WO2016092559A1

WO2016092559A1 - Substituted pyrazole derivatives having activity as fungicides

Info

Publication number: WO2016092559A1
Application number: PCT/IN2015/000443
Authority: WO
Inventors: Tetsuya Imai; Surendra Kumar KUMAWAT; Manish Kumar SINGH; Ashish BHATT; Srinivas VENUVENKA; Vivek Kumar PANDEY; Dhuni Lal YADAV; Mahaveer Singh CHOUHAN; Jawed ASHRAF Md; Richu DHIR
Original assignee: OAT and IIL India Laboratories Pvt Ltd
Current assignee: OAT and IIL India Laboratories Pvt Ltd
Priority date: 2014-12-12
Filing date: 2015-12-07
Publication date: 2016-06-16
Anticipated expiration: 2017-06-12
Also published as: TW201629018A

Abstract

An object of the present invention is to provide a heterocyclic compound or a salt thereof that controls a pest. The present invention provides a heterocyclic compound represented by Formula (1): or a salt thereof, wherein R¹ and R⁴ are identical or different and each represents substituted or unsubstituted aryl, or a substituted or unsubstituted heteroaryl group, R² represents substituted or unsubstituted C_1-4 alkyl, R³ represents substituted or unsubstituted aryl or a substituted or unsubstituted heteroaryl group, X represents C(=Y), CR⁵R⁶, NH, or NR⁷, Y represents oxygen or sulfur, R⁵ and R⁶ are identical or different and each represents hydrogen, or the like, R⁷ represents C_1-4 alkyl, C_1-4 alkylcarbonyl, or C_1-4 alkoxycarbonyl, and the bond represented by: is a single bond or a double bond.

Description

DESCRIPTION

Title, of Invention:

SUBSTITUTED PYRAZOLE DERIVATIVES HAVING ACTIVITY AS FUNGICIDES

Technical Field

The present invention relates to a novel hetero compound and use thereof.

Background Art

As a result of the long-term use of fungicides, recent years have seen the emergence of fungi that are resistant to chemicals. It has thus become difficult to accomplish control by the use of known fungicides.

Under such circumstances, there is a demand for the development of new types of fungicides that are expected to achieve fungicidal activity not only against chemical-sensitive fungi, but also against chemical-resistant fungi.

For example, WO 2013/164295 (Patent Literature (PTL) 1) discloses the compound represented by Formula (A) below. PTL 1 discloses that this compound exhibits insecticidal activity.

However, PTL 1 nowhere discloses that this compound exhibits fungicidal activity.

Citation List

Patent Literature

PTL 1: WO 2013/164295

Summary of Invention

Technical Problem An object of the present invention is to provide a heterocyclic compound or a salt thereof that controls a pest.

Another object of the present invention is to provide a new type of fungicide that exhibits excellent fungicidal activity not only against chemical-sensitive fungi, but also against chemical-resistant fungi.

Solution to Problem

The present inventors conducted extensive research to achieve the above objects, and succeeded in synthesizing a compound represented by the following Formula (1) or a salt thereof that has fungicidal activity. The present inventors have conducted further research based on the above findings. The present invention has thereby been accomplished.

More specifically, the present invention includes the following embodiments:

Item 1:

A heterocyclic compound represented by Formula (1) :

or a salt thereof,

wherein R¹ and R⁴ are identical or different and each represents substituted or unsubstituted aryl, or a substituted or

unsubstituted heteroaryl group,

R² represents substituted or unsubstituted C_1-4 alkyl,

R³ represents substituted or unsubstituted aryl or a substituted or unsubstituted heteroaryl group,

X: represents C(=Y), CR⁵R⁶, NH, or NR⁷,

Y represents oxygen or sulfur,

R⁵ and R⁶ are identical or different and each represents hydrogen, hydroxy, thiol, halogen, C_1-4 alkyl, C_1-4 haloalkyl, C_1-4 alkoxy C_1-4 alkyl, C_1-4 haloalkoxy C_1-4 alkyl, C_2-4 alkenyl, C_2-4 alkynyl, C_3-8 cycloalkyl, C_3-8 cycloalkyl C_1-4 alkyl, C_1-4 alkylcarbonyl, C_1-4 alkylcarbonyloxy, C_1-4 alkoxy, C_1-4 haloalkoxy, C_1-4 alkylthio, C_1-4 haloalkylthio, C_1-4 alkylsulfonyl, C_1-4 alkylsulfinyl, arylthio, arylsulfonyl, arylsulfinyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or

unsubstituted aryl C_1-4 alkyl, or a substituted or unsubstituted heteroaryl group,

: R⁷ represents C_1-4 alkyl, C_1-4 alkylcarbonyl, or C_1-4 alkoxycarbonyl, and

the bond represented by: is a single bond o-r a double bond.

Item 2:

The heterocyclic compound or a salt thereof according to Item 1, wherein R¹ represents substituted aryl.

Item 3:

The heterocyclic compound or a salt thereof according .·^' to Item 1 or 2, wherein R³ represents substituted aryl.

Item 4:

The heterocyclic compound or a salt thereof according to any one of Items 1 to 3, wherein R⁴ represents a substituted or unsubstituted heter.oaryl group.

Item 5:

The heterocyclic compound or a salt thereof according to any one of Items 1 to 4, wherein R⁴ is substituted or

unsubstituted pyridyl.

Item 6:

A pest-controlling agent containing the heterocyclic compound or a salt thereof of any one of Items 1 to 5.

Item 7:

A fungicide containing the heterocyclic compound or a salt thereof of any one of Items 1 to 5. Advantageous Effects of Invention

The heterocyclic compound or a salt thereof according to the present invention achieves an excellent fungicidal effect on fungal plant pathogens. Additionally, the heterocyclic compound or a salt thereof according to the present invention is useful as a new type of fungicide that exhibits excellent fungicidal activity not only against chemical-sensitive fungi, but also against chemical-resistant fungi.

Description of Embodiments

Heterocyclic compound or a salt thereof

The present invention is directed to a compound represented by Formula (1) :

or a salt thereof (hereinafter sometimes referred to as "compound (1) of the present invention" or "compound (1)"),

wherein

R¹ and R⁴ are identical or different and each represents

substituted or unsubstituted aryl, or a substituted or

unsubstituted heteroaryl group,

R² represents substituted or unsubstituted C_1-4 alkyl,

X represents C(-Y), CR⁵R⁶, NH, or NR⁷,

Y represents oxygen or sulfur,

R⁵ and R⁶ are identical or different and each represents hydrogen, hydroxy, thiol, halogen, C_1-4 alkyl, C_1-4 haloalkyl, C_1-4 alkoxy C_1-4 alkyl, C_1-4 haloalkoxy C_1-4 alkyl, C_2-4 alkenyl, C_2-4 alkynyl, C_3-8 cycloalkyl, C_3-8 cycloalkyl C_1-4 alkyl, C_1-4 alkylcarbonyl, C_1-4 alkylcarbonyloxy, C_1-4 alkoxy, C_1-4 haloalkoxy, C_1-4 alkylthio, C_1-4 haloalkylthio, C_1-4 alkylsulfonyl, alkylsulfinyl, arylthio, arylsulfonyl, arylsulfinyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or

R⁷ represents C_1-4 alkyl, C_1-4 alkylcarbonyl, or C_1-4 alkoxycarbonyl, and

the bond represented by:

is a single bond or a double bond.

The following shows specific examples of each group as used in this specification.

Examples of aryl include, but are not particularly limited to, phenyl, 1-naphthyl, 2-naphthyl, and the like.

Examples of a heteroaryl group include, but are not particularly limited to, thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, imidazolyl, oxadiazolyl,

triazolyl, tetrazolyl, pyridyl, pyridazinyl, thiadiazolyl, pyrimidinyl, triazinyl, indolyl, isoindolyl, quinazolyl,

carbazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl,

benzisothiazolyl, benzimidazolyl, indazolyl, quinolyl,

isoquinolyl, pyridoindolyl, benzofuranyl, and the like. These heteroaryl groups include those substituted at any substitutable position with an oxo or thioketone group. These heteroaryl groups may optionally be substituted at any substitutable position with 1 to 5 .(preferably 1 to 3) substituents.

Examples of C_1-4 alkyl include, but are not particularly limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and like C_1-4 straight-chain or branched- chain alkyl.

Examples of halogen include, but are not particularly limited to, fluorine, chlorine, bromine, iodine, and the like.

Examples of C_1-4 haloalkyl include, but are not particularly limited to, fluoromethyl, chloromethyl, bromomethyl, iodomethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2- fluoroethyl, 2-chloroethyl, 2, 2, 2-trifluoroethyl,

pentafluoroethyl, 1-fluoropropyl, 2-chloropropyl, 3-fluoropropyl, 3-chloropropyl, 3, 3, 3-trifluoropropyl, 1-fluorobutyl, 1- chlorobutyl, 4-fluorobutyl, 4, 4, 4-trifluorobutyl, and like

straight-chain or branched-chain alkyl substituted with 1 to 9, and preferably 1 to 5, halogen atoms.

Examples of C_1-4 alkoxy C_1-4 alkyl include, but are not particularly limited to, methoxymethyl, ethoxymethyl, n- propoxymethyl, isopropoxymethyl, n-butoxymethyl, sec-butoxymethyl, 2-methoxyethyl, and like alkoxyalkyl in which C_1-4 straight-chain or branched-chain alkyl is substituted with C_1-4 straight-chain or branched-chain alkoxy.

Examples of C_1-4 haloalkoxy C_1-4 alkyl include, but are not particularly limited to, fluoromethoxymethyl,

chloromethoxymethyl, bromomethoxymethy1, iodomethoxymethyl, difluoromethoxymethyl, trifluoromethoxymethyl, 2,2,2- trifluoromethoxymethyl, and like straight-chain or branched-chain alkoxyalkyl substituted with 1 to 9, preferably 1 to 5, halogen atoms .

Examples of C₂.₄ alkenyl include, but are not particularly limited to, vinyl, allyl, 2-butenyl, 3-butenyl, 1- methylallyl, and the like.

Examples of C_2-4 alkynyl include, but are not particularly limited to, ethynyl, 1-propynyl, l-methyl-2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, and the like.

Examples of C_3-8 cycloalkyl include, but are not particularly limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and the like.

Examples of C_3-8 cycloalkyl C_1-4 alkyl include, but are not particularly limited to, cyclopropylmethyl, cyclobutylethyl, and the like.

Examples of C_1-4 alkylcarbonyl include, but are not particularly limited to, methylcarbonyl (acetyl), ethylcarbonyl (propionyl), n-propylcarbonyl (butyryl) , isopropylcarbonyl

(isobutyryl) , n-butylcarbonyl (valeryl), isobutylcarbonyl

(isovaleryl) , sec-butylcarbonyl, tert-butylcarbonyl, and like C_1-4 straight-chain or branched-chain alkylcarbonyl groups.

Examples of C_1-4 alkoxycarbonyl include, but are not particularly limited to, methoxycarbonyl, ethoxycarbonyl, n- propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl,

isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, and like C_1-4 straight-chain or branched-chain alkoxycarbonyl groups.

Examples of C_1-4 alkylcarbonyloxy include, but are not . particularly limited to, methylcarbonyloxy (acetyloxy) ,

ethylcarbonyloxy (propionyloxy) , n-propylcarbonyloxy,

(butyryloxy) , isopropylcarbonyloxy (isobutyryloxy) , n- butylcarbonyloxy (valeryloxy) , isobutylcarbonyloxy

(isovaleryloxy) , sec-butylcarbonyloxy, tert-butylcarbonyloxy, and like C_1-4 straight-chain or branched-chain alkylcarbonyloxy ' groups.

Examples of C_1-4 alkoxy include, but are not

particularly limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, and like C_1-4 straight-chain or branched-chain alkoxy.

Examples of C_1-4 haloalkoxy include, but are not particularly limited to, fluoromethoxy, bromomethoxy, iodomethoxy, difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 1-fluoroethoxy, pentafluoroethoxy, and like C_1-4 straight-chain or branched-chain alkoxy substituted with 1 to 9, preferably 1 to 5, halogen atoms.

Examples of C_1-4 alkylthio include, but are not particularly limited to, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, see-butylthio, tert- butylthio, and like C_1-4 straight-chain or branched-chain

alkylthio.

Examples of C_1-4 alkylsulfonyl include, but are not particularly limited to, methylsulfonyl, ethylsulfonyl, n- propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl,

isobutylsulfonyl, sec-butylsulfonyl, tert-butylsulfonyl, and like C_1-4 straight-chain or branched-chain alkylsulfonyl groups.

Examples of C_1-4 alkylsulfinyl include, but are not particularly limited to, methylsulfinyl, ethylsulfinyl, n- propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl,

isobutylsulfinyl, sec-butylsulfinyl, tert-butylsulfinyl, and like C_1-4 straight-chain or branched-chain alkylsulfinyl groups.

Examples of aryloxy include, but are not particularly limited to, phenyloxy, 1-naphthyloxy, 2-naphthyloxy, and the like

Examples of arylthio include, but are not particularly limited to, phenylthio, 1-naphthylthio, 2-naphthylthio, and the like.

Examples of arylsulfonyl include, but are not particularly limited to, phenylsulfonyl, 1-naphthylsulfonyl, 2- naphthylsulfonyl, and the like.

Examples of arylsulfinyl include, but are not particularly limited to, phenylsulfinyl, 1-naphthylsulfinyl, 2- naphthylsulfinyl, and the like.

Examples of aryl C_1-4 alkyl include phenylmethyl, phenylethyl, phenyl-n-propyl, 1-naphthylmethyl, 2-naphthylmethyl, and the like.

The substituted aryl or substituted heteroaryl group refers to an aryl group or heteroaryl group mentioned above that is substituted with one or more substituents. The number of substituents is preferably 1 to 5, and more preferably 1 to 3.

The substituted C_1-4 alkyl refers to a C_1-4 alkyl group mentioned above that is substituted with one or more substituents The number of substituents is preferably 1 to 5, and more

preferably 1 to 3.

Examples of "substituents" for the substituted C_1-4 alkyl, substituted aryl, and substituted heteroaryl groups include, but are not particularly limited to, halogen, nitro, cyano, hydroxy (hydroxyl group), thiol, C_1-4 alkyl, C_1-4 haloalkyl, C_1-4 alkoxy C_1-4 alkyl, C_1-4 haloalkoxy alkyl, C_2-4 alkenyl, C_2-4 alkynyl, C_3-8 cycloalkyl, C_3-8 cycloalkyl alkyl, C_1-4

alkylcarbonyl, C_1-4 alkoxycarbonyl, C_1-4 alkylcarbonyloxy, C_1-4 alkoxy, C_1-4 haloalkoxy, C_1-4 alkylthio, C_1-4 haloalkylthio, C_1-4 alkylsulfonyl, C_1-4 alkylsulfinyl, aryloxy, arylthio, arylsulfonyl, arylsulfinyl, substituted or unsubstituted aryl, substituted or unsubstituted aryl C_1-4 alkyl, a substituted or unsubstituted heteroaryl group, and the like.

Of these, preferable substituents are halogen, nitro, cyano, C_1-4 alkyl, C_1-4 haloalkyl, C_1-4 alkoxy, haloalkoxy, C_1-4 alkylthio, and aryloxy, and more preferable substituents are chlorine, fluorine, bromine, nitro, cyano, methyl,

trifluoromethyl, methoxy, trifluoromethoxy, methylthio, and phenoxy.

Preferable substituents for, in particular, substituted aryl or a substituted heteroaryl group represented by R¹ are halogen, C_1-4 haloalkyl, and C_1-4 alkoxy, and more preferable substituents therefor are chlorine, fluorine, bromine,

trifluoromethyl, methoxy, and trifluoromethoxy. The number of substituents is as mentioned above.

A preferable substituent for substituted alkyl represented by R² is halogen, and a more preferable substituent is fluorine. The number of substituents is as mentioned above.

Preferable substituents for substituted aryl or substituted heteroaryl group are halogen, C_1-4 haloalkyl, C_1-4 alkoxy, C_1-4 haloalkoxy, C_1-4 alkylthio, and aryloxy, and more preferable substituents are chlorine, fluorine, trifluoromethyl, methoxy, trifluoromethoxy, methylthio, and phenoxy. The number of substituents is as mentioned above.

Preferable substituents for substituted aryl or substituted heteroaryl group represented by R⁴ are halogen, nitro-,^' cyano, C_1-4 alkyl, and C_1-4 haloalkyl, and more preferable

substituents are chlorine, fluorine, nitro, cyano, methyl, and trifluoromethyl. The number of substituents is as mentioned above.

X represents C(=Y), CR⁵R⁶ NH, or NR⁷, preferably C(=Y), CR⁵R⁶, or NH, and more preferably C(=0), CHOH, CHC1, CHOC(=0)CH₃, CHSCH₃, CHSC2H5, CHSO2CH3, or NH.

Y represents oxygen or sulfur, and preferably oxygen. R⁵ and R⁶ are identical or different and each represents hydrogen, hydroxy, thiol, halogen, C_1-4 alkyl, C_1-4

: haloalkyl, C_1-4 alkoxy C_1-4 alkyl, C_1-4 haloalkoxy C_1-4 alkyl, C_2-4 aikenyl, C_2-4 alkynyl, C_3-8 cycloalkyl, C_3-8 cycloalkyl C_1-4 alkyl, C_1-4 alkylcarbonyl, C_1-4 alkylcarbonyloxy, C_1-4 alkoxy, C_1-4

haloalkoxy, C_1-4 alkylthio, C_1-4 alkylsulfonyl, C_1-4 alkylsulfinyl, arylsulfonyl, arylsulfinyl, substituted or unsubstituted aryl, substituted or unsubstituted aryl C_1-4 alkyl, or a substituted or unsubstituted heteroaryl group, preferably hydrogen, hydroxy, thiol, halogen, C_1-4 alkylcarbonyloxy, C_1-4 alkylthio, or C_1-4 alkylsulfonyl, and more preferably hydrogen, hydroxy, chlorine, methylcarbonyloxy, methylthio, ethylthio, or methylsulfonyl .

R⁷ represents hydrogen, C_1-4 alkyl, substituted or unsubstituted C_1-4 alkoxy, substituted or unsubstituted aryl, C_1-4 alkylcarbonyl, or C_1-4 alkoxycarbonyl, and preferably hydrogen.

The dotted line is a single bond or a double bond.

The substituted aryl is preferably an aryl group having one to three haloge'n atoms, an aryl group having one to three nitro groups, an aryl group having one to three cyano groups, an aryl group having one to three C_1-4 alkyl groups, an aryl group having one to three C_1-4 haloalkyl groups, an aryl group having one to two halogen atoms and one to two C_1-4 haloalkyl groups, an aryl group having one to three aryloxy groups, an aryl group having one to three C_1-4 alkoxy groups, an aryl group having one to three C_1-4 haloalkoxy groups, or an aryl group having one to three C_1-4 alkylthio groups; more preferably an aryl group having one to three chlorine atoms, an aryl group having one to three bromine atoms, an aryl group having one to three fluorine atoms, an aryl group having one to two fluorine atoms and one to two chlorine atoms, an aryl group having one to three trifluoromethyl groups, an aryl group having one to two trifluoromethyl groups and one to two fluorine atoms, an aryl group having one to three phenyloxy groups, an aryl group having one to three methoxy groups, an aryl group having one to three trifluoromethoxy groups, or an aryl group having one to three methylthio groups. The substituted heteroaryl group is preferably a heteroaryl group having one to three halogen atoms, a heteroaryl group having one to three nitro groups, a heteroaryl group having one to three cyano groups, a heteroaryl group having one to three C_1-4 alkyl groups, a heteroaryl group having one to three C_1-4 haloalkyl groups, a heteroaryl group having one to two halogen atoms and one to two C_1-4 haloalkyl groups, a heteroaryl group having one to three aryloxy groups, a heteroaryl group having one to three C_1-4 alkoxy groups, a heteroaryl group having one to three C_1-4 haloalkoxy groups, or a heteroaryl group having one to three C_1-4 alkylthio groups; and more preferably a heteroaryl group having one to three chlorine atoms, a heteroaryl group having one to three bromine atoms, a heteroaryl group having one to three fluorine atoms, a heteroaryl group having one to two fluorine atoms and one to two chlorine atoms, a heteroaryl group having one to three trifluoromethyl groups, a heteroaryl group having one to two trifluoromethyl groups and one to two fluorine atoms, a heteroaryl group having one to three phenyloxy groups, a heteroaryl group having one to three methoxy groups, a heteroaryl group having one to three trifluoromethoxy groups, or a

heteroaryl group having one to three methylthio groups.

The substituted or unsubstituted heteroaryl group is particularly preferably 2-pyridyl, 3-pyridyl, 4-pyridyl, 5- fluoro-2-pyridyl, 5-chloro-2-pyridyl, 3, 5-dichloro-2-pyridyl, 5- methy1-2-pyridyl, 3-methyl-2-pyridyl, 5-trifluoromethyl-2-pyridyl, 4-trifluoromethyl-2-pyridyl, 3-trifluoromethyl-2-pyridyl, 6- trifluoromethyl-2-pyridyl, 3-chloro-5-trifluoromethyl-2-pyridyl, 3-nitro-5-trifluoromethyl-2-pyridyl, 3-cyano-2-pyridyl, 5-chloro- 3-pyridyl, 5-trifluoromethyl-3-pyridyl, 2-fluoro-6- trifluoromethyl-3-pyridyl, 5-pyrimidinyl, 2-pyrimidinyl, 2- thienyl, or 3-thienyl.

The salt of the heterocyclic compound represented by Formula (1) may be any type of salt as long as it is

agriculturally acceptable. Examples of salt include hydrochloride salt, sulfate salt, nitrate salt, and like inorganic acid salts; acetate salt, methanesulfonic acid salt, and like organic acid salts; sodium salt, potassium salt, and like alkali metal salts; magnesium salt, calcium salt, and like alkaline earth metal salts; dimethylammonium, triethylammonium, and like quaternary ammonium salts;* and the like.

Compound (1) of the present invention encompasses a pyrazole compound represented by the following Formula (1A) (hereinafter referred to as "compound 1A") and a dihydropyrazole compound represented by Formula (IB) (hereinafter referred to as "compound IB").

(wherein R¹, R², R³, R⁴, and X are as defined above.)

Among compounds (1) of the present invention, a preferable compound is a compound in which R^l and R⁴ are not simultaneously unsubstituted aryl.

Of these, a more preferable compound of the present invention is a compound or a salt thereof in which R¹ and R⁴ are identical or different and each represents substituted aryl or a substituted or unsubstituted heteroaryl group,

R² represents substituted or unsubstituted C_1-4 alkyl,

R³ represents substituted aryl, or a substituted or unsubstituted heteroaryl group,

X represents C(-O), CR*R⁶, NH, or NR⁷,

Y represents oxygen,

R⁹ and R⁶ are identical or different and each represents hydrogen; hydroxy, thiol, halogen, C_1-4 alkyl, C_1-4 haloalkyl, C_1-4 alkoxy C_1-4 alkyl, C_1-4 haloalkoxy C_1-4 alkyl, C₂.₄ alkenyl, C_2-4 alkynyl, C_3-8 cycloalkyl, C_3-8 cycloalkyl C_1-4 alkyl, C_1-4 alkylcarbonyl, C_1-4 alkylcarbonyloxy, C_1-4 alkoxy, C_1-4 haloalkoxy, C_1-4 alkylthio, C_1-4 alkylsulfonyl, C_1-4 alkylsulfinyl, arylsulfonyl, arylsulfinyl, substituted or unsubstituted aryl, substituted or unsubstituted aryl C_1-4 alkyl, or a substituted or unsubstituted heteroaryl group,

R⁷ represents hydrogen, C_1-4 alkylcarbonyl, or C_1-4 alkoxycarbonyl, and

the bond represented by:

is a single bond or a double bond.

A more particularly preferable compound of the present invention is a compound or a salt thereof in which

R¹ represents 2, 4-disubstituted aryl,

R² represents substituted or unsubstituted C_1-4 alkyl,

R³ represents 2, 4-disubstituted aryl or 3-substituted aryl,

R⁴ represents substituted or .unsubstituted 3-pyridyl,

X represents C(=0), CR⁵R⁶, or NH,

Y represents oxygen,

R⁵ and R⁶ are identical or different and each represents hydrogen, hydroxy, thiol, halogen, C_1-4 alkylcarbonyloxy, C_1-4 alkylthio, or C_1-4 alkylsulfonyl, and

the bond represented by: is a single bond or a double bond.

When compound (1) of the present invention has isomers such as optical isomers, stereoisomers, regioisomers, and the like, any of the isomers and mixtures thereof are included within the scope of compound (1) . For example, when compound (1) has optical isomers, the optical isomer separated from a racemic mixture is also included within the scope of compound (1) . Each of such isomers may be obtained as a single compound by known synthesis and separation means (e.g., concentration, solvent extraction, column chromatography, and recrystallization) .

Process for preparing a heterocyclic compound or a salt thereof

The process for preparing compound (1) of the present invention is not particularly limited, and various processes, such as Reaction Scheme 1, Reaction Scheme 2, Reaction Scheme 3, Reaction Scheme 4, Reaction Scheme 5, and Reaction Scheme 6, may be used.

Reaction Scheme 1

As shown in Reaction Scheme 1, a dihydropyrazole compound represented by Formula (lB-1) or a salt thereof

(hereinafter referred to as "compound (lB-1)") is prepared by reacting a hydrazide compound represented by Formula (2)

(hereinafter referred to as "compound (2)") with an unsaturated ketone compound represented by Formula (3) (hereinafter referred to as "compound (3)") in the^' presence of a base. Reaction Scheme 1

(wherein R¹, R², R³, and R⁴ are as defined above, and the wavy lines represent optical isomers.)

In the reaction of compound (2) and compound (3), the proportions of these compounds used are not particularly limited, and may be suitably selected from a wide range. The latter is usually used in an amount of about 1 to 5 moles per mole of the former, and preferably about an equimolar amount with respect to the latter.

The reaction above is performed after a step (a chlorination step) in which compound (2) is chlorinated to produce a chloride of compound (2) . After the chlorination step, the chloride of compound (2) is reacted with compound (3) to produce compound (lB-1) .

In the chlorination step, a chlorinating agent may be used. Examples of such a chlorinating agent include, but are not particularly limited to, chlorine, phosphorus oxychloride (P0C1₃), and the like. These chlorinating agents may be used alone or in a combination of two or more.

The chlorinating agent is usually used in an amount of 1 mole or more, preferably 1 to 10 moles, and more preferably 1 to 8 moles, per mole of compound (2) . When, for example,

phosphorus oxychloride, which can also function as a solvent, is used as a chlorinating agent, the excess of phosphorus

oxychloride, after the completion of the chlorination step, may be removed under reduced pressure so as to be used in the

subsequent reaction.

Examples of the base used in the step for reacting compound (2) or a chlorination product of compound (2) with compound (3) include, but are not particularly limited to, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, and like alkali metal carbonate salts; sodium

hydroxide, potassium hydroxide, and like alkali metal hydroxides; sodium hydride, potassium hydride, and like alkali metal hydrides, and other inorganic bases; sodium methoxide, sodium ethoxide, potassium tert-butoxide, and like alkali metal alkoxides; and triethylamine, pyridine, and other organic bases. These bases may be used alone, or in a combination of two or more.

The base may be used in a stoichiometric amount or more than the stoichiometric amount, with respect to compound (2) .

Specifically, the base is preferably used in an amount of 1 to 5 moles, and more pre-ferably 1 to 3 moles, per mole of compound (2) . When used, triethylamine, pyridine, or like organic base may be used in large excess to serve also as a reaction solvent.

The above reaction may be carried out in a suitable solvent or in the absence of a solvent. When the reaction is carried out in a solvent, usable solvents for the reaction are not limited insofar as they are inert to the reaction. Examples of solvents include n-hexane, cyclohexane, n-heptane, and like aliphatic or alicyclic hydrocarbons; benzene, chlorobenzene, toluene, xylene, and like aromatic hydrocarbons; methylene chloride, I, 2-dichloroethane, chloroform, carbon tetrachloride, and like halogenated hydrocarbons; diethyl ether, tetrahydrofuran (THF) , 1,4-dioxane, 1, 2-dimethoxyethane, and like ethers; N,N- dimethylformamide (DMF) , and like amides; dimethylsulfoxide, and like sulfoxides; and the like. These solvents may be used alone or in a combination of two or more, as required.

The reaction temperature of the above reaction is usually in, although not limited, the range of -20°C to the boiling point of the solvent used. The reaction is preferably performed under reflux of the solvent. The reaction time varies according to, for example, the reaction temperature. The reaction is usually completed in about 0.5 to about 24 hours.

Reaction Scheme 2

As shown in Reaction Scheme 2, a dihydropyrazole compound represented by Formula (1B-2) or a salt thereof

(hereinafter referred to as "compound (1B-2)") is prepared by reducing compound (lB-1) in a solvent. Reaction Scheme 2

Reaction Scheme 3

As shown in Reaction Scheme 3, a pyrazole compound represented by Formula (1A-2) or a salt thereof (hereinafter referred to as "compound (1A-2)"), or a compound (1B-2) is prepared by reducing compound (lA-1) in a solvent.

Reaction Scheme 3

(wherein R¹, R², R³, and R⁴ are as defined above, and the wavy lines represent optical isomers . )

In the reduction reaction in Reaction Scheme 2 or Reaction Scheme 3 above, a reducing agent may be used. Examples of such a reducing agent include, but are not particularly limited to, boron compounds, and the like. Examples of boron compounds include sodium borohydride, potassium borohydride, and like alkali metal borohydride compounds; sodium

triacetoxyborohydride; sodium cyanoborohydride; and the like.

These reducing agents may be used alone or in a combination of two or more.

The reducing agent is used in an amount of preferably 1 to 3 moles, and more preferably 1.5 to 2.5 moles, per mole of compound (lB-1) or compound (lA-1) .

Examples of solvents include, but are not particularly limited to, methanol, ethanol, isopropanol, and like lower alcohols; diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2- dimethoxyethane, and like

ether-based solvents; benzene, toluene, and like aromatic hydrocarbon-based solvents; and the like. Of these solvents, lower alcohols are preferable, and 2-propanol is more preferable. These solvents may be used alone or in a combination of two or more.

The reaction temperature of the above reaction is usually in, although not limited, the range of -10°C to the boiling point of the solvent used. The reaction is preferably performed at room temperature. The reaction time varies according to, for example, the reaction temperature. The reaction is usually completed in about 0.5 to about 24 hours. Reaction Scheme 4

As shown in Reaction Scheme 4, a pyrazole compound represented by Formula (lA-1) (hereinafter referred to as

"compound (lA-1)") is prepared by oxidizing compound (lB-1) in a solvent .

Reaction Scheme 4

An oxidizing agent may be used for the oxidation above. Examples of such an oxidizing agent include, but are not

particularly limited to, lead compounds, such as lead oxide (PbO₂, Pb₃O₄) , lead tetraacetate (Pb(OAc)₄), lead trifluoroacetate

(Pb (OCOCF₃) 4) ; copper compounds, such as copper chloride, copper acetate, copper benzoate, copper carbonate, and copper nitrate; iron compounds, such as iron chloride, iron acetate, iron sulfate, and iron nitrate; manganese compounds, such as manganese chloride, manganese acetate, manganese oxide; zinc compounds, such as zinc chloride and zinc acetate; and the like. These oxidizing agents may be used alone or in a combination of two or more.

The amount of the oxidizing agent used is not particularly limited. The oxidizing agent used is usually 1 mole or more, preferably 1 to 3 moles, and more preferably 1.5 to 2.5 moles, per mole of compound (lB-1) .

Examples of solvents include n-hexane, cyclohexane, n- heptane, and like aliphatic or alicyclic hydrocarbons; benzene, chlorobenzene, toluene, xylene, and like aromatic hydrocarbons; methylene chloride, 1, 2-dichloroethane, chloroform, carbon

tetrachloride, and like halogenated hydrocarbons; diethyl ether, tetrahydrofuran (THF) , 1,4-dioxane, 1, 2-dimethoxyethane, and like ethers; Ν,Ν-dimethylfoirmamide (DMF), and like amides;

dimethylsulfoxide, .and like sulfoxides; and the like. These solvents may be used alone or in a combination of two or more.

The reaction temperature of the above reaction is usually in, although not limited, the range of -10°C to the boiling point of the solvent used. The reaction is preferably performed at room temperature. The reaction time varies according to, for example, the reaction temperature. The reaction is usually completed in about 0.5 to about 24 hours.

Reaction Scheme 5

As shown in Reaction Scheme 5, a pyrazole compound represented by Formula (ΙΑ'-l) (hereinafter referred to as

"compound (ΙΑ'-l)") is prepared by reacting an amino compound represented by Formula (4) (hereinafter referred to as "compound (4)") with a compound represented by Formula (5) (hereinafter referred to as "compound (5)") in a solvent in the presence of a catalyst and a base. Reaction Scheme 5

(wherein R¹, R², R³, and R⁴ are as defined above, and

Z represents a leaving group)

Examples of the leaving group represented by Z include chlorine, bromine, iodine, and like halogen atoms; and

substituted or unsubstituted alkyl sulfonate, substituted or unsubstituted aryl sulfonate,- and the like.

Specific examples of compound (5) include substituted or unsubstituted aryl halide, substituted or unsubstituted heteroaryl halide, and the like, with substituted or

unsubstituted aryl halide and substituted or unsubstituted pyridyl halide being preferable.

Compound (5) is usually used in an amount of 1 mole or more, preferably 1 to 10 moles, and more preferably 1 to 5 moles, per mole of compound (4) .

Examples of bases include, but are not particularly limited to, sodium carbonate, potassium carbonate, cesium

carbonate, sodium bicarbonate, potassium bicarbonate, and like alkali metal carbonate salts; sodium hydroxide, potassium

hydroxide, and like alkali metal hydroxides; sodium hydride, potassium hydride, and like alkali metal hydrides, and other inorganic bases; sodium methoxide, sodium ethoxide, potassium tert-butoxide, and like alkali metal alkoxides; and triethylamine N> N-diisopropylethylamine, pyridine, 1,8- diazabicyclo [5.4.0] undec-7-ene (DBU), and other organic bases. These bases may be used alone or in a combination of two or more.

The base may be used in a stoichiometric amount or more than the stoichiometric amount, with respect to compound (4) .

Specifically, the base is preferably used in an amount of 1 to 5 moles, and more preferably 1 to 3 moles, per mole of compound (4)

The reaction may be performed in the presence of a catalyst. Examples of the catalyst include metal catalysts (e.g., metal and metal salts), copper salt complexes (e.g., a copper salt complex of copper iodide with Ν,Ν'-dimethyl-ethylenediamine, proline, or bipyridyl) , palladium complexes (e.g.,

tris(dibenzylidene-acetone)dipalladium (0), palladium acetate, and complexes of xantphos), and the like.

The amount of the catalyst used is not particularly limited. The catalyst is usually used in an amount of 0.001 to 1 mole, preferably 0.01 to 0.5 moles, and more preferably 0.05 to 0.3 moles, per mole of compound (4) .

Examples of solvents include n-hexane, cyclohexane, n- heptane, and like aliphatic or alicyclic hydrocarbons; benzene, chlorobenzene, toluene, xylene, and like aromatic hydrocarbons; methylene chloride, 1, 2-dichloroethane, chloroform, carbon tetrachloride, and like halogenated hydrocarbons; diethyl ether, tetrahydrofuran (THF) , 1, 4-dioxane, 1, 2-dimethoxyethane, and like ethers; N,N-dimethylformamide (DMF) , and like amides;

dimethylsulfoxide and like sulfoxides; acetonitrile; and the like These solvents may be used alone or in a combination of two or more.

The reaction temperature of the above reaction is usually in, although not limited, the range of -10°C to the boiling point of the solvent used. The reaction is preferably performed under reflux. The reaction time varies according to, for example, the reaction temperature. The reaction is usually completed in about 0.5 to about 24 hours.

Reaction Scheme 6

As shown in Reaction Scheme 6, a pyrazole compound represented by Formula (1Α'-2) (hereinafter referred to as

"compound (1Α'-2)") is prepared by reacting compound (IA'-Γ) with a: compound represented by Formula (6) (hereinafter referred to as "compound (6)") in a solvent, whether in the presence of a base or not.

Reaction Scheme 6

(wherein R¹, R², R³, R⁴, and R⁷ are as defined above, and

Z represents a leaving group.)

Examples of the leaving group represented by Z of compound (6) include chlorine, bromine, iodine, and like halogen atoms; and substituted or unsubstituted alkyl sulfonate,

substituted or unsubstituted aryl sulfonate, and the like.

Specific examples of compound (6) include methyl halide, ethyl halide, acetyl halide, methoxycarbonyl halide, and the like

Compound (6) is usually used in an amount of 1 mole or more, preferably 1 to 10 moles, and more preferably 1 to 5 moles, per mole of compound (1A'-1).

hydroxide, and like alkali metal hydroxides; sodium hydride, potassium hydride, and like alkali metal hydrides, and other inorganic bases; sodium methoxide, sodium ethoxide, potassium tert-butoxide, and like alkali metal alkoxides; and triethylamine, Ν,Ν-diisopropylethylamine, pyridine, 1,8- diazabicyclo[5.4.0]undec-7-ene (DBU) , and other organic bases.

These bases may be used alone or in a combination of two or more.

The base may be used in a stoichiometric amount or more than the stoichiometric amount, with respect to compound (1A'-1). Specifically, the base is preferably used in an amount of Ϊ to 5 moles, and more preferably 1 to 3 moles, per mole of compound (1A'-1) .

tetrachloride, and like halogenated hydrocarbons; diethyl ether, tetrahydrofuran (THF) , 1,4-dioxane, 1, 2-dimethoxyethane, and like ethers; Ν,Ν-dimethylformamide (DMF), and like amides;

The reaction temperature of the above reaction is usually in, although not limited, the range of -10°C to the boiling point of the solvent used. The reaction is preferably performed under reflux. The reaction time varies according to, for example, the reaction temperature. The reaction is usually completed in about 0.5 to about 24 hours .

Compound (2), compound (3), compound (4), and compound (5), used as starting materials in Reaction Scheme 1 or Reaction Scheme 5 above are known compounds or compounds easily prepared by a known method.

Each compound (1) obtained after the completion of the reactions shown in Reaction Scheme 1 to Reaction Scheme 6 may be easily isolated from the reaction mixture and purified by known isolation and purification techniques, such as filtration, solvent extraction, distillation, recrystallization, and column chromatography.

When compound (1) has regioisomers, each regioisomer may be separated by a usual separation step, such as silica gel chromatography.

Pest-Controlling Agent

Compound (1) of the present invention may be used as an active ingredient of a pest-controlling agent. Examples of^" pest- controlling agents include agents (fungicides or virucides) for controlling plant diseases that cause problems in the

: agricultural and horticultural fields; agents (agricultural and horticultural insecticide, miticides, nematicides, or soil insecticides) for controlling pests, mites, nematode, or soil pests that all cause problems in the agricultural and

horticultural fields; animal-ectoparasite-controlling agents (e.g., pulicide, ixodicide, and pedivulicideon) , and the like.

For use as an active ingredient of a pest-controlling agent, it is possible to use compound (1) of the present

invention as is with no additional components. However, it is usually preferable to use the compound by combining with a solid carrier, liquid carrier, or gaseous carrier (propellant) , and optionally with a surfactant and other adjuvants for

pharmaceutical preparation, and formulating the resulting mixture into various forms .such as oil solutions, emulsions, wettable powders, flowable preparations, granules, dusts, aerosols, fumigants, or the like, according to known preparation methods.

Compound (1) of the present invention is usually contained in these formulations in a proportion of 0.01 to 95 wt%, and preferably 0.1 to 50 wt%.

Examples of solid carriers usable in the formulations include solid carriers in a fine powder or granular form, such as clay (e.g., kaolin clay, diatomaceous earth, synthetic hydrated silicon dioxide, bentonite, Fubasami clay, and acid clay) , talc, ceramic, other inorganic minerals (e.g., celite, quartz, sulfur, active carbon, calcium carbonate, and hydrated silica), and chemical fertilizers (e.g., ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, and ammonium chloride); and the like.

Examples of liquid carriers include water, alcohols (e.g., methanol and ethanol), ketones (e.g., acetone and

methylethylketone) , aromatic hydrocarbons (e.g., benzene, toluene, xylene, ethylbenzene, and methylnaphthalene) , aliphatic

hydrocarbons (e.g., hexane, cyclohexane, kerosene, and light oil), esters (e.g., ethyl acetate and butyl acetate), nitriles (e.g., acetonitrile and isobutyronitrile) , ethers (e.g., diisopropyl ether and dioxane), acid amides (e.g., N, W-dimethylformamide and N,N-dimethylacetamide) , halogenated hydrocarbons (e.g.,

dichloromethane, trichloroethane, and carbon tetrachloride) , dimethylsulfoxide, soybean oil, cottonseed oil, and like

vegetable oils, and the like.

Examples of gaseous carriers include butane gas, LPG (liquefied petroleum gas) , dimethyl ether, carbon dioxide gas, and the like.

Examples of surfactants include alkyl sulfates, alkyl sulfonates, alkylaryl sulfonates, alkyl aryl ethers,

polyoxyethylene adducts thereof, polyethylene glycol ethers, polyhydric alcohol esters, sugar alcohol derivatives, and the like.

Examples of adjuvants for pharmaceutical preparation include fixing agents, dispersants, stabilizers, and the like.

Examples of the fixing agents and dispersants include casein, gelatin, polysaccharides (e.g., starch, gum arabic, cellulose derivatives, and alginic acid), lignin derivatives, bentonite, sugars, and water-soluble synthetic polymers (e.g., polyvinyl alcohol, polyvinyl pyrrolidone, and polyacrylic acids) .

Examples of stabilizers include PAP (acidic isopropyl phosphate), BHT (2, 6-di-tert-butyl-4-methylphenol) , BHA (mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol) , vegetable oils, mineral oils, fatty acids, and fatty acid esters, and the like.

For the pest-controlling agent of the present invention, it is preferable to use compound (1) as is, or by diluting it with water or the like. The pest-controlling agent of the present invention may be used by mixing with, for example, other pest- controlling agents, such as known insecticides, nematicides, acaricides, fungicides, herbicides, plant-growth-controlling agents, synergists, soil conditioners, animal feeds, and the like, or it may be used simultaneously with these agents without mixing.

The amount of the pest-controlling agent of the invention is not limited, and may be suitably selected from a wide range according to various conditions such as the

concentration of active ingredient, the form of preparation, type of disease or pest to be treated, type of plant, severity of disease, time for application, method of application, chemicals to be used in combination (insecticide, nematicide, miticide, fungicide, herbicide, plant growth control agent, synergist, soil conditioner, etc.), and amount and type of fertilizer.

When used as a fungicide, compound (1) of the present invention is usually used in an amount of 0.01 to 500 g/100 m², and preferably 1 to 200 g/100 m².

When used as a miticide, compound (1) of the present invention is usually used in an amount of 0.1 to 500 g/100 m², and preferably 1 to 200 g/100 m².

When the emulsion, wettable powder, flowable preparation, or the like is used by diluting with water, the concentration is 0.1 to 1,000 ppm, and preferably 1 to 500 ppm. The granules, dusts, or the like can be used as is without

dilution. The amount or concentration of application of the compound may be suitably increased or decreased according to the type of formulation, time of application, place of application, method of application, type of insect, severity of damage, and the like.

Compound (1) of the present invention is characterized by having a particularly excellent fungicidal activity and a broad spectrum of activity. The compound may be used for

controlling plant diseases ascribed to various fungal pathogens or resistant fungal pathogens. Examples of such fungal pathogens include those that cause cucumber gray mold, rice plant blast, rice plant sheath blight, apple powdery mildew, apple Alternaria blotch, persimmon powdery mildew, grape powdery mildew, barley powdery mildew, wheat powdery mildew, cucumber powdery mildew, cucumber gray mold, tomato late blight, strawberry powdery mildew, tobacco powdery mildew, and the like.

Compound (1) of the present invention is effectively used as an agricultural and horticultural insecticide, miticide, nematicide, or a soil insecticide. Specifically, compound (1) of the present invention is effective for controlling

pests, such as green peach aphids, cotton aphids, and like

aphids; diamondback moths, cabbage armyworms, common cutworms, codling moths, bollworms, tobacco budworms, gypsy moths, rice leafrollers, smaller tea tortrix moths, Colorado potato beetles, cucurbit leaf beetles, boll weevils, plant hoppers, leafhoppers, scales, bugs, whiteflies, thrips, grasshoppers, anthomyiid flies/ scarabs, black cutworms, cutworms, ants, and agricultural pest insects; slugs, snails, and like gastropods; rat mite,

cockroaches, houseflies, house mosquitoes, and like hygiene- harming insects; angoumois grain moths, adzuki bean weevils, red flour beetles, mealworms, and like stored-grain insects;

casemaking clothes moths, black carpet beetles, subterranean termites, and like clothes-harming insects and house- and

household-harming insects; and the like,

mites, such as two-spotted spider mites, carmine spider mites, . citrus red mites, Kanzawa spider mites, European red mites, broad mites, pink citrus rust mites, bulb mites, and like plant- parasitic mites; Tyrophagus putrescentiae, Dermatophagoides farinae, Chelacaropsis moorei, and like house dust mites; and the like, and

soil pests, such as root-knot nematodes, cyst nematodes, root- lesion nematodes, white-tip nematode, strawberry bud nematode, pine wood nematode, and like plant parasitic nematodes; pill bugs, sow bugs, and like isopods; and the like.

The pest-controlling agent of the present invention is also effective for controlling various pests resistant to

chemicals such as organophosphorus agents, carbamate agents, synthetic pyrethroid agents, and neonicotinoid agent. Examples

The present invention is described in more detail with reference to the following Examples; however, the present

invention is not limited to these Examples.

Production Example 1; Production of N'-(2- chlorophenyl) acetohydrazide

To a cooled solution of 1- (chlorophenyl) hydrazine (3.0 g, 21.12 mmol, 1 equiv.) in dichloromethane (40 ml), was slowly added triethyl amine (6.41 g, 63.36 mmol, 3 equiv.) followed by acetic anhydride (2.59 g, 25.35 mmol, 1.2 equiv.). The resulting mixture was then stirred at room temperature for 3 hrs. The reaction mixture was then poured into cold water and extracted with dichloromethane. The combined organic layer was washed with distilled water, dried over sodium sulfate, filtered, and

concentrated under reduced pressure to get 2.5 g of the crude product. The crude product thus obtained was used in the

subsequent reaction without any purification.

1H NMR (DMSO-d⁶): δ 9.79 (bs, 1H) , 7.37 (bs, 1H) , 7.28-7.26 (m, 1H), 7.17-7.13 (m, 1H) , 6.76-6.72 (m, 2H) , 1.92 (s, 3H) . Production Example- 2: Production of (E) -3- (4-chloro- fluorophenyl) -1- (pyridin-3-yl)prop-2-en-l-one

To a solution of 1- (pyridin-3-yl) ethanone (4.00 g, 33.05 mmol, 1 equiv.) and 2-fluoro, 4-chlorobenzaldehyde (7.8 g, 49.58 mmol, 1.5 equiv.) in a mixture of THF/water (40/20 ml), was slowly added aqueous NaOH solution (1.3 g, 33.05 mmol, 1.0 equiv., in 10 ml distilled water) . The resulting mixture was then stirred at room temperature for 12 hrs. The reaction mixture was then extracted with ethyl acetate. The organic layer was washed with distilled water, dried over sodium sulfate, filtered, and

concentrated under reduced pressure to get a crude product. The crude product thus obtained was purified by column chromatography on silica gel with a mixture of ethyl acetate and n-hexane as an eluent to obtain 1.90 g of the title compound.

1H NMR (DMSO-d⁶): δ 9.32 (d, J = 1.6 Hz, 1H) , 8.85-8.83 (m, 1H), 8.48-8.45 (m, 1H) , 8.22 (t, J = 8.4 Hz, 1H) , 8.05 (d, J = 15.6 Hz, 1H), 7.80 (d, J= 15.6 Hz, 1H) , 7.63-7.58 (m, 2H) , 7.45- 7.43 (m, 1H) .

Example 1: Production of (4- (4-chloro-2-fluorophenyl) -1- (2- chlorophenyl) -4, 5-dihydro-3-methyl-lH-pyrazol-5-yl) (pyridin-3-yl) methanone (1B-71)

A mixture of N' - (2-chlorophenyl) acetohydrazide (0.88 g, 4.82 mmol, 1.4 equiv.) in phosphorus oxychloride (P0C1₃, 2.64 g,

17.20 mmol, 5 equiv.) was refluxed for 3 hrs under nitrogen atmosphere and volatiles were then removed under reduced pressure.

The crude thus obtained was diluted with chloroform (10 ml) and was slowly added triethyl amine (0.696 g, 6.88 mmol, 2.0 equiv.) followed by (Έ) -3- (4-chloro-fluorophenyl) -1- (pyridin-3- yl)prop-2-en-l-one (0.90 g, 3.44 mmol, 1 equiv.). The reaction mixture was then refluxed for 10 hrs.

The reaction mixture was then poured into cold water and extracted with dichloromethane. The combined organic layer was washed with distilled water, dried over sodium sulfate, filtered, and concentrated under reduced pressure to get a crude product. The crude product thus obtained was purified by column

chromatography on silica gel with a mixture of ethyl acetate and n-hexane as an eluent to obtain 0.50 g of the title compound.

Table 3 shows ¹H-NMR data of the thus obtained title compound 1B-71.

Example 2: Production of (4- (4-chloro-2-fluorophenyl) -1- (2- chlorophenyl) -4, 5-dihydro-3-methyl-lH-pyrazol-5-yl) (pyridin-3- yl)methanol (1B-75)

To a cooled solution of (4- (4-chloro-2-fluorophenyl) -1- (2- chlorophenyl) -4, 5-dihydro-methyl-lH-pyrazol-5-yl) (pyridin-3- yl)methanone (1B-71, 0.12 g, 0.28 mmol, 1 equiv. ) in methanol (5 ml) was added sodium borohydride (0.01 g, 0.28 mmol, 1 equiv.) portionwise under nitrogen atmosphere. The resulting mixture was then stirred at room temperature for 30 min. After distillation of solvent under reduced pressure, the reaction mixture was^" extracted with ethyl acetate. The combined organic layer was washed with distilled water, dried over sodium sulfate, filtered, and concentrated under reduced pressure to get a crude product. The crude product thus obtained was purified by column

chromatography on silica gel with a mixture of ethyl acetate and n-hexane as an eluent to obtain 0.10 g of the title compound.

Table 3 shows ¹H-NMR data of the thus obtained title compound 1B-75.

Example 3: Production of (4- (4-chloro-2-fluorophenyl) -1- (2- chlorophenyl) -3-methyl-lH-pyrazol-5-yl) (pyridin-3-yl)methanone (1A-77)

To a solution of (4- (4-chloro-2-fluorophenyl) -1- (2- chlorophenyl) -4, 5-dihydro-3-methyl-lH-pyrazol-5-yl) (pyridin-3- yl)methanone (1B-71, 0.30 g, 0.70 mmol, 1 equiv.) in

dichloromethane (10 ml) was portionwise added lead tetraacetate (0.37 g, 0.84 mmol, 1.2 equiv.) at room temperature under nitrogen atmosphere. The reaction mixture was then stirred at room temperature for 18 hrs and after that filtered through a celite bed. The filtrate was then diluted with dichloromethane, and the organic layer was then washed with distilled water, dried over sodium sulfate, filtered, and concentrated under reduced pressure to get a crude product. The crude product thus obtained was purified by column chromatography on silica gel with a mixture of ethyl acetate and n-hexane as an eluent to obtain 0.22 g of the title compound 1A-77.

Table 1 shows ¹H-NMR data of the thus obtained title compound 1A-77.

Example 4: Production of (4- (2, 4-dichlorophenyl) -1- (2, 4- difluorophenyl) -3-methyl-lH-pyrazol-5-yl) (pyridin-3-yl)methanol (lA-80)

To a solution of (4- (2, 4-dichlorophenyl) -1- (2, 4- diflu^'orophenyl) -3-methyl-lH-pyrazol-5-yl) (pyridin-3-yl)methanone (1A-77, 0.10 g, 0.22 mmol, 1 equiv. ) in methanol (5 ml) was added sodium borohydride (0.008 g, 0.22 mmol, 1 equiv.) portionwise under nitrogen atmosphere. The reaction mixture was then stirred at room temperature for 30 min. After distillation of solvent under reduced pressure, the mixture was extracted with ethyl acetate. The combined organic layer was washed with distilled water, dried over sodium sulfate, filtered, and concentrated under reduced pressure to get a crude product. The crude product thus obtained was purified by column chromatography on silica gel with a mixture of ethyl acetate and n-hexane as an eluent to obtain 0.07 g of the title compound 1A-80.

Table 1 shows ¹H-NMR data of the thus obtained title compound 1A-80.

Example 5: Production of (4- (4-chloro-2-fluorophenyl) -1- (4- chlorophenyl) -4, 5-dihydro-3-methyl-lH-pyrazol-5-yl) (pyridin-3- yl)methanone (1B-72)

A mixture of N' - (4-chlorophenyl) acetohydrazide (0.98 g,

5.36 mmol, 1.4 equiv.) in P0C1₃ (2.94 g, 19.15 mmol, 5 equiv.) was refluxed for 3 hrs under nitrogen atmosphere and volatiles were then removed under reduced pressure.

The crude thus obtained was diluted with chloroform (10 ml) and to this was slowly added triethyl amine. (0.78 g, 7.66 mmol, 2.0 equiv.) followed by (E) -3- (4-chloro-2-fluorophenyl) -1- (pyridin-3-yl)prop-:2-en-l-one (1.0 g, 3.83 rnmol, 1 equiv.). The resulting mixture was then refluxed for 10 hrs. The reaction mixture was then poured into cooled water and extracted with dichloromethane . The combined organic layer was washed with distilled water, dried over sodium sulfate, filtered, and concentrated under reduced pressure to get a crude product. The crude product thus obtained was purified by column chromatography on silica gel with a mixture of ethyl acetate and n-hexane as an eluent to obtain 0.70 g of the title compound IB-72.

Table 3 shows ¹H-NMR data of the thus obtained title compound IB-72.

Example 6: Production of (4- (4-chloro-2-fluorophenyl) -1- (4- chlorophenyl) -4, 5-dihydro-3-methyl-lH-pyrazol-5-yl) (pyridin-3- yl)methanol (1B-76)

To a cooled solution of (4- (4-chloro-2-fluorophenyl) -1- (4- chlorophenyl) -4, 5-dihydro-methyl-lH-pyrazol-5-yl) (pyridin-3- yl)methanone (IB-72, 0.1 g, 0.23 rnmol, 1 equiv.) in methanol (5 ml) was added sodium borohydride (0.086 g, 0.234 rnmol, 1 equiv.) portionwise under nitrogen atmosphere. The reaction mixture was then stirred at room temperature for 30 min. After distillation of solvent under reduced pressure, the mixture was extracted with ethyl acetate. The combined organic layer was washed^' with distilled water, dried over sodium sulfate, filtered, and concentrated under reduced pressure to get a crude product. The crude product thus obtained was purified by column chromatography on silica gel with a mixture of ethyl acetate and n-hexane as an eluent to obtain 0.70 g of the title compound 1B-76.

Table 3 shows ¹H-NMR data of the thus obtained title compound 1B-76.

Example 7: Production of (4-(4-chloro-2-fluorophenyl) -1- (4- chlorophenyl) -3-methyl-lH-pyrazol-5-yl) (pyridin-3-yl)methanone (lA-78)

To a solution of (4- (4-chloro-2-fluorophenyl) -1- (4- chlorophenyl) -4, 5-dihydro-3-methyl-lH-pyrazol-5-yl) (pyridin-3- yl)methanone (1B-72, 0.30 g, 0.70 iranol, 1 equiv. ) in dichloromethane (10 ml) was added portionwise lead tetraacetate (0.43 g, 0.983 mmol, 1.4 equiv.) at room temperature under nitrogen atmosphere. The reaction mixture was then stirred at room temperature for 18 hrs and after that filtered through a celite bed. The" filtrate was then diluted with dichloromethane and the organic layer was then washed with distilled water, dried over sodium sulfate, filtered, and concentrated under reduced pressure to get a crude product. The crude product thus obtained was purified by column chromatography on silica gel with a mixture of ethyl acetate and n-hexane as an eluent to obtain 0.20 g of the title compound 1A-78.

Table 1 shows ¹H-NMR data of the thus obtained title compound 1A-78.

Example 8: Production of (4-.(4-chloro-2-fluorophenyl) -1- (4- chlorophenyl) -3-methyl-lH-pyrazol-5-yl) (pyridin-3-yl)methanol (1A-79)

To a solution of (4- (4-chloro-2-fluorophenyl) -1- (4- chlorophenyl) -3-methyl-lH-pyrazol-5-yl) (pyridin-3-yl) methanone (1—78, 0.10 g, 0.23 mmol, 1 equiv.) in methanol (5 ml) was added sodium borohydride (0.008 g, 0.22 mmol, 1 equiv.) portionwise under nitrogen atmosphere. The reaction mixture was then stirred at room temperature for 30 min. After distillation of solvent under reduced pressure, the mixture was extracted with ethyl acetate. The combined organic layer was washed with distilled water, dried over sodium sulfate, filtered, and concentrated under reduced pressure to get a crude product. The crude product thus obtained was purified by column chromatography on silica gel with a mixture of ethyl acetate and n-hexane as an eluent to obtain 0.07 g of the title compound 1A-79.

