Pyrazole compound and agricultural or horticultural germicide

Abstract

Provided is a compound that has germicidal activity with respect to pathogenic germs in agricultural or horticultural plants, said compound being represented by formula (I). (In the formula, R1 represents a C1-6 alkyl group or the like, R2 represents a hydrogen atom, a C1-6 alkyl group, or the like, A represents a divalent hydrocarbon group or the like, R3 represents a hydrogen atom, R4 represents a hydrogen atom or the like, R5 represents a hydrogen atom, a C1-6 alkyl group, or the like, B represents a phenylene group, a 5-6 membered heterocyclylene group, *1-CO-NRa-*2, *1-NRa-*2, an oxygen atom, a sulfur atom, or a single bond, *1 represents a bond with carbon to which the symbol * has been provided in formula (I), *2 represents a bond with Q2, Ra represents a hydrogen atom or the like, Q1 represents a 5-6 membered heterocyclyl group or the like, and Q2 represents a C1-6 alkyl group, a phenyl group, a 9-10 membered heterocyclyl group, or the like.)

Description

Pyrazole compounds and agricultural and horticultural fungicides

[0001] The present invention relates to a pyrazole compound and an agricultural and horticultural fungicide. More specifically, the present invention relates to a pyrazole compound that has excellent fungicidal activity against pathogens that affect agricultural and horticultural plants, is highly safe, and can be synthesized industrially advantageously, and to an agricultural and horticultural fungicide containing the pyrazole compound as an active ingredient. This application claims priority based on Japanese Patent Application No. 2023-218024, filed on December 25, 2023, the contents of which are incorporated herein by reference.

[0002] Various compounds have been proposed that have fungicidal activity against pathogens that affect agricultural and horticultural plants. In order for such compounds to be practically used as agricultural and horticultural fungicides, they must not only have sufficiently high efficacy but also be unlikely to develop fungicide resistance, not cause phytotoxicity to plants or soil contamination, and have low toxicity to livestock, fish, etc.

[0003] Incidentally, Patent Document 1 discloses compounds represented by formula (P-10) and the like.

[0004]

[0005] WO 2023 / 012044 Al

[0006] The object of the present invention is to provide a pyrazole compound which has excellent fungicidal activity against pathogenic bacteria that affect agricultural and horticultural plants, is highly safe, and can be synthesized industrially in an advantageous manner, and to provide an agricultural and horticultural fungicide containing the same as an active ingredient.

[0007] As a result of intensive research aimed at solving the above problems, the present invention has been completed, including the following aspects: <1> A compound represented by formula (I) or a salt thereof.

[0008]

[0009] In formula (I), R １ represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, or a substituted or unsubstituted C3-6 cycloalkyl group; R ２represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylcarbonyloxy group, a substituted or unsubstituted C1-6 alkoxycarbonyloxy group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1- A represents a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, a substituted or unsubstituted phenyloxy group, a substituted or unsubstituted naphthyloxy group, a substituted or unsubstituted 5- to 6-membered heterocyclyloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a nitro group, a cyano group, or a halogeno group; A represents a substituted or unsubstituted divalent hydrocarbon group or a substituted or unsubstituted heteroatom-containing divalent organic group; Q represents a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, a substituted or unsubstituted phenyloxy group, a substituted or unsubstituted naphthyloxy group, a substituted or unsubstituted 5- to 6-membered heterocyclyloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a nitro group, a cyano group, or a halogeno group; １ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group; R ３ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a halogeno group; R ４ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a halogeno group; R ５represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a formyl group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group; B represents a substituted or unsubstituted phenylene group, a substituted or unsubstituted 5- to 6-membered heterocyclylene group, a group represented by the formula: ＊１ -CO-NR ａ - ＊２ a group represented by the formula: ＊１ -NR ａ - ＊２ *1 represents a bond to the carbon atom marked with * in formula (I), *2 represents a group represented by Q in formula (I), an oxygen atom, a sulfur atom, or a single bond. ２ indicates a bond with R ａ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a formyl group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group, ２ represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- or 6-membered heterocyclyl group, or a substituted or unsubstituted 9-10-membered heterocyclyl group.

[0010] <2> In the formula (I), R １ is a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C3-6 cycloalkyl group, R ２is a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, A is a substituted or unsubstituted divalent hydrocarbon group, R ３ and R ４ is a hydrogen atom, and R ５ is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C2-6 alkenyl group, B is a substituted or unsubstituted phenylene group, a substituted or unsubstituted 5- or 6-membered heterocyclylene group, a group represented by the formula: ＊１ —CO—NH— ＊２ a group represented by the formula: ＊１ -NH- ＊２ When B is a substituted or unsubstituted phenylene group, Q is a group represented by the following formula: ２ is a substituted or unsubstituted phenyl group or a substituted or unsubstituted 5- to 6-membered heterocyclyl group, and when B is a single bond, Q ２ is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group, and when B is a substituted or unsubstituted 5- to 6-membered heterocyclylene group, Q ２ is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group, and B is a group of the formula: ＊１ —CO—NH— ＊２ When Q is a group represented by ２ is a substituted or unsubstituted phenyl group, and B is a group of the formula: ＊１ -NH- ＊２ When Q is a group represented by ２ is a substituted or unsubstituted C1-6 alkyl group, and when B is an oxygen atom, Q ２ is a substituted or unsubstituted C1-6 alkyl group, or a salt thereof.

[0011] <3> An agricultural and horticultural fungicide containing, as an active ingredient, at least one selected from the group consisting of the compound according to <1> or <2> and a salt thereof.

[0012] The pyrazole compound of the present invention has excellent fungicidal activity against pathogenic bacteria that affect agricultural and horticultural plants, is highly safe, and can be synthesized industrially advantageously. The agricultural and horticultural fungicide of the present invention can effectively control diseases of agricultural and horticultural plants.

[0013] The pyrazole compound of the present invention is a compound represented by formula (I) (hereinafter, may be referred to as compound (I)) or a salt of compound (I).

[0014]

[0015] In formula (I), R １ represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, or a substituted or unsubstituted C3-6 cycloalkyl group; R ２ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylcarbonyloxy group, a substituted or unsubstituted C1-6 alkoxycarbonyloxy group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1- A represents a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, a substituted or unsubstituted phenyloxy group, a substituted or unsubstituted naphthyloxy group, a substituted or unsubstituted 5- to 6-membered heterocyclyloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a nitro group, a cyano group, or a halogeno group; A represents a substituted or unsubstituted divalent hydrocarbon group or a substituted or unsubstituted heteroatom-containing divalent organic group; Q represents a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, a substituted or unsubstituted phenyloxy group, a substituted or unsubstituted naphthyloxy group, a substituted or unsubstituted 5- to 6-membered heterocyclyloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a nitro group, a cyano group, or a halogeno group; １represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group; R ３ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a halogeno group; R ４ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a halogeno group; R ５ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a formyl group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group; B represents a substituted or unsubstituted phenylene group, a substituted or unsubstituted 5- to 6-membered heterocyclylene group, a group represented by the formula: ＊１ -CO-NR ａ - ＊２ a group represented by the formula: ＊１ -NR ａ - ＊２ *1 represents a bond to the carbon atom marked with * in formula (I), *2 represents a group represented by Q in formula (I), an oxygen atom, a sulfur atom, or a single bond. ２ indicates a bond with R ａ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a formyl group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group, ２represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- or 6-membered heterocyclyl group, or a substituted or unsubstituted 9-10-membered heterocyclyl group.

[0016] In the present invention, the term "unsubstituted" refers to only the core group. When the name of the core group alone is used without the term "substituted," it means "unsubstituted" unless otherwise specified. On the other hand, the term "substituted" means that any hydrogen atom in the core group has been replaced with a group (substituent) of the same or different structure as the core group. Therefore, a "substituent" is another group bonded to the core group. The number of substituents may be one or more. The two or more substituents may be the same or different. A term such as "C1-6" indicates that the core group has 1 to 6 carbon atoms, for example. This number of carbon atoms does not include the number of carbon atoms in the substituent. For example, a butyl group having an ethoxy group as a substituent is classified as a C2 alkoxy C4 alkyl group. The "substituent" is not particularly limited as long as it is chemically permissible and provides the effects of the present invention.

[0017] Examples of groups that can serve as "substituents" include: C1-6 alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, n-pentyl, and n-hexyl; C2-6 alkenyl groups such as vinyl, 1-propenyl, 2-propenyl (allyl), 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, and 2-methyl-2-propenyl; C2-6 alkynyl groups such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, and 1-methyl-2-propynyl;

[0018] C3-6 cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups; aryl groups such as phenyl, tolyl, xylyl, trimethylphenyl, and naphthyl groups; phenyl C1-6 alkyl groups such as benzyl and phenethyl groups; 3- to 6-membered heterocyclyl groups; 3- to 6-membered heterocyclyl C1-6 alkyl groups;

[0019] hydroxyl groups; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy groups; C2-6 alkenyloxy groups such as vinyloxy, allyloxy, propenyloxy, and butenyloxy groups; C2-6 alkynyloxy groups such as ethynyloxy and propargyloxy groups; phenoxy and naphthoxy groups; phenyl C1-6 alkoxy groups such as benzyloxy and phenethyloxy groups; 5- to 6-membered heteroaryloxy groups such as thiazolyloxy and pyridyloxy groups; 5- to 6-membered heteroaryl C1-6 alkyloxy groups such as thiazolylmethyloxy and pyridylmethyloxy groups;

[0020] a formyl group; a C1-6 alkylcarbonyl group such as an acetyl group or a propionyl group; a formyloxy group; a C1-6 alkylcarbonyloxy group such as an acetyloxy group or a propionyloxy group; a benzoyl group; a C1-6 alkoxycarbonyl group such as a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, an n-butoxycarbonyl group or a t-butoxycarbonyl group; a C1-6 alkoxycarbonyloxy group such as a methoxycarbonyloxy group, an ethoxycarbonyloxy group, an n-propoxycarbonyloxy group, an i-propoxycarbonyloxy group, an n-butoxycarbonyloxy group or a t-butoxycarbonyloxy group; a carboxyl group;

[0021] halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group; C1-6 haloalkyl groups such as a chloromethyl group, a chloroethyl group, a trifluoromethyl group, a 1,2-dichloro-n-propyl group, a 1-fluoro-n-butyl group, and a perfluoro-n-pentyl group; C2-6 haloalkenyl groups such as a 2-chloro-1-propenyl group and a 2-fluoro-1-butenyl group; C2-6 haloalkynyl groups such as a 4,4-dichloro-1-butynyl group, a 4-fluoro-1-pentynyl group, and a 5-bromo-2-pentynyl group; C1-6 haloalkoxy groups such as a trifluoromethoxy group, a 2-chloro-n-propoxy group, and a 2,3-dichlorobutoxy group; C2-6 haloalkenyloxy groups such as a 2-chloropropenyloxy group and a 3-bromobutenyloxy group; C1-6 haloalkylcarbonyl groups such as a chloroacetyl group, a trifluoroacetyl group, or a trichloroacetyl group;

[0022] amino groups; C1-6 alkyl-substituted amino groups such as methylamino, dimethylamino, and diethylamino; anilino and naphthylamino groups; phenyl C1-6 alkylamino groups such as benzylamino and phenethylamino; formylamino groups; C1-6 alkylcarbonylamino groups such as acetylamino, propanoylamino, butyrylamino, and i-propylcarbonylamino; C1-6 alkoxycarbonylamino groups such as methoxycarbonylamino, ethoxycarbonylamino, n-propoxycarbonylamino, and i-propoxycarbonylamino; unsubstituted or substituted aminocarbonyl groups such as aminocarbonyl, dimethylaminocarbonyl, phenylaminocarbonyl, and N-phenyl-N-methylaminocarbonyl; imino C1-6 alkyl groups such as iminomethyl, (1-imino)ethyl, and (1-imino)-n-propyl; Substituted or unsubstituted N-hydroxyimino C1-6 alkyl groups such as an N-hydroxy-iminomethyl group, a (1-(N-hydroxy)-imino)ethyl group, a (1-(N-hydroxy)-imino)propyl group, an N-methoxy-iminomethyl group, or a (1-(N-methoxy)-imino)ethyl group; an aminocarbonyloxy group; a C1-6 alkyl-substituted aminocarbonyloxy group such as an ethylaminocarbonyloxy group or a dimethylaminocarbonyloxy group;

[0023] a mercapto group; a C1-6 alkylthio group such as a methylthio group, an ethylthio group, an n-propylthio group, an i-propylthio group, an n-butylthio group, an i-butylthio group, an s-butylthio group, or a t-butylthio group; a C1-6 haloalkylthio group such as a trifluoromethylthio group or a 2,2,2-trifluoroethylthio group; a phenylthio group or a naphthylthio group; a 5- or 6-membered heteroarylthio group such as a thiazolylthio group or a pyridylthio group;

[0024] C1-6 alkylsulfinyl groups such as methylsulfinyl, ethylsulfinyl, and t-butylsulfinyl groups; C1-6 haloalkylsulfinyl groups such as trifluoromethylsulfinyl and 2,2,2-trifluoroethylsulfinyl groups; phenylsulfinyl groups; 5- to 6-membered heteroarylsulfinyl groups such as thiazolylsulfinyl and pyridylsulfinyl groups;

[0025] C1-6 alkylsulfonyl groups such as methylsulfonyl, ethylsulfonyl, and t-butylsulfonyl groups; C1-6 haloalkylsulfonyl groups such as trifluoromethylsulfonyl and 2,2,2-trifluoroethylsulfonyl groups; phenylsulfonyl groups; 5- to 6-membered heteroarylsulfonyl groups such as thiazolylsulfonyl and pyridylsulfonyl groups; C1-6 alkylsulfonyloxy groups such as methylsulfonyloxy, ethylsulfonyloxy, and t-butylsulfonyloxy groups; C1-6 haloalkylsulfonyloxy groups such as trifluoromethylsulfonyloxy and 2,2,2-trifluoroethylsulfonyloxy groups;

[0026] Tri-C1-6 alkyl-substituted silyl groups such as trimethylsilyl, triethylsilyl, and t-butyldimethylsilyl; triphenylsilyl group; cyano group; and nitro group.

[0027] Furthermore, any hydrogen atom in these "substituents" may be substituted with a group of a different structure. In this case, examples of the "substituent" include a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a halogeno group, a cyano group, and a nitro group.

[0028] Furthermore, the above-mentioned "3- to 6-membered heterocyclyl group" contains 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms as ring-constituting atoms. The heterocyclyl group may be either monocyclic or polycyclic. In a polycyclic heterocyclyl group, as long as at least one ring is a heterocycle, the remaining rings may be saturated alicyclic, unsaturated alicyclic, or aromatic. Examples of the "3- to 6-membered heterocyclyl group" include 3- to 6-membered saturated heterocyclyl groups, 5- to 6-membered heteroaryl groups, and 5- to 6-membered partially unsaturated heterocyclyl groups.

[0029] Examples of the "3- to 6-membered saturated heterocyclyl group" include an aziridinyl group, an epoxy group, a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, and a dioxanyl group.

[0030] Examples of "5-membered heteroaryl groups" include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups. Examples of "6-membered heteroaryl groups" include pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl groups. Examples of "5- to 6-membered partially unsaturated heterocyclyl groups" include 5-membered partially unsaturated heterocyclyl groups such as pyrrolinyl, dihydrofuranyl, dihydrothiophenyl, imidazolinyl, pyrazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, and isothiazolinyl groups; and 6-membered partially unsaturated heterocyclyl groups such as dihydropyranyl.

[0031] Q in formula (I) １ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- or 6-membered heterocyclyl group, or a substituted or unsubstituted 9- or 10-membered heterocyclyl group.

[0032] Q in formula (I) ２represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- or 6-membered heterocyclyl group, or a substituted or unsubstituted 9-10-membered heterocyclyl group.

