Five-membered heteroaryl compound and agricultural and horticultural bactericide

Abstract

This five-membered heteroaryl compound is represented formula (Z-I) (wherein Q1 and Q2 each independently represent a phenyl group or the like; B1, B2 and B3 each independently represent an oxygen atom, a nitrogen atom, NR1 or CR2; R1 represents an alkyl group or the like; R2 represents a hydrogen atom or the like; Za represents an oxygen atom or the like; T represents a partial structure (T-1) or (T-2); Z represents an oxygen atom or the like; R6 represents a hydrogen atom or the like; Zb represents an alkoxy group or the like: R7 represents RcCO- or the like; Rc represents an alkyl group or the like; R4 and R5 each independently represent a hydrogen atom or the like; and n represents an integer of 1 to 3).

Description

Five-membered heteroaryl compounds and agricultural and horticultural fungicides

[0001] The present invention relates to a five-membered heteroaryl compound and an agricultural and horticultural fungicide. More specifically, the present invention relates to a five-membered heteroaryl compound that has excellent fungicidal activity against pathogens that affect agricultural and horticultural plants, is highly safe, and can be synthesized industrially advantageously, and to an agricultural and horticultural fungicide containing the compound as an active ingredient. This application claims priority based on Japanese Patent Application No. 2023-131664 filed in Japan on August 10, 2023, Japanese Patent Application No. 2024-007491 filed in Japan on January 22, 2024, and Japanese Patent Application No. 2024-068592 filed in Japan on April 19, 2024, the contents of which are incorporated herein by reference.

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

[0003] Incidentally, Patent Document 1 discloses a compound represented by formula (A) or the like.

[0004]

[0005] Special Publication No. 2022-508277

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

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

[0008]

[0009] [wherein in the formula (Z-I), Q １represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group; Q ２ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group, and a partial structure of the following formula (III):

[0010]

[0011] In B １ represents an oxygen atom, a nitrogen atom, a group of the formula: NR １ or a group represented by the formula: CR ２ B represents a group represented by ２ represents an oxygen atom, a nitrogen atom, a group of the formula: NR １ or a group represented by the formula: CR ２ B represents a group represented by ３ represents an oxygen atom, a nitrogen atom, a group of the formula: NR １ or a group represented by the formula: CR ２ B represents a group represented by １ , B ２ , and B ３ any one of which is an oxygen atom or a group represented by the formula: NR １ and the remaining two are a nitrogen atom or a group represented by the formula: CR ２ R １ each independently represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C3-6 cycloalkyl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group; R ２are each independently 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 C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylcarbonyloxy group, a substituted or unsubstituted C1-6 alkoxycarbonyloxy group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C a 1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5-6 membered heterocyclyl group, a substituted or unsubstituted phenyloxy group, a substituted or unsubstituted naphthyloxy group, a substituted or unsubstituted 5-6 membered heterocyclyloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a nitro group, a cyano group, or a halogeno group, carbon atoms marked with * and + in the partial structure correspond to carbon atoms marked with * and + in the formula (Z-I), Z ａ represents an oxygen atom or a sulfur atom, T represents the partial structure (T-1) or the partial structure (T-2),

[0012]

[0013] In the partial structure (T-1) or partial structure (T-2), the arrow with + is bonded to the carbon atom with + in the partial structure of formula (III), and the other arrow is bonded to the carbon atom with + in formula (Z-I). ７ In the partial structure (T-1), Z represents an oxygen atom or a sulfur atom, and R ６represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a formyl group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group, ｂ represents a C1-6 alkoxy group or a C1-6 alkylthio group, R ７ 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 group of the formula: R ｃ a group represented by —CO—, a group represented by the formula: R ｃ a group represented by —CS—, a group represented by the formula: R ｃ a group represented by —CO—CO—, R ｃ -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- or 6-membered heterocyclyl group, or a cyano group, ｃ each independently represent 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- to 6-membered heterocyclyl group, or a substituted or unsubstituted 3- to 6-membered heterocyclyloxy group; R ４ each independently 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- or 6-membered heterocyclyl group, or a halogeno group; R５ each independently represent 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- or 6-membered heterocyclyl group, or a halogeno group, and R ４ and R ５ may combine with each other to form a divalent organic group, and n represents an integer of 1 to 3.] (2) The compound or salt thereof according to (1), wherein formula (Z-I) is represented by formula (I).

[0014]

[0015] [wherein in the formula (I), Q １ , Q ２ , B １ , B ２ , B ３ , Z ａ , R ４ , R ５ , R ７ and n is Q in formula (Z-I). １ , Q ２ , B １ , B ２ , B ３ , Z ａ , R ４ , R ５ , R ７ and n have the same meaning as Z and R ６ represents Z and R in the partial structure (T-1). ６ (3) The Z ａ is an oxygen atom, Z is an oxygen atom, and R ６ is a hydrogen atom, ７ is a formyl group, the formula: R ｃ a group represented by —CO—, a group represented by the formula: R ｃ a group represented by —CS—, a group represented by the formula: R ｃ a group represented by —CO—CO—, or R ｃ -SO ２-, wherein n is a group represented by the formula (1), and n is 1. (4) An agricultural and horticultural fungicide containing, as an active ingredient, at least one selected from the group consisting of the compounds and salts thereof according to any one of the formulas (1) to (3). (5) A method for producing a compound represented by formula (I-1), comprising a step of reacting a compound represented by formula (im-1) with a compound represented by formula (im-2) in the presence of an acid scavenger.

[0016]

[0017] [wherein Q １ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group; Q ２ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group, and the following partial structure:

[0018]

[0019] In B １ represents an oxygen atom, a nitrogen atom, a group of the formula: NR １ or a group represented by the formula: CR ２ B represents a group represented by ２ represents an oxygen atom, a nitrogen atom, a group of the formula: NR １ or a group represented by the formula: CR ２ B represents a group represented by ３ represents an oxygen atom, a nitrogen atom, a group of the formula: NR １ or a group represented by the formula: CR ２ B represents a group represented by １ , B ２ , and B ３ any one of which is an oxygen atom or a group represented by the formula: NR １ and the remaining two are a nitrogen atom or a group represented by the formula: CR ２ R is a group represented by １each independently represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C3-6 cycloalkyl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group; R ２ are each independently 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 C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylcarbonyloxy group, a substituted or unsubstituted C1-6 alkoxycarbonyloxy group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C represents a 1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5-6 membered heterocyclyl group, a substituted or unsubstituted phenyloxy group, a substituted or unsubstituted naphthyloxy group, a substituted or unsubstituted 5-6 membered heterocyclyloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a nitro group, a cyano group, or a halogeno group, carbon atoms marked with * and + in the partial structure correspond to carbon atoms marked with * and + in formula (I-1) or formula (im-1), Z ａ represents an oxygen atom or a sulfur atom, Z represents an oxygen atom or a sulfur atom, R ４ each independently 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- or 6-membered heterocyclyl group, or a halogeno group; R ５each independently represent 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- or 6-membered heterocyclyl group, or a halogeno group, and R ４ and R ５ may combine with each other to form a divalent organic group, n represents an integer of 1 to 3, and R ６ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a formyl group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group, R ７a is a formyl group, the formula: R ｃ a group represented by —CO—, a group represented by the formula: R ｃ a group represented by —CS—, a group represented by the formula: R ｃ a group represented by —CO—CO—, or R ｃ -SO ２ - represents a group represented by R ｃ each independently represent 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- to 6-membered heterocyclyl group, or a substituted or unsubstituted 3- to 6-membered heterocyclyloxy group, and G represents a halogeno group.] (6) A method for producing a compound represented by formula (I-2), comprising a step of reacting a compound represented by formula (im-3) with a compound represented by formula (im-4) using oxygen as an oxidizing agent in the presence of an organic base and a copper catalyst.

[0020]

[0021] [wherein Q １ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group; Q ２ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group, and the following partial structure:

[0022]

[0023] In B １ represents an oxygen atom, a nitrogen atom, a group of the formula: NR １ or a group represented by the formula: CR ２ B represents a group represented by ２ represents an oxygen atom, a nitrogen atom, a group of the formula: NR １ or a group represented by the formula: CR ２ B represents a group represented by ３ represents an oxygen atom, a nitrogen atom, a group of the formula: NR １ or a group represented by the formula: CR ２ B represents a group represented by １ , B ２ , and B ３ any one of which is an oxygen atom or a group represented by the formula: NR １ and the remaining two are a nitrogen atom or a group represented by the formula: CR ２ R is a group represented by １ each independently represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C3-6 cycloalkyl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group; R ２are each independently 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 C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylcarbonyloxy group, a substituted or unsubstituted C1-6 alkoxycarbonyloxy group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C represents a 1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5-6 membered heterocyclyl group, a substituted or unsubstituted phenyloxy group, a substituted or unsubstituted naphthyloxy group, a substituted or unsubstituted 5-6 membered heterocyclyloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a nitro group, a cyano group, or a halogeno group; carbon atoms marked with * and + in the partial structure correspond to carbon atoms marked with * and + in formula (I-2) or formula (im-3); Z represents an oxygen atom or a sulfur atom; R ４ each independently 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- or 6-membered heterocyclyl group, or a halogeno group; R ５ each independently represent 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- or 6-membered heterocyclyl group, or a halogeno group, and R ４ and R ５may combine with each other to form a divalent organic group, n represents an integer of 1 to 3, and R ６ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a formyl group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group, R ７a is a formyl group, the formula: R ｃ a group represented by —CO—, a group represented by the formula: R ｃ a group represented by —CS—, a group represented by the formula: R ｃ a group represented by —CO—CO—, or R ｃ -SO ２ - represents a group represented by R ｃ each independently represent 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- to 6-membered heterocyclyl group, or a substituted or unsubstituted 3- to 6-membered heterocyclyloxy group.] (7) A method for producing a compound represented by formula (I-3), comprising reacting a compound represented by formula (im-5) and a compound represented by formula (im-6) with U in formula (im-5). １ When is a hydroxyl group, U １ When is a halogeno group, the production method comprises a step of reacting in the presence of an acid scavenger.

[0024]

[0025] [wherein Q １ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group; Q２ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group, and the following partial structure:

[0026]

[0027] In B １ represents an oxygen atom, a nitrogen atom, a group of the formula: NR １ or a group represented by the formula: CR ２ B represents a group represented by ２ represents an oxygen atom, a nitrogen atom, a group of the formula: NR １ or a group represented by the formula: CR ２ B represents a group represented by ３ represents an oxygen atom, a nitrogen atom, a group of the formula: NR １ or a group represented by the formula: CR ２ B represents a group represented by １ , B ２ , and B ３ any one of which is an oxygen atom or a group represented by the formula: NR １ and the remaining two are a nitrogen atom or a group represented by the formula: CR ２ R １ each independently represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C3-6 cycloalkyl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group; R ２are each independently 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 C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylcarbonyloxy group, a substituted or unsubstituted C1-6 alkoxycarbonyloxy group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C represents a 1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5-6 membered heterocyclyl group, a substituted or unsubstituted phenyloxy group, a substituted or unsubstituted naphthyloxy group, a substituted or unsubstituted 5-6 membered heterocyclyloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a nitro group, a cyano group, or a halogeno group, carbon atoms marked with * and + in the partial structure correspond to carbon atoms marked with * and + in formula (I-3) or formula (im-5), Z ａ represents an oxygen atom or a sulfur atom, R ４ each independently 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- or 6-membered heterocyclyl group, or a halogeno group; R ５ each independently represent 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- or 6-membered heterocyclyl group, or a halogeno group, and R ４ and R ５may combine with each other to form a divalent organic group, n represents an integer of 1 to 3, and R ６ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a formyl group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group, R ７a is a formyl group, the formula: R ｃ a group represented by —CO—, a group represented by the formula: R ｃ a group represented by —CS—, a group represented by the formula: R ｃ a group represented by —CO—CO—, or R ｃ -SO ２ - represents a group represented by R ｃ each independently represent 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, or a substituted or unsubstituted 3-6 membered heterocyclyloxy group; U １ represents a hydroxyl group or a halogeno group.] (8) A compound represented by formula (im-5A) or a salt thereof:

[0028]

[0029] [In the above formula (im-5A), Q １ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group; R １ represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C3-6 cycloalkyl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group; R２ａ represents a C1-6 haloalkyl group, a cyano group, or a halogeno group; U ４ represents a carboxyl group, a C1-6 alkoxycarbonyl group, or a halogenocarbonyl group.] (9) A compound represented by formula (im-5B) or a salt thereof:

[0030]

[0031] [In the above formula (im-5B), Q １ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group; R １ａ represents a substituted or unsubstituted C2-6 alkyl group or a substituted or unsubstituted C3-6 cycloalkyl group, U ４ represents a carboxyl group, a C1-6 alkoxycarbonyl group, or a halogenocarbonyl group.] (10) A compound represented by formula (im-25) or a salt thereof:

[0032]

[0033] [In the formula (im-25), Q １ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group; R １ａ represents a substituted or unsubstituted C2-6 alkyl group, or a substituted or unsubstituted C3-6 cycloalkyl group.

[0034] The five-membered heteroaryl compound of the present invention has excellent fungicidal activity against pathogenic bacteria that affect agricultural and horticultural plants, is highly safe, and can be synthesized industrially advantageously. The agricultural and horticultural fungicide of the present invention can effectively control diseases of agricultural and horticultural plants.

[0035] The 5-membered heteroaryl compound of the present invention is a compound represented by formula (ZI) (hereinafter, may be referred to as compound (ZI)) or a salt of compound (ZI).

[0036]

[0037] In the present invention, the term "unsubstituted" refers to only the core group. When the name of the core group alone is used without the term "substituted," it means "unsubstituted" unless otherwise specified. On the other hand, the term "substituted" means that any hydrogen atom in the core group has been replaced with a group (substituent) of the same or different structure as the core group. Therefore, a "substituent" is another group bonded to the core group. The number of substituents may be one or more. The two or more substituents may be the same or different. A term such as "C1-6" indicates that the core group has 1 to 6 carbon atoms, for example. This number of carbon atoms does not include the number of carbon atoms in the substituent. For example, a butyl group having an ethoxy group as a substituent is classified as a C2 alkoxy C4 alkyl group. The "substituent" is not particularly limited as long as it is chemically permissible and provides the effects of the present invention.

[0038] Examples of groups that can serve as "substituents" include: C1-6 alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, n-pentyl, and n-hexyl; C2-6 alkenyl groups such as vinyl, 1-propenyl, 2-propenyl (allyl), 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, and 2-methyl-2-propenyl; C2-6 alkynyl groups such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, and 1-methyl-2-propynyl;

[0039] C3-6 cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups; aryl groups such as phenyl, tolyl, xylyl, trimethylphenyl, and naphthyl groups; phenyl C1-6 alkyl groups such as benzyl and phenethyl groups; 3- to 6-membered heterocyclyl groups; 3- to 6-membered heterocyclyl C1-6 alkyl groups;

[0040] hydroxyl groups; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy groups; C2-6 alkenyloxy groups such as vinyloxy, allyloxy, propenyloxy, and butenyloxy groups; C2-6 alkynyloxy groups such as ethynyloxy and propargyloxy groups; phenoxy and naphthoxy groups; phenyl C1-6 alkoxy groups such as benzyloxy and phenethyloxy groups; 5- to 6-membered heteroaryloxy groups such as thiazolyloxy and pyridyloxy groups; 5- to 6-membered heteroaryl C1-6 alkyloxy groups such as thiazolylmethyloxy and pyridylmethyloxy groups;

[0041] a formyl group; a C1-6 alkylcarbonyl group such as an acetyl group or a propionyl group; a formyloxy group; a C1-6 alkylcarbonyloxy group such as an acetyloxy group or a propionyloxy group; a benzoyl group; a C1-6 alkoxycarbonyl group such as a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, an n-butoxycarbonyl group or a t-butoxycarbonyl group; a C1-6 alkoxycarbonyloxy group such as a methoxycarbonyloxy group, an ethoxycarbonyloxy group, an n-propoxycarbonyloxy group, an i-propoxycarbonyloxy group, an n-butoxycarbonyloxy group or a t-butoxycarbonyloxy group; a carboxyl group;

[0042] halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group; C1-6 haloalkyl groups such as a chloromethyl group, a chloroethyl group, a trifluoromethyl group, a 1,2-dichloro-n-propyl group, a 1-fluoro-n-butyl group, and a perfluoro-n-pentyl group; C2-6 haloalkenyl groups such as a 2-chloro-1-propenyl group and a 2-fluoro-1-butenyl group; C2-6 haloalkynyl groups such as a 4,4-dichloro-1-butynyl group, a 4-fluoro-1-pentynyl group, and a 5-bromo-2-pentynyl group; C1-6 haloalkoxy groups such as a trifluoromethoxy group, a 2-chloro-n-propoxy group, and a 2,3-dichlorobutoxy group; C2-6 haloalkenyloxy groups such as a 2-chloropropenyloxy group and a 3-bromobutenyloxy group; C1-6 haloalkylcarbonyl groups such as a chloroacetyl group, a trifluoroacetyl group, or a trichloroacetyl group;

[0043] amino groups; C1-6 alkyl-substituted amino groups such as methylamino, dimethylamino, and diethylamino; anilino and naphthylamino groups; phenyl C1-6 alkylamino groups such as benzylamino and phenethylamino; formylamino groups; C1-6 alkylcarbonylamino groups such as acetylamino, propanoylamino, butyrylamino, and i-propylcarbonylamino; C1-6 alkoxycarbonylamino groups such as methoxycarbonylamino, ethoxycarbonylamino, n-propoxycarbonylamino, and i-propoxycarbonylamino; unsubstituted or substituted aminocarbonyl groups such as aminocarbonyl, dimethylaminocarbonyl, phenylaminocarbonyl, and N-phenyl-N-methylaminocarbonyl; imino C1-6 alkyl groups such as iminomethyl, (1-imino)ethyl, and (1-imino)-n-propyl; Substituted or unsubstituted N-hydroxyimino C1-6 alkyl groups such as an N-hydroxy-iminomethyl group, a (1-(N-hydroxy)-imino)ethyl group, a (1-(N-hydroxy)-imino)propyl group, an N-methoxy-iminomethyl group, or a (1-(N-methoxy)-imino)ethyl group; an aminocarbonyloxy group; a C1-6 alkyl-substituted aminocarbonyloxy group such as an ethylaminocarbonyloxy group or a dimethylaminocarbonyloxy group;

[0044] a mercapto group; a C1-6 alkylthio group such as a methylthio group, an ethylthio group, an n-propylthio group, an i-propylthio group, an n-butylthio group, an i-butylthio group, an s-butylthio group, or a t-butylthio group; a C1-6 haloalkylthio group such as a trifluoromethylthio group or a 2,2,2-trifluoroethylthio group; a phenylthio group or a naphthylthio group; a 5- or 6-membered heteroarylthio group such as a thiazolylthio group or a pyridylthio group;

[0045] C1-6 alkylsulfinyl groups such as methylsulfinyl, ethylsulfinyl, and t-butylsulfinyl groups; C1-6 haloalkylsulfinyl groups such as trifluoromethylsulfinyl and 2,2,2-trifluoroethylsulfinyl groups; phenylsulfinyl groups; 5- to 6-membered heteroarylsulfinyl groups such as thiazolylsulfinyl and pyridylsulfinyl groups;

[0046] C1-6 alkylsulfonyl groups such as methylsulfonyl, ethylsulfonyl, and t-butylsulfonyl groups; C1-6 haloalkylsulfonyl groups such as trifluoromethylsulfonyl and 2,2,2-trifluoroethylsulfonyl groups; phenylsulfonyl groups; 5- to 6-membered heteroarylsulfonyl groups such as thiazolylsulfonyl and pyridylsulfonyl groups; C1-6 alkylsulfonyloxy groups such as methylsulfonyloxy, ethylsulfonyloxy, and t-butylsulfonyloxy groups; C1-6 haloalkylsulfonyloxy groups such as trifluoromethylsulfonyloxy and 2,2,2-trifluoroethylsulfonyloxy groups;

[0047] Tri-C1-6 alkyl-substituted silyl groups such as trimethylsilyl, triethylsilyl, and t-butyldimethylsilyl; triphenylsilyl group; cyano group; and nitro group.

[0048] Furthermore, any hydrogen atom in these "substituents" may be substituted with a group of a different structure. In this case, examples of the "substituent" include a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a halogeno group, a cyano group, and a nitro group.

[0049] Furthermore, the above-mentioned "3- to 6-membered heterocyclyl group" contains 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms as ring-constituting atoms. The heterocyclyl group may be either monocyclic or polycyclic. In a polycyclic heterocyclyl group, as long as at least one ring is a heterocycle, the remaining rings may be saturated alicyclic, unsaturated alicyclic, or aromatic. Examples of the "3- to 6-membered heterocyclyl group" include 3- to 6-membered saturated heterocyclyl groups, 5- to 6-membered heteroaryl groups, and 5- to 6-membered partially unsaturated heterocyclyl groups.

[0050] Examples of the "3- to 6-membered saturated heterocyclyl group" include an aziridinyl group, an epoxy group, an azetidinyl group, an oxetanyl group, a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, and a dioxanyl group.

[0051] Examples of "5-membered heteroaryl groups" include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups. Examples of "6-membered heteroaryl groups" include pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl groups. Examples of "5- to 6-membered partially unsaturated heterocyclyl groups" include 5-membered partially unsaturated heterocyclyl groups such as pyrrolinyl, dihydrofuranyl, dihydrothiophenyl, imidazolinyl, pyrazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, and isothiazolinyl groups; and 6-membered partially unsaturated heterocyclyl groups such as dihydropyranyl.

[0052] Q in formula (Z-I) １ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- or 6-membered heterocyclyl group, or a substituted or unsubstituted 9- or 10-membered heterocyclyl group.

[0053] Q in formula (Z-I) ２represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- or 6-membered heterocyclyl group, or a substituted or unsubstituted 9- or 10-membered heterocyclyl group.

[0054] A heterocyclyl group contains at least one heteroatom selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom as a ring-constituting atom. The heterocyclyl group may be either monocyclic or polycyclic. In a polycyclic heterocyclyl group, as long as at least one ring is a heterocycle, the remaining rings may be saturated alicyclic, unsaturated alicyclic, or aromatic.

[0055] Q １ or Q ２ Examples of the "5- to 6-membered heterocyclyl group" in the above formula include a 5- to 6-membered saturated heterocyclyl group, a 5- to 6-membered heteroaryl group, and a 5- to 6-membered partially unsaturated heterocyclyl group.

[0056] Q １ or Q ２ Examples of the "5- to 6-membered saturated heterocyclyl group" in the above formula include a pyrrolidinyl group, a tetrahydrofuranyl group, a tetrahydropyranyl group, a thiazolidinyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, and a dioxanyl group.

[0057] Q １ or Q ２ Examples of the "5-membered heteroaryl group" in the above formula include a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, and a tetrazolyl group.

[0058] Q １ or Q ２ Examples of the "6-membered heteroaryl group" in the above formula include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group.

[0059] Q １ or Q ２Examples of the "5- to 6-membered partially unsaturated heterocyclyl group" in the above formula (I) 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.

[0060] Q １ or Q ２ Examples of the "9-membered heterocyclyl group" in the above formula include an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothienyl group, an indazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a benzothiazolyl group, a benzisothiazolyl group, and a benzodioxolanyl group.

[0061] Q １ or Q ２ Examples of the "10-membered heterocyclyl group" in the above formula include a quinolinyl group, an isoquinolinyl group, a cinnolinyl group, a phthalazinyl group, a quinazolinyl group, and a quinoxalinyl group.

[0062] Q １ or Q ２In the above, substituents on the "5- to 6-membered heterocyclyl group", "phenyl group", "naphthyl group" or "9- to 10-membered heterocyclyl group" include a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a hydroxyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C1-6 alkoxy group substituted with a C1-6 alkoxy group, a C1-6 alkylcarbonyl group, a C1-6 alkylthio group, a C1-6 alkylsulfonyl group, a C3-6 cycloalkyl group, a phenyl group, a 5-membered heteroaryl group, a 6-membered heteroaryl group, a cyano group, a nitro group, a tri-C1-6 alkylsilyl group; an amino group substituted with a C1-6 alkyl group or a C1-6 alkylcarbonyl group; a carboxamide group substituted with a C1-6 alkyl; Preferred are: a phenyl group substituted by one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 5-membered heteroaryl group substituted by one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or a 6-membered heteroaryl group substituted by one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group.

[0063] Q １ or Q ２ Two substituents on the "5- to 6-membered heterocyclyl group," "phenyl group," "naphthyl group," or "9- to 10-membered heterocyclyl group" in the above formula (I) may be taken together 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 be taken together to form a divalent organic group. Examples of the divalent organic group include C3-6 alkylene groups such as trimethylene and tetramethylene; C1-3 alkylenedioxy groups such as methylenedioxy and dimethylenedioxy; and the like. For example, two substituents on a phenyl group may be taken together to form a trimethylene group, and Q １ or Q ２It is preferred to form an indanyl group as follows.

[0064] Among these, Q in formula (Z-I) １ is preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9-membered heterocyclyl group, more preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted pyridyl group, or a substituted or unsubstituted benzodioxolanyl group, even more preferably a substituted or unsubstituted phenyl group or a substituted or unsubstituted thiazolyl group, and particularly preferably a substituted or unsubstituted phenyl group. １The substituents on the "5- to 6-membered heterocyclyl group", "phenyl group", "naphthyl group" or "9- to 10-membered heterocyclyl group" in the above formula (I) are more preferably a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C1-6 alkylcarbonyl group, a C1-6 alkylthio group, a C1-6 alkylsulfonyl group, a C3-6 cycloalkyl group, a phenyl group, a phenyloxy group, a cyano group, a nitro group, a tri-C1-6 alkylsilyl group; an amino group substituted with a C1-6 alkyl group or a C1-6 alkylcarbonyl group; and / or a carboxamide group substituted with a C1-6 alkyl; and even more preferably a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 cycloalkyl group, a C1-6 alkylcarbonyl group, a C1-6 alkylsulfonyl group, a C3-6 cycloalkyl group, a phenyl group, a phenyloxy group, a cyano group, a nitro group, a tri-C1-6 alkylsilyl group; an amino group substituted with a C1-6 alkyl group or a C1-6 alkylcarbonyl group; and / or a carboxamide group substituted with a C1-6 alkyl. and / or an amino group substituted with a C1-6 alkyl group, a C1-6 haloalkoxy group, a C1-6 alkylcarbonyl group, a C1-6 alkylthio group, a C3-6 cycloalkyl group, a cyano group, a nitro group; and / or a C1-6 alkyl group, even more preferably a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C1-6 alkylthio group, a C3-6 cycloalkyl group, a cyano group, and / or an amino group substituted with a C1-6 alkyl group, and particularly preferably a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C1-6 alkylthio group, a C3-6 cycloalkyl group, a cyano group, and / or an amino group substituted with a C1-6 alkyl group. Among these, the substituent on the "phenyl group" is preferably one or more of a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C1-6 alkylthio group, a C3-6 cycloalkyl group, a cyano group, and an amino group substituted with a C1-6 alkyl group, and more preferably one or more of a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C1-6 alkylthio group, a C3-6 cycloalkyl group, a cyano group, and an amino group substituted with a C1-6 alkyl group.The substituent on the "5- to 6-membered heterocyclyl group" is more preferably a C1-6 haloalkyl group, and the substituent on the "thiazolyl group" is more preferably a C1-6 haloalkyl group. １ When the "5- to 6-membered heterocyclyl group", "phenyl group", "naphthyl group" or "9- to 10-membered heterocyclyl group" in Q has a substituent, the number of the substituents is preferably 1 or 2. １ may represent an indanyl group in which two substituents on the phenyl group are taken together to form a trimethylene group.

[0065] Q in formula (Z-I) ２ Q more preferably represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted benzodioxolanyl group, a substituted or unsubstituted benzothiazolyl group, or a substituted or unsubstituted quinolinyl group, and even more preferably represents a substituted or unsubstituted phenyl group. ２ The substituent on the "phenyl group", "naphthyl group", "5- to 6-membered heterocyclyl group", or "9- to 10-membered heterocyclyl group" in the above formula (I) is more preferably a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C1-6 alkoxy group substituted with a C1-6 alkoxy group, a C1-6 alkylthio group, a C1-6 alkylsulfonyl group, a cyano group, or an amino group substituted with a C1-6 alkyl group, and even more preferably a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C1-6 alkoxy group substituted with a C1-6 alkoxy group, a C1-6 alkylthio group, a cyano group, or an amino group substituted with a C1-6 alkyl group. ２ When the "phenyl group", "naphthyl group", "5- to 6-membered heterocyclyl group" or "9- to 10-membered heterocyclyl group" in Q has a substituent, the number of the substituents is preferably 1 or 2, and more preferably 2. ２also preferably denotes an indanyl group in which two substituents on the phenyl group together form a trimethylene group.

[0066] Each symbol in the partial structure of the following formula (III) has the following meaning.

[0067]

[0068] The carbon atoms marked with * and + in the partial structure correspond to the carbon atoms marked with * and + in formula (Z-I). １ represents an oxygen atom, a nitrogen atom, a group of the formula: NR １ or a group represented by the formula: CR ２ represents a group represented by the formula: ２ represents an oxygen atom, a nitrogen atom, a group of the formula: NR １ or a group represented by the formula: CR ２ represents a group represented by the formula: ３ represents an oxygen atom, a nitrogen atom, a group of the formula: NR １ or a group represented by the formula: CR ２ where B represents a group represented by １ , B ２ , and B ３ any one of which is an oxygen atom or a group represented by the formula: NR １ and the remaining two are a nitrogen atom or a group represented by the formula: CR ２ It is a group represented by the formula:

[0069] Specific examples of the partial structure of formula (III) include the following:

[0070]

[0071] R １ R each independently represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C3-6 cycloalkyl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group. ２are each independently 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 C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylcarbonyloxy group, a substituted or unsubstituted C1-6 alkoxycarbonyloxy group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C It represents a 1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5-6 membered heterocyclyl group, a substituted or unsubstituted phenyloxy group, a substituted or unsubstituted naphthyloxy group, a substituted or unsubstituted 5-6 membered heterocyclyloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a nitro group, a cyano group, or a halogeno group.

[0072] R １ and R ２ The "C1-6 alkyl group" in the formula may be a straight chain or a branched chain. １ Examples of the "C1-6 alkyl group" in the above formula include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an i-propyl group, an i-butyl group, an s-butyl group, a t-butyl group, an i-pentyl group, a neopentyl group, a 2-methylbutyl group, an i-hexyl group, and the like.

[0073] R １ and R ２ Examples of the "C3-6 cycloalkyl group" in the above formula include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.

[0074] R ２Examples of the "C2-6 alkenyl group" in the above formula include vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, and 5-hexenyl group.

[0075] R ２ Examples of the "C2-6 alkynyl group" in the above formula include ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl group, and the like.

[0076] R ２ Examples of the "C1-6 alkoxy group" in the above formula include a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group, and a t-butoxy group.

[0077] R ２ Examples of the "C1-6 alkylcarbonyl group" in the above formula include an acetyl group, a propionyl group, an n-propylcarbonyl group, an i-propylcarbonyl group, an n-butylcarbonyl group, and a t-butylcarbonyl group.

[0078] R ２ Examples of the "C1-6 alkoxycarbonyl group" in the above formula include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, an n-butoxycarbonyl group, and a t-butoxycarbonyl group.

[0079] R ２Examples of the "C1-6 alkylcarbonyloxy group" in the above formula include an acetyloxy group, a propionyloxy group, an n-propylcarbonyloxy group, an i-propylcarbonyloxy group, an n-butylcarbonyloxy group, and a t-butylcarbonyloxy group.

[0080] R ２ Examples of the "C1-6 alkoxycarbonyloxy group" in the above formula include a methoxycarbonyloxy group, an ethoxycarbonyloxy group, an n-propoxycarbonyloxy group, an i-propoxycarbonyloxy group, an n-butoxycarbonyloxy group, and a t-butoxycarbonyloxy group.

[0081] R ２ Examples of the "C1-6 alkylthio group" in the above formula include a methylthio group, an ethylthio group, an n-propylthio group, an n-butylthio group, an n-pentylthio group, an n-hexylthio group, an i-propylthio group, and an i-butylthio group.

[0082] R ２ Examples of the "C1-6 alkylsulfinyl group" in the above formula include a methylsulfinyl group, an ethylsulfinyl group, and a t-butylsulfinyl group.

[0083] R ２ Examples of the "C1-6 alkylsulfonyl group" in the above formula include a methylsulfonyl group, an ethylsulfonyl group, and a t-butylsulfonyl group.

[0084] R １ , R ２In the above, examples of the substituent on the "C1-6 alkyl group", "C2-6 alkenyl group", "C2-6 alkynyl group", "C1-6 alkoxy group", "C1-6 alkylcarbonyl group", "C1-6 alkoxycarbonyl group", "C1-6 alkylcarbonyloxy group", "C1-6 alkoxycarbonyloxy group", "C1-6 alkylthio group", "C1-6 alkylsulfinyl group", or "C1-6 alkylsulfonyl group" include a fluoro group, a chloro ... halogeno groups such as a bromo group or an iodo group, hydroxyl group, C alkoxy groups such as a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group or a t-butoxy group, C haloalkoxy groups such as a 2-chloro-n-propoxy group, a 2,3-dichlorobutoxy group or a trifluoromethoxy group, a C cycloalkyl group, a phenyl group, a 5-membered heteroaryl group, a 6-membered heteroaryl group, a cyano group; A phenyl group substituted by one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 5-membered heteroaryl group substituted by one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or a 6-membered heteroaryl group substituted by one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group is preferred, and one or more of a halogeno group, a C1-6 alkoxy group, or a C3-6 cycloalkyl group is more preferred.

[0085] R １ and R ２ The "5- to 6-membered heterocyclyl group" in the above formula (I) is a group containing 1, 2, 3, or 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms as ring constituent atoms. When there are two or more heteroatoms, they may be the same or different. The "5- to 6-membered heterocyclyl group" includes Q １ or Q ２Examples of the heterocyclyl group include those described in the "5- to 6-membered heterocyclyl group" in the above. For example, a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a tetrahydro-2H-pyranyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, a dioxanyl group; a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group, an oxazolinyl group, an isoxazolinyl group; a dihydropyranyl group; a pyrrolyl group, a furanyl group, a tetrahydro-2H-pyranyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxanyl group; a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group, an oxazolinyl group, an isoxazolinyl group; a dihydropyranyl group; a pyrrolyl group, a furanyl group, a tetrahydro-2H-py ... a pyrrolidinyl group, a dihydrofuranyl group, a pyrrolidinyl group, a tetrahydro-2H-pyranyl group, Examples thereof include an aryl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, a tetrazolyl group; a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, and the like, and a pyrazolinyl group, a thiazolyl group, or a pyridyl group is preferred, and a thiazolyl group or a pyridyl group is more preferred.

[0086] R ２ Examples of the "5- to 6-membered heterocyclyloxy group" in the above formula include a pyrrolidinyloxy group, a tetrahydrofuranyloxy group, a thiazolidinyloxy group, a tetrahydro-2H-pyranyloxy group, a piperidyloxy group, a piperazinyloxy group, a morpholinyloxy group, a dioxolanyloxy group, a dioxanyloxy group; a pyrrolinyloxy group, a dihydrofuranyloxy group, an imidazolinyloxy group, a pyrazolinyloxy group, an oxazolinyloxy group, an isoxazolinyloxy group; a dihydropyranyloxy group, and the like.

[0087] R １ , R ２In the above, substituents on the "C3-6 cycloalkyl group", "phenyl group", "naphthyl group", "5- to 6-membered heterocyclyl group", "phenyloxy group", "naphthyloxy group", and "5- to 6-membered heterocyclyloxy group" include a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a hydroxyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, a 5-membered heteroaryl group, a 6-membered heteroaryl group, and a cyano group; a phenyl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 5-membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or A 6-membered heteroaryl group substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group is preferred, and a halogeno group is more preferred.

[0088] R ２ The "amino group" in ２ A "substituted amino group" is a group represented by NH ２ The hydrogen atoms in the group represented by the formula (I) are substituted with other groups.

[0089] R ２ The "aminocarbonyl group" in ２ A "substituted aminocarbonyl group" is a group represented by NH ２ The hydrogen atom in the group represented by CO is substituted with something other than the hydrogen atom.

[0090] R ２Examples of the substituent on the "amino group" or "aminocarbonyl group" in the above formula (I) are preferably 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.

[0091] R ２ Examples of the "halogeno group" in the above formula include a fluoro group, a chloro group, a bromo group, and an iodo group.

[0092] Among these, R １ are each independently preferably a C1-6 alkyl group; a C1-6 alkyl group substituted with a halogeno group, a C1-6 alkoxy group, or a C3-6 cycloalkyl group; a C3-6 cycloalkyl group; or a 5- or 6-membered heterocyclyl group, more preferably a C1-6 alkyl group; a C1-6 alkyl group substituted with a halogeno group, a C1-6 alkoxy group, or a C3-6 cycloalkyl group; a C3-6 cycloalkyl group; a thiazolyl group, or a pyridyl group, and even more preferably a C1-6 alkyl group; a C1-6 alkyl group substituted with a halogeno group, a C1-6 alkoxy group, or a C3-6 cycloalkyl group; or a C3-6 cycloalkyl group. R ２preferably each independently represent a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a cyano group, or a halogeno group, and more preferably represent a hydrogen atom; a C1-6 alkyl group; a C3-6 cycloalkyl group; a cyano group; or a halogeno group.

[0093] The partial structure of formula (III) is preferably the partial structure of formula (III-1), the partial structure of formula (III-2), the partial structure of formula (III-4), the partial structure of formula (III-5), the partial structure of formula (III-6), the partial structure of formula (III-9), or the partial structure of formula (III-15), more preferably the partial structure of formula (III-1), the partial structure of formula (III-2), the partial structure of formula (III-5), or the partial structure of formula (III-15), and even more preferably the partial structure of formula (III-1) or the partial structure of formula (III-5).

[0094] The partial structure of the formula (III-1) is preferably a partial structure of the following formula (III-1-a): ２ａ represents a hydrogen atom, a C1-6 alkyl group, a C3-6 cycloalkyl group, a cyano group, or a halogeno group, and preferably represents a hydrogen atom, a C1-6 alkyl group, a C3-6 cycloalkyl group, or a halogeno group.

[0095]

[0096] Z in formula (Z-I) ａ represents an oxygen atom or a sulfur atom. ａ is preferably an oxygen atom.

[0097] T in formula (ZI) represents the partial structure (T-1) or the partial structure (T-2).

[0098]

[0099] In the partial structures (T-1) and (T-2), the arrow with + is bonded to the carbon atom with + in the partial structure of the formula (III), and the other arrow is bonded to the carbon atom with + in the formula (Z-I). ７ It bonds to the nitrogen atom of

[0100] Z in the partial structure (T-1) represents an oxygen atom or a sulfur atom, and preferably represents an oxygen atom.

[0101] R in partial structure (T-1) ６ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a formyl group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group.

[0102] R ６ In the above, "substituted or unsubstituted C1-6 alkyl group", "substituted or unsubstituted C2-6 alkenyl group", "substituted or unsubstituted C2-6 alkynyl group", "substituted or unsubstituted C1-6 alkylcarbonyl group", "substituted or unsubstituted C1-6 alkoxycarbonyl group", "substituted or unsubstituted C3-6 cycloalkyl group", "substituted or unsubstituted phenyl group", "substituted or unsubstituted naphthyl group", and "substituted or unsubstituted 5- to 6-membered heterocyclyl group" are R ２ Among these, R in the partial structure (T-1) ６ is preferably a hydrogen atom or an unsubstituted C1-6 alkyl group, more preferably a hydrogen atom.

[0103] In the partial structure (T-2), Z ｂ represents a C1-6 alkoxy group or a C1-6 alkylthio group. ｂ The "C1-6 alkoxy group" and "C1-6 alkylthio group" in R ２ Among these, Z in the partial structure (T-2) can be mentioned. ｂ is preferably a methoxy group or a methylthio group.

[0104] Among these, T in formula (Z-1) preferably represents the partial structure (T-1).

[0105] R in formula (Z-I) ４ each independently 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- or 6-membered heterocyclyl group, or a halogeno group.

[0106] R in formula (Z-I) ５ each independently 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- or 6-membered heterocyclyl group, or a halogeno group.

[0107] R ４ and R ５ In the above, "substituted or unsubstituted C1-6 alkyl group", "substituted or unsubstituted C2-6 alkenyl group", "substituted or unsubstituted C2-6 alkynyl group", "substituted or unsubstituted C3-6 cycloalkyl group", "substituted or unsubstituted phenyl group", "substituted or unsubstituted naphthyl group", "substituted or unsubstituted 5- to 6-membered heterocyclyl group", and "halogeno group" are R ２ The same examples as those given above can be mentioned.

[0108] R on the same carbon atom ４ and R ５ may combine with each other to form a divalent organic group. Examples of the divalent organic group include C2-5 alkylene groups such as dimethylene, trimethylene, and tetramethylene.

[0109] Among these, R in formula (Z-I) ４ and R ５is preferably a hydrogen atom or a C1-6 alkyl group, more preferably a hydrogen atom.