• Table 1 shows ¹H-NMR data of the thus obtained title compound 1A-79.

Production Example 3: Production of 2- (2, 4-difluorophenyl) -3- oxobutanenitrile

To a stirred solution of xylene (60 ml) and ethanol (30 ml), sodium ethoxide (17.7 g, 0.261 moles, 2.0 equiv.) was added at 0°C within 10 minutes. After 10 minutes the solution was heated to 55°C. After 30 minutes, a solution of 2-(2,4- difluorophenyl)acetonitrile (20.0 g, 0.13 moles, and 1.0 equiv.) in acetic acid (80 ml) was slowly added to the reaction mixture. The reaction mass was stirred at 55°C for 6 hrs. After the reaction, the solution was cooled, and the solvent was evaporated under pressure through an evaporator. Cold water (100 ml) was poured into the reaction mixture, and the resulting mixture was treated with aqueous IN HC1 solution and maintained at a pH of 2- 3 in an ice cooling bath. The reaction mass was extracted with ethyl acetate (4x50 ml), the organic layer was washed with distilled water, dried over sodium sulfate, filtered, and

concentrated under reduced pressure to get 2.5 g of the crude product. The crude product thus obtained was treated with n- pentane and ether to get 2- (2, 4-difluorophenyl) -3- oxobutanenitrile (20.5 g) as a solid product.

• ¹H NMR (CDC1₃) d: 7.42-7.38 (m, 1H) , 7.01-6.91 (m, 2H) , 4.93 (s, 1H) , 2.36 (s, 3H) .

Production Example 4; Production of 1, 4-bis (2, 4-difluorophenyl) - 3-methyl-lH-pyrazol-5-amine

To a solution of 2- (2, 4-difluorophenyl) -3-oxobutanenitrile (1.0 g, 0.005 moles, 1.0 equiv.) in ethanol (15 ml) was added sodium acetate (0.49 g, 0.006 moles, 1.2 equiv.) portionwise followed by 1- (2, 4-difluorophenyl) hydrazine hydrochloride (1.25 g 0.007 moles, 1.5 equiv.). The reaction solution was stirred at 90°C for 10 hrs. After the reaction, the solution was cooled, and the solvent was evaporated under reduced pressure through an evaporator. Cold water (20 ml) was poured into the reaction mixture, and the resulting mixture was treated with aqueous IN HC1 solution and maintained at a pH of 2-3 in an ice cooling bath The reaction solution was extracted with ethyl acetate (4*50 ml), the organic layer was washed with brine solution, dried over sodium sulfate, filtered, and concentrated under reduced pressure to get the crude product. The crude product thus obtained was treated with n-pentane and ether to get 1, 4-bis (2,4- difluorophenyl)-3-methyl-lH-pyrazol-5-amine (1.4 g) as a brown solid product.

1H NMR (DMSO-d6) 6: 7.56-7.46 (m, 2H) , 7.42-7.36 (m, 1H) ,

7.30-7.21 (m, 1H) , 6.98 (m, 1H) , 5.17 (br. s, 2H) , 1.99 (s, 3H).),

Production Example 5: 1- (2, 4-dichlorophenyl) -4- (2, 4- difluorophenyl)-3-methyl-lH-pyrazol-5-amine

To a solution of 2- (2, 4-difluorophenyl) -3-oxobutanenitrile

(1.0 g., 0.005 moles, 1.0 equiv.) in ethanol (15 ml) was added sodium acetate (0.49 g, 0.006 moles, 1.2 equiv.) portionwise followed by 1- (2, 4-dichlorophenyl) hydrazine hydrochloride (1.5 g, 0.007 moles, 1.5 equiv.). The reaction solution was stirred at 90°C for 10 hrs. After the reaction, the solution was cooled, and the solvent was evaporated under reduced pressure through an evaporator. Cold water (20 ml) was poured into the reaction mixture, and the solution was extracted with ethyl acetate (4*50 ml) . The organic layer was washed with brine solution, dried over sodium sulfate, filtered, and concentrated under reduced pressure to get the crude product. The crude product thus obtained was treated with n-pentane and ether to get 1- (2, 4-dichlorophenyl) -4- (2, 4-difluorophenyl) -3-methyl-lH-pyrazol-5-amine (1.5 g) as a brown solid product.

1H NMR (DMSO-d6) 6: 7.83 (s, 1H) , 7.58-7.50 (m, 2H) ,

7.39 (dd, J= 8.4 Hz, 15.2 Hz, 1H) , 7.29-7.24 (m, 1H) , 7.13-7.08 (m, 1H), 5.16 (bs, 2H) , 2.00 (s, 3H) .

Example 9: Production of N- (1, 4-bis (2, 4-difluorophenyl) -3-methyl- lH-pyrazol-5-yl) pyridine-3-amine (ΙΑ' -89)

To a solution of 1, 4-bis (2, 4-difluorophenyl) -3-methyl-lH- pyrazol-5-amine (0.3 g, 0.0009 moles, 1.0 equiv.) in toluene (10 ml) was added cesium carbonate (1.21 g, 0.0037 moles, 4.0 equiv.) portionwise followed by 3-bromopyridine (0.148 g, 0.0009 moles, 1.0 equiv.) drop wise. The reaction solution was purged with nitrogen gas for 20 minutes. After 20 minute, palladium (II) acetate (0.063 g, 0.00009 moles, 0.1 equiv.) followed by

xanthphos (0.108 g, 0.0001 moles, 0.2 equiv.) was added under nitrogen atmosphere and again purged for 5 minutes. The reaction mixture was stirred at 100°C for about 8 hrs.

After the reaction, the reaction solution was cooled and filtered through a celite bed. The filtrate was evaporated under reduced pressure through an evaporator. The resulting concentrate was diluted with water (10 ml) and extracted with ethyl acetate (3x10 ml) and the organic layer was washed with brine solution and dried over anhydrous sodium sulfate, filtered, and

concentrated under reduced pressure to get a crude product. The crude product was purified by column chromatography on silica gel with a mixture of ethyl acetate and n-hexane (40:60) as an eluent to obtain 0.23 g of the title compound lA'-89 as a white solid product.

Table 2 shows ¹H-NMR data of the thus obtained title compound 1A' -89.

Example 10: Production of N- (1- (2, 4-dichlorophenyl) -4- (2, 4- difluorophenyl)-3-methyl-lH-pyrazol-5-yl) pyridin-3-amine (1A' - 91)

To a solution of 1- (2, 4-dichlorophenyl) -4- (2, 4- difluorophenyl)-3-methyl-lH-pyrazol-5-amine (0.3 g, 0.0008 moles, 1.0 equiv.) in toluene (10 ml) was added cesium carbonate (1.1 g, 0.0033 moles, 4.0 equiv.) portionwise followed by 3-bromopyridine (0.134 g, 0.0008 moles, 1.0 equiv.) drop wise. The reaction solution was purged with nitrogen gas for 20 minutes. After 20 minutes, palladium (II) acetate (0.057 g, 0.00008 moles, 0.1 equiv.), followed by xanthphos (0.098 g, 0.0001 moles, 0.2 equiv.), was added under nitrogen atmosphere and again purged for. 5 minutes. The reaction mixture was stirred at 100°C for about 8 hrs.

After the reaction, the reaction solution was cooled and filtered through a celite bed. The filtrate was evaporated under reduced pressure through an evaporator. The resulting concentrate . was diluted with water (10 ml) and extracted with ethyl acetate (3x10 ml) and the organic layer was washed with brine solution, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to get a crude product. The crude product was purified by column chromatography on silica gel with a mixture of ethyl acetate and n-hexane (40:60) as an eluent to obtain 0.155 g of the title compound 1A'-91 as a white solid product .

Table 2 shows ¹H-NMR data of the thus obtained title compound 1A'-91.

Example 11:

The compounds shown in Tables 1, 2, and 3, other than the compounds obtained in Examples 1 to 10, were produced by methods similar to the methods described in Examples 1 to 10.

Tables 1, 2 and 3 show MS and ¹H-NMR data of the thus obtained compounds of the present invention.

The abbreviations in Tables 1, 2 and 3 are as indicated below.

F: fluoro

CI : chloro

Br: bromo

Me: methyl

Et: ethyl

Ph: phenyl

CF₃: trifluoromethyl

OCF₃: trifluoromethoxy

OH: hydroxy

OMe: methoxy

OAc: acetyl

CN: cyano

NO₂: nitro

S: sulfur atom

0: oxygen atom

Py: pyridyl M. Pt..:melting point MS:mass spectrometry No. : compound number

Table 1

Table 2

Table 3

Preparation Example 1: Emulsions

10 parts of each compound of the invention was dissolved in 45 -parts of Solvesso 150 and 35 parts of ΛΓ- methylpyrrolidone. 10 parts of an emulsifier (trade name: Sorpol 3005X, produced by Toho Chemical Industry Co., Ltd.) was added thereto. The mixtures were mixed by stirring to give 10%

emulsions .

Preparation Example 2: Wettable powders

20 parts of each compound of the invention was added to a mixture of 2 parts of sodium lauryl sulfate, 4 parts of sodium lignin sulfonate, 20 parts of fine powder of synthetic hydrated silicon dioxide, and 54 parts of clay. The mixtures were mixed by stirring with a juice mixer to give 20% wettable powders.

