2,6-Dioxo-3,6-dihydropyrimidine compounds, agricultural and horticultural fungicides, nematicides, and medical and veterinary antifungals

Abstract

The present invention addresses the problem of providing: a 2,6-dioxo-3,6-dihydropyrimidine compound which has excellent bactericidal activity, is safe, and can be industrially advantageously synthesized; and an agricultural and horticultural bactericide, nematicide, and medical and veterinary antifungal agent containing the same as an active ingredient.　The compound according to the present invention is a compound represented by formula (II) or a salt thereof.　In formula (II), each Y1 is an oxygen atom or a sulfur atom; Y2 is an oxygen atom or a sulfur atom; Z is a group represented by C-X1 or a nitrogen atom; X1 is a hydrogen atom, a halogeno group, or the like; X2 is a group represented by R1O-N=CR6- or the like; R1 is a substituted or unsubstituted linear C1-6 alkyl group or the like; R6 is a substituted or unsubstituted linear C1-6 alkyl group or the like; X3 is a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted linear C2-6 alkenyl group or the like; A is a substituted or unsubstituted C1-6 alkylene group, a substituted or unsubstituted C2-6 alkenylene group, or the like; and Q is a substituted or unsubstituted C6-10 aryl group or a substituted or unsubstituted 5-10 membered-ring heteroaryl group.

Description

[Technical field]

[0001] The present invention relates to a 2,6-dioxo-3,6-dihydropyrimidine compound and an agricultural and horticultural fungicide. More specifically, the present invention relates to a 2,6-dioxo-3,6-dihydropyrimidine compound that has excellent fungicidal and antibacterial activity, is safe, and can be synthesized industrially in an advantageous manner, and to an agricultural and horticultural fungicide containing the same as an active ingredient. Furthermore, the present invention relates to a nematicide containing the compound as an active ingredient. Furthermore, the present invention relates to an antifungal agent for medical and veterinary use that contains the compound as an active ingredient. This application claims priority to Japanese Patent Application No. 2019-195484 filed on October 28, 2019 and Japanese Patent Application No. 2020-053191 filed on March 24, 2020, the contents of which are incorporated herein by reference. [Background technology]

[0002] Various compounds have been proposed that have a pesticidal activity against crop diseases in the cultivation of agricultural and horticultural crops. In order to use such compounds as agricultural and horticultural fungicides, they are required to not only have a sufficiently high efficacy, but also to be unlikely to develop drug resistance, not to cause phytotoxicity to plants or soil contamination, and to have low toxicity to livestock and fish.

[0003] Incidentally, Patent Document 1 discloses a compound represented by formula (A) and the like. [ka] [Prior art documents] [Patent documents]

[0004] [Patent Document 1] WO 2013 / 071169 A Summary of the Invention [Problem to be solved by the invention]

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

[0006] As a result of intensive research by the present inventors to solve the above problems, they have completed the present invention including the following aspects.

[0007] [1] A compound represented by formula (II) or a salt thereof. [ka] [In formula (II), Y 1 represents an oxygen atom or a sulfur atom; Y 2 represents an oxygen atom or a sulfur atom; Z is for CX 1 represents a group or a nitrogen atom represented by the formula: 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 C1-6 alkylthio ... unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C3-6 cycloalkyloxy group, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted C6-10 aryloxy group, substituted or unsubstituted C6-10 arylthio group, substituted or unsubstituted C6-10 arylsulfinyl group, substituted or unsubstituted C6-10 arylsulfonyl group, substituted or unsubstituted 5-6 membered heterocyclyl group, substituted or unsubstituted 5-6 membered heterocyclyloxy group, nitro group, 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 1 A group represented by -CO-O-, R 1 -CO-NR 5 -, R 2 A group represented by -O-CO-O-, R 2 -O-CO-NR 5 -, R 3 R 4 A group represented by N-CO-O-, R 3 R 4 N-CO-NR 5 -, R 2 SO2-NR 5 -, R 3 R 4 A group represented by N-SO2- or R 1 ON=CR 6 - represents a group represented by the formula: R 1each 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- or 6-membered heterocyclyl group, R 2 each 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- or 6-membered heterocyclyl group, R 3 each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group, R 4 each 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 may be taken together to form a divalent organic group, R 5 each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, R 6 represents a hydrogen atom, a halogeno group, an amino group, a substituted or unsubstituted mono-C1-6 alkylamino group, a substituted or unsubstituted di-C1-6 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- or 6-membered heterocyclyl group; X 2 is R 1 ON=CR 6-, R 1 CO-ON=CR 6 -, R 3 R 4 N-CO-ON=CR 6 -, R 3 R 4 NN=CR 6 -, or R 7 -N=CR 6 R represents a group represented by -; 1 , R 3 , R 4 , and R 6 X 1 In It has the same meaning as them;R 7 represents a substituted or unsubstituted 5-membered heterocyclyl group; X 3 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, R 1 -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 heterocyclyl group. [2] The compound or salt thereof according to [1], wherein the formula (II) is represented by the 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 3the substituent on the linear C1-6 alkyl group, the substituent on the linear C2-6 alkenyl group, the substituent on the linear C2-6 alkynyl group, the substituent on the C3-6 cycloalkyl group, the substituent on the C6-10 aryl group, or the substituent on the 4- to 6-membered heterocyclyl group in 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 C 3-6 cycloalkyl group, substituted or unsubstituted C3-6 cycloalkyloxy group, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted C6-10 aryloxy group, substituted or unsubstituted C6-10 arylthio group, substituted or unsubstituted C6-10 arylsulfinyl group, substituted or unsubstituted C6-10 arylsulfonyl group, substituted or unsubstituted 3-10 membered heterocyclyl group, substituted or unsubstituted 3-10 membered heterocyclyloxy group, nitro group, cyano group, R a A group represented by -CO-, a carboxy group, R b A group represented by -O-CO-, R c R d A group represented by N-, R c R d A 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 -, R a -CO-CO-NR e -, R a -CO-NR e -NR e -, 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 -, R c R d A group represented by N-CO-O-, R c R d N-CO-NR e -, R c R d N-CO-CO-NR e -, R a -CS-NR e -, R c R d N-CS-NR e -, R b SO2-NR e -, R c R d A group represented by N-SO2-, R a ON=CR f -, R h R j A group represented by C=NO-, R a -C(=NR g )-NR e -, R c R d NC(=NR g )-, 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 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 beach 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 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- or 6-membered heterocyclyl group, R d each 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 may be taken together to form a divalent organic group, R e each 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 represents a hydrogen atom, an amino group, or a substituted or unsubstituted C1-6 alkyl group, 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 h each independently represents a substituted or unsubstituted C1 to C6 alkyl group, or a substituted or unsubstituted C6 to C10 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 may together form a divalent organic group; When there are two or more substituents on the linear C1-6 alkyl group, two of them may combine together to form a divalent organic group; The compound or a salt thereof according to [1] or [2]. [4] The substituent on the C1-6 alkylene group or the C2-6 alkenylene group in A is, 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 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 C1-6 alkylthio ... Unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C3-6 cycloalkyloxy group, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted C6-10 aryloxy group, substituted or unsubstituted C6-10 arylthio group, substituted or unsubstituted C6-10 arylsulfinyl group, substituted or unsubstituted C6-10 arylsulfonyl group, substituted or unsubstituted 3-6 membered heterocyclyl group, substituted or unsubstituted 3-6 membered heterocyclyloxy group, nitro group, 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 -, R b1 A group represented by -O-CO-O-, R b1 -O-CO-NR e1 -, R c1 R d1 A group represented by N-CO-O-, R c1 R d1 N-CO-NR e1 -, R b1SO2-NR e1 -, R c1 R d1 A group represented by N-SO2-, R a1 ON=CR f1 -, R g1 R h1 Groups represented by C=NO-, oxo group (O=), thioxo group (S=), R a1 A divalent group represented by -N=, R a1 A divalent group represented by ON=, R c1 R d1 A divalent group represented by NN=, R a1 -CO-NR e1 A divalent group represented by -N=, R b1 -O-CO-NR e1 A divalent group 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 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- or 6-membered heterocyclyl group, R b1 each 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- or 6-membered heterocyclyl group, R c1 each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group, R d1each 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 may be taken together to form a divalent organic group, R e1 each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, R f1 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, R g1 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- or 6-membered heterocyclyl group, R h1 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, where R g1 and R h1 may together form a divalent organic group; When there are two or more substituents on the C1-6 alkylene group or the C2-6 alkenylene group, two of them may combine together to form a divalent organic group; The compound or a salt thereof according to any one of [1] to [3]. [5] An agricultural and horticultural fungicide comprising, as an active ingredient, at least one selected from the group consisting of the compound according to any one of [1] to [4] and a salt thereof. [6] The agricultural and horticultural fungicide according to [5], which is for use in seed treatment. [7] A nematicide comprising, as an active ingredient, at least one selected from the group consisting of the compound according to any one of [1] to [4] and a salt thereof. [8] An antifungal agent for medical or veterinary use, comprising as an active ingredient at least one selected from the group consisting of the compound according to any one of [1] to [4] and salts thereof. [9] A compound represented by formula (III) or a salt thereof. [ka] [In formula (III), X 1 is 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 C1-6 alkylthio ... unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C3-6 cycloalkyloxy group, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted C6-10 aryloxy group, substituted or unsubstituted C6-10 arylthio group, substituted or unsubstituted C6-10 arylsulfinyl group, substituted or unsubstituted C6-10 arylsulfonyl group, substituted or unsubstituted 5-6 membered heterocyclyl group, substituted or unsubstituted 5-6 membered heterocyclyloxy group, nitro group, 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 1 A group represented by -CO-O-, R 1 -CO-NR 5 -, R 2 A group represented by -O-CO-O-, R 2 -O-CO-NR 5 -, R 3 R 4 A group represented by N-CO-O-, R 3 R 4 N-CO-NR 5 -, R 2 SO2-NR 5 -, R 3 R 4A group represented by N-SO2- or R 1 ON=CR 6 - represents a group represented by the formula: R 1 each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group, R 2 each 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- or 6-membered heterocyclyl group, R 3 each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group, R 4 each 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 may be taken together to form a divalent organic group, R 5 each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, R 6represents a hydrogen atom, a halogeno group, an amino group, a substituted or unsubstituted mono-C1-6 alkylamino group, a substituted or unsubstituted di-C1-6 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- or 6-membered heterocyclyl group; X 2 is R 1 ON=CR 6 -, R 1 CO-ON=CR 6 -, R 3 R 4 N-CO-ON=CR 6 -, R 3 R 4 NN=CR 6 -, or R 7 -N=CR 6 R represents a group represented by -; 1 , R 3 , R 4 , and R 6 X 1 R 7 represents a substituted or unsubstituted 5-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 heterocyclyl group.

[10] A compound represented by formula (IV) or a salt thereof. [ka] [In formula (IV), 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 C1-6 alkylthio ... unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C3-6 cycloalkyloxy group, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted C6-10 aryloxy group, substituted or unsubstituted C6-10 arylthio group, substituted or unsubstituted C6-10 arylsulfinyl group, substituted or unsubstituted C6-10 arylsulfonyl group, substituted or unsubstituted 5-6 membered heterocyclyl group, substituted or unsubstituted 5-6 membered heterocyclyloxy group, nitro group, 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 1 A group represented by -CO-O-, R 1 -CO-NR 5 -, R 2 A group represented by -O-CO-O-, R 2 -O-CO-NR 5 -, R 3 R 4 A group represented by N-CO-O-, R 3 R 4 N-CO-NR 5 -, R 2 SO2-NR 5 -, R 3 R 4 A group represented by N-SO2- or R 1 ON=CR 6 - represents a group represented by the formula: R 1each 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- or 6-membered heterocyclyl group, R 2 each 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- or 6-membered heterocyclyl group, R 3 each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group, R 4 each 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 may be taken together to form a divalent organic group, R 5 each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, R 6 represents a hydrogen atom, a halogeno group, an amino group, a substituted or unsubstituted mono-C1-6 alkylamino group, a substituted or unsubstituted di-C1-6 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- or 6-membered heterocyclyl group; X 2 is R 1 ON=CR 6-, R 1 CO-ON=CR 6 -, R 3 R 4 N-CO-ON=CR 6 -, R 3 R 4 NR 3 R 4 NN=CR 6 -, or R 7 -N=CR 6 R represents a group represented by -; 1 , R 3 , R 4 , and R 6 X 1 R 7 represents a substituted or unsubstituted 5-membered heterocyclyl group; X 3 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, R 1 -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 represents a hydrogen atom or a C1-6 alkoxymethyl group. Effect of the Invention

[0008] The dihydropyrimidine compound of the present invention has excellent bactericidal and antibacterial activity, is reliable in effectiveness, is safe, and can be synthesized industrially with advantage. The agricultural and horticultural fungicide and nematicide of the present invention have excellent pest control effects, do not cause phytotoxicity to plants, and are less toxic to humans, livestock and fish and have less impact on the environment. The medical and veterinary antifungal agent of the present invention has excellent antibacterial effects and is less toxic to humans, livestock and fish. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[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 the present invention, the term "unsubstituted" means that only the group that serves as the mother nucleus is present. When only the name of the group that serves as the mother nucleus is described, it means "unsubstituted" unless otherwise specified. On the other hand, the term "substituted" means that any hydrogen atom of the core group is replaced with a group having the same or different structure as the core group. Therefore, a "substituent" is another group bonded to the core group. The number of substituents may be one or more. The two or more substituents may be the same or different.

[0012] The "substituents" are not particularly limited as long as they are chemically permissible and have the effect of the present invention. Specific examples of groups which can be "substituents" include the following groups. halogeno groups such as fluoro, chloro, bromo, and iodo 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 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, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-methyl-3-butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 2-methyl-3-pentynyl, 1-hexynyl, and 1,1-dimethyl-2-butynyl;

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

[0014] Hydroxyl; C1-6 alkoxy groups, such as a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group, or a t-butoxy group; C2-6 alkenyloxy groups such as a vinyloxy group, an allyloxy group, a propenyloxy group, or a butenyloxy group; 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 and propionyl groups; Formyloxy group; C1-6 alkylcarbonyloxy groups such as acetyloxy and propionyloxy; C1-6 alkoxycarbonyl groups, such as a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, an n-butoxycarbonyl group, or a t-butoxycarbonyl group;

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

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

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

[0019] Mercapto group; C1-6 alkylthio groups, such as a methylthio group, an ethylthio group, an n-propylthio group, an i-propylthio group, an n-butylthio group, an i-butylthio group, an s-butylthio group, or a t-butylthio group; C1-6 haloalkylthio groups, such as a trifluoromethylthio group and a 2,2,2-trifluoroethylthio group; C2-6 alkenylthio groups such as vinylthio groups and allylthio groups; C2-6 alkynylthio groups, such as an ethynylthio group or a propargylthio group; C1-6 alkylsulfinyl groups such as a methylsulfinyl group, an ethylsulfinyl group, or a t-butylsulfinyl group; C1-6 haloalkylsulfinyl groups such as a trifluoromethylsulfinyl group and a 2,2,2-trifluoroethylsulfinyl group; C2-6 alkenylsulfinyl groups, such as an allylsulfinyl group; C2-6 alkynylsulfinyl groups, such as a propargylsulfinyl group; C1-6 alkylsulfonyl groups such as a methylsulfonyl group, an ethylsulfonyl group, or a t-butylsulfonyl group; C1-6 haloalkylsulfonyl groups such as a trifluoromethylsulfonyl group or a 2,2,2-trifluoroethylsulfonyl group; C2-6 alkenylsulfonyl groups, such as an allylsulfonyl group; C2-6 alkynylsulfonyl groups, such as a propargylsulfonyl group; Aminothiocarbonyl group; C1-6 alkylsulfoximino groups such as S,S-dimethylsulfoximino groups;

[0020] Tri-C1-6 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 core group is 1-6. This number of carbon atoms does not include the number of carbon atoms in the substituent. For example, an ethoxybutyl group is classified as a C2 alkoxyC4 alkyl group because the core group is a butyl group and the substituent is an ethoxy group.

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

[0023] Examples of the 3- to 6-membered saturated heterocyclyl group include an aziridinyl group, an epoxy group, an azetidinyl group, an oxetanyl group, a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a tetrahydro-2H-pyranyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, and a dioxanyl group.

[0024] Examples of the 5-membered heteroaryl group include a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, and a tetrazolyl group. Examples of the 6-membered heteroaryl group include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group. Examples of the 5-membered partially unsaturated heterocyclyl group include a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group, and an oxazolinyl group. Examples of the 6-membered partially unsaturated heterocyclyl group include an isoxazolinyl group and a dihydropyranyl group. In these "substituents", any hydrogen atom may be substituted with a group of a different structure.

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

[0026] [Z] Z is CX 1 represents a group represented by the following formula:

[0027] [X 1 〕 X 1 is 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 C1-6 alkylthio ... unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C3-6 cycloalkyloxy group, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted C6-10 aryloxy group, substituted or unsubstituted C6-10 arylthio group, substituted or unsubstituted C6-10 arylsulfinyl group, substituted or unsubstituted C6-10 arylsulfonyl group, substituted or unsubstituted 5-6 membered heterocyclyl group, substituted or unsubstituted 5-6 membered heterocyclyloxy group, nitro group, 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 1 A group represented by -CO-O-, R 1 -CO-NR 5 -, R 2 A group represented by -O-CO-O-, R 2 -O-CO-NR 5 -, R 3 R 4 A group represented by N-CO-O-, R 3 R4 N-CO-NR 5 -, R 2 SO2-NR 5 -, R 3 R 4 A group represented by N-SO2- or R 1 ON=CR 6 - represents a group represented by the formula:

[0028] R 1 each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group. R 2 each 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- or 6-membered heterocyclyl group. R 3 each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group. R 4 each independently represents a hydrogen atom, a substituted or unsubstituted C1 to 6 alkyl group, or a substituted or unsubstituted C6 to 10 aryl group. Here, R 3 and R 4 may be taken together to form a divalent organic group. R 5 each independently represents a hydrogen atom, a substituted or unsubstituted C1 to 6 alkyl group, or a substituted or unsubstituted C6 to 10 aryl group. R 6represents 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- or 6-membered heterocyclyl group.

[0029] X 1 Examples of the "halogeno group" in the above formula include a fluoro group, a chloro group, a bromo group, and an iodo group.

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

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

[0032] X 1 Examples of the "C2-6 alkynyl group" in the above formula include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-methyl-2-propynyl group, a 2-methyl-3-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 3-pentynyl group, a 4-pentynyl group, a 1-methyl-2-butynyl group, a 2-methyl-3-pentynyl group, a 1-hexynyl group, and a 1,1-dimethyl-2-butynyl group.

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

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

[0035] X 1In the above, examples of the 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" include halogeno groups such as fluoro group, chloro group, bromo group, and iodo group; hydroxyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, C1-6 alkoxy groups such as 2-chloro-n-propoxy group, i-butoxy group, and t-butoxy group; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, and trifluoromethoxy group; C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, and cyclohexyl group; C6-10 aryl groups such as phenyl group and 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 of the following substituents: C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups, such as a methoxyphenyl group; 5-membered heteroaryl groups such as a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, or a tetrazolyl group; C1-6 alkyl groups, C1 Preferred are a 5-membered heteroaryl group substituted by one or more substituents selected from a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group; a 6-membered heteroaryl group such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, or a triazinyl group; a 6-membered heteroaryl group substituted by one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group; or a cyano group.

[0036] X 1Examples of the "C3-6 cycloalkyl group" in the above formula include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. X 1 Examples of the "C3-6 cycloalkyloxy group" in the above formula include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, and a cyclohexyloxy group.

[0037] X 1 Examples of the "C6-10 aryl group" in the above formula include a phenyl group, a naphthyl group, an indanyl group, an indenyl group, and a tetralinyl group. X 1 Examples of the "C6-10 aryloxy group" in the above formula include a phenoxy group and a naphthoxy group.

[0038] X 1 Examples of the "C6-10 arylthio group" in the above formula include a phenylthio group and a naphthylthio group. X 1 Examples of the "C6-10 arylsulfinyl group" in the above formula include a phenylsulfinyl group and a naphthylsulfinyl group. X 1 Examples of the "C6-10 arylsulfonyl group" in the above formula include a phenylsulfonyl group and a naphthylsulfonyl group.

