethyl, methyltetraprole, ipflufenoquin, florylpicoxamid, fluoxapiprolin, cyclobutrifluram, metarylpicoxamid, and fluopimomide.

When the agricultural and horticultural fungicide of the present invention is used in combination with a compound having insecticidal activity, acaricidal activity, nematocidal activity, herbicidal activity, or plant growth regulating activity that can be mixed or used in conjunction with the compound of the present invention, a synergistic effect such as a reduction in the amount of drug as well as a reduction in the amount of control can be expected. In addition, when the fungicide is used in combination with a repellent or synergist, a more effective control effect such as a synergistic effect can be expected. Specific examples of such active compounds include the following.

Organophosphorus agents, such as acephate, azinphos-methyl, chlorpyrifos, diazinon, dichlorvos, dimeton-S-methyl, dimethoate, dimethylvinphos, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methidathion, monocrotophos, crotophos, naled, oxideprofos, parathion, phenthoate, phosalone, pirimiphos-methyl, pyridafenthion, profenofos, prothiofos, propaphos, pyraclofos, salithion, sulprofos, thiometon, tetrachlorvinfos, trichlorphon, vamidothion, and the like;
Carbamates such as alanycarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, furathiocarb, isoprocarb, methomyl, metolcarb, pirimicarb, propoxur, thiodicarb, and the like;
Organochlorines, such as aldrin, chlordane, DDT (p,p'-DDT), endosulfan, lindane, etc.;

Pyrethroids, such as acrinathrin, allethrin, bifenthrin, cycloprothrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, deltamethrin, etofenprox, fenpropathrin, fenvalerate, flucythrinate , flufenprox, fluvalinate, furamethrin, halofenprox, imiprothrin, permethrin, phenothrin, prallethrin, pyrethrins, resmethrin, silafluofen, tefluthrin, tralomethrin, transfluthrin, etc.;
Neonicotinoid agents, such as acetamiprid, clothianidin, dinotefran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, and the like;
Diamide agents, such as chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubenziamide, tetraniliprole, and the like;
Phenylpyrazole agents, such as ethiprole, fipronil, acetoprole, pyrafluoprole, pyriprole, etc.;
Nereistoxins, such as bensultap, cartap, thiocyclam, thiosultap, etc.;
Insect growth regulators such as phenylbenzoyl ureas and diacylhydrazines, for example, chlorfluazuron, diflubenzuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron, buprofezin, chromafenozide, halofenozide, methoxyfenozide, tebufenozide, cyromazine, etc.;
Juvenile hormone agents, such as diofenolan, fenoxycarb, hydroprene, methoprene, pyriproxyfen, and the like;

Insecticidal substances produced by microorganisms, such as abamectin, emamectin-benzoate, ivermectin, lepimectin, milbemectin, nemadectin, nikkomycin, polyoxin complex, spinetram, spinosad, BT agents, etc.;
insecticidal substances derived from natural products, for example, anabasine, azadirachtin, deguelin, fatty acid glyceride, hydroxypropyl starch, soybean lecithin, nicotine, nornicotine, sodium oleate, petroleum oil, propylene glycol monolaurate, rapeseed oil, rotenone, sorbitan fatty acid ester, starch, etc.;
Other insecticides include afidpyropen, benzpyrimoxan, broflanilide, chlorfenapyr, diafenthiuron, dichloromezotiaz, dimpropyridaz, and DBEDC (Dodecylbenzenesulphonic acidbisethylenediamine copper [II] salt), flonicamid, flometoquin, flufenerim, flupyradifurone, flupyrimin, fluralaner, fluhexafon, fluxametamide, hydramethylnon, indoxacarb, isocycloseram, metaflumizone, metaldehyde, nicotine sulfate sulfate), oxazosulfyl, pymetrozine, pyridalyl, pyrifluquinazon, spirotetramat, sulfoxaflor, tolfenpyrad, triazamate, triflumezopyrim, tyclopyrazoflor, and the like;

Acaricides such as acequinocyl, acinonapyr, amidoflumet, amitraz, azocyclotin, benzoximate, bifenazate, binapacryl, phenisobromorate, chinomethionat, clofentezine, cyenopyrafen, cyflumetofen, tricyclohexyltin hydroxide, dicofol, dienochlor, etoxazole, fenazaflor, fenazaquin, fenbutatin oxide oxide), fenothiocarb, fenpyroximate, fluacrypyrim, hexythiazox, pyrimidifen, polynactins, propargite, pyflubumide, pyridaben, spirodiclofen, spiropidion, spiromesifen, tebufenpyrad, tetradifon and flupentiofenox, etc.:
Nematicides, such as aluminum phosphide, benclothiaz, cadusafos, ethoprophos, fluazaindolizine, fluensulfone, fosthiazate, furfural, imicyafos, levamisol hydrochloride, mesulfenfos, metam-ammonium, methyl isocyanate, morantel tartarate, oxamyl, thioxazafen, etc.;
Examples of poison bait include chlorphacinone, coumatetralyl, diphacinone, sodium fluoracetate, warfarin, and the like.

Examples of compounds with herbicidal activity include aclonifen, acifluofen-sodium, alachlor, alloxydim, amicarbazone, amidosulfuron, anilofos, asulam, atrazine, azimsulfuron, benfuresate, bensulfuron-methyl, bentazone, benthiocarb, benzobicyclon, benzofenap, bialaphos, and bifenox. , bromobutide, bromoxynil, butamifos, cafenstrole, calcium peroxide, carbetamide, cinosulfuron, clomeprop, cyclosulfamuron, cyhalofop-butyl, daimuron, desmedipham, diclofop-methyl, diflufenican, dimefuron, dimethametryn, dinoterube dinoterb), diquat, diuron, esprocarb, ethiozin, ethofumesate, ethoxysulfuron, etobenzanid, fenoxaprop-P-ethyl, fentrazamide, flucarbazone, flufenacet, flurtamone,

fluthiacet-methyl, foramsulfuron, glufosinate-ammonium, glyphosate-isopropylamine, glyphosate-trimesium, imazapyr, imazosulfuron, indanofan, iodosulfuron, ioxynil-octanoate, isoproturon, isoxadifen, isoxaflutole, lactofen, linuron , mefenacet, mesosulfuron, metamitron, methabenzthiazuron, metosulam, metribuzin, naproxamide, neburon, oxadiargyl, oxadiazon, oxaziclomefone, paraquat, pendimethalin, pentoxazone, phenmedipham, pretilachlor, propoxycarbazone, prosulfocarb, pyraclonil, pyraflufe n-ethyl, pyrazolate, pyrazosulfuron ethyl Examples include n-ethyl), pyributicarb, pyriftalid, pyriminobac-methyl, quizalofop-ethyl, sethoxydim, simazine, sulcotrione, sulfentrazone, thenylchlor, triaziflam, and tribufos.

In addition, examples of compounds having a plant growth regulating effect include 1-naphthylacetamide, 4-CPA, benzylaminopurine, butralin, calcium chloride, calcium formate, calcium peroxide, calcium sulfate, chlormequat chloride, choline, cyanamide, cyclanilide, daminozide, decyl alcohol, dichlorprop, ethephon, ethychlozate, flurprimidol, forchlorfenuron, gibberellic acid, indolebutyric acid, potassium maleic hydrazide ... It can also be used in a mixture with benzoyl peroxidase, ...
Repellents, such as capsaicin, carane-3,4-diol, citronellal, deet, dimethyl phthalate, hinokitiol, limonene, linalool, menthol, menthone, naphthalene, thiram, etc.;
Examples of synergists include methylenedioxynaphthalene, naphthyl propynyl ether, nitrobenzyl thiocyanate, octachlorodipropyl ether, pentyny! phthalimide, phenyl salioxon, piperonyl butoxide, safrole, sesamex, sesamin, sulfoxide, triphenyl phosphate, and verbutin.