[0033] A heterocyclyl group contains at least one heteroatom selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom as a ring-constituting atom. The heterocyclyl group may be either monocyclic or polycyclic. In a polycyclic heterocyclyl group, as long as at least one ring is a heterocycle, the remaining rings may be saturated alicyclic, unsaturated alicyclic, or aromatic.

[0034] Q １ or Q ２ Examples of the "5- to 6-membered heterocyclyl group" in the above formula include a 5- to 6-membered saturated heterocyclyl group, a 5- to 6-membered heteroaryl group, and a 5- to 6-membered partially unsaturated heterocyclyl group.

[0035] Q １ or Q ２ Examples of the "5- to 6-membered saturated heterocyclyl group" in the above formula include a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, a dioxanyl group, and the like.

[0036] Q １ or Q ２ Examples of the "5-membered heteroaryl group" in the above formula include a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, and a tetrazolyl group.

[0037] Q １ or Q ２ Examples of the "6-membered heteroaryl group" in the above formula include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group.

[0038] Q １ or Q ２ Examples of the "5- to 6-membered partially unsaturated heterocyclyl group" in the above formula include 5-membered partially unsaturated heterocyclyl groups such as pyrrolinyl group, dihydrofuranyl group, dihydrothiophenyl group, imidazolinyl group, pyrazolinyl group, oxazolinyl group, isoxazolinyl group, isoxazolinonyl group, thiazolinyl group, and isothiazolinyl group; and 6-membered partially unsaturated heterocyclyl groups such as dihydropyranyl group and pyridazinonyl group.

[0039] Q １ or Q ２ Examples of the "9-membered heterocyclyl group" in the above formula include an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothienyl group, an indazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a benzothiazolyl group, and a benzisothiazolyl group.

[0040] Q １ or Q ２ Examples of the "10-membered heterocyclyl group" in the above formula include a quinolinyl group, an isoquinolinyl group, a cinnolinyl group, a phthalazinyl group, a quinazolinyl group, and a quinoxalinyl group.

[0041] Q １ or Q ２In the above, substituents on the "phenyl group", "naphthyl group", "5- to 6-membered heterocyclyl group" or "9- to 10-membered heterocyclyl group" include: a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a hydroxyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a C1-6 alkylthio group, a C1-6 alkylsulfonyl group, a phenyl group, a 5-membered heteroaryl group, a 6-membered heteroaryl group, a cyano group; a phenyl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 5-membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or A 6-membered heteroaryl group substituted by one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group is preferred, at least one selected from the group consisting of a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C1-6 alkylsulfonyl group, and a cyano group is more preferred, and at least one selected from the group consisting of a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, and a cyano group is even more preferred.

[0042] Q ２ The "C1-6 alkyl group" in the above may be a straight chain or a branched chain. ２ Examples of the "C1-6 alkyl group" in the above formula include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an i-propyl group, an i-butyl group, an s-butyl group, a t-butyl group, an i-pentyl group, a neopentyl group, a 2-methylbutyl group, an i-hexyl group, and the like.

[0043] Q ２Examples of the "C2-6 alkenyl group" in the above formula include vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, and 5-hexenyl group.

[0044] Q ２ Examples of the "C2-6 alkynyl group" in the above formula include ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl group, and the like.

[0045] Q ２ In the above, preferred substituents on the "C1-6 alkyl group", "C1-6 alkenyl group", and "C2-6 alkynyl group" are: a halogeno group, a hydroxyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, a 5-membered heteroaryl group, a 6-membered heteroaryl group, and a cyano group; a phenyl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 5-membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or a 6-membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group.

[0046] Among these, Q １is preferably a substituted or unsubstituted phenyl group; a substituted or unsubstituted thiazolyl group; a substituted or unsubstituted pyridyl group; a substituted or unsubstituted pyridazinyl group; a substituted or unsubstituted pyridazinonyl group; or a substituted or unsubstituted quinolinyl group, and is preferably a phenyl group; a phenyl group substituted with a halogeno group; a thiazolyl group substituted with a halogeno group; a pyridyl group; a pyridyl group substituted with at least one substituent selected from the group consisting of a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C1-6 alkylthio group, a C1-6 alkylsulfonyl group, and a phenyl group substituted with a halogeno group; A pyridazinyl group substituted with at least one substituent selected from the group consisting of a halogeno group and a C1-6 alkyl group; a pyridazinonyl group substituted with at least one substituent selected from the group consisting of a halogeno group and a C1-6 alkyl group; or an unsubstituted quinolinyl group is more preferred, and a thiazolyl group substituted with a halogeno group; a pyridyl group; a pyridyl group substituted with at least one substituent selected from the group consisting of a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C1-6 alkylthio group, and a phenyl group substituted with a halogeno group; a thiazolyl group substituted with a halogeno group; or an unsubstituted quinolinyl group is even more preferred. The number of substituents on the phenyl group, thiazolyl group, or pyridyl group is more preferably 1 or 2, and even more preferably 1.

[0047] Q ２is preferably a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted isoxazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted tetrazolyl group, or a substituted or unsubstituted isoxazolinonyl group, and is selected from the group consisting of a C1-6 alkyl group; a C2-6 alkynyl group substituted with a phenyl group substituted with a halogeno group; a phenyl group substituted with at least one substituent selected from the group consisting of a halogeno group, a C1-6 alkyl group, and a C1-6 alkoxy group; a pyridyl group substituted with a halogeno group; a pyrazinyl group substituted with a halogeno group; a halogeno group and a C1-6 alkoxy group. a pyrimidinyl group substituted by at least one substituent selected from the group consisting of a pyridazinyl group substituted by a halogeno group; an isoxazolyl group substituted by a cyano group; a triazolyl group substituted by a halogeno group; a tetrazolyl group; a tetrazolyl group substituted by a C1-6 alkyl group; or an isoxazolinonyl group is more preferred, and a C1-6 alkyl group; a C2-6 alkynyl group substituted by a phenyl group substituted by a halogeno group; a phenyl group substituted by at least one substituent selected from the group consisting of a halogeno group, a C1-6 alkyl group, and a C1-6 alkoxy group; a pyridyl group substituted by a halogeno group; a pyrazinyl group substituted by a halogeno group; a pyrimidinyl group substituted by a C1-6 alkoxy group; a pyridazinyl group substituted by a halogeno group; an isoxazolyl group substituted by a cyano group; or a tetrazolyl group substituted by a C1-6 alkyl group is even more preferred. The number of substituents on the phenyl group, pyridyl group, and pyrimidinyl group is preferably 1 to 3, more preferably 1 or 2, and even more preferably 2.

[0048] In formula (I), R １ represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, or a substituted or unsubstituted C3-6 cycloalkyl group.

[0049] R １ The "C1-6 alkyl group" in the formula may be a straight chain or a branched chain. １ Examples of the "C1-6 alkyl group" in the above formula include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an i-propyl group, an i-butyl group, an s-butyl group, a t-butyl group, an i-pentyl group, a neopentyl group, a 2-methylbutyl group, an i-hexyl group, and the like.

[0050] R １ Examples of the "C2-6 alkenyl group" in the above formula include vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, and 5-hexenyl group.

[0051] R １ Examples of the "C2-6 alkynyl group" in the above formula include ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl group, and the like.

[0052] R １ Examples of the "C3-6 cycloalkyl group" in the above formula include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.

[0053] R １In the above, preferred substituents on the "C1-6 alkyl group", "C1-6 alkenyl group", and "C2-6 alkynyl group" are: a halogeno group, a hydroxyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, a 5-membered heteroaryl group, a 6-membered heteroaryl group, and a cyano group; a phenyl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 5-membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or a 6-membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group.

[0054] R １ Preferred substituents on the "C3-6 cycloalkyl group" in the above formula are a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a hydroxyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, a 5-membered heteroaryl group, a 6-membered heteroaryl group, and a cyano group; a phenyl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 5-membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or a 6-membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group.

[0055] Among these, R １is preferably a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C3-6 cycloalkyl group, more preferably an unsubstituted C1-6 alkyl group or an unsubstituted C3-6 cycloalkyl group, and even more preferably a methyl group, an ethyl group or a cyclopropyl group.

[0056] In formula (I), R ２ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylcarbonyloxy group, a substituted or unsubstituted C1-6 alkoxycarbonyloxy group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1- a substituted or unsubstituted 5- to 6-membered heterocyclyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, a substituted or unsubstituted phenyloxy group, a substituted or unsubstituted naphthyloxy group, a substituted or unsubstituted 5- to 6-membered heterocyclyloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a nitro group, a cyano group, or a halogeno group.

[0057] R ２ In the above, the "C1-6 alkyl group", "C2-6 alkenyl group", "C2-6 alkynyl group", and "C3-6 cycloalkyl group" are R １ The same can be mentioned as those in

[0058] R ２ Examples of the "C1-6 alkoxy group" in the above formula include a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group, and a t-butoxy group.

[0059] R ２Examples of the "C1-6 alkylcarbonyl group" in the above formula include an acetyl group, a propionyl group, an n-propylcarbonyl group, an i-propylcarbonyl group, an n-butylcarbonyl group, and a t-butylcarbonyl group.

[0060] R ２ Examples of the "C1-6 alkoxycarbonyl group" in the above formula include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, an n-butoxycarbonyl group, and a t-butoxycarbonyl group.

[0061] R ２ Examples of the "C1-6 alkylcarbonyloxy group" in the above formula include an acetyloxy group, a propionyloxy group, an n-propylcarbonyloxy group, an i-propylcarbonyloxy group, an n-butylcarbonyloxy group, and a t-butylcarbonyloxy group.

[0062] R ２ Examples of the "C1-6 alkoxycarbonyloxy group" in the above formula include a methoxycarbonyloxy group, an ethoxycarbonyloxy group, an n-propoxycarbonyloxy group, an i-propoxycarbonyloxy group, an n-butoxycarbonyloxy group, and a t-butoxycarbonyloxy group.

[0063] R ２ Examples of the "C1-6 alkylthio group" in the above formula include a methylthio group, an ethylthio group, an n-propylthio group, an n-butylthio group, an n-pentylthio group, an n-hexylthio group, an i-propylthio group, and an i-butylthio group.

[0064] R ２ Examples of the "C1-6 alkylsulfinyl group" in the above formula include a methylsulfinyl group, an ethylsulfinyl group, and a t-butylsulfinyl group.

[0065] R ２ Examples of the "C1-6 alkylsulfonyl group" in the above formula include a methylsulfonyl group, an ethylsulfonyl group, and a t-butylsulfonyl group.

[0066] R２ In the above, substituents on the "C1-6 alkyl group," "C2-6 alkenyl group," "C2-6 alkynyl group," "C1-6 alkoxy group," "C1-6 alkylcarbonyl group," "C1-6 alkoxycarbonyl group," "C1-6 alkylcarbonyloxy group," "C1-6 alkoxycarbonyloxy group," "C1-6 alkylthio group," "C1-6 alkylsulfinyl group," or "C1-6 alkylsulfonyl group" include a halogeno group, a hydroxyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, a 5-membered heteroaryl group, a 6-membered heteroaryl group, and a cyano group; a phenyl group substituted by one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; A 5-membered heteroaryl group substituted by one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group; or a 6-membered heteroaryl group substituted by one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group is preferred.

[0067] R ２ The "5- to 6-membered heterocyclyl group" in １ or Q ２ The same can be mentioned as those in

[0068] R ２ The "5- to 6-membered heterocyclyloxy group" in the above formula is a group in which the hydrogen atom in the hydroxyl group is replaced with a "5- to 6-membered heterocyclyl group".

[0069] R ２In the above, substituents for the "C3-6 cycloalkyl group", "phenyl group", "naphthyl group", "5- to 6-membered heterocyclyl group", "phenoxy group", "naphthyloxy group", and "5- to 6-membered heterocyclyloxy group" include a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a hydroxyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, a 5-membered heteroaryl group, a 6-membered heteroaryl group, and a cyano group; a phenyl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 5-membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or A 6-membered heteroaryl group substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group is preferred.

[0070] R ２ The "amino group" in ２ A "substituted amino group" is a group represented by NH ２ The hydrogen atoms in the group represented by the formula (I) are substituted with other groups.

[0071] R ２ The "aminocarbonyl group" in ２ The "substituted aminocarbonyl group" is a group represented by CONH ２ The hydrogen atoms in the group represented by the formula (I) are substituted with other groups.

[0072] R ２Preferred substituents on the "amino group" or "aminocarbonyl group" in the above formula (I) are a C1-6 alkyl group, a C1-6 haloalkyl group, a C3-6 cycloalkyl group, a phenyl group, a 5-membered heteroaryl group, or a 6-membered heteroaryl group; a phenyl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 5-membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or a 6-membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group.

[0073] R ２ Examples of the "halogeno group" in the above formula include a fluoro group, a chloro group, a bromo group, and an iodo group.

[0074] In formula (I), R ３ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a halogeno group. ４ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a halogeno group.

[0075] R ３ or R ４ The "substituted or unsubstituted C1-6 alkyl group" and "halogeno group" in １ and / or R ２ The same can be mentioned as those in

[0076] Among these, R ３ and R ４ is preferably a hydrogen atom.

[0077] In formula (I), R ５represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a formyl group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group.

[0078] R ５ In the above, "substituted or unsubstituted C1-6 alkyl group", "substituted or unsubstituted C2-6 alkenyl group", "substituted or unsubstituted C2-6 alkynyl group", "substituted or unsubstituted C1-6 alkylcarbonyl group", "substituted or unsubstituted C1-6 alkoxycarbonyl group", "substituted or unsubstituted C3-6 cycloalkyl group", "substituted or unsubstituted phenyl group", "substituted or unsubstituted naphthyl group", and "substituted or unsubstituted 5- to 6-membered heterocyclyl group" are R １ and / or R ２ The same can be mentioned as those in

[0079] Among these, R ５ is preferably a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C2-6 alkenyl group, more preferably a hydrogen atom, an unsubstituted C1-6 alkyl group, a C1-6 alkyl group substituted with a phenyl group, or an unsubstituted C2-6 alkenyl group, and even more preferably a hydrogen atom.

[0080] In formula (I), A represents a substituted or unsubstituted divalent hydrocarbon group or a substituted or unsubstituted divalent organic group containing a hetero atom.

[0081] Examples of divalent hydrocarbon groups include C1-4 alkylene groups such as methylene, dimethylene, trimethylene, propane-1,2-diyl, tetramethylene, butane-1,2-diyl, butane-1,3-diyl, and butane-2,3-diyl; C2-4 alkenylene groups such as ethylene-1,2-diyl, 1-propylene-1,2-diyl, and propylene-1,3-diyl; C3-6 cycloalkylene groups such as cyclopentane-1,1-diyl, cyclopentane-1,2-diyl, cyclopentane-1,3-diyl, cyclohexane-1,1-diyl, cyclohexane-1,2-diyl, cyclohexane-1,3-diyl, and cyclohexane-1,4-diyl; Examples include C1-4 alkylene, C3-6 cycloalkylene, C1-4 alkylene groups such as methylene-cyclopentane-1,1-diyl-methylene group, phenylene group, naphthylene group, and the like.

