JP2014024840A - Condensed heterocyclic compound and pest control use thereof - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a compound having pest control efficacy.SOLUTION: A condensed heterocyclic compound represented by the formula (1) [where, Arepresents a nitrogen atom or =CR-, Arepresents a nitrogen atom or =CR-, Rrepresents a C1-C6 chain hydrocarbon group or the like, R, R, Rand Ridentically or differently represent a C1-C6 chain hydrocarbon group or the like, Rand Ridentically or differently represent a C1-C6 chain hydrocarbon group or the like or a hydrogen atom, Rrepresents a C1-C6 chain hydrocarbon group having one phenyl group or the like, Rand Ridentically or differently represent a C1-C6 chain hydrocarbon group which may have one or more halogen atoms or the like, and n represents 0, 1 or 2] or an N-oxide thereof is provided.

Description

  The present invention relates to certain fused heterocyclic compounds and their use for pest control.

So far, various compounds have been studied and put into practical use for the purpose of controlling pests.
In addition, certain types of fused heterocyclic compounds (for example, see Patent Document 1) are known.

JP-T-1-501473

  An object of the present invention is to provide a compound having an excellent control effect against pests and a method for controlling pests using the compound.

  As a result of intensive studies to solve the above-mentioned problems, the present inventors have found that the condensed heterocyclic compound represented by the following formula (1) has an excellent control effect against pests, and have led to the present invention. .

[1]
Formula (1)
[Where:
A ¹ represents a nitrogen atom or = CR ⁹ - represents,
A ² represents a nitrogen atom or = CR ^10- ,
R ¹ may have a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from group X, or one or more atoms or groups selected from group Y. Represents a C3-C6 alicyclic hydrocarbon group,
R ² , R ³ , R ⁴ and R ⁵ are the same or different and are selected from the group Z and a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from the group X. one or more atoms or phenyl group which may have a group, one or more atoms 5 or or may have a group 6-membered heterocyclic group selected from the group Z, -OR ^11, -S (O) _m R ¹¹ , —S (O) ₂ NR ¹¹ R ¹² , —NR ¹¹ R ¹² , —NR ¹¹ CO ₂ R ¹² , —NR ¹¹ C (O) R ¹² , —CO ₂ R ¹¹ , —C (O) represents R ¹² , —C (O) NR ¹¹ R ¹² , —SF ₅ , a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R ⁶ and R ⁷ are the same or different and are each a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from group X, one or more atoms selected from group Z, or A phenyl group which may have a group, a 5- or 6-membered heterocyclic group which may have one or more atoms or groups selected from group Z, —OR ¹¹ , —S (O) _m R ¹¹ , —S (O) ₂ NR ¹¹ R ¹² , —NR ¹¹ R ¹² , —NR ¹¹ CO ₂ R ¹² , —NR ¹¹ C (O) R ¹² , —CO ₂ R ¹¹ , —C (O) R ¹¹ , a cyano group, a nitro group, a halogen atom, -SF ₅ or a hydrogen atom,
R ⁸ is a C1-C6 chain hydrocarbon group having one phenyl group (wherein the phenyl group may have one or more atoms or groups selected from group Z), or 1 C1-C6 chain hydrocarbon group having a 5- or 6-membered heterocyclic group (wherein the 5- or 6-membered heterocyclic group has one or more atoms or groups selected from group Z) Represents)
R ⁹ and R ¹⁰ are the same or different and are a C1-C6 chain hydrocarbon group which may have one or more halogen atoms, —OR ¹¹ , —S (O) _m R ¹¹ , —NR ¹¹ R _{^{12, -CO 2 R 11, -C}} (O) R 11, a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R ¹¹ and R ¹² are the same or different and each represents a C1-C6 chain hydrocarbon group or hydrogen atom which may have one or more halogen atoms,
m represents 0, 1 or 2, and n represents 0, 1 or 2.
Here, R ⁶ and R ⁷ do not simultaneously represent a hydrogen atom, and in —S (O) _m R ¹¹ , when m is 1 or 2, R ¹¹ does not represent a hydrogen atom.
Group X: C3-C6 cycloalkyl group optionally having one or more halogen atoms or one or more C1-C3 alkyl groups, C1-C6 alkoxy optionally having one or more halogen atoms A group, a C2-C6 alkenyloxy group optionally having one or more halogen atoms, a C2-C6 alkynyloxy group optionally having one or more halogen atoms, and having one or more halogen atoms. A C1-C6 alkylsulfanyl group which may have one or more, a C1-C6 alkylsulfinyl group which may have one or more halogen atoms, a C1-C6 alkylsulfonyl which may have one or more halogen atoms A C2-C6 alkylcarbonyl group which may have one or more halogen atoms, a C2-C6 alkoxy group which may have one or more halogen atoms Boniru group, cyano group, hydroxy group and the group consisting of halogen atoms.
Group Y: C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, C1-C6 alkoxy group optionally having one or more halogen atoms, one or more halogen atoms A group consisting of a C2-C6 alkenyloxy group optionally having one, a C2-C6 alkynyloxy group optionally having one or more halogen atoms, a hydroxy group and a halogen atom.
Group Z: C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, C1-C6 alkoxy group optionally having one or more halogen atoms, one or more halogen atoms A C1-C6 alkylsulfanyl group optionally having one or more, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6 optionally having one or more halogen atoms Alkylsulfonyl group, C2-C6 alkylcarbonyl group optionally having one or more halogen atoms, C2-C6 alkoxycarbonyl group optionally having one or more halogen atoms, one or more halogen atoms A C1-C6 alkylamino group optionally having one or more, a C2-C8 dialkylamino group optionally having one or more halogen atoms, a halogen atom, a cyano group, and The group consisting of Toro group. ]
Or a N-oxide thereof (hereinafter referred to as the present compound).

[2]
R ² , R ³ , R ⁴ and R ⁵ are the same or different and are selected from group Z, a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from group X one or more atoms or phenyl group which may have a group, one or more atoms 5 or or may have a group 6-membered heterocyclic group selected from the group Z, -OR ^11, -S (O) _m R ¹¹ , —SF ₅ , a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R ⁶ and R ⁷ are the same or different and may have one or more atoms or groups selected from group X, a C1-C6 chain hydrocarbon group, —OR ¹¹ , —S (O) _m R ¹¹ , —SF ₅ , a halogen atom or a hydrogen atom,
R ⁹ and R ¹⁰ are each a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR ¹¹ , —S (O) _m R ¹¹ , a halogen atom or a hydrogen atom [1 ] The compound of description.

[3]
R ¹ is a C1-C6 alkyl group optionally having one or more atoms or groups selected from the group consisting of halogen atoms and cyclopropyl groups (wherein the cyclopropyl group is one or more halogen atoms) Or may have one or more C1-C3 alkyl groups), may have one or more halogen atoms, may have C2-C6 alkenyl groups, or may have one or more halogen atoms. A good C2-C6 alkynyl group, or a cyclopropyl group optionally having one or more halogen atoms,
R ² , R ⁴ and R ⁵ are the same or different and are a halogen atom or a hydrogen atom,
R ³ has a C1-C6 alkyl group optionally having one or more halogen atoms, a C2-C6 alkenyl group optionally having one or more halogen atoms, and one or more halogen atoms. An optionally substituted C2-C6 alkynyl group, a 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is a C1-C3 alkyl group optionally having a halogen atom, One or more atoms or groups selected from the group consisting of a C1-C3 alkoxy group which may have a halogen atom and a halogen atom may be present.), —OR ¹¹ , —S (O) _m R ¹¹ , a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R ⁶ is a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ¹¹ , —S (O) _m R ¹¹ , —SF ₅ or a halogen atom;
R ⁷ is a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ¹¹ , —S (O) _m R ¹¹ , a halogen atom or a hydrogen atom;
R ¹¹ is a C1-C6 alkyl group optionally having one or more halogen atoms,
R ⁸ is a C1-C6 alkyl group having one phenyl group (wherein the phenyl group may be a cyano group, a C1-C3 alkyl group optionally having a halogen atom, or a halogen atom). A C1-C3 alkoxy group, and one or more atoms or groups selected from the group consisting of halogen atoms.) C1-C6 having one 5- or 6-membered aromatic heterocyclic group An alkyl group (wherein the 5- or 6-membered aromatic heterocyclic group is a C1-C3 alkyl group optionally having a halogen atom, a C1-C3 alkoxy group optionally having a halogen atom, and a halogen atom); Which may have one or more atoms or groups selected from the group consisting of atoms), or a C1-C6 alkyl group having one tetrahydrofuryl group (wherein the tetrahydrofuryl group). Has one or more atoms or groups selected from the group consisting of a C1-C3 alkyl group optionally having a halogen atom, a C1-C3 alkoxy group optionally having a halogen atom, and a halogen atom. You may have)
R ⁹ and R ¹⁰ are each a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ¹¹ , —S (O) _m R ¹¹ , a halogen atom, or a hydrogen atom. Compound.
[4]
A ¹ is = CR ⁹ - a [1] to [3] A compound according to any one.
[5]
The compound according to any one of [1] to [3], wherein A ¹ is a nitrogen atom.
[6]
A ¹ is = CR ⁹ - a, ^{A 2} is a nitrogen atom [1] to [3] The compound according to one any.
[7]
A ¹ is nitrogen atom, ^{A 2} is = ^{CR 10} - is [1] to [3] A compound according to any one.
[8]
The compound according to any one of [1] to [3], wherein A ¹ is = CR ⁹ -and A ² is = CR ^10- .
[9]
A ¹ is = CH-
R ⁷ is a hydrogen atom,
R ¹ is a C1-C6 alkyl group optionally having one or more atoms or groups selected from the group consisting of halogen atoms and cyclopropyl groups (wherein the cyclopropyl group is one or more halogen atoms) Or may have one or more C1-C3 alkyl groups), may have one or more halogen atoms, may have C2-C6 alkenyl groups, or may have one or more halogen atoms. A good C2-C6 alkynyl group, or a cyclopropyl group optionally having one or more halogen atoms,
R ² , R ⁴ and R ⁵ are the same or different and are a halogen atom or a hydrogen atom,
R ³ has a C1-C6 alkyl group that may have one or more halogen atoms, a C2-C6 alkenyl group that may have one or more halogen atoms, and one or more halogen atoms An optionally substituted C2-C6 alkynyl group, a 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is a C1-C3 alkyl group optionally having a halogen atom, a halogen One or more atoms or groups selected from the group consisting of a C1-C3 alkoxy group which may have an atom, and a halogen atom; and -OR ²⁰ (wherein R ²⁰ represents Represents a C1-C6 alkyl group optionally having one or more halogen atoms.), -S (O) _m R ²¹ (wherein R ²¹ may have one or more halogen atoms). Represents a good C1-C6 alkyl group m represents 0, 1 or 2.), a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R ⁶ may be a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ²² (wherein R ²² is a C1-C6 alkyl group optionally having one or more halogen atoms) -S (O) _m R ²³ (wherein R ²³ represents a C1-C6 alkyl group optionally having one or more halogen atoms, and m represents 0, 1 or 2). .), - a SF ₅ or halogen atom,
R ⁸ is a C1-C6 alkyl group having one phenyl group (wherein the phenyl group may be a cyano group, a C1-C3 alkyl group optionally having a halogen atom, or a halogen atom). A C1-C3 alkoxy group, and one or more atoms or groups selected from the group consisting of halogen atoms.) C1-C6 having one 5- or 6-membered aromatic heterocyclic group An alkyl group (wherein the 5- or 6-membered aromatic heterocyclic group is a C1-C3 alkyl group optionally having a halogen atom, a C1-C3 alkoxy group optionally having a halogen atom, and a halogen atom); Which may have one or more atoms or groups selected from the group consisting of atoms), or a C1-C6 alkyl group having one tetrahydrofuryl group (wherein the tetrahydrofuryl group). Has one or more atoms or groups selected from the group consisting of a C1-C3 alkyl group optionally having a halogen atom, a C1-C3 alkoxy group optionally having a halogen atom, and a halogen atom. You may have)
R ¹⁰ may be a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ²⁴ (wherein R ²⁴ is a C1-C6 alkyl group optionally having one or more halogen atoms) ), —S (O) _m R ²⁵ (wherein R ²⁵ represents a C1-C6 alkyl group optionally having one or more halogen atoms, and m represents 0, 1 or 2). ), A halogen atom or a hydrogen atom,
The compound according to [1], wherein n is 0, 1 or 2.

[10]
A ¹ is = CH-
R ⁷ is a hydrogen atom,
R ¹ is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a cyclopropyl group optionally having one or more halogen atoms, or a C1-C6 alkyl group having a cyclopropyl group (wherein the cyclo The propyl group may have one or more halogen atoms or one or more C1-C3 alkyl groups).
R ² , R ⁴ and R ⁵ are hydrogen atoms,
R ³ has a C1-C6 alkyl group that may have one or more halogen atoms, a C2-C6 alkenyl group that may have one or more halogen atoms, and one or more halogen atoms An optionally substituted C2-C6 alkynyl group, a pyridyl group (wherein the pyridyl group is a C1-C3 alkyl group optionally having a halogen atom, a C1-C3 alkoxy group optionally having a halogen atom, And a pyrimidinyl group (wherein the pyrimidinyl group is a C1-C3 alkyl group optionally having a halogen atom). it may have optionally C1-C3 may be alkoxy groups having a halogen atom, and one or more atoms or groups selected from the group consisting of halogen atom), -. oR ² , ^{(Wherein, R 20} is one or more halogen atoms optionally may C1-C6 alkyl group which may have ^{_{a.) - S (O) m}} R 21 ( ^wherein halogen ^{R 21} is 1 or more An optionally substituted C1-C6 alkyl group, and m is 0, 1 or 2.), a halogen atom or a hydrogen atom,
R ⁶ is a C1-C6 haloalkyl group, —OR ²² (wherein R ²² is a C1-C6 haloalkyl group), —S (O) _m R ²³ (wherein R ²³ is a C1-C6 haloalkyl group) There, m is 0, 1 or 2), -. a SF ₅ or halogen atom,
R ⁸ is a C1-C6 alkyl group having one phenyl group (wherein the phenyl group may have a cyano group, a C1-C3 alkyl group optionally having a halogen atom, or a halogen atom). A C1-C3 alkoxy group, which may have one or more atoms or groups selected from the group consisting of halogen atoms.) A C1-C6 alkyl group having one thiazolyl group (wherein the thiazolyl group) Has one or more atoms or groups selected from the group consisting of a C1-C3 alkyl group optionally having a halogen atom, a C1-C3 alkoxy group optionally having a halogen atom, and a halogen atom. A C1-C6 alkyl group having one pyridyl group (wherein the pyridyl group is a C1-C3 alkyl group optionally having a halogen atom, a halogen atom). A C1-C3 alkoxy group optionally having one or more atoms and one or more atoms or groups selected from the group consisting of halogen atoms), or a C1-C6 having a tetrahydrofuryl group An alkyl group (wherein the tetrahydrofuryl group is selected from the group consisting of a C1-C3 alkyl group optionally having a halogen atom, a C1-C3 alkoxy group optionally having a halogen atom, and a halogen atom); Which may have one or more atoms or groups).
The compound according to [1], wherein R ¹⁰ is a hydrogen atom or a halogen atom.

[11]
A ² is = CH-
R ⁶ is a hydrogen atom,
R ¹ is a C1-C6 alkyl group optionally having one or more atoms or groups selected from the group consisting of halogen atoms and cyclopropyl groups (wherein the cyclopropyl group is
May have one or more halogen atoms or one or more C1-C3 alkyl groups),
A C2-C6 alkenyl group which may have one or more halogen atoms, a C2-C6 alkynyl group which may have one or more halogen atoms, or one or more halogen atoms A good cyclopropyl group,
R ² , R ⁴ and R ⁵ are the same or different and are a halogen atom or a hydrogen atom,
R ³ has a C1-C6 alkyl group that may have one or more halogen atoms, a C2-C6 alkenyl group that may have one or more halogen atoms, and one or more halogen atoms An optionally substituted C2-C6 alkynyl group, a 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is a C1-C3 alkyl group optionally having a halogen atom, a halogen One or more atoms or groups selected from the group consisting of a C1-C3 alkoxy group which may have an atom, and a halogen atom; and -OR ²⁰ (wherein R ²⁰ represents Represents a C1-C6 alkyl group optionally having one or more halogen atoms.), -S (O) _m R ²¹ (wherein R ²¹ may have one or more halogen atoms). Represents a good C1-C6 alkyl group m represents 0, 1 or 2.), a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R ⁷ may be a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ²² (wherein R ²² is a C1-C6 alkyl group optionally having one or more halogen atoms) -S (O) _m R ²³ (wherein R ²³ represents a C1-C6 alkyl group optionally having one or more halogen atoms, and m represents 0, 1 or 2). .), - a SF ₅ or halogen atom,
R ⁸ is a C1-C6 alkyl group having one phenyl group (wherein the phenyl group may be a cyano group, a C1-C3 alkyl group optionally having a halogen atom, or a halogen atom). A C1-C3 alkoxy group, and one or more atoms or groups selected from the group consisting of halogen atoms.
A C1-C6 alkyl group having one 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group may be a C1-C3 alkyl group optionally having a halogen atom, A C1-C3 alkoxy group optionally having a halogen atom, and one or more atoms or groups selected from the group consisting of halogen atoms), or a C1-C6 having a tetrahydrofuryl group An alkyl group (wherein the tetrahydrofuryl group is selected from the group consisting of a C1-C3 alkyl group optionally having a halogen atom, a C1-C3 alkoxy group optionally having a halogen atom, and a halogen atom); One or more atoms or groups may be present).
R ⁹ is a C1-C6 alkyl group which may have one or more halogen atoms, —OR ²⁴ (wherein R ²⁴ is a C1-C6 alkyl group which may have one or more halogen atoms). ), —S (O) _m R ²⁵ (wherein R ²⁵ represents a C1-C6 alkyl group optionally having one or more halogen atoms, and m represents 0, 1 or 2). ), A halogen atom or a hydrogen atom,
The compound according to [1], wherein n is 0, 1 or 2.

[12]
A ² is ═CH—, R ⁶ is a hydrogen atom,
R ¹ is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a cyclopropyl group optionally having one or more halogen atoms, or a C1-C6 alkyl group having a cyclopropyl group (wherein the cyclo The propyl group may have one or more halogen atoms or one or more C1-C3 alkyl groups).
R ² , R ⁴ and R ⁵ are hydrogen atoms,
R ³ has a C1-C6 alkyl group that may have one or more halogen atoms, a C2-C6 alkenyl group that may have one or more halogen atoms, and one or more halogen atoms An optionally substituted C2-C6 alkynyl group, a pyridyl group (wherein the pyridyl group is a halogen atom, a C1-C3 alkyl group which may have a halogen atom, and a C1- which may have a halogen atom) 1 or more atoms or groups selected from the group consisting of C3 alkoxy groups, and a pyrimidinyl group (wherein the pyrimidinyl group may have a halogen atom or a halogen atom) C3 alkyl group, and a halogen atom may have one or more atoms or groups selected from the group consisting of may also be C1-C3 alkoxy group which the have), -. oR ² , ^{(Wherein, R 20} is one or more halogen atoms optionally may C1-C6 alkyl group which may have ^{_{a.) - S (O) m}} R 21 ( ^wherein halogen ^{R 21} is 1 or more An optionally substituted C1-C6 alkyl group, and m is 0, 1 or 2.), a halogen atom or a hydrogen atom,
R ⁷ is a C1-C6 haloalkyl group, —OR ²² (wherein R ²² is a C1-C6 haloalkyl group), —S (O) _m R ²³ (wherein R ²³ is a C1-C6 haloalkyl group) There, m is 0, 1 or 2), -. a SF ₅ or halogen atom,
R ⁸ is a C1-C6 alkyl group having one phenyl group (wherein the phenyl group may have a cyano group, a C1-C3 alkyl group optionally having a halogen atom, or a halogen atom). One or more atoms or groups selected from the group consisting of C1-C3 alkoxy groups and halogen atoms may be present).
A C1-C6 alkyl group having one thiazolyl group (wherein the thiazolyl group is a C1-C3 alkyl group optionally having a halogen atom, a C1-C3 alkoxy group optionally having a halogen atom, And may have one or more atoms or groups selected from the group consisting of halogen atoms).
A C1-C6 alkyl group having one pyridyl group (wherein the pyridyl group is a C1-C3 alkyl group optionally having a halogen atom, a C1-C3 alkoxy group optionally having a halogen atom, And one or more atoms or groups selected from the group consisting of halogen atoms), or a C1-C6 alkyl group having one tetrahydrofuryl group (wherein the tetrahydrofuryl group is a halogen atom) A C1-C3 alkyl group which may have an atom, a C1-C3 alkoxy group which may have a halogen atom, and one or more atoms or groups selected from the group consisting of a halogen atom; Is good.)
The compound according to [1], wherein R ⁹ is a hydrogen atom or a halogen atom.

[13]
A ¹ is ═CH—, R ² , R ⁴ , R ⁵ , and R ⁷ are hydrogen atoms,
A ² is a nitrogen atom or = CR ^10- (wherein R ¹⁰ represents a halogen atom or a hydrogen atom);
R ¹ is an ethyl group, a cyclopropyl group, or a cyclopropylmethyl group;
R ⁸ is benzyl group, 2-methylbenzyl group, 3-methylbenzyl group, 4-methylbenzyl group, 2-chlorobenzyl group, 3-chlorobenzyl group, 4-chlorobenzyl group, 2-cyanobenzyl group, 3- Cyanobenzyl group, 4-cyanobenzyl group, 2-fluorobenzyl group, 3-fluorobenzyl group, 4-fluorobenzyl group, phenyl-ethyl group, (2-chloro-phenyl) -ethyl group, (3-chloro-phenyl) ) -Ethyl group, (4-chloro-phenyl) -ethyl group, (2-methyl-phenyl) -ethyl group, (3-methyl-phenyl) -ethyl group, (4-methyl-phenyl) -ethyl group, ( 2-chloro-thiazol-5-yl) -methyl group, (thiazol-5-yl) -methyl group, (2-bromo-thiazol-5-yl) -methyl group, (2-methyl) Ru-thiazol-5-yl) -methyl group, (2-trifluoromethyl-thiazol-5-yl) -methyl group, (2-chloro-thiazol-5-yl) -ethyl group, (thiazol-5-yl) ) -Ethyl group, (2-chloro-pyridin-5-yl) -methyl group, (pyridin-3-yl) -methyl group, (pyridin-2-yl) -methyl group, (pyridin-4-yl)- Methyl group, (6-fluoro-pyridin-3-yl) -methyl group, (6-bromo-pyridin-3-yl) -methyl group, (6-trifluoromethyl-pyridin-3-yl) -methyl group, (6-methyl-pyridin-3-yl) -methyl group, (6-chloro-5-fluoro-pyridin-3-yl) -methyl group, (5,6-dichloro-pyridin-3-yl) -methyl group , (Pyridin-3-yl) -e Group, (6-chloro-pyridin-3-yl) -ethyl group, (pyrimidin-5-yl) -methyl group, (2-chloro-pyrimidin-5-yl) -methyl group, (2-methyl-pyrimidine) -5-yl) -methyl group, (5-chloro-pyrazin-2-yl) -methyl group, (tetrahydro-furan-3-yl) -methyl group, or (tetrahydro-furan-3-yl) -ethyl group And
R ³ is a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ²⁰ (wherein R ²⁰ is a C1-C6 alkyl optionally having one or more halogen atoms) -S (O) _m R ²¹ (wherein R ²¹ represents a C1-C6 alkyl group optionally having one or more halogen atoms, and m represents 0, 1, or 2). Represents a halogen atom or a hydrogen atom,
R ⁶ is a C1-C6 haloalkyl group, —OR ²² (wherein R ²² represents a C1-C6 haloalkyl group), —S (O) _m R ²³ (wherein R ²³ is a C1-C6 haloalkyl group). the stands, m represents 0, 1 or 2), -. a SF ₅ or halogen atom,
The compound according to [1], wherein n is 0, 1 or 2.

[14]
A ² is ═CH—, R ² , R ⁴ , R ⁵ , and R ⁶ are hydrogen atoms,
A ¹ is nitrogen atom or = CR ⁹ - (wherein, ^{R 9} represents a hydrogen atom or a halogen atom.), And
R ¹ is an ethyl group, a cyclopropyl group, or a cyclopropylmethyl group;
R ⁸ is benzyl group, 2-methylbenzyl group, 3-methylbenzyl group, 4-methylbenzyl group, 2-chlorobenzyl group, 3-chlorobenzyl group, 4-chlorobenzyl group, 2-cyanobenzyl group, 3- Cyanobenzyl group, 4-cyanobenzyl group, 2-fluorobenzyl group, 3-fluorobenzyl group, 4-fluorobenzyl group, phenyl-ethyl group, (2-chloro-phenyl) -ethyl group, (3-chloro-phenyl) ) -Ethyl group, (4-chloro-phenyl) -ethyl group, (2-methyl-phenyl) -ethyl group, (3-methyl-phenyl) -ethyl group, (4-methyl-phenyl) -ethyl group, ( 2-chloro-thiazol-5-yl) -methyl group, (thiazol-5-yl) -methyl group, (2-bromo-thiazol-5-yl) -methyl group, (2-methyl) Ru-thiazol-5-yl) -methyl group, (2-trifluoromethyl-thiazol-5-yl) -methyl group, (2-chloro-thiazol-5-yl) -ethyl group, (thiazol-5-yl) ) -Ethyl group, (2-chloro-pyridin-5-yl) -methyl group, (pyridin-3-yl) -methyl group, (pyridin-2-yl) -methyl group, (pyridin-4-yl)- Methyl group, (6-fluoro-pyridin-3-yl) -methyl group, (6-bromo-pyridin-3-yl) -methyl group, (6-trifluoromethyl-pyridin-3-yl) -methyl group, (6-methyl-pyridin-3-yl) -methyl group, (6-chloro-5-fluoro-pyridin-3-yl) -methyl group, (5,6-dichloro-pyridin-3-yl) -methyl group , (Pyridin-3-yl) -e Group, (6-chloro-pyridin-3-yl) -ethyl group, (pyrimidin-5-yl) -methyl group, (2-chloro-pyrimidin-5-yl) -methyl group, (2-methyl-pyrimidine) -5-yl) -methyl group, (5-chloro-pyrazin-2-yl) -methyl group, (tetrahydro-furan-3-yl) -methyl group, or (tetrahydro-furan-3-yl) -ethyl group And
R ³ is a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ²⁰ (wherein R ²⁰ is a C1-C6 alkyl optionally having one or more halogen atoms) -S (O) _m R ²¹ (wherein R ²¹ represents a C1-C6 alkyl group optionally having one or more halogen atoms, and m represents 0, 1, or 2). And R ⁷ is a C1-C6 haloalkyl group, —OR ²² (wherein R ²² represents a C1-C6 haloalkyl group), —S (O) _m R ^23. (Wherein R ²³ represents a C1-C6 haloalkyl group, m represents 0, 1 or 2), —SF ₅ or a halogen atom;
The compound according to [1], wherein n is 0, 1 or 2.
[15]
[1]-[14] A pest control composition comprising the compound according to any one of [1] to [14] and an inert carrier.
[16]
[1] to [14] A method for controlling pests, wherein an effective amount of the compound according to any one of [1] to [14] is applied to pests or habitats of pests.

  Since the compound of the present invention has excellent control activity against pests, it is useful as an active ingredient of pest control agents.

  Examples of groups used in the description of the present specification will be described below.

  In the compound of the present invention, N-oxide is a compound in which a nitrogen atom constituting a ring on a heterocyclic group is oxidized. Examples of the heterocyclic group that can form an N-oxide include a pyridine ring.

The notation of the Ca—Cb chain hydrocarbon group in the present specification represents a linear or branched saturated or unsaturated hydrocarbon group having a to b carbon atoms.
Examples of the “C1-C6 chain hydrocarbon group” include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, neopentyl group, hexyl. A C1-C6 alkyl group such as a group;
Vinyl group, 1-propenyl group, 2-propenyl group, 1-methylvinyl group, 2-methyl-1-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 1- A C2-C6 alkenyl group such as a hexenyl group;
Examples thereof include C2-C6 alkynyl groups such as ethynyl group, propargyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group, 1-hexynyl group and the like.

The notation of the Ca—Cb alkyl group represents a linear or branched hydrocarbon group having a to b carbon atoms.
Examples of the “C1-C6 alkyl group” include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a neopentyl group, and a hexyl group. C1-C6 alkyl group etc. are mentioned.

The notation of a Ca-Cb alkenyl group is a linear or branched chain having a carbon number of a to b and an unsaturated hydrocarbon group having one or more double bonds in the molecule. Represent.
Examples of the “C2-C6 alkenyl group” include vinyl group, 1-propenyl group, 2-propenyl group, 1-methylvinyl group, 2-methyl-1-propenyl group, 1-butenyl group, 2-butenyl group, 3- C2-C6 alkenyl groups such as butenyl, 1-pentenyl and 1-hexenyl

The notation of the Ca-Cb alkynyl group represents an unsaturated hydrocarbon group having a linear or branched chain having a to b carbon atoms and having one or more triple bonds in the molecule. .
Examples of the “C2-C6 alkynyl group” include ethynyl group, propargyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group, 1-hexynyl group and the like.

The notation of a Ca—Cb alkoxy group represents a linear or branched alkyl-O— group having a to b carbon atoms.
Examples of the “C1-C6 alkoxy group” include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butyloxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, a pentyloxy group, and a neopentyloxy group. And a hexyloxy group.

The notation of a Ca-Cb alkenyloxy group is a linear or branched chain having a carbon number of a to b, and an alkenyl-O- group having one or more double bonds in the molecule. Represents.
Examples of the “C2-C6 alkenyloxy group” include a vinyloxy group, 1-propenyloxy group, 2-propenyloxy group, 1-methylvinyloxy group, 2-methyl-1-propenyloxy group, 1-butenyloxy group, 2 -Butenyloxy group, 3-butenyloxy group, 1-pentenyloxy group, 1-hexenyloxy group and the like can be mentioned.

The notation of a Ca-Cb alkynyloxy group is an alkynyl-O- group which is linear or branched having 1 to 2 carbon atoms and has one or more triple bonds in the molecule. Represent.
Examples of the “C2-C6 alkynyloxy group” include ethynyloxy group, propargyloxy group, 2-butynyloxy group, 3-butynyloxy group, 1-pentynyloxy group, 1-hexynyloxy group and the like.

The notation of the Ca—Cb alkylsulfanyl group represents a linear or branched alkyl-S— group having a to b carbon atoms.
Examples of the “C1-C6 alkylsulfanyl group” include a methylsulfanyl group, an ethylsulfanyl group, a propylsulfanyl group, an isopropylsulfanyl group, a butylsulfanyl group, a pentylsulfanyl group, and a hexylsulfanyl group.

The notation of the Ca—Cb alkylsulfinyl group represents a linear or branched alkyl-S (O) — group having a to b carbon atoms.
Examples of the “C1-C6 alkylsulfinyl group” include a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, an isopropylsulfinyl group, a butylsulfinyl group, a pentylsulfinyl group, and a hexylsulfinyl group.

The notation of a Ca—Cb alkylsulfonyl group represents a linear or branched alkyl-S (O) ₂ — group having a to b carbon atoms.
Examples of the “C1-C6 alkylsulfonyl group” include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, an isopropylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, and a hexylsulfonyl group.

The notation of the Ca—Cb alkylcarbonyl group represents a linear or branched alkyl-C (O) — group having a to b carbon atoms.
Examples of the “C2-C6 alkylcarbonyl group” include acetyl group, propionyl group, butyryl group, pentanoyl group, hexanoyl group and the like.

The notation of the Ca—Cb alkoxycarbonyl group represents a linear or branched alkyl-O—C (O) — group having a to b carbon atoms.
Examples of the “C2-C6 alkoxycarbonyl group” include methoxycarbonyl group, ethoxycarbonyl group, propyloxycarbonyl group, butyloxycarbonyl group, pentyloxycarbonyl group, tert-butyloxycarbonyl group and the like.

The notation of the Ca—Cb alicyclic hydrocarbon group represents a cyclic non-aromatic hydrocarbon group having a to b carbon atoms.
Examples of the “C3-C6 alicyclic hydrocarbon group” include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-cyclohexenyl group, a 2-cyclohexenyl group, and a 3-cyclohexenyl group.

The notation of Ca—Cb cycloalkyl group represents a cyclic alkyl group having a to b carbon atoms.
Examples of the “C3-C6 cycloalkyl group” include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.

The notation of a Ca—Cb alkylamino group represents a linear or branched alkyl-NH— group having a to b carbon atoms.
Examples of the “C1-C6 alkylamino group” include a methylamino group, an ethylamino group, a propylamino group, an isopropylamino group, and a butylamino group.

The notation of the Ca-Cb dialkylamino group may be the same or different from each other in the number of carbon atoms of the alkyl group. Represents a group.
Examples of the “C2-C8 dialkylamino group” include a dimethylamino group, a diethylamino group, and a dipropylamino group.

The notation of the Ca-Cb alkoxyalkyl group may be the same or different from each other in the number of carbon atoms of the alkyl group, and a linear or branched alkyl group in which the total number of carbon atoms is a to b. Represents an O-alkyl group.
Examples of the “C1-C6 alkoxyalkyl group” include a methoxymethyl group, an ethoxymethyl group, a 1- (methoxy) ethyl group, a 2- (methoxy) ethyl group, a 1- (ethoxy) ethyl group, and 2- (ethoxy) ethyl. Groups and the like.

In the present specification, the expression “which may have one or more atoms or groups selected from group X” means that when it has two or more atoms or groups selected from group X, those The atoms or groups selected from group X may be the same as or different from each other.
In the present specification, the expression “which may have one or more atoms or groups selected from group Y” means that when it has two or more atoms or groups selected from group Y, those The atoms or groups selected from group Y may be the same as or different from each other.
In the present specification, the expression “which may have one or more atoms or groups selected from group Z” means that when it has two or more atoms or groups selected from group Z, those The atoms or groups selected from group Z may be the same as or different from each other.
In the present specification, the expression “may have one or more halogen atoms” means that when two or more halogen atoms are present, the halogen atoms may be the same as or different from each other. May be. The “one or more” is, for example, 1, 2, or 3.

  In the compound of the present invention, “halogen atom” means a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

In the compound of the present invention, the expression “C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from group X” is selected from group X in which a hydrogen atom bonded to a carbon atom is selected. Represents a linear or branched hydrocarbon group having 1 to 6 carbon atoms, optionally substituted by an atom or group, wherein two or more atoms or groups selected from group X are If present, the atoms or groups selected from the group X may be the same as or different from each other.
Examples of the “C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from group X” include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, and an isobutyl group. , Sec-butyl group, tert-butyl group, pentyl group, neopentyl group, hexyl group, methoxymethyl group, ethoxymethyl group, propyloxymethyl group, isopropyloxymethyl group, butyloxymethyl group, sec-butyloxymethyl group Tert-butyloxymethyl group, 2-methoxyethyl group, 2-ethoxyethyl group, 2-propyloxyethyl group, 2-isopropyloxyethyl group, 2-butyloxyethyl group, 2-sec-butyloxyethyl group, 2-tert-butyloxyethyl group, trifluoromethyl group, trichloromethyl group, 2 Fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group and pentafluoroethyl group, methylsulfanylethyl group, ethylsulfanylethyl group, methylsulfinylethyl group, methylsulfonylethyl group, 2- C1-C6 which may have one or more atoms or groups selected from group X such as hydroxyethyl group, cyclopropylmethyl group, 1-methylcyclopropylmethyl group, 2,2-difluorocyclopropylmethyl group An alkyl group;
Vinyl group, 1-propenyl group, 2-propenyl group, 1-methylvinyl group, 2-methyl-1-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 1- A C2-C6 alkenyl group optionally having one or more atoms or groups selected from group X such as hexenyl group, 1,1-difluoroallyl group, pentafluoroallyl group;
One or more selected from group X such as ethynyl group, propargyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group, 1-hexynyl group and 4,4,4-trifluoro-2-butynyl group C2-C6 alkynyl groups which may have an atom or group are mentioned and are selected in the range of each designated number of carbon atoms.

In the compound of the present invention, the notation of “C3-C6 alicyclic hydrocarbon group optionally having one or more atoms or groups selected from group Y” indicates that the hydrogen atom bonded to the carbon atom is selected from group Y Represents a cyclic non-aromatic hydrocarbon group having 3 to 6 carbon atoms, optionally substituted by any atom or group having at least two atoms or groups selected from group Y The atoms or groups selected from group Y may be the same as or different from each other.
Examples of the “C3-C6 alicyclic hydrocarbon group optionally having one or more atoms or groups selected from group Y” include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and 1-cyclohexenyl. Group, 2-cyclohexenyl group, 3-cyclohexenyl group, 1-methylcyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2-methoxycyclohexyl group, 3-methoxycyclohexyl group, Examples include 4-methoxycyclohexyl group, 1-fluorocyclohexyl group, 2-fluorocyclohexyl group, 3-fluorocyclohexyl group, and 4-fluorocyclohexyl group.

In the compound of the present invention, the expression “C1-C6 chain hydrocarbon group optionally having one or more halogen atoms” is a carbon atom in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. A linear or branched hydrocarbon group having a number of 1 to 6 and when having two or more halogen atoms, these halogen atoms may be the same or mutually in phase. May be different.
Examples of the “C1-C6 chain hydrocarbon group optionally having one or more halogen atoms” include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, tert-butyl, pentyl, neopentyl, hexyl, trifluoromethyl, trichloromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl and pentafluoro A C1-C6 alkyl group optionally having one or more halogen atoms such as an ethyl group and a heptafluoroisopropyl group;
Vinyl group, 1-propenyl group, 2-propenyl group, 1-methylvinyl group, 2-methyl-1-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 1- A C2-C6 alkenyl group optionally having one or more halogen atoms such as a hexenyl group, a 1,1-difluoroallyl group, a pentafluoroallyl group;
Having one or more halogen atoms such as ethynyl group, propargyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group, 1-hexynyl group and 4,4,4-trifluoro-2-butynyl group C2-C6 alkynyl groups that may be present are selected, each selected within the range of the number of carbon atoms specified.

In the compound of the present invention, the expression “phenyl group optionally having one or more atoms or groups selected from group Z” is arbitrarily selected depending on the atom or group selected from group Z in which a hydrogen atom bonded to a carbon atom is selected. Represents a substituted phenyl group, and in this case, when having two or more atoms or groups selected from group Z, the atoms or groups selected from group Z are the same or different from each other; May be.
Examples of the “phenyl group optionally having one or more atoms or groups selected from group Z” include a phenyl group, a 2-cyanophenyl group, a 3-cyanophenyl group, a 4-cyanophenyl group, 2 -Methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2,3-difluorophenyl group, 2,4-difluorophenyl group 2,5-difluorophenyl group, 2,6-difluorophenyl group, 3,4-difluorophenyl group, 3,5-difluorophenyl group, 2,3,4,5,6-pentafluorophenyl group, 2- Chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group, 2 Iodophenyl group, 3-iodophenyl group, 4-iodophenyl group, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 2-trifluoromethoxyphenyl group, 3- Trifluoromethoxyphenyl group, 4-trifluoromethoxyphenyl group, 2-trifluoromethylsulfanylphenyl group, 3-trifluoromethylsulfanylphenyl group, 4-trifluoromethylsulfanylphenyl group, 4-methoxycarbonylphenyl group, 4- Nitrophenyl group, 4-cyanophenyl group, 4-methylaminophenyl group, 4-dimethylaminophenyl group, 4-methylsulfinylphenyl group, 4-methylsulfonylphenyl group, 4-acetylphenyl group and 4-methoxycarbonylphenyl Le group.

In the compound of the present invention, the “heterocyclic group” means a heterocyclic compound residue containing one or more heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom in addition to the carbon atom in the ring structure. Represents.
In the compounds of the present invention, the 5-membered heterocyclic group means a 5-membered aromatic heterocyclic group or a 5-membered non-aromatic heterocyclic group, and the 6-membered heterocyclic group means a 6-membered aromatic heterocyclic group. Or a 6-membered non-aromatic heterocyclic group is meant.

In the compound of the present invention, the “heterocyclic group” in the “5- or 6-membered heterocyclic group optionally having one or more atoms or groups selected from group Z” means a nitrogen atom in addition to the carbon atom in the ring structure. Represents a heterocyclic compound residue containing one or more heteroatoms selected from the group consisting of an atom, an oxygen atom and a sulfur atom, and has at least two atoms or groups selected from group Z The atoms or groups selected from the group Z may be the same as or different from each other.
In the compounds of the present invention, the 5- or 6-membered heterocyclic group means a 5- or 6-membered aromatic heterocyclic group or a 5- or 6-membered non-aromatic heterocyclic group.
Examples of the “5- or 6-membered heterocyclic group optionally having one or more atoms or groups selected from group Z” include pyrrolidin-1-yl group, 3,3,4,4-tetrafluoropyrrolidine One or more atoms selected from the group Z such as a -1-yl group, a tetrahydrofuryl group (eg, tetrahydrofuran-2-yl group, tetrahydrofuran-3-yl group), a piperidyl group, a morpholinyl group, and a thiomorpholinyl group Or a 5- or 6-membered non-aromatic heterocyclic group which may have a group;
2-pyrrolyl group, 2-furyl group, 3-furyl group, 5-pyrazolyl group, 4-pyrazolyl group, 1-pyrrolyl group, 1-methyl-2-pyrrolyl group, 2-methylsulfanyl-1-pyrrolyl group, 2 -Methylsulfinyl-1-pyrrolyl group, 2-methylsulfonyl-1-pyrrolyl group, 2-methylamino-1-pyrrolyl group, 2-dimethylamino-1-pyrrolyl group, 5-bromo-2-furyl group, 5- Nitro-2-furyl group, 5-cyano-2-furyl group, 5-methoxy-2-furyl group, 5-acetyl-2-furyl group, 5-methoxycarbonyl-2-furyl group, 2-methyl-3- Furyl group, 2,5-dimethyl-3-furyl group, 2,4-dimethyl-3-furyl group, 5-methyl-2-thienyl group, 3-methyl-2-thienyl group, 1-methyl-3-tri Fluoromethyl -Pyrazolyl group, 5-chloro-1,3-dimethyl-4-pyrazolyl group, pyrazol-1-yl group, 3-chloro-pyrazol-1-yl group, 3-bromopyrazol-1-yl group, 4-chloro Pyrazol-1-yl group, 4-bromopyrazol-1-yl group, imidazol-1-yl group, 1,2,4-triazol-1-yl group, 3-chloro-1,2,4-triazole-1 -Yl group, 1,2,3,4-tetrazol-1-yl group, 1,2,3,5-tetrazol-1-yl group, 2-thienyl group, 3-thienyl group, 3-trifluoromethyl- 1,2,4-triazol-1-yl group, 4-trifluoromethylpyrazol-1-yl group, pyrazinyl group, 5-chloro-pyrazin-2-yl group, 2-pyrimidinyl group, 4-pyrimidinyl group, 5 -Pirimiji Group, 2-chloro-pyrimidin-5-yl group, 2-methyl-pyrimidin-5-yl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 6-methyl-pyridin-3-yl group 2-chloro-pyridin-5-yl group, 3-chloro-pyridin-2-yl group, 4-chloro-pyridin-2-yl group, 5-chloro-pyridin-2-yl group, 6-chloro-pyridine 2-yl group, 6-chloro-pyridin-3-yl group, 6-bromo-pyridin-3-yl group, 2-fluoro-pyridin-5-yl group, 3-fluoro-pyridin-2-yl group, 4-fluoro-pyridin-2-yl group, 5-fluoro-pyridin-2-yl group, 6-fluoro-pyridin-2-yl group, 6-fluoro-pyridin-3-yl group, 5,6-dichloro- Pyridin-3-yl group, 6-chloro- 5-fluoro-pyridin-3-yl group, 3-chloro-5-trifluoromethyl-pyridin-2-yl group, 5-trifluoromethyl-pyridin-2-yl group, 6-trifluoromethyl-pyridine-3 -Yl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-chloro-5-thiazolyl, 2-bromo-5-thiazolyl, 2-methyl-5-thiazolyl, and 2-tri Examples thereof include a 5- or 6-membered aromatic heterocyclic group which may have one or more atoms or groups selected from the group Z such as a fluoromethyl-5-thiazolyl group.

  Examples of the “C1-C6 alkoxy group optionally having one or more halogen atoms” in the compound of the present invention include a methoxy group, a trifluoromethoxy group, an ethoxy group, a 2,2,2-trifluoroethoxy group, Examples include propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, sec-butyloxy group, tert-butyloxy group, pentyloxy group and hexyloxy group.

  Examples of the “C2-C6 alkenyloxy group optionally having one or more halogen atoms” in the compound of the present invention include a 2-propenyloxy group, a 2-methyl-2-propenyloxy group, a 2-butenyloxy group, Examples include 3-butenyloxy group, 2-pentenyloxy group, 2-hexenyloxy group, 3,3-difluoroallyloxy group, and 3,3-dichloroallyloxy group.

  Examples of the “C2-C6 alkynyloxy group optionally having one or more halogen atoms” in the compound of the present invention include a propargyloxy group, 2-butynyloxy group, 3-butynyloxy group, 2-pentynyloxy group, Examples include 2-hexynyloxy group and 4,4,4-trifluoro-2-butynyloxy group.

  Examples of the “C1-C6 alkylsulfanyl group optionally having one or more halogen atoms” in the compound of the present invention include a methylsulfanyl group, an ethylsulfanyl group, a propylsulfanyl group, an isopropylsulfanyl group, a butylsulfanyl group, and pentyl. Examples thereof include a sulfanyl group, a hexylsulfanyl group, a trifluoromethylsulfanyl group, a 2,2,2-trifluoroethylsulfanyl group, and a pentafluoroethylsulfanyl group.

  Examples of the “C1-C6 alkylsulfinyl group optionally having one or more halogen atoms” in the compound of the present invention include a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, an isopropylsulfinyl group, a butylsulfinyl group, and pentyl. Examples thereof include a sulfinyl group, a hexylsulfinyl group, a trifluoromethylsulfinyl group, a 2,2,2-trifluoroethylsulfinyl group, and a pentafluoroethylsulfinyl group.

  Examples of the “C1-C6 alkylsulfonyl group optionally having one or more halogen atoms” in the compound of the present invention include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, an isopropylsulfonyl group, a butylsulfonyl group, and pentyl. Examples include a sulfonyl group, a hexylsulfonyl group, a trifluoromethylsulfonyl group, a 2,2,2-trifluoroethylsulfonyl group, and a pentafluoroethylsulfonyl group.

  Examples of the “C2-C6 alkylcarbonyl group optionally having one or more halogen atoms” in the compound of the present invention include acetyl group, propionyl group, butyryl group, pentanoyl group, hexanoyl group and trifluoroacetyl group. It is done.

  Examples of the “C2-C6 alkoxycarbonyl group optionally having one or more halogen atoms” in the compound of the present invention include a methoxycarbonyl group, an ethoxycarbonyl group, a propyloxycarbonyl group, a butyloxycarbonyl group, and a pentyloxycarbonyl. Group, tert-butyloxycarbonyl group and 2,2,2-trifluoroethyloxycarbonyl group.

  Examples of the “C3-C6 cycloalkyl group optionally having one or more halogen atoms” in the compound of the present invention include a cyclopropyl group, a 2,2-difluorocyclopropyl group, and a 2,2-dichlorocyclopropyl group. 2,2-dibromocyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group.

  Examples of the “C1-C6 alkylamino group optionally having one or more halogen atoms” in the compound of the present invention include a methylamino group, an ethylamino group, a 2,2,2-trifluoroethylamino group, propyl An amino group, isopropylamino group, and butylamino group are mentioned.

  Examples of the “C2-C8 dialkylamino group optionally having one or more halogen atoms” in the compound of the present invention include a dimethylamino group, a diethylamino group, and a bis (2,2,2-trifluoroethyl) amino group. And a dipropylamino group.

  Examples of the “C2-C6 alkoxyalkyl group optionally having one or more halogen atoms” in the compound of the present invention include a methoxymethyl group, an ethoxymethyl group, a 1- (methoxy) ethyl group, and 2- (methoxy). An ethyl group, 1- (ethoxy) ethyl group, 2- (ethoxy) ethyl group, etc. are mentioned.

  In the compound of the present invention, “5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, and a halogen atom” And may have one or more atoms or groups selected from the group consisting of C1-C3 alkoxy groups that may have a substituent. -Furyl group, 5-pyrazolyl group, 4-pyrazolyl group, 1-pyrrolyl group, 1-methyl-2-pyrrolyl group, 5-bromo-2-furyl group, 5-methoxy-2-furyl group, 2-methyl- 3-furyl group, 2,5-dimethyl-3-furyl group, 2,4-dimethyl-3-furyl group, 5-methyl-2-thienyl group, 3-methyl-2-thienyl group, 1-methyl-3 -Trifluoromethyl-5-pi Zolyl group, 5-chloro-1,3-dimethyl-4-pyrazolyl group, pyrazol-1-yl group, 3-chloro-pyrazol-1-yl group, 3-bromopyrazol-1-yl group, 4-chloropyrazole -1-yl group, 4-bromopyrazol-1-yl group, imidazol-1-yl group, 1,2,4-triazol-1-yl group, 3-chloro-1,2,4-triazole-1- Yl group, 1,2,3,4-tetrazol-1-yl group, 1,2,3,5-tetrazol-1-yl group, 2-thienyl group, 3-thienyl group, 3-trifluoromethyl-1 2,4-triazol-1-yl group, 4-trifluoromethylpyrazol-1-yl group, pyrazinyl group, 4-pyrimidinyl group, 5-pyrimidinyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group Group, 3- Fluoro-2-pyridyl group, 4-fluoro-2-pyridyl group, 5-fluoro-2-pyridyl group, 6-fluoro-2-pyridyl group, 2-pyrimidinyl group, 3-chloro-5-trifluoromethylpyridine- Examples include 2-yl group and 5-trifluoromethylpyridin-2-yl group.

In the compound of the present invention, “C1-C6 haloalkyl group” is represented by a linear or branched chain having 1 to 6 carbon atoms in which one or more hydrogen atoms bonded to carbon atoms are substituted with halogen atoms. In this case, when it has two or more halogen atoms, these halogen atoms may be the same as or different from each other.
Examples of the “C1-C6 haloalkyl group” include a fluoromethyl group, a chloromethyl group, a bromomethyl group, an iodomethyl group, a difluoromethyl group, a dichloromethyl group, a trifluoromethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, and trichloromethyl. Group, 2-fluoroethyl group, 2-chloroethyl group, 2-bromoethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, pentafluoroethyl group, heptafluoropropyl group and heptafluoroisopropyl Groups and the like.

  Examples of the “C1-C6 perfluoroalkyl group” in the compound of the present invention include a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, and a heptafluoroisopropyl group.

As this invention compound, the following compounds are mentioned, for example.
Formula (1-1-1)
[Where:
A ^2a represents a nitrogen atom or = CR ^10a- ,
R ^1a is a C1-C6 alkyl group optionally having one or more atoms or groups selected from the group consisting of halogen atoms and cyclopropyl groups (wherein the cyclopropyl group is one or more halogen atoms) Or may have one or more C1-C3 alkyl groups), may have one or more halogen atoms, may have C2-C6 alkenyl groups, or may have one or more halogen atoms. Represents a good C2-C6 alkynyl group, or a cyclopropyl group optionally having one or more halogen atoms,
R ^2a , R ^4a and R ^5a are the same or different and represent a halogen atom or a hydrogen atom,
R ^3a has a C1-C6 alkyl group which may have one or more halogen atoms, a C2-C6 alkenyl group which may have one or more halogen atoms, and one or more halogen atoms. An optionally substituted C2-C6 alkynyl group, a 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is a halogen atom, a C1-C3 alkyl optionally having a halogen atom) Group, and optionally one or more atoms or groups selected from the group consisting of C1-C3 alkoxy groups optionally having halogen atoms, and -OR ^20a (where R ^20a is Represents a C1-C6 alkyl group optionally having one or more halogen atoms.), —S (O) _m R ^21a (wherein R ^21a may have one or more halogen atoms). Good C1-C6 alk It represents a group, m represents 0, 1 or 2.), A cyano group, a nitro group, a halogen atom or a hydrogen atom,
R ^6a is a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ^22a (wherein R ^22a is a C1-C6 alkyl group optionally having one or more halogen atoms) ), —S (O) _m R ^23a (wherein R ^23a represents a C1-C6 alkyl group optionally having one or more halogen atoms, and m represents 0, 1 or 2). .), - SF _5, or a halogen atom,
R ^8a is a C1-C6 alkyl group having one phenyl group (wherein the phenyl group has a cyano group, a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, and a halogen atom). And optionally having one or more atoms or groups selected from the group consisting of C1-C3 alkoxy groups.) C1-C6 having one 5- or 6-membered aromatic heterocyclic group An alkyl group (wherein the 5- or 6-membered aromatic heterocyclic group is a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, and a C1-C3 alkoxy optionally having a halogen atom); Which may have one or more atoms or groups selected from the group consisting of groups), or a C1-C6 alkyl group having one tetrahydrofuryl group (wherein the tetrahydrofuryl The group is one or more atoms or groups selected from the group consisting of a C1-C3 alkyl group which may have a halogen atom, a C1-C3 alkoxy group which may have a halogen atom, and a halogen atom. Which may have)
R ^10a is a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ^24a (wherein R ^24a is a C1-C6 alkyl group optionally having one or more halogen atoms) -S (O) _m R ^25a (wherein R ^25a represents a C1-C6 alkyl group optionally having one or more halogen atoms, and m represents 0, 1 or 2). ), Represents a halogen atom or a hydrogen atom,
n represents 0, 1 or 2. Or a N-oxide thereof.

Formula (1-1-2)
[Where:
A ^2a represents a nitrogen atom or = CR ^10a- ,
R ^1a is a C1-C6 alkyl group optionally having one or more atoms or groups selected from the group consisting of halogen atoms and cyclopropyl groups (wherein the cyclopropyl group is one or more halogen atoms) Or may have one or more C1-C3 alkyl groups), may have one or more halogen atoms, may have C2-C6 alkenyl groups, or may have one or more halogen atoms. Represents a good C2-C6 alkynyl group, or a cyclopropyl group optionally having one or more halogen atoms,
R ^2a , R ^4a and R ^5a are the same or different and represent a halogen atom or a hydrogen atom,
R ^3a has a C1-C6 alkyl group which may have one or more halogen atoms, a C2-C6 alkenyl group which may have one or more halogen atoms, and one or more halogen atoms. An optionally substituted C2-C6 alkynyl group, a 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is a halogen atom, a C1-C3 alkyl optionally having a halogen atom) Group, and optionally one or more atoms or groups selected from the group consisting of C1-C3 alkoxy groups optionally having halogen atoms, and -OR ^20a (where R ^20a is Represents a C1-C6 alkyl group optionally having one or more halogen atoms.), —S (O) _m R ^21a (wherein R ^21a may have one or more halogen atoms). Good C1-C6 alk It represents a group, m represents 0, 1 or 2.), A cyano group, a nitro group, a halogen atom or a hydrogen atom,
R ^7a is a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ^22a (wherein R ^22a is a C1-C6 alkyl group optionally having one or more halogen atoms) ), —S (O) _m R ^23a (wherein R ^23a represents a C1-C6 alkyl group optionally having one or more halogen atoms, and m represents 0, 1 or 2). .), - SF _5, or a halogen atom,
R ^8a is a C1-C6 alkyl group having one phenyl group (wherein the phenyl group has a cyano group, a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, and a halogen atom). And optionally having one or more atoms or groups selected from the group consisting of C1-C3 alkoxy groups) or C1-C6 having one 5- or 6-membered aromatic heterocyclic group. An alkyl group (wherein the 5- or 6-membered aromatic heterocyclic group is a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, and a C1-C3 alkoxy optionally having a halogen atom); Which may have one or more atoms or groups selected from the group consisting of groups), or a C1-C6 alkyl group having one tetrahydrofuryl group (wherein the tetrahydrofuryl group). The group is one or more atoms or groups selected from the group consisting of a C1-C3 alkyl group optionally having a halogen atom, a C1-C3 alkoxy group optionally having a halogen atom, and a halogen atom. Which may have
R ^10a is a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ^24a (wherein R ^24a is a C1-C6 alkyl group optionally having one or more halogen atoms) -S (O) _m R ^25a (wherein R ^25a represents a C1-C6 alkyl group optionally having one or more halogen atoms, and m represents 0, 1 or 2). ), Represents a halogen atom or a hydrogen atom,
n represents 0, 1 or 2. Or a N-oxide thereof.

Formula (1-2-1)
[Where:
A ^1b represents a nitrogen atom or = CR ^9b- ,
R ^1b is a C1-C6 alkyl group optionally having one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclopropyl group is
May have one or more halogen atoms or one or more C1-C3 alkyl groups),
A C2-C6 alkenyl group which may have one or more halogen atoms, a C2-C6 alkynyl group which may have one or more halogen atoms, or one or more halogen atoms Represents a good cyclopropyl group,
R ^2b , R ^4b and R ^5b are the same or different and represent a halogen atom or a hydrogen atom,
R ^3b has a C1-C6 alkyl group which may have one or more halogen atoms, a C2-C6 alkenyl group which may have one or more halogen atoms, and one or more halogen atoms. An optionally substituted C2-C6 alkynyl group, a 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is a halogen atom, a C1-C3 alkyl optionally having a halogen atom) Group, and optionally having one or more atoms or groups selected from the group consisting of C1-C3 alkoxy groups optionally having halogen atoms), -OR ^20b (where R ^20b is Represents a C1-C6 alkyl group optionally having one or more halogen atoms.), —S (O) _m R ^21b (wherein R ^21b may have one or more halogen atoms). Good C1-C6 alk It represents a group, m represents 0, 1 or 2.), A cyano group, a nitro group, a halogen atom or a hydrogen atom,
R ^6b is a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ^22b (wherein R ^22b is a C1-C6 alkyl group optionally having one or more halogen atoms) ), —S (O) _m R ^23b (wherein R ^23b represents a C1-C6 alkyl group optionally having one or more halogen atoms, and m represents 0, 1 or 2). .), - SF _5, or a halogen atom,
R ^8b is a C1-C6 alkyl group having one phenyl group (wherein the phenyl group has a cyano group, a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, and a halogen atom). And optionally having one or more atoms or groups selected from the group consisting of C1-C3 alkoxy groups.) C1-C6 having one 5- or 6-membered aromatic heterocyclic group An alkyl group (wherein the 5- or 6-membered aromatic heterocyclic group is a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, and a C1-C3 alkoxy optionally having a halogen atom); Which may have one or more atoms or groups selected from the group consisting of groups), or a C1-C6 alkyl group having one tetrahydrofuryl group (wherein the tetrahydrofuryl The group is one or more atoms or groups selected from the group consisting of a C1-C3 alkyl group which may have a halogen atom, a C1-C3 alkoxy group which may have a halogen atom, and a halogen atom. Which may have)
R ^9b is a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ^24b (wherein R ^24b is a C1-C6 alkyl group optionally having one or more halogen atoms) ), -S (O) _m R ^25b (where R ^25b represents a C1-C6 alkyl group optionally having one or more halogen atoms, and m represents 0, 1 or 2). ), Represents a halogen atom or a hydrogen atom,
n represents 0, 1 or 2. Or a N-oxide thereof.

Formula (1-2-2)
[Where:
A ^1b represents a nitrogen atom or = CR ^9b- ,
R ^1b is a C1-C6 alkyl group optionally having one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclopropyl group is
May have one or more halogen atoms or one or more C1-C3 alkyl groups),
A C2-C6 alkenyl group which may have one or more halogen atoms, a C2-C6 alkynyl group which may have one or more halogen atoms, or one or more halogen atoms Represents a good cyclopropyl group,
R ^2b , R ^4b and R ^5b are the same or different and represent a halogen atom or a hydrogen atom,
R ^3b has a C1-C6 alkyl group which may have one or more halogen atoms, a C2-C6 alkenyl group which may have one or more halogen atoms, and one or more halogen atoms. An optionally substituted C2-C6 alkynyl group, a 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is a halogen atom, a C1-C3 alkyl optionally having a halogen atom) Group, and optionally having one or more atoms or groups selected from the group consisting of C1-C3 alkoxy groups optionally having halogen atoms), -OR ^20b (where R ^20b is Represents a C1-C6 alkyl group optionally having one or more halogen atoms.), —S (O) _m R ^21b (wherein R ^21b may have one or more halogen atoms). Good C1-C6 alk It represents a group, m represents 0, 1 or 2.), A cyano group, a nitro group, a halogen atom or a hydrogen atom,
R ^7b is a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ^22b (wherein R ^22b is a C1-C6 alkyl group optionally having one or more halogen atoms) ), —S (O) _m R ^23b (wherein R ^23b represents a C1-C6 alkyl group optionally having one or more halogen atoms, and m represents 0, 1 or 2). .), - SF _5, or a halogen atom,
R ^8b is a C1-C6 alkyl group having one phenyl group (wherein the phenyl group has a cyano group, a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, and a halogen atom). And optionally having one or more atoms or groups selected from the group consisting of C1-C3 alkoxy groups.) C1-C6 having one 5- or 6-membered aromatic heterocyclic group An alkyl group (wherein the 5- or 6-membered aromatic heterocyclic group is a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, and a C1-C3 alkoxy optionally having a halogen atom); Which may have one or more atoms or groups selected from the group consisting of groups), or a C1-C6 alkyl group having one tetrahydrofuryl group (wherein the tetrahydrofuryl The group is one or more atoms or groups selected from the group consisting of a C1-C3 alkyl group which may have a halogen atom, a C1-C3 alkoxy group which may have a halogen atom, and a halogen atom. Which may have)
R ^9b is a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ^24b (wherein R ^24b is a C1-C6 alkyl group optionally having one or more halogen atoms) ), -S (O) _m R ^25b (where R ^25b represents a C1-C6 alkyl group optionally having one or more halogen atoms, and m represents 0, 1 or 2). ), Represents a halogen atom or a hydrogen atom,
n represents 0, 1 or 2. Or a N-oxide thereof.

Formula (1-3-1)
[Where:
R ^1c represents an ethyl group, a cyclopropyl group, or a cyclopropylmethyl group,
R ^8c is a cyano group, a halogen atom or a C1-C3 alkyl group optionally having a C1-C3 alkyl group optionally having a halogen atom, a halogen atom or a C1-C3 alkyl group optionally having a halogen atom. May have a pyridylmethyl group which may have, a halogen atom or a thiazolylmethyl group which may have a C1-C3 alkyl group which may have a halogen atom, a halogen atom or a halogen atom. An imidazolylmethyl group optionally having a C1-C3 alkyl group, a halogen atom or a tetrahydrofurylmethyl group optionally having a C1-C3 alkyl group optionally having a halogen atom, a halogen atom or a halogen atom A pyrazolylmethyl group optionally having a C1-C3 alkyl group, It may have a halogen atom or a C1-C3 alkyl group optionally having a C1-C3 alkyl group optionally having a halogen atom, or a C1-C3 alkyl group optionally having a halogen atom or a halogen atom. A good pyrimidinylmethyl group, a cyano group, a halogen atom or a C1-C3 alkyl group optionally having a halogen atom, a phenylethyl group optionally having a C1-C3 alkyl group, a halogen atom or a C1-optionally having a halogen atom A thiazolylethyl group optionally having a C3 alkyl group, a pyridylethyl group optionally having a C1-C3 alkyl group optionally having a halogen atom or a halogen atom, or a tetrahydrofurylethyl group;
R ^3c is a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ^20c (wherein R ^20c is a C1-C6 alkyl optionally having one or more halogen atoms) -S (O) _m R ^21c (where R ^21c represents a C1-C6 alkyl group optionally having one or more halogen atoms, and m represents 0, 1 or 2). Represents a halogen atom or a hydrogen atom,
R ^6c is a C1-C6 haloalkyl group, —OR ^22c (where R ^22c represents a C1-C6 haloalkyl group), —S (O) _m R ^23c (where R ^23c is a C1-C6 haloalkyl group) the stands, m represents 0, 1 or 2), -. SF ₅ or a halogen atom,
n represents 0, 1 or 2. ]
Or a N-oxide thereof.

Formula (1-3-2)
[Where:
R ^1c represents an ethyl group, a cyclopropyl group, or a cyclopropylmethyl group,
R ^8c is a cyano group, a halogen atom or a C1-C3 alkyl group optionally having a C1-C3 alkyl group optionally having a halogen atom, a halogen atom or a C1-C3 alkyl group optionally having a halogen atom. May have a pyridylmethyl group which may have, a halogen atom or a thiazolylmethyl group which may have a C1-C3 alkyl group which may have a halogen atom, a halogen atom or a halogen atom. An imidazolylmethyl group optionally having a C1-C3 alkyl group, a halogen atom or a tetrahydrofurylmethyl group optionally having a C1-C3 alkyl group optionally having a halogen atom, a halogen atom or a halogen atom A pyrazolylmethyl group optionally having a C1-C3 alkyl group, It may have a halogen atom or a C1-C3 alkyl group optionally having a C1-C3 alkyl group optionally having a halogen atom, or a C1-C3 alkyl group optionally having a halogen atom or a halogen atom. A good pyrimidinylmethyl group, a cyano group, a halogen atom or a C1-C3 alkyl group optionally having a halogen atom, a phenylethyl group optionally having a C1-C3 alkyl group, a halogen atom or a C1-optionally having a halogen atom A thiazolylethyl group optionally having a C3 alkyl group, a pyridylethyl group optionally having a C1-C3 alkyl group optionally having a halogen atom or a halogen atom, or a tetrahydrofurylethyl group;
R ^3c is a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ^20c (wherein R ^20c is a C1-C6 alkyl optionally having one or more halogen atoms) -S (O) _m R ^21c (where R ^21c represents a C1-C6 alkyl group optionally having one or more halogen atoms, and m represents 0, 1 or 2). Represents a halogen atom or a hydrogen atom,
R ^7c is a C1-C6 haloalkyl group, —OR ^22c (where R ^22c represents a C1-C6 haloalkyl group), —S (O) _m R ^23c (where R ^23c is a C1-C6 haloalkyl group) the stands, m represents 0, 1 or 2), -. SF ₅ or a halogen atom,
n represents 0, 1 or 2. ]
Or a N-oxide thereof.

Formula (1-4-1)
[Where:
R ^1d represents an ethyl group, a cyclopropyl group, or a cyclopropylmethyl group,
R ^{8d is a} cyano group, a halogen atom or a C1-C3 alkyl optionally having a C1-C3 alkyl group optionally having a halogen atom, a C1-C3 alkyl optionally having a halogen atom or a halogen atom. A pyridylmethyl group which may have a group, a halogen atom or a thiazolylmethyl group which may have a C1-C3 alkyl group which may have a halogen atom, a halogen atom or a halogen atom An imidazolylmethyl group optionally having a C1-C3 alkyl group, a halogen atom or a tetrahydrofurylmethyl group optionally having a C1-C3 alkyl group optionally having a halogen atom, a halogen atom or a halogen Pyrazolylmethyl group optionally having C1-C3 alkyl group optionally having atom A halogen atom or a pyrazinylmethyl group optionally having a C1-C3 alkyl group optionally having a halogen atom, a halogen atom or a C1-C3 alkyl group optionally having a halogen atom May be a pyrimidinylmethyl group, a cyano group, a halogen atom or a C1-C3 alkyl group optionally having a halogen atom, a phenylethyl group optionally having a C1-C3 alkyl group, a halogen atom or a C1 optionally having a halogen atom -Represents a thiazolylethyl group optionally having -C3 alkyl group, a halogen atom or a pyridylethyl group optionally having C1-C3 alkyl group optionally having a halogen atom, or a tetrahydrofurylethyl group,
R ^3d is
One or more halogen atoms optionally may C1-C6 alkyl group which may ^{have, -OR 20d (wherein} the ^{R 20d} represents one or more halogen atoms optionally may C1-C6 alkyl group optionally having. ), -S (O) _m R ^21d (where R ^21d represents a C1-C6 alkyl group optionally having one or more halogen atoms, and m represents 0, 1 or 2), Represents a halogen atom or a hydrogen atom,
R ^6d is a C1-C6 haloalkyl group, —OR ^22d (where R ^22d represents a C1-C6 haloalkyl group), —S (O) _m R ^23d (where R ^23d is a C1-C6 haloalkyl group) the stands, m represents 0, 1 or 2), -. SF ₅ or a halogen atom,
n represents 0, 1 or 2. ]
Or a N-oxide thereof.

Formula (1-4-2)
[Where:
R ^1d represents an ethyl group, a cyclopropyl group, or a cyclopropylmethyl group,
R ^8d is a cyano group, a halogen atom or a C1-C3 alkyl group optionally having a C1-C3 alkyl group optionally having a halogen atom, a halogen atom or a C1-C3 alkyl group optionally having a halogen atom. May have a pyridylmethyl group which may have, a halogen atom or a thiazolylmethyl group which may have a C1-C3 alkyl group which may have a halogen atom, a halogen atom or a halogen atom. An imidazolylmethyl group optionally having a C1-C3 alkyl group, a halogen atom or a tetrahydrofurylmethyl group optionally having a C1-C3 alkyl group optionally having a halogen atom, a halogen atom or a halogen atom A pyrazolylmethyl group optionally having a C1-C3 alkyl group, It may have a halogen atom or a C1-C3 alkyl group optionally having a C1-C3 alkyl group optionally having a halogen atom, or a C1-C3 alkyl group optionally having a halogen atom or a halogen atom. A good pyrimidinylmethyl group, a cyano group, a halogen atom or a C1-C3 alkyl group optionally having a halogen atom, a phenylethyl group optionally having a C1-C3 alkyl group, a halogen atom or a C1-optionally having a halogen atom A thiazolylethyl group optionally having a C3 alkyl group, a pyridylethyl group optionally having a C1-C3 alkyl group optionally having a halogen atom or a halogen atom, or a tetrahydrofurylethyl group;
R ^3d is a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ^20d (wherein R ^20d is a C1-C6 alkyl ^optionally having one or more halogen atoms) -S (O) _m R ^21d (where R ^21d represents a C1-C6 alkyl group optionally having one or more halogen atoms, and m represents 0, 1 or 2). Represents a halogen atom or a hydrogen atom,
R ^7d is a C1-C6 haloalkyl group, —OR ^22d (where R ^22d represents a C1-C6 haloalkyl group), —S (O) _m R ^23d (where R ^23d is a C1-C6 haloalkyl group) the stands, m represents 0, 1 or 2), -. SF ₅ or a halogen atom,
n represents 0, 1 or 2. ]
Or a N-oxide thereof.

Formula (1-5-1)
[Where:
R ^1e represents an ethyl group, a cyclopropyl group, or a cyclopropylmethyl group,
R ^8e is a cyano group, a halogen atom or a C1-C3 alkyl group optionally having a C1-C3 alkyl group optionally having a halogen atom, a C1-C3 alkyl group optionally having a halogen atom or a halogen atom. May have a pyridylmethyl group which may have, a halogen atom or a thiazolylmethyl group which may have a C1-C3 alkyl group which may have a halogen atom, a halogen atom or a halogen atom. An imidazolylmethyl group optionally having a C1-C3 alkyl group, a halogen atom or a tetrahydrofurylmethyl group optionally having a C1-C3 alkyl group optionally having a halogen atom, a halogen atom or a halogen atom A pyrazolylmethyl group optionally having a C1-C3 alkyl group, It may have a halogen atom or a C1-C3 alkyl group optionally having a C1-C3 alkyl group optionally having a halogen atom, or a C1-C3 alkyl group optionally having a halogen atom or a halogen atom. A good pyrimidinylmethyl group, a cyano group, a halogen atom or a C1-C3 alkyl group optionally having a halogen atom, a phenylethyl group optionally having a C1-C3 alkyl group, a halogen atom or a C1-optionally having a halogen atom A thiazolylethyl group optionally having a C3 alkyl group, a pyridylethyl group optionally having a C1-C3 alkyl group optionally having a halogen atom or a halogen atom, or a tetrahydrofurylethyl group;
R ^3e is a C1-C6 alkyl group ^optionally having one or more halogen atoms, —OR ^20e (wherein R ^20e is a C1-C6 alkyl ^optionally having one or more halogen atoms) -S (O) _m R ^21e (wherein R ^21e represents a C1-C6 alkyl group optionally having one or more halogen atoms, and m represents 0, 1 or 2). Represents a halogen atom or a hydrogen atom,
R ^6e is a C1-C6 haloalkyl group, —OR ^22e (where R ^22e represents a C1-C6 haloalkyl group), —S (O) _m R ^23e (where R ^23e is a C1-C6 haloalkyl group) the stands, m represents 0, 1 or 2), -. SF ₅ or a halogen atom,
n represents 0, 1 or 2. ]
Or a N-oxide thereof.

Formula (1-5-2)
[Where:
R ^1e represents an ethyl group, a cyclopropyl group, or a cyclopropylmethyl group,
R ^8e is a cyano group, a halogen atom or a C1-C3 alkyl group optionally having a C1-C3 alkyl group optionally having a halogen atom, a C1-C3 alkyl group optionally having a halogen atom or a halogen atom. May have a pyridylmethyl group which may have, a halogen atom or a thiazolylmethyl group which may have a C1-C3 alkyl group which may have a halogen atom, a halogen atom or a halogen atom. An imidazolylmethyl group optionally having a C1-C3 alkyl group, a halogen atom or a tetrahydrofurylmethyl group optionally having a C1-C3 alkyl group optionally having a halogen atom, a halogen atom or a halogen atom A pyrazolylmethyl group optionally having a C1-C3 alkyl group, It may have a halogen atom or a C1-C3 alkyl group optionally having a C1-C3 alkyl group optionally having a halogen atom, or a C1-C3 alkyl group optionally having a halogen atom or a halogen atom. A good pyrimidinylmethyl group, a cyano group, a halogen atom or a C1-C3 alkyl group optionally having a halogen atom, a phenylethyl group optionally having a C1-C3 alkyl group, a halogen atom or a C1-optionally having a halogen atom A thiazolylethyl group optionally having a C3 alkyl group, a pyridylethyl group optionally having a C1-C3 alkyl group optionally having a halogen atom or a halogen atom, or a tetrahydrofurylethyl group;
R ^3e is a C1-C6 alkyl group ^optionally having one or more halogen atoms, —OR ^20e (wherein R ^20e is a C1-C6 alkyl ^optionally having one or more halogen atoms) -S (O) _m R ^21e (wherein R ^21e represents a C1-C6 alkyl group optionally having one or more halogen atoms, and m represents 0, 1 or 2). Represents a halogen atom or a hydrogen atom,
R ^7e is a C1-C6 haloalkyl group, —OR ^22e (where R ^22e represents a C1-C6 haloalkyl group), —S (O) _m R ^23e (where R ^23e is a C1-C6 haloalkyl group) the stands, m represents 0, 1 or 2), -. SF ₅ or a halogen atom,
n represents 0, 1 or 2. ]
Or a N-oxide thereof.

In the formula (1), compounds wherein A ¹ is a nitrogen atom;
In the formula (1), compounds wherein A ² is a nitrogen atom;
In the formula (1), compounds wherein A ¹ is ═CR ⁹ —;
In the formula (1), compounds wherein A ² is ═CR ¹⁰ —;
In the formula (1), compounds wherein A ¹ is ═CR ⁹ — and A ² is a nitrogen atom;
In the formula (1), compounds wherein A ¹ is ═CR ⁹ — and A ² is ═CR ¹⁰ —;
In formula (1), a compound wherein A ¹ is a nitrogen atom and A ² is ═CR ¹⁰ —;

In the formula (1), R ¹ may have one or more atoms or groups selected from the group consisting of halogen atoms and cyclopropyl groups (wherein the cyclopropyl group is One or more halogen atoms or one or more C1-C3 alkyl groups), a C2-C6 alkenyl group optionally having one or more halogen atoms, one or more halogens A compound that is a C2-C6 alkynyl group optionally having atoms, or a cyclopropyl group optionally having one or more halogen atoms;

In formula (1), R ³ may have one or more atoms or groups selected from group X, and may be one or more atoms or groups selected from group Z. A phenyl group which may have, a 5-membered heterocyclic group which may have one or more atoms or groups selected from group Z, and one or more atoms or groups selected from group Z An optionally substituted 6-membered heterocyclic group, —OR ¹¹ , —S (O) _m R ¹¹ , —SF ₅ , a cyano group, a nitro group, a halogen atom or a hydrogen atom;
In the formula (1), R ³ is a C1-C6 alkyl group optionally having one or more halogen atoms, a C2-C6 alkenyl group optionally having one or more halogen atoms, one C2-C6 alkynyl group which may have the above halogen atom, 5-membered aromatic heterocyclic group (wherein the aromatic heterocyclic group may have a halogen atom or a halogen atom, C1-C3 One or more atoms or substituents selected from the group consisting of an alkyl group and a C1-C3 alkoxy group optionally having a halogen atom), a 6-membered aromatic heterocyclic group ( Here, the aromatic heterocyclic group is selected from the group consisting of a halogen atom, a C1-C3 alkyl group which may have a halogen atom, and a C1-C3 alkoxy group which may have a halogen atom. More than one atom Or may have a substituent), —OR ¹¹ (wherein R ¹¹ is a C1-C6 alkyl group optionally having one or more halogen atoms), —S ( O) _m R ¹¹ (wherein R ¹¹ is a C1-C6 alkyl group optionally having one or more halogen atoms), a compound which is a cyano group, a nitro group, a halogen atom or a hydrogen atom;
In formula (1), R ² , R ⁴ , and R ⁵ are the same or different and each may have one or more atoms or groups selected from group X, a C1-C6 chain hydrocarbon group, A phenyl group optionally having one or more atoms or groups selected from group Z, a 5-membered heterocyclic group optionally having one or more atoms or groups selected from group Z, from group Z; 6-membered heterocyclic group optionally having one or more atoms or groups selected, —OR ¹¹ , —S (O) _m R ¹¹ , —SF ₅ , cyano group, nitro group, halogen atom or hydrogen atom A compound which is
In the formula (1), compounds wherein R ² , R ⁴ and R ⁵ are the same or different and are a halogen atom or a hydrogen atom;
In formula (1), R ⁶ and R ⁷ are the same or different and may have one or more atoms or groups selected from group X, a C1-C6 chain hydrocarbon group, —OR ¹¹ , A compound which is —S (O) _m R ¹¹ , —SF ₅ , a halogen atom or a hydrogen atom;
In Formula (1), R ⁶ may have one or more atoms or groups selected from Group X, a C1-C6 chain hydrocarbon group, —OR ¹¹ , —S (O) _m R ^11. , -SF _5, a halogen atom or a hydrogen atom, the compound ^{R 7} is a halogen atom or a hydrogen atom;
In Formula (1), R ⁶ may have one or more atoms or groups selected from Group X, a C1-C6 chain hydrocarbon group, —OR ¹¹ , —S (O) _m R ^11. , —SF ₅ or a halogen atom, and R ⁷ is a halogen atom or a hydrogen atom;
In the formula (1), R ⁶ may be a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ¹¹ (wherein R ¹¹ has one or more halogen atoms, Or -S (O) _m R ¹¹ (wherein R ¹¹ is a C1-C6 alkyl group optionally having one or more halogen atoms), an -SF ₅ or halogen atom, the compound ^{R 7} is a halogen atom or a hydrogen atom;
In formula (1), R ⁷ may have one or more atoms or groups selected from group X, a C1-C6 chain hydrocarbon group, —OR ¹¹ , —S (O) _m R ^11. , -SF _5, a halogen atom or a hydrogen atom, ^{R 6} is halogen atom or a hydrogen atom;
In formula (1), R ⁷ may have one or more atoms or groups selected from group X, a C1-C6 chain hydrocarbon group, —OR ¹¹ , —S (O) _m R ^11. , —SF ₅ or a halogen atom, and R ⁶ is a halogen atom or a hydrogen atom;
In Formula (1), R ⁷ may be a C1-C6 alkyl group that may have one or more halogen atoms, —OR ¹¹ (wherein R ¹¹ has one or more halogen atoms, Or -S (O) _m R ¹¹ (wherein R ¹¹ is a C1-C6 alkyl group optionally having one or more halogen atoms), an -SF ₅ or halogen atom, ^{R 6} is halogen atom or a hydrogen atom;

In formula (1), R ⁸ is a C1-C6 chain hydrocarbon group having one phenyl group (wherein the phenyl group has one or more atoms or groups selected from group Z; A C1-C6 chain hydrocarbon group having one 5-membered heterocyclic group (wherein the 5-membered heterocyclic group has one or more atoms or groups selected from the group Z) Or a C1-C6 chain hydrocarbon group having one 6-membered heterocyclic group (wherein the 6-membered heterocyclic group has one or more atoms or groups selected from the group Z). A compound that may be)

In the formula (1), R ⁸ is a C1-C6 chain hydrocarbon group having one phenyl group (wherein the phenyl group is a cyano group, a halogen atom, or a C1- (It may have one or more atoms or substituents selected from the group consisting of a C3 alkyl group and a C1-C3 alkoxy group optionally having a halogen atom.) One 5-membered aromatic A C1-C6 alkyl group having a heterocyclic group (wherein the 5-membered aromatic heterocyclic group has a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, and a halogen atom; Or a C1-C6 alkyl group having one 6-membered aromatic heterocyclic group (which may have one or more atoms or substituents selected from the group consisting of C1-C3 alkoxy groups). Here, the 6-membered aromatic compound The cyclic group is one or more atoms selected from the group consisting of a halogen atom, a C1-C3 alkyl group which may have a halogen atom, and a C1-C3 alkoxy group which may have a halogen atom, or A compound which may have a substituent;

In Formula (1), R ⁸ is a C1-C6 alkyl group having one phenyl group (wherein the phenyl group is a cyano group, a halogen atom, or a C1-C3 alkyl group optionally having a halogen atom). And one or more atoms or substituents selected from the group consisting of C1-C3 alkoxy groups optionally having halogen atoms.) One 5-membered aromatic heterocyclic group (Wherein the 5-membered aromatic heterocyclic group is a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, and a C1 optionally having a halogen atom) A C1-C6 alkyl group having one or more atoms or substituents selected from the group consisting of -C3 alkoxy groups) or one 6-membered aromatic heterocyclic group, wherein 6-membered aromatic heterocyclic group Represents one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally having halogen atoms, and a C1-C3 alkoxy group optionally having halogen atoms. A compound that may be present);
In Formula (1), R ⁸ is a C1-C6 alkyl group having one phenyl group (wherein the phenyl group is a cyano group, a halogen atom, or a C1-C3 alkyl group optionally having a halogen atom). , And optionally having one or more atoms or substituents selected from the group consisting of C1-C3 alkoxy groups optionally having halogen atoms) C1-C6 having one thiazolyl group An alkyl group (wherein the thiazolyl group is selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, and a C1-C3 alkoxy group optionally having a halogen atom) C 1 -C 6 alkyl group having one imidazolyl group (wherein the imidazolyl group is a halogen atom, halo It may have one or more atoms or substituents selected from the group consisting of a C1-C3 alkyl group which may have a gen atom and a C1-C3 alkoxy group which may have a halogen atom. C1-C6 alkyl group having one furyl group (wherein the furyl group has a halogen atom, a C1-C3 alkyl group which may have a halogen atom, and a halogen atom). And optionally having one or more atoms or substituents selected from the group consisting of C1-C3 alkoxy groups.) A C1-C6 alkyl group having one tetrahydrofuryl group (wherein The tetrahydrofuryl group is selected from the group consisting of a halogen atom, a C1-C3 alkyl group that may have a halogen atom, and a C1-C3 alkoxy group that may have a halogen atom. Or a C1-C6 alkyl group having one pyrazolyl group (wherein the pyrazolyl group has a halogen atom or a halogen atom). And may have one or more atoms or substituents selected from the group consisting of a C1-C3 alkyl group which may have a halogen atom and a C1-C3 alkoxy group which may have a halogen atom. C1-C6 alkyl group having a pyridyl group (wherein the pyridyl group is a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, and a C1-C3 alkoxy optionally having a halogen atom) One or more atoms or substituents selected from the group consisting of groups) or a C1-C6 alkyl group having one pyrimidinyl group (wherein the pyrimidine The ru group is one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group that may have a halogen atom, and a C1-C3 alkoxy group that may have a halogen atom. It may have a group. )
A compound which is

In the formula (1), R ⁸ is a C1-C6 alkyl group having one phenyl group (wherein the phenyl group is a cyano group, a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, And optionally having one or more atoms or substituents selected from the group consisting of C1-C3 alkoxy groups optionally having halogen atoms) C1-C6 alkyl having one thiazolyl group A group (wherein the thiazolyl group is one selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, and a C1-C3 alkoxy group optionally having a halogen atom) Or a C1-C6 alkyl group having one pyridyl group (wherein the pyridyl group has a halogen atom or a halogen atom). And may have one or more atoms or substituents selected from the group consisting of a C1-C3 alkyl group which may have a C1-C3 alkoxy group which may have a halogen atom.
A compound which is
In the formula (1), R ⁸ is benzyl group, 3-methylbenzyl group, 4-methylbenzyl group, 2-cyanobenzyl group, 3-cyanobenzyl group, 2-chlorobenzyl group, 3-chlorobenzyl group, 4 -Chlorobenzyl group, 2-methylbenzyl group, 4-cyanobenzyl group, 2-fluorobenzyl group, 3-fluorobenzyl group, 4-fluorobenzyl group, phenyl-ethyl group, (2-chloro-phenyl) -ethyl group , (3-chloro-phenyl) -ethyl group, (4-chloro-phenyl) -ethyl group, (2-methyl-phenyl) -ethyl group, (3-methyl-phenyl) -ethyl group, (4-methyl- Phenyl) -ethyl group, (2-chloro-thiazol-5-yl) -methyl group, (thiazol-5-yl) -methyl group, (2-bromo-thiazol-5-yl)- Methyl group, (2-methyl-thiazol-5-yl) -methyl group, (2-trifluoromethyl-thiazol-5-yl) -methyl group, (2-chloro-thiazol-5-yl) -ethyl group, (Thiazol-5-yl) -ethyl group, (2-chloropyridin-5-yl) -methyl group, (pyridin-3-yl) -methyl group, (pyridin-2-yl) -methyl group, (pyridine- 4-yl) -methyl group, (6-fluoro-pyridin-3-yl) -methyl group, (6-bromo-pyridin-3-yl) -methyl group, (6-trifluoromethyl-pyridin-3-yl) ) -Methyl group, (6-methyl-pyridin-3-yl) -methyl group, (6-chloro-5-fluoro-pyridin-3-yl) -methyl group, (5,6-dichloro-pyridin-3- Yl) -methyl group, (pyridyl -3-yl) -ethyl group, (6-chloro-pyridin-3-yl) -ethyl group, (pyrimidin-5-yl) -methyl group, (2-chloro-pyrimidin-5-yl) -methyl group, (2-methyl-pyrimidin-5-yl) -methyl group, (5-chloro-pyrazin-2-yl) -methyl group, (tetrahydro-furan-3-yl) -methyl group, or (tetrahydro-furan-3) A compound which is an -yl) -ethyl group;
In the formula (1), R ⁸ is benzyl group, 4-chlorobenzyl group, 3-chlorobenzyl group, 2-chlorobenzyl group, 4-methylbenzyl group, 3-methylbenzyl group, 2-methylbenzyl group, ( A compound that is a 2-chlorothiazol-5-yl) -methyl group, a (pyridin-3-yl) -methyl group, or a (2-chloropyridin-5-yl) -methyl group;

In Formula (1), A ¹ is ═CR ⁹ —, and R ⁹ may have one or more atoms or groups selected from Group X, C 1 -C 6 chain hydrocarbon group, —OR ¹¹ , a compound which is —S (O) _m R ¹¹ , a halogen atom or a hydrogen atom;
In Formula (1), A ¹ is ═CR ⁹ —, R ⁹ is a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ¹¹ (wherein R ¹¹ is one A C1-C6 alkyl group which may have the above halogen atoms.), —S (O) _m R ¹¹ (wherein R ¹¹ may have one or more halogen atoms). A -C6 alkyl group), a compound which is a halogen atom or a hydrogen atom;

In Formula (1), A ¹ is ═CR ⁹ —, and R ⁹ may have one or more atoms or groups selected from Group X, C 1 -C 6 chain hydrocarbon group, —OR ¹¹ , a compound which is —S (O) _m R ¹¹ , a halogen atom or a hydrogen atom;
In Formula (1), A ¹ is ═CR ⁹ —, R ⁹ is a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ¹¹ (wherein R ¹¹ is one A C1-C6 alkyl group which may have the above halogen atoms.), —S (O) _m R ¹¹ (wherein R ¹¹ may have one or more halogen atoms). A -C6 alkyl group), a compound which is a halogen atom or a hydrogen atom;
In the formula (1), compounds wherein A ¹ is ═CR ⁹ — and R ⁹ is a halogen atom or a hydrogen atom;
In the formula (1), compounds wherein A ¹ is ═CR ⁹ — and R ⁹ is a hydrogen atom;
In formula (1), A ² is ═CR ¹⁰ —, and R ¹⁰ may have one or more atoms or groups selected from group X, a C1-C6 chain hydrocarbon group, a halogen atom or A compound that is a hydrogen atom;
In Formula (1), A ² is ═CR ¹⁰ —, and R ¹⁰ is a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ¹¹ (wherein R ¹¹ is one A C1-C6 alkyl group which may have the above halogen atoms.), —S (O) _m R ¹¹ (wherein R ¹¹ may have one or more halogen atoms). A -C6 alkyl group), a compound which is a halogen atom or a hydrogen atom;
In the formula (1), compounds wherein A ² is ═CR ¹⁰ — and R ¹⁰ is a halogen atom or a hydrogen atom;
In the formula (1), compounds wherein A ² is ═CR ¹⁰ — and R ¹⁰ is a hydrogen atom;

In Formula (1), R ¹ may have one or more atoms or groups selected from the group consisting of halogen atoms and cyclopropyl groups (wherein the cyclopropyl group is A compound that may have one or more halogen atoms or one or more C1-C3 alkyl groups), or a cyclopropyl group that may have one or more halogen atoms;
In Formula (1), R ¹ is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a cyclopropyl group optionally having one or more halogen atoms, or a C4-C9 cyclopropylalkyl group (wherein The cyclopropyl group may have one or more halogen atoms or one or more C1-C3 alkyl groups);
In the formula (1), compounds wherein R ¹ is a methyl group, ethyl group, propyl group, isopropyl group, cyclopropyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group or cyclopropylmethyl group;
In the formula (1), compounds wherein R ¹ is an ethyl group, a cyclopropyl group, or a cyclopropylmethyl group;
In the formula (1), compounds wherein R ¹ is an ethyl group;
In Formula (1), R ³ may have one or more halogen atoms, a C1-C6 alkyl group, one or more halogen atoms may have a C2-C6 alkenyl group, one or more A C2-C6 alkynyl group and a pyridyl group which may have a halogen atom (wherein the pyridyl group has a halogen atom, a C1-C3 alkyl group which may have a halogen atom, and a halogen atom) And optionally having one or more atoms or substituents selected from the group consisting of C1-C3 alkoxy groups), pyrimidinyl groups (wherein the pyrimidinyl group has a halogen atom or a halogen atom). One or more atoms or substituents selected from the group consisting of a C1-C3 alkyl group which may optionally have a C1-C3 alkoxy group which may have a halogen atom; -OR ^20a (wherein R ^20a is a C1-C6 alkyl group optionally having one or more halogen atoms), -S (O) _m R ^21a (wherein , R ^21a is a C1-C6 alkyl group optionally having one or more halogen atoms, and m is 0, 1 or 2.), a compound which is a halogen atom or a hydrogen atom;
In the formula (1), R ³ may be a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ^20b (wherein R ^20b may have one or more halogen atoms) Represents a good C1-C6 alkyl group.), —S (O) _m R ^21b (where R ^21b represents a C1-C6 alkyl group optionally having one or more halogen atoms, and m represents 0). 1 or 2), a compound that is a halogen atom or a hydrogen atom;
In the formula (1), R ³ is a methyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, an ethyl group, an ethenyl group, an ethynyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, —CF _2. CF ₃ , —CF ₂ CF ₂ CF ₃ , —CF (CF ₃ ) ₂ , —CF ₂ CF ₂ CF ₂ CF ₃ , —OCF ₃ , —OCF ₂ CF ₃ , —SCF ₃ , —S (O) CF _{3 , -S (O) 2 CF 3} , -SCF 2 CF 3, -S (O) CF 2 CF 3, -S (O) 2 CF 2 CF 3, 2- pyridyl group, 5-trifluoromethyl-2- A compound which is a pyridyl group, a 2-pyrimidinyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
In the formula (1), R ³ is a methyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, an ethyl group, an ethenyl group, an ethynyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, —CF _2. CF ₃ , —CF ₂ CF ₂ CF ₃ , —CF (CF ₃ ) ₂ , —CF ₂ CF ₂ CF ₂ CF ₃ , —OCF ₃ , —OCF ₂ CF ₃ , —SCF ₃ , —S (O) CF ₃ , —S (O) ₂ CF ₃ , —SCF ₂ CF ₃ , —S (O) CF ₂ CF ₃ , —S (O) ₂ CF ₂ CF ₃ , fluorine atom, chlorine atom, bromine atom, iodine atom or hydrogen A compound that is an atom;

A compound in which R ² , R ⁴ and R ⁵ are all hydrogen atoms in formula (1);

In Formula (1), R ⁶ is a C1-C6 haloalkyl group, —OR ^22b (where R ^22b is a C1-C6 haloalkyl group), —S (O) _m R ^23b (where R ^23b is . a C1-C6 haloalkyl group, m is 0, 1 or 2), - a SF ₅ or halogen atom, the compound ^{R 7} is a halogen atom or a hydrogen atom;
In Formula (1), R ⁶ is a C1-C6 haloalkyl group, —OR ^22b (where R ^22b is a C1-C6 haloalkyl group), —S (O) _m R ^23b (where R ^23b is . a C1-C6 haloalkyl group, m is 0, 1 or 2) or a -SF _5, compound ^{R 7} is a halogen atom or a hydrogen atom;
In Formula (1), R ⁶ is a C1-C6 haloalkyl group, —OR ^22b (where R ^22b is a C1-C6 haloalkyl group), —S (O) _m R ^23b (where R ^23b is A C1-C6 haloalkyl group, m is 0, 1, or 2) or a halogen atom, and R ⁷ is a halogen atom or a hydrogen atom;
In the formula (1), R ⁶ is a C1-C6 haloalkyl group, —OR ^22b (where R ^22b is a C1-C6 haloalkyl group) or —S (O) _m R ^23b (where R ^23b is A compound having a C1-C6 haloalkyl group, m is 0, 1 or 2), and R ⁷ is a halogen atom or a hydrogen atom;
In the formula (1), R ⁶ is a C1-C6 perfluoroalkyl group, —OR ^22b (where R ^22b is a C1-C6 perfluoroalkyl group) or —S (O) _m R ^23b (wherein , R ^23b is a C1-C6 perfluoroalkyl group), and R ⁷ is a halogen atom or a hydrogen atom;
In the formula (1), R ⁶ is a trifluoromethyl group, —CF ₂ CF ₃ , —CF ₂ CF ₂ CF ₃ , —CF (CF ₃ ) ₂ , —OCF ₃ , —OCF ₂ CF ₃ , —SCF ₃ , _{-S (O) CF 3, -S} (O) 2 CF 3, -SCF 2 CF 3, -S (O) CF 2 CF 3, -S (O) 2 CF 2 CF 3, SF 5, a fluorine atom, A compound which is a chlorine atom, a bromine atom or an iodine atom, and R ⁷ is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
In the formula (1), R ⁷ is a C1-C6 haloalkyl group, —OR ^22b (where R ^22b is a C1-C6 haloalkyl group), —S (O) _m R ^23b (where R ^23b is . a C1-C6 haloalkyl group, m is 0, 1 or 2), - a SF ₅ or halogen atom, ^{R 6} is halogen atom or a hydrogen atom;
In the formula (1), R ⁷ is a C1-C6 haloalkyl group, —OR ^22b (where R ^22b is a C1-C6 haloalkyl group), —S (O) _m R ^23b (where R ^23b is . a C1-C6 haloalkyl group, m is 0, 1 or 2) or a -SF _5, ^{R 6} is halogen atom or a hydrogen atom;
In the formula (1), R ⁷ is a C1-C6 haloalkyl group, —OR ^22b (where R ^22b is a C1-C6 haloalkyl group), —S (O) _m R ^23b (where R ^23b is A C1-C6 haloalkyl group, m is 0, 1 or 2) or a halogen atom, and R ⁶ is a halogen atom or a hydrogen atom;
In the formula (1), R ⁷ is a C1-C6 haloalkyl group, —OR ^22b (where R ^22b is a C1-C6 haloalkyl group) or —S (O) _m R ^23b (where R ^23b is A compound having a C1-C6 haloalkyl group, m is 0, 1 or 2), and R ⁶ is a halogen atom or a hydrogen atom;
In the formula (1), R ⁷ is a C1-C6 perfluoroalkyl group, —OR ^22b (where R ^22b is a C1-C6 perfluoroalkyl group) or —S (O) _m R ^23b (wherein R ^23b is a C1-C6 perfluoroalkyl group), and R ⁶ is a halogen atom or a hydrogen atom;
In the formula (1), R ⁷ is a trifluoromethyl group, —CF ₂ CF ₃ , —CF ₂ CF ₂ CF ₃ , —CF (CF ₃ ) ₂ , —OCF ₃ , —OCF ₂ CF ₃ , —SCF ₃ , _{-S (O) CF 3, -S} (O) 2 CF 3, -SCF 2 CF 3, -S (O) CF 2 CF 3, -S (O) 2 CF 2 CF 3, SF 5, a fluorine atom, A compound which is a chlorine atom, a bromine atom or an iodine atom, and R ⁶ is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;

In the formula (1), compounds wherein A ¹ is ═CR ⁹ — and R ⁹ is a halogen atom or a hydrogen atom;
In the formula (1), compounds wherein A ¹ is ═CR ⁹ — and R ⁹ is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
In the formula (1), compounds wherein A ¹ is ═CR ⁹ — and R ⁹ is a fluorine atom or a hydrogen atom;

In the formula (1), compounds wherein A ² is ═CR ¹⁰ — and R ¹⁰ is a halogen atom or a hydrogen atom;
In formula (1), a compound wherein A ² is ═CR ¹⁰ — and R ¹⁰ is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
In the formula (1), compounds wherein A ² is ═CR ¹⁰ — and R ¹⁰ is a fluorine atom or a hydrogen atom;

In equation (1),
A ¹ is nitrogen atom or = CR ⁹ - and is,
A ² is a nitrogen atom or = CR ^10- ,
R ² , R ³ , R ⁴ or R ⁵ are the same or different and are selected from group Z, a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from group X one or more atoms or phenyl group which may have a group, one or more atoms 5 or or may have a group 6-membered heterocyclic group selected from the group Z, -OR ^11, -S (O) _m R ¹¹ , —SF ₅ , a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R ⁶ and R ⁷ are the same or different and may have one or more atoms or groups selected from group X, a C1-C6 chain hydrocarbon group, —OR ¹¹ , —S (O) _m R ¹¹ , —SF ₅ , a halogen atom or a hydrogen atom,
R ⁸ is a C1-C6 chain hydrocarbon group having one phenyl group (wherein the phenyl group may have one or more atoms or groups selected from group Z), one A C1-C6 chain hydrocarbon group having a 5- or 6-membered heterocyclic group (wherein the 5- or 6-membered heterocyclic group may have one or more atoms or groups selected from the group Z) Good)
R ⁹ is a C1-C6 chain hydrocarbon group which may have one or more halogen atoms, —OR ¹¹ , —S (O) _m R ¹¹ , a halogen atom or a hydrogen atom,
A compound in which R ¹⁰ is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR ¹¹ , —S (O) _m R ¹¹ , a halogen atom or a hydrogen atom.

In equation (1),
A ¹ is nitrogen atom or = CR ⁹ - and is,
A ² is a nitrogen atom or = CR ^10- ,
R ¹ is a C1-C6 alkyl group optionally having one or more atoms or groups selected from the group consisting of halogen atoms and cyclopropyl groups (wherein the cyclopropyl group is one or more halogen atoms) Or may have one or more C1-C3 alkyl groups), may have one or more halogen atoms, may have C2-C6 alkenyl groups, or may have one or more halogen atoms. A good C2-C6 alkynyl group, or a cyclopropyl group optionally having one or more halogen atoms,
R ² , R ⁴ and R ⁵ are the same or different and are a halogen atom or a hydrogen atom,
R ³ has a C1-C6 alkyl group optionally having one or more halogen atoms, a C2-C6 alkenyl group optionally having one or more halogen atoms, and one or more halogen atoms. An optionally substituted C2-C6 alkynyl group, a 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is a halogen atom or a C1-C3 optionally having a halogen atom) alkyl group, and may have one or more atoms or groups selected from the group consisting of may also be C1-C3 alkoxy group optionally having a halogen ^{atom), -. oR 11, -S} (O) _m R ¹¹ , a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R ⁶ is a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ¹¹ , —S (O) _m R ¹¹ , —SF ₅ or a halogen atom;
R ⁷ is a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ¹¹ , —S (O) _m R ¹¹ , a halogen atom or a hydrogen atom;
R ¹¹ is a C1-C6 alkyl group optionally having one or more halogen atoms,
R ⁸ is a C1-C6 alkyl group having one phenyl group (wherein the phenyl group has a cyano group, a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, and a halogen atom). And optionally having one or more atoms or groups selected from the group consisting of C1-C3 alkoxy groups), or C1- having a 5- or 6-membered aromatic heterocyclic group. C6 alkyl group (wherein the 5- or 6-membered aromatic heterocyclic group is a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, and a C1-C3 optionally having a halogen atom) And may have one or more atoms or groups selected from the group consisting of alkoxy groups).
R ⁹ is a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ¹¹ , —S (O) _m R ¹¹ , a halogen atom or a hydrogen atom;
R ¹⁰ is 1 or more halogen atoms optionally may C1-C6 alkyl group which may _{^{have, -OR 11, -S (O)}} m R 11, a compound is a halogen atom or a hydrogen atom.

In equation (1),
A ¹ is nitrogen atom or = CR ⁹ - and is,
A ² is a nitrogen atom or = CR ^10- ,
R ¹ is an ethyl group,
R ² , R ⁴ and R ⁵ are hydrogen atoms,
R ³ is a C1-C6 alkyl group which may have one or more halogen atoms or a hydrogen atom,
R ⁶ and R ⁷ are the same or different and are a C1-C6 alkyl group optionally having one or more halogen atoms, or a halogen atom,
R ⁸ is a C1-C6 alkyl group having one phenyl group (wherein the phenyl group may have a cyano group, a halogen atom, or a C1-C3 alkyl group), or one C1-C6 alkyl group having a 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group may have a halogen atom or a C1-C3 alkyl group) And
A compound in which R ⁹ and R ¹⁰ are a halogen atom or a hydrogen atom.

In equation (1),
A ¹ is nitrogen atom or = CR ⁹ - and is,
A ² is a nitrogen atom or = CR ^10- ,
R ¹ is an ethyl group,
R ² , R ⁴ and R ⁵ are hydrogen atoms,
R ³ is a C1-C6 alkyl group which may have one or more halogen atoms or a hydrogen atom,
R ⁶ and R ⁷ are the same or different and are a C1-C6 alkyl group optionally having one or more halogen atoms, or a halogen atom,
R ⁸ is a cyano group, a halogen atom or a C1-C3 alkyl optionally having a C1-C3 alkyl group optionally having a halogen atom, a C1-C3 alkyl optionally having a halogen atom or a halogen atom. A pyridylmethyl group which may have a group, a halogen atom or a thiazolylmethyl group which may have a C1-C3 alkyl group which may have a halogen atom, a halogen atom or a halogen atom An imidazolylmethyl group optionally having a C1-C3 alkyl group, a halogen atom or a tetrahydrofurylmethyl group optionally having a C1-C3 alkyl group optionally having a halogen atom, a halogen atom or a halogen A pyrazolylmethyl group optionally having a C1-C3 alkyl group optionally having an atom, It may have a halogen atom or a C1-C3 alkyl group optionally having a C1-C3 alkyl group optionally having a halogen atom, or a C1-C3 alkyl group optionally having a halogen atom or a halogen atom. A good pyrimidinylmethyl group, a cyano group, a halogen atom or a C1-C3 alkyl group optionally having a halogen atom, a phenylethyl group optionally having a C1-C3 alkyl group, a halogen atom or a C1-optionally having a halogen atom A thiazolylethyl group optionally having a C3 alkyl group, a halogen atom or a pyridylethyl group optionally having a C1-C3 alkyl group optionally having a halogen atom, or a tetrahydrofurylethyl group,
A compound in which R ⁹ and R ¹⁰ are a halogen atom or a hydrogen atom.

In equation (1),
A ¹ is nitrogen atom or = CR ⁹ - and is,
A ² is a nitrogen atom or = CR ^10- ,
R ¹ is an ethyl group,
R ² , R ⁴ and R ⁵ are hydrogen atoms,
R ³ is a C1-C3 alkyl group optionally having one or more fluorine atoms or a hydrogen atom,
R ⁶ and R ⁷ are the same or different and are a C1-C6 alkyl group optionally having one or more halogen atoms, or a halogen atom,
R ⁸ is a cyano group, a halogen atom or a C1-C3 alkyl optionally having a C1-C3 alkyl group optionally having a halogen atom, a C1-C3 alkyl optionally having a halogen atom or a halogen atom. A pyridylmethyl group which may have a group, a halogen atom or a thiazolylmethyl group which may have a C1-C3 alkyl group which may have a halogen atom, a halogen atom or a halogen atom An imidazolylmethyl group optionally having a C1-C3 alkyl group, a halogen atom or a tetrahydrofurylmethyl group optionally having a C1-C3 alkyl group optionally having a halogen atom, a halogen atom or a halogen A pyrazolylmethyl group optionally having a C1-C3 alkyl group optionally having an atom, It may have a halogen atom or a C1-C3 alkyl group optionally having a C1-C3 alkyl group optionally having a halogen atom, or a C1-C3 alkyl group optionally having a halogen atom or a halogen atom. A good pyrimidinylmethyl group, a cyano group, a halogen atom or a C1-C3 alkyl group optionally having a halogen atom, a phenylethyl group optionally having a C1-C3 alkyl group, a halogen atom or a C1-optionally having a halogen atom A thiazolylethyl group optionally having a C3 alkyl group, a halogen atom or a pyridylethyl group optionally having a C1-C3 alkyl group optionally having a halogen atom, or a tetrahydrofurylethyl group, and R ⁹ And a compound wherein R ¹⁰ is a halogen atom or a hydrogen atom.

In equation (1),
A ¹ is nitrogen atom or = CR ⁹ - and is,
A ² is a nitrogen atom or = CR ^10- ,
R ¹ is an ethyl group,
R ² , R ⁴ and R ⁵ are hydrogen atoms,
R ³ is a C1-C3 alkyl group optionally having one or more fluorine atoms or a hydrogen atom,
R ⁶ and R ⁷ are the same or different and are a C1-C6 alkyl group optionally having one or more halogen atoms, or a halogen atom,
R ⁸ is a benzyl group optionally having a halogen atom or a C1-C3 alkyl group, a pyridylmethyl group optionally having a halogen atom or a C1-C3 alkyl group, or a halogen atom or a C1-C3 alkyl group A thiazolylmethyl group optionally having
A compound in which R ⁹ and R ¹⁰ are a halogen atom or a hydrogen atom.

In the formula (1-1-1), compounds wherein A ^2a is a nitrogen atom;
In the formula (1-1-1), compounds wherein A ^2a is ═CR ^10a —;

In formula (1-1-1), R ^1a may have one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclo A propyl group may have one or more halogen atoms or one or more C1-C3 alkyl groups), or a compound that is a cyclopropyl group optionally having one or more halogen atoms;
In Formula (1-1-1), R ^1a is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a cyclopropyl group optionally having one or more halogen atoms, or a C4-C9 cyclopropylalkyl group. (Here, the cyclopropyl group may have one or more halogen atoms or one or more C1-C3 alkyl groups.)
A compound which is
In the formula (1-1-1), R ^1a represents a methyl group, an ethyl group, a propyl group, an isopropyl group, a cyclopropyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, or a cyclopropylmethyl group. A compound which is
In the formula (1-1-1), compounds wherein R ^1a is an ethyl group, a cyclopropyl group, or a cyclopropylmethyl group;
In the formula (1-1-1), compounds wherein R ^1a is an ethyl group;
In formula (1-1-1), R ^3a may have one or more halogen atoms, a C1-C6 alkyl group, and one or more halogen atoms may have a C2-C6 alkenyl group. C2-C6 alkynyl group, pyridyl group optionally having one or more halogen atoms (wherein the pyridyl group is a halogen atom, a C1-C3 alkyl group optionally having halogen atom, and halogen One or more atoms or substituents selected from the group consisting of C1-C3 alkoxy groups optionally having atoms, and pyrimidinyl groups (wherein the pyrimidinyl groups are halogen atoms, One or more atoms or substituents selected from the group consisting of a C1-C3 alkyl group optionally having a halogen atom and a C1-C3 alkoxy group optionally having a halogen atom -OR ^20a (wherein R ^20a is a C1-C6 alkyl group optionally having one or more halogen atoms), -S (O) _m R ^21a (wherein R ^21a is a C1-C6 alkyl group optionally having one or more halogen atoms, and m is 0, 1 or 2), a compound which is a halogen atom or a hydrogen atom ;
In the formula (1-1-1), R ^{3a optionally} has one or more halogen atoms, a C1-C6 alkyl group, —OR ^20a (wherein R ^20a has one or more halogen atoms. Represents an optionally substituted C1-C6 alkyl group), —S (O) _m R ^21a (wherein R ^21a represents a C1-C6 alkyl group optionally having one or more halogen atoms). , M represents 0, 1 or 2), a compound which is a halogen atom or a hydrogen atom;
In the formula (1-1-1), R ^3a is a methyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, an ethyl group, an ethenyl group, an ethynyl group, a fluoromethyl group, a difluoromethyl group, or a trifluoromethyl group. _{, -CF 2 CF 3, -CF 2} CF 2 CF 3, -CF (CF 3) 2, -CF 2 CF 2 CF 2 CF 3, -OCF 3, -OCF 2 CF 3, -SCF 3, -S ( _{O) CF 3, -S (O} ) 2 CF 3, -SCF 2 CF 3, -S (O) CF 2 CF 3, -S (O) 2 CF 2 CF 3, 2- pyridyl group, 5-trifluoromethyl A compound which is a methyl-2-pyridyl group, a 2-pyrimidinyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
In Formula (1-1-1), R ^3a is a methyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, an ethyl group, an ethenyl group, an ethynyl group, a fluoromethyl group, a difluoromethyl group, or trifluoromethyl. _{group, -CF 2 CF 3, -CF 2} CF 2 CF 3, -CF (CF 3) 2, -CF 2 CF 2 CF 2 CF 3, -OCF 3, -OCF 2 CF 3, -SCF 3, -S (O) CF ₃ , —S (O) ₂ CF ₃ , —SCF ₂ CF ₃ , —S (O) CF ₂ CF ₃ , —S (O) ₂ CF ₂ CF ₃ , fluorine atom, chlorine atom, bromine atom , A compound that is an iodine atom or a hydrogen atom;

In the formula (1-1-1), compounds wherein R ^2a , R ^4a and R ^5a are all hydrogen atoms;

In Formula (1-1-1), R ^6a is a C1-C6 haloalkyl group, —OR ^22a (where R ^22a is a C1-C6 haloalkyl group), —S (O) _m R ^23a (wherein , ^{R 23a} is C1-C6 haloalkyl group, m is 0, 1 or 2), - SF ₅ or the compound is a halogen atom.;
In Formula (1-1-1), R ^6a is a C1-C6 haloalkyl group, —OR ^22a (where R ^22a is a C1-C6 haloalkyl group), —S (O) _m R ^23a (wherein , ^{R 23a} is C1-C6 haloalkyl group, m is 0, 1 or 2) or compound is -SF _5.;
In Formula (1-1-1), R ^6a is a C1-C6 haloalkyl group, —OR ^22a (where R ^22a is a C1-C6 haloalkyl group), —S (O) _m R ^23a (wherein , R ^23a is a C1-C6 haloalkyl group, and m is 0, 1, or 2.) or a halogen atom;
In Formula (1-1-1), R ^6a is a C1-C6 haloalkyl group, —OR ^22a (where R ^22a is a C1-C6 haloalkyl group) or —S (O) _m R ^23a (wherein , R ^23a is a C1-C6 haloalkyl group and m is 0, 1 or 2);
In Formula (1-1-1), R ^6a is a C1-C6 perfluoroalkyl group, —OR ^22a (wherein R ^22a is a C1-C6 perfluoroalkyl group) or —S (O) _m R ^A compound wherein R ^23a is a C1-C6 perfluoroalkyl group;
In Formula (1-1-1), R ^6a is a trifluoromethyl group, —CF ₂ CF ₃ , —CF ₂ CF ₂ CF ₃ , —CF (CF ₃ ) ₂ , —OCF ₃ , —OCF ₂ CF _{3 , -SCF 3, -S (O)} CF 3, -S (O) 2 CF 3, -SCF 2 CF 3, -S (O) CF 2 CF 3, -S (O) 2 CF 2 CF 3, SF ₅ , a compound which is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom;

In Formula (1-1-1), R ^8a is a C1-C6 alkyl group having one phenyl group (wherein the phenyl group is a cyano group, a halogen atom, or a C1 which may have a halogen atom) One or more atoms or substituents selected from the group consisting of a -C3 alkyl group and a C1-C3 alkoxy group optionally having a halogen atom.) 1 thiazolyl group Having a C1-C6 alkyl group (wherein the thiazolyl group comprises a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, and a C1-C3 alkoxy group optionally having a halogen atom) A C1-C6 alkyl group having one imidazolyl group (wherein the imidazolyl group is a halogen atom, which may have one or more atoms or substituents selected from the group). It has one or more atoms or substituents selected from the group consisting of an atom, a C1-C3 alkyl group optionally having a halogen atom, and a C1-C3 alkoxy group optionally having a halogen atom. C1-C6 alkyl group having one furyl group (wherein the furyl group has a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, and a halogen atom). And optionally having one or more atoms or substituents selected from the group consisting of C1-C3 alkoxy groups.) C1-C6 alkyl group having one tetrahydrofuryl group (wherein The tetrahydrofuryl group includes a halogen atom, a C1-C3 alkyl group which may have a halogen atom, and a C1-C3 alkoxy group which may have a halogen atom. Or a C1-C6 alkyl group having one pyrazolyl group (wherein the pyrazolyl group is a halogen atom or a halogen atom). (It may have one or more atoms or substituents selected from the group consisting of a C1-C3 alkyl group which may have a C1-C3 alkoxy group which may have a halogen atom.) C1-C6 alkyl group having one pyridyl group (wherein the pyridyl group may have a halogen atom, a C1-C3 alkyl group which may have a halogen atom, and a halogen atom) One or more atoms or substituents selected from the group consisting of C1-C3 alkoxy groups) or a C1-C6 alkyl group having one pyrimidinyl group (wherein The pyrimidinyl group is one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group which may have a halogen atom, and a C1-C3 alkoxy group which may have a halogen atom. It may have a group. )
A compound which is
In Formula (1-1-1), R ^8a is a C1-C6 alkyl group having one phenyl group (wherein the phenyl group may have a cyano group, a halogen atom, or a halogen atom) (It may have one or more atoms or groups selected from the group consisting of a C1-C3 alkyl group and a C1-C3 alkoxy group optionally having a halogen atom.) One thiazolyl group Having a C1-C6 alkyl group (wherein the thiazolyl group comprises a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, and a C1-C3 alkoxy group optionally having a halogen atom) One or more atoms or groups selected from the group), or a C1-C6 alkyl group having one pyridyl group (wherein the pyridyl group is a halogen atom, halo, It may have one or more atoms or groups selected from the group consisting of a C1-C3 alkyl group that may have a gen atom and a C1-C3 alkoxy group that may have a halogen atom. .)
A compound which is
In the formula (1-1-1), R ^8a is benzyl group, 4-chlorobenzyl group, 3-chlorobenzyl group, 2-chlorobenzyl group, 4-methylbenzyl group, 3-methylbenzyl group, 2-methyl. A compound which is a benzyl group, (2-chlorothiazol-5-yl) -methyl group, (pyridin-3-yl) -methyl group, or (2-chloropyridin-5-yl) -methyl group;

In the formula (1-1-1), compounds wherein A ^2a is ═CR ^10a — and R ^10a is a halogen atom or a hydrogen atom;
In the formula (1-1-1), compounds wherein A ^2a is ═CR ^10a — and R ^10a is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
In the formula (1-1-1), compounds wherein A ^2a is ═CR ^10a — and R ^10a is a fluorine atom or a hydrogen atom;

In the formula (1-1-2), compounds wherein A ^2a is a nitrogen atom;
In the formula (1-1-2), compounds wherein A ^2a is = CR ^10a- ;

In Formula (1-1-2), R ^1a may have one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclo A propyl group may have one or more halogen atoms or one or more C1-C3 alkyl groups), or a compound that is a cyclopropyl group optionally having one or more halogen atoms;
In Formula (1-1-2), R ^1a is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a cyclopropyl group optionally having one or more halogen atoms, or a C4-C9 cyclopropylalkyl group. Wherein the cyclopropyl group may have one or more halogen atoms or one or more C1-C3 alkyl groups;
In Formula (1-1-2), R ^1a is a methyl group, an ethyl group, a propyl group, an isopropyl group, a cyclopropyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, or a cyclopropylmethyl group. A compound;
In the formula (1-1-2), compounds wherein R ^1a is an ethyl group, a cyclopropyl group, or a cyclopropylmethyl group;
In the formula (1-1-2), compounds wherein R ^1a is an ethyl group;
In the formula (1-1-2), R ^3a may have one or more halogen atoms, a C1-C6 alkyl group, and one or more halogen atoms may have a C2-C6 alkenyl group. C2-C6 alkynyl group, pyridyl group optionally having one or more halogen atoms (wherein the pyridyl group is a halogen atom, a C1-C3 alkyl group optionally having halogen atom, and halogen One or more atoms or substituents selected from the group consisting of C1-C3 alkoxy groups optionally having atoms, and pyrimidinyl groups (wherein the pyrimidinyl groups are halogen atoms, One or more atoms or substituents selected from the group consisting of a C1-C3 alkyl group optionally having a halogen atom and a C1-C3 alkoxy group optionally having a halogen atom -OR ^20a (wherein R ^20a is a C1-C6 alkyl group optionally having one or more halogen atoms), -S (O) _m R ^21a (wherein R ^21a is a C1-C6 alkyl group optionally having one or more halogen atoms, and m is 0, 1 or 2), a compound which is a halogen atom or a hydrogen atom ;
In the formula (1-1-2), R ^{3a optionally} has one or more halogen atoms, a C1-C6 alkyl group, —OR ^20a (wherein R ^20a has one or more halogen atoms. Represents an optionally substituted C1-C6 alkyl group), —S (O) _m R ^21a (wherein R ^21a represents a C1-C6 alkyl group optionally having one or more halogen atoms). , M represents 0, 1 or 2), a compound which is a halogen atom or a hydrogen atom;
In the formula (1-1-2), R ^3a is a methyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, an ethyl group, an ethenyl group, an ethynyl group, a fluoromethyl group, a difluoromethyl group, or a trifluoromethyl group. _{, -CF 2 CF 3, -CF 2} CF 2 CF 3, -CF (CF 3) 2, -CF 2 CF 2 CF 2 CF 3, -OCF 3, -OCF 2 CF 3, -SCF 3, -S ( _{O) CF 3, -S (O} ) 2 CF 3, -SCF 2 CF 3, -S (O) CF 2 CF 3, -S (O) 2 CF 2 CF 3, 2- pyridyl group, 5-trifluoromethyl A compound which is a methyl-2-pyridyl group, a 2-pyrimidinyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
In Formula (1-1-2), R ^3a is a methyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, an ethyl group, an ethenyl group, an ethynyl group, a fluoromethyl group, a difluoromethyl group, or trifluoromethyl. _{group, -CF 2 CF 3, -CF 2} CF 2 CF 3, -CF (CF 3) 2, -CF 2 CF 2 CF 2 CF 3, -OCF 3, -OCF 2 CF 3, -SCF 3, -S (O) CF ₃ , —S (O) ₂ CF ₃ , —SCF ₂ CF ₃ , —S (O) CF ₂ CF ₃ , —S (O) ₂ CF ₂ CF ₃ , fluorine atom, chlorine atom, bromine atom , A compound that is an iodine atom or a hydrogen atom;

In the formula (1-1-2), compounds wherein R ^2a , R ^4a and R ^5a are all hydrogen atoms;

In Formula (1-1-2), R ^7a is a C1-C6 haloalkyl group, —OR ^22a (where R ^22a is a C1-C6 haloalkyl group), —S (O) _m R ^23a (wherein , ^{R 23a} is C1-C6 haloalkyl group, m is 0, 1 or 2), - SF ₅ or the compound is a halogen atom.;
In Formula (1-1-2), R ^7a is a C1-C6 haloalkyl group, —OR ^22a (where R ^22a is a C1-C6 haloalkyl group), —S (O) _m R ^23a (wherein , ^{R 23a} is C1-C6 haloalkyl group, m is 0, 1 or 2) or compound is -SF _5.;
In Formula (1-1-2), R ^7a is a C1-C6 haloalkyl group, —OR ^22a (where R ^22a is a C1-C6 haloalkyl group), —S (O) _m R ^23a (wherein , R ^23a is a C1-C6 haloalkyl group, and m is 0, 1, or 2.) or a halogen atom;
In Formula (1-1-2), R ^7a is a C1-C6 haloalkyl group, —OR ^22a (where R ^22a is a C1-C6 haloalkyl group) or —S (O) _m R ^23a (wherein , R ^23a is a C1-C6 haloalkyl group and m is 0, 1 or 2);
In Formula (1-1-2), R ^7a is a C1-C6 perfluoroalkyl group, —OR ^22a (wherein R ^22a is a C1-C6 perfluoroalkyl group) or —S (O) _m R ^A compound wherein R ^23a is a C1-C6 perfluoroalkyl group;
In Formula (1-1-2), R ^7a is a trifluoromethyl group, —CF ₂ CF ₃ , —CF ₂ CF ₂ CF ₃ , —CF (CF ₃ ) ₂ , —OCF ₃ , —OCF ₂ CF _{3 , -SCF 3, -S (O)} CF 3, -S (O) 2 CF 3, -SCF 2 CF 3, -S (O) CF 2 CF 3, -S (O) 2 CF 2 CF 3, SF ₅ , a compound which is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom;

In Formula (1-1-2), R ^8a is a C1-C6 alkyl group having one phenyl group (wherein the phenyl group is a cyano group, a halogen atom, or a halogen atom optionally having a halogen atom) One or more atoms or substituents selected from the group consisting of a -C3 alkyl group and a C1-C3 alkoxy group optionally having a halogen atom.) 1 thiazolyl group Having a C1-C6 alkyl group (wherein the thiazolyl group comprises a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, and a C1-C3 alkoxy group optionally having a halogen atom) A C1-C6 alkyl group having one imidazolyl group (wherein the imidazolyl group is a halogen atom, which may have one or more atoms or substituents selected from the group). It has one or more atoms or substituents selected from the group consisting of an atom, a C1-C3 alkyl group optionally having a halogen atom, and a C1-C3 alkoxy group optionally having a halogen atom. C1-C6 alkyl group having one furyl group (wherein the furyl group has a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, and a halogen atom). And optionally having one or more atoms or substituents selected from the group consisting of C1-C3 alkoxy groups.) C1-C6 alkyl group having one tetrahydrofuryl group (wherein The tetrahydrofuryl group includes a halogen atom, a C1-C3 alkyl group which may have a halogen atom, and a C1-C3 alkoxy group which may have a halogen atom. Or a C1-C6 alkyl group having one pyrazolyl group (wherein the pyrazolyl group is a halogen atom or a halogen atom). (It may have one or more atoms or substituents selected from the group consisting of a C1-C3 alkyl group which may have a C1-C3 alkoxy group which may have a halogen atom.) C1-C6 alkyl group having one pyridyl group (wherein the pyridyl group may have a halogen atom, a C1-C3 alkyl group which may have a halogen atom, and a halogen atom) One or more atoms or substituents selected from the group consisting of C1-C3 alkoxy groups) or a C1-C6 alkyl group having one pyrimidinyl group (wherein The pyrimidinyl group is one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group which may have a halogen atom, and a C1-C3 alkoxy group which may have a halogen atom. It may have a group. A compound which is
In Formula (1-1-2), R ^8a is a C1-C6 alkyl group having one phenyl group (wherein the phenyl group may have a cyano group, a halogen atom, or a halogen atom) (It may have one or more atoms or groups selected from the group consisting of a C1-C3 alkyl group and a C1-C3 alkoxy group optionally having a halogen atom.) One thiazolyl group Having a C1-C6 alkyl group (wherein the thiazolyl group comprises a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, and a C1-C3 alkoxy group optionally having a halogen atom) One or more atoms or groups selected from the group) or a C1-C6 alkyl group having one pyridyl group (wherein the pyridyl group is a halogen atom, a halogen atom). May have one or more atoms or groups selected from the group consisting of a C1-C3 alkyl group which may have a hydrogen atom and a C1-C3 alkoxy group which may have a halogen atom. A compound that is
In the formula (1-1-2), R ^8a is benzyl group, 4-chlorobenzyl group, 3-chlorobenzyl group, 2-chlorobenzyl group, 4-methylbenzyl group, 3-methylbenzyl group, 2-methyl. A compound which is a benzyl group, (2-chlorothiazol-5-yl) -methyl group, (pyridin-3-yl) -methyl group, or (2-chloropyridin-5-yl) -methyl group;

In the formula (1-1-2), compounds wherein A ^2a is ═CR ^10a — and R ^10a is a halogen atom or a hydrogen atom;
In the formula (1-1-2), compounds wherein A ^2a is ═CR ^10a — and R ^10a is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
In the formula (1-1-2), compounds wherein A ^2a is ═CR ^10a — and R ^10a is a fluorine atom or a hydrogen atom;

In the formula (1-2-1), compounds wherein A ^1b is a nitrogen atom;
In the formula (1-2-1), compounds wherein A ^1b is ═CR ^10b —;

In Formula (1-2-1), R ^1b may have one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclo A propyl group may have one or more halogen atoms or one or more C1-C3 alkyl groups), or a compound that is a cyclopropyl group optionally having one or more halogen atoms;
In Formula (1-2-1), R ^1b is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a cyclopropyl group optionally having one or more halogen atoms, or a C4-C9 cyclopropylalkyl group. Wherein the cyclopropyl group may have one or more halogen atoms or one or more C1-C3 alkyl groups;
In Formula (1-2-1), R ^1b is a methyl group, an ethyl group, a propyl group, an isopropyl group, a cyclopropyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, or a cyclopropylmethyl group. A compound;
In the formula (1-2-1), compounds wherein R ^1b is an ethyl group, a cyclopropyl group, or a cyclopropylmethyl group;
In the formula (1-2-1), compounds wherein R ^1b is an ethyl group;
In the formula (1-2-1), R ^3b may have one or more halogen atoms, a C1-C6 alkyl group, and one or more halogen atoms may have a C2-C6 alkenyl group. C2-C6 alkynyl group, pyridyl group optionally having one or more halogen atoms (wherein the pyridyl group is a halogen atom, a C1-C3 alkyl group optionally having halogen atom, and halogen One or more atoms or substituents selected from the group consisting of C1-C3 alkoxy groups optionally having atoms, and pyrimidinyl groups (wherein the pyrimidinyl groups are halogen atoms, One or more atoms or substituents selected from the group consisting of a C1-C3 alkyl group optionally having a halogen atom and a C1-C3 alkoxy group optionally having a halogen atom -OR ^20b (wherein R ^20b is a C1-C6 alkyl group optionally having one or more halogen atoms), -S (O) _m R ^21b (wherein R ^21b is a C1-C6 alkyl group optionally having one or more halogen atoms, and m is 0, 1 or 2), a compound which is a halogen atom or a hydrogen atom ;
In Formula (1-2-1), R ^{3b optionally} has one or more halogen atoms, a C1-C6 alkyl group, —OR ^20b (where R ^20b has one or more halogen atoms). Represents an optionally substituted C1-C6 alkyl group), —S (O) _m R ^21b (where R ^21b represents a C1-C6 alkyl group optionally having one or more halogen atoms). , M represents 0, 1 or 2), a compound which is a halogen atom or a hydrogen atom;
In Formula (1-2-1), R ^3b is a methyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, an ethyl group, an ethenyl group, an ethynyl group, a fluoromethyl group, a difluoromethyl group, or a trifluoromethyl group. _{, -CF 2 CF 3, -CF 2} CF 2 CF 3, -CF (CF 3) 2, -CF 2 CF 2 CF 2 CF 3, -OCF 3, -OCF 2 CF 3, -SCF 3, -S ( _{O) CF 3, -S (O} ) 2 CF 3, -SCF 2 CF 3, -S (O) CF 2 CF 3, -S (O) 2 CF 2 CF 3, 2- pyridyl group, 5-trifluoromethyl A compound which is a methyl-2-pyridyl group, a 2-pyrimidinyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
In Formula (1-2-1), R ^3b is a methyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, an ethyl group, an ethenyl group, an ethynyl group, a fluoromethyl group, a difluoromethyl group, or trifluoromethyl. _{group, -CF 2 CF 3, -CF 2} CF 2 CF 3, -CF (CF 3) 2, -CF 2 CF 2 CF 2 CF 3, -OCF 3, -OCF 2 CF 3, -SCF 3, -S (O) CF ₃ , —S (O) ₂ CF ₃ , —SCF ₂ CF ₃ , —S (O) CF ₂ CF ₃ , —S (O) ₂ CF ₂ CF ₃ , fluorine atom, chlorine atom, bromine atom , A compound that is an iodine atom or a hydrogen atom;

In the formula (1-2-1), compounds wherein R ^2b , R ^4b and R ^5b are all hydrogen atoms;

In Formula (1-2-1), R ^6b is a C1-C6 haloalkyl group, —OR ^22b (where R ^22b is a C1-C6 haloalkyl group), —S (O) _m R ^23b (wherein , ^{R 23b} is a C1-C6 haloalkyl group, m is 0, 1 or 2), - SF ₅ or the compound is a halogen atom.;
In Formula (1-2-1), R ^6b is a C1-C6 haloalkyl group, —OR ^22b (where R ^22b is a C1-C6 haloalkyl group), —S (O) _m R ^23b (wherein , ^{R 23b} is a C1-C6 haloalkyl group, m is 0, 1 or 2) or compound is -SF _5.;
In Formula (1-2-1), R ^6b is a C1-C6 haloalkyl group, —OR ^22b (where R ^22b is a C1-C6 haloalkyl group), —S (O) _m R ^23b (wherein , R ^23b is a C1-C6 haloalkyl group, and m is 0, 1 or 2.) or a halogen atom;
In Formula (1-2-1), R ^6b is a C1-C6 haloalkyl group, —OR ^22b (where R ^22b is a C1-C6 haloalkyl group) or —S (O) _m R ^23b (wherein , R ^23b is a C1-C6 haloalkyl group, and m is 0, 1 or 2);
In Formula (1-2-1), R ^6b is a C1-C6 perfluoroalkyl group, —OR ^22b (where R ^22b is a C1-C6 perfluoroalkyl group) or —S (O) _m R ^A compound which is ^23b (wherein R ^23b is a C1-C6 perfluoroalkyl group);
In Formula (1-2-1), R ^6b is a trifluoromethyl group, —CF ₂ CF ₃ , —CF ₂ CF ₂ CF ₃ , —CF (CF ₃ ) ₂ , —OCF ₃ , —OCF ₂ CF _{3 , -SCF 3, -S (O)} CF 3, -S (O) 2 CF 3, -SCF 2 CF 3, -S (O) CF 2 CF 3, -S (O) 2 CF 2 CF 3, SF ₅ , a compound which is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom;

In formula (1-2-1), R ^8b is a C1-C6 alkyl group having one phenyl group (wherein the phenyl group is a cyano group, a halogen atom, or a C1 which may have a halogen atom) One or more atoms or substituents selected from the group consisting of a -C3 alkyl group and a C1-C3 alkoxy group optionally having a halogen atom.) 1 thiazolyl group Having a C1-C6 alkyl group (wherein the thiazolyl group comprises a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, and a C1-C3 alkoxy group optionally having a halogen atom) A C1-C6 alkyl group having one imidazolyl group (wherein the imidazolyl group is a halogen atom, which may have one or more atoms or substituents selected from the group). It has one or more atoms or substituents selected from the group consisting of an atom, a C1-C3 alkyl group optionally having a halogen atom, and a C1-C3 alkoxy group optionally having a halogen atom. C1-C6 alkyl group having one furyl group (wherein the furyl group has a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, and a halogen atom). And optionally having one or more atoms or substituents selected from the group consisting of C1-C3 alkoxy groups.) C1-C6 alkyl group having one tetrahydrofuryl group (wherein The tetrahydrofuryl group includes a halogen atom, a C1-C3 alkyl group which may have a halogen atom, and a C1-C3 alkoxy group which may have a halogen atom. Or a C1-C6 alkyl group having one pyrazolyl group (wherein the pyrazolyl group is a halogen atom or a halogen atom). (It may have one or more atoms or substituents selected from the group consisting of a C1-C3 alkyl group which may have a C1-C3 alkoxy group which may have a halogen atom.) C1-C6 alkyl group having one pyridyl group (wherein the pyridyl group may have a halogen atom, a C1-C3 alkyl group which may have a halogen atom, and a halogen atom) One or more atoms or substituents selected from the group consisting of C1-C3 alkoxy groups) or a C1-C6 alkyl group having one pyrimidinyl group (wherein The pyrimidinyl group is one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group which may have a halogen atom, and a C1-C3 alkoxy group which may have a halogen atom. It may have a group. A compound which is
In Formula (1-2-1), R ^8b is a C1-C6 alkyl group having one phenyl group (wherein the phenyl group may have a cyano group, a halogen atom, or a halogen atom) (It may have one or more atoms or groups selected from the group consisting of a C1-C3 alkyl group and a C1-C3 alkoxy group optionally having a halogen atom.) One thiazolyl group Having a C1-C6 alkyl group (wherein the thiazolyl group comprises a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, and a C1-C3 alkoxy group optionally having a halogen atom) One or more atoms or groups selected from the group), or a C1-C6 alkyl group having one pyridyl group (wherein the pyridyl group is a halogen atom, halo, It may have one or more atoms or groups selected from the group consisting of a C1-C3 alkyl group that may have a gen atom and a C1-C3 alkoxy group that may have a halogen atom. A compound that is
In the formula (1-2-1), R ^8b is benzyl group, 4-chlorobenzyl group, 3-chlorobenzyl group, 2-chlorobenzyl group, 4-methylbenzyl group, 3-methylbenzyl group, 2-methyl. A compound which is a benzyl group, (2-chlorothiazol-5-yl) -methyl group, (pyridin-3-yl) -methyl group, or (2-chloropyridin-5-yl) -methyl group;

In the formula (1-2-1), compounds wherein A ^1b is ═CR ^9b —, and R ^9b is a halogen atom or a hydrogen atom;
In the formula (1-2-1), compounds wherein A ^1b is ═CR ^9b — and R ^9b is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
In the formula (1-2-1), compounds wherein A ^1b is ═CR ^9b — and R ^9b is a fluorine atom or a hydrogen atom;

In the formula (1-2-2), compounds wherein A ^1b is a nitrogen atom;
In the formula (1-2-2), compounds wherein A ^1b is ═CR ^9b —;

In Formula (1-2-2), R ^1b may have one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclo A propyl group may have one or more halogen atoms or one or more C1-C3 alkyl groups), or a compound that is a cyclopropyl group optionally having one or more halogen atoms;
In Formula (1-2-2), R ^1b is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a cyclopropyl group optionally having one or more halogen atoms, or a C4-C9 cyclopropylalkyl group. Wherein the cyclopropyl group may have one or more halogen atoms or one or more C1-C3 alkyl groups;
In Formula (1-2-2), R ^1b is a methyl group, an ethyl group, a propyl group, an isopropyl group, a cyclopropyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, or a cyclopropylmethyl group. A compound;
In the formula (1-2-2), compounds wherein R ^1b is an ethyl group, a cyclopropyl group, or a cyclopropylmethyl group;
In the formula (1-2-2), compounds wherein R ^1b is an ethyl group;
In the formula (1-2-2), R ^3b may have one or more halogen atoms, a C1-C6 alkyl group, and one or more halogen atoms may have a C2-C6 alkenyl group. C2-C6 alkynyl group, pyridyl group optionally having one or more halogen atoms (wherein the pyridyl group is a halogen atom, a C1-C3 alkyl group optionally having halogen atom, and halogen One or more atoms or substituents selected from the group consisting of C1-C3 alkoxy groups optionally having atoms, and pyrimidinyl groups (wherein the pyrimidinyl groups are halogen atoms, One or more atoms or substituents selected from the group consisting of a C1-C3 alkyl group optionally having a halogen atom and a C1-C3 alkoxy group optionally having a halogen atom -OR ^20b (wherein R ^20b is a C1-C6 alkyl group optionally having one or more halogen atoms), -S (O) _m R ^21b (wherein R ^21b is a C1-C6 alkyl group optionally having one or more halogen atoms, and m is 0, 1 or 2), a compound which is a halogen atom or a hydrogen atom ;
In the formula (1-2-2), R ^3b may have one or more halogen atoms, a C1-C6 alkyl group, —OR ^20b (wherein R ^20b has one or more halogen atoms. Represents an optionally substituted C1-C6 alkyl group), —S (O) _m R ^21b (where R ^21b represents a C1-C6 alkyl group optionally having one or more halogen atoms). , M represents 0, 1 or 2), a compound which is a halogen atom or a hydrogen atom;
In Formula (1-2-2), R ^3b is a methyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, an ethyl group, an ethenyl group, an ethynyl group, a fluoromethyl group, a difluoromethyl group, or a trifluoromethyl group. _{, -CF 2 CF 3, -CF 2} CF 2 CF 3, -CF (CF 3) 2, -CF 2 CF 2 CF 2 CF 3, -OCF 3, -OCF 2 CF 3, -SCF 3, -S ( _{O) CF 3, -S (O} ) 2 CF 3, -SCF 2 CF 3, -S (O) CF 2 CF 3, -S (O) 2 CF 2 CF 3, 2- pyridyl group, 5-trifluoromethyl A compound which is a methyl-2-pyridyl group, a 2-pyrimidinyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
In the formula (1-2-2), R ^3b is a methyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, an ethyl group, an ethenyl group, an ethynyl group, a fluoromethyl group, a difluoromethyl group, or trifluoromethyl. _{group, -CF 2 CF 3, -CF 2} CF 2 CF 3, -CF (CF 3) 2, -CF 2 CF 2 CF 2 CF 3, -OCF 3, -OCF 2 CF 3, -SCF 3, -S (O) CF ₃ , —S (O) ₂ CF ₃ , —SCF ₂ CF ₃ , —S (O) CF ₂ CF ₃ , —S (O) ₂ CF ₂ CF ₃ , fluorine atom, chlorine atom, bromine atom , A compound that is an iodine atom or a hydrogen atom;

In the formula (1-2-2), compounds wherein R ^2b , R ^4b and R ^5b are all hydrogen atoms;

In the formula (1-2-2), R ^7b is a C1-C6 haloalkyl group, —OR ^22b (where R ^22b is a C1-C6 haloalkyl group), —S (O) _m R ^23b (wherein , ^{R 23b} is a C1-C6 haloalkyl group, m is 0, 1 or 2), - SF ₅ or the compound is a halogen atom.;
In the formula (1-2-2), R ^7b is a C1-C6 haloalkyl group, —OR ^22b (where R ^22b is a C1-C6 haloalkyl group), —S (O) _m R ^23b (wherein , ^{R 23b} is a C1-C6 haloalkyl group, m is 0, 1 or 2) or compound is -SF _5.;
In the formula (1-2-2), R ^7b is a C1-C6 haloalkyl group, —OR ^22b (where R ^22b is a C1-C6 haloalkyl group), —S (O) _m R ^23b (wherein , R ^23b is a C1-C6 haloalkyl group, and m is 0, 1 or 2.) or a halogen atom;
In Formula (1-2-2), R ^7b is a C1-C6 haloalkyl group, —OR ^22b (where R ^22b is a C1-C6 haloalkyl group) or —S (O) _m R ^23b (wherein , R ^23b is a C1-C6 haloalkyl group, and m is 0, 1 or 2);
In Formula (1-2-2), R ^7b is a C1-C6 perfluoroalkyl group, —OR ^22b (wherein R ^22b is a C1-C6 perfluoroalkyl group) or —S (O) _m R ^A compound which is ^23b (wherein R ^23b is a C1-C6 perfluoroalkyl group);
In Formula (1-2-2), R ^7b is a trifluoromethyl group, —CF ₂ CF ₃ , —CF ₂ CF ₂ CF ₃ , —CF (CF ₃ ) ₂ , —OCF ₃ , —OCF ₂ CF _{3 , -SCF 3, -S (O)} CF 3, -S (O) 2 CF 3, -SCF 2 CF 3, -S (O) CF 2 CF 3, -S (O) 2 CF 2 CF 3, SF ₅ , a compound which is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom;

In formula (1-2-2), R ^8b is a C1-C6 alkyl group having one phenyl group (wherein the phenyl group is a cyano group, a halogen atom, or a halogen atom optionally having a halogen atom) One or more atoms or substituents selected from the group consisting of a -C3 alkyl group and a C1-C3 alkoxy group optionally having a halogen atom.) 1 thiazolyl group Having a C1-C6 alkyl group (wherein the thiazolyl group comprises a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, and a C1-C3 alkoxy group optionally having a halogen atom) A C1-C6 alkyl group having one imidazolyl group (wherein the imidazolyl group is a halogen atom, which may have one or more atoms or substituents selected from the group). It has one or more atoms or substituents selected from the group consisting of an atom, a C1-C3 alkyl group optionally having a halogen atom, and a C1-C3 alkoxy group optionally having a halogen atom. C1-C6 alkyl group having one furyl group (wherein the furyl group has a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, and a halogen atom). And optionally having one or more atoms or substituents selected from the group consisting of C1-C3 alkoxy groups.) C1-C6 alkyl group having one tetrahydrofuryl group (wherein The tetrahydrofuryl group includes a halogen atom, a C1-C3 alkyl group which may have a halogen atom, and a C1-C3 alkoxy group which may have a halogen atom. Or a C1-C6 alkyl group having one pyrazolyl group (wherein the pyrazolyl group is a halogen atom or a halogen atom). (It may have one or more atoms or substituents selected from the group consisting of a C1-C3 alkyl group which may have a C1-C3 alkoxy group which may have a halogen atom.) C1-C6 alkyl group having one pyridyl group (wherein the pyridyl group may have a halogