Pyrazole compounds and fungicides for agriculture and horticulture

Abstract

To provide a pyrazole compound having excellent bactericidal activity against pathogenic bacteria that affect agricultural and horticultural plants, being excellent in safety, and being industrially advantageously synthesized, and a fungicide for agricultural and horticultural use containing the same as an active ingredient. 【Solution means】A compound represented by formula (I) or a salt thereof. TIFF2026067600000010.tif44170 (Q 1 、Q 2 ; a substituted or unsubstituted phenyl group, etc., Z; an oxygen atom or a sulfur atom, R 1 ; a substituted or unsubstituted C1-6 alkyl group, etc., R 2 、R 3 、R 4 、R 5 ; a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, etc.)

Description

[Technical Field]

[0001] This invention relates to pyrazole compounds and fungicides for agricultural and horticultural use. More specifically, this invention relates to pyrazole compounds that have excellent fungicidal activity against pathogenic bacteria affecting agricultural and horticultural plants, are highly safe, and can be synthesized industrially advantageously, as well as fungicides for agricultural and horticultural use containing the same as an active ingredient. [Background technology]

[0002] Various compounds with fungicidal activity against pathogens affecting agricultural and horticultural plants have been proposed. For such compounds to be used as fungicides in agriculture and horticulture, they must not only be sufficiently effective, but also resistant to pesticide development, not cause phytotoxicity to plants or soil contamination, and have low toxicity to livestock and fish.

[0003] Incidentally, Patent Document 1 discloses compounds such as compound number F-0230.

[0004] [ka] [Prior art documents] [Patent Documents]

[0005] [Patent Document 1] International Publication No. 2024 / 162284 [Overview of the Initiative] [Problems that the invention aims to solve]

[0006] The object of the present invention is to provide a pyrazole compound that has excellent fungicidal activity against pathogenic fungi affecting agricultural and horticultural plants, is highly safe, and can be synthesized industrially advantageously, as well as an agricultural and horticultural fungicide containing the same as an active ingredient. [Means for solving the problem]

[0007] As a result of diligent research to solve the above problems, we have completed the present invention, which encompasses the following forms. (1) A compound represented by formula (I) or a salt thereof.

[0008] [ka]

[0009] [In the above formula (I), Q 1 This 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. Q 2 This 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. Z represents an oxygen atom or a sulfur atom. R 1 This represents a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C3-6 cycloalkyl group. R 2 This 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. R 3 This includes 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, formula: R a A base represented by -CO-, formula: R a The base represented by -CS-, formula: R aA group represented by -CO-CO-, R a A group represented by -SO2-, 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 member heterocyclyl group, or a cyano group, R a each independently represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C3-6 cycloalkoxy group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted amino 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 3-6 member heterocyclyl group, a substituted or unsubstituted phenoxy group, a substituted or unsubstituted naphthyloxy group, or a substituted or unsubstituted 3-6 member heterocyclyloxy group, R 4 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 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 member heterocyclyl 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 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 member heterocyclyl group, or a halogeno group. ]] (2) R 3 is a group represented by the formula: R a1 -CO-, and R a1 represents a substituted or unsubstituted C1-6 alkoxy group, or a substituted or unsubstituted C3-6 cycloalkoxy group, the compound according to (1) or a salt thereof.

[0010] (3) A fungicide for agricultural and horticultural use, comprising at least one selected from the group consisting of the compounds described in (1) or (2) above and their salts, as an active ingredient. [Effects of the Invention]

[0011] The pyrazole compounds of the present invention have excellent fungicidal activity against pathogenic fungi that affect agricultural and horticultural plants, are highly safe, and can be synthesized industrially advantageously. The fungicides of the present invention can effectively control diseases of agricultural and horticultural plants. [Modes for carrying out the invention]

[0012] The pyrazole compound of the present invention is a compound represented by formula (I) (hereinafter sometimes referred to as compound (I)) or a salt of compound (I).

[0013] [ka]

[0014] In this invention, the term "unsubstituted" means that only the core group is present. When the term "substituted" is not used and only the name of the core group is given, it means "unsubstituted" unless otherwise specified. On the other hand, the term "substituted" means that one of the hydrogen atoms of the parent group is replaced by a group (substituent) that has the same or a different structure as the parent group. Therefore, a "substituent" is another group bonded to the parent group. There may be one substituent or two or more substituents. The two or more substituents may be the same or different. Terms such as "C1-6" indicate that the parent group has 1 to 6 carbon atoms. This number of carbon atoms does not include the number of carbon atoms in substituents. For example, a butyl group with an ethoxy group as a substituent is classified as a C2 alkoxy C4 alkyl group. The "substituents" are chemically acceptable and not particularly limited insofar as they have the effects of the present invention.

[0015] The following are examples of groups that can act as "substituents". C1-6 alkyl groups such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, and n-hexyl group; C2-6 alkenyl groups such as vinyl group, 1-propenyl group, 2-propenyl group (allyl group), 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, and 2-methyl-2-propenyl group; C2-6 alkynyl groups such as ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, and 1-methyl-2-propynyl group;

[0016] 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-C6 alkyl groups such as benzyl and phenethyl groups; 3-6 member heterocyclyl group; 3-6 member heterocyclyl C1-6 alkyl group;

[0017] Hydroxyl group; 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 groups, allyloxy groups, propenyloxy groups, and butenyloxy groups; C2-6 alkynyloxy groups such as ethynyloxy groups and propargyloxy groups; Phenoxy group, naphthoxy group; Phenyl C1-6 alkoxy groups such as benzyloxy and phenethyloxy groups; 5-6 member heteroaryloxy groups such as thiazolyloxy and pyridyloxy groups; 5-6 member heteroaryl C1-6 alkyloxy groups such as thiazolylmethyloxy group and pyridylmethyloxy group;

[0018] Formyl group; C1-6 alkylcarbonyl groups such as acetyl groups and propionyl groups; Formyloxy group; C1-6 alkylcarbonyloxy groups such as acetyloxy groups and propionyloxy groups; Benzoyl group; C1-6 alkoxycarbonyl groups such as methoxycarbonyl groups, ethoxycarbonyl groups, n-propoxycarbonyl groups, i-propoxycarbonyl groups, n-butoxycarbonyl groups, and t-butoxycarbonyl groups; C1-6 alkoxycarbonyloxy groups such as methoxycarbonyloxy groups, ethoxycarbonyloxy groups, n-propoxycarbonyloxy groups, i-propoxycarbonyloxy groups, n-butoxycarbonyloxy groups, and t-butoxycarbonyloxy groups; Carboxyl group;

[0019] Halogeno groups such as fluoro groups, chloro groups, bromo groups, and iod groups; C1-6 haloalkyl groups such as chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, 1-fluoro-n-butyl, and perfluoro-n-pentyl groups; C2-6 haloalkenyl groups such as 2-chloro-1-propenyl group and 2-fluoro-1-butenyl group; C2-6 haloalkynyl groups such as 4,4-dichloro-1-butynyl, 4-fluoro-1-pentynyl, and 5-bromo-2-pentynyl; C1-6 haloalkoxy groups such as trifluoromethoxy, 2-chloro-n-propoxy, and 2,3-dichlorobutoxy; C2-6 haloalkenyloxy groups such as 2-chloropropenyloxy groups and 3-bromobutenyloxy groups; C1-6 haloalkylcarbonyl groups such as chloroacetyl, trifluoroacetyl, and trichloroacetyl groups;

[0020] amino group; C1-6 alkyl-substituted amino groups such as methylamino groups, dimethylamino groups, and diethylamino groups; Anilino group, naphthylamino group; Phenyl C1-C6 alkylamino groups such as benzylamino groups and phenethylamino groups; Formylamino group; C1-6 alkylcarbonylamino groups such as acetylamino groups, propanoylamino groups, butyrylamino groups, and i-propylcarbonylamino groups; C1-6 alkoxycarbonylamino groups such as methoxycarbonylamino groups, ethoxycarbonylamino groups, n-propoxycarbonylamino groups, and i-propoxycarbonylamino groups; Unsubstituted or substituted aminocarbonyl groups such as aminocarbonyl groups, dimethylaminocarbonyl groups, phenylaminocarbonyl groups, and N-phenyl-N-methylaminocarbonyl groups; Imino C1-6 alkyl groups such as iminomethyl group, (1-imino)ethyl group, and (1-imino)-n-propyl group; Substituted or unsubstituted N-hydroxyimino C1-6 alkyl groups such as N-hydroxyiminomethyl group, (1-(N-hydroxy)-imino)ethyl group, (1-(N-hydroxy)-imino)propyl group, N-methoxyiminomethyl group, and (1-(N-methoxy)-imino)ethyl group; aminocarbonyloxy group; C1-6 alkyl-substituted aminocarbonyloxy groups such as ethylaminocarbonyloxy groups and dimethylaminocarbonyloxy groups;

[0021] Mercapto group; C1-6 alkylthio groups such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, and t-butylthio group; C1-6 haloalkylthio groups such as trifluoromethylthio group and 2,2,2-trifluoroethylthio group; Phenylthio group, naphthylthio group; 5-6 member heteroarylthio groups such as thiazolylthio groups and pyridylthio groups;

[0022] C1-6 alkyl sulfinyl groups such as methyl sulfinyl group, ethyl sulfinyl group, and t-butyl sulfinyl group; C1-6 haloalkylsulfinyl groups such as trifluoromethylsulfinyl group and 2,2,2-trifluoroethylsulfinyl group; Phenyl sulfinyl group; 5-6 member heteroaryl sulfinyl groups such as thiazolyl sulfinyl groups and pyridyl sulfinyl groups;

[0023] C1-6 alkylsulfonyl groups such as methylsulfonyl groups, ethylsulfonyl groups, and t-butylsulfonyl groups; C1-6 haloalkylsulfonyl groups such as trifluoromethylsulfonyl group and 2,2,2-trifluoroethylsulfonyl group; Phenylsulfonyl group; 5-6 member heteroarylsulfonyl groups such as thiazolylsulfonyl groups and pyridylsulfonyl groups; C1-6 alkyl sulfonyl groups such as methyl sulfonyloxy groups, ethyl sulfonyloxy groups, and t-butyl sulfonyloxy groups; C1-6 haloalkylsulfonyloxy groups such as trifluoromethylsulfonyloxy groups and 2,2,2-trifluoroethylsulfonyloxy groups;

[0024] TriC1-6 alkyl-substituted silyl groups such as trimethylsilyl group, triethylsilyl group, and t-butyldimethylsilyl group; Triphenylsilyl group; Cyano group; nitro group.