[0082] The heteroatom-containing divalent organic group is a divalent group containing a carbon atom and a heteroatom. The heteroatom may provide a bond, or the carbon atom may provide a bond. The heteroatom is not particularly limited, but examples thereof include a nitrogen atom, an oxygen atom, and a sulfur atom. Examples of heteroatom-containing divalent organic groups include amino C1-3 alkylene groups such as aminomethylene, aminodimethylene, and aminotrimethylene; C1-3 alkyleneamino C1-3 alkylene groups such as methyleneaminomethylene; thio C1-3 alkylene groups such as thiomethylene, thiodimethylene, and thiotrimethylene; C1-3 alkylenethio C1-3 alkylene groups such as methylenethiomethylene, dimethylthiodimethylene, and dimethylthiomethylene; oxy C1-3 alkylene groups such as oxymethylene, oxydimethylene, and oxytrimethylene; C1-3 alkyleneoxy C1-3 alkylene groups such as methyleneoxymethylene, dimethyleneoxydimethylene, and dimethyleneoxymethylene; sulfinyl C1-3 alkylene groups; Examples include a sulfonyl C1-3 alkylene group; a C1-3 alkylenesulfinyl C1-3 alkylene group; a C1-3 alkylenesulfonyl C1-3 alkylene group; and a heterocyclylene group.

[0083] Of these, preferred examples of A include a dimethylene group, a trimethylene group, a tetramethylene group, a 2-substituted propane-1,3-diyl group, a 2,2-disubstituted propane-1,3-diyl group, a 1,1-disubstituted propane-1,3-diyl group, a cyclopentane-1,3-diyl group, a 2-(cyclopentane-1,1-diyl)-propane-1,3-diyl group, a methyleneoxymethylene group, a methylenethiomethylene group, a methyleneaminomethylene group, an aminodimethylene group, a methylene-substituted aminomethylene group, a substituted aminodimethylene group, etc. Of these, it is more preferred that A is a C1-4 alkylene group or a C3-6 cycloalkylene group.

[0084] Preferred substituents on the "divalent hydrocarbon group" or "heteroatom-containing divalent organic group" are a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a hydroxyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, a 5-membered heteroaryl group, a 6-membered heteroaryl group, and a cyano group; a phenyl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 5-membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or a 6-membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group. In nitrogen atom-containing divalent organic groups such as "amino C1-3 alkylene group" and "C1-3 alkyleneamino C1-3 alkylene group," examples of the substituent that can be bonded to the nitrogen atom include C1-6 alkyl groups and C1-6 haloalkyl groups.

[0085] There may be multiple substituents on the "divalent hydrocarbon group" or "heteroatom-containing divalent organic group". These may be the same or different. Furthermore, the substituent on the "divalent hydrocarbon group" or "heteroatom-containing divalent organic group" may be a divalent organic group that can form a ring on the "divalent hydrocarbon group" or "heteroatom-containing divalent organic group". A divalent organic group is a divalent group containing carbon atoms. Examples of divalent organic groups include C2-5 alkylene groups such as dimethylene, trimethylene, tetramethylene, and pentamethylene.

[0086] In formula (I), B represents a substituted or unsubstituted phenylene group, a substituted or unsubstituted 5- to 6-membered heterocyclylene group, a group represented by the formula: ＊１ -CO-NR ａ - ＊２ a group represented by the formula: ＊１ -NR ａ - ＊２In addition, *1 indicates the bond to the carbon marked with * in formula (I), and *2 indicates the bond to the carbon marked with * in formula (I), and Q in formula (I) ２ Shows the combination with R. ａ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a formyl group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group.

[0087] Examples of the "phenylene group" in B include a 1,2-phenylene group, a 1,3-phenylene group, and a 1,4-phenylene group.

[0088] A heterocyclylene group is a divalent group containing at least one heteroatom selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom as a ring-constituting atom. The heterocyclylene group may be a saturated heterocyclylene group, an unsaturated heterocyclylene group, or a heteroarylene group.

[0089] Examples of the "5- to 6-membered saturated heterocyclylene group" in B include a pyrrolidinylene group, a tetrahydrofuranylene group, a thiazolidinylene group, a piperidinylene group, a piperazinylene group, and a morpholinylene group.

[0090] Examples of the "5-membered heteroarylene group" for B include a pyrrolylene group, a furylene group, a thienylene group, an imidazolylene group, a pyrazolylene group, an oxazolylene group, an isoxazolylene group, a thiazolylene group, an isothiazolylene group, a triazolylene group, an oxadiazolylene group, a thiadiazolylene group, a tetrazolylene group, etc. Among these, an imidazolylene group, a pyrazolylene group, an oxazolylene group, an isoxazolylene group, a thiazolylene group, an isothiazolylene group, a triazolylene group, an oxadiazolylene group, a thiadiazolylene group, a tetrazolylene group is preferred, and a pyrazolylene group, an oxazolylene group, an isoxazolylene group, a thiazolylene group, a triazolylene group, an oxadiazolylene group, a thiadiazolylene group, an isothiazolylene group, a tetrazolylene group is more preferred.

[0091] Examples of the "6-membered heteroarylene group" for B include a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, etc. Among these, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, and a pyridazinylene group are preferred, and a pyridazinylene group is more preferred.

[0092] Examples of the "5- to 6-membered partially unsaturated heterocyclylene group" for B include 5-membered partially unsaturated heterocyclyl groups such as dihydropyrrolinylene group, dihydrofurylene group, dihydrothienylene group, dihydroimidazolylene group, dihydropyrazolylene group, dihydrooxazolylene group, dihydroisoxazolylene group, dihydrothiazolylene group, and dihydroisothiazolylene group; and 6-membered partially unsaturated heterocyclylene groups such as dihydropyranylene group. Among these, a dihydroisoxazolylene group is preferred.

[0093] Substituents on the "phenylene group" and "5- to 6-membered heterocyclylene group" in B include: a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a hydroxyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, a 5-membered heteroaryl group, a 6-membered heteroaryl group, and a cyano group; a phenyl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 5-membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or A 6-membered heteroaryl group substituted by one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group is preferred, a C1-6 alkyl group is more preferred, and a methyl group is even more preferred.

[0094] R ａ In the above, "substituted or unsubstituted C1-6 alkyl group", "substituted or unsubstituted C2-6 alkenyl group", "substituted or unsubstituted C2-6 alkynyl group", "substituted or unsubstituted C1-6 alkylcarbonyl group", "substituted or unsubstituted C1-6 alkoxycarbonyl group", "substituted or unsubstituted C3-6 cycloalkyl group", "substituted or unsubstituted phenyl group", "substituted or unsubstituted naphthyl group", and "substituted or unsubstituted 5- to 6-membered heterocyclyl group" are R １ and / or R ２ The same can be mentioned as those in

[0095] Among these, B is a substituted or unsubstituted phenylene group, a substituted or unsubstituted 5- to 6-membered heterocyclylene group, a group represented by the formula: ＊１ -CO-NR ａ - ＊２ a group represented by the formula: ＊１ -NR ａ - ＊２

[0039] A group represented by the formula (I), an oxygen atom, or a single bond is preferred, and examples thereof include a phenylene group, an imidazolylene group, an imidazolylene group substituted with a C1-6 alkyl group, a pyrazolylene group, a pyrazolylene group substituted with a C1-6 alkyl group, a pyrimidinylene group, an oxazolylene group, an isoxazolylene group, a thiazolylene group, an isothiazolylene group, a triazolylene group, an oxadiazolylene group, a thiadiazolylene group, a tetrazolylene group, a pyridinylene group, a pyrazinylene group, a pyridazinylene group, a dihydroisoxazolylene group, a dihydroisoxazolylene group substituted with a C1-6 alkyl group, ＊１ —CO—NH— ＊２ , ＊１ -NH- ＊２ , an oxygen atom, or a single bond, and examples thereof include an imidazolylene group, a pyrazolylene group, a pyrazolylene group substituted with a C1-6 alkyl group, an oxazolylene group, an isoxazolylene group, a thiazolylene group, an isothiazolylene group, a triazolylene group, an oxadiazolylene group, a thiadiazolylene group, a tetrazolylene group, a pyridazinylene group, a dihydroisoxazolylene group, a dihydroisoxazolylene group substituted with a C1-6 alkyl group, ＊１ —CO—NH— ＊２ , ＊１ -NH- ＊２ , an oxygen atom, or a single bond.

[0096] In the formula (I), R １ is a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C3-6 cycloalkyl group, R ２ is a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, A is a substituted or unsubstituted divalent hydrocarbon group, R ３ and R ４ is a hydrogen atom, and R ５ is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C2-6 alkenyl group, B is a substituted or unsubstituted phenylene group, a substituted or unsubstituted 5- or 6-membered heterocyclylene group, a group represented by the formula: ＊１ —CO—NH— ＊２ a group represented by the formula: ＊１ -NH-＊２ It is preferably a group represented by the following formula:

[0097] In the formula (I), when B is a substituted or unsubstituted phenylene group, Q ２ is preferably a substituted or unsubstituted phenyl group or a substituted or unsubstituted 5- to 6-membered heterocyclyl group. More preferably, when B is a substituted or unsubstituted phenylene group, R １ is a substituted or unsubstituted C1-6 alkyl group, R ２ is a hydrogen atom, A is a C1-4 alkylene group, and R ３ , R ４ and R ５ is a hydrogen atom, and Q ２ is a substituted or unsubstituted phenyl group or a substituted or unsubstituted triazolyl group. ２ is more preferably a phenyl group substituted with a halogeno group or a triazolyl group substituted with a halogeno group. １ is preferably a substituted or unsubstituted 5- or 6-membered heterocyclyl group, more preferably a substituted or unsubstituted pyridyl group, and even more preferably a pyridyl group substituted with at least one substituent selected from the group consisting of a halogeno group, a C1-6 haloalkyl group, and a phenyl group substituted with a halogeno group.

[0098] In the formula (I), when B is a single bond, Q ２ is preferably a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group. More preferably, when B is a single bond, R １ is a substituted or unsubstituted C1-6 alkyl group, R ２ is a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, A is a C1-4 alkylene group, and R ３ , R ４ and R ５ is a hydrogen atom, and Q ２is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted isoxazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyridazinyl group, or a substituted or unsubstituted isoxazolinonyl group. ２ is an unsubstituted C1-6 alkyl group; a C2-6 alkynyl group substituted with a phenyl group substituted with a halogeno group; a phenyl group substituted with a halogeno group; an isoxazolyl group substituted with a cyano group; a pyridyl group substituted with a halogeno group; a pyrazinyl group substituted with a halogeno group; a pyrimidinyl group substituted with a halogeno group; a pyrimidinyl group substituted with a C1-6 alkoxy group; a pyridazinyl group substituted with a halogeno group; or an unsubstituted isoxazolyl group It is an oxazolinonyl group, and even more preferably an unsubstituted C1-6 alkyl group; a C2-6 alkynyl group substituted with a phenyl group substituted with a halogeno group; a phenyl group substituted with a halogeno group; an isoxazolyl group substituted with a cyano group; a pyridyl group substituted with a halogeno group; a pyrazinyl group substituted with a halogeno group; a pyrimidinyl group substituted with a C1-6 alkoxy group; or a pyridazinyl group substituted with a halogeno group. １ is preferably a substituted or unsubstituted phenyl group or a substituted or unsubstituted 5- or 6-membered heterocyclyl group, more preferably a substituted or unsubstituted phenyl group or a substituted or unsubstituted pyridyl group, even more preferably an unsubstituted phenyl group; or a pyridyl group substituted with at least one substituent selected from the group consisting of a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, and a C1-6 alkoxy group, and even more preferably a pyridyl group substituted with a halogeno group.

[0099] In the formula (I), when B is a substituted or unsubstituted 5- or 6-membered heterocyclylene group, Q ２is preferably a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group. More preferably, when B is a substituted or unsubstituted imidazolylene group, a substituted or unsubstituted pyrazolylene group, a substituted or unsubstituted oxazolylene group, a substituted or unsubstituted isoxazolylene group, a substituted or unsubstituted thiazolylene group, a substituted or unsubstituted isothiazolylene group, a substituted or unsubstituted triazolylene group, a substituted or unsubstituted oxadiazolylene group, a substituted or unsubstituted thiadiazolylene group, a substituted or unsubstituted tetrazolylene group, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted pyrazinylene group, a substituted or unsubstituted pyridazinylene group, a substituted or unsubstituted pyrimidinylene group, or a substituted or unsubstituted dihydroisoxazolylene group, R １ is a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C3-6 cycloalkyl group, R ２ is a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, A is a C1-4 alkylene group, and R ３ and R ４ is a hydrogen atom, and R ５ is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C2-6 alkenyl group, and Q ２ is an unsubstituted C1-6 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, or a substituted or unsubstituted tetrazolyl group. ２is more preferably an unsubstituted C1-6 alkyl group; a phenyl group substituted with at least one substituent selected from the group consisting of a halogeno group, a C1-6 alkyl group, and a C1-6 alkoxy group; a pyridyl group substituted with a halogeno group; an unsubstituted tetrazolyl group; or a tetrazolyl group substituted with a C1-6 alkyl group, and even more preferably a phenyl group substituted with at least one substituent selected from the group consisting of a halogeno group, a C1-6 alkyl group, and a C1-6 alkoxy group; a pyridyl group substituted with a halogeno group; or a tetrazolyl group substituted with a C1-6 alkyl group. Furthermore, when B is a substituted or unsubstituted 5- or 6-membered heterocyclylene group, Q １is preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group, more preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted pyridazinonyl group, or a substituted or unsubstituted quinolinyl group, and is preferably an unsubstituted phenyl group; a phenyl group substituted with a halogeno group; a thiazolyl group substituted with a halogeno group; an unsubstituted pyridyl group; a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C1-6 alkylthio group, a C1-6 alkylsulfol group, or a halogeno group-substituted phenyl group. a pyridyl group substituted with at least one substituent selected from the group consisting of a halogeno group and a C1-6 alkyl group; a pyridazinonyl group substituted with at least one substituent selected from the group consisting of a halogeno group and a C1-6 alkyl group; or an unsubstituted quinolinyl group, and even more preferably an unsubstituted phenyl group; a thiazolyl group substituted with a halogeno group; an unsubstituted pyridyl group; a pyridyl group substituted with at least one substituent selected from the group consisting of a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, and a C1-6 alkylthio group; or an unsubstituted quinolinyl group.

[0100] In the formula (I), B is a group represented by the formula: ＊１ —CO—NH— ＊２ When Q is a group represented by ２ is preferably a substituted or unsubstituted phenyl group. More preferably, B is a group of the formula: ＊１ —CO—NH— ＊２ When R is a group represented by １ is a substituted or unsubstituted C1-6 alkyl group, R ２ is a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, A is a C1-4 alkylene group, and R ３ , R４ and R ５ is a hydrogen atom, and Q ２ is a substituted or unsubstituted phenyl group. ２ is more preferably a phenyl group substituted with a halogeno group. ＊１ —CO—NH— ＊２ When Q is a group represented by １ is preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group, more preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, or a substituted or unsubstituted quinolinyl group, even more preferably an unsubstituted phenyl group; a pyridyl group substituted with at least one substituent selected from the group consisting of a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, and a C1-6 alkoxy group, or an unsubstituted quinolinyl group, and particularly preferably a pyridyl group substituted with at least one substituent selected from the group consisting of a halogeno group, a C1-6 alkyl group, and a C1-6 alkoxy group, or an unsubstituted quinolinyl group.

[0101] In the formula (I), B is a group represented by the formula: ＊１ -NH- ＊２ When Q is a group represented by ２ is preferably a substituted or unsubstituted C1-6 alkyl group. More preferably, B is a group of the formula: ＊１ -NH- ＊２ When R is a group represented by １ is a substituted or unsubstituted C1-6 alkyl group, R ２ is a hydrogen atom, A is a C1-4 alkylene group, and R ３ , R ４ and R ５ is a hydrogen atom, and Q ２ is a substituted or unsubstituted C1-6 alkyl group. ＊１ -NH- ＊２ When Q is a group represented by １is preferably a substituted or unsubstituted 5- or 6-membered heterocyclyl group, more preferably a substituted or unsubstituted pyridyl group, and even more preferably a pyridyl group substituted with a halogeno group.