The compounds of the present invention can be used as biological pesticides, for example, in the preparation of viruses such as Cytoplasmic polyhedrosis virus (CPV), Entomopox virus (EPV), Granulosis virus (GV), and Nuclear polyhedrosis virus (NPV), as well as in the preparation of insecticides such as Beauveria bassiana, Beauveria brongniartii, Monacrosporium phymatophagum, Paecilomyces fumosoroseus, Pasteuria penetrans, Steinernema carpocapsae, Steinernema glaseri, and Steinernema kushidae. Microbial pesticides used as insecticides or nematocides, such as Agrobacterium radiobactor, Bacillus subtilis, non-pathogenic Erwinia carotovora, non-pathogenic Fusarium oxysporum, Pseudomonas CAB-02, Pseudomonas fluorescens, Talaromyces flavus, Trichoderma atroviride, Trichoderma lignorum, etc.; Microbial pesticides used as fungicides, such as Xanthomonas campestris, A similar effect can be expected by mixing it with biological pesticides used as herbicides such as P. campestris.

In addition, as biological pesticides, for example, Amblyseius californicus, Amblyseius cucumeris, Amblyseius degenerans, Aphidius colemani, Aphidoletes aphidimyza, Chrysoperia carnea, Dacnusa sibirica, Diglyphus isaea, Encarsia formosa, Eretmocerus eremicus, Franklinothrips vespiformis, Harmonia axyridis, Hemiptarsenus It can also be used in combination with natural enemies such as Neochrysocharis formosa, Orius sauteri, Orius strigicollis, Phytoseiulus persimilis, Pilophorus typicus, and Piocoris varius, as well as pheromones such as codlelure, cuelure, geraniol, gyptol, liblure, looplure, methyl eugenol, orfralure, peachflure, phycilure, pyrimalure, and turpentine.

The agricultural and horticultural fungicide of the present invention can be used to prevent or exterminate harmful organisms that cause harm in agriculture, indoors, forests, livestock, hygiene, etc. Specific application scenes, target pests, and application methods are shown below, but the contents of the present invention are not limited thereto.
The agricultural and horticultural fungicide of the present invention can be effectively used on agricultural crops, for example, edible crops (rice, barley, wheat, rye, oats, and other wheat varieties; potatoes, sweet potatoes, taro, yams, and other potatoes; beans, such as soybeans, adzuki beans, broad beans, peas, kidney beans, and peanuts; corn, millet, buckwheat, and the like); vegetables (Brassicaceae crops, such as cabbage, Chinese cabbage, radish, turnip, broccoli, cauliflower, and komatsuna; Cucurbitaceae crops, such as pumpkin, cucumber, watermelon, melon, zucchini, yugao, and bitter melon; Solanaceae crops, such as eggplant, tomato, bell pepper, chili pepper, and shishito pepper; okra, and the like. Malvaceae crops, Chenopodiaceae crops such as spinach and common burdock, Apiaceae crops such as carrots, mitsuba, parsley, celery, and burdock, Asteraceae crops such as lettuce and burdock, garlic, onions, green onions, Chinese chives, shallots, and other alliums, asparagus, shiso, lotus root, etc.), mushrooms (shiitake mushrooms, mushrooms, etc.), fruit trees and fruits (citrus fruits, apples, pears, peaches, plums, cherries, pears, apricots, grapes, persimmons, loquats, figs, akebia, blueberries, raspberries, pineapples, mangoes, kiwi fruits, bananas, strawberries, olives, walnuts, chestnuts, almonds, etc.),

It is used in the cultivation of ornamental crops such as spices (lavender, rosemary, thyme, sage, pepper, ginger, etc.), specialty crops (tobacco, tea, sugar beet, sugar cane, rushes, sesame, konjac, hops, cotton, hemp, olives, rubber, coffee, rapeseed, sunflowers, mulberry, etc.), pasture and feed crops (legume pasture grasses such as timothy, clover, alfalfa, corn, sorghum, orchard grass, etc.), turf grasses (Korean grass, bentgrass, etc.), forest trees (Japanese spruce, pines, Japanese cypress, cedar, Japanese cypress, etc.), and ornamental plants (herbaceous plants and flowers such as chrysanthemums, roses, carnations, lilies, lisianthus, perennial baby's breath, statice, orchids, garden trees such as ginkgo, cherry blossoms, and aoki trees, etc.).

The pathogens targeted by the agricultural and horticultural fungicide composition of the present invention are, for example, fungi and bacteria such as Eumycota, Myxomycota, Bacteriomycota, and Actinomycota, and the fungicide composition can be used to control diseases caused by these fungi and bacteria.
Specific examples of diseases include rice blast disease (Pyricularia oryzae), brown spot disease (Cochliobolus miyabeanus), sheath blight disease (Rhizoctonia solani), brown spot disease (Pantoea ananatis), Gibberella fujikuroi, damping-off disease (Pythium graminicolum), brown stripe disease (Acidovorax avenae subsp. avenae), brown sheath disease (Pseudomonas fuscovaginae), and white leaf blight disease (Xanthomonas oryzae pv. oryzae), bacterial blight (Burkholderia plantarii), etc.; powdery mildew of wheat (Erysiphe graminis), red mold disease (Gibberella zeae), red rust disease (Puccinia striiformis, P. graminis, P. recondita, P. hordei), snow mold disease (Typhula sp., Micronectriella nivalis), naked smut (Ustilago tritici, U. nuda), cattle smut (Tilletia caries),

Eyespot disease (Pseudocercosporella herpotrichoides), cloud disease (Rhynchosporium secalis), leaf blight (Septoria tritici), leaf spot disease (Leptosphaeria nodorum), net spot disease (Pyrenophora teres), hail disease (Helminthosporium zonatum Ikata), black node disease (Pseudomonas syringae pv. japonica), etc.; black spot disease of citrus fruits (Diaporthe citri), scab disease (Elsinoe fawcetti), fruit rot disease (Penicillium digitatum, P. italicum), brown rot (Phytophthora citrophthora, P. nicotianae), black spot (Phyllostictina citricarpa), etc.; Monilia mali, brown spot (Diplocarpon mali) of apple,

Canker (Valsa mali), Powdery mildew (Podosphaera leucotricha), Leaf spot (Alternaria mali), Black spot (Venturia inaequalis), Black spot (Mycospherella pomi), Anthracnose (Colletotrichum acutatum, Colletotrichum gloeosporioides), Ring spot (Botryosphaeria berengeriana), Red star (Gymnosporangium yamadae), Sooty spot (Zygophiala jamaicensis), Sooty spot (Gloeodes pomigena), etc.; pear black spot (Venturia nashicola, V. pirina), powdery mildew (Phyllactinia mali), black spot (Alternaria kikuchiana), red spot (Gymnosporangium haraeanum),

Brown rot (Monilinia fructigena), ring spot (Botryosphaeria berengeriana), etc.; brown rot (Monilinia fructicola), anthracnose (Glomerella cingulata), young fruit sclerotinia (Monilinia kusanoi), etc.; brown rot (Monilinia fructicola), black spot (Cladosporium carpophilum), phomopsis rot (Phomopsis sp.), bacterial hole (Xanthomonas campestris pv. pruni), etc.; black rot (Elsinoe ampelina), late blight (Colletotrichum acutatum, Glomerella cingulata), powdery mildew (Uncinula necator), rust (Phakopsora ampelopsidis), black rot (Guignardia bidwellii), downy mildew (Plasmopara viticola), black spot (Cladosporium viticolum), crown gall bacterial disease (Agrobacterium vitis), etc.; anthracnose of persimmon (Gloeosporium kaki), powdery mildew (Phyllactinia kakicola), leaf drop (Cercospora kaki, Mycoshaerella nawae), kiwifruit angular spot (Phomopsis sp.), anthracnose (Colletotrichum gloeosporioides, Colletotrichum acutatum), white root rot (Rosellinia necatrix),

