Bicyclic heterocyclic compound and fungicide for agricultural and horticultural use containing same as active ingredient

Abstract

The present invention relates to a compound which is represented by formula (1), or a salt thereof. (In formula (1), Het represents formula (2), and the definitions of the groups in formula (1) and formula (2) are as described in the description.)

Description

Bicyclic heterocyclic compounds and agricultural and horticultural fungicides containing the same as active ingredients

[0001] The present invention relates to a bicyclic heterocyclic compound and an agricultural chemical containing the compound as an active ingredient.

[0002] Controlling diseases of agricultural and horticultural crops plays an important role in ensuring stable agricultural production. For this purpose, various fungicides are used. However, long-term use of fungicides can lead to the emergence of drug-resistant bacteria, so there is a strong demand for new fungicides that are effective against not only drug-susceptible bacteria but also drug-resistant bacteria.

[0003] Incidentally, as 2H-benzo[e][1,3]oxazine compounds, for example, Patent Documents 1 and 2 disclose 2,2-disubstituted-4-(quinolin-3-yl)-2H-benzo[e][1,3]oxazine compounds, and for example, Patent Document 3 discloses 2,2-disubstituted-4-(pyridin-3-yl)-2H-benzo[e][1,3]oxazine compounds. As 2H-benzo[e][1,3]thiazine compounds, for example, Patent Document 1 discloses 2,2-disubstituted-4-(quinolin-3-yl)-2H-benzo[e][1,3]thiazine compounds, and for example, Patent Document 4 discloses 2,2-disubstituted-4-(pyridin-3-yl)-2H-benzo[e][1,3]thiazine compounds. Furthermore, as benzo[d]imidazole compounds and pyrazolo[1,5-a]pyridine compounds having a nitrogen-containing 5-6 fused heterocycle, for example, Patent Document 5 discloses a 1-(1H-benzo[d]imidazol-1-yl)-3,3,4,4-tetrasubstituted-3,4-dihydroisoquinoline compound, and for example, Patent Document 6 discloses a 3,3,4,4-tetrasubstituted-1-(pyrazolo[1,5-a]pyridin-3-yl)-3,4-dihydroisoquinoline compound.

[0004] International Publication No. WO 2009 / 119089, International Publication No. WO 2022 / 243109, International Publication No. WO 2022 / 243107, International Publication No. WO 2023 / 111215, International Publication No. WO 2016 / 156085, International Publication No. WO 2017 / 025510

[0005] However, there are problems such as the control effect of conventional control agents against plant diseases being insufficient, and the emergence of pathogens resistant to drugs limiting the use of control agents. To solve such problems, new control agents are needed. An object of the present invention is to provide a novel compound, an agricultural and horticultural pest control agent and an agricultural and horticultural fungicide containing the compound or a salt thereof, and a method for controlling plant diseases.

[0006] The present inventors have found that a compound having a specific structure can solve the above problems, and have completed the present invention.

[0007] That is, the present invention includes the following aspects: [1] A compound represented by the following formula (1) or a salt thereof: [In formula (1), R １ and R ２ each independently represent a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group optionally substituted with a substituent A, a C2 to C6 alkenyl group optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, a C1 to C6 acyl group optionally substituted with a substituent A, an aryl group optionally substituted with a substituent B, and a heteroaryl group optionally substituted with a substituent B; -C(=O)NRaRb (wherein Ra and Rb each independently represent a hydrogen atom, a C1 to C6 alkyl group optionally substituted with a substituent A, a group selected from the group consisting of a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 acyl group, and -C(=O)ORc (wherein Rc represents a group selected from the group consisting of a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent A, a C1-C6 haloalkyl group, and a C3-C8 cycloalkyl group); or Ra and Rb together with the nitrogen atom to which they are bonded form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group, or an azocanyl group) and -C(=O)ORc (wherein Rc has the same meaning as defined above); １ and R ２may be taken together to form a C3-C8 cycloalkyl ring which may be substituted with a substituent A, or a C3-C8 saturated or unsaturated heterocyclic ring which may be substituted with a substituent A; Het represents formula (2), In formula (2), R ３ , R ４ , and R ５ are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1 to C6 alkyl group which may be substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be substituted with a substituent A, a C1 to C6 alkoxy group which may be substituted with a substituent A, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group which may be substituted with a substituent A, a C2 to C6 alkenyl group which may be substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be substituted with a substituent A, a C2 to C6 haloalkynyl group, a C2 to C6 cycloalkoxy group which may be substituted with a substituent A, C6 alkenyloxy group, C2 to C6 haloalkenyloxy group, C3 to C6 alkynyloxy group optionally substituted by substituent A, C3 to C6 haloalkynyloxy group, -NRaRb (wherein Ra and Rb are as defined above), -C(=O)NRaRb (wherein Ra and Rb are as defined above), -C(=O)ORc (wherein Rc is as defined above), -OC(=O)Rc (wherein Rc is as defined above), and -L-Rd (wherein Rd represents a group selected from the group consisting of a C1 to C6 alkyl group and a C1 to C6 haloalkyl group, and L is S, S(=O), or SO ２ represents a group selected from the group consisting of: ３ and R ４ together form a C5-C10 unsaturated ring which may be substituted with a substituent A; n represents an integer of 0 to 4; R ６represents a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1 to C6 alkyl group which may be substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be substituted with a substituent A, a C1 to C6 alkoxy group which may be substituted with a substituent A, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group which may be substituted with a substituent A, a C2 to C6 alkenyl group which may be substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be substituted with a substituent A, a C2 to C6 haloalkynyl group, a C2 to C6 alkenyl group which may be substituted with a substituent A represents a group selected from the group consisting of an oxy group, a C2 to C6 haloalkenyloxy group, a C3 to C6 alkynyloxy group optionally substituted by substituent A, a C3 to C6 haloalkynyloxy group, -NRaRb (wherein Ra and Rb are as defined above), -C(=O)ORc (wherein Rc is as defined above), -C(=O)NRaRb (wherein Ra and Rb are as defined above), -C(=O)ORc (wherein Rc is as defined above), -OC(=O)Rc (wherein Rc is as defined above), and -L-Rd (wherein L and Rd are as defined above); R ７ represents a group selected from the group consisting of a lone electron pair, a hydrogen atom, a C1 to C6 alkyl group which may be substituted with a substituent A, a C1 to C6 haloalkyl group, a C2 to C6 alkenyl group which may be substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be substituted with a substituent A, a C2 to C6 haloalkynyl group, and an acyl group which may be substituted with a substituent A; G １ , G ２ , and G ３ each independently represents a group selected from the group consisting of carbon atoms and nitrogen atoms (provided that G １ , G ２ , and G ３ At least one of the groups is a carbon atom; ４ and G ５each independently represents a group selected from the group consisting of a nitrogen atom and CRx; Rx is a hydrogen atom, a halogen atom, a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group optionally substituted with a substituent A, a C1 to C6 alkoxy group optionally substituted with a substituent A, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group optionally substituted with a substituent A, a C2 to C6 alkenyl group optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, a C2 to C6 alkenyloxy group optionally substituted with a substituent A, represents a group selected from the group consisting of a C2 to C6 haloalkenyloxy group, a C3 to C6 alkynyloxy group optionally substituted with a substituent A, a C3 to C6 haloalkynyloxy group, -NRaRb (wherein Ra and Rb are as defined above), -C(=O)NRaRb (wherein Ra and Rb are as defined above), -C(=O)ORc (wherein Rc is as defined above), and -L-Rd (wherein L and Rd are as defined above); a bond containing a dashed line represents a single bond or a double bond; X is O, S, S(=O), SO ２and NRe; Re represents a group selected from the group consisting of a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent A, a C1-C6 haloalkyl group, a C2-C6 alkenyl group optionally substituted with substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with substituent A, and a C2-C6 haloalkynyl group; Substituent A is a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 cycloalkoxy group, a C1-C6 alkenyloxy group, a C1-C6 haloalkenyloxy group, a C1-C6 alkynyloxy group, a C1-C6 haloalkynyloxy group, a C1-C6 acyl group, an aryl group optionally substituted with substituent B, a heteroaryl group optionally substituted with substituent B, a substituted aryl group ... Substituent B is at least one selected from the group consisting of a phenoxy group which may be optionally substituted with a substituent B, -NRaRb (wherein Ra and Rb are as defined above), -C(=O)NRaRb (wherein Ra and Rb are as defined above), -C(=O)ORc (wherein Rc is as defined above), -OC(=O)Rc (wherein Rc is as defined above), and -L-Rd (wherein L and Rd are as defined above); Substituent B is at least one selected from the group consisting of a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1 to C6 alkyl group which may be substituted with Substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, and Rd-L- (wherein Rd is as defined above). ] [2] G ４ and G ５ [3] The compound or salt thereof according to [1], wherein at least one of R ３ , R ４ , and R ５each independently represents a group selected from the group consisting of a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1 to C6 alkyl group which may be substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be substituted with a substituent A, a C1 to C6 alkoxy group which may be substituted with a substituent A, a C2 to C6 alkenyl group which may be substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be substituted with a substituent A, a C2 to C6 haloalkynyl group, a C2 to C6 alkenyloxy group which may be substituted with a substituent A, a C2 to C6 haloalkenyloxy group, a C3 to C6 alkynyloxy group which may be substituted with a substituent A, and a C3 to C6 haloalkynyloxy group, or R ３ and R ４ together form a C5-C10 unsaturated ring which may be substituted with a substituent A; n represents an integer of 0 to 2; R ６ represents a group selected from the group consisting of a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group optionally substituted with a substituent A, a C1 to C6 alkoxy group optionally substituted with a substituent A, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group optionally substituted with a substituent A, a C2 to C6 alkenyl group optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, a C2 to C6 alkenyloxy group optionally substituted with a substituent A, a C2 to C6 haloalkenyloxy group, a C3 to C6 alkynyloxy group optionally substituted with a substituent A, a C3 to C6 haloalkynyloxy group, and -NRaRb (wherein Ra and Rb are as defined above); R ７ represents a group selected from the group consisting of a lone electron pair, a hydrogen atom, a C1-C6 alkyl group which may be substituted with a substituent A, a C1-C6 haloalkyl group, and an acyl group which may be substituted with a substituent A; G ４ and G ５each independently represents a group selected from the group consisting of a nitrogen atom and CRx; Rx represents a group selected from the group consisting of a hydrogen atom, a halogen atom, a C1 to C6 alkyl group which may be substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be substituted with a substituent A, a C1 to C6 alkoxy group which may be substituted with a substituent A, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group which may be substituted with a substituent A, a C2 to C6 alkenyl group which may be substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be substituted with a substituent A, and a C2 to C6 haloalkynyl group; the compound or salt thereof according to [1] or [2]. In [1] to [3], R １ and R ２ each independently represents a group selected from the group consisting of a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group optionally substituted with a substituent A, a C2 to C6 alkenyl group optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, a C1 to C6 acyl group optionally substituted with a substituent A, an aryl group optionally substituted with a substituent B, and a heteroaryl group optionally substituted with a substituent B, or R １ and R ２ may be taken together to form a C3-C8 cycloalkyl ring which may be substituted with a substituent A, or a C3-C8 saturated or unsaturated heterocyclic ring which may be substituted with a substituent A, or R １ and R ２ each independently represents a group selected from the group consisting of a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group optionally substituted with a substituent A, a C2 to C6 alkenyl group optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, a C1 to C6 acyl group optionally substituted with a substituent A, an aryl group optionally substituted with a substituent B, and a heteroaryl group optionally substituted with a substituent B, or R１ and R ２ may be taken together to form a C3-C8 cycloalkyl ring which may be substituted with a substituent A. [4] G ４ and G ５ [5] The compound or salt thereof according to any one of [1] to [3], wherein at least one of R １ and R ２ each independently represents a group selected from the group consisting of a C1 to C6 alkyl group which may be substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C1 to C6 acyl group which may be substituted with a substituent A, an aryl group which may be substituted with a substituent B, a heteroaryl group which may be substituted with a substituent B, and -C(=O)ORc (wherein Rc has the same meaning as defined above), or R １ and R ２ together form a C3-C8 cycloalkyl ring which may be substituted with a substituent A, or a C3-C8 saturated or unsaturated heterocyclic ring which may be substituted with a substituent A; R ３ , R ４ , and R ５ each independently represents a group selected from the group consisting of a hydrogen atom, a halogen atom, a C1 to C6 alkyl group which may be substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be substituted with a substituent A, a C1 to C6 alkoxy group which may be substituted with a substituent A, and a C2 to C6 alkenyl group which may be substituted with a substituent A, or R ３ and R ４ together form a C5-C10 unsaturated ring which may be substituted with a substituent A; n represents an integer of 0 to 2; R ６represents a group selected from the group consisting of a halogen atom, a C1 to C6 alkyl group which may be substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be substituted with a substituent A, a C1 to C6 alkoxy group which may be substituted with a substituent A, a C3 to C8 cycloalkoxy group which may be substituted with a substituent A, a C2 to C6 alkenyl group which may be substituted with a substituent A, and -NRaRb (wherein Ra and Rb are as defined above); R ７ represents a lone pair of electrons; １ , G ２ and G ３ at least one of represents a carbon atom and at least one of represents a nitrogen atom; ４ and G ５ each independently represents a group selected from the group consisting of a nitrogen atom and CRx; Rx represents a group selected from the group consisting of a hydrogen atom and a C1-C6 alkyl group optionally substituted with a substituent A; the bond containing the dashed line represents a single bond or a double bond; X represents O, S, S(=O), and SO ２ [5A] The compound or salt thereof according to any one of [1] to [4], wherein R represents a group selected from the group consisting of １ and R ２are each independently a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a pentyl group, an isopentyl group, a 1-methylbutyl group, a 2-methylbutyl group, a neopentyl group, a 1-ethylpropyl group, a 1,2-dimethylpropyl group, a hexyl group, a chloromethyl group, a cyclopropyl group, a cyclobutyl group, a 1-butenyl group, a 4-methyl-3-pentenyl group, an acetyl group, a phenyl group, a 2-fluorophenyl group, a 3-fluorophenyl group, a 4-fluorophenyl group, a 2-chlorophenyl group, a 3-chlorophenyl group, a 4-chlorophenyl group, a 2-methylphenyl group, a 3-methylphenyl group, R represents a phenyl group, a 4-methylphenyl group, a 2-methoxyphenyl group, a 3-methoxyphenyl group, a 4-methoxyphenyl group, a 5-chlorothiophen-2-yl group, an ethoxycarbonyl group, a methoxymethyl group, a methoxyethyl group, an ethoxyethyl group, a methylthiomethyl group, a methylsulfonylmethyl group, a 2-amino-2-oxoethyl group, a 2-(methylamino)-2-oxoethyl group, a 2-(dimethylamino)-2-oxoethyl group, a 2-carboxymethyl group, a 2-methoxy-2-oxoethyl group, a 2-ethoxy-2-oxoethyl group, a 3-methoxy-3-oxopropyl group, a 3-cyanopropyl group, or a 2-phenethyl group; １ and R ２ [5B] The compound or salt thereof according to any one of [1] to [5], wherein R ３ and R ４ each independently represents a hydrogen atom, a fluoro group, a chloro group, a bromo group, a methyl group, an ethyl group, a difluoromethyl group, a trifluoromethyl group, a cyclopropyl group, a methoxy group, a vinyl group, or a 1-propen-2-yl group; R ３ and R ４ [5C] The compound or salt thereof according to any one of [1] to [5], wherein R ５ [5D] The compound or salt thereof according to any one of [1] to [5], wherein R is a hydrogen atom or a methyl group. ６[5E] The compound or salt thereof according to any one of [1] to [5], wherein R is a fluoro group, a chloro group, a bromo group, a methyl group, an ethyl group, a propyl group, a cyclopropyl group, a methoxy group, a vinyl group, a 1-propen-2-yl group, a methylamino group, an ethylamino group, a dimethylamino group, an ethylmethylamino group, or a t-butoxycarbonylamino group. [5F] The compound or salt thereof according to any one of [1] to [5], wherein R ７ represents a lone pair of electrons, and R ７ [5G] The compound or salt thereof according to any one of [1] to [5], wherein the bond including the dashed line portion formed by the nitrogen atom to which is bonded represents a double bond. ２ The compound or salt thereof according to any one of [1] to [5] represents a group selected from the group consisting of:

[0014] In addition, in [5A] to [5G], [5] in the description "a compound or salt thereof according to any one of [1] to [5]" is used to mean including the preceding [5A] to [5G]. In addition, in "any one of [1] to [5]" in the following [9] to

[12] , when [5] is used, it is used to mean including [5A] to [5G]. [6] Formula (2) is selected from the group consisting of the following formulas (2-1), (2-2), (2-3), (2-4), (2-5), (2-6), (2-7), (2-8), (2-9), (2-10), and (2-11), R ３ , R ４ , and R ｘ [7] The compound or salt thereof according to any one of [1] to [5], wherein Rx is a hydrogen atom or a methyl group. [7] Formula (2) is selected from the group consisting of the following formulae (2-1), (2-2), (2-3), (2-5), (2-6), (2-8), and (2-9): R ３ , R ４ , and R ｘ is the same as defined above, and preferably Rx represents a hydrogen atom or a methyl group. [8] The compound or salt thereof according to any one of [1] to [5], wherein formula (2) is selected from the group consisting of the following formulas (2-2), (2-3), (2-6), and (2-9): R３ , R ４ , and R ｘ is as defined above, and preferably Rx represents a hydrogen atom or a methyl group, the compound or salt thereof according to any one of [1] to [5]. [9] An agricultural and horticultural pest control agent containing the compound or salt thereof according to any one of [1] to [8].

[10] An agricultural and horticultural fungicide containing the compound or salt thereof according to any one of [1] to [8].

[11] A method for controlling plant diseases, comprising applying the compound or salt thereof according to any one of [1] to [8], or the agricultural and horticultural pest control agent according to [9], to plants, plant seeds, or soil for cultivating plants.

[12] A method for controlling plant diseases, comprising applying the compound or salt thereof according to any one of [1] to [8], or the agricultural and horticultural fungicide according to

[10] , to plants, plant seeds, or soil for cultivating plants.

[0008] According to the present invention, it is possible to provide a novel compound, an agricultural and horticultural pest control agent and agricultural and horticultural fungicide containing the compound or a salt thereof, and a method for controlling plant diseases.

[0009] Hereinafter, a mode for carrying out the present invention (hereinafter referred to as "the present embodiment") will be described in detail. The present embodiment is an example for explaining the present invention, and is not intended to limit the present invention to the following content. The present invention can be carried out by appropriately modifying it within the scope of its gist.

[0010] The abbreviations used in this specification are explained below. DMF: N,N-dimethylformamide, THF: tetrahydrofuran, Me: methyl group, Et: ethyl group, Pr: propyl group, Bu: butyl group, Ac: acetyl group, Ph: phenyl group, i: iso, sec: secondary, t: tertiary, c: cyclo, o: ortho, m: meta, p: para, =: double bond, ≡: triple bond. In the table columns, Pr and Bu without a prefix mean normal.

[0011] The definitions of the terms used in this specification are explained below. In this specification, "optionally substituted" means that it may or may not be substituted with a substituent, and is synonymous with "substituted or unsubstituted." When the number of substituents is not specified, the number of substituents is not particularly limited.

[0012] As used herein, "Cx-Cy" means having x to y carbon atoms. Here, x and y are integers, and it is understood that all integers between x and y are individually disclosed. For example, C1-C6 means having 1, 2, 3, 4, 5, or 6 carbon atoms, C2-C6 means having 2, 3, 4, 5, or 6 carbon atoms, C3-C8 means having 3, 4, 5, 6, 7, or 8 carbon atoms, C3-C6 means having 3, 4, 5, or 6 carbon atoms, and C1-C3 means having 1, 2, or 3 carbon atoms.

[0013] In this specification, a "C1 to C6 alkyl group" refers to a linear or branched hydrocarbon group having 1 to 6 carbon atoms. Examples of a "C1 to C6 alkyl group" include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a 1-methylbutyl group, a 2-methylbutyl group, a neopentyl group, a 1-ethylpropyl group, a 1,2-dimethylpropyl group, an n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 3-methylpentyl group, a 4-methylpentyl group, a 1,1-dimethylbutyl group, a 2,2-dimethylbutyl group, a 3,3-dimethylbutyl group, a 1,2-dimethylbutyl group, a 1,3-dimethylbutyl group, a 2,3-dimethylbutyl group, a 2-ethylbutyl group, a 1-isopropylpropyl group, a 1,1,2-trimethylpropyl group, and a 1,2,2-trimethylpropyl group.

[0014] In this specification, examples of the "halogen atom" include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0015] In this specification, a "C1 to C6 haloalkyl group" refers to a group in which at least one hydrogen atom in the C1 to C6 alkyl group is substituted with a halogen atom. When two or more hydrogen atoms are substituted with halogen atoms, the halogen atoms may be the same or different, and the number of substituted halogen atoms is not particularly limited as long as they can exist as substituents. Examples of the "C1 to C6 haloalkyl group" include a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a monochloromethyl group, a dichloromethyl group, a monobromomethyl group, a dibromomethyl group, a monoiodomethyl group, a diiodomethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, a trichloromethyl group, a 1-fluoroethyl group, a 2-fluoroethyl group, a 1,1-difluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2, Examples include a 2-tetrafluoroethyl group, a pentafluoroethyl group, a 2,2,2-trichloroethyl group, a 3,3-difluoropropyl group, a 3,3,3-trifluoropropyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a 2,2,2-trifluoro-1-(trifluoromethyl)ethyl group, a nonafluorobutyl group, a nonafluoro-sec-butyl group, a 3,3,4,4,5,5,5-heptafluoropentyl group, an undecafluoropentyl group, and a tridecafluorohexyl group.

[0016] In this specification, a "C3 to C8 cycloalkyl group" refers to a cyclic hydrocarbon group having 3 to 8 carbon atoms. Examples of a "C3 to C8 cycloalkyl group" include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

[0017] In this specification, a "C2 to C6 alkenyl group" refers to a C2 to C6 alkyl group, among the C1 to C6 alkyl groups, that has at least one double bond. When geometric isomers exist, the alkyl group may be an E-isomer, a Z-isomer, or a combination thereof. Examples of the "C2 to C6 alkenyl group" include a vinyl group, an allyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1,3-butadienyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 4-pentenyl group, a 3-methyl-2-butenyl group, a 1-hexenyl group, a 2-hexenyl group, a 3-hexenyl group, a 4-hexenyl group, a 5-hexenyl group, a 4-methyl-3-pentenyl group, and a 3-methyl-2-pentenyl group.

[0018] In this specification, a "C2 to C6 haloalkenyl group" refers to the C2 to C6 alkenyl group in which at least one hydrogen atom has been substituted with a halogen atom. When two or more hydrogen atoms are substituted with halogen atoms, the halogen atoms may be the same or different, and the number of substituted halogen atoms is not particularly limited as long as they can exist as substituents. Examples of the "C2 to C6 haloalkenyl group" include a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 2,2-dichlorovinyl group, a 3-fluoroallyl group, a 3,3-difluoroallyl group, a 3,3-dichloroallyl group, a 4,4-difluoro-3-butenyl group, a 5,5-difluoro-4-pentenyl group, and a 6,6-difluoro-5-hexenyl group.

[0019] In this specification, a "C3 to C10 cycloalkenyl group" refers to a cyclic hydrocarbon group having 3 to 10 carbon atoms and having at least one double bond. Examples of a "C3 to C10 cycloalkenyl group" include a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, a cyclopentadienyl group, and a cyclohexenyl group.

[0020] In this specification, the term "C2 to C6 alkenyloxy group" refers to a group in which one of two bonds of an oxygen atom is bonded to the C2 to C6 alkenyl group, and the term "C2 to C6 alkenyloxy group" refers to a group in which the C2 to C6 alkenyl group is bonded via an oxygen atom. Examples of a "C2 to C6 alkenyloxy group" include a vinyloxy group, a 1-propenyloxy group, an allyloxy group, a 1-butenyloxy group, a 2-butenyloxy group, a 3-butenyloxy group, a 1-pentenyloxy group, a 2-pentenyloxy group, a 3-pentenyloxy group, a 4-pentenyloxy group, a 3-methyl-2-butenyloxy group, a 1-hexenyloxy group, a 2-hexenyloxy group, a 3-hexenyloxy group, a 4-hexenyloxy group, a 5-hexenyloxy group, a 3-methyl-2-pentenyloxy group, and a 4-methyl-3-pentenyloxy group.

[0021] In this specification, a "C2 to C6 haloalkenyloxy group" refers to a group in which one of two bonds of an oxygen atom is bonded to the C2 to C6 haloalkenyl group, and a "C2 to C6 haloalkenyloxy group" refers to a C2 to C6 haloalkenyl group bonded via an oxygen atom. Examples of the "C2 to C6 haloalkenyloxy group" include a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 2,2-dichlorovinyloxy group, a 3-fluoroallyloxy group, a 3,3-difluoroallyloxy group, a 3,3-dichloroallyloxy group, a 4,4-difluoro-3-butenyloxy group, a 5,5-difluoro-4-pentenyloxy group, and a 6,6-difluoro-5-hexenyloxy group.

[0022] In this specification, a "C2 to C6 alkynyl group" refers to the C1 to C6 alkyl group described above, which has at least one triple bond. Examples of the "C2 to C6 alkynyl group" include an ethynyl group, a 1-propynyl group, a propargyl 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, a 1,1-dimethyl-2-propynyl group, a 1-hexynyl group, a 2-hexynyl group, a 3-hexynyl group, a 4-hexynyl group, and a 5-hexynyl group.

[0023] As used herein, a "C2-C6 haloalkynyl group" refers to the C2-C6 alkynyl group in which at least one hydrogen atom has been substituted with a halogen atom. When two or more hydrogen atoms are substituted with halogen atoms, the halogen atoms may be the same or different, and the number of halogen atoms substituted is not particularly limited, as long as they can exist as substituents. Examples of the "C2 to C6 haloalkynyl group" include a 2-fluoroethynyl group, a 2-chloroethynyl group, a 2-bromoethynyl group, a 2-iodoethynyl group, a 3,3-difluoro-1-propynyl group, a 3-chloro-3,3-difluoro-1-propynyl group, a 3-bromo-3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, a 4,4-difluoro-1-butynyl group, a 4,4-difluoro-2-butynyl group, a 4-chloro-4,4-difluoro-1-butynyl group, a 4-chloro-4,4-difluoro-2-butynyl group, a 4-bromo-4,4-difluoro-1 -butynyl group, 4-bromo-4,4-difluoro-2-butynyl group, 4,4,4-trifluoro-1-butynyl group, 4,4,4-trifluoro-2-butynyl group, 5,5-difluoro-3-pentynyl group, 5-chloro-5,5-difluoro-3-pentynyl group, 5-bromo-5,5-difluoro-3-pentynyl group, 5,5,5-trifluoro-3-pentynyl group, 6,6-difluoro-4-hexynyl group, 6-chloro-6,6-difluoro-4-hexynyl group, 6-bromo-6,6-difluoro-4-hexynyl group, 6,6,6-trifluoro-4-hexynyl group, and the like.

[0024] In this specification, a "C3 to C6 alkynyloxy group" refers to a group in which one of two bonds of an oxygen atom is bonded to the C2 to C6 alkynyl group, and a "C3 to C6 alkynyloxy group" refers to a C2 to C6 alkynyl group bonded via an oxygen atom. Examples of the "C3 to C6 alkynyloxy group" include a propargyloxy group, a 2-butynyloxy group, a 3-butynyloxy group, a 2-pentynyloxy group, a 3-pentynyloxy group, a 4-pentynyloxy group, a 1,1-dimethyl-2-propynyloxy group, a 2-hexynyloxy group, a 3-hexynyloxy group, a 4-hexynyloxy group, and a 5-hexynyloxy group.

[0025] In the present specification, a "C3 to C6 haloalkynyloxy group" is a group in which one of two bonds of an oxygen atom is bonded to the C2 to C6 haloalkynyl group, and a "C3 to C6 haloalkynyloxy group" is a group in which the C3 to C6 haloalkynyl group is bonded via an oxygen atom. Examples of the "C3 to C6 haloalkynyloxy group" include a 1,1-difluoro-2-propynyloxy group, a 4,4-difluoro-2-butynyloxy group, a 4-chloro-4,4-difluoro-2-butynyloxy group, a 4-bromo-4,4-difluoro-2-butynyloxy group, a 4,4,4-trifluoro-2-butynyloxy group, a 5,5-difluoro-3-pentynyloxy group, a 5-chloro-5,5- Examples thereof include a difluoro-3-pentynyloxy group, a 5-bromo-5,5-difluoro-3-pentynyloxy group, a 5,5,5-trifluoro-3-pentynyloxy group, a 6,6-difluoro-4-hexynyloxy group, a 6-chloro-6,6-difluoro-4-hexynyloxy group, a 6-bromo-6,6-difluoro-4-hexynyloxy group, and a 6,6,6-trifluoro-4-hexynyloxy group.

[0026] In this specification, the term "C1 to C6 acyl group" refers to a formyl group or a carbonyl group bonded to a C1 to C5 alkyl group. Examples of the "C1 to C6 acyl group" include a formyl group, an acetyl group, a propionyl group, a butyryl group, an isobutyryl group, a pentanoyl group, a 2-methylbutanoyl group, a 3-methylbutanoyl group, a pivaloyl group, a hexanoyl group, a 2-methylpentanoyl group, a 3-methylpentanoyl group, a 4-methylpentanoyl group, a 2,2-dimethylbutanoyl group, a 2,3-dimethylbutanoyl group, a 2-ethylbutanoyl group, and a 3-ethylbutanoyl group.