[0102] In the formula (I), when B is an oxygen atom, Q ２ is preferably a substituted or unsubstituted C1-6 alkyl group. More preferably, when B is an oxygen atom, R １ is a substituted or unsubstituted C1-6 alkyl group, R ２ is a hydrogen atom, A is a C1-4 alkylene group, and R ３ , R ４ and R ５ is a hydrogen atom, and Q ２ is a substituted or unsubstituted C1-6 alkyl group. Furthermore, when B is an oxygen atom, Q １ is preferably a substituted or unsubstituted 5- or 6-membered heterocyclyl group, more preferably a substituted or unsubstituted pyridyl group, and even more preferably a pyridyl group substituted with a halogeno group.

[0103] Among these, B in the formula (I) is a substituted or unsubstituted 5- to 6-membered heterocyclylene group, a group represented by the formula: ＊１ —CO—NH— ＊２ a group represented by the formula: ＊１ -NH- ＊２ A substituted or unsubstituted 5- or 6-membered heterocyclylene group or a group represented by the formula: ＊１ —CO—NH— ＊２ It is more preferable that the group is a group represented by the following formula:

[0104] The salt of compound (I) is not particularly limited as long as it is an agriculturally and horticulturally acceptable salt. Examples of the salt of compound (I) include salts of inorganic acids such as hydrochloric acid and sulfuric acid; salts of organic acids such as acetic acid and lactic acid; salts of alkali metals such as lithium, sodium, and potassium; salts of alkaline earth metals such as calcium and magnesium; salts of transition metals such as iron and copper; ammonia; salts of organic bases such as triethylamine, tributylamine, pyridine, and hydrazine.

[0105] The method for producing Compound (I) or a salt of Compound (I) is not particularly limited. For example, Compound (I) or a salt of Compound (I) can be obtained by a combination of known chemical reactions described in the Examples, etc. Alternatively, a salt of Compound (I) can be obtained from Compound (I) by a known method.

[0106] Compound (I) can be synthesized, for example, according to the following reaction scheme 1.

[0107]

[0108] A compound represented by formula (3) (hereinafter, sometimes referred to as compound (3)) is obtained by reacting compound (1) with a compound represented by formula (2) in the presence of a base. Subsequently, the cyano group in compound (3) is reduced with a reducing agent such as dimethylsulfide borane to obtain a compound represented by formula (4) (hereinafter, sometimes referred to as compound (4)). Finally, the obtained compound (4) and a compound represented by formula (5) are condensed with a condensing agent to obtain compound (I). In the above reaction scheme 1, R １ , R ２ , A, B and Q ２ are the same groups as in formula (I), and X represents a halogeno group such as a chloro group, a bromo group, or an iodo group.

[0109] Compound (1) can be produced, for example, by the following reaction scheme 2.

[0110]

[0111] A compound represented by formula (6) (hereinafter sometimes referred to as compound (6)) is reacted with a compound represented by formula (7) and a base to obtain a compound represented by formula (8) (hereinafter sometimes referred to as compound (8)). Subsequently, compound (8) is reacted with a cyanide salt represented by formula (9) (e.g., sodium cyanide or potassium cyanide) and a base to obtain a compound represented by formula (10) (hereinafter sometimes referred to as compound (10)). Subsequently, compound (10) is reacted with a hydrazine compound represented by formula (11) (hereinafter sometimes referred to as compound (11)) to obtain a compound represented by formula (12), which is then cyanated by reacting with p-toluenesulfonylmethyl isocyanide (TosMIC reagent) to obtain compound (1). In the above reaction scheme 2, R １ , R ２ and A are the same groups as in formula (I), and MCN represents an alkali metal cyanide.

[0112] In compound (1), R ２ The compound in which is hydrogen (hereinafter, sometimes referred to as compound (14)) can be produced, for example, by the following reaction scheme 3.

[0113]

[0114] Compound (6) is reacted with N,N-dimethylformamide dimethyl acetal, and then reacted with compound (11) to obtain a compound represented by formula (13) (hereinafter, sometimes referred to as compound (13)). Subsequently, compound (13) is cyanated by reacting with p-toluenesulfonylmethyl isocyanide (TosMIC reagent) to obtain compound (14). In Reaction Scheme 3, R １ and A are each the same groups as in formula (I).

[0115] The agricultural and horticultural fungicide of the present invention contains at least one active ingredient selected from the group consisting of compound (I) and a salt of compound (I). The amount of active ingredient (I) contained in the agricultural and horticultural fungicide of the present invention is not particularly limited as long as it exhibits a fungicidal effect.

[0116] The agricultural and horticultural fungicide of the present invention can be used to control plant diseases caused by a wide variety of filamentous fungi, for example, fungi belonging to the phylum Oomycetes, Ascomycetes, Deuteromycetes, Basidiomycetes, and Zygomycetes.

[0117] Examples of plant diseases (pathogens) that can be controlled are shown below. Sugar beet: Cercospora beticola, Aphanomyces cochlioides, Root rot (Thanatephorus cucumeris), Leaf rot (Thananatephorus cucumeris), Rust (Uromyces betae), Powdery mildew (Oidium sp.), Spot disease (Ramularia beticola), Seedling damping off (Aphanomyces cochlioides, Pythium Groundnut: Mycosphaerella arachidis, Ascochyta sp., Puccinia arachidis, Pythium debaryanum, Alternaria alternata, Sclerotium rolfsii, Mycosphaerella berkeleyi, Calonectria ilicicola) etc. Cucumber: Powdery mildew (Sphaerotheca fuliginea), downy mildew (Pseudoperonospora cubensis), vine blight (Mycosphaerella melonis), vine splitting (Fusarium oxysporum), sclerotinia sclerotiorum, gray mold (Botrytis cinerea), anthracnose (Colletotrichum orbiculare), black spot (Cladosporium cucumerinum), brown spot (Corynespora cassiicola), seedling damping-off (Pythium debaryanum, Rhizoctonia solani Kuhn), Phomopsis root rot (Phomopsis sp.), bacterial spot (Pseudomonas syringae pv. Lachrymans), etc. Tomato: Gray mold (Botrytis cinerea), leaf mold (Cladosporium fulvum), late blight (Phytophthora infestans), hemi-wilt (Verticillium albo-atrum, Verticilliumdahliae), powdery mildew (Oidium neolycopersici), ring blight (Alternaria solani), sooty mold (Pseudocercospora fuligena), bacterial wilt (Ralstonia solanacearum), sclerotinia sclerotiorum, etc. Eggplant: gray mold (Botrytis cinerea), black blight (Corynespora melongenae), powdery mildew (Erysiphe cichoracearum), sooty mold (Mycovellosiella nattrassii), sclerotinia sclerotiorum, verticillium wilt (Verticillium dahliae), brown spot (Phomopsis vexans), etc. Pepper: late blight (Phytophthora capsici), gray mold (Botrytis cinerea), sclerotinia sclerotiorum), anthracnose (Colletotrichum aenigma, Colletotrichum capsici, Colletotrichum fructicola, Colletotrichum jiangxiense), powdery mildew (Leveillula taurica), etc. Strawberry: Gray mold (Botrytis cinerea), powdery mildew (Sphaerotheca humuli), anthracnose (Colletotrichum acutatum, Colletotrichum fragariae), late blight (Phytophthora cactorum), soft rot (Rhizopus stolonifer), chlorosis (Fusarium oxysporum), wilt (Verticillium dahliae), sclerotinia sclerotiorum), etc. Onion: Gray rot (Botrytis allii), gray mold (Botrytis cinerea), white spot leaf blight (Botrytis squamosa), Peronospora destructor, white late blight (Phytophthora porri), Ciborinia allii, BotrytisOnions: soft rot (Pectobacterium carotovorum), downy mildew (Peronospora destructor), leaf blight (Pleospora allii), black sclerotinia rot (Sclerotium cepivorum), rust (Puccinia allii), white leaf blight (Botrytis squamosa), southern blight (Sclerotium rolfsii), red root rot (Pyrenochaeta terrestris), etc. Leeks: soft rot (Pectobacterium carotovorum), downy mildew (Peronospora destructor), leaf blight (Pleospora allii), black sclerotinia rot (Sclerotium cepivorum), rust (Puccinia allii), white leaf blight (Botrytis squamosa), southern blight (Sclerotium rolfsii), red root rot (Pyrenochaeta terrestris), etc. Cabbages: clubroot (Plasmodiophora brassicae), soft rot (Erwinia carotovora), black rot (Xanthomonas campesrtis pv. campestris), black spot bacterial disease (Pseudomonas syringae pv. maculicola, P. s. pv. alisalensis), downy mildew (Peronospora parasitica), sclerotinia rot (Sclerotinia sclerotiorum), black mold (Alternaria brassicicola), gray mold (Botrytis cinerea), root rot (Phoma lingam), Pythium rot (Pythium aphanidermatum, Pythium ultimum), white rust (Albugo macrospora), etc. Lettuces: rot (Pseudomonas cichorii, Pseudomonas marginalis), soft rot (Pectobacterium carotovorum), downy mildew (Bremia lactucae), gray mold (Botrytis cinerea), sclerotinia rot (Sclerotinia sclerotiorum), Mirafiori lettuce big-vein ophiovirus, root rot (Fusarium oxysporum), basal rot (Rhizoctoniasolani), powdery mildew (Golovinomyces orontii), etc. Green beans: Sclerotinia sclerotiorum, gray mold (Botrytis cinerea), anthracnose (Colletotrichum lindemuthianum), angular spot (Phaeoisariopsis griseola), etc. Peas: Brown spot (Mycosphaerella blight), gray mold (Botrytis cinerea), Sclerotinia sclerotiorum, powdery mildew (Erysiphe pisi), etc.

[0118] Apple: Powdery mildew (Podosphaera leucotricha), black spot (Venturia inaequalis), monilinia (Monilinia mali), black spot (Mycosphaerella pomi), canker (Valsa mali), leaf spot (Alternaria mali), red spot (Gymnosporangium yamadae), ring spot (Botryosphaeria berengeriana), anthracnose (Glomerella cingulata, Colletotrichum acutatum), brown spot (Diplocarpon mali), sooty spot (Zygophiala jamaicensis), sooty spot (Gloeodes pomigena), purple root rot (Helicobasidium mompa), white root rot (Rosellinia necatrix), gray mold (Botrytis cinerea), fire blight (Erwinia amylovora), silver leaf (Chondrostereum) purpureum), crown gall (Rhizobium radiobacter, Rhizobium rhizogenes), etc. Plum: Black spot (Cladosporium carpophilum), gray mold (Botrytis cinerea), brown rot (Monilinia mumecola), sooty spot (Peltaster sp.), fruit blister (Taphrina pruni), brown hole (Phloeosporella padi), etc. Persimmon: Powdery mildew (Phyllactinia kakicola), anthracnose (Gloeosporium kaki), angular leaf spot (Cercospora kaki), circular leaf spot (Mycosphaerella nawae), gray mold (Botrytis cinerea), sooty spot (Zygophiala jamaicensis), etc. Peach: Brown rot (Monilinia fructicola, Monilinia fructigena), black spot (Cladosporium carpophilum), Phomopsis sp., Xanthomonas campestris pv.Plum: leaf curl (Taphrina pruni), leaf blister (Taphrina deformans), anthracnose (Colletotrichum gloeosporioides), brown spot (Phloeosporella padi), wood ear (Coriolus versicolor), etc. Almond: gray mold (Monilinia laxa), leaf spot (Stigmina carpophila), scab (Cladosporium carpophilum), leaf swelling disease (Polystigma rubrum), Alternaria leaf spot (Alternaria alternata), anthracnose (Colletotrichum gloeospoides), etc. Peach: gray mold (Monilinia fructicola), anthracnose (Colletotrichum acutatum), black spot (Alternaria sp.), Young fruit sclerotinia (Monilinia kusanoi), Brown hole (Mycosphaerella cerasella), Powdery mildew (Podosphaera tridactyla), etc. Grapes: Gray mold (Botrytis cinerea), Powdery mildew (Uncinula necator), Late rot (Glomerella cingulata, Colletotrichum acutatum), Downy mildew (Plasmopara viticola), Black rot (Elsinoe ampelina), Brown spot (Pseudocercospora vitis), Black rot (Guignardia bidwellii), White rot (Coniella castaneicola), Rust (Phakopsora ampelopsidis), White cotton snow (causative agent unidentified), Crown gall (Rhizobium radiobacter, Rhizobium vitis), etc. Pears: Black spot (Venturia nashicola), Red spot (Gymnosporangium asiaticum), black spot (Alternaria kikuchiana), ring spot (Botryosphaeria berengeriana), powdery mildew (Phyllactinia mali), canker (Phomopsis fukushii), brown spot (Stempphylium vesicarium), anthracnose (Glomerella cingulata), etc. Tea: ring spot (Pestalotiopsis longiseta, P. theae), anthracnose (Colletotrichum theae-sinensis), net blight (Exobasidium reticulatum), red burn (Pseudomonas syringae), blight (Exobasidium vexans), etc. Citrus: scab (Elsinoe fawcettii), blue mold (Penicillium italicum), green mold (Penicillium digitatum), gray mold (Botrytis cinerea), black spot (Diaporthe citri), canker disease (Xanthomonas campestris pv. Citri), powdery mildew (Oidium sp.), late blight (Phytophthora citrophthora), anthracnose (Colletotrichum fioriniae), etc. Kiwifruit: blossom rot (Pseudomonas marginalis, Pseudomonas syringae, Pseudomonas viridiflava), canker (Pseudomonas syringae), gray mold (Botrytis cinerea), fruit soft rot (Botryosphaeria dothidea, Diaporthe sp., Lasiodiplodia theobromae), sooty spot (Pseudocercospora actinidiae), etc. Olive: anthracnose (Colletotrichum acutatum, Colletotrichum gloeosporioides), peacock spot (Spilocaea oleaginea), etc. Chestnut: anthracnose (Colletotrichum gloeosporioides), etc.

[0119] Wheat: powdery mildew (Blumeria graminis f.sp. tritici), scab (Gibberella zeae, Fusarium avenaceum, Fusarium culmorum, Fusarium crookwellense, Microdochium nivale), brown rust (Puccinia recondita), yellow rust (Puccinia striiformis), brown snow blight (Pythium iwayamai), red snow blight (Monographella nivalis), eyespot (Pseudocercosporella herpotrichoides), leaf blotch (Septoria tritici), glume blotch (Leptosphaeria nodorum), pink snow mold (Typhula incarnata), large snow mold (Myriosclerotinia borealis), take-all (Gaeumannomyces graminis), ergot (Claviceps purpurea), common bunt (Tilletia caries), loose smut (Ustilago nuda), rice blast (Pyricularia grisea), damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.) etc. Barley: leaf stripe (Pyrenophora graminea), net blotch (Pyrenophora teres), leaf scald (Rhynchosporium secalis), loose smut (Ustilago tritici, U. nuda), damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.)) etc. Rice: Blast (Pyricularia oryzae), Sheath blight (Rhizoctonia solani), Bakanae disease (Gibberella fujikuroi), Hemophilus leaf blight (Cochliobolus miyabeanus), Seedling damping-off (Pythium graminicola), Bacterial leaf blight (Xanthomonas oryzae), Bacterial seedling blight (Burkholderia plantarii), Brown stripe (Acidovorax avenae), Bacterial grain rot (Burkholderia glumae), Stripe blight (Cercospora oryzae), Rice smut (Ustilaginoidea virens), Brown rice (Alternaria alternata, Curvularia intermedia), Black rice (Alternaria padwickii), Pink rice (Epicoccum purpurascens), etc. Tobacco: Sclerotinia sclerotiorum, Powdery mildew (Erysiphe cichoracearum), late blight (Phytophthora nicotianae), etc.