Biwa brown spot (Phyllosticta eriobotryae), angular spot (Pseudocercospora eriobotryae), etc.; cucumber anthracnose (Colletotrichum lagenarium), powdery mildew (Podosphaera xanthii, Sphaerotheca fuliginea, Oidiopsis taurica), vine wilt (Didymella bryoniae), vine split (Fusarium oxysporum), downy mildew (Pseudoperonospora cubensis), late blight (Phytophthora sp. ), seedling damping-off (Pythium sp., Rhizoctonia solani), etc.; cucumber bacterial spot disease (Pseudomonas syringae pv. lochrymans), edge rot disease (Pseudomonas viridiflava), brown spot disease (Xanthomonas campestris pv. cucurbitae), etc.; melon bacterial brown spot disease (Xanthomonas campestris pv. cucurbitae), hairy root disease (Agrobacterium rhizogens), canker disease (Streptomyces sp.), etc.; watermelon fruit blotch bacterial disease (Acidovorax avenae pv. citrulli), etc.; solanaceous vegetable bacterial wilt disease (Ralstonia solanacearum), etc.; tomato ring spot disease (Alternaria solani), leaf mold disease (Cladosporium fulvum),

Phytophthora infestans, Pseudocercospora fuligena, Erysiphe cichoracearum, Clavibacter michiganense subsp. michiganense, Pseudomonas corrugata, Pectobacterium carotovorum subsp. carotovorum, etc.; Eggplant brown spot disease (Phomopsis vexans), Erysiphe cichoracearum), sooty mold (Mycovellosiella nattrassii), black blight (Corynespora melongenae),

Paracercospora egenula, brown rot (Phytophthora capsici), Verticillium dahliae, etc.; downy mildew (Peronospora parasitica) on cruciferous vegetables, black spot disease (Alternaria japonica), vitiligo disease (Cercosporella brassicae) soft rot (Pectobacterium carotovorum subsp. carotovorum), yellowing disease (Verticillium dahliae), etc.; cabbage rot disease (Pseudomonas syringae) pv. marginalis), black rot (Xanthomonas campestris pv. campestris), etc.; lettuce downy mildew (Bremia lactucae), bottom rot (Rhizoctonia solani), rot (Pseudomonas cichorii, Pseudomonas viridiflava),

Bacterial spot disease (Xanthomonas campestris pv. vitians), onion downy mildew (Peronospora destructor), black spot disease (Alternaria porri), rust disease (Puccinia allii), southern blight (Sclerotium rolfsii), etc.; soybean purple spot disease (Cercospora kikuchii), anthracnose disease (Colletotrichum truncatum, Colletotrichum trifolii, Glomerella glycines, Gloeosporium sp.),

Downy mildew (Peronospora manshurica), stem rot (Phytophthora sojae), black rot (Elsinoe glycines), black spot (Diaporthe phaseolum var. sojae), bacterial spot (Pseudomonas savastanoi pv. glycinea), leaf spot (Xanthomonas campestris pv. glycines), etc.; bean anthracnose (Colletotrichum lindemthianum), halo blight (Pseudomonas savastanoi pv. phaseolicola), leaf rot (Xanthomonas campestris pv. phaseoli), leaf rot (Rhizoctonia solani), etc.;

Black spot disease (Cercospora personata), brown spot disease (Cercospora arachidicola) of peas, etc.; powdery mildew (Erysiphe pisi) of peas, etc.; summer blight (Alternaria solani), late blight (Phytophthora infestans), leaf rot disease fungus (Rhizoctonia solani), soft rot disease (Pectobacterium carotovorum subsp. carotovorum) of potatoes, powdery mildew (Sphaerotheca humuli), anthracnose (Colletotrichum gloeosporioides, Colletotrichum actatum, Glomerella cingulata), Late blight (Phytophthora nicotianae), Ring blight (Dendrophoma obscurans), Bacterial bud blight ( Pseudomonas marginalis pv. marginalis) etc.;

Brown round spot disease (Pseudocercospora theae), anthracnose disease (Discula theae-sinensis), ring spot disease (Pestalothiopsis theae, Pestalotiopsis longiseta), net blight disease (Exobasidium reticulatum), blight disease (Exobasidium vexans), white spot disease (Elsinoe leucospila), red burn disease (Pseudomonas syringae pv. theae), canker disease (Xanthomonas campestris pv. theicola), etc. of tea; red spot disease (Alternaria longipes), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), late blight (Phytophthora nicotianae), damping-off (Ralstonia solanacearum), cavitation disease (Pectobacterium carotovorum subsp. carotovorum), etc.; sugar beet brown spot disease (Cercospora beticola);

Root rot (Rhizoctonia solani, Thanatephorus cucumeris), damping off (Aphanomyces cochliodes), etc.; black spot of roses (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa), etc.; brown spot of chrysanthemums (Septoria chrysanthemi-indici), white rust (Puccinia horiana), crown gall (Agrobacterium tumefaciens), etc.; gray mold of eggplant, cucumber, lettuce, and other crops (Botrytis cinerea), sclerotinia rot (Sclerotinia sclerotiorum); snow mold disease of turfgrass (Pythium iwayamai, Tyohula incarnate, Fusarium nivale, Sclerotinia borealis), powdery mildew (Erysiphe graminis), fary ring disease (Lycoperdon perlatum, Lepista subnudo, Marasmius oreades),

Pseudoleaf rot (Ceratobasidium spp.), damping off (Gaemannomyces graminis), Curvularia leaf blight (Curvularia geniculata), leaf rot (Rhizoctonia solani), Pythium disease (Pythium periplocum, Pythium vanterpoolii), rust (Puccinia spp.), dollar spot (Sclerotinia homoeocarpa), etc.; red burn disease of bentgrass (Pythium aphanidermatum), anthracnose (Colletotrichum sp.), Shark skin blight of Botryosphaeria (Botryosphaeria sp.), Anthracnose (Glomerella cingulata), Ring spot disease of hydrangea (Phoma exigua), Spot disease (Phyllosticta hydrangeae), Brown spot disease (Corynespora cassiicola), Leaf rot disease (Rhizoctonia solani), Powdery mildew (Oidium sp.), Anthracnose (Glomerella cingulata),

Ring spot disease (Cercospora hydroangeae), sooty spot disease of ginkgo (Gonatobotryum apiculatum), red blotch disease (Erythricium salmonicolor), red spot disease of moss (Gymnosporangium yamadae), white root rot disease (Rosellinia necatrix), black spot disease of maples (Rhytisma acerinum), ring leaf blight (Cristulariella moricola), canker disease (Diaporthe sp.), sooty spot disease (Cercospora sp.), anthracnose disease (Colletotrichum gloeosporioides), red leaf spot disease (Erythricium salmonicolor), powdery mildew (Uncinula sp., Sawadaea sp., Oidium sp.), white spot disease of oak (Phomatospora albomaculans), powdery mildew (Uncinula sp.,

Microsphaera alphitoides, Erysiphe gracilis, pine rot disease (Armillaria mellea), heart rot disease (Phaeolus schweinitzii), brown spot disease of bilberry (Septoria chinensis), canker disease (Diaporthe melanocarpa, Diaporthe alleghaniensis), camphor tree anthracnose (Glomerella cingulata), gardenia sooty mold disease (Passalora okinawaensis), leaf spot disease (Phaeosphaerella gardeniae), Zelkova brown spot disease (Pseudocercospora zelkova), Armillaria mellea, Phyllactinia magnolia,