[0039] X 1 The "5- or 6-membered heterocyclyl group" in the above is a group containing 1, 2, 3, or 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms as ring constituent atoms. When there are two or more heteroatoms, they may be the same or different. Examples of the "5- or 6-membered heterocyclyl group" include 5- or 6-membered saturated heterocyclyl groups, 5- or 6-membered heteroaryl groups, and 5- or 6-membered partially unsaturated heterocyclyl groups.

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

[0041] X 1 The "5- or 6-membered heterocyclyloxy group" in the above formula has a structure in which a 5- or 6-membered heterocyclyl group and an oxy group are bonded. Specific examples include a thiazolyloxy group and a pyridyloxy group.

[0042] X 1In the above, examples of the substituent on the "C3-6 cycloalkyl group", "C3-6 cycloalkyloxy group", "C6-10 aryl group", "C6-10 aryloxy group", "C6-10 arylthio group", "C6-10 arylsulfinyl group", "C6-10 arylsulfonyl group", "5- to 6-membered heterocyclyl group", or "5- to 6-membered heterocyclyloxy group" include halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group; a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, C1-6 alkyl groups such as s-butyl, i-butyl, t-butyl, n-pentyl, and n-hexyl; C1-6 haloalkyl groups such as chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, and 1-fluoro-n-butyl; hydroxyl; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy; 2-chloro-n-propoxy, 2,3-dichlorobutoxy, C1-6 haloalkoxy groups such as trifluoromethoxy 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 groups, 4-methoxyphenyl groups, 4-chlorophenyl groups, 4-trifluoromethylphenyl groups, and 4-trifluoromethoxyphenyl groups; pyrrolyl groups, furyl groups, thienyl groups, imidazolyls, 5-membered heteroaryl groups such as a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, or a tetrazolyl group; 5-membered heteroaryl groups substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group; 6-membered heteroaryl groups such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, or a triazinyl group;A 6-membered heteroaryl group substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group; or a cyano group is preferred. Furthermore, as a substituent on a "C3-6 cycloalkyl group", a "C3-6 cycloalkyloxy group", a "5- or 6-membered heterocyclyl group", or a "5- or 6-membered heterocyclyloxy group", an oxo group is also preferred.

[0043] X 1 "R 1 In the group represented by -CO-, R 1 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- or 6-membered heterocyclyl group.

[0044] R 1 Examples of the "C1-6 alkyl group" in the above formula include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an i-propyl group, an i-butyl group, an s-butyl group, an t-butyl group, an i-pentyl group, a neopentyl group, a 2-methylbutyl group, and an i-hexyl group. R 1 Examples of the "C2-6 alkenyl group" in the above formula include a vinyl group and a 1-propenyl group. R 1 Examples of the "C2-6 alkynyl group" in the above formula include an ethynyl group and a 1-propynyl group. R 1In the above, examples of the substituents on the "C1-6 alkyl group", "C2-6 alkenyl group", or "C2-6 alkynyl group" include halogeno groups such as fluoro, chloro, bromo, and iodo 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, trifluoromethy C1-6 haloalkoxy groups such as oxy 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; C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloaryl groups such as 4-methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group, etc. a C6-10 aryl group substituted with one or more substituents of an alkyl group, an alkyl group, or a C1-6 haloalkoxy group; a 5-membered heteroaryl group such as a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, or a tetrazolyl group; a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkoxy group, or a C2-6 haloalkoxy group; and a cyano group are preferred. Preferred are a 5-membered heteroaryl group substituted by one or more substituents of any one of a C1-6 alkyl group, a C1-6 alkoxy group, or a C1-6 haloalkoxy group; a 6-membered heteroaryl group such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, or a triazinyl group; a 6-membered heteroaryl group substituted by one or more substituents of any one 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.

[0045] R 1 Examples of the "C3-6 cycloalkyl group" in the above formula include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. R 1Examples of the "C6-10 aryl group" in the above formula include a phenyl group, a naphthyl group, an indenyl group, an indanyl group, and a tetralinyl group.

[0046] R 1 The "5- or 6-membered heterocyclyl group" in the above is a group containing 1, 2, 3, or 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms as ring constituent atoms. When there are two or more heteroatoms, they may be the same or different. Examples of the "5- or 6-membered heterocyclyl group" include 5- or 6-membered saturated heterocyclyl groups, 5- or 6-membered heteroaryl groups, and 5- or 6-membered partially unsaturated heterocyclyl groups. Examples of the 5- to 6-membered saturated heterocyclyl group include a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a tetrahydro-2H-pyranyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, and a dioxanyl group. Examples of the 5- or 6-membered heteroaryl group include 5-membered heteroaryl groups such as a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, and a tetrazolyl group; and 6-membered heteroaryl groups such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group. Examples of 5- to 6-membered partially unsaturated heterocyclyl groups include 5-membered partially unsaturated heterocyclyl groups such as a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group, and an oxazolinyl group; and 6-membered partially unsaturated heterocyclyl groups such as an isoxazolinyl group and a dihydropyranyl group.

[0047] R 1In the above, examples of the substituents on the "C3-6 cycloalkyl group", "C6-10 aryl group", or "5- or 6-membered heterocyclyl group" include halogeno groups such as fluoro, chloro, bromo, and iodo 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, 1-fluoro-n-butyl, and the like; C1-6 haloalkyl groups such as the phenyl 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, and t-butoxy group; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, and trifluoromethoxy group; C6-10 aryl groups such as phenyl group and naphthyl group; 4-methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, and 4-trifluoromethylphenyl group. a C6-10 aryl 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, such as a 4-trifluoromethoxyphenyl group; a 5-membered heteroaryl group such as a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, or a tetrazolyl group; Preferred are a 5-membered heteroaryl group substituted by one or more substituents selected from the group consisting of an alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group; a 6-membered heteroaryl group such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group; a 6-membered heteroaryl group substituted by one or more substituents selected from the group consisting of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group; or a cyano group. Furthermore, as a substituent on the "C3-6 cycloalkyl group" or the "5- or 6-membered heterocyclyl group", an oxo group is also preferred.

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

[0049] X 1 "R 2 In the group represented by -O-CO-, R 2 represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group. R 2 Specific examples of the substituents in 1 The same examples as those given above can be mentioned.

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

[0051] X 1 "R 3 R 4 In the group represented by N-, R 3 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- or 6-membered heterocyclyl group; R 4 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 Specific examples of the substituents in 1 The same examples as those given above can be mentioned.

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

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

[0054] X 1 "R 3 R 4 In the group represented by N-CO-, R 3 and R 4 is the above "R 3 R 4 The meanings are the same as those in "a group represented by N-." "R 3 R 4Specific examples of the "group represented by N-CO-" include a carbamoyl group, an N,N-dimethylaminocarbonyl group, an N-(i-propyl)aminocarbonyl group, and an N-(i-propyl)-N-methylaminocarbonyl group.

[0055] X 1 "R 1 In the group represented by -CO-O-, R 1 is the above "R 1 The meaning is the same as that of the group represented by -CO-. "R 1 Specific examples of the "group represented by --CO--O--" include an acetyloxy group, an i-propylcarbonyloxy group, and the like.

[0056] X 1 "R 1 -CO-NR 5 In the group represented by "-", R 1 is the above "R 1 The meaning is the same as that of the group represented by -CO-. R 5 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. R 5 Specific examples of the substituents in 1 The same examples as those given above can be mentioned. "R 1 -CO-NR 5 Specific examples of the "group represented by -" include an acetylamino group, an i-propylcarbonylamino group, and the like.

[0057] X 1 "R 2 In the group represented by -O-CO-O-, R 2 is the above "R 2 -O-CO- group" has the same meaning as that in "a group represented by -O-CO-". "R 2Specific examples of the "group represented by --O--CO--O--" include a methoxycarbonyloxy group, an ethoxycarbonyloxy group, and the like.

[0058] X 1 "R 2 -O-CO-NR 5 In the group represented by "-", R 2 is the above "R 2 -O-CO- group" has the same meaning as that in "R 5 is the above "R 1 -CO-NR 5 -" has the same meaning as that in "a group represented by the formula "-". "R 2 -O-CO-NR 5 A specific example of the "group represented by -" is a methoxycarbonylamino group.

[0059] X 1 "R 3 R 4 In the group represented by N-CO-O-, R 3 and R 4 is the above "R 3 R 4 The meanings are the same as those in "a group represented by N-." "R 3 R 4 Specific examples of the "group represented by N-CO-O-" include a carbamoyloxy group, an N,N-dimethylaminocarbonyloxy group, and the like.

[0060] X 1 "R 3 R 4 N-CO-NR 5 In the group represented by "-", R 3 and R 4 is the above "R 3 R 4 The meanings are the same as those in "Group represented by N-" 5 is the above "R 1 -CO-NR 5 -" has the same meaning as that in "a group represented by the formula "-". "R3 R 4 N-CO-NR 5 Specific examples of the "group represented by -" include a carbamoylamino group, an N,N-dimethylaminocarbonylamino group, and the like.

[0061] X 1 "R 2 SO2-NR 5 In the group represented by "-", R 2 is the above "R 2 -O-CO- group" has the same meaning as that in "R 5 is the above "R 1 -CO-NR 5 -" has the same meaning as that in "a group represented by the formula "-". "R 2 SO2-NR 5 Specific examples of the "group represented by -" include a methanesulfonylamino group.

[0062] X 1 "R 3 R 4 In the group represented by N-SO2-, R 3 and R 4 is the above "R 3 R 4 The meanings are the same as those in "a group represented by N-." "R 3 R 4 A specific example of the "group represented by N-SO2-" is an N,N-dimethylaminosulfonyl group.

[0063] X 1 "R 1 ON=CR 6 In the group represented by "-", R 1 is the above "R 1 The meaning is the same as that of the group represented by -CO-. R 6represents a hydrogen atom, a halogeno group, an amino group, a substituted or unsubstituted mono-C1-6 alkylamino group, a substituted or unsubstituted di-C1-6 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- or 6-membered heterocyclyl group. R 6 Specific examples of the "substituted or unsubstituted C1-6 alkyl group" or "substituted or unsubstituted 5-6 heterocyclyl group" in the above are R 1 The same examples as those given above can be mentioned. R 6 Examples of the "halogeno group" in the above formula include a fluoro group, a chloro group, a bromo group, and an iodo group. R 6 Examples of the "mono C1-6 alkylamino group" in the "substituted or unsubstituted mono C1-6 alkylamino group" include a methylamino group, an ethylamino group, and an i-propylamino group. R 6 Examples of the "di-C1-6 alkylamino group" in the "substituted or unsubstituted di-C1-6 alkylamino group" include a dimethylamino group, a diethylamino group, and an N-methyl-Ni-propylamino group. R 6 Examples of the "C1 to 6 alkoxy group" in the "substituted or unsubstituted C1 to 6 alkoxy group" include a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, an i-propoxy group, an i-butoxy group, an s-butoxy group, a t-butoxy group, and an i-hexyloxy group. R 6 Examples of the "C1 to 6 alkylthio group" in the "substituted or unsubstituted C1 to 6 alkylthio group" include a methylthio group, an ethylthio group, an n-propylthio group, an n-butylthio group, an n-pentylthio group, an n-hexylthio group, and an i-propylthio group. R 6The substituents on the "C1-6 alkoxy group", "mono C1-6 alkylamino group", "di C1-6 alkylamino group", or "C1-6 alkylthio group" in 1 In the above, examples of the substituent on the "C1-6 alkyl group" include the same substituents as those exemplified above. "R 1 ON=CR 6 Specific examples of the "group represented by -" include a (hydroxyimino)methyl group, an (ethoxyimino)methyl group, and a 1-(i-propoxyimino)ethyl group.

[0064] In the present invention, preferred X 1 Examples of X include a hydrogen atom and a substituted or unsubstituted C1 to C6 alkyl group. 1 is more preferably a hydrogen atom.

[0065] [X 2 〕 X 2 is R 1 ON=CR 6 -, R 1 CO-ON=CR 6 -, R 3 R 4 N-CO-ON=CR 6 -, R 3 R 4 NN=CR 6 -, or R 7 -N=CR 6 - represents a group represented by the formula: Also, R 1 , R 3 , R 4 , and R 6 X 1 These terms have the same meaning as those in the above. R 7 represents a substituted or unsubstituted 5-membered heterocyclyl group. X 2 Specific examples of the substituents in 1 The same examples as those given above can be mentioned. R 7The "5-membered heterocyclyl group" in the above formula contains 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms as ring constituent atoms. Examples of the "5-membered heterocyclyl group" include a 5-membered saturated heterocyclyl group, a 5-membered heteroaryl group, and a 5-membered partially unsaturated heterocyclyl group. Examples of the 5-membered saturated heterocyclyl group include a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, and a dioxolanyl group. Examples of the 5-membered heteroaryl group include a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, and a tetrazolyl group. Examples of the 5-membered partially unsaturated heterocyclyl group include a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group, and an oxazolinyl group.

[0066] R 7In the above, examples of the substituents on the "5-membered heterocyclyl group" include halogeno groups such as fluoro, chloro, bromo, and iodo 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. alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy; haloalkoxy groups such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, and trifluoromethoxy; aryl groups such as phenyl and naphthyl; 4-chlorophenyl, 4-trifluoromethylphenyl, and 4-trifluoromethoxyphenyl. a C6-10 aryl group substituted with one or more substituents of a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group, such as a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 5-membered ring heteroaryl group such as a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, or a tetrazolyl group; a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, Preferred are a 5-membered heteroaryl group substituted with one or more substituents of a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 6-membered heteroaryl group such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, or a triazinyl group; a 6-membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or a cyano group.

[0067] In the present invention, preferred X 2 As for R 1 ON=CR 6 Examples of the groups include those represented by the formula: R1 is preferably 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- or 6-membered heterocyclyl group. R 6 is preferably a hydrogen atom or a substituted or unsubstituted C1 to C6 alkyl group. "R 1 ON=CR 6 Specific examples of the "group represented by -" include a (hydroxyimino)methyl group, an (ethoxyimino)methyl group, a 1-(ethoxyimino)ethyl group, and a 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 heterocyclyl group.

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

[0070] The "5- to 10-membered heterocyclyl group" in Q is a group containing 1, 2, 3, or 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms as ring constituent atoms. When there are two or more heteroatoms, they may be the same or different. It may be either a monocyclic or polycyclic ring. Examples of the "5- to 10-membered heterocyclyl group" include a 5- to 6-membered saturated heterocyclyl group, a 5- to 10-membered heteroaryl group, and a 5- to 10-membered partially unsaturated heterocyclyl group.

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

[0072] Examples of the substituents on the "C6-10 aryl group" or "5- to 10-membered heterocyclyl group" in Q include halogeno groups such as fluoro, chloro, bromo, and iodo 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, 1,2-dichloro-n-propyl, and the like. C1-6 haloalkyl groups such as 1-fluoro-n-butyl and 1-fluoro-n-butyl groups; C1-6 alkoxy C1-6 alkyl groups such as methoxymethyl; hydroxyl groups; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy groups; hydroxy C1-6 alkoxy groups such as hydroxyethoxy; C1-6 alkoxy alkoxy groups such as methoxymethoxy and methoxyethoxy groups; trimethylsilyloxyethoxy group, t-butyldimethylsilyloxy group, silyloxyethoxy group and other tri-C1-6 alkyl-substituted silyloxy C1-6 alkoxy groups; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, and trifluoromethoxy group; C3-6 cycloalkyl C1-6 alkoxy groups; C6-10 aryl C1-6 alkoxy groups; (C6-10 aryl substituted with one or more of the following substituents: C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group) C1-6 alkoxy group; a 5-membered heteroaryl C1-6 alkoxy group; a (5-membered heteroaryl 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) C1-6 alkoxy group; a 6-membered heteroaryl C1-6 alkoxy group; a (6-membered heteroaryl 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) C1-6 alkoxy 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, 2,2,2-trifluoroethylsulfinyl group C1-6 haloalkylsulfonyl groups such as cyclopropyl, cyclobutyl, and cyclopentyl groups; C3-6 cycloalkyl groups substituted with one or more of the following substituents: C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, C1-6 haloalkoxy groups, and cyano groups; C3-6 cycloalkenyl groups such as cyclopropenyl, cyclobutenyl, and cyclopentenyl groups; C6-10 aryl groups such as phenyl and naphthyl groups; 4-methylphenyl groups, 4- C6-10 aryl groups 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, such as a methoxyphenyl group, a 4-chlorophenyl group, a 4-fluorophenyl group, a 4-trifluoromethylphenyl group, or a 4-trifluoromethoxyphenyl group; 3- to 4-membered saturated heterocyclyl groups such as an aziridinyl group, an epoxy group, an azetidinyl group, or an oxetanyl group; a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, or a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 5- or 6-membered saturated heterocyclyl group such as a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a tetrahydro-2H-pyranyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, or a dioxanyl group; a 5- or 6-membered saturated heterocyclyl group such as a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group;Five-membered heteroaryl groups such as pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl; five-membered heteroaryl groups substituted with one or more substituents selected from the group consisting of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group; six-membered heteroaryl groups such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group; any of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group. a 6-membered heteroaryl group substituted by one or more substituents; a 5-membered partially saturated heterocyclyl group such as a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group, or an oxazolinyl group; a 5-membered partially saturated heterocyclyl group substituted by one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 6-membered partially unsaturated heterocyclyl group such as an isoxazolinyl group or a dihydropyranyl group; a 6-membered partially saturated heterocyclyl group substituted by one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; R Q1 A group represented by -CO- (wherein R Q1represents a hydrogen atom; a C1-6 alkyl group; a C1-6 alkyl group substituted with one or more substituents of a halogeno 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 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) C1-6 alkyl group; (a 5-6-membered heteroaryl 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) C1-6 alkyl group; a C2-6 alkenyl group; a C2-6 haloalkenyl group; a C2- R represents a C6-6 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, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, a C1-6 haloalkoxy group, or a cyano group; a C6-10 aryl group; a C6-10 aryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 5-6 membered heteroaryl group; or a 5-6 membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group. Q1 The same applies to . ); Carboxy group; R Q2 A group represented by -O-CO- (wherein R Q2is a C1-6 alkyl group; a C1-6 alkyl group substituted with one or more substituents of a halogeno 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 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) C1-6 alkyl group; (a 5-6-membered heteroaryl 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) C1-6 alkyl group; a C2-6 alkenyl group; a C2-6 haloalkenyl group ; a C2-6 alkynyl group; a C2-6 haloalkynyl group; a C3-6 cycloalkyl group; a C3-6 cycloalkyl group substituted with a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, a C1-6 haloalkoxy group, or a cyano group; a C6-10 aryl group; a C6-10 aryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 5-6 membered heteroaryl group; or a 5-6 membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group. Q2 The same applies to . ); R Q1 R Q1 A group represented by N- (wherein R Q1 may be the same or different. Q1 may combine together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group; R Q1 R Q1 A group represented by N-CO- (R in the formula Q1 may be the same or different. Q1 may combine together 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 -, wherein R Q3 represents a hydrogen atom; a C1-6 alkyl group; a C1-6 alkyl group substituted with one or more substituents of a halogeno 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 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) C1-6 alkyl group; or a (5-6 membered heteroaryl 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) C1-6 alkyl group. Q3 The same applies to . ); R Q2 A group represented by -O-CO-O-; R Q2 -O-CO-NR Q3 -; R Q1 R Q1 A group represented by N-CO-O- (R in the formula Q1 may be the same or different. Q1 may combine together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group; R Q1 R Q1 N-CO-NR Q3 - (wherein R Q1 may be the same or different. q1 may combine together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group. Q2 SO2-NR Q3 -; R Q1 R Q1 A group represented by N-SO2- (where R Q1 may be the same or different. Q1may combine together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group; R Q1 -ON=C(R Q4 )-, where R Q4 represents a hydrogen atom or a C1-6 alkyl group. Q1 )2C=NO- (wherein R Q1 may be the same or different. Q1 may combine together 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, as the substituent on the "5- to 10-membered heterocyclyl group", an oxo group is also preferred.

[0073] [X 3 〕 X 3 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, R 1 It represents a group represented by -CO-, a substituted or unsubstituted C3 to 6 cycloalkyl group, a substituted or unsubstituted C6 to 10 aryl group, or a substituted or unsubstituted 4 to 6-membered heterocyclyl group.

[0074] X 3 Examples of the "straight-chain C1-6 alkyl group" in the above formula include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, and an n-hexyl group. X 3 Examples of the "straight-chain C2-6 alkenyl group" in the above formula include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 4-pentenyl group, a 1-hexenyl group, a 2-hexenyl group, a 3-hexenyl group, a 4-hexenyl group, and a 5-hexenyl group. X3 Examples of the "straight-chain C2-6 alkynyl group" in the above formula include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 3-pentynyl group, a 4-pentynyl group, and a 1-hexynyl group. X 3 Examples of the "four-membered heterocyclyl group" in the above formula include an azetidinyl group and an oxetanyl group. X 3 Other specific examples of the substituents in 1 The same examples as those given above can be mentioned.