[0120] Tulips: Gray mold (Botrytis cinerea), brown spot (Botrytis tulipae), leaf rot (Rhizoctonia solani), bulb rot (Fusarium oxysporum), skin rot (Rhizoctonia solani), etc. Roses: Black spot (Diplocarpon rosae), powdery mildew (Erysiphe simulans, Podosphaera pannosa), gray mold (Botrytis cinerea), etc. Chrysanthemums: Gray mold (Botrytis cinerea), white rust (Puccinia horiana), downy mildew (Paraperonospora minor, Peronospora danica), Pythium damping-off (Pythium aphanidermatum, Pythium dissotocum, Pythium helicoides, Pythium oedochilum, Pythium sylvaticum), damping-off (Rhizoctonia solani), Fusarium wilt (Fusarium solani), etc. Gerbera: Gray mold (Botrytis cinerea), powdery mildew (Podosphaera xanthii), etc. Lily: Leaf blight (Botrytis elliptica, Pestalotiopsis sp.), Gray mold (Botrytis cinerea), etc. Sunflower: Downy mildew (Plasmopara halstedii), Sclerotinia sclerotiorum, Gray mold (Botrytis cinerea), etc. Bentgrass: Snow mold (Sclerotinia borealis), Large patch (Rhizoctonia solani), Brown patch (Rhizoctonia solani), Dollar spot (Sclerotinia homoeocarpa), Blast (Pyricularia sp.)), red blight (Pythium aphanidermatum), anthracnose (Colletotrichum graminicola), etc. Orchardgrass: powdery mildew (Erysiphe graminis), etc. Soybean: purple spot (Cercospora kikuchii), downy mildew (Peronospora manshurica), stem rot (Phytophthora sojae), rust (Phakopsora pachyrhizi), sclerotinia sclerotiorum, anthracnose (Colletotrichum truncatum), gray mold (Botrytis cinerea), black rot (Elsinoe glycines), black spot (Diaporthe phaseolorum var. sojae), damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), etc.

[0121] Potato: late blight (Phytophthora infestans), summer blight (Alternaria solani), black spot (Thanatephorus cucumeris), half-leaf wilt (Verticillium albo-atrum, V. dahliae, V. nigrescens), black leg (Pectobacterium atrosepticum), soft rot (Pectobacterium carotovorum), gray mold (Botrytis cinerea), common scab (Streptomyces spp.), sclerotinia sclerotiorum, etc. Dioscorea: leaf blight (Cylindrosporium dioscoreae), anthracnose (Colletotrichum gloeosporioides), blue mold (Penicillium sclerotigenum), etc. Sweet potato: purple root rot (Helicobasidium mompa), fusarium wilt (Fusarium oxysporum), etc. Taro: Late blight (Phytophthora colocasiae), stem rot (Rhizoctonia solani), etc. Ginger: Rhizome rot (Pythium ultimum, Pythium myriotylum), white spot (Phyllosticta zingiberis), etc. Banana: Panama disease (Fusarium oxysporum), Sigatoka disease (Mycosphaerella fijiensis, M. musicola), etc. Mango: Anthracnose (Colletotrichum aenigma), canker (Xanthomonas campestris), stem rot (Diaporthe pseudophoenicicola, Lasiodiplodia theobromae, Lasiodiplodia spp., Neofusicoccum parvum, Neofusicoccum sp.), Gray mold (Botrytis cinerea), etc. Rapeseed: Sclerotinia sclerotiorum, Root rot (Phoma lingam), Black spot (Alternaria brassicae), Powdery mildew (Erysiphe cruciferarum, Erysiphe cichoracearum, Oidium matthiolae), Downy mildew (Peronospora parasitica), etc. Coffee: Rust (Hemileia vastatrix), Anthracnose (Colletotrichum coffeanum), Brown eye (Cercospora coffeicola), etc. Sugarcane: Brown rust (Puccinia melanocephala), etc. Maize: Hail leaf spot (Gloeocercospora sorghi), Rust (Puccinia sorghi), Southern rust (Puccinia polysora), Ear smut (Ustilago maydis), Southern leaf blight (Cochliobolus heterostrophus), sooty blight (Setosphaeria turcica), damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), etc. Cotton: Seedling damping-off (Pythium sp.), rust (Phakopsora gossypii), white mold (Mycosphaerella areola), anthracnose (Glomerella gossypii), etc. Hops: Downy mildew (Pseudoperonospora humuli), powdery mildew (Oidium sp., Podosphaera macularis), gray mold (Botrytis cinerea), etc.

[0122] The agricultural and horticultural fungicide of the present invention is preferably used on plants such as grains, vegetables, root vegetables, potatoes, fruit trees, trees such as tea, coffee and cacao, pasture grasses, turf grasses, and cotton.

[0123] The agricultural and horticultural fungicide of the present invention can be applied to various parts of plants, such as leaves, stems, stalks, flowers, buds, fruits, seeds, sprouts, roots, tubers, tuberous roots, shoots, cuttings, etc. It can also be applied to improved varieties and varieties of these plants, cultivated varieties, mutants, hybrids, and genetically modified organisms (GMOs).

[0124] The agricultural and horticultural fungicide of the present invention can be used for seed treatment, foliage spray, soil application, water surface application, etc., which are carried out to control various diseases that occur in agricultural and horticultural crops including flowers, turf, and pasture grass.

[0125] The agricultural and horticultural fungicide of the present invention may contain other components in addition to the active ingredient (I). Examples of such other components include known carriers used for formulation. Examples of such other components include conventionally known fungicides, insecticides / miticides, nematicides, soil pesticides, plant regulators, synergists, fertilizers, soil conditioners, and animal feed (hereinafter sometimes referred to as active ingredient (II)). The agricultural and horticultural fungicide of the present invention may exhibit a synergistic effect by containing the active ingredients (I) and (II). The agricultural and horticultural fungicide of the present invention may also be mixed or used in combination with an agricultural or horticultural agent containing the active ingredient (II). Mixing or use in combination may produce a synergistic effect.

[0126] Specific examples of fungicides as the active ingredient (II) are shown below. (1) Nucleic acid biosynthesis inhibitors: (a) RNA polymerase I inhibitors: benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M, oxadixyl, clozylacon, ofrace; (b) Adenosine deaminase inhibitors: bupirimate, dimethirimol, ethirimol; (c) DNA / RNA synthesis inhibitors: hymexazole, octhilinone; (d) DNA topoisomerase II inhibitors: oxolinic acid; (e) DHODH inhibitors: ipflufenoquin, quinofumelin;

[0127] (2) Mitotic inhibitors and cell division inhibitors: (a) β-tubulin polymerization inhibitors: benomyl, carbendazim, chlorphenazole, fuberidazole, thiabendazole, thiophanate, thiophanate methyl, diethofencarb, zoxamide, ethaboxam; (b) cell division inhibitors: pencycuron; (c) spectrin-like protein delocalization inhibitors: fluopicolide, fluopimomide; (d) actin / myosin / fimbrin function: fenamacryl, metrafenone, pyriophenone; (e) tubulin dynamics modulators: pyridaclomethyl;

[0128] (3) Respiratory inhibitors: (a) Complex I-NADH oxidoreductase inhibitors: diflumetrim, tolfenpyrad, fenazaquin; (b) Complex II-succinate dehydrogenase inhibitors: benodanil, flutolanil, mepronil, isofetamide, fluopyram, cyclobutrifluram, fenfuram, flumecyclox, carboxin, oxycarboxin, thifluzamide, benzovindiflupyr, bixafen, fluxapyroxad, furametpyr, isopyrazam, penflufen, penthiopyrad, sedaxane, boscalid, pydiflumetofen, isoflucipram, pyraziflumid, inpirfluxam; (c) Complex III - ubiquinol oxidase Qo inhibitors: azoxystrobin, cumoxystrobin, methoxystrobin, enoxastrobin, flufenoxystrobin, picoxystrobin, pyraoxystrobin, pyraclostrobin, pyrametostrobin, triclopiricarb, kresoxim-methyl, trifloxystrobin, dimoxystrobin, phenaminestrobin, metominostrobin, orysastrobin, famoxadone, fluoxastrobin, fenamidone, pyribencarb, methyltetraprole, mandestrobin; (d) Complex III - ubiquinol reductase Qi inhibitors: cyazofamid, amisulbrom, fenpicoxamide, florylpicoxamide; (e) oxidative phosphorylation uncouplers: binapacryl, meptyldinocap, dinocap, fluazinam; (f) Oxidative phosphorylation inhibitors (inhibitors of ATP synthase): fentin acetate, fentin chloride, fentin hydroxide; (g) ATP production inhibitors: silthiofam; (h) Complex III: Qx (unknown) inhibitor of cytochrome bc1 (ubiquinone reductase): ametoctradine;

[0129] (4) Amino acid and protein synthesis inhibitors: (a) methionine biosynthesis inhibitors: andoprim, cyprodinil, mepanipyrim, pyrimethanil; (b) protein synthesis inhibitors: blasticidin-S, kasugamycin, kasugamycin hydrochloride, streptomycin, oxytetracycline; (c) leucyl-tRNA synthetase inhibitors: tavaborole;

[0130] (5) Signal transduction inhibitors: (a) Signal transduction inhibitors: quinoxyfen, proquinazid; (b) MAP / histidine kinase inhibitors in osmotic signal transduction: fenpiclonil, fludioxonil, chlozolinate, dimethaclon, iprodione, procymidone, vinclozolin;

[0131] (6) Lipid and cell membrane synthesis inhibitors: (a) phospholipid biosynthesis and methyltransferase inhibitors: edifenphos, iprobenfos, pyrazophos, isoprothiolane; (b) lipid peroxidizing agents: biphenyl, chloroneb, dicloran, quintozene, tecnazene, tolclofos-methyl, etridiazole; (c) agents acting on cell membranes: iodocarb, propamocarb, propamocarb hydrochloride, propamocarb fosetylate, prothiocarb; (d) agents disrupting cell membranes: extracts of Gosei-kajeput (tea tree); (e) agents specifically binding to ergosterol: natamycin;

[0132] (7) Cell membrane sterol biosynthesis inhibitors: (a) C14 demethylation inhibitors in sterol biosynthesis: triforine, pyrifenox, pyrisoxazole, fenarimol, flurprimidol, nuarimol, imazalil, imazalil sulfate, oxpoconazole, oxpoconazole fumarate, pefurazoate, prochloraz, triflumizole, biniconazole, azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazol, difenoconazole, diniconazole, diniconazole-M, epoxi Siconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, fluconazole, fluconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, fluquinconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, prothioconazole, voriconazole, mefentrifluconazole; (b) Inhibitors of Δ14 reductase and Δ8→Δ7-isomerase in sterol biosynthesis: aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph, fenpropidin, piperalin, spiroxamine; (c) Inhibitors of 3-ketoreductase in C4 demethylation of the sterol biosynthesis pathway: fenhexamid, fenpyrazamine; (d) Inhibitors of squalene epoxidase in the sterol biosynthesis pathway: pyributicarb, naftifine, terbinafine;

[0133] (8) Cell wall synthesis inhibitors: (a) chitin synthase inhibitors: polyoxin, polyoxolim; (b) cellulose synthase inhibitors: dimethomorph, flumorph, pyrimorph, benthiavalicarb, benthiavalicarb isopropyl, iprovalicarb, valifenalate, mandipropamide;

[0134] (9) Melanin biosynthesis inhibitors (a) Reductase inhibitors of melanin biosynthesis: fthalide, pyroquilon, tricyclazole; (b) Dehydratase inhibitors of melanin biosynthesis: carpropamid, diclocymet, fenoxanil; (c) Polyketide synthesis inhibitors of melanin biosynthesis: tolprocarb;

[0135] (10) Resistance inducers of host plants: (a) Agents acting on the salicylic acid synthesis pathway: acibenzolar-S-methyl, probenazole, tiadinil, isotianil, diclobenthiazox; (b) Others: ipfentrifluconazole, laminarin, giant knotweed extract; fosetyl aluminum, fosetyl calcium, fosetyl sodium, phosphoric acid, phosphate, phosphorous acid, phosphite;

[0136] (11) Agents of unknown activity: cymoxanil, fosetyl aluminum, phosphoric acid, phosphate salts, tecloftalam, triazoxide, flusulfamide, diclomedine, metasulfocarb, cyflufenamid, metrafenone, pyriophenone, dodine, dodine free base, fluthianil, ferimzone, tebufloquine, picarbutrazox, validamycin;

[0137] (12) Agents with multiple action points: copper (copper salts), Bordeaux mixture, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide; Ambam, Ferbam, Mancozeb, Maneb, Mancopper, Metiram, Metiram zinc, Polycarbamate, Propineb, Thiram, Zineb, Ziram, Captan, Captafol, Folpet, Chlorothalonil, Dichlofluanid, Tolylfluanid, Guazathine, Guazathine acetate, Iminoctadine triacetate, Iminoctadine tribesylate, Anilazine, Dithianone, Chinomethionate, Fluorimide, Metasulfocarb;

[0138] (13) Other agents: DBEDC, fluorofolpet, bis(8-quinolinolato)copper(II), propamidine, chloropicrin, cyproflam, Agrobacterium, bethoxadin, diphenylamine, methylisothianate (MITC), mildeomycin, capsaicin, kufuraneb, cyprosulfamide, dazomet, debacarb, dichlorophen, difenzoquat, difenzoquat methylsulfonate, flumetber, irumamycin, natamycin, nitrotar isopropyl, oxamocarb, pyrrolnitrin, tolnifanide, zaliramide, algophase, amicarthiazol, oxathiapiprolin, fluoxapiprolin, benthazole, trichlamide, uniconazole, oxyfenthiin, pyrapropoin, fluindapir, aminopyrifen, dipimethitron;

[0139] (14) Biological preparations with multiple mechanisms of action: Trichoderma atroviride I-1237 strain, Trichoderma atroviride SKT-1 strain, Trichoderma atroviride LU132 strain, Trichoderma atroviride SC1 strain, Trichoderma atroviride SKT-1 strain, Trichoderma atroviride 77B strain; Trichoderma asperellum T34 strain, Trichoderma asperellum kd strain; Trichoderma harzianum strain T-22; Trichoderma virens strain G-41; Clonostachys rosea strain J1146, Clonostachys rosea strain CR-7; Coniothyrium minitans strain CON / M / 91-08; Hanseniaspora ubaraum strain BC18Y; Talaromyces flavus strain SAY-Y-94-01; Saccharomyces cerevisiae strain LAS02, Saccharomyces cerevisiae strain DDSF623; Bacillus amyloliquefaciens strain QST713, Bacillus amyloliquefaciens strain FZB24, Bacillus amyloliquefaciens strain MBI600, Bacillus amyloliquefaciens strain D747, Bacillus amyloliquefaciens strain F727, Bacillus amyloliquefaciens strain AT-332; Bacillus subtilis strain AFS032321, Bacillus subtilis strain Y1336, Bacillus subtilis strain HAI-0404, Bacillus subtilis strain RTI477; Bacillus berezensis strain RTI301; PHC25279; Gluconobacter selinus strain BC18B; Pseudomonas chlororaphis strain ASF009; Pseudomonas rhodesiae strain HAI-0804; Streptomyces griseoviridis strain K61, and Streptomyces ridix strain WYEC108.

[0140] Specific examples of insecticides, acaricides, nematicides, soil pesticides, anthelmintics, etc. as the active ingredient (II) are shown below.