Preparation Example 3: Granules

2 parts of sodium dodecylbenzenesulfonate, 10 parts of bentonite, and 83 parts of clay were added to 5 parts of each compound of the invention, and each mixture was sufficiently mixed by stirring. An appropriate amount of water was added thereto. The resulting mixtures were further stirred and

granulated with a granulator. The granules were air-dried to give 5% granules.

Preparation Example 4: Dusts

1 part of each compound of the invention was dissolved in an appropriate amount of acetone. 5 parts of fine powder of : synthetic hydrated silicon dioxide, 0.3 parts of acidic isopropyl phosphate (PAP), and 93.7 parts of clay were added thereto. The mixtures were mixed by stirring with a juice mixer, and acetone was removed by evaporation to give 1% dust. Preparation Example 5: Flowable preparations

20 parts of each compound of the invention was mixed with 20 parts of water containing 3 parts of polyoxyethylene tristyrylphenyl ether phosphoric acid ester triethanolamine and 0.2 parts of Rhodorsil 426R. The mixtures were subjected to wet pulverization with a DYNO-Mill, and mixed with 60 parts of water ·· containing 8 parts of propylene glycol and 0.32 parts of xanthan gum to give 20% suspensions in water.

Test Examples are given below to demonstrate that the compounds of the invention are useful as an active ingredient for fungicides .

Test Ex-ample 1; Fungicidal test on cucumber gray mold

A small amount of mycelia of Botrytis cinerea was collected from a culture tube, and aseptically transferred to a potato dextrose agar (PDA) plate. The plate on which Botrytis cinerea was seeded was kept in the dark for five days, then under blacklight-blue (BLB) irradiation for four days, and finally in the dark at 20°C for four days.

Meanwhile, 100 ml of a YG (0.2% yeast extract + 1% glucose) solution was prepared using distilled water. 20 ml^" of the YG solution was poured into the culture plate, and the surface was scraped with a brush. The obtained suspension was filtered through tissue paper. The filtrate thus obtained was diluted with the YG solution to 1 x 10⁶ cfu of spores per ml.

A solution of each compound of the invention (200 ppm) was sprayed on fresh, excised cucumbers at the three-leaf stage or later . A cotyledon of the treated plant was cut and placed on . moist' tissue paper on a plastic tray. 50 μl of the spore

suspension (YG solution) was dropped on the middle of the

cotyledon by using a micropipette. A small piece of absorbent cotton was then placed on the spore suspension drop, and 50 μl of the YG solution was again dropped on the absorbent cotton. The plastic tray containing the cotyledon was placed in a box

containing water at the bottom, and maintained at room

temperature (20°C) .

Five days after inoculation, the radial growth of the fungus was measured, and the activity of each compound was calculated as a preventive value according to the following equation. : Equation

Preventive value = {1- (average radius of lesions in treated plant/average radius of lesions in untreated plant) }x100

The compounds that exhibited a disease control value of 50% or more at 500 ppm are as follows:

Compound Nos.: 1A-29, 1A-30, 1A-53, 1A-62, 1A-67, 1A-93, 1A-112, 1A-113, 1A-121;

1A'-13, lA'-24, 1Α'-28, 1Α'-29, 1Α'-30, 1A'-31, 1A' -32, .1A' -33, lA'-37, lA'-38, 1Α'-60, 1A'-61, 1Α'-64, 1Α'-65, 1Α'-66, 1Α'-67, ^; lA'-75;

1B-42, 1B-56, 1B-57, 1B-66, 1B-70, 1B-103, 1B-105, 1B-107, 1B-108, 1B-112, 1B-115.

Test Example 2: Fungicidal test on cucumber powdery mildew

An aqueous solution of Sorpol 355 (produced by Toho Chemical Industry Co., Ltd.) (100 ppm) was added to a methanol solution of each test compound to give sample solutions (500 ppm) . Each sample solution was spread on cucumbers (14 days after seeding) planted in a pot (7.5 cm in diameter), and air-dried. A suspension containing spores of cucumber powdery mildew (1.0 * 10⁵ cells/ml) was sprayed on each plant using a spray gun. After air drying, the plant was left to stand in an acrylic resin

greenhouse and, after 10 days, was checked for the severity of disease. The preventive value was calculated, in comparison with the severity of disease in an untreated plant.

The preventive value was calculated by using the following equation, in comparison with the severity of disease in an untreated plant.

Equation

Preventive value = {1- (average radius of lesions in treated plant/average radius of lesions in untreated plant) }*100 The compounds that exhibited a disease control value of 80% or more at 500 ppm are as follows:

Compound Nos . : 1A-18, 1A-20, 1A-22, 1A-25, 1A-28, 1A-29, 1A-30, 1A-31, 1A-32, 1A-33, 1A-34, 1A-35, 1A-36, 1A-37, 1A-38, 1A-44, 1A-45, 1A-50, 1A-51, 1A-52, 1A-53, 1A-56, 1A-57, 1A-58, 1A-59, 1A-60, 1A-61, 1A-62, 1A-63, 1A-64, 1A-65, 1A-66, 1A-67, 1A-68, 1A-70, 1A-71, 1A-73, 1A-76, 1A-79, 1A-80, 1A-83, 1A-84, 1A-85, 1A-86, 1A-87, 1A-88, 1A-89, 1A-90, 1A-91, 1A-92, 1A-93, 1A-95, 1A-96, 1A-97, 1A-98, 1A-99, lA-100, 1A-105, 1A-106, 1A-107, 1A- 108, 1A-109, lA-110, lA-111, 1A-112, 1A-113, 1A-114, 1A-115, 1A- 116, 1A-117, 1A-118, 1A-119, 1A-120, 1A-121, 1A-122, 1A-123, 1A- 124;

1A'-1, lA'-9, 1A'-1O, 1A'-1l, 1A'-13, 1A'-14, 1A'-16, 1A'-17, IK' -21, lA'-23, lA'-34, 1Α'-35, 1Α'-36, 1Α'-37, 1Α'-54, 1Α'-56, 1Α'-59, 1Α'-64, 1Α'-65, 1Α'-74, lA'-76, lA'-78, 1Α'-79, 1Α'-85, lA'-86, lA'-87, 1Α'-88, 1Α'-89, 1Α'-90, 1A'-91, 1Α'-92, 1Α'^'-94, lA'-95, lA'-96, 1Α'-97, 1Α'-98, ΙΑ'-ΙΟΙ, 1A'-104, 1A'-106, 1A' - 107, 1A'-108, 1A'-109, lA'-HO, 1A'-1ll, 1A'-112, 1A'-113, 1A'- 114, 1A'-115, 1A'-116, 1A'-117, 1A'-118, 1A'-119, 1A'-120, 1A' - 121, 1A'-122, 1A'-123, 1A'-124;

1B-7, 1B-22, 1B-28, 1B-30, 1B-31, 1B-32, 1B-33, 1B-34, 1B-35, 1B- 36, 1B-38, lB-41, 1B-43, 1B-45, 1B-46, 1B-47, 1B-50, 1B-51, 1B-52, 1B-53, 1B-54, 1B-55, 1B-56, 1B-57, 1B-59, 1B-60, 1B-61, 1B-63, 1B-64, 1B-65, 1B-66, 1B-67, 1B-69, 1B-70, 1B-72, 1B-73, 1B-75, 1B-76, 1B-78, 1B-79, 1B-80, 1B-81, 1B-82, 1B-83, 1B-84, 1B-85, 1B-86, 1B-87, 1B-88, 1B-89, 1B-90, 1B-91, 1B-92, 1B-93, 1B-94, 1B-95, 1B-96, 1B-97, 1B-98, 1B-99, lB-100, lB-101, 1B-102, 1B-103, 1B-104, 1B-105, 1B-106, 1B-107, 1B-108, 1B-109, lB-110, IB-Ill, 1B-112, 1B-115, 1B-116, 1B-117, 1B-118.

Claims

[Claim 1]

A heterocyclic compound represented by Formula (1) :

or a salt thereof,

unsubstituted heteroaryl group,

R² represents substituted or unsubstituted C_1-4 alkyl,

X represents C(=Y), CR⁵R⁶, NH, or NR⁷,

Y represents oxygen or sulfur,

R⁵ and R⁶ are identical or different and each represents hydrogen, hydroxy, thiol, . halogen, C_1-4 alkyl, C_1-4 haloalkyl, C_1-4 alkoxy C_1-4 alkyl, C_1-4 haloalkoxy C_1-4 alkyl, C₂-4 alkenyl, C2-4 alkynyl, C_3-8 cycloalkyl, C_3-8 cycloalkyl C_1-4 alkyl, C_1-4 alkylcarbonyl, C_1-4 alkylcarbonyloxy, C_1-4 alkoxy, C_1-4 haloalkoxy, C_1-4 alkylthio, C_1-4 haloalkylthio, C_1-4 alkylsulfonyl, C_1-4 alkylsulfinyl, arylthio, arylsulfonyl, arylsulfinyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or

R⁷ represents C_1-4 alkyl, alkylcarbonyl, or C_1-4 alkoxycarbonyl, and

the bond represented by: is a single bond or a double bond. [Claim 2·]

The heterocyclic compound or a salt thereof according to claim 1, wherein R¹ represents substituted aryl. [Claim 3]

The heterocyclic compound or a salt thereof according to claim 1 or 2, wherein R³ represents substituted aryl.

[Claim 4]

The heterocyclic compound or a salt thereof according to any one of claims 1 to 3, wherein R⁴ represents a substituted or unsubstituted heteroaryl group.

[Claim 5]

The heterocyclic compound or a salt thereof according to any one of claims 1 to 4, wherein R⁴ is substituted or unsubstituted pyridyl.

[Claim 6]

A pest-controlling agent containing the heterocyclic compound or a salt thereof of any one of claims 1 to 5.

[Claim 7]

A fungicide containing the heterocyclic compound or a salt thereof of any one of claims 1 to 5.