2,6-Dioxo-3,6-Dihydropyrimidine compounds

Abstract

To provide a 2,6-dioxo-3,6-dihydropyrimidine compound that has excellent bactericidal activity, has excellent safety, and can be industrially favorably synthesized, and an agricultural and horticultural fungicide, a nematicide, and an antifungal agent for use in medicine / animals that contain the compound as an active ingredient.SOLUTION: A compound represented by Formula (II) or a salt thereof is provided.SELECTED DRAWING: None

Description

[Technical Field]

[0001] This invention relates to 2,6-dioxo-3,6-dihydropyrimidine compounds and fungicides for agricultural and horticultural use. More specifically, this invention relates to 2,6-dioxo-3,6-dihydropyrimidine compounds that are excellent in bactericidal and antimicrobial activity, are safe, and can be synthesized industrially advantageously, as well as fungicides for agricultural and horticultural use containing the same as an active ingredient. Furthermore, this invention relates to nematicides containing the above compound as an active ingredient. Furthermore, this invention relates to antifungal agents for medical and veterinary use containing the above compound as an active ingredient. This application claims priority to Japanese Patent Application No. 2019-195484, filed on 28 October 2019, and Japanese Patent Application No. 2020-053191, filed on 24 March 2020, and the contents thereof are incorporated herein by reference. [Background technology]

[0002] Various compounds have been proposed that possess control activity against crop diseases in the cultivation of agricultural and horticultural crops. For such compounds to be used as fungicides in agriculture and horticulture, they must not only be sufficiently effective, but also be less likely to cause drug resistance, not cause phytotoxicity to plants or soil contamination, and have low toxicity to livestock and fish.

[0003] Incidentally, Patent Document 1 discloses compounds represented by formula (A), among others. [ka] [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] WO 2013 / 071169 A [Overview of the Initiative] [Problems that the invention aims to solve]

[0005] The object of the present invention is to provide a 2,6-dioxo-3,6-dihydropyrimidine compound (hereinafter sometimes simply referred to as "dihydropyrimidine compound") that is excellent in bactericidal and antimicrobial activity, is safe, and can be synthesized industrially advantageously, and a fungicide for agricultural and horticultural use containing the same as an active ingredient. Furthermore, the object is to provide a nematicide containing the above compound as an active ingredient. Furthermore, the object is to provide a medical and veterinary antifungal agent containing the above compound as an active ingredient. [Means for solving the problem]

[0006] As a result of diligent research to solve the above problems, the inventors have completed the present invention, which encompasses the following aspects.

[0007] [1] A compound represented by formula (II) or a salt thereof. [ka] [In formula (II), Y 1 This indicates an oxygen atom or a sulfur atom; Y 2 This indicates an oxygen atom or a sulfur atom; Z is CX 1 This indicates a group or nitrogen atom represented by; X 1is a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C2-6 alkenyloxy group, a substituted or unsubstituted C2-6 alkynyloxy group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C3-6 cycloalkyloxy group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted C6-10 arylthio group, a substituted or unsubstituted C6-10 arylsulfinyl group, a substituted or unsubstituted C6-10 arylsulfonyl group, a substituted or unsubstituted 5-6 membered heterocyclyl group, a substituted or unsubstituted 5-6 membered heterocyclyloxy group, a nitro group, a cyano group, R 1 a group represented by -CO-, a carboxy group, R 2 a group represented by -O-CO-, R 3 R 4 a group represented by N-, R 3 R 4 a group represented by N-CO-, R<X 1 a group represented by -CO-O-, R 1 -CO-NR 5 a group represented by -, R 2 a group represented by -O-CO-O-, R 2 -O-CO-NR 5 a group represented by -, R 3 R 4 [[ID=!28]]a group represented by N-CO-O-, R 3 R 4 N-CO-NR 5 a group represented by -, R 2 SO2-NR 5 a group represented by -, R 3 R 4 a group represented by N-SO2-, or R 1 O-N=CR 6 represents a group represented by -; R 1Each of these 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 C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R 2 Each of these independently represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R 3 Each of these 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 C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R 4 Each of these independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. Here, R 3 and R 4 These may combine to form a divalent organic group. R 5 Each of these independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. R 6 This represents a hydrogen atom, a halogen group, an amino group, a substituted or unsubstituted monoC1-6 alkylamino group, a substituted or unsubstituted diC1-6 alkylamino group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, or a substituted or unsubstituted 5-6 membered heterocyclyl group; X 2 R 1 ON=CR 6- represents a group, R 1 CO-ON=CR 6 - represents a group, R 3 R 4 N-CO-ON=CR 6 - represents a group, R 3 R 4 NN=CR 6 - A group represented by -, or R 7 -N=CR 6 - indicates the group; R 1 , R 3 , R 4 , and R 6 X 1 It shows a similar meaning to those in R; 7 This represents a substituted or unsubstituted five-membered heterocyclyl group; X 3 R is a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted linear C2-6 alkenyl group, a substituted or unsubstituted linear C2-6 alkynyl group, 1 This refers to a group represented by -CO-, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 4-6 membered heterocyclyl group; A represents a substituted or unsubstituted C1-6 alkylene group, a substituted or unsubstituted C2-6 alkenylene group, a substituted or unsubstituted C2-6 alkynylene group, or a substituted or unsubstituted C3-6 cycloalkylene group; Q represents a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-10 membered heterocycline ring. [2] The compound or salt thereof described in [1], wherein formula (II) is represented by formula (I). [ka] [In formula (I), X 1 , X 2 , X 3 A and Q have the same meanings as those in [1]. [3] X 3Substituents on linear C1-6 alkyl groups, linear C2-6 alkenyl groups, linear C2-6 alkynyl groups, C3-6 cycloalkyl groups, C6-10 aryl groups, or 4-6 membered ring heterocyclyl groups in the above, Halogeno group, substituted or unsubstituted C1-6 alkyl group, substituted or unsubstituted C2-6 alkenyl group, substituted or unsubstituted C2-6 alkynyl group, hydroxyl group, substituted or unsubstituted C1-6 alkoxy group, substituted or unsubstituted C2-6 alkenyloxy group, substituted or unsubstituted C2-6 alkynyloxy group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alkylsulfinyl group, substituted or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted C 3-6 cycloalkyl groups, substituted or unsubstituted C3-6 cycloalkyloxy groups, substituted or unsubstituted C6-10 aryl groups, substituted or unsubstituted C6-10 aryloxy groups, substituted or unsubstituted C6-10 arylthio groups, substituted or unsubstituted C6-10 arylsulfinyl groups, substituted or unsubstituted C6-10 arylsulfonyl groups, substituted or unsubstituted 3-10 membered heterocyclyl groups, substituted or unsubstituted 3-10 membered heterocyclyloxy groups, nitro groups, cyano groups, R a Groups represented by -CO-, carboxyl groups, R b A group represented by -O-CO-, R c R d The group represented by N-, R c R d The group represented by N-CO-, R c R d N-NR d A group represented by -CO-, R a A group represented by -CO-O-, R a -CO-NR e - represents a group, R a -CO-CO-NR e - represents a group, R a -CO-NR e -NR e - represents a group, R a -CO-NR e -NR e A group represented by -CO-, Rb A group represented by -O-CO-O-, R b -O-CO-NR e A group represented by -, R c R d A group represented by N-CO-O-, R c R d N-CO-NR e A group represented by -, R c R d N-CO-CO-NR e A group represented by -, R a -CS-NR e A group represented by -, R c R d N-CS-NR e A group represented by -, R b SO2-NR e A group represented by -, R c R d A group represented by N-SO2-, R a O-N=CR f A group represented by -, R h R j A group represented by C=N-O-, R a -C(=NR g )-NR e A group represented by -, R c R d N-C(=NR g )- A group represented by, R h R i A group represented by S(=O)=N-CO-, and R h R i One or more substituents selected from the group consisting of a group represented by S=N-CO-; R a Each is 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 C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 3-10 membered heterocyclyl group, R bEach of these independently represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-10 membered heterocyclyl group. R c Each of these 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 C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R d Each of these independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a substituted or unsubstituted C6-10 aryl group, where R c and R d These may combine to form a divalent organic group. R e Each of these independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a substituted or unsubstituted C6-10 aryl group. R f This represents a hydrogen atom, an amino group, or a substituted or unsubstituted C1-6 alkyl group. R g Each of these independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. R h Each of these independently represents a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. R i Each independently represents a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, where R h and R i These may also combine to form a divalent organic group; If there are two or more substituents on a linear C1-6 alkyl group, two of them may combine to form a divalent organic group; The compound or salt thereof described in [1] or [2]. [4] The substituents on the C1-6 alkylene group or C2-6 alkenylene group in A are Halogeno group, substituted or unsubstituted C1-6 alkyl group, substituted or unsubstituted C2-6 alkenyl group, substituted or unsubstituted C2-6 alkynyl group, hydroxyl group, substituted or unsubstituted C1-6 alkoxy group, substituted or unsubstituted C2-6 alkenyloxy group, substituted or unsubstituted C2-6 alkynyloxy group, mercapto group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alkylsulfinyl group, substituted or unsubstituted C1-6 alkylsulfonyl group, substituted or Unsubstituted C3-6 cycloalkyl groups, substituted or unsubstituted C3-6 cycloalkyloxy groups, substituted or unsubstituted C6-10 aryl groups, substituted or unsubstituted C6-10 aryloxy groups, substituted or unsubstituted C6-10 arylthio groups, substituted or unsubstituted C6-10 arylsulfinyl groups, substituted or unsubstituted C6-10 arylsulfonyl groups, substituted or unsubstituted 3-6 membered heterocyclyl groups, substituted or unsubstituted 3-6 membered heterocyclyloxy groups, nitro groups, cyano groups, R a1 Groups represented by -CO-, carboxyl groups, R b1 A group represented by -O-CO-, R c1 R d1 The group represented by N-, R c1 R d1 The group represented by N-CO-, R a1 A group represented by -CO-O-, R a1 -CO-NR e1 - represents a group, R b1 A group represented by -O-CO-O-, R b1 -O-CO-NR e1 - represents a group, R c1 R d1 The group represented by N-CO-O-, R c1 R d1 N-CO-NR e1 - represents a group, R b1SO2-NR e1 - represents a group, R c1 R d1 The group represented by N-SO2-, R a1 ON=CR f1 - represents a group, R g1 R h1 Groups represented by C=NO-, oxo groups (O=), thioxo groups (S=), R a1 A divalent base represented by -N=, R a1 A divalent base represented by ON=, R c1 R d1 A divalent base represented by NN=, R a1 -CO-NR e1 A divalent base represented by -N=, R b1 -O-CO-NR e1 A divalent base represented by -N=, R b1 SO2-NR e1 One or more substituents selected from the group consisting of divalent groups represented by -N=; R a1 Each of these 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 C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R b1 Each of these independently represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R c1 Each of these 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 C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R d1Each of these independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, where R c1 and R d1 These may combine to form a divalent organic group. R e1 Each of these independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. R f1 This represents a hydrogen atom, or a substituted or unsubstituted C1-6 alkyl group. R g1 This represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R h1 R represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, where R g1 and R h1 These may also combine to form a divalent organic group; If there are two or more substituents on a C1-6 alkylene group or a C2-6 alkenylene group, two of them may combine to form a divalent organic group; A compound or salt thereof as described in any of [1] to [3]. A fungicide for agricultural and horticultural use containing, as an active ingredient, at least one selected from the group consisting of compounds described in any of [5], [1] to [4], and salts thereof. [6] A fungicide for agricultural and horticultural use as described in [5], for seed treatment. A nematicide containing at least one selected from the group consisting of compounds described in any of [7] [1] to [4] and salts thereof as an active ingredient. A medical or veterinary antifungal agent containing, as an active ingredient, at least one selected from the group consisting of compounds described in any of [8], [1] to [4], and salts thereof. [9] A compound represented by formula (III) or a salt thereof. [ka] [In formula (III), X 1 This includes hydrogen atoms, halogen groups, substituted or unsubstituted C1-6 alkyl groups, substituted or unsubstituted C2-6 alkenyl groups, substituted or unsubstituted C2-6 alkynyl groups, hydroxyl groups, substituted or unsubstituted C1-6 alkoxy groups, substituted or unsubstituted C2-6 alkenyloxy groups, substituted or unsubstituted C2-6 alkynyloxy groups, substituted or unsubstituted C1-6 alkylthio groups, substituted or unsubstituted C1-6 alkylsulfinyl groups, substituted or unsubstituted C1-6 alkylsulfonyl groups, substituted or Unsubstituted C3-6 cycloalkyl groups, substituted or unsubstituted C3-6 cycloalkyloxy groups, substituted or unsubstituted C6-10 aryl groups, substituted or unsubstituted C6-10 aryloxy groups, substituted or unsubstituted C6-10 arylthio groups, substituted or unsubstituted C6-10 arylsulfinyl groups, substituted or unsubstituted C6-10 arylsulfonyl groups, substituted or unsubstituted 5-6 membered heterocyclyl groups, substituted or unsubstituted 5-6 membered heterocyclyloxy groups, nitro groups, cyano groups, R 1 Groups represented by -CO-, carboxyl groups, R 2 A group represented by -O-CO-, R 3 R 4 The group represented by N-, R 3 R 4 The group represented by N-CO-, R 1 A group represented by -CO-O-, R 1 -CO-NR 5 - represents a group, R 2 A group represented by -O-CO-O-, R 2 -O-CO-NR 5 - represents a group, R 3 R 4 The group represented by N-CO-O-, R 3 R 4 N-CO-NR 5 - represents a group, R 2 SO2-NR 5 - represents a group, R 3 R 4A group represented by N-SO2-, or R 1 ON=CR 6 - indicates the group represented by; R 1 Each of these 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 C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R 2 Each of these independently represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R 3 Each of these 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 C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R 4 Each of these independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. Here, R 3 and R 4 These may combine to form a divalent organic group. R 5 Each of these independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. R 6This represents a hydrogen atom, a halogen group, an amino group, a substituted or unsubstituted monoC1-6 alkylamino group, a substituted or unsubstituted diC1-6 alkylamino group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, or a substituted or unsubstituted 5-6 membered heterocyclyl group; X 2 R 1 ON=CR 6 - represents a group, R 1 CO-ON=CR 6 - represents a group, R 3 R 4 N-CO-ON=CR 6 - represents a group, R 3 R 4 NN=CR 6 - A group represented by -, or R 7 -N=CR 6 - indicates the group; R 1 , R 3 , R 4 , and R 6 X 1 It shows a similar meaning to those in R; 7 This represents a substituted or unsubstituted five-membered heterocyclyl group; A represents a substituted or unsubstituted C1-6 alkylene group, a substituted or unsubstituted C2-6 alkenylene group, a substituted or unsubstituted C2-6 alkynylene group, or a substituted or unsubstituted C3-6 cycloalkylene group; Q represents a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-10 membered heterocycline ring.

[10] A compound represented by formula (IV) or a salt thereof. [ka] [In formula (IV), X 1This includes hydrogen atoms, halogen groups, substituted or unsubstituted C1-6 alkyl groups, substituted or unsubstituted C2-6 alkenyl groups, substituted or unsubstituted C2-6 alkynyl groups, hydroxyl groups, substituted or unsubstituted C1-6 alkoxy groups, substituted or unsubstituted C2-6 alkenyloxy groups, substituted or unsubstituted C2-6 alkynyloxy groups, substituted or unsubstituted C1-6 alkylthio groups, substituted or unsubstituted C1-6 alkylsulfinyl groups, substituted or unsubstituted C1-6 alkylsulfonyl groups, substituted or Unsubstituted C3-6 cycloalkyl groups, substituted or unsubstituted C3-6 cycloalkyloxy groups, substituted or unsubstituted C6-10 aryl groups, substituted or unsubstituted C6-10 aryloxy groups, substituted or unsubstituted C6-10 arylthio groups, substituted or unsubstituted C6-10 arylsulfinyl groups, substituted or unsubstituted C6-10 arylsulfonyl groups, substituted or unsubstituted 5-6 membered heterocyclyl groups, substituted or unsubstituted 5-6 membered heterocyclyloxy groups, nitro groups, cyano groups, R 1 Groups represented by -CO-, carboxyl groups, R 2 A group represented by -O-CO-, R 3 R 4 The group represented by N-, R 3 R 4 The group represented by N-CO-, R 1 A group represented by -CO-O-, R 1 -CO-NR 5 - represents a group, R 2 A group represented by -O-CO-O-, R 2 -O-CO-NR 5 - represents a group, R 3 R 4 The group represented by N-CO-O-, R 3 R 4 N-CO-NR 5 - represents a group, R 2 SO2-NR 5 - represents a group, R 3 R 4 A group represented by N-SO2-, or R 1 ON=CR 6 - indicates the group represented by; R 1Each of these 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 C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R 2 Each of these independently represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R 3 Each of these 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 C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R 4 Each of these independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. Here, R 3 and R 4 These may combine to form a divalent organic group. R 5 Each of these independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. R 6 This represents a hydrogen atom, a halogen group, an amino group, a substituted or unsubstituted monoC1-6 alkylamino group, a substituted or unsubstituted diC1-6 alkylamino group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, or a substituted or unsubstituted 5-6 membered heterocyclyl group; X 2 R 1 ON=CR 6- represents a group, R 1 CO-ON=CR 6 - represents a group, R 3 R 4 N-CO-ON=CR 6 - represents a group, R 3 R 4 NR 3 R 4 NN=CR 6 - A group represented by -, or R 7 -N=CR 6 - indicates the group; R 1 , R 3 , R 4 , and R 6 X 1 It shows a similar meaning to those in R; 7 This represents a substituted or unsubstituted five-membered heterocyclyl group; X 3 R is a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted linear C2-6 alkenyl group, a substituted or unsubstituted linear C2-6 alkynyl group, 1 This refers to a group represented by -CO-, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 4-6 membered heterocyclyl group; X 4 This represents a hydrogen atom or a C1-6 alkoxymethyl group. [Effects of the Invention]

[0008] The dihydropyrimidine compounds of the present invention exhibit excellent bactericidal and antimicrobial activity, reliable efficacy, superior safety, and can be synthesized industrially advantageously. The fungicides and nematicides for agricultural and horticultural use of the present invention have excellent control effects, do not cause phytotoxicity to plants, and have little toxicity to humans, livestock, or fish, as well as little impact on the environment. The medical and veterinary antifungal agents of the present invention have excellent antibacterial effects and low toxicity to humans, animals, and fish. [Modes for carrying out the invention]

[0009] [Dihydropyrimidine compounds] The dihydropyrimidine compound of the present invention is a compound represented by formula (II) (hereinafter sometimes referred to as compound (II)) or a salt of compound (II). [ka] Preferably, it is a compound represented by formula (I) (hereinafter sometimes referred to as compound (I)) or a salt of compound (I).

[0010] [ka]

[0011] In this invention, the term "unsubstituted" means that only the core group is present. When only the name of the core group is mentioned, it means "unsubstituted" unless otherwise specified. On the other hand, the term "substituted" means that one of the hydrogen atoms of the parent group is replaced by a group with the same or different structure as the parent group. Therefore, a "substituent" is another group bonded to the parent group. There may be one substituent or two or more substituents. The two or more substituents may be the same or different.

[0012] The "substituents" are chemically acceptable and not particularly limited insofar as they have the effects of the present invention. The following are specific examples of groups that can act as "substituents." Halogeno groups such as fluoro groups, chloro groups, bromo groups, and iod groups; C1-6 alkyl groups such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, and n-hexyl group; C2-6 alkenyl groups such as vinyl group, 1-propenyl group, 2-propenyl group, 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; C2-6 alkynyl groups such as ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, and 1,1-dimethyl-2-butynyl group;

[0013] C3-6 cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups; C3-6 cycloalkenyl groups such as 2-cyclopropenyl, 2-cyclopentenyl, and 3-cyclohexenyl groups; C6-10 aryl groups such as phenyl and naphthyl groups; C6-10 aryl C1-6 alkyl groups such as benzyl and phenethyl groups; A heterocyclyl group with 3 to 6 members; 3-6 membered heterocyclyl C1-6 alkyl groups;

[0014] Hydroxyl group; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy groups; C2-6 alkenyloxy groups such as vinyloxy groups, allyloxy groups, propenyloxy groups, and butenyloxy groups; C2-6 alkynyloxy groups such as ethynyloxy groups and propargyloxy groups; C6-10 aryloxy groups such as phenoxy and naphthoxy groups; C6-10 aryl C1-6 alkoxy groups such as benzyloxy groups and phenethyloxy groups;

[0015] Carboxy group; Formyl group; C1-6 alkylcarbonyl groups such as acetyl groups and propionyl groups; Formyloxy group; C1-6 alkylcarbonyloxy groups such as acetyloxy groups and propionyloxy groups; C1-6 alkoxycarbonyl groups such as methoxycarbonyl groups, ethoxycarbonyl groups, n-propoxycarbonyl groups, i-propoxycarbonyl groups, n-butoxycarbonyl groups, and t-butoxycarbonyl groups;

[0016] C1-6 haloalkyl groups such as chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, 1-fluoro-n-butyl, and perfluoro-n-pentyl groups; C2-6 haloalkenyl groups such as 2-chloro-1-propenyl group and 2-fluoro-1-butenyl group; C2-6 haloalkynyl groups such as 4,4-dichloro-1-butynyl, 4-fluoro-1-pentynyl, and 5-bromo-2-pentynyl; C3-6 halocycloalkyl groups such as 3,3-difluorocyclobutyl group; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, trifluoromethoxy, and 2,2,2-trifluoroethoxy; C2-6 haloalkenyloxy groups such as 2-chloropropenyloxy groups and 3-bromobutenyloxy groups; C1-6 haloalkylcarbonyl groups such as chloroacetyl, trifluoroacetyl, and trichloroacetyl groups;

[0017] amino group; C1-6 alkyl-substituted amino groups such as methylamino groups, dimethylamino groups, and diethylamino groups; C6-10 arylamino groups such as anilino groups and naphthylamino groups; C6-10 aryl C1-6 alkylamino groups such as benzylamino groups and phenethylamino groups;

[0018] Formylamino group; C1-6 alkylcarbonylamino groups such as acetylamino group, propionylamino group, butyrylamino group, and i-propylcarbonylamino group; C1-6 alkoxycarbonylamino groups such as methoxycarbonylamino groups, ethoxycarbonylamino groups, n-propoxycarbonylamino groups, and i-propoxycarbonylamino groups; Unsubstituted or substituted aminocarbonyl groups such as carbamoyl groups, dimethylaminocarbonyl groups, phenylaminocarbonyl groups, and N-phenyl-N-methylaminocarbonyl groups; Imino C1-6 alkyl groups such as iminomethyl group, (1-imino)ethyl group, and (1-imino)-n-propyl group; Substituted or unsubstituted N-hydroxyimino C1-6 alkyl groups such as N-hydroxyiminomethyl group, (1-(N-hydroxy)-imino)ethyl group, (1-(N-hydroxy)-imino)propyl group, N-methoxyiminomethyl group, and (1-(N-methoxy)-imino)ethyl group; aminocarbonyloxy group; C1-6 alkyl-substituted aminocarbonyloxy groups such as ethylaminocarbonyloxy groups and dimethylaminocarbonyloxy groups;

[0019] Mercapto group; C1-6 alkylthio groups such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, and t-butylthio group; C1-6 haloalkylthio groups such as trifluoromethylthio group and 2,2,2-trifluoroethylthio group; C2-6 alkenylthio groups such as vinylthio groups and allylthio groups; C2-6 alkynylthio groups such as ethynylthio groups and propargylthio groups; C1-6 alkyl sulfinyl groups such as methyl sulfinyl group, ethyl sulfinyl group, and t-butyl sulfinyl group; C1-6 haloalkylsulfinyl groups such as trifluoromethylsulfinyl group and 2,2,2-trifluoroethylsulfinyl group; C2-6 alkenyl sulfinyl groups such as allyl sulfinyl groups; C2-6 alkynylsulfinyl groups such as propargylsulfinyl groups; C1-6 alkylsulfonyl groups such as methylsulfonyl groups, ethylsulfonyl groups, and t-butylsulfonyl groups; C1-6 haloalkylsulfonyl groups such as trifluoromethylsulfonyl group and 2,2,2-trifluoroethylsulfonyl group; C2-6 alkenylsulfonyl groups such as allylsulfonyl groups; C2-6 alkynylsulfonyl groups such as propargylsulfonyl groups; aminothiocarbonyl group; C1-6 alkyl sulfoxiimino groups such as S,S-dimethyl sulfoxiimino groups;

[0020] TriC1-6 alkyl-substituted silyl groups such as trimethylsilyl group, triethylsilyl group, and t-butyldimethylsilyl group; Tri-C6-10 aryl-substituted silyl groups such as triphenylsilyl groups; Cyano group; Nitro group;

[0021] Terms such as "C1-6" indicate that the number of carbon atoms in the parent group is 1 to 6. This number of carbon atoms does not include the number of carbon atoms in the substituent. For example, the ethoxybutyl group is classified as a C2 alkoxy C4 alkyl group because its parent group is a butyl group and its substituent is an ethoxy group.

[0022] Furthermore, the above-mentioned "3- to 6-membered heterocyclyl group" includes 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms as constituent atoms of the ring. Examples of "3- to 6-membered heterocyclyl groups" include 3- to 6-membered saturated heterocyclyl groups, 5- to 6-membered heteroaryl groups, and 5- to 6-membered partially unsaturated heterocyclyl groups.

[0023] Examples of saturated heterocyclyl groups with 3 to 6 members include azilidinyl group, epoxy group, azetidinyl group, oxetanyl group, pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, tetrahydro-2H-pyranyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, and dioxanyl group.

[0024] Examples of 5-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups. Examples of six-membered heteroaryl groups include pyridyl, pyrazinyl, pyrimidinyl, pyridadinyl, and triazinyl groups. Examples of partially unsaturated heterocyclyl groups in a five-membered ring include pyrrolinyl groups, dihydrofuranyl groups, imidazolinyl groups, pyrazolinyl groups, and oxazolinyl groups. Examples of partially unsaturated heterocyclyl groups in a six-membered ring include isoxazolinyl groups and dihydropyranyl groups. These "substituents" may have any hydrogen atom in the substituent substituted with a group of a different structure.

[0025] [Y 1 , Y 2 ] Y 1 Y represents an oxygen atom or a sulfur atom. 2 This represents an oxygen atom or a sulfur atom. In the present invention, preferred Y 1is an oxygen atom, and is preferred Y 2 It is an oxygen atom.

[0026] [Z] Z is CX 1 This indicates a group or nitrogen atom represented by [the specified element].

[0027] [X 1 ] X 1 This includes hydrogen atoms, halogen groups, substituted or unsubstituted C1-6 alkyl groups, substituted or unsubstituted C2-6 alkenyl groups, substituted or unsubstituted C2-6 alkynyl groups, hydroxyl groups, substituted or unsubstituted C1-6 alkoxy groups, substituted or unsubstituted C2-6 alkenyloxy groups, substituted or unsubstituted C2-6 alkynyloxy groups, substituted or unsubstituted C1-6 alkylthio groups, substituted or unsubstituted C1-6 alkylsulfinyl groups, substituted or unsubstituted C1-6 alkylsulfonyl groups, substituted or Unsubstituted C3-6 cycloalkyl groups, substituted or unsubstituted C3-6 cycloalkyloxy groups, substituted or unsubstituted C6-10 aryl groups, substituted or unsubstituted C6-10 aryloxy groups, substituted or unsubstituted C6-10 arylthio groups, substituted or unsubstituted C6-10 arylsulfinyl groups, substituted or unsubstituted C6-10 arylsulfonyl groups, substituted or unsubstituted 5-6 membered heterocyclyl groups, substituted or unsubstituted 5-6 membered heterocyclyloxy groups, nitro groups, cyano groups, R 1 Groups represented by -CO-, carboxyl groups, R 2 A group represented by -O-CO-, R 3 R 4 The group represented by N-, R 3 R 4 The group represented by N-CO-, R 1 A group represented by -CO-O-, R 1 -CO-NR 5 - represents a group, R 2 A group represented by -O-CO-O-, R 2 -O-CO-NR 5 - represents a group, R 3 R 4 The group represented by N-CO-O-, R 3 R4 N-CO-NR 5 - represents a group, R 2 SO2-NR 5 - represents a group, R 3 R 4 A group represented by N-SO2-, or R 1 ON=CR 6 This indicates a group represented by -.