[0141] (1) Acetylcholinesterase (AChE) inhibitors (a) Carbamate acetylcholinesterase (AChE) inhibitors: alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, xylylcarb, fenothiocarb, MIPC, MPMC, MTMC, aldoxycarb, alixycarb, aminocarb, bufencarb, cloethocarb, metam sodium, promecarb;(b) Organophosphate acetylcholinesterase (AChE) inhibitors: acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, fenflur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyaphos, isofenphos, isocarbophos, isopropyl = O- (methoxyaminothiophosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, para Thionemethyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion, bromophos-ethyl, BRP, carbophenothion, cyanofenphos, CYAP, demeton-S-methylsulfone, dialifos, diclofenthion, dioxabenzophos, etrimphos, fensulfothion, flupyrazophos, fonofos, formothion, fosmetilan, isazophos, iodofenphos, methacrifos, pirimiphos-ethyl, phosphocarb, propafos, protoate, sulprofos;

[0142] (2) GABA-activated chloride ion (chloride ion) channel blockers: acetoprole, chlordane, endosulfan, ethiprole, fipronil, pyrafluprole, pyriprole, camphechlor, heptachlor, dienochlor, and flufiprole;

[0143] (3) Sodium channel modulators (a) Pyrethroid sodium channel modulators: acrinathrin, allethrin, d-cis-trans-allethrin, d-trans-allethrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentenyl-isomer, bioresmethrin, cycloprothrin, cyfluthrin, β-cyfluthrin, cyhalothrin, λ-cyhalothrin, γ-cyhalothrin, cypermethrin, α-cypermethrin, β-cypermethrin, θ-cypermethrin Permethrin, ζ-cypermethrin, cyphenothrin [(1R)-trans isomer], deltamethrin, empenthrin [(EZ)-(1R)-isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, τ-fluvalinate, halfenprox, imiprothrin, kadesrin, permethrin, phenothrin thrin [(1R)-trans isomer], prallethrin, pyrethrum, pyrethrin, resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomer], tralomethrin, transfluthrin, allethrin, pyrethrin I, pyrethrin II, profluthrin, dimefluthrin, bioethanomethrin, biopermethrin, transpermethrin, fenfluthrin, fenpyrithrin, flubrocythrinate, flufenprox, metofluthrin, protrifenbut, pyresmethrin, telallethrin, κ-bifenthrin, chloroprallethrin, heptafluthrin, meperfluthrin, ε-metofluthrin, monfluorothrin, ε-monfluorothrin, κ-tefluthrin, tetramethylfluthrin, bioethanomethrin; (b) Sodium channel modulators (DDTs): DDT, methoxychlor;

[0144] (4) Nicotinic acetylcholine receptor (nAChR) competitive modulators: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam, nicotine, sulfoxaflor, flupyradifurone, triflumezopyrim, dichloromezothiazol, flupirimine; (5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators: spinetoram, spinosad; (6) Glutamate-activated chloride ion (chloride ion) channel (GluCl) allosteric modulators: abamectin, emamectin, emamectin benzoate, lepimectin, milbemectin, ivermectin, selamectin, doramectin, eprinomectin, ivermectin, moxidectin, selamectin, milbemycin, milbemycin oxime, nemadectin;

[0145] (7) Juvenile hormone analogues: hydroprene, kinoprene, methoprene, fenoxycarb, pyriproxyfen, diofenolan, epofenonane, triprene; (8) Other non-specific (multi-site) inhibitors: methyl bromide, alkyl halides, chloropicrin, sodium aluminum fluoride, sulfuryl fluoride, borax, boric acid, disodium octaborate, sodium borate, sodium metaborate, tartar emetic, dazomet, metam, metam potassium salt, metam sodium salt; (9) Chordotonal organ TRPV channel modulators: flonicamid, pymetrozine, pyrifluquinazone, afidopiropen; (10) Mite growth inhibitors: clofentezine, diflobidazine, hexythiazox, etoxazole; (11) Microbial-derived insect midgut membrane disruptors: Proteins found in Bacillus thuringiensis subspecies israerenci, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, Bt crops: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1; Bacillus sphaericus;

[0146] (12) Mitochondrial ATP synthase inhibitors: diafenthiuron, azocyclotine, cyhexatin, fenbutatin oxide, propargite, tetradifon; (13) oxidative phosphorylation uncouplers that disrupt the proton gradient: chlorfenapyr, DNOC, sulfuramide, binapacryl, dinobuton, dinocap; (14) nicotinic acetylcholine receptor (nAChR) channel blockers: bensultap, cartap hydrochloride, nereistoxin, thiocyclam, thiosultap-sodium salt; (15) chitin biosynthesis inhibitors, type 0: bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, buprofezin, fluazuron; (16) chitin biosynthesis inhibitors, type 1: (17) Molting inhibitors: cyromazine; (18) Molting hormone (ecdysone) receptor agonists: chromafenozide, halofenozide, methoxyfenozide, tebufenozide;

[0147] (19) Octopamine receptor agonists: amitraz, demiditraz, chlordimeform; (20) Mitochondrial electron transport chain complex III inhibitors: hydramethylnon, acequinocyl, fluacrypyrim, bifenazate; (21) Mitochondrial electron transport chain complex I inhibitors (METI): fenazaquin, fenpiroximate, pyridaben, pyrimidifen, tebufenpyrad, tolfenpyrad, rotenone; (22) Voltage-dependent sodium channel blockers: indoxacarb, metaflumizone; (23) Acetyl-CoA carboxylase inhibitors: spirodiclofen, spiromesifen, spirotetramat, spiropidione; (24) Mitochondrial electron transport chain complex IV inhibitors: aluminum phosphide, calcium phosphide, zinc phosphide, phosphine, cyanide, calcium cyanide, sodium cyanide, potassium cyanide; (25) Mitochondrial electron transport chain complex II inhibitors: Cyenopyrafen, cyflumetofen, piflubumid;

[0148] (28) Ryanodine receptor modulators: chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide, cyhalodiamide, tetrachlorantraniliprole, tetraniliprole; (29) Chordotonal organ modulators, target site unspecified: flonicamide; (30) GABA-gated chloride ion (chloride ion) channel allosteric modulators: broflanilide, fluxamethamide, isocycloceram, afoxolaner, fluralaner, lotineral, sarolaner; (31) Other insecticides, acaricides: Azadirachtin, benzoximate, bifenazate, bromopropylate, chinomethionate, cryolite, dicofol, lime sulfur mixture, mancozeb, pyridalyl, benclothiaz, sulfur, amidoflumet, 1,3-dichloropropene, DCIP, phenisobromorate, benzomate, metaldehyde, chlorbenzilate, clothiazoben, dicyclanil, fenoxacrim, fentrifanil, flubenzimine, fluphenazine, gossiplura, japonirua, methoxadiazone, petroleum oil, potassium oleate, tetrasulfur, triarane, afidopiropen, flufifol, fluensulfone, meperfluthrin, tetramethylfluthrin, tralopyril, dimefluthrin, methylneodecane Amide, fluralaner, afoxolaner, fluxametamide, 5-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-(1H-1,2,4-triazol-1-yl)benzonitrile (CAS: 943137-49-3), broflanilide, other metadiamides, Steinernema carpocapsae, Steinernema glaceri, Pasteuria penetrans, Pecilomyces tenuipes, Pecilomyces fumosoroseus, Beauveria bassiana, Beauveria brongniartii, Metarhizium anisopliae, Verticillium lecanii, acinonapyr, benzpyrimoxane, flometoquin, fluhexafon, oxazosulfil, cyclopyrazoflor.

[0149] (32) Anthelmintics: (a) Benzimidazoles: fenbendazole, albendazole, triclabendazole, oxibendazole, mebendazole, oxfendazole, perbendazole, flubendazole, febantel, netobimin, thiophanate, thiabendazole, cambandazole; (b) Salicylanilides: closantel, oxyclozanide, rafoxanide, niclosamide; (c) Substituted phenols: nitroxynil, nitroscanate; (d) Pyrimidines: pyrantel, morantel; (e) Imidazothiazoles: levamisole, tetramisole; (f) Tetrahydropyrimidines: praziquantel, epsiprantel; (g) Other anthelmintics: Cyclodien, riania, clorsulon, metronidazole, demiditraz, piperazine, diethylcarbamazine, dichlorophen, monepantel, tribendimidine, amidantel, thiacetarsamide, melarsomine, arsenamide.

[0150] Specific examples of plant regulators as the active ingredient (II) are shown below: abscisic acid, kinetin, benzylaminopurine, 1,3-diphenylurea, forchlorfenuron, thidiazuron, chlorfenuron, dihydrozeatin, gibberellin A, gibberellin A4, gibberellin A7, gibberellin A3, 1-methylcyclopropane, N-acetylaminoethoxyvinylglycine (also known as abiglycine), aminooxyacetic acid, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyric acid, dichlorprop, phenothionyl ol, 1-naphthylacetamide, ethychlozate, cloxifonac, maleic hydrazide, 2,3,5-triiodobenzoic acid, salicylic acid, methyl salicylate, (-)-jasmonic acid, methyl jasmonate, (+)-strigol, (+)-deoxystrigol, (+)-orobanchol, (+)-sorgolactone, 4-oxo-4-(2-phenylethyl)aminobutyric acid, ethephon, chlormequat, mepiquat chloride, benzyladenine, 5-aminolevulinic acid, daminozide.

[0151] {Formulation} The agricultural and horticultural fungicide of the present invention is not particularly limited by its formulation. For example, it can be in the form of a wettable powder, emulsifiable concentrate, dust, granule, water-soluble powder, suspension, water-dispersible granule, tablet, etc. The method of preparation into a formulation is not particularly limited, and a known preparation method can be adopted depending on the formulation. In addition, the compound represented by formula (I) or its salt may be directly used as an agricultural and horticultural fungicide.

[0152] Some formulation examples are shown below. The formulations shown below are merely illustrative and can be modified within the scope of the present invention, and the present invention is not limited by the following formulation examples. Hereinafter, the term "compound of the present invention" means "a compound represented by formula (I) or a salt thereof," and may be a single compound represented by formula (I) or a salt thereof, or a mixture of two or more compounds represented by formula (I) or their salts. "Parts" means "parts by mass" unless otherwise specified.

[0153] (Formulation Example 1: Wettable Powder) 40 parts of the compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfate, and 3 parts of alkylnaphthalene sulfonate are uniformly mixed and then finely pulverized to obtain a wettable powder containing 40% by mass of the active ingredient.

[0154] Formulation Example 2: Emulsifiable concentrate 30 parts of the compound of the present invention, 33 parts of xylene, 30 parts of dimethylformamide, and 7 parts of polyoxyethylene alkyl allyl ether are mixed and dissolved to obtain an emulsifiable concentrate containing 30% by mass of the active ingredient.

[0155] (Formulation Example 3: Granules) 5 parts of the compound of the present invention, 40 parts of talc, 38 parts of clay, 10 parts of bentonite, and 7 parts of sodium alkyl sulfate are uniformly mixed, then finely pulverized, and then granulated to a particle diameter of 0.5 to 1.0 mm to obtain granules containing 5% by mass of the active ingredient.

[0156] Formulation Example 4: Granules 5 parts of the compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of dioctyl sulfosuccinate sodium salt, and 1 part of potassium phosphate are uniformly mixed and pulverized, and then water is added thereto and kneaded. Thereafter, the mixture is granulated and dried to obtain granules containing 5% by mass of the active ingredient.

[0157] Formulation Example 5: Suspension 10 parts of the compound of the present invention, 4 parts of polyoxyethylene alkyl allyl ether, 2 parts of sodium polycarboxylate, 10 parts of glycerin, 0.2 parts of xanthan gum, and 73.8 parts of water are mixed and wet-pulverized to a particle size of 3 microns or less to obtain a suspension containing 10% by mass of the active ingredient.

[0158] (Formulation Example 6: Water Dispersible Granules) 40 parts of the compound of the present invention, 36 parts of clay, 10 parts of potassium chloride, 1 part of sodium alkylbenzenesulfonate, 8 parts of sodium ligninsulfonate, and 5 parts of a formaldehyde condensate of sodium alkylbenzenesulfonate are uniformly mixed and finely pulverized. An appropriate amount of water is then added thereto, and the mixture is kneaded to form a clay-like substance. The clay-like substance is granulated and then dried to obtain a water dispersible granule containing 40% by mass of the active ingredient.

[0159] Next, the present invention will be explained in more detail by showing compound production examples, but the present invention is not limited to the following examples in any way.

[0160] Production Example 1 N-((4-(6-chloropyridin-2-yl)-1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)methyl)-5-(2,4-difluorophenyl)isoxazole-3-carboxamide (Compound No. A-1)) was produced by the following steps.

[0161] (Step 1) Conversion of 1-methyl-4,5,6,7-tetrahydro-1H-indazole-4-carbonitrile to 4-(6-chloropyridin-2-yl)-1-methyl-4,5,6,7-tetrahydro-1H-indazole-4-carbonitrile

[0162]

[0163] A 50 mL recovery flask was charged with argon gas and charged with 1-methyl-4,5,6,7-tetrahydro-1H-indazole-4-carbonitrile (0.59 g) and tetrahydrofuran (18.5 ml). A diisopropylamide lithium solution (2.0 M, 2.4 ml) was added dropwise at −78°C. After the addition, the mixture was stirred for 35 minutes. To this mixture, 2,6-dichloropyridine (0.82 g) was added at −78°C. The mixture was then slowly warmed to room temperature over 1.5 hours. Water was added to the resulting solution, which was then extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting concentrate was purified by silica gel column chromatography to yield 0.78 g of 4-(6-chloropyridin-2-yl)-1-methyl-4,5,6,7-tetrahydro-1H-indazole-4-carbonitrile.

[0164] (Step 2) Conversion of 4-(6-chloropyridin-2-yl)-1-methyl-4,5,6,7-tetrahydro-1H-indazole-4-carbonitrile to (4-(6-chloropyridin-2-yl)-1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)methanamine

[0165]

[0166] 4-(6-chloropyridin-2-yl)-1-methyl-4,5,6,7-tetrahydro-1H-indazole-4-carbonitrile (0.32 g) and tetrahydrofuran (3.5 ml) were placed in an argon-purged 50 mL recovery flask, and 90% by mass dimethylsulfide borane (0.37 ml) was added. The mixture was then stirred at 60°C for 6 hours. The resulting solution was concentrated under reduced pressure, and methanol and 1 M hydrochloric acid were added to the concentrate, followed by stirring at room temperature. Aqueous sodium hydroxide was added to the concentrate, followed by extraction with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to yield 0.18 g of a crude product containing (4-(6-chloropyridin-2-yl)-1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)methanamine. This crude product was used in the next step without further purification.

[0167] (Step 3) Conversion of (4-(6-chloropyridin-2-yl)-1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)methanamine to the target product (Compound No. A-1)

[0168]

[0169] The crude product (65 mg) containing (4-(6-chloropyridin-2-yl)-1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)methanamine was dissolved in dimethylformamide (1.2 mL). 5-(2,4-difluorophenyl)isoxazole-3-carboxylic acid (53 mg), N,N-diisopropylethylamine (91 mg), and 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (89 mg) were added, followed by stirring at room temperature for 40 minutes. 1M hydrochloric acid was added to the resulting solution, which was then extracted with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting concentrate was purified by silica gel column chromatography to obtain 35.8 mg of the target compound.

[0170] [Production Example 2] N1-((4-(6-chloropyridin-2-yl)-1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)methyl)-N2-(2,4-difluorophenyl)oxamide [English name: N1-((4-(6-chloropyridin-2-yl)-1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)methyl)-N2-(2,4-difluorophenyl)oxalamide (Compound No. A-3)] was produced by the following steps.

[0171] (Step 1) Conversion of ethyl 2-chloro-2-glyoxylate to ethyl 2-((2,4-difluorophenyl)amino)-2-oxoacetate

[0172]

[0173] 2,4-Difluoroaniline (6.0 g) and triethylamine (5.6 g) were dissolved in tetrahydrofuran (37 ml), and ethyl 2-chloro-2-glyoxylate (6.7 g) was added dropwise at 0°C, followed by stirring at room temperature for 1.5 hours. The resulting solution was concentrated under reduced pressure, and water and 10% by mass hydrochloric acid were added, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate and then saturated brine, and concentrated under reduced pressure to obtain 10.4 g of a crude product containing ethyl 2-((2,4-difluorophenyl)amino)-2-glyoxylate. This was used in the next step without purification.