[0025] Furthermore, in these "substituents," any hydrogen atom in the substituent may be substituted with a group of a different structure. Examples of such "substituents" include C1-6 alkyl groups, C1-6 haloalkyl groups, C1-6 alkoxy groups, C1-6 haloalkoxy groups, halogeno groups, cyano groups, and nitro groups.

[0026] Furthermore, the above-mentioned "3-6 membered heterocyclyl group" refers to a group that contains 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms as constituent atoms of the ring. The heterocyclyl group may be monocyclic or polycyclic. In a polycyclic heterocyclyl group, at least one ring may be heterocyclic, and the remaining rings may be saturated alicyclic, unsaturated alicyclic, or aromatic rings. Examples of "3-6 membered heterocyclyl groups" include 3-6 membered saturated heterocyclyl groups, 5-6 membered heteroaryl groups, and 5-6 membered partially unsaturated heterocyclyl groups.

[0027] Examples of "3-6 member saturated heterocyclyl groups" include azilidinyl group, epoxy group, azetidinyl group, oxetanyl group, pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, and dioxanyl group.

[0028] Examples of "5-membered heteroaryl groups" include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups. Examples of "six-membered heteroaryl groups" include pyridyl groups, pyrazinyl groups, pyrimidinyl groups, pyridadinyl groups, and triazinyl groups. Examples of "5-6 membered partially unsaturated heterocyclyl groups" include 5-membered partially unsaturated heterocyclyl groups such as pyrrolinyl group, dihydrofuranyl group, dihydrothiophenyl group, imidazolinyl group, pyrazolinyl group, oxazolinyl group, isoxazolinyl group, thiazolinyl group, and isothiazolinyl group; and 6-membered partially unsaturated heterocyclyl groups such as dihydropyranyl group.

[0029] Q in equation (I) 1 This 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. Among these, Q 1 It is preferable that it is a substituted phenyl group.

[0030] Q in equation (I) 2 This 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. Among these, Q 2 It is preferable that it is a substituted phenyl group.

[0031] A heterocyclyl group contains at least one heteroatom selected from the group consisting of nitrogen, oxygen, and sulfur atoms as a constituent atom of the ring. A heterocyclyl group may be monocyclic or polycyclic. In a polycyclic heterocyclyl group, at least one ring may be heterocyclic, and the remaining rings may be saturated alicyclic, unsaturated alicyclic, or aromatic rings.

[0032] Q 1 or Q 2 Examples of "5-6 member heterocyclyl groups" in this context include 5-6 member saturated heterocyclyl groups, 5-6 member heteroaryl groups, and 5-6 member partially unsaturated heterocyclyl groups.

[0033] Q 1 or Q 2Examples of "5-6 member saturated heterocyclyl groups" in this context include pyrrolidinyl group, tetrahydrofuranyl group, tetrahydropyranyl group, thiazolidinyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, and dioxanyl group.

[0034] Q 1 or Q 2 Examples of "5-membered heteroaryl groups" in this context include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups.

[0035] Q 1 or Q 2 Examples of "six-membered heteroaryl groups" in this context include pyridyl groups, pyrazinyl groups, pyrimidinyl groups, pyridadinyl groups, and triazinyl groups.

[0036] Q 1 or Q 2 Examples of "5-6 membered partially unsaturated heterocyclyl groups" in this context include 5-membered partially unsaturated heterocyclyl groups such as pyrrolinyl group, dihydrofuranyl group, dihydrothiophenyl group, imidazolinyl group, pyrazolinyl group, oxazolinyl group, isoxazolinyl group, thiazolinyl group, and isothiazolinyl group; and 6-membered partially unsaturated heterocyclyl groups such as dihydropyranyl group.

[0037] Q 1 or Q 2 Examples of "9-membered heterocyclyl groups" in this context include indolyl groups, isoindolyl groups, benzofuranyl groups, benzothienyl groups, indazolyl groups, benzimidazolyl groups, benzoxazolyl groups, benzoisoxaozolyl groups, benzothiazolyl groups, benzoisothiazolyl groups, and benzodioxolanyl groups.

[0038] Q 1 or Q 2Examples of "10-membered heterocyclyl groups" in this context include quinolinyl groups, isoquinolinyl groups, synnolinyl groups, phthalazinyl groups, quinazolinyl groups, and quinoxalinyl groups.

[0039] Q 1 or Q 2 Substituents on the "5-6 member heterocyclyl group", "phenyl group", "naphthyl group", or "9-10 member heterocyclyl group" include: halogeno group, C1-6 alkyl group, C1-6 haloalkyl group, hydroxyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, C1-6 alkoxy group substituted with a C1-6 alkoxy group, C1-6 alkylcarbonyl group, C1-6 alkylthio group, C1-6 alkylsulfonyl group, C3-6 cycloalkyl group, phenyl group, phenyloxy group, 5 member heteroaryl group, 6 member heteroaryl group, cyano group, nitro group, triC1-6 alkylsilyl group; amino group substituted with a C1-6 alkyl group or C1-6 alkylcarbonyl group; carboxamide group substituted with a C1-6 alkyl group; Phenyl groups substituted with one or more substituents of any C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups; 5-membered heteroaryl groups substituted with one or more substituents of any C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups; or 6-membered heteroaryl groups substituted with one or more substituents of any C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups are preferred. Among these, Q 1 or Q 2 The substituents on the "5-6 membered heterocyclyl group," "phenyl group," "naphthyl group," or "9-10 membered heterocyclyl group" are preferably a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, or a C1-6 alkoxy group.

[0040] Q 1 or Q 2Two substituents on a "5-6 member heterocyclyl group," "phenyl group," "naphthyl group," or "9-10 member heterocyclyl group" may combine to form a divalent organic group, or two substituents on a phenyl group substituted with two substituents, a 5-membered heteroaryl group substituted with two substituents, or a 6-membered heteroaryl group substituted with two substituents may combine to form a divalent organic group. Examples of divalent organic groups include C3-6 alkylene groups such as trimethylene groups and tetramethylene groups; and C1-3 alkyleneoxy groups such as methylenedioxy groups and dimethyledioxy groups.

[0041] In formula (I), Z represents an oxygen atom or a sulfur atom, preferably an oxygen atom.

[0042] R in equation (I) 1 This represents a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C3-6 cycloalkyl group. Among these, R 1 It is preferable that the alkyl group is a C1-6 alkyl group.

[0043] R 1 The "C1-6 alkyl group" in this can be a straight chain or a branched chain. 1 Examples of "C1-6 alkyl groups" in this context include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s-butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, and i-hexyl group.

[0044] R 1 Examples of "C3-6 cycloalkyl groups" in this context include cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, and cyclohexyl groups.

[0045] R 1Substituents on the "C1-6 alkyl group" include: halogen groups such as fluoro, chloro, bromo, and iod groups; C1-6 alkoxy groups such as hydroxyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy groups; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, and trifluoromethoxy groups; C3-6 cycloalkyl groups; phenyl groups; 5-membered heteroaryl groups; 6-membered heteroaryl groups; and cyano groups; as well as phenyl groups substituted with one or more substituents of any C1-6 alkyl groups, C1-6 alkoxy groups, halogen groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups; A five-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 six-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 is preferred, and one or more substituents of a halogeno group, a C1-6 alkoxy group, or a C3-6 cycloalkyl group are more preferred.

[0046] R 1Preferably, the substituents on the "C3-6 cycloalkyl group" in this 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, or 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, with a halogeno group being more preferred.

[0047] R in equation (I) 2 This 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. Among these, R 2 It is preferable that it be a hydrogen atom.

[0048] R 2 In this context, "substituted or unsubstituted C1-6 alkyl groups" and "substituted or unsubstituted C3-6 cycloalkyl groups" are defined as R 1 The same examples given in the previous section can be cited.

[0049] R 2Examples of "C2-6 alkenyl groups" in this context 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.

[0050] R 2 Examples of "C2-6 alkynyl groups" in this context 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, and 1,1-dimethyl-2-butynyl group.

[0051] R 2 Examples of "C1-6 alkylcarbonyl groups" in this context include acetyl group, propionyl group, n-propylcarbonyl group, i-propylcarbonyl group, n-butylcarbonyl group, and t-butylcarbonyl group.

[0052] R 2 Examples of "C1-6 alkoxycarbonyl groups" in this context include methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, and t-butoxycarbonyl group.

[0053] R 2Substituents on the "C2-6 alkenyl group", "C2-6 alkynyl group", "C1-6 alkylcarbonyl group", or "C1-6 alkoxycarbonyl group" include: halogen groups such as fluoro, chloro, bromo, and iod groups; C1-6 alkoxy groups such as hydroxyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy groups; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, and trifluoromethoxy groups; C3-6 cycloalkyl groups; phenyl groups; 5-membered heteroaryl groups; 6-membered heteroaryl groups; and cyano groups; or phenyl groups substituted with one or more substituents of a C1-6 alkyl group, C1-6 alkoxy group, halogen group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; A five-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 six-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 is preferred, and one or more substituents of a halogeno group, a C1-6 alkoxy group, or a C3-6 cycloalkyl group are more preferred.

[0054] R 2 In this context, a "5-6 membered heterocyclyl group" is a group that contains one, two, three, or four heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms as constituent atoms of the ring. When there are two or more heteroatoms, they may be the same or different. As for "5-6 member heterocyclyl groups", Q 1 or Q 2Examples of the groups listed under "5-6 membered heterocyclyl groups" include pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, tetrahydro-2H-pyranyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, dioxanyl group; pyrrolidyl group, dihydrofuranyl group, imidazolinyl group, pyrazolinyl group, oxazolinyl group, isoxazolinyl group; dihydropyranyl group; pyrrolyl group, f Examples include lyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group; pyridyl group, pyrazinyl group, pyrimidinyl group, pyridadinyl group, triazinyl group, etc. Preferably, pyrazolinyl group, thiazolyl group, or pyridyl group, and more preferably thiazolyl group or pyridyl group.

[0055] R 2 Preferably, substituents on the "phenyl group," "naphthyl group," or "5-6 member heterocyclyl group" in the above 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-member heteroaryl group, a 6-member heteroaryl group, or 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-member 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-member 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, with a halogeno group being more preferred.

[0056] R in equation (I) 3 This includes 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, formula: Ra A base represented by -CO-, formula: R a The base represented by -CS-, formula: R a A group represented by -CO-CO-, R a The group is represented by -SO2-, 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, or a cyano group. R a Each of these independently represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C3-6 cycloalkoxy group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted amino 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 3-6 membered heterocyclyl group, a substituted or unsubstituted phenoxy group, a substituted or unsubstituted naphthyloxy group, or a substituted or unsubstituted 3-6 membered heterocyclyloxy group.

[0057] Among these, R 3 is, formula:R a It is preferable that the group is represented by -CO-. Also, R a The group is preferably a substituted or unsubstituted C1-6 alkoxy group, or a substituted or unsubstituted C3-6 cycloalkoxy group, and more preferably a C1-6 alkoxy group.

[0058] R 3 In this context, "substituted or unsubstituted C1-6 alkyl groups", "substituted or unsubstituted C2-6 alkenyl groups", "substituted or unsubstituted C2-6 alkynyl groups", "substituted or unsubstituted C3-6 cycloalkyl groups", "substituted or unsubstituted phenyl groups", "substituted or unsubstituted naphthyl groups", and "substituted or unsubstituted 5-6 membered heterocyclyl groups" are as follows: 1 and R 2 The same examples given in the previous section can be cited.

[0059] Ra In this context, "substituted or unsubstituted C1-6 alkyl groups", "substituted or unsubstituted C3-6 cycloalkyl groups", "substituted or unsubstituted phenyl groups", and "substituted or unsubstituted naphthyl groups" are R 1 and R 2 The same examples given in the previous section can be cited.

[0060] R a Examples of "C1-6 alkoxy groups" in this context include methoxy groups, ethoxy groups, n-propoxy groups, i-propoxy groups, n-butoxy groups, s-butoxy groups, i-butoxy groups, and t-butoxy groups.

[0061] R a Examples of "C1-6 alkylthio groups" in this context include methylthio group, ethylthio group, n-propylthio group, n-butylthio group, n-pentylthio group, n-hexylthio group, i-propylthio group, and i-butylthio group.

[0062] R aSubstituents on the "C1-6 alkoxy group" or "C1-6 alkylthio group" in the above include: halogen groups such as fluoro, chloro, bromo, and iod groups; C1-6 alkoxy groups such as hydroxyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy groups; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, and trifluoromethoxy groups; C3-6 cycloalkyl groups; phenyl groups; 5-membered heteroaryl groups; 6-membered heteroaryl groups; and cyano groups; or phenyl groups substituted with one or more substituents of a C1-6 alkyl group, C1-6 alkoxy group, halogen group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; A five-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 six-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 is preferred, and one or more substituents of a halogeno group, a C1-6 alkoxy group, or a C3-6 cycloalkyl group are more preferred.

[0063] R a Examples of "C3-6 cycloalkoxy groups" in this context include cyclopropyloxy group, cyclobutyloxy group, and cyclopentyloxy group.

[0064] R aThe "3-6 member heterocyclyl group" in this context includes azilidinyl group, epoxy group, azetidinyl group, oxetanyl group, pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, dioxanyl group, pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothia Examples include zolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridadinyl group, triazinyl group, pyrrolinyl group, dihydrofuranyl group, dihydrothiophenyl group, imidazolinyl group, pyrazolinyl group, oxazolinyl group, isoxazolinyl group, thiazolinyl group, isothiazolinyl group, and dihydropyranyl group.

[0065] R a Among the "3- to 6-membered heterocyclyloxy groups" in this context, examples of "3- to 4-membered heterocyclyloxy groups" include aziridinyloxy groups, epoxyoxy groups, 3-azetidinyloxy groups, and 3-oxetanyloxy groups.

[0066] R a Among the "3-6 member heterocyclyloxy groups" in this context, examples of "5-6 member heterocyclyloxy groups" include pyrrolidinyloxy group, tetrahydrofuranyloxy group, thiazolidinyloxy group, tetrahydro-2H-pyranyloxy group, piperidyloxy group, piperazinyloxy group, morpholinyloxy group, dioxolanyloxy group, dioxanyloxy group; pyrrolidinyloxy group, dihydrofuranyloxy group, imidazolinyloxy group, pyrazolinyloxy group, oxazolinyloxy group, isoxazolinyloxy group; and dihydropyranyloxy group.

[0067] R aSubstituents on the "C3-6 cycloalkoxy group", "3-6 member heterocyclyl group", "phenoxy group", "naphthyloxy group", and "3-6 member heterocyclyloxy group" include: halogeno group, C1-6 alkyl group, C1-6 haloalkyl group, hydroxyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, phenyl group, 5-membered heteroaryl group, 6-membered heteroaryl group, cyano group; phenyl group substituted with one or more substituents of any C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; 5-membered heteroaryl group substituted with one or more substituents of any C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or 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 is preferred.

[0068] R a In this context, an "amino group" is a group represented by NH2. A "substituted amino group" is a group in which a hydrogen atom in the NH2 group has been replaced with something else.

[0069] R aPreferably, the substituents on the "amino group" in are a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxycarbonyl 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, more preferably a C1-6 alkyl group or a C1-6 alkoxycarbonyl group, and even more preferably a C1-6 alkyl group.

[0070] R in equation (I) 4 This 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 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, or a halogeno group. Among these, R 4 It is preferably a hydrogen atom or a C1-6 alkyl group, and more preferably a hydrogen atom.

[0071] R in equation (I) 5 This 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 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, or a halogeno group. Among these, R 4is preferably a hydrogen atom or a C1-6 alkyl group, more preferably a hydrogen atom.

[0072] R 4 and R 5 Examples of the "substituted or unsubstituted C1-6 alkyl group", "substituted or unsubstituted C2-6 alkenyl group", "substituted or unsubstituted C2-6 alkynyl group", "substituted or unsubstituted C3-6 cycloalkyl group", "substituted or unsubstituted phenyl group", "substituted or unsubstituted naphthyl group", and "substituted or unsubstituted 5-6 member heterocyclyl group" for R 1 and R 2 can be the same as those exemplified for R

[0073] R 4 and R 5 Examples of the "halogeno group" for R

[0074] R 4 and R 5 on the same carbon atom may together form a divalent organic group. Here, examples of the divalent organic group include C2-5 alkylene groups such as dimethylene group, trimethylene group, and tetramethylene group.

[0075] 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.

[0076] The production method of 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 known production method described in Examples and the like. Also, a salt of compound (I) can be obtained from compound (I) by a known method.

[0077] Production method of compound (I) Production method 1 The compound of formula (I-1) can be produced by a method including a reaction step of a compound of formula (im-1) and a compound of formula (im-2) as shown in Scheme 1.

[0078]

Chemical formula

[0079] Here, the compound of formula (I-1) is a compound among compounds (I) in which R <​​​​​​​​​​​​​​​​​​​​​​​​​​Examples of condensation reagents include, but are not limited to, halogenating reagents (e.g., phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus trichloride oxide, oxalyl chloride, or thionyl chloride), dehydrating agents (e.g., ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate, or methanesulfonyl chloride), and carbonyl diimidazole. The reaction temperature is set as appropriate, but for example, it is around 0°C to 40°C. The reaction time is set as appropriate, but for example, it is around 1 hour to 24 hours.

[0081] In addition, the compound of formula (I-1) can also be produced by reacting the compound of formula (im-1), in which U is a hydroxyl group, with an organic base in the presence of a condensation reagent. 1-hydroxybenzotriazole can also be used in combination. The organic base is not particularly limited, but tertiary amines such as triethylamine and diisopropylethylamine are preferably used. The condensation reagent is not particularly limited, but examples include carbodiimides such as N,N'-dicyclohexylcarbodiimide (DCC), carbodiimide salts such as 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 1-hydroxy-7-azobenzotriazole (HOAt), O-(7-azabenzotriazole-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU), and propylphosphonic anhydride. Carbodiimide salts (1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride) and HATU are preferred. The reaction temperature is set as appropriate, but for example, it is around 0°C to 40°C. The reaction time is set as appropriate, but for example, it is around 1 hour to 24 hours.