Spot disease (Phyllosticta concentrica), canker disease of cherry trees (Nectria galligena), crown gall disease (Agrobacterium tumefaciens), powdery mildew (Podosphaera longiseta, Podosphaera tridactyla), witches' broom disease (Taphrina wiesneri), young fruit sclerotinia disease (Monilinia kasanoi), bamboo shoot disease (Armillaria mellea), canker disease (Valsa ambiens), pomegranate scab disease (Sphaceloma punicae), powdery mildew of sarusube (Uncinuliella australia), brown spot disease (Pseudocercospora lythracearum), ring leaf blight (Cristulariella moricola), sooty mold disease of hawthorn (Pseudocercospora crataegi), white spot disease of chinquapin (Bagcheea albo-maculans), leaf blister disease (Taphrina kusanoi), anthracnose disease of rhododendrons (Colletotrichum gloeosporioides), leaf spot disease (Pseudocercospora handelii), white root rot (Rosellinia necatrix), cedar branch blight (Sclerotium sp.), red wilt (Cercospora sequoiae),

Microscopic sclerotinia disease (Macrophomma phaseolina), red leaf blight of scutellaria (Ascochyta sp.), powdery mildew of azaleas (Microsphaera izuensis), brown spot disease (Septoria azaleae), white root rot disease (Rosellinia necatrix), damping-off disease (Rhizoctonia solani), leaf spot disease (Pseudocercospora handelii), spot disease (Phyllosticta maxima), flower rot disease (Ovulinia azaleae), witches' broom disease (Exobasidium pentasporium), camellia root rot (Phytophthora cinnamomi), anthracnose (Glomerella cingulata), false acacia rot (Armillariella mellea), rose powdery mildew (Sphaerotheca pannosa, Oidium sp.),

Downy mildew (Peronospora sparsa), leaf spot (Cercospora rosicola, Mycosphaerella rosicola), late blight (Phytophthora megasperma), black spot (Marssonina rosae, Diplocarpon rosae), canker (Cryptosporella umbrina), white root rot (Rosellinia necatrix), Japanese cypress leaf spot (Armillariella mellea), Pestalotia disease (Pestalothiopsis sp.), Fuji club (Erwinia herbicola pv.) millettiae), poinsettia root rot (Rythium sp.), peony blight (Phytophthora cactorum), powdery mildew (Erysiphe paeoniae),

Bloom blight (Alternaria sp.), anthracnose (Gloeosporium sp.), brown spot (Pseudocercospora varicolor), sclerotinia sclerotiorum, damping off (Botrytis paeoniae), white root rot (Rosellinia necatrix), powdery mildew (Oidium euonymi-japonici), brown spot (Pseudocercospora destructiva), pine club (Cronartium quercuum), seedling damping off (Rhizoctonia solani, Fusarium sp., Pythium sp., Leaf blight (Pseudocercospora pini-densiflorae), Black spot disease of pineapple (Coccoidea querricola), Powdery mildew of dogwood (Microsphaera pulchra),

Pseudocercospora cornicola, Marzonina leaf drop of willows (Marssonina brunnea), Cercospora epicoccoides, Pseudocercospora spiraeicola, powdery mildew (Sphaerotheca spiraeae), powdery mildew of lilacs (Microsphaera syringae-japonicae), Sclerotinia sclerotiorum, Fusarium oxysporum f. sp. batatas), powdery mildew of carnation (Oidium dianthi), powdery mildew of gerbera (Sphaerotheca fuliginea), anthracnose (Colletotrichum sp.), sclerotinia sclerotiorum, chrysanthemum wilt (Fusarium oxysporum),

Powdery mildew (Erysiphe cichoracearum), Sclerotinia sclerotiorum, Verticillium dahliae, Fusarium wilt (Fusarium solani), Snapdragon anthracnose (Colletotrichum gloeosporioides), Powdery mildew (Oidium subgenus Reticuloidium), Sclerotinia sclerotiorum, Cosmos anthracnose (Colletotrichum acutatum, Gloeosporium sp.), powdery mildew (Sphaerotheca fusca), sclerotinia sclerotiorum, powdery mildew of perennial gypsophila (Oidium sp.), damping-off (Fusarium moniliforme),

Sclerotinia sclerotiorum, powdery mildew of sweet pea (Oidium sp.), wilt (Fusarium sp.), verticillium wilt (Verticillium dahliae), anthracnose (Glomerella cingulata, Colletotrichum gloeosporioides), anthracnose of statice (Glomerella cingulata), powdery mildew (Oidium sp.), stock wilt (Fusarium oxysporum Schlechtendahl: Fries f. sp. conglutinans), Sclerotinia sclerotiorum, anthracnose (Colletotrichum gloeosporioides, Colletotrichum higginsianum), damping-off (Fusarium avenaceum), Verticillium dahliae, Lisianthus anthracnose (Colletotrichum acutatum),

Stalk rot (Fusarium avenaceum), powdery mildew (Oidium sp.), sclerotinia sclerotiorum, sunflower powdery mildew (Sphaerotheca fusca, Erysiphe cichoracearum), sclerotinia sclerotiorum, brown spot (Septoria helianthi), verticillium wilt (Verticillium dahliae), petunia powdery mildew (Sphaerotheca fuliginea, Oidium sp.), sclerotinia sclerotiorum), and marigold verticillium wilt (Verticillium dahliae).

The agricultural and horticultural fungicide of the present invention is an agent which is highly safe to crops and useful organisms and has low toxicity to various organisms such as fish and warm-blooded animals.
The agricultural and horticultural fungicide of the present invention has excellent fungicidal activity even against resistant bacteria that are resistant to existing agents such as benzimidazole agents, dicarboximide agents, anilinopyrimidine agents, strobilurin agents, SDHI agents, and fluazinam agents, which are causing problems.
The agricultural and horticultural fungicide of the present invention can also be used to prevent and treat diseases of the skin, digestive system, respiratory system, and other organs of humans, livestock, and pets.

Specific examples of pathogenic bacteria that are the cause of disease include fungi such as tinea fungi Trichophyton rubrum and Trichophyton mentagrophytes, candida fungi Candida albicans, and aspergillus fungi Aspergillus fumigatus, gram-negative bacteria such as Escherichia coli and Pseudomonas aeruginosa, and gram-positive bacteria such as Staphylococcus aureus.

The compound of the present invention can be used as a mixture with compounds having insecticidal, acaricidal, or nematocidal activity, as well as with other active compounds other than those, in addition to compounds having fungicidal activity. In order to control diseases and/or weeds that occur simultaneously during the period of use, by mixing with a compound having fungicidal, herbicidal, or plant growth regulating activity, a synergistic effect such as a reduction in the amount of drug as well as a reduction in the control effort can be expected. In addition, by mixing with a repellent, synergist, etc., a more effective control effect such as a synergistic effect can be expected.

The agricultural and horticultural fungicide of the present invention can be used as it is, or in a form generally available for use as an agricultural chemical, such as a wettable powder, a wettable granule, a dry flowable agent, a water-soluble agent, an emulsion, a liquid agent, an oil agent, an aqueous suspension agent or an aqueous emulsion, or other flowable agent, capsule, powder, granule, fine granule, bait, tablet, spray, aerosol, or the like. The agricultural and horticultural fungicide of the present invention generally contains 0.1 to 99.9% by mass, preferably 0.2 to 80% by mass, of the active ingredients in total.

To obtain the above formulation, various pesticide adjuvants that have been conventionally used in the technical field of agricultural and horticultural fungicides can be used as appropriate. Such pesticide adjuvants can be used, for example, for the purpose of improving the effect, stabilizing, and improving the dispersibility of agricultural and horticultural fungicides. Examples of pesticide adjuvants include carriers (diluents), spreading agents, emulsifiers, wetting agents, dispersants, and disintegrants.