[0110] R in formula (Z-I) ７ 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 group of the formula: R ｃ a group represented by —CO—, a group represented by the formula: R ｃ a group represented by —CS—, a group represented by the formula: R ｃ a group represented by —CO—CO—, R ｃ -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- or 6-membered heterocyclyl group, or a cyano group.

[0111] R ７ In the above, "substituted or unsubstituted C1-6 alkyl group", "substituted or unsubstituted C2-6 alkenyl group", "substituted or unsubstituted C2-6 alkynyl group", "substituted or unsubstituted C3-6 cycloalkyl group", "substituted or unsubstituted phenyl group", "substituted or unsubstituted naphthyl group", and "substituted or unsubstituted 5- to 6-membered heterocyclyl group" are R ２ The same examples as those given above can be mentioned.

[0112] R ｃ each independently represent 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, or a substituted or unsubstituted 3-6 membered heterocyclyloxy group.

[0113] R ｃIn the above, "substituted or unsubstituted C1-6 alkyl group", "substituted or unsubstituted C1-6 alkoxy group", "substituted or unsubstituted amino group", "substituted or unsubstituted C3-6 cycloalkyl group", "substituted or unsubstituted C1-6 alkylthio group", "substituted or unsubstituted phenyl group", "substituted or unsubstituted naphthyl group", "substituted or unsubstituted 5- to 6-membered heterocyclyl group", and "substituted or unsubstituted 5- to 6-membered heterocyclyloxy group" are R ２ The same examples as those given above can be mentioned.

[0114] R ｃ Examples of the "C3-6 cycloalkoxy group" in the above formula include a cyclopropyloxy group, a cyclobutyloxy group, and a cyclopentyloxy group.

[0115] R ｃ Examples of the "3- to 4-membered heterocyclyl group" in the above formula include an aziridinyl group, an epoxy group, an azetidinyl group, and an oxetanyl group.

[0116] R ｃ Examples of the "3- to 4-membered heterocyclyloxy group" in the above formula include an aziridinyloxy group, an epoxyoxy group, a 3-azetidinyloxy group, and a 3-oxetanyloxy group.

[0117] R ｃIn the above, substituents on the "C3-6 cycloalkoxy group", "3- to 4-membered heterocyclyl group", and "3- to 4-membered heterocyclyloxy group" include a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a hydroxyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, a 5-membered heteroaryl group, a 6-membered heteroaryl group, and a cyano group; a phenyl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 5-membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or A 6-membered heteroaryl group substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group is preferred.

[0118] R ７ represents a hydrogen atom; a C1-6 alkyl group; a C1-6 haloalkyl group; a formyl group; a group of the formula: R ｃ a group represented by the formula: R ｃ A group represented by —CS—; ｃ a group represented by —CO—CO—; R ｃ -SO ２ -; or a phenyl group substituted with a C1-6 alkyl group is preferred, and a formyl group, a group represented by the formula: R ｃ a group represented by —CO—, a group represented by the formula: R ｃ a group represented by —CS—, a group represented by the formula: R ｃ a group represented by —CO—CO—, or R ｃ -SO ２ A group represented by the formula: R ｃ A group represented by —CO— is even more preferred. ｃare preferably each independently a C1-6 alkyl group; a C1-6 haloalkyl group; a C1-6 alkyl group substituted with a C1-6 alkoxy group; a C1-6 alkoxy group; a C1-6 haloalkoxy group; a C1-6 alkoxy group substituted with a C3-6 cycloalkyl group; a C1-6 alkoxy group substituted with a phenyl group; a C3-6 cycloalkoxy group; a C1-6 alkylthio group; an amino group substituted with a C1-6 alkyl group; a C3-6 cycloalkyl group; a phenyl group; a pyrazolyl group substituted with a C1-6 alkyl group; an oxetanyl group; or an oxetanyloxy group, and more preferably represent a C1-6 alkyl group; a C1-6 alkyl group substituted with a C1-6 alkoxy group; a C1-6 alkoxy group; a C1-6 alkoxy group substituted with a C3-6 cycloalkyl group; a C1-6 alkoxy group substituted with a phenyl group; a C3-6 cycloalkoxy group; or an oxetanyloxy group.

[0119] n is the number of repetitions of the structural unit in [ ] and represents an integer of 1 to 3. n is preferably 1 or 2, and more preferably 1.

[0120] The 5-membered heteroaryl compound of the present invention is preferably a compound represented by formula (I) (hereinafter, may be referred to as compound (I)) or a salt thereof. Each symbol in formula (I) has the same meaning as in formula (Z-I).

[0121]

[0122] An example of the 5-membered heteroaryl compound of the present invention is a compound represented by the following formula (IA) or a salt thereof. Each symbol in formula (IA) has the same meaning as in formula (Z-I), and R ７ａ is a formyl group, the formula: R ｃ a group represented by —CO—, a group represented by the formula: R ｃ a group represented by —CS—, a group represented by the formula: R ｃ a group represented by —CO—CO—, or R ｃ -SO ２ represents a group represented by -. ｃ is the R ７ is the same as defined in ７ａis preferably represented by the formula: R ｃ It represents a group represented by —CO—.

[0123]

[0124] The salt of compound (Z-I) is not particularly limited as long as it is an agriculturally and horticulturally acceptable salt. Examples of the salt of compound (Z-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; and salts of organic bases such as triethylamine, tributylamine, pyridine, and hydrazine.

[0125] The method for producing compound (Z-I) or a salt of compound (Z-I) is not particularly limited. For example, compound (Z-I) or a salt of compound (Z-I) can be obtained by a known production method described in the Examples, etc. Furthermore, a salt of compound (Z-I) can be obtained from compound (Z-I) by a known method.

[0126] Methods for Producing Compound (I) Production Method 1 The compound of formula (I-1) can be produced by a method comprising a step of reacting a compound of formula (im-1) with a compound of formula (im-2), as shown in Scheme 1.

[0127]

[0128] Here, the compound of formula (I-1) is a compound (I) in which R ７ is a formyl group, formula: R ｃ a group represented by —CO—, a group represented by the formula: R ｃ a group represented by —CS—, a group represented by the formula: R ｃ a group represented by —CO—CO—, or R ｃ -SO ２ -" (hereinafter referred to as R ７ａ It is a compound that is sometimes written as R ７ａ is preferably represented by the formula: R ｃThe compound of formula (im-1) is a compound in which G is a halogeno group and the other symbols are the same as defined in the compound of formula (I-1). The compound of formula (im-2) is a compound in which the symbols are the same as defined in the compound of formula (I-1).

[0129] The compound of formula (I-1) can be produced by reacting the compound of formula (im-1) with the compound of formula (im-2) by a well-known method. The reaction may be carried out in the presence of an acid scavenger. Examples of the acid scavenger include common inorganic bases and organic bases, and alkali metal carbonates, alkaline earth metal acetates, tertiary amines, or aromatic amines are preferably used. The reaction temperature is appropriately set, but is, for example, about 60°C to 120°C. The reaction time is appropriately set, but is, for example, about 1 hour to 24 hours.

[0130] Compounds of formula (im-2) may be commercially available or may be prepared by known methods. Compounds of formula (im-1) may be prepared by one or more of the methods described herein (see Preparation Method 4).

[0131] Preparation Method 2 The compound of formula (I-2) can be prepared by a method comprising the step of reacting a compound of formula (im-3) with a compound of formula (im-4), as shown in Scheme 2.

[0132]

[0133] Here, the compound of formula (I-2) is a compound (I) having Z ａ is oxygen, and R ７ is a formyl group, formula: R ｃ a group represented by —CO—, a group represented by the formula: R ｃ a group represented by —CS—, a group represented by the formula: R ｃ a group represented by —CO—CO—, or R ｃ -SO ２ -" (hereinafter referred to as R ７ａ It is a compound that is sometimes written as R ７ａ is preferably of the formula: R ｃThe compound of formula (im-3) is a compound in which the symbols are the same as those defined in the compound of formula (I-2). The compound of formula (im-4) is a compound represented by Q １ is a compound which is the same as defined in the compound of formula (I-2).

[0134] The compound of formula (I-2) can be produced by reacting the compound of formula (im-3) with the compound of formula (im-4) using oxygen as an oxidant in the presence of an organic base and a copper catalyst. This is the so-called Chang-Lam-Evans coupling. The copper catalyst is not particularly limited, but divalent copper catalysts such as copper(II) chloride, copper(II) bromide, copper(II) oxide, copper(II) acetate, copper(II) sulfate, copper(II) bis(2,2,6,6-tetramethyl-3,5-heptanedioate), and copper(II) trifluoromethanesulfonate are used, with copper(II) acetate being preferred. The organic base is not particularly limited, but tertiary amines such as triethylamine and aromatic amines such as pyridine are used, with aromatic amines such as pyridine being preferred. The reaction temperature is set appropriately, but is, for example, about 0°C to 40°C. The reaction time is set appropriately, but is, for example, about 6 to 48 hours.

[0135] Compounds of formula (im-4) are commercially available or may be prepared by known methods. Compounds of formula (im-3) can be prepared by one or more of the methods described herein (see Preparation Method 5).

[0136] Preparation Method 3 The compound of formula (I-3) can be prepared by a method comprising the step of reacting a compound of formula (im-5) with a compound of formula (im-6), as shown in Scheme 3.

[0137]

[0138] The compound of formula (I-3) is a compound of formula (I) in which Z is an oxygen atom and R ７ is a formyl group, formula: R ｃ a group represented by —CO—, a group represented by the formula: R ｃ a group represented by —CS—, a group represented by the formula: R ｃa group represented by —CO—CO—, or R ｃ -SO ２ -" (hereinafter referred to as R ７ａ It is a compound that is sometimes written as R ７ａ is preferably of the formula: R ｃ The compound of formula (im-5) is a group represented by U １ is a hydroxyl group or a halogeno group, preferably a hydroxyl group. The other symbols are the same as those defined in the compound of formula (I). The compound of formula (im-6) is a compound in which the symbols are the same as those defined in the compound of formula (I-3).

[0139] The compound of formula (I-3) is U １ is a hydroxyl group, with a compound of formula (im-6) in the presence of a condensation reagent. Examples of the condensation reagent 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), carbonyldiimidazole, etc. The reaction temperature is appropriately set, but is, for example, about 0°C to 40°C. The reaction time is appropriately set, but is, for example, about 1 hour to 24 hours.

[0140] In addition, the compound of formula (I-3) can be １is 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 for example, a tertiary amine such as triethylamine or diisopropylethylamine is preferably used. The condensation reagent is not particularly limited, but for example, 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-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU), propylphosphonic anhydride, etc. can be used, and carbodiimide salts (1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride) and HATU are preferably used. The reaction temperature is set appropriately, for example, about 0° C. to 40° C. The reaction time is set appropriately, for example, about 1 hour to 24 hours.

[0141] The compound of formula (I-3) is U １ It can also be prepared by reacting a compound of formula (im-5), in which is a halogen atom, with a compound of formula (im-6) in the presence of an acid scavenger by a well-known method. Examples of the acid scavenger include common inorganic bases and organic bases, and alkali metal carbonates, alkaline earth metal acetates, tertiary amines, or aromatic amines are preferably used.

[0142] The compound of formula (im-5) may be commercially available or may be prepared according to the methods described in the literature (e.g., JP-T-2022-508277A and JP-T-2022-514651A). It can also be prepared by one or more of the methods described herein (see Preparation Methods 6 and 7). The compound of formula (im-6) may be commercially available or may be prepared by one or more of the methods described herein (see Preparation Methods 8 and 9).

[0143] Here, the compound of formula (I-3) can be converted to a compound in which Z is a sulfur atom by using a thione oxidizing agent. Examples of thione oxidizing agents include, but are not limited to, sulfur, hydrosulfic acid, sodium sulfide, sodium hydrosulfide, boron trisulfide, bis(diethylaluminum) sulfide, ammonium sulfide, phosphorus pentasulfide, Lawesson's reagent, and the like. If necessary, the reaction may be carried out in the presence of an inorganic base or an organic base. Alkali metal carbonates, alkaline earth metal acetates, tertiary amines, or aromatic amines are preferred.

[0144] Preparation Method 4 The compound of formula (im-1a) can be prepared by a method comprising the step of reacting a compound of formula (im-7) with a compound of formula (im-6), as shown in Scheme 4.

[0145]

[0146] The compound of formula (im-1a) is a compound of formula (im-1) in which Z is an oxygen atom. The compound of formula (im-7) is a compound of formula (im-7) in which G is a halogeno group and U １ is a hydroxyl group or a halogeno group, and the other symbols are the same as defined in the compound of formula (im-1). The reagents and reaction conditions used in Production Method 4 can be the same as those described in Production Method 3.

[0147] The compound of formula (im-7) may be commercially available.

[0148] Here, the compound of formula (im-1a) can be converted into a compound in which Z is a sulfur atom by using a thione oxidizing agent. The conversion method can be the same as that described in Production Method 3.

[0149] Preparation Method 5 The compound of formula (im-3a) can be prepared by a method comprising the step of reacting a compound of formula (im-8) with a compound of formula (im-6), as shown in Scheme 5.

[0150]

[0151] Here, the compound of formula (im-3a) is a compound of formula (im-3) in which Z is an oxygen atom. The compound of formula (im-8) is a compound of formula (im-8) in which U １ is a hydroxyl group or a halogeno group, preferably a hydroxyl group. The other symbols are the same as those defined in the compound of formula (im-3). The reagents and reaction conditions used in Production Method 5 can be the same as those described in Production Method 3.

[0152] Compounds of formula (im-8) may be commercially available or may be prepared by one or more of the methods described herein (see Preparation Method 7).

[0153] Here, the compound of formula (im-3a) can be converted into a compound in which Z is a sulfur atom by using a thione oxidizing agent. The conversion method can be the same as that described in Production Method 3.

[0154] Preparation Method 6 The compound of formula (im-5) can be prepared by a method comprising the steps of reacting the compound of formula (im-9) with the compound of formula (im-2), and converting the compound of formula (im-10) obtained by the reaction into the compound of formula (im-5), as shown in Scheme 6.

[0155]

[0156] The compound of formula (im-9) is U ２ is a C1-6 alkoxy group, G is a halogeno group, and the other symbols are the same as defined in the compound of formula (im-5). ２ is a C1-6 alkoxy group, and the other symbols are the same as defined in the compound of formula (im-5).

[0157] The compound of formula (im-10) can be produced by reacting the compound of formula (im-9) with the compound of formula (im-2) by a well-known method. The reaction may be carried out in the presence of an acid scavenger. Examples of the acid scavenger include common inorganic bases and organic bases. Alkali metal carbonates, alkaline earth metal acetates, tertiary amines, or aromatic amines are preferred, with alkali metal carbonates such as cesium carbonate and tertiary amines such as dimethylglycine being more preferred. A copper catalyst such as copper iodide may also be used in combination. The reaction temperature may be appropriately set, but is, for example, about 100°C to 200°C. The reaction time may be appropriately set, but is, for example, about 0.5 hours to 6 hours.

[0158] U １ The compound of formula (im-5) in which is a hydroxyl group can be produced by hydrolyzing the compound of formula (im-10) under acidic or basic conditions. Examples include a method using trifluoroacetic acid under acidic conditions, and a method using lithium hydroxide under basic conditions in a mixed solvent system of tetrahydrofuran (THF) and water, or a mixed solvent system of an alcohol such as methanol, THF, and water. Among these, the method using basic conditions is preferred. The hydrolysis temperature is appropriately set, but is, for example, about 0°C to 60°C. The hydrolysis time is appropriately set, but is, for example, about 1 hour to 24 hours. U １ The compound of formula (im-5) in which is a halogeno group is １ The compound of formula (im-5) can be produced by reacting the compound of formula (im-5) in which is a hydroxyl group with a halogenating reagent.

[0159] The compound of formula (im-9) may be commercially available or may be prepared by known methods.

[0160] Preparation Method 7 The compound of formula (im-5a) can be prepared by a method comprising the steps of reacting the compound of formula (im-12) with formula (im-13) and converting the compound of formula (im-10a) obtained by the reaction into the compound of formula (im-5a), as shown in Scheme 7. Also, the compound of formula (im-8a) can be prepared by a method comprising the step of converting the compound of formula (im-12). The compound of formula (im-12) can also be prepared by a method comprising the steps of reacting the compound of formula (im-11) with a boron compound and oxidizing the compound.

[0161]

[0162] Here, the compound of formula (im-5a) is a compound of formula (im-5) in which Z ａ is a compound in which the oxygen atom is

[0163] The compound of formula (im-11) is U ２ is a C1-6 alkoxy group, and the other symbols are the same as defined in the compound of formula (Z-I). ２ is a C1-6 alkoxy group, and the other symbols are the same as defined in the compound of formula (Z-I). １ is a compound having the same definition as in the compound of formula (Z-I). ２ is a C1-6 alkoxy group, and the other symbols are the same as defined in the compound of formula (Z-I). The compound of formula (im-8a) is the same as the compound of formula (im-8).

[0164] The compound of formula (im-10a) can be produced by reacting the compound of formula (im-12) with the compound of formula (im-13) using oxygen as a reoxidant in the presence of an organic base and a copper catalyst. This is the so-called Chang-Lam-Evans coupling. The copper catalyst is not particularly limited, but divalent copper catalysts such as copper(II) chloride, copper(II) bromide, copper(II) oxide, copper(II) acetate, copper(II) sulfate, copper(II) bis(2,2,6,6-tetramethyl-3,5-heptanedioate), and copper(II) trifluoromethanesulfonate can be used, with copper(II) acetate being preferred. The organic base is not particularly limited, but tertiary amines such as triethylamine and aromatic amines such as pyridine can be used, with aromatic amines such as pyridine being preferred. The reaction temperature is set appropriately, but is, for example, approximately 0°C to 40°C. The reaction time is set appropriately, but is, for example, approximately 6 to 48 hours.

[0165] U １ The compound of formula (im-5a) in which is a hydroxyl group can be produced by hydrolyzing the compound of formula (im-10a) under acidic or basic conditions. Examples include a method using trifluoroacetic acid under acidic conditions, and a method using lithium hydroxide under basic conditions in a mixed solvent system of THF and water, or a mixed solvent system of an alcohol such as methanol, THF, and water. Among these, the method using basic conditions is preferred. The hydrolysis temperature is appropriately set, but is, for example, about 0°C to 60°C. The hydrolysis time is appropriately set, but is, for example, about 1 hour to 24 hours. U １ The compound of formula (im-5a) in which is a halogeno group is １ The compound of formula (im-5a) can be produced by reacting the compound of formula (im-5a) in which is a hydroxyl group with a halogenating reagent.

[0166] U １The compound of formula (im-8a) in which is a hydroxyl group can be produced by hydrolyzing the compound of formula (im-12) under acidic or basic conditions. Examples include a method in which trifluoroacetic acid is used under acidic conditions, and a method in which lithium hydroxide is used in a mixed solvent of THF and water under basic conditions. Among these, the method in which acidic conditions are used is preferred. The hydrolysis temperature is appropriately set, but is, for example, about 0°C to 60°C. The hydrolysis time is appropriately set, but is, for example, about 1 hour to 24 hours. U １ The compound of formula (im-8a) in which is a halogeno group is １ The compound of formula (im-8a) can be produced by reacting the compound of formula (im-8a) in which is a hydroxyl group with a halogenating reagent.

[0167] The compound of formula (im-13) may be commercially available or may be prepared by known methods.

[0168] The compound of formula (im-12) may be commercially available or may be produced by a known method. Alternatively, the compound of formula (im-12) can be produced by reacting the compound of formula (im-11) with a boron compound in the presence of a palladium catalyst to convert it into an organoboron compound, followed by oxidation. The method for converting it into an organoboron compound is the so-called Miyaura-Ishiyama boronation reaction. The palladium catalyst is not particularly limited, and examples thereof include tetrakis(triphenylphosphine)palladium(0), bis(dibenzylideneacetone)palladium(0), tris(dibenzylideneacetone)dipalladium(0), bis(triphenylphosphine)palladium(II) dichloride, [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), and [1,1'-bis(di-tert-butylphosphino)ferrocene]dichloropalladium(II), with [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) being preferred. The boron compound is not particularly limited, and examples thereof include bis(pinacolato)diborane, pinacolborane, and diboronic acid, with bis(pinacolato)diboron being preferred. The obtained organoboron compound can be oxidized with hydrogen peroxide under basic conditions to produce a compound of formula (im-12), in which the carbon-boron bond is replaced with a carbon-oxygen bond. The compound of formula (im-11) may be commercially available or may be produced by a known method.