[0082] The compound of formula (I-1) can also be produced by reacting the compound of formula (im-1), in which U is a halogen atom, with the compound of formula (im-2) in the presence of an acid scavenger, using a well-known method. Examples of acid scavengers include general inorganic and organic bases, with alkali metal carbonates, alkaline earth metal acetates, tertiary amines, or aromatic amines being preferred.

[0083] The compound of formula (im-1) may be commercially available or may be prepared according to a method described in the literature (e.g., WO2024 / 162284 A1). The compound of formula (im-2) may be commercially available. It can also be produced by one or more of the methods described herein (see production methods 2 and 3).

[0084] Manufacturing method 2 The compound of formula (im-2a) can be produced by a method that includes a reaction step between the compound of formula (im-3) and the compound of formula (im-4), as shown in Scheme 2, and a reaction step between the compound of formula (im-5) obtained by that reaction and hydrazines.

[0085] [ka]

[0086] Here, the compound of formula (im-2a) is one of the compounds of formula (im-2) with R 2 It is a compound in which the atom is a hydrogen atom. The compound of formula (im-3) is R 3a This is the same as the one defined for the compound of formula (im-2). The compound of formula (im-4) is U 1 This is a compound in which is a hydroxyl group or a halogeno group, and the other symbols are the same as those defined in the compound of formula (im-2). The compound represented by formula (im-5) is a compound in which the symbols in the formula are the same as those defined for the compound represented by formula (im-2).

[0087] The compound of formula (im-5) is U 1The compound of formula (im-4), in which the group is a hydroxyl group, can be produced by reacting it with the compound of formula (im-3) in the presence of a dialkyl azodicarboxylate and triphenylphosphine. This is known as the Mitsunobu reaction. Examples of dialkyl azodicarboxylates include, but are not limited to, diethyl azodicarboxylate and diisopropyl azodicarboxylate.

[0088] The compound of formula (im-5) is U 1 A compound of formula (im-4), in which is a halogen atom, can be produced by reacting it with a compound of formula (im-5) in the presence of an acid scavenger using a well-known method. The reaction time is set as appropriate, but is typically between 1 and 24 hours. The reaction temperature is also set as appropriate, but is typically between 0°C and 100°C. Examples of acid scavengers include common inorganic and organic bases. Preferably, alkali metal carbonates such as potassium carbonate, alkaline earth metal acetates, tertiary amines, or aromatic amines are used, with alkali metal carbonates being more preferred.

[0089] The compound of formula (im-2a) can be produced by reacting the compound of formula (im-5) with hydrazines. The hydrazines are not particularly limited, but for example, hydrazine monohydrate and methylhydrazine can be used, with hydrazine monohydrate being preferred. The compound of formula (im-3) may be a commercially available product, or the compound of formula:NH2-NH-R 3a Compound represented by (R 3a This is the same as defined in the compound of formula (im-2). It may also be prepared by reacting with phthalic anhydride. The compound of formula (im-4) may be commercially available or may be manufactured by a well-known method.

[0090] Manufacturing method 3 The compound of formula (im-2b) can be produced by a method that includes a reaction step between the compound of formula (im-2a) and the compound of formula (im-6), as shown in Scheme 3.

[0091] [ka]

[0092] Here, the compound of formula (im-2b) is one of the compounds of formula (im-2), R 2 The group other than the hydrogen atom (hereinafter, R 2a It is a compound that is sometimes written as such. The compound of formula (im-6) is G 1 R is a halogen group, 2a This is the same compound as defined in formula (im-2b).

[0093] The compound of formula (im-2b) can be produced by reacting the compound of formula (im-2a) with the compound of formula (im-6). The reaction is preferably carried out in the presence of an inorganic base. The compound of formula (im-6) may be commercially available or may be manufactured by a well-known method.

[0094] The fungicide for agricultural and horticultural use of the present invention contains at least one selected from the group consisting of compound (I) and salts of compound (I) as an active ingredient (hereinafter sometimes referred to as active ingredient (I)). The amount of active ingredient (I) contained in the fungicide for agricultural and horticultural use of the present invention is not particularly limited as long as it exhibits a fungicidal effect.

[0095] The fungicide for agricultural and horticultural use of the present invention can be used to control plant diseases caused by a wide range of filamentous fungi, such as those belonging to the algae (Oomycetes), ascomycetes, deuteromycetes, basidiomycetes, and zygomycetes.

[0096] Examples of plant diseases (pathogens) that are subject to control 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 ultimum) etc. Peanuts: Brown spot disease (Mycosphaerella arachidis), stain spot disease (Ascochyta sp.), rust disease (Puccinia arachidis), damping-off disease (Pythium debaryanum), rust spot disease (Alternaria alternata), white mold disease (Sclerotium rolfs II), black rot (Mycosphaerella berkeleyi), black root rot (Calonectria ilicicola), etc. Cucumbers: Powdery mildew (Sphaerotheca fuliginea), downy mildew (Pseudoperonospora cubensis), vine blight (Mycosphaerella melonis), vine wilt (Fusarium oxysporum), sclerotinia sclerotiorum, gray mold (Botrytis cinerea), anthracnose (Colletotrichum orbiculare), black spot (Cladosporium cucumerinum), brown spot (Corynespora cassIIcola), seedling blight (Pythium debaryanum, Rhizoctonia solani Kuhn), Phomopsis root rot (Phomopsis sp.), bacterial leaf spot (Pseudomonas syringae pv. Lachrymans), etc. Tomatoes: Botrytis cinerea, Cladosporium fulvum, Phytophthora infestans, Verticillium albo-atrum, Verticillium dahliae, Oidium neolycopersici, Alternaria solani, 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 nattrass II), sclerotinia sclerotiorum, verticillium wilt (Verticillium dahliae), brown spot disease (Phomopsis vexans), etc. Chili peppers: Late blight (Phytophthora capsici), gray mold (Botrytis cinerea), sclerotinia rot (Sclerotinia sclerotiorum), anthracnose (Colletotrichum aenigma, Colletotrichum capsici, Colletotrichum fructicola, Colletotrichum jiangxiense), powdery mildew (Leveillula taurica), etc. Strawberries: Gray mold (Botrytis cinerea), powdery mildew (Sphaerotheca humuli), anthracnose (Colletotrichum acutatum, Colletotrichum fragariae), late blight (Phytophthora cactorum), soft rot (Rhizopus stolonifer), fusarium wilt (Fusarium oxysporum), wilt (Verticillium dahliae), sclerotinia sclerotiorum, etc. Onions: Grey rot (Botrytis allii), Grey mould (Botrytis cinerea), White spot leaf blight (Botrytis squamosa), Downy mildew (Peronospora destructor), White blight (Phytophthora porri), Small sclerotinia disease (Ciborinia allii), Small sclerotinia rot (Botrytis squamosa), Dry rot (Fusarium oxysporum), Red root rot (Pyrenochaeta terrestris), Black rot sclerotinia disease (Sclerotium cepivorum), Rust (Puccinia allii), Southern blight (Sclerotium rolfsii), etc. Leeks: Soft rot (Pectobacterium carotovorum), Downy mildew (Peronospora destructor), Leaf blight (Pleospora allii), Black rot sclerotinia disease (Sclerotium cepivorum), Rust (Puccinia allii), White spot 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 campestris pv. campestris), Black spot bacterial disease (Pseudomonas syringae pv. maculicola, P. s. pv. alisalensis), Downy mildew (Peronospora parasitica), Sclerotinia rot (Sclerotinia sclerotiorum), Black smut (Alternaria brassicicola), Grey mould (Botrytis cinerea), Root rot (Phoma lingam), Pythium rot (Pythium aphanidermatum, Pythium ultimum), White rust (Albugo macrospora), etc. Lettuce: Diseases such as rot (Pseudomonas cichorII, Pseudomonas marginalis), soft rot (Pectobacterium carotovorum), downy mildew (Bremia lactucae), gray mold (Botrytis cinerea), sclerotinia sclerotiorum, big vein disease (Mirafiori lettuce big-vein ophiovirus), root rot (Fusarium oxysporum), bottom blight (Rhizoctonia solani), powdery mildew (Golovinomyces orontII), etc. Green beans: Sclerotinia sclerotiorum, gray mold (Botrytis cinerea), anthracnose (Colletotrichum lindemuthianum), horn blotch (Phaeoisariopsis griseola), etc. Peas: Brown spot disease (Mycosphaerella blight), gray mold (Botrytis cinerea), sclerotinia sclerotiorum, powdery mildew (Erysiphe pisi), etc.