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

[0076] Examples of the substituent on a linear C1-6 alkyl group, a linear C2-6 alkenyl group, a linear C2-6 alkynyl group, a C3-6 cycloalkyl group, a C6-10 aryl group, or a 4- to 6-membered heterocyclyl group include one or more substituents selected from the following group of substituents (hereinafter, this substituent may be represented by the symbol "G"). In addition, when there are two or more substituents (G), two of them may combine together to form a divalent organic group. The following are examples of the substituent groups. 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 C 3-6 cycloalkyl group, substituted or unsubstituted C3-6 cycloalkyloxy group, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted C6-10 aryloxy group, substituted or unsubstituted C6-10 arylthio group, substituted or unsubstituted C6-10 arylsulfinyl group, substituted or unsubstituted C6-10 arylsulfonyl group, substituted or unsubstituted 3-10 membered heterocyclyl group, substituted or unsubstituted 3-10 membered heterocyclyloxy group, nitro group, cyano group, R a A group represented by -CO-, a carboxy group, R b A group represented by -O-CO-, R c R d A group represented by N-, R c R d A 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 -, R a -CO-CO-NR e -, R a -CO-NR e -NR e -, 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 -, R c R d A group represented by N-CO-O-, R c Rd N-CO-NR e -, R c R d N-CO-CO-NR e -, R a -CS-NR e -, R c R d N-CS-NR e -, R b SO2-NR e -, R c R d A group represented by N-SO2-, R a ON=CR f -, R h R j A group represented by C=NO-, R a -C(=NR g )-NR e -, R c R d NC(=NR g )-, R h R i A group represented by S(=O)=N-CO-, R h R i A group represented by S=N-CO-.

[0077] In the above substituent group, R a each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 3-10 membered heterocyclyl group. R b each 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- or 6-membered heterocyclyl group. R ceach 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- or 6-membered heterocyclyl group. R d each 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 may be taken together to form a divalent organic group. R e each 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 represents a hydrogen atom, an amino group, or a substituted or unsubstituted C1 to C6 alkyl group. R g each independently represents a hydrogen atom, a substituted or unsubstituted C1 to 6 alkyl group, or a substituted or unsubstituted C6 to 10 aryl group. R h each independently represents a substituted or unsubstituted C1 to 6 alkyl group, or a substituted or unsubstituted C6 to 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 may be taken together to form a divalent organic group.

[0078] The "halogeno group" in G includes a fluoro group, a chloro group, a bromo group, an iodo group and the like.

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

[0080] Examples of the "C2-6 alkenyl group" in G include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-methyl-2-propenyl group, a 2-methyl-2-propenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 4-pentenyl group, a 1-methyl-2-butenyl group, a 2-methyl-2-butenyl group, a 1-hexenyl group, a 2-hexenyl group, a 3-hexenyl group, a 4-hexenyl group, and a 5-hexenyl group.

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

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

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

[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 halogeno groups such as fluoro group, chloro group, bromo group, and iodo group; hydroxyl group; C1-6 alkyl groups such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, and t-butoxy group. 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-methylfuran a C6-10 aryl 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, such as a phenyl group, a 4-methoxyphenyl group, a 4-chlorophenyl group, a 4-trifluoromethylphenyl group, or a 4-trifluoromethoxyphenyl group; a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, or a tetrazolyl group; and the like; a 5-membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 6-membered heteroaryl group such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, or a triazinyl group; a 6-membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or a cyano group is preferred.

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

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

[0087] Examples of the "C6-10 arylthio group" for G include a phenylthio group, a naphthylthio group, and the like. Examples of the "C6-10 arylsulfinyl group" for G include a phenylsulfinyl group, a naphthylsulfinyl group, and the like. Examples of the "C6-10 arylsulfonyl group" for G include a phenylsulfonyl group, a naphthylsulfonyl group, and the like.

[0088] The "3- to 10-membered heterocyclyl group" in G is a group containing 1, 2, 3, or 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms as ring constituent atoms. When there are two or more heteroatoms, they may be the same or different. It may be either a monocyclic or polycyclic ring. Examples of the "3- to 10-membered heterocyclyl group" 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 the 3- to 6-membered saturated heterocyclyl group include an aziridinyl group, an epoxy group, an azetidinyl group, an oxetanyl group, a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a tetrahydro-2H-pyranyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, and a dioxanyl group. Examples of the 5- to 10-membered heteroaryl group include 5-membered heteroaryl groups such as pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl; 6-membered heteroaryl groups such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; 9-membered heteroaryl groups such as indolyl, isoindolyl, benzofuranyl, benzothienyl, indazolyl, benzimidazolyl, benzoxazolyl, benzoisoxazolyl, benzothiazolyl, and benzoisothiazolyl; and 10-membered heteroaryl groups such as quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, and quinoxalinyl. Examples of 5- to 10-membered partially unsaturated heterocyclyl groups include 5-membered partially unsaturated heterocyclyl groups such as a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group, and an oxazolinyl group; 6-membered partially unsaturated heterocyclyl groups such as an isoxazolinyl group and a dihydropyranyl group; 9-membered partially unsaturated heterocyclyl groups such as an indolinyl group, an isoindolinyl group, a 2,3-dihydrobenzofuranyl group, and a 1,3-dihydrobenzofuranyl group; and 10-membered partially unsaturated heterocyclyl groups such as a 1,2,3,4-tetrahydroquinolinyl group.

[0090] The "3- to 10-membered heterocyclyloxy group" in G has a structure in which a 3- to 10-membered heterocyclyl group and an oxy group are bonded together. Specific examples include a thiazolyloxy group and a pyridyloxy group.

[0091] Examples of the substituent on the "C3-6 cycloalkyl group", "C3-6 cycloalkyloxy group", "C6-10 aryl group", "C6-10 aryloxy group", "C6-10 arylthio group", "C6-10 arylsulfinyl group", "C6-10 arylsulfonyl group", "3-10 membered heterocyclyl group", or "3-10 membered heterocyclyloxy group" in G include halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group; a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, an i-butyl group, an aryloxy group, an arylthio group, an arylsulfinyl group, an arylsulfonyl group, an arylthio ... C1-6 alkyl groups such as butyl, t-butyl, n-pentyl, and n-hexyl; C1-6 haloalkyl groups such as chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, and 1-fluoro-n-butyl; hydroxyl; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy; C1-6 haloaryl groups such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, and trifluoromethoxy. alkoxy group; a C3-6 cycloalkyl C1-6 alkoxy group; a C6-10 aryl C1-6 alkoxy group; (a C6-10 aryl 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) C1-6 alkoxy group; a 5-membered heteroaryl C1-6 alkoxy group; (a 5-membered heteroaryl 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) Heteroaryl) C1-6 alkoxy groups; 6-membered heteroaryl C1-6 alkoxy groups; (6-membered heteroaryl 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) C1-6 alkoxy group; C1-6 alkylthio groups such as a methylthio group and an ethylthio group: C1-6 alkylsulfinyl groups such as a methylsulfinyl group and an ethylsulfinyl group; C1-6 alkylsulfonyl groups such as a methylsulfonyl group and an 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; 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 haloa a C3-6 cycloalkyl group substituted with one or more of the following substituents: an alkyl group, a C1-6 haloalkoxy group, or a cyano group; a C3-6 cycloalkenyl group; a C6-10 aryl group such as a phenyl group or a naphthyl group; or a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group such as a 4-methylphenyl group, a 4-methoxyphenyl group, a 4-chlorophenyl group, a 4-trifluoromethylphenyl group, or a 4-trifluoromethoxyphenyl group. C6-10 aryl groups substituted with a group; 3- to 4-membered saturated heterocyclyl groups such as aziridinyl, epoxy, azetidinyl, and oxetanyl groups; 3- to 4-membered saturated heterocyclyl groups substituted with one or more of the following substituents: C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, and C1-6 haloalkoxy groups; pyrrolidinyl groups, tetrahydrofuranyl groups, thiazolidinyl groups, tetrahydro-2H-pyranyl groups, piperidyl groups, piperazinyl groups, morpholinyl groups, and dioxolanyl groups. , dioxanyl group, and other 5- or 6-membered saturated heterocyclyl groups; 5- or 6-membered saturated heterocyclyl groups 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; 5-membered heteroaryl groups such as a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, or a tetrazolyl group;Five-membered heteroaryl groups 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; six-membered heteroaryl groups such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, or a triazinyl group; six-membered heteroaryl groups substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolyl group, partially unsaturated 5-membered heterocyclyl groups such as an nyl group or an oxazolinyl group; partially saturated 5-membered heterocyclyl groups 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; partially unsaturated 6-membered heterocyclyl groups such as an isoxazolinyl group or a dihydropyranyl group; partially saturated 6-membered heterocyclyl groups 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; R G1 A group represented by -CO- (wherein R G1represents a hydrogen atom; a C1-6 alkyl group; a C1-6 alkyl group substituted with one or more substituents of a halogeno 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 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) C1-6 alkyl group; (a 5-6-membered heteroaryl 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) C1-6 alkyl group; a C2-6 alkenyl group; a C2-6 haloalkenyl group; a C2- R represents a C6-6 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, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, a C1-6 haloalkoxy group, or a cyano group; a C6-10 aryl group; a C6-10 aryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 5-6 membered heteroaryl group; or a 5-6 membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group. G1 The same applies to . ); Carboxy group; R G2 A group represented by -O-CO- (wherein R G2is a C1-6 alkyl group; a C1-6 alkyl group substituted with one or more substituents of a halogeno 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 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) C1-6 alkyl group; (a 5-6-membered heteroaryl 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) C1-6 alkyl group; a C2-6 alkenyl group; a C2-6 haloalkenyl group ; a C2-6 alkynyl group; a C2-6 haloalkynyl group; a C3-6 cycloalkyl group; a C3-6 cycloalkyl group substituted with a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, a C1-6 haloalkoxy group, or a cyano group; a C6-10 aryl group; a C6-10 aryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 5-6 membered heteroaryl group; or a 5-6 membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group. G2 The same applies to . ); R G1 R G1 A group represented by N- (wherein R q1 may be the same or different. G1 may combine together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group; R G1 R G1 A group represented by N-CO- (R in the formula G1 may be the same or different. G1 may combine together 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 -, wherein R G3 represents a hydrogen atom; a C1-6 alkyl group; a C1-6 alkyl group substituted with one or more substituents of a halogeno 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 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) C1-6 alkyl group; or a (5-6 membered heteroaryl 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) C1-6 alkyl group. G3 The same applies to . ); R G2 A group represented by -O-CO-O-; R G2 -O-CO-NR G3 -; R G1 R G1 A group represented by N-CO-O- (R in the formula G1 may be the same or different. G1 may combine together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group; R G1 R G1 N-CO-NR G3 - (wherein R G1 may be the same or different. G1 may combine together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group. G2 SO2-NR G3 -; R G1 R G1 A group represented by N-SO2- (R in the formula G1 may be the same or different. G1may combine together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group; R G1 -ON=C(R G4 )-, where R G4 represents a hydrogen atom or a C1-6 alkyl group. G1 )2C=NO- (wherein R G1 may be the same or different. G1 may combine together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group; A pentafluorosulfanyl group, a nitro group, or a cyano group is preferred. Furthermore, as a substituent on a "C3-6 cycloalkyl group", a "C3-6 cycloalkyloxy group", a "3-10 membered heterocyclyl group", or a "3-10 membered heterocyclyloxy group", an oxo group is also preferred.

[0092] "R" in G a In the group represented by -CO-, R a represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a 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 the "C1-6 alkyl group" in the above formula include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an i-propyl group, an i-butyl group, an s-butyl group, an t-butyl group, an i-pentyl group, a neopentyl group, a 2-methylbutyl group, and an i-hexyl group. R a Examples of the "C2-6 alkenyl group" in the above formula include a vinyl group and a 1-propenyl group. R aExamples of the "C2-6 alkynyl group" in the above formula include an ethynyl group and a 1-propynyl group. R aIn the above, examples of the substituents on the "C1-6 alkyl group", "C2-6 alkenyl group", or "C2-6 alkynyl group" include halogeno groups such as fluoro, chloro, bromo, and iodo 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; C1-6 alkylthio groups such as methylthio and ethylthio groups; C1-6 alkylsulfinyl groups such as methylsulfonyl and ethylsulfonyl; C1-6 alkylsulfonyl groups such as methylsulfonyl and ethylsulfonyl; carboxy groups; C1-6 alkoxycarbonyl groups such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, i-propoxycarbonyl, n-butoxycarbonyl and t-butoxycarbonyl; C3-6 cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl; C6-10 aryl groups such as phenyl and naphthyl. a C6-10 aryl group substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group, such as a 4-methylphenyl group, a 4-methoxyphenyl group, a 4-chlorophenyl group, a 4-trifluoromethylphenyl group, or a 4-trifluoromethoxyphenyl group; a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, a 5-membered heteroaryl group such as an aryl group or a tetrazolyl group; a 5-membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 6-membered heteroaryl group such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, or a triazinyl group; a 6-membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group;Or a cyano group is preferred.

[0094] R a Examples of the "C3-6 cycloalkyl group" in the above formula include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. R a Examples of the "C6-10 aryl group" in the above formula include a phenyl group, a naphthyl group, an indenyl group, an indanyl group, and a tetralinyl group.

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

[0096] R aIn the above, examples of the substituents on the "C3-6 cycloalkyl group", "C6-10 aryl group", or "3- to 10-membered heterocyclyl group" include halogeno groups such as fluoro, chloro, bromo, and iodo 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 haloaryl groups such as chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, and 1-fluoro-n-butyl groups; alkyl 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; 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, and C1-6 haloalkoxy groups) C6-10 aryl substituted with one or more substituents)C1-6 alkoxy group; 5-membered heteroaryl C1-6 alkoxy group; (5-membered heteroaryl substituted with one or more substituents of C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group)C1-6 alkoxy group; 6-membered heteroaryl C1-6 alkoxy group; (one or more substituents of C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group) (a 6-membered heteroaryl substituted with) C1-6 alkoxy groups; C1-6 alkylthio groups such as a methylthio group and an ethylthio group: C1-6 alkylsulfinyl groups such as a methylsulfinyl group and an ethylsulfinyl group; C1-6 alkylsulfonyl groups such as a methylsulfonyl group and an ethylsulfonyl group; C1-6 haloalkylthio groups such as a trifluoromethylthio group and a 2,2,2-trifluoroethylthio group: C1-6 haloalkylsulfinyl groups such as a trifluoromethylsulfinyl group and a 2,2,2-trifluoroethylsulfinyl group;C1-6 haloalkylsulfonyl groups such as trifluoromethylsulfonyl and 2,2,2-trifluoroethylsulfonyl; C3-6 cycloalkyl groups such as cyclopropyl, cyclobutyl and cyclopentyl; C3-6 cycloalkyl groups substituted with one or more of the following substituents: C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, C1-6 haloalkoxy groups, and cyano groups; C3-6 cycloalkenyl groups; C6-10 aryl groups such as phenyl and naphthyl; 4-methylphenyl groups, 4-methylphenyl groups, a C6-10 aryl group substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group, such as an aryloxyphenyl group, a 4-chlorophenyl group, a 4-trifluoromethylphenyl group, and a 4-trifluoromethoxyphenyl group; a 3- or 4-membered saturated heterocyclyl group, such as an aziridinyl group, an epoxy group, an azetidinyl group, and an oxetanyl group; a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group; a 3- or 4-membered saturated heterocyclyl group substituted with one or more substituents of any one of an oxy group; a 5- or 6-membered saturated heterocyclyl group such as a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a tetrahydro-2H-pyranyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, or a dioxanyl group; a 5- or 6-membered saturated heterocyclyl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a pyrrolyl group, a furyl group , thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group, and other 5-membered ring heteroaryl groups; 5-membered ring heteroaryl groups 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; 6-membered ring heteroaryl groups such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, and other groups;6-membered heteroaryl groups 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; 5-membered partially unsaturated heterocyclyl groups such as a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group, or an oxazolinyl group; 5-membered partially saturated heterocyclyl groups 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; 6-membered partially unsaturated heterocyclyl groups such as an isoxazolinyl group or a dihydropyranyl group; 6-membered partially saturated heterocyclyl groups 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; R q1 A group represented by -CO- (wherein R q1represents a hydrogen atom; a C1-6 alkyl group; a C1-6 alkyl group substituted with one or more substituents of a halogeno 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 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) C1-6 alkyl group; (a 5-6-membered heteroaryl 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) C1-6 alkyl group; a C2-6 alkenyl group; a C2-6 haloalkenyl group; a C2- R represents a C6-6 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, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, a C1-6 haloalkoxy group, or a cyano group; a C6-10 aryl group; a C6-10 aryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 5-6 membered heteroaryl group; or a 5-6 membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group. q1 The same applies to . ); Carboxy group; R q2 A group represented by -O-CO- (wherein R q2is a C1-6 alkyl group; a C1-6 alkyl group substituted with one or more substituents of a halogeno 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 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) C1-6 alkyl group; (a 5-6-membered heteroaryl 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) C1-6 alkyl group; a C2-6 alkenyl group; a C2-6 haloalkenyl group; a C2-6 a R represents an 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, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, a C1-6 haloalkoxy group, or a cyano group; a C6-10 aryl group; a C6-10 aryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 5-6 membered heteroaryl group; or a 5-6 membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group. q2 Same in ); R q1 R q1 A group represented by N- (wherein R q1 may be the same or different. q1 may combine together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group; R q1 R q1 A group represented by N-CO- (R in the formula q1 may be the same or different. q1may combine together 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 -, wherein R q3 represents a hydrogen atom; a C1-6 alkyl group; a C1-6 alkyl group substituted with one or more substituents of a halogeno 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 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) C1-6 alkyl group; or a (5-6 membered heteroaryl 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) C1-6 alkyl group. q3 The same applies in . ); R q2 A group represented by -O-CO-O-; R q2 -O-CO-NR q3 -; R q1 R q1 A group represented by N-CO-O- (R in the formula q1 may be the same or different. q1 may combine together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group; R q1 R q1 N-CO-NR q3 - (wherein R q1 may be the same or different. q1 may combine together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group. q2 SO2-NR q3 -; R q1 R q1 A group represented by N-SO2- (R in the formulaq1 may be the same or different. q1 may combine together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group; R q1 -ON=C(R q4 )-, where R q4 represents a hydrogen atom or a C1-6 alkyl group. q1 )2C=NO- (wherein R q1 may be the same or different. q1 may combine together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group; A pentafluorosulfanyl group, a nitro group, or a cyano group is preferred. Furthermore, as a substituent on the "C3-6 cycloalkyl group" or the "3-10-membered heterocyclyl group", an oxo group is also preferred.

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

[0098] "R" in G b In the group represented by -O-CO-, R b 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- or 6-membered heterocyclyl group. R b Specific examples of the substituents in a The same examples as those given above can be mentioned.

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

[0100] "R" in G c R d In the group represented by N-, R c 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- or 6-membered heterocyclyl group; R d 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 Specific examples of the substituents in a The same examples as those given above can be mentioned. R d Examples of the "C1-6 alkoxy group" in the above formula include a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, an i-propoxy group, an i-butoxy group, an s-butoxy group, a t-butoxy group, and an i-hexyloxy group. R dIn the above, examples of the substituents on the "C1-6 alkoxy group" include halogeno groups such as fluoro, chloro, bromo, and iodo 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 a C3-6 cycloalkyl group such as a cyclohexyl group; a C6-10 aryl group such as a phenyl group or a naphthyl group; a C6-10 aryl group substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group, such as a 4-methylphenyl group, a 4-methoxyphenyl group, a 4-chlorophenyl group, a 4-trifluoromethylphenyl group, or a 4-trifluoromethoxyphenyl group; or a cyano group.

[0101] Here, R c and R d may be taken together to form a divalent organic group. Examples of the divalent organic group that can be formed include a substituted or unsubstituted C2-5 alkylene group, a substituted or unsubstituted C1-3 alkyleneoxyC1-3 alkylene group, a substituted or unsubstituted C1-3 alkylenethioC1-3 alkylene group, and a substituted or unsubstituted C1-3 alkyleneiminoC1-3 alkylene group. Further examples include silicon-containing divalent hydrocarbon groups such as -CH2CH2-Si(CH3)2-CH2CH2-. Examples of the "C2-5 alkylene group" include a dimethylene group, a trimethylene group, and a tetramethylene group. Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group. Examples of the "C1-3 alkylene thio C1-3 alkylene group" include a dimethylene thiodimethylene group. Examples of the "C1-3 alkyleneimino C1-3 alkylene group" include a dimethyleneiminodimethylene group. Here, the imino group of the "C1-3 alkylene alkylene imino C1-3 alkylene group" means -NH-. Preferred substituents on the "C2-5 alkylene group", "C1-3 alkyleneoxy C1-3 alkylene group", "C1-3 alkylenethio C1-3 alkylene group" and "C1-3 alkyleneimino C1-3 alkylene group" are halogeno groups such as a fluoro group, a chloro group, a bromo group or an iodo group; C1-6 alkyl groups such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, an i-butyl group or a t-butyl group; a methylidene group; or C1-6 haloalkyl groups such as a chloromethyl group, a chloroethyl group, a trifluoromethyl group, a 1,2-dichloro-n-propyl group or a 1-fluoro-n-butyl group.

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

[0103] "R" in G c R d In the group represented by N-CO-, R c and R d is the above "R c R d The meanings are the same as those in "a group represented by N-." "R c R d Specific examples of the "group represented by N-CO-" include a carbamoyl group, an N,N-dimethylaminocarbonyl group, an N-(i-propyl)aminocarbonyl group, and an 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 dis the above "R c R d The meanings are the same as those in "a group represented by N-." "R c R d N-NR d A specific example of the group represented by --CO-- is 2,2-dimethylhydrazine-1-carbonyl group.

[0105] "R" in G a In the group represented by -CO-O-, R a is the above "R a The meaning is the same as that of the group represented by -CO-. "R a A specific example of the group represented by --CO--O-- is an acetyloxy group.

[0106] "R" in G a -CO-NR e In the group represented by "-", R a is the above "R a The meaning is the same as that of the group represented by -CO-. R e 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 Specific examples of the substituents in a The same examples as those given above can be mentioned. "R a -CO-NR e Specific examples of the "group represented by -" include an acetylamino group, a propionylamino group, a butyrylamino group, and an i-propylcarbonylamino group.

[0107] "R" in G a -CO-CO-NR e In the group represented by "-", R a is the above "R a -CO- group" has the same meaning as that in "R e is the same as "Ra -CO-NR e -" has the same meaning as that in "a group represented by the formula "-". "R a -CO-CO-NR e A specific example of the "group represented by -" is an oxopropanamide group.

[0108] "R" in G a -CO-NR e -NR e In the group represented by "-", R a is the above "R a -CO- group" has the same meaning as that in "R e is the same as "R a -CO-NR e -" has the same meaning as that in "a group represented by the formula "-". "R a -CO-NR e -NR e Specific examples of the "group represented by -" include an acetylhydrazinyl group, an i-propylcarbonylhydrazinyl group, and the like.

[0109] "R" in G a -CO-NR e -NR e In the group represented by -CO-, R a is the above "R a -CO- group" has the same meaning as that in "R e is the same as "R a -CO-NR e -" has the same meaning as that in "a group represented by the formula "-". "R a -CO-NR e -NR e A specific example of the "group represented by --CO--" is a 2-acetylhydrazine-1-carbonyl group.

[0110] "R" in G b In the group represented by -O-CO-O-, R b is the above "R b-O-CO- group" has the same meaning as that in "a group represented by -O-CO-". "R b Specific examples of the "group represented by --O--CO--O--" include a methoxycarbonyloxy group, an ethoxycarbonyloxy group, and the like.

[0111] "R" in G b -O-CO-NR e In the group represented by "-", R b is the above "R b -O-CO- group" has the same meaning as that in "R e is the above "R b -CO-NR e -" has the same meaning as that in "a group represented by the formula "-". "R b -O-CO-NR e A specific example of the "group represented by -" is a methoxycarbonylamino group.

[0112] "R" in G c R d In the group represented by N-CO-O-, R c and R d is the above "R c R d The meanings are the same as those in "a group represented by N-." "R c R d Specific examples of the "group represented by N-CO-O-" include a carbamoyloxy group, an N,N-dimethylaminocarbonyloxy group, and the like.

[0113] "R" in G c R d N-CO-NR e In the group represented by "-", R c and R d is the above "R c R d The meanings are the same as those in "Group represented by N-" e is the above "R a -CO-NR e -" has the same meaning as that in "a group represented by the formula "-". "R c R d N-CO-NR e Specific examples of the "group represented by -" include a carbamoylamino group, an N,N-dimethylaminocarbonylamino group, and the like.

[0114] "R" in G c R d N-CO-CO-NR e In the group represented by "-", R c and R d is the above "R c R d The meanings are the same as those in "Group represented by N-" e is the above "R a -CO-NR e -" has the same meaning as that in "a group represented by the formula "-". "R c R d N-CO-CO-NR e Specific examples of the "group represented by -" include a 2-(methylamino)-2-oxoacetamide group, a 2-(t-butylamino)-2-oxoacetamide group, and the like.

[0115] "R" in G a -CS-NR e In the group represented by "-", R a is the above "R a -CO- group" has the same meaning as that in "R e is the same as "R a -CO-NR e -" has the same meaning as that in "a group represented by the formula "-". "R a -CS-NR e Specific examples of the "group represented by -" include an ethanethioamide group, a propanethioamide group, and a 2-methylpropanethioamide group.

[0116] "R" in G c R d N-CS-NR e In the group represented by "-", R c and Rd is the above "R c R d The meanings are the same as those in "Group represented by N-" e is the above "R a -CO-NR e -" has the same meaning as that in "a group represented by the formula "-". "R c R d N-CS-NR e A specific example of the "group represented by -" is a 3,3-dimethylthioureido group.

[0117] "R" in G b SO2-NR e In the group represented by "-", R b is the above "R b -O-CO- group" has the same meaning as that in "R e is the above "R a -CO-NR e -" has the same meaning as that in "a group represented by the formula "-". "R b SO2-NR e Specific examples of the "group represented by -" include a methanesulfonylamino group.

[0118] "R" in G c R d In the group represented by N-SO2-, R c and R d is the above "R c R d The meanings are the same as those in "a group represented by N-." "R c R d A specific example of the "group represented by N-SO2-" is an N,N-dimethylaminosulfonyl group.

[0119] "R" in G a ON=CR f In the group represented by "-", R a is the above "R a The meaning is the same as that of the group represented by -CO-. R f represents a hydrogen atom, an amino group, or a substituted or unsubstituted C1 to C6 alkyl group. R f Specific examples of the substituents in a The same examples as those given above can be mentioned. "R a ON=CR f Specific examples of the "group represented by -" include a (hydroxyimino)methyl group, an (ethoxyimino)methyl group, and the like.

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

[0121] "R" in G c R d NC(=NR g In the group represented by the formula "R c and R d is the above "R c R d The meanings are the same as those in "Group represented by N-" g is the above "R a -C(=NR g )-NR e -" has the same meaning as that in "a group represented by the formula "-".

[0122] "R" in G h Ri 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; R i each independently represents a substituted or unsubstituted C1 to 6 alkyl group, or a substituted or unsubstituted C6 to 10 aryl group. R h or R i Specific examples of the substituents in a The same examples as those given above can be mentioned.

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

[0124] "R" in G h R i In the group represented by S=N-CO-, R h or R i is the above "R h R iThe meanings are the same as those in "a 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 is the above "R h R j The meaning is the same as that of "a group represented by S=NO-". "R h R j Specific examples of the "group represented by C=NO-" include a (propan-2-ylideneamino)oxy group.

[0126] When there are two or more substituents (G), examples of the divalent organic group that can be formed by combining two of them include a substituted or unsubstituted C1-5 alkylene group, a substituted or unsubstituted oxyC1-4 alkylene group, a substituted or unsubstituted oxyC2-3 alkyleneoxy group, and a substituted or unsubstituted C1-3 alkyleneoxyC1-3 alkylene group. Examples of the "C1-5 alkylene group" include a methylene group, a dimethylene group, a trimethylene group, and a tetramethylene group. Examples of the "oxy C1-4 alkylene group" include an oxymethylene group and an oxydimethylene group. Examples of the "oxy C2-3 alkyleneoxy group" include an oxydimethyleneoxy group. Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group. Preferred substituents on the "C1-5 alkylene group", "oxy C1-4 alkylene group", "oxy C2-3 alkyleneoxy group", and "C1-3 alkyleneoxy C1-3 alkylene group" are halogeno groups such as fluoro, chloro, bromo, and iodo groups; C1-6 alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, and t-butyl groups; or C1-6 haloalkyl groups such as chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, and 1-fluoro-n-butyl groups.

[0127] In the present invention, preferred examples of G include a halogeno 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, 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 C6-10 aryl group, a substituted or unsubstituted 3-10 membered heterocyclyl group, R b A group represented by -O-CO-, R c R d A group represented by N-, R c R d A group represented by N-CO-, R a A group represented by -CO-O-, R a -CO-NR e -, R b -O-CO-NR e -, R c R d A group represented by N-CO-O-, R c R d N-CO-NR e -, R c R d N-CS-NR e -, R b SO2-NR e -, R a ON=CR f -, or R h R iExamples thereof include a 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 the "C1-6 alkylene group" in A include a methylene group, a dimethylene group, a trimethylene group, and a tetramethylene group. Examples of the "C2-6 alkenylene group" in A include a vinylene group (-CH=CH-), a divinylene group (-CH=CH-CH=CH-), a propenylene group (-CH=CH-CH2-, -CH2-CH=CH-), and the like. Examples of the "C2-6 alkynylene group" in A include an ethynylene group (-C≡C-), a propynylene group (-CH2-C≡C-, -C≡C-CH2-), and the like. Examples of the "C3-6 cycloalkylene group" in A include a 1,2-cyclopropylene group, a 1,2-cyclobutanediyl group, and a 1,3-cyclobutanediyl group.

[0130] In the present invention, preferred examples of A include a substituted or unsubstituted C1-6 alkylene group or a substituted or unsubstituted C2-6 alkenylene group. Examples of the substituent on the C1-6 alkylene group or the C2-6 alkenylene group include one or more substituents selected from the following group of substituents (hereinafter, this substituent may be represented by the symbol "Ga"). In addition, when there are two or more substituents (Ga), two of them may combine together to form a divalent organic group. The following are examples of the substituent groups. 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 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 C1-6 alkylthio ... Unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C3-6 cycloalkyloxy group, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted C6-10 aryloxy group, substituted or unsubstituted C6-10 arylthio group, substituted or unsubstituted C6-10 arylsulfinyl group, substituted or unsubstituted C6-10 arylsulfonyl group, substituted or unsubstituted 3-6 membered heterocyclyl group, substituted or unsubstituted 3-6 membered heterocyclyloxy group, nitro group, 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 -, R b1 A group represented by -O-CO-O-, R b1 -O-CO-NR e1 -, R c1 R d1 A group represented by N-CO-O-, R c1 R d1 N-CO-NR e1 -, R b1 SO2-NR e1 -, R c1 R d1 A group represented by N-SO2-, R a1 ON=CR f1 -, R g1 R h1Groups represented by C=NO-, oxo group (O=), thioxo group (S=), R a1 A divalent group represented by -N=, R a1 A divalent group represented by ON=, R c1 R d1 A divalent group represented by NN=, R a1 -CO-NR e1 A divalent group represented by -N=, R b1 -O-CO-NR e1 A divalent group represented by -N=, R b1 SO2-NR e1 A divalent group represented by -N=.

[0131] In the above substituent group, R a1 each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group, R b1 each 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- or 6-membered heterocyclyl group, R c1 each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group, R d1 each 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 may be taken together to form a divalent organic group. Re1 each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, R f1 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, R g1 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- or 6-membered heterocyclyl group, R h1 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, where R g1 and R h1 may be taken together to form a divalent organic group.

[0132] Examples of the "halogeno group" in Ga include a fluoro group, a chloro group, a bromo group, and an iodo group.

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

[0134] Examples of the "C2-6 alkenyl group" for Ga include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-methyl-2-propenyl group, a 2-methyl-2-propenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 4-pentenyl group, a 1-methyl-2-butenyl group, a 2-methyl-2-butenyl group, a 1-hexenyl group, a 2-hexenyl group, a 3-hexenyl group, a 4-hexenyl group, and a 5-hexenyl group.

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

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

[0137] Examples of the "C1-6 alkylthio group" for Ga include a methylthio group, an ethylthio group, an n-propylthio group, an n-butylthio group, an n-pentylthio group, an n-hexylthio group, and an i-propylthio group. Examples of the "C1-6 alkylsulfinyl group" for Ga include a methylsulfinyl group, an ethylsulfinyl group, and a t-butylsulfinyl group. Examples of the "C1-6 alkylsulfonyl group" for Ga include a methylsulfonyl group, an ethylsulfonyl group, and a t-butylsulfonyl group.

[0138] 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 Ga include halogeno groups such as fluoro group, chloro group, bromo group, and iodo 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, and t-butoxy group; 2-chloro-n-propoxy group, 2,3-dichloro-n-propoxy group, Preferred are C1-6 haloalkoxy groups such as a chlorobutoxy group, trifluoromethoxy group, etc.; C3-6 cycloalkyl groups such as a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, etc.; C6-10 aryl groups such as a phenyl group, naphthyl group, etc.; C6-10 aryl groups 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, such as a 4-methylphenyl group, a 4-methoxyphenyl group, a 4-chlorophenyl group, a 4-trifluoromethylphenyl group, or a 4-trifluoromethoxyphenyl group; or a cyano group.

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

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

[0141] Examples of the "C6-10 arylthio group" for Ga include a phenylthio group and a naphthylthio group. Examples of the "C6-10 arylsulfinyl group" for Ga include a phenylsulfinyl group and a naphthylsulfinyl group. Examples of the "C6-10 arylsulfonyl group" for Ga include a phenylsulfonyl group and a naphthylsulfonyl group.

[0142] The "3- to 6-membered heterocyclyl group" in Ga is a group containing 1, 2, 3, or 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms as ring constituent atoms. When there are two or more heteroatoms, they may be the same or different. Examples of the "3- to 6-membered heterocyclyl group" include 3- to 6-membered saturated heterocyclyl groups, 5- to 6-membered heteroaryl groups, and 5- to 6-membered partially unsaturated heterocyclyl groups.

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

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

[0145] Examples of the substituent on the "C3-6 cycloalkyl group", "C3-6 cycloalkyloxy group", "C6-10 aryl group", "C6-10 aryloxy group", "C6-10 arylthio group", "C6-10 arylsulfinyl group", "C6-10 arylsulfonyl group", "3- to 6-membered heterocyclyl group", or "3- to 6-membered heterocyclyloxy group" in Ga include halogeno groups such as fluoro group, chloro group, bromo group, and iodo group; 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; chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, and 1-fluoro-n-butyl group. Preferred are a C1-6 haloalkyl group; a hydroxyl group; a C1-6 alkoxy group such as a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group, or a t-butoxy group; a C1-6 haloalkoxy group such as a 2-chloro-n-propoxy group, a 2,3-dichlorobutoxy group, or a trifluoromethoxy group; a C6-10 aryl group such as a phenyl group or a naphthyl group; a C6-10 aryl 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, such as a 4-methylphenyl group, a 4-methoxyphenyl group, a 4-chlorophenyl group, a 4-trifluoromethylphenyl group, or a 4-trifluoromethoxyphenyl group; or a cyano group.

[0146] "R" in Ga a1 In the group represented by -CO-, R a1represents 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- or 6-membered heterocyclyl group.

[0147] R a1 Examples of the "C1-6 alkyl group" in the above formula include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an i-propyl group, an i-butyl group, an s-butyl group, an t-butyl group, an i-pentyl group, a neopentyl group, a 2-methylbutyl group, and an i-hexyl group. R a1 Examples of the "C2-6 alkenyl group" in the above formula include a vinyl group and a 1-propenyl group. R a1 Examples of the "C2-6 alkynyl group" in the above formula include an ethynyl group and a 1-propynyl group. R a1 In the above, examples of the substituents on the "C1-6 alkyl group", "C2-6 alkenyl group", or "C2-6 alkynyl group" include halogeno groups such as fluoro, chloro, bromo, and iodo 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 alkoxy groups such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, and trifluoromethoxy groups; Preferred are 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 halogeno groups, C1-6 haloalkyl groups, and C1-6 haloalkoxy groups, such as 4-chlorophenyl, 4-trifluoromethylphenyl, and 4-trifluoromethoxyphenyl groups; or cyano groups.

[0148] R a1Examples of the "C3-6 cycloalkyl group" in the above formula include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. R a1 Examples of the "C6-10 aryl group" in the above formula include a phenyl group and a naphthyl group.

[0149] R a1 The "5- or 6-membered heterocyclyl group" in the above is a group containing 1, 2, 3, or 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms as ring constituent atoms. When there are two or more heteroatoms, they may be the same or different. Examples of the "5- or 6-membered heterocyclyl group" include 5- or 6-membered saturated heterocyclyl groups, 5- or 6-membered heteroaryl groups, and 5- or 6-membered partially unsaturated heterocyclyl groups. Examples of the 5- to 6-membered saturated heterocyclyl group include a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a tetrahydro-2H-pyranyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, and a dioxanyl group. Examples of the 5- or 6-membered heteroaryl group include 5-membered heteroaryl groups such as a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, and a tetrazolyl group; and 6-membered heteroaryl groups such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group. Examples of 5- to 6-membered partially unsaturated heterocyclyl groups include 5-membered partially unsaturated heterocyclyl groups such as a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group, and an oxazolinyl group; and 6-membered partially unsaturated heterocyclyl groups such as an isoxazolinyl group and a dihydropyranyl group.

[0150] R a1In the above, examples of the substituents on the "C3-6 cycloalkyl group", "C6-10 aryl group", or "5- or 6-membered heterocyclyl group" include halogeno groups such as fluoro, chloro, bromo, and iodo 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, Preferred are 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, and C1-6 haloalkoxy groups, such as 4-methylphenyl, 4-methoxyphenyl, 4-chlorophenyl, 4-trifluoromethylphenyl, and 4-trifluoromethoxyphenyl groups; or cyano groups.

[0151] "R a1 Specific examples of the "group represented by --CO--" include a formyl group, an acetyl group, and the like.

[0152] "R" in Ga b1 In the group represented by -O-CO-, R b1 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- or 6-membered heterocyclyl group. R b1 Specific examples of the substituents in a1 The same examples as those given above can be mentioned.

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

[0154] "R" in Ga c1 R d1 In the group represented by N-, R c1 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- or 6-membered heterocyclyl group; R d1 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 Specific examples of the substituents in a1 The same examples as those given above can be mentioned. Here, R c1 and R d1 may be taken together to form a divalent organic group. Examples of the divalent organic group that can be formed include a substituted or unsubstituted C2-5 alkylene group or a substituted or unsubstituted C1-3 alkyleneoxy C1-3 alkylene group. Examples of the "C2-5 alkylene group" include a dimethylene group, a trimethylene group, and a tetramethylene group. Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group. Preferred substituents on the "C2-5 alkylene group" or the "C1-3 alkyleneoxy C1-3 alkylene group" are halogeno groups such as a fluoro group, a chloro group, a bromo group, or an iodo group; C1-6 alkyl groups such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, an i-butyl group, or a t-butyl group; or C1-6 haloalkyl groups such as a chloromethyl group, a chloroethyl group, a trifluoromethyl group, a 1,2-dichloro-n-propyl group, or a 1-fluoro-n-butyl group.

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

[0156] "R" in Ga c1 R d1 In the group represented by N-CO-, R c1 and R d1 is the above "R c1 R d1 The meanings are the same as those in "a group represented by N-." "R c1 R d1 Specific examples of the "group represented by N-CO-" include a carbamoyl group, an N,N-dimethylaminocarbonyl group, an N-(i-propyl)aminocarbonyl group, and an N-(i-propyl)-N-methylaminocarbonyl group.

[0157] "R" in Ga a1 In the group represented by -CO-O-, R a1 is the above "R a1 The meaning is the same as that of the group represented by -CO-. "R a1 A specific example of the group represented by --CO--O-- is an acetyloxy group.

[0158] "R" in Ga a1 -CO-NR e1 In the group represented by "-", R a1 is the above "R a1The meaning is the same as that of the group represented by -CO-. R e1 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. R e1 Specific examples of the substituents in a1 The same examples as those given above can be mentioned. "R a1 -CO-NR e1 A specific example of the "group represented by -" is an acetylamino group.