[0174] (Step 2) Conversion of ethyl 2-((2,4-difluorophenyl)amino)-2-glyoxylate to 2-((2,4-difluorophenyl)amino)-2-glyoxylic acid [English name: 2-((2,4-difluorophenyl)amino)-2-oxoacetic acid]

[0175]

[0176] The crude product (9.3 g) containing ethyl 2-((2,4-difluorophenyl)amino)-2-glyoxylate was dissolved in methanol (122 ml), and 9 M sodium hydroxide (9.0 g) was added, followed by stirring at room temperature for 1.5 hours. The resulting solution was concentrated under reduced pressure, and water and 10% by mass hydrochloric acid were added and stirred. The precipitated crystals were filtered, washed with water, and dried to obtain 8.5 g of 2-((2,4-difluorophenyl)amino)-2-glyoxylic acid.

[0177] (Step 3) Conversion of 2-((2,4-difluorophenyl)amino)-2-glyoxylic acid to the target product (Compound No. A-3)

[0178]

[0179] The crude product (47 mg) containing (4-(6-chloropyridin-2-yl)-1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)methanamine was dissolved in dimethylformamide (0.8 mL), and 2-((2,4-difluorophenyl)amino)-2-glyoxylic acid (34 mg), N,N-diisopropylethylamine (66 mg), and 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (65 mg) were added, followed by stirring at room temperature for 1 hour. 1 M hydrochloric acid was added to the resulting solution, which was then extracted with ethyl acetate. The resulting organic layer was concentrated under reduced pressure, and the concentrate was purified by silica gel column chromatography to yield 14.8 mg of the target product.

[0180] [Production Example 3] Synthesis of 5-(2,4-difluorophenyl)-N-((1-methyl-4-(6-(trifluoromethyl)pyridin-2-yl)-4,5,6,7-tetrahydro-1H-indazol-4-yl)methyl)isoxazole-3-carboxamid (Compound No. A-35)

[0181] (Step 1-1) Synthesis of 1-methyl-4-(6-(trifluoromethyl)pyridin-2-yl)-4,5,6,7-tetrahydro-1H-indazol-4-ol

[0182]

[0183] 2-Bromo-6-trifluoromethylpyridine (4.52 g) was dissolved in tetrahydrofuran (20 mL) and stirred at room temperature. Cerium(III) chloride (4.93 g) was added to the solution, and the mixture was stirred at -78°C. Butyllithium (2.6 M) (7.5 mL) was added to the solution, and the mixture was stirred at the same temperature for 1 hour. 1-Methyl-1,5,6,7-tetrahydro-4H-indazol-4-one (1.50 g) was then added, and the mixture was slowly heated to 0°C and stirred for 1 hour. Water was poured into the reaction solution, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to yield 2.57 g of the target product.

[0184] (Step 1-2) Synthesis of 1-methyl-4-(6-(trifluoromethyl)pyridin-2-yl)-4,5,6,7-tetrahydro-1H-indazole-4-carbonitrile

[0185]

[0186] 1-Methyl-4-(6-(trifluoromethyl)pyridin-2-yl)-4,5,6,7-tetrahydro-1H-indazol-4-ol (0.59 g) was dissolved in methylene chloride (20 mL) and stirred at room temperature. To this solution, trimethylsilylnitrile (0.89 g), lithium carbonate (30 mg), and iodine (0.91 g) were added sequentially, and the mixture was stirred at room temperature for 3 hours. Aqueous sodium thiosulfate solution was poured into the reaction solution, and the mixture was extracted with methylene chloride. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain 0.23 g of the target product.

[0187] (Step 1-3) Synthesis of (1-methyl-4-(6-(trifluoromethyl)pyridin-2-yl)-4,5,6,7-tetrahydro-1H-indazol-4-yl)methanamine

[0188]

[0189] 1-Methyl-4-(6-(trifluoromethyl)pyridin-2-yl)-4,5,6,7-tetrahydro-1H-indazole-4-carbonitrile (0.50 g) was dissolved in tetrahydrofuran (5 mL) and stirred at 0°C. Dimethylsulfide borane (0.41 g) was added dropwise to the solution, and the mixture was further stirred at room temperature for 66 hours. Methanol and hydrochloric acid (dioxane solution) were sequentially added to the reaction solution. The resulting solution was concentrated under reduced pressure, and ethyl acetate was added. The mixture was then washed with aqueous sodium hydroxide, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain 0.43 g of the target product.

[0190] (Step 1-4) Synthesis of 5-(2,4-difluorophenyl)-N-((1-methyl-4-(6-(trifluoromethyl)pyridin-2-yl)-4,5,6,7-tetrahydro-1H-indazol-4-yl)methyl)isoxazole-3-carboxamide

[0191]

[0192] (1-Methyl-4-(6-(trifluoromethyl)pyridin-2-yl)-4,5,6,7-tetrahydro-1H-indazol-4-yl)methanamide (0.075 g) was dissolved in dimethylformamide (5 mL) and stirred at room temperature. Diisopropylethylamine (0.13 g), 5-(2,4-difluorophenyl)isoxazole-3-carboxylic acid (65 mg), and (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (PyBOP) (0.14 g) were added sequentially and stirred at room temperature for 2 hours. Aqueous ammonium chloride solution was poured into the reaction solution and extracted with ethyl acetate. The resulting organic layer was washed with aqueous sodium bicarbonate, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to yield 0.07 g of the target product.

[0193] Preparation Example 4 N-((4-(6-chloropyridin-2-yl)-1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)methyl)-5-(3,4-difluorophenyl)-1,2,4-oxadiazole-3-carboxamide [English name: N-((4-(6-chloropyridin-2-yl)-1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)methyl)-5-(3,4-difluorophenyl)-1,2,4-oxadiazole-3-carboxamide (Compound No. A-69)] was prepared by the following steps.

[0194] (Step 1) Conversion of (4-(6-chloropyridin-2-yl)-1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)methanamine to (Z)-2-amino-N-((4-(6-chloropyridin-2-yl)-1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)methyl)-2-(hydroxyimino)acetamide

[0195]

[0196] (4-(6-chloropyridin-2-yl)-1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)methanamine (0.83 g) was dissolved in ethanol (3 mL), and N,N-diisopropylethylamine (0.78 g) and ethyl (Z)-2-amino-2-(hydroxyimino)acetate (0.79 g) were added thereto, followed by stirring at room temperature for 1 hour. 1 M hydrochloric acid was added to the resulting solution, which was then extracted with ethyl acetate. The resulting organic layer was concentrated under reduced pressure, and the concentrate was purified by silica gel column chromatography to yield 0.55 g of (Z)-2-amino-N-((4-(6-chloropyridin-2-yl)-1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)methyl)-2-(hydroxyimino)acetamide.

[0197] (Step 2) Conversion of (Z)-2-amino-N-((4-(6-chloropyridin-2-yl)-1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)methyl)-2-(hydroxyimino)acetamide to the target product (Compound No. A-69)

[0198]

[0199] (Z)-2-amino-N-((4-(6-chloropyridin-2-yl)-1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)methyl)-2-(hydroxyimino)acetamide (73 mg) was dissolved in ethyl acetate (0.2 mL), and to this was added triethylamine (61 mg), 3,4-difluorobenzoic acid (41 mg), and a propylphosphonic anhydride solution (50% by mass, 0.13 g), followed by stirring at 80°C for 2 hours. Water was added to the resulting solution, which was then extracted with ethyl acetate. The resulting organic layer was concentrated under reduced pressure, and the concentrate was purified by silica gel column chromatography to obtain 40 mg of the target product.

[0200] Production Example 5 Pentyl ((4-(6-chloropyridin-2-yl)-1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)methyl)carbamate (Compound No. A-94) was produced by the following steps.

[0201] (Step 1) Conversion of (4-(6-chloropyridin-2-yl)-1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)methanamine to the target product (Compound No. A-94)

[0202]

[0203] (4-(6-chloropyridin-2-yl)-1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)methanamine (0.10 g) and triethylamine (0.11 g) were dissolved in 1,4-dioxane (1.8 mL), and triphosgene (0.11 g) was added to the solution at 0°C. The mixture was then stirred at room temperature for 2 hours. The resulting solution was concentrated under reduced pressure, dissolved in tetrahydrofuran (1.8 mL), and triethylamine (0.11 g) and 1-pentanol (38 mg) were added. The mixture was then stirred at room temperature for 6 hours. Water was added to the resulting solution, and the mixture was extracted with ethyl acetate. The resulting organic layer was concentrated under reduced pressure, and the concentrate was purified by silica gel column chromatography to obtain 43 mg of the target product.

[0204] The compounds shown in Table 1 were prepared using the same procedures as in the above examples. The melting point or appearance (amorphous or viscous oil) is noted in the properties column. For compounds with an amorphous or viscous oil appearance, the LCMS retention time is noted.

[0205] LCMS (SQD2) retention times were determined as follows. A system consisting of an ultra-high-performance, high-resolution liquid chromatograph (ACQUITY UPLC H-Class, manufactured by Waters), an HPLC / UHPLC detector (ACQUITY UPLC Photodiode Array (PDA) eλ Detector, manufactured by Waters), and a single quadrupole MS detector (LC / MS) (SQ Detector 2 detector, positive and negative ion electrospray mode and atmospheric pressure chemical ionization mode) was equipped with a CORTECS UPLC C18 column (manufactured by Waters, 2.1 x 50 mm, 1.6 μm). Measurements were performed at a temperature of 40°C, a flow rate of 0.6 mL / min, and a 2 μL injection. Water containing 0.1% formic acid was used as mobile phase (A), and acetonitrile was used as mobile phase (B). The concentration of the mobile phase (B) was maintained at 30% by mass for 0.15 minutes, then the concentration of the mobile phase (B) was increased at a constant rate from 30% by mass to 95% by mass over 1.35 minutes, maintained at 95% by mass for 0.5 minutes, then the concentration of the mobile phase (B) was immediately decreased to 30% by mass, and finally the concentration of the mobile phase (B) was maintained at 30% by mass for 0.50 minutes.

[0206] LCMS (QDa) retention times were determined as follows. A system consisting of an ultra-high-performance, high-resolution liquid chromatograph (ACQUITY UPLC H-Class, manufactured by Waters), an HPLC / UHPLC detector (ACQUITY UPLC Photodiode Array (PDA) eλ Detector, manufactured by Waters), and a single quadrupole MS detector (LC / MS) (ACQUITY QDa Detector in positive and negative ion electrospray mode) was equipped with a CORTECS UPLC C18 column (manufactured by Waters, 2.1 x 50 mm, 1.6 μm). Measurements were performed at a temperature of 40°C, a flow rate of 0.6 mL / min, and a 2 μL injection. Water containing 0.1% formic acid was used as mobile phase (A), and acetonitrile was used as mobile phase (B). The concentration of mobile phase (B) was maintained at 30% by mass for 0.15 minutes, then increased from 30% by mass to 95% by mass over 1.35 minutes at a constant rate, maintained at 95% by mass for 0.5 minutes, then immediately decreased to 30% by mass, and finally maintained at 30% by mass for 0.50 minutes.

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266] Among the compounds described as AMORPHOUS or VISCOUS OIL in the column of physical properties in the table above, compounds A-72, A-84, A-95, A-96, A-109, A-110, A-112, A-133, A-134, A-151, A-171, A-173, A-174 and A-176 are as follows: 1 The H-NMR data is shown below. Compound A-72: 1 H-NMR (400 MHz, CDCl3): δ1.61-1.65(m, 1H), 1.90-2.02(m, 2H), 2.24-2.30(m, 1H), 2.60-2.63(m, 2H), 3.78(s, 3H), 3.86(d, 3H), 3.97-4.06(m, 2H), 6.92-7.01(m, 3H), 7.04(s, 1H), 7.18(dd, 1H), 7.26-7.32(m, 1H), 7.36(s, 1H), 7.50(t, 1H), 8.16(br-t, 1H). Compound A-84: 1H-NMR(400 MHz, CDCl3): δ1.62-1.69(m, 1H), 1.99-2.13(m, 2H), 2.60-2.67(m, 1H), 3.80(s, 3H), 3.88(dd, 1H), 4.24(dd, 1H), 7.00(dd, 1H), 7.02-7.13(m, 2H), 7.23(dd, 1H),7.26(s, 1H), 7.54(t, 1H), 8.60-8.65(m, 1H), 9.17-9.19(m, 1H). Compound A-95: 1 H-NMR (400 MHz,CDCl3): δ0.93(t, 3H), 1.32-1.41(m, 2H), 1.51-1.68(m, 3H), 1.81-1.88(m, 1H), 1.93-2.02(m, 1H), 2.10-2.15(m, 1H), 2.22(t, 2H), 2.60(t, 2H), 3.68(dd, 1H), 3.78(s, 3H), 3.89(d, 1H), 6.94(d, 1H), 7.05(br-m, 1H), 7.18(d, 1H), 7.24(s, 1H), 7.50(t, 1H). Compound A-96: 1 H-NMR(400 MHz, CDCl3): δ0.86-0.89(m, 3H), 1.26-1.37(m, 6H), 1.51-1.69(m, 3H), 1.82-1.88(m, 1H), 1.93-2.02(m, 1H), 2.09-2.15(m, 1H), 2.22(t, 2H), 2.58-2.61(m, 2H), 3.68(dd, 1H), 3.78(s, 3H), 3.89(d, 1H), 6.94(dd, 1H), 7.04-7.05(br-m, 1H), 7.18(dd, 1H), 7.24(s, 1H), 7.50(t, 1H). Compound A-109: 1H-NMR (400 MHz,CDCl3): δ1.64-1.69(m, 1H), 2.01-2.08(m, 3H), 2.64-2.69(m, 2H), 3.78(dd, 1H), 3.82(s, 3H),4.26(dd, 1H), 7.20(s, 1H), 7.27(d, 1H), 7.32(t, 1H), 7.59(dd, 1H), 7.63(ddd, 1H), 7.75-7.79(m, 2H), 8.03(t, 1H), 8.40-8.42(m, 1H). Compound A-110: 1 H-NMR (400 MHz,CDCl3): δ1.63-1.67(m, 1H), 2.00-2.08(m, 3H), 2.64-2.68(m, 2H), 3.77(dd, 1H), 3.82(s, 3H),4.25(dd, 1H), 7.20(s, 1H), 7.27(d, 1H), 7.32(t, 1H), 7.57-7.61(m, 3H), 7.72-7.79(m, 3H), 8.39-8.41(m, 1H). Compound A-112: 1 H-NMR (400 MHz,CDCl3): δ1.60-1.66(m, 1H), 1.91-2.03(m, 2H), 2.18-2.23(m, 1H), 2.62(t, 2H), 3.80(s, 3H), 3.95(dd, 1H), 4.08(dd, 1H), 6.96-7.03(m, 3H), 7.20(dd, 1H), 7.31(s, 1H), 7.52(t, 1H), 7.68-7.74(m, 1H), 8.09(s, 1H), 8.46-8.49(m, 1H). Compound A-133: 1H-NMR (400 MHz, CDCl3): δ 1.56 - 1.64 (m, 1H), 1.86 - 2.04 (m, 2H), 2.20 - 2.26 (m, 1H), 2.59 - 2.62 (m, 2H), 3.79 (s, 3H), 3.94 (dd, 1H), 4.07 (d, 1H), 6.98 (dd, 1H), 7.20 (dd, 1H), 7.31 (s, 1H), 7.51 (t, 1H), 7.95 (dd, 1H), 8.06 (dd, 1H), 8.65 (dd, 1H), 9.11 (br-t, 1H). Compound A-134: 1 H-NMR (400 MHz, CDCl3): δ 1.60 - 1.70 (m, 1H), 1.95 - 2.17 (m, 3H), 2.64 - 2.67 (m, 2H), 3.81 (s, 3H), 3.90 (dd, 1H), 4.16 (d, 1H), 6.96 (dd, 1H), 7.20 (dd, 1H), 7.22 (s, 1H), 7.53 (t, 1H), 7.70 (d, 1H), 8.11 - 8.12 (br-m, 1H), 8.44 (d, 1H). Compound A-151: 1 H-NMR (400 MHz, CDCl3): δ 1.27 - 1.38 (m, 1H), 1.91 - 2.06 (m, 2H), 2.18 - 2.30 (m, 1H), 2.62 (t, 2H), 3.79 (s, 3H), 4.08 - 4.25 (m, 2H), 6.80 (dd, 1H), 6.96 - 7.01 (m, 2H), 7.07 - 7.11 (m, 1H), 7.36 (s, 1H), 7.66 (dd, 1H), 8.06 (dd, 1H), 8.22 (dd, 1H), 8.34 (d, 1H), 8.69 - 8.75 (m, 1H). Compound A-171: 1H-NMR (400 MHz, CDCl3): δ 1.46 (s, 9H), 1.71 - 1.74 (m, 1H), 1.94 - 2.05 (m, 2H), 2.10 - 2.15 (m, 1H), 2.63 - 2.67 (m, 2H), 3.79 (s, 3H), 3.92 - 3.96 (dd, 1H), 4.14 - 4.20 (dd, 1H), 6.83 (d, 1H), 6.94 - 7.05 (m, 2H), 7.08 (d, 1H), 7.20 (dd, 1H), 7.21 (s, 1H), 7.48 (t, 1H), 8.92 - 7.98 (m, 1H), 8.60 - 8.62 (m, 1H). Compound A-173: 1 H-NMR (400 MHz, CDCl3): δ 1.47 (s, 9H), 1.72 - 1.76 (m, 1H), 1.85 - 1.91 (m, 1H), 1.97 - 2.05 (m, 1H), 2.06 - 2.10 (m, 1H), 2.64 (t, 2H), 3.79 (s, 3H), 3.91 (dd, 1H), 4.02 (dd, 1H), 6.81 (d, 1H), 6.87 - 6.92 (m, 2H), 7.18 (s, 1H), 7.20 (dd, 1H), 7.48 (t, 1H), 8.30 - 8.35 (m, 1H), 8.97 - 8.98 (m, 1H), 9.43 (s, 1H). Compound A-174: 1 H-NMR (400 MHz, CDCl3): δ 1.44 (s, 9H), 1.60 - 1.63 (m, 1H), 1.89 - 1.99 (m, 2H), 2.16 - 2.21 (m, 1H), 2.62 (t, 2H), 3.69 (dd, 1H), 3.79 (s, 3H), 4.04 (dd, 1H), 6.80 (d, 1H), 6.84 - 6.93 (m, 2H), 7.21 (dd, 1H), 7.25 (s, 1H), 7.48 (t, 1H), 7.52 - 7.56 (m, 1H), 8.78 - 8.79 (m, 1H). Compound A-176: 1H-NMR(400 MHz, CDCl3): δ1.66-1.74(m, 1H), 1.91-2.04(m, 2H), 2.17-2.26(m, 1H), 2.64(t, 2H), 2.74(s, 3H), 3.80(s, 3H), 4.05-4.15(m, 2H), 6.72(dd, 1H), 6.99-7.04(m, 1H), 7.06-7.10(m, 2H), 7.29(s, 1H), 7.36(t, 1H), 8.40-8.45(m, 1H), 8.48-8.51(m, 1H).

[0267] The effects of the present invention will be illustrated by the following fungicidal effect test and disease control test.

[0268] (Test of fungicidal effect against Botrytis cinerea) A spore suspension of Botrytis cinerea (Vogel medium) was prepared. The compound of the present invention was added to dimethyl sulfoxide to obtain a drug solution. Equal amounts (volume basis) of this drug solution and the spore suspension were mixed to obtain a test solution with a concentration of the compound of the present invention of 25 ppm by mass. The test solution was dropped into a 96-well microplate (drug-treated group). Equal amounts (volume basis) of dimethyl sulfoxide and the spore suspension were mixed to obtain a control solution. The control solution was dropped into a 96-well microplate (untreated group). These were left to stand at 20°C in a dark place and cultured for 5 days. The turbidity (OD) at a wavelength of 405 nm was measured using a microplate reader. The growth inhibition rate was calculated using the following formula: Growth inhibition rate (%) = 100 - 100 × {[(OD of drug-treated group after incubation) - (OD of drug-treated group before incubation)] / [(OD of untreated group after incubation) - (OD of untreated group before incubation)]}

[0269] Compound numbers A-1, A-2, A-3, A-4, A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-15, A-16, A-17, A-20, A-22, A-23, A-25, A-29, A-33, A-34, A-35, A-36, A-37, A-39, A-40, A-41, A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A-50, A-51, A-53, A-54, A-65, A-74, A-94, A-96, A-97, and A-104 were tested for fungicidal effect against Botrytis cinerea. All of the compounds showed a growth inhibition rate of 75% or more.

[0270] (Test of fungicidal effect against apple anthracnose fungus) The turbidity was measured and the growth inhibition rate was calculated in the same manner as in the test of fungicidal effect against Botrytis cinerea, except that the spore suspension of Botrytis cinerea (Vogel medium) was replaced with a spore suspension of Colletotrichum acutatum (Czapek medium) and the temperature and period of standing were changed to 25°C and 4 days, respectively.

[0271] Compound numbers A-1, A-2, A-3, A-4, A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-15, A-16, A-17, A-20, A-22, A-23, A-29, A-33, A-34, A-35, A-36, A-37, A-39, A-40, A-41 The fungicidal effects of the compounds A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A-50, A-51, A-52, A-53, A-54, A-65, A-74, A-93, A-94, A-95, A-96, A-97, and A-104 on apple anthracnose were tested. All compounds showed growth inhibition rates of 75% or more.

[0272] (Test of bactericidal effect against grape late rot fungus) The turbidity was measured in the same manner as in the test of bactericidal effect against grape late rot fungus, except that the spore suspension of Botrytis cinerea (Vogel medium) was replaced with a spore suspension of Glomerella cingulata (Vogel medium) and the temperature and period of standing were changed to 25°C and 3 days, respectively, and the growth inhibition rate was calculated.

[0273] Compound numbers A-1, A-2, A-3, A-4, A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-15, A-16, A-17, A-20, A-22, A-23, A-25, A-29, A-33, A-34, A-35, A-36, A-37, A-38, A-39, A-40 The fungicidal effects of the compounds A-41, A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A-50, A-51, A-52, A-53, A-54, A-65, A-74, A-93, A-94, A-95, A-96, A-97, and A-104 on grape late rot fungi were tested. All compounds showed growth inhibition rates of 75% or more.

[0274] (Test of fungicidal effect against apple brown spot fungus) The turbidity was measured and the growth inhibition rate was calculated in the same manner as in the test of fungicidal effect against Botrytis cinerea, except that the spore suspension of Botrytis cinerea (Vogel medium) was replaced with a spore suspension of Alternaria mali (SD medium) and the temperature and period of standing were changed to 25°C and 4 days, respectively.

[0275] Compound numbers A-1, A-2, A-3, A-4, A-7, A-8, A-10, A-11, A-12, A-13, A-14, A-15, A-16, A-17, A-20, A-22, A-23, A-25, A-29, A-33, A-34, A-35, A-36, A-37, A-39, A-40, A-41 The fungicidal effects of the compounds A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A-50, A-51, A-52, A-53, A-54, A-65, A-74, A-93, A-94, A-95, A-96, A-97, and A-104 on apple brown spot pathogen were tested. All compounds showed growth inhibition rates of 75% or more.

[0276] (Test for control of cucumber gray mold) 5 parts by mass of the compound of the present invention, 93.5 parts by mass of N,N-dimethylformamide, and 1.5 parts by mass of polyoxyethylene sorbitan monolaurate were mixed to obtain an emulsifiable concentrate (1) containing 5% by mass of the active ingredient.

[0277] Water was added to the emulsion (1) to obtain a drug solution containing the compound of the present invention at a concentration of 125 ppm by mass. Subsequently, the drug solution was sprayed onto cucumber seedlings (variety "Jihai", cotyledon stage) grown in seedling pots, followed by air drying. A conidial suspension of Botrytis cinerea was then added dropwise to the seedlings to inoculate them with Botrytis cinerea conidial spores (treated group). As a control, a conidial suspension of Botrytis cinerea was added dropwise to cucumber seedlings not sprayed with the drug solution to inoculate them with Botrytis cinerea conidial spores (untreated group). These were then placed in a moist chamber at 20°C. Four days after inoculation, the lesion area ratio on the leaves of the cucumber seedlings was measured, and the control titer was calculated using the following formula:

[0278] Control value (%) = 100 - {lesion area rate in treated area / lesion area rate in untreated area} x 100

[0279] Compound numbers A-1, A-2, A-3, A-5, A-11, A-12, A-13, A-14, A-15, A-16, A-18, A-20, A-21, A-23, A-24, A-25, A-26, A-28, A-29, A-31, A- 33, A-34, A-35, A-36, A-37, A-40, A-41, A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A-50, A-51, A-56, A-57, A-58, A-59, A A control test of cucumber gray mold was conducted on A-60, A-62, A-69, A-74, A-77, A-87, A-91, A-94, A-96, A-97, A-103, A-108, A-112, A-115, A-118, A-125, A-128, A-133, A-147, A-148, A-149, A-153, A-154, A-162, A-168, A-169, A-170, A-175, A-176, A-183, and A-184 at a concentration of 125 ppm by mass. All compounds showed a control value of 75% or more.

[0280] (Test for Control of Apple Scab) Water was added to the emulsion (1) to give a concentration of the compound of the present invention of 125 ppm by mass, and the compound was dissolved to obtain a drug solution. The drug solution was then sprayed onto apple seedlings (cultivar "Orin", 3-4 leaf stage) grown in nursery pots, followed by air drying. The treated apple seedlings were then inoculated with conidia of the apple scab fungus (Venturia inaequalis) (treated group). As a control, apple seedlings not sprayed with the drug solution were inoculated with conidia of the apple scab fungus (Venturia inaequalis) (untreated group). These were then placed in a moist chamber at 20°C, with a 12-hour cycle of light and dark. 12 to 14 days after inoculation, the lesion area ratio on the leaves of the apple seedlings was measured, and the control titer was calculated.

[0281] Compound numbers A-1, A-2, A-3, A-11, A-12, A-14, A-15, A-17, A-29, A-33, A-34, A-35, A-36, A-37, A-40, A-41, A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A-58, A-59, A-61, A-6 Control tests of apple scab were carried out on A-9, A-70, A-73, A-74, A-76, A-77, A-81, A-84, A-85, A-86, A-87, A-88, A-89, A-91, A-92, A-93, A-94, A-96, A-104, A-107, A-108, A-112, A-115, and A-118. All compounds showed a control rate of 75% or more.

[0282] (Test for Control of Wheat Powdery Mildew) Water was added to the above emulsion (1) so that the concentration of the compound of the present invention was 125 ppm by mass, and the compound was dissolved to obtain a chemical solution. Subsequently, the chemical solution was sprayed onto wheat seedlings (variety "Chihoku", 1- to 2-leaf stage) grown in seedling pots and air-dried. Subsequently, conidia of wheat powdery mildew (Erysiphe graminis f.sp. tritici) were sprinkled on the seedlings for inoculation (treated group). As a control, conidia of wheat powdery mildew (Erysiphe graminis f.sp. tritici) were sprinkled on wheat seedlings that had not been sprayed with the chemical solution (untreated group). These were then left to stand in a greenhouse at 20°C. Six days after inoculation, the lesion area ratio on the leaves of the wheat seedlings was measured, and the control titer was calculated.

[0283] Compound numbers A-1, A-2, A-3, A-11, A-12, A-14, A-15, A-17, A-18, A-29, A-33, A-34, A-35, A-36, A-37, A-40, A-41, A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A-69, A In a wheat powdery mildew control test, A-74, A-77, A-78, A-85, A-87, A-88, A-94, A-112, A-118, A-126, A-128, A-132, A-147, A-148, A-154, A-162, A-168, A-169, A-170, and A-175 were tested. All compounds showed a control rate of 75% or more.

[0284] Since all of the compounds randomly selected from the compounds of the present invention exhibit the effects described above, it can be understood that the compounds of the present invention, including compounds not listed as examples, have a bactericidal effect, do not cause phytotoxicity to plants, and have little toxicity to humans, livestock, and fish, and little impact on the environment.

[0285] The pyrazole compound of the present invention has excellent fungicidal activity against pathogenic bacteria that affect agricultural and horticultural plants, is highly safe, and can be synthesized industrially advantageously. The agricultural and horticultural fungicide of the present invention can effectively control diseases of agricultural and horticultural plants.

Claims

1. A compound represented by formula (I) or a salt thereof. [In formula (I), １ R represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, or a substituted or unsubstituted C3-6 cycloalkyl group, ２ R represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylcarbonyloxy group, a substituted or unsubstituted C1-6 alkoxycarbonyloxy group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5-6 membered heterocyclyl group, a substituted or unsubstituted phenyloxy group, a substituted or unsubstituted naphthyloxy group, a substituted or unsubstituted 5-6 membered heterocyclyloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a nitro group, a cyano group, or a halogeno group, １ A represents a substituted or unsubstituted divalent hydrocarbon group or a substituted or unsubstituted heteroatom-containing divalent organic group, ３ Q represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5-6 membered heterocyclyl group, or a substituted or unsubstituted 9-10 membered heterocyclyl group, ４ R represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a halogeno group, ５ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a formyl group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group; B represents a substituted or unsubstituted phenylene group, a substituted or unsubstituted 5-6 membered heterocyclylene group, a group represented by the formula: ＊１ -CO-NR ａ - ＊２ a group represented by the formula: ＊１ -NR ａ - ＊２ an oxygen atom, a sulfur atom, or a single bond; *1 represents a bond to the carbon marked with * in formula (I); *2 represents a bond to Q ２ in formula (I); R ａ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a formyl group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group; Q ２ represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5-6 membered heterocyclyl group, or a substituted or unsubstituted 9-10 membered heterocyclyl group.] 2. In the formula (I), R １ is a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C3-6 cycloalkyl group, R ２ is a hydrogen atom, or a substituted or unsubstituted C1-6 alkyl group, A is a substituted or unsubstituted divalent hydrocarbon group, R ３ and R ４ are hydrogen atoms, R ５ is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C2-6 alkenyl group, B is a substituted or unsubstituted phenylene group, a substituted or unsubstituted 5-6 membered heterocyclylene group, a group represented by the formula: ＊１ -CO-NH- ＊２ a group represented by the formula: ＊１ -NH- ＊２ a group represented by the formula, an oxygen atom, or a single bond, when B is a substituted or unsubstituted phenylene group, Q ２ is a substituted or unsubstituted phenyl group or a substituted or unsubstituted 5-6 membered heterocyclyl group, when B is a single bond, Q ２ is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group, when B is a substituted or unsubstituted 5-6 membered heterocyclylene group, Q ２ is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group, when B is a group represented by the formula: ＊１ -CO-NH ａ - ＊２ when it is a group represented by the formula, Q ２ is a substituted or unsubstituted phenyl group, when B is a group represented by the formula: ＊１ -NH- ＊２ when it is a group represented by the formula, Q ２ is a substituted or unsubstituted C1-6 alkyl group, when B is an oxygen atom, Q ２ is a substituted or unsubstituted C1-6 alkyl group, the compound or a salt thereof according to claim 1.

3. An agricultural and horticultural fungicide containing at least one selected from the group consisting of the compound according to claim 1 or 2 and a salt thereof as an active ingredient.

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