[0097] Apples: Powdery mildew (Podosphaera leucotricha), black spot (Venturia inaequalis), Monilinia mali, black spot (Mycosphaerella pomi), canker (Valsa mali), leaf spot (Alternaria mali), cedar-apple rust (Gymnosporangium yamadae), ring spot (Botryosphaeria berengeriana), anthracnose (Glomerella cingulata, Colletotrichum acutatum), brown spot (Diplocarpon mali), sooty spot (Zygophiala jamaicensis), sooty mold (Gloeodes pomigena), purple root rot (Helicobasidium mompa), white root rot (Rosellinia necatrix), gray mold (Botrytis cinerea), burn (Erwinia) Diseases such as amylovora, silver leaf disease (Chondrostereum purpureum), and crown gall disease (Rhizobium radiobacter, Rhizobium rhizogenes) Japanese apricot (Ume): Black spot disease (Cladosporium carpophilum), gray mold (Botrytis cinerea), gray mold (Monilinia mumecola), sooty mold (Peltaster sp.), fruit rot (Taphrina pruni), brown hole disease (Phloeosporella padi), etc. Persimmons: Powdery mildew (Phyllactinia kakicola), anthracnose (Gloeosporium kaki), horn spot leaf spot (Cercospora kaki), round leaf spot leaf spot (Mycosphaerella nawae), gray mold (Botrytis cinerea), sooty spot (Zygophiala jamaicensis), etc. Peaches: Monilinia fructicola, Monilia fructigena, Cladosporium carpophilum, Phomopsis sp., Xanthomonas campestris pv. pruni, Taphrina deformans, Colletotrichum gloeosporioides, Phloeosporella padi), Kawaratake disease (Coriolus versicolor), etc. Almonds: Gray mold (Monilinia laxa), leaf spot (Stigmina carpophila), black spot (Cladosporium carpophilum), leaf blisters (Polystigma rubrum), leaf spot disease (Alternaria alternata), anthracnose (Colletotrichum gloeospoides), etc. Prunus: Monilinia fructicola, Colletotrichum acutatum, Alternaria sp., Monilinia kusanoi, Mycosphaerella cerasella, Podosphaera tridactyla, etc. Grapes: Gray mold (Botrytis cinerea), powdery mildew (Uncinula necator), late blight (Glomerella cingulata, Colletotrichum acutatum), downy mildew (Plasmopara viticola), black rot (Elsinoe ampelina), brown spot (Pseudocercospora vitis), black rot (Guignardia bidwell II), white rot (Coniella castaneicola), rust (Phakopsora ampelopsidis), white snow disease (pathogen unidentified), crown gall disease (Rhizobium radiobacter, Rhizobium vitis), etc. Pears: Black spot (Venturia nashicola), cedar-apple rust (Gymnosporangium asiaticum), black spot (Alternaria kikuchiana), ring spot (Botryosphaeria berengeriana), powdery mildew (Phyllactinia mali), canker (Phomopsis fukushII), brown spot (Stemphylium vesicarium), anthracnose (Glomerella cingulata), etc. Tea: Ring spot disease (Pestalotiopsis longiseta, P. theae), anthracnose (Colletotrichum theae-sinensis), net blight (Exobasidium reticulatum), red blight (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 (Xanthomonas campestris pv. Citri), powdery mildew (Oidium sp.), late blight (Phytophthora citrophthora), anthracnose (Colletotrichum fioriniae), etc. Kiwifruit: Bacterial flower blight (Pseudomonas marginalis, Pseudomonas syringae, Pseudomonas viridiflava), canker (Pseudomonas syringae), gray mold (Botrytis cinerea), soft rot (Botryosphaeria dothidea, Diaporthe sp., Lasiodiplodia theobromae), sooty mold (Pseudocercospora actinidiae), etc. Olive: Anthracnose (Colletotrichum acutatum, Colletotrichum gloeosporioides), Peacock spot (Spilocaea oleaginea), etc. Oak: Anthracnose (Colletotrichum gloeosporioides), etc.

[0098] 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), Pink snow blight (Monographella nivalis), Eyespot (Pseudocercosporella herpotrichoides), Leaf blotch (Septoria tritici), Glume blotch (Leptosphaeria nodorum), Snow blight (Typhula incarnata), Large sclerotinia snow blight (Myriosclerotinia borealis), Take-all (Gaeumannomyces graminis), Ergot (Claviceps purpurea), Common bunt (Tilletia caries), Loose smut (Ustilago nuda), Blast (Pyricularia grisea), Damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), etc. Barley: Pyrenophora graminea, Pyrenophora teres, Rhynchosporium secalis, Ustilago tritici, U.nuda, Damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.) etc. Rice: Blast disease (Pyricularia oryzae), sheath blight (Rhizoctonia solani), bakanae disease (Gibberella fujikuroi), sesame leaf spot (Cochliobolus miyabeanus), seedling blight (Pythium graminicola), bacterial leaf spot (Xanthomonas oryzae), bacterial seedling blight (Burkholderia plantar II), brown stripe disease (Acidovorax avenae), bacterial grain blight (Burkholderia glumae), leaf blight (Cercospora oryzae), rice blast (Ustilaginoidea virens), brown rice (Alternaria alternata, Curvularia intermedia), black rice (Alternaria padwick II), reddish rice (Epicoccum purpurascens), etc. Tobacco: Sclerotinia sclerotiorum, powdery mildew (Erysiphe cichoracearum), plague (Phytophthora nicotianae), etc. Tulips: Gray mold (Botrytis cinerea), brown spot (Botrytis tulipae), leaf blight (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 wilt (Pythium aphanidermatum, Pythium dissotocum, Pythium helicoides, Pythium oedochilum, Pythium sylvaticum), wilt (Rhizoctonia solani), Fusarium wilt (Fusarium solani), etc. Gerbera: Gray mold (Botrytis cinerea), powdery mildew (Podosphaera xanthII), etc. Lilies: Leaf blight (Botrytis elliptica, Pestalotiopsis sp.), gray mold (Botrytis cinerea), etc. Sunflowers: Downy mildew (Plasmopara halsted II), Sclerotinia sclerotiorum, Gray mold (Botrytis cinerea), etc. Bentgrass: Snow mold (Sclerotinia borealis), Large patch (Rhizoctonia solani), Brown patch (Rhizoctonia solani), Dollar spot (Sclerotinia homoeocarpa), Rice blast (Pyricularia sp.), Red blight (Pythium aphanidermatum), Anthracnose (Colletotrichum graminicola), etc. Orchardgrass: Powdery mildew (Erysiphe graminis), etc. Soybeans: Purple spot disease (Cercospora kikuchII), downy mildew (Peronospora manshurica), stem blight (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. Potatoes: Late blight (Phytophthora infestans), summer blight (Alternaria solani), black spot disease (Thanatephorus cucumeris), Verticillium albo-atrum, V. dahliae, V. nigrescens, black foot disease (Pectobacterium atrosepticum), soft rot (Pectobacterium carotovorum), gray mold (Botrytis cinerea), scab (Streptomyces spp.), sclerotinia sclerotiorum, etc. Japanese yam (Dioscorea japonica): Leaf blotch (Cylindrosporium dioscoreae), anthracnose (Colletotrichum gloeosporioides), blue mold (Penicillium sclerotigenum), etc. Sweet potatoes: Purple root rot (Helicobasidium mompa), vine wilt (Fusarium oxysporum), etc. Taro: Late blight (Phytophthora colocasiae), stem rot (Rhizoctonia solani), etc. Ginger: Rhizome rot (Pythium ultimum, Pythium myriotylum), white spot disease (Phyllosticta zingiberis), etc. Bananas: 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 disease (Hemileia vastatrix), anthracnose (Colletotrichum coffeanum), brown eye disease (Cercospora coffeicola), etc. Sugarcane: Brown rust disease (Puccinia melanocephala), etc. Corn: Gloeocercospora sorghi, Puccinia sorghi, Puccinia polysora, Ustilago maydis, Cochliobolus heterostrophus, Setosphaeria turcica, Damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), etc. Cotton: Seedling blight (Pythium sp.), rust (Phakopsora gossypII), white mold (Mycosphaerella areola), anthracnose (Glomerella gossypII), etc. Hops: susceptible to downy mildew (Pseudoperonospora humuli), powdery mildew (Oidium sp., Podosphaera macularis), gray mold (Botrytis cinerea), etc.

[0099] The fungicide for agricultural and horticultural use of the present invention is preferably used on plants such as grains, vegetables, root vegetables, potatoes, fruit trees, trees such as tea, coffee, and cocoa, pasture grasses, turfgrasses, and cotton.

[0100] The fungicide for agricultural and horticultural use of the present invention can be applied to various parts of plants, such as leaves, stems, stalks, flowers, buds, fruits, seeds, sprouts, roots, tubers, rhizomes, shoots, and cuttings. Furthermore, it can be used to target improved varieties, cultivars, and even mutants, hybrids, and genetically modified organisms (GMOs) of these plants.

[0101] The fungicide for agricultural and horticultural use of the present invention can be used for seed treatment, foliar application, soil application, water surface application, etc., to control various diseases that occur in agricultural and horticultural crops, including flowers, turf, and pasture grass.

[0102] The fungicide for agricultural and horticultural use of the present invention may contain other components besides the active ingredient (I). Examples of other components include known carriers used for formulation. Other components may include conventionally known fungicides, insecticides / acaricides, nematicides, soil pesticides, plant growth regulators, synergists, fertilizers, soil conditioners, animal feed, etc. (hereinafter sometimes referred to as active ingredient (II)). The fungicide for agricultural and horticultural use of the present invention may exhibit a synergistic effect by containing both active ingredient (I) and active ingredient (II).