[0159] "R" in Ga b1 In the group represented by -O-CO-O-, R b1 is the above "R b1 -O-CO- group" has the same meaning as that in "a group represented by -O-CO-". "R b1 Specific examples of the "group represented by --O--CO--O--" include a methoxycarbonyloxy group, an ethoxycarbonyloxy group, and the like.

[0160] "R" in Ga b1 -O-CO-NR e1 In the group represented by "-", R b1 is the above "R b1 -O-CO- group" has the same meaning as that in "R e1 is the above "R b1 -CO-NR e1 -" has the same meaning as that in "a group represented by the formula "-". "R b1 -O-CO-NR e1 A specific example of the "group represented by -" is a methoxycarbonylamino group.

[0161] "R" in Ga c1 R d1 In the group represented by N-CO-O-, R c1 and R d1 is the above "R c1 R d1The meanings are the same as those in "a group represented by N-." "R c1 R d1 Specific examples of the "group represented by N-CO-O-" include a carbamoyloxy group, an N,N-dimethylaminocarbonyloxy group, and the like.

[0162] "R" in Ga c1 R d1 N-CO-NR e1 In the group represented by "-", R c1 and R d1 is the above "R c1 R d1 The meanings are the same as those in "Group represented by N-" e1 is the above "R a1 -CO-NR e1 -" has the same meaning as that in "a group represented by the formula "-". "R c1 R d1 N-CO-NR e1 Specific examples of the "group represented by -" include a carbamoylamino group, an N,N-dimethylaminocarbonylamino group, and the like.

[0163] "R" in Ga b1 SO2-NR e1 In the group represented by "-", R b1 is the above "R b1 -O-CO- group" has the same meaning as that in "R e1 is the above "R a1 -CO-NR e1 -" has the same meaning as that in "a group represented by the formula "-". "R b1 SO2-NR e1 Specific examples of the "group represented by -" include a methanesulfonylamino group.

[0164] "R" in Ga c1 R d1 In the group represented by N-SO2-, R c1 and R d1 is the above "R c1 R d1The meanings are the same as those in "a group represented by N-." "R c1 R d1 A specific example of the "group represented by N-SO2-" is an N,N-dimethylaminosulfonyl group.

[0165] "R" in Ga a1 ON=CR f1 In the group represented by "-", R a1 is the above "R a1 The meaning is the same as that of the group represented by -CO-. R f1 represents a hydrogen atom, or a substituted or unsubstituted C1-6 alkyl group. R f1 Specific examples of the substituents in a The same examples as those given above can be mentioned. "R a1 ON=CR f1 Specific examples of the "group represented by -" include a (hydroxyimino)methyl group, an (ethoxyimino)methyl group, and the like.

[0166] "R" in Ga g1 R h1 In the group represented by C=NO-, R g1 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- or 6-membered heterocyclyl group; R h1 represents a hydrogen atom, or a substituted or unsubstituted C1-6 alkyl group. R g1 or R h1 Specific examples of the substituents in a1 The same examples as those given above can be mentioned. Here, R g1 and R h1 may be taken together to form a divalent organic group. Examples of the divalent organic group that can be formed include a substituted or unsubstituted C2-5 alkylene group or a substituted or unsubstituted C1-3 alkyleneoxy C1-3 alkylene group. Examples of the "C2-5 alkylene group" include a dimethylene group, a trimethylene group, and a tetramethylene group. Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group. Preferred substituents on the "C2-5 alkylene group" or the "C1-3 alkyleneoxy C1-3 alkylene group" are halogeno groups such as a fluoro group, a chloro group, a bromo group, or an iodo group; C1-6 alkyl groups such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, an i-butyl group, or a t-butyl group; or C1-6 haloalkyl groups such as a chloromethyl group, a chloroethyl group, a trifluoromethyl group, a 1,2-dichloro-n-propyl group, or a 1-fluoro-n-butyl group. "R g1 R h1 Specific examples of the "group represented by C=NO-" include a (propan-2-ylideneamino)oxy group.

[0167] "R" in Ga a1 In the "divalent group represented by -N=", R a1 is the above "R a1 The meaning is the same as that of the group represented by -CO-. "R a1 Specific examples of the divalent group represented by -N= include an imino group (HN=) and a methylimino group.

[0168] "R" in Ga a1 In the "divalent group represented by ON=", R a1 is the above "R a1 The meaning is the same as that of the group represented by -CO-. "R a1 Specific examples of the divalent group represented by ON= include an N-hydroxyimino group and an N-methoxyimino group.

[0169] "R" in Ga c1 R d1 In the "divalent group represented by NN=", R c1 and R d1 is the above "R c1 R d1 The meanings are the same as those in "a group represented by N-." "R c1 R d1 A specific example of the divalent group represented by NN= is a 2,2-dimethylhydrazinylidene group.

[0170] "R" in Ga a1 -CO-NR e1 In the "divalent group represented by -N=", R a1 is the above "R a1 -CO- group" has the same meaning as that in "R e1 is the above "R a1 -CO-NR e1 -" has the same meaning as that in "a group represented by the formula "-".

[0171] "R" in Ga b1 -O-CO-NR e1 In the "divalent group represented by -N=", R b1 is the above "R b1 -O-CO- group" has the same meaning as that in "R e1 is the above "R a1 -CO-NR e1 -" has the same meaning as that in "a group represented by the formula "-".

[0172] "R" in Ga b1 SO2-NR e1 In the "divalent group represented by -N=", R b1 is the above "R b1 -O-CO- group" has the same meaning as that in "R e1 is the above "R a1 -CO-NR e1 -" has the same meaning as that in "a group represented by the formula "-".

[0173] When there are two or more substituents (Ga), examples of the divalent organic group that can be formed by combining two of them include a substituted or unsubstituted C1-5 alkylene group, a substituted or unsubstituted oxyC1-4 alkylene group, a substituted or unsubstituted oxyC2-3 alkyleneoxy group, and a substituted or unsubstituted C1-3 alkyleneoxyC1-3 alkylene group. Examples of the "C1-5 alkylene group" include a methylene group, a dimethylene group, a trimethylene group, and a tetramethylene group. Examples of the "oxy C1-4 alkylene group" include an oxymethylene group and an oxydimethylene group. Examples of the "oxy C2-3 alkyleneoxy group" include an oxydimethyleneoxy group. Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group. Preferred substituents on the "C1-5 alkylene group", "oxy C1-4 alkylene group", "oxy C2-3 alkyleneoxy group", and "C1-3 alkyleneoxy C1-3 alkylene group" are halogeno groups such as fluoro, chloro, bromo, and iodo groups; C1-6 alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, and t-butyl groups; or C1-6 haloalkyl groups such as chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, and 1-fluoro-n-butyl groups.

[0174] In the present invention, preferred examples of Ga include 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 C3-6 cycloalkyloxy group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted 5- or 6-membered heterocyclyloxy group, R a1 A group represented by -CO-O-, an oxo group (O=), or R a1 Examples include a divalent group represented by ON=. In this case, a preferred example of the substituted or unsubstituted 5- or 6-membered heterocyclyloxy group is a tetrahydro-2H-pyran-4-yl group.

[0175] In the present invention, more preferred examples of Ga include 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, R a1 A group represented by -CO-O-, an oxo group (O=), or R a1 Examples include a divalent group 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. For example, it can 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) of the present invention or a salt of compound (II) can be obtained by a known method such as those described in the Examples. In addition, a salt of compound (II) can be obtained from compound (II) by a known method.

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

[0179] [ka]

[0180] In formula (I-1), X 1# represents X in formula (II). 1 or by common practice, X 1 The structure that can be derived to X 2# represents X in formula (II). 2 or by common practice, X 2 The structure that can be derived to X 3# represents X in formula (II). 3 or by common practice, X 3 The structure that can be derived from Q # represents the same meaning as Q in formula (II) or a structure which can be derived to Q by a general method. # has the same meaning as A in formula (II) or represents a structure which can be derived to A by a general method. The symbols in formula (III-1) have the same meanings as those in formula (I-1). X in formula (A) 3# has the same meaning as in formula (I-1). L represents a leaving group. For example, when a compound of formula (A) having a leaving group such as a methanesulfonyloxy group in L is used, the compound can be prepared by reacting in the presence of an inorganic base. For example, when 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) Compounds of formula (III-1) can be prepared by condensing compounds of formula (B) and formula (C), as shown in Reaction Scheme 2 below.

[0182] [ka]

[0183] The symbols in formula (B) have the same meanings as those in formula (I-1). The symbols in formula (C) have the same meanings as those in formula (I-1). Hal represents a halogeno group. For example, it can be prepared by reacting a compound of formula (B) with a compound of formula (C) in the presence of an inorganic base.

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

[0185] [ka]

[0186] R in formula (B-1) 1 and R 6 has the same meaning as in formula (II). 1# has the same meaning as in formula (I-1). R in formula (D) 6 has the same meaning as in formula (II). 1# has the same meaning as in formula (I-1). R in formula (E) 1 has the same meaning as in formula (II). The compound of formula (E) may be used in the form of its hydrochloride. For example, it can be prepared by reacting a compound of formula (D) with a compound of formula (E) in an alcohol solvent.

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

[0188] [ka]

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

[0190] (Reaction Scheme 5) Compounds of formula (I-1) may also be prepared by condensing compounds of formula (IV-1) with compounds of formula (C), as shown in Reaction Scheme 5 below.

[0191] [ka]

[0192] The symbols in formula (IV-1) have the same meanings as those in formula (I-1). The symbols in formula (C) have the same meanings as those in formula (I-1). Hal represents a halogeno group. For example, it can be prepared by reacting a compound of formula (IV-1) with a compound of formula (C) in the presence of an inorganic base.

[0193] [Production intermediates] The compound represented by the following formula (III) or a salt thereof can be used as a production intermediate in producing the compound represented by formula (II).

[0194] [ka]

[0195] In formula (III), X1 is 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 C1-6 alkylthio ... unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C3-6 cycloalkyloxy group, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted C6-10 aryloxy group, substituted or unsubstituted C6-10 arylthio group, substituted or unsubstituted C6-10 arylsulfinyl group, substituted or unsubstituted C6-10 arylsulfonyl group, substituted or unsubstituted 5-6 membered heterocyclyl group, substituted or unsubstituted 5-6 membered heterocyclyloxy group, nitro group, 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 1 A group represented by -CO-O-, R 1 -CO-NR 5 -, R 2 A group represented by -O-CO-O-, R 2 -O-CO-NR 5 -, R 3 R 4 A group represented by N-CO-O-, R 3 R 4 N-CO-NR 5 -, R 2 SO2-NR 5 -, R 3 R 4 A group represented by N-SO2- or R 1 ON=CR 6 - represents a group represented by the formula: R 1each 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- or 6-membered heterocyclyl group, R 2 each 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- or 6-membered heterocyclyl group, R 3 each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group, R 4 each 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 may be taken together to form a divalent organic group, R 5 each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, R 6 represents a hydrogen atom, a halogeno group, an amino group, a substituted or unsubstituted mono-C1-6 alkylamino group, a substituted or unsubstituted di-C1-6 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- or 6-membered heterocyclyl group; X 2 is R 1 ON=CR 6-, R 1 CO-ON=CR 6 -, R 3 R 4 N-CO-ON=CR 6 -, R 3 R 4 NN=CR 6 -, or R 7 -N=CR 6 R represents a group represented by -; 1 , R 3 , R 4 , and R 6 X 1 R 7 represents a substituted or unsubstituted 5-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 heterocyclyl group.

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

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

[0198] [ka]

[0199] In formula (IV), 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 C1-6 alkylthio ... unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C3-6 cycloalkyloxy group, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted C6-10 aryloxy group, substituted or unsubstituted C6-10 arylthio group, substituted or unsubstituted C6-10 arylsulfinyl group, substituted or unsubstituted C6-10 arylsulfonyl group, substituted or unsubstituted 5-6 membered heterocyclyl group, substituted or unsubstituted 5-6 membered heterocyclyloxy group, nitro group, 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 1 A group represented by -CO-O-, R 1 -CO-NR 5 -, R 2 A group represented by -O-CO-O-, R 2 -O-CO-NR 5 -, R 3 R 4 A group represented by N-CO-O-, R 3 R 4 N-CO-NR 5 -, R 2 SO2-NR 5 -, R 3 R 4 A group represented by N-SO2- or R 1 ON=CR 6 - represents a group represented by the formula: R 1each 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- or 6-membered heterocyclyl group, R 2 each 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- or 6-membered heterocyclyl group, R 3 each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group, R 4 each 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 may be taken together to form a divalent organic group, R 5 each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, R 6 represents a hydrogen atom, a halogeno group, an amino group, a substituted or unsubstituted mono-C1-6 alkylamino group, a substituted or unsubstituted di-C1-6 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- or 6-membered heterocyclyl group; X 2 is R 1 ON=CR 6-, R 1 CO-ON=CR 6 -, R 3 R 4 N-CO-ON=CR 6 -, R 3 R 4 NN=CR 6 -, or R 7 -N=CR 6 R represents a group represented by -; 1 , R 3 , R 4 , and R 6 X 1 R 7 represents a substituted or unsubstituted 5-membered heterocyclyl group; X 3 represents 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- or 6-membered heterocyclyl group; X 4 represents a hydrogen atom or a C1-6 alkoxymethyl group.

[0200] X in formula (IV) 4 The symbols other than have the same meanings as those in formula (II). X 4 Examples of the "C1-6 alkoxy group" in the "C1-6 alkoxymethyl group" include a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, an i-propoxy group, an i-butoxy group, an s-butoxy group, a t-butoxy group, and an i-hexyloxy group.

[0201] An example of the intermediates used in the production of the compound (II) of the present invention is shown in the following Table 1. In the table, the melting point (mp) is also shown as a physical property of each compound.

[0202] [Table 1] TIFF0007651464000016.tif255139

[0203] Among the compounds listed in Table 1, those that have the properties of amorphous or viscous oil 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] [Agricultural and horticultural fungicides] The agricultural and horticultural fungicide of the present invention contains at least one selected from compound (II) and its salt as an active ingredient. The amount of compound (II) or its salt contained in the agricultural and horticultural fungicide of the present invention is not particularly limited as long as it shows a fungicidal effect.

[0205] The agricultural and horticultural fungicide of the present invention can be used to control plant diseases caused by a wide variety of filamentous fungi, for example, fungi belonging to the phylum Oomycetes, Ascomycetes, Deuteromycetes, Basidiomycetes, and Zygomycetes.

[0206] Examples of plant diseases (pathogens) that can be controlled are shown below. Sugar beet: Cercospora beticola, Aphanomyces cochlioides, Root rot (Thanatephorus cucumeris), Leaf rot (Thananatephorus cucumeris), Rust (Uromyces betae), Powdery mildew (Oidium sp.), Spot disease (Ramularia beticola), Seedling damping off (Aphanomyces cochlioides, Pythium ultimum) etc. Peanut: Brown spot disease (Mycosphaerella arachidis), soil blotch disease (Ascochyta sp.), rust disease (Puccinia arachidis), damping off disease (Pythium debaryanum), rust spot disease (Alternaria alternata), white mold disease (Sclerotium rolfsii), black spot disease (Mycosphaerella berkeleyi), black root rot (Calonectria ilicicola), etc. Cucumber: Powdery mildew (Sphaerotheca fuliginea), Downy mildew (Pseudoperonospora cubensis), Vine wilt (Mycosphaerella melonis), Vine splitting (Fusarium oxysporum), Sclerotinia sclerotiorum, Gray mold (Botrytis cinerea), Anthracnose (Colletotrichum orbiculare), Black spot (Cladosporium cucumerinum), Brown spot (Corynespora cassiicola), Seedling damping-off (Pythium debaryanum, Rhizoctonia solani Kuhn), Phomopsis root rot (Phomopsis sp.), Bacterial spot (Pseudomonas syringae pv. Lachrymans), etc. Tomatoes: Botrytis cinerea, Cladosporium fulvum, Phytophthora infestans, Verticillium albo-atrum, Verticillium dahliae, Oidium neolycopersici, Alternaria solani, Pseudocercospora fuligena), bacterial wilt (Ralstonia solanacearum), Sclerotinia sclerotiorum, etc. Eggplant: Gray mold (Botrytis cinerea), black blight (Corynespora melongenae), powdery mildew (Erysiphe cichoracearum), sooty mold (Mycovellosiella nattrassii), sclerotinia sclerotiorum, half-leaf wilt (Verticillium dahliae), brown spot (Phomopsis vexans), etc. Pepper: late blight (Phytophthora capsici), gray mold (Botrytis cinerea), sclerotinia sclerotiorum, anthracnose (Colletotrichum aenigma, Colletotrichum capsici, Colletotrichum fructicola, Colletotrichum jiangxiense), powdery mildew (Leveillula taurica), etc. Strawberry: Gray mold (Botrytis cinerea), powdery mildew (Sphaerotheca humuli), anthracnose (Colletotrichum acutatum, Colletotrichum fragariae), late blight (Phytophthora cactorum), soft rot (Rhizopus stolonifer), yellows (Fusarium oxysporum), wilt (Verticillium dahliae), sclerotinia sclerotiorum, etc. Onions: Grey rot (Botrytis allii), Grey mould (Botrytis cinerea), White spot blight (Botrytis squamosa), Downy mildew (Peronospora destructor), White blight (Phytophthora porri), Ciborinia allii, Sclerotium rot (Botrytis squamosa), Dry rot (Fusarium oxysporum), Red root rot (Pyrenochaeta terrestris), Black rot sclerotium disease (Sclerotium cepivorum), Rust (Puccinia allii), Southern blight (Sclerotium rolfsii), etc. Leeks: Soft rot (Pectobacterium carotovorum), Downy mildew (Peronospora destructor), Leaf blight (Pleospora allii), Black rot sclerotium disease (Sclerotium cepivorum), Rust (Puccinia allii), White spot blight (Botrytis squamosa), Southern blight (Sclerotium rolfsii), Red root rot (Pyrenochaeta terrestris), etc. Cabbages: Clubroot (Plasmodiophora brassicae), Soft rot (Erwinia carotovora), Black rot (Xanthomonas campesrtis pv. campestris), Black spot bacteriosis (Pseudomonas syringae pv. maculicola, P. s. pv. alisalensis), Downy mildew (Peronospora parasitica), Sclerotinia rot (Sclerotinia sclerotiorum), Black sooty mould (Alternaria brassicicola), Grey mould (Botrytis cinerea), Root rot (Phoma lingam), Pythium rot (Pythium aphanidermatum, Pythium ultimum), White rust (Albugo macrospora), etc. Lettuce: Rot (Pseudomonas cichorii, Pseudomonas marginalis), Soft rot (Pectobacterium carotovorum), Downy mildew (Bremia lactucae), Gray mold (Botrytis cinerea), Sclerotinia sclerotiorum, Big-vein disease (Mirafiori lettuce big-vein ophiovirus), Root rot (Fusarium oxysporum), Bottom rot (Rhizoctonia solani), Powdery mildew (Golovinomyces orontii), etc. Beans: Sclerotinia sclerotiorum, Botrytis cinerea, Colletotrichum lindemuthianum, Phaeoisariopsis griseola, etc. Pea: Brown spot (Mycosphaerella blight), Gray mold (Botrytis cinerea), Sclerotinia sclerotiorum, Powdery mildew (Erysiphe pisi), etc.