[0028] R 1 Each of these 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 C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R 2 Each of these independently represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R 3 Each of these 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 C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R 4 Each of these independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. Here, R 3 and R 4 These may combine to form a divalent organic group. R 5 Each of these independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. R 6This represents a hydrogen atom, a halogeno group, an amino group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, or a substituted or unsubstituted 5-6 membered heterocyclyl group.

[0029] X 1 Examples of "halogeno groups" in this context include fluoro groups, chloro groups, bromo groups, and iod groups.

[0030] X 1 The "C1-6 alkyl group" in this expression may be a straight chain or a branched chain. 1 Examples of "C1-6 alkyl groups" in this context include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s-butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, and i-hexyl group.

[0031] X 1 Examples of "C2-6 alkenyl groups" in this context include vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, and 5-hexenyl group.

[0032] X 1 Examples of "C2-6 alkynyl groups" in this context include ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, and 1,1-dimethyl-2-butynyl group.

[0033] X 1 Examples of "C1-6 alkoxy groups" in this context include methoxy group, ethoxy group, n-propoxy group, n-butoxy group, n-pentyloxy group, n-hexyloxy group, i-propoxy group, i-butoxy group, s-butoxy group, t-butoxy group, and i-hexyloxy group. X 1 Examples of "C2-6 alkenyloxy groups" in this context include vinyloxy groups, allyloxy groups, propenyloxy groups, and butenyloxy groups. X 1 Examples of "C2-6 alkynyloxy groups" in this context include ethynyloxy groups and propargyloxy groups.

[0034] X 1 Examples of "C1-6 alkylthio groups" in this context include methylthio group, ethylthio group, n-propylthio group, n-butylthio group, n-pentylthio group, n-hexylthio group, and i-propylthio group. X 1 Examples of "C1-6 alkylsulfinyl groups" in this context include methylsulfinyl groups, ethylsulfinyl groups, and t-butylsulfinyl groups. X 1 Examples of "C1-6 alkylsulfonyl groups" in this context include methylsulfonyl groups, ethylsulfonyl groups, and t-butylsulfonyl groups.

[0035] X 1Substituents on the "C1-6 alkyl group", "C2-6 alkenyl group", "C2-6 alkynyl group", "C1-6 alkoxy group", "C2-6 alkenyloxy group", "C2-6 alkynyloxy group", "C1-6 alkylthio group", "C1-6 alkylsulfinyl group", or "C1-6 alkylsulfonyl group" include halogen groups such as fluoro groups, chloro groups, bromo groups, and iod groups; hydroxyl groups; methoxy groups, ethoxy groups, n-propoxy groups, i-propoxy groups, n-butoxy groups, and s-butoxy groups. C1-6 alkoxy groups such as xy group, i-butoxy group, t-butoxy group; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group; C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group; C6-10 aryl groups such as phenyl group, naphthyl group; 4-methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoro C6-10 aryl groups substituted with one or more substituents such as methoxyphenyl groups, C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups; 5-membered heteroaryl groups such as pyrrolyl groups, furyl groups, thienyl groups, imidazolyl groups, pyrazolyl groups, oxazolyl groups, isoxazolyl groups, thiazolyl groups, isothiazolyl groups, triazolyl groups, oxadiazolyl groups, thiadiazolyl groups, and tetrazolyl groups; C1-6 alkyl groups, C1 A 5-membered ring heteroaryl group substituted with one or more substituents of a ~6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 6-membered ring heteroaryl group such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridadinyl group, or a triazinyl group; a 6-membered ring 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 cyano group is preferred.

[0036] X 1Examples of "C3-6 cycloalkyl groups" in this context include cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, and cyclohexyl groups. X 1 Examples of "C3-6 cycloalkyloxy groups" in this context include cyclopropyloxy group, cyclobutyloxy group, cyclopentyloxy group, and cyclohexyloxy group.

[0037] X 1 Examples of "C6-10 aryl groups" in this context include phenyl group, naphthyl group, indanyl group, indenyl group, tetralinyl group, and others. X 1 Examples of "C6-10 aryloxy groups" in this context include phenoxy groups and naphthoxy groups.

[0038] X 1 Examples of "C6-10 arylthio groups" in this context include phenylthio groups and naphthylthio groups. X 1 Examples of "C6-10 arylsulfinyl groups" in this context include phenylsulfinyl groups and naphthylsulfinyl groups. X 1 Examples of "C6-10 arylsulfonyl groups" in this context include phenylsulfonyl groups and naphthylsulfonyl groups.

[0039] X 1 In this context, a "5-6 membered heterocyclyl group" is a group that contains one, two, three, or four heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms as constituent atoms of the ring. When there are two or more heteroatoms, they may be the same or different. Examples of "5-6 membered heterocyclyl groups" include 5-6 membered saturated heterocyclyl groups, 5-6 membered heteroaryl groups, and 5-6 membered partially unsaturated heterocyclyl groups.

[0040] Examples of saturated heterocyclyl groups with 5-6 member rings include pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, tetrahydro-2H-pyranyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, and dioxanyl group. Examples of 5- to 6-membered heteroaryl groups include 5-membered heteroaryl groups such as pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups; and 6-membered heteroaryl groups such as pyridyl, pyrazinyl, pyrimidinyl, pyridadinyl, and triazinyl groups. Examples of partially unsaturated heterocyclyl groups with 5- to 6 member rings include pyrrolinyl groups, dihydrofuranyl groups, imidazolinyl groups, pyrazolinyl groups, and oxazolinyl groups; and partially unsaturated heterocyclyl groups with 6 member rings, such as isoxazolinyl groups and dihydropyranyl groups.

[0041] X 1 In this context, a "5-6 membered heterocyclyloxy group" has a structure in which a 5-6 membered heterocyclyl group is bonded to an oxy group. Specific examples include thiazolyloxy groups and pyridyloxy groups.

[0042] X 1Substituents on "C3-6 cycloalkyl groups", "C3-6 cycloalkyloxy groups", "C6-10 aryl groups", "C6-10 aryloxy groups", "C6-10 arylthio groups", "C6-10 arylsulfinyl groups", "C6-10 arylsulfonyl groups", "5-6 membered heterocyclyl groups", or "5-6 membered heterocyclyloxy groups" include halogeno groups such as fluoro groups, chloro groups, bromo groups, and iod groups; methyl groups, ethyl groups, n-propyl groups, i-propyl groups, n-butyl groups, C1-6 alkyl groups such as s-butyl, i-butyl, t-butyl, n-pentyl, and n-hexyl groups; C1-6 haloalkyl groups such as chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, and 1-fluoro-n-butyl groups; hydroxyl groups; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy groups; 2-chloro-n-propoxy and 2,3-dichlorobutoxy groups, C1-6 haloalkoxy groups such as trifluoromethoxy; C6-10 aryl groups such as phenyl and naphthyl groups; C6-10 aryl groups substituted with one or more substituents of any C1-6 alkyl, C1-6 alkoxy, halogeno, C1-6 haloalkyl, or C1-6 haloalkoxy groups, such as 4-methylphenyl, 4-methoxyphenyl, 4-chlorophenyl, 4-trifluoromethylphenyl, and 4-trifluoromethoxyphenyl; pyrrolyl, furyl, thienyl, and imidazoly Five-membered heteroaryl groups such as C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups; six-membered heteroaryl groups such as pyridyl groups, pyrazinyl groups, pyrimidinyl groups, pyridadinyl groups, or triazinyl groups;A 6-membered ring 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 cyano group is preferred. Furthermore, oxo groups are also preferred as substituents on "C3-6 cycloalkyl groups," "C3-6 cycloalkyloxy groups," "5-6 membered heterocyclyl groups," or "5-6 membered heterocyclyloxy groups."

[0043] X 1 In "R" 1 In the group represented by -CO-, R 1 This represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group.

[0044] R 1 Examples of "C1-6 alkyl groups" in this context include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s-butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, and i-hexyl group. R 1 Examples of "C2-6 alkenyl groups" in this context include vinyl groups and 1-propenyl groups. R 1 Examples of "C2-6 alkynyl groups" in this context include the ethynyl group and the 1-propynyl group. R 1Substituents on the "C1-6 alkyl group", "C2-6 alkenyl group", or "C2-6 alkynyl group" include halogen groups such as fluoro, chloro, bromo, and iod groups; hydroxyl groups; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy groups; 2-chloro-n-propoxy, 2,3-dichlorobutoxy, and trifluorometh C1-6 haloalkoxy groups such as xy groups; C3-6 cycloalkyl groups such as cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, and cyclohexyl groups; C6-10 aryl groups such as phenyl groups and naphthyl groups; C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, and C1-6 halo groups such as 4-methylphenyl groups, 4-methoxyphenyl groups, 4-chlorophenyl groups, 4-trifluoromethylphenyl groups, and 4-trifluoromethoxyphenyl groups. C6-10 aryl groups substituted with one or more substituents of a aryl group or a C1-6 haloalkoxy group; 5-membered heteroaryl groups such as pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups; C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkoxy groups A 5-membered ring heteroaryl group substituted with one or more substituents of a chyl group or a C1-6 haloalkoxy group; a 6-membered ring heteroaryl group such as a pyridyl group, pyrazinyl group, pyrimidinyl group, pyridadinyl group, or triazinyl group; a 6-membered ring 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 cyano group is preferred.

[0045] R 1 Examples of "C3-6 cycloalkyl groups" in this context include cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, and cyclohexyl groups. R 1Examples of "C6-10 aryl groups" in this context include phenyl, naphthyl, indenyl, indanyl, and tetralinyl groups.

[0046] R 1 In this context, a "5-6 membered heterocyclyl group" is a group that contains one, two, three, or four heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms as constituent atoms of the ring. When there are two or more heteroatoms, they may be the same or different. Examples of "5-6 membered heterocyclyl groups" include 5-6 membered saturated heterocyclyl groups, 5-6 membered heteroaryl groups, and 5-6 membered partially unsaturated heterocyclyl groups. Examples of saturated heterocyclyl groups with 5-6 member rings include pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, tetrahydro-2H-pyranyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, and dioxanyl group. Examples of 5- to 6-membered heteroaryl groups include 5-membered heteroaryl groups such as pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups; and 6-membered heteroaryl groups such as pyridyl, pyrazinyl, pyrimidinyl, pyridadinyl, and triazinyl groups. Examples of partially unsaturated heterocyclyl groups with 5- to 6 member rings include pyrrolinyl, dihydrofuranyl, imidazolinyl, pyrazolinyl, and oxazolinyl groups (5-member rings); and partially unsaturated heterocyclyl groups with 6 member rings, such as isoxazolinyl and dihydropyranyl groups.

[0047] R 1Substituents on the "C3-6 cycloalkyl group", "C6-10 aryl group", or "5-6 membered heterocyclyl group" in this context include halogen groups such as fluoro, chloro, bromo, and iod groups; 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 groups; chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, and 1-fluoro-n-butyl groups. C1-6 haloalkyl groups such as hydroxyl groups; hydroxyl groups; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy groups; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, and trifluoromethoxy groups; C6-10 aryl groups such as phenyl and naphthyl groups; 4-methylphenyl, 4-methoxyphenyl, 4-chlorophenyl, and 4-trifluoromethylphenyl groups C6-10 aryl groups substituted with one or more substituents such as a C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group, such as a 4-trifluoromethoxyphenyl group; 5-membered heteroaryl groups such as pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group, etc.; C1-6 alkyl A 5-membered ring heteroaryl group substituted with one or more substituents of a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 6-membered ring heteroaryl group such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridadinyl group, or a triazinyl group; a 6-membered ring 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 cyano group is preferred. Furthermore, oxo groups are also preferred as substituents on the "C3-6 cycloalkyl group" or the "5-6 membered heterocyclyl group".

[0048] "R 1 Specific examples of groups represented by "-CO-" include the formyl group, acetyl group, propionyl group, butyryl group, and i-propylcarbonyl group.

[0049] X 1 In "R" 2 In the group represented by -O-CO-, R 2 This represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R 2 A specific example of a substituent in R 1 The same examples given in the previous section can be cited.

[0050] "R 2 Specific examples of groups represented by "-O-CO-" include the methoxycarbonyl group, ethoxycarbonyl group, and t-butoxycarbonyl group.

[0051] X 1 In "R" 3 R 4 In the group represented by N-, R 3 R represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. 4 This represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. R 3 or R 4 A specific example of a substituent in R 1 The same examples given in the previous section can be cited.

[0052] Here, R 3 and R 4 These may combine to form a divalent organic group. Examples of divalent organic groups that can be formed include substituted or unsubstituted C2-5 alkylene groups or substituted or unsubstituted C1-3 alkylene oxy C1-3 alkylene groups. Examples of "C2-5 alkylene groups" include dimethylene groups, trimethylene groups, and tetramethylene groups. Examples of "C1-3 alkylene oxy C1-3 alkylene groups" include the dimethylene oxydimethylene group. Preferred substituents on the "C2-5 alkylene group" or "C1-3 alkyleneoxy C1-3 alkylene group" are halogeno groups such as fluoro groups, chloro groups, bromo groups, and iod groups; C1-6 alkyl groups such as methyl groups, ethyl groups, n-propyl groups, i-propyl groups, n-butyl groups, s-butyl groups, i-butyl groups, and t-butyl groups; or C1-6 haloalkyl groups such as chloromethyl groups, chloroethyl groups, trifluoromethyl groups, 1,2-dichloro-n-propyl groups, and 1-fluoro-n-butyl groups.

[0053] "R 3 R 4 Specific examples of groups represented by "N-" include amino groups, methylamino groups, dimethylamino groups, and i-propylamino groups.

[0054] X 1 In "R" 3 R 4 In the group represented by N-CO-, R 3 and R 4 The above "R 3 R 4 This has the same meaning as in "groups represented by N-". "R 3 R 4Specific examples of groups represented by "N-CO-" include the carbamoyl group, N,N-dimethylaminocarbonyl group, N-(i-propyl)aminocarbonyl group, and N-(i-propyl)-N-methylaminocarbonyl group.

[0055] X 1 In "R" 1 In the group represented by -CO-O-, R 1 The above "R 1 This has the same meaning as in "a group represented by -CO-". "R 1 Examples of groups represented by "-CO-O-" include the acetyloxy group and the i-propylcarbonyloxy group.

[0056] X 1 In "R" 1 -CO-NR 5 - in the group represented by -, R 1 The above "R 1 This has the same meaning as in "a group represented by -CO-". R 5 This represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. R 5 A specific example of a substituent in R 1 The same examples given in the previous section can be cited. "R 1 -CO-NR 5 Examples of groups represented by "-" include the acetylamino group and the i-propylcarbonylamino group.

[0057] X 1 In "R" 2 In the group represented by -O-CO-O-, R 2 The above "R 2 This has a similar meaning to that of the "group represented by -O-CO-". "R 2Specific examples of groups represented by "-O-CO-O-" include the methoxycarbonyloxy group and the ethoxycarbonyloxy group.

[0058] X 1 In "R" 2 -O-CO-NR 5 - in the group represented by -, R 2 The above "R 2 This has a similar meaning to that in the group represented by -O-CO-. 5 The above "R 1 -CO-NR 5 This indicates a similar meaning to that in "the base represented by -". "R 2 -O-CO-NR 5 Specific examples of the group represented by "-" include the methoxycarbonylamino group.

[0059] X 1 In "R" 3 R 4 In the group represented by N-CO-O-, R 3 and R 4 The above "R 3 R 4 This has the same meaning as in "groups represented by N-". "R 3 R 4 Specific examples of groups represented by "N-CO-O-" include the carbamoyloxy group and the N,N-dimethylaminocarbonyloxy group.

[0060] X 1 In "R" 3 R 4 N-CO-NR 5 - in the group represented by -, R 3 and R 4 The above "R 3 R 4 This has the same meaning as in "groups represented by N-". 5 The above "R 1 -CO-NR 5 This indicates a similar meaning to that in "the base represented by -". "R3 R 4 N-CO-NR 5 Specific examples of the group represented by "-" include the carbamoylamino group and the N,N-dimethylaminocarbonylamino group.

[0061] X 1 In "R" 2 SO2-NR 5 - in the group represented by -, R 2 The above "R 2 This has a similar meaning to that in the group represented by -O-CO-. 5 The above "R 1 -CO-NR 5 This indicates a similar meaning to that in "the base represented by -". "R 2 SO2-NR 5 Specific examples of the group represented by "-" include the methanesulfonylamino group.

[0062] X 1 In "R" 3 R 4 In the group represented by N-SO2-, R 3 and R 4 The above "R 3 R 4 This has the same meaning as in "groups represented by N-". "R 3 R 4 Specific examples of the group represented by "N-SO2-" include the N,N-dimethylaminosulfonyl group.

[0063] X 1 In "R" 1 ON=CR 6 - in the group represented by -, R 1 The above "R 1 This has the same meaning as in "a group represented by -CO-". R 6This represents a hydrogen atom, a halogen group, an amino group, a substituted or unsubstituted monoC1-6 alkylamino group, a substituted or unsubstituted diC1-6 alkylamino group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R 6 Specific examples of "substituted or unsubstituted C1-6 alkyl groups" or "substituted or unsubstituted 5-6 heterocyclyl groups" in R 1 The same examples given in the previous section can be cited. R 6 Examples of "halogeno groups" in this context include fluoro groups, chloro groups, bromo groups, and iod groups. R 6 Examples of "monoC1-6 alkylamino groups" in "substituted or unsubstituted monoC1-6 alkylamino groups" include methylamino groups, ethylamino groups, and i-propylamino groups. R 6 Examples of "substituted or unsubstituted diC1-6 alkylamino groups" in this context include dimethylamino group, diethylamino group, and N-methyl-Ni-propylamino group. R 6 Examples of "substituted or unsubstituted C1-6 alkoxy groups" in this context include methoxy group, ethoxy group, n-propoxy group, n-butoxy group, n-pentyloxy group, n-hexyloxy group, i-propoxy group, i-butoxy group, s-butoxy group, t-butoxy group, and i-hexyloxy group. R 6 Examples of "substituted or unsubstituted C1-6 alkylthio groups" in this context include methylthio group, ethylthio group, n-propylthio group, n-butylthio group, n-pentylthio group, n-hexylthio group, i-propylthio group, and others. R 6In this context, the substituents on the "C1-6 alkoxy group", "monoC1-6 alkylamino group", "diC1-6 alkylamino group", or "C1-6 alkylthio group" are R 1 The same substituents exemplified as substituents on the "C1-6 alkyl group" can be cited in the above example. "R 1 ON=CR 6 Specific examples of groups represented by "-" include the (hydroxyimino)methyl group, the (ethoxyimino)methyl group, and the 1-(i-propoxyimino)ethyl group.

[0064] In the present invention, preferred X 1 Examples include hydrogen atoms or substituted or unsubstituted C1-6 alkyl groups. 1 Hydrogen atoms are even more preferable.

[0065] [X 2 ] X 2 R 1 ON=CR 6 - represents a group, R 1 CO-ON=CR 6 - represents a group, R 3 R 4 N-CO-ON=CR 6 - represents a group, R 3 R 4 NN=CR 6 - A group represented by -, or R 7 -N=CR 6 This indicates a group represented by -. Also, R 1 , R 3 , R 4 , and R 6 X 1 It has a similar meaning to those in [the context of the text]. R 7 This represents a substituted or unsubstituted five-membered heterocyclyl group. X 2 A concrete example of substituents in X 1 The same examples given in the previous section can be cited. R 7In this context, a "five-membered heterocyclyl group" refers to a ring composed of 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms. Examples of "five-membered heterocyclyl groups" include five-membered saturated heterocyclyl groups, five-membered heteroaryl groups, and five-membered partially unsaturated heterocyclyl groups. Examples of saturated heterocyclyl groups with a five-membered ring include pyrrolidinyl groups, tetrahydrofuranyl groups, thiazolidinyl groups, and dioxolanyl groups. Examples of 5-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups. Examples of partially unsaturated heterocyclyl groups in a five-membered ring include pyrrolinyl groups, dihydrofuranyl groups, imidazolinyl groups, pyrazolinyl groups, and oxazolinyl groups.

[0066] R 7Substituents on the "5-membered ring heterocyclyl group" include halogen groups such as fluoro, chloro, bromo, and iod groups; 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 groups; and C1-6 haloalkyl groups such as chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, and 1-fluoro-n-butyl groups. C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy groups; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, and trifluoromethoxy; C6-10 aryl groups such as phenyl and naphthyl groups; 4-chlorophenyl, 4-trifluoromethylphenyl, and 4-trifluoromethoxyphenyl groups. C6-10 aryl groups substituted with one or more substituents of a halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; 5-membered heteroaryl groups such as pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group, etc.; C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, A 5-membered ring heteroaryl group substituted with one or more substituents of a C1-6 haloalkyl group or a C1-6 haloalkoxy group; a 6-membered ring heteroaryl group such as a pyridyl group, pyrazinyl group, pyrimidinyl group, pyridadinyl group, or triazinyl group; a 6-membered ring 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 cyano group is preferred.

[0067] In the present invention, preferred X 2 For example, R 1 ON=CR 6 One example of a base represented by - can be given. For R1, 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 C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group is preferred. R 6 Preferably, the element is a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group. "R 1 ON=CR 6 Specific examples of the group represented by "-" include the (hydroxyimino)methyl group, the (ethoxyimino)methyl group, the 1-(ethoxyimino)ethyl group, and the 1-(i-propoxyimino)ethyl group.

[0068] [Q] Q represents a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-10 membered heterocycline ring.

[0069] Examples of "C6-10 aryl groups" in Q include phenyl groups, naphthyl groups, indenyl groups, indanyl groups, and tetralinyl groups.

[0070] In Q, a "5- to 10-membered heterocyclyl group" refers to a group containing one, two, three, or four heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms as constituent atoms of the ring. When there are two or more heteroatoms, they may be the same or different. It may be either monocyclic or polycyclic. Examples of "5- to 10-membered heterocyclyl groups" include saturated heterocyclyl groups with 5- to 6 members, heteroaryl groups with 5- to 10 members, and partially unsaturated heterocyclyl groups with 5- to 10 members.

[0071] Examples of saturated heterocyclyl groups with 5-6 member rings include pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, tetrahydro-2H-pyranyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, and dioxanyl group. Examples of 5- to 10-membered heteroaryl groups include: 5-membered heteroaryl groups such as pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups; 6-membered heteroaryl groups such as pyridyl, pyrazinyl, pyrimidinyl, pyridadinyl, and triazinyl groups; 9-membered heteroaryl groups such as indolyl, isoindolyl, benzofuranyl, benzothienyl, indazolyl, benzimidazolyl, benzoxazolyl, benzoisoxaozolyl, benzothiazolyl, and benzoisothiazolyl groups; and 10-membered heteroaryl groups such as quinolinyl, isoquinolinyl, synnolinyl, phthalazinyl, quinazolyl, and quinoxalinyl groups. Examples of partially unsaturated heterocyclyl groups with 5 to 10 member rings include: partially unsaturated heterocyclyl groups with 5 member rings such as pyrrolinyl group, dihydrofuranyl group, imidazolinyl group, pyrazolinyl group, and oxazolinyl group; partially unsaturated heterocyclyl groups with 6 member rings such as isoxazolinyl group and dihydropyranyl group; partially unsaturated heterocyclyl groups with 9 member rings such as indolinyl group, isoindolinyl group, 2,3-dihydrobenzofuranyl group, and 1,3-dihydrobenzofuranyl group; and partially unsaturated heterocyclyl groups with 10 member rings such as 1,2,3,4-tetrahydroquinolinyl group.

[0072] Substituents on the "C6-10 aryl group" or "5-10 membered heterocyclyl group" in Q include halogen groups such as fluoro, chloro, bromo, and iod groups; 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 groups; C2-6 alkenyl groups such as vinyl groups; C2-6 alkynyl groups such as ethynyl groups; chloromethyl, chloroethyl, trifluoromethyl, and 1,2-dichloro-n-propyl groups. C1-6 haloalkyl groups such as pyr group and 1-fluoro-n-butyl group; C1-6 alkoxyC1-6 alkyl groups such as methoxymethyl group; hydroxyl group; C1-6 alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; hydroxyC1-6 alkoxy groups such as hydroxyethoxy group; C1-6 alkoxyalkoxy groups such as methoxymethoxy group and methoxyethoxy group; trimethylsilyloxyethoxy group, t-butyldimethylsilyl Tri-C1-6 alkyl-substituted silyloxy-C1-6 alkoxy groups such as lyloxyethoxy groups; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy groups, 2,3-dichlorobutoxy groups, and trifluoromethoxy groups; C3-6 cycloalkyl-C1-6 alkoxy groups; C6-10 aryl-C1-6 alkoxy groups; (C6-10 aryl) C1-6 alkoxy groups substituted with one or more substituents of any of the following: C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups; 5 Heteroaryl C1-6 alkoxy groups of a five-membered ring; (heteroaryl C1-6 alkoxy groups of five members substituted with one or more substituents of a C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group); heteroaryl C1-6 alkoxy groups of six-membered rings; (heteroaryl C1-6 alkoxy groups of six members substituted with one or more substituents of a C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group);C1-6 alkylthio groups such as methylthio group and ethylthio group; C1-6 alkylsulfinyl groups such as methylsulfinyl group and ethylsulfinyl group; C1-6 alkylsulfonyl groups such as methylsulfonyl group and ethylsulfonyl group; C1-6 haloalkylthio groups such as trifluoromethylthio group and 2,2,2-trifluoroethylthio group; C1-6 haloalkylsulfinyl groups such as trifluoromethylsulfinyl group and 2,2,2-trifluoroethylsulfinyl group; trifluoromethylsulfonyl group and 2,2,2-trifluoroethylsulfinyl C1-6 haloalkylsulfonyl groups such as cysulfonyl groups; C3-6 cycloalkyl groups such as cyclopropyl groups, cyclobutyl groups, and cyclopentyl groups; C3-6 cycloalkyl groups substituted with one or more substituents of any C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, C1-6 haloalkoxy groups, or cyano groups; C3-6 cycloalkenyl groups such as cyclopropenyl groups, cyclobutenyl groups, and cyclopentenyl groups; C6-10 aryl groups such as phenyl groups and naphthyl groups; 4-methylphenyl groups, 4- C6-10 aryl groups substituted with one or more substituents of any C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups, such as methoxyphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, 4-trifluoromethylphenyl group, and 4-trifluoromethoxyphenyl group; saturated heterocyclyl groups of 3-4 membered rings such as azilidinyl group, epoxy group, azetidinyl group, and oxetanyl group; C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or saturated heterocyclyl groups of 3-4 membered rings substituted with one or more substituents of any C1-6 haloalkoxy groups; saturated heterocyclyl groups of 5-6 membered rings such as pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, tetrahydro-2H-pyranyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, dioxanyl group, etc.; saturated heterocyclyl groups of 5-6 membered rings substituted with one or more substituents of any C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group;Five-membered heteroaryl groups such as pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups; five-membered heteroaryl groups substituted with one or more substituents of any C1-6 alkyl, C1-6 alkoxy, halogeno, C1-6 haloalkyl, or C1-6 haloalkoxy groups; six-membered heteroaryl groups such as pyridyl, pyrazinyl, pyrimidinyl, pyridadinyl, and triazinyl groups; any of C1-6 alkyl, C1-6 alkoxy, halogeno, C1-6 haloalkyl, or C1-6 haloalkoxy groups Six-membered heteroaryl groups substituted with one or more substituents; five-membered partially unsaturated heterocyclyl groups such as pyrrolinyl, dihydrofuranyl, imidazolinyl, pyrazolinyl, and oxazolinyl groups; five-membered partially saturated heterocyclyl groups substituted with one or more substituents of any C1-6 alkyl, C1-6 alkoxy, halogeno, C1-6 haloalkyl, or C1-6 haloalkoxy groups; six-membered partially unsaturated heterocyclyl groups such as isoxazolinyl and dihydropyranyl groups; six-membered partially saturated heterocyclyl groups substituted with one or more substituents of any C1-6 alkyl, C1-6 alkoxy, halogeno, C1-6 haloalkyl, or C1-6 haloalkoxy groups; R Q1 A group represented by -CO- (wherein R is R in the formula) Q1C1-6 alkyl groups; C1-6 alkyl groups substituted with one or more substituents of a halogen group, C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, phenyl group, or 5-6 membered heteroaryl group; (C6-10 aryl groups substituted with one or more substituents of a C1-6 alkyl group, C1-6 alkoxy group, halogen group, C1-6 haloalkyl group, or C1-6 haloalkoxy group) C1-6 alkyl groups; (5-6 membered heteroaryl groups substituted with one or more substituents of a C1-6 alkyl group, C1-6 alkoxy group, halogen group, C1-6 haloalkyl group, or C1-6 haloalkoxy group) C1-6 alkyl groups; C2-6 alkenyl groups; C2-6 haloalkenyl groups; C2- This represents a 6-alkynyl group; a C2-6 haloalkynyl group; a C3-6 cycloalkyl group; a C3-6 cycloalkyl group substituted with one or more substituents of a C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, C1-6 haloalkoxy group, or cyano group; a C6-10 aryl group; a C6-10 aryl group substituted with one or more substituents of a C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; a 5-6 membered heteroaryl group; or a 5-6 membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group. The following R Q1 The same applies to this case as well. Carboxy group; R Q2 A group represented by -O-CO- (wherein R in the formula) Q2C1-6 alkyl groups; C1-6 alkyl groups substituted with one or more substituents of a halogen group, C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, phenyl group, or 5-6 membered heteroaryl group; (C6-10 aryl groups substituted with one or more substituents of a C1-6 alkyl group, C1-6 alkoxy group, halogen group, C1-6 haloalkyl group, or C1-6 haloalkoxy group) C1-6 alkyl groups; (5-6 membered heteroaryl groups substituted with one or more substituents of a C1-6 alkyl group, C1-6 alkoxy group, halogen group, C1-6 haloalkyl group, or C1-6 haloalkoxy group) C1-6 alkyl groups; C2-6 alkenyl groups; C2-6 haloalkenyl groups ;C2-6 alkynyl group;C2-6 haloalkynyl group;C3-6 cycloalkyl group;C3-6 cycloalkyl group substituted with a C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, C1-6 haloalkoxy group, or cyano group;C6-10 aryl group;C6-10 aryl group substituted with one or more substituents of a C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group;5-6 membered heteroaryl group;or;5-6 membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group;The following R Q2 The same applies to this case as well. R Q1 R Q1 The group represented by N- (R in the formula) Q1 They may be the same or different. Q1 These groups may combine to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group. R Q1 R Q1 The group represented by N-CO- (R in the formula) Q1 They may be the same or different. Q1 These groups may combine to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group. R Q1 A group represented by -CO-O-; R Q1 -CO-NR Q3 - is represented by the base (wherein R Q3 This represents a hydrogen atom; a C1-6 alkyl group; a C1-6 alkyl group substituted with one or more substituents from among a halogen group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, or a 5-6 membered heteroaryl group; a C6-10 aryl (substituted with one or more substituents from among a C1-6 alkyl group, a C1-6 alkoxy group, a halogen group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group); or a C1-6 alkyl group (a 5-6 membered heteroaryl (substituted with one or more substituents from among a C1-6 alkyl group, a C1-6 alkoxy group, a halogen group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group). The following R Q3 The same applies to this case as well. R Q2 A base represented by -O-CO-O-; R Q2 -O-CO-NR Q3 - represents the base; R Q1 R Q1 The group represented by N-CO-O- (R in the formula) Q1 They may be the same or different. Q1 These groups may combine to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group. R Q1 R Q1 N-CO-NR Q3 - is represented by the base (R in the formula) Q1 They may be the same or different. q1 These groups may combine to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group. Q2 SO2-NR Q3 - represents the base; R Q1 R Q1 The group represented by N-SO2- (R in the formula) Q1 They may be the same or different. Q1These groups may combine to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group. R Q1 -ON=C(R Q4 )- represents a base (where R in the formula Q4 This represents a hydrogen atom or a C1-6 alkyl group. Q1 )The group represented by 2C=NO- (R in the formula Q1 They may be the same or different. Q1 These groups may combine to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group. A pentafluorosulfanyl group, a trimethylsilylethynyl group, a nitro group, or a cyano group is preferred. Furthermore, oxo groups are also preferred as substituents on the "5-10 membered heterocyclyl group".