[0103] Specific examples of fungicides as active ingredient (II) that can be mixed with or used in combination with the fungicide for agricultural and horticultural use of the present invention are shown below. (1) Nucleic acid biosynthesis inhibitors: (a) RNA polymerase I inhibitors: Benalaxil, Benalaxil-M, Flalaxil, Metalaxil, Metalaxil-M, Oxadixyl, Clodilacon, Offrace; (b) Adenosine deaminase inhibitors: Bupirimate, dimethylmol, etylimole; (c) DNA / RNA synthesis inhibitors: Himexazole, octylinone; (d) DNA topoisomerase II inhibitor: oxolinic acid;

[0104] (2) Mitosis inhibitors and cell division inhibitors: (a) β-tubulin polymerization inhibitors: benomyl, carbendazim, chlorfenazole, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, diethofencarb, zoxamide, etaboxam; (b) Cell division inhibitor: Pencyclon; (c) Delocalization inhibitors of spectrin-like proteins: fluopicole, fluopimomid;

[0105] (3) Respiratory inhibitors: (a) Complex I-NADH oxidoreductase inhibitors: diflumetrim, tolfenpyrad; (b) Complex II succinate dehydrogenase inhibitors: benodanil, flutolanil, mepronil, isofetamide, fluopyram, fenflam, flumecyclox, carboxyne, oxycarboxyne, tifluzamide, benzovindiflupir, bixafen, fluxapiroxad, flametopyr, isopyrazam, penflufen, penthiopyrad, sedaxane, boscalid, pidiflumetofen, isoflucipram, pyraziflumid, impilfluxam; (c) Complex III-ubiquinol oxidase Qo inhibitors: Azoxystrobin, chemoxystrobin, cmethoxystrobin, enoxastrobin, fluphenoxystrobin, picoxystrobin, pyraoxystrobin, pyraclostrobin, pyrametostrobin, triclopyricarb, kresoxime-methyl, trifloxystrobin, dimoxystrobin, phenaminestrobin, metminostrobin, orysastrobin, famoxadone, fluoxastrobin, fenamidon, pyribencarb, methyltetraprole, mandestrobin; (d) Complex III-ubiquinol reductase Qi inhibitors: cyazofamide, amisulbrom, fenpicoxamide; (e) Uncoupling agents for oxidative phosphorylation: Binapacril, Meptildinocap, Dinocap, Fluazinam, Felimzon; (f) Oxidative phosphorylation inhibitors (inhibitors of ATP synthase): fentin acetate, fentin chloride, fentin hydroxide; (g) ATP production inhibitor: Silthiofam; (h) Complex III: Qx (unknown) inhibitor of cytochrome bc1 (ubiquinone reductase): ametoctrazine;

[0106] (4) Amino acids and protein synthesis inhibitors: (a) Methionine biosynthesis inhibitors: andprim, cyprodinil, mepanipyrim, pyrimethanil; (b) Protein synthesis inhibitors: blastosidine-S, kasugamycin, kasugamycin hydrochloride, streptomycin, oxytetracycline;

[0107] (5) Signal transduction inhibitors: (a) Signal transduction inhibitors: quinoxifen, proquinazide; (b) MAP / histidine kinase inhibitors in osmotic signaling: fenpiclonil, fludioxonil, clozolinate, iprodione, procymidone, vinclozoline;

[0108] (6) Lipid and cell membrane synthesis inhibitors: (a) Phospholipid biosynthesis and methyltransferase inhibitors: edifenphos, ipropenphos, pyrazophos, isoprothiolane; (b) Lipid peroxidants: biphenyl, chloreneb, dichlorane, quintozen, technazen, tolclophosmethyl, etridiazole; (c) Agents that act on cell membranes: iodocarb, propamocarb, propamocarb hydrochloride, propamocarb fosetilate, prothiocarb; (d) Microorganisms that disrupt the cell membrane of pathogenic bacteria: Bacillus subtilis, Bacillus subtilis strain QST713, Bacillus subtilis strain FZB24, Bacillus subtilis strain MBI600, Bacillus subtilis strain D747, Bacillus amyloliquefaciens; (e) Cell membrane disrupting agent: Extract of tea tree;

[0109] (7) Inhibitors of cell membrane sterol biosynthesis: (a) Inhibitors of C14 demethylation in sterol biosynthesis: Triforine, Pyriphenox, Pyrisoxazole, Fenalimol, Flurprimidol, Nualimol, Imazalil, Imazalil sulfate, Oxpoconazole, Oxpoconazole fumarate, Peflazoate, Prochloraz, Triflumizole, Viniconazole, Azaconazole, Vitertanol, Bromuconazole, Cyproconazole, Diclobutrazol, Difenoconazole, Diniconazol, Diniconazol-M, Epox Siconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafole, fluconazole, fluconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, mycrobutanil, penconazole, propiconazole, fluquinconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, prothioconazole, voriconazole, mefentrifluconazole; (b) Inhibitors of Δ14 reductase and Δ8→Δ7-isomerase in sterol biosynthesis: algimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph, fenpropidine, piperalin, spiroxamine; (c) 3-ketoreductase inhibitors in C4 demethylation of the sterol biosynthesis pathway: fenhexamide, fenpyrazamine; (d) Squalene epoxidase inhibitors of the sterol biosynthesis pathway: pyributicarb, naphthifine, terbinafine;

[0110] (8) Cell wall synthesis inhibitors: (a) Trehalase inhibitors: validamycin; (b) Chitin synthase inhibitors: polyoxin, polyoxorim; (c) Cellulose synthase inhibitors: Dimethomorph, Flumorph, Pyrimorph, Benciavalicarb, Benciavalicarb isopropyl, Iprovalicarb, Valifenarate, Mandipropamide;

[0111] (9) Melanin biosynthesis inhibitors (a) Inhibitors of melanin biosynthesis reductase: phthalide, pyroquilon, tricyclazole; (b) Inhibitors of melanin biosynthesis dehydration enzymes: carpropamide, diclocimet, phenoxanil; (c) Polyketide synthesis inhibitor for melanin biosynthesis: Tolprocarb;

[0112] (10) Resistance inducers for host plants: (a) Agents that act on the salicylic acid synthesis pathway: acibenzoral-S-methyl; (b) Others: Probenazole, thiadinil, isothianil, diclobentiazox, ipfentrifluconazole, laminarin, knotweed extract, phosphorous acid, phosphate;

[0113] (11) Agents of unknown action: cymoxanil, fosetyl aluminum, phosphoric acid, phosphate, tecrophthalam, triazoxide, fursulfamide, diclomedin, metasulfocarb, cyflufenamide, metraphenone, pyrophenone, dozin, dozin free base, fluthianil;

[0114] (12) Agents with multiple sites of action: copper (copper salts), Bordeaux mixture, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide, Farbam, Mancozeb, Maneb, Mancapper, Methylam, polycarbamate, propineb, Thiram, Zineb, Ziram, Captan, Captafol, Forpet, chlorothalonil, diclofluanide, tolfluanide, guazatin, guazatin triacetate (also known as iminoctadine triacetate), iminoctadine triabethylate, anilazine, dithianone, quinomethionate, fluorimide;

[0115] (13) Other agents: DBEDC, fluoroforpet, guazatin acetate, bis(8-quinolinolate)copper(II), propamidine, chloropicrin, cyproflam, Agrobacterium, bethoxazine, diphenylamine, methylisothiocyanate (MITC), mildeomycin, capsaicin, cufraneb, cyprosulfamide, dazomet, debacarb, dichlorophene, diphenzoquat, diphenzoquat methylsulfonate, flumetbel, fosetyl calcium, fosetyl sodium, irumamycin, natamycin, nitrotar isopropyl, oxamocarb, pyrrolnitrin, tebufloxin, torniphanide, zarilamid, algophase, amica Luthiazole, oxathiapiproline, fluoxapiproline, methylam zinc, benthazole, triclamide, uniconazole, oxyfenthiin, picarbtrazox, diclobentiazox, quinofumerine, thiram, ambam, Agrobacterium radiobacter, Coniothirium minitans, Pseudomonas fluorescein, Pseudomonas rhodesia, Talaromyces flavus, Trichoderma atroviride, nonpathogenic Ervinia carotobora, Bacillus simplex, Variovorax paradoxus, Lactobacillus plantarum, floryl picoxamide, pyrapropoin, fluindapyr, aminopyriphen, pyridaclomethyl, ibufluphenoquine, dipimethitron;

[0116] Specific examples of active ingredients (II) that can be mixed with or used in combination with the fungicide for agricultural and horticultural use of the present invention, such as insecticides, acaricides, nematicides, soil pesticides, and insecticides, are shown below.