[0207] Apple: Powdery mildew (Podosphaera leucotricha), black spot (Venturia inaequalis), Monilinia mali, black spot (Mycosphaerella pomi), canker (Valsa mali), leaf spot (Alternaria mali), red spot (Gymnosporangium yamadae), ring spot (Botryosphaeria berengeriana), anthracnose (Glomerella cingulata, Colletotrichum acutatum), brown spot (Diplocarpon mali), sooty spot (Zygophiala jamaicensis), sooty spot (Gloeodes pomigena), purple root rot (Helicobasidium mompa), white root rot (Rosellinia necatrix), gray mold (Botrytis cinerea), fire blight (Erwinia amylovora), silver leaf disease (Chondrostereum purpureum), crown gall disease (Rhizobium radiobacter, Rhizobium rhizogenes), etc. Plum: Black spot (Cladosporium carpophilum), Gray mold (Botrytis cinerea), Gray spot (Monilinia mumecola), Sooty spot (Peltaster sp.), Fruit rot (Taphrina pruni), Brown hole (Phloeosporella padi), etc. Persimmon: Powdery mildew (Phyllactinia kakicola), Anthracnose (Gloeosporium kaki), Angular leaf spot (Cercospora kaki), Circular leaf spot (Mycosphaerella nawae), Gray mold (Botrytis cinerea), Sooty spot (Zygophiala jamaicensis), etc. Peaches: Monilinia fructicola, Monilia fructigena, Cladosporium carpophilum, Phomopsis sp., Xanthomonas campestris pv. pruni, Taphrina deformans, Colletotrichum gloeosporioides, Phloeosporella padi), Kawaratake disease (Coriolus versicolor), etc. Almond: Brown spot (Monilinia laxa), spot (Stigmina carpophila), black spot (Cladosporium carpophilum), leaf blisters (Polystigma rubrum), leaf spot (Alternaria alternata), anthracnose (Colletotrichum gloeospoides), etc. Prunus: Monilinia fructicola, Colletotrichum acutatum, Alternaria sp., Monilinia kusanoi, Mycosphaerella cerasella, Powdery mildew (Podosphaera tridactyla), etc. Grapes: Gray mold (Botrytis cinerea), powdery mildew (Uncinula necator), late rot (Glomerella cingulata, Colletotrichum acutatum), downy mildew (Plasmopara viticola), black rot (Elsinoe ampelina), brown spot (Pseudocercospora vitis), black rot (Guignardia bidwellii), white rot (Coniella castaneicola), rust (Phakopsora ampelopsidis), white snow disease (pathogen unidentified), crown gall (Rhizobium radiobacter, Rhizobium vitis), etc. Pear: Black spot (Venturia nashicola), red spot (Gymnosporangium asiaticum), black spot (Alternaria kikuchiana), ring spot (Botryosphaeria berengeriana), powdery mildew (Phyllactinia mali), canker (Phomopsis fukushii), brown spot (Stemphylium vesicarium), anthracnose (Glomerella cingulata), etc. Tea: ring spot disease (Pestalotiopsis longiseta, P. theae), anthracnose disease (Colletotrichum theae-sinensis), net blight disease (Exobasidium reticulatum), red burn disease (Pseudomonas syringae), blight disease (Exobasidium vexans), etc. Citrus: scab (Elsinoe fawcettii), blue mold (Penicillium italicum), green mold (Penicillium digitatum), gray mold (Botrytis cinerea), black spot (Diaporthe citri), canker (Xanthomonas campestris pv.Citri), powdery mildew (Oidium sp.), late blight (Phytophthora citrophthora), anthracnose (Colletotrichum fioriniae), etc. Kiwifruit: Bacterial blossom rot (Pseudomonas marginalis, Pseudomonas syringae, Pseudomonas viridiflava), canker (Pseudomonas syringae), gray mold (Botrytis cinerea), fruit soft rot (Botryosphaeria dothidea, Diaporthe sp., Lasiodiplodia theobromae), sooty spot (Pseudocercospora actinidiae), etc. オリーブ:Anthrax (Colletotrichum acutatum, Colletotrichum gloeosporioides), Peacock spot (Spilocaea oleaginea)など クリ:Anthrax (Colletotrichum gloeosporioides)など

[0208] Summary: Blumeria graminis f.sp. tritici, Gibberella zeae, Fusarium avenaceum, Fusarium culmorum, Fusarium crookwellense, Microdochium nivale, Puccinia recondita, Puccinia striiformis, Pythium iwayamai, Monographella nivalis, Pseudocercosporella herpotrichoides, Septoria tritici, Leptosphaeria nodorum, Typhula incarnata, Myriosclerotinia borealis, Gaeumannomyces damping off graminis), ergot (Claviceps purpurea), black spike disease (Tilletia caries), naked black spike disease (Ustilago nuda), Imochi disease (Pyricularia grisea), Damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.) Barley: Pyrenophora graminea, Pyrenophora teres, Rhynchosporium secalis, Ustilago tritici, U.nuda, Damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.) etc. Rice: Blast disease (Pyricularia oryzae), Sheath blight (Rhizoctonia solani), Gibberella fujikuroi, Cochliobolus miyabeanus, Seedling blight (Pythium graminicola), Bacterial leaf blight (Xanthomonas oryzae), Bacterial seedling blight (Burkholderia plantarii), Brown stripe (Acidovorax avenae), Bacterial grain rot (Burkholderia glumae), Stripe blight (Cercospora oryzae), Rice smut (Ustilaginoidea virens), Brown rice (Alternaria alternata, Curvularia intermedia), Black rice (Alternaria padwickii), Pink rice (Epicoccum purpurascens), etc. Tobacco: Sclerotinia sclerotiorum, powdery mildew, Phytophthora nicotianae, etc. Tulips: Gray mold (Botrytis cinerea), brown spot (Botrytis tulipae), leaf rot (Rhizoctonia solani), bulb rot (Fusarium oxysporum), bark rot (Rhizoctonia solani), etc. Roses: Black spot (Diplocarpon rosae), powdery mildew (Erysiphe simulans, Podosphaera pannosa), gray mold (Botrytis cinerea), etc. Chrysanthemum: Gray mold (Botrytis cinerea), white rust (Puccinia horiana), downy mildew (Paraperonospora minor, Peronospora danica), Pythium damping-off (Pythium aphanidermatum, Pythium dissotocum, Pythium helicoides, Pythium oedochilum, Pythium sylvaticum), damping-off (Rhizoctonia solani), Fusarium damping-off (Fusarium solani), etc. Gerbera: Gray mold (Botrytis cinerea), powdery mildew (Podosphaera xanthii), etc. Lilies: Leaf blight (Botrytis elliptica, Pestalotiopsis sp.), gray mold (Botrytis cinerea), etc. Sunflower: Downy mildew (Plasmopara halstedii), Sclerotinia sclerotiorum, Gray mold (Botrytis cinerea), etc. Bentgrass: Snow mold (Sclerotinia borealis), large patch (Rhizoctonia solani), brown patch (Rhizoctonia solani), dollar spot (Sclerotinia homoeocarpa), blast (Pyricularia sp.), red burn (Pythium aphanidermatum), anthracnose (Colletotrichum graminicola), etc. Orchard grass: Powdery mildew (Erysiphe graminis), etc. Soybean: Purple spot (Cercospora kikuchii), Downy mildew (Peronospora manshurica), Stem rot (Phytophthora sojae), Rust (Phakopsora pachyrhizi), Sclerotinia sclerotiorum, Anthracnose (Colletotrichum truncatum), Gray mold (Botrytis cinerea), Black rot (Elsinoe glycines), Black spot (Diaporthe phaseolorum var. sojae), Damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), etc. Potato: late blight (Phytophthora infestans), summer blight (Alternaria solani), black spot (Thanatephorus cucumeris), half-leaf wilt (Verticillium albo-atrum, V. dahliae, V. nigrescens), black leg disease (Pectobacterium atrosepticum), soft rot (Pectobacterium carotovorum), gray mold (Botrytis cinerea), scab (Streptomyces spp.), sclerotinia sclerotiorum, etc. Yam: Leaf blight (Cylindrosporium dioscoreae), anthracnose (Colletotrichum gloeosporioides), blue mold (Penicillium sclerotigenum), etc. Sweet potato: Helicobasidium mompa, Fusarium oxysporum, etc. Taro: blight (Phytophthora colocasiae), stem rot (Rhizoctonia solani), etc. Ginger: Rhizome rot (Pythium ultimum, Pythium myriotylum), white spot (Phyllosticta zingiberis), etc. Banana: Panama disease (Fusarium oxysporum), Sigatoka disease (Mycosphaerella fijiensis, M. musicola), etc. Mango: Anthracnose (Colletotrichum aenigma), canker (Xanthomonas campestris), stem rot (Diaporthe pseudophoenicicola, Lasiodiplodia theobromae, Lasiodiplodia spp., Neofusicoccum parvum, Neofusicoccum sp.), gray mold (Botrytis cinerea), etc. Rapeseed: Sclerotinia sclerotiorum, Phoma lingam, Alternaria brassicae, Powdery mildew (Erysiphe cruciferarum, Erysiphe cichoracearum, Oidium matthiolae), Downy mildew (Peronospora parasitica), etc. Coffee: Rust (Hemileia vastatrix), Anthracnose (Colletotrichum coffeanum), Brown eye disease (Cercospora coffeicola), etc. Sugarcane: Brown rust (Puccinia melanocephala), etc. Corn: hail blight (Gloeocercospora sorghi), rust (Puccinia sorghi), southern rust (Puccinia polysora), ear smut (Ustilago maydis), brown spot (Cochliobolus heterostrophus), sooty blight (Setosphaeria turcica), damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), etc. Cotton: Seedling damping-off (Pythium sp.), rust (Phakopsora gossypii), white mold (Mycosphaerella areola), anthracnose (Glomerella gossypii), etc. Hops: Downy mildew (Pseudoperonospora humuli), powdery mildew (Oidium sp., Podosphaera macularis), gray mold (Botrytis cinerea), etc.

[0209] [Nematocides] The dihydropyrimidine compounds of the present invention are also excellent in controlling effects against various nematodes which affect plant growth. The nematicide of the present invention contains at least one selected from compound (II) and its salt as an active ingredient. The amount of compound (II) or its salt contained in the nematicide of the present invention is not particularly limited as long as it shows a nematode control effect.

[0210] Specific examples of various plant parasitic nematodes that can be controlled by the nematicide of the present invention are given below. (1) Tylenchida (a) from the family Anguinidae, e.g., from Anguina spp., Anguina funesta, Anguina tritici; from Ditylenchus spp., Ditylenchus destructor, Ditylenchus dipsaci, Ditylenchus myceliophagus; (b) Aphelenchoididae, for example, Aphelenchoides spp., such as Aphelenchoides besseyi, Aphelenchoides fragariae, Aphelenchoides ritzemabosi, and Aphelenchoides besseyi; Bursaphelenchus spp., such as Bursaphelenchus xylophilus; (c) from the family Belonolaimidae, e.g., from Belonolaimus spp., Belonolaimus longicaudatus; from Tylenchorhynchus spp., Tylenchorhynchus claytoni, Tylenchorhynchus dubius; (d) Criconematidae, e.g., Criconema mutabile; (e) Dolichodoridae, e.g., Dolichodorus mediterraneus; (f) Ecphyadophoridae, e.g., Ecphyadophora tenuissima (g) Hemicycliophoridae, e.g., Loofia thienemanni; (h) from the family Heteroderidae, for example, from Globodera spp., Globodera rostochiensis, Globodera pallida, Globodera tabacum; from Heterodera spp., Heterodera avenae, Heterodera cruciferae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii; (i) from the family Hoplolaimidae, for example, from Helicotylenchus spp., Helicotylenchus dihystera, Helicotylenchus multicinctus; from Hoplolaimus spp., Hoplolaimus columbus, Hoplolaimus galeatus; others, Rotylenchus robustus, Rotylenchus reniformis; (j) from the family Meloidogynidae, for example, Meloidogyne spp., Meloidogyne arenaria, Meloidogyne chitwoodi, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne thamesi; (k) Nothotylenchidae, e.g., Nothotylenchus acris; (l) Paratylenchidae, for example, Paratylenchus spp., Paratylenchus curvitatus, Paratylenchus elachistus; (m) the family Pratylenchidae, for example, Pratylenchus spp., such as Pratylenchus brachyurus, Pratylenchus coffeae, Pratylenchus curvitatus, Pratylenchus fallax, Pratylenchus goodeyi, Pratylencus neglectus, Pratylenchus penetrans, Pratylenchus scribneri, Pratylenchus vulnus, and Pratylenchus corn. (Pratylenchus zeae);Others include the false root-knot nematode (Nacobbus aberrans), the banana root-miner nematode (Radopholus similis), the citrus root nematode (Tylenchulus semipenetrans), and the citrus root-miner nematode (Radopholus citrophilus).

[0211] (2) Order Dorylaimida (a) From the family Longidoridae, for example, from the genus Longidorus, Longidorus elongates; from the genus Xiphinema, Xiphinema americanum, Xiphinema brevicolle, Xiphinema index, Xiphinema diversicaudatum.

[0212] (3) Triplonchida (a) Family Trichodoridae, e.g., Trichodorus primitivus, Paratrichodorus minor.

[0213] [Application method / mixture] The agricultural and horticultural fungicide or nematicide of the present invention is preferably used on plants such as grains, vegetables, root vegetables, potatoes, fruit trees, trees such as tea, coffee, and cacao, pasture grasses, turf grasses, and cotton.

[0214] The agricultural and horticultural fungicide of the present invention can be applied to various parts of plants, such as leaves, stems, stalks, flowers, buds, fruits, seeds, sprouts, roots, tubers, tuberous roots, shoots, cuttings, etc. The nematicide can be applied to roots, tubers, tuberous roots, etc. In addition, improved varieties, varieties, cultivated varieties, mutants, hybrids, and genetically modified organisms (GMOs) of these plants can also be targeted.

[0215] The agricultural and horticultural fungicide of the present invention can be used for seed treatment, foliage spray, soil application, water surface application, etc., which are carried out to control various diseases that occur in agricultural and horticultural crops including flowers, turf, and pasture grass. The nematicide can be used for seed treatment, soil application, etc.

[0216] The agricultural and horticultural fungicide or nematicide 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. Examples of other components include conventionally known fungicides, insecticides / acaricides, nematicides, soil pesticides, plant regulators, synergists, fertilizers, soil conditioners, animal feed, etc. By containing such other components, a synergistic effect may be achieved. That is, one embodiment of the present invention includes an agricultural and horticultural fungicide which contains one or more additional fungicides.

[0217] Specific examples of fungicides that can be mixed or used in combination with the agricultural and horticultural fungicide or nematicide of the present invention are shown below. (1) Nucleic acid biosynthesis inhibitors: (a) RNA polymerase I inhibitors: benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M; oxadixyl; clozylacon, ofrace; (b) Adenosine deaminase inhibitors: bupirimate, dimethirimol, ethirimol; (c) DNA / RNA synthesis inhibitors: hymexazole, octhilinone; (d) DNA topoisomerase II inhibitor: oxolinic acid.

[0218] (2) Mitosis inhibitors and cytostatics: (a) β-tubulin polymerization inhibitors: benomyl, carbendazim, chlorphenazole, fuberidazole, thiabendazole; thiophanate, thiophanate methyl; diethofencarb; zoxamide; ethaboxam; (b) Cytostatic agent: pencycuron; (c) Spectrin-like protein delocalization inhibitors: fluopicolide, fluopimomide.

[0219] (3) Respiratory inhibitors: (a) Complex I-NADH oxidoreductase inhibitors: diflumetrim; tolfenpyrad; (b) Complex II-succinate dehydrogenase inhibitors: benodanil, flutolanil, mepronil; isofetamide; fluopyram; fenfuram, flumeciclox; carboxin, oxycarboxin; thifluzamide; benzovindiflupyr, bixafen, fluxapyroxad, furametpyr, isopyrazam, penflufen, penthiopyrad, sedaxane; boscalid, pydiflumetofen, isofluciflam, pyraziflumide, inpyrfluxam; (c) Complex III-ubiquinol oxidase Qo inhibitors: azoxystrobin, cumoxystrobin, cumethoxystrobin, enoxastrobin, flufenoxystrobin, picoxystrobin, pyraoxystrobin; pyraclostrobin, pyrametostrobin, triclopyricarb; kresoxim-methyl, trifloxystrobin; dimoxystrobin, phenaminestrobin, metominostrobin, orysastrobin; famoxadone; fluoxastrobin; fenamidone; pyribencarb; methyltetraprole; mandestrobin; (d) Complex III-ubiquinol reductase Qi inhibitors: cyazofamid; amisulbrom; fenpicoxamide; (e) Uncouplers of oxidative phosphorylation: binapacryl, meptyldinocap, dinocap; fluazinam; ferimzone; (f) Oxidative phosphorylation inhibitors (inhibitors of ATP synthase): fentin acetate, fentin chloride, fentin hydroxide; (g) ATP production inhibitors: silthiofam; (h) Complex III: Qx (unknown) inhibitor of cytochrome bc1 (ubiquinone reductase): ametoctrazine.

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

[0221] (5) Signal transduction inhibitors: (a) Signal transduction inhibitors: quinoxyfen, proquinazid; (b) MAP·histidine kinase inhibitors in osmotic signaling: fenpiclonil, fludioxonil; chlozolinate, iprodione, procymidone, vinclozolin.

[0222] (6) Lipid and cell membrane synthesis inhibitors: (a) Phospholipid biosynthesis, methyltransferase inhibitors: edifenphos, iprobenfos, pyrazophos; isoprothiolane; (b) Lipid peroxidants: biphenyl, chloroneb, dicloran, quintozene, tecnazene, tolclofos-methyl; etridiazole; (c) Agents acting on cell membranes: iodocarb, propamocarb, propamocarb hydrochloride, propamocarb fosetylate, prothiocarb; (d) Microorganisms that disrupt pathogen cell membranes: Bacillus subtilis, Bacillus subtilis QST713, Bacillus subtilis FZB24, Bacillus subtilis MBI600, and Bacillus subtilis D747; (e) Cell membrane disrupting agent: Tea tree extract.

[0223] (7) Cell membrane sterol biosynthesis inhibitors: (a) Inhibitors of demethylation at C14 in sterol biosynthesis: Triforine; Pyrifenox, Pyrisoxazole; Fenarimol, Flurprimidol, Nuarimol; Imazalil, Imazalil sulfate, Oxpoconazole, Pefurazoate, Prochloraz, Triflumizole, Biniconazole; Azaconazole, Bitertanol, Bromuconazole, Cyproconazole, Diclobutrazol, Difenoconazole, Diniconazole, Diniconazole-M, Epoxyconazole azole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, fluconazole, fluconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole; prothioconazole, voriconazole, mefentrifluconazole; (b) Inhibitors of Δ14 reductase and Δ8→Δ7-isomerase in sterol biosynthesis: aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph; fenpropidin, piperalin; spiroxamine; (c) 3-ketoreductase inhibitors in the C4 demethylation of sterol biosynthesis: fenhexamid; fenpyrazamine; (d) Squalene epoxidase inhibitors of the sterol biosynthesis system: pyributicarb; naftifine, terbinafine.

[0224] (8) Cell wall synthesis inhibitors: (a) Trehalase inhibitor: validamycin; (b) Chitin synthase inhibitors: polyoxins, polyoxolim; (c) Cellulose synthase inhibitors: dimethomorph, flumorph, pyrimorph; benthiavalicarb, iprovalicarb, valifenalate; mandipropamide.

[0225] (9) Melanin biosynthesis inhibitors (a) Reductase inhibitors of melanin biosynthesis: fthalide; pyroquilon; tricyclazole; (b) Dehydratase inhibitors of melanin biosynthesis: Carpropamid; Diclocymet; Fenoxanil; (c) Polyketide synthesis inhibitor of melanin biosynthesis: tolprocarb.

[0226] (10) Resistance inducer in host plants: (a) Agents acting on the salicylic acid synthesis pathway: acibenzolar-S-methyl; (b) Others: probenazole, tiadinil, isotianil, diclobenthiazox, ipfentrifluconazole, laminarin, and Japanese knotweed extract.

[0227] (11) Agents of unknown activity: cymoxanil, fosetylaluminum, phosphoric acid (phosphate salts), tecloftalam, triazoxide, flusulfamide, diclomedine, metasulfocarb, cyflufenamid, metrafenone, pyriophenone, dodine, dodine free base, and flutianil.

[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; ferbam, mancozeb, maneb, mancopper, metiram, polycarbamate, propineb, thiram, zineb, ziram; captan, captafol, folpet; chlorothalonil; dichlofluanid, tolylfluanid; guazatine, guazatine acetate, iminoctadine triacetate, iminoctadine trialbesilate; anilazine; dithianone; quinomethionate; fluoroimide.

[0229] (13) Other agents: DBEDC, fluorofolpet, bis(8-quinolinolato)copper(II), propamidine, chloropicrin, cyproflam, Agrobacterium, bethoxazin, diphenylamine, methylisothianate (MITC), mildeomycin, capsaicin, khufuraneb, cyprosulfamide, dazomet, debacarb, dichlorophen, difenzoquat, difenzoquat methylsulfonate, flumetober, fosetyl calcium, fosetyl sodium, irumamycin, natamycin, nitrotar isopropyl, oxamocarb, pyrrolnitrin, tebufloquine, tolnifanide, zaliramide, algophase, amicarthiazol Arthiazol, Oxathiapiprolin, Fluoxapiprolin, Metiram Zinc, Benthiazole, Trichlamide, Uniconazole, Oxyfenthiin, Picarbutrazox, Quinofumelin, Florylpicoxamid, Pyrapropoyne, Fluindapyr, Aminopyrifen, Pyridachlomethyl, Ipflufenoquin, Dipimethitron.

[0230] Specific examples of insecticides, miticides, nematicides, soil pesticides, anthelmintics and the like that can be mixed or used in combination with the agricultural and horticultural fungicide or nematicide of the present invention are shown below. (1A) Acetylcholinesterase (AChE) inhibitors (carbamate type): Alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, xylylcarb.

[0231] (1B) Acetylcholinesterase (AChE) inhibitors (organophosphorus): Acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos, Dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, funfur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyaphos, isofenphos, isopropyl O-(methoxyaminothiophosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton methyl, parathion, parathion methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimphos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion.

[0232] (2) GABAergic chloride channel blockers: Chlordane, endosulfan; ethiprole, fipronil. Fulfiprole. (3A) Sodium channel modulators (pyrethroids): Acrinathrin, allethrin, d-cis-trans-allethrin, d-trans-allethrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentenyl-isomer, bioresmethrin, cycloprothrin, cyfluthrin, β-cyfluthrin, cyhalothrin, λ-cyhalothrin, γ-cyhalothrin, cypermethrin, α-cypermethrin, β-cypermethrin, θ-cypermethrin, ζ-cypermethrin, cyphenothrin [(1R)-trans isomer], deltamethrin, en Pentrin [(EZ)-(1R)-isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprithrin, kadesrin, permethrin, fenothrin [(1R)-trans isomer], prallethrin, pyrethrins, resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomer], tralomethrin, transfluthrin. κ-bifenthrin, chloropralesulfon, heptafluthrin, meperfluthrin, ε-metofluthrin, monfluorothrin, ε-monfluorothrin, κ-tefluthrin, tetramethylfluthrin; bioethanomethrin. (3B) Sodium channel modulators (DDTs): DDT, methoxychlor.

[0233] (4) Nicotinic acetylcholine receptor (nAChR) competitive modulators: Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam; nicotine; sulfoxaflor; flupyradifurone; triflumezopyrim. Dichloromezothiaz, flupirimine. (5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators: Spinetoram, spinosad. (6) Glutamate-gated chloride channel (GluCl) allosteric modulators: Abamectin, Emamectin, Emamectin Benzoate, Lepimectin, Milbemectin. Doramectin, eprinomectin, ivermectin, moxidectin, selamectin. (7) Juvenile hormone analogues: Hydroprene, kinoprene, methoprene; fenoxycarb; pyriproxyfen. (8) Other non-specific (multi-site) inhibitors: Methyl bromide, alkyl halides; chloropicrin; sodium aluminum fluoride, sulfuryl fluoride; borax, boric acid, disodium octaborate, sodium borate, sodium metaborate; tartar emetic; dazomet, metam, metam potassium, metam sodium. (9) Chordotonal TRPV channel modulators: Pymetrozine, pyrifluquinazone; afidopiropen.

[0234] (10) Mite growth inhibitors: Clofentezine, diflavidazine, hexythiazox; etoxazole. (11) Microbial-derived insect midgut membrane disrupting agents: Bt subsp. israelensis, Bt subsp. aizawai, Bt subsp. kurstaki, Bt subsp. tenebrionis; Proteins found in Bt crops: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1; Bacillus sphaericus. (12) Mitochondrial ATP synthase inhibitors: Diafenthiuron; azocyclotin, cyhexatin, fenbutatin oxide; propargite; tetradifon. (13) Oxidative phosphorylation uncouplers that disrupt the proton gradient: Chlorfenapyr, DNOC, sulfuramide. (14) Nicotinic acetylcholine receptor (nAChR) channel blockers: Bensultap, Cartap hydrochloride, Thiosultap-sodium salt. (15) Chitin biosynthesis inhibitor, type 0: Bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron. (16) Chitin biosynthesis inhibitors, type 1: Buprofezin. (17) Molting inhibitor: Cyromazine. (18) Ecdysone receptor agonist: Chromafenozide, halofenozide, methoxyfenozide, tebufenozide. (19) Octopamine receptor agonists: Amitraz.

[0235] (20) Mitochondrial electron transport complex III inhibitors: Hydramethylnon; acequinocyl; fluacrypyrim; bifenazate. (21) Mitochondrial electron transport complex I inhibitor (METI): Fenazaquin, fenpyroximate, pyridaben, pyrimidifen, tebufenpyrad, tolfenpyrad; rotenone. (22) Voltage-dependent sodium channel blockers: Indoxacarb; Metaflumizone. (23) Acetyl-CoA carboxylase inhibitors: Spirodiclofen, spiromesifen, spirotetramat. Spiropydione. (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 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: Flonicamid. (30) GABA-gated chloride channel allosteric modulators: Broflanilide, fluxamethamide. Isocycloserum; afoxolaner, fluralaner, lotineral, sarolaner. Other insecticides and acaricides: Azadirachtin, benzoximate, bromopropylate, quinomethionate, dicofol, lime sulfur, mancozeb, pyridalyl, sulfur. Acinonapyr, benzpyrimoxane, flometoquin, fluhexafon, oxazosulfil, cyclopyrazoflor.

[0236] Deworming agent: (a) Benzimidazoles: fenbendazole, albendazole, triclabendazole, oxibendazole, mebendazole, oxfendazole, perbendazole, flubendazole; febantel, netobimin, thiophanate; thiabendazole, cambendazole; (b) Salicylanilides: closantel, oxyclozanide, rafoxanide, niclosamide; (c) Substituted phenols: nitroxynil, nitrosanoate; (d) Pyrimidines: pyrantel, morantel; (e) Imidazothiazoles: levamisole, tetramisole; (f) Tetrahydropyrimidines: praziquantel, epsiprantel; (g) Other anthelmintics: cyclodiene, ryanine, clorsulon, metronidazole, demiditraz; piperazine, diethylcarbamazine, dichlorophen, monepantel, tribendimidine, amidantel; thiacetarsamide, melarsomine, arsenamide.

[0237] Specific examples of plant regulators which can be mixed or used in combination with the agricultural and horticultural fungicide or nematicide of the present invention are given below. Abscisic acid, kinetin, benzylaminopurine, 1,3-diphenylurea, forchlorfenuron, thidiazuron, chlorfenuron, dihydrozeatin, gibberellin A, gibberellin A4, gibberellin A7, gibberellin A3, 1-methylcyclopropane, N-acetylaminoethoxyvinylglycine (also known as abiglycine), aminooxyacetic acid, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyric acid, dichlorprop, f Ethylthiol, 1-naphthylacetamide, ethychlozate, cloxyfonac, maleic hydrazide, 2,3,5-triiodobenzoic acid, salicylic acid, methyl salicylate, (-)-jasmonic acid, methyl jasmonate, (+)-strigol, (+)-deoxystrigol, (+)-orobanchol, (+)-sorgolactone, 4-oxo-4-(2-phenylethyl)aminobutyric acid; ethephon, chlormequat, mepiquat chloride, benzyladenine, 5-aminolevulinic acid.

[0238] [Formulation] The agricultural and horticultural fungicide or nematicide of the present invention is not particularly limited by its formulation. For example, it can be in the form of a wettable powder, an emulsifiable concentrate, a dust, a granule, a water-soluble powder, a suspension, a granular wettable powder, or a tablet. The method of preparation into a formulation is not particularly limited, and a known preparation method can be adopted according to the formulation. Some formulation examples are shown below. The formulations shown below are merely examples, and may be modified within the scope of the present invention. The present invention is not limited by the following formulation examples. "Parts" refers to "parts by weight" unless otherwise specified.

[0239] (Formulation Example 1: Wettable powder) 40 parts of the dihydropyrimidine compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfate and 3 parts of alkylnaphthalene sulfonate are uniformly mixed and finely ground to obtain a wettable powder with an active ingredient content of 40%. (Formulation Example 2: Emulsion) 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 are mixed and dissolved to obtain an emulsifiable concentrate having an active ingredient content of 30%. (Formulation Example 3: Granules) 5 parts of the dihydropyrimidine compound of the present invention, 40 parts of talc, 38 parts of clay, 10 parts of bentonite and 7 parts of sodium alkyl sulfate are uniformly mixed and finely ground, and then granulated to a particle diameter of 0.5 to 1.0 mm to obtain a granule containing 5% of the active ingredient. (Formulation Example 4: Granules) 5 parts of the dihydropyrimidine compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of dioctyl sulfosuccinate sodium salt, and 1 part of potassium phosphate were uniformly mixed and pulverized. Water was added to the mixture, which was then thoroughly kneaded. The mixture was then granulated and dried to obtain a granule containing 5% of the active ingredient. (Formulation Example 5: Suspension) 10 parts of the dihydropyrimidine compound of the present invention, 4 parts of polyoxyethylene alkyl allyl ether, 2 parts of sodium polycarboxylate, 10 parts of glycerin, 0.2 parts of xanthan gum and 73.8 parts of water are mixed and wet-pulverized until the particle size is 3 microns or less to obtain a suspension containing 10% of the active ingredient. (Formulation Example 6: Granular Water Dispersible) 40 parts of the dihydropyrimidine compound of the present invention, 36 parts of clay, 10 parts of potassium chloride, 1 part of sodium alkylbenzenesulfonate, 8 parts of sodium ligninsulfonate, and 5 parts of a formaldehyde condensate of sodium alkylbenzenesulfonate are mixed uniformly 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 water dispersible agent containing 40% of the active ingredient.

[0240] [Antifungal agents for medical and veterinary use (veterinary medicine)] The dihydropyrimidine compounds of the present invention can be used as preventive or therapeutic agents for controlling harmful pathogens, particularly fungi, that infect humans or animals. The medical / veterinary antifungal agent of the present invention contains at least one selected from compound (II) and its salt 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 shows an antifungal effect.

[0241] In this specification, the term "animal" refers to vertebrate animals (V ertebrata) such as pets, livestock, poultry, animals kept for exhibition in zoos and aquariums, etc., captive wild animals, and research and experimental animals.

[0242] For example, the following animals may be mentioned, 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, mink, elephants, bears, kangaroos, foxes, dogs, cats, squirrels, rabbits, mice, rats, guinea pigs, hamsters, monkeys, and ferrets. Birds such as pigeons, parakeets, parrots, Java sparrows, Bengalese finches, canaries, chickens, ducks, turkeys, wild ducks, pheasants, peacocks, ostriches, swans, sparrows, quails, owls, eagles, hawks, and cormorants. Reptiles such as chameleons, iguanas, lizards, snakes, turtles, crocodiles, geckos, etc. Amphibians such as frogs and newts. Fish such as carp, goldfish, killifish, tropical fish, yellowtail, sea bream, amberjack, salmon, mackerel, sea bass, grouper, tuna, horse mackerel, flounder, and pufferfish.

[0243] Examples of fungi (molds) as pathogenic bacteria to which the medical and veterinary antifungal agent of the present invention can be applied are shown below, although the specific examples are not limited to these. For example, the genus Absidia, such as Absidia corymbifera; the genus Acremonium; the genus Alternaria, such as Alternaria alternata; the genus Aspergillus, such as Aspergillus flavus, Aspergillus fumigatus, Aspergillus nidulans, Aspergillus niger, Aspergillus parasiticus, Aspergillus terreus; the genus Bipolaris; the genus Blastomyces, such as Blastomyces dermatitidis; the genus Blumeria, such as Blumeria graminis; the genus Candida, such as Candida albicans, Candida glabrata, Candida krusei, Candida parapsilosis, Candida tropicalis; the genus Cladosporium, such as Cladosporium cladosporoides, Cladosporium herbarium; the genus Coccidioides, such as Coccidioides immitis, Coccidioides posadasii; and the genus Colletotrichium trifolii. the genus Colletotrichium such as Cryptococcus neoformans; the genus Curvularia such as Curvularia lunata; the genus Encephalitozoon such as Encephalitozoon cuniculi; the genus Epicoccum such as Epicoccum nigrum; the genus Epidermophyton such as Epidermophyton floccosum; the genus Exophiala; the genus Exserohilum such as Exserohilum rostratum; the genus Fusarium such as Fusarium graminarium, Fusarium solani, Fusarium sporotrichoides; the genus Fonsecaea such as Fonsecaea monophora; the genus Histoplasma such as Histoplasma capsulatum;Leptosphaeria species such as Leptosphaeria nodorum; Malassezia species such as Malassezia globosa; Microsporum species such as Microsporum canis; Mycosphaerella species such as Mycosphaerella graminicola; Neurospora species; Paecilomyces species such as Paecilomyces lilanicus and Paecilomyces varioti; Penicillium species such as Penicillium chrysogenum; Phytophthora species such as Phytophthora capsici and Phytophthora infestans; Plasmopara species such as Plasmopara viticola; Pneumocystis species such as Pneumocystis jirovecii; Pyricularia species such as Pyricularia oryzae; Pythium species such as Pythium ultimum; Puccinia species such as Puccinia coronata and Puccinia graminis; Rhizoctonia Rhizoctonia species such as solani; Rhizomucor species; Scedosporium species such as Fusarium apiospermum and Scedosporium prolificans; Scopulariopsis species such as Scopulariopsis brevicaulis; Sporothrix species such as Sporothrix schenckii; Talaromyces species such as Talaromyces marneffei; Trichophyton species such as Trichophyton mentagrophytes, Trichophyton interdigitale, Trichophyton rubrum, Trichophyton tonsurans, and Trichophyton verrucosum; Trichosporon species such as Trichosporon asahii and Trichosporon beigelii; Ustilago species, etc.; Among these, the antifungal agent of the present invention is suitable for use against the genus Aspergillus, Trichophyton or Candida, and is particularly suitable for use against Aspergillus fumigatus or Trichophyton tonsurans.

[0244] Examples of fungal infections to which the medical and veterinary antifungal agent of the present invention can be applied are shown below, although the specific examples are not limited to these.

[0245] The medical and veterinary antifungal agent of the present invention can be applied to both systemic fungal infections and superficial fungal infections. Specific examples of fungal infections include Aspergillus diseases such as pulmonary aspergillosis and systemic aspergillosis (which is likely to occur in immunosuppressed patients such as bone marrow recipients or AIDS patients), Candida diseases such as systemic candidiasis, Cryptococcus meningitis, rhinocerebral mucomycosis, pulmonary mucormycosis, blastomycosis, histoplasmosis, coccidiomycosis, paracoccidiomycosis, lobomycosis, keratomycosis, sporotrichosis, chromoblastomycosis, chromomycosis, phaeohyphomycosis, zygomycosis, cryptococcosis, disseminated sporotrichosis, ringworm, and the like. These include tinea capitis, tinea corporis, tinea cruris, tinea pedis (athlete's foot), tinea unguium (toenail fungus), candidiasis of the skin, mouth, or vagina, Malassezia, chronic mucocutaneous candidiasis, Pneumocystis pneumonia, and Marneffei penicilliosis. The antifungal agent of the present invention can also be applied to allergic diseases caused by fungi, such as allergic bronchopulmonary asthma (ABPA); asthma, rhinosinusitis, or sinusitis.

[0246] The medical / veterinary antifungal agent of the present invention may contain pharma- ceutical acceptable additives. The additives are not particularly limited as long as they are used in known medical drugs. They are naturally sterile and non-pyrogenic. In addition, the additives may be appropriately selected depending on the dosage form and administration method of the antifungal agent.

[0247] The dosage form that the medical / veterinary antifungal agent of the present invention can take is not particularly limited, and examples thereof include solid preparations such as tablets, powders, granules, capsules, troches (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; gas preparations such as aerosols and vapors; and nanoparticle preparations. The medical antifungal agent of the present invention can be administered by a known method, for example, subcutaneous, intravenous, intramuscular, intrasternal injection, etc., percutaneous administration such as insertion into the anus, vagina, etc., application, spraying, or dropping onto the skin surface, oral administration such as taking it by mouth, or nasal administration by inhalation, etc.

[0248] In the case of a solid preparation for oral administration, examples of additives that can be used in the medical / veterinary antifungal agent of the present invention include solubilizing agents 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 gums, gelatin, methylcellulose, carboxymethylcellulose, or polyvinylpyrrolidone; disaggregating agents such as starch, alginic acid, alginates, or sodium starch glycolate; effervescing mixtures; dyes; sweeteners; wetting agents such as lecithin, polysorbates, lauryl sulfates, or other non-toxic and pharmacologically inactive substances generally used in pharmaceutical preparations. 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 a liquid preparation for oral administration, examples of additives that can be used in the medical / veterinary antifungal agent of the present invention include solubilizing agents such as cyclodextrin or modified cyclodextrin, sucrose, glycerin, mannitol, sorbitol, natural gum, agar, sodium alginate, pectin, methylcellulose, carboxymethylcellulose, polyvinyl alcohol, and the like.

[0250] In the case of a liquid preparation for intramuscular injection, additives that can be used in the medical / veterinary antifungal agent of the present invention include sterilized water, olive oil, ethyl oleate, glycols such as propylene glycol, solubilizing agents such as cyclodextrin, modified cyclodextrin, etc. Furthermore, an appropriate amount of lidocaine hydrochloride can be added as necessary.

[0251] In the case of a liquid preparation for intravenous injection, additives that can be used in the medical / veterinary antifungal agent of the present invention include carriers such as sterile water, solubilizing agents such as cyclodextrin, modified cyclodextrin, etc. These can also be included in the form of a sterilized isotonic saline solution.

[0252] The amount of compound (II) or a salt thereof contained in the medical / veterinary antifungal agent of the present invention is preferably 85% by weight or less, more preferably 50% by weight or less, based on the weight of the antifungal agent. The dosage of the medical / veterinary antifungal agent of the present invention can be appropriately selected depending on the administration method, the type of infecting fungus, the age, body weight, symptoms, etc. For example, for adults, in the case of oral or parenteral (injection, drip, etc.) administration, 0.1 to 100 mg / kg-body weight can be administered once or several times a day. Furthermore, the medical / veterinary antifungal agent of the present invention can be used in combination with other drugs other than compound (II).

[0253] Next, the present invention will be described in more detail with reference to synthesis examples, although the present invention is not limited to the following synthesis examples in any way. 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 No. 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 potassium carbonate (0.81 g) and 2-bromo-5'-fluoro-2'-methoxyacetophenone (1.45 g) were added under ice cooling, and the mixture was stirred at room temperature for 3 hours. Water was added to the reaction solution, and the resulting solid was filtered. The obtained 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 at 45° C. overnight. Water was added to the reaction solution, extracted with ethyl acetate, washed with water and saturated saline, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate) to obtain 2.13 g of the target compound. Yield: 68% The obtained objective 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] 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 (0.15 g) was dissolved in methanol (1.5 ml) and tetrahydrofuran (1.5 ml), and sodium borohydride (12 mg) was added under ice cooling and stirred for 1 hour. The reaction mixture was added with a saturated aqueous solution of ammonium chloride, extracted with ethyl acetate, washed with water and saturated saline, and then dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the resulting residue was dissolved in tetrahydrofuran (1.5 ml), to which acrylonitrile (0.2 g) and 40% aqueous potassium hydroxide solution (0.1 ml) were added, followed by stirring at room temperature overnight. Water was added to the reaction solution, extracted with chloroform, and then dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate) to obtain 0.08 g of the target compound. Yield: 48% The obtained objective 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), and acetic acid (20 ml) was added thereto and stirred at room temperature for 7 hours. Water was added to the reaction solution, extracted with ethyl acetate, washed with saturated aqueous sodium bicarbonate and saturated saline, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, 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 to give a residue, which was dissolved in chloroform (20 ml) and ethanol (20 ml). Pyridine (0.40 g) and isopropoxyamine hydrochloride (0.6 g) were added at room temperature, 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 objective 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 potassium carbonate (2.20 g) and 2-bromo-5'-fluoro-2'-methoxyacetophenone (4.00 g) were added under ice cooling, and the mixture was stirred at room temperature for 3 hours. Water was added to the reaction solution, and the resulting solid was filtered. The obtained 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 solution, extracted with ethyl acetate, washed with water and saturated saline, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: chloroform / ethyl acetate) to obtain 4.60 g of the target compound. Yield: 61% The obtained objective 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] tert-butyl(2-(5-acetyl-3-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)ethyl)carbamate (1.60 g) was dissolved in 1,4-dioxane (50 ml), and 4N hydrogen chloride / 1,4-dioxane solution (15 ml) was added and stirred at room temperature for 8 hours. The reaction mixture was concentrated, and the resulting residue was dissolved in methylene chloride (50 ml), and triethylamine (1.5 ml) and isobutyric acid chloride (0.7 ml) were added thereto, followed by stirring 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 objective 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 No. 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 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 objective 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 sodium borohydride (20 mg) was added under ice cooling and stirred for 30 minutes. A saturated aqueous solution of ammonium chloride was added to the reaction solution, extracted with ethyl acetate, washed with water and saturated saline, and then dried over anhydrous sodium sulfate. The resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 0.25 g of the target compound. Yield: 99% The obtained objective 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), and acrylonitrile (0.27 g) and 40% potassium hydroxide aqueous solution (0.3 ml) were added thereto, followed by stirring at room temperature overnight. Water was added to the reaction solution, extracted with chloroform, and then dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate) to obtain 0.12 g of the target compound. Yield: 47% The obtained objective 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 (Compounds 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 (15.4 g) was dissolved in ethanol (200 ml) and chloroform (100 ml), and 2-(aminooxy)propane hydrochloride (14.0 g) was added thereto, followed by stirring at 45° C. for 3 hours. Water was added to the reaction solution, extracted with methylene chloride, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 20.6 g of the target compound. Yield: 98% The obtained objective 1 The H-NMR spectrum is shown below. 1H-NMR (DMSO-D6) δ: 11.26 (1H, s), 11.11 (1H, d, J = 5.9 Hz), 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 solution, and the resulting solid was filtered to obtain 3.39 g of the target product. Yield 90% The obtained objective 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 No. 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), 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 solution was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate), and the resulting product was dissolved in 1,4-dioxane (7 ml), and 4N hydrogen chloride / 1,4-dioxane solution (7 ml) was added and stirred at room temperature for 4 hours. The reaction solution was concentrated, and the resulting residue was dissolved in methylene chloride (7 ml), and triethylamine (3 ml) and isobutanoyl chloride (0.1 ml) were added under ice cooling and stirred for 30 minutes. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: chloroform / ethyl acetate) to obtain 0.45 g of the target compound. Yield: 60% The obtained objective 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 (Compounds 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 sodium borohydride (18 mg) was added under ice cooling and stirred for 20 minutes. A saturated aqueous solution of ammonium chloride was added to the reaction solution, extracted with ethyl acetate, washed with water and saturated saline, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain the target compounds A-74 (0.11 g) and A-75 (0.11 g). The yields were 44% for each compound. The obtained objective 1 The H-NMR spectrum is shown below. Compound No. 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 No. 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 (compounds 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 desired product. Yield: 99% The obtained objective 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 (production 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), 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 solution was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate), and the resulting product was dissolved in 1,4-dioxane (20 ml), and 4N hydrogen chloride / 1,4-dioxane solution (12 ml) was added and stirred at room temperature for 3 hours. The reaction solution was concentrated, and the resulting residue was dissolved in methylene chloride (40 ml), and triethylamine (3 ml) and isobutanoyl chloride (1.3 ml) were added under ice cooling and stirred for 30 minutes. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: chloroform / ethyl acetate) to obtain 2.90 g of the target compound. Yield: 77% The obtained objective 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 17% boron tribromide methylene chloride solution (1.5 ml) was added under ice cooling and stirred overnight. A saturated aqueous solution of sodium bicarbonate was added to the reaction solution, which was extracted with methylene chloride and then dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the resulting residue was purified by silica gel chromatography (eluent: hexane / ethyl acetate) to obtain 0.32 g of the desired product. Yield: 72% The obtained objective 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 No. 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 2-bromo-1-(2-(trifluoromethoxy)phenyl)ethan-1-one (0.25 g) and potassium carbonate (0.10 g) were added under ice cooling and stirred overnight. Water was added to the reaction mixture, which was then extracted with ethyl acetate and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, 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 objective 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 (compounds 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 sodium borohydride (15 mg) was added under ice cooling and stirred for 40 minutes. A saturated aqueous solution of ammonium chloride was added to the reaction solution, extracted with ethyl acetate, washed with water and saturated saline, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain the target compounds C-193 (0.90 g) and C-194 (0.90 g). The yields were 47% for each. The obtained objective 1 The H-NMR spectrum is shown below. Compound No. 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 No. 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] Some of the compounds of the present invention produced in the same manner as in the above Examples are shown in Table 2. In the table, the melting point (mp) is also shown as a physical property of each compound.

[0292] [Table 2] TIFF0007651464000035.tif236146TIFF0007651464000036.tif236146TIFF0007651464000037.tif236146TIFF00076514640 00038.tif236146TIFF0007651464000039.tif236146TIFF0007651464000040.tif236146TIFF0007651464000041.tif144146

[0293] Furthermore, some of the compounds of the present invention produced in the same manner as in the above Examples are shown in Table 3. In the table, the melting point (mp) is also shown as a physical property of each compound. In addition, if the compound is a stereoisomer, this is indicated in the Special Notes. [Table 3] TIFF0007651464000043.tif228163TIFF0007651464000044.tif228163TIFF0007651464000045.tif228163TIFF000 7651464000046.tif228163TIFF0007651464000047.tif228163TIFF0007651464000048.tif228163TIFF00076514640 00049.tif235169TIFF0007651464000050.tif228167TIFF0007651464000051.tif228167TIFF0007651464000052.t if228167TIFF0007651464000053.tif228167TIFF0007651464000054.tif231167TIFF0007651464000055.tif169167

[0294] Furthermore, some of the compounds of the present invention produced in the same manner as in the above Examples are shown in Table 4. In the table, the melting point (mp) is also shown as a physical property of each compound. In addition, if the compound is a stereoisomer, this is indicated in the special notes. [Table 4] TIFF0007651464000057.tif226167

[0295] Among the compounds listed in Tables 2 to 4, those having the properties of amorphous or viscous oil are listed in Table 5 below. 1 H-NMR data is shown. [Table 5] TIFF0007651464000059.tif240164TIFF0007651464000060.tif255162TIFF0007651464000061.tif118164

[0296] Furthermore, some of the compounds of the present invention produced in the same manner as in the above Examples are shown in Table 6. The melting point (mp) is also shown in the table as a physical property of each compound. In addition, if the compound is a stereoisomer, this is indicated in the special notes. [Table 6] TIFF0007651464000063.tif227170TIFF0007651464000064.tif221170TIFF0007651464000065.tif221170TIFF0007651464000066.tif221170TIFF0007651464000067.tif223170TIFF0007651464000068.tif223170TIFF0007651464000069.tif223170TIFF0007651464000070.tif223170TIFF0007651464000071.tif224170TIFF0007651464000072.tif223170TIFF0007651464000073.tif223170TIFF0007651464000074.tif223170TIFF0007651464000075.tif224170TIFF0007651464000076.tif223170TIFF0007651464000077.tif223170TIFF0007651464000078.tif223170TIFF0007651464000079.tif223170TIFF0007651464000080.tif223170TIFF0007651464000081.tif223170TIFF0007651464000082.tif223170TIFF0007651464000083.tif223170TIFF0007651464000084.tif223170TIFF0007651464000085.tif223170TIFF0007651464000086.tif223170TIFF0007651464000087.tif223170TIFF0007651464000088.tif223170TIFF0007651464000089.tif223170TIFF0007651464000090.tif223170TIFF0007651464000091.tif223170TIFF0007651464000092.tif223170TIFF0007651464000093.tif223170TIFF0007651464000094.tif223170TIFF0007651464000095.tif223170TIFF0007651464000096.tif223170TIFF0007651464000097.tif223170TIFF0007651464000098.tif223170TIFF000765146400 0099.tif223170TIFF0007651464000100.tif223170TIFF0007651464000101.tif223170TIFF0007651464000102.tif224170TIFF0007651 464000103.tif223170TIFF0007651464000104.tif223170TIFF0007651464000105.tif223170TIFF0007651464000106.tif223170TIFF00 07651464000107.tif223170TIFF0007651464000108.tif223170TIFF0007651464000109.tif223170TIFF0007651464000110.tif139170.

[0297] Furthermore, some of the compounds of the present invention produced in the same manner as in the above Examples are shown in Table 7. The melting point (mp) is also shown in the table as a physical property of each compound. In addition, if the compound is a stereoisomer, this is indicated in the special notes. [Table 7] TIFF0007651464000112.tif227170TIFF0007651464000113.tif227170TIFF000 7651464000114.tif225170TIFF0007651464000115.tif225170TIFF0007651464 000116.tif225170TIFF0007651464000117.tif225170TIFF0007651464000118. tif225170TIFF0007651464000119.tif225170TIFF0007651464000120.tif22517 0TIFF0007651464000121.tif225170TIFF0007651464000122.tif225170TIFF00 07651464000123.tif225170TIFF0007651464000124.tif225170TIFF0007651464 000125.tif225170TIFF0007651464000126.tif225170TIFF0007651464000127. tif225170TIFF0007651464000128.tif225170TIFF0007651464000129.tif51170

[0298] Among the compounds listed in Tables 6 and 7, those that have the properties of amorphous or viscous oil are listed in Table 8 below. 1 H-NMR data is shown. [Table 8] TIFF0007651464000131.tif227170TIFF0007651464000132.tif238170TIFF0007651464000133.tif228170TIFF00076514640 00134.tif230170TIFF0007651464000135.tif243170TIFF0007651464000136.tif234170TIFF0007651464000137.tif147170

[0299] [Biological Testing] The usefulness of the dihydropyrimidine compounds of the present invention as active ingredients of agricultural and horticultural fungicides will be demonstrated by the following test examples. 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) 5 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 (registered trademark) 20) were mixed and dissolved to obtain an emulsion (I) containing 5% of the active ingredient.

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

[0304] [Number 1] Control value (%) = 100 - {lesion area rate in treated area / lesion area rate in untreated area} x 100

[0305] (Test Example 1) Apple scab control test Water was added to the emulsion (I) so that the dihydropyrimidine compound had a concentration of 125 ppm, and the compound was dissolved to obtain a drug solution. The drug solution was then sprayed onto apple seedlings (variety "Orin", 3-4 leaf stage) grown in seedling pots. After air drying, the seedlings were inoculated with conidia of the apple spot fungus (Venturia inaequalis) (treated group). As a control, apple seedlings that had not been sprayed with the drug solution were inoculated in the same manner (untreated group). The seedlings were placed in a moist room at 20°C, with light and dark cycles repeated every 12 hours. Two weeks after the inoculation, the leaves of the apple seedlings were visually observed to determine the lesion area ratio, and the control value was calculated.

[0306] Control tests for apple scab were carried out on the dihydropyrimidine compounds shown in Tables 9 and 10. All of the compounds showed a control value of 75% or more.

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

[0308] A wheat powdery mildew control test was carried out on the dihydropyrimidine compounds shown in Tables 9 and 10. All of the compounds showed a control value of 75% or more.

[0309] (Test Example 3) Wheat leaf rust control test Water was added to the emulsion (I) so that the dihydropyrimidine compound had a concentration of 125 ppm, and the compound was dissolved to obtain a drug solution. The drug solution was then sprayed onto wheat seedlings (variety "Norin 61", 1-2 leaf stage) grown in seedling pots. After air drying, the wheat seedlings sprayed with the drug solution were inoculated by sprinkling uredospores of wheat leaf rust fungus (Puccinia recondita) on them (treated area). As a control, wheat seedlings not sprayed with the drug solution were inoculated in the same manner as above (untreated area). They were then left to stand in a greenhouse at 20°C. Twelve days after the inoculation, the leaves of the wheat seedlings were visually observed to determine the lesion area ratio, and the control value was calculated.

[0310] A wheat leaf rust control test was carried out on the dihydropyrimidine compounds shown in Tables 9 and 10. All of the compounds showed a control value of 75% or more.

[0311] (Test Example 4) Cucumber gray mold control test Water was added to the emulsion (I) so that the dihydropyrimidine compound had a concentration of 125 ppm, and the compound was dissolved to obtain a drug solution. The drug solution was then sprayed onto cucumber seedlings (variety "Jihai", cotyledon stage) grown in seedling pots. After air drying, a conidiospore suspension of Botrytis cinerea was dropwise inoculated onto the seedlings (treated group). As a control, cucumber seedlings not sprayed with the drug solution were dropwise inoculated onto the seedlings in the same manner as above (untreated group). The seedlings were then left to stand in a moist room at 20°C. Four days after the inoculation, the leaves of the cucumber seedlings were visually observed to determine the lesion area ratio, and the control value was calculated.

[0312] A cucumber gray mold control test was carried out on the dihydropyrimidine compounds shown in Tables 9 and 10. All of the compounds showed a control value 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 weight of dihydropyrimidine compound / seed weight was 100g / 100kg. These seeds were sown in pots, and 8 to 10 days later, they were inoculated by sprinkling conidia of wheat powdery mildew fungus (Erysiphe graminis f.sp.tritici) on them (treated area). As a control, wheat seedlings that had not been treated with the drug were inoculated in the same manner as above (untreated area). They were then left to stand in a greenhouse at 20°C. Seven days after the inoculation, the leaves of the wheat seedlings were visually observed to determine the lesion area ratio, and the control value was calculated.

[0314] A wheat powdery mildew seed treatment test was carried out on the dihydropyrimidine compounds shown in Table 11. All of the compounds showed a control value of 75% or more.

[0315] [Table 11]

[0316] (Test Example 6) Wheat Powdery Mildew Soil Drench Treatment Test Wheat seeds (variety "Chihoku") were sown in pots (5.5cm x 5.5cm) and 10mL of a solution of dihydropyrimidine compounds (emulsion (I) mixed with water to give a concentration of 100ppm) was irrigated, and 8-10 days later, conidia of wheat powdery mildew fungus (Erysiphe graminis f.sp.tritici) were sprinkled on the pots to inoculate them (treated area). As a control, wheat seedlings that had not been treated with the drug were inoculated in the same manner as above (untreated area). They were then left to stand in a greenhouse at 20℃. Seven days after the inoculation, the leaves of the wheat seedlings were visually observed to determine the lesion area ratio, and the control value was calculated.

[0317] A soil drench treatment test for wheat powdery mildew was carried out on the dihydropyrimidine compounds shown in Table 12. All of the compounds showed a control value of 75% or more.

[0318] [Table 12]

[0319] The usefulness of the dihydropyrimidine compound of the present invention as an active ingredient of a nematicide is demonstrated by the following test examples. (Test Example 7) Efficacy against sweet potato root-knot nematode A suspension containing about 50 2nd instar larvae (L2) of Meloidogyne incognita per 0.16 mL was poured into a 96-well microplate at 160 μL per well, and then a drug solution in which the dihydropyrimidine compound concentration was adjusted to 125 ppm by adding water to emulsion (I) was poured at 40 μL per well. The plate was left at 20° C. for 4 days. After that, the survival rate was determined and the killing rate was calculated. Individuals that did not move for 10 seconds were determined as dead. The test was performed in duplicate.

[0320] Compounds A-28, A-64, C-92, and C-145 were tested for their efficacy against Meloidogyne incognita. All compounds showed nematode killing rates of 60% or more.

[0321] The usefulness of the dihydropyrimidine compound of the present invention as an active ingredient of an antifungal agent for medical and veterinary use is demonstrated in the following test examples. (Test Example 8) Antibacterial test against Fusarium graminearum Water was added to Emulsion (I) so that the dihydropyrimidine compound had a concentration of 125 ppm, and the dihydropyrimidine compound was dissolved therein to obtain a drug solution. Spores of Fusarium graminearum were added and dispersed in potato sucrose yeast extract medium, and the above-mentioned drug solution was added and mixed so that the concentration of dihydropyrimidine compounds in the culture solution was 15.6 ppm. These were then dispensed into a 96-well microplate and cultured in the dark at 20°C for 4 days. After the cultivation, the turbidity was measured at a wavelength of 405 nm using a microplate reader, and the growth inhibition rate (%) of Fusarium graminearum was calculated in comparison with the untreated case.

[0322] Antibacterial tests were carried out against Fusarium graminearum for the dihydropyrimidine compounds listed in Table 13. All of the compounds showed excellent growth inhibition rates of 50% or more.

[0323] [Table 13]

[0324] (Test Example 9) Antibacterial test against Aspergillus niger Aspergillus niger spores were added and dispersed in Vogel's medium, and dihydropyrimidine compounds dissolved in dimethyl sulfoxide were added and mixed to a concentration of 25 ppm. These were then dispensed onto a 96-well microplate and cultured in the dark at 25°C for 4 days. After the cultivation, the turbidity was measured at a wavelength of 405 nm using a microplate reader, and the growth inhibition rate (%) of Aspergillus niger was calculated in comparison with the untreated case.

[0325] The dihydropyrimidine compounds shown in Table 14 were subjected to an antibacterial test against Aspergillus niger. All of the compounds showed an excellent growth inhibition rate of 50% or more.

[0326] [Table 14] [Industrial Applicability]

[0327] Since randomly selected dihydropyrimidine compounds of the present invention exhibit the above-mentioned effects, the dihydropyrimidine compounds of the present invention, including compounds not listed above, have bactericidal, antibacterial and nematicidal effects, do not cause phytotoxicity to plants, and have low toxicity to humans, livestock and fish and low impact on the environment, and are useful as agricultural chemicals, nematicides, and medical and veterinary antifungal agents.

Claims

1. A compound represented by formula (I) or a salt thereof. 【Chemistry 1】 [In formula (I), X １ represents a hydrogen atom; X ２ is R １ O-N=CR ６ represents a group represented by -, R １ represents a substituted or unsubstituted C1-6 alkyl group, R ６ is a hydrogen atom, or represents a substituted or unsubstituted C1-6 alkyl group; X ３ is a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or represents a substituted or unsubstituted 4- to 6-membered heterocyclyl group; X ３ The substituents on the linear C1-6 alkyl group, C3-6 cycloalkyl group, C6-10 aryl group and 4- to 6-membered heterocyclyl group in a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, Hydroxyl group, a substituted or unsubstituted C1-6 alkoxy 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 C6-10 aryl group, a substituted or unsubstituted 3- to 10-membered heterocyclyl group, Cyano group, R ａ a group represented by -CO-, R ｂ A group represented by —O—CO—, R ｃ R ｄ A group represented by N-, R ｃ R ｄ A group represented by N—CO—, R ａ A group represented by —CO—O—, R ａ -CO-NR ｅ A group represented by -, R ａ -CO-CO-NR ｅ A group represented by -, 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 ｃ R ｄ N-CS-NR ｅ A group represented by -, R ｂ SO ２ -NR ｅ A group represented by -, R ａ O-N=CR ｆ -, and R ｈ R ｉ A group represented by C=N-O- One or more substituents selected from the group consisting of: R ａ are each independently Hydrogen atoms, 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 represents a substituted or unsubstituted 3- to 10-membered heterocyclyl group; R ｂ are each independently a substituted or unsubstituted C1-6 alkyl group, or represents a substituted or unsubstituted C3-6 cycloalkyl group, R ｃ are each independently Hydrogen atoms, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C3-6 cycloalkyl group, or represents a substituted or unsubstituted C6-10 aryl group, R ｄ are each independently Hydrogen atoms, a substituted or unsubstituted C1-6 alkyl group, or represents a substituted or unsubstituted C1-6 alkoxy group, Here, R ｃ and R ｄ may be taken together to form a divalent organic group, R ｅ are each independently Hydrogen atoms, a substituted or unsubstituted C1-6 alkyl group, or represents a substituted or unsubstituted C1-6 alkoxy group, R ｆ teeth, a hydrogen atom, or represents an amino group, R ｈ are each independently represents a substituted or unsubstituted C1-6 alkyl group, R ｉ are each independently represents a substituted or unsubstituted C1-6 alkyl group, Here, R ｈ and R ｉ may be taken together to form a divalent organic group; A represents a substituted or unsubstituted C1-6 alkylene group; The substituent on the C1-6 alkylene group in A is Hydroxyl group, Substituted or unsubstituted C1-6 alkoxy group an oxo group (O=), or R ａ１ A divalent group represented by O-N=, R ａ１ represents a substituted or unsubstituted C1-6 alkyl group; Q represents a substituted or unsubstituted C6-10 aryl group.

2. 10. An agricultural and horticultural fungicide comprising as an active ingredient at least one selected from the group consisting of the compound according to claim 1 and salts thereof.

3. The agricultural and horticultural fungicide according to claim 2, which is for use in seed treatment.

4. A nematicide comprising at least one selected from the group consisting of the compound according to claim 1 and salts thereof as an active ingredient.

5. 13. An antifungal agent for medical or veterinary use, comprising as an active ingredient at least one selected from the group consisting of the compound according to claim 1 and salts thereof.

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