[0073] [X 3 ] X 3 R is a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted linear C2-6 alkenyl group, a substituted or unsubstituted linear C2-6 alkynyl group, 1 This represents a group represented by -CO-, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 4-6 membered heterocyclyl group.

[0074] X 3 Examples of "linear C1-6 alkyl groups" in this context include methyl, ethyl, n-propyl, n-butyl, n-pentyl, and n-hexyl groups. X 3 Examples of "linear C2-6 alkenyl groups" in this context include vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, and 5-hexenyl group. X3 Examples of "linear C2-6 alkynyl groups" in this context include ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, and 1-hexynyl group. X 3 Examples of "four-membered heterocyclyl groups" in this context include the azetidinyl group and the oxetanyl group. X 3 Other specific examples of substituents in X 1 The same examples given in the previous section can be cited.

[0075] In the present invention, preferred X 3 Examples include substituted or unsubstituted linear C1-6 alkyl groups, substituted or unsubstituted C3-6 cycloalkyl groups, or substituted or unsubstituted C6-10 aryl groups.

[0076] Substituents on linear C1-6 alkyl groups, linear C2-6 alkenyl groups, linear C2-6 alkynyl groups, C3-6 cycloalkyl groups, C6-10 aryl groups, or heterocyclyl groups of 4-6 membered rings can be one or more substituents selected from the following group of substituents (hereinafter, these substituents may be represented by the symbol "G"). Furthermore, if there are two or more substituents (G), two of them may combine to form a divalent organic group. The substituent groups are shown below. Halogeno group, substituted or unsubstituted C1-6 alkyl group, substituted or unsubstituted C2-6 alkenyl group, substituted or unsubstituted C2-6 alkynyl group, hydroxyl group, substituted or unsubstituted C1-6 alkoxy group, substituted or unsubstituted C2-6 alkenyloxy group, substituted or unsubstituted C2-6 alkynyloxy group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alkylsulfinyl group, substituted or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted C 3-6 cycloalkyl groups, substituted or unsubstituted C3-6 cycloalkyloxy groups, substituted or unsubstituted C6-10 aryl groups, substituted or unsubstituted C6-10 aryloxy groups, substituted or unsubstituted C6-10 arylthio groups, substituted or unsubstituted C6-10 arylsulfinyl groups, substituted or unsubstituted C6-10 arylsulfonyl groups, substituted or unsubstituted 3-10 membered heterocyclyl groups, substituted or unsubstituted 3-10 membered heterocyclyloxy groups, nitro groups, cyano groups, R a Groups represented by -CO-, carboxyl groups, R b A group represented by -O-CO-, R c R d The group represented by N-, R c R d The group represented by N-CO-, R c R d N-NR d A group represented by -CO-, R a A group represented by -CO-O-, R a -CO-NR e - represents a group, R a -CO-CO-NR e - represents a group, R a -CO-NR e -NR e - represents a group, R a -CO-NR e -NR e A group represented by -CO-, R b A group represented by -O-CO-O-, R b -O-CO-NR e - represents a group, R c R d The group represented by N-CO-O-, R c Rd N-CO-NR e - represents a group, R c R d N-CO-CO-NR e - represents a group, R a -CS-NR e - represents a group, R c R d N-CS-NR e - represents a group, R b SO2-NR e - represents a group, R c R d The group represented by N-SO2-, R a ON=CR f - represents a group, R h R j The group represented by C=NO-, R a -C(=NR g )-NR e - represents a group, R c R d NC (=NR) g )- represents a group, R h R i The group represented by S(=O)=N-CO-, R h R i The group represented by S=N-CO-

[0077] Among the above group of substituents, R a Each of these 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 C6-10 aryl group, or a substituted or unsubstituted 3-10 membered heterocyclyl group. R b Each of these independently represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R cEach of these 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 C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R d Each of these independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a substituted or unsubstituted C6-10 aryl group, where R c and R d These may combine to form a divalent organic group. R e Each of these independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a substituted or unsubstituted C6-10 aryl group. R f This represents a hydrogen atom, an amino group, or a substituted or unsubstituted C1-6 alkyl group. R g Each of these independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. R h Each of these independently represents a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. R i Each independently represents a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, where R h and R i These may combine to form a divalent organic group.

[0078] Examples of "halogeno groups" in G include fluoro groups, chloro groups, bromo groups, and iod groups.

[0079] The "C1-6 alkyl group" in G may be a straight chain or a branched chain. Examples of "C1-6 alkyl groups" in G include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s-butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, and i-hexyl group.

[0080] Examples of "C2-6 alkenyl groups" in G 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.

[0081] Examples of "C2-6 alkynyl groups" in G include ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, and 1,1-dimethyl-2-butynyl group.

[0082] Examples of "C1-6 alkoxy groups" in G include methoxy group, ethoxy group, n-propoxy group, n-butoxy group, n-pentyloxy group, n-hexyloxy group, i-propoxy group, i-butoxy group, s-butoxy group, t-butoxy group, and i-hexyloxy group. Examples of "C2-6 alkenyloxy groups" in G include vinyloxy groups, allyloxy groups, propenyloxy groups, and butenyloxy groups. Examples of "C2-6 alkynyloxy groups" in G include ethynyloxy groups and propargyloxy groups.

[0083] Examples of "C1-6 alkylthio groups" in G include methylthio group, ethylthio group, n-propylthio group, n-butylthio group, n-pentylthio group, n-hexylthio group, and i-propylthio group. Examples of "C1-6 alkylsulfinyl groups" in G include methylsulfinyl groups, ethylsulfinyl groups, and t-butylsulfinyl groups. Examples of "C1-6 alkylsulfonyl groups" in G include methylsulfonyl groups, ethylsulfonyl groups, and t-butylsulfonyl groups.

[0084] Substituents on the "C1-6 alkyl group", "C2-6 alkenyl group", "C2-6 alkynyl group", "C1-6 alkoxy group", "C2-6 alkenyloxy group", "C2-6 alkynyloxy group", "C1-6 alkylthio group", "C1-6 alkylsulfinyl group", or "C1-6 alkylsulfonyl group" in G include halogen groups such as fluoro groups, chloro groups, bromo groups, and iod groups; hydroxyl groups; C1-... groups such as methoxy groups, ethoxy groups, n-propoxy groups, i-propoxy groups, n-butoxy groups, s-butoxy groups, i-butoxy groups, and t-butoxy groups. 6-alkoxy groups; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, and trifluoromethoxy; C1-6 alkylthio groups such as methylthio and ethylthio; C1-6 alkylsulfinyl groups such as methylsulfinyl and ethylsulfinyl; C1-6 alkylsulfonyl groups such as methylsulfonyl and ethylsulfonyl; C3-6 cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl; C6-10 aryl groups such as phenyl and naphthyl; 4-methyl phosphate C6-10 aryl groups substituted with one or more substituents of any C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups, such as phenyl groups, 4-methoxyphenyl groups, 4-chlorophenyl groups, 4-trifluoromethylphenyl groups, and 4-trifluoromethoxyphenyl groups; pyrrolyl groups, furyl groups, thienyl groups, imidazolyl groups, pyrazolyl groups, oxazolyl groups, isoxazolyl groups, thiazolyl groups, isothiazolyl groups, triazolyl groups, oxadiazolyl groups, thiadiazolyl groups, and tetrazolyl groups. Preferred are 5-membered heteroaryl groups such as: 5-membered ring heteroaryl groups; 5-membered ring heteroaryl groups substituted with one or more substituents of any C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups; 6-membered ring heteroaryl groups such as pyridyl groups, pyrazinyl groups, pyrimidinyl groups, pyridadinyl groups, triazinyl groups; 6-membered ring heteroaryl groups substituted with one or more substituents of any C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups; or cyano groups.

[0085] Examples of "C3-6 cycloalkyl groups" in G include cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, and cyclohexyl groups. Examples of "C3-6 cycloalkyloxy groups" in G include cyclopropyloxy group, cyclobutyloxy group, cyclopentyloxy group, and cyclohexyloxy group.

[0086] Examples of "C6-10 aryl groups" in G include phenyl groups and naphthyl groups. Examples of "C6-10 aryloxy groups" in G include phenoxy groups and naphthoxy groups.

[0087] Examples of "C6-10 arylthio groups" in G include phenylthio groups and naphthylthio groups. Examples of "C6-10 aryl sulfinyl groups" in G include phenyl sulfinyl groups and naphthyl sulfinyl groups. Examples of "C6-10 arylsulfonyl groups" in G include phenylsulfonyl groups and naphthylsulfonyl groups.

[0088] In G, a "3- to 10-membered heterocyclyl group" is a group that contains one, two, three, or four heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms as constituent atoms of the ring. When there are two or more heteroatoms, they may be the same or different. It may be either monocyclic or polycyclic. Examples of "3- to 10-membered heterocyclyl groups" include 3- to 6-membered saturated heterocyclyl groups, 5- to 10-membered heteroaryl groups, and 5- to 10-membered partially unsaturated heterocyclyl groups.

[0089] Examples of saturated heterocyclyl groups with 3 to 6 members include azilidinyl group, epoxy group, azetidinyl group, oxetanyl group, pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, tetrahydro-2H-pyranyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, and dioxanyl group. Examples of 5- to 10-membered heteroaryl groups include: 5-membered heteroaryl groups such as pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups; 6-membered heteroaryl groups such as pyridyl, pyrazinyl, pyrimidinyl, pyridadinyl, and triazinyl groups; 9-membered heteroaryl groups such as indolyl, isoindolyl, benzofuranyl, benzothienyl, indazolyl, benzimidazolyl, benzoxazolyl, benzoisoxaozolyl, benzothiazolyl, and benzoisothiazolyl groups; and 10-membered heteroaryl groups such as quinolinyl, isoquinolinyl, synnolinyl, phthalazinyl, quinazolyl, and quinoxalinyl groups. Examples of partially unsaturated heterocyclyl groups with 5 to 10 member rings include: partially unsaturated heterocyclyl groups with 5 member rings such as pyrrolinyl group, dihydrofuranyl group, imidazolinyl group, pyrazolinyl group, and oxazolinyl group; partially unsaturated heterocyclyl groups with 6 member rings such as isoxazolinyl group and dihydropyranyl group; partially unsaturated heterocyclyl groups with 9 member rings such as indolinyl group, isoindolinyl group, 2,3-dihydrobenzofuranyl group, and 1,3-dihydrobenzofuranyl group; and partially unsaturated heterocyclyl groups with 10 member rings such as 1,2,3,4-tetrahydroquinolinyl group.

[0090] In G, the "3- to 10-membered heterocyclyloxy group" has a structure in which a 3- to 10-membered heterocyclyl group is bonded to an oxy group. Specific examples include thiazolyloxy groups and pyridyloxy groups.

[0091] Substituents on G include "C3-6 cycloalkyl groups", "C3-6 cycloalkyloxy groups", "C6-10 aryl groups", "C6-10 aryloxy groups", "C6-10 arylthio groups", "C6-10 arylsulfinyl groups", "C6-10 arylsulfonyl groups", "3-10 membered heterocyclyl groups", or "3-10 membered heterocyclyloxy groups", such as halogeno groups like fluoro groups, chloro groups, bromo groups, and iod groups; methyl groups, ethyl groups, n-propyl groups, i-propyl groups, n-butyl groups, s-butyl groups, i- C1-6 alkyl groups such as butyl group, t-butyl group, n-pentyl group, n-hexyl group; C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group; hydroxyl group; C1-6 alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; C1-6 haloalkyl groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group Glucooxy group; C3-6 cycloalkyl C1-6 alkoxy group; C6-10 aryl C1-6 alkoxy group; (C6-10 aryl) C1-6 alkoxy group substituted with one or more substituents of any C1-6 alkyl, C1-6 alkoxy, halogeno, C1-6 haloalkyl, or C1-6 haloalkoxy group; 5-membered ring heteroaryl C1-6 alkoxy group; (5-membered ring substituted with one or more substituents of any C1-6 alkyl, C1-6 alkoxy, halogeno, C1-6 haloalkyl, or C1-6 haloalkoxy group) Heteroaryl)C1-6 alkoxy groups; 6-membered heteroaryl C1-6 alkoxy groups; (6-membered heteroaryl)C1-6 alkoxy groups substituted with one or more substituents of any of the following: C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups; C1-6 alkylthio groups such as methylthio groups and ethylthio groups; C1-6 alkylsulfinyl groups such as methylsulfinyl groups and ethylsulfinyl groups; C1-6 alkylsulfonyl groups such as methylsulfonyl groups and ethylsulfonyl groups;C1-6 haloalkylthio groups such as trifluoromethylthio group and 2,2,2-trifluoroethylthio group; C1-6 haloalkylsulfinyl groups such as trifluoromethylsulfinyl group and 2,2,2-trifluoroethylsulfinyl group; C1-6 haloalkylsulfonyl groups such as trifluoromethylsulfonyl group and 2,2,2-trifluoroethylsulfonyl group; C3-6 cycloalkyl groups such as cyclopropyl group and cyclobutyl group; C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 halo C3-6 cycloalkyl groups substituted with one or more substituents of a lucyl group, a C1-6 haloalkoxy group, or a cyano group; C3-6 cycloalkenyl groups; C6-10 aryl groups such as phenyl groups and naphthyl groups; and one or more substitutions of C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups, such as 4-methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, and 4-trifluoromethoxyphenyl group. C6-10 aryl groups substituted with groups; saturated heterocyclyl groups of 3-4 membered rings such as azilidinyl groups, epoxy groups, azetidinyl groups, and oxetanyl groups; saturated heterocyclyl groups of 3-4 membered rings substituted with one or more substituents of C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups; pyrrolidinyl groups, tetrahydrofuranyl groups, thiazolidinyl groups, tetrahydro-2H-pyranyl groups, piperidyl groups, piperazinyl groups, morpholinyl groups, and dioxolanyl groups. , a saturated heterocyclyl group of 5-6 member rings such as a dioxanyl group; a saturated heterocyclyl group of 5-6 member rings substituted with one or more substituents of a C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; a heteroaryl group of 5 member rings such as a pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group, etc.Five-membered heteroaryl groups substituted with one or more substituents of any C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups; six-membered heteroaryl groups such as pyridyl groups, pyrazinyl groups, pyrimidinyl groups, pyridadinyl groups, and triazinyl groups; six-membered heteroaryl groups substituted with one or more substituents of any C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups; pyrrolinyl groups, dihydrofuranyl groups, imidazolinyl groups, pyrazoli Partially unsaturated heterocyclyl groups of five-membered rings, such as nyl groups and oxazolinyl groups; partially saturated heterocyclyl groups of five-membered rings substituted with one or more substituents of any of the following: C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups; partially unsaturated heterocyclyl groups of six-membered rings, such as isoxazolinyl groups and dihydropyranyl groups; partially saturated heterocyclyl groups of six-membered rings substituted with one or more substituents of any of the following: C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups; R G1 A group represented by -CO- (wherein R is R in the formula) G1C1-6 alkyl groups; C1-6 alkyl groups substituted with one or more substituents of a halogen group, C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, phenyl group, or 5-6 membered heteroaryl group; (C6-10 aryl groups substituted with one or more substituents of a C1-6 alkyl group, C1-6 alkoxy group, halogen group, C1-6 haloalkyl group, or C1-6 haloalkoxy group) C1-6 alkyl groups; (5-6 membered heteroaryl groups substituted with one or more substituents of a C1-6 alkyl group, C1-6 alkoxy group, halogen group, C1-6 haloalkyl group, or C1-6 haloalkoxy group) C1-6 alkyl groups; C2-6 alkenyl groups; C2-6 haloalkenyl groups; C2- This represents a 6-alkynyl group; a C2-6 haloalkynyl group; a C3-6 cycloalkyl group; a C3-6 cycloalkyl group substituted with one or more substituents of a C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, C1-6 haloalkoxy group, or cyano group; a C6-10 aryl group; a C6-10 aryl group substituted with one or more substituents of a C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; a 5-6 membered heteroaryl group; or a 5-6 membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group. The following R G1 The same applies to this case as well. Carboxy group; R G2 A group represented by -O-CO- (wherein R in the formula) G2C1-6 alkyl groups; C1-6 alkyl groups substituted with one or more substituents of a halogen group, C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, phenyl group, or 5-6 membered heteroaryl group; (C6-10 aryl groups substituted with one or more substituents of a C1-6 alkyl group, C1-6 alkoxy group, halogen group, C1-6 haloalkyl group, or C1-6 haloalkoxy group) C1-6 alkyl groups; (5-6 membered heteroaryl groups substituted with one or more substituents of a C1-6 alkyl group, C1-6 alkoxy group, halogen group, C1-6 haloalkyl group, or C1-6 haloalkoxy group) C1-6 alkyl groups; C2-6 alkenyl groups; C2-6 haloalkenyl groups ;C2-6 alkynyl group;C2-6 haloalkynyl group;C3-6 cycloalkyl group;C3-6 cycloalkyl group substituted with a C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, C1-6 haloalkoxy group, or cyano group;C6-10 aryl group;C6-10 aryl group substituted with one or more substituents of a C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group;5-6 membered heteroaryl group;or;5-6 membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group;The following R G2 The same applies to this case as well. R G1 R G1 The group represented by N- (R in the formula) q1 They may be the same or different. G1 These groups may combine to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group. R G1 R G1 The group represented by N-CO- (R in the formula) G1 They may be the same or different. G1 These groups may combine to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group. R G1 A group represented by -CO-O-; R G1 -CO-NR G3 - is represented by the base (wherein R G3 This represents a hydrogen atom; a C1-6 alkyl group; a C1-6 alkyl group substituted with one or more substituents from among a halogen group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, or a 5-6 membered heteroaryl group; a C6-10 aryl (substituted with one or more substituents from among a C1-6 alkyl group, a C1-6 alkoxy group, a halogen group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group); or a C1-6 alkyl group (a 5-6 membered heteroaryl (substituted with one or more substituents from among a C1-6 alkyl group, a C1-6 alkoxy group, a halogen group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group). The following R G3 The same applies to this case as well. R G2 A base represented by -O-CO-O-; R G2 -O-CO-NR G3 - represents the base; R G1 R G1 The group represented by N-CO-O- (R in the formula) G1 They may be the same or different. G1 These groups may combine to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group. R G1 R G1 N-CO-NR G3 - is represented by the base (R in the formula) G1 They may be the same or different. G1 These groups may combine to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group. G2 SO2-NR G3 - represents the base; R G1 R G1 The group represented by N-SO2- (R in the formula) G1 They may be the same or different. G1These groups may combine to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group. R G1 -ON=C(R G4 )- represents a base (where R in the formula G4 This represents a hydrogen atom or a C1-6 alkyl group. G1 )The group represented by 2C=NO- (R in the formula G1 They may be the same or different. G1 These groups may combine to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group. A pentafluorosulfanil group, a nitro group, or a cyano group is preferred. Furthermore, oxo groups are also preferred as substituents on "C3-6 cycloalkyl groups," "C3-6 cycloalkyloxy groups," "3-10 membered heterocyclyl groups," or "3-10 membered heterocyclyloxy groups."

[0092] "R" in G a In the group represented by -CO-, R a This represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 3-10 membered heterocyclyl group.

[0093] R a Examples of "C1-6 alkyl groups" in this context include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s-butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, and i-hexyl group. R a Examples of "C2-6 alkenyl groups" in this context include vinyl groups and 1-propenyl groups. R aExamples of "C2-6 alkynyl groups" in this context include the ethynyl group and the 1-propynyl group. R aSubstituents on the "C1-6 alkyl group", "C2-6 alkenyl group", or "C2-6 alkynyl group" include: halogen groups such as fluoro, chloro, bromo, and iod groups; hydroxyl groups; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy groups; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, and trifluoromethoxy groups; and C1-6 alkylthio groups such as methylthio and ethylthio groups. C1-6 alkyl sulfinyl groups such as ethyl sulfinyl and ethyl sulfinyl groups; C1-6 alkyl sulfonyl groups such as methyl sulfonyl and ethyl sulfonyl groups; carboxyl groups; C1-6 alkoxycarbonyl groups such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, i-propoxycarbonyl, n-butoxycarbonyl, and t-butoxycarbonyl groups; C3-6 cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups; C6-10 alkyl groups such as phenyl and naphthyl groups. aryl groups; C6-10 aryl groups substituted with one or more substituents of any C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups, such as 4-methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, and 4-trifluoromethoxyphenyl group; pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group Heteroaryl groups of five members, such as lyl groups and tetrazolyl groups; heteroaryl groups of five members substituted with one or more substituents of any C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups; heteroaryl groups of six members, such as pyridyl groups, pyrazinyl groups, pyrimidinyl groups, pyridadinyl groups, and triazinyl groups; heteroaryl groups of six members substituted with one or more substituents of any C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups;Alternatively, a cyano group is preferred.

[0094] R a Examples of "C3-6 cycloalkyl groups" in this context include cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, and cyclohexyl groups. R a Examples of "C6-10 aryl groups" in this context include phenyl, naphthyl, indenyl, indanyl, and tetralinyl groups.

[0095] R a In this context, a "3- to 10-membered heterocyclyl group" refers to a group containing one, two, three, or four heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms as constituent atoms of the ring. When there are two or more heteroatoms, they may be the same or different. The group may be monocyclic or polycyclic. Examples of "3- to 10-membered heterocyclyl groups" include 3- to 6-membered saturated heterocyclyl groups, 5- to 10-membered heteroaryl groups, and 5- to 10-membered partially unsaturated heterocyclyl groups. Examples of saturated heterocyclyl groups with 3 to 6 members include azilidinyl group, epoxy group, azetidinyl group, oxetanyl group, pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, tetrahydro-2H-pyranyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, and dioxanyl group. Examples of 5- to 10-membered heteroaryl groups include: 5-membered heteroaryl groups such as pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups; 6-membered heteroaryl groups such as pyridyl, pyrazinyl, pyrimidinyl, pyridadinyl, and triazinyl groups; 9-membered heteroaryl groups such as indolyl, isoindolyl, benzofuranyl, benzothienyl, indazolyl, benzimidazolyl, benzoxazolyl, benzoisoxaozolyl, benzothiazolyl, and benzoisothiazolyl groups; and 10-membered heteroaryl groups such as quinolinyl, isoquinolinyl, synnolinyl, phthalazinyl, quinazolyl, and quinoxalinyl groups. Examples of partially unsaturated heterocyclyl groups with 5 to 10 member rings include: partially unsaturated heterocyclyl groups with 5 member rings such as pyrrolinyl group, dihydrofuranyl group, imidazolinyl group, pyrazolinyl group, and oxazolinyl group; partially unsaturated heterocyclyl groups with 6 member rings such as isoxazolinyl group and dihydropyranyl group; partially unsaturated heterocyclyl groups with 9 member rings such as indolinyl group, isoindolinyl group, 2,3-dihydrobenzofuranyl group, and 1,3-dihydrobenzofuranyl group; and partially unsaturated heterocyclyl groups with 10 member rings such as 1,2,3,4-tetrahydroquinolinyl group.