[0027] In this specification, the term "aryl group" may be either a monocyclic aryl group or a fused polycyclic aryl group. Examples of the "aryl group" include a phenyl group, a naphthyl group, a phenanthrenyl group, and an anthracenyl group.

[0028] In this specification, the term "heteroaryl group" may be either a monocyclic heteroaryl group or a fused polycyclic heteroaryl group, and is an aromatic ring group containing one or more heteroatoms (e.g., oxygen atom, nitrogen atom, sulfur atom, etc.) as ring-constituting atoms. Examples of the "heteroaryl group" include a pyrrolyl group, a furyl group, a thienyl group, a pyrazolyl group, an imidazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a tetrazolyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a quinolyl group, an isoquinolyl group, a naphthyridinyl group, a quinoxalinyl group, a cinnolinyl group, a quinazolinyl group, a phthalazinyl group, an imidazopyridyl group, an imidazothiazolyl group, an aryl group, a ... Examples thereof include an azolyl group, an imidazoxazolyl group, a benzothiazolyl group, a benzoxazolyl group, a benzimidazolyl group, an indolyl group, an isoindolyl group, an indazolyl group, a pyrrolopyridyl group, a thienopyridyl group, a furopyridyl group, a benzothiadiazolyl group, a benzoxadiazolyl group, a pyridopyrimidinyl group, a benzofuryl group, a benzothienyl group, a benzo[1,3]dioxole group, a thienofuryl group, a chromenyl group, a chromanyl group, a coumarinyl group, and a quinolonyl group.

[0029] In this specification, a "C3 to C8 saturated or unsaturated heterocyclic ring" refers to a saturated or unsaturated ring composed of 3 to 8 carbon atoms and at least one heteroatom (for example, an oxygen atom, a nitrogen atom, or a sulfur atom). Examples of the "C3 to C8 saturated or unsaturated heterocyclic ring" include azetidine, oxetane, thietane, pyrrolidine, imidazolidine, triazolidine, tetrazolidine, pyrazolidine, tetrahydrofuran, tetrahydrothiophene, tetrahydrooxazole (oxazolidine), tetrahydroisoxazole (isoxazolidine), tetrahydrothiazole (thiazolidine), tetrahydroisothiazole (isothiazolidine), tetrahydrofurazan, tetrahydrooxadiazole (oxadiazolidine), tetrahydrothiadiazole (thiadiazolidine), dioxolane, and dithiolane. , piperidine, piperazine, perhydropyrimidine, perhydropyridazine, tetrahydropyran, tetrahydrothiopyran, tetrahydrooxazine, tetrahydrooxadiazine, tetrahydrothiazine, tetrahydrothiadiazine, morpholine, thiomorpholine, oxathiane, dioxane, dithiane, thiophene, furan, pyrrole, selenophene, thiazole, oxazole, imidazole, selenazole, thiadiazole, oxadiazole ring, triazole ring, pyridine ring, pyran ring, pyrazine ring, pyrimidine ring, thienothiophene ring, benzothiophene ring, and the like.

[0030] In this specification, the term "C1 to C6 alkoxy group" refers to a group in which one of two bonds of an oxygen atom is bonded to the C1 to C6 alkyl group, and the term "C1 to C6 alkoxy group" refers to a group in which the C1 to C6 alkyl group is bonded via an oxygen atom. Examples of the "C1 to C6 alkoxy group" include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, a pentyloxy group, an isopentyloxy group, a 1-methylbutoxy group, a 2-methylbutoxy group, a neopentyloxy group, a 1-ethylpropyloxy group, a 1,2-dimethylpropyloxy group, a hexyloxy group, a 1-methylpentyloxy group, a 2-methylbut ... Examples thereof include a methylpentyloxy group, a 3-methylpentyloxy group, a 4-methylpentyloxy group, a 1,1-dimethylbutoxy group, a 2,2-dimethylbutoxy group, a 3,3-dimethylbutoxy group, a 1,2-dimethylbutoxy group, a 1,3-dimethylbutoxy group, a 2,3-dimethylbutoxy group, a 2-ethylbutoxy group, a 1-isopropylpropyloxy group, a 1,1,2-trimethylpropyloxy group, and a 1,2,2-trimethylpropyloxy group.

[0031] In this specification, the term "C1-C6 haloalkoxy group" refers to the above-mentioned C1-C6 alkoxy group in which a hydrogen atom is optionally substituted with one or more halogen atoms. When substituted with two or more halogen atoms, these halogen atoms may be the same or different, and there is no particular limitation on the number of substitutions, as long as they can exist as substituents. Specific examples of C1 to C6 haloalkoxy groups include difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, pentafluoroethoxy, 2,2,2-trichloroethoxy, 3,3-difluoropropyloxy, 3,3,3-trifluoropropyloxy, heptafluoropropyloxy, heptafluoroisopropyloxy, 2,2,2-trifluoro-1-(trifluoromethyl)-ethoxy, nonafluorobutoxy, nonafluoro-sec-butoxy, 3,3,4,4,5,5,5-heptafluoropentyloxy, undecafluoropentyloxy, and tridecafluorohexyloxy.

[0032] In this specification, the term "C2-C6 alkenyloxy group" refers to the above-mentioned C2-C6 alkenyl group bonded via an oxygen atom. When geometric isomers exist, they may be either the E- or Z-isomer alone, or a mixture of the E- and Z-isomers in any proportion, and are not particularly limited as long as the number of carbon atoms is within the specified range. Specific examples of C2 to C6 alkenyloxy groups include vinyloxy group, 1-propenyloxy group, allyloxy group, 1-butenyloxy group, 2-butenyloxy group, 3-butenyloxy group, 1-pentenyloxy group, 2-pentenyloxy group, 3-pentenyloxy group, 4-pentenyloxy group, 3-methyl-2-butenyloxy group, 1-hexenyloxy group, 2-hexenyloxy group, 3-hexenyloxy group, 4-hexenyloxy group, 5-hexenyloxy group, 4-methyl-3-pentenyloxy group, and 3-methyl-2-pentenyloxy group.

[0033] As used herein, the term "C2 to C6 haloalkenyloxy group" refers to the C2 to C6 alkenyloxy group in which one or more hydrogen atoms have been arbitrarily substituted with one or more halogen atoms. When substituted with two or more halogen atoms, these halogen atoms may be the same or different, and there is no particular limitation on the number of substitutions, as long as they can exist as substituents. Specific examples of C2 to C6 haloalkenyloxy groups include a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 2,2-dichlorovinyloxy group, a 3-fluoroallyloxy group, a 3,3-difluoroallyloxy group, a 3,3-dichloroallyloxy group, a 4,4-difluoro-3-butenyloxy group, a 5,5-difluoro-4-pentenyloxy group, and a 6,6-difluoro-5-hexenyloxy group.

[0034] In this specification, the term "C3 to C6 alkynyloxy group" refers to a C3 to C6 alkynyl group, among the above-mentioned C2 to C6 alkynyl groups, in which the C3 to C6 alkynyl group is bonded via an oxygen atom. Specific examples of the C3 to C6 alkynyloxy group include a propargyloxy group, a 2-butynyloxy group, a 3-butynyloxy group, a 2-pentynyloxy group, a 3-pentynyloxy group, a 4-pentynyloxy group, a 1,1-dimethyl-2-propynyloxy group, a 2-hexynyloxy group, a 3-hexynyloxy group, a 4-hexynyloxy group, and a 5-hexynyloxy group.

[0035] In this specification, the term "C3 to C6 haloalkynyloxy group" refers to the C3 to C6 alkynyloxy group in which one or more hydrogen atoms have been arbitrarily substituted with one or more halogen atoms. When substituted with two or more halogen atoms, these halogen atoms may be the same or different, and there is no particular limitation on the number of substitutions as long as they can exist as substituents. Specific examples of the C3 to C6 haloalkynyloxy group include 1,1-difluoro-2-propynyloxy group, 4,4-difluoro-2-butynyloxy group, 4-chloro-4,4-difluoro-2-butynyloxy group, 4-bromo-4,4-difluoro-2-butynyloxy group, 4,4,4-trifluoro-2-butynyloxy group, 5,5-difluoro-3-pentynyloxy group, 5-chloro-5,5-difluoro-2-butynyloxy group, 5,5-difluoro-3-pentynyloxy group, ... Examples thereof include a fluoro-3-pentynyloxy group, a 5-bromo-5,5-difluoro-3-pentynyloxy group, a 5,5,5-trifluoro-3-pentynyloxy group, a 6,6-difluoro-4-hexynyloxy group, a 6-chloro-6,6-difluoro-4-hexynyloxy group, a 6-bromo-6,6-difluoro-4-hexynyloxy group, and a 6,6,6-trifluoro-4-hexynyloxy group.

[0036] In this specification, a "C3 to C8 cycloalkoxy group" refers to a group in which one of two bonds of an oxygen atom is bonded to the C3 to C8 cycloalkyl group, and a "C3 to C8 cycloalkoxy group" refers to a C3 to C8 cycloalkyl group bonded via an oxygen atom. Examples of the "C3 to C8 cycloalkoxy group" include a cyclopropyloxy group, cyclobutoxy group, cyclopentyloxy group, cyclohexyloxy group, cycloheptyloxy group, and cyclooctyloxy group.

[0037] In this specification, the "C5 to C10 unsaturated ring" refers to an unsaturated ring composed of 5 to 10 carbon atoms which may contain a heteroatom (for example, an oxygen atom, a nitrogen atom, or a sulfur atom). The "C5 to C10 unsaturated ring" may or may not have aromaticity. Examples of the "C5 to C10 unsaturated ring" include the aryl group, the heteroaryl group, the unsaturated heterocycle, and the cycloalkenyl group.

[0038] [Compound] One embodiment of the present invention is a compound represented by the following formula (1), or a salt thereof. Formula (1):

[0039] Formula (1) will be described below. R in Formula (1) １ and R ２ When these are different, the compound represented by formula (1) is either the R-configuration or the S-configuration, or is a mixture of the R-configuration and the S-configuration in any ratio.

[0040] R in formula (1) １ and R ２are each independently a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group optionally substituted with a substituent A, a C2 to C6 alkenyl group optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, a C1 to C6 acyl group optionally substituted with a substituent A, an aryl group optionally substituted with a substituent B, a heteroaryl group optionally substituted with a substituent B, and -C(=O)NRaRb (wherein Ra and Rb are each independently a hydrogen atom, a C1 to C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 acyl group, and —C(═O)ORc (wherein Rc represents a group selected from the group consisting of a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent A, a C1-C6 haloalkyl group, and a C3-C8 cycloalkyl group); or Ra and Rb together with the nitrogen atom to which they are bonded form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group, or an azocanyl group) and —C(═O)ORc (wherein Rc has the same meaning as defined above); or R １ and R ２ taken together represent a C3 to C8 cycloalkyl group which may be substituted with a substituent A, or a C3 to C8 saturated or unsaturated heterocycle which may be substituted with a substituent A.

[0041] Among them, R １ and R ２each independently represent a group selected from the group consisting of a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group optionally substituted with a substituent A, a C2 to C6 alkenyl group optionally substituted with a substituent A, a C1 to C6 acyl group optionally substituted with a substituent A, an aryl group optionally substituted with a substituent B, or -C(=O)ORc (wherein Rc represents a group selected from the group consisting of a hydrogen atom, a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group, and a C3 to C8 cycloalkyl group); or Ra and Rb together with the nitrogen atom to which they are bonded form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group, or an azocanyl group; or R １ and R ２ together preferably represent a C3-C8 cycloalkyl ring which may be substituted with a substituent A.

[0042] R in formula (1) １ and R ２ The C1 to C6 alkyl group in the "C1 to C6 alkyl group which may be substituted with a substituent A" has the same meaning as defined above and is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a s-butyl group, a pentyl group, an isopentyl group, a 1-methylbutyl group, a 2-methylbutyl group, a neopentyl group, a 1-ethylpropyl group, a 1,2-dimethylpropyl group, or a hexyl group, more preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a pentyl group, or an isopentyl group. When the C1 to C6 alkyl group has a substituent A, a hydrogen atom in the C1 to C6 alkyl group is optionally substituted with a substituent A.

[0043] R in formula (1) １ and R ２The "C1 to C6 haloalkyl group" in the above formula has the same meaning as defined above, and is preferably a difluoromethyl group, a trifluoromethyl group, a monochloromethyl group, a dichloromethyl group, a diiodomethyl group, a chlorodifluoromethyl group, a 1,1-difluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 2,2,2-trichloroethyl group, a 3,3-difluoropropyl group, or a 3,3,3-trifluoropropyl group.

[0044] R in formula (1) １ and R ２ The C3 to C8 cycloalkyl group in the "C3 to C8 cycloalkyl group which may be substituted with a substituent A" in the above is as defined above, and is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, more preferably a cyclopropyl group or a cyclobutyl group. When the C3 to C8 cycloalkyl group has a substituent A, a hydrogen atom in the C3 to C8 cycloalkyl group is optionally substituted with a substituent A.

[0045] R in formula (1) １ and R ２ The C2-C6 alkenyl group in the "C2-C6 alkenyl group which may be substituted with substituent A" has the same meaning as defined above, and is preferably a vinyl group, a 1-propenyl group, an allyl 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 3-methyl-2-butenyl group, or a 4-methyl-3-pentenyl group. When the C2-C6 alkenyl group has substituent A, a hydrogen atom in the C2-C6 alkenyl group is optionally substituted with substituent A.

[0046] R in formula (1) １ and R ２ The "C2 to C6 haloalkenyl group" in the formula (I) has the same meaning as defined above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 3-fluoroallyl group, a 3,3-difluoroallyl group, or a 4,4-difluoro-3-butenyl group.

[0047] R in formula (1) １ and R ２The C2-C6 alkynyl group in the "C2-C6 alkynyl group which may be substituted with substituent A" has the same meaning as defined above, and is preferably an ethynyl group, a 1-propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, or a 3-butynyl group. When the C2-C6 alkynyl group has substituent A, a hydrogen atom in the C2-C6 alkynyl group is optionally substituted with substituent A.

[0048] R in formula (1) １ and R ２ The "C2 to C6 haloalkynyl group" in the above formula has the same meaning as defined above, and is preferably a 2-fluoroethynyl group, a 2-chloroethynyl group, a 2-bromoethynyl group, a 2-iodoethynyl group, a 3,3-difluoro-1-propynyl group, a 3-chloro-3,3-difluoro-1-propynyl group, a 3-bromo-3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, a 4,4-difluoro-1-butynyl group, a 4,4-difluoro-2-butynyl group, a 4-chloro-4,4-difluoro-1-butynyl group, a 4-chloro-4,4-difluoro- Examples of fluoroethynyl include 4-fluoroethynyl, 4-bromo-4,4-difluoro-1-butynyl, 4-bromo-4,4-difluoro-2-butynyl, 4,4,4-trifluoro-1-butynyl, and 4,4,4-trifluoro-2-butynyl groups, and more preferably 2-fluoroethynyl, 3,3-difluoro-1-propynyl, 3,3,3-trifluoro-1-propynyl, 4,4-difluoro-1-butynyl, 4,4-difluoro-2-butynyl, 4,4,4-trifluoro-1-butynyl, and 4,4,4-trifluoro-2-butynyl groups.

[0049] R in formula (1) １ and R ２ The C1-C6 acyl group in the "C1-C6 acyl group which may be substituted with a substituent A" has the same meaning as defined above, and is preferably a formyl group, an acetyl group, a propionyl group, a butyryl group, or an isobutyryl group, and more preferably an acetyl group or a propionyl group. When the C1-C6 acyl group has a substituent A, a hydrogen atom in the C1-C6 acyl group is optionally substituted with a substituent A.

[0050] R in formula (1)１ and R ２ The aryl group in the "aryl group which may be substituted with a substituent B" in the formula (I) has the same meaning as defined above, and is preferably a phenyl group. When the aryl group has a substituent B, a hydrogen atom in the aryl group is optionally substituted with the substituent B.

[0051] R in formula (1) １ and R ２ The heteroaryl group in the "heteroaryl group which may be substituted with substituent B" in (I) has the same meaning as defined above, and is preferably a pyridyl group, a pyrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group, a furyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a triazolyl group, an oxadiazolyl group, or a tetrazolyl group, and more preferably a thienyl group. When the heteroaryl group has substituent B, a hydrogen atom in the heteroaryl group is optionally substituted with substituent B.

[0052] R in formula (1) １ and R ２In the formula, Ra and Rb of "-C(=O)NRaRb" have the same meanings as defined above. Preferable examples of "-C(=O)NRaRb" include an aminocarbonyl group, a methylaminocarbonyl group, an ethylaminocarbonyl group, a (methoxymethyl)aminocarbonyl group, a (2-methoxyethyl)aminocarbonyl group, a (cyanomethyl)aminocarbonyl group, a (2-cyanoethyl)aminocarbonyl group, a dimethylaminocarbonyl group, an ethylmethylaminocarbonyl group, a diethylaminocarbonyl group, a (methoxymethyl)methylaminocarbonyl group, a (2-methoxyethyl)methylaminocarbonyl group, a (cyanomethyl)methylaminocarbonyl group, a (2-cyano

[0033] The aryl group is preferably an aminocarbonyl group, a methylaminocarbonyl group, a dimethylaminocarbonyl group, an ethylmethylaminocarbonyl group, or a diethylaminocarbonyl group, and more preferably an aminocarbonyl group, a methylaminocarbonyl group, or a dimethylaminocarbonyl group.

[0053] Rc in "-C(=O)ORc" in R1 and R2 of formula (1) has the same meaning as defined above. "-C(=O)ORc" is preferably a carboxy group, a methoxycarbonyl group, an ethoxycarbonyl group, a propyloxycarbonyl group, an isopropyloxycarbonyl group, a butoxycarbonyl group, an isobutoxycarbonyl group, a difluoromethoxycarbonyl group, a trifluoromethoxycarbonyl group, a 2,2-difluoroethoxycarbonyl group, a 2,2,2-trifluoroethoxycarbonyl group, a 3,3-difluoropropyloxycarbonyl group, a 3,3,3-trifluoropropyloxy group, a cyclo

[0033] In the case where the substituent A is present, a hydrogen atom in the C1-C6 alkyl group is optionally substituted with the substituent A. In the case where the substituent A is present, a hydrogen atom in the C1-C6 alkyl group is optionally substituted with the substituent A. In the case where the substituent A is present, a hydrogen atom in the C1-C6 alkyl group is optionally substituted with the substituent A. In the case where the substituent A is present, a hydrogen atom in the C1-C6 alkyl group is optionally substituted with the substituent A. In the case where the substituent A is present, a hydrogen atom in the C1-C6 alkyl group is optionally substituted with the substituent A. In the case where the substituent A is present, a hydrogen atom in the C1-C6 alkyl group is optionally substituted with the substituent A. In the case where the substituent A is present, a hydrogen atom in the C1-C6 alkyl group is optionally substituted with the substituent A.

[0054] R in formula (1) １ and R ２ "R" in １ and R ２ and , taken together, form a C3-C8 cycloalkyl group which may be substituted with a substituent A" has the same meaning as defined above and is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, more preferably a cyclopropyl group or a cyclobutyl group. When the C3-C8 cycloalkyl group has a substituent A, a hydrogen atom in the C3-C8 cycloalkyl group is optionally substituted with a substituent A.

[0055] R in formula (1) １ and R ２ "R" in １ and R ２and (iii) optionally substituted with a substituent A," the C3-C8 saturated or unsaturated heterocyclic ring has the same meaning as defined above, and is preferably a 3-oxetanyl group, a 3-thietanyl group, a 3-tetrahydrofuranyl group, a 3-tetrahydrothiophenyl group, a 3-tetrahydropyranyl group, a 4-tetrahydropyranyl group, a 3-tetrahydrothiopyranyl group, or a 4-tetrahydrothiopyranyl group. When the C3-C8 saturated or unsaturated heterocyclic ring has a substituent A, a hydrogen atom in the C3-C8 saturated or unsaturated heterocyclic ring is optionally substituted with a substituent A.

[0056] Hereinafter, Het in formula (1) will be described in detail. Het in formula (1) represents a partial structure represented by formula (2). Furthermore, the wavy line in formula (2) represents the bond in formula (1).

[0057] R in formula (2) ３ and R ４are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1 to C6 alkyl group which may be substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be substituted with a substituent A, a C1 to C6 alkoxy group which may be substituted with a substituent A, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group which may be substituted with a substituent A, a C2 to C6 alkenyl group which may be substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be substituted with a substituent A, a C2 to C6 haloalkynyl group, or a C2 to C6 alkyl group which may be substituted with a substituent A. a C2 to C6 alkenyloxy group, a C2 to C6 haloalkenyloxy group, a C3 to C6 alkynyloxy group optionally substituted with substituent A, a C3 to C6 haloalkynyloxy group, -NRaRb (wherein Ra and Rb each independently represent a hydrogen atom, a C1 to C6 alkyl group optionally substituted with substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, a C1 to C6 acyl group, or -C(=O)ORc (wherein Rc represents a hydrogen atom, a C1 to C6 alkyl group optionally substituted with substituent A, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group); Ra and Rb together with the nitrogen atom to which they are bonded form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group, or an azocanyl group; —C(═O)NRaRb (wherein Ra and Rb are as defined above); —C(═O)ORc (wherein Rc is as defined above); —OC(═O)Rc (wherein Rc is as defined above); or —L-Rd (wherein Rd is a C1-C6 alkyl group or a C1-C6 haloalkyl group, and L is S, S(═O), or SO2); or R ３ and R ４ together represent an unsaturated ring of C5 to C10 which may be substituted with a substituent A.

[0058] Among them, R ３ and R ４each independently represents a group selected from the group consisting of a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1 to C6 alkyl group which may be substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be substituted with a substituent A, a C1 to C6 alkoxy group which may be substituted with a substituent A, a C2 to C6 alkenyl group which may be substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be substituted with a substituent A, a C2 to C6 haloalkynyl group, a C2 to C6 alkenyloxy group which may be substituted with a substituent A, a C2 to C6 haloalkenyloxy group, a C3 to C6 alkynyloxy group which may be substituted with a substituent A, and a C3 to C6 haloalkynyloxy group, or R ３ and R ４ together preferably represent a C5-C10 unsaturated ring optionally substituted with a substituent A, and in particular R ３ and R ４ each independently represents a group selected from the group consisting of a hydrogen atom, a halogen atom, a C1 to C6 alkyl group which may be substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be substituted with a substituent A, a C1 to C6 alkoxy group which may be substituted with a substituent A, and a C2 to C6 alkenyl group which may be substituted with a substituent A, or R ３ and R ４ together preferably represent a C5-C10 unsaturated ring which may be substituted with a substituent A.

[0059] R and R in formula (2) ４ includes a hydrogen atom, a hydroxyl group, a cyano group, and a nitro group.

[0060] R and R in formula (2) ４ The halogen atom in has the same meaning as defined above, and is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, and more preferably a fluorine atom, a chlorine atom, or a bromine atom.

[0061] R and R in formula (2) ４The C1-C6 alkyl group in the "C1-C6 alkyl group which may be substituted with a substituent A" in the above is defined as above, and is preferably a methyl group, an ethyl group, or a propyl group, more preferably a methyl group or an ethyl group, and particularly preferably a methyl group. When the C1-C6 alkyl group has a substituent A, a hydrogen atom in the C1-C6 alkyl group is optionally substituted with a substituent A.

[0062] R and R in formula (2) ４ The "C1 to C6 haloalkyl group" in the above formula has the same meaning as defined above and is preferably a difluoromethyl group, a trifluoromethyl group, a 1,1-difluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 2,2,2-trichloroethyl group, a 3,3-difluoropropyl group, or a 3,3,3-trifluoropropyl group, more preferably a difluoromethyl group, a trifluoromethyl group, a 1,1-difluoroethyl group, a 2,2-difluoroethyl group, or a 2,2,2-trifluoroethyl group, and even more preferably a difluoromethyl group or a trifluoromethyl group.

[0063] R and R in formula (2) ４ The C3 to C8 cycloalkyl group in the "C3 to C8 cycloalkyl group which may be substituted with a substituent A" in the above is as defined above, and is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, more preferably a cyclopropyl group or a cyclobutyl group, and even more preferably a cyclopropyl group. When the C3 to C8 cycloalkyl group has a substituent A, a hydrogen atom in the C3 to C8 cycloalkyl group is optionally substituted with a substituent A.

[0064] R and R in formula (2) ４The C1-C6 alkoxy group in the "C1-C6 alkoxy group which may be substituted with a substituent A" has the same meaning as defined above and is preferably a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, or an isobutoxy group, more preferably a methoxy group or an ethoxy group, and even more preferably a methoxy group. When the C1-C6 alkoxy group has a substituent A, a hydrogen atom in the C1-C6 alkoxy group is optionally substituted with a substituent A.

[0065] R and R in formula (2) ４ The "C1 to C6 haloalkoxy group" in the above formula has the same meaning as defined above and is preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 3,3-difluoropropyloxy group, or a 3,3,3-trifluoropropyloxy group, more preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, or a 2,2,2-trifluoroethoxy group, and even more preferably a difluoromethoxy group or a trifluoromethoxy group.

[0066] R and R in formula (2) ４ The C3 to C8 cycloalkoxy group in the "C3 to C8 cycloalkoxy group which may be substituted with a substituent A" has the same meaning as defined above and is preferably a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, or a cyclohexyloxy group, more preferably a cyclopropyloxy group or a cyclobutoxy group. When the C3 to C8 cycloalkoxy group has a substituent A, a hydrogen atom in the C3 to C8 cycloalkoxy group is optionally substituted with a substituent A.

[0067] R and R in formula (2) ４The C2-C6 alkenyl group in the "C2-C6 alkenyl group which may be substituted with substituent A" has the same meaning as defined above and is preferably a vinyl group, a 1-propenyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, or a 3-butenyl group, more preferably a vinyl group, a 1-propenyl group, or an allyl group. When the C2-C6 alkenyl group has substituent A, a hydrogen atom in the C2-C6 alkenyl group is optionally substituted with substituent A.

[0068] R and R in formula (2) ４ The "C2 to C6 haloalkenyl group" has the same meaning as defined above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 3-fluoroallyl group, a 3,3-difluoroallyl group, or a 4,4-difluoro-3-butenyl group.

[0069] R and R in formula (2) ４ The C2-C6 alkynyl group in the "C2-C6 alkynyl group which may be substituted with substituent A" has the same meaning as defined above and is preferably an ethynyl group, a 1-propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, or a 3-butynyl group, more preferably an ethynyl group. When the C2-C6 alkynyl group has substituent A, a hydrogen atom in the C2-C6 alkynyl group is optionally substituted with substituent A.

[0070] R and R in formula (2) ４ The "C2 to C6 haloalkynyl group" in the above formula has the same meaning as defined above, and is preferably a 2-fluoroethynyl group, a 2-chloroethynyl group, a 2-bromoethynyl group, or a 2-iodoethynyl group, and more preferably a 2-fluoroethynyl group.

[0071] R and R in formula (2) ４ The C2-C6 alkenyloxy group in the "C2-C6 alkenyloxy group which may be substituted with substituent A" has the same meaning as defined above and is preferably a vinyloxy group, a 1-propenyloxy group, or an allyloxy group, more preferably an allyloxy group. When the C2-C6 alkenyloxy group has substituent A, a hydrogen atom in the C2-C6 alkenyloxy group is optionally substituted with substituent A.

[0072] R and R in formula (2) ４ The "C2 to C6 haloalkenyloxy group" in the above formula has the same meaning as defined above and is preferably a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 3-fluoroallyloxy group, or a 3,3-difluoroallyloxy group, and more preferably a 2-fluorovinyloxy group or a 2,2-difluorovinyloxy group.

[0073] R and R in formula (2) ４ The C3 to C6 alkynyloxy group in the "C3 to C6 alkynyloxy group which may be substituted with substituent A" has the same meaning as defined above and is preferably a propargyloxy group, a 2-butynyloxy group, or a 3-butynyloxy group, more preferably a propargyloxy group. When the C3 to C6 alkynyloxy group has substituent A, a hydrogen atom in the C3 to C6 alkynyloxy group is optionally substituted with substituent A.

[0074] R and R in formula (2) ４ The "C3 to C6 haloalkynyloxy group" in the above formula has the same meaning as defined above and is preferably a 4,4-difluoro-2-butynyloxy group, a 4-chloro-4,4-difluoro-2-butynyloxy group, a 4-bromo-4,4-difluoro-2-butynyloxy group, or a 4,4,4-trifluoro-2-butynyloxy group, and more preferably a 4,4-difluoro-2-butynyloxy group or a 4,4,4-trifluoro-2-butynyloxy group.

[0075] R and R in formula (2) ４In the formula, Ra and Rb in "RaRbN-" are as defined above. "RaRbN-" is preferably an amino group, a methylamino group, an ethylamino group, a (methoxymethyl)amino group, a (2-methoxyethyl)amino group, a (cyanomethyl)amino group, a (2-cyanoethyl)amino group, a dimethylamino group, an ethylmethylamino group, a diethylamino group, a (methoxymethyl)methylamino group, a (2-methoxyethyl)methylamino group, a (cyanomethyl)methylamino group, a (2-cyanoethyl)methylamino group, a 2,2-difluoroethylamino group, a 2,2,2-trifluoroethylamino group, a cyclopropylamino group, a (cyclopropyl)methylamino group, a pyrrolidinyl group, or a piperidinyl group, more preferably an amino group, a methylamino group, a dimethylamino group, an ethylmethylamino group, or a diethylamino group, and even more preferably an amino group, a methylamino group, or a dimethylamino group.

[0076] R and R in formula (2) ４In the formula, Ra and Rb of "-C(=O)NRaRb" have the same meanings as defined above. Preferable examples of "-C(=O)NRaRb" include an aminocarbonyl group, a methylaminocarbonyl group, an ethylaminocarbonyl group, a (methoxymethyl)aminocarbonyl group, a (2-methoxyethyl)aminocarbonyl group, a (cyanomethyl)aminocarbonyl group, a (2-cyanoethyl)aminocarbonyl group, a dimethylaminocarbonyl group, an ethylmethylaminocarbonyl group, a diethylaminocarbonyl group, a (methoxymethyl)methylaminocarbonyl group, a (2-methoxyethyl)methylaminocarbonyl group, a (cyanomethyl)methylaminocarbonyl group, a (2-cyano

[0033] The aryl group is preferably an aminocarbonyl group, a methylaminocarbonyl group, a dimethylaminocarbonyl group, an ethylmethylaminocarbonyl group, or a diethylaminocarbonyl group, and more preferably an aminocarbonyl group, a methylaminocarbonyl group, or a dimethylaminocarbonyl group.

[0077] R and R in formula (2) ４Rc in "-C(=O)ORc" has the same meaning as defined above. "-C(=O)ORc" is preferably a carboxy group, a methoxycarbonyl group, an ethoxycarbonyl group, a propyloxycarbonyl group, an isopropyloxycarbonyl group, a butoxycarbonyl group, an isobutoxycarbonyl group, a difluoromethoxycarbonyl group, a trifluoromethoxycarbonyl group, a 2,2-difluoroethoxycarbonyl group, a 2,2,2-trifluoroethoxycarbonyl group, a 3,3-difluoropropyloxycarbonyl group, or a 3,3,3-trifluoropropyloxy group. A cyclopropyloxycarbonyl group, a cyclobutoxycarbonyl group, a cyclopentyloxycarbonyl group, or a cyclohexyloxycarbonyl group is more preferred, and a methoxycarbonyl group, an ethoxycarbonyl group, a difluoromethoxycarbonyl group, a trifluoromethoxycarbonyl group, a 2,2-difluoroethoxycarbonyl group, a 2,2,2-trifluoroethoxycarbonyl group, or a cyclopropyloxycarbonyl group is even more preferred. When the C1-C6 alkyl group has a substituent A, a hydrogen atom in the C1-C6 alkyl group is optionally substituted with the substituent A.

[0078] R and R in formula (2) ４Rc in "-OC(=O)Rc" has the same meaning as defined above. Preferable examples of "-OC(=O)Rc" include a formyloxy group, an acetyloxy group, a methoxyacetyloxy group, a cyanoacetyloxy group, a propionyloxy group, a difluoroacetyloxy group, a trifluoroacetyloxy group, a cyclopropanecarbonyloxy group, a methoxycarbonyloxy group, an ethoxycarbonyloxy group, a 2,2-difluoroethoxycarbonyloxy group, a 2,2,2-trifluoroethoxycarbonyloxy group, a 3,3,3-trifluoropropyloxycarbonyloxy group, a cyclopropyloxycarbonyloxy group, an aminocarbonyloxy group, a methylaminocarbonyloxy group, an ethylaminocarbonyloxy group, a (methoxymethyl)aminocarbonyloxy group, a (2-methoxyethyl)aminocarbonyloxy group, a (cyanomethyl)aminocarbonyloxy group, Examples of the alkyl group include a (2-cyanoethyl)aminocarbonyloxy group, a dimethylaminocarbonyloxy group, an ethylmethylaminocarbonyloxy group, a diethylaminocarbonyloxy group, a (methoxymethyl)methylaminocarbonyloxy group, a (2-methoxyethyl)methylaminocarbonyloxy group, a (cyanomethyl)methylaminocarbonyloxy group, a (2-cyanoethyl)methylaminocarbonyloxy group, a 2,2-difluoroethylaminocarbonyloxy group, a 2,2,2-trifluoroethylaminocarbonyloxy group, a cyclopropylaminocarbonyloxy group, a (cyclopropyl)methylaminocarbonyloxy group, a pyrrolidinylcarbonyloxy group, and a piperidinylcarbonyloxy group, and more preferably a formyloxy group, an acetyloxy group, or a trifluoroacetyloxy group.

[0079] R and R in formula (2) ４ In the formula, Rd and L in "Rd-L-" have the same meanings as defined above. "Rd-L-" is preferably a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, or a trifluoromethanesulfonyl group, and more preferably a methylthio group, a methanesulfinyl group, or a methanesulfonyl group.

[0080] R and R in formula (2) ４ "R" in ３ and R ４ and R 1 to R 2 are taken together to form a C5 to C10 unsaturated ring which may be substituted with a substituent A," the C5 to C10 unsaturated ring has the same meaning as defined above, and is preferably a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, or a phenyl group.

[0081] R in formula (2) ５ represents a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1 to C6 alkyl group which may be substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be substituted with a substituent A, a C1 to C6 alkoxy group which may be substituted with a substituent A, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group which may be substituted with a substituent A, a C2 to C6 alkenyl group which may be substituted with a substituent A, a C2 to C6 haloalkoxy group, and Rb are each independently selected from the group consisting of -N-, ...

[0082] Among them, R ５is preferably a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1 to C6 alkyl group which may be substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be substituted with a substituent A, a C1 to C6 alkoxy group which may be substituted with a substituent A, a C2 to C6 alkenyl group which may be substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be substituted with a substituent A, a C2 to C6 haloalkynyl group, a C2 to C6 alkenyloxy group which may be substituted with a substituent A, a C2 to C6 haloalkenyloxy group, a C3 to C6 alkynyloxy group which may be substituted with a substituent A, or a C3 to C6 haloalkynyloxy group, and in particular, R ５ is preferably a hydrogen atom, a halogen atom, or a C1 to C6 alkyl group which may be substituted with a substituent A.

[0083] R in formula (2) ５ includes a hydrogen atom, a hydroxyl group, a cyano group, and a nitro group.

[0084] R in formula (2) ５ The "halogen atom" in the formula (I) has the same meaning as defined above, and is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, and more preferably a fluorine atom, a chlorine atom, or a bromine atom.

[0085] R in formula (2) ５ The C1-C6 alkyl group in the "C1-C6 alkyl group which may be substituted with a substituent A" has the same definition as above, and is preferably a methyl group, an ethyl group, or a propyl group, more preferably a methyl group or an ethyl group, and even more preferably a methyl group. When the C1-C6 alkyl group has a substituent A, a hydrogen atom in the C1-C6 alkyl group is optionally substituted with a substituent A.

[0086] R in formula (2) ５The "C1 to C6 haloalkyl group" in the above formula has the same meaning as defined above, and is preferably a difluoromethyl group, a trifluoromethyl group, a 1,1-difluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 2,2,2-trichloroethyl group, a 3,3-difluoropropyl group, or a 3,3,3-trifluoropropyl group, more preferably a difluoromethyl group, a trifluoromethyl group, a 1,1-difluoroethyl group, a 2,2-difluoroethyl group, or a 2,2,2-trifluoroethyl group, and even more preferably a difluoromethyl group or a trifluoromethyl group.

[0087] R in formula (2) ５ The C3 to C8 cycloalkyl group in the "C3 to C8 cycloalkyl group which may be substituted with a substituent A" in the above is as defined above, and is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, more preferably a cyclopropyl group or a cyclobutyl group, and even more preferably a cyclopropyl group. When the C3 to C8 cycloalkyl group has a substituent A, a hydrogen atom in the C3 to C8 cycloalkyl group is optionally substituted with a substituent A.

[0088] R in formula (2) ５ The C1-C6 alkoxy group in the "C1-C6 alkoxy group which may be substituted with a substituent A" has the same meaning as defined above and is preferably a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, or an isobutoxy group, more preferably a methoxy group or an ethoxy group, and even more preferably a methoxy group. When the C1-C6 alkoxy group has a substituent A, a hydrogen atom in the C1-C6 alkoxy group is optionally substituted with a substituent A.

[0089] R in formula (2) ５The "C1 to C6 haloalkoxy group" in the above formula has the same meaning as defined above and is preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 3,3-difluoropropyloxy group, or a 3,3,3-trifluoropropyloxy group, more preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, or a 2,2,2-trifluoroethoxy group, and even more preferably a difluoromethoxy group or a trifluoromethoxy group.

[0090] R in formula (2) ５ The C3 to C8 cycloalkoxy group in the "C3 to C8 cycloalkoxy group which may be substituted with a substituent A" has the same meaning as defined above and is preferably a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, or a cyclohexyloxy group, more preferably a cyclopropyloxy group or a cyclobutoxy group. When the C3 to C8 cycloalkoxy group has a substituent A, a hydrogen atom in the C3 to C8 cycloalkoxy group is optionally substituted with a substituent A.

[0091] R in formula (2) ５ The C2-C6 alkenyl group in the "C2-C6 alkenyl group which may be substituted with substituent A" has the same meaning as defined above, and is preferably a vinyl group, a 1-propenyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, or a 3-butenyl group, and more preferably a vinyl group, a 1-propenyl group, or an allyl group. When the C2-C6 alkenyl group has substituent A, a hydrogen atom in the C2-C6 alkenyl group is optionally substituted with substituent A.

[0092] R in formula (2) ５ The "C2 to C6 haloalkenyl group" has the same meaning as defined above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 3-fluoroallyl group, a 3,3-difluoroallyl group, or a 4,4-difluoro-3-butenyl group.

[0093] R in formula (2) ５The C2-C6 alkynyl group in the "C2-C6 alkynyl group which may be substituted with substituent A" has the same meaning as defined above, and is preferably an ethynyl group, a 1-propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, or a 3-butynyl group, and more preferably an ethynyl group. When the C2-C6 alkynyl group has substituent A, a hydrogen atom in the C2-C6 alkynyl group is optionally substituted with substituent A.

[0094] R in formula (2) ５ The "C2 to C6 haloalkynyl group" in the formula (I) has the same meaning as defined above, and is preferably a 2-fluoroethynyl group, a 2-chloroethynyl group, a 2-bromoethynyl group, or a 2-iodoethynyl group, and more preferably a 2-fluoroethynyl group.

[0095] R in formula (2) ５ The C2-C6 alkenyloxy group in the "C2-C6 alkenyloxy group which may be substituted with substituent A" has the same meaning as defined above and is preferably a vinyloxy group, a 1-propenyloxy group, or an allyloxy group, more preferably an allyloxy group. When the C2-C6 alkenyloxy group has substituent A, a hydrogen atom in the C2-C6 alkenyloxy group is optionally substituted with substituent A.

[0096] R in formula (2) ５ The "C2 to C6 haloalkenyloxy group" in the above formula has the same meaning as defined above and is preferably a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 3-fluoroallyloxy group, or a 3,3-difluoroallyloxy group, and more preferably a 2-fluorovinyloxy group or a 2,2-difluorovinyloxy group.

[0097] R in formula (2) ５ The C3 to C6 alkynyloxy group in the "C3 to C6 alkynyloxy group which may be substituted with substituent A" has the same meaning as defined above and is preferably a propargyloxy group, a 2-butynyloxy group, or a 3-butynyloxy group, more preferably a propargyloxy group. When the C3 to C6 alkynyloxy group has substituent A, a hydrogen atom in the C3 to C6 alkynyloxy group is optionally substituted with substituent A.

[0098] R in formula (2) ５ The "C3 to C6 haloalkynyloxy group" in the above formula has the same meaning as defined above and is preferably a 4,4-difluoro-2-butynyloxy group, a 4-chloro-4,4-difluoro-2-butynyloxy group, a 4-bromo-4,4-difluoro-2-butynyloxy group, or a 4,4,4-trifluoro-2-butynyloxy group, and more preferably a 4,4-difluoro-2-butynyloxy group or a 4,4,4-trifluoro-2-butynyloxy group.

[0099] R in formula (2) ５ In the formula, Ra and Rb in "RaRbN-" are as defined above. "RaRbN-" is preferably an amino group, a methylamino group, an ethylamino group, a (methoxymethyl)amino group, a (2-methoxyethyl)amino group, a (cyanomethyl)amino group, a (2-cyanoethyl)amino group, a dimethylamino group, an ethylmethylamino group, a diethylamino group, a (methoxymethyl)methylamino group, a (2-methoxyethyl)methylamino group, a (cyanomethyl)methylamino group, a (2-cyanoethyl)methylamino group, a 2,2-difluoroethylamino group, a 2,2,2-trifluoroethylamino group, a cyclopropylamino group, a (cyclopropyl)methylamino group, a pyrrolidinyl group, or a piperidinyl group, more preferably an amino group, a methylamino group, a dimethylamino group, an ethylmethylamino group, or a diethylamino group, and even more preferably an amino group, a methylamino group, or a dimethylamino group.

[0100] R in formula (2) ５In the formula, Ra and Rb of "-C(=O)NRaRb" have the same meanings as defined above. Preferable examples of "-C(=O)NRaRb" include an aminocarbonyl group, a methylaminocarbonyl group, an ethylaminocarbonyl group, a (methoxymethyl)aminocarbonyl group, a (2-methoxyethyl)aminocarbonyl group, a (cyanomethyl)aminocarbonyl group, a (2-cyanoethyl)aminocarbonyl group, a dimethylaminocarbonyl group, an ethylmethylaminocarbonyl group, a diethylaminocarbonyl group, a (methoxymethyl)methylaminocarbonyl group, a (2-methoxyethyl)methylaminocarbonyl group, a (cyanomethyl)methylaminocarbonyl group, a (2-cyano

[0033] The aryl group is preferably an aminocarbonyl group, a methylaminocarbonyl group, a dimethylaminocarbonyl group, an ethylmethylaminocarbonyl group, or a diethylaminocarbonyl group, and more preferably an aminocarbonyl group, a methylaminocarbonyl group, or a dimethylaminocarbonyl group.

[0101] R in formula (2) ５Rc in "-C(=O)ORc" has the same meaning as defined above. "-C(=O)ORc" is preferably a carboxy group, a methoxycarbonyl group, an ethoxycarbonyl group, a propyloxycarbonyl group, an isopropyloxycarbonyl group, a butoxycarbonyl group, an isobutoxycarbonyl group, a difluoromethoxycarbonyl group, a trifluoromethoxycarbonyl group, a 2,2-difluoroethoxycarbonyl group, a 2,2,2-trifluoroethoxycarbonyl group, a 3,3-difluoropropyloxycarbonyl group, or a 3,3,3-trifluoropropyloxy group. A cyclopropyloxycarbonyl group, a cyclobutoxycarbonyl group, a cyclopentyloxycarbonyl group, or a cyclohexyloxycarbonyl group is more preferred, and a methoxycarbonyl group, an ethoxycarbonyl group, a difluoromethoxycarbonyl group, a trifluoromethoxycarbonyl group, a 2,2-difluoroethoxycarbonyl group, a 2,2,2-trifluoroethoxycarbonyl group, or a cyclopropyloxycarbonyl group is even more preferred. When the C1-C6 alkyl group has a substituent A, a hydrogen atom in the C1-C6 alkyl group is optionally substituted with the substituent A.

[0102] R in formula (2) ５Rc in "-OC(=O)Rc" has the same meaning as defined above. Preferable examples of "-OC(=O)Rc" include a formyloxy group, an acetyloxy group, a methoxyacetyloxy group, a cyanoacetyloxy group, a propionyloxy group, a difluoroacetyloxy group, a trifluoroacetyloxy group, a cyclopropanecarbonyloxy group, a methoxycarbonyloxy group, an ethoxycarbonyloxy group, a 2,2-difluoroethoxycarbonyloxy group, a 2,2,2-trifluoroethoxycarbonyloxy group, a 3,3,3-trifluoropropyloxycarbonyloxy group, a cyclopropyloxycarbonyloxy group, an aminocarbonyloxy group, a methylaminocarbonyloxy group, an ethylaminocarbonyloxy group, a (methoxymethyl)aminocarbonyloxy group, a (2-methoxyethyl)aminocarbonyloxy group, a (cyanomethyl)aminocarbonyloxy group, Examples of the alkyl group include a (2-cyanoethyl)aminocarbonyloxy group, a dimethylaminocarbonyloxy group, an ethylmethylaminocarbonyloxy group, a diethylaminocarbonyloxy group, a (methoxymethyl)methylaminocarbonyloxy group, a (2-methoxyethyl)methylaminocarbonyloxy group, a (cyanomethyl)methylaminocarbonyloxy group, a (2-cyanoethyl)methylaminocarbonyloxy group, a 2,2-difluoroethylaminocarbonyloxy group, a 2,2,2-trifluoroethylaminocarbonyloxy group, a cyclopropylaminocarbonyloxy group, a (cyclopropyl)methylaminocarbonyloxy group, a pyrrolidinylcarbonyloxy group, and a piperidinylcarbonyloxy group, and more preferably a formyloxy group, an acetyloxy group, or a trifluoroacetyloxy group.

[0103] R in formula (2) ５ In the formula, Rd and L in "Rd-L-" have the same meanings as defined above. "Rd-L-" is preferably a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, or a trifluoromethanesulfonyl group, and more preferably a methylthio group, a methanesulfinyl group, or a methanesulfonyl group.

[0104] In formula (2), G１ , G ２ , and G ３ each independently represents a carbon atom or a nitrogen atom (provided that G １ , G ２ , and G ３ At least one of the groups represented by the formula (2) is a carbon atom. １ , G ２ , and G ３ is G １ , G ２ , and G ３ Any one of the groups is a nitrogen atom.

[0105] In formula (2), G ４ and G ５ each independently represents a nitrogen atom or CRx. ４ and G ５ When each of these represents CRx, Rx may be the same or different. ４ and G ５ is G ４ and G ５ Any one of the groups is a nitrogen atom.

[0106] Rx in formula (2) is a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1 to C6 alkyl group which may be substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be substituted with a substituent A, a C1 to C6 alkoxy group which may be substituted with a substituent A, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group which may be substituted with a substituent A, a C2 to C6 alkenyl group which may be substituted with a substituent A, a C2 to C6

[0049] It represents a haloalkenyl group, a C2 to C6 alkynyl group which may be substituted with a substituent A, a C2 to C6 haloalkynyl group, a C2 to C6 alkenyloxy group which may be substituted with a substituent A, a C2 to C6 haloalkenyloxy group, a C3 to C6 alkynyloxy group which may be substituted with a substituent A, a C3 to C6 haloalkynyloxy group, -NRaRb (where Ra and Rb are as defined above), -C(=O)NRaRb (where Ra and Rb are as defined above), -C(=O)ORc (where Rc is as defined above), -OC(=O)Rc (where Rc is as defined above), or -L-Rd (where Rd and L are as defined above).

[0107] Among these, Rx is preferably a hydrogen atom, a halogen atom, a C1 to C6 alkyl group which may be substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be substituted with a substituent A, a C1 to C6 alkoxy group which may be substituted with a substituent A, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group which may be substituted with a substituent A, a C2 to C6 alkenyl group which may be substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be substituted with a substituent A, or a C2 to C6 haloalkynyl group, and particularly preferably Rx is a hydrogen atom or a C1 to C6 alkyl group which may be substituted with a substituent A.

[0108] The C1-C6 alkyl group in the "C1-C6 alkyl group which may be substituted with a substituent A" in Rx of formula (2) has the same definition as above, and is preferably a methyl group, an ethyl group, or a propyl group, more preferably a methyl group or an ethyl group, and even more preferably a methyl group. When the C1-C6 alkyl group has a substituent A, a hydrogen atom in the C1-C6 alkyl group is optionally substituted with the substituent A.

[0109] The "C1-C6 haloalkyl group" for Rx in formula (2) has the same meaning as defined above and is preferably a difluoromethyl group, a trifluoromethyl group, a 1,1-difluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 2,2,2-trichloroethyl group, a 3,3-difluoropropyl group, or a 3,3,3-trifluoropropyl group, more preferably a difluoromethyl group, a trifluoromethyl group, a 1,1-difluoroethyl group, a 2,2-difluoroethyl group, or a 2,2,2-trifluoroethyl group, and even more preferably a difluoromethyl group or a trifluoromethyl group.

[0110] The C3 to C8 cycloalkyl group in the "C3 to C8 cycloalkyl group which may be substituted with a substituent A" for Rx in formula (2) has the same meaning as defined above and is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, more preferably a cyclopropyl group or a cyclobutyl group, and even more preferably a cyclopropyl group. When the C3 to C8 cycloalkyl group has a substituent A, a hydrogen atom in the C3 to C8 cycloalkyl group is optionally substituted with a substituent A.

[0111] The C1-C6 alkoxy group in the "C1-C6 alkoxy group which may be substituted with a substituent A" in Rx of formula (2) has the same meaning as defined above and is preferably a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, or an isobutoxy group, more preferably a methoxy group or an ethoxy group, and even more preferably a methoxy group. When the C1-C6 alkoxy group has a substituent A, a hydrogen atom in the C1-C6 alkoxy group is optionally substituted with a substituent A.

[0112] The "C1 to C6 haloalkoxy group" for Rx in formula (2) has the same meaning as defined above and is preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 3,3-difluoropropyloxy group, or a 3,3,3-trifluoropropyloxy group, more preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, or a 2,2,2-trifluoroethoxy group, and even more preferably a difluoromethoxy group or a trifluoromethoxy group.

[0113] The C3 to C8 cycloalkoxy group in the "C3 to C8 cycloalkoxy group which may be substituted with a substituent A" for Rx in formula (2) has the same meaning as defined above and is preferably a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, or a cyclohexyloxy group, more preferably a cyclopropyloxy group or a cyclobutoxy group. When the C3 to C8 cycloalkoxy group has a substituent A, a hydrogen atom in the C3 to C8 cycloalkoxy group is optionally substituted with a substituent A.

[0114] The C2-C6 alkenyl group in the "C2-C6 alkenyl group which may be substituted with substituent A" for Rx in formula (2) has the same meaning as defined above and is preferably a vinyl group, a 1-propenyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, or a 3-butenyl group, and more preferably a vinyl group, a 1-propenyl group, or an allyl group. When the C2-C6 alkenyl group has substituent A, a hydrogen atom in the C2-C6 alkenyl group is optionally substituted with substituent A.

[0115] The "C2 to C6 haloalkenyl group" for Rx in formula (2) has the same meaning as defined above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 3-fluoroallyl group, a 3,3-difluoroallyl group, or a 4,4-difluoro-3-butenyl group.

[0116] The C2-C6 alkynyl group in the "C2-C6 alkynyl group optionally substituted with substituent A" for Rx in formula (2) has the same meaning as defined above and is preferably an ethynyl group, a 1-propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, or a 3-butynyl group, and more preferably an ethynyl group. When the C2-C6 alkynyl group has substituent A, a hydrogen atom in the C2-C6 alkynyl group is optionally substituted with substituent A.

[0117] The "C2 to C6 haloalkynyl group" for Rx in formula (2) has the same meaning as defined above, and is preferably a 2-fluoroethynyl group, a 2-chloroethynyl group, a 2-bromoethynyl group, or a 2-iodoethynyl group, and more preferably a 2-fluoroethynyl group.

[0118] The C2-C6 alkenyloxy group in the "C2-C6 alkenyloxy group which may be substituted with substituent A" for Rx in formula (2) has the same meaning as defined above and is preferably a vinyloxy group, a 1-propenyloxy group, or an allyloxy group, more preferably an allyloxy group. When the C2-C6 alkenyloxy group has substituent A, a hydrogen atom in the C2-C6 alkenyloxy group is optionally substituted with substituent A.

[0119] The "C2 to C6 haloalkenyloxy group" for Rx in formula (2) has the same meaning as defined above and is preferably a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 3-fluoroallyloxy group, or a 3,3-difluoroallyloxy group, and more preferably a 2-fluorovinyloxy group or a 2,2-difluorovinyloxy group.

[0120] The C3 to C6 alkynyloxy group in the "C3 to C6 alkynyloxy group optionally substituted with substituent A" for Rx in formula (2) has the same meaning as defined above and is preferably a propargyloxy group, a 2-butynyloxy group, or a 3-butynyloxy group, more preferably a propargyloxy group. When the C3 to C6 alkynyloxy group has substituent A, a hydrogen atom in the C3 to C6 alkynyloxy group is optionally substituted with substituent A.

[0121] The "C3 to C6 haloalkynyloxy group" for Rx in formula (2) has the same meaning as defined above and is preferably a 4,4-difluoro-2-butynyloxy group, a 4-chloro-4,4-difluoro-2-butynyloxy group, a 4-bromo-4,4-difluoro-2-butynyloxy group, or a 4,4,4-trifluoro-2-butynyloxy group, and more preferably a 4,4-difluoro-2-butynyloxy group or a 4,4,4-trifluoro-2-butynyloxy group.

[0122] Ra and Rb of "RaRbN-" in Rx of formula (2) are as defined above. "RaRbN-" is preferably an amino group, a methylamino group, an ethylamino group, a (methoxymethyl)amino group, a (2-methoxyethyl)amino group, a (cyanomethyl)amino group, a (2-cyanoethyl)amino group, a dimethylamino group, an ethylmethylamino group, a diethylamino group, a (methoxymethyl)methylamino group, a (2-methoxyethyl)methylamino group, a (cyanomethyl)methylamino group, a (2-cyanoethyl)methylamino group, a 2,2-difluoroethylamino group, a 2,2,2-trifluoroethylamino group, a cyclopropylamino group, a (cyclopropyl)methylamino group, a pyrrolidinyl group, or a piperidinyl group, more preferably an amino group, a methylamino group, a dimethylamino group, an ethylmethylamino group, or a diethylamino group, and even more preferably an amino group, a methylamino group, or a dimethylamino group.

[0123] Ra and Rb of "-C(=O)NRaRb" in Rx of formula (2) have the same meanings as defined above. Preferable examples of "-C(=O)NRaRb" include an aminocarbonyl group, a methylaminocarbonyl group, an ethylaminocarbonyl group, a (methoxymethyl)aminocarbonyl group, a (2-methoxyethyl)aminocarbonyl group, a (cyanomethyl)aminocarbonyl group, a (2-cyanoethyl)aminocarbonyl group, a dimethylaminocarbonyl group, an ethylmethylaminocarbonyl group, a diethylaminocarbonyl group, a (methoxymethyl)methylaminocarbonyl group, a (2-methoxyethyl)methylaminocarbonyl group, a (cyanomethyl)methylaminocarbonyl group, a (2-cyano

[0033] The aryl group is preferably an aminocarbonyl group, a methylaminocarbonyl group, a dimethylaminocarbonyl group, an ethylmethylaminocarbonyl group, or a diethylaminocarbonyl group, and more preferably an aminocarbonyl group, a methylaminocarbonyl group, or a dimethylaminocarbonyl group.

[0124] Rc in "-C(=O)ORc" in Rx of formula (2) has the same meaning as defined above. "-C(=O)ORc" is preferably a carboxy group, a methoxycarbonyl group, an ethoxycarbonyl group, a propyloxycarbonyl group, an isopropyloxycarbonyl group, a butoxycarbonyl group, an isobutoxycarbonyl group, a difluoromethoxycarbonyl group, a trifluoromethoxycarbonyl group, a 2,2-difluoroethoxycarbonyl group, a 2,2,2-trifluoroethoxycarbonyl group, a 3,3-difluoropropyloxycarbonyl group, or a 3,3,3-trifluoropropyloxy group. A cyclopropyloxycarbonyl group, a cyclobutoxycarbonyl group, a cyclopentyloxycarbonyl group, or a cyclohexyloxycarbonyl group is more preferred, and a methoxycarbonyl group, an ethoxycarbonyl group, a difluoromethoxycarbonyl group, a trifluoromethoxycarbonyl group, a 2,2-difluoroethoxycarbonyl group, a 2,2,2-trifluoroethoxycarbonyl group, or a cyclopropyloxycarbonyl group is even more preferred. When the C1-C6 alkyl group has a substituent A, a hydrogen atom in the C1-C6 alkyl group is optionally substituted with the substituent A.

[0125] Rc in "-OC(=O)Rc" in Rx of formula (2) has the same meaning as defined above. Preferred examples of "-OC(=O)Rc" include a formyloxy group, an acetyloxy group, a methoxyacetyloxy group, a cyanoacetyloxy group, a propionyloxy group, a difluoroacetyloxy group, a trifluoroacetyloxy group, a cyclopropanecarbonyloxy group, a methoxycarbonyloxy group, an ethoxycarbonyloxy group, a 2,2-difluoroethoxycarbonyloxy group, a 2,2,2-trifluoroethoxycarbonyloxy group, a 3,3,3-trifluoropropyloxycarbonyloxy group, a cyclopropyloxycarbonyloxy group, an aminocarbonyloxy group, a methylaminocarbonyloxy group, an ethylaminocarbonyloxy group, a (methoxymethyl)aminocarbonyloxy group, a (2-methoxyethyl)aminocarbonyloxy group, and a (cyanomethyl)aminocarbonyloxy group. Examples of the alkyl group include a (2-cyanoethyl)aminocarbonyloxy group, a dimethylaminocarbonyloxy group, an ethylmethylaminocarbonyloxy group, a diethylaminocarbonyloxy group, a (methoxymethyl)methylaminocarbonyloxy group, a (2-methoxyethyl)methylaminocarbonyloxy group, a (cyanomethyl)methylaminocarbonyloxy group, a (2-cyanoethyl)methylaminocarbonyloxy group, a 2,2-difluoroethylaminocarbonyloxy group, a 2,2,2-trifluoroethylaminocarbonyloxy group, a cyclopropylaminocarbonyloxy group, a (cyclopropyl)methylaminocarbonyloxy group, a pyrrolidinylcarbonyloxy group, and a piperidinylcarbonyloxy group, and more preferably a formyloxy group, an acetyloxy group, or a trifluoroacetyloxy group.

[0126] Rd and L in "Rd-L-" in Rx of formula (2) are as defined above. "Rd-L-" is preferably a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, or a trifluoromethanesulfonyl group, and more preferably a methylthio group, a methanesulfinyl group, or a methanesulfonyl group.

[0127] In formula (2), the bond including the dashed line is The bond including the dashed line in formula (2) represents a double bond or a single bond.

[0128] G in formula (2) １ , G ２ , G ３ , G ４ , G ５ Preferred specific examples of partial structures formed by combinations of bonds including the broken line portions are shown below. (In the following specific examples, R ３ , R ４ , R ５ , and R ｘ has the same meaning as above.)

[0129] G in formula (2) １ , G ２ , G ３ , G ４ , G ５ More preferred specific examples of the partial structure formed by a combination of bonds including the broken line portion are shown below.

[0130] G in formula (2) １ , G ２ , G ３ , G ４ , G ５ Further preferred specific examples of the partial structure formed by a combination of bonds including the broken line portion are shown below.

[0131] R in formula (1) ６represents a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1 to C6 alkyl group which may be substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be substituted with a substituent A, a C1 to C6 alkoxy group which may be substituted with a substituent A, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group which may be substituted with a substituent A, a C2 to C6 alkenyl group which may be substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be substituted with a substituent A, a C2 to C6 haloalkynyl group, a C2 to C6

[0049] represents an alkenyloxy group, a C2 to C6 haloalkenyloxy group, a C3 to C6 alkynyloxy group optionally substituted by substituent A, a C3 to C6 haloalkynyloxy group, or -NRaRb (wherein Ra and Rb are as defined above), -C(=O)ORc (wherein Rc is as defined above), -C(=O)NRaRb (wherein Ra and Rb are as defined above), -C(=O)ORc (wherein Rc is as defined above), -OC(=O)Rc (wherein Rc is as defined above), or -L-Rd (wherein L and Rd are as defined above).

[0132] Among them, R ６represents a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1 to C6 alkyl group which may be substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be substituted with a substituent A, a C1 to C6 alkoxy group which may be substituted with a substituent A, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group which may be substituted with a substituent A, a C2 to C6 alkenyl group which may be substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be substituted with a substituent A, a C2 to C6 haloalkynyl group, a C2 to C6 alkenyloxy group which may be substituted with a substituent A, a C2 to C6 haloalkenyloxy group, a C3 to C6 alkynyloxy group which may be substituted with a substituent A, a C3 to C6 haloalkynyl An oxy group, or -NRaRb (wherein Ra and Rb are as defined above), -C(=O)ORc (wherein Rc is as defined above), -C(=O)NRaRb (wherein Ra and Rb are as defined above), - or -L-Rd (wherein L and Rd are as defined above), is preferred, and in particular, R6 is a halogen atom, a C1 to C6 alkyl group which may be substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be substituted with a substituent A, a C1 to C6 alkoxy group which may be substituted with a substituent A, a C3 to C8 cycloalkoxy group which may be substituted with a substituent A, a C2 to C6 alkenyl group which may be substituted with a substituent A, or -NRaRb (wherein Ra and Rb are as defined above), Preferred is -C(=O)NRaRb (wherein Ra and Rb have the same meanings as defined above), - or -L-Rd (wherein L and Rd have the same meanings as defined above).

[0133] R in formula (1) ６ includes a hydroxyl group, a cyano group, and a nitro group.

[0134] R in formula (1) ６ The halogen atom in has the same meaning as defined above, and is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, and more preferably a fluorine atom, a chlorine atom, or a bromine atom.

[0135] R in formula (1) ６The C1-C6 alkyl group in the "C1-C6 alkyl group which may be substituted with a substituent A" has the same definition as above, and is preferably a methyl group, an ethyl group, or a propyl group, more preferably a methyl group or an ethyl group, and even more preferably a methyl group. When the C1-C6 alkyl group has a substituent A, a hydrogen atom in the C1-C6 alkyl group is optionally substituted with a substituent A.

[0136] R in formula (1) ６ The "C1 to C6 haloalkyl group" in the above formula has the same meaning as defined above, and is preferably a difluoromethyl group, a trifluoromethyl group, a 1,1-difluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 2,2,2-trichloroethyl group, a 3,3-difluoropropyl group, or a 3,3,3-trifluoropropyl group, more preferably a difluoromethyl group, a trifluoromethyl group, a 1,1-difluoroethyl group, a 2,2-difluoroethyl group, or a 2,2,2-trifluoroethyl group, and even more preferably a difluoromethyl group or a trifluoromethyl group.

[0137] R in formula (1) ６ The C3 to C8 cycloalkyl group in the "C3 to C8 cycloalkyl group which may be substituted with a substituent A" in the above is as defined above, and is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, more preferably a cyclopropyl group or a cyclobutyl group, and even more preferably a cyclopropyl group. When the C3 to C8 cycloalkyl group has a substituent A, a hydrogen atom in the C3 to C8 cycloalkyl group is optionally substituted with a substituent A.

[0138] R in formula (1) ６ The C1-C6 alkoxy group in the "C1-C6 alkoxy group which may be substituted with a substituent A" has the same meaning as defined above and is preferably a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, or an isobutoxy group, more preferably a methoxy group or an ethoxy group, and even more preferably a methoxy group. When the C1-C6 alkoxy group has a substituent A, a hydrogen atom in the C1-C6 alkoxy group is optionally substituted with a substituent A.

[0139] R in formula (1) ６ The "C1 to C6 haloalkoxy group" in the above formula has the same meaning as defined above and is preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 3,3-difluoropropyloxy group, or a 3,3,3-trifluoropropyloxy group, more preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, or a 2,2,2-trifluoroethoxy group, and even more preferably a difluoromethoxy group or a trifluoromethoxy group.

[0140] R in formula (1) ６ The C3 to C8 cycloalkoxy group in the "C3 to C8 cycloalkoxy group which may be substituted with a substituent A" has the same meaning as defined above and is preferably a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, or a cyclohexyloxy group, more preferably a cyclopropyloxy group or a cyclobutoxy group. When the C3 to C8 cycloalkoxy group has a substituent A, a hydrogen atom in the C3 to C8 cycloalkoxy group is optionally substituted with a substituent A.

[0141] R in formula (1) ６ The C2-C6 alkenyl group in the "C2-C6 alkenyl group which may be substituted with substituent A" has the same meaning as defined above, and is preferably a vinyl group, a 1-propenyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, or a 3-butenyl group, and more preferably a vinyl group, a 1-propenyl group, or an allyl group. When the C2-C6 alkenyl group has substituent A, a hydrogen atom in the C2-C6 alkenyl group is optionally substituted with substituent A.

[0142] R in formula (1) ６ The "C2 to C6 haloalkenyl group" has the same meaning as defined above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 3-fluoroallyl group, a 3,3-difluoroallyl group, or a 4,4-difluoro-3-butenyl group.

[0143] R in formula (1) ６The C2-C6 alkynyl group in the "C2-C6 alkynyl group which may be substituted with substituent A" has the same meaning as defined above, and is preferably an ethynyl group, a 1-propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, or a 3-butynyl group, and more preferably an ethynyl group. When the C2-C6 alkynyl group has substituent A, a hydrogen atom in the C2-C6 alkynyl group is optionally substituted with substituent A.

[0144] R in formula (1) ６ The "C2 to C6 haloalkynyl group" in the formula (I) has the same meaning as defined above, and is preferably a 2-fluoroethynyl group, a 2-chloroethynyl group, a 2-bromoethynyl group, or a 2-iodoethynyl group, and more preferably a 2-fluoroethynyl group.

[0145] R in formula (1) ６ The C2-C6 alkenyloxy group in the "C2-C6 alkenyloxy group which may be substituted with substituent A" has the same meaning as defined above and is preferably a vinyloxy group, a 1-propenyloxy group, or an allyloxy group, more preferably an allyloxy group. When the C2-C6 alkenyloxy group has substituent A, a hydrogen atom in the C2-C6 alkenyloxy group is optionally substituted with substituent A.

[0146] R in formula (1) ６ The "C2 to C6 haloalkenyloxy group" in the above formula has the same meaning as defined above and is preferably a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 3-fluoroallyloxy group, or a 3,3-difluoroallyloxy group, and more preferably a 2-fluorovinyloxy group or a 2,2-difluorovinyloxy group.

[0147] R in formula (1) ６ The C3 to C6 alkynyloxy group in the "C3 to C6 alkynyloxy group which may be substituted with substituent A" has the same meaning as defined above and is preferably a propargyloxy group, a 2-butynyloxy group, or a 3-butynyloxy group, more preferably a propargyloxy group. When the C3 to C6 alkynyloxy group has substituent A, a hydrogen atom in the C3 to C6 alkynyloxy group is optionally substituted with substituent A.

[0148] R in formula (1) ６ The "C3 to C6 haloalkynyloxy group" in the above formula has the same meaning as defined above and is preferably a 4,4-difluoro-2-butynyloxy group, a 4-chloro-4,4-difluoro-2-butynyloxy group, a 4-bromo-4,4-difluoro-2-butynyloxy group, or a 4,4,4-trifluoro-2-butynyloxy group, and more preferably a 4,4-difluoro-2-butynyloxy group or a 4,4,4-trifluoro-2-butynyloxy group.

[0149] R in formula (1) ６ In the formula, Ra and Rb in "RaRbN-" are as defined above. "RaRbN-" is preferably an amino group, a methylamino group, an ethylamino group, a (methoxymethyl)amino group, a (2-methoxyethyl)amino group, a (cyanomethyl)amino group, a (2-cyanoethyl)amino group, a dimethylamino group, an ethylmethylamino group, a diethylamino group, a (methoxymethyl)methylamino group, a (2-methoxyethyl)methylamino group, a (cyanomethyl)methylamino group, a (2-cyanoethyl)methylamino group, a 2,2-difluoroethylamino group, a 2,2,2-trifluoroethylamino group, a cyclopropylamino group, a (cyclopropyl)methylamino group, a pyrrolidinyl group, or a piperidinyl group, more preferably an amino group, a methylamino group, a dimethylamino group, an ethylmethylamino group, or a diethylamino group, and even more preferably an amino group, a methylamino group, or a dimethylamino group.

[0150] R in formula (1) ６In the formula, Ra and Rb of "-C(=O)NRaRb" have the same meanings as defined above. Preferable examples of "-C(=O)NRaRb" include an aminocarbonyl group, a methylaminocarbonyl group, an ethylaminocarbonyl group, a (methoxymethyl)aminocarbonyl group, a (2-methoxyethyl)aminocarbonyl group, a (cyanomethyl)aminocarbonyl group, a (2-cyanoethyl)aminocarbonyl group, a dimethylaminocarbonyl group, an ethylmethylaminocarbonyl group, a diethylaminocarbonyl group, a (methoxymethyl)methylaminocarbonyl group, a (2-methoxyethyl)methylaminocarbonyl group, a (cyanomethyl)methylaminocarbonyl group, a (2-cyano

[0033] The aryl group is preferably an aminocarbonyl group, a methylaminocarbonyl group, a dimethylaminocarbonyl group, an ethylmethylaminocarbonyl group, or a diethylaminocarbonyl group, and more preferably an aminocarbonyl group, a methylaminocarbonyl group, or a dimethylaminocarbonyl group.

[0151] R in formula (1) ６Rc in "-C(=O)ORc" has the same meaning as defined above. "-C(=O)ORc" is preferably a carboxy group, a methoxycarbonyl group, an ethoxycarbonyl group, a propyloxycarbonyl group, an isopropyloxycarbonyl group, a butoxycarbonyl group, an isobutoxycarbonyl group, a difluoromethoxycarbonyl group, a trifluoromethoxycarbonyl group, a 2,2-difluoroethoxycarbonyl group, a 2,2,2-trifluoroethoxycarbonyl group, a 3,3-difluoropropyloxycarbonyl group, or a 3,3,3-trifluoropropyloxycarbonyl group.

[0033] In the case where the C1-C6 alkyl group has a substituent A, the substituent A is optionally substituted with a hydrogen atom of the C1-C6 alkyl group.

[0152] R in formula (1) ６Rc in "-OC(=O)Rc" has the same meaning as defined above. Preferable examples of "-OC(=O)Rc" include a formyloxy group, an acetyloxy group, a methoxyacetyloxy group, a cyanoacetyloxy group, a propionyloxy group, a difluoroacetyloxy group, a trifluoroacetyloxy group, a cyclopropanecarbonyloxy group, a methoxycarbonyloxy group, an ethoxycarbonyloxy group, a 2,2-difluoroethoxycarbonyloxy group, a 2,2,2-trifluoroethoxycarbonyloxy group, a 3,3,3-trifluoropropyloxycarbonyloxy group, a cyclopropyloxycarbonyloxy group, an aminocarbonyloxy group, a methylaminocarbonyloxy group, an ethylaminocarbonyloxy group, a (methoxymethyl)aminocarbonyloxy group, a (2-methoxyethyl)aminocarbonyloxy group, a (cyanomethyl)aminocarbonyloxy group, Examples of the alkyl group include a (2-cyanoethyl)aminocarbonyloxy group, a dimethylaminocarbonyloxy group, an ethylmethylaminocarbonyloxy group, a diethylaminocarbonyloxy group, a (methoxymethyl)methylaminocarbonyloxy group, a (2-methoxyethyl)methylaminocarbonyloxy group, a (cyanomethyl)methylaminocarbonyloxy group, a (2-cyanoethyl)methylaminocarbonyloxy group, a 2,2-difluoroethylaminocarbonyloxy group, a 2,2,2-trifluoroethylaminocarbonyloxy group, a cyclopropylaminocarbonyloxy group, a (cyclopropyl)methylaminocarbonyloxy group, a pyrrolidinylcarbonyloxy group, and a piperidinylcarbonyloxy group, and more preferably a formyloxy group, an acetyloxy group, or a trifluoroacetyloxy group.

[0153] R in formula (1) ６ In the formula, Rd and L in "Rd-L-" have the same meanings as defined above. "Rd-L-" is preferably a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, or a trifluoromethanesulfonyl group, and more preferably a methylthio group, a methanesulfinyl group, or a methanesulfonyl group.

[0154] R in formula (1)７ represents a lone electron pair, a hydrogen atom, a C1 to C6 alkyl group which may be substituted with a substituent A, a C1 to C6 haloalkyl group, a C2 to C6 alkenyl group which may be substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be substituted with a substituent A, a C2 to C6 haloalkynyl group, or an acyl group which may be substituted with a substituent A.

[0155] Among them, R ７ is preferably a lone electron pair, a hydrogen atom, a C1-C6 alkyl group which may be substituted with a substituent A, a C1-C6 haloalkyl group or an acyl group which may be substituted with a substituent A, and particularly preferably R ７ is preferably a lone pair of electrons. ７ is a lone pair, R ７ The bond including the dashed line portion constituted by the nitrogen atom to which is bonded represents a double bond, and the compound represented by formula (1) has a structure represented by the following formula:

[0156] R in formula (1) ７ contains a lone pair of electrons, a hydrogen atom.

[0157] R in formula (1) ７ The C1 to C6 alkyl group in the "C1 to C6 alkyl group which may be substituted with a substituent A" in formula (1) has the same definition as above and is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a s-butyl group, a pentyl group, or a hexyl group, and more preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, or an isobutyl group. When having a substituent A, a hydrogen atom in the C1 to C6 alkyl group is optionally substituted with a substituent A. The "C1 to C6 haloalkyl group" in R7 of formula (1) has the same definition as above and is preferably a difluoromethyl group, a trifluoromethyl group, a 1,1-difluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 2,2,2-trichloroethyl group, a 3,3-difluoropropyl group, or a 3,3,3-trifluoropropyl group.

[0158] R in formula (1) ７The C2-C6 alkenyl group in the "C2-C6 alkenyl group which may be substituted with a substituent A" has the same meaning as defined above, and is preferably a vinyl group, a 1-propenyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, or a 3-butenyl group. When the C2-C6 alkenyl group has a substituent A, a hydrogen atom in the C2-C6 alkenyl group is optionally substituted with a substituent A.

[0159] R in formula (1) ７ The "C2 to C6 haloalkenyl group" in the formula (1) has the same definition as above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 3-fluoroallyl group, a 3,3-difluoroallyl group, or a 4,4-difluoro-3-butenyl group. The C2 to C6 alkynyl group in the "C2 to C6 alkynyl group which may be substituted with a substituent A" in R7 of formula (1) has the same definition as above, and is preferably an ethynyl group, a 1-propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, or a 3-butynyl group. When the C2 to C6 alkynyl group has a substituent A, a hydrogen atom in the C2 to C6 alkynyl group is optionally substituted with a substituent A.

[0160] R in formula (1) ７The "C2 to C6 haloalkynyl group" in the above expression is as defined above, and is preferably a 2-fluoroethynyl group, a 2-chloroethynyl group, a 2-bromoethynyl group, a 2-iodoethynyl group, a 3,3-difluoro-1-propynyl group, a 3-chloro-3,3-difluoro-1-propynyl group, a 3-bromo-3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, a 4,4-difluoro-1-butynyl group, a 4,4-difluoro-2-butynyl group, a 4-chloro-4,4-difluoro-1-butynyl group, a 4-chloro-4,4-difluoro- Examples of the fluoroethynyl group include 4-fluoroethynyl, 4-bromo-4,4-difluoro-1-butynyl, 4-bromo-4,4-difluoro-2-butynyl, 4,4,4-trifluoro-1-butynyl, and 4,4,4-trifluoro-2-butynyl groups, and more preferably 2-fluoroethynyl, 3,3-difluoro-1-propynyl, 3,3,3-trifluoro-1-propynyl, 4,4-difluoro-1-butynyl, 4,4-difluoro-2-butynyl, 4,4,4-trifluoro-1-butynyl, and 4,4,4-trifluoro-2-butynyl groups.

[0161] R in formula (1) ７ The C1-C6 acyl group in the "C1-C6 acyl group which may be substituted with a substituent A" has the same meaning as defined above, and is preferably a formyl group, an acetyl group, a propionyl group, a butyryl group, or an isobutyryl group, and more preferably an acetyl group or a propionyl group. When the C1-C6 acyl group has a substituent A, a hydrogen atom in the C1-C6 acyl group is optionally substituted with a substituent A.

[0162] n represents an integer of 0 to 4. The integer n is preferably 0 to 2, and more preferably 0 or 1.

[0163] R in formula (1) ７ The bond including the broken line portion formed by the nitrogen atom to which R is bonded will be described in detail. ７ The bond containing the dashed line part that is formed by the nitrogen atom to which is bonded is R in formula (1) represents a portion represented by ７When the bond including the broken line portion formed by the nitrogen atom to which is bonded is a double bond, the compound is represented by formula (1a) or a salt thereof.

[0164] R in formula (1) ７ When the bond including the broken line portion formed by the nitrogen atom to which is bonded is a single bond, the compound represented by formula (1b) or a salt thereof is represented by formula (1b).

[0165] Formula (1b) is R １ and R ２ are the same, it is either the R or S isomer alone, or a mixture of the R and S isomers in any ratio. Alternatively, when R and R are different, it is a diastereomeric mixture of only one of the (R,R) isomer, (R,S) isomer, (S,R) isomer, and (S,S) isomer, or any mixture of the (R,R) isomer, (R,S) isomer, (S,R) isomer, and (S,S) isomer.

[0166] X in formula (1) is O, S, S(=O), SO ２ , or NRe. Among them, X represents O, S, S(═O), or SO ２ is preferred.

[0167] Re in formula (1) represents a hydrogen atom, a C1-C6 alkyl group which may be substituted with a substituent A, a C1-C6 haloalkyl group, a C2-C6 alkenyl group which may be substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be substituted with a substituent A, a C2-C6 haloalkynyl group, or a C1-C6 acyl group.

[0168] Re in formula (1) includes a hydrogen atom.

[0169] The C1-C6 alkyl group in the "C1-C6 alkyl group which may be substituted with a substituent A" in Re of formula (1) has the same definition as above, and is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a s-butyl group, a pentyl group, or a hexyl group, and more preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, or an isobutyl group. When the C1-C6 alkyl group has a substituent A, a hydrogen atom in the C1-C6 alkyl group is optionally substituted with the substituent A.

[0170] The "C1-C6 haloalkyl group" for Re in formula (1) has the same meaning as defined above, and is preferably a difluoromethyl group, a trifluoromethyl group, a 1,1-difluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 2,2,2-trichloroethyl group, a 3,3-difluoropropyl group, or a 3,3,3-trifluoropropyl group.

[0171] The C2-C6 alkenyl group in the "C2-C6 alkenyl group which may be substituted with a substituent A" in Re of formula (1) has the same meaning as defined above, and is preferably a vinyl group, a 1-propenyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, or a 3-butenyl group. When the C2-C6 alkenyl group has a substituent A, a hydrogen atom in the C2-C6 alkenyl group is optionally substituted with the substituent A.

[0172] The "C2 to C6 haloalkenyl group" in Re of formula (1) has the same meaning as defined above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 3-fluoroallyl group, a 3,3-difluoroallyl group, or a 4,4-difluoro-3-butenyl group.

[0173] The C2-C6 alkynyl group in the "C2-C6 alkynyl group which may be substituted with substituent A" in Re of formula (1) has the same meaning as defined above, and is preferably an ethynyl group, a 1-propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, or a 3-butynyl group. When the C2-C6 alkynyl group has substituent A, a hydrogen atom in the C2-C6 alkynyl group is optionally substituted with substituent A.

[0174] The "C2 to C6 haloalkynyl group" in Re of formula (1) has the same meaning as defined above, and is preferably a 2-fluoroethynyl group, a 2-chloroethynyl group, a 2-bromoethynyl group, a 2-iodoethynyl group, a 3,3-difluoro-1-propynyl group, a 3-chloro-3,3-difluoro-1-propynyl group, a 3-bromo-3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, a 4,4-difluoro-1-butynyl group, a 4,4-difluoro-2-butynyl group, a 4-chloro-4,4-difluoro-1-butynyl group, a 4-chloro-4,4-difluoro- Difluoro-2-butynyl group, 4-bromo-4,4-difluoro-1-butynyl group, 4-bromo-4,4-difluoro-2-butynyl group, 4,4,4-trifluoro-1-butynyl group, or 4,4,4-trifluoro-2-butynyl group, and more preferably 2-fluoroethynyl group, 3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1-propynyl group, 4,4-difluoro-1-butynyl group, 4,4-difluoro-2-butynyl group, 4,4,4-trifluoro-1-butynyl group, or 4,4,4-trifluoro-2-butynyl group.

[0175] The C1-C6 acyl group in the "C1-C6 acyl group which may be substituted with a substituent A" in Re of formula (1) has the same meaning as defined above, and is preferably a formyl group, an acetyl group, a propionyl group, a butyryl group, or an isobutyryl group, and more preferably an acetyl group or a propionyl group. When the C1-C6 acyl group has a substituent A, a hydrogen atom in the C1-C6 acyl group is optionally substituted with a substituent A.

[0176] In this specification, "substituent A" means a hydroxyl group, a cyano group, a C3 to C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C1 to C6 cycloalkoxy group, a C1 to C6 alkenyloxy group, a C1 to C6 haloalkenyloxy group, a C1 to C6 alkynyloxy group, a C1 to C6 haloalkynyloxy group, a C1-C6 acyl group, an aryl group optionally substituted with substituent B, a heteroaryl group optionally substituted with substituent B, or a cycloalkoxy group optionally substituted with substituent B. and represents at least one selected from the group consisting of an aryl group, a phenoxy group optionally substituted by a substituent B, —NRaRb (wherein Ra and Rb are as defined above), —C(═O)NRaRb (wherein Ra and Rb are as defined above), —C(═O)ORc (wherein Rc is as defined above), —OC(═O)Rc (wherein Rc is as defined above), and —L-Rd (wherein L and Rd are as defined above).

[0177] Among these, "substituent A" is a hydroxyl group, a cyano group, a C3 to C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1-C6 acyl group, an aryl group which may be substituted with substituent B, a phenoxy group which may be substituted with substituent B, -C(=O)NRaRb (wherein Ra and Rb are as defined above), -C(=O)ORc (wherein Rc is as defined above), -OC(=O)Rc (wherein Rc is as defined above), In particular, "substituent A" is preferably a cyano group, a C1-C6 alkoxy group, an aryl group which may be substituted with substituent B, -C(=O)NRaRb (wherein Ra and Rb are as defined above), -C(=O)ORc (wherein Rc is as defined above), or -L-Rd (wherein L and Rd are as defined above).

[0178] Specific preferred examples of the substituent A include a hydroxyl group and a cyano group; C3 to C8 cycloalkyl groups include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group; C1 to C6 alkoxy groups include a methoxy group, an ethoxy group, a propyloxy group, and an isopropyloxy group; C1 to C6 acyl groups include an acetyl group, a propionyl group, a butyryl group, and an isobutyryl group; aryl groups optionally substituted with a substituent B include a phenyl group (when having a substituent B, a hydrogen atom in the aryl group is optionally substituted with a substituent B); heteroaryl groups optionally substituted with a substituent B include a pyridyl group, a pyrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group, a furyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a triazolyl group, an oxadiazolyl group, or a tetrazolyl group (when having a substituent B, a hydrogen atom in the heteroaryl group is optionally substituted with a substituent B); Substituent B: As the optionally substituted phenoxy group, there may be mentioned a phenoxy group (when having substituent B, a hydrogen atom in the phenoxy group is optionally substituted with substituent B); "-NRaRb" (wherein Ra and Rb are as defined above) may be mentioned an amino group, a methylamino group, an ethylamino group, a (methoxymethyl)amino group, a (2-methoxyethyl)amino group, a (cyanomethyl)amino group, a (2-cyanoethyl)amino group, a dimethylamino group, an ethylmethylamino group, a diethylamino group, a (methoxymethyl)methylamino group, a (2-methoxyethyl)methylamino group, a (cyanomethyl)methylamino group, a (2-cyanoethyl)methylamino group, a 2,2-difluoroethylamino group, a 2,2,2-trifluoroethylamino group, a cyclopropylamino group, a (cyclopropyl)methylamino group, a pyrrolidinyl group, or a piperidinyl group; "-C(=O)NRaRb" (wherein Ra and Rb are as defined above) may be mentioned an amino group, a methylamino group, an ethylamino group, a (methoxymethyl)amino group, a (2-methoxyethyl)methylamino group, a (cyanomethyl)methylamino group, a (2-cyanoethyl)methylamino group, a 2,2-difluoroethylamino group, a 2,2,2-trifluoroethylamino group, a cyclopropylamino group, a (cyclopropyl)methylamino group, a pyrrolidinyl group, or a piperidinyl group;) an aminocarbonyl group, a methylaminocarbonyl group, an ethylaminocarbonyl group, a (methoxymethyl)aminocarbonyl group, a (2-methoxyethyl)aminocarbonyl group, a (cyanomethyl)aminocarbonyl group, a (2-cyanoethyl)aminocarbonyl group, a dimethylaminocarbonyl group, an ethylmethylaminocarbonyl group, a diethylaminocarbonyl group, a (methoxymethyl)methylaminocarbonyl group, a (2-methoxyethyl)methylaminocarbonyl group, a (cyanomethyl)methylaminocarbonyl group, a (2-cyanoethyl)methylaminocarbonyl group, a 2,2-difluoroethylaminocarbonyl group, a 2,2,2-trifluoroethylaminocarbonyl group, a cyclopropylaminocarbonyl group, a (cyclopropyl)methylaminocarbonyl group, a pyrrolidinyl group, or a piperidinyl group; "-C(=O)ORc" (wherein Rc is as defined above) includes a carboxy group, an ethoxycarbonyl group, a propyloxycarbonyl group, an isopropyloxycarbonyl group, a butoxycarbonyl group, an isobutoxycarbonyl group, a difluoromethoxycarbonyl group, a trifluoromethoxycarbonyl group, a 2,2-difluoroethoxycarbonyl group, a 2,2,2-trifluoroethoxycarbonyl group, a 3,3-difluoropropyloxycarbonyl group, a 3,3,3-trifluoropropyloxy group, a cyclopropyloxycarbonyl group, a cyclobutoxycarbonyl group, a cyclopentyloxycarbonyl group, or a cyclohexyloxycarbonyl group; "-OC(=O)Rc" (wherein Rc is as defined above) includes a carboxy group, an ethoxycarbonyl group, a propyloxycarbonyl group, an isopropyloxycarbonyl group, a butoxycarbonyl group, an isobutoxycarbonyl group, a difluoromethoxycarbonyl group, a trifluoromethoxycarbonyl group, a 2,2-difluoroethoxycarbonyl group, a 2,2,2-trifluoroethoxycarbonyl group, a 3,3-difluoropropyloxycarbonyl group, a 3,3,3-trifluoropropyloxy group, a cyclopropyloxycarbonyl group, a cyclobutoxycarbonyl group, a cyclopentyloxycarbonyl group, or a cyclohexyloxycarbonyl group;), a formyloxy group, an acetyloxy group, a methoxyacetyloxy group, a cyanoacetyloxy group, a propionyloxy group, a difluoroacetyloxy group, a trifluoroacetyloxy group, a cyclopropanecarbonyloxy group, a methoxycarbonyloxy group, an ethoxycarbonyloxy group, a 2,2-difluoroethoxycarbonyloxy group, a 2,2,2-trifluoroethoxycarbonyloxy group, a 3,3,3-trifluoropropyloxycarbonyloxy group, a cyclopropyloxycarbonyloxy group, an aminocarbonyloxy group, a methylaminocarbonyloxy group, an ethylaminocarbonyloxy group, a (methoxymethyl)aminocarbonyloxy group, a (2-methoxyethyl)aminocarbonyloxy group, a (cyano a (2-cyanoethyl)aminocarbonyloxy group, a (methyl)aminocarbonyloxy group, a (2-cyanoethyl)aminocarbonyloxy group, a dimethylaminocarbonyloxy group, an ethylmethylaminocarbonyloxy group, a diethylaminocarbonyloxy group, a (methoxymethyl)methylaminocarbonyloxy group, a (2-methoxyethyl)methylaminocarbonyloxy group, a (cyanomethyl)methylaminocarbonyloxy group, a (2-cyanoethyl)methylaminocarbonyloxy group, a 2,2-difluoroethylaminocarbonyloxy group, a 2,2,2-trifluoroethylaminocarbonyloxy group, a cyclopropylaminocarbonyloxy group, a (cyclopropyl)methylaminocarbonyloxy group, a pyrrolidinylcarbonyloxy group, or a piperidinylcarbonyloxy group; and "-L-Rd" (wherein L and Rd are as defined above) is a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfonyl group, or a trifluoromethanesulfonyl group.

[0179] More preferred specific examples of the substituent A include a cyano group; a cyclopropyl group and a cyclobutyl group as the C3 to C8 cycloalkyl group; a methoxy group and an ethoxy group as the C1 to C6 alkoxy group; a phenyl group as the aryl group which may be substituted with a substituent B (when having a substituent B, a hydrogen atom in the aryl group is optionally substituted with a substituent B); a pyridyl group as the heteroaryl group which may be substituted with a substituent B (when having a substituent B, a hydrogen atom in the heteroaryl group is optionally substituted with a substituent B); a methylamino group, an ethylamino group, a dimethylamino group, an ethylmethylamino group, a diethylamino group as "-NRaRb" (wherein Ra and Rb are as defined above); an aminocarbonyl group, a methylaminocarbonyl group, an ethylaminocarbonyl group, a dimethylaminocarbonyl group as "-C(=O)NRaRb" (wherein Ra and Rb are as defined above); "-C(=O)ORc" (wherein Rc has the same meaning as defined above) includes a carboxy group, a methoxycarbonyl group, an ethoxycarbonyl group, a propyloxycarbonyl group, and an isopropyloxycarbonyl group; "-OC(=O)Rc" (wherein Rc has the same meaning as defined above) includes an acetyloxy group, a methoxyacetyloxy group, a cyanoacetyloxy group, and a propionyloxy group; and "-L-Rd" (wherein L and Rd have the same meaning as defined above) includes a methylthio group, a methanesulfinyl group, and a methanesulfonyl group.

[0180] More preferred specific examples of the substituent A include a cyano group; a cyclopropyl group and a cyclobutyl group as the C3 to C8 cycloalkyl group; a methoxy group and an ethoxy group as the C1 to C6 alkoxy group; a phenyl group as the aryl group optionally substituted with a substituent B (when having a substituent B, a hydrogen atom in the aryl group is optionally substituted with a substituent B); a methylamino group and a dimethylamino group as "-NRaRb" (wherein Ra and Rb are as defined above); a methylaminocarbonyl group and a dimethylaminocarbonyl group as "-C(=O)NRaRb" (wherein Ra and Rb are as defined above); a carboxy group, a methoxycarbonyl group, an ethoxycarbonyl group and a propyloxycarbonyl group as "-C(=O)ORc" (wherein Rc is as defined above); "-OC(=O)Rc" (wherein Rc has the same meaning as defined above) includes an acetyloxy group and a propionyloxy group; and "-L-Rd" (wherein L and Rd have the same meaning as defined above) includes a methylthio group and a methanesulfonyl group.

[0181] In this specification, "substituent B" represents at least one selected from the group consisting of a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, and -L-Rd (wherein L and Rd are as defined above).

[0182] Among these, the substituent B is preferably a halogen atom, a cyano group, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, a C1 to C6 alkoxy group, or a C1 to C6 haloalkoxy group.

[0183] Specific preferred examples of the substituent B in formula (1) include a cyano group; halogen atoms such as fluorine, chlorine, bromine, or iodine; C1-C6 alkyl groups such as methyl, ethyl, propyl, or isopropyl; C1-C6 haloalkyl groups such as difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 3,3-difluoropropyl, or 3,3,3-trifluoropropyl; C3-C8 cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl; C1-C6 alkoxy groups such as methoxy, ethoxy, propyloxy, or isopropyloxy; The C1 to C6 haloalkoxy group is a fluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 3,3-difluoropropyloxy group, or a 3,3,3-trifluoropropyloxy group, and more preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, or a 2,2,2-trifluoroethoxy group; and the C3 to C8 cycloalkoxy group is a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, or a cyclohexyloxy group, and more preferably a cyclopropyloxy group.

[0184] More preferred specific examples of the substituent B in formula (1) include a cyano group, a fluorine atom or a chlorine atom as a halogen atom, a methyl group or an ethyl group as a C1 to C6 alkyl group, a difluoromethyl group or a trifluoromethyl group as a C1 to C6 haloalkyl group, a cyclopropyl group or a cyclobutyl group as a C3 to C8 cycloalkyl group, a methoxy group or an ethoxy group as a C1 to C6 alkoxy group, a difluoromethoxy group or a trifluoromethoxy group as a C1 to C6 haloalkoxy group, and a cyclopropyloxy group or a cyclobutoxy group as a C3 to C8 cycloalkoxy group.

[0185] The compound represented by formula (1) may contain an asymmetric atom. In this case, the ratio of isomers may be a single isomer or a mixture ratio of any proportion, and is not particularly limited.

[0186] The compound represented by formula (1) may contain geometric isomers. In this case, the ratio of the isomers may be a single isomer or a mixture ratio of any proportion, and is not particularly limited.

[0187] The compound represented by formula (1) may form a salt, such as an acid salt of hydrochloric acid, sulfuric acid, acetic acid, fumaric acid, or maleic acid, or a metal salt of sodium, potassium, or calcium, but is not particularly limited as long as it can be used as an agricultural or horticultural fungicide.

[0188] The above-described R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , X, G １ , G ２ , G ３ , G ４ , G ５ The range of all compounds obtained by arbitrarily combining the preferred ranges of Het, the bond including the broken line portion, the substituent A, and the substituent B is also considered to be described as the range of formula (1) of the present invention or the intermediate compound for its production.

[0189] The compound represented by formula (1) or a salt thereof is preferably the following compound or a salt thereof: １represents a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group optionally substituted with a substituent A, a C2 to C6 alkenyl group optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, a C1 to C6 acyl group optionally substituted with a substituent A, an aryl group optionally substituted with a substituent B, and a heteroaryl group optionally substituted with a substituent B; -C(=O)NRaRb (wherein Ra and Rb each independently represent a hydrogen atom, a C1 to C6 alkyl group optionally substituted with a substituent A, C1 to C6 a group selected from the group consisting of a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, a C1 to C6 acyl group, and -C(=O)ORc (wherein Rc represents a group selected from the group consisting of a hydrogen atom, a C1 to C6 alkyl group optionally substituted with substituent A, a C1 to C6 haloalkyl group, and a C3 to C8 cycloalkyl group), or Ra and Rb together with the nitrogen atom to which they are bonded form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group, or an azocanyl group) and -C(=O)ORc (wherein Rc has the same meaning as defined above); ２ represents a C1 to C6 alkyl group which may be substituted with a substituent A. Among these, preferably represents a methyl group or an ethyl group, or １ and R ２ may be taken together to form a C3-C8 cycloalkyl ring which may be substituted with a substituent A, or a C3-C8 saturated or unsaturated heterocyclic ring which may be substituted with a substituent A; Het represents formula (2), In formula (2), R ３ and R ４ each independently represents a group selected from the group consisting of a hydrogen atom, a halogen atom, a C1 to C6 alkyl group which may be substituted with a substituent A, a C3 to C8 cycloalkyl group which may be substituted with a substituent A, a C1 to C6 alkoxy group which may be substituted with a substituent A, and a C2 to C6 alkenyl group which may be substituted with a substituent A, or R ３ and R ４together form an unsaturated C5-C10 ring which may be substituted with a substituent A; R ５ represents a hydrogen atom; n represents an integer of 0 to 2; R ６ represents a group selected from the group consisting of a halogen atom, a C1 to C6 alkyl group which may be substituted with a substituent A, a C3 to C8 cycloalkyl group which may be substituted with a substituent A, a C1 to C6 alkoxy group which may be substituted with a substituent A, a C2 to C6 alkenyl group which may be substituted with a substituent A, and -NRaRb (wherein Ra and Rb have the same meanings as defined above); R ７ represents a lone pair of electrons; １ , G ２ , and G ３ each independently represents a group selected from the group consisting of carbon atoms and nitrogen atoms (provided that G １ , G ２ , and G ３ At least one of the groups is a carbon atom; ４ and G ５ each independently represents a group selected from the group consisting of a nitrogen atom and CRx; Rx represents a hydrogen atom or a C1-C6 alkyl group optionally substituted with a substituent A, and among these, preferably represents a hydrogen atom or a methyl group; the dashed line represents a double bond; X represents O, S, and SO ２Substituent A represents a group selected from the group consisting of a hydroxyl group, a cyano group, a C3 to C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C1 to C6 cycloalkoxy group, a C1 to C6 alkenyloxy group, a C1 to C6 haloalkenyloxy group, a C1 to C6 alkynyloxy group, a C1 to C6 haloalkynyloxy group, a C1-C6 acyl group, an aryl group optionally substituted with substituent B, a heteroaryl group optionally substituted with substituent B, Substituent B is at least one selected from the group consisting of a phenoxy group which may be optionally substituted with a substituent B, -NRaRb (wherein Ra and Rb are as defined above), -C(=O)NRaRb (wherein Ra and Rb are as defined above), -C(=O)ORc (wherein Rc is as defined above), -OC(=O)Rc (wherein Rc is as defined above), and -L-Rd (wherein L and Rd are as defined above); Substituent B is at least one selected from the group consisting of a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1 to C6 alkyl group which may be substituted with Substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, and Rd-L- (wherein Rd is as defined above). Formula (2) is preferably any of structures A to C described in the Examples.

[0190] Next, specific compounds of the present invention are those represented by formula (1) (wherein X in formula 1 is an oxygen atom or a sulfur atom, n is an integer of 0 to 4, and the bond including the dashed line is a double bond or a single bond) and R shown in Table 1. １ and R ２ (where R １ and R ２ has the same meaning as defined above. １ -1 to R １ -543 and R ２ -1 to R ２ -543 and R shown in Table 2 ３ and R ４ (where R ３ and R ４ has the same meaning as defined above. ３ -1 to R３ -75 and R ４ -1 to R ４ -75 and R shown in Table 3 ５ (where R ５ has the same meaning as defined above. ５ -1 to R ５ -81 and R shown in Table 4 ６ (where R ６ has the same meaning as defined above. ６ -1 to R ６ -80 and R shown in Table 5 ７ (where R ７ has the same meaning as defined above. ７ -1 to R ７ These compounds are represented by a combination of -111 and Het (here, Het has the same meaning as above) with structural formulas HetA-1 to HetA-16, HetB-1 to HetB-15, and HetC-1 to HetC16 (here, the bond position cut by the wavy line in Table 6 represents the position to which Het in Formula 1 is bonded) shown in Table 6. These compounds are for illustrative purposes only, and the present invention is not limited thereto. Furthermore, in the table below, for example, "-2-F-Ph" means a structure in which a fluorine atom is bonded to the 2-position of a phenyl group. The same applies hereinafter in this specification.

[0191] Table 1:

[0192] Table 2:

[0193] Table 3:

[0194] Table 4:

[0195] Table 5:

[0196] Table 6:

[0197]

[0198]

[0199] Examples of methods for producing the compound represented by formula (1) are given below. The methods for producing the compound of the present invention are not limited to Production Methods A to AH.

[0200] [Manufacturing method A] In the formula, R ８ represents a C1-C6 alkyl group optionally substituted with a substituent A, and R １ , R ２ , R ６ , and n have the same meanings as above.

[0201] Production method A is a method for obtaining a compound represented by formula (5), and is a production method comprising reacting a compound represented by formula (3) with a compound represented by formula (4) in the presence of an acid. Formula (3) used in this reaction can be obtained as a commercially available product or can be produced by a known method. Compound represented by formula (4) used in this reaction can be obtained as a commercially available product or can be produced by a known method.

[0202] The amount of the compound represented by formula (4) used in this reaction may be at least 1 equivalent relative to the compound represented by formula (3), and is not particularly limited as long as the target reaction proceeds, but is preferably at least 1 equivalent and no more than 200 equivalents. When formula (4) is liquid, it can also be used as a solvent.

[0203] The acid used in this reaction is exemplified by inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as acetic acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, and pyridinium p-toluenesulfonate. There is no particular limitation on the acid as long as the desired reaction proceeds, but p-toluenesulfonic acid is preferred.

[0204] A solvent can be used in this reaction, but is not necessarily required. The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, and examples thereof include acidic solvents such as acetic acid and methanesulfonic acid; ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; alcohol solvents such as methanol, ethanol, and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate; nitrile solvents such as acetonitrile; amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide; urea solvents such as 1,3-dimethyl-2-imidazolidinone; and halogenated solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in combination of two or more in any desired ratio. Preferred examples of the solvent include acidic solvents and benzene solvents, and more preferably acetic acid and toluene. The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (3).

[0205] The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually from 50° C. to 180° C. or below the boiling point of the solvent.

[0206] As a post-treatment for the reaction, a separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, any of the following can be used: an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc.; an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc.; or saline solution. During the separation operation, if necessary, a water-immiscible solvent can be added, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in combination of two or more in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield.

[0207] The reaction mixture containing the compound represented by formula (5) obtained above can be dehydrated with a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential. The reaction mixture containing the compound represented by formula (5) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound is not decomposed. The reaction mixture containing the compound represented by formula (5) obtained after solvent distillation can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, or the like. The solvent can be appropriately selected depending on the desired purity.

[0208] [Manufacturing method B] In the formula, R １ , R ２ , R ６ , and n have the same meanings as above.

[0209] Production method B is a method for obtaining a compound represented by formula (5), which comprises reacting a compound represented by formula (3) with a compound represented by formula (6) in the presence of an acid. The compound represented by formula (6) used in this reaction is commercially available or can be produced by a known method.

[0210] Production method B can be carried out in accordance with production method A by using a compound represented by formula (6) instead of the compound represented by formula (4) in production method A.

[0211] [Manufacturing method C] In the formula, R ９ represents a C1-C6 alkyl group, and R １０ and R １１ each independently represents a hydrogen atom, a C1-C6 alkyl group which may be substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be substituted with a substituent A, a C2-C6 alkenyl group which may be substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be substituted with a substituent A, a C2-C6 haloalkynyl group, a C1-C6 acyl group which may be substituted with a substituent A, an aryl group which may be substituted with a substituent B, or a heteroaryl group which may be substituted with a substituent B; R １ , R ６ , and n have the same meanings as above.

[0212] Production method C is a method for obtaining a compound represented by formula (5a), which comprises reacting a compound represented by formula (3) with a compound represented by formula (7) in the presence of an acid. The compound represented by formula (7) used in this reaction is commercially available or can be produced by a known method.

[0213] Production method C can be carried out in accordance with production method A by using a compound represented by formula (7) instead of the compound represented by formula (4) in production method A.

[0214] [Manufacturing method D] In the formula, R １ , R ２ , R ６ , R ８, and n have the same meanings as above.

[0215] Production method D is a production method for obtaining a benzothiazine compound represented by formula (9), which comprises cleaving the N-S bond of a compound represented by formula (8) using a reducing agent, followed by N,S-acetalization with a compound represented by formula (4).

[0216] First, the reaction for synthesizing the compound represented by formula (8) into 2-mercaptobenzamide will be described. Reducing agents for synthesizing 2-mercaptobenzamide include Raney nickel, catalytic reduction using a palladium catalyst and hydrogen, molybdenum complexes such as molybdenum hexacarbonyl, iron powder, zinc powder, and samarium iodide. When used in this reaction, the amount of reducing agent is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (8) and the target reaction proceeds, but is preferably 1 equivalent or more and 10 equivalents or less.

[0217] A solvent can be used in this reaction, but is not necessarily required. The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, and examples thereof include acidic solvents such as acetic acid and methanesulfonic acid; ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; alcohol solvents such as methanol, ethanol, and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate; nitrile solvents such as acetonitrile; amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide; urea solvents such as 1,3-dimethyl-2-imidazolidinone; and halogenated solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in combination of two or more in any desired ratio. Preferably, the solvent is an acidic solvent, and more preferably, acetic acid. The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (8).

[0218] The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually from -10°C to 150°C or below the boiling point of the solvent.

[0219] The reaction mixture containing the 2-mercaptobenzamide derivative obtained above can be used as is in the next reaction, but the solvent can be distilled off under reduced pressure as long as the compound is not decomposed. The reaction mixture containing the 2-mercaptobenzamide derivative obtained after solvent distillation can be used as is in the next reaction, but it can also be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. This can be set appropriately depending on the desired purity.

[0220] Next, the N,S-acetalization reaction of the compound represented by formula (4) with the 2-mercaptobenzamide derivative obtained above will be described. The compound represented by formula (4) used in this reaction can be commercially available or can be produced by a known method. The amount of the compound represented by formula (4) used in this reaction may be 1 equivalent or more relative to the compound represented by formula (8), and is not particularly limited as long as the desired reaction proceeds, but is preferably 1 equivalent or more and 200 equivalents or less.

[0221] The acid used in this reaction is exemplified by inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as acetic acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, and pyridinium p-toluenesulfonate. There is no particular limitation on the acid as long as the desired reaction proceeds, but p-toluenesulfonic acid is preferred.

[0222] A solvent can be used in this reaction, but is not necessarily required. The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, and examples thereof include acidic solvents such as acetic acid and methanesulfonic acid; ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; alcohol solvents such as methanol, ethanol, and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate; nitrile solvents such as acetonitrile; amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide; urea solvents such as 1,3-dimethyl-2-imidazolidinone; and halogenated solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in combination of two or more in any desired ratio. Preferred examples of the solvent include acidic solvents and benzene solvents, and more preferably acetic acid and toluene. The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (8).

[0223] The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually from 50° C. to 180° C. or below the boiling point of the solvent.

[0224] As a post-treatment for the reaction, a separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, any of the following can be used: an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc.; an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc.; or saline solution. During the separation operation, if necessary, a water-immiscible solvent can be added, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in combination of two or more in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield.

[0225] The reaction mixture containing the compound represented by formula (9) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

[0226] The reaction mixture containing the compound represented by formula (9) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound is not decomposed. The reaction mixture containing the compound represented by formula 5 obtained after solvent distillation can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. The solvent may be appropriately selected depending on the desired purity.

[0227] [Manufacturing method E] In the formula, R １ , R ２ , R ６ , and n have the same meanings as above.

[0228] Production method E is a production method for obtaining a benzothiazine compound represented by formula (9), which comprises cleaving the N-S bond of a compound represented by formula (8) using a reducing agent, followed by N,S-acetalization with a compound represented by formula (6). The compound represented by formula (6) used in this reaction is commercially available or can be produced by known methods.

[0229] Production method E can be carried out in accordance with production method D by using a compound represented by formula (6) instead of the compound represented by formula (4).

[0230] [Manufacturing method F] In the formula, R １３ represents a halogen atom, Xa represents an oxygen atom and a sulfur atom, R １ , R ２ , R ６ , and n have the same meanings as above.

[0231] Production method F is a method for obtaining a compound represented by formula (11), and comprises subjecting a compound represented by formula (10) to a halogenation reaction in a solvent. Examples of halogenating agents that can be used in this reaction include thionyl chloride, oxalyl chloride, phosphoryl chloride, sulfuryl chloride, phosphorus trichloride, phosphorus pentachloride, phosphorus tribromide, Vilsmeier reagent, etc. The amount of halogenating agent used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (10) as long as the desired reaction proceeds, but is preferably 1 equivalent or more and 10 equivalents or less.

[0232] When carrying out this reaction, DMF can be used as a catalyst. The amount of the catalyst used in this reaction is not particularly limited as long as the target reaction proceeds with respect to the compound represented by formula (10), but is preferably 0.1 equivalents or more and 10 equivalents or less.

[0233] A solvent can be used in this reaction, but is not necessarily required. The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include ether solvents such as diethyl ether, diisopropyl ether, methyl t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate; nitrile solvents such as acetonitrile; amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide; urea solvents such as 1,3-dimethyl-2-imidazolidinone; and halogenated solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in combination of two or more in any desired ratio. The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is typically 1 to 200 times by weight relative to the compound represented by formula (10).

[0234] The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually from −10° C. to 150° C. or below the boiling point of the solvent.

[0235] The reaction mixture containing the compound represented by formula (11) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose. The reaction mixture containing the compound represented by formula (11) obtained after solvent distillation can be used as is in the next reaction, but can also be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. The solvent may be appropriately selected depending on the desired purity.

[0236] [Manufacturing method G] R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R １３ , G ４ , G ５, Xa, and n are as defined above.

[0237] Production method G is a method for obtaining the compound of the present invention represented by formula (1-1), and is a production method comprising subjecting a compound represented by formula (11) and a compound represented by formula (12) to an addition-elimination reaction in a solvent under basic conditions. The compound represented by formula (12) used in this reaction is commercially available or can be produced by a known method.

[0238] The base used in this reaction is an organic base such as triethylamine, tributylamine, diisopropylethylamine, pyridine, collidine, or 2,6-lutidine, an inorganic base such as sodium carbonate, potassium carbonate, cesium carbonate, or tripotassium phosphate, or a metal hydride such as sodium hydride. The amount of the base used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually from 1 to 10 times by weight relative to the compound represented by formula (11).

[0239] A solvent can be used in this reaction, but is not necessarily required. The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include ether solvents such as diethyl ether, diisopropyl ether, methyl t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate; nitrile solvents such as acetonitrile; amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide; urea solvents such as 1,3-dimethyl-2-imidazolidinone; and halogenated solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in combination of two or more in any desired ratio. The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is typically 1 to 200 times by weight relative to the compound represented by formula (11).

[0240] The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually from 50° C. to 180° C. or below the boiling point of the solvent.

[0241] As a post-treatment for the reaction, a separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, any of the following can be used: an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc.; an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc.; or saline solution. During the separation operation, if necessary, a water-immiscible solvent can be added, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in combination of two or more in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield.

[0242] The reaction mixture containing the compound of the present invention represented by formula (1-1) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential. The reaction mixture containing the compound of the present invention represented by formula (1-1) obtained above can be distilled under reduced pressure to remove the solvent, as long as the compound is not decomposed.

[0243] The reaction mixture containing the compound of the present invention represented by formula (1-1) obtained after distilling off the solvent can be used as it is in the next reaction, but can also be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. The purification process may be appropriately set depending on the desired purity.

[0244] [Manufacturing method H] In the formula, R １４is a hydrogen atom or a C1-C6 alkyl group, and R １ , R ２ , R ６ , R １３ , Xa, and n are as defined above.

[0245] Production method H is a method for obtaining a compound represented by formula (13), which comprises reacting a compound represented by formula (11) with a terminal alkyne compound in a solvent in the presence of a transition metal and a base, thereby obtaining the compound by Sonogashira coupling.

[0246] The terminal alkyne compound used in this reaction can be commercially available or produced by known methods. Trimethylsilylacetylene can also be used as the terminal alkyne compound. In this case, it is necessary to introduce a trimethylsilylethynyl group into the compound represented by formula (11) and then perform desilylation. Desilylation can be performed with reference to non-patent literature such as Journal of the American Chemical Society, Vol. 131, No. 2, pp. 634-643 (2009) and Journal of Organometallic Chemistry, Vol. 696, No. 25, pp. 4039-4045 (2011). The amount of the terminal alkyne compound used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (11) and the desired reaction proceeds, but is preferably 1 equivalent or more and 10 equivalents or less.

[0247] The transition metals used in this reaction may have a ligand, and include palladiums such as palladium acetate, [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride, tris(dibenzylideneacetone)dipalladium, tetrakis(triphenylphosphine)palladium, and bis(triphenylphosphine)palladium dichloride. Coppers such as copper chloride, copper bromide, and copper iodide are also used. The amounts of the transition metals used in this reaction are not particularly limited, as long as the palladiums and coppers are each 0.001 equivalents or more relative to the compound represented by formula (11), and are not particularly limited as long as the desired reaction proceeds. The preferred amounts are 0.001 equivalents or more and 1 equivalent or less for both.

[0248] Examples of the base used in this reaction include organic amines such as triethylamine, tributylamine, isopropylamine, diethylamine, diisopropylamine, and diisopropylethylamine, and inorganic bases such as sodium carbonate, potassium carbonate, and cesium carbonate. The amount of the base used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (11) and the desired reaction proceeds, but is preferably 1 equivalent or more and 50 equivalents or less. Furthermore, liquid organic bases can be used as solvents.

[0249] To efficiently proceed with this reaction, a phosphine ligand such as tri-t-butylphosphine or 2-dicyclohexylphosphino-2'4'6'-triisopropylbiphenyl can be added, but is not essential. The amount of the phosphine ligand used in this reaction is 0.001 equivalents or more and 1 equivalent or less relative to the compound represented by formula (11), but is not particularly limited as long as the target reaction proceeds.

[0250] The base used in this reaction is an inorganic base such as sodium carbonate, potassium carbonate, cesium carbonate, tripotassium phosphate, etc., or a metal alkoxide such as sodium methoxide, sodium ethoxide, potassium t-butoxide, etc. The amount of the base used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (11) and the target reaction proceeds, but is preferably 1 equivalent or more and 50 equivalents or less.

[0251] The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples thereof include ether solvents such as diethyl ether, diisopropyl ether, methyl t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc., benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, etc., ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, etc., nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, etc., urea solvents such as 1,3-dimethyl-2-imidazolidinone, halogenated solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride, etc., organic amine solvents such as triethylamine, tributylamine, isopropylamine, diethylamine, diisopropylamine, diisopropylethylamine, etc. These solvents can be used alone or in combination of two or more in any ratio. The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (11).

[0252] The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually from 0° C. to 150° C. or below the boiling point of the solvent.

[0253] As a post-treatment for the reaction, a separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When an aqueous solution is used, any of the following can be used: an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, or the like; an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, or the like; an aqueous solution containing a sulfur-containing salt such as sodium thiosulfate or sodium sulfite; or saline. During the separation operation, if necessary, a water-immiscible solvent can be added, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, or chloroform; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in combination of two or more in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield.

[0254] The reaction mixture containing the compound represented by formula (13) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential. The reaction mixture containing the compound represented by formula (13) obtained above can be distilled under reduced pressure to remove the solvent, as long as the compound is not decomposed.

[0255] The reaction mixture containing the compound represented by formula (13) obtained after distilling off the solvent can be used as it is in the next reaction, but can also be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. The purification process may be appropriately set depending on the desired purity.

[0256] [Manufacturing method I] In the formula, R １ , R ２ , R ３ , R ４ , R ６ , R １４ , G４ , G ５ , Xa, and n are as defined above.

[0257] Production method I is a production method for obtaining the compounds of the present invention represented by formula (1-2) and formula (1-3), and comprises reacting a compound represented by formula (13) with a compound represented by formula (14) in a solvent under basic conditions.

[0258] The compound represented by formula (1-2) and the compound represented by formula (1-3) obtained by this reaction may be either alone or a mixture in any proportion, and the ratio between them is not particularly limited. The compound represented by formula (14) used in this reaction can be obtained as a commercially available product or produced by a known method. The compound represented by formula (14) used in this reaction has a counter anion. The counter anion in formula (14) is not particularly limited as long as the target reaction proceeds, but examples include a fluoride ion, chloride ion, bromide ion, iodide ion, trifluoroacetate ion, 2,4-dinitrophenolate ion, and mesitylenesulfonate ion.

[0259] The amount of the compound of formula (14) used in this reaction may be 1 equivalent or more relative to the compound of formula (13), and is not particularly limited as long as the target reaction proceeds, but is preferably 1 equivalent or more and 10 equivalents or less.

[0260] The base used in this reaction includes organic bases such as triethylamine, tributylamine, diisopropylethylamine, pyridine, collidine, and 2,6-lutidine, and inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, and tripotassium phosphate.

[0261] A solvent can be used in this reaction, but is not necessarily required. The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include ether solvents such as diethyl ether, diisopropyl ether, methyl t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; alcohol solvents such as methanol, ethanol, and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate; nitrile solvents such as acetonitrile; amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide; urea solvents such as 1,3-dimethyl-2-imidazolidinone; and halogenated solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in combination of two or more in any desired ratio. Preferred solvents include acidic solvents and benzene solvents. The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (13).

[0262] The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually from -10°C to 150°C or below the boiling point of the solvent.

[0263] As a post-treatment for the reaction, a separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, any of the following can be used: an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc.; an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc.; or saline solution. During the separation operation, if necessary, a water-immiscible solvent can be added, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in combination of two or more in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield.

[0264] The reaction mixture containing the compound of the present invention represented by formula (1-2) and the compound of the present invention represented by formula (1-3) obtained above can be used to remove moisture with a drying agent such as sodium sulfate, magnesium sulfate, etc., but this is not essential. The reaction mixture containing the compound of the present invention represented by formula (1-2) and the compound of the present invention represented by formula (1-3) obtained above can be subjected to solvent distillation under reduced pressure as long as the compounds do not decompose.

[0265] The reaction mixture containing the compound of the present invention represented by formula (1-2) and the compound of the present invention represented by formula (1-3) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. This can be appropriately set depending on the desired purity.

[0266] [Manufacturing method J] In the formula, R １ , R ２ , R ３ , R ４ , R ６ , R１３ , Xa, and n are as defined above.

[0267] Production method J is a method for obtaining the compound of the present invention represented by formula (1-4), and includes cross-coupling via C—H activation in which a compound represented by formula (11) is reacted with a pyrazolopyrimidine derivative (15) in a solvent in the presence of a transition metal and a base.

[0268] The compound of formula (15) used in this reaction is commercially available or can be produced by a known method. The amount of the compound of formula (15) used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound of formula (11), as long as the target reaction proceeds, but is preferably 1 equivalent or more and 10 equivalents or less.

[0269] The transition metal used in this reaction is palladium, nickel, ruthenium, etc., and may have a ligand. Preferred examples include palladium compounds such as palladium acetate, [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride, tris(dibenzylideneacetone)dipalladium, tetrakis(triphenylphosphine)palladium, bis(triphenylphosphine), and palladium dichloride. The amount of the transition metal used in this reaction is 0.001 equivalents or more and 1 equivalent or less relative to the compound represented by formula (11), but is not particularly limited as long as the desired reaction proceeds.

[0270] To efficiently proceed with this reaction, a phosphine ligand such as triphenylphosphine, tricyclohexylphosphine, tri-tert-butylphosphonium tetrafluoroborate, etc. can be added. The amount of the phosphine ligand used in this reaction is 0.001 equivalents or more and 1 equivalent or less relative to the compound represented by formula (11), but is not particularly limited as long as the target reaction proceeds.

[0271] The base used in this reaction is an inorganic base such as sodium carbonate, potassium carbonate, cesium carbonate, tripotassium phosphate, etc., or a metal alkoxide such as sodium methoxide, sodium ethoxide, potassium t-butoxide, etc. The amount of the base used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (11) and the target reaction proceeds, but is preferably 1 equivalent or more and 50 equivalents or less.

[0272] The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples thereof include water, ether solvents such as diethyl ether, diisopropyl ether, methyl t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, and benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene. These solvents can be used alone or in combination of two or more in any desired ratio. The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (11).

[0273] The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is typically 30°C or higher and 100°C or lower, or below the boiling point of the solvent. Post-reaction treatment can be performed by adding water or an appropriate aqueous solution to the reaction mixture to perform a liquid separation operation. When using an aqueous solution, any of the following can be used: an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, or the like; an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, or the like; an aqueous solution containing a sulfur-containing salt such as sodium thiosulfate or sodium sulfite; or saline. During the liquid separation operation, it is possible to add, as necessary, a water-immiscible solvent, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, or chloroform; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in combination of two or more in any proportion. The number of separations is not particularly limited and can be carried out depending on the desired purity and yield.

[0274] The reaction mixture containing the compound of the present invention represented by formula (1-4) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential. The reaction mixture containing the compound of the present invention represented by formula (1-4) obtained above can be distilled under reduced pressure to remove the solvent, as long as the compound is not decomposed.

[0275] The reaction mixture containing the compound of the present invention represented by formula (1-4) obtained after distilling off the solvent can be used as it is in the next reaction, but can also be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. The purification process may be appropriately set depending on the desired purity.

[0276] [Manufacturing method K] Het-B represents an organic boronic acid, and R １ , R ２ , R ６ , R １３ , Xa, Het, and n are as defined above.

[0277] Production method K is a method for obtaining the compound of the present invention represented by formula (1-5), and includes reacting a compound represented by formula (11) with an organoboronic acid compound represented by formula (16) in a solvent by Suzuki-Miyaura coupling.

[0278] The compound represented by formula (16) used in this reaction is an organic boronic acid such as an organic boronic acid or an organic boronic acid ester, and can be obtained as a commercial product or produced by a known method. The amount of the compound represented by formula (16) used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (11) as long as the target reaction proceeds, but is preferably 1 equivalent or more and 10 equivalents or less.

[0279] The transition metals used in this reaction include palladium, nickel, ruthenium, etc., which may have a ligand. Preferred examples include palladium compounds such as palladium acetate, [1,1'-bis(diphenylphosphino),ferrocene]palladium dichloride, tris(dibenzylideneacetone)dipalladium, tetrakis(triphenylphosphine)palladium, bis(triphenylphosphine), and palladium dichloride.

[0280] The amount of the transition metal used in this reaction is 0.001 equivalents or more and 1 equivalent or less relative to the compound represented by formula (11), but is not particularly limited as long as the desired reaction proceeds.

[0281] To efficiently proceed with this reaction, a phosphine ligand such as triphenylphosphine, tricyclohexylphosphine, etc. can be added. The amount of the phosphine ligand used in this reaction is 0.001 equivalents or more and 1 equivalent or less relative to the compound represented by formula (11), but is not particularly limited as long as the target reaction proceeds.

[0282] The base used in this reaction is an inorganic base such as sodium carbonate, potassium carbonate, cesium carbonate, tripotassium phosphate, etc., or a metal alkoxide such as sodium methoxide, sodium ethoxide, potassium t-butoxide, etc. The amount of the base used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (11) and the target reaction proceeds, but is preferably 1 equivalent or more and 50 equivalents or less.

[0283] The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples thereof include water, ether solvents such as diethyl ether, diisopropyl ether, methyl t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, and benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene. These solvents can be used alone or in combination of two or more in any desired ratio. The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (11).

[0284] The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is typically 30°C or higher and 100°C or lower, or below the boiling point of the solvent. Post-reaction treatment can be performed by adding water or an appropriate aqueous solution to the reaction mixture to perform a liquid separation operation. When using an aqueous solution, any of the following can be used: an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, or the like; an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, or the like; an aqueous solution containing a sulfur-containing salt such as sodium thiosulfate or sodium sulfite; or saline. During the liquid separation operation, it is possible to add, as necessary, a water-immiscible solvent, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, or chloroform; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in combination of two or more in any proportion. The number of separations is not particularly limited and can be carried out depending on the desired purity and yield.

[0285] The reaction mixture containing the compound of the present invention represented by formula (1-5) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential. The reaction mixture containing the compound of the present invention represented by formula (1-5) obtained above can be distilled under reduced pressure to remove the solvent, as long as the compound is not decomposed.

[0286] The reaction mixture containing the compound of the present invention represented by formula (1-5) obtained after distilling off the solvent can be used as it is in the next reaction, but can also be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. The purification process may be appropriately set depending on the desired purity.

[0287] [Manufacturing method L] In the formula, R１ , R ２ , R ６ , R ８ , Xa, and n are as defined above.

[0288] Production method L is a method for obtaining a compound represented by formula (18), which comprises reacting a compound represented by formula (17) with a compound represented by formula (4) in the presence of an ammonium salt.

[0289] The compound represented by formula (17) used in this reaction can be commercially available or prepared by known methods. The compound represented by formula (4) used in this reaction can be commercially available or prepared by known methods. The amount of formula (4) used in this reaction may be 1 equivalent or more relative to the compound represented by formula (17), and is not particularly limited as long as the desired reaction proceeds, but is preferably 1 equivalent or more and 200 equivalents or less. Furthermore, when formula (4) is liquid, it can also be used as a solvent.

[0290] Examples of the ammonium salt used in this reaction include ammonium chloride, ammonium acetate, ammonium sulfate, ammonium phosphate, etc. There are no particular limitations as long as the target reaction proceeds, but ammonium acetate is preferred.

[0291] A solvent can be used in this reaction, but is not necessarily required. The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, and examples thereof include acidic solvents such as acetic acid and methanesulfonic acid; ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; alcohol solvents such as methanol, ethanol, and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate; nitrile solvents such as acetonitrile; amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide; urea solvents such as 1,3-dimethyl-2-imidazolidinone; and halogenated solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in combination of two or more in any desired ratio. Preferred examples of the solvent include acidic solvents and benzene solvents, and more preferably acetic acid and toluene. The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (17).

[0292] The temperature during this reaction is not particularly limited as long as the desired reaction proceeds, but is typically between 50°C and 180°C, or below the boiling point of the solvent. Post-reaction treatment can involve adding water or an appropriate aqueous solution to the reaction mixture to perform a separation operation. When using an aqueous solution, any of the following can be used: an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, or the like; an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, or the like; or saline. During the separation operation, if necessary, a water-immiscible solvent can be added, such as a benzene-based solvent (e.g., toluene, xylene, benzene, chlorobenzene, dichlorobenzene); an ester-based solvent (e.g., ethyl acetate, isopropyl acetate, butyl acetate); an ether-based solvent (e.g., diethyl ether, diisopropyl ether, methyl t-butyl ether); a halogen-based solvent (e.g., dichloromethane, dichloroethane, chloroform, carbon tetrachloride); or a hydrocarbon-based solvent (e.g., hexane, heptane, cyclohexane, methylcyclohexane). These solvents can be used alone or in combination of two or more in any ratio. The number of separations is not particularly limited, and can be carried out depending on the desired purity and yield.

[0293] The reaction mixture containing the compound represented by formula (18) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential. The reaction mixture containing the compound represented by formula (18) obtained above can be distilled under reduced pressure to remove the solvent, as long as the compound is not decomposed.

[0294] The reaction mixture containing the compound represented by formula (18) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. The method may be appropriately set depending on the desired purity.

[0295] [Manufacturing method M] In the formula, R １ , R ２ , R ６ , Xa, and n are as defined above.

[0296] Production method M is a method for obtaining a compound represented by formula (18), and comprises reacting a compound represented by formula (17) with a compound represented by formula (5) in the presence of an ammonium salt. Production method M can be carried out in accordance with production method L by using a compound represented by formula (5) instead of the compound represented by formula (4) in production method L.

[0297] [Manufacturing method N] In the formula, R １ , R ２ , R ６ , R １３ , Xa, and n are as defined above.

[0298] Production method N is a method for obtaining a compound represented by formula (19), which comprises subjecting a compound represented by formula (18) to a halogenation reaction in a solvent using a halogenating agent.

[0299] To efficiently proceed with this reaction, azobisisobutyronitrile, 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile), benzoyl peroxide, etc. may be added. The amount of the radical initiator used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 0.01 equivalents or more and 1.0 equivalents or less relative to the compound represented by formula (18).

[0300] Examples of halogenating agents used in this reaction include N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3-diiodo-5,5-dimethylhydantoin, bromine, cupric bromide, etc. The amount of halogenating agent used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (18) as long as the desired reaction proceeds, but is usually 1 equivalent or more and 5 equivalents or less.

[0301] The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples thereof include halogenated benzene solvents such as chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate, halogenated solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. These solvents can be used alone or in combination of two or more in any desired ratio. The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (18).

[0302] The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is typically from 20°C to 150°C or below the boiling point of the solvent. Post-reaction treatment can be performed by adding water or an appropriate aqueous solution to the reaction mixture to perform a liquid separation operation. When using an aqueous solution, any of the following can be used: an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, or the like; an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, or the like; an aqueous solution containing a sulfur-containing salt such as sodium thiosulfate or sodium sulfite; or saline. During the liquid separation operation, it is possible to add, as necessary, a water-immiscible solvent, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, or chloroform; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in combination of two or more in any proportion. The number of separations is not particularly limited and can be carried out depending on the desired purity and yield.

[0303] The reaction mixture containing the compound represented by formula (19) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential. The reaction mixture containing the compound represented by formula (19) obtained above can be distilled under reduced pressure to remove the solvent, as long as the compound is not decomposed.

[0304] The reaction mixture containing the compound represented by formula (19) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. The method may be appropriately set depending on the desired purity.

[0305] [Manufacturing method O] In the formula, R １４ represents a C1-C6 alkyl group, and R １ , R ２ , R ３ , R ４ , R ６ , R １３ , G ４ , Xa and n are as defined above.

[0306] Production method O is a production method for obtaining the compound of the present invention represented by formula (1-6), which comprises reacting a compound represented by formula (19) with a compound represented by formula (20) in a solvent under basic conditions.

[0307] The compound of formula (20) used in this reaction can be commercially available or can be produced by a known method. The amount of the compound of formula (20) used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound of formula (19), and is preferably 1 equivalent or more and 10 equivalents or less, as long as the target reaction proceeds.

[0308] The base used in this reaction includes organic bases such as triethylamine, tributylamine, diisopropylethylamine, pyridine, collidine, and 2,6-lutidine, and inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, and tripotassium phosphate.

[0309] A solvent can be used in this reaction, but is not necessarily required. The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include ether solvents such as diethyl ether, diisopropyl ether, methyl t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; alcohol solvents such as methanol, ethanol, and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate; nitrile solvents such as acetonitrile; amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide; urea solvents such as 1,3-dimethyl-2-imidazolidinone; and halogenated solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in combination of two or more in any desired ratio. Preferred solvents include acidic solvents and benzene solvents. The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (19).

[0310] The temperature during this reaction is not particularly limited as long as the desired reaction proceeds, but is typically between −10° C. and 150° C., or below the boiling point of the solvent. Post-reaction treatment can involve adding water or an appropriate aqueous solution to the reaction mixture to separate the reaction mixture. When using an aqueous solution, any of the following can be used: an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, or the like; an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, or the like; or saline. During the separation, if necessary, a water-immiscible solvent can be added: a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in combination in any ratio. The number of separations is not particularly limited, and can be carried out depending on the desired purity and yield.

[0311] The reaction mixture containing the compound of the present invention represented by formula (1-6) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential. The reaction mixture containing the compound of the present invention represented by formula (1-6) obtained above can be distilled under reduced pressure to remove the solvent, as long as the compound does not decompose.

[0312] The reaction mixture containing the compound of the present invention represented by formula (1-6) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. The method may be appropriately set depending on the desired purity.

[0313] [Manufacturing method P] In the formula, M represents a metal cation such as sodium, potassium, copper, etc., and R １ , R ２ , R６ , R １３ , Xa, and n are as defined above.

[0314] Production method P is a production method for obtaining a compound represented by formula (22), which comprises reacting a compound represented by formula (19) with a cyanating agent represented by formula (21) in a solvent under basic conditions.

[0315] The cyanating agent represented by formula (21) used in this reaction is commercially available or can be produced by a known method. The amount of the cyanating agent represented by formula (21) used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (19), and is preferably 1 equivalent or more and 10 equivalents or less, as long as the target reaction proceeds.

[0316] The base used in this reaction includes organic bases such as triethylamine, tributylamine, diisopropylethylamine, pyridine, collidine, and 2,6-lutidine, and inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, and tripotassium phosphate.

[0317] A solvent can be used in this reaction, but is not necessarily required. The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include ether solvents such as diethyl ether, diisopropyl ether, methyl t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; alcohol solvents such as methanol, ethanol, and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate; nitrile solvents such as acetonitrile; amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide; urea solvents such as 1,3-dimethyl-2-imidazolidinone; and halogenated solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in combination of two or more in any desired ratio. Preferred solvents include acidic solvents and benzene solvents. The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (19).

[0318] The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually from -10°C to 150°C or below the boiling point of the solvent.

[0319] As a post-treatment for the reaction, a separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, any of the following can be used: an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc.; an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc.; or saline solution. During the separation operation, if necessary, a water-immiscible solvent can be added, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in combination of two or more in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield.

[0320] The reaction mixture containing the compound represented by formula (22) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential. The reaction mixture containing the compound represented by formula (22) obtained above can be distilled under reduced pressure to remove the solvent, as long as the compound is not decomposed.

[0321] The reaction mixture containing the compound represented by formula (22) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. The method may be appropriately set depending on the desired purity.

[0322] [Manufacturing method Q] In the formula, Xb represents a hydroxyl group and NRaRb (wherein Ra and Rb have the same meanings as defined above), and R １ , R ２ , R ６ , Xa, and n are as defined above.

[0323] Production method Q is a production method for obtaining a compound represented by formula (23), which comprises subjecting a compound represented by formula (22) to a formylation reaction in a solvent.

[0324] Examples of formylating agents used in this reaction include DMF, N,N-dimethylformamide dimethyl acetal, 4-formylmorpholine, hexamethylenetetramine, N-methylformanilide, N,N-diethyl-N'-formyl-N'-methoxyurea, cyanomethyl formate, ethyl bromodifluoroacetate, ethyl formate, methyl formate, 1-formylpiperidine, N-formylsaccharin, triethyl orthoformate, trimethyl orthoformate, Vilsmeier reagent, paraformaldehyde, Bredereck reagent, etc. The amount of formylating agent used in this reaction may be 1 equivalent or more relative to the compound represented by formula (22), and is not particularly limited as long as the desired reaction proceeds, but is preferably 1 equivalent or more and 10 equivalents or less.

[0325] Examples of the base used in this reaction include metal hydrides such as sodium hydride, metal alkoxides such as sodium methoxide, sodium ethoxide, sodium t-butoxide, and the like, organolithium compounds such as methyllithium, butyllithium, sec-butyllithium, t-butyllithium, hexyllithium, and the like, and metal amides such as lithium diisopropylamide, lithium hexamethyldisilazane, sodium hexamethyldisilazane, and potassium hexamethyldisilazane, and the like.

[0326] A solvent can be used in this reaction, but is not necessarily required. The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include ether solvents such as diethyl ether, diisopropyl ether, methyl t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; alcohol solvents such as methanol, ethanol, and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate; nitrile solvents such as acetonitrile; amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide; urea solvents such as 1,3-dimethyl-2-imidazolidinone; and halogenated solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in combination of two or more in any desired ratio. Preferred solvents include acidic solvents and benzene solvents. The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (22).

[0327] The temperature during this reaction is not particularly limited as long as the desired reaction proceeds, but is typically between −10° C. and 150° C., or below the boiling point of the solvent. Post-reaction treatment can involve adding water or an appropriate aqueous solution to the reaction mixture to separate the reaction mixture. When using an aqueous solution, any of the following can be used: an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, or the like; an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, or the like; or saline. During the separation, if necessary, a water-immiscible solvent can be added: a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in combination in any ratio. The number of separations is not particularly limited, and can be carried out depending on the desired purity and yield.

[0328] The reaction mixture containing the compound represented by formula (23) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential. The reaction mixture containing the compound represented by formula (23) obtained above can be distilled under reduced pressure to remove the solvent, as long as the compound is not decomposed.

[0329] The reaction mixture containing the compound represented by formula (23) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. The method may be appropriately set depending on the desired purity.

[0330] [Manufacturing method R] In the formula, R １５is a hydrogen atom or a protecting group that can be removed under acidic conditions, such as a t-butoxycarbonyl group, a methoxymethyl group, or a p-methoxybenzyl group, and R １ , R ２ , R ６ , Xa, Xb, and n are as defined above.

[0331] Production method R is a production method for obtaining a compound represented by formula (25) and a compound represented by formula (26), and is a production method comprising reacting a compound represented by formula (23) with a compound represented by formula (24) in a solvent. The ratio of the compound represented by formula (25) and the compound represented by formula (26) obtained by this reaction is not particularly limited and may be either one alone or a mixture in any ratio.

[0332] The amount of the compound represented by formula (24) used in this reaction may be 1 equivalent or more relative to the amount of the compound represented by formula (23), and is not particularly limited as long as the desired reaction proceeds, but is preferably 1 equivalent or more and 10 equivalents or less.

[0333] To efficiently proceed with this reaction, an acid catalyst can be used, but is not essential. When an acid is used in this reaction, examples include inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as acetic acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, and pyridinium p-toluenesulfonate. The acid is not particularly limited as long as the desired reaction proceeds, but p-toluenesulfonic acid is preferred. When an acid is used in this reaction, the amount of acid used is 0.001 equivalents or more and 1 equivalent or less relative to the compound represented by formula (23), but is not particularly limited as long as the desired reaction proceeds.

[0334] A solvent can be used in this reaction, but is not necessarily required. The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include ether solvents such as diethyl ether, diisopropyl ether, methyl t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; alcohol solvents such as methanol, ethanol, and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate; nitrile solvents such as acetonitrile; amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide; urea solvents such as 1,3-dimethyl-2-imidazolidinone; and halogenated solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in combination of two or more in any desired ratio. Preferred solvents include acidic solvents and benzene solvents. The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (23).

[0335] The temperature during this reaction is not particularly limited as long as the desired reaction proceeds, but is typically between −10° C. and 150° C., or below the boiling point of the solvent. Post-reaction treatment can involve adding water or an appropriate aqueous solution to the reaction mixture to separate the reaction mixture. When using an aqueous solution, any of the following can be used: an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, or the like; an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, or the like; or saline. During the separation, if necessary, a water-immiscible solvent can be added: a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in combination in any ratio. The number of separations is not particularly limited and can be carried out depending on the desired purity and yield. The reaction mixture containing the compound represented by formula (25) and the compound represented by formula (26) obtained above can be dehydrated with a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential. The reaction mixture containing the compound represented by formula (25) and the compound represented by formula (26) obtained above can be subjected to solvent distillation under reduced pressure as long as the compounds are not decomposed. The reaction mixture containing the compound represented by formula (25) and the compound represented by formula (26) obtained after solvent distillation can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, or the like. The number of separations can be appropriately set depending on the desired purity.

[0336] [Manufacturing method S] In the formula, R １ , R ２ , R ３ , R ４ , R ６ , R１５ , Xa, and n are as defined above.

[0337] Production method S is a production method for obtaining the compound of the present invention represented by formula (1-4), which comprises reacting a compound represented by formula (25), a compound represented by formula (26), and a compound represented by formula (27) in a solvent under acidic conditions.

[0338] The ratio of the compound represented by formula (25) and the compound represented by formula (26) used in this reaction is not particularly limited, and may be either one alone or a mixture of any ratio. The compound represented by formula (27) used in this reaction may be 1 equivalent or more relative to the compound represented by formula (25) and the compound represented by formula (26), and is not particularly limited as long as the target reaction proceeds, but is preferably 1 equivalent or more and 10 equivalents or less.

[0339] The acid used in this reaction is exemplified by inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as acetic acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, and pyridinium p-toluenesulfonate, and is not particularly limited as long as the desired reaction proceeds. However, hydrochloric acid is preferred.

[0340] A solvent can be used in this reaction, but is not necessarily required. The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include ether solvents such as diethyl ether, diisopropyl ether, methyl t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; alcohol solvents such as methanol, ethanol, and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate; nitrile solvents such as acetonitrile; amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide; urea solvents such as 1,3-dimethyl-2-imidazolidinone; and halogenated solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in combination of two or more in any desired ratio. Preferred solvents include acidic solvents and benzene solvents. The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (25) and the compound represented by formula (26).

[0341] The temperature during this reaction is not particularly limited as long as the desired reaction proceeds, but is typically between −10° C. and 150° C., or below the boiling point of the solvent. Post-reaction treatment can involve adding water or an appropriate aqueous solution to the reaction mixture to separate the reaction mixture. When using an aqueous solution, any of the following can be used: an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, or the like; an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, or the like; or saline. During the separation, if necessary, a water-immiscible solvent can be added: a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in combination in any ratio. The number of separations is not particularly limited, and can be carried out depending on the desired purity and yield.

[0342] The reaction mixture containing the compound of the present invention represented by formula (1-4) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential. The reaction mixture containing the compound of formula (1-4) obtained above can be distilled under reduced pressure to remove the solvent, as long as the compound is not decomposed.

[0343] The reaction mixture containing the compound of the present invention represented by formula (1-4) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. The method may be appropriately set depending on the desired purity.

[0344] [Manufacturing method T] In the formula, R １ , R ２ , R ３ , R ４ , R６ , R ８ , R １５ , Xa, and n are as defined above.

[0345] Production method T is a production method for obtaining the compound of the present invention represented by formula (1-4), and comprises reacting a compound represented by formula (25), a compound represented by formula (26), and a compound represented by formula (28) in a solvent under acidic conditions. Production method T can be carried out in accordance with production method S by using the compound represented by formula (28) instead of the compound represented by formula (27) in production method S.

[0346] [Manufacturing method U] In the formula, R １ , R ２ , R ３ , R ４ , R ６ , R ８ , R １５ , Xa, and n are as defined above.

[0347] Production method U is a production method for obtaining the compound of the present invention represented by formula (1-4), and comprises reacting a compound represented by formula (25), a compound represented by formula (26), and a compound represented by formula (29) in a solvent under acidic conditions. Production method U can be carried out in accordance with production method S by using the compound represented by formula (29) instead of the compound represented by formula (27) in production method S.

[0348] [Manufacturing method V] In the formula, R ３ , R ４ , R ６ , G ４ , G ５ , Xa, and n are as defined above.

[0349] Production method V is a production method for obtaining compounds represented by formula (31-1) and formula (31-2), and comprises reacting a compound represented by formula (30) with a compound represented by formula (14) in a solvent under basic conditions.

[0350] The compound represented by formula (31-1) and the compound represented by formula (31-2) obtained by this reaction may be either alone or a mixture of any proportions, and the ratio is not particularly limited. The compound represented by formula (14) used in this reaction can be obtained as a commercially available product or can be produced by a known method. The compound represented by formula (30) used in this reaction can be obtained as a commercially available product or can be produced by a known method.

[0351] The compound represented by formula (14) used in this reaction has a counter anion. The counter anion of formula (14) is not particularly limited as long as the desired reaction proceeds, but examples include fluoride ion, chloride ion, bromide ion, iodide ion, trifluoroacetate ion, 2,4-dinitrophenolate ion, mesitylenesulfonate ion, etc. The amount of formula (14) used in this reaction may be 1 equivalent or more relative to the compound represented by formula (30), and is not particularly limited as long as the desired reaction proceeds, but is preferably 1 equivalent or more and 10 equivalents or less.

[0352] The base used in this reaction includes organic bases such as triethylamine, tributylamine, diisopropylethylamine, pyridine, collidine, and 2,6-lutidine, and inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, and tripotassium phosphate.

[0353] A solvent can be used in this reaction, but is not necessarily required. The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include ether solvents such as diethyl ether, diisopropyl ether, methyl t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; alcohol solvents such as methanol, ethanol, and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate; nitrile solvents such as acetonitrile; amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide; urea solvents such as 1,3-dimethyl-2-imidazolidinone; and halogenated solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in combination of two or more in any desired ratio. Preferred solvents include acidic solvents and benzene solvents. The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (30).

[0354] The temperature during this reaction is not particularly limited as long as the desired reaction proceeds, but is typically between −10° C. and 150° C., or below the boiling point of the solvent. Post-reaction treatment can involve adding water or an appropriate aqueous solution to the reaction mixture to separate the reaction mixture. When using an aqueous solution, any of the following can be used: an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, or the like; an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, or the like; or saline. During the separation, if necessary, a water-immiscible solvent can be added: a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in combination in any ratio. The number of separations is not particularly limited, and can be carried out depending on the desired purity and yield.

[0355] The reaction mixture containing the compound represented by formula (31-1) and the compound represented by formula (31-2) obtained above can be dehydrated with a drying agent such as sodium sulfate, magnesium sulfate, etc., but this is not essential. The reaction mixture containing the compound represented by formula (31-1) and the compound represented by formula (31-2) obtained above can be distilled under reduced pressure to remove the solvent, as long as the compounds are not decomposed.

[0356] The reaction mixture containing the compound represented by formula (31-1) and the compound represented by formula (31-2) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. This can be appropriately set depending on the desired purity.

[0357] [Manufacturing method W] In the formula, R ３ , R４ , R ６ , R １３ , and n have the same meanings as above.

[0358] Production method W is a production method for obtaining a compound represented by formula (34), which comprises reacting a compound represented by formula (32) with a compound represented by formula (33) in a solvent under Lewis acid conditions.

[0359] The amount of the compound of formula (33) used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound of formula (32), as long as the desired reaction proceeds, but is preferably 1 equivalent or more and 10 equivalents or less.

[0360] When a Lewis acid is used in this reaction, examples of the Lewis acid include boron compounds such as boron trifluoride diethyl ether complex, boron trifluoride phenol complex, and boron tribromide; iron compounds such as iron(III) chloride; aluminum compounds such as aluminum chloride and aluminum isopropoxide; titanium compounds such as titanium chloride and titanium tetraisopropoxide; gallium compounds such as gallium chloride and gallium isopropoxide; indium compounds such as indium chloride; scandium compounds such as scandium chloride; and ytterbium compounds such as ytterbium chloride, among which aluminum chloride and iron chloride are preferred.

[0361] A solvent can be used in this reaction, but is not necessarily required. The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include ether solvents such as diethyl ether, diisopropyl ether, methyl t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; alcohol solvents such as methanol, ethanol, and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate; nitrile solvents such as acetonitrile; amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide; urea solvents such as 1,3-dimethyl-2-imidazolidinone; and halogenated solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in combination of two or more in any desired ratio. Preferred solvents include acidic solvents and benzene solvents. The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (32).

[0362] The temperature during this reaction is not particularly limited as long as the desired reaction proceeds, but is typically between −10° C. and 150° C., or below the boiling point of the solvent. Post-reaction treatment can involve adding water or an appropriate aqueous solution to the reaction mixture to separate the reaction mixture. When using an aqueous solution, any of the following can be used: an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, or the like; an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, or the like; or saline. During the separation, if necessary, a water-immiscible solvent can be added: a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in combination in any ratio. The number of separations is not particularly limited, and can be carried out depending on the desired purity and yield.

[0363] The reaction mixture containing the compound represented by formula (34) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential. The reaction mixture containing the compound represented by formula (34) obtained above can be distilled under reduced pressure to remove the solvent, as long as the compound is not decomposed.

[0364] The reaction mixture containing the compound represented by formula (34) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. The method may be appropriately set depending on the desired purity.

[0365] [Manufacturing method X] In the formula, R １ , R ２ , R ６ , R ８, Xa, Het, and n are as defined above.

[0366] Production method X is a method for obtaining the compound of the present invention represented by formula (1-7), which comprises reacting a compound represented by formula (35) with a compound represented by formula (4) in the presence of an ammonium salt.

[0367] The compound represented by formula (35) can be produced based on the production method or Reference Examples. The compound represented by formula (35) used in this reaction can be produced based on Production Method V, Production Method W, or Reference Examples. The compound represented by formula (4) used in this reaction can be commercially available or produced by known methods. The compound represented by formula (4) used in this reaction may be at least 1 equivalent relative to the compound represented by formula (35), and is not particularly limited as long as the desired reaction proceeds, but is preferably at least 1 equivalent and no more than 200 equivalents. Furthermore, when the compound represented by formula (4) is liquid, it can also be used as a solvent.

[0368] Examples of the ammonium salt used in this reaction include ammonium chloride, ammonium acetate, ammonium sulfate, ammonium phosphate, etc. There are no particular limitations as long as the target reaction proceeds, but ammonium acetate is preferred.

[0369] A solvent can be used in this reaction, but is not necessarily required. The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, and examples thereof include acidic solvents such as acetic acid and methanesulfonic acid; ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; alcohol solvents such as methanol, ethanol, and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate; nitrile solvents such as acetonitrile; amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide; urea solvents such as 1,3-dimethyl-2-imidazolidinone; and halogenated solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in combination of two or more in any desired ratio. Preferred examples of the solvent include acidic solvents and benzene solvents, and more preferably acetic acid and toluene. The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (35).

[0370] The temperature during this reaction is not particularly limited as long as the desired reaction proceeds, but is typically between 50°C and 180°C, or below the boiling point of the solvent. Post-reaction treatment can involve adding water or an appropriate aqueous solution to the reaction mixture to perform a separation operation. When using an aqueous solution, any of the following can be used: an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, or the like; an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, or the like; or saline. During the separation operation, if necessary, a water-immiscible solvent can be added, such as a benzene-based solvent (e.g., toluene, xylene, benzene, chlorobenzene, dichlorobenzene); an ester-based solvent (e.g., ethyl acetate, isopropyl acetate, butyl acetate); an ether-based solvent (e.g., diethyl ether, diisopropyl ether, methyl t-butyl ether); a halogen-based solvent (e.g., dichloromethane, dichloroethane, chloroform, carbon tetrachloride); or a hydrocarbon-based solvent (e.g., hexane, heptane, cyclohexane, methylcyclohexane). These solvents can be used alone or in combination of two or more in any ratio. The number of separations is not particularly limited, and can be carried out depending on the desired purity and yield.

[0371] The reaction mixture containing the compound of the present invention represented by formula (1-7) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential. The reaction mixture containing the compound of the present invention represented by formula (1-7) obtained above can be distilled under reduced pressure to remove the solvent, as long as the compound is not decomposed.

[0372] The reaction mixture containing the compound of the present invention represented by formula (1-7) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. The method may be appropriately set depending on the desired purity.

[0373] [Manufacturing method Y] In the formula, R １ , R ２ , R ６ , R ８, Xa, Het and n are as defined above.

[0374] Production method Y is a method for obtaining the compound of the present invention represented by formula (1-7), and comprises reacting a compound represented by formula (35) with a compound represented by formula (5) in the presence of an ammonium salt. Production method Y can be carried out in accordance with production method X by using a compound represented by formula (5) instead of the compound represented by formula (4).

[0375] [Manufacturing method Z] In the formula, Ox represents an oxidizing agent, m represents an integer of 1 or 2, and R １ , R ２ , R ６ , Het and n have the same meanings as defined above.

[0376] Production method Z is a production method for the compound of the present invention represented by formula (1-9), which comprises reacting the compound of the present invention represented by formula (1-8) with an oxidizing agent (Ox) in a solvent.

[0377] Examples of the oxidizing agent used in this reaction include peroxides such as hydrogen peroxide and meta-chloroperbenzoic acid. Transition metals such as sodium tungstate can also be added. The amount of the oxidizing agent used in this reaction is usually 1.0 equivalent to 1.2 equivalents relative to the compound of the present invention represented by formula (1-8) when producing S(=O), and 1.0 equivalent to 1.2 equivalents when producing SO ２ When producing the compound (I), the amount of the compound is usually 2 to 10 equivalents. When a transition metal is added, the amount is usually 0.001 to 1 equivalent.

[0378] The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples thereof include aqueous solvents, acidic solvents such as acetic acid, benzene-based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene, nitrile-based solvents such as acetonitrile, and halogenated solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in combination of two or more in any desired ratio. The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound of the present invention represented by formula (1-8).

[0379] The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is typically between −10° C. and 120° C. or below, or below the boiling point of the solvent. Post-reaction treatment can be performed by adding water or an appropriate aqueous solution to the reaction mixture to perform a liquid separation operation. When using an aqueous solution, any of the following can be used: an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, or the like; an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, or the like; an aqueous solution containing a sulfur-containing salt such as sodium thiosulfate or sodium sulfite; or saline. During the liquid separation operation, it is possible to add, as necessary, a water-immiscible solvent, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in combination of two or more in any proportion. The number of separations is not particularly limited and can be carried out depending on the desired purity and yield.

[0380] The reaction mixture containing the compound of the present invention represented by formula (1-9) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential. The reaction mixture containing the compound of the present invention represented by formula (1-9) obtained above can be distilled under reduced pressure to remove the solvent, as long as the compound does not decompose.

[0381] The reaction mixture containing the compound of the present invention represented by formula (1-9) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. The method may be appropriately set depending on the desired purity.

[0382] [Manufacturing method AA] In the formula, Lv represents a leaving group such as a methanesulfonyl group, a trifluoromethanesulfonyl group, a p-toluenesulfonyl group, or a halogen atom; R ５ａ represents a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group optionally substituted with a substituent A, a C2 to C6 alkenyl group optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group optionally substituted with a substituent A, or a C2 to C6 haloalkynyl group; R １ , R ２ , R ３ , R ４ , R ６ , G ４ , G ５ , Xa and n are as defined above.

[0383] Production method AA is a method for synthesizing the compound of the present invention represented by formula (1-11), which is obtained by combining the compound of the present invention represented by formula (1-10) and R ５ａ The compound of the present invention represented by formula (1-10) used in this reaction can be prepared by the method of Preparation Method E or the method of Reference Example. ５ａ -Lv is commercially available or can be produced by known methods.

[0384] Examples of the base used in this reaction include metal hydrides such as sodium hydride, organolithium compounds such as methyllithium, butyllithium, sec-butyllithium, t-butyllithium, and hexyllithium, and metal amides such as lithium diisopropylamide, lithium hexamethyldisilazane, sodium hexamethyldisilazane, and potassium hexamethyldisilazane. The amount of the base used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound of the present invention represented by formula (1-10), and is preferably 1 equivalent or more and 10 equivalents or less, as long as the desired reaction proceeds.

[0385] The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, and examples thereof include ether solvents such as diethyl ether, diisopropyl ether, methyl t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, and benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene. These solvents can be used alone or in combination of two or more in any desired ratio.

[0386] The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound of the present invention represented by formula (1-10).

[0387] The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is typically between −80°C and 100°C, or below the boiling point of the solvent. Post-treatment of the reaction can be performed by adding water or an appropriate aqueous solution to the reaction mixture to perform a liquid separation operation. When using an aqueous solution, any of the following can be used: an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, or the like; an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, or the like; an aqueous solution containing a sulfur-containing salt such as sodium thiosulfate or sodium sulfite; or saline. During the liquid separation operation, it is possible to add, as necessary, a water-immiscible solvent, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, or chloroform; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in combination of two or more in any desired ratio. The number of separations is not particularly limited and can be carried out depending on the desired purity and yield. The reaction mixture containing the compound of the present invention represented by formula (1-11) obtained above can be dehydrated with a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential. The reaction mixture containing the compound of formula (1-11) obtained above can be subjected to solvent distillation under reduced pressure, as long as the compound is not decomposed. The reaction mixture containing the compound of the present invention represented by formula (1-11) obtained after solvent distillation can be used as is in the next reaction, or can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, or the like. The number of separations can be appropriately determined depending on the desired purity.

[0388] [Manufacturing method AB] In the formula, R ４ａ represents a halogen atom, R ４ｂrepresents a C1-C6 alkyl group which may be substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be substituted with a substituent A, a C2-C6 alkenyl group which may be substituted with a substituent A, or a C2-C6 haloalkenyl group; R ４ｂ -B represents an organic boronic acid, the bond including the broken line is a single bond or a double bond, and forms an aromatic ring; R １ , R ２ , R ３ , R ５ , R ６ , G １ , G ２ , G ３ , G ４ , G ５ , Xa and n are as defined above.

[0389] The production method AB is a method for synthesizing the compound of the present invention represented by formula (1-11), which comprises reacting the compound of the present invention represented by formula (1-10) with an organic boronic acid (R ４ｂ -B) in a solvent in the presence of a transition metal and a base, thereby obtaining the compound by Suzuki-Miyaura coupling.

[0390] The compound of the present invention represented by (1-10) used in this reaction can be produced by referring to Production Method G, Production Method I, Production Method J, Production Method K, Production Method O, Production Method S, Production Method T, Production Method U, Production Method X, Production Method Y or Reference Examples. ４ｂ -B represents an organic boronic acid such as an organic boronic acid or an organic boronic acid ester, and can be obtained as a commercial product or produced by a known method. ４ｂ The amount of -B is not particularly limited as long as it is 1 equivalent or more relative to the compound of the present invention represented by formula (1-10) and the target reaction proceeds, but is preferably 1 equivalent or more and 10 equivalents or less.

[0391] The transition metal used in this reaction is palladium, nickel, ruthenium, etc., and may have a ligand. Preferred examples include palladium compounds such as palladium acetate, [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride, tris(dibenzylideneacetone)dipalladium, tetrakis(triphenylphosphine)palladium, bis(triphenylphosphine), and palladium dichloride. The amount of the transition metal used in this reaction is 0.001 equivalents or more and 1 equivalent or less relative to the compound of the present invention represented by formula (1-10), but is not particularly limited as long as the desired reaction proceeds.

[0392] To efficiently proceed with this reaction, a phosphine ligand such as triphenylphosphine, tricyclohexylphosphine, etc. can be added. The amount of the phosphine ligand used in this reaction is 0.001 equivalents or more and 1 equivalent or less relative to the compound of the present invention represented by formula (1-10), but is not particularly limited as long as the desired reaction proceeds.

[0393] The base used in this reaction is an inorganic base such as sodium carbonate, potassium carbonate, cesium carbonate, tripotassium phosphate, etc., or a metal alkoxide such as sodium methoxide, sodium ethoxide, potassium t-butoxide, etc. The amount of the base used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound of the present invention represented by formula (1-10), as long as the desired reaction proceeds, but is preferably 1 equivalent or more and 50 equivalents or less.

[0394] The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples thereof include water, ether solvents such as diethyl ether, diisopropyl ether, methyl t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, and benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene. These solvents can be used alone or in combination of two or more in any desired ratio. The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound of the present invention represented by formula (1-10).

[0395] The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is typically 30°C or higher and 100°C or lower, or below the boiling point of the solvent. Post-reaction treatment can be performed by adding water or an appropriate aqueous solution to the reaction mixture to perform a liquid separation operation. When using an aqueous solution, any of the following can be used: an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, or the like; an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, or the like; an aqueous solution containing a sulfur-containing salt such as sodium thiosulfate or sodium sulfite; or saline. During the liquid separation operation, it is possible to add, as necessary, a water-immiscible solvent, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, or chloroform; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in combination of two or more in any desired ratio. The number of separations is not particularly limited and can be carried out depending on the desired purity and yield. The reaction mixture containing the compound of the present invention represented by formula (1-11) obtained above can be dehydrated with a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential. The reaction mixture containing the compound of formula (1-11) obtained above can be subjected to solvent distillation under reduced pressure, as long as the compound is not decomposed. The reaction mixture containing the compound of the present invention represented by formula (1-11) obtained after solvent distillation can be used as is in the next reaction, or can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, or the like. The number of separations can be appropriately determined depending on the desired purity.

[0396] [Manufacturing method AC] In the formula, R ３ａ represents a halogen atom, R ３ｂrepresents a C1-C6 alkyl group which may be substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be substituted with a substituent A, a C2-C6 alkenyl group which may be substituted with a substituent A, or a C2-C6 haloalkenyl group; R ３ｂ -B represents an organic boronic acid, and R １ , R ２ , R ４ , R ５ , R ６ , G １ , G ２ , G ３ , G ４ , G ５ , Xa, the bond including the broken line portion, and n have the same meanings as defined above.

[0397] Production method AC is a method for synthesizing the compound of the present invention represented by formula (1-13), which comprises reacting the compound of the present invention represented by formula (1-12) with an organic boronic acid (R ３ｂ -B) in a solvent in the presence of a transition metal and a base, thereby obtaining the compound by Suzuki-Miyaura coupling.

[0398] The compound of the present invention represented by formula (1-13) used in this reaction can be produced by referring to Production Method G, Production Method I, Production Method J, Production Method K, Production Method O, Production Method S, Production Method T, Production Method U, Production Method X, Production Method Y or Reference Examples. Production Method AC can be carried out in accordance with Production Method AB by using the compound of the present invention represented by formula (1-12) instead of the compound of the present invention represented by formula (1-10) in Production Method AB.

[0399] [Manufacturing method AD] In the formula, R4c represents a C2-C6 alkynyl group optionally substituted with a substituent A, a C2-C6 haloalkynyl group, or a C2-C6 haloalkenyl group; R １ , R ２ , R ３ , R ４ａ , R ５ , R ６ , G １ , G ２ , G ３ , G ４ , G ５, Xa, the bond including the broken line portion, and n have the same meanings as defined above.

[0400] Production method AD is a method for synthesizing the compound of the present invention represented by formula (1-14), which comprises reacting the compound of the present invention represented by formula (1-10) with a terminal alkyne compound in a solvent in the presence of a transition metal and a base, thereby obtaining the compound by Sonogashira coupling.

[0401] The terminal alkyne compound used in this reaction can be commercially available or produced by known methods. Trimethylsilylacetylene can also be used as the terminal alkyne compound. In this case, it is necessary to introduce a trimethylsilylethynyl group into the compound of the present invention represented by formula (1-10) and then perform desilylation. Desilylation can be performed with reference to non-patent literature such as Journal of the American Chemical Society, Vol. 131, No. 2, pp. 634-643 (2009) and Journal of Organometallic Chemistry, Vol. 696, No. 25, pp. 4039-4045 (2011). The amount of the terminal alkyne compound used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound of the present invention represented by formula (1-10) so long as the desired reaction proceeds, but is preferably 1 equivalent or more and 10 equivalents or less.

[0402] The transition metals used in this reaction may have a ligand, and include palladiums such as palladium acetate, [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride, tris(dibenzylideneacetone)dipalladium, tetrakis(triphenylphosphine)palladium, and bis(triphenylphosphine)palladium dichloride. Coppers such as copper chloride, copper bromide, and copper iodide are also used. The amounts of the transition metals used in this reaction are not particularly limited, as long as the palladiums and coppers are each 0.001 equivalents or more relative to the compound of the present invention represented by formula (1-10), and the amounts are not particularly limited as long as the desired reaction proceeds. The preferred amounts are 0.001 equivalents or more and 1 equivalent or less for both.

[0403] Examples of the base used in this reaction include organic amines such as triethylamine, tributylamine, isopropylamine, diethylamine, diisopropylamine, and diisopropylethylamine, and inorganic bases such as sodium carbonate, potassium carbonate, and cesium carbonate. The amount of the base used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound of the present invention represented by formula (1-10) and the desired reaction proceeds, but is preferably 1 equivalent or more and 50 equivalents or less. Furthermore, liquid organic bases can be used as solvents.

[0404] To efficiently proceed with this reaction, a phosphine ligand such as tri-t-butylphosphine or 2-dicyclohexylphosphino-2'4'6'-triisopropylbiphenyl can be added, but is not essential. The amount of the phosphine ligand used in this reaction is 0.001 equivalents or more and 1 equivalent or less relative to the compound of the present invention represented by formula (1-10), but is not particularly limited as long as the desired reaction proceeds.

[0405] The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples thereof include ether solvents such as diethyl ether, diisopropyl ether, methyl t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc., benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, etc., ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, etc., nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, etc., urea solvents such as 1,3-dimethyl-2-imidazolidinone, halogenated solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride, etc., organic amine solvents such as triethylamine, tributylamine, isopropylamine, diethylamine, diisopropylamine, diisopropylethylamine, etc. These solvents can be used alone or in combination of two or more in any ratio. The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound of the present invention represented by formula (1-10).

[0406] The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is typically from 0°C to 150°C or below the boiling point of the solvent. As a post-treatment for the reaction, water or an appropriate aqueous solution can be added to the reaction mixture to perform a liquid separation operation. When an aqueous solution is used, any of the following can be used: an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, or the like; an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, or the like; an aqueous solution containing a sulfur-containing salt such as sodium thiosulfate or sodium sulfite; or saline. During the liquid separation operation, it is possible to add, as necessary, a water-immiscible solvent, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, or chloroform; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in combination of two or more in any proportion. The number of separations is not particularly limited and can be carried out depending on the desired purity and yield. The reaction mixture containing the compound of the present invention represented by formula (1-14) obtained above can be dehydrated with a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential. The reaction mixture containing the compound of formula (1-14) obtained above can be subjected to solvent distillation under reduced pressure, as long as the compound is not decomposed. The reaction mixture containing the compound of the present invention represented by formula (1-14) obtained after solvent distillation can be used as is in the next reaction, or can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, or the like. The number of separations can be appropriately determined depending on the desired purity.

[0407] [Manufacturing method AE] In the formula, R3c represents a C2-C6 alkynyl group optionally substituted with a substituent A, a C2-C6 haloalkynyl group, or a C2-C6 haloalkenyl group; R １ , R ２ , R ３ａ , R ４ , R ５ , R ６ , G １ , G ２ , G ３ , G ４ , G ５ , Xa, the bond including the broken line portion, and n have the same meanings as defined above.

[0408] Production Method I is a method for synthesizing the compound of the present invention represented by formula (1-15), which comprises reacting the compound of the present invention represented by formula (1-12) with a terminal alkyne compound in a solvent in the presence of a transition metal and a base by Sonogashira coupling. Production Method AE can be carried out in accordance with Production Method AD by using the compound of the present invention represented by formula (1-12) instead of the compound of the present invention represented by formula (1-10) in Production Method AD.

[0409] [Manufacturing method AF] In the formula, R ６ａ represents a halogen atom, R ６ｂ represents a C1-C6 alkyl group which may be substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be substituted with a substituent A, a C2-C6 alkenyl group which may be substituted with a substituent A, or a C2-C6 haloalkenyl group; R ６ｂ -B represents an organic boronic acid, and R １ , R ２ , Xa and Het have the same meanings as defined above.

[0410] Production method AF is a method for synthesizing the compound of the present invention represented by formula (1-17), which comprises reacting the compound of the present invention represented by formula (1-16) with an organic boronic acid (R ６ｂ -B) in a solvent in the presence of a transition metal and a base, thereby obtaining the compound by Suzuki-Miyaura coupling.

[0411] The compound of the present invention represented by formula (1-16) used in this reaction can be produced by referring to Production Method G, Production Method I, Production Method J, Production Method K, Production Method O, Production Method S, Production Method T, Production Method U, Production Method X, Production Method Y, or Reference Examples. Production Method AF can be carried out in accordance with Production Method AB by using the compound represented by formula (1-16) instead of the compound represented by formula (1-10) in Production Method AB.

[0412] [Manufacturing method AG] In the formula, R １ , R ２ , R ６ａ , Xa, Het, Ra and Rb have the same meanings as defined above.

[0413] Production method AG is a production method for obtaining the compound of the present invention represented by formula (1-18), which comprises subjecting the compound of the present invention represented by formula (1-16) and a compound represented by RaRbNH to a coupling reaction in a solvent in the presence of a transition metal and a base.

[0414] The RaRb-NH used in this reaction is commercially available or can be produced by a known method. The amount of RaRb-NH used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound of the present invention represented by formula (1-16), as long as the desired reaction proceeds, but is preferably 1 equivalent or more and 100 equivalents or less. Furthermore, when RaRbNH is in a liquid form, it can be used as a solvent.

[0415] The transition metals used in this reaction may have a ligand, and include copper compounds such as copper powder, copper chloride, copper bromide, copper iodide, and copper acetate, and palladium compounds such as palladium acetate, [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride, tris(dibenzylideneacetone)dipalladium, tetrakis(triphenylphosphine)palladium, and bis(triphenylphosphine)palladium dichloride. The amount of the transition metals used in this reaction is not particularly limited as long as it is 0.001 equivalents or more relative to the compound of the present invention represented by formula (1-16), and is not particularly limited as long as the desired reaction proceeds. The preferred amounts are 0.001 equivalents or more and 1 equivalent or less for both compounds.

[0416] To efficiently proceed with this reaction, when a palladium transition metal is used, a phosphine ligand such as triphenylphosphine, 1,1'-bis(diphenylphosphino)ferrocene, tri-t-butylphosphine, 2-dicyclohexylphosphino-2'4'6'-triisopropylbiphenyl, or 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene can be added. When a copper transition metal is used, an amine ligand such as N,N'-dimethylcyclohexane-1,2-diamine or N,N'-dimethylethylenediamine, or an oxime ligand such as 1-(pyridin-2-yl)ethan-1-one oxime can be added, but this is not essential. The amount of the ligand used in this reaction is 0.001 equivalents or more and 1 equivalent or less relative to the compound of the present invention represented by formula (1-16), but is not particularly limited as long as the desired reaction proceeds.

[0417] The base used in this reaction includes inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, and tripotassium phosphate; metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium t-butoxide; and organic bases such as triethylamine, tributylamine, and diisopropylethylamine. The amount of the base used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (1-17) and the desired reaction proceeds, but is preferably 1 equivalent or more and 50 equivalents or less.

[0418] The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples thereof include organic amine solvents represented by R a R b NH ; alcohol solvents such as methanol, ethanol, isopropyl alcohol, and t-butyl alcohol; ether solvents such as diethyl ether, diisopropyl ether, methyl t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; benzene solvents such as benzene, toluene, xylene, and mesitylene; ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate; nitrile solvents such as acetonitrile; amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide; and urea solvents such as 1,3-dimethyl-2-imidazolidinone. These solvents can be used alone or in combination of two or more in any desired ratio. The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is typically 3 to 200 times by weight relative to the compound of the present invention represented by Formula (1-16).

[0419] The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is typically from 0°C to 180°C or below the boiling point of the solvent. As a post-treatment for the reaction, water or an appropriate aqueous solution can be added to the reaction mixture to perform a liquid separation operation. When an aqueous solution is used, any of the following can be used: an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, or the like; an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, or the like; an aqueous solution containing a sulfur atom-containing salt such as sodium thiosulfate or sodium sulfite; or saline. During the liquid separation operation, it is possible to add, as necessary, a water-immiscible solvent, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, or chloroform; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in combination of two or more in any proportion. The number of separations is not particularly limited and can be carried out depending on the desired purity and yield.

[0420] The reaction mixture containing the compound of the present invention represented by formula (1-18) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential. The reaction mixture containing the compound of the present invention represented by formula (1-18) obtained above can be distilled under reduced pressure to remove the solvent, as long as the compound is not decomposed.

[0421] The reaction mixture containing the compound of the present invention represented by formula (1-18) obtained after distilling off the solvent can be used as it is in the next reaction, but can also be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. The purification process may be appropriately set depending on the desired purity.

[0422] [Manufacturing method AH] In the formula, R１ , R ２ , R ３ , R ４ , R ６ , R １３ , Xa, and n are as defined above.

[0423] Production method AH is a method for obtaining the compound of the present invention represented by formula (1-19), and includes cross-coupling via C—H activation in which a compound represented by formula (11) is reacted with an imidazopyridazine derivative (36) in a solvent in the presence of a transition metal and a base.

[0424] The compound of formula (36) used in this reaction is commercially available or can be produced by a known method. The amount of the compound of formula (36) used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound of formula (11) as long as the target reaction proceeds, but is preferably 1 equivalent or more and 10 equivalents or less.

[0425] The transition metal used in this reaction is palladium, nickel, ruthenium, etc., and may have a ligand. Preferred examples include palladium compounds such as palladium acetate, [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride, tris(dibenzylideneacetone)dipalladium, tetrakis(triphenylphosphine)palladium, bis(triphenylphosphine), and palladium dichloride. The amount of the transition metal used in this reaction is 0.001 equivalents or more and 1 equivalent or less relative to the compound represented by formula (11), but is not particularly limited as long as the desired reaction proceeds.

[0426] To efficiently proceed with this reaction, a phosphine ligand such as triphenylphosphine, tricyclohexylphosphine, tri-tert-butylphosphonium tetrafluoroborate, etc. can be added. The amount of the phosphine ligand used in this reaction is 0.001 equivalents or more and 1 equivalent or less relative to the compound represented by formula (11), but is not particularly limited as long as the target reaction proceeds.

[0427] The base used in this reaction is an inorganic base such as sodium carbonate, potassium carbonate, cesium carbonate, tripotassium phosphate, etc., or a metal alkoxide such as sodium methoxide, sodium ethoxide, potassium t-butoxide, etc. The amount of the base used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (11) and the target reaction proceeds, but is preferably 1 equivalent or more and 50 equivalents or less.

[0428] The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples thereof include water, ether solvents such as diethyl ether, diisopropyl ether, methyl t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, and benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene. These solvents can be used alone or in combination of two or more in any desired ratio. The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (11).

[0429] The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is typically 30°C or higher and 100°C or lower, or below the boiling point of the solvent. Post-reaction treatment can be performed by adding water or an appropriate aqueous solution to the reaction mixture to perform a liquid separation operation. When using an aqueous solution, any of the following can be used: an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, or the like; an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, or the like; an aqueous solution containing a sulfur-containing salt such as sodium thiosulfate or sodium sulfite; or saline. During the liquid separation operation, it is possible to add, as necessary, a water-immiscible solvent, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, or chloroform; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in combination of two or more in any proportion. The number of separations is not particularly limited and can be carried out depending on the desired purity and yield.

[0430] The reaction mixture containing the compound of the present invention represented by formula (1-19) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential. The reaction mixture containing the compound of the present invention represented by formula (1-19) obtained above can be distilled under reduced pressure to remove the solvent, as long as the compound does not decompose.

[0431] The reaction mixture containing the compound of the present invention represented by formula (1-19) obtained after distilling off the solvent can be used as it is in the next reaction, but can also be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. The purification process may be appropriately set depending on the desired purity.

[0432] The compound represented by formula (1) can be produced by any combination of the above-described production methods A to AH. Alternatively, the compound represented by formula (1) can be produced by any combination of known methods and production methods A to AH.

[0433] [Agricultural and horticultural pest control agent] One embodiment of the present invention is an agricultural and horticultural pest control agent containing a compound represented by formula (1) or a salt thereof (hereinafter simply referred to as "compound (1)"). Compound (1) can exterminate and prevent organisms harmful to plants or plant parts (fruits, flowers, leaves, stems, rhizomes, roots, seeds, etc.), and can also protect plants from organisms harmful to plants or plant parts. Therefore, it is preferably used as an agricultural and horticultural pest control agent, for example, it is preferably used as a fungicide, insecticide, herbicide, plant growth regulator, etc., and it is more preferably used as an agricultural and horticultural fungicide. That is, one embodiment of the present invention may be an agricultural and horticultural fungicide containing compound (1). Hereinafter, agricultural and horticultural pest control agents and agricultural and horticultural fungicides are also referred to as "agricultural and horticultural pest control agents, etc."

[0434] Examples of organisms harmful to plants include fungi, bacteria, spiroplasma, phytoplasma, viruses, viroids, parasitic higher plants, nematodes, etc. Compound (1) is particularly effective for controlling fungi. These harmful organisms may cause plant diseases, and may cause, for example, abnormal systemic pathological symptoms such as wilting, damping-off, yellowing, dwarfing, and spindly growth in plants such as agricultural crops, flowers, flowering trees, and trees, as well as local pathological symptoms such as spots, leaf withering, mosaic, leaf curling, branch withering, root rot, root galls, and galls.

[0435] Harmful fungi include fungi that cause fungal diseases (i.e., pathogens), such as Pseudomonas, oomycetes, zygomycetes, ascomycetes, basidiomycetes, and fungi imperfecti. Examples of Pseudomonas include Plasmodiophora root clubroot, potato powdery scab, and sugar beet root rot fungus. Examples of oomycetes include Phytophthora blight, downy mildew, fungi of the genus Pythium, and fungi of the genus Aphanomyces. Examples of zygomycetes include fungi of the genus Rhizopus. Examples of ascomycetes include peach leaf curl fungus, corn leaf blight fungus, rice blast fungus, powdery mildew fungus, anthracnose fungus, Fusarium head blight fungus, Gibberella bakanae fungus, and sclerotinia rot fungus. Examples of basidiomycetes include rust fungi, smut fungi, purple root rot fungi, blast fungi, sheath blight fungi, etc. Examples of imperfect fungi include gray mold fungi, fungi of the genus Alternaria, fungi of the genus Fusarium, fungi of the genus Penicillium, fungi of the genus Rhizoctonia, and southern blight fungi.

[0436] The agricultural and horticultural pest control agent of this embodiment is effective against the following types of plant diseases. Specific diseases and their pathogens are listed below, but the present invention is not limited to these.

[0437] Magnaporthe grisea, Thanatephorus cucumeris, Ceratobasidium setariae, Waitea circinata, Thanatephorus cucumeris, Sclerotinia hydrophilum, Waitea circinata, Entyloma dactylidis, Magnaporthe grisea salvinii)、Ceratobasidium cornigerum)、Goma leaf blight)、Cochliobolus miyabeaanus)、Sphaerurulina oryzinana)、Gaka seedling blight)、Gibberella fujikuruoi)、Seedling damping-off disease)、Pythium spp.、Fusarium spp.、Trichoderma spp.、Rhizopus spp.、Rhizoctonia solanini)、Mucor sp.、Phoma spp. )、Seedling rot (Pythium spp.、Achlya spp.、Dictyucchus spp.)、Claviceps virens )、Black spike disease (Tilletia barclayana )、Brown rice (Curvularia spp.、Alternaria spp.)、Chlorophylla macrospora )、Bacterial leaf blight (Xanthoma oryzae pp.、Oryzae spp.)、Brown streak disease (Acidovoraxa avenae subsp. )、 avenae), Erwinia anaananas, Burkholderia plantaria, Burkholderia glumae, Pseudomonas fuscovaginae, Pseudomonas syringae pv. oryzae, Erwinia chrysanthemum wilt, Phytoplasma oryzae, and Ricestripe. tenuivirus), atrophy disease (Rice dwarf reovirus);Blumeriagra minis f. sp. hordei; f. Striformis, Puccinia graminis, Puccinia recondita, Puccinia hordei), leaf spot (Pyrenophora) graminea, Pyrenophora teres), red かび disease (Gibberella zeae, Fusarium culmorum、fusarium avenaceum, Monographella nivalis, snow rot (Typhula) incarnata、Typhula ishikariensis, Monographella nivalis), Ustilago nuda, Naked Kuro disease (Tiletia) caries, Tilletia controversa), Pseudocercosporella herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia herpotricularia spp., Pyrenophora spp.), damping-off (Gaeumannnomyces graminis), anthracnose (Colletotrichum graminicola), ergot (Claviceps purpururea), leaf spot (Cochliobolus sativus), black knot (Pseudomonas syringae pv.syringae);Fusarium head blight (Gibberella zeae, etc.), seedling damping-off (Fusarium avenaceum, Penicillium spp., Pythium spp., Rhizoctonia spp.), rust (Puccinia spp.) of corn sorghi), sesame leaf blight (Cochliobolus heterostrophus), smut (Ustilago maydis), anthrax (Colletotrichum graminicola), northern spot disease (Cochliobolus) carbonum), Gray Leaf Spot disease (Cercospora zeae-maydis), brown stripe (Acidovorax avenae subsp. avenae), bacterial streak (Burkholderia andropogonis), bacterial lodging (Erwinia chrysanthemi pv. zeae), bacterial wilt (Erwinia stewartii); grape downy mildew (Plasmopara viticola), rust (Physopella ampelopsidis), powdery mildew (Uncinula necator), black rot (Elsinoe ampelina), late rot (Glomerella cingulata, Colletotrichum acutatum), black rot (Guignardia bidwellii), fusarium wilt (Phomopsis viticola), sooty spot (Zygophiala jamaicensis), gray mold (Botrytis cinerea), bud blight (Diaporthe medusaea), purple root rot (Helicobasidium mompa), white root rot (Rosellinia necatrix), crown gall (Agrobacterium vitis);Apple powdery mildew (Podosphaera leucotricha), black scab (Venturia inaequalis), leaf spot (Alternari amali), red scab (Gymnosporangium yamadae), monilia disease (Monilinia mali), canker (Valsa ceratosperma), ring spot (Botryosphaeria berengeriana), anthracnose (Colletotrichum acutatum, Glomerella cingulata), sooty spot (Zygophiala jamaicensis), sooty blotch (Gloeodes pomigena), black spot (Mycosphaerella pomi), purple root rot (Helicobasidium mompa), white root rot (Rosellinia necatrix), canker (Phomopsis mali, Diaporthe tanakae), brown spot (Diplocarpon mali), apple fire blight (Erwinia amylovora), crown gall (Agrobacterium tumefaciens), hairy root disease (Agrobacterium rhizogenes); pear black spot (Alternaria kikuchiana), black scab (Venturia nashicola), red spot (Gymnosporangium asiaticum), ring spot (Botryosphaeria berengeriana f.sp.piricola), canker (Phomopsis fukushii), bacterial branch blight (Erwinia sp.), crown gall (Agrobacterium tumefaciens), rust canker (Erwinia chrysanthemi pv. chrysanthemi), bacterial blossom rot (Pseudomonas syringae pv. syringae); pear blight (Phytophthora cactorum, Phytophthora syringae), bacterial branch blight (Erwinia sp.);Peach black scab (Cladosporium carpophilum), Phomopsis rot (Phomopsis sp.), Late blight (Phytophthora sp.), Anthracnose (Colletotrichum gloeosporioides), Leaf curl (Taphrina deformans), Bacterial perforation (Xanthomonas campestris pv. pruni), Crown gall (Agrobacterium tumefaciens); Cherry anthracnose (Glomerella cingulata), Young fruit stem rot (Monilinia kusanoi), Brown rot (Monilinia fructicola), crown gall (Agrobacterium tumefaciens), resin bacterial disease (Pseudomonas syringae pv. syringae); persimmon anthracnose (Glomerella cingulata), leaf drop (Cercospora kaki; Mycosphaerella nawae), powdery mildew (Phyllactinia kakikora), crown gall (Agrobacterium tumefaciens); citrus black spot (Diaporthe citri), green mold (Penicillium digitatum), blue mold (Penicillium italicum), scab (Elsinoe fawcettii), brown rot (Phytophthora citrophthora), canker (Xanthomonas campestris pv. citri), brown spot bacterial disease (Pseudomonas syringae pv. syringae), greening disease (Liberibacter asiaticus), crown gall disease (Agrobacterium tumefaciens); gray mold (Botrytis cinerea) of tomatoes, cucumbers, beans, strawberries, potatoes, cabbage, eggplant, lettuce, etc.; Sclerotinia sclerotiorum of tomatoes, cucumbers, beans, strawberries, potatoes, rapeseed, cabbage, eggplant, lettuce, etc.;Seedling damping-off of various vegetables such as tomatoes, cucumbers, beans, radishes, watermelons, eggplants, rapeseeds, peppers, spinach, and sugar beets (Rhizoctonia spp., Pythium spp., Fusarium spp., Phythophthora spp., Sclerotinia sclerotiorum, etc.); bacterial wilt of solanaceous plants (Ralstonia solanacearum); downy mildew of cucurbits (Pseudoperonospora cubensis), powdery mildew (Sphaerotheca fuliginea), and anthracnose (Colletotrichum orbiculare), vine blight (Didymella bryoniae), vine split disease (Fusarium oxysporum), late blight (Phytophthora parasitica, Phytophthora Xanthomonas campestris pv. cucurbitae), soft rot (Erwinia carotovora subsp. carotovora), bacterial spot disease (Pseudomonas) syringae pv. lachrymans), bacterial edge blight (Pseudomonas marginalis pv. marginalis), canker (Streptomyces sp.), hairy root disease (Agrobacterium rhizogenes), cucumber mosaic virus;Tomato target spot (Alternaria solani), leaf mold (Fulvia fulva), late blight (Phytophthora infestans), Fusarium wilt (Fusarium oxysporum), root rot (Pythium myriotylum, Pythium dissotocum), anthracnose (Colletotrichum gloesporioides), bacterial canker (Clavibacter michiganensis), bacterial leaf spot (Pseudomonas corrugata), black bacterial leaf spot (Pseudomonas viridiflava), soft rot (Erwinia carotovora subsp. carotovora), leaf knot disease (Crynebacterium sp.), aster yellows (Phytoplasma asteris), tobacco leaf curl subgroup III geminivirus; Eggplant powdery mildew (Sphaerotheca fuliginea, etc.), sooty mold (Mycovellosiella nattrassii), late blight (Phytophthora infestans), brown rot (Phytophthora capsici), brown bacterial leaf spot (Pseudomonas cichorii), bacterial leaf spot (Pseudomonas corrugata), stem rot bacteria (Erwinia chrysanthemi), soft rot (Erwinia carotovora subsp. carotovora), bacterial leaf spot (Pseudomonas sp.); Rapeseed black spot (Alternaria brassicae), black rot (Xhantomonas campestris pv. campestris), black bacterial leaf spot (Pseudomonas syringae pv. maculicola), soft rot (Erwinia carotovora).Black spot (Alternaria brassicae, etc.), white spot (Cercosporella brassicae), root rot (Phoma lingam), clubroot (Plasmodiophora brassicae), downy mildew (Peronospora parasitica), black rot (Xhantomonas campestris pv. campestris), black spot bacterial disease (Pseudomonas syringae pv. maculicola), anthracnose (Colletotrichum higgincianum), black soot disease (Alternaria brassicicola), white rust (Albugo macrospora), soft rot (Erwinia carotovora subsp. carotovora) of cruciferous vegetables; Foot rot (Thanatephorus cucumeris), fusarium wilt (Fusarium oxysporum), black soot disease (Alternaria brassisicola) of cabbage; Bottom rot (Rhizoctonia solani), yellowing disease (Verticillium dahliae) of Chinese cabbage; Rust (Puccinia allii), black spot (Alternaria porri), southern blight (Sclerotium rolfsii), white blight (Phytophthora porri), black rot sclerotinia disease (Sclerotium cepivorum), wilt disease (Fusarium oxysporum), downy mildew (Peronospora destructor), sclerotinia rot disease (Botrytis squamosa), leaf blight (Stemphylium sp.) of onion; Soft rot (Erwinia carotovora subsp. carotovora), bacterial leaf spot (Pseudomonas syringae pv. syringae), rot disease (Erwinia rhapontici), scale rot disease (Burkholderia gladioli), fusarium wilt (Phytoplasma asteris) of potato;Garlic soft rot (Erwinia carotovora subsp. carotovora), spring rot (Pseudomonas marginalis pv. marginalis); soybean purple spot (Cercospora kikuchii), black rot (Elsinoe glycines), black spot (Diaporthe phaseolorum), Rhizoctonia root rot (Rhizoctonia solani), stem rot (Phytophthora sojae), downy mildew (Peronospora manshurica), rust (Phakopsora pachyrhizi), anthrax (Colletotrichum truncatum, etc.), brown ring disease (Corynespora cassicola), spotted disease (Cercospora sojina), brown spot disease (Septoria) Pv. glycinea), bacterial spot disease (Pseudomonas syringae pv. glycinea); anthracnose disease of kidney beans (Colletotrichum) lindemuthianum), bacterial wilt (Ralstonia solanacearum), halo blight (Pseudomonas syringae pv. phaseolicola), bacterial brown spot (Pseudomonas viridiflava), leaf burn (Xanthomonas campestris pv. phaseoli); black spot of peanut (Mycosphaerella berkeleyi), brown spot (Mycosphaerella arachidis), bacterial wilt (Ralstonia solanacearum); powdery mildew of pea (Erysiphe pisi), downy mildew (Peronospora pisi), vine blight (Pseudomonas syringae pv. pisi), vine rot bacterial disease (Xhanthomonas campestris pv. pisi); Downy mildew of broad bean (Peronospora viciae), late blight (Phytophthora nicotianae);Potato summer blight (Alternaria solani), black spot (Thanatephorus cucumeris), late blight (Phytophthora infestans), silver scurf (Helminthosporium solani), dry rot (Fusarium oxysporum, Fusarium solani), powdery scab (Spongospora subterranea), bacterial wilt (Ralstonia solanacearum), black leg (Erwinia carotovora subsp. atroseptica), common scab (Streptomyces scabies, Streptomyces acidiscabies), soft rot (Erwinia carotovora subsp. carotovora), sticky rot (Clostridium spp.), ring rot (Clavibacter michiganensis subsp. Diaporthe destruens, damping-off (Streptomyces ipomoeae) of sweet potato; Cercospora beticola, downy mildew (Peronospora) of sugar beet schachtii), black root disease (Aphanomyces cochioides), Janome disease (Phoma betae), crown gall (Agrobacterium tumefaciens), powdery mildew (Erysiphe betae), leaf spot (Ramularia beticola), scab (Streptomyces scabies), bacterial spot (Pseudomonas syringae pv. aptata); carrot leaf blight (Alternaria dauci), clubroot (Rhizobacter dauci), crown gall (Agrobacterium tumefaciens), streptomyces scab (Streptomyces spp.), soft rot (Erwinia carotovora subsp. carotovora);Strawberry powdery mildew (Sphaerotheca aphanis var. aphanis), late blight (Phytophthora nicotianae, etc.), anthracnose (Glomerella cingulata, etc.), fruit rot (Pythium ultimum), bacterial wilt (Ralstonia solanacearum), bacterial angular spot (Xanthomonas campestris), bacterial bud blight (Pseudomonas marginalis pv. marginalis); tea net blight (Exobasidium reticulatum), white spot (Elsinoe leucospila), anthracnose (Colletotrichum theae-sinensis), ring spot (Pestalothiopsis longiseta), red burn (Pseudomonas syringae pv. theae), canker (Xanthomonas campestris pv. theicola), witches' broom (Pseudomonas sp.); tobacco red star (Alternaria alternata), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum gloeosporioides), late blight (Phytophthora nicotianae), wildfire (Pseudomonas syringae pv. tabaci), bacterial yellow blight (Pseudomonas syringae pv. mellea), cavity disease (Erwinia carotovora subsp. carotovora), damping-off (Ralstonia solanacearum), tobacco mosaic virus; coffee rust (Hemileia vastatrix);Banana black Sigatoka disease (Mycosphaerella minima, Mycosphaerella musae, Mycosphaerella musicola, Cercospora musae, Metasphaeria musae), yellow Sigatoka disease (Pseudocercospora musae), Panama disease (Fusarium oxysporum), bunchy top disease (Banana bunchy top virus), mosaic disease (Cucumber mosaic virus), stem rot (Ceratocystis paradoxa, Colletotrichum musae, Lasiodiplodia theobromae, Botryodiplodia theobromae, fruit drop (Colletotrichum musae), black rot (Botryodiplodia theobromae), black spot (Macrophomma musae), black mold (Rhizopus stolonifer), thin stripe (Cercospora musaecola), southern blight (Sclerotium rolfsii), anthracnose (Colletotrichum musae), round star disease (Sclerotrichum musae), stem rot (Marasmius semiustus); sunflower sclerotinia (Sclerotinia sclerotiorum), corner spot (Xanthomonas campestris pv. malvacearum), cavity (Erwinia carotovora subsp. carotovora), bacterial spot (Pseudomonas syringae pv. helianthi); rose scab (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa, etc.), late blight (Phytophthora megasperma), downy mildew (Peronospora sparsa), crown gall disease (Agrobacterium tumefaciens);Chrysanthemum brown spot (Septoria obesa), white rust (Puccinia horiana), late blight (Phytophthora cactorum), bacterial spot (Pseudomonas cichorii), soft rot (Erwinia carotovora subsp. carotovora), crown gall (Agrobacterium tumefaciens), hairy root disease (Agrobacterium rhizogenes), greening disease (Phytoplasma aurantifolia); turf brown patch (Rhizoctonia solani), dollar spot (Sclerotinia Homoeocarpa), Curvularia sp., Puccinia zoysiae, Cochliobolus sp., Rhynchosporium secalis), damping-off (Gaeumannomyces graminis), anthracnose (Colletotrichum sp.), snow rot brown small-grain sclerotia (Typhula incarnata), snow-rot black small-grain sclerotia (Typhulaishikariensis), snow-rot large-grain sclerotinia (Myriosclerotinia borealis), fairy ring disease (Marasmius) Pythium disease (Pythium aphanidermatum, etc.), Blast disease (Pyricularia grisea, Phanidermatum, etc.), Blast disease (Pyricularia grisea, etc.) grisea), Pseudomonas syringae pv. atropurprea, Pseudomonas syringae pv. avenae), Drechslera sp., Bipolaris sorokiniana, Drechslera sp. poae), summer patch disease (Magnaporthe poae), necrotrophic ringspot disease (Ophiosphaerella korrae, Ophiosphaerella herpotricha, Ophiosphaerella spp.), etc.;

[0438] The agricultural and horticultural pest control agent of the present embodiment may contain one or more types of compound (1), and preferably contains one type of compound (1).

[0439] In this embodiment, the content of compound (1) in the agricultural and horticultural pest control agent, etc. is not particularly limited as long as it is an amount that allows formulation, but is, for example, preferably 0.1 to 50 mass%, more preferably 1 to 40 mass%, and even more preferably 5 to 30 mass%, relative to 100 mass% of the agricultural and horticultural pest control agent, etc. The content of compound (1) in the agricultural and horticultural pest control agent, etc. may be determined from the charge ratio during production of the agricultural and horticultural pest control agent, etc., or may be the content listed on the product package.

[0440] The agricultural and horticultural pest control agent of this embodiment may contain only compound (1), or may contain compound (1) and optional components, such as solid carriers, liquid carriers, gaseous carriers, colorants, solvents / oils, sugars, water-soluble polymers, preservatives / fungicides, inorganic salts, UV screening agents, latexes / emulsions, fragrances, mineral powders, dispersants, stabilizers, surfactants, etc.

[0441] The formulation of the agricultural and horticultural pest control agent of this embodiment is not particularly limited, but examples include dusts, granules, powders, hydrated powders, water-soluble powders, emulsions, liquids, oils, flowables, aerosols, pastes, fumigants, fumigants, liniments, microcapsules, and packs.

[0442] [Method for producing agricultural and horticultural pest control agents, etc.] The method for producing the agricultural and horticultural pest control agents, etc. of this embodiment is not particularly limited as long as it is a method that can produce a composition containing compound (1), and known production methods can be used depending on the dosage form. Examples of the method for producing the agricultural and horticultural pest control agents, etc. include a method of mixing compound (1) with any component.

[0443] [Method for controlling plant diseases] One embodiment of the present invention is a method for controlling plant diseases, which comprises applying an agricultural and horticultural pest control agent or the like to a plant, a plant seed, or the soil in which a plant is grown.

[0444] In this embodiment, a plant is a living organism that belongs to a biological category in contrast to animals and generally refers to an organism that lives in a fixed location. Examples of plants include fruit trees, vegetables, grains, ornamental plants, trees, and other plants. Examples of fruit trees include citrus fruits such as mandarins and lemons, pome fruits such as pears, apples, and persimmons, stone fruits such as peaches and ...

Claims

1. A compound represented by the following formula (1) or a salt thereof: [In formula (1), R １ and R ２ each independently represents a C1 to C6 alkyl group which may be substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be substituted with a substituent A, a C2 to C6 alkenyl group which may be substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be substituted with a substituent A, a C2 to C6 haloalkynyl group, a C1 to C6 acyl group which may be substituted with a substituent A, an aryl group which may be substituted with a substituent B, and a heteroaryl group which may be substituted with a substituent B; -C(=O)NRaRb (wherein Ra and Rb each independently represent a hydrogen atom, a C1 to C6 alkyl group which may be substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 acyl group, and -C(=O)ORc (wherein Rc represents a group selected from the group consisting of a hydrogen atom, a C1-C6 alkyl group which may be substituted with a substituent A, a C1-C6 haloalkyl group, and a C3-C8 cycloalkyl group); or Ra and Rb together with the nitrogen atom to which they are bonded form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group, or an azocanyl group; and -C(=O)ORc (wherein Rc has the same meaning as defined above); １ and R ２ may be taken together to form a C3-C8 cycloalkyl ring which may be substituted with a substituent A, or a C3-C8 saturated or unsaturated heterocycle which may be substituted with a substituent A; Het represents formula (2), In formula (2), R ３ , R ４ , and R ５ are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1 to C6 alkyl group which may be substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be substituted with a substituent A, a C1 to C6 alkoxy group which may be substituted with a substituent A, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group which may be substituted with a substituent A, a C2 to C6 alkenyl group which may be substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be substituted with a substituent A, a C2 to C6 haloalkynyl group, a C2 to C6 alkenyloxy groups, C2 to C6 haloalkenyloxy groups, C3 to C6 alkynyloxy groups which may be substituted by substituent A, C3 to C6 haloalkynyloxy groups, -NRaRb (wherein Ra and Rb are as defined above), -C(=O)NRaRb (wherein Ra and Rb are as defined above), -C(=O)ORc (wherein Rc is as defined above), -OC(=O)Rc (wherein Rc is as defined above), and -L-Rd (wherein Rd represents a group selected from the group consisting of C1 to C6 alkyl groups and C1 to C6 haloalkyl groups, and L is S, S(=O), and SO ２ represents a group selected from the group consisting of: ３ and R ４ together form a C5-C10 unsaturated ring which may be substituted with a substituent A; n represents an integer of 0 to 4; R ６ represents a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1 to C6 alkyl group which may be substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be substituted with a substituent A, a C1 to C6 alkoxy group which may be substituted with a substituent A, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group which may be substituted with a substituent A, a C2 to C6 alkenyl group which may be substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be substituted with a substituent A, a C2 to C6 haloalkynyl group, a C2 to C6 alkenyloxy group which may be substituted with a substituent A, R represents a group selected from the group consisting of an oxy group, a C2-C6 haloalkenyloxy group, a C3-C6 alkynyloxy group which may be substituted by a substituent A, a C3-C6 haloalkynyloxy group, -NRaRb (wherein Ra and Rb are as defined above), -C(=O)ORc (wherein Rc are as defined above), -C(=O)NRaRb (wherein Ra and Rb are as defined above), -C(=O)ORc (wherein Rc is as defined above), -OC(=O)Rc (wherein Rc is as defined above), and -L-Rd (wherein L and Rd are as defined above); ７ represents a group selected from the group consisting of a lone electron pair, a hydrogen atom, a C1-C6 alkyl group which may be substituted with a substituent A, a C1-C6 haloalkyl group, a C2-C6 alkenyl group which may be substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be substituted with a substituent A, a C2-C6 haloalkynyl group, and an acyl group which may be substituted with a substituent A; G １ , G ２ , and G ３ each independently represents a group selected from the group consisting of carbon atoms and nitrogen atoms (provided that G １ , G ２ , and G ３ At least one of is a carbon atom; ４ and G ５ each independently represents a group selected from the group consisting of a nitrogen atom and CRx; Rx is a hydrogen atom, a halogen atom, a C1-C6 alkyl group which may be substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be substituted with a substituent A, a C1-C6 alkoxy group which may be substituted with a substituent A, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group which may be substituted with a substituent A, a C2-C6 alkenyl group which may be substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be substituted with a substituent A, a C2-C6 haloalkynyl group, a C2-C6 alkenyloxy group which may be substituted with a substituent A, represents a group selected from the group consisting of a C2-C6 haloalkenyloxy group, a C3-C6 alkynyloxy group which may be substituted with a substituent A, a C3-C6 haloalkynyloxy group, -NRaRb (wherein Ra and Rb are as defined above), -C(=O)NRaRb (wherein Ra and Rb are as defined above), -C(=O)ORc (wherein Rc is as defined above), and -L-Rd (wherein L and Rd are as defined above); the bond containing the dashed line represents a single bond or a double bond; X represents O, S, S(=O), SO ２ and NRe; Re represents a group selected from the group consisting of a hydrogen atom, a C1-C6 alkyl group which may be substituted with a substituent A, a C1-C6 haloalkyl group, a C2-C6 alkenyl group which may be substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be substituted with a substituent A, and a C2-C6 haloalkynyl group; Substituent A is a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 cycloalkoxy group, a C1-C6 alkenyloxy group, a C1-C6 haloalkenyloxy group, a C1-C6 alkynyloxy group, a C1-C6 haloalkynyloxy group, a C1-C6 acyl group, an aryl group which may be substituted with a substituent B, a heteroaryl group which may be substituted with a substituent B, a substituted aryl group ... A phenoxy group which may be appropriately substituted with a substituent B, -NRaRb (wherein Ra and Rb are as defined above), -C(=O)NRaRb (wherein Ra and Rb are as defined above), -C(=O)ORc (wherein Rc is as defined above), -OC(=O)Rc (wherein Rc is as defined above), and -L-Rd (wherein L and Rd are as defined above); the substituent B is at least one selected from the group consisting of a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C6 alkyl group which may be substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, and a C3-C8 cycloalkoxy group, and Rd-L- (wherein Rd is as defined above). ] 2. G ４ and G ５ The compound or salt thereof according to claim 1 , wherein at least one of is a nitrogen atom.

3. R ３ , R ４ , and R ５ each independently represents a group selected from the group consisting of a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1 to C6 alkyl group which may be substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be substituted with a substituent A, a C1 to C6 alkoxy group which may be substituted with a substituent A, a C2 to C6 alkenyl group which may be substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be substituted with a substituent A, a C2 to C6 haloalkynyl group, a C2 to C6 alkenyloxy group which may be substituted with a substituent A, a C2 to C6 haloalkenyloxy group, a C3 to C6 alkynyloxy group which may be substituted with a substituent A, and a C3 to C6 haloalkynyloxy group, ３ and R ４ together form a C5-C10 unsaturated ring which may be substituted with a substituent A; n represents an integer of 0 to 2; R ６ represents a group selected from the group consisting of halogen atoms, hydroxyl groups, cyano groups, nitro groups, C1 to C6 alkyl groups which may be substituted with a substituent A, C1 to C6 haloalkyl groups, C3 to C8 cycloalkyl groups which may be substituted with a substituent A, C1 to C6 alkoxy groups which may be substituted with a substituent A, C1 to C6 haloalkoxy groups, C3 to C8 cycloalkoxy groups which may be substituted with a substituent A, C2 to C6 alkenyl groups which may be substituted with a substituent A, C2 to C6 haloalkenyl groups, C2 to C6 alkynyl groups which may be substituted with a substituent A, C2 to C6 haloalkynyl groups, C2 to C6 alkenyloxy groups which may be substituted with a substituent A, C2 to C6 haloalkenyloxy groups, C3 to C6 alkynyloxy groups which may be substituted with a substituent A, C3 to C6 haloalkynyloxy groups, and -NRaRb (wherein Ra and Rb are as defined above); R ７ represents a group selected from the group consisting of a lone electron pair, a hydrogen atom, a C1-C6 alkyl group which may be substituted with a substituent A, a C1-C6 haloalkyl group, and an acyl group which may be substituted with a substituent A; G ４ and G ５ each independently represents a group selected from the group consisting of a nitrogen atom and CRx; Rx represents a group selected from the group consisting of a hydrogen atom, a halogen atom, a C1 to C6 alkyl group which may be substituted with substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be substituted with substituent A, a C1 to C6 alkoxy group which may be substituted with substituent A, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group which may be substituted with substituent A, a C2 to C6 alkenyl group which may be substituted with substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be substituted with substituent A, and a C2 to C6 haloalkynyl group; The compound according to claim 1 or a salt thereof.

4. G ４ and G ５ The compound or salt thereof according to claim 3, wherein at least one of is a nitrogen atom.

5. R １ and R ２ each independently represents a group selected from the group consisting of a C1-C6 alkyl group which may be substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be substituted with a substituent A, a C2-C6 alkenyl group which may be appropriately substituted with a substituent A, a C1-C6 acyl group which may be substituted with a substituent A, an aryl group which may be substituted with a substituent B, a heteroaryl group which may be substituted with a substituent B, and -C(=O)ORc (wherein Rc has the same meaning as defined above), or R １ and R ２ together form a C3-C8 cycloalkyl ring which may be substituted with a substituent A, or a C3-C8 saturated or unsaturated heterocycle which may be substituted with a substituent A; R ３ , R ４ , and R ５ each independently represents a group selected from the group consisting of a hydrogen atom, a halogen atom, a C1-C6 alkyl group which may be substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be substituted with a substituent A, a C1-C6 alkoxy group which may be substituted with a substituent A, and a C2-C6 alkenyl group which may be substituted with a substituent A, or R ３ and R ４ together form a C5-C10 unsaturated ring which may be substituted with a substituent A; n represents an integer of 0 to 2; R ６ represents a group selected from the group consisting of a halogen atom, a C1-C6 alkyl group which may be substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be substituted with a substituent A, a C1-C6 alkoxy group which may be substituted with a substituent A, a C3-C8 cycloalkoxy group which may be substituted with a substituent A, a C2-C6 alkenyl group which may be substituted with a substituent A, and -NRaRb (wherein Ra and Rb are as defined above); R ７ represents a lone pair of electrons; １ , G ２ and G ３ At least one of represents a carbon atom and at least one represents a nitrogen atom; G ４ and G ５ each independently represents a group selected from the group consisting of a nitrogen atom and CRx; Rx represents a group selected from the group consisting of a hydrogen atom and a C1-C6 alkyl group which may be substituted with a substituent A; the bond including the dashed line represents a single bond or a double bond; X represents O, S, S(=O) and SO ２ The compound according to claim 3 or a salt thereof, wherein:

6. Formula (2) is selected from the group consisting of the following formulas (2-1), (2-2), (2-3), (2-4), (2-5), (2-6), (2-7), (2-8), (2-9), (2-10), and (2-11), R ３ , R ４ , and R ｘ The compound or salt thereof according to claim 5 , wherein:

7. Formula (2) is selected from the group consisting of the following formulas (2-1), (2-2), (2-3), (2-5), (2-6), (2-8), and (2-9), ３ , R ４ , and R ｘ The compound or salt thereof according to claim 5 , wherein:

8. Formula (2) is selected from the group consisting of the following formulas (2-2), (2-3), (2-6), and (2-9), ３ , R ４ , and R ｘ The compound or salt thereof according to claim 5 , wherein:

9. An agricultural and horticultural pest control agent comprising the compound or salt thereof according to claim 1.

10. An agricultural or horticultural fungicide comprising the compound or salt thereof according to claim 1.

11. A method for controlling plant diseases, which comprises applying the agricultural and horticultural pest control agent according to claim 9 to a plant, a plant seed, or the soil in which a plant is grown.

12. A method for controlling plant diseases, which comprises applying the agricultural and horticultural fungicide according to claim 10 to a plant, a plant seed, or the soil in which a plant is grown.

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