Liquid carriers include water, aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol, butanol and glycol, ketones such as acetone, amides such as dimethylformamide, sulfoxides such as DMSO, methylnaphthalene, cyclohexane, animal and vegetable oils, fatty acids, etc. Also, solid carriers include clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, montmorillonite, bentonite, feldspar, quartz, alumina, sawdust, nitrocellulose, starch, gum arabic, etc.

As the emulsifier or dispersant, a conventional surfactant can be used, for example, anionic surfactants such as higher alcohol sodium sulfate, stearyl trimethyl ammonium chloride, polyoxyethylene alkyl phenyl ether, lauryl betaine, cationic surfactants, nonionic surfactants, amphoteric surfactants, etc. can be used. In addition, a spreading agent; a wetting agent such as dialkyl sulfosuccinate; a fixing agent such as carboxymethyl cellulose or polyvinyl alcohol; a disintegrating agent such as sodium lignin sulfonate or sodium lauryl sulfate, etc. can be used.

To control pathogens such as fungi, the agent is usually sprayed on the stems and leaves of plants in areas where damage caused by these pathogens has occurred or is likely to occur. In addition, the agent can be applied to the soil and absorbed through the roots by mixing into the entire soil layer, applying in rows, applying in side rows, mixing into bed soil, treating cell seedlings, treating in planting holes, treating the base of plants, top dressing, treating in rice boxes, applying to the water surface, etc. In addition, the agent can be used for seed treatment such as soaking seeds in the agent, seed dressing, treating with Calper, applying to nutrient solution in nutrient solution (hydroponic) cultivation, smoking, or injecting into tree trunks, etc.

When using the agricultural and horticultural fungicide of the compound of the present invention, the total amount of active ingredient is generally 0.01 to 1000 g, preferably 0.1 to 100 g, per 10 ares, although this varies depending on the type of pathogen, the amount of occurrence, the type of crop or tree to be treated, the cultivation form, and the growth state, etc. To treat this, in the case of wettable powders, wettable granules, dry flowables, water-soluble powders, emulsions, liquids, aqueous suspensions, aqueous emulsions, and other flowables, capsules, etc., the agent is diluted with water and sprayed on crops, etc. in an amount of generally 10 to 1000 liters per 10 ares, although this varies depending on the type of plant to be treated, the cultivation form, and the growth state, etc. In addition, in the case of powders, sprays, or aerosols, the agent may be applied to crops, etc. in the form of the formulation.

In cases where the target pathogen mainly harms plants in the soil, or where the agent is absorbed through the roots to control the target pathogen, examples of application methods include applying the formulation, diluted with or without water, to the base of the plant or to a seedling bed, spraying granules to the base of the plant or to a seedling bed, spraying a dust, wettable powder, wettable granule, granule, etc. before sowing or transplanting and mixing with the entire soil, and spraying a dust, wettable powder, wettable granule, granule, fine granule, etc. in planting holes, rows, etc. before sowing or planting the plant. For wettable powders, wettable granules, water-soluble concentrates, emulsions, liquids, aqueous suspensions, aqueous emulsions, and other flowable agents, capsules, etc., the agent may be diluted with water and sprayed or irrigated into the soil surface so that the entire treatment area is evenly distributed. In the case of powders, granules, fine granules, baits, etc., the formulations may be applied evenly to the soil surface over the entire area to be treated. Spraying or irrigation may be performed around the seeds, crops, or trees to be protected from damage. The active ingredient may also be mechanically dispersed by tilling during or after spraying. When treating the soil, the total amount of active ingredient applied will vary depending on the type and amount of pathogen, the type and cultivation form/growing condition of the target crop or tree, and the type of soil, but generally 0.01 to 1000 g, preferably 0.1 to 500 g, of the active ingredient is applied per 10 ares.

The method of application to rice seedling boxes may vary depending on the time of application, such as application at the time of sowing, application during the greening period, or application at the time of transplanting. For example, powders, water dispersible granules, granules, and fine granules can be used as is, while water dispersible agents, water dispersible granules, water soluble agents, emulsions, liquid agents, aqueous suspensions, aqueous emulsions, and other flowable agents, and capsules can be diluted with water and applied. Application can also be by mixing with the culture soil, and the culture soil can be mixed with the powder or granules, for example, by mixing with the bed soil, covering soil, or the entire culture soil. Alternatively, the culture soil and various formulations can simply be layered alternately and applied.

For application to paddy fields, solid preparations such as jumbo formulations, pack formulations, granules, and granular water dispersible agents, or liquid preparations such as flowables and emulsions are usually sprayed on flooded paddy fields. In addition, at the time of rice planting, appropriate preparations can be sprayed or injected directly or mixed with fertilizers and then sprayed on the soil. Also, by using liquids such as water dispersible agents, emulsions, and flowables at the water inlet or irrigation equipment, where water flows into the paddy field, application can be labor-saving in conjunction with the water supply.

Examples of seed treatment methods include a method in which seeds are immersed in a liquid or solid formulation, diluted or undiluted, to allow the agent to adhere to and penetrate the seeds, a method in which a solid or liquid formulation is mixed with the seeds and powder-coated to allow the agent to adhere to the surface of the seeds, a method in which the formulation is mixed with an adhesive carrier such as a resin or a polymer and then coated on the seeds, a method in which the formulation is sprayed around the seeds at the same time as planting, etc. The "seed" to be subjected to the seed treatment means a plant body in the early stage of cultivation used for plant propagation, and examples thereof include, in addition to the seed itself, bulbs, tubers, seed potatoes, sprouts, bulbils, bulbs, or plant bodies for vegetative propagation for cultivation by cuttings. Furthermore, the term "soil" or "cultivation carrier" for plants in the case of application refers to a support for cultivating crops, particularly a support for growing roots, and the material is not particularly limited as long as it is a material in which plants can grow, and may be so-called soil, seedling mat, water, etc., and specific materials include, for example, sand, pumice, vermiculite, diatomaceous earth, agar, gel-like substances, polymeric substances, rock wool, glass wool, wood chips, bark, etc. When used, the total amount of active ingredients per kilogram of seeds is 0.001 to 50 g, preferably 0.01 to 10 g.
As treatments for cultivated plants to be transplanted during the sowing and seedling raising stages, in addition to direct treatment of seeds, irrigation of liquid agents or spraying of granules on seedling beds is preferred. It is also preferred to apply granules to planting holes at the time of planting or to mix them into cultivation carriers near the transplanting site.

The agricultural and horticultural fungicide of the present invention can be used to prevent and treat the occurrence and spread of diseases of organs such as the skin, digestive system, and respiratory system by parasitizing on or inside the body of humans, livestock, and pets. In such a situation, the compound of the present invention can be mixed in a small amount into food or feed, or administered orally as an appropriate orally ingestible compounded pharmaceutical composition, such as tablets, pills, capsules, pastes, gels, beverages, medicated feed, medicated drinking water, medicated follow-up feed, sustained-release large pills, or other sustained-release devices that are retained in the gastrointestinal tract, containing a pharma-ceutical acceptable carrier or coating material, or administered transdermally as a spray, powder, grease, cream, ointment, emulsion, lotion, spot-on, pour-on, shampoo, etc. In order to achieve the effect by such a method, the total amount of the compound of the present invention is generally 0.0001 to 0.1%, preferably 0.001 to 0.01%, by mass.

The present invention will be explained in more detail below with reference to examples, formulation examples, and test examples, but the scope of the present invention is not limited in any way by these examples, formulation examples, and test examples.