[0117] (1) Acetylcholinesterase (AChE) inhibitors (a) Carbamate acetylcholinesterase (AChE) inhibitors: Alanicarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarbox, Butoxycarb, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Phenobucarb, Formetanate, Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pyrimicarb, Propoxul, Thiodicarb, Thiofanox, Triazamate, Trimetacarb, XMC, Xylylcarb, Phenothiocarb, MIPC, MPMC, MTMC, Aldoxycarb, Alixicarb, Aminocarb, Bufencarb, Chloetocarb, Metam sodium, Promecarb; (b) Organophosphorus acetylcholinesterase (AChE) inhibitors: Acephate, Azamethiphos, Adinphos-ethyl, Adinphos-methyl, Kazsaphos, Chlorethoxyphos, Chlorfenvinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinon, Dichlorvos, Diclotophos, Dimethoate, Dimethylvinphos, Disulfon, EPN, Ethion, Etoprophos, Fanflu, Phenamiphos, Fenitrothion, Fenthion, Fostiazate, Heptenophos, Imisiaphos, Isofenphos, Isocarbophos, Isopropyl-O-(methoxyaminothiophosphoryl) salicylate, Isoxathion, Malathion, Mecarbam, Metamidophos, Methidathion, Mevinphos, Monoclotophos, Nared, Omethoate, Oxydimetonmethyl, Parathion, Para Thione methyl, fenthoate, phorate, fosalon, fosmet, phosphamidone, foxim, pyrimiphos methyl, profenofos, propetamfos, prothiofos, pyraclofos, pyridaphenthion, quinalfos, sulfotep, tebupyrimfos, temefos, terbufos, tetrachlorvinfos, thiometon, triazofos, trichlorfon, bamidothion, bromophos-ethyl, BRP, carbophenthion, cyanophenthion, CYAP, demeton-S-methylsulfone, dialifos, diclofenthion, dioxabenzofos, etrimfos, fensulfothion, flupyrazofos, honofos, formothion, fosmetylane, isazofos, iodophenthion, methacryfos, pyrimiphos-ethyl, phosphocarb, propafos, protoate, sulprofos;

[0118] (2) GABAergic chloride ion channel blockers: Acetoprole, chlordane, endosulfan, ethiprole, fipronil, pyrafluprole, pyriprole, campechlor, heptachlor, dienochlor, flufiprol;

[0119] (3) Sodium channel modulator (a) Pyrethroid sodium channel modulators: Acrinatrin, allethrin, d-cistrans-allethrin, d-trans-allethrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentenyl isomer, biorethmetrin, cycloprothrin, cyfluthrin, β-cyfluthrin, cyhalothrin, λ-cyhalothrin, γ-cyhalothrin, cypermethrin, α-cypermethrin, β-cypermethrin, θ-cypermethrin Lumethrin, ζ-cypermethrin, cyphenothrin [(1R)-trans isomer], deltamethrin, empenthrin [(EZ)-(1R)-isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucitrinate, flumethrin, τ-fluvalinate, halfenprox, imiprothrin, cadesrin, permethrin, phenothrin Phosphorus [(1R)-trans isomer], prallethrin, pyrethram, pyrethrin, resmethrin, silafluofen, tefluthrin, tetramesrin, tetramesrin [(1R)-isomer], tralomethrin, transfluthrin, allethrin, pyrethrin I, pyrethrin II, profluthrin, dimefluthrin, bioetanomethrin, biopermethrin, transpermethrin, fenfluthrin, fenpyritrin, flubrocitrinate, flufenprox, metofluthrin, protrifenbut, pyrethmethrin, terarethrin, κ-bifenthrin, chloroprarethrin, heptafluthrin, meperfluthrin, ε-metofluthrin, monfluorothrin, ε-monfluorothrin, κ-tefluthrin, tetramethylfluthrin, bioetanomethrin; (b) Sodium channel modulators (DDTs): DDT, methoxychloride;

[0120] (4) Nicotinic acetylcholine receptor (nAChR) competitive modulators: Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam, nicotine, sulfoxaflor, flupyridiflon, triflumesopyrim, dichloromesothiaz, flupyrim; (5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators: Spinetram, Spinosad; (6) Glutamate-mediated chloride ion (chloride ion) channel (GluCl) allosteric modulator: Abamectin, emamectin, emamectin benzoate, lepimectin, milbemectin, ivermectin, selamectin, doramectin, eprinomectin, ivermectin, moxidectin, selamectin, milbemycin, milbemycin oxime, nemadectin;

[0121] (7) Juvenile hormone analogues: Hydroprene, quinoprene, methoprene, phenoxycarb, pyriproxyfen, diofenolan, epophenonane, triprene; (8) Other nonspecific (multisite) inhibitors: Methyl bromide, alkyl halides, chloropicrin, sodium aluminum fluoride, sulfuryl fluoride, borax, boric acid, disodium octaborate, sodium borate, sodium metaborate, tartrate, dazomet, metam, potassium metam, sodium metam; (9) String organ TRPV channel modulator: Flonicamide, Pymetrozine, Pyrifluquinazon, Afidopiropene; (10) Mite growth inhibitors: Clofentezine, diflovidazine, hexythiazox, etoxazole; (11) Microbial-derived insect midgut endometrium disruptors: Proteins contained in Bacillus thuringiensis subspecies islaerensi, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies krustaki, Bacillus thuringiensis subspecies tenebryonis, and Bt crops: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1; Bacillus sphaericus;

[0122] (12) Mitochondrial ATP synthase inhibitors: Diafenthiurone, azocyclotin, cyhexatin, fenbutatin oxide, propargit, tetradiphon; (13) Oxidative phosphorylation uncoupling agents that disrupt the proton gradient: Chlorfenapir, DNOC, sulfuramide, binapacril, dinovton, dinocup; (14) Nicotinic acetylcholine receptor (nAChR) channel blockers: Bensultap, cartap hydrochloride, nereistoxin, thiocyclam, thiosultap sodium salt; (15) Chitin biosynthesis inhibitors, type 0: Bistriflurone, Chlorfluazurone, Diflubenzuron, Flucycloxurone, Flufenoxurone, Hexaflumurone, Lufenuron, Novalon, Noviflumurone, Teflubenzuron, Triflumurone, Buprofezin, Fluazurone; (16) Chitin biosynthesis inhibitors, type 1: Buprofezin; (17) Molting inhibitors: Cyromazine; (18) Ecdysone receptor agonists: Chromafenozide, halofenozide, methoxyfenozide, tebufenozide;

[0123] (19) Octopamine receptor agonists: Amitraz, Demiditraz, Chlordimeform; (20) Mitochondrial electron transport chain complex III inhibitors: Hydramethylnon, acequinosyl, fluacrypyrim, bifenazate; (21) Mitochondrial electron transport chain complex I inhibitors (METI): Phenazaquine, fenpyroximate, pyridaben, pyrimidifen, tebufenpyrad, tolfenpyrad, rotenone; (22) Voltage-gated 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, piflubumide;

[0124] (26) ryanodine receptor modulators: Chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide, cyhalodiamid, tetrachlorantraniliprole, tetraniliprole; (27) Chord tone organ modulator target region unidentified: flonicamide; (28) GABAergic chloride ion channel allosteric modulator: Broflanilide, fluxamethamide, isocycloseram, afoxolaner, fluralaner, rotineral, sarolaner; (29) Other insecticides and acaricides: Azadirachtin, benzoximate, bifenazate, bromopropylate, quinomethionate, cryolite, dicofor, lime sulfur mixture, mancozeb, pyridaryl, benkrothiaz, sulfur, amidoflumet, 1,3-dichloropropene, DCIP, phenisobromolate, benzomate, metaldehyde, chlorbenzilate, clothiazoben, dicyclanil, phenoxacrim, fentriphanil, flubendimine, flufenazine, gossiplura, japonila, methoxadiazone, petroleum (oil), potassium oleate, tetrasul, triaracene, afidopiropene, flufiprol, fluensulfone, meperflusrin, tetramethylflusrin, tralopiryl, dimeflusrin, methylneodecane Amides, fluralaner, afoxolaner, fluxamethamide, 5-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-(1H-1,2,4-triazole-1-yl)benzonitrile (CAS: 943137-49-3), brofuranilide, other metadiamides, Steiner's nema capocapsae, Steiner's nema glacerai, Pastouria penetrans, Pechylomyces stenuipes, Pechylomyces phmosoroseus, Beauveria bassiana, Beauveria bronniati, Metaridium anisoplie, Verticillium lecani, Acinonapyr, Benzpyrimoxane, Frometoxin, Fluhexaphon, Oxazosulfyl, Cyclopyrazoflor.

[0125] (30) Anthelmintics: (a) Benzimidazole derivatives: Fenbendazole, albendazole, triclabendazole, oxybendazole, mebendazole, oxfendazole, perbendazole, flubendazole, febantel, netobimin, thiophanate, thiabendazole, cambendazole; (b) Salicylanilide derivatives: Closantel, oxyclozanide, lafoxanide, niclosamide; (c) Substituted phenols: nitroxynyl, nitroscanates; (d) Pyrimidines: pyrantel, morantel; (e) Imidazothiazole derivatives: Lebamisol, Tetramisol; (f) Tetrahydropyrimidine derivatives: praziquantel, epsiplantel; (g) Other anthelmintics: cyclodiene, liania, chlorthrone, metronidazole, demiditraz, piperazine, diethylcarbamazine, dichlorophene, monepantel, tripenzimidine, amidantel, thiaacetalthamide, melarsomine, arsenamide.

[0126] Specific examples of plant growth regulators as active ingredient (II) that can be mixed with or used in combination with the fungicide for agricultural and horticultural use of the present invention are shown below. Abscisic acid, kinetin, benzylaminopurine, 1,3-diphenylurea, forchlorfenuron, thidiazurone, 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, phenothic acid Ole, 1-Naphthylacetamide, Ethiclozate, Cloxihonac, Hydrazide Maleate, 2,3,5-Triiodobenzoic Acid, Salicylic Acid, Methyl Salicylate, (-)-Jasmonic Acid, Methyl Jasmonate, (+)-Strigol, (+)-Deoxystrigol, (+)-Orobancol, (+)-Solgolactone, 4-Oxo-4-(2-Phenylethyl)aminobutyric Acid, Ethephon, Chlormecoat, Mepicote Chloride, Benzyladenine, 5-Aminolevulinic Acid, Daminozide. [Examples]

[0127] {Formulation} The fungicide for agricultural and horticultural use of the present invention is not particularly limited in terms of dosage form. For example, dosage forms such as wettable powders, emulsions, powders, granules, water-soluble powders, suspensions, granular wettable powders, and tablets can be used. The method of preparing the formulation is not particularly limited, and known preparation methods can be used depending on the dosage form.