[0169] Preparation Method 8 As shown in Scheme 8, the compound of formula (im-6a) can be prepared by a method comprising a step of reacting the compound of formula (im-19) with the compound of formula (im-20), and a step of reacting the compound of formula (im-21) obtained by the reaction with a hydrazine.

[0170]

[0171] Here, the compound of formula (im-6a) is a compound of formula (im-6) in which R ６ is a hydrogen atom. The compound of formula (im-19) is a compound in which R ７ａis the same as defined in the compound of formula (im-6). The compound of formula (im-20) is ３ is a hydroxyl group or a halogeno group, and the other symbols are the same as defined in the compound of formula (im-6). The compound of formula (im-21) is a compound in which the symbols are the same as defined in the compound of formula (im-6).

[0172] The compound of formula (im-21) is U ３ is a hydroxyl group, with a compound of formula (im-19) in the presence of a dialkyl azodicarboxylate and triphenylphosphine. This is the so-called Mitsunobu reaction. Examples of dialkyl azodicarboxylates include, but are not limited to, diethyl azodicarboxylate and diisopropyl azodicarboxylate.

[0173] The compound of formula (im-21) is U ３ The compound of formula (im-20), in which is a halogen atom, can be produced by reacting the compound of formula (im-19) with the compound of formula (im-19) in the presence of an acid scavenger by a well-known method. The reaction time is appropriately set, for example, about 1 hour to 24 hours. The reaction temperature is appropriately set, for example, about 0°C to 100°C. Examples of the acid scavenger include common inorganic bases and organic bases. Alkali metal carbonates such as potassium carbonate, alkaline earth metal acetates, tertiary amines, or aromatic amines are preferred, and alkali metal carbonates are more preferred.

[0174] The compound of formula (im-6a) can be produced by reacting the compound of formula (im-21) with a hydrazine. The hydrazine is not particularly limited, but for example, hydrazine monohydrate, methylhydrazine, etc. can be used, with hydrazine monohydrate being preferred. The compound of formula (im-19) may be commercially available, or may be a compound of formula: NH ２ -NH-R ７ａ A compound represented by the formula (R ７ａis the same as defined in the compound of formula (im-6). The compound of formula (im-20) may be commercially available or may be prepared by a known method.

[0175] Preparation Method 9 The compound of formula (im-6c) can be prepared by a method comprising the step of reacting the compound of formula (im-6a) with the compound of formula (im-23), as shown in Scheme 9.

[0176]

[0177] Here, the compound of formula (im-6c) is a compound of formula (im-6) in which R ６ is a group other than a hydrogen atom (hereinafter referred to as R ６ａ The compound of formula (im-23) is a compound represented by the formula G ２ is a halogeno group, and R ６ａ is a compound which is the same as defined in formula (im-6c).

[0178] The compound of formula (im-6c) can be produced by reacting the compound of formula (im-6a) with the compound of formula (im-23). ​​The reaction is preferably carried out in the presence of an inorganic base. The compound of formula (im-23) may be commercially available or may be produced by a known method.

[0179] Preparation Method 10 The compound of formula (im-5c) can be prepared by a method comprising the steps of reacting the compound of formula (im-24) with the compound of formula (im-2a), and converting the compound of formula (im-25) obtained by the reaction into the compound of formula (im-5c), as shown in Scheme 10.

[0180]

[0181] In the compound of formula (im-24), G is a halogeno group, and R １ａ is a compound having the same definition as that in the compound of formula (im-5B) below. １is a compound having the same definition as that in the compound of formula (im-5B) below. １ and R １ａ is the same as defined in the compound of formula (im-5B) below. １ represents a hydroxyl group or a halogeno group, and Q １ and R １ａ is the same as defined in the compound of the following formula (im-5B).

[0182] The compound of formula (im-25) can be produced by reacting the compound of formula (im-24) with the compound of formula (im-2a) by a well-known method. The reaction may be carried out in the presence of an acid scavenger. Examples of the acid scavenger include common inorganic bases and organic bases. Alkali metal carbonates, alkaline earth metal acetates, tertiary amines, or aromatic amines are preferred, and alkali metal carbonates such as potassium carbonate and cesium carbonate, and tertiary amines such as dimethylglycine are more preferred. The reaction temperature is appropriately set, but is, for example, about 100°C to 200°C. The reaction time is appropriately set, but is, for example, about 0.5 hours to 6 hours.

[0183] U １ The compound of formula (im-5c) in which is a hydroxyl group can be produced by hydrolyzing the compound of formula (im-25) under acidic or basic conditions. Examples include a method using trifluoroacetic acid under acidic conditions, and a method using lithium hydroxide under basic conditions in a mixed solvent system of tetrahydrofuran (THF) and water, or a mixed solvent system of an alcohol such as methanol, THF, and water. Among these, the method using basic conditions is preferred. The hydrolysis temperature is appropriately set, but is, for example, about 0°C to 60°C. The hydrolysis time is appropriately set, but is, for example, about 1 hour to 24 hours.

[0184] Alternatively, when an amide is obtained without hydrolyzing to a carboxylic acid using an aqueous solution of an alkali metal hydroxide such as sodium hydroxide in an alcohol solvent such as ethanol, the carboxylic acid can be obtained by reacting with sodium nitrite and a nitrite ester in an acetic acid solvent. The reaction temperature is appropriately set, but is, for example, about 0°C to 100°C, preferably about 0°C to 10°C. The hydrolysis time is appropriately set, but is, for example, about 1 hour to 6 hours.

[0185] U １ The compound of formula (im-5c) in which is a halogeno group is １ is a hydroxyl group, with a halogenating reagent. Compounds of formula (im-24) may be commercially available or may be prepared by known methods.

[0186] Method for producing compound (I') In compound (Z-I), when T in formula (Z-I) is partial structure (T-2), the compound is represented by the following formula (I'): Each symbol in formula (I') has the same meaning as in formula (Z-I).

[0187]

[0188] The compound represented by formula (I') (hereinafter sometimes referred to as compound (I')) is ｂ When Z is a C1-6 alkylthio group, it can be produced by thioamidating compound (I) using a thione oxidizing agent such as Lawesson's reagent, followed by reaction with the corresponding alkyl halide. ｂ When is a C1-6 alkoxy group, it can be produced by reacting with an oxonium salt such as trimethyloxonium tetrafluoroborate or triethyloxonium tetrafluoroborate.

[0189] Production Intermediates The compound represented by the following formula (im-5A) or a salt thereof can be a production intermediate for compound (ZI).

[0190]

[0191] In formula (im-5A), R １and Q １ is the same as defined in the compound of formula (Z-I). １ is preferably a C1-6 alkyl group. １ is preferably a substituted or unsubstituted phenyl group or a substituted or unsubstituted thiazolyl group. The substituent on the "phenyl group" is preferably a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 alkylthio group, a C3-6 cycloalkyl group, or an amino group substituted with a C1-6 alkyl group, and more preferably a halogeno group, a C1-6 alkyl group, or a C1-6 haloalkyl group. The substituent on the "thiazolyl group" is preferably a C1-6 haloalkyl group. R ２ａ represents a C1-6 haloalkyl group, a cyano group, or a halogeno group. ２ａ is preferably a cyano group or a halogeno group. ４ represents a carboxyl group, a C1-6 alkoxycarbonyl group, or a halogenocarbonyl group. ４ is preferably a carboxyl group or a C1-6 alkoxycarbonyl group.

[0192] Production Intermediates The compound represented by the following formula (im-5B) or a salt thereof can be a production intermediate for compound (ZI).

[0193]

[0194] In formula (im-5B), Q １ is the same as defined in the compound of formula (Z-I). １ is preferably a substituted or unsubstituted phenyl group. The substituent on the "phenyl group" is preferably a halogeno group, a C1-6 alkyl group, or a C1-6 haloalkyl group, more preferably a C1-6 haloalkyl group. １ａrepresents a substituted or unsubstituted C2-6 alkyl group or a substituted or unsubstituted C3-6 cycloalkyl group. The substituent on the "C2-6 alkyl group" and the "C3-6 cycloalkyl group" is preferably a halogeno group. Among these, R １ａ is preferably a t-butyl group. ４ represents a carboxyl group, a C1-6 alkoxycarbonyl group, or a halogenocarbonyl group. ４ is preferably a carboxyl group or a C1-6 alkoxycarbonyl group.

[0195] A compound represented by the following formula (d-1) (hereinafter may be referred to as compound (d-1)) or a compound represented by formula (d-2) (hereinafter may be referred to as compound (d-2)) can be a production intermediate for compound (Z-I).

[0196]

[0197] Production Intermediates The compound represented by the following formula (im-25) or a salt thereof can be a production intermediate for compound (ZI).

[0198]

[0199] In formula (im-25), Q １ is the same as defined in the compound of formula (Z-I). １ is preferably a substituted or unsubstituted phenyl group. The substituent on the "phenyl group" is preferably a halogeno group, a C1-6 alkyl group, or a C1-6 haloalkyl group, more preferably a halogeno group or a C1-6 haloalkyl group, and even more preferably a C1-6 haloalkyl group. R １ａ represents a substituted or unsubstituted C2-6 alkyl group or a substituted or unsubstituted C3-6 cycloalkyl group. The substituent on the "C2-6 alkyl group" and the "C3-6 cycloalkyl group" is preferably a halogeno group. Among these, R １ａ is preferably an unsubstituted C2-6 alkyl group, more preferably a t-butyl group.

[0200] The agricultural and horticultural fungicide of the present invention contains at least one active ingredient selected from the group consisting of compound (Z-I) and a salt of compound (Z-I) (hereinafter, sometimes referred to as active ingredient (Z-I)). The amount of active ingredient (Z-I) contained in the agricultural and horticultural fungicide of the present invention is not particularly limited as long as it exhibits a fungicidal effect.

[0201] The agricultural and horticultural fungicide of the present invention can be used to control plant diseases caused by a wide variety of filamentous fungi, for example, fungi belonging to the phylum Oomycetes, Ascomycetes, Deuteromycetes, Basidiomycetes, and Zygomycetes.

[0202] Examples of plant diseases (pathogens) that can be controlled are shown below. Sugar beet: Cercospora beticola, Aphanomyces cochlioides, Root rot (Thanatephorus cucumeris), Leaf rot (Thananatephorus cucumeris), Rust (Uromyces betae), Powdery mildew (Oidium sp.), Spot disease (Ramularia beticola), Seedling damping off (Aphanomyces cochlioides, Pythium ultimum), etc. Peanuts: Mycosphaerella arachidis, Ascochyta sp., Puccinia arachidis, Pythium debaryanum, Alternaria alternata, Sclerotium rolfsII, Mycosphaerella berkeleyi), black root rot (Calonectria ilicicola), etc. Cucumber: Powdery mildew (Sphaerotheca fuliginea), downy mildew (Pseudoperonospora cubensis), vine blight (Mycosphaerella melonis), vine splitting (Fusarium oxysporum), sclerotinia sclerotiorum, gray mold (Botrytis cinerea), anthracnose (Colletotrichum orbiculare), black spot (Cladosporium cucumerinum), brown spot (Corynespora cassIIcola), damping-off (Pythium debaryanum, Rhizoctonia solani Kuhn), Phomopsis root rot (Phomopsis sp.), bacterial spot (Pseudomonas syringae pv. Lachrymans), etc. Tomato: Gray mold (Botrytis cinerea), leaf mold (Cladosporium fulvum), late blight (Phytophthora infestans), hemi-wilt (Verticillium albo-atrum, Verticilliumdahliae), powdery mildew (Oidium neolycopersici), ring blight (Alternaria solani), sooty mold (Pseudocercospora fuligena), bacterial wilt (Ralstonia solanacearum), sclerotinia sclerotiorum, etc. Eggplant: gray mold (Botrytis cinerea), black blight (Corynespora melongenae), powdery mildew (Erysiphe cichoracearum), sooty mold (Mycovellosiella nattrass II), sclerotinia sclerotiorum, verticillium wilt (Verticillium dahliae), brown spot (Phomopsis vexans), etc. Pepper: late blight (Phytophthora capsici), gray mold (Botrytis cinerea), sclerotinia sclerotiorum), anthracnose (Colletotrichum aenigma, Colletotrichum capsici, Colletotrichum fructicola, Colletotrichum jiangxiense), powdery mildew (Leveillula taurica), etc. Strawberry: Gray mold (Botrytis cinerea), powdery mildew (Sphaerotheca humuli), anthracnose (Colletotrichum acutatum, Colletotrichum fragariae), late blight (Phytophthora cactorum), soft rot (Rhizopus stolonifer), chlorosis (Fusarium oxysporum), wilt (Verticillium dahliae), sclerotinia sclerotiorum, etc. Onion: Gray rot (Botrytis all II), gray mold (Botrytis cinerea), white spot leaf blight (Botrytis squamosa), Peronospora destructor, white blight (Phytophthora porri), Ciborinia allII, BotrytisOnions: Soft rot (Pectobacterium carotovorum), Downy mildew (Peronospora destructor), Leaf blight (Pleospora allII), Sclerotinia rot (Sclerotium cepivorum), Rust (Puccinia allII), White spot blight (Botrytis squamosa), Southern blight (Sclerotium rolfsII), Red root rot (Pyrenochaeta terrestris), etc. Garlic: Soft rot (Pectobacterium carotovorum), Downy mildew (Peronospora destructor), Leaf blight (Pleospora allII), Sclerotinia rot (Sclerotium cepivorum), Rust (Puccinia allII), White spot blight (Botrytis squamosa), Southern blight (Sclerotium rolfsII), Red root rot (Pyrenochaeta terrestris), etc. Cabbage: Clubroot (Plasmodiophora brassicae), Soft rot (Erwinia carotovora), Black rot (Xanthomonas campesrtis pv. campestris), Black spot bacterial disease (Pseudomonas syringae pv. maculicola, P. s. pv. alisalensis), Downy mildew (Peronospora parasitica), Sclerotinia rot (Sclerotinia sclerotiorum), Black mold (Alternaria brassicicola), Gray mold (Botrytis cinerea), Root rot (Phoma lingam), Pythium rot (Pythium aphanidermatum, Pythium ultimum), White rust (Albugo macrospora), etc. Lettuce: Rot (Pseudomonas cichorII, Pseudomonas marginalis), Soft rot (Pectobacterium carotovorum), Downy mildew (Bremia lactucae), Gray mold (Botrytis cinerea), Sclerotinia rot (Sclerotinia sclerotiorum), Mirafiori lettuce big-vein ophiovirus, Root rot (Fusarium oxysporum), Foot rot (Rhizoctoniasolani), powdery mildew (Golovinomyces oront II), etc. Green beans: Sclerotinia sclerotiorum, gray mold (Botrytis cinerea), anthracnose (Colletotrichum lindemuthianum), angular spot (Phaeoisariopsis griseola), etc. Peas: Ascocus blight (Mycosphaerella blight), gray mold (Botrytis cinerea), Sclerotinia sclerotiorum, powdery mildew (Erysiphe pisi), etc.

[0203] Apple: Powdery mildew (Podosphaera leucotricha), black spot (Venturia inaequalis), monilinia (Monilinia mali), black spot (Mycosphaerella pomi), canker (Valsa mali), leaf spot (Alternaria mali), red spot (Gymnosporangium yamadae), ring spot (Botryosphaeria berengeriana), anthracnose (Glomerella cingulata, Colletotrichum acutatum), brown spot (Diplocarpon mali), sooty spot (Zygophiala jamaicensis), sooty spot (Gloeodes pomigena), purple root rot (Helicobasidium mompa), white root rot (Rosellinia necatrix), gray mold (Botrytis cinerea), fire blight (Erwinia amylovora), silver leaf (Chondrostereum) purpureum), crown gall (Rhizobium radiobacter, Rhizobium rhizogenes), etc. Plum: Black spot (Cladosporium carpophilum), gray mold (Botrytis cinerea), brown rot (Monilinia mumecola), sooty spot (Peltaster sp.), fruit blister (Taphrina pruni), brown hole (Phloeosporella padi), etc. Persimmon: Powdery mildew (Phyllactinia kakicola), anthracnose (Gloeosporium kaki), angular leaf spot (Cercospora kaki), circular leaf spot (Mycosphaerella nawae), gray mold (Botrytis cinerea), sooty spot (Zygophiala jamaicensis), etc. Peach: Brown rot (Monilinia fructicola, Monilinia fructigena), black spot (Cladosporium carpophilum), Homopsis sp., Boring bacterial disease (Xanthomonas campestris pv.Plum: leaf curl (Taphrina pruni), leaf blister (Taphrina deformans), anthracnose (Colletotrichum gloeosporioides), brown shot hole disease (Phloeosporella padi), kawaratake disease (Coriolus versicolor), etc. Almond: gray mold (Monilinia laxa), spot disease (Stigmina carpophila), scab (Cladosporium carpophilum), leaf swelling disease (Polystigma rubrum), Alternaria leaf spot (Alternaria alternata), anthracnose (Colletotrichum gloeospoides), etc. Peach: gray mold (Monilinia fructicola), anthracnose (Colletotrichum acutatum), black spot disease (Alternaria sp.), Young fruit sclerotinia (Monilinia kusanoi), Brown hole (Mycosphaerella cerasella), Powdery mildew (Podosphaera tridactyla), etc. Grapes: Gray mold (Botrytis cinerea), Powdery mildew (Uncinula necator), Late rot (Glomerella cingulata, Colletotrichum acutatum), Downy mildew (Plasmopara viticola), Black rot (Elsinoe ampelina), Brown spot (Pseudocercospora vitis), Black rot (Guignardia bidwell II), White rot (Coniella castaneicola), Rust (Phakopsora ampelopsidis), White cotton snow (causative agent unidentified), Crown gall (Rhizobium radiobacter, Rhizobium vitis), etc. Pears: Black spot (Venturia nashicola), Red spot (Gymnosporangium asiaticum), black spot (Alternaria kikuchiana), ring spot (Botryosphaeria berengeriana), powdery mildew (Phyllactinia mali), canker (Phomopsis fukush II), brown spot (Stempphylium vesicarium), anthracnose (Glomerella cingulata), etc. Tea: ring spot (Pestalotiopsis longiseta, P. theae), anthracnose (Colletotrichum theae-sinensis), net blight (Exobasidium reticulatum), red burn (Pseudomonas syringae), blight (Exobasidium vexans), etc. Citrus: scab (Elsinoe fawcett II), 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: blossom rot (Pseudomonas marginalis, Pseudomonas syringae, Pseudomonas viridiflava), canker (Pseudomonas syringae), gray mold (Botrytis cinerea), fruit soft rot (Botryosphaeria dothidea, Diaporthe sp., Lasiodiplodia theobromae), sooty spot (Pseudocercospora actinidiae), etc. Olive: anthracnose (Colletotrichum acutatum, Colletotrichum gloeosporioides), peacock spot (Spilocaea oleaginea), etc. Chestnut: anthracnose (Colletotrichum gloeosporioides), etc.

[0204] Wheat: powdery mildew (Blumeria graminis f.sp. tritici), scab (Gibberella zeae, Fusarium avenaceum, Fusarium culmorum, Fusarium crookwellense, Microdochium nivale), brown rust (Puccinia recondita), yellow rust (Puccinia striiformis), brown snow blight (Pythium iwayamai), red snow blight (Monographella nivalis), eyespot (Pseudocercosporella herpotrichoides), leaf blotch (Septoria tritici), glume blotch (Leptosphaeria nodorum), pink snow mold (Typhula incarnata), gray snow mold (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: leaf stripe (Pyrenophora graminea), net blotch (Pyrenophora teres), scald (Rhynchosporium secalis), loose smut (Ustilago tritici, U. nuda), damping-off (Pythium spp., Fusarium spp., Rhizoctonia spp.), seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), etc. Rice: blast (Pyricularia oryzae), sheath blight (Rhizoctonia solani), bakanae disease (Gibberella fujikuroi), sesame leaf blight (Cochliobolusmiyabeanus), damping-off (Pythium graminicola), white leaf blight (Xanthomonas oryzae), bacterial seedling blight (Burkholderia plantar II), brown stripe (Acidovorax avenae), bacterial grain rot (Burkholderia glumae), streak leaf blight (Cercospora oryzae), rice smut (Ustilaginoidea virens), brown rice (Alternaria alternata, Curvularia intermedia), black-bellied rice (Alternaria padwick II), pink rice (Epicoccum purpurascens), etc. Tobacco: Sclerotinia sclerotiorum, powdery mildew (Erysiphe cichoracearum), late blight (Phytophthora nicotianae), etc. Tulip: Gray mold (Botrytis cinerea), brown spot (Botrytis tulipae), leaf rot (Rhizoctonia solani), bulb rot (Fusarium oxysporum), skin rot (Rhizoctonia solani), etc. Roses: black spot (Diplocarpon rosae), powdery mildew (Erysiphe simulans, Podosphaera pannosa), gray mold (Botrytis cinerea), etc. Chrysanthemums: gray mold (Botrytis cinerea), white rust (Puccinia horiana), downy mildew (Paraperonospora minor, Peronospora danica), Pythium damping-off (Pythium aphanidermatum, Pythium dissotocum, Pythium helicoides, Pythium oedochilum, Pythium sylvaticum), damping-off (Rhizoctonia solani), Fusarium damping-off (Fusarium solani), etc. Gerberas: gray mold (Botrytis cinerea), powdery mildew (Podosphaera xanth II), etc. Lily: leaf blight (Botrytis elliptica, Pestalotiopsissp.), Gray mold (Botrytis cinerea), etc. Sunflower: 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), Blast (Pyricularia sp.), Red burn (Pythium aphanidermatum), Anthracnose (Colletotrichum graminicola), etc. Orchardgrass: Powdery mildew (Erysiphe graminis), etc. Soybean: Purple spot (Cercospora kikuch II), Downy mildew (Peronospora manshurica), Stem rot (Phytophthora sojae), Rust (Phakopsora pachyrhizi), Sclerotinia sclerotiorum, Anthracnose (Colletotrichum truncatum), Gray mold (Botrytis cinerea), Black rot (Elsinoe glycines), Black spot (Diaporthe phaseolorum var. sojae), Damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), etc. Potato: Late blight (Phytophthora infestans), Summer blight (Alternaria solani), Black spot (Thanatephorus cucumeris), Verticillium wilt (Verticillium albo-atrum, V. dahliae, V. nigrescens), Black leg (Pectobacterium atrosepticum), soft rot (Pectobacterium carotovorum), gray mold (Botrytis cinerea), common scab (Streptomycesspp.), Sclerotinia sclerotiorum, etc. Yam: Leaf blight (Cylindrosporium dioscoreae), Anthracnose (Colletotrichum gloeosporioides), Blue mold (Penicillium sclerotigenum), etc. Sweet potato: Purple root rot (Helicobasidium mompa), Fusarium oxysporum, etc. Taro: Late blight (Phytophthora colocasiae), Stem rot (Rhizoctonia solani), etc. Ginger: Rhizome rot (Pythium ultimum, Pythium myriotylum), White spot (Phyllosticta zingiberis), etc. Banana: Panama disease (Fusarium oxysporum), Sigatoka disease (Mycosphaerella fijiensis, M. musicola), etc. Mango: Anthracnose (Colletotrichum aenigma), canker (Xanthomonas campestris), stem rot (Diaporthe pseudophoenicicola, Lasiodiplodia theobromae, Lasiodiplodia spp., Neofusicoccum parvum, Neofusicoccum sp.), gray mold (Botrytis cinerea), etc. Rapeseed: Sclerotinia sclerotiorum, root rot (Phoma lingam), black spot (Alternaria brassicae), powdery mildew (Erysiphe cruciferarum, Erysiphe cichoracearum, Oidium matthiolae), downy mildew (Peronospora parasitica), etc. Coffee: Rust (Hemileia vastatrix), anthracnose (Colletotrichum coffeanum), brown eye (Cercospora coffeicola), etc. Sugarcane: Brown rust (Puccinia melanocephala) etc. Corn: Hail leaf spot (Gloeocercospora sorghi), rust (Pucciniasorghi), southern rust (Puccinia polysora), ear smut (Ustilago maydis), southern leaf blight (Cochliobolus heterostrophus), sooty leaf blight (Setosphaeria turcica), damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), etc. Cotton: damping off (Pythium sp.), rust (Phakopsora gossyp II), white mold (Mycosphaerella areola), anthracnose (Glomerella gossyp II), etc. Hops: downy mildew (Pseudoperonospora humuli), powdery mildew (Oidium sp., Podosphaera macularis), gray mold (Botrytis cinerea), etc.

[0205] The agricultural and horticultural fungicide of the present invention is preferably used on plants such as grains, vegetables, root vegetables, potatoes, fruit trees, trees such as tea, coffee and cacao, pasture grasses, turf grasses, and cotton.

[0206] The agricultural and horticultural fungicide of the present invention can be applied to various parts of plants, such as leaves, stems, stalks, flowers, buds, fruits, seeds, sprouts, roots, tubers, tuberous roots, shoots, cuttings, etc. It can also be applied to improved varieties and varieties of these plants, cultivated varieties, mutants, hybrids, and genetically modified organisms (GMOs).

[0207] The agricultural and horticultural fungicide of the present invention can be used for seed treatment, foliage spray, soil application, water surface application, etc., which are carried out to control various diseases that occur in agricultural and horticultural crops including flowers, turf, and pasture grass.

[0208] The agricultural and horticultural fungicide of the present invention may contain other components in addition to the active ingredient (Z-I). Examples of other components include known carriers used for formulation. Examples of other components include conventionally known fungicides, insecticides / miticides, nematicides, soil pesticides, plant regulators, synergists, fertilizers, soil conditioners, animal feed, etc. (hereinafter, sometimes referred to as the active ingredient (II)). The agricultural and horticultural fungicide of the present invention may exhibit a synergistic effect by containing the active ingredient (Z-I) and the active ingredient (II).

[0209] Specific examples of fungicides as the active ingredient (II) that can be mixed or used in combination with the agricultural and horticultural fungicide of the present invention are shown below. (1) Nucleic acid biosynthesis inhibitors: (a) RNA polymerase I inhibitors: benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M, oxadixyl, clozylacon, ofrace; (b) adenosine deaminase inhibitors: bupirimate, dimethirimol, ethirimol; (c) DNA / RNA synthesis inhibitors: hymexazole, octhilinone; (d) DNA topoisomerase II inhibitors: oxolinic acid;

[0210] (2) Mitosis inhibitors and cytostatic agents: (a) β-tubulin polymerization inhibitors: benomyl, carbendazim, chlorphenazole, fuberidazole, thiabendazole, thiophanate, thiophanate methyl, diethofencarb, zoxamide, ethaboxam; (b) cytostatic agents: pencycuron; (c) spectrin-like protein delocalization inhibitors: fluopicolide, fluopimomide;

[0211] (3) Respiratory inhibitors: (a) Complex I-NADH oxidoreductase inhibitors: diflumetrim, tolfenpyrad; (b) Complex II-succinate dehydrogenase inhibitors: benodanil, flutolanil, mepronil, isofetamide, fluopyram, fenfuram, flumecyclox, carboxin, oxycarboxin, thifluzamide, benzovindiflupyr, bixafen, fluxapyroxad, furametpyr, isopyrazam, penflufen, penthiopyrad, sedaxane, boscalid, pydiflumetofen, isoflucipram, pyraziflumid, inpirfluxam; (c) Complex III-ubiquinol oxidase Qo inhibitors: azoxystrobin, cumoxystrobin, methoxystrobin, enoxastrobin, flufenoxystrobin, picoxystrobin, pyraoxystrobin, pyraclostrobin, pyrametostrobin, triclopyricarb, kresoxim-methyl, trifloxystrobin, dimoxystrobin, phenaminestrobin, metominostrobin, orysastrobin, famoxadone, fluoxastrobin, fenamidone, pyribencarb, methyltetraprole, mandestrobin; (d) Complex III-ubiquinol reductase Qi inhibitors: cyazofamid, amisulbrom, fenpicoxamide; (e) oxidative phosphorylation uncouplers: binapacryl, meptyldinocap, dinocap, fluazinam, ferimzone; (f) Oxidative phosphorylation inhibitors (inhibitors of ATP synthase): fentin acetate, fentin chloride, fentin hydroxide; (g) ATP production inhibitors: silthiofam; (h) Complex III: Qx (unknown) inhibitor of cytochrome bc1 (ubiquinone reductase): ametoctradine;

[0212] (4) Amino acid and protein synthesis inhibitors: (a) methionine biosynthesis inhibitors: andoprim, cyprodinil, mepanipyrim, pyrimethanil; (b) protein synthesis inhibitors: blasticidin-S, kasugamycin, kasugamycin hydrochloride, streptomycin, oxytetracycline;

[0213] (5) Signal transduction inhibitors: (a) Signal transduction inhibitors: quinoxyfen, proquinazid; (b) MAP / histidine kinase inhibitors in osmotic signal transduction: fenpiclonil, fludioxonil, chlozolinate, iprodione, procymidone, vinclozolin;

[0214] (6) Lipid and cell membrane synthesis inhibitors: (a) phospholipid biosynthesis, methyltransferase inhibitors: edifenphos, iprobenfos, pyrazophos, isoprothiolane; (b) lipid peroxidizing agents: biphenyl, chloroneb, dicloran, quintozene, tecnazene, tolclofos methyl, etridiazole; (c) agents acting on cell membranes: iodocarb, propamocarb, propamocarb hydrochloride, propamocarb focetylate, prothiocarb; (d) microorganisms that disrupt pathogen cell membranes: Bacillus subtilis, Bacillus subtilis QST713 strain, Bacillus subtilis FZB24 strain, Bacillus subtilis MBI600 strain, Bacillus subtilis D747 strain, Bacillus amyloliquefaciens; (e) Cell membrane disrupting agent: Tea tree extract;

[0215] (7) Cell membrane sterol biosynthesis inhibitors: (a) C14 demethylation inhibitors in sterol biosynthesis: triforine, pyrifenox, pyrisoxazole, fenarimol, flurprimidol, nuarimol, imazalil, imazalil sulfate, oxpoconazole, oxpoconazole fumarate, pefurazoate, prochloraz, triflumizole, biniconazole, azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazol, difenoconazole, diniconazole, diniconazole-M, epoxidized Siconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, fluconazole, fluconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, fluquinconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, prothioconazole, voriconazole, mefentrifluconazole; (b) Inhibitors of Δ14 reductase and Δ8→Δ7-isomerase in sterol biosynthesis: aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph, fenpropidin, piperalin, spiroxamine; (c) Inhibitors of 3-ketoreductase in C4 demethylation in the sterol biosynthesis system: fenhexamid, fenpyrazamine; (d) Inhibitors of squalene epoxidase in the sterol biosynthesis system: pyributicarb, naftifine, terbinafine;

[0216] (8) Cell wall synthesis inhibitors: (a) trehalase inhibitors: validamycin; (b) chitin synthase inhibitors: polyoxin, polyoxolim; (c) cellulose synthase inhibitors: dimethomorph, flumorph, pyrimorph, benthiavalicarb, benthiavalicarb isopropyl, iprovalicarb, valifenalate, mandipropamid;

[0217] (9) Melanin biosynthesis inhibitors (a) Reductase inhibitors of melanin biosynthesis: fthalide, pyroquilon, tricyclazole; (b) Dehydratase inhibitors of melanin biosynthesis: carpropamid, diclocymet, fenoxanil; (c) Polyketide synthesis inhibitors of melanin biosynthesis: tolprocarb;

[0218] (10) Resistance inducers of host plants: (a) Agents acting on the salicylic acid synthesis pathway: acibenzolar-S-methyl; (b) Others: probenazole, tiadinil, isotianil, diclobenthiazox, ipfentrifluconazole, laminarin, giant knotweed extract, phosphorous acid, phosphites;

[0219] (11) Agents of unknown activity: cymoxanil, fosetyl aluminum, phosphoric acid, phosphate salts, tecloftalam, triazoxide, flusulfamide, diclomedine, metasulfocarb, cyflufenamid, metrafenone, pyriophenone, dodine, dodine free base, fluthianil;

[0220] (12) Agents with multiple action sites: copper (copper salts), Bordeaux mixture, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide, ferbam, mancozeb, maneb, mancopper, metiram, polycarbamate, propineb, thiram, zineb, ziram, captan, captafol, folpet, chlorothalonil, dichlofluanid, tolylfluanid, guazatine, guazatine triacetate (also known as iminoctadine triacetate), iminoctadine tribesylate, anilazine, dithianone, chinomethionate, fluorimide;

[0221] (13) Other agents: DBEDC, fluorofolpet, guazatine acetate, bis(8-quinolinolato)copper(II), propamidine, chloropicrin, cyproflam, Agrobacterium, bethoxadin, diphenylamine, methyl isothiocyanate (MITC), mildeomycin, capsaicin, kufuraneb, cyprosulfamide, dazomet, debacarb, dichlorophen, difenzoquat, difenzoquat methylsulfonate, flumetober, fosetyl calcium, fosetyl sodium, irumamycin, natamycin, nitrotar isopropyl, oxamocarb, pyrrolnitrin, tebufloquin, tolnifanide, zaliramide, algophase, amica Luthiazole, oxathiapiprolin, fluoxapiprolin, metiram zinc, benthiazole, triclamide, uniconazole, oxyfenthiin, picarbutrazox, diclobenthiazox, quinofumelin, thiuram, ambam, Agrobacterium radiobacter, Coniothyrium minitans, Pseudomonas fluorescens, Pseudomonas rhodesia, Talaromyces flavus, Trichoderma atroviride, non-pathogenic Erwinia carotovora, Bacillus simplex, Variovorax paradoxus, Lactobacillus plantarum, florylpicoxamide, pyrapropoin, fluindapyr, aminopyrifen, pyridaclomethyl, ipflufenoquin, dipimethitron;

[0222] Specific examples of insecticides, miticides, nematicides, soil pesticides, anthelmintics and the like that can be used as the active ingredient (II) in admixture with or in combination with the agricultural and horticultural fungicide of the present invention are shown below.

[0223] (1) Acetylcholinesterase (AChE) inhibitors (a) Carbamate acetylcholinesterase (AChE) inhibitors: alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, xylylcarb, fenothiocarb, MIPC, MPMC, MTMC, aldoxycarb, alixycarb, aminocarb, bufencarb, cloethocarb, metam sodium, promecarb;(b) organophosphorus acetylcholinesterase (AChE) inhibitors: acephate, azamethiphos, azinphos ethyl, azinphos methyl, cadusafos, chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos methyl, coumaphos, cyanophos, demeton -S- methyl, diazinon, dichlorvos, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, fanflu, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyaphos, isofenphos, isocarbophos, isopropyl = O- (methoxyaminothiophosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton methyl, parathion, para Thionemethyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion, bromophos-ethyl, BRP, carbophenothion, cyanofenphos, CYAP, demeton-S-methylsulfone, dialifos, diclofenthion, dioxabenzophos, etrimphos, fensulfothion, flupyrazophos, fonofos, formothion, fosmetilan, isazophos, iodofenphos, methacrifos, pirimiphos-ethyl, phosphocarb, propafos, protoate, sulprofos;

[0224] (2) GABA-gated chloride ion (chloride ion) channel blockers: acetoprole, chlordane, endosulfan, ethiprole, fipronil, pyrafluprole, pyriprole, camphechlor, heptachlor, dienochlor, flufifrol;

[0225] (3) Sodium channel modulators (a) Pyrethroid sodium channel modulators: acrinathrin, allethrin, d-cis-trans-allethrin, d-trans-allethrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentenyl-isomer, bioresmethrin, cycloprothrin, cyfluthrin, β-cyfluthrin, cyhalothrin, λ-cyhalothrin, γ-cyhalothrin, cypermethrin, α-cypermethrin, β-cypermethrin, θ-cypermethrin Lumethrin, ζ-cypermethrin, cyphenothrin [(1R)-trans isomer], deltamethrin, empenthrin [(EZ)-(1R)-isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, τ-fluvalinate, halfenprox, imiprothrin, kadesrin, permethrin, fenothrin phosphorus [(1R)-trans isomer], prallethrin, pyrethrum, pyrethrin, resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomer], tralomethrin, transfluthrin, allethrin, pyrethrin I, pyrethrin II, profluthrin, dimefluthrin, bioethanomethrin, biopermethrin, transpermethrin, fenfluthrin, fenpyrithrin, flubrocythrinate, flufenprox, metofluthrin, protrifenbut, pyresmethrin, telallethrin, κ-bifenthrin, chloroprallethrin, heptafluthrin, meperfluthrin, ε-metofluthrin, monfluorothrin, ε-monfluorothrin, κ-tefluthrin, tetramethylfluthrin, bioethanomethrin; (b) Sodium channel modulators (DDTs): DDT, methoxychlor;

[0226] (4) Nicotinic acetylcholine receptor (nAChR) competitive modulators: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam, nicotine, sulfoxaflor, flupyradifurone, triflumezopyrim, dichloromezothiazol, flupirimine; (5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators: spinetoram, spinosad; (6) Glutamate-gated chloride ion (chloride ion) channel (GluCl) allosteric modulators: abamectin, emamectin, emamectin benzoate, lepimectin, milbemectin, ivermectin, selamectin, doramectin, eprinomectin, ivermectin, moxidectin, selamectin, milbemycin, milbemycin oxime, nemadectin;

[0227] (7) Juvenile hormone analogues: hydroprene, kinoprene, methoprene, fenoxycarb, pyriproxyfen, diofenolan, epofenonane, triprene; (8) Other non-specific (multi-site) inhibitors: methyl bromide, alkyl halides, chloropicrin, sodium aluminum fluoride, sulfuryl fluoride, borax, boric acid, disodium octaborate, sodium borate, sodium metaborate, tartar emetic, dazomet, metam, metam potassium salt, metam sodium salt; (9) Chordotonal organ TRPV channel modulators: flonicamid, pymetrozine, pyrifluquinazone, afidopiropen; (10) Mites growth inhibitors: clofentezine, diflobidazine, hexythiazox, etoxazole; (11) Microorganism-derived insect midgut membrane disruptors: Proteins found in Bacillus thuringiensis subspecies israerenci, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, Bt crops: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1; Bacillus sphaericus;

[0228] (12) Mitochondrial ATP synthase inhibitors: diafenthiuron, azocyclotine, cyhexatin, fenbutatin oxide, propargite, tetradifon; (13) oxidative phosphorylation uncouplers that disrupt the proton gradient: chlorfenapyr, DNOC, sulfuramide, binapacryl, dinobuton, dinocap; (14) nicotinic acetylcholine receptor (nAChR) channel blockers: bensultap, cartap hydrochloride, nereistoxin, thiocyclam, thiosultap-sodium salt; (15) chitin biosynthesis inhibitors, type 0: bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, buprofezin, fluazuron; (16) chitin biosynthesis inhibitors, type 1: (17) Molting inhibitors: cyromazine; (18) Molting hormone (ecdysone) receptor agonists: chromafenozide, halofenozide, methoxyfenozide, tebufenozide;

[0229] (19) Octopamine receptor agonists: amitraz, demiditraz, chlordimeform; (20) Mitochondrial electron transport chain complex III inhibitors: hydramethylnon, acequinocyl, fluacrypyrim, bifenazate; (21) Mitochondrial electron transport chain complex I inhibitors (METI): fenazaquin, fenpyroximate, pyridaben, pyrimidifen, tebufenpyrad, tolfenpyrad, rotenone; (22) Voltage-dependent sodium channel blockers: indoxacarb, metaflumizone; (23) Acetyl CoA carboxylase inhibitors: spirodiclofen, spiromesifen, spirotetramat, spiropidione; (24) Mitochondrial electron transport chain complex IV inhibitors: aluminum phosphide, calcium phosphide, zinc phosphide, phosphine, cyanide, calcium cyanide, sodium cyanide, potassium cyanide; (25) mitochondrial electron transport chain complex II inhibitors: cyenopyrafen, cyflumetofen, piflubumid;

[0230] (28) Ryanodine receptor modulators: chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide, cyhalodiamide, tetrachlorantraniliprole, tetraniliprole; (29) Chordotonal organ modulator target site unspecified: flonicamide; (30) GABA-gated chloride ion (chloride ion) channel allosteric modulators: broflanilide, fluxamethamide, isocycloceram, afoxolaner, fluralaner, lotineral, sarolaner; (31) Other insecticides, acaricides: Azadirachtin, benzoximate, bifenazate, bromopropylate, chinomethionate, cryolite, dicofol, lime sulfur mixture, mancozeb, pyridalyl, benclotiaz, sulfur, amidoflumet, 1,3-dichloropropene, DCIP, phenisobromorate, benzomate, metaldehyde, chlorbenzilate, clothiazoben, dicyclanil, fenoxacrim, fentrifanil, flubenzimine, fluphenazine, gossiplura, japonirua, methoxadiazone, petroleum oil, potassium oleate, tetrasulfur, triarane, afidopiropen, flufifol, fluensulfone, meperfluthrin, tetramethylfluthrin, tralopyril, dimefluthrin, methylneodecane Amide, fluralaner, afoxolaner, fluxametamide, 5-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-(1H-1,2,4-triazol-1-yl)benzonitrile (CAS: 943137-49-3), broflanilide, other metadiamides, Steinernema carpocapsae, Steinernema glaceri, Pasteuria penetrans, Pecilomyces tenuipes, Pecilomyces fumosoroseus, Beauveria bassiana, Beauveria brongniartii, Metarhizium anisopliae, Verticillium lecanii, acinonapyr, benzpyrimoxane, flometoquin, fluhexafon, oxazosulfil, cyclopyrazoflor.