Example 1
Synthesis of N-[2-(2,4-dichlorophenyl)-2,2-difluoroethyl]-8-methyl-5-[3-(trifluoromethyl)phenoxy]imidazo[1,5-a]pyridine-7-carboxamide (compound number: A-2)

1-1: Synthesis of 2-chloro-5-fluoro-3-methylpyridine-4-carboxylic acid Commercially available 2-chloro-5-fluoro-3-methylpyridine (5 g) was dissolved in tetrahydrofuran (80 ml) and stirred at -80 ° C for 30 minutes. Lithium diisopropylamide (1.1 M hexane solution, 40 ml) was then added dropwise, and the mixture was stirred at the same temperature for 1 hour and 30 minutes, and dry ice was added little by little. The reaction solution was further stirred at room temperature for 1 hour, and then cooled on ice and acidified with 1N hydrochloric acid. The mixture was then extracted with ethyl acetate, washed with saturated saline, and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure to obtain 6 g of a white solid (yield 93%).

1-2: Synthesis of ethyl 2-chloro-5-fluoro-3-methylpyridine-4-carboxylate
2-Chloro-5-fluoro-3-methylpyridine-4-carboxylic acid (5g) was dissolved in tetrahydrofuran (70ml), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (5.8g), dimethylaminopyridine (400mg) and ethanol (8ml) were added, and the mixture was stirred at room temperature for 5 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate, washed with water, saturated sodium bicarbonate water, and saturated saline, and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure, and column chromatography was performed to obtain 4.5g of a colorless oil (yield 80%).

1-3: Synthesis of ethyl 2-cyano-5-fluoro-3-methylpyridine-4-carboxylate 2-Chloro-5-fluoro-3-methylpyridine-4-carboxylate (1 g) was dissolved in N,N-dimethylformamide (15 ml) in a reaction vessel, tetrakistriphenylphosphine palladium (600 mg) and zinc cyanide (600 mg) were added, the vessel was sealed, and the mixture was stirred at 120 ° C for 30 minutes while irradiating with microwaves. After completion of the reaction, the mixture was filtered through Celite, and water was added to the residue. Then, the mixture was extracted with ethyl acetate and washed with saturated saline. After concentration under reduced pressure, column chromatography was performed to obtain 930 mg of a colorless oil (yield 97%).

1-4: Synthesis of ethyl 2-cyano-3-methyl-5-[3-(trifluoromethyl)phenoxy]pyridine-4-carboxylate 60% sodium hydride (900 mg) was suspended in N,N-dimethylformamide (65 ml), and 3-trifluoromethylphenol (2.7 ml) was added dropwise under ice cooling. After stirring at the same temperature for 30 minutes, the mixture was stirred at room temperature for 30 minutes. After confirming that the generation of bubbles had ceased, the mixture was returned to ice cooling, and ethyl 2-cyano-5-fluoro-3-methylpyridine-4-carboxylate (4 g) was added. The mixture was stirred overnight at room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, 10% NaOH aqueous solution, and saturated saline, and dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, column chromatography was performed to obtain 6.7 g of a colorless oil (yield 99%).

1-5: Synthesis of ethyl 2-(aminomethyl)-3-methyl-5-[3-(trifluoromethyl)phenoxy]pyridine-4-carboxylate
Ethyl 2-cyano-3-methyl-5-[3-(trifluoromethyl)phenoxy]pyridine-4-carboxylate (4 g) was dissolved in ethanol (50 ml), di-tert-butyl dicarbonate (3.4 g) and palladium-activated carbon (10% activated, 600 mg) were added, and the mixture was substituted with hydrogen. After stirring at room temperature for 3 hours, the mixture was filtered through Celite, and the remaining liquid was concentrated under reduced pressure. The resulting compound was dissolved in methylene chloride (30 ml), 4M hydrochloric acid/dioxane (20 ml) was added, and the mixture was stirred at room temperature for 5 hours. The reaction liquid was concentrated under reduced pressure and made basic with saturated sodium bicarbonate water. The mixture was extracted with ethyl acetate, washed with saturated saline, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 2.2 g of a pale yellow oil (2-step yield 52%).

1-6: Synthesis of ethyl 2-(formamidomethyl)-3-methyl-5-[3-(trifluoromethyl)phenoxy]pyridine-4-carboxylate
Ethyl 2-(aminomethyl)-3-methyl-5-[3-(trifluoromethyl)phenoxy]pyridine-4-carboxylate (2.2 g) was dissolved in ethyl formate (5 ml) and stirred under reflux for 2 hours. The solvent was removed under reduced pressure to give 2.2 g of a brown oil (yield 93%).

1-7: Synthesis of ethyl 8-methyl-6-[3-(trifluoromethyl)phenoxy]imidazo[1,5-a]pyridine-7-carboxylate
2-(Formamidomethyl)-3-methyl-5-[3-(trifluoromethyl)phenoxy]pyridine-4-carboxylate ethyl (1 g) was dissolved in toluene (5 ml) and phosphoryl chloride (2 ml) was added dropwise. The reaction solution was stirred under heating and reflux for 2 hours. The reaction solution was added to ice water, made basic with aqueous sodium hydroxide solution, extracted with chloroform, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 1 g of a black oil (yield 99%).

1-8: Synthesis of 8-methyl-6-[3-(trifluoromethyl)phenoxy]imidazo[1,5-a]pyridine-7-carboxylic acid
Ethyl 8-methyl-6-[3-(trifluoromethyl)phenoxy]imidazo[1,5-a]pyridine-7-carboxylate (1 g) was dissolved in ethanol (10 ml), 10% aqueous sodium hydroxide solution (2 ml) was added, and the mixture was stirred at room temperature for 3 hours. The reaction solution was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The mixture was washed with water and saturated saline, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain 600 mg of a brown solid (yield 66%).

1-9: Synthesis of N-[2-(2,4-dichlorophenyl)-2,2-difluoroethyl]-8-methyl-6-[3-(trifluoromethyl)phenoxy]imidazo[1,5-a]pyridine-7-carboxamide
8-Methyl-6-[3-(trifluoromethyl)phenoxy]imidazo[1,5-a]pyridine-7-carboxylic acid (160 mg) was dissolved in pyridine (3 ml), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (190 mg), 1-hydroxybenzotriazole monohydrate (220 mg) and 2-(2,4-dichlorophenyl)-2,2-difluoroethylamine (110 mg) were added, and the mixture was stirred at room temperature for 5 hours. After completion of the reaction, the mixture was concentrated under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate and washed with saturated saline. After concentration under reduced pressure, column chromatography was performed to obtain 77 mg of a brown oil (yield 28%).

Table 1 below lists the compound of Example 1 as well as other compounds of the present invention that were prepared in a manner similar to that of Example 1.

Table 1

The NMR data for the compounds of the present invention prepared in the examples are as follows:

The following Tables 3 and 4 show the chemical formula and NMR data of the intermediate of the present invention represented by formula (II), which was produced in the same manner as in the Examples.

（II）

(II)

Table 3

The NMR data for the intermediate of the present invention obtained is as follows:

The following Tables 5 and 6 show the chemical formula and NMR data of the intermediate of the present invention represented by formula (XVI), which was prepared in the same manner as in the Examples.

（ＸＶＩ）

(XVI)

Table 5

The NMR data of the intermediate of the present invention represented by the compound formula (XVI) obtained above is as follows:

The following are examples of formulations of agricultural and horticultural fungicides. Note that parts are by weight.

The following formulation examples are used to specifically explain formulations containing the compound of the present invention, but the compound of the present invention, auxiliary ingredients, and the amounts of these to be added are not limited to the following formulation examples. Note that all parts in the formulation examples are by weight.