[0128] The following are some examples of formulations. The formulations shown below are merely illustrative and can be modified within the bounds of the spirit of the present invention; the present invention is not limited in any way by these examples. Unless otherwise specified, "parts" refers to "parts by mass."

[0129] (Example of formulation 1: Wettable powder) 40 parts of the pyrazole compound of the present invention, 53 parts of diatomaceous earth, 4 parts of a higher alcohol sulfate ester, and 3 parts of an alkylnaphthalene sulfonate are uniformly mixed, and then finely ground to obtain a wettable powder containing 40% by mass of the active ingredient.

[0130] (Formulation example 2: Emulsion) 30 parts of the pyrazole 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 emulsion containing 30% by mass of the active ingredient.

[0131] (Formulation example 3: Granules) Five parts of the pyrazole compound of the present invention, forty parts of talc, thirty-eight parts of clay, ten parts of bentonite, and seven parts of alkyl sodium sulfate are uniformly mixed, then finely ground, and subsequently granulated to a particle diameter of 0.5 to 1.0 mm to obtain granules containing 5% by mass of the active ingredient.

[0132] (Formulation example 4: Granules) Five parts of the pyrazole compound of the present invention, seventy-three parts of clay, twenty-tenths of bentonite, one part of sodium dioctyl sulfosuccinate, and one part of potassium phosphate are uniformly mixed and pulverized, then water is added and kneaded. After that, the mixture is granulated and dried to obtain granules containing 5% by mass of the active ingredient.

[0133] (Formulation example 5: Suspension) Ten parts of the pyrazole compound of the present invention, four parts of polyoxyethylene alkyl allyl ether, two parts of sodium polycarboxylate, ten parts of glycerin, 0.2 parts of xanthan gum, and 73.8 parts of water are mixed and wet-ground until the particle size is 3 microns or less to obtain a suspension containing 10% by mass of the active ingredient.

[0134] (Formulation example 6: Granular wettable powder) Forty parts of the pyrazole compound of the present invention, 36 parts of clay, 10 parts of potassium chloride, 1 part of sodium alkylbenzene sulfonate, 8 parts of sodium lignin sulfonate, and 5 parts of formaldehyde condensate of sodium alkylbenzene sulfonate are uniformly mixed and finely ground. Then, an appropriate amount of water is added and kneaded to form a clay-like substance. The clay-like substance is granulated and then dried to obtain a granular wettable powder containing 40% by mass of the active ingredient.

[0135] Next, the present invention will be explained in more detail by showing examples of compound preparation. However, the present invention is not limited in any way by the following examples. [Manufacturing Example 1] Methyl 2-(3-(tert-butyl)-1-methyl-5-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-4-carbonyl)-1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate (compound 1)) was produced by the following process.

[0136] [ka]

[0137] 0.040 g of 3-(tert-butyl)-1-methyl-5-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-4-carboxylic acid was dissolved in 1.0 mL of tetrahydrofuran. To this, 0.050 g of methyl 1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate, 0.091 g of 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate, and 0.050 mL of triethylamine were added, and the mixture was stirred overnight at room temperature. The reaction mixture was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate) to obtain 0.018 g of the target product (yield 29%).

[0138] The compounds shown in Table 1 were prepared using the same process as in the above manufacturing example. The melting point or appearance (viscous oil) is indicated in the properties column. For compounds with a viscous oil appearance, the LCMS retention time is indicated.

[0139] The LCMS(SQD2) retention time was determined using the following method. A system consisting of an ultrafast high-resolution liquid chromatograph (ACQUITY UPLC H-Class: Waters), an HPLC / UHPLC detector (ACQUITY UPLC photodiode array (PDA) eλ detector (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 fitted with a CORTECS UPLC C18 column (Waters, 2.1 × 50 mm, 1.6 μm), and measurements were taken at 40°C, a flow rate of 0.6 mL / min, and a 2 μL injection. Water containing 0.1% by mass of 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 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 immediately decreased to 30% by mass, and finally maintained at 30% by mass for 0.50 minutes.

[0140] [Table 1]

[0141] The effects of the present invention are illustrated by the following sterilization efficacy tests and disease control tests.

[0142] (Test of fungicidal effect against gray mold fungus) A spore suspension of gray mold fungus (Botrytis cinerea, Vogel medium) was prepared. The pyrazole compound of the present invention was added to dimethyl sulfoxide to obtain a drug solution. This drug solution and the aforementioned spore suspension were mixed in equal volumes (by volume) to obtain a test solution in which the pyrazole compound of the present invention was concentrated at 25 ppm by volume. The test solution was dropped onto a 96-well microplate (drug treatment area). Dimethyl sulfoxide and the aforementioned spore suspension were mixed in equal volumes (by volume) to obtain a control solution. The control solution was dropped onto a 96-well microplate (untreated area). These were cultured at 20°C in the dark for 5 days. 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 culture)-(OD of drug-treated group before culture)] / [(OD of untreated group after culturing) - (OD of untreated group before culturing)]}

[0143] Fungicide efficacy tests were conducted on compounds 1-3 against gray mold fungus. All compounds showed a growth inhibition rate of 75% or more.

[0144] (Test of fungicidal effect against grape late blight fungus) The spore suspension of Botrytis cinerea (Vogel medium) was replaced with a spore suspension of Glomerella cingulata (Vogel medium), and the temperature and duration of the standing period were changed to 25°C and 3 days, respectively. Turbidity was measured and the growth inhibition rate was calculated using the same method as in the fungicidal efficacy test against Botrytis cinerea.

[0145] The fungicidal efficacy of compounds 1-3 against grape late blight fungus was tested. All compounds showed a growth inhibition rate of 75% or more.

[0146] (Fungicide efficacy test against apple anthracnose fungus) The spore suspension of gray mold fungus (Botrytis cinerea, Vogel medium) was replaced with a spore suspension of apple anthracnose fungus (Colletotrichum acutatum, Czapek medium), and the temperature and duration of the standing period were changed to 25°C and 4 days, respectively. Turbidity was measured and the growth inhibition rate was calculated using the same method as in the fungicidal efficacy test against gray mold fungus.

[0147] The fungicidal efficacy of compounds 1-3 against apple anthracnose fungus was tested. All compounds showed a growth inhibition rate of 75% or more.

[0148] (Test of fungicidal effect against wheat red mold) The spore suspension of gray mold fungus (Botrytis cinerea, Vogel medium) was replaced with a spore suspension of wheat red mold fungus (Fusarium graminearum, SD medium), and the temperature and duration of the standing period were changed to 25°C and 4 days, respectively. Turbidity was measured and the growth inhibition rate was calculated using the same method as in the fungicidal efficacy test against gray mold fungus.

[0149] Fungicide efficacy tests were conducted on compounds 1-3 against Fusarium head blight. All compounds showed a growth inhibition rate of 75% or more.

[0150] (Control trial for cucumber gray mold disease) 5 parts by mass of the pyrazole 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 emulsion (1) with an active ingredient of 5% by mass.

[0151] Water was added to the emulsion (1) to obtain a chemical solution in which the concentration of the pyrazole compound of the present invention was 125 ppm by mass or 25 ppm by mass. Subsequently, the chemical solution was sprayed onto cucumber seedlings (cultivar "Jishashi" strain, cotyledon stage) cultivated in nursery pots, and then air-dried. Thereafter, a suspension of conidia of Botrytis cinerea was dropped and inoculated thereon (treatment group). As a control, a suspension of conidia of Botrytis cinerea was dropped and inoculated onto cucumber seedlings without spraying the chemical solution (non-treatment group). They were left standing in a humid chamber at 20°C. Four days after inoculation, the leaves of the cucumber seedlings were visually observed, and the control value was calculated from the lesion area ratio by the following formula.

[0152] Control value (%) = 100 - {lesion area ratio in the treatment group / lesion area ratio in the non-treatment group} × 100

[0153] Control tests against Botrytis cinerea of Compounds 1 to 3 were conducted at a concentration of 125 ppm by mass. All of the compounds showed a control value of 75% or more.

Industrial Applicability

[0154] The pyrazole compound of the present invention has excellent bactericidal activity against pathogenic bacteria that affect agricultural and horticultural plants, is excellent in safety, and can be synthesized industrially advantageously. The agricultural and horticultural bactericide 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. 【Chemistry 1】 [In the above formula (I), Q １ This 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. Q ２ This 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. Z represents an oxygen atom or a sulfur atom. R １ This represents a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C3-6 cycloalkyl group. R ２ This 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. R ３ is 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 group represented by the formula: R ａ -CO-, a group represented by the formula: R ａ -CS-, a group represented by the formula: R ａ -CO-CO-, R ａ -SO ２ -, 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 member heterocyclyl group, or a cyano group, R ａ Each of these independently represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C3-6 cycloalkoxy group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted amino 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 3-6 membered heterocyclyl group, a substituted or unsubstituted phenoxy group, a substituted or unsubstituted naphthyloxy group, or a substituted or unsubstituted 3-6 membered heterocyclyloxy group. R ４ This 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 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, or a halogeno group. R ５ This 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 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, or a halogeno group.

2. R ３ However, formula: R ａ１ It is a group represented by -CO-, R ａ１ The compound or salt thereof according to claim 1, wherein is a substituted or unsubstituted C1-6 alkoxy group, or a substituted or unsubstituted C3-6 cycloalkoxy group.

3. A fungicide for agricultural and horticultural use, comprising at least one selected from the group consisting of the compound described in claim 1 or 2 and its salts, as an active ingredient.

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