[0231] (32) Anthelmintics: (a) benzimidazoles: fenbendazole, albendazole, triclabendazole, oxibendazole, mebendazole, oxfendazole, perbendazole, flubendazole, febantel, netobimin, thiophanate, thiabendazole, cambandazole; (b) salicylanilides: closantel, oxyclozanide, rafoxanide, niclosamide; (c) substituted phenols: nitroxynil, nitroscanate; (d) pyrimidines: pyrantel, morantel; (e) imidazothiazoles: levamisole, tetramisole; (f) tetrahydropyrimidines: praziquantel, epsiprantel; (g) other anthelmintics: Cyclodien, riania, clorsulon, metronidazole, demiditraz, piperazine, diethylcarbamazine, dichlorophen, monepantel, tribendimidine, amidantel, thiacetarsamide, melarsomine, arsenamide.

[0232] Specific examples of plant regulators as the active ingredient (II) that can be mixed or used in combination with the agricultural and horticultural fungicide of the present invention are shown below: abscisic acid, kinetin, benzylaminopurine, 1,3-diphenylurea, forchlorfenuron, thidiazuron, chlorfenuron, dihydrozeatin, gibberellin A, gibberellin A4, gibberellin A7, gibberellin A3, 1-methylcyclopropane, N-acetylaminoethoxyvinylglycine (also known as abiglycine), aminooxyacetic acid, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyric acid, dichlorprop, phenothionyl ol, 1-naphthylacetamide, ethychlozate, cloxifonac, maleic hydrazide, 2,3,5-triiodobenzoic acid, salicylic acid, methyl salicylate, (-)-jasmonic acid, methyl jasmonate, (+)-strigol, (+)-deoxystrigol, (+)-orobanchol, (+)-sorgolactone, 4-oxo-4-(2-phenylethyl)aminobutyric acid, ethephon, chlormequat, mepiquat chloride, benzyladenine, 5-aminolevulinic acid, daminozide.

[0233] {Formulation} The agricultural and horticultural fungicide of the present invention is not particularly limited by its formulation. For example, it may be in the form of a wettable powder, emulsifiable concentrate, dust, granule, water-soluble powder, suspension, water-dispersible granule, tablet, etc. The method for preparing the formulation is not particularly limited, and a known preparation method can be used depending on the formulation.

[0234] Some formulation examples are shown below. Note that the formulations shown below are merely examples and can be modified within the scope of the present invention, and the present invention is not limited by the following formulation examples. Unless otherwise specified, "parts" means "parts by mass."

[0235] (Formulation Example 1: Wettable Powder) 40 parts of the 5-membered heteroaryl compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfate, and 3 parts of alkyl naphthalene sulfonate are uniformly mixed and then finely pulverized to obtain a wettable powder containing 40% by mass of the active ingredient.

[0236] Formulation Example 2: Emulsifiable concentrate 30 parts of the 5-membered heteroaryl compound of the present invention, 33 parts of xylene, 30 parts of dimethylformamide, and 7 parts of polyoxyethylene alkyl allyl ether are mixed and dissolved to obtain an emulsifiable concentrate containing 30% by mass of the active ingredient.

[0237] (Formulation Example 3: Granules) 5 parts of the 5-membered heteroaryl compound of the present invention, 40 parts of talc, 38 parts of clay, 10 parts of bentonite, and 7 parts of sodium alkyl sulfate are uniformly mixed, then finely pulverized, and then granulated to particle diameters of 0.5 to 1.0 mm to obtain granules containing 5% by mass of the active ingredient.

[0238] Formulation Example 4: Granules 5 parts of the 5-membered heteroaryl compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of dioctyl sulfosuccinate sodium salt, and 1 part of potassium phosphate are uniformly mixed and pulverized, and then water is added thereto and kneaded. The mixture is then granulated and dried to obtain granules containing 5% by mass of the active ingredient.

[0239] Formulation Example 5: Suspension 10 parts of the 5-membered heteroaryl compound of the present invention, 4 parts of polyoxyethylene alkyl allyl ether, 2 parts of a sodium salt of polycarboxylic acid, 10 parts of glycerin, 0.2 parts of xanthan gum, and 73.8 parts of water are mixed and wet-pulverized until the particle size becomes 3 microns or less, to obtain a suspension containing 10% by mass of the active ingredient.

[0240] (Formulation Example 6: Water Dispersible Granules) 40 parts of the 5-membered heteroaryl compound of the present invention, 36 parts of clay, 10 parts of potassium chloride, 1 part of sodium alkylbenzenesulfonate, 8 parts of sodium ligninsulfonate, and 5 parts of a formaldehyde condensate of sodium alkylbenzenesulfonate are uniformly mixed and finely pulverized. An appropriate amount of water is then added to the mixture, and the mixture is kneaded to form a clay-like substance. The clay-like substance is granulated and then dried to obtain a water dispersible granule containing 40% by mass of the active ingredient.

[0241] Next, the present invention will be explained in more detail by showing compound production examples, but the present invention is not limited to the following examples in any way.

[0242] [Production Example 1] Methyl 1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate was produced in the following steps. Step 1: Conversion to methyl (2,4-dimethylbenzyl)(1,3-dioxoisoindolin-2-yl)carbamate

[0243]

[0244] Compound 12 (0.5 g) was dissolved in acetonitrile (3 mL). To this solution, 1-(bromomethyl)-2,4-dimethylbenzene (0.54 g), potassium carbonate (0.3 g), and benzyltriethylammonium chloride (0.07 g) were added at room temperature and stirred at 80°C for 2 hours. The resulting solution was poured into ice water. This was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to give compound 13 (0.4 g, 51% yield).

[0245] Step 2: Conversion to methyl 1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate

[0246]

[0247] Compound 13 (0.3 g) was dissolved in ethanol (3 mL). Hydrazine monohydrate (0.22 mL) was added to the solution at room temperature and stirred at 50°C for 1 hour. The solid was filtered, and the resulting solution was poured into ice water, extracted with ethyl acetate, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give compound 14 (0.17 g, 98% yield).

[0248] Production Example 2 Methyl 1-(2,4-dimethylbenzyl)-2-(1-methyl-4-(3-(trifluoromethyl)phenoxy)-1H-1,2,3-triazole-5-carbonyl)hydrazine-1-carboxylate (compound c-6)) was produced by the following steps.

[0249] Step 1: Conversion to isopropyl 4-bromo-1-methyl-1H-1,2,3-triazole-5-carboxylate

[0250]

[0251] Compound 42 (0.62 g) was dissolved in N,N-dimethylformamide (6 mL). To this solution, isopropyl iodide (0.61 g) and potassium carbonate (0.54 g) were added at room temperature, and the mixture was stirred at 60°C for 1 hour. The mixture was then purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain compound 43 (0.58 g, yield 78%).

[0252] Step 2: Conversion to isopropyl 1-methyl-4-(3-(trifluoromethyl)phenoxy)-1H-1,2,3-triazole-5-carboxylate

[0253]

[0254] Compound 43 (0.25 g) was dissolved in toluene (4.5 mL). 3-(Trifluoromethyl)phenol (0.49 g), cesium carbonate (0.65 g), copper iodide (19 mg), and dimethylglycine (21 mg) were added. The mixture was stirred at 165°C for 1 hour in a microwave reactor. The mixture was then purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to give compound 44 (0.14 g, 43% yield).

[0255] Step 3: Conversion to 1-methyl-4-(3-(trifluoromethyl)phenoxy)-1H-1,2,3-triazole-5-carboxylic acid

[0256]

[0257] Compound 44 (0.14 g) was dissolved in tetrahydrofuran (3 mL) and water (1 mL). Lithium hydroxide monohydrate (0.09 g) was added to the solution at room temperature and stirred for 18 hours. Dilute hydrochloric acid was added to the resulting solution, which was then extracted with ethyl acetate. The extract was washed with saturated brine. The solution was then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give compound 45 (0.12 g, 97% yield).

[0258] Step 4: Conversion to methyl 1-(2,4-dimethylbenzyl)-2-(1-methyl-4-(3-(trifluoromethyl)phenoxy)-1H-1,2,3-triazole-5-carbonyl)hydrazine-1-carboxylate

[0259]

[0260] Compound 45 (0.03 g) was dissolved in dichloromethane (1 mL). Compound 14 (23 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (29 mg), 1-hydroxybenzotriazole (1 mg), and triethylamine (0.034 mL) were added and stirred at room temperature for 18 hours. The resulting solution was poured into ice water, extracted with ethyl acetate, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) and preparative HPLC (developing solvent: water / acetonitrile) to obtain compound c-6 (6 mg, 13% yield).

[0261] Production Example 3 Methyl 1-(2,4-dimethylbenzyl)-2-(1-methyl-4-((4-(trifluoromethyl)pyridin-2-yl)oxy)-1H-pyrazole-5-carbonyl)hydrazine-1-carboxylate (English name: Methyl 1-(2,4-dimethylbenzyl)-2-(1-methyl-4-((4-(trifluoromethyl)pyridin-2-yl)oxy)-1H-pyrazole-5-carbonyl)hydrazine-1-carboxylate (compound c-12)) was produced by the following steps.

[0262] Step 1: Conversion to tert-butyl 4-iodo-1-methyl-1H-pyrazole-5-carboxylate

[0263]

[0264] Compound 46 (20 g) was dissolved in tetrahydrofuran (265 mL). 4-Dimethylaminopyridine (2.9 g) and di-tert-butyl dicarbonate (26 g) were added, and the mixture was stirred at 40°C for 7 hours. Dilute hydrochloric acid was added to the resulting solution, and the mixture was extracted with ethyl acetate. The extracted phase was washed with brine. The mixture was then dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the mixture was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain compound 47 (22.05 g, yield 90%).

[0265] Step 2: Conversion to tert-butyl 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-5-carboxylate

[0266]

[0267] Compound 47 (21.57 g) was dissolved in dimethyl sulfoxide (350 mL). To this solution, bis(pinacolato)diboron (35.6 g), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (2.9 g), and potassium acetate (20.6 g) were added, and the mixture was stirred at 70 °C for 7 hours under a nitrogen atmosphere. Water was added to the resulting solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine. The mixture was then dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the mixture was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain compound 48 (18.99 g, yield 88%).

[0268] Step 3: Conversion to tert-butyl 4-hydroxy-1-methyl-1H-pyrazole-5-carboxylate

[0269]

[0270] Compound 48 (18.99 g) was dissolved in a mixed solvent of tetrahydrofuran (123 mL) and water (123 mL). Sodium hydroxide (4.9 g) was added and the mixture was stirred under ice cooling. 30% hydrogen peroxide (14 g) was added and the mixture was stirred at room temperature for 1 hour. Dilute hydrochloric acid was added to the resulting solution, and the mixture was extracted with ethyl acetate. The extracted phase was washed with saturated saline. The mixture was then dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the mixture was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain compound 49 (9.43 g, yield 77%).

[0271] Step 4: Conversion to tert-butyl 1-methyl-4-((4-(trifluoromethyl)pyridin-2-yl)oxy)-1H-pyrazole-5-carboxylate

[0272]

[0273] Compound 49 (0.396 g) was dissolved in N,N-dimethylformamide (10 mL). 2-Chloro-4-(trifluoromethyl)pyridine (0.73 g) and potassium carbonate (0.55 g) were added, and the mixture was stirred at 80°C for 7 hours. Water was added to the resulting solution, and the mixture was extracted with ethyl acetate. The extracted phase was washed with saturated brine. The mixture was then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The mixture was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to quantitatively obtain compound 50 (0.75 g, 100% yield).

[0274] Step 5: Conversion to 1-methyl-4-((4-(trifluoromethyl)pyridin-2-yl)oxy)-1H-pyrazole-5-carboxylic acid

[0275]

[0276] Compound 50 (0.75 g) was dissolved in dichloromethane (10 mL). Trifluoroacetic acid (2 mL) was added and the mixture was stirred at room temperature overnight. The resulting solution was concentrated to give compound 51 (0.74 g, 100% yield).

[0277] Step 6: Conversion to methyl 1-(2,4-dimethylbenzyl)-2-(1-methyl-4-((4-(trifluoromethyl)pyridin-2-yl)oxy)-1H-pyrazole-5-carbonyl)hydrazine-1-carboxylate

[0278]

[0279] Compound 51 (0.1 g) was dissolved in N,N-dimethylformamide (1 mL). To this solution, compound 14 (0.1 g), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU) (0.26 g), and N,N-diisopropylethylamine (0.09 g) were added and stirred at room temperature for 1 hour. The resulting solution was purified by preparative HPLC (developing solvent: water / acetonitrile) to obtain compound c-12 (0.093 g, 55% yield).

[0280] Production Example 4 Methyl 2-(5-(3-bromo-2-fluorophenoxy)-1-methyl-1H-pyrazole-4-carbonyl)-1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate (compound c-19)) was produced by the following steps.

[0281] Step 1: Conversion to Ethyl 5-(3-bromo-2-fluorophenoxy)-1-methyl-1H-pyrazole-4-carboxylate

[0282]

[0283] Compound 52 (0.17 g) was dissolved in N,N-dimethylformamide (3 mL). 3-Bromo-2-fluorophenol (0.181 g) and cesium carbonate (0.62 g) were added, and the mixture was stirred at 130 °C overnight. Water was added to the resulting solution, and the mixture was extracted with ethyl acetate. The extracted phase was washed with brine. The mixture was then dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the mixture was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to give compound 53 (0.11 g, yield 51%).

[0284] Step 2: Conversion to 5-(3-bromo-2-fluorophenoxy)-1-methyl-1H-pyrazole-4-carboxylic acid

[0285]

[0286] Compound 53 (0.11 g) was dissolved in a mixture of THF (3 mL), methanol (1 mL), and water (1 mL). Lithium hydroxide monohydrate (0.054 g) was added and stirred overnight at room temperature. Dilute hydrochloric acid was added to the resulting solution, which was then extracted with ethyl acetate. The extract was washed with saturated brine. The solvent was then removed under reduced pressure to give compound 54 (0.1 g, 100% yield).

[0287] Step 3: Conversion to methyl 2-(5-(3-bromo-2-fluorophenoxy)-1-methyl-1H-pyrazole-4-carbonyl)-1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate

[0288]

[0289] Compound 54 (0.1 g) was dissolved in N,N-dimethylformamide (1 mL). To this solution, compound 14 (0.1 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.09 g), 1-hydroxybenzotriazole (0.07 g), and triethylamine (0.06 g) were added and stirred overnight at room temperature. The resulting solution was purified by preparative HPLC (developing solvent: water / acetonitrile) to obtain compound c-19 (0.061 g, 40% yield).

[0290] Production Example 5 Methyl 2-(4-(3-bromo-2-fluorophenoxy)-1-methyl-1H-pyrazole-5-carbonyl)-1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate (compound c-13)) was produced by the following steps.

[0291] Step 1: Conversion to 3-(3-bromo-2-fluorophenoxy)-4-(dimethylamino)but-3-en-2-one

[0292]

[0293] Compound 55 (10.93 g) was dissolved in N,N-dimethylformamide dimethyl acetal (12 mL) and stirred for 2 hours at 100° C. The resulting solution was evaporated under reduced pressure and purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to give compound 56 (7.38 g, yield 58%).

[0294] Step 2: Conversion to 4-(3-bromo-2-fluorophenoxy)-5-methyl-1H-pyrazole

[0295]

[0296] Compound 56 (7.78 g) was dissolved in methanol (30 mL). Hydrazine hydrate (3 mL) was added to the solution, and the mixture was stirred at 80°C for 5 hours. Saturated aqueous sodium bicarbonate was added to the resulting solution, and the mixture was extracted with ethyl acetate. The extracted phase was washed with saturated brine. The mixture was then dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the mixture was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to give compound 57 (2.34 g, yield 33%).

[0297] Step 3: Conversion to 4-(3-bromo-2-fluorophenoxy)-1-methyl-1H-pyrazole-5-carboxylic acid

[0298]

[0299] Compound 57 (2.07 g) was dissolved in N,N-dimethylformamide (23 mL). Potassium carbonate (2.1 g) and methyl iodide (1.4 g) were added to the solution, which was then stirred overnight at room temperature. Water was added to the resulting solution, which was then extracted with ethyl acetate. The extract was washed with saturated saline solution. The solution was then dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the crude product was obtained by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate). The resulting crude product was dissolved in a mixed solvent of tert-butanol (17 mL) and water (8 mL). Potassium hydroxide (1.2 g) and potassium permanganate (2.2 g) were added to the solution with stirring at room temperature, and the mixture was heated to reflux overnight. The resulting solution was filtered through Celite®, and dilute hydrochloric acid was added to the filtrate, which was then extracted with ethyl acetate. The extract was washed with saturated saline solution. Thereafter, the residue was dried over anhydrous magnesium hydroxide, the solvent was evaporated under reduced pressure, and the residue was purified by preparative HPLC (developing solvent: water / acetonitrile) to obtain Compound 58 (0.47 g, yield 20%).

[0300] Step 4: Conversion to methyl 2-(4-(3-bromo-2-fluorophenoxy)-1-methyl-1H-pyrazole-5-carbonyl)-1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate

[0301]

[0302] Compound 58 (0.03 g) was dissolved in N,N-dimethylformamide (1 mL). To this solution, compound 14 (0.03 g), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU) (0.055 g), and N,N-diisopropylethylamine (0.025 g) were added and stirred overnight at room temperature. The resulting solution was purified by preparative HPLC (developing solvent: water / acetonitrile) to obtain compound c-13 (0.011 g, 22% yield).

[0303] Production Example 6 Methyl 2-(4-(3-bromophenoxy)-1-methyl-1H-pyrazole-5-carbonyl)-1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate (compound c-1)) was produced by the following steps.

[0304] Step 1: Conversion to methyl 4-(3-bromophenoxy)-1-methyl-1H-pyrazole-5-carboxylate

[0305]

[0306] Compound 59 (0.154 g) was dissolved in dichloromethane (5 mL). To this solution, 3-bromophenylboronic acid (0.29 g), copper acetate monohydrate (0.29 g), and pyridine (2.0 g) were added and stirred at room temperature for 2 days. The solvent was removed from the resulting solution by distillation under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain compound 60 (0.198 g, yield 65%).

[0307] Step 2: Conversion to 4-(3-bromophenoxy)-1-methyl-1H-pyrazole-5-carboxylic acid

[0308]

[0309] Compound 60 (0.198 g) was dissolved in a mixture of tetrahydrofuran (2 mL), methanol (0.6 mL), and water (0.6 mL). Lithium hydroxide monohydrate (0.14 g) was added and stirred overnight at room temperature. Dilute hydrochloric acid was added to the resulting solution, which was then extracted with ethyl acetate. The extract was washed with saturated brine. The mixture was then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give compound 61 (0.185 g, 98% yield).

[0310] Step 3: Conversion to methyl 2-(4-(3-bromophenoxy)-1-methyl-1H-pyrazole-5-carbonyl)-1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate

[0311]

[0312] Compound 61 (0.05 g) was dissolved in N,N-dimethylformamide (3 mL). To this solution, compound 14 (0.052 g), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU) (0.138 g), and N,N-diisopropylethylamine (0.043 g) were added and stirred overnight at room temperature. The resulting solution was purified by preparative HPLC (developing solvent: water / acetonitrile) to obtain compound c-1 (0.033 g, 43% yield).

[0313] [Production Example 7] Methyl 2-(4-(3-bromophenoxy)-3-chloro-1-methyl-1H-pyrazole-5-carbonyl)-1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate (compound c-35) was produced in the following steps. Step 1: Conversion to tert-butyl 3-chloro-4-hydroxy-1-methyl-1H-pyrazole-5-carboxylate

[0314]

[0315] tert-Butyl 4-hydroxy-1-methyl-1H-pyrazole-5-carboxylate (0.50 g) was dissolved in N,N-dimethylformamide (8.4 mL). N-chlorosuccinimide (0.40 g) was added to the solution, and the mixture was stirred at room temperature for 16 hours. The reaction mixture was then purified directly by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 0.43 g (73% yield) of tert-butyl 3-chloro-4-hydroxy-1-methyl-1H-pyrazole-5-carboxylate.

[0316] Step 2: Conversion to 3-chloro-4-hydroxy-1-methyl-1H-pyrazole-5-carboxylic acid

[0317]

[0318] tert-Butyl 3-chloro-4-hydroxy-1-methyl-1H-pyrazole-5-carboxylate (0.43 g) was dissolved in dichloromethane (6.2 mL). Trifluoroacetic acid (2 mL) was added and the mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated using an evaporator to give 0.33 g (100% yield) of 3-chloro-4-hydroxy-1-methyl-1H-pyrazole-5-carboxylic acid.