Formulation Example 1 Emulsion The compound of the present invention (10 parts), xylene (60 parts), N-methyl-2-pyrrolidone (20 parts), and Sorpol 3005X (a mixture of a nonionic surfactant and an anionic surfactant, trade name, manufactured by Toho Chemical Industry Co., Ltd.) (10 parts) were uniformly mixed and dissolved to obtain an emulsion.

Formulation Example 2 Wettable Powder The compound of the present invention (20 parts), Toxil GU-N (white carbon, Oriental Silicas Corporation) (20 parts), Sorpol 5096 (polyoxyethylene styryl phenyl ether sulfate, Toho Chemical Industry Co., Ltd.) (10 parts), and SS Clay (clay, Showa KDE Corporation) (50 parts) were mixed and pulverized using a pulverizer to obtain a wettable powder.

Formulation Example 3 Water-soluble Compound The compound of the present invention (5 parts), Lunox P-65L (sodium alkylbenzenesulfonate, Toho Chemical Industry Co., Ltd.) (3 parts), and sodium hydrogen carbonate (reagent) (92 parts) were uniformly mixed and then pulverized using a pulverizer to obtain a water-soluble compound.

Production Example 4 Water Dispersible Granule The compound of the present invention (20 parts), Demol N (naphthalenesulfonate formalin condensate, Kao Corporation, trade name) (5 parts), Airroll CT-1L (dioctyl sulfosuccinate, Toho Chemical Industry Co., Ltd., trade name) (1 part), Cellogen 701A (carboxymethylcellulose, Daiichi Kogyo Seiyaku Co., Ltd.) (1 part), and Kaolin clay (kaolinite, Takehara Chemical Industry Co., Ltd., trade name) (73 parts) were uniformly mixed and ground in an air mill. Water was added to this mixture and thoroughly kneaded, followed by extrusion granulation, drying and sizing to obtain a water dispersible granule.

Formulation Example 5 Flowable The compound of the present invention (20 parts), Sorpol 7948 (polyoxyalkylene tristyryl phenyl ether sodium sulfate, Toho Chemical Industry Co., Ltd.) (5 parts), propylene glycol (reagent) (10 parts), and water (40 parts) were mixed in advance and wet-pulverized in a bead mill to obtain a slurry. Next, KELZAN (xanthan gum, Sansho Co., Ltd.) (0.2 parts) was thoroughly mixed and dispersed in water (24.8 parts) to prepare a gel-like material, which was thoroughly mixed with the pulverized slurry to obtain a flowable.

Formulation Example 6 EW-1
The compound of the present invention (20 parts) and New Calgen D-230 (polyoxyethylene castor oil, Takemoto Oil Co., Ltd.) (15 parts) are mixed and homogenized, and then water (59.8 parts) is gradually added while stirring to obtain a dispersion. This dispersion is dispersed in propylene glycol (reagent) (5.0 parts) and KELZAN (xanthan gum, Sansho Co., Ltd.) (0.2 parts) is added to obtain an emulsion preparation.

Formulation Example 7 EW-2
The compound of the present invention (10 parts) was dissolved in xylene (10 parts) and mixed with Rheodol 430V (polyoxyethylene sorbitol tetraoleate, Kao Corporation) (24 parts) to obtain a dispersion. This dispersion and water (50.8 parts) were dispersed in a homogenizer, and KELZAN (xanthan gum, Sansho Corporation) (0.2 parts) dispersed in propylene glycol (reagent) (5.0 parts) was added to obtain an emulsion preparation.

Formulation Example 8 Microemulsion A microemulsion was obtained by uniformly mixing the compound of the present invention (10 parts), xylene (reagent) (20 parts), Newcalgen D-230 (polyoxyethylene castor oil, Takemoto Oil & Fat Co., Ltd.) (20 parts), Airroll CT-1L (dioctyl sodium sulfosuccinate, Toho Chemical Industry Co., Ltd.) (2.0 parts), and water (48 parts).

Formulation Example 9 Liquid Preparation The compound of the present invention (20 parts), N-methyl-2-pyrrolidone (reagent) (70 parts), and Newcalgen D-230 (polyoxyethylene castor oil, Takemoto Oil Co., Ltd.) (10 parts) were uniformly mixed and dissolved to obtain a liquid preparation.

Formulation Example 10 Granule-1
The compound of the present invention (5 parts), Airroll CT-1L (dioctyl sodium sulfosuccinate, Toho Chemical Industry Co., Ltd.) (2 parts), Bentonite Sado (bentonite, Kunimine Kogyo Co., Ltd.) (30 parts), and NK-300 (clay, Showa KDE Co., Ltd.) (63 parts) were uniformly mixed, water was added, and the mixture was thoroughly kneaded, followed by extrusion granulation and drying/sizing to obtain granules.

Formulation Example 11 Granules-2
The compound of the present invention (5 parts) was dissolved in methanol (reagent), and the solution was adsorbed onto Ishikawa Light No. 2 (95 parts) using a tumbling granulator, followed by drying to obtain granules.

Formulation Example 12 Microgranules-1
The compound of the present invention (2 parts) was dissolved in methanol (reagent), and the solution was adsorbed onto Ishikawa Light No. 4 (98 parts) using a tumbling granulator, followed by drying to obtain fine granules.

Formulation Example 13: Microgranules-2
The compound of the present invention (5 parts) and Toxil GU-N (5 parts) were mixed and then pulverized using a fine grinding machine, and uniformly mixed with Iide quartz sand (silica sand, JFE Mineral Co., Ltd.) (80 parts). This mixture was further mixed while spraying an aqueous solution of Toxanon GR-31A (polycarboxylic acid type surfactant, Sanyo Chemical Industries, Ltd.) (10 parts) diluted with water to obtain a granular composition. This granular composition was dried to obtain a fine granule.

Formulation Example 14: Powder The compound of the present invention (5 parts), Toxil GU-N (5 parts) and Omori Micro Clay (clay, Omori Sangyo Co., Ltd.) (90 parts) were uniformly mixed and then pulverized using a pulverizer to obtain a powder.

Formulation Example 15 DL Dust The compound of the present invention (5 parts), propylene glycol (0.5 parts) and DL clay (94.5 parts) were uniformly mixed and then pulverized using a pulverizer to obtain a dust.

Formulation Example 16: Seed coating powder The compound of the present invention (10 parts), Poval PVA-117 (polyvinyl alcohol, Kuraray Trading Co., Ltd.) (1 part) and Omori fine clay (89 parts) were uniformly mixed and pulverized using a pulverizer to obtain a powder. The powder was mixed with pre-moistened seeds and air-dried to obtain coated seeds.

Formulation Example 17 Seed Coating Flowable The compound of the present invention (10 parts), Sorpol 7948 (5 parts), propylene glycol (reagent) (10 parts), and water (40 parts) were mixed in advance and wet-milled with a bead mill. Next, KELZAN (xanthan gum, Sansho Co., Ltd.) (0.2 parts) and water (29.8 parts) were thoroughly mixed and dispersed, and AMECOAT HCA/83 (acrylic acid polymer, SOLVAY) (5 parts) was mixed to prepare a gel-like material. The milled slurry and the prepared gel-like material were thoroughly mixed to obtain a flowable. This flowable was mixed with seeds and air-dried to obtain coated seeds.

Formulation Example 18 Oil suspension formulation The compound of the present invention (20 parts), Newkalgen C-120 (POE tristyrylphenyl ether, Takemoto Oil Co., Ltd., trade name) (5 parts), Rheodol TW-O120V (POE sorbitan monooleate, Kao Corporation, trade name) (10 parts), oleic acid methyl ester (Kanto Chemical Co., Ltd., reagent) (62 parts), and Esben NZ (organic bentonite, Hojun Co., Ltd., trade name) (3 parts) were thoroughly mixed and dispersed, and the resulting slurry dispersion was wet-pulverized to obtain an oil suspension formulation.