[0096] R aSubstituents on the "C3-6 cycloalkyl group", "C6-10 aryl group", or "3-10 membered heterocyclyl group" in this context include halogeno groups such as fluoro, chloro, bromo, and iod groups; 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 groups; and C1-6 halomethyl groups such as chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, and 1-fluoro-n-butyl groups. Cyl group; hydroxyl group; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy groups; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, and trifluoromethoxy groups; C3-6 cycloalkyl C1-6 alkoxy groups; C6-10 aryl C1-6 alkoxy groups; (any of C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups) C6-10 aryl)C1-6 alkoxy groups substituted with one or more substituents; 5-membered ring heteroaryl C1-6 alkoxy groups; 5-membered ring heteroaryl)C1-6 alkoxy groups substituted with one or more substituents of any of the following: C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups; 6-membered ring heteroaryl C1-6 alkoxy groups; (one or more substituents of any of the following: C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups) substituted 6-membered ring heteroaryl) C1-6 alkoxy groups; C1-6 alkylthio groups such as methylthio groups and ethylthio groups: C1-6 alkylsulfinyl groups such as methylsulfinyl groups and ethylsulfinyl groups; C1-6 alkylsulfonyl groups such as methylsulfonyl groups and ethylsulfonyl groups; C1-6 haloalkylthio groups such as trifluoromethylthio groups and 2,2,2-trifluoroethylthio groups: C1-6 haloalkylsulfinyl groups such as trifluoromethylsulfinyl groups and 2,2,2-trifluoroethylsulfinyl groups;C1-6 haloalkylsulfonyl groups such as trifluoromethylsulfonyl group and 2,2,2-trifluoroethylsulfonyl group; C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, and cyclopentyl group; C3-6 cycloalkyl groups substituted with one or more substituents of any C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, C1-6 haloalkoxy group, or cyano group; C3-6 cycloalkenyl group; C6-10 aryl groups such as phenyl group and naphthyl group; 4-methylphenyl group, 4-methylphenyl group C6-10 aryl groups substituted with one or more substituents of any C1-6 alkyl, C1-6 alkoxy, halogeno, C1-6 haloalkyl, or C1-6 haloalkoxy groups, such as toxyphenyl, 4-chlorophenyl, 4-trifluoromethylphenyl, and 4-trifluoromethoxyphenyl; saturated heterocyclyl groups of 3-4 membered rings, such as azilidinyl, epoxy, azetidinyl, and oxetanyl groups; C1-6 alkyl, C1-6 alkoxy, halogeno, C1-6 haloalkyl, or C1-6 haloalkoxy groups. Saturated heterocyclyl groups of 3-4 membered rings substituted with one or more substituents of xy groups; saturated heterocyclyl groups of 5-6 membered rings such as pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, tetrahydro-2H-pyranyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, and dioxanyl group; saturated heterocyclyl groups of 5-6 membered rings substituted with one or more substituents of C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups; pyrrolyl group, furyl group , 5-membered heteroaryl groups such as thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group, etc.; 5-membered heteroaryl groups substituted with one or more substituents of any C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; 6-membered heteroaryl groups such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridadinyl group, triazinyl group, etc.Heteroaryl groups of six-membered rings substituted with one or more substituents of any C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups; partially unsaturated heterocyclyl groups of five-membered rings such as pyrrolinyl groups, dihydrofuranyl groups, imidazolinyl groups, pyrazolinyl groups, and oxazolinyl groups; partially saturated heterocyclyl groups of five-membered rings substituted with one or more substituents of any C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups; partially unsaturated heterocyclyl groups of six-membered rings such as isoxazolinyl groups and dihydropyranyl groups; partially saturated heterocyclyl groups of six-membered rings substituted with one or more substituents of any C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups; R q1 A group represented by -CO- (wherein R is R in the formula) q1C1-6 alkyl groups; C1-6 alkyl groups substituted with one or more substituents of a halogen group, C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, phenyl group, or 5-6 membered heteroaryl group; (C6-10 aryl groups substituted with one or more substituents of a C1-6 alkyl group, C1-6 alkoxy group, halogen group, C1-6 haloalkyl group, or C1-6 haloalkoxy group) C1-6 alkyl groups; (5-6 membered heteroaryl groups substituted with one or more substituents of a C1-6 alkyl group, C1-6 alkoxy group, halogen group, C1-6 haloalkyl group, or C1-6 haloalkoxy group) C1-6 alkyl groups; C2-6 alkenyl groups; C2-6 haloalkenyl groups; C2- This represents a 6-alkynyl group; a C2-6 haloalkynyl group; a C3-6 cycloalkyl group; a C3-6 cycloalkyl group substituted with one or more substituents of a C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, C1-6 haloalkoxy group, or cyano group; a C6-10 aryl group; a C6-10 aryl group substituted with one or more substituents of a C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; a 5-6 membered heteroaryl group; or a 5-6 membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group. The following R q1 The same applies to this case as well. Carboxy group; R q2 A group represented by -O-CO- (wherein R in the formula) q2C1-6 alkyl groups; C1-6 alkyl groups substituted with one or more substituents of a halogen group, C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, phenyl group, or 5-6 membered heteroaryl group; (C6-10 aryl groups substituted with one or more substituents of a C1-6 alkyl group, C1-6 alkoxy group, halogen group, C1-6 haloalkyl group, or C1-6 haloalkoxy group) C1-6 alkyl groups; (5-6 membered heteroaryl groups substituted with one or more substituents of a C1-6 alkyl group, C1-6 alkoxy group, halogen group, C1-6 haloalkyl group, or C1-6 haloalkoxy group) C1-6 alkyl groups; C2-6 alkenyl groups; C2-6 haloalkenyl groups; C2-6 This indicates a lucynyl group; a C2-6 haloalkynyl group; a C3-6 cycloalkyl group; a C3-6 cycloalkyl group substituted with one or more substituents of a C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, C1-6 haloalkoxy group, or cyano group; a C6-10 aryl group; a C6-10 aryl group substituted with one or more substituents of a C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; a 5-6 membered heteroaryl group; or a 5-6 membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group. The following R q2 The same applies to this. R q1 R q1 The group represented by N- (R in the formula) q1 They may be the same or different. q1 These groups may combine to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group. R q1 R q1 The group represented by N-CO- (R in the formula) q1 They may be the same or different. q1These groups may combine to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group. R q1 A group represented by -CO-O-; R q1 -CO-NR q3 - is represented by the base (wherein R q3 This represents a hydrogen atom; a C1-6 alkyl group; a C1-6 alkyl group substituted with one or more substituents from among a halogen group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, or a 5-6 membered heteroaryl group; a C6-10 aryl (substituted with one or more substituents from among a C1-6 alkyl group, a C1-6 alkoxy group, a halogen group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group); or a C1-6 alkyl group (a 5-6 membered heteroaryl (substituted with one or more substituents from among a C1-6 alkyl group, a C1-6 alkoxy group, a halogen group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group). The following R q3 The same applies to this. R q2 A base represented by -O-CO-O-; R q2 -O-CO-NR q3 - represents the base; R q1 R q1 The group represented by N-CO-O- (R in the formula) q1 They may be the same or different. q1 These groups may combine to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group. R q1 R q1 N-CO-NR q3 - is represented by the base (R in the formula) q1 They may be the same or different. q1 These groups may combine to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group. q2 SO2-NR q3 - represents the base; R q1 R q1 The group represented by N-SO2- (R in the formula)q1 They may be the same or different. q1 These groups may combine to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group. R q1 -ON=C(R q4 )- represents a base (where R in the formula q4 This represents a hydrogen atom or a C1-6 alkyl group. q1 )The group represented by 2C=NO- (R in the formula q1 They may be the same or different. q1 These groups may combine to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group. A pentafluorosulfanil group, a nitro group, or a cyano group is preferred. Furthermore, oxo groups are also preferred as substituents on the "C3-6 cycloalkyl group" or the "3-10 membered heterocyclyl group".

[0097] "R a Specific examples of groups represented by "-CO-" include the formyl group, acetyl group, and i-propylcarbonyl group.

[0098] "R" in G b In the group represented by -O-CO-, R b This represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R b A specific example of a substituent in R is a The same examples given in the previous section can be cited.

[0099] "R bSpecific examples of groups represented by "-O-CO-" include the methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, and t-butoxycarbonyl group.

[0100] "R" in G c R d In the group represented by N-, R c R represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. d This represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a substituted or unsubstituted C6-10 aryl group. R c or R d A specific example of a substituent in R is a The same examples given in the previous section can be cited. R d Examples of "C1-6 alkoxy groups" in this context include methoxy group, ethoxy group, n-propoxy group, n-butoxy group, n-pentyloxy group, n-hexyloxy group, i-propoxy group, i-butoxy group, s-butoxy group, t-butoxy group, and i-hexyloxy group. R dSubstituents on the "C1-6 alkoxy group" in this include halogen groups such as fluoro, chloro, bromo, and iod groups; hydroxyl groups; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy groups; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, and trifluoromethoxy groups; cyclopropyl, cyclobutyl, and cyclopentyl groups. Preferred are C3-6 cycloalkyl groups such as cyclohexyl groups; C6-10 aryl groups such as phenyl groups and naphthyl groups; C6-10 aryl groups substituted with one or more substituents of C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups, such as 4-methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, and 4-trifluoromethoxyphenyl group; or cyano groups.

[0101] Here, R c and R d These may combine to form a divalent organic group. Examples of divalent organic groups that can be formed include substituted or unsubstituted C2-5 alkylene groups, substituted or unsubstituted C1-3 alkyleneoxy C1-3 alkylene groups, substituted or unsubstituted C1-3 alkylentho C1-3 alkylene groups, or substituted or unsubstituted C1-3 alkyleneimino C1-3 alkylene groups. Furthermore, examples of silicon-containing divalent hydrocarbon groups include -CH2CH2-Si(CH3)2-CH2CH2-. Examples of "C2-5 alkylene groups" include dimethylene groups, trimethylene groups, and tetramethylene groups. Examples of "C1-3 alkylene oxy C1-3 alkylene groups" include the dimethylene oxydimethylene group. Examples of "C1-3 alkylenthiole C1-3 alkylene group" include the dimethylenthiole dimethylene group. Examples of "C1-3 alkylene iminoC1-3 alkylene group" include the dimethylene iminodimethylene group. Here, the imino group in "C1-3 alkylene alkylene imino C1-3 alkylene group" refers to -NH-. Preferred substituents on the "C2-5 alkylene group", "C1-3 alkyleneoxy C1-3 alkylene group", "C1-3 alkylentio C1-3 alkylene group", and "C1-3 alkyleneimino C1-3 alkylene group" are halogeno groups such as fluoro groups, chloro groups, bromo groups, and iod groups; C1-6 alkyl groups such as methyl groups, ethyl groups, n-propyl groups, i-propyl groups, n-butyl groups, s-butyl groups, i-butyl groups, and t-butyl groups; methylidene groups; or C1-6 haloalkyl groups such as chloromethyl groups, chloroethyl groups, trifluoromethyl groups, 1,2-dichloro-n-propyl groups, and 1-fluoro-n-butyl groups.

[0102] "R c R d Specific examples of groups represented by "N-" include amino groups, methylamino groups, dimethylamino groups, and i-propylamino groups.

[0103] "R" in G c R d In the group represented by N-CO-, R c and R d The above "R c R d This has the same meaning as in "groups represented by N-". "R c R d Specific examples of groups represented by "N-CO-" include the carbamoyl group, N,N-dimethylaminocarbonyl group, N-(i-propyl)aminocarbonyl group, and N-(i-propyl)-N-methylaminocarbonyl group.

[0104] "R" in G c R d N-NR d In the group represented by -CO-, R c and R dThe above "R c R d This has the same meaning as in "groups represented by N-". "R c R d N-NR d Specific examples of groups represented by "-CO-" include the 2,2-dimethylhydrazine-1-carbonyl group.

[0105] "R" in G a In the group represented by -CO-O-, R a The above "R a This has the same meaning as in "a group represented by -CO-". "R a Specific examples of groups represented by "-CO-O-" include the acetyloxy group.

[0106] "R" in G a -CO-NR e - in the base represented by -, R a The above "R a This has the same meaning as in "a group represented by -CO-". R e This represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a substituted or unsubstituted C6-10 aryl group. R e A specific example of a substituent in R a The same examples given in the previous section can be cited. "R a -CO-NR e Specific examples of groups represented by "-" include acetylamino group, propionylamino group, butyrylamino group, and i-propylcarbonylamino group.

[0107] "R" in G a -CO-CO-NR e - in the base represented by -, R a The above "R a This has the same meaning as in "groups represented by -CO-". e The above "Ra -CO-NR e This indicates a similar meaning to that in "the base represented by -". "R a -CO-CO-NR e Specific examples of groups represented by "-" include the oxopropanamide group.

[0108] "R" in G a -CO-NR e -NR e - in the base represented by -, R a The above "R a This has the same meaning as in "groups represented by -CO-". e The above "R a -CO-NR e This indicates a similar meaning to that in "the base represented by -". "R a -CO-NR e -NR e Specific examples of the group represented by "-" include the acetylhydrazinyl group and the i-propylcarbonylhydrazinyl group.

[0109] "R" in G a -CO-NR e -NR e In the group represented by -CO-, R a The above "R a This has the same meaning as in "groups represented by -CO-". e The above "R a -CO-NR e This indicates a similar meaning to that in "the base represented by -". "R a -CO-NR e -NR e Specific examples of groups represented by "-CO-" include the 2-acetylhydrazine-1-carbonyl group.

[0110] "R" in G b In the group represented by -O-CO-O-, R b The above "R bThis has a similar meaning to that of the "group represented by -O-CO-". "R b Specific examples of groups represented by "-O-CO-O-" include the methoxycarbonyloxy group and the ethoxycarbonyloxy group.

[0111] "R" in G b -O-CO-NR e - in the group represented by -, R b The above "R b This has a similar meaning to that in the group represented by -O-CO-. e The above "R b -CO-NR e This indicates a similar meaning to that in "the base represented by -". "R b -O-CO-NR e Specific examples of the group represented by "-" include the methoxycarbonylamino group.

[0112] "R" in G c R d In the group represented by N-CO-O-, R c and R d The above "R c R d This has the same meaning as in "groups represented by N-". "R c R d Specific examples of groups represented by "N-CO-O-" include the carbamoyloxy group and the N,N-dimethylaminocarbonyloxy group.

[0113] "R" in G c R d N-CO-NR e - in the group represented by -, R c and R d The above "R c R d This has the same meaning as in "groups represented by N-". e The above "R a -CO-NR e This indicates a similar meaning to that in "the base represented by -". "R c R d N-CO-NR e Specific examples of the group represented by "-" include the carbamoylamino group and the N,N-dimethylaminocarbonylamino group.

[0114] "R" in G c R d N-CO-CO-NR e - in the group represented by -, R c and R d The above "R c R d This has the same meaning as in "groups represented by N-". e The above "R a -CO-NR e This indicates a similar meaning to that in "the base represented by -". "R c R d N-CO-CO-NR e Specific examples of the group represented by "-" include the 2-(methylamino)-2-oxoacetamide group and the 2-(t-butylamino)-2-oxoacetamide group.

[0115] "R" in G a -CS-NR e - in the group represented by -, R a The above "R a This has the same meaning as in "groups represented by -CO-". e The above "R a -CO-NR e This indicates a similar meaning to that in "the base represented by -". "R a -CS-NR e Specific examples of groups represented by "-" include the ethanethioamide group, the propanethioamide group, and the 2-methylpropanethioamide group.

[0116] "R" in G c R d N-CS-NR e - in the group represented by -, R c and Rd The above "R c R d This has the same meaning as in "groups represented by N-". e The above "R a -CO-NR e This indicates a similar meaning to that in "the base represented by -". "R c R d N-CS-NR e Specific examples of the group represented by "-" include the 3,3-dimethylthioureide group.

[0117] "R" in G b SO2-NR e - in the group represented by -, R b The above "R b This has a similar meaning to that in the group represented by -O-CO-. e The above "R a -CO-NR e This indicates a similar meaning to that in "the base represented by -". "R b SO2-NR e Specific examples of the group represented by "-" include the methanesulfonylamino group.

[0118] "R" in G c R d In the group represented by N-SO2-, R c and R d The above "R c R d This has the same meaning as in "groups represented by N-". "R c R d Specific examples of the group represented by "N-SO2-" include the N,N-dimethylaminosulfonyl group.

[0119] "R" in G a ON=CR f - in the group represented by -, R a The above "R a This has the same meaning as in "a group represented by -CO-". R f represents a hydrogen atom, an amino group, or a substituted or unsubstituted C1-6 alkyl group. R f Specific examples of the substituents in a can be the same as those exemplified in “R a O-N=CR f -represented groups” include, for example, a (hydroxyimino)methyl group, an (ethoxyimino)methyl group, and the like.

[0120] In “R a -C(=NR g )-NR e -represented groups” in G, R a has the same meaning as that in the above “R a -CO-represented groups”. R e has the same meaning as that in the above “R a -CO-NR e -represented groups”. R g each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. R g Specific examples of the substituents in a can be the same as those exemplified in

[0121] In “R c R d N-C(=NR g )-represented groups” in G, R c and R d have the same meaning as those in the above “R[[ID=5​​​​​​​​​​​​​​​​​i In the group represented by S(=O)=N-CO-, R h Each independently represents a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, and R i Each of these independently represents a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. R h or R i A specific example of a substituent in R is a The same examples given in the previous section can be cited.

[0123] Here, R h and R i These may combine to form a divalent organic group. Examples of divalent organic groups that can be formed include substituted or unsubstituted C2-5 alkylene groups or substituted or unsubstituted C1-3 alkylene oxy C1-3 alkylene groups. Examples of "C2-5 alkylene groups" include dimethylene groups, trimethylene groups, and tetramethylene groups. Examples of "C1-3 alkylene oxy C1-3 alkylene groups" include the dimethylene oxydimethylene group. Preferred substituents on the "C2-5 alkylene group" or "C1-3 alkyleneoxy C1-3 alkylene group" are halogeno groups such as fluoro groups, chloro groups, bromo groups, and iod groups; C1-6 alkyl groups such as methyl groups, ethyl groups, n-propyl groups, i-propyl groups, n-butyl groups, s-butyl groups, i-butyl groups, and t-butyl groups; or C1-6 haloalkyl groups such as chloromethyl groups, chloroethyl groups, trifluoromethyl groups, 1,2-dichloro-n-propyl groups, and 1-fluoro-n-butyl groups.

[0124] "R" in G h R i In the group represented by S=N-CO-, R h or R i The above "R h R iThis has the same meaning as in the group represented by S(=O)=N-CO-.

[0125] "R" in G h R j In the group represented by C=NO-, R h and R j The above "R h R j This has the same meaning as in the group represented by S=NO-. "R h R j Specific examples of groups represented by C=NO- include the (propane-2-ylideneamino)oxy group.

[0126] When there are two or more substituents (G), examples of divalent organic groups that can be formed by two of them together include substituted or unsubstituted C1-5 alkylene groups, substituted or unsubstituted oxy C1-4 alkylene groups, substituted or unsubstituted oxy C2-3 alkylene oxy groups, or substituted or unsubstituted C1-3 alkylene oxy C1-3 alkylene groups. Examples of "C1-5 alkylene groups" include methylene groups, dimethylene groups, trimethylene groups, and tetramethylene groups. Examples of "oxy C1-4 alkylene groups" include oxymethylene groups and oxydimethylene groups. Examples of "oxy C2-3 alkylene oxy groups" include oxydimethylene oxy groups. Examples of "C1-3 alkylene oxy C1-3 alkylene groups" include the dimethylene oxydimethylene group. Preferred substituents on the "C1-5 alkylene group", "oxy C1-4 alkylene group", "oxy C2-3 alkylene oxy group", and "C1-3 alkylene oxy C1-3 alkylene group" are halogeno groups such as fluoro groups, chloro groups, bromo groups, and iod groups; C1-6 alkyl groups such as methyl groups, ethyl groups, n-propyl groups, i-propyl groups, n-butyl groups, s-butyl groups, i-butyl groups, and t-butyl groups; or C1-6 haloalkyl groups such as chloromethyl groups, chloroethyl groups, trifluoromethyl groups, 1,2-dichloro-n-propyl groups, and 1-fluoro-n-butyl groups.

[0127] In the present invention, preferred Gs include halogeno groups, substituted or unsubstituted C1-6 alkyl groups, substituted or unsubstituted C1-6 alkoxy groups, substituted or unsubstituted C1-6 alkylthio groups, substituted or unsubstituted C1-6 alkylsulfinyl groups, substituted or unsubstituted C1-6 alkylsulfonyl groups, substituted or unsubstituted C3-6 cycloalkyl groups, substituted or unsubstituted C6-10 aryl groups, substituted or unsubstituted 3-10 membered heterocyclyl groups, and R b A group represented by -O-CO-, R c R d The group represented by N-, R c R d The group represented by N-CO-, R a A group represented by -CO-O-, R a -CO-NR e - represents a group, R b -O-CO-NR e - represents a group, R c R d The group represented by N-CO-O-, R c R d N-CO-NR e - represents a group, R c R d N-CS-NR e - represents a group, R b SO2-NR e - represents a group, R a ON=CR f - A group represented by -, or R h R iOne example is the group represented by C=NO-.

[0128] [A] A represents a substituted or unsubstituted C1-6 alkylene group, a substituted or unsubstituted C2-6 alkenylene group, a substituted or unsubstituted C2-6 alkynylene group, or a substituted or unsubstituted C3-6 cycloalkylene group.

[0129] Examples of "C1-6 alkylene groups" in A include methylene groups, dimethylene groups, trimethylene groups, and tetramethylene groups. Examples of "C2-6 alkenylene groups" in A include vinylene groups (-CH=CH-), divinylene groups (-CH=CH-CH=CH-), and propenylene groups (-CH=CH-CH2-, -CH2-CH=CH-). Examples of "C2-6 alkynylene groups" in A include ethynylene groups (-C≡C-) and propynylene groups (-CH2-C≡C-, -C≡C-CH2-). Examples of the "C3-6 cycloalkylene group" in A include the 1,2-cyclopropylene group, the 1,2-cyclobutanediyl group, and the 1,3-cyclobutanediyl group.

[0130] In the present invention, preferred A members include substituted or unsubstituted C1-6 alkylene groups or substituted or unsubstituted C2-6 alkenylene groups. The substituents on the C1-6 alkylene group or the C2-6 alkenylene group can be one or more substituents selected from the following group of substituents (hereinafter, this substituent may be represented by the symbol "Ga"). Furthermore, if there are two or more substituents (Ga), two of them may combine to form a divalent organic group. The substituent groups are shown below. A halogen group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C2-6 alkenyloxy group, a substituted or unsubstituted C2-6 alkynyloxy group, a mercapto group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C3-6 cycloalkyloxy group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted C6-10 arylthio group, a substituted or unsubstituted C6-10 arylsulfinyl group, a substituted or unsubstituted C6-10 arylsulfonyl group, a substituted or unsubstituted 3-6 membered heterocyclyl group, a substituted or unsubstituted 3-6 membered heterocyclyloxy group, a nitro group, a cyano group, R a1 A group represented by -CO-, a carboxy group, R b1 A group represented by -O-CO-, R c1 R d1 A group represented by N-, R c1 R d1 A group represented by N-CO-, R a1 A group represented by -CO-O-, R a1 -CO-NR e1 A group represented by -, R b1 A group represented by -O-CO-O-, R b1 -O-CO-NR e1 A group represented by -, R c1 R d1 A group represented by N-CO-O-, R c1 R d1 N-CO-NR e1 A group represented by -, R b1 SO2-NR e1 A group represented by -, R c1 R d1 A group represented by N-SO2-, R a1 O-N=CR f1 A group represented by -, R g1 R h1Groups represented by C=NO-, oxo groups (O=), thioxo groups (S=), R a1 A divalent base represented by -N=, R a1 A divalent base represented by ON=, R c1 R d1 A divalent base represented by NN=, R a1 -CO-NR e1 A divalent base represented by -N=, R b1 -O-CO-NR e1 A divalent base represented by -N=, R b1 SO2-NR e1 A divalent base represented by -N=.

[0131] Among the above group of substituents, R a1 Each of these 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 C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R b1 Each of these independently represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R c1 Each of these 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 C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R d1 Each of these independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, where R c1 and R d1 These may combine to form a divalent organic group. Re1 Each of these independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. R f1 This represents a hydrogen atom, or a substituted or unsubstituted C1-6 alkyl group. R g1 This represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R h1 R represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, where R g1 and R h1 These may combine to form a divalent organic group.

[0132] Examples of "halogeno groups" in Ga include fluoro groups, chloro groups, bromo groups, and iod groups.

[0133] The "C1-6 alkyl group" in Ga may be a linear or branched chain. Examples of "C1-6 alkyl groups" in Ga include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s-butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, and i-hexyl group.

[0134] Examples of "C2-6 alkenyl groups" in Ga 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.

[0135] Examples of "C2-6 alkynyl groups" in Ga include ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, and 1,1-dimethyl-2-butynyl group.

[0136] Examples of "C1-6 alkoxy groups" in Ga include methoxy group, ethoxy group, n-propoxy group, n-butoxy group, n-pentyloxy group, n-hexyloxy group, i-propoxy group, i-butoxy group, s-butoxy group, t-butoxy group, and i-hexyloxy group. Examples of "C2-6 alkenyloxy groups" in Ga include vinyloxy groups, allyloxy groups, propenyloxy groups, and butenyloxy groups. Examples of "C2-6 alkynyloxy groups" in Ga include ethynyloxy groups and propargyloxy groups.

[0137] Examples of "C1-6 alkylthio groups" in Ga include methylthio group, ethylthio group, n-propylthio group, n-butylthio group, n-pentylthio group, n-hexylthio group, and i-propylthio group. Examples of "C1-6 alkyl sulfinyl groups" in Ga include methyl sulfinyl group, ethyl sulfinyl group, and t-butyl sulfinyl group. Examples of "C1-6 alkylsulfonyl groups" in Ga include methylsulfonyl groups, ethylsulfonyl groups, and t-butylsulfonyl groups.

[0138] Substituents on "C1-6 alkyl groups", "C2-6 alkenyl groups", "C2-6 alkynyl groups", "C1-6 alkoxy groups", "C2-6 alkenyloxy groups", "C2-6 alkynyloxy groups", "C1-6 alkylthio groups", "C1-6 alkylsulfinyl groups", or "C1-6 alkylsulfonyl groups" in Ga include halogen groups such as fluoro groups, chloro groups, bromo groups, and iod groups; hydroxyl groups; C1-6 alkoxy groups such as methoxy groups, ethoxy groups, n-propoxy groups, i-propoxy groups, n-butoxy groups, s-butoxy groups, i-butoxy groups, and t-butoxy groups; 2-chloro-n-propoxy groups, 2,3-di Preferred are C1-6 haloalkoxy groups such as chlorobutoxy and trifluoromethoxy groups; C3-6 cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups; C6-10 aryl groups such as phenyl and naphthyl groups; C6-10 aryl groups substituted with one or more substituents of C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups, such as 4-methylphenyl, 4-methoxyphenyl, 4-chlorophenyl, 4-trifluoromethylphenyl, and 4-trifluoromethoxyphenyl groups; or cyano groups.

[0139] Examples of "C3-6 cycloalkyl groups" in Ga include cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, and cyclohexyl groups. Examples of "C3-6 cycloalkyloxy groups" in Ga include cyclopropyloxy group, cyclobutyloxy group, cyclopentyloxy group, and cyclohexyloxy group.

[0140] Examples of "C6-10 aryl groups" in Ga include phenyl, naphthyl, indenyl, indanyl, and tetralinyl groups. Examples of "C6-10 aryloxy groups" in Ga include phenoxy groups and naphthoxy groups.

[0141] Examples of "C6-10 arylthio groups" in Ga include phenylthio groups and naphthylthio groups. Examples of "C6-10 arylsulfinyl groups" in Ga include phenylsulfinyl groups and naphthylsulfinyl groups. Examples of "C6-10 arylsulfonyl groups" in Ga include phenylsulfonyl groups and naphthylsulfonyl groups.

[0142] In Ga, a "3- to 6-membered heterocyclyl group" is a group that contains one, two, three, or four heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms as constituent atoms of the ring. When there are two or more heteroatoms, they may be the same or different. Examples of "3- to 6-membered heterocyclyl groups" include saturated heterocyclyl groups, heteroaryl groups, and partially unsaturated heterocyclyl groups.

[0143] Examples of saturated heterocyclyl groups with 3 to 6 members include azilidinyl group, epoxy group, azetidinyl group, oxetanyl group, pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, tetrahydro-2H-pyranyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, and dioxanyl group. Examples of 5- to 6-membered heteroaryl groups include 5-membered heteroaryl groups such as pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups; and 6-membered heteroaryl groups such as pyridyl, pyrazinyl, pyrimidinyl, pyridadinyl, and triazinyl groups. Examples of partially unsaturated heterocyclyl groups with 5- to 6 member rings include pyrrolinyl groups, dihydrofuranyl groups, imidazolinyl groups, pyrazolinyl groups, and oxazolinyl groups; and partially unsaturated heterocyclyl groups with 6 member rings, such as isoxazolinyl groups and dihydropyranyl groups.

[0144] In Ga, a "3- to 6-membered heterocyclyloxy group" has a structure in which a 3- to 6-membered heterocyclyl group is bonded to an oxy group. Specific examples include thiazolyloxy groups and pyridyloxy groups.

[0145] Substituents on Ga include "C3-6 cycloalkyl groups", "C3-6 cycloalkyloxy groups", "C6-10 aryl groups", "C6-10 aryloxy groups", "C6-10 arylthio groups", "C6-10 arylsulfinyl groups", "C6-10 arylsulfonyl groups", "3-6 membered heterocyclyl groups", or "3-6 membered heterocyclyloxy groups". These substituents include halogeno groups such as fluoro groups, chloro groups, bromo groups, and iod groups; C1-6 alkyl groups such as methyl groups, ethyl groups, n-propyl groups, i-propyl groups, n-butyl groups, s-butyl groups, i-butyl groups, t-butyl groups, n-pentyl groups, and n-hexyl groups; and chloromethyl groups, chloroethyl groups, trifluoromethyl groups, 1,2-dichloro-n-propyl groups, and 1-fluoro-n-butyl groups. C1-6 haloalkyl groups; hydroxyl groups; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy groups; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, and trifluoromethoxy; C6-10 aryl groups such as phenyl and naphthyl groups; C6-10 aryl groups substituted with one or more substituents of C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups, such as 4-methylphenyl, 4-methoxyphenyl, 4-chlorophenyl, 4-trifluoromethylphenyl, and 4-trifluoromethoxyphenyl; or cyano groups are preferred.

[0146] "R" in Ga a1 In the group represented by -CO-, R a1This 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 C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group.

[0147] R a1 Examples of "C1-6 alkyl groups" in this context include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s-butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, and i-hexyl group. R a1 Examples of "C2-6 alkenyl groups" in this context include vinyl groups and 1-propenyl groups. R a1 Examples of "C2-6 alkynyl groups" in this context include the ethynyl group and the 1-propynyl group. R a1 Substituents on the "C1-6 alkyl group", "C2-6 alkenyl group", or "C2-6 alkynyl group" include halogen groups such as fluoro, chloro, bromo, and iod groups; hydroxyl groups; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy groups; and C1-6 alkyl groups such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, and trifluoromethoxy groups. 6-haloalkoxy groups; C3-6 cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups; C6-10 aryl groups such as phenyl and naphthyl groups; C6-10 aryl groups substituted with one or more substituents of a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group, such as 4-chlorophenyl, 4-trifluoromethylphenyl, and 4-trifluoromethoxyphenyl groups; or cyano groups are preferred.

[0148] R a1Examples of "C3-6 cycloalkyl groups" in this context include cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, and cyclohexyl groups. R a1 Examples of "C6-10 aryl groups" in this context include phenyl groups and naphthyl groups.

[0149] R a1 In this context, a "5-6 membered heterocyclyl group" is a group that contains one, two, three, or four heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms as constituent atoms of the ring. When there are two or more heteroatoms, they may be the same or different. Examples of "5-6 membered heterocyclyl groups" include 5-6 membered saturated heterocyclyl groups, 5-6 membered heteroaryl groups, and 5-6 membered partially unsaturated heterocyclyl groups. Examples of saturated heterocyclyl groups with 5-6 member rings include pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, tetrahydro-2H-pyranyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, and dioxanyl group. Examples of 5- to 6-membered heteroaryl groups include 5-membered heteroaryl groups such as pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups; and 6-membered heteroaryl groups such as pyridyl, pyrazinyl, pyrimidinyl, pyridadinyl, and triazinyl groups. Examples of partially unsaturated heterocyclyl groups with 5- to 6 member rings include pyrrolinyl groups, dihydrofuranyl groups, imidazolinyl groups, pyrazolinyl groups, and oxazolinyl groups; and partially unsaturated heterocyclyl groups with 6 member rings, such as isoxazolinyl groups and dihydropyranyl groups.

[0150] R a1Substituents on the "C3-6 cycloalkyl group", "C6-10 aryl group", or "5-6 membered heterocyclyl group" in the above include: halogen groups such as fluoro, chloro, bromo, and iod groups; 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 groups; C1-6 haloalkyl groups such as chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, and 1-fluoro-n-butyl groups; hydroxyl groups; methoxy, ethoxy, n-propoxy, i-propoxy, and n-butoxy groups. Preferably, C1-6 alkoxy groups such as s-butoxy, i-butoxy, and t-butoxy groups; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, and trifluoromethoxy groups; C6-10 aryl groups such as phenyl and naphthyl groups; C6-10 aryl groups substituted with one or more substituents of C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups, such as 4-methylphenyl, 4-methoxyphenyl, 4-chlorophenyl, 4-trifluoromethylphenyl, and 4-trifluoromethoxyphenyl groups; or cyano groups.

[0151] "R a1 Examples of groups represented by "-CO-" include the formyl group and the acetyl group.

[0152] "R" in Ga b1 In the group represented by -O-CO-, R b1 This represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R b1 A specific example of a substituent in R is a1 The same examples given in the previous section can be cited.

[0153] "R b1 Specific examples of groups represented by "-O-CO-" include the methoxycarbonyl group, ethoxycarbonyl group, and t-butoxycarbonyl group.

[0154] "R" in Ga c1 R d1 In the group represented by N-, R c1 R represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. d1 This represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. R c1 or R d1 A specific example of a substituent in R is a1 The same examples given in the previous section can be cited. Here, R c1 and R d1 These may combine to form a divalent organic group. Examples of divalent organic groups that can be formed include substituted or unsubstituted C2-5 alkylene groups or substituted or unsubstituted C1-3 alkylene oxy C1-3 alkylene groups. Examples of "C2-5 alkylene groups" include dimethylene groups, trimethylene groups, and tetramethylene groups. Examples of "C1-3 alkylene oxy C1-3 alkylene groups" include the dimethylene oxydimethylene group. Preferred substituents on the "C2-5 alkylene group" or "C1-3 alkyleneoxy C1-3 alkylene group" are halogeno groups such as fluoro groups, chloro groups, bromo groups, and iod groups; C1-6 alkyl groups such as methyl groups, ethyl groups, n-propyl groups, i-propyl groups, n-butyl groups, s-butyl groups, i-butyl groups, and t-butyl groups; or C1-6 haloalkyl groups such as chloromethyl groups, chloroethyl groups, trifluoromethyl groups, 1,2-dichloro-n-propyl groups, and 1-fluoro-n-butyl groups.

[0155] "R c1 R d1 Specific examples of groups represented by "N-" include amino groups, methylamino groups, and dimethylamino groups.

[0156] "R" in Ga c1 R d1 In the group represented by N-CO-, R c1 and R d1 The above "R c1 R d1 This has the same meaning as in "groups represented by N-". "R c1 R d1 Specific examples of groups represented by "N-CO-" include the carbamoyl group, N,N-dimethylaminocarbonyl group, N-(i-propyl)aminocarbonyl group, and N-(i-propyl)-N-methylaminocarbonyl group.

[0157] "R" in Ga a1 In the group represented by -CO-O-, R a1 The above "R a1 This has the same meaning as in "a group represented by -CO-". "R a1 Specific examples of groups represented by "-CO-O-" include the acetyloxy group.

[0158] "R" in Ga a1 -CO-NR e1 - in the group represented by -, R a1 The above "R a1This has the same meaning as in "a group represented by -CO-". R e1 This represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. R e1 A specific example of a substituent in R is a1 The same examples given in the previous section can be cited. "R a1 -CO-NR e1 Specific examples of groups represented by "-" include the acetylamino group.

[0159] "R" in Ga b1 In the group represented by -O-CO-O-, R b1 The above "R b1 This has a similar meaning to that of the "group represented by -O-CO-". "R b1 Specific examples of groups represented by "-O-CO-O-" include the methoxycarbonyloxy group and the ethoxycarbonyloxy group.

[0160] "R" in Ga b1 -O-CO-NR e1 - in the group represented by -, R b1 The above "R b1 This has a similar meaning to that in the group represented by -O-CO-. e1 The above "R b1 -CO-NR e1 This indicates a similar meaning to that in "the base represented by -". "R b1 -O-CO-NR e1 Specific examples of the group represented by "-" include the methoxycarbonylamino group.

[0161] "R" in Ga c1 R d1 In the group represented by N-CO-O-, R c1 and R d1 The above "R c1 R d1This has the same meaning as in "groups represented by N-". "R c1 R d1 Specific examples of groups represented by "N-CO-O-" include the carbamoyloxy group and the N,N-dimethylaminocarbonyloxy group.

[0162] "R" in Ga c1 R d1 N-CO-NR e1 - in the base represented by -, R c1 and R d1 The above "R c1 R d1 This has the same meaning as in "groups represented by N-". e1 The above "R a1 -CO-NR e1 This indicates a similar meaning to that in "the base represented by -". "R c1 R d1 N-CO-NR e1 Specific examples of the group represented by "-" include the carbamoylamino group and the N,N-dimethylaminocarbonylamino group.

[0163] "R" in Ga b1 SO2-NR e1 - in the base represented by -, R b1 The above "R b1 This has a similar meaning to that in the group represented by -O-CO-. e1 The above "R a1 -CO-NR e1 This indicates a similar meaning to that in "the base represented by -". "R b1 SO2-NR e1 Specific examples of the group represented by "-" include the methanesulfonylamino group.

[0164] "R" in Ga c1 R d1 In the group represented by N-SO2-, R c1 and R d1 The above "R c1 R d1This has the same meaning as in "groups represented by N-". "R c1 R d1 Specific examples of the group represented by "N-SO2-" include the N,N-dimethylaminosulfonyl group.

[0165] "R" in Ga a1 ON=CR f1 - in the group represented by -, R a1 The above "R a1 This has the same meaning as in "a group represented by -CO-". R f1 This represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group. R f1 A specific example of a substituent in R is a The same examples given in the previous section can be cited. "R a1 ON=CR f1 Specific examples of groups represented by "-" include the (hydroxyimino)methyl group and the (ethoxyimino)methyl group.

[0166] "R" in Ga g1 R h1 In the group represented by C=NO-, R g1 R represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. h1 This represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group. R g1 or R h1 A specific example of a substituent in R is a1 The same examples given in the previous section can be cited. Here, R g1 and R h1 These may combine to form a divalent organic group. Examples of divalent organic groups that can be formed include substituted or unsubstituted C2-5 alkylene groups or substituted or unsubstituted C1-3 alkylene oxy C1-3 alkylene groups. Examples of "C2-5 alkylene groups" include dimethylene groups, trimethylene groups, and tetramethylene groups. Examples of "C1-3 alkylene oxy C1-3 alkylene groups" include the dimethylene oxydimethylene group. Preferred substituents on the "C2-5 alkylene group" or "C1-3 alkyleneoxy C1-3 alkylene group" are halogeno groups such as fluoro groups, chloro groups, bromo groups, and iod groups; C1-6 alkyl groups such as methyl groups, ethyl groups, n-propyl groups, i-propyl groups, n-butyl groups, s-butyl groups, i-butyl groups, and t-butyl groups; or C1-6 haloalkyl groups such as chloromethyl groups, chloroethyl groups, trifluoromethyl groups, 1,2-dichloro-n-propyl groups, and 1-fluoro-n-butyl groups. "R g1 R h1 Specific examples of groups represented by C=NO- include the (propane-2-ylideneamino)oxy group.

[0167] "R" in Ga a1 Among the divalent base represented by -N=, R a1 The above "R a1 This has the same meaning as in "a group represented by -CO-". "R a1 Examples of divalent groups represented by -N= include the imino group (HN=) and the methylimino group.

[0168] "R" in Ga a1 Among the divalent base represented by ON=, R a1 The above "R a1 This has the same meaning as in "a group represented by -CO-". "R a1 Specific examples of divalent groups represented by "ON=" include the N-hydroxyimino group and the N-methoxyimino group.

[0169] "R" in Ga c1 R d1 In the divalent base represented by NN=, R c1 and R d1 The above "R c1 R d1 This has the same meaning as in "groups represented by N-". "R c1 R d1 Specific examples of divalent groups represented by NN= include the 2,2-dimethylhydrazinylidene group.

[0170] "R" in Ga a1 -CO-NR e1 Among the divalent base represented by -N=, R a1 The above "R a1 This has the same meaning as in "groups represented by -CO-". e1 The above "R a1 -CO-NR e1 This indicates a similar meaning to that in "the base represented by -".

[0171] "R" in Ga b1 -O-CO-NR e1 Among the divalent base represented by -N=, R b1 The above "R b1 This has a similar meaning to that in the group represented by -O-CO-. e1 The above "R a1 -CO-NR e1 This indicates a similar meaning to that in "the base represented by -".

[0172] "R" in Ga b1 SO2-NR e1 Among the divalent base represented by -N=, R b1 The above "R b1 This has a similar meaning to that in the group represented by -O-CO-. e1 The above "R a1 -CO-NR e1 This indicates a similar meaning to that in "the base represented by -".

[0173] When there are two or more substituents (Ga), examples of divalent organic groups that can be formed by two of them together include substituted or unsubstituted C1-5 alkylene groups, substituted or unsubstituted oxy C1-4 alkylene groups, substituted or unsubstituted oxy C2-3 alkylene oxy groups, or substituted or unsubstituted C1-3 alkylene oxy C1-3 alkylene groups. Examples of "C1-5 alkylene groups" include methylene groups, dimethylene groups, trimethylene groups, and tetramethylene groups. Examples of "oxy C1-4 alkylene groups" include oxymethylene groups and oxydimethylene groups. Examples of "oxy C2-3 alkylene oxy groups" include oxydimethylene oxy groups. Examples of "C1-3 alkylene oxy C1-3 alkylene groups" include the dimethylene oxydimethylene group. Preferred substituents on the "C1-5 alkylene group", "oxy C1-4 alkylene group", "oxy C2-3 alkylene oxy group", and "C1-3 alkylene oxy C1-3 alkylene group" are halogeno groups such as fluoro groups, chloro groups, bromo groups, and iod groups; C1-6 alkyl groups such as methyl groups, ethyl groups, n-propyl groups, i-propyl groups, n-butyl groups, s-butyl groups, i-butyl groups, and t-butyl groups; or C1-6 haloalkyl groups such as chloromethyl groups, chloroethyl groups, trifluoromethyl groups, 1,2-dichloro-n-propyl groups, and 1-fluoro-n-butyl groups.

[0174] In the present invention, preferred Ga are hydroxyl groups, substituted or unsubstituted C1-6 alkoxy groups, substituted or unsubstituted C2-6 alkenyloxy groups, substituted or unsubstituted C2-6 alkynyloxy groups, substituted or unsubstituted C3-6 cycloalkyloxy groups, substituted or unsubstituted C6-10 aryloxy groups, substituted or unsubstituted 5-6 membered ring heterocyclyloxy groups, R a1 A group represented as -CO-O-, an oxo group (O=), or R a1 We can list the divalent base represented by ON=. In this case, a preferred substituted or unsubstituted 5- to 6-membered heterocyclyloxy group is the tetrahydro-2H-pyran-4-yl group.

[0175] In the present invention, more preferred Ga are hydroxyl groups, substituted or unsubstituted C1-6 alkoxy groups, substituted or unsubstituted C2-6 alkenyloxy groups, substituted or unsubstituted C2-6 alkynyloxy groups, and R a1 A group represented as -CO-O-, an oxo group (O=), or R a1 We can list the divalent base represented by ON=.

[0176] 〔salt〕 The salt of compound (II) is not particularly limited as long as it is an agriculturally and horticulturally acceptable salt. Examples 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; salts of organic bases such as triethylamine, tributylamine, pyridine, and hydrazine; and ammonia.

[0177] [Manufacturing method] The method for producing compound (II) or a salt of compound (II) is not limited. For example, compound (II) or a salt of compound (II) of the present invention can be obtained by known methods as described in the examples. Alternatively, a salt of compound (II) can be obtained from compound (II) by known methods.

[0178] (Reaction Scheme 1) For example, among compound (II), the compound of formula (I-1) shown below can be prepared by condensing the compound of formula (III-1) and the compound of formula (A), as shown in reaction scheme 1 below.

[0179] [ka]

[0180] In formula (I-1), X 1# X in equation (II) 1 It has a similar meaning, or by general methods, X 1 This shows a structure that can be guided to X. 2# X in equation (II) 2 It has a similar meaning, or by general methods, X 2 This shows a structure that can be guided to X. 3# X in equation (II) 3 It has a similar meaning, or by general methods, X 3 This shows a structure that can be guided to Q. # This either has the same meaning as Q in equation (II), or represents a structure that can be derived to Q by a general method. # This either has the same meaning as A in equation (II), or represents a structure that can be derived to A by general methods. The symbols in equation (III-1) have the same meaning as those in equation (I-1). X in equation (A) 3# The symbol has the same meaning as in formula (I-1). L indicates a leaving group. For example, when using a compound of formula (A) having a leaving group such as a methanesulfonyloxy group in L, it can be prepared by reacting it in the presence of an inorganic base. For example, if a compound of formula (A) in which L is a hydroxyl group is used, it can be prepared by using the Mitsunobu reaction.

[0181] (Reaction Scheme 2) The compound of formula (III-1) can be prepared by condensing the compound of formula (B) and the compound of formula (C), as shown in reaction scheme 2 below.

[0182] [ka]

[0183] The symbols in formula (B) have the same meaning as those in formula (I-1). The symbols in formula (C) have the same meaning as those in formula (I-1). Hal indicates a halogen group. For example, the compound of formula (B) and the compound of formula (C) can be prepared by reacting them in the presence of an inorganic base.

[0184] (Reaction Scheme 3) Among the compounds of formula (B), X 2 Part R 1 ON=CR 6 The compound of formula (B-1), which has a group represented by -, can be prepared by condensing the compound of formula (D) and the compound of formula (E), as shown in reaction scheme 3 below.

[0185] [ka]

[0186] R in equation (B-1) 1 and R 6 X has the same meaning as in equation (II). 1# This has the same meaning as in equation (I-1). R in equation (D) 6 X has the same meaning as in equation (II). 1# This has the same meaning as in equation (I-1). R in equation (E) 1 The symbol has the same meaning as in formula (II). Note that the hydrochloride salt of the compound in formula (E) may also be used. For example, it can be prepared by reacting the compound of formula (D) with the compound of formula (E) in an alcohol solvent.

[0187] (Reaction Scheme 4) Among the compounds of formula (I-1), X 2 Part R 1 ON=CR 6 The compound of formula (I-2), which has a group represented by -, can be prepared by condensing the compound of formula (F) and the compound of formula (E), as shown in the reaction scheme 4 below.

[0188] [ka]

[0189] R in equation (I-2) 1 and R 6 The symbol has the same meaning as in equation (II). The other symbols have the same meaning as in equation (I-1). R in equation (F) 6 The symbol has the same meaning as in equation (II). The other symbols have the same meaning as in equation (I-1). R in equation (E) 1 The symbol has the same meaning as in formula (II). Note that the hydrochloride salt of the compound in formula (E) may also be used. For example, it can be prepared by reacting the compound of formula (D) with the compound of formula (E) in an alcohol solvent.

[0190] (Reaction Scheme 5) The compound of formula (I-1) can also be prepared by condensing the compound of formula (IV-1) with the compound of formula (C), as shown in reaction scheme 5 below.

[0191] [ka]

[0192] The symbols in formula (IV-1) have the same meaning as those in formula (I-1). The symbols in formula (C) have the same meaning as those in formula (I-1). Hal indicates a halogen group. For example, the compound of formula (IV-1) and the compound of formula (C) can be prepared by reacting them in the presence of an inorganic base.

[0193] [Manufacturing intermediates] The compound represented by formula (III) below, or a salt thereof, can be used as a manufacturing intermediate in the production of the compound represented by formula (II).

[0194] [ka]

[0195] In formula (III), X1 This includes hydrogen atoms, halogen groups, substituted or unsubstituted C1-6 alkyl groups, substituted or unsubstituted C2-6 alkenyl groups, substituted or unsubstituted C2-6 alkynyl groups, hydroxyl groups, substituted or unsubstituted C1-6 alkoxy groups, substituted or unsubstituted C2-6 alkenyloxy groups, substituted or unsubstituted C2-6 alkynyloxy groups, substituted or unsubstituted C1-6 alkylthio groups, substituted or unsubstituted C1-6 alkylsulfinyl groups, substituted or unsubstituted C1-6 alkylsulfonyl groups, substituted or Unsubstituted C3-6 cycloalkyl groups, substituted or unsubstituted C3-6 cycloalkyloxy groups, substituted or unsubstituted C6-10 aryl groups, substituted or unsubstituted C6-10 aryloxy groups, substituted or unsubstituted C6-10 arylthio groups, substituted or unsubstituted C6-10 arylsulfinyl groups, substituted or unsubstituted C6-10 arylsulfonyl groups, substituted or unsubstituted 5-6 membered heterocyclyl groups, substituted or unsubstituted 5-6 membered heterocyclyloxy groups, nitro groups, cyano groups, R 1 Groups represented by -CO-, carboxyl groups, R 2 A group represented by -O-CO-, R 3 R 4 The group represented by N-, R 3 R 4 The group represented by N-CO-, R 1 A group represented by -CO-O-, R 1 -CO-NR 5 - represents a group, R 2 A group represented by -O-CO-O-, R 2 -O-CO-NR 5 - represents a group, R 3 R 4 The group represented by N-CO-O-, R 3 R 4 N-CO-NR 5 - represents a group, R 2 SO2-NR 5 - represents a group, R 3 R 4 A group represented by N-SO2-, or R 1 ON=CR 6 - indicates the group represented by; R 1Each of these 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 C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R 2 Each of these independently represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R 3 Each of these 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 C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R 4 Each of these independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. Here, R 3 and R 4 These may combine to form a divalent organic group. R 5 Each of these independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. R 6 This represents a hydrogen atom, a halogen group, an amino group, a substituted or unsubstituted monoC1-6 alkylamino group, a substituted or unsubstituted diC1-6 alkylamino group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, or a substituted or unsubstituted 5-6 membered heterocyclyl group; X 2 R 1 ON=CR 6- represents a group, R 1 CO-ON=CR 6 - represents a group, R 3 R 4 N-CO-ON=CR 6 - represents a group, R 3 R 4 NN=CR 6 - A group represented by -, or R 7 -N=CR 6 - indicates the group; R 1 , R 3 , R 4 , and R 6 X 1 It shows a similar meaning to those in R; 7 This represents a substituted or unsubstituted five-membered heterocyclyl group; A represents a substituted or unsubstituted C1-6 alkylene group, a substituted or unsubstituted C2-6 alkenylene group, a substituted or unsubstituted C2-6 alkynylene group, or a substituted or unsubstituted C3-6 cycloalkylene group; Q represents a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-10 membered heterocycline ring.

[0196] The symbols in equation (III) have the same meaning as those in equation (II).

[0197] The compound represented by formula (IV) below, or a salt thereof, can be used as a manufacturing intermediate in the production of the compound represented by formula (II).

[0198] [ka]

[0199] In formula (IV), X 1This includes hydrogen atoms, halogen groups, substituted or unsubstituted C1-6 alkyl groups, substituted or unsubstituted C2-6 alkenyl groups, substituted or unsubstituted C2-6 alkynyl groups, hydroxyl groups, substituted or unsubstituted C1-6 alkoxy groups, substituted or unsubstituted C2-6 alkenyloxy groups, substituted or unsubstituted C2-6 alkynyloxy groups, substituted or unsubstituted C1-6 alkylthio groups, substituted or unsubstituted C1-6 alkylsulfinyl groups, substituted or unsubstituted C1-6 alkylsulfonyl groups, substituted or Unsubstituted C3-6 cycloalkyl groups, substituted or unsubstituted C3-6 cycloalkyloxy groups, substituted or unsubstituted C6-10 aryl groups, substituted or unsubstituted C6-10 aryloxy groups, substituted or unsubstituted C6-10 arylthio groups, substituted or unsubstituted C6-10 arylsulfinyl groups, substituted or unsubstituted C6-10 arylsulfonyl groups, substituted or unsubstituted 5-6 membered heterocyclyl groups, substituted or unsubstituted 5-6 membered heterocyclyloxy groups, nitro groups, cyano groups, R 1 Groups represented by -CO-, carboxyl groups, R 2 A group represented by -O-CO-, R 3 R 4 The group represented by N-, R 3 R 4 The group represented by N-CO-, R 1 A group represented by -CO-O-, R 1 -CO-NR 5 - represents a group, R 2 A group represented by -O-CO-O-, R 2 -O-CO-NR 5 - represents a group, R 3 R 4 The group represented by N-CO-O-, R 3 R 4 N-CO-NR 5 - represents a group, R 2 SO2-NR 5 - represents a group, R 3 R 4 A group represented by N-SO2-, or R 1 ON=CR 6 - indicates the group represented by; R 1Each of these 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 C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R 2 Each of these independently represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R 3 Each of these 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 C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R 4 Each of these independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. Here, R 3 and R 4 These may combine to form a divalent organic group. R 5 Each of these independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. R 6 This represents a hydrogen atom, a halogen group, an amino group, a substituted or unsubstituted monoC1-6 alkylamino group, a substituted or unsubstituted diC1-6 alkylamino group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, or a substituted or unsubstituted 5-6 membered heterocyclyl group; X 2 R 1 ON=CR 6- represents a group, R 1 CO-ON=CR 6 - represents a group, R 3 R 4 N-CO-ON=CR 6 - represents a group, R 3 R 4 NN=CR 6 - A group represented by -, or R 7 -N=CR 6 - indicates the group; R 1 , R 3 , R 4 , and R 6 X 1 It shows a similar meaning to those in R; 7 This represents a substituted or unsubstituted five-membered heterocyclyl group; X 3 This refers to a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted linear C2-6 alkenyl group, a substituted or unsubstituted linear C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group; X 4 This represents a hydrogen atom or a C1-6 alkoxymethyl group.

[0200] X in equation (IV) 4 All other symbols have the same meaning as those in equation (II). X 4 Examples of "C1-6 alkoxy methyl groups" include methoxy group, ethoxy group, n-propoxy group, n-butoxy group, n-pentyloxy group, n-hexyloxy group, i-propoxy group, i-butoxy group, s-butoxy group, t-butoxy group, and i-hexyloxy group.

[0201] Table 1 below shows an example of a manufacturing intermediate used in the production of compound (II) of the present invention. The melting point (mp) of each compound is also shown in the table.

[0202] [Table 1] TIFF0007846807000016.tif208113

[0203] Of the compounds listed in Table 1, those having amorphous or viscous oil properties are described below. 1 H-NMR data is shown. Compound 11: 1 H-NMR (CDCl3) 7.49(1H, s), 5.21-3.70(7H, m), 3.43(3H, s),2.16(3H, s), 1.35-1.20(9H, m).

[0204] [Fungicides for agricultural and horticultural use] The fungicide for agricultural and horticultural use of the present invention contains at least one selected from compound (II) and its salts as an active ingredient. The amount of compound (II) or its salt contained in the fungicide for agricultural and horticultural use of the present invention is not particularly limited as long as it exhibits a fungicidal effect.

[0205] The fungicide for agricultural and horticultural use of the present invention can be used to control plant diseases caused by a wide range of filamentous fungi, such as those belonging to the algae (Oomycetes), ascomycetes, deuteromycetes, basidiomycetes, and zygomycetes.

[0206] Examples of plant diseases (pathogens) that are subject to control are shown below. Sugar beet: Cercospora beticola, Aphanomyces cochlioides, Root rot (Thanatephorus cucumeris), Leaf rot (Thananatephorus cucumeris), Rust (Uromyces betae), Powdery mildew (Oidium sp.), Spot disease (Ramularia beticola), Seedling damping off (Aphanomycescochlioides, Pythium ultimum) etc. Peanuts: Brown spot disease (Mycosphaerella arachidis), stain spot disease (Ascochyta sp.), rust disease (Puccinia arachidis), damping-off disease (Pythium debaryanum), rust spot disease (Alternaria alternata), white mold disease (Sclerotium rolfsii), black rot (Mycosphaerella berkeleyi), black root rot (Calonectriailicicola), etc. Cucumbers: Powdery mildew (Sphaerotheca fuliginea), downy mildew (Pseudoperonospora cubensis), vine blight (Mycosphaerellamelonis), vine wilt (Fusarium oxysporum), sclerotinia rot (Sclerotinia sclerotiorum), gray mold (Botrytiscinerea), anthracnose (Colletotrichum orbiculare), black spot (Cladosporium cucumerinum), brown spot (Corynesporacassiicola), seedling blight (Pythium debaryanum, Rhizoctonia solani Kuhn), Phomopsis root rot (Phomopsis sp.), bacterial leaf spot (Pseudomonas syringae pv. Lachrymans), etc. Tomatoes: Botrytis cinerea, Cladosporium fulvum, Phytophthorainfestans, Verticillium albo-atrum, Verticillium dahliae, Oidium neolycopersici, Alternaria solani, Pseudocercospora fuligena), bacterial wilt (Ralstonia solanacearum), sclerotinia sclerotiorum, etc. Eggplant: Gray mold (Botrytis cinerea), black blight (Corynespora melongenae), powdery mildew (Erysiphecichoracearum), sooty mold (Mycovellosiella nattrassii), sclerotinia rot (Sclerotinia sclerotiorum), verticillium wilt (Verticillium dahliae), brown spot disease (Phomopsis vexans), etc. Chili peppers: Late blight (Phytophthora capsici), gray mold (Botrytis cinerea), sclerotinia rot (Sclerotinias clerotiorum), anthracnose (Colletotrichum aenigma, Colletotrichum capsici, Colletotrichum fructicola, Colletotrichum jiangxiense), powdery mildew (Leveillula taurica), etc. Strawberries: Gray mold (Botrytis cinerea), powdery mildew (Sphaerotheca humuli), anthracnose (Colletotrichumacutatum, Colletotrichum fragariae), late blight (Phytophthora cactorum), soft rot (Rhizopusstolonifer), fusarium wilt (Fusarium oxysporum), wilt (Verticillium dahliae), sclerotinia rot (Sclerotinias clerotiorum), etc. Onions: Botrytis allii, Botrytis cinerea, Botrytis squamosa, Peronospora destructor, Phytophthoraporri, Ciborinia allii, Botrytis squamosa, Fusarium oxysporum), red root rot (Pyrenochaeta terrestris), black rot sclerotium (Sclerotiumcepivorum), rust (Puccinia allii), white silk rot (Sclerotium rolfsii), etc. Allium: soft rot (Pectobacterium carotovorum), downy mildew (Peronospora destructor), leaf blight (Pleospora allii), black rot sclerotium (Sclerotium cepivorum), rust (Puccinia allii), white spot leaf blight (Botrytis squamosa), white silk rot (Sclerotium rolfsii), red root rot (Pyrenochaeta) terrestris) etc. Cabbage: Clubroot (Plasmodiophora brassicae), soft rot (Erwinia carotovora), black rot (Xanthomonas campesrtis pv. campestris), bacterial black spot (Pseudomonas syringa pv. maculicola, P. s. pv. alisalensis), downy mildew (Peronospora parasitica), sclerotinia rot (Sclerotinias clerotiorum), sooty mold (Alternaria brassicola), gray mold (Botrytis cinerea), root rot (Phoma lingam), Pythium rot (Pythium aphanidermatum, Pythium ultimum), white rust (Albugo macrospora), etc. Lettuce: Diseases such as rot (Pseudomonas cichorii, Pseudomonas marginalis), soft rot (Pectobacterium carotovorum), downy mildew (Bremialactucae), gray mold (Botrytis cinerea), sclerotinia sclerotiorum, big-vein disease (Mirafiorilettuce big-vein ophiovirus), root rot (Fusarium oxysporum), bottom blight (Rhizoctonia solani), powdery mildew (Golovinomycesorontii), etc. Green beans: Sclerotinia sclerotiorum, gray mold (Botrytis cinerea), anthracnose (Colletotrichumlindemuthianum), horn blotch (Phaeoisariopsis griseola), etc. Peas: Brown spot disease (Mycosphaerella blight), gray mold (Botrytis cinerea), sclerotinia rot (Sclerotinias clerotiorum), powdery mildew (Erysiphe pisi), etc.

[0207] Apples: Powdery mildew (Podosphaera leucotricha), black spot (Venturia inaequalis), Monilinia mali, black spot (Mycosphaerella pomi), canker (Valsa mali), leaf spot (Alternaria mali), cedar-apple rust (Gymnosporangium yamadae), ring spot (Botryosphaeria berengeriana), anthracnose (Glomerellacingulata, Colletotrichum acutatum), brown spot (Diplocarpon mali), sooty spot (Zygophialajamaicensis), sooty mold (Gloeodes pomigena), purple root rot (Helicobasidium mompa), white root rot (Rosellinianecatrix), gray mold (Botrytis cinerea), burn (Erwinia) Diseases such as amylovora, silver leaf disease (Chondrostereum purpureum), and crown gall disease (Rhizobium radiobacter, Rhizobium rhizogenes) Japanese apricot (Ume): Black spot disease (Cladosporium carpophilum), gray mold (Botrytis cinerea), gray mold (Monilinia mumecola), sooty mold (Peltaster sp.), fruit rot (Taphrina pruni), brown hole disease (Phloeosporella padi), etc. Persimmons: Powdery mildew (Phyllactinia kakicola), anthracnose (Gloeosporium kaki), horn spot leaf spot (Cercospora kaki), round leaf spot leaf spot (Mycosphaerella nawae), gray mold (Botrytis cinerea), sooty spot (Zygophiala jamaicensis), etc. Peaches: Monilinia fructicola, Moniliafructigena, Cladosporium carpophilum, Phomopsis sp., Xanthomonas campestrispv. pruni, Taphrina deformans, Colletotrichum gloeosporioides), brown borer disease (Phloeosporellapadi), kawaratake disease (Coriolus versicolor), etc. Almonds: Gray mold (Monilinia laxa), leaf spot (Stigmina carpophila), black spot (Cladosporium carpophilum), leaf blisters (Polystigma rubrum), leaf spot disease (Alternaria alternata), anthracnose (Colletotrichum gloeospoides), etc. Cherry: Gray mold (Monilinia fructicola), anthracnose (Colletotrichum acutatum), black spot (Alternaria sp.), young fruit sclerotinia rot (Monilinia kusanoi), brown hole (Mycosphaerella cerasella), powdery mildew (Podosphaera tridactyla), etc. Grapes: Gray mold (Botrytis cinerea), powdery mildew (Uncinula necator), late blight (Glomerella cingulata, Colletotrichum acutatum), downy mildew (Plasmoparaviticola), black rot (Elsinoe ampelina), brown spot (Pseudocercospora vitis), black rot (Guignardia bidwellii), white rot (Coniella castaneicola), rust (Phakopsora ampelopsidis), white snow disease (pathogen unidentified), crown gall disease (Rhizobium radiobacter, Rhizobium vitis), etc. Pears: Black spot (Venturia nashicola), red-apple rust (Gymnosporangium asiaticum), black spot (Alternariakikuchiana), ring spot (Botryosphaeria berengeriana), powdery mildew (Phyllactinia mali), canker (Phomopsis fukushii), brown spot (Stemphylium vesicarium), anthracnose (Glomerellacingulata), etc. Tea: Ring spot disease (Pestalotiopsis longiseta, P. theae), anthracnose (Colletotrichum theae-sinensis), net blight (Exobasidium reticulatum), red blight (Pseudomonassyringae), blight (Exobasidium vexans), etc. Citrus: Scab (Elsinoe fawcettii), blue mold (Penicillium italicum), green mold (Penicillium digitatum), gray mold (Botrytis cinerea), black spot (Diaporthe citri), canker (Xanthomonascampestris pv. Citri), powdery mildew (Oidium sp.), late blight (Phytophthora citrophthora), anthracnose (Colletotrichumfioriniae), etc. Kiwifruit: Bacterial flower blight (Pseudomonas marginalis, Pseudomonas syringae, Pseudomonas viridiflava), canker (Pseudomonas syringae), gray mold (Botrytis cinerea), soft rot (Botryosphaeria dothidea, Diaporthe sp., Lasiodiplodia theobromae), sooty mold (Pseudocercosporaactinidiae), etc. Olives: Anthracnose (Colletotrichum acutatum, Colletotrichumgloeosporioides), Peacock spot (Spilocaeaoleaginea), etc. Chestnut: Anthracnose (Colletotrichum gloeosporioides), etc.

[0208] 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), snow mold (Typhula incarnata), large 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 disease (Pyricularia oryzae), sheath blight (Rhizoctonia solani), bakanae disease (Gibberella fujikuroi), sesame leaf spot (Cochliobolus miyabeanus), seedling blight (Pythium graminicola), bacterial leaf spot (Xanthomonas oryzae), bacterial seedling blight (Burkholderia plantarii), brown stripe disease (Acidovoraxavenae), bacterial grain blight (Burkholderia glumae), streaky leaf spot (Cercospora oryzae), rice blast (Ustilaginoideavirens), brown rice (Alternaria alternata, Curvularia intermedia), black-bellied rice (Alternaria padwickii), red-colored rice (Epicoccum purpurascens), etc. Tobacco: Sclerotinia sclerotiorum, powdery mildew (Erysiphe cichoracearum), plague (Phytophthoranicotianae), etc. Tulips: Gray mold (Botrytis cinerea), brown spot (Botrytis tulipae), leaf blight (Rhizoctonia solani), bulb rot (Fusarium oxysporum), skin rot (Rhizoctonia solani), etc. Roses: Black spot (Diplocarpon rosae), powdery mildew (Erysiphe simulans, Podosphaera pannosa), gray mold (Botrytis cinerea), etc. Chrysanthemums: Gray mold (Botrytis cinerea), white rust (Puccinia horiana), downy mildew (Paraperonospora minor, Peronospora danica), Pythium wilt (Pythium aphanidermatum, Pythium dissotocum, Pythium helicoides, Pythium oedochilum, Pythium sylvaticum), wilt (Rhizoctonia solani), Fusarium wilt (Fusarium solani), etc. Gerbera: Gray mold (Botrytis cinerea), powdery mildew (Podosphaera xanthii), etc. Lilies: Leaf blight (Botrytis elliptica, Pestalotiopsis sp.), gray mold (Botrytis cinerea), etc. Sunflowers: Downy mildew (Plasmopara halstedii), Sclerotinia sclerotiorum, Gray mold (Botrytiscinerea), etc. Bentgrass: Snow mold (Sclerotinia borealis), Large patch (Rhizoctonia solani), Brown patch (Rhizoctonia solani), Dollar spot (Sclerotinia homoeocarpa), Blast (Pyricularia sp.), Red blight (Pythium aphanidermatum), Anthracnose (Colletotrichum graminicola), etc. Orchardgrass: Powdery mildew (Erysiphe graminis), etc. Soybeans: Purple spot disease (Cercospora kikuchii), downy mildew (Peronospora manshurica), stem blight (Phytophthora sojae), rust (Phakopsora pachyrhizi), sclerotinia sclerotiorum, anthracnose (Colletotrichumtruncatum), gray mold (Botrytis cinerea), black rot (Elsinoe glycines), black spot (Diaporthe phaseolorum var. sojae), damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), etc. Potatoes: Late blight (Phytophthora infestans), summer blight (Alternaria solani), black spot disease (Thanatephorus cucumeris), Verticillium albo-atrum, V. dahliae, V. nigrescens, black foot disease (Pectobacterium atrosepticum), soft rot (Pectobacterium carotovorum), gray mold (Botrytiscinerea), scab (Streptomyces spp.), sclerotinia sclerotiorum, etc. Japanese yam (Dioscorea japonica): Leaf blotch (Cylindrosporium dioscoreae), anthracnose (Colletotrichum gloeosporioides), blue mold (Penicillium sclerotigenum), etc. Sweet potatoes: Purple root rot (Helicobasidium mompa), vine wilt (Fusarium oxysporum), etc. Taro: Late blight (Phytophthora colocasiae), stem rot (Rhizoctonia solani), etc. Ginger: Rhizome rot (Pythium ultimum, Pythiummyriotylum), white spot disease (Phyllosticta zingiberis), etc. Bananas: Panama disease (Fusarium oxysporum), Sigatoka disease (Mycosphaerella fijiensis, M. musicola), etc. Mango: Anthracnose (Colletotrichum aenigma), canker (Xanthomonas campestris), stem rot (Diaporthepseudophoenicicola, 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 (Peronosporaparasitica), etc. Coffee: Rust disease (Hemileia vastatrix), anthracnose (Colletotrichum coffeanum), brown eye disease (Cercosporacoffeicola), etc. Sugarcane: Brown rust disease (Puccinia melanocephala), etc. Corn: Gloeocercospora sorghi, Puccinia sorghi, Puccinia polysora, Ustilago maydis, Cochliobolusheterostrophus, Setosphaeria turcica, Damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), etc. Cotton: Seedling blight (Pythium sp.), rust (Phakopsora gossypii), white mold (Mycosphaerella areola), anthracnose (Glomerella gossypii), etc. Hops: Downy mildew (Pseudoperonospora humuli), powdery mildew (Oidium sp., Podosphaera macularis), gray mold (Botrytis cinerea), etc.

[0209] [Nematicides] The dihydropyrimidine compounds of the present invention are also excellent at controlling various nematodes that affect plant growth. The nematicidal agent of the present invention contains at least one selected from compound (II) and a salt thereof as an active ingredient. The amount of compound (II) or a salt thereof contained in the nematicidal agent of the present invention is not particularly limited as long as it exhibits a nematode control effect.

[0210] Specific examples of various plant-parasitic nematodes that can be controlled by the nematicide of the present invention are shown below. (1) Tylenchida (a) Species of the Anguinidae family, for example, Anguina spp., such as Anguina funesta and Anguina tritici; and species of the Ditylenchus spp., such as Ditylenchus destructor, Ditylenchus dipsaci, and Ditylenchus myceliophagus. (b) Species of the family Aphelenchoididae, such as the genus Aphelenchoides, including the rice stem nematode (Aphelenchoidesbesseyi), the strawberry nematode (Aphelenchoides fragariae), the leaf nematode (Aphelenchoides ritzemabosi), and the rice stem nematode (Aphelenchoidesbesseyi); and species of the genus Bursaphelenchus, including the pine wood nematode (Bursaphelenchus xylophilus); (c) Belonolaimidae family, for example, Belonolaimus spp. species such as Belonolaimus longicaudatus; Tylenchorhynchus spp. species such as Tylenchorhynchus claytoni and Tylenchorhynchus dubius; (d) A member of the family Criconematidae, for example, Criconema mutabile; (e) A member of the family Dolichodoridae, for example, Dolichodorus mediterraneus; (f) Ecphyadophoridae, for example, Ecphyadophora tenuissima (g) A species of the family Hemicycliophoridae, for example, Loofia thienemanni; (h) Species of the Heteroderidae family, for example, Globodera spp., such as potato cyst nematode (Globoderarostochiensis), potato white cyst nematode (Globodera pallida), and tobacco cyst nematode (Globodera tabacum); species of the Heterodera spp., such as wheat cyst nematode (Heterodera avenae), Heterodera cruciferae, soybean cyst nematode (Heterodera glycines), sugar beet cyst nematode (Heterodera schachtii), and clover cyst nematode (Heterodera trifolii); (i) Species of the family Hopolaimidae, for example, Helicotylenchus spp., such as Helicotylenchus dihystera and Helicotylenchus multicinctus; species of the genus Hopolaimus, such as Hopolaimus columbus and Hopolaimus galeatus; and other species such as Rotylenchus robustus and Rotylenchulus reniformis; (j) Species of the family Meloidogynidae, such as the genus Meloidogyne (Meloidogyne spp.), including Meloidogynearenaria, Meloidogyne chitwoodi, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, and Meloidogyne thamesi; (k) A member of the family Nothotylenchidae, for example, the strawberry nematode (Nothotylenchus acris); (l) Species of the genus Paratylenchus, such as Paratylenchus curvitatus and Paratylenchus elachistus, belonging to the family Paratylenchidae; (m) Species of the family Pratylenchidae, such as the genus Pratylenchus, including Pratylenchus brachyurus, Pratylenchus coffeae, Pratylenchus curvitatus, Pratylenchus fallax, Pratylenchus goodeyi, Pratylenchus neglectus, Pratylenchus spenetrans, Pratylenchus scribneri, Pratylenchus vulnus, and sorghum nematode. (Pratylenchuszeae); Other species include the false root-knot nematode (Nacobbus aberrans), the banana root-mining nematode (Radopholus similis), the citrus nematode (Tylenchulussemipenetrans), and the citrus root-mining nematode (Radopholus citrophilus).

[0211] (2) Dorylaimida (a) Longidoridae family, for example, Longidorus spp. species such as Longidoruselongates; Xipinema genus species such as Xipinema americanum, Xipinema brevicole, Xipinema index, and Xipinema diversicaudatum.

[0212] (3) Triplonchida (a) Trichodoridae family, for example, Trichodorus primitivus and Paratrichodorus minor.

[0213] [Application Method / Mixing Agent] The fungicide or nematicide for agricultural and horticultural use of the present invention is preferably used on plants such as grains, vegetables, root vegetables, potatoes, fruit trees, trees such as tea, coffee, and cocoa, pasture grasses, turfgrasses, and cotton.

[0214] The fungicide for agricultural and horticultural use of the present invention can be applied to various parts of plants, such as leaves, stems, stalks, flowers, buds, fruits, seeds, sprouts, roots, tubers, rhizomes, shoots, and cuttings. The nematicide can be applied to roots, tubers, rhizomes, etc. Furthermore, it can be used to target improved varieties, cultivars, and even mutants, hybrids, and genetically modified organisms (GMOs) of these plants.

[0215] The fungicide for agricultural and horticultural use of the present invention can be used for seed treatment, foliar application, soil application, water surface application, etc., to control various diseases occurring in agricultural and horticultural crops, including flowers, turf, and pasture grass. The nematicide can be used for seed treatment, soil application, etc.

[0216] The fungicide or nematicide for agricultural and horticultural use of the present invention may contain components other than the dihydropyrimidine compound of the present invention. Examples of other components include known carriers used for formulation. Other examples of other components include conventionally known fungicides, insecticides / acaricides, nematicides, soil pesticides, plant growth regulators, synergists, fertilizers, soil conditioners, and animal feed. The inclusion of such other components may result in synergistic effects. In other words, one embodiment of the present invention is a fungicide for agricultural and horticultural use that includes one or more further fungicides.

[0217] Specific examples of fungicides that can be mixed with or used in combination with the fungicide or nematicide of the present invention are shown below. (1) Nucleic acid biosynthesis inhibitors: (a) RNA polymerase I inhibitors: Benalaxil, Benalaxil-M, Flalaxil, Metalaxil, Metalaxil-M; Oxadixil; Clodilacon, Offrace; (b) Adenosine deaminase inhibitors: Bupirimate, dimethylmol, etylimole; (c) DNA / RNA synthesis inhibitors: Himexazole, octylinone; (d) DNA topoisomerase II inhibitor: oxolinic acid.

[0218] (2) Mitosis inhibitors and cell division inhibitors: (a) β-tubulin polymerization inhibitors: benomyl, carbendazim, chlorfenazole, fuberidazole, thiabendazole; thiophanate, thiophanate-methyl; diethofencarb; zoxamide; etaboxam; (b) Cell division inhibitor: Pencyclon; (c) Spectrin-like protein delocalization inhibitors: fluopicole, fluopimomide.

[0219] (3) Respiratory inhibitors: (a) Complex I-NADH oxidoreductase inhibitors: diflumetrim; tolfenpyrad; (b) Complex II succinate dehydrogenase inhibitors: benodanil, flutolanil, mepronil; isofetamide; fluopyram; fenflam, flumecyclox; carboxyne, oxycarboxyne; tifluzamide; benzovindiflupir, bixafen, fluxapiroxad, flametopyr, isopyrazam, penflufen, penthiopyrad, sedaxane; boscalid, pidiflumetofen, isoflusifram, pyraziflumid, impyrfluxam; (c) Complex III-ubiquinol oxidase Qo inhibitors: Azoxystrobin, chemoxystrobin, cmethoxystrobin, enoxastrobin, fluphenoxystrobin, picoxystrobin, pyraoxystrobin; pyraclostrobin, pyrametostrobin, triclopyricarb; kresoxime-methyl, trifloxystrobin; dimoxystrobin, phenaminestrobin, metminostrobin, orysastrobin; famoxadone; fluoxastrobin; fenamidon; pyribencarb; methyltetraprole; mandestrobin; (d) Complex III-ubiquinol reductase Qi inhibitors: cyazofamide; amisulbrom; fenpicoxamide; (e) Uncoupling agents for oxidative phosphorylation: Binapacril, Meptildinocap, Dinocap; Fluazinam; Felimzon; (f) Oxidative phosphorylation inhibitors (inhibitors of ATP synthase): fentin acetate, fentin chloride, fentin hydroxide; (g) ATP production inhibitor: Silthiofam; (h) Complex III: Qx (unknown) inhibitor of cytochrome bc1 (ubiquinone reductase): Ametoctrazine.

[0220] (4) Amino acids and protein synthesis inhibitors: (a) Methionine biosynthesis inhibitors: andprim, cyprodinil, mepanipyrim, pyrimethanil; (b) Protein synthesis inhibitors: blastosidine-S, kasugamycin, kasugamycin hydrochloride, streptomycin, oxytetracycline.

[0221] (5) Signal transduction inhibitors: (a) Signal transduction inhibitors: quinoxifen, proquinazide; (b) MAP histidine kinase inhibitors in osmotic signaling: fenpiclonil, fludioxonil; clozolinate, iprodione, procymidone, vinclozoline.

[0222] (6) Lipid and cell membrane synthesis inhibitors: (a) Phospholipid biosynthesis and methyltransferase inhibitors: edifenphos, iprobenphos, pyrazophos; isoprothiolane; (b) Lipid peroxidants: biphenyl, chloreneb, dichlorane, quintozen, technazen, tolclophosmethyl; etridiazole; (c) Agents that act on cell membranes: iodocarb, propamocarb, propamocarb hydrochloride, propamocarb fosetilate, prothiocarb; (d) Microorganisms that disrupt the cell membrane of pathogenic bacteria: Bacillus subtilis, Bacillus subtilis strain QST713, Bacillus subtilis strain FZB24, Bacillus subtilis strain MBI600, Bacillus subtilis strain D747; (e) Cell membrane disrupting agent: Extract of tea tree.

[0223] (7) Inhibitors of cell membrane sterol biosynthesis: (a) Inhibitors of C14 demethylation in sterol biosynthesis: Triforine; Pyriphenox, Pyrisoxazole; Fenalimol, Flurprimidol, Nualimol; Imazalil, Imazalil sulfate, Oxpoconazole, Peflazoate, Prochloraz, Triflumizole, Viniconazole; Azaconazole, Vitertanol, Bromuconazole, Cyproconazole, Diclobutrazol, Difenoconazole, Diniconazol, Diniconazol-M, Epoxyconazole Zole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafole, fluconazole, fluconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, mycrobutanil, penconazole, propiconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole; prothioconazole, voriconazole, mefentrifluconazole; (b) Inhibitors of Δ14 reductase and Δ8→Δ7-isomerase in sterol biosynthesis: algimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph; fenpropidine, piperalin; spiroxamine; (c) 3-ketoreductase inhibitors in C4 demethylation of the sterol biosynthesis pathway: fenhexamide; fenpyrazamine; (d) Squalene epoxidase inhibitors of the sterol biosynthesis pathway: pyributicarb; naphthifine, terbinafine.

[0224] (8) Cell wall synthesis inhibitors: (a) Trehalase inhibitor: validamycin; (b) Chitin synthase inhibitors: polyoxin, polyoxorim; (c) Cellulose synthase inhibitors: dimethomorph, flumorph, pyrimorph; benthiavalicarb, iproavalicarb, valifenarate; mandipropamide.

[0225] (9) Melanin biosynthesis inhibitors (a) Melanin biosynthesis reductase inhibitors: phthalide; pyroquilon; tricyclazole; (b) Inhibitors of melanin biosynthesis dehydration enzymes: carpropamide; diclocimet; phenoxanil; (c) Polyketide synthesis inhibitor of melanin biosynthesis: Tolprocarb.

[0226] (10) Resistance inducers for host plants: (a) Agents that act on the salicylic acid synthesis pathway: acibenzoral-S-methyl; (b) Others: Probenazole, thiadinil, isothianil, diclobentiazox, ipfentrifluconazole, laminarin, Japanese knotweed extract.

[0227] (11) Agents with unknown mode of action: cymoxanil, fosetyl aluminum, phosphate, tecrophthalam, triazoxide, flusulfamide, diclomedin, metasulfocarb, cyflufenamide, metraphenone, pyrophenone, dozin, dozin free base, fluthianil.

[0228] (12) Agents with multiple sites of action: copper (copper salts), Bordeaux mixture, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide; Farbam, Mancozeb, Maneb, Mancapper, Methylam, polycarbamate, propineb, Thiram, Zineb, Ziram; Captan, Captahol, Forpet; Chlorothalonil; Diclofluanide, Tollfluanide; Guazatine, Guazatine acetate, Iminoctadine triacetate, Iminoctadine trialbesilate; Anilazine; Dithianone; Quinomethionate; Fluorimide.

[0229] (13) Other agents: DBEDC, fluoroforpet, bis(8-quinolinolate)copper(II), propamidine, chloropicrin, cyproflam, agrobacterium, bethoxazine, diphenylamine, methylisothianate (MITC), mildeomycin, capsaicin, cufraneb, cyprosulfamide, dazomet, debacarb, dichlorophene, diphenzoquat, diphenzoquat methylsulfonate, flumetbel, fosetyl calcium, fosetyl sodium, irumamycin, natamycin, nitrotar isopropyl, oxamocarb, pyrrolnitrin, tebufloxin, torniphanide, zarilamid, algophase, amicalthiazole (Amic Arthiazol, oxathiapiprolin, fluoxapiprolin, zinc methylam, benthazole, triclamide, uniconazole, oxyfenthiin, picarbutrazox, quinofumelin, florylpicoxamid, pyrapropoyne, fluindapyr, aminopyrifen, pyridaclomethyl, ipflufenoquin, dipimethitron.

[0230] Specific examples of insecticides, acaricides, nematicides, soil pesticides, and insecticides that can be mixed with or used in combination with the fungicide or nematicide of the present invention are shown below. (1A) Acetylcholinesterase (AChE) inhibitors (carbamates): Aranicarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxime, Butoxycarboxime, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Phenobucarb, Formetanate, Frathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pyrimikab, Propoxul, Thiodicarb, Thiofanox, Triazamate, Trimetacarb, XMC, Xylylcarb.

[0231] (1B) Acetylcholinesterase (AChE) inhibitors (organophosphates): Acephate, Azamethiphos, Adinphos-ethyl, Adinphos-methyl, Kazsaphos, Chloretoxyphos, Chlorfenvinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Dimeton-S-methyl, Diazinon, Dichlorvos, Diclotophos, Dimethoate, Dimethylvinphos, Disulfon, EPN, Ethion, Etoprophos, Fanflu, Phenamiphos, Fenitrothion, Fenthion, Fostiazate, Heptenophos, Imisiaphos, Isofenphos, Isopropyl-O-(methoxyaminothiophosphoryl) Salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monoclotophos, naled, omethoate, oxydimeton methyl, parathion, parathion methyl, fenthoate, phosalon, phosmet, phosphamidone, foxim, pyrimiphos methyl, profenophos, propetamphos, prothiophos, pyraclophos, pyridafenthion, quinalphos, sulfotep, tebupyrimphos, temephos, terbuphos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, bamidothion.

[0232] (2) GABAergic chloride ion channel blockers: Chlordane, endosulfan; ethiprole, fipronil. Flufiprol. (3A) Sodium channel modulator (pyrethroid type): Acrinatrin, allethrin, d-cis-trans-allethrin, d-trans-allethrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentenyl-isomer, biorethmetrin, cycloprothrin, cyfluthrin, β-cyfluthrin, cyhalothrin, λ-cyhalothrin, γ-cyhalothrin, cypermethrin, α-cypermethrin, β-cypermethrin, θ-cypermethrin, ζ-cypermethrin, cyphenothrin [(1R)-trans isomer], deltamethrin, ene Penthrin [(EZ)-(1R)-isomer], esfenvalerate, etofenprox, fenpropatrin, fenvalerate, flucitrinate, flumethrin, τ-fluvalinate, halfenprox, imiprithrin, cadesrin, permethrin, phenothrin [(1R)-trans isomer], prallethrin, pyrethrin, resmethrin, silafluofen, tefluthrin, tetramesrin, tetramesrin [(1R)-isomer], tralomethrin, transfluthrin. κ-Bifenthrin, Chloroplatrethrin, Heptafluthrin, Meperfluthrin, ε-Metofluthrin, Monfluorothrin, ε-Monfluorothrin, κ-Tefluthrin, Tetramethylfluthrin; Bioetanomethrin. (3B) Sodium channel modulators (DDTs): DDT, methoxychloride.

[0233] (4) Nicotinic acetylcholine receptor (nAChR) competitive modulators: Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam; nicotine; sulfoxaflor; flupyradiflon; triflumezopyrim. Dichloromesothiaz, flupyrimine. (5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators: Spinetram, Spinosad. (6) Glutamate-mediated chloride ion (chloride ion) channel (GluCl) allosteric modulator: Abamectin, emamectin, emamectin benzoate, lepimectin, milbemectin. Doramectin, eprinomectin, ivermectin, moxidectin, selamectin. (7) Juvenile hormone analogues: Hydroprene, quinoprene, methoprene; phenoxycarb; pyriproxyfen. (8) Other nonspecific (multisite) inhibitors: Methyl bromide, alkyl halides; chloropicrin; sodium aluminum fluoride, sulfuryl fluoride; borax, boric acid, disodium octaborate, sodium borate, sodium metaborate; tartaric acid; dazomet, metam, potassium metam, sodium metam. (9) String organ TRPV channel modulator: Pymetrozine, pyrifluquinazone; afidopiropen.

[0234] (10) Mite growth inhibitors: Clofentezine, diflovidazine, hexythiazox; etoxazole. (11) Microbial-derived insect midgut endometrium disruptors: Bt subsp. israelensis, Bt subsp. aizawai, Bt subsp. kurstaki, Bt subsp. tenebrionis; Proteins contained in Bt crops: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1; Bacillus sphaericus. (12) Mitochondrial ATP synthase inhibitors: Diafenthiurone; azocyclotin, cyhexatin, fenbutatin oxide; propargit; tetradiphon. (13) Oxidative phosphorylation uncoupling agents that disrupt the proton gradient: Chlorfenapir, DNOC, sulfurmid. (14) Nicotinic acetylcholine receptor (nAChR) channel blockers: Bensultap, cartap hydrochloride, thiocyclam, thiosultap sodium salt. (15) Chitin biosynthesis inhibitors, type 0: Bistriflurone, Chlorfluazulone, Diflubenzuron, Flucycloxron, Flufenoxron, Hexaflumurone, Lufenuron, Novalon, Noviflumurone, Teflubenzuron, Triflumurone. (16) Chitin biosynthesis inhibitors, type 1: Buprofezin. (17) Molting inhibitors: Shiromazine. (18) Ecdysone receptor agonists: Chromafenozide, halofenozide, methoxyfenozide, tebufenozide. (19) Octopamine receptor agonists: Amitraz.

[0235] (20) Mitochondrial electron transport chain complex III inhibitors: Hydramethylnon; acequinosyl; fluacrypyrim; bifenazate. (21) Mitochondrial electron transport chain complex I inhibitors (METI): Phenazaquine, fenpyroximate, pyridaben, pyrimidifen, tebufenpyrad, tolfenpyrad; rotenone. (22) Voltage-gated sodium channel blockers: Indoxacarb; metaflumizone. (23) Acetyl-CoA carboxylase inhibitors: Spirodiclofen, spiromesifen, spirotetramat. Spiropidione. (24) Mitochondrial electron transport chain complex IV inhibitors: Aluminum phosphide, calcium phosphide, zinc phosphide, phosphine; calcium cyanide, sodium cyanide, potassium cyanide. (25) Mitochondrial electron transport chain complex II inhibitors: Cyenopyrafen, cyflumetofen; Piflubumid. (28) ryanodine receptor modulators: Chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide. Cyhalodiamide, tetrachlorantraniliprole, tetraniliprole. (29) Chord tone organ modulator Target region unspecified: Floricamide. (30) GABAergic chloride ion channel allosteric modulator: Broflanilide, fluxamethamide. Isocycloceramic; afoxolaner, fluralaner, rotineral, sarolaner. Other insecticides and acaricides: Azadirachtin, benzoximate, bromopropylate, quinomethionate, dicofor, lime sulfur mixture, mancozeb, pyridaryl, sulfur. Acinonapil, benzpyrimoxane, flomethquin, fluhexafone, oxazosulfyl, ticlopyrazoflor.

[0236] Insecticide: (a) Benzimidazole derivatives: fenbendazole, albendazole, triclabendazole, oxybendazole, mebendazole, oxfendazole, perbendazole, flubendazole; febantel, netobimin, thiophanate; thiabendazole, cambendazole; (b) Salicylanilide derivatives: Closantel, oxyclozanide, lafoxanide, niclosamide; (c) Substituted phenols: nitroxynyl, nitroscanate; (d) Pyrimidines: pyrantel, morantel; (e) Imidazothiazole derivatives: Lebamisol, Tetramisol; (f) Tetrahydropyrimidine derivatives: praziquantel, epsiplantel; (g) Other anthelmintics: cyclodiene, liania, chlorthrone, metronidazole, demiditraz; piperazine, diethylcarbamazine, dichlorophene, monepantel, tripenzimidine, amidantel; thiaacetalsamide, melarsomine, arsenamide.

[0237] Specific examples of plant growth regulators that can be mixed with or used in combination with the fungicide or nematicide for agricultural and horticultural use of the present invention are shown below. Abscisic acid, kinetin, benzylaminopurine, 1,3-diphenylurea, forchlorfenuron, thidiazurone, chlorfenuron, dihydrozeatin, gibberellin A, gibberellin A4, gibberellin A7, gibberellin A3, 1-methylcyclopropane, N-acetylaminoethoxyvinylglycine (also known as abiglycine), aminooxyacetic acid, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyric acid, dichlorprop, f Enothiol, 1-naphthylacetamide, eticlozate, cloxyfonac, maleate hydrazide, 2,3,5-triiodobenzoic acid, salicylic acid, methyl salicylate, (-)-jasmonic acid, methyl jasmonate, (+)-strigol, (+)-deoxystrigol, (+)-orobancol, (+)-solgolactone, 4-oxo-4-(2-phenylethyl)aminobutyric acid; etephon, chlormecoat, mepicote chloride, benzyladenine, 5-aminolevulinic acid.

[0238] [Pharmaceutical formulation] The fungicide or nematicide for agricultural and horticultural use of the present invention is not particularly limited by its dosage form. For example, dosage forms such as wettable powders, emulsions, powders, granules, water-soluble powders, suspensions, granular wettable powders, and tablets can be used. The method of preparing the formulation is not particularly limited, and known preparation methods can be used depending on the dosage form. The following are some examples of formulations. The formulations shown below are merely illustrative and can be modified as long as they do not contradict the spirit of the present invention. The present invention is not limited in any way by the following formulation examples. Unless otherwise specified, "parts" means "parts by weight."

[0239] (Example of formulation 1: Wettable powder) Forty parts of the dihydropyrimidine compound of the present invention, 53 parts of diatomaceous earth, 4 parts of a higher alcohol sulfate ester, and 3 parts of an alkylnaphthalene sulfonate are uniformly mixed and finely ground to obtain a wettable powder with an active ingredient content of 40%. (Formulation example 2: Emulsion) A mixture of 30 parts of the dihydropyrimidine compound of the present invention, 33 parts of xylene, 30 parts of dimethylformamide, and 7 parts of polyoxyethylene alkyl allyl ether is dissolved to obtain an emulsion containing 30% of the active ingredient. (Formulation example 3: Granules) Five parts of the dihydropyrimidine compound of the present invention, forty parts of talc, thirty-eight parts of clay, ten parts of bentonite, and seven parts of alkyl sodium sulfate are uniformly mixed, finely ground, and then granulated to a particle diameter of 0.5 to 1.0 mm to obtain granules containing 5% of the active ingredient. (Formulation example 4: Granules) Five parts of the dihydropyrimidine compound of the present invention, seventy-three parts of clay, twenty-tenths of bentonite, one part of sodium dioctyl sulfosuccinate, and one part of potassium phosphate were uniformly mixed and pulverized. Water was added to this mixture and kneaded thoroughly. Then, the mixture was granulated and dried to obtain granules containing 5% of the active ingredient. (Formulation example 5: Suspension) Ten parts of the dihydropyrimidine compound of the present invention, four parts of polyoxyethylene alkyl allyl ether, two parts of sodium polycarboxylate, ten parts of glycerin, 0.2 parts of xanthan gum, and 73.8 parts of water are mixed and wet-ground until the particle size is 3 microns or less to obtain a suspension containing 10% of the active ingredient. (Formulation example 6: Granular wettable powder) Forty parts of the dihydropyrimidine compound of the present invention, 36 parts of clay, 10 parts of potassium chloride, 1 part of sodium alkylbenzene sulfonate, 8 parts of sodium lignin sulfonate, and 5 parts of formaldehyde condensate of sodium alkylbenzene sulfonate are uniformly mixed and finely ground, then an appropriate amount of water is added and kneaded to form a clay-like substance. The clay-like substance is granulated and then dried to obtain a granular wettable powder containing 40% of the active ingredient.

[0240] [Medical and veterinary antifungal agents] The dihydropyrimidine compounds of the present invention can be used as preventive and therapeutic agents for controlling harmful pathogens, particularly fungi, that infect humans or animals. The medical and veterinary antifungal agent of the present invention contains at least one selected from compound (II) and its salts as an active ingredient. The amount of compound (II) or its salt contained in the medical antifungal agent of the present invention is not particularly limited as long as it exhibits antifungal effects.

[0241] In this specification, "animal" refers to vertebrates (Vertebrata) such as pets, livestock, poultry, exhibit animals kept in zoos and aquariums, captured wild animals, and research and experimental animals.

[0242] For example, the following animals are listed, but the specific examples of animals are not limited to these. Mammals such as sheep, goats, pigs, horses, cows, water buffalo, donkeys, mules, camels, llamas, alpacas, wild boars, reindeer, deer, minks, elephants, bears, kangaroos, foxes, dogs, cats, squirrels, rabbits, mice, rats, guinea pigs, hamsters, monkeys, and ferrets. Birds such as pigeons, parakeets, parrots, finches, zebra finches, canaries, chickens, ducks, turkeys, geese, peacocks, ostriches, swans, sparrows, quail, owls, eagles, hawks, and cormorants. Reptiles such as chameleons, iguanas, lizards, snakes, turtles, crocodiles, and geckos. Amphibians such as frogs and newts. Fish such as carp, goldfish, medaka, tropical fish, yellowtail, sea bream, greater amberjack, salmon, mackerel, sea bass, grouper, tuna, horse mackerel, flounder, and pufferfish.

[0243] Examples of fungi (molds) that can be treated with the medical and veterinary antifungal agents of the present invention are listed below. However, these are not the only examples. For example, the genera Absidia (such as absidia corymbifera); Acremonium; Alternaria (such as Alternaria alternata); Aspergillus (such as Aspergillus flavus, Aspergillus fumigatus, Aspergillus nidulans, Aspergillus niger, Aspergillus parasiticus, Aspergillus terreus); Bipolaris; Blastomyces (such as Blastomyces dermatitidis); Blumeria (such as Blumeria graminis); Candida (such as Candida albicans, Candida glabrata, Candida krusei, Candida parapsilosis, Candida tropicalis); Cladosporium (such as Cladosporium cladosporoides, Cladosporium herbarium); Coccidioides (such as Coccidioides immitis, Coccidioides posadasii); Colletotrichium trifolii The genera Colletotrichium, Cryptococcus, Curvularia, Encephalitozoon, Encephalitozoon cuniculi, Epicoccum, Epidermophyton, Exophiala, Exserohilum, Fusarium, Fusarium graminarium, Fusarium solani, Fusarium sporotrichoides, Fonsecaea, Histoplasma, Histoplasma capsulatum;The genera Leptosphaeria (e.g., Leptosphaeria nodorum), Malassezia (e.g., Malassezia globosa), Microsporum (e.g., Microsporum canis), Mycosphaerella (e.g., Mycosphaerella graminicola), Neurospora, Paecilomyces (e.g., Paecilomyces lilanicus, Paecilomyces varioti), Penicillium (e.g., Penicillium chrysogenum), Phytophthora (e.g., Phytophthora capsici, Phytophthora infestans), Plasmopara (e.g., Plasmopara viticola), Pneumocystis (e.g., Pneumocystis jirovecii), Pyricularia (e.g., Pyricularia oryzae), Pythium (e.g., Pythium ultimum), Puccinia (e.g., Puccinia coronata, Puccinia graminis), and Rhizoctonia The genera Rhizoctonia (e.g., solani), Rhizomucor, Scedosporium (e.g., Fusarium apiospermum, Scedosporium prolificans), Scopulariopsis (e.g., Scopulariopsis brevicaulis), Sporothrix (e.g., Sporothrix schenckii), Talaromyces (e.g., Talaromyces marneffei), Trichophyton (e.g., Trichophyton mentagrophytes, Trichophyton interdigitale, Trichophyton rubrum, Trichophyton tonsurans, Trichophyton verrucosum), Trichophyton (e.g., Trichosporonasahii, Trichosporon beigelii), Ustilago, etc. Among these, the antifungal agent of the present invention is suitable against the genera Aspergillus, Trichophyton, or Candida, and is particularly suitable against Aspergillus fumigatus or Trichophyton tonsurans.

[0244] Examples of fungal infections to which the medical and veterinary antifungal agents of the present invention can be applied are listed below. However, these are not the only examples.

[0245] The medical and veterinary antifungal agents of the present invention can be applied to both systemic fungal infections and superficial fungal infections. Specific examples of fungal infections include aspergillosis (such as pulmonary aspergillosis and systemic aspergillosis, which is more likely to occur in immunosuppressed patients such as bone marrow recipients or AIDS patients), candidiasis (such as systemic candidiasis), cryptococcal meningitis, rhinocerebral mucomycosis, pulmonary mucormycosis, blastomycosis, histoplasmosis, coccidiomycosis, paracoccidiomycosis, lobomycosis, keratomycosis, sporotrichumosis, chromoblastomycosis, chromomycosis, pheophifomycosis, zygomycosis, cryptococcosis, disseminated sporotrichumosis, and tinea (ring). Examples include tinea capitis (worm), tinea capitis (ringworm), tinea corporis (ringworm), tinea cruris (jock itch), tinea pedis (athlete's foot), onychomycosis (nail fungus), candidiasis of the skin, mouth, or vagina, Malassezia infection, chronic mucocutaneous candidiasis, Pneumocystis pneumonia, and penicillium malnefei. Furthermore, the antifungal agent of the present invention is also applicable to allergic diseases caused by fungi, such as allergic bronchopulmonary asthma (ABPA); asthma, rhinosinusitis, or sinusitis.

[0246] The medical and veterinary antifungal agents of the present invention may contain pharmaceutically acceptable excipients. The excipients are not particularly limited as long as they are used in known medical agents. These excipients are, of course, sterile and non-pyrogenic. Furthermore, the excipients can be appropriately selected depending on the dosage form and administration method of the antifungal agent.

[0247] The dosage forms of the medical and veterinary antifungal agents of the present invention are not particularly limited and include solid preparations such as tablets, powders, granules, capsules, lozenges, and pellets; liquid preparations such as syrups, emulsions, suspensions, solutions, pour-on preparations, and spot-on preparations; semi-solid preparations such as ointments and gels; gaseous preparations such as aerosols and vapors; and nanoparticle formulations. The medical antifungal agent of the present invention can be administered by known methods. Examples of administration methods include injection (subcutaneous, intravenous, intramuscular, intrasternal, etc.); transdermal administration such as insertion into the anus or vagina, application or spraying to the skin surface, or dripping; oral administration such as swallowing by mouth; and nasal administration by inhalation.

[0248] In the case of solid formulations for oral administration, examples of additives that can be used in the medical and veterinary antifungal agents of the present invention include: solubilizers such as cyclodextrin or modified cyclodextrin; diluents such as lactose, dextrose, saccharose, cellulose, corn starch, or potato starch; lubricants such as silica, talc, stearic acid, magnesium stearate, or calcium stearate, or polyethylene glycol; binders such as starch, arabic gum, gelatin, methylcellulose, carboxymethylcellulose, or polyvinylpyrrolidone; disaggregating agents such as starch, alginic acid, alginate, or sodium starch glycolate; effervescing mixtures; colorants; sweeteners; wetting agents such as lecithin, polysorbate, or lauryl sulfate; or non-toxic and pharmacologically inactive substances generally used in pharmaceutical formulations. These additives can be incorporated into the medical antifungal agent of the present invention by known methods such as mixing, granulation, tableting, sugar coating, or film coating.

[0249] In the case of liquid formulations for oral administration, examples of additives that can be used in the medical and veterinary antifungal agents of the present invention include solubilizers such as cyclodextrin or modified cyclodextrin, saccharose, glycerin, mannitol, sorbitol, natural gum, agar, sodium alginate, pectin, methylcellulose, carboxymethylcellulose, or polyvinyl alcohol.

[0250] For liquid formulations intended for intramuscular injection, suitable additives for use in the medical and veterinary antifungal agents of the present invention include sterile water, olive oil, ethyl oleate, glycols such as propylene glycol, cyclodextrin, modified cyclodextrin, and other solubilizers. Furthermore, an appropriate amount of lidocaine hydrochloride may be added as needed.

[0251] For liquid formulations intended for intravenous injection, examples of additives that can be used in the medical and veterinary antifungal agents of the present invention include carriers such as sterile water; and solubilizers such as cyclodextrin and modified cyclodextrin. These can also be included in the form of a sterile isotonic saline solution.

[0252] The amount of compound (II) or its salt contained in the medical and veterinary antifungal agent of the present invention is preferably 85% by weight or less, more preferably 50% by weight or less, relative to the weight of the antifungal agent. The dosage of the medical and veterinary antifungal agent of the present invention can be appropriately selected depending on the method of administration, the type of fungus causing the infection, the patient's age, weight, symptoms, etc. For example, for adults, when administered orally or parenterally (by injection, intravenous drip, etc.), it can be administered once or several times a day at a dose of 0.1 to 100 mg / kg-body weight. Furthermore, the medical and veterinary antifungal agents of the present invention can be used in combination with other agents other than compound (II).

[0253] Next, the present invention will be described in more detail by showing examples of synthesis. However, the present invention is not limited in any way by the following examples of synthesis. [Example 1] Synthesis of 2-(3-(2-(2-cyanoethoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-5-((isopropoxyimino)methyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)-N-isopropylpropanamide (compound number A-14) (Process 1) Synthesis of 2-(5-(((tert-butyldimethylsilyl)oxy)methyl)-3-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)-N-isopropylpropanamide

[0254] [ka]

[0255] 5-(((tert-butyldimethylsilyl)oxy)methyl)pyrimidine-2,4(1H,3H)-dione (1.50 g) was dissolved in N,N-dimethylformamide (60 ml), and under ice cooling, potassium carbonate (0.81 g) and 2-bromo-5'-fluoro-2'-methoxyacetophenone (1.45 g) were added, and the mixture was stirred at room temperature for 3 hours. Water was added to the reaction mixture, and the resulting solid was filtered. The resulting solid was dissolved in N,N-dimethylformamide (60 ml), potassium carbonate (0.98 g) and 2-bromo-N-isopropylpropanamide (1.40 g) were added, and the mixture was stirred overnight at 45°C. Water was added to the reaction mixture, extracted with ethyl acetate, washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was removed by reduced pressure distillation, and the resulting residue was purified by silica gel column chromatography (eluent: hexane / ethyl acetate) to obtain 2.13 g of the target compound. Yield: 68% The obtained target 1 The H-NMR spectrum is shown below. 1 H-NMR (CDCl3) δ: 7.63-6.97 (3H, m), 7.08 (1H, s),5.47-5.01 (4H, m), 4.54 (2H,s), 4.10-4.03 (1H, m), 3.98 (3H, s), 1.61(3H, d),1.12 (6H, d), 0.91(9H, s), 0.12(6H, s) (Process 2) Synthesis of 2-(5-(((tert-butyldimethylsilyl)oxy)methyl)-3-(2-(2-cyanoethoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)-N-isopropylpropanamide

[0256] [ka]

[0257] 0.15 g of 2-(5-(((tert-butyldimethylsilyl)oxy)methyl)-3-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)-N-isopropylpropanamide was dissolved in 1.5 ml of methanol and 1.5 ml of tetrahydrofuran, and under ice cooling, sodium borohydride (12 mg) was added and the mixture was stirred for 1 hour. Saturated ammonium chloride aqueous solution was added to the reaction mixture, extracted with ethyl acetate, washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was dissolved in tetrahydrofuran (1.5 ml). Acrylonitrile (0.2 g) and 40% potassium hydroxide aqueous solution (0.1 ml) were added, and the mixture was stirred overnight at room temperature. Water was added to the reaction mixture, extracted with chloroform, and then dried over anhydrous sodium sulfate. The solvent was removed by reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: hexane / ethyl acetate) to obtain 0.08 g of the target compound. Yield: 48% The obtained target 1 The H-NMR spectrum is shown below. 1 H-NMR (CDCl3) δ: 7.19-6.82 (4H, m), 5.82-5.07 (3H, m),4.49 (2H, s), 4.20-3.41(5H, m), 3.82 (3H, s), 2.53(2H, t), 1.55(3H, d),1.12(6H, d), 0.91(9H, s), 0.12(6H, s) (Step 3) Synthesis of 2-(3-(2-(2-cyanoethoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-5-((isopropoxyimino)methyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)-N-isopropylpropanamide

[0258] [ka]

[0259] 2-(5-(((tert-butyldimethylsilyl)oxy)methyl)-3-(2-(2-cyanoethoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)-N-isopropylpropanamide (2.00 g) was dissolved in tetrahydrofuran (8 ml) and water (8 ml), acetic acid (20 ml) was added, and the mixture was stirred at room temperature for 7 hours. Water was added to the reaction mixture, extracted with ethyl acetate, washed with saturated sodium bicarbonate aqueous solution and saturated brine, and then dried with anhydrous sodium sulfate. The solvent was removed by vacuum distillation, and the resulting residue was dissolved in chloroform (80 ml), manganese dioxide (2.00 g) was added, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was filtered, and the mother liquor was concentrated. The resulting residue was dissolved in chloroform (20 ml) and ethanol (20 ml). At room temperature, pyridine (0.40 g) and isopropoxyamine hydrochloride (0.6 g) were added, and the mixture was stirred for 30 minutes. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate) to obtain 1.26 g of the target compound (E:Z = 1:1). Yield: 70% The obtained target 1 The H-NMR spectrum is shown below. 1H-NMR (CDCl3) δ: 8.84-7.51(2H, m) 7.14-6.80(3H, m),5.85-5.07 (3H, m), 4.40-3.41 (6H, m), 3.82 (3H, s), 2.65-2.51(2H, m), 1.55(3H,d), 1.29-1.13(12H, m)

[0260] [Example 2] Synthesis of N-(2-(3-(2-(2-cyanoethoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-5-(1-(ethoxyimino)ethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)ethyl)isobutyramide (compound number A-38) (Process 1) Synthesis of tert-butyl(2-(5-acetyl-3-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)ethyl)carbamate

[0261] [ka]

[0262] 5-acetyluracil (2.50 g) was dissolved in N,N-dimethylformamide (80 ml), and under ice cooling, potassium carbonate (2.20 g) and 2-bromo-5'-fluoro-2'-methoxyacetophenone (4.00 g) were added, and the mixture was stirred at room temperature for 3 hours. Water was added to the reaction mixture, and the resulting solid was filtered. The resulting solid was dissolved in N,N-dimethylformamide (120 ml), potassium carbonate (2.40 g) and tert-butyl N-(2-bromoethyl)carbamate (4.80 g) were added, and the mixture was stirred at 80°C for 5 hours. Water was added to the reaction mixture, extracted with ethyl acetate, washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was removed by reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: chloroform / ethyl acetate) to obtain 4.60 g of the target compound. Yield: 61% The obtained target 1 The H-NMR spectrum is shown below. 1 H-NMR (CDCl3) δ: 8.09 (1H, s), 7.64-6.99 (3H, m), 5.21(2H, s), 4.87 (1H, m), 4.17-3.42 (4H, m), 4.00 (3H, s), 2.65(3H, s), 1.40 (9H,s) (Process 2) Synthesis of N-(2-(5-acetyl-3-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)ethyl)isobutyramide

[0263] [ka]

[0264] 1.60 g of tert-butyl(2-(5-acetyl-3-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)ethyl)carbamate was dissolved in 50 ml of 1,4-dioxane, 15 ml of 4 N hydrogen chloride / 1,4-dioxane solution was added, and the mixture was stirred at room temperature for 8 hours. The reaction mixture was concentrated, and the resulting residue was dissolved in methylene chloride (50 ml). Triethylamine (1.5 ml) and isobutyrate chloride (0.7 ml) were added, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: chloroform / ethyl acetate) to obtain 0.95 g of the target compound. Yield: 64% The obtained target 1 The H-NMR spectrum is shown below. 1 H-NMR (CDCl3) δ: 8.10 (1H, s), 7.64-7.00 (3H, m), 6.00(1H, m), 5.21(2H, s), 4.22-3.57 (4H, m), 4.00 (3H, s), 2.64(3H, s), 2.34-2.27(1H,m), 1.10 (6H,d) (Step 3) Synthesis of N-(2-(5-(1-(ethoxyimino)ethyl)-3-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)ethyl)isobutyramide (compound number A-36)

[0265] [ka]

[0266] N-(2-(5-acetyl-3-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)ethyl)isobutyramide (0.50 g) was dissolved in chloroform (8 ml) and ethanol (8 ml), and pyridine (0.10 g) and ethoxyamine hydrochloride (0.12 g) were added at room temperature and the mixture was stirred for 3 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate) to obtain 0.45 g of the target compound. Yield: 82% The obtained target 1 The H-NMR spectrum is shown below. 1H-NMR (CDCl3) δ: 7.64-7.00 (3H, m), 7.33(1H, s), 6.15(1H, m),5.13 (2H, s), 4.20-3.53 (6H, m), 3.99 (3H, s), 2.34-2.27(1H, m),2.19(3H, s), 1.27(3H, t), 1.10 (6H, d) (Step 4) Synthesis of N-(2-(5-(1-(ethoxyimino)ethyl)-3-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)ethyl)isobutyramide (Compound No. A-37)

[0267] [ka]

[0268] N-(2-(5-(1-(ethoxyimino)ethyl)-3-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)ethyl)isobutyramide (0.25 g) was dissolved in methanol (4 ml) and tetrahydrofuran (4 ml), and under ice cooling, sodium borohydride (20 mg) was added and the mixture was stirred for 30 minutes. A saturated ammonium chloride aqueous solution was added to the reaction mixture, extracted with ethyl acetate, washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate) to obtain 0.25 g of the target compound. Yield: 99% The obtained target 1 The H-NMR spectrum is shown below. 1H-NMR (CDCl3) δ: 7.40(1H, s),7.35-6.80 (3H, m),5.90-5.48 (2H, m), 4.44-3.24 (9H, m), 3.85 (3H, s), 2.34-2.27(1H, m), 2.14(3H,s), 1.27(3H, t), 1.10 (6H, d) (Step 5) Synthesis of N-(2-(3-(2-(2-cyanoethoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-5-(1-(ethoxyimino)ethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)ethyl)isobutyramide

[0269] [ka]

[0270] N-(2-(5-(1-(ethoxyimino)ethyl)-3-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)ethyl)isobutyramide (0.23 g) was dissolved in tetrahydrofuran (4 ml), acrylonitrile (0.27 g) and 40% potassium hydroxide aqueous solution (0.3 ml) were added, and the mixture was stirred overnight at room temperature. Water was added to the reaction mixture, extracted with chloroform, and then dried over anhydrous sodium sulfate. The solvent was removed by reduced pressure distillation, and the resulting residue was purified by silica gel column chromatography (eluent: hexane / ethyl acetate) to obtain 0.12 g of the target compound. Yield: 47% The obtained target 1 The H-NMR spectrum is shown below. 1H-NMR (CDCl3) δ: 7.46(1H, s),7.15-6.83 (3H, m),6.28-5.18 (2H, m), 4.32-3.48 (10H, m), 3.84 (3H, s), 2.64(2H, t), 2.34-2.27(1H, m), 2.16(3H, s), 1.30(3H, t), 1.10 (6H, d)

[0271] [Example 3] Synthesis of N-((2S)-1-(3-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-5-((E)-1-(isopropoxyimino)ethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)propan-2-yl)isobutyramide (compound numbers A-74 and A-75) (Process 1) Synthesis of (E)-5-(1-(isopropoxyimino)ethyl)pyrimidine-2,4(1H,3H)-dione

[0272] [ka]

[0273] 5-acetylpyrimidine-2,4(1H,3H)-dione (15.4g) was dissolved in ethanol (200ml) and chloroform (100ml), 2-(aminooxy)propane hydrochloride (14.0g) was added, and the mixture was stirred at 45°C for 3 hours. Water was added to the reaction mixture, extracted with methylene chloride, and then dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain 20.6 g of the target compound. Yield: 98% The obtained target 1 The H-NMR spectrum is shown below. 1H-NMR (DMSO-D6) δ: 11.26 (1H, s), 11.11 (1H, d, J = 5.9Hz), 7.42 (1H, d, J = 5.9 Hz), 4.31-4.25 (1H, m), 1.99 (3H, s), 1.20 (6H, d, J=6.3 Hz). (Process 2) Synthesis of (E)-1-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-5-(1-(isopropoxyimino)ethyl)pyrimidine-2,4(1H,3H)-dione (production intermediate 7)

[0274] [ka]

[0275] (E)-5-(1-(isopropoxyimino)ethyl)pyrimidine-2,4(1H,3H)-dione (2.11 g) was dissolved in N,N-dimethylformamide (30 ml), potassium carbonate (1.50 g) and 2-bromo-5'-fluoro-2'-methoxyacetophenone (2.55 g) were added, and the mixture was stirred at room temperature for 3 hours. Water was added to the reaction mixture, and the resulting solid was filtered to obtain 3.39 g of the target product. Yield: 90% The obtained target 1 The H-NMR spectrum is shown below. 1 H-NMR (CDCl3) δ: 8.23 ​​(1H, s), 7.67-6.98(3H, m),7.34(1H, s), 5.13(2H, s), 4.35-4.32 (1H, m), 3.98(3H, s), 2.19 (3H, s), 1.25(6H, d, J = 6.3 Hz). (Step 3) Synthesis of (S,E)-N-(1-(3-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-5-(1-(isopropoxyimino)ethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)propan-2-yl)isobutyramide (compound number C-221)

[0276] [ka]

[0277] (E)-1-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-5-(1-(isopropoxyimino)ethyl)pyrimidine-2,4(1H,3H)-dione (0.56 g) was dissolved in tetrahydrofuran (7 ml), and tert-butyl (S)-(1-hydroxypropan-2-yl)carbamate (0.38 g), triphenylphosphine (0.58 g), and bis(2-methoxyethyl) azodicarboxylate (0.52 g) were added, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was purified by silica gel column chromatography (eluent: hexane / ethyl acetate). The resulting solution was dissolved in 1,4-dioxane (7 ml), and 4 N hydrogen chloride / 1,4-dioxane solution (7 ml) was added. The mixture was stirred at room temperature for 4 hours. The reaction mixture was concentrated, and the resulting residue was dissolved in methylene chloride (7 ml). Under ice cooling, triethylamine (3 ml) and isobutanoyl chloride (0.1 ml) were added, and the mixture was stirred for 30 minutes. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: chloroform / ethyl acetate) to obtain 0.45 g of the target compound. Yield: 60% The obtained target 1 The H-NMR spectrum is shown below. 1H-NMR (CDCl3) δ: 7.62-6.99 (3H, m), 7.30(1H, s), 6.08-2.20(8H, m), 3.98 (3H, s),2.15(3H, s), 1.25-1.03 (15H, m) (Step 4) Synthesis of N-((2S)-1-(3-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-5-((E)-1-(isopropoxyimino)ethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)propan-2-yl)isobutyramide (compound numbers A-74 and A-75)

[0278] [ka]

[0279] (S,E)-N-(1-(3-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-5-(1-(isopropoxyimino)ethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)propan-2-yl)isobutyramide (0.25 g) was dissolved in methanol (2 ml) and tetrahydrofuran (2 ml), and under ice cooling, sodium borohydride (18 mg) was added and the mixture was stirred for 20 minutes. A saturated aqueous solution of ammonium chloride was added to the reaction mixture, extracted with ethyl acetate, washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was removed by vacuum distillation, and the resulting residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate) to obtain the target compounds A-74 (0.11 g) and A-75 (0.11 g). The yield for each compound was 44%. The obtained target 1 The H-NMR spectrum is shown below. Compound number A-75: 1H-NMR (CDCl3) δ: 7.38(1H, s),7.36-6.79 (3H, m), 5.64-4.22(7H, m), 3.84 (3H, s), 3.80-3.11(2H, m), 2.25-2.16(1H, m), 2.12(3H, s),1.24-1.02(15H, m) Compound number A-74: 1 H-NMR (CDCl3) δ: 7.42(1H, s),7.39-6.79 (3H, m), 5.72-2.16(10H, m), 3.84 (3H, s), 2.14(3H, s), 1.27-1.02(15H, m)

[0280] [Example 4] Synthesis of N-((2S)-1-(3-(2-hydroxy-2-(2-(trifluoromethoxy)phenyl)ethyl)-5-((E)-1-(isopropoxyimino)ethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)propan-2-yl)isobutyramide (compound numbers C-193 and C-194) (Process 1) Synthesis of (E)-5-(1-(isopropoxyimino)ethyl)-1-(methoxymethyl)pyrimidine-2,4(1H,3H)-dione

[0281] [ka]

[0282] (E)-5-(1-(isopropoxyimino)ethyl)pyrimidine-2,4(1H,3H)-dione (2.50 g) was dissolved in methylene chloride (140 ml), N,O-bis(trimethylsilyl)acetamide (10 ml) was added, and the mixture was stirred at room temperature for 1 hour. Then chloromethyl methyl ether (1.3 ml) was added and the mixture was stirred at room temperature overnight. The reaction mixture was purified by silica gel chromatography (eluent: hexane-ethyl acetate) to obtain 3.00 g of the target product. Yield: 99% The obtained target 1 The H-NMR spectrum is shown below. 1 H-NMR (CDCl3) δ: 8.32 (1H, s), 7.53 (1H, s), 5.15 (2H,s), 4.40-4.34 (1H, m), 3.44 (3H, s), 2.16 (3H, s), 1.27 (6H, d, J = 15.2 Hz). (Process 2) Synthesis of (S,E)-N-(1-(5-(1-(isopropoxyimino)ethyl)-3-(methoxymethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)propan-2-yl)isobutyramide (manufacturing intermediate 10)

[0283] [ka]

[0284] (E)-5-(1-(isopropoxyimino)ethyl)-1-(methoxymethyl)pyrimidine-2,4(1H,3H)-dione (2.50 g) was dissolved in tetrahydrofuran (25 ml), and tert-butyl (S)-(1-hydroxypropan-2-yl)carbamate (2.50 g), triphenylphosphine (3.80 g), and bis(2-methoxyethyl) azodicarboxylate (3.40 g) were added, and the mixture was stirred at room temperature for 7 hours. The reaction mixture was purified by silica gel column chromatography (eluent: hexane / ethyl acetate). The resulting solution was dissolved in 1,4-dioxane (20 ml), and 4 N hydrogen chloride / 1,4-dioxane solution (12 ml) was added. The mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated, and the resulting residue was dissolved in methylene chloride (40 ml). Under ice cooling, triethylamine (3 ml) and isobutanoyl chloride (1.3 ml) were added, and the mixture was stirred for 30 minutes. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: chloroform / ethyl acetate) to obtain 2.90 g of the target compound. Yield: 77% The obtained target 1 The H-NMR spectrum is shown below. 1 H-NMR (CDCl3) δ: 7.49 (1H, s), 5.93 (1H, d, J = 8.2 Hz),5.19-5.13 (2H, m), 4.42-4.32 (2H, m), 4.15-3.87 (2H, m), 3.43 (3H, s),2.30-2.18 (1H, m), 2.14 (3H, s), 1.37-0.93 (15H, m). (Step 3) Synthesis of (S,E)-N-(1-(5-(1-(isopropoxyimino)ethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)propan-2-yl)isobutyramide (production intermediate 9)

[0285] [ka]

[0286] (S,E)-N-(1-(5-(1-(isopropoxyimino)ethyl)-3-(methoxymethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)propan-2-yl)isobutyramide (0.50 g) was dissolved in methylene chloride (15 ml), and under ice cooling, 1.5 ml of 17% boron tribromide methylene chloride solution was added and the mixture was stirred overnight. Saturated sodium bicarbonate aqueous solution was added to the reaction mixture, extracted with methylene chloride, and then dried over anhydrous sodium sulfate. The solvent was removed by reduced pressure distillation, and the resulting residue was purified by silica gel chromatography (eluent: hexane-ethyl acetate) to obtain 0.32 g of the target product. Yield: 72% The obtained target 1 The H-NMR spectrum is shown below. 1 H-NMR (CDCl3) δ: 9.33 (1H, d, J = 6.3 Hz), 7.42 (1H, d,J= 6.3 Hz), 5.94 (1H, d, J = 8.2 Hz), 4.48-3.84 (4H, m), 2.25-2.21 (1H, m),2.12 (3H, s), 1.26-1.01 (15H, m). (Step 4) Synthesis of (S,E)-N-(1-(5-(1-(isopropoxyimino)ethyl)-2,6-dioxo-3-(2-oxo-2-(2-(trifluoromethoxy)phenyl)ethyl)-3,6-dihydropyrimidin-1(2H)-yl)propan-2-yl)isobutyramide (compound number C-195)

[0287] [ka]

[0288] (S,E)-N-(1-(5-(1-(isopropoxyimino)ethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)propan-2-yl)isobutyramide (0.20 g) was dissolved in N,N-dimethylformamide (3 ml), and under ice cooling, 2-bromo-1-(2-(trifluoromethoxy)phenyl)ethan-1-one (0.25 g) and potassium carbonate (0.10 g) were added, and the mixture was stirred overnight. Water was added to the reaction mixture, and after extraction with ethyl acetate, the mixture was dried over anhydrous sodium sulfate. The solvent was removed by reduced pressure distillation, and the resulting residue was purified by silica gel chromatography (eluent: hexane-ethyl acetate) to obtain 0.23 g of the target product. Yield: 72% The obtained target 1 The H-NMR spectrum is shown below. 1 H-NMR (CDCl3) δ: 7.98-7.36 (4H, m), 7.33 (1H, s),6.07-3.90 (7H, m), 2.28-2.21 (1H, m), 2.17 (3H, s), 1.26-1.05 (15H, m). (Step 5) Synthesis of N-((2S)-1-(3-(2-hydroxy-2-(2-(trifluoromethoxy)phenyl)ethyl)-5-((E)-1-(isopropoxyimino)ethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)propan-2-yl)isobutyramide (compound numbers C-193 and C-194)

[0289] [ka]

[0290] (S,E)-N-(1-(5-(1-(isopropoxyimino)ethyl)-2,6-dioxo-3-(2-oxo-2-(2-(trifluoromethoxy)phenyl)ethyl)-3,6-dihydropyrimidin-1(2H)-yl)propan-2-yl)isobutyramide (0.19 g) was dissolved in methanol (2 ml) and tetrahydrofuran (2 ml), and under ice cooling, sodium borohydride (15 mg) was added and the mixture was stirred for 40 minutes. Saturated ammonium chloride aqueous solution was added to the reaction mixture, extracted with ethyl acetate, washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was removed by vacuum distillation, and the resulting residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate) to obtain the target compounds C-193 (0.90 g) and C-194 (0.90 g). The yield for each compound was 47%. The obtained target 1 The H-NMR spectrum is shown below. Compound number C-194: 1 H-NMR (CDCl3) δ: 7.76-7.27 (4H, m), 7.41 (1H, s),5.75-5.43 (3H, m), 4.77-4.24 (4H, m), 3.81-3.13 (2H, m), 2.21-2.18 (1H, m),2.12 (3H, s), 1.28-1.00 (15H, m). Compound number C-193: 1 H-NMR (CDCl3) δ: 7.84-7.35 (4H, m), 7.42 (1H, s),5.64-3.74 (9H, m), 2.25-2.18 (1H, m), 2.14 (3H, s), 1.28-1.01 (15H, m).

[0291] Table 2 shows some of the compounds of the present invention produced by the same method as in the above-described examples. The melting point (mp) of each compound is also shown in the table.

[0292] [Table 2] TIFF0007846807000035.tif183113TIFF0007846807000036.tif183113TIFF0007846807000037.tif183113TIFF00078468070 00038.tif183113TIFF0007846807000039.tif183113TIFF0007846807000040.tif183113TIFF0007846807000041.tif167170

[0293] Furthermore, Table 3 shows some of the compounds of the present invention produced by the same method as in the above-described examples. The melting point (mp) of each compound is also shown in the table. If a compound is a stereoisomer, this is indicated in the special notes. [Table 3] TIFF0007846807000043.tif236170TIFF0007846807000044.tif236170TIFF0007846807000045.tif236170TIFF000 7846807000046.tif236170TIFF0007846807000047.tif236170TIFF0007846807000048.tif236170TIFF00078468070 00049.tif236170TIFF0007846807000050.tif231170TIFF0007846807000051.tif231170TIFF0007846807000052.t if231170TIFF0007846807000053.tif231170TIFF0007846807000054.tif234170TIFF0007846807000055.tif189170

[0294] Furthermore, Table 4 shows some of the compounds of the present invention produced by the same method as in the above-described examples. The melting point (mp) of each compound is also shown in the table. In the case of stereoisomers, this is indicated in the special notes. [Table 4] TIFF0007846807000057.tif230170

[0295] Of the compounds listed in Tables 2 to 4, those compounds having amorphous or viscous oil properties are shown in Table 5 below. 1 H-NMR data is shown. [Table 5] TIFF0007846807000059.tif249170TIFF0007846807000060.tif178113TIFF0007846807000061.tif121170

[0296] Furthermore, Table 6 shows some of the compounds of the present invention produced by the same method as in the above-described examples. The melting point (mp) of each compound is also shown in the table. In the case of stereoisomers, this is indicated in the special notes. [Table 6] TIFF0007846807000063.tif226170TIFF0007846807000064.tif220170TIFF0007846807000065.tif220170TIFF0007846807000066.tif220170TIFF0007846807000067.tif222170TIFF0007846807000068.tif222170TIFF0007846807000069.tif222170TIFF0007846807000070.tif222170TIFF0007846807000071.tif223170TIFF0007846807000072.tif222170TIFF0007846807000073.tif222170TIFF0007846807000074.tif222170TIFF0007846807000075.tif223170TIFF0007846807000076.tif222170TIFF0007846807000077.tif222170TIFF0007846807000078.tif222170TIFF0007846807000079.tif222170TIFF0007846807000080.tif222170TIFF0007846807000081.tif222170TIFF0007846807000082.tif222170TIFF0007846807000083.tif222170TIFF0007846807000084.tif222170TIFF0007846807000085.tif222170TIFF0007846807000086.tif222170TIFF0007846807000087.tif222170TIFF0007846807000088.tif222170TIFF0007846807000089.tif222170TIFF0007846807000090.tif222170TIFF0007846807000091.tif222170TIFF0007846807000092.tif222170TIFF0007846807000093.tif222170TIFF0007846807000094.tif222170TIFF0007846807000095.tif222170TIFF0007846807000096.tif222170TIFF0007846807000097.tif222170TIFF0007846807000098.tif222170TIFF000784680700 0099.tif222170TIFF0007846807000100.tif222170TIFF0007846807000101.tif222170TIFF0007846807000102.tif223170TIFF0007846 807000103.tif222170TIFF0007846807000104.tif222170TIFF0007846807000105.tif222170TIFF0007846807000106.tif222170TIFF00 07846807000107.tif222170TIFF0007846807000108.tif222170TIFF0007846807000109.tif222170TIFF0007846807000110.tif141170.

[0297] Furthermore, Table 7 shows some of the compounds of the present invention produced by the same method as in the above-described examples. The melting point (mp) of each compound is also shown in the table. In the case of stereoisomers, this is indicated in the special notes. [Table 7] TIFF0007846807000112.tif225170TIFF0007846807000113.tif225170TIFF000 7846807000114.tif224170TIFF0007846807000115.tif224170TIFF0007846807 000116.tif224170TIFF0007846807000117.tif224170TIFF0007846807000118. tif224170TIFF0007846807000119.tif224170TIFF0007846807000120.tif22417 0TIFF0007846807000121.tif224170TIFF0007846807000122.tif224170TIFF00 07846807000123.tif224170TIFF0007846807000124.tif224170TIFF0007846807 000125.tif224170TIFF0007846807000126.tif224170TIFF0007846807000127. tif224170TIFF0007846807000128.tif224170TIFF0007846807000129.tif51170

[0298] Of the compounds listed in Tables 6 and 7, those having amorphous or viscous oil properties are shown in Table 8 below. 1 H-NMR data is shown. [Table 8] TIFF0007846807000131.tif226170TIFF0007846807000132.tif237170TIFF0007846807000133.tif227170TIFF00078468070 00134.tif229170TIFF0007846807000135.tif242170TIFF0007846807000136.tif233170TIFF0007846807000137.tif149170

[0299] [Biology Test] The following test examples demonstrate that the dihydropyrimidine compound of the present invention is useful as an active ingredient in agricultural and horticultural fungicides. The dihydropyrimidine compounds used in the tests are shown in Tables 9 and 10 below for each test. The compound numbers in Table 9 correspond to the compound numbers in Tables 2 to 4. The compound numbers in Table 10 correspond to the compound numbers in Tables 6 and 7.

[0300] [Table 9]

[0301] [Table 10]

[0302] (Preparation of test emulsion) Five parts by weight of the dihydropyrimidine compound of the present invention, 93.5 parts by weight of N,N-dimethylformamide, and 1.5 parts by weight of polyoxyethylene sorbitan monolaurate (TWEEN® 20) were mixed and dissolved to obtain an emulsion (I) containing 5% of the active ingredient.

[0303] The control value was calculated using the following formula.

[0304] [Mathematics 1] Control value (%) = 100 - {Percentage of lesion area in treated area / Percentage of lesion area in untreated area} × 100

[0305] (Test Example 1) Apple Scab Disease Control Test Water was added to emulsion (I) to obtain a drug solution by dissolving the dihydropyrimidine compound at a concentration of 125 ppm. Subsequently, the drug solution was sprayed onto apple seedlings (variety "Ohrin", 3-4 leaf stage) grown in seedling pots. After air drying, conidia of the apple scab fungus (Venturia inaequalis) were inoculated (treated group). As a control, apple seedlings that were not sprayed with the drug solution were similarly inoculated (untreated group). These were then placed in a humid chamber at 20°C with alternating light and dark cycles every 12 hours. Two weeks after inoculation, the leaves of young apple seedlings were visually observed to determine the diseased area percentage, and the control efficacy was calculated.

[0306] The dihydropyrimidine compounds listed in Tables 9 and 10 were subjected to control tests for apple scab disease. All compounds showed a control efficacy of 75% or more.

[0307] (Test Example 2) Wheat powdery mildew control test Water was added to emulsion (I) to obtain a drug solution by dissolving the dihydropyrimidine compound at a concentration of 125 ppm. Subsequently, the drug solution was sprayed onto wheat seedlings (variety "Chihoku", 1-2 leaf stage) grown in seedling pots. After air drying, conidia of the wheat powdery mildew fungus (Erysiphe graminis f.sp. tritici) were sprinkled on and inoculated (treated group). As a control, wheat seedlings that were not sprayed with the drug solution were inoculated in the same manner as above (untreated group). These were then left to stand in a greenhouse at 20°C. Six days after inoculation, the leaves of wheat seedlings were visually observed to determine the diseased area percentage, and the control efficacy was calculated.

[0308] The dihydropyrimidine compounds listed in Tables 9 and 10 were tested for the control of wheat powdery mildew. All compounds showed a control efficacy of 75% or more.

[0309] (Test Example 3) Wheat Rust Disease Control Test Water was added to emulsion (I) to obtain a drug solution by dissolving the dihydropyrimidine compound at a concentration of 125 ppm. Subsequently, the drug solution was sprayed onto wheat seedlings (variety "Norin 61", 1-2 leaf stage) cultivated in seedling pots. After air drying, the wheat seedlings sprayed with the drug solution were inoculated with summer spores of the wheat rust fungus (Puccinia recondita) (treated group). As a control, wheat seedlings that were not sprayed with the drug solution were inoculated in the same manner as above (untreated group). These were then left to stand in a greenhouse at 20°C. Twelve days after inoculation, the leaves of wheat seedlings were visually inspected to determine the diseased area percentage, and the control efficacy was calculated.

[0310] The dihydropyrimidine compounds listed in Tables 9 and 10 were tested for the control of wheat rust disease. All compounds showed a control efficacy of 75% or more.

[0311] (Test Example 4) Cucumber gray mold control test Water was added to emulsion (I) to obtain a drug solution by dissolving the dihydropyrimidine compound at a concentration of 125 ppm. Subsequently, the drug solution was sprayed onto cucumber seedlings (variety "Jibai" type, cotyledon stage) grown in seedling pots. After air drying, a conidial suspension of cucumber gray mold fungus (Botrytis cinerea) was inoculated by drop (treated group). As a control, cucumber seedlings that were not sprayed with the drug solution were inoculated by drop in the same manner as above (untreated group). These were then left to stand in a humid chamber at 20°C. Four days after inoculation, the leaves of cucumber seedlings were visually inspected to determine the diseased area percentage, and the control value was calculated.

[0312] Dihydropyrimidine compounds listed in Tables 9 and 10 were tested for the control of cucumber gray mold. All compounds showed a control efficacy of 75% or more.

[0313] (Test Example 5) Wheat powdery mildew seed treatment test Wheat seeds (variety "Chihoku") were treated with emulsion (I) so that the ratio (weight of dihydropyrimidine compound) / (weight of seed) was 100g / 100kg. These seeds were sown in pots and inoculated with conidia of the wheat powdery mildew fungus (Erysiphe graminis f.sp. tritici) 8-10 days later (treated group). As a control, untreated wheat seedlings were inoculated in the same manner as above (untreated group). These were then left to stand in a greenhouse at 20°C. Seven days after inoculation, the leaves of wheat seedlings were visually observed to determine the diseased area percentage, and the control efficacy was calculated.

[0314] The dihydropyrimidine compounds listed in Table 11 were used in a seed treatment test for wheat powdery mildew. All of the compounds showed a control efficacy of 75% or more.

[0315] [Table 11]

[0316] (Test Example 6) Wheat powdery mildew soil drenching treatment test Wheat seeds (variety "Chihoku") were sown in pots (5.5 cm x 5.5 cm), and 10 mL of a fungicide solution (emulsion (I) with water to a concentration of 100 ppm of dihydropyrimidine compound) was irrigated into the pots. After 8-10 days, conidia of the wheat powdery mildew fungus (Erysiphe graminis f.sp. tritici) were sprinkled on top to inoculate the pots (treated group). As a control, wheat seedlings that were not treated with the fungicide were inoculated in the same manner as above (untreated group). These were then left to stand in a greenhouse at 20°C. Seven days after inoculation, the leaves of wheat seedlings were visually observed to determine the diseased area percentage, and the control efficacy was calculated.

[0317] Dihydropyrimidine compounds listed in Table 12 were subjected to soil drenching treatment tests for wheat powdery mildew. All compounds showed control efficacy of 75% or more.

[0318] [Table 12]

[0319] The following test examples demonstrate that the dihydropyrimidine compound of the present invention is useful as an active ingredient in nematicides. (Test Example 7) Efficacy against sweet potato root-knot nematodes In a 96-well microplate, 160 μL of a suspension containing approximately 50 second-instar larvae (L2) of sweet potato root-knot nematode per 0.16 mL was added to each well. Then, 40 μL of a drug solution prepared by adding water to emulsion (I) to make a dihydropyrimidine compound concentration of 125 ppm was added to each well. The plate was left at 20°C for 4 days. Subsequently, viability was determined and the nematode kill rate was calculated. Individuals that showed no movement for 10 seconds were considered dead. The experiment was performed in two replicates.

[0320] Efficacy tests were conducted on sweet potato root-knot nematodes for compounds A-28, A-64, C-92, and C-145. All compounds achieved a nematode kill rate of 60% or more against sweet potato root-knot nematodes.

[0321] The following test examples demonstrate that the dihydropyrimidine compounds of the present invention are useful as active ingredients in medical and veterinary antifungal agents. (Test Example 8) Antimicrobial test against Fusarium graminearum Water was added to emulsion (I) to a concentration of the dihydropyrimidine compound of 125 ppm, and the compound was dissolved to obtain a drug solution. Spores of Fusarium graminearum were added to potato sucrose yeast extract medium and dispersed. The above-mentioned drug solution was then added and mixed to achieve a dihydropyrimidine compound concentration of 15.6 ppm in the culture medium. These mixtures were then dispensed onto 96-well microplates and incubated in the dark at 20°C for 4 days. After culturing, turbidity at a wavelength of 405 nm was measured using a microplate reader, and the percentage of Fusarium graminearum growth inhibition was determined compared to the untreated case.

[0322] Antimicrobial tests were conducted against Fusarium graminearum using the dihydropyrimidine compounds listed in Table 13. All compounds showed excellent growth inhibition rates of 50% or more.

[0323] [Table 13]

[0324] (Test Example 9) Antimicrobial test against Aspergillus niger Aspergillus niger spores were added to Vogel medium and dispersed, and then a dihydropyrimidine compound dissolved in dimethyl sulfoxide was added and mixed to a concentration of 25 ppm. These mixtures were then dispensed onto 96-well microplates and incubated in the dark at 25°C for 4 days. After culturing, turbidity at a wavelength of 405 nm was measured using a microplate reader, and the percentage of Aspergillus niger growth inhibition was determined compared to the untreated case.

[0325] Antimicrobial tests were conducted against Aspergillus niger for the dihydropyrimidine compounds listed in Table 14. All compounds showed excellent growth inhibition rates of 50% or more.

[0326] [Table 14] [Industrial applicability]

[0327] Since randomly selected dihydropyrimidine compounds from the present invention exhibit the effects described above, the dihydropyrimidine compounds of the present invention, including compounds not exemplified, possess bactericidal, antibacterial, and nematicidal effects, do not cause phytotoxicity to plants, have low toxicity to humans, livestock, and fish, and have little impact on the environment, making them useful as pesticides, nematicides, and antifungal agents for medical and veterinary use.

Claims

[Claim 1] A compound represented by formula (III) or a salt thereof. 【Chemistry 1】 [In formula (III), X １ This represents a hydrogen atom; X ２ R １ O-N=CR ６ The group represented by - is shown; R １ This represents a C1-6 alkyl group, R ６ is a hydrogen atom or It shows C1-6 alkyl groups; A represents a substituted or unsubstituted C1-6 alkylene group. The substituents on the C1-6 alkylene groups in A are Hydroxyl group, C1-6 alkoxy groups which may be substituted with cyano groups, Oxo group (O=), or R ａ１ It is a divalent group represented as O-N=, R ａ１ This represents a C1-6 alkyl group; Q represents a substituted or unsubstituted C6-10 aryl group. The substituents on the C6-10 aryl groups in Q are C1-6 alkoxy groups, Halogeno group, Hydroxyl group, C1-6 alkyl groups, C2-6 alkenyl groups, Cyano group, aminocarbonyl group, C1-6 alkylthio groups, C1-6 alkylsulfonyl groups, amino group, Nitro group, or It is a C1-6 haloalkoxy group.

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