[0319] Step 3: Conversion to methyl 2-(3-chloro-4-hydroxy-1-methyl-1H-pyrazole-5-carbonyl)-1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate

[0320]

[0321] 3-Chloro-4-hydroxy-1-methyl-1H-pyrazole-5-carboxylic acid (0.33 g) was dissolved in N,N-dimethylformamide (6.2 mL). Methyl 1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate (0.85 g), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU) (1.7 g), and triethylamine (0.94 g) were added and stirred at 60 °C for 4 hours. After filtration, the mixture was purified by preparative liquid chromatography (eluent: water / acetonitrile) to give 0.31 g (45% yield) of methyl 2-(3-chloro-4-hydroxy-1-methyl-1H-pyrazole-5-carbonyl)-1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate.

[0322] Step 4: Conversion to methyl 2-(4-(3-bromophenoxy)-3-chloro-1-methyl-1H-pyrazole-5-carbonyl)-1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate

[0323]

[0324] Methyl 2-(3-chloro-4-hydroxy-1-methyl-1H-pyrazole-5-carbonyl)-1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate (0.10 g) was dissolved in dichloromethane (0.91 mL). Copper acetate (0.074 g), pyridine (0.043 g), and (3-bromophenyl)boronic acid (0.22 g) were added. After stirring at room temperature for 16 hours, the reaction solvent was concentrated using an evaporator. Purification by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) afforded 0.007 g (5% yield) of methyl 2-(4-(3-bromophenoxy)-3-chloro-1-methyl-1H-pyrazole-5-carbonyl)-1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate.

[0325] [Production Example 8] Methyl 2-(4-(3-bromophenoxy)-1-(tert-butyl)-1H-pyrazole-5-carbonyl)-1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate (compound C-114) was produced in the following steps. Step 1: Conversion to 3-(3-bromophenoxy)-4-(dimethylamino)but-3-en-2-one

[0326]

[0327] 1-(3-Bromophenoxy)propan-2-one (38.35 g) was dissolved in N,N-dimethylformamide dimethyl acetal (33.8 mL), and the resulting solution was stirred overnight at 80° C. The reaction solution was evaporated under reduced pressure, and then purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate). The resulting purified product was washed with diethyl ether and hexane to obtain 28 g of the target compound (yield: 58%).

[0328] Step 2: Conversion to 4-(3-bromophenoxy)-1-(tert-butyl)-5-methyl-1H-pyrazol

[0329]

[0330] 3-(3-Bromophenoxy)-4-(dimethylamino)but-3-en-2-one (17 g) was dissolved in 1,4-dioxane (300 mL). Tertiary-butylhydrazine hydrochloride (8.9 g) and concentrated hydrochloric acid (5.5 mL) were added, and the mixture was stirred at 60°C for 3 hours. Saturated aqueous sodium bicarbonate was added to the reaction mixture, which was then extracted with ethyl acetate. The extract was washed with saturated brine. The mixture was then dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 14.61 g of the target compound (79% yield).

[0331] Step 3: Conversion to 4-(3-bromophenoxy)-1-(tert-butyl)-1H-pyrazole-5-carboxylic acid

[0332]

[0333] 4-(3-Bromophenoxy)-1-(tert-butyl)-5-methyl-1H-pyrazole (14.61 g) was dissolved in a mixed solvent of tert-butanol (105 mL) and water (52.5 mL). Potassium hydroxide (5.3 g) and potassium permanganate (22.4 g) were added to the mixture while stirring at room temperature, and the mixture was stirred at 100°C for 5 hours. The reaction mixture was filtered through Celite®, diluted hydrochloric acid was added, and the mixture was extracted with dichloromethane. The extract was washed with saturated brine. The mixture was then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give 9.56 g of the target compound (60% yield).

[0334] Step 5: Conversion to methyl 2-(4-(3-bromophenoxy)-1-(tert-butyl)-1H-pyrazole-5-carbonyl)-1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate

[0335]

[0336] 4-(3-Bromophenoxy)-1-(tert-butyl)-1H-pyrazole-5-carboxylic acid (0.05 g) was dissolved in tetrahydrofuran (1 mL). To this solution, methyl 1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate (0.046 g), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU) (0.11 g), and triethylamine (0.05 g) were added and stirred overnight at room temperature. The reaction mixture was evaporated under reduced pressure and purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate) to obtain 0.06 g of the desired product (yield: 80%).

[0337] Production Example 9 Methyl 2-(1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-1,2,3-triazole-5-carbonyl)-1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate (English name: methyl 2-(1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-1,2,3-triazole-5-carbonyl)-1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate (compound c-97) was produced by the following steps.

[0338] Step 1: Conversion to 4,5-dibromo-1-(tert-butyl)-1H-1,2,3-triazole

[0339]

[0340] 4,5-Dibromo-1H-1,2,3-triazole (3.4 g), tert-butanol (2.2 g), and p-toluenesulfonic acid monohydrate (0.57 g) were added to toluene (50 mL) and stirred for 3 hours at 70° C. After the solvent was distilled off, the residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 4,5-dibromo-1-(tert-butyl)-1H-1,2,3-triazole (1.8 g).

[0341] Step 2: Conversion to 4-bromo-1-(tert-butyl)-1H-1,2,3-triazole-5-carboxylic acid

[0342]

[0343] 4,5-Dibromo-1-(tert-butyl)-1H-1,2,3-triazole (1.7 g) was dissolved in tetrahydrofuran (15 mL) at 0 °C, and isopropylmagnesium chloride-lithium chloride complex (1.4 g) was added and stirred for 2 hours. Carbon dioxide (10 g) was then bubbled through. The reaction was quenched with 1 M HCl, extracted with ethyl acetate, and the solvent was evaporated to give 4-bromo-1-(tert-butyl)-1H-1,2,3-triazole-5-carboxylic acid (1.5 g).

[0344] Step 3: Conversion to isopropyl 4-bromo-1-(tert-butyl)-1H-1,2,3-triazole-5-carboxylate

[0345]

[0346] 4-Bromo-1-(tert-butyl)-1H-1,2,3-triazole-5-carboxylic acid (1.5 g), isopropyl iodide (3.1 g), and potassium carbonate (2.5 g) were added to N,N-dimethylformamide (20 mL) and stirred at 45°C for 3 hours. Water was added, and the mixture was extracted with ethyl acetate. The solvent was then evaporated. Purification by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) gave isopropyl 4-bromo-1-(tert-butyl)-1H-1,2,3-triazole-5-carboxylate (1.4 g, 80% yield).

[0347] Step 4: Conversion to isopropyl 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-1,2,3-triazole-5-carboxylate

[0348]

[0349] To toluene (2.5 mL) were added α,α,α-trifluoro-m-cresol (0.32 g), isopropyl 4-bromo-1-(tert-butyl)-1H-1,2,3-triazole-5-carboxylate (0.29 g), N,N-dimethylglycine (21 mg), and copper iodide (19 mg). The mixture was irradiated in a microwave oven at 150°C for 1.5 hours. Purification by silica gel column chromatography (eluent: n-hexane / ethyl acetate) afforded 0.20 g of isopropyl 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-1,2,3-triazole-5-carboxylate.

[0350] Step 5: Conversion to 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-1,2,3-triazole-5-carboxylic acid

[0351]

[0352] Isopropyl 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-1,2,3-triazole-5-carboxylate (0.20 g) was dissolved in tetrahydrofuran (0.50 mL), water (0.17 mL), and methanol (0.50 mL). Lithium hydroxide monohydrate (73 mg) was added and the mixture was stirred at 25°C for 16 hours. The reaction was quenched with 1N hydrochloric acid, and the mixture was separated with ethyl acetate and dried over magnesium sulfate. The solvent was evaporated to give 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-1,2,3-triazole-5-carboxylic acid (0.12 g).

[0353] Step 6: Conversion to methyl 2-(1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-1,2,3-triazole-5-carbonyl)-1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate

[0354]

[0355] 1-(tert-Butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-1,2,3-triazole-5-carboxylic acid (0.060 g), methyl 1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate (30 mg), triethylamine (36 mg), and 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU) (68 mg) were added sequentially to tetrahydrofuran (0.39 mL) and stirred at 25°C for 18 hours. Purification by preparative chromatography gave methyl 2-(1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-1,2,3-triazole-5-carbonyl)-1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate (0.062 g).

[0356] [Production Example 10] Methyl 2-(1-(tert-butyl)-4-(3-chlorophenoxy)-1H-1,2,3-triazole-5-carbonyl)-1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate (compound number: c-131) was produced in the following steps. Step 1: Conversion to 4-bromo-1-(tert-butyl)-1H-1,2,3-triazole-5-carboxamide

[0357]

[0358] 4-Bromo-1-(tert-butyl)-1H-1,2,3-triazole-5-carboxylic acid (0.50 g) was dissolved in N,N-dimethylformamide (6.7 mL). Ammonium chloride (0.21 g), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU) (1.1 g), and triethylamine (0.61 g) were added. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The resulting organic layer was concentrated using an evaporator and purified by silica gel column chromatography to give 4-bromo-1-(tert-butyl)-1H-1,2,3-triazole-5-carboxamide (0.36 g, 73% yield).

[0359] Step 2: Conversion to 4-bromo-1-(tert-butyl)-1H-1,2,3-triazole-5-carbonitrile

[0360]

[0361] 4-Bromo-1-(tert-butyl)-1H-1,2,3-triazole-5-carboxamide (0.050 g) was dissolved in dichloromethane (0.67 mL). Trifluoroacetic anhydride (0.13 g) and triethylamine (72 mg) were added, and the mixture was stirred at 25°C for 1 hour. The reaction mixture was quenched with saturated aqueous sodium bicarbonate and then extracted with ethyl acetate. The resulting organic layer was concentrated using an evaporator. The residue was separated by silica gel column chromatography and purified by amino silica gel column chromatography to give 4-bromo-1-(tert-butyl)-1H-1,2,3-triazole-5-carbonitrile (0.039 g, 84% yield).

[0362] Step 3: Conversion to 1-(tert-butyl)-4-(3-chlorophenoxy)-1H-1,2,3-triazole-5-carbonitrile

[0363]

[0364] 1-Chloro-3-hydroxybenzene (73 mg), 4-bromo-1-(tert-butyl)-1H-1,2,3-triazole-5-carbonitrile (0.10 g), and potassium carbonate (90 mg) were added to dimethyl sulfoxide (2.2 mL) and stirred at 120°C for 4 hours. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The resulting organic layer was concentrated using an evaporator. Purification by silica gel chromatography afforded 1-(tert-butyl)-4-(3-chlorophenoxy)-1H-1,2,3-triazole-5-carbonitrile (0.09 g, 70% yield).

[0365] Step 4: Conversion to 1-(tert-butyl)-4-(3-chlorophenoxy)-1H-1,2,3-triazole-5-carboxamide

[0366]

[0367] 1-(tert-butyl)-4-(3-chlorophenoxy)-1H-1,2,3-triazole-5-carbonitrile (0.15 g) and sodium hydroxide (4 M, 2.7 mL) were added to ethanol (2.7 mL) and stirred at 100°C for 12 hours. The reaction mixture was quenched with 1N hydrochloric acid and extracted with ethyl acetate. The resulting organic layer was dried over magnesium sulfate. The solvent was removed using an evaporator to give 1-(tert-butyl)-4-(3-chlorophenoxy)-1H-1,2,3-triazole-5-carboxamide (0.16 g).

[0368] Step 5: Conversion to 1-(tert-butyl)-4-(3-chlorophenoxy)-1H-1,2,3-triazole-5-carboxylic acid

[0369]

[0370] 1-(tert-butyl)-4-(3-chlorophenoxy)-1H-1,2,3-triazole-5-carboxamide (0.16 g) and sodium nitrite (0.11 g) were added to trifluoroacetic acid (1.8 mL) at 0°C and stirred at 0°C for 2 hours. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The resulting organic layer was dried over magnesium sulfate. The solvent was removed using an evaporator to give 1-(tert-butyl)-4-(3-chlorophenoxy)-1H-1,2,3-triazole-5-carboxylic acid (0.13 g, 81% yield).

[0371] Step 6: Conversion to methyl 2-(1-(tert-butyl)-4-(3-chlorophenoxy)-1H-1,2,3-triazole-5-carbonyl)-1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate

[0372]

[0373] 1-(tert-butyl)-4-(3-chlorophenoxy)-1H-1,2,3-triazole-5-carboxylic acid (41 mg), methyl 1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate (35 mg), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU) (80 mg), and triethylamine (42 mg) were added to tetrahydrofuran (0.70 mL) and stirred at 25°C for 16 hours. The reaction mixture was purified by preparative HPLC (developing solvent: water / acetonitrile) to obtain methyl 2-(1-(tert-butyl)-4-(3-chlorophenoxy)-1H-1,2,3-triazole-5-carbonyl)-1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate (0.040 g, yield: 59%).

[0374] Preparation Example 11 Methyl 2-(3-chloro-1-isopropyl-4-((4-(trifluoromethyl)thiazol-2-yl)oxy)-1H-pyrazole-5-carbonyl)-1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate (compound number: c-137) was prepared by the following steps.

[0375] Step 1: Conversion to ethyl 3-chloro-1-isopropyl-4-((4-(trifluoromethyl)thiazol-2-yl)oxy)-1H-pyrazole-5-carboxylate

[0376]

[0377] Ethyl 3-chloro-4-hydroxy-1-isopropyl-1H-pyrazole-5-carboxylate (0.059 g) was dissolved in N,N-dimethylformamide (2.5 mL). 2-Chloro-4-(trifluoromethyl)thiazole (0.071 g) and potassium carbonate (0.070 g) were added, and the mixture was stirred at 60°C for 17 hours. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The extract was washed with saturated brine. The mixture was then dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to give 0.053 g (54% yield) of ethyl 3-chloro-1-isopropyl-4-((4-(trifluoromethyl)thiazol-2-yl)oxy)-1H-pyrazole-5-carboxylate.

[0378] Step 2: Conversion to 3-chloro-1-isopropyl-4-((4-(trifluoromethyl)thiazol-2-yl)oxy)-1H-pyrazole-5-carboxylic acid

[0379]

[0380] Ethyl 3-chloro-1-isopropyl-4-((4-(trifluoromethyl)thiazol-2-yl)oxy)-1H-pyrazole-5-carboxylate (0.053 g) was dissolved in tetrahydrofuran (0.82 mL), methanol (0.28 mL), and water (0.28 mL). Lithium hydroxide monohydrate (0.023 g) was added and stirred at room temperature for 1.5 hours. Dilute hydrochloric acid was added to the reaction mixture, which was then extracted with ethyl acetate. The extract was washed with saturated brine. The mixture was then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give 0.047 g (97% yield) of 3-chloro-1-isopropyl-4-((4-(trifluoromethyl)thiazol-2-yl)oxy)-1H-pyrazole-5-carboxylic acid.

[0381] Step 3: Conversion to methyl 2-(3-chloro-1-isopropyl-4-((4-(trifluoromethyl)thiazol-2-yl)oxy)-1H-pyrazole-5-carbonyl)-1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate

[0382]

[0383] 3-Chloro-1-isopropyl-4-((4-(trifluoromethyl)thiazol-2-yl)oxy)-1H-pyrazole-5-carboxylic acid (0.034 g) was dissolved in tetrahydrofuran (1 mL). To this solution, methyl 1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate (0.030 g), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (0.073 g), and triethylamine (0.029 g) were added and stirred at room temperature for 16 hours. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 0.044 g (yield 84%) of methyl 2-(3-chloro-1-isopropyl-4-((4-(trifluoromethyl)thiazol-2-yl)oxy)-1H-pyrazole-5-carbonyl)-1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate.

[0384] Preparation Example 12 Methyl 1-(2,4-dimethylbenzyl)-2-(1-(thiazol-2-yl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carbonyl)hydrazine-1-carboxylate (compound number: c-120) was prepared by the following steps.

[0385] Step 1: Conversion to ethyl 1-(thiazol-2-yl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylate

[0386]

[0387] Ethyl 4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylate (150 mg) was dissolved in N,N-dimethylformamide dimethyl acetal (2 mL), and 2-bromo-1,3-thiazole (81.9 mg) and cesium carbonate (406.3 mg) were added thereto and stirred at 100°C for 3 hours. The reaction solution was filtered, followed by addition of water and extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered, and then evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 110 mg of the target compound (yield: 58%).

[0388] Step 2: Conversion to 1-(thiazol-2-yl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid

[0389]

[0390] Ethyl 1-(thiazol-2-yl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylate (110 mg) was dissolved in a mixed solvent of methanol (2 mL) and water (1 mL). To this solution, lithium hydroxide monohydrate (24 mg) was added with stirring at room temperature, and the mixture was stirred at room temperature for 2 hours. Dilute hydrochloric acid was added to the reaction solution, and the reaction solution was evaporated under reduced pressure. The resulting residue was purified by preparative HPLC (developing solvent: water / acetonitrile) to obtain 71.1 mg of the target compound (yield 100%).

[0391] Step 3: Conversion to methyl 1-(2,4-dimethylbenzyl)-2-(1-(thiazol-2-yl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carbonyl)hydrazine-1-carboxylate

[0392]

[0393] 1-(Thiazol-2-yl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid (20 mg) was dissolved in tetrahydrofuran (1 mL). To this solution, methyl 1-(2,4-dimethylbenzyl)hydrazine-1-carboxylate (17.6 mg), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (42.8 mg), and triethylamine (17.1 mg) were added and stirred overnight at room temperature. The reaction mixture was evaporated under reduced pressure and purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate) to obtain 9 mg of the desired product (30% yield).

[0394] The compounds shown in Table 1 were prepared using the same process as in the above Preparation Examples. The melting point or appearance (amorphous or viscous oil) is recorded in the Properties column. For compounds with an amorphous or viscous oil appearance, the LCMS retention time is also recorded.

[0395] LCMS (SQD2) retention times were determined as follows. A system comprised of an ultra-high-performance, high-resolution liquid chromatograph (ACQUITY UPLC H-Class, manufactured by Waters), an HPLC / UHPLC detector (ACQUITY UPLC Photodiode Array (PDA) eλ Detector, manufactured by Waters), and a single quadrupole MS detector (LC / MS) (SQ Detector 2 detector, positive and negative ion electrospray mode and atmospheric pressure chemical ionization mode) was equipped with a CORTECS UPLC C18 column (manufactured by Waters, 2.1 x 50 mm, 1.6 μm). Measurements were performed at a temperature of 40°C, a flow rate of 0.6 mL / min, and a 2 μL injection. Water containing 0.1% by weight of formic acid was used as mobile phase (A), and acetonitrile was used as mobile phase (B). The concentration of the mobile phase (B) was maintained at 30% by mass for 0.15 minutes, then the concentration of the mobile phase (B) was increased at a constant rate from 30% by mass to 95% by mass over 1.35 minutes, maintained at 95% by mass for 0.5 minutes, then the concentration of the mobile phase (B) was immediately decreased to 30% by mass, and finally the concentration of the mobile phase (B) was maintained at 30% by mass for 0.50 minutes.

[0396] LCMS (QDa) retention times were determined as follows. A CORTECS UPLC C18 column (Waters, 2.1 x 50 mm, 1.6 μm) was attached to a system consisting of an ultra-high-performance, high-resolution liquid chromatograph (ACQUITY UPLC H-Class, manufactured by Waters), an HPLC / UHPLC detector (ACQUITY UPLC Photodiode Array (PDA) eλ Detector (Waters)), and a single quadrupole MS detector (LC / MS) (ACQUITY QDa Detector (positive and negative ion electrospray mode)). The temperature was 40°C, the flow rate was 0.6 mL / min, and the injection volume was 2 μL. Water containing 0.1% formic acid was used as the mobile phase (A), and acetonitrile was used as the mobile phase (B). The concentration of mobile phase (B) was maintained at 30% by mass for 0.15 minutes, then increased from 30% by mass to 95% by mass over 1.35 minutes at a constant rate, maintained at 95% by mass for 0.5 minutes, then immediately decreased to 30% by mass, and finally maintained at 30% by mass for 0.50 minutes.

[0397]

[0398]

[0399]

[0400]

[0401]

[0402]

[0403]

[0404]

[0405]

[0406]

[0407]

[0408]

[0409]

[0410]

[0411]

[0412]

[0413]

[0414]

[0415]

[0416]

[0417]

[0418]

[0419]

[0420]

[0421]

[0422]

[0423]

[0424]

[0425]

[0426]

[0427]

[0428]

[0429]

[0430]

[0431]

[0432]

[0433]

[0434]

[0435]

[0436] Compounds that can be production intermediates are shown in the following Tables 3, 4 and 5. The structural formulas of the production intermediates are shown together with the LCMS (SQD2) retention times.

[0437]

[0438]

[0439]

[0440]

[0441]

[0442]

[0443]

[0444]

[0445]

[0446]

[0447]

[0448]

[0449]

[0450]

[0451]

[0452]

[0453]

[0454] The effects of the present invention will be illustrated by the following fungicidal effect test and disease control test.

[0455] (Test of fungicidal effect against gray mold fungus) A spore suspension of gray mold fungus (Botrytis cinerea, Vogel medium) was prepared. A five-membered heteroaryl compound of the present invention was added to dimethyl sulfoxide to obtain a drug solution. Equal amounts (volume basis) of this drug solution and the spore suspension were mixed to obtain a test solution with a concentration of the five-membered heteroaryl compound of the present invention of 25 ppm by volume. The test solution was dropped into a 96-well microplate (drug-treated group). Equal amounts (volume basis) of dimethyl sulfoxide and the spore suspension were mixed to obtain a control solution. The control solution was dropped into a 96-well microplate (untreated group). These were left to stand at 20°C in a dark place and cultured for 5 days. The turbidity (OD) at a wavelength of 405 nm was measured using a microplate reader. The growth inhibition rate was calculated using the following formula: Growth inhibition rate (%) = 100 - 100 × {[(OD of drug-treated group after incubation) - (OD of drug-treated group before incubation)] / [(OD of untreated group after incubation) - (OD of untreated group before incubation)]}

[0456] Compounds c-1, c-2, c-6, c-9 to c-11, c-13 to c-18, c-20, c-22 to c-24, c-26 to c-35, c-38 to c-45, c-47 to c-51, c-53 to c-60, c-62, c-64 to c-67, c-70 to c-83, c-86, c-87, c-89 to c-104, c-106 to c-118, c-121 to c-137, c-139 to c-156 were subjected to fungicidal effect tests against Botrytis cinerea. All compounds showed growth inhibition rates of 75% or more.

[0457] (Test of bactericidal effect against grape late rot fungus) The turbidity was measured in the same manner as in the test of bactericidal effect against grape late rot fungus, except that the spore suspension of Botrytis cinerea (Vogel medium) was replaced with a spore suspension of Glomerella cingulata (Vogel medium) and the temperature and period of standing were changed to 25°C and 3 days, respectively, and the growth inhibition rate was calculated.

[0458] The fungicidal effect of compounds c-1, c-2, c-4 to c-6, c-9 to c-11, c-13 to c-18, c-20, c-22 to c-24, c-26 to c-35, c-38 to c-67, c-70 to c-83, c-86 to c-104, c-106 to c-118, and c-121 to c-156 on grape late rot fungi was tested. All compounds showed growth inhibition rates of 75% or more.

[0459] (Test of fungicidal effect against apple anthracnose fungus) The turbidity was measured and the growth inhibition rate was calculated in the same manner as in the test of fungicidal effect against Botrytis cinerea, except that the spore suspension of Botrytis cinerea (Vogel medium) was replaced with a spore suspension of Colletotrichum acutatum (Czapek medium) and the temperature and period of standing were changed to 25°C and 4 days, respectively.

[0460] The fungicidal effects of compounds c-1, c-2, c-4 to c-6, c-9 to c-11, c-13 to c-18, c-20, c-22 to c-24, c-26 to c-35, c-38 to c-45, c-47 to c-51, c-53 to c-60, c-62, c-64 to c-67, c-70 to c-83, c-86, c-87, c-89 to c-104, c-106 to c-118, and c-121 to c-156 on apple anthracnose were tested. All compounds showed growth inhibition rates of 75% or more.

[0461] (Test of fungicidal effect against wheat head blight fungus) The turbidity was measured in the same manner as in the test of fungicidal effect against Botrytis cinerea, except that the spore suspension of Botrytis cinerea (Vogel medium) was replaced with a spore suspension of Fusarium graminearum (SD medium) and the temperature and period of standing were changed to 25°C and 4 days, respectively, and the growth inhibition rate was calculated.

[0462] The fungicidal effect of compounds c-14, c-15, c-18, c-20, c-22 to c-24, c-27, c-28, c-32, c-33, c-35, c-38 to c-44, c-48, c-49, c-53, c-55, c-56, c-60, c-62, c-64 to c-67, c-72 to c-74, and c-76 to c-83 on wheat Fusarium head blight fungus was tested. All compounds showed growth inhibition rates of 75% or more.

[0463] (Test for control of cucumber gray mold) 5 parts by mass of the 5-membered heteroaryl compound of the present invention, 93.5 parts by mass of N,N-dimethylformamide, and 1.5 parts by mass of polyoxyethylene sorbitan monolaurate were mixed to obtain an emulsifiable concentrate (1) containing 5% by mass of the active ingredient.

[0464] Water was added to the emulsion (1) to obtain a drug solution containing the 5-membered heteroaryl compound of the present invention at a concentration of 125 ppm by mass or 25 ppm by mass. The drug solution was then sprayed onto cucumber seedlings (variety "Jihai", cotyledon stage) grown in seedling pots and then air-dried. A conidial suspension of Botrytis cinerea, the causative agent of gray mold of cucumber, was then dropwise inoculated onto the seedlings (treated group). As a control, a conidial suspension of Botrytis cinerea was dropwise inoculated onto cucumber seedlings that had not been sprayed with the drug solution (untreated group). These were then placed in a moist 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 using the following formula:

[0465] Control value (%) = 100 - {lesion area rate in treated area / lesion area rate in untreated area} x 100

[0466] Compounds c-16 to c-18, c-20, c-22, c-23, c-27 to c-30, c-32 to c-34, c-38 to c-42, c-44, c-45, c-47 to c-49, c-55 to c-58, c-60, c-64 to c-67, c-70 to c-78, c-80 to c-83, c-86, c-87, c-90 Control tests of cucumber gray mold were conducted at a concentration of 125 ppm by mass for compounds c-95, c-97 to c-103, c-106, c-109 to c-117, c-121, c-122, c-124, c-127 to c-136, c-140 to c-149, c-151 to c-153, c-155, and c-156. All compounds showed a control value of 75% or more.

[0467] Compounds c-16 to c-18, c-20, c-22, c-23, c-27 to c-30, c-33, c-38 to c-42, c-44, c-45, c-49, c-55, c-60, c-64 to c-67, c-71, c-72, c-74, c-76 to c-78, c-80, c-81, c-83, c-86, c-87, c-90 to c-95, c-97 to c-103, c-106, c-109 to c-116 were tested for control of cucumber gray mold at a concentration of 25 ppm by mass. All compounds showed a control value of 75% or more.

[0468] (Control test for apple scab) Water was added to the emulsion (1) so that the concentration of the 5-membered heteroaryl compound of the present invention was 125 ppm by mass, and the compound was dissolved to obtain a drug solution. The drug solution was then sprayed onto apple seedlings (cultivar "Orin", 3- to 4-leaf stage) grown in nursery pots, followed by air drying. The treated apple seedlings were then inoculated with conidia of the apple scab fungus (Venturia inaequalis) (treated group). As a control, apple seedlings not sprayed with the drug solution were inoculated in the same manner (untreated group). These were then placed in a moist chamber at 20°C, with a 12-hour cycle of light and dark. Twelve to fourteen days after inoculation, the leaves of the apple seedlings were visually observed, and the control value was calculated from the lesion area percentage using the formula used to calculate the control value in the above-mentioned cucumber gray mold control test.

[0469] Control tests of apple scab were conducted on compounds c-2, c-11, c-18 to c-20, c-23, c-27, c-28, c-33, c-34, c-39 to c-42, c-44, c-48, c-55, c-60, c-64, c-65, c-67, c-71 to c-74, c-77, c-82, c-83, c-87, c-91 to c-100, c-102, c-103, c-106, c-109, c-110, c-117, c-122, and c-124 to c-126. All compounds showed a control value of 75% or more.

[0470] (Test for Control of Wheat Powdery Mildew) Water was added to the above emulsion (1) so that the concentration of the 5-membered heteroaryl compound of the present invention became 125 ppm by mass, and the compound was dissolved to obtain a drug solution. Subsequently, the drug solution was sprayed onto wheat seedlings (variety "Chihoku", 1- to 2-leaf stage) grown in seedling pots and air-dried. Subsequently, conidia of wheat powdery mildew (Erysiphe graminis f.sp. tritici) were sprinkled on the seedlings for inoculation (treated group). As a control, conidia of wheat powdery mildew (Erysiphe graminis f.sp. tritici) were sprinkled on wheat seedlings that had not been sprayed with the drug solution (untreated group). These were then left to stand in a greenhouse at 20°C. Six days after inoculation, the leaves of the wheat seedlings were visually observed to determine the lesion area ratio, and the control value was calculated in the same manner as in the previous test.

[0471] Compounds c-15 to c-18, c-20, c-22, c-23, c-27, c-28, c-33, c-38 to c-42, c-44, c-48, c-60, c-64, c-65, c-67, c-71 to c-74, c-76 to c-83, c-86, c-91 to c-95, c-97, c-98, c-100 to c-103, c-106, c-109 to c-113, c-124, c-125, c-127, and c-131 to c-136 were tested for wheat powdery mildew control. All compounds showed a control value of 75% or more.

[0472] Since all of the five-membered heteroaryl compounds of the present invention selected at random exhibit the effects described above, it can be understood that the five-membered heteroaryl compounds of the present invention, including compounds not listed as examples, have fungicidal effects and do not cause phytotoxicity to plants.

[0473] The five-membered heteroaryl compound of the present invention has excellent fungicidal activity against pathogenic bacteria that affect agricultural and horticultural plants, is highly safe, and can be synthesized industrially advantageously. The agricultural and horticultural fungicide of the present invention can effectively control diseases of agricultural and horticultural plants.

Claims

1. A compound represented by formula (ZI) or a salt thereof. In the formula (Z-I), Q １ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group; Q ２ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group, and a partial structure of the following formula (III): In the １ represents an oxygen atom, a nitrogen atom, a group of the formula: NR １ or a group represented by the formula: CR ２ B represents a group represented by the formula: ２ represents an oxygen atom, a nitrogen atom, a group of the formula: NR １ or a group represented by the formula: CR ２ B represents a group represented by the formula: ３ represents an oxygen atom, a nitrogen atom, a group of the formula: NR １ or a group represented by the formula: CR ２ B represents a group represented by the formula: １ , B ２ , and B ３ Any one of the groups is an oxygen atom or a group represented by the formula: NR １ and the remaining two are a nitrogen atom or a group represented by the formula: CR ２ R is a group represented by １ each independently represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C3-6 cycloalkyl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group; R ２ are each independently 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 C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylcarbonyloxy group, a substituted or unsubstituted C1-6 alkoxycarbonyloxy group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C a 1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5-6 membered heterocyclyl group, a substituted or unsubstituted phenyloxy group, a substituted or unsubstituted naphthyloxy group, a substituted or unsubstituted 5-6 membered heterocyclyloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a nitro group, a cyano group, or a halogeno group; the carbon atoms marked with * and + in the partial structure of formula (III) correspond to the carbon atoms marked with * and + in formula (Z-I); Z ａ represents an oxygen atom or a sulfur atom, T represents a partial structure (T-1) or a partial structure (T-2), In the partial structure (T-1) or partial structure (T-2), the arrow marked with + is bonded to the carbon atom marked with + in the partial structure of the formula (III), and the other arrow is bonded to the carbon atom marked with + in the formula (Z-I). ７ In the partial structure (T-1), Z represents an oxygen atom or a sulfur atom, and R ６ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a formyl group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group; ｂ represents a C1-6 alkoxy group or a C1-6 alkylthio group; R ７ 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, ｃ A group represented by the formula: R ｃ A group represented by the formula: R ｃ A group represented by —CO—CO—, R ｃ -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- to 6-membered heterocyclyl group, or a cyano group; ｃ 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 membered heterocyclyl group, or a substituted or unsubstituted 3-6 membered heterocyclyloxy group; R ４ each independently 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- to 6-membered heterocyclyl group, or a halogeno group; R ５ each independently 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- to 6-membered heterocyclyl group, or a halogeno group, ４ and R ５ may combine with each other to form a divalent organic group, and n is an integer of 1 to 3.

2. The compound according to claim 1, wherein the formula (ZI) is represented by formula (I) or a salt thereof. In the formula (I), Q １ , Q ２ , B １ , B ２ , B ３ , Z ａ , R ４ , R ５ , R ７ and n is Q in formula (Z-I). １ , Q ２ , B １ , B ２ , B ３ , Z ａ , R ４ , R ５ , R ７ and n have the same meaning as Z and R ６ represents Z and R in the partial structure (T-1). ６ It has the same meaning as:

3. Said Z ａ is an oxygen atom, Z is an oxygen atom, R ６ is a hydrogen atom, ７ is a formyl group, the formula: R ｃ A group represented by the formula: R ｃ A group represented by the formula: R ｃ A group represented by —CO—CO—, or R ｃ -SO ２ The compound or salt thereof according to claim 2 , wherein n is a group represented by the formula:

4. An agricultural and horticultural fungicide comprising as an active ingredient at least one selected from the group consisting of the compound and its salt according to any one of claims 1 to 3.

5. A method for producing a compound represented by formula (I-1), comprising a step of reacting a compound represented by formula (im-1) with a compound represented by formula (im-2) in the presence of an acid scavenger. In the above formula, Q １ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group; Q ２ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group, and has the following partial structure: In the １ represents an oxygen atom, a nitrogen atom, a group of the formula: NR １ or a group represented by the formula: CR ２ B represents a group represented by the formula: ２ represents an oxygen atom, a nitrogen atom, a group of the formula: NR １ or a group represented by the formula: CR ２ B represents a group represented by the formula: ３ represents an oxygen atom, a nitrogen atom, a group of the formula: NR １ or a group represented by the formula: CR ２ B represents a group represented by the formula: １ , B ２ , and B ３ Any one of the groups is an oxygen atom or a group represented by the formula: NR １ and the remaining two are a nitrogen atom or a group represented by the formula: CR ２ R is a group represented by １ each independently represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C3-6 cycloalkyl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group; R ２ are each independently 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 C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylcarbonyloxy group, a substituted or unsubstituted C1-6 alkoxycarbonyloxy group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C a 1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5-6 membered heterocyclyl group, a substituted or unsubstituted phenyloxy group, a substituted or unsubstituted naphthyloxy group, a substituted or unsubstituted 5-6 membered heterocyclyloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a nitro group, a cyano group, or a halogeno group, carbon atoms marked with * and + in the partial structure correspond to carbon atoms marked with * and + in the formula (I-1) or the formula (im-1), Z ａ represents an oxygen atom or a sulfur atom; Z represents an oxygen atom or a sulfur atom; R ４ each independently 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- to 6-membered heterocyclyl group, or a halogeno group; R ５ each independently 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- to 6-membered heterocyclyl group, or a halogeno group, ４ and R ５ may combine with each other to form a divalent organic group, n represents an integer of 1 to 3, R ６ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a formyl group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group; R ７a is a formyl group, the formula: R ｃ A group represented by the formula: R ｃ A group represented by the formula: R ｃ A group represented by —CO—CO—, or R ｃ -SO ２ R represents a group represented by -; ｃ 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 membered heterocyclyl group, or a substituted or unsubstituted 3-6 membered heterocyclyloxy group; G represents a halogeno group.

6. A method for producing a compound represented by formula (I-2), comprising a step of reacting a compound represented by formula (im-3) with a compound represented by formula (im-4) in the presence of an organic base and a copper catalyst using oxygen as an oxidizing agent. In the above formula, Q １ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group; Q ２ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group, and has the following partial structure: In the １ represents an oxygen atom, a nitrogen atom, a group of the formula: NR １ or a group represented by the formula: CR ２ B represents a group represented by the formula: ２ represents an oxygen atom, a nitrogen atom, a group of the formula: NR １ or a group represented by the formula: CR ２ B represents a group represented by the formula: ３ represents an oxygen atom, a nitrogen atom, a group of the formula: NR １ or a group represented by the formula: CR ２ B represents a group represented by the formula: １ , B ２ , and B ３ Any one of the groups is an oxygen atom or a group represented by the formula: NR １ and the remaining two are a nitrogen atom or a group represented by the formula: CR ２ R is a group represented by １ each independently represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C3-6 cycloalkyl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group; R ２ are each independently 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 C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylcarbonyloxy group, a substituted or unsubstituted C1-6 alkoxycarbonyloxy group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C a 1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5-6 membered heterocyclyl group, a substituted or unsubstituted phenyloxy group, a substituted or unsubstituted naphthyloxy group, a substituted or unsubstituted 5-6 membered heterocyclyloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a nitro group, a cyano group, or a halogeno group; the carbon atoms marked with * and + in the partial structure correspond to the carbon atoms marked with * and + in the formula (I-2) or the formula (im-3); Z represents an oxygen atom or a sulfur atom; R ４ each independently 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- to 6-membered heterocyclyl group, or a halogeno group; R ５ each independently 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- to 6-membered heterocyclyl group, or a halogeno group, ４ and R ５ may combine with each other to form a divalent organic group, n represents an integer of 1 to 3, R ６ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a formyl group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group; R ７a is a formyl group, the formula: R ｃ A group represented by the formula: R ｃ A group represented by the formula: R ｃ A group represented by —CO—CO—, or R ｃ -SO ２ R represents a group represented by -; ｃ 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 membered heterocyclyl group, or a substituted or unsubstituted 3-6 membered heterocyclyloxy group.

7. A method for producing a compound represented by formula (I-3), comprising reacting a compound represented by formula (im-5) and a compound represented by formula (im-6) with U １ When is a hydroxyl group, U １ When is a halogeno group, the production method includes a step of reacting in the presence of an acid scavenger. In the above formula, Q １ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group; Q ２ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group, and has the following partial structure: In the １ represents an oxygen atom, a nitrogen atom, a group of the formula: NR １ or a group represented by the formula: CR ２ B represents a group represented by the formula: ２ represents an oxygen atom, a nitrogen atom, a group of the formula: NR １ or a group represented by the formula: CR ２ B represents a group represented by the formula: ３ represents an oxygen atom, a nitrogen atom, a group of the formula: NR １ or a group represented by the formula: CR ２ B represents a group represented by the formula: １ , B ２ , and B ３ Any one of the groups is an oxygen atom or a group represented by the formula: NR １ and the remaining two are a nitrogen atom or a group represented by the formula: CR ２ R is a group represented by １ each independently represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C3-6 cycloalkyl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group; R ２ are each independently 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 C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylcarbonyloxy group, a substituted or unsubstituted C1-6 alkoxycarbonyloxy group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C a 1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5-6 membered heterocyclyl group, a substituted or unsubstituted phenyloxy group, a substituted or unsubstituted naphthyloxy group, a substituted or unsubstituted 5-6 membered heterocyclyloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a nitro group, a cyano group, or a halogeno group, carbon atoms marked with * and + in the partial structure correspond to carbon atoms marked with * and + in the formula (I-3) or the formula (im-5), Z ａ represents an oxygen atom or a sulfur atom; R ４ each independently 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- to 6-membered heterocyclyl group, or a halogeno group; R ５ each independently 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- to 6-membered heterocyclyl group, or a halogeno group, ４ and R ５ may combine with each other to form a divalent organic group, n represents an integer of 1 to 3, R ６ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a formyl group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group; R ７a is a formyl group, the formula: R ｃ A group represented by the formula: R ｃ A group represented by the formula: R ｃ A group represented by —CO—CO—, or R ｃ -SO ２ R represents a group represented by -; ｃ 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 membered heterocyclyl group, or a substituted or unsubstituted 3-6 membered heterocyclyloxy group; U １ represents a hydroxyl group or a halogeno group.

8. A compound represented by formula (im-5A) or a salt thereof. In the formula (im-5A), Q １ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group; R １ represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C3-6 cycloalkyl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group; R ２ａ represents a C1-6 haloalkyl group, a cyano group, or a halogeno group; U ４ represents a carboxyl group, a C1-6 alkoxycarbonyl group, or a halogenocarbonyl group.

9. A compound represented by formula (im-5B) or a salt thereof. In the formula (im-5B), Q １ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group; R １ａ represents a substituted or unsubstituted C2-6 alkyl group or a substituted or unsubstituted C3-6 cycloalkyl group; U ４ represents a carboxyl group, a C1-6 alkoxycarbonyl group, or a halogenocarbonyl group.

10. A compound represented by formula (im-25) or a salt thereof. In the formula (im-25), Q １ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group; R １ａ represents a substituted or unsubstituted C2-6 alkyl group, or a substituted or unsubstituted C3-6 cycloalkyl group.

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