Next, the usefulness of the compounds of the present invention as active ingredients of fungicides will be demonstrated by test examples. The compounds of the present invention are indicated by the compound numbers in Table 1, and the compounds used for comparison are indicated by the compound symbols below.

Test Example 1: Test against cucumber gray mold Eight days after sowing, the cotyledon part was cut off, leaving about 2 cm of the hypocotyl of a cucumber seedling (variety: Sagami Hanshiro-Ketsuri). A paper towel sufficiently moistened with water was laid on the bottom of a plastic case of 32 cm x 24 cm x 4.5 cm (length x width x height), and a net was placed on the paper towel. The above-mentioned cut cotyledons were arranged on the net so that the cut surface of the hypocotyl was attached to the moistened lead paper. 40 μl of spore suspension (spore concentration: 1.0 x 10 ⁶ spores/ml) was dropped on the center of the cotyledon, and a paper disk of 8 mm in diameter was placed on it. 40 μl of a water dilution of the emulsion prepared according to Formulation Example 1 was dropped on the paper disk. The plastic case was covered with a lid and sealed with vinyl tape, and then kept at room temperature of 20° C. for 72 hours. Thereafter, the degree of disease was investigated according to the following criteria, and the control value was calculated according to the following formula.

Disease severity: 0 (no disease), disease severity: 6.25 (slight infestation marks), disease severity: 12.5 (spots extend to 5-8mm inside the paper disc), disease severity: 25 (spots extend to 2mm around the paper disc), disease severity: 50 (spots extend to 5mm to 10mm around the paper disc), disease severity: 100 (spots extend to 10mm or more around the paper disc)

Control value = [1-(disease severity in treated area/disease severity in untreated area)] x 100

As a result, the compounds shown by the following compound numbers exhibited a control effect of 80 or more at 400 ppm.

A-1, A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-9

The compound of the present invention represented by the general formula (I) exhibits a high control effect against various fungi that have developed resistance to conventional fungicides, and exerts the intended effect at a low dosage. Therefore, it is a highly safe compound with reduced problems such as residual toxicity and environmental pollution, and is a useful compound as an agricultural and horticultural agent.

Claims (3)

The following formula (I):

(Wherein,
R ¹ represents hydrogen, a C ₁ -C ₆ alkyl group, a C ₃ -C ₆ cycloalkyl group, or a C ₁ -C ₆ alkoxy group;
R ² and R ³ each independently represent a hydrogen atom or a C ₁ -C ₆ alkyl group, and R ² and R ³ may together form a C ₃ -C ₆ cycloalkyl group;
R ⁴ and R ⁵ each independently represent a hydrogen atom, a halogen atom, or a C ₁ -C ₆ alkyl group, and R ⁴ and R ⁵ may together form a C ₃ -C ₆ cycloalkyl group;
R ⁶ represents a hydrogen atom, a halogen atom, a C ₁ -C ₆ alkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ haloalkyl group, a C ₁ -C ₆ haloalkoxy group, a C ₁ -C ₆ alkylthio group, a C ₁ -C ₆ alkylsulfinyl group, a C ₁ -C ₆ alkylsulfonyl group, an unsubstituted or substituted phenyl group with Z ¹ , or an unsubstituted or substituted 5- to 10-membered heteroaryl group with Z ¹ ;
^R7 represents a hydrogen atom, a halogen atom, a cyano group, a _C1 -C6 alkyl group, a C3- _C6 cycloalkyl group, a _C1 - _C6 alkoxy group, a _C1 - _C6 haloalkyl group, _{a C1} - _C6 haloalkoxy group _, a _C3 - _C6 cycloalkyl group, a _C1 - _C6 alkylthio group, a _C1 - _C6 alkylsulfinyl group, a _C1 - _C6 alkylsulfonyl group, an unsubstituted or substituted phenyl group with ^Z2 , or an unsubstituted or substituted heteroaryl group with ^Z2 ;
^R8 represents a hydrogen atom, a halogen atom, a _C1 -C6 alkyl group, a C1- _C6 alkoxy group, _{a C1} - _C6 haloalkyl group, a _C1 - _C6 haloalkoxy group, a _C3 - _C6 cycloalkyl group, a _C1 - _C6 alkylthio _group , a _C1 - _C6 alkylsulfyl group, a _C1 - _C6 alkylsulfonyl group, an unsubstituted or substituted phenyl group with ^Z3 , or an unsubstituted or substituted heteroaryl group with ^Z3 ;
R ⁹ represents a hydrogen atom, a halogen atom, a C ₁ -C ₆ alkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₆ alkoxy group, or a C ₁ -C ₆ haloalkyl group;
n and m each represent 0 or 1, provided that n+m is 1 or 2;
Y represents an oxygen atom or a bond;
^A1 represents a phenyl group, a naphthyl group or a 5- to 10-membered heteroaryl group which may be unsubstituted or substituted with a substituent ^Z4 ;
^A2 represents a phenyl group, a naphthyl group, a phenoxy group, a naphthyloxy group, a 5- to 10-membered heteroaryl group, or a 5- to 10-membered heteroaryloxy group, which may be unsubstituted or substituted by a substituent ^Z5 ;
The substituent Z ¹ represents a halogen atom, a C ₁ -C ₆ alkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₆ alkoxy group, a nitro group, a cyano group, a C ₁ -C ₆ haloalkyl group, or a C ₁ -C ₆ haloalkoxy group, the number of the substituent Z ¹ may be one or more, and when there are two or more substituents, they may be the same or different from each other;
The substituent ^Z2 represents a halogen atom, a _C1 - _C6 alkyl group, a C3- _C6 cycloalkyl group, a _C1 - _C6 alkoxy group, a nitro group _, a cyano group, a _C1 - _C6 haloalkyl group, or a _C1 - _C6 haloalkoxy group, and the number of the substituent ^Z2 may be one or more, and when two or more substituents are present, they may be the same or different from each other;
The substituent ^Z3 represents a halogen atom, a _C1 - _C6 alkyl group, a C3- _C6 cycloalkyl group, a _C1 - _C6 alkoxy group, a nitro group _, a cyano group, a _C1 - _C6 haloalkyl group, or a _C1 - _C6 haloalkoxy group, and the number of the substituent ^Z3 may be one or more, and when two or more substituents are present, they may be the same or different from each other;
The substituent ^Z4 represents a halogen atom, a _C1 - _C6 alkyl group, a C3- _C6 cycloalkyl group, a _C1 - _C6 alkoxy group, a nitro group _, a cyano group, a _C1 - _C6 haloalkyl group, or a _C1 - _C6 haloalkoxy group, and may be one or more than ^one , and when two or more substituents are present, they may be the same or different from each other;
The substituent ^Z5 represents a halogen atom, a _C1 - _C6 alkyl group, a C3- _C6 cycloalkyl group, a _C1 - _C6 alkoxy group, a _nitro group, a cyano group, a _C1 - _C6 haloalkyl group, or a _C1 - _C6 haloalkoxy group, and the number of the substituent ^Z5 may be one or more, and when two or more substituents are present, they may be the same or different.
or a salt thereof. A method for producing the fused heteroarylcarboxamide derivative (I) according to claim 1, comprising the steps of:
The following formula (II):

(wherein R ⁶ , R ⁷ , R ⁸ , R ⁹ and A ¹ are as defined in formula (I) above).
and a carboxylic acid derivative represented by the formula:
The following formula (XIV):

(wherein ^R1 , ^R2 , ^R3 , ^R4 , ^R5 , ^A2 , Y, n and m are as defined in formula (I) above).
and reacting the compound represented by the formula (I) with an amine derivative represented by the formula (I). An agricultural and horticultural agent comprising the fused heteroarylcarboxamide derivative (I) or a salt thereof according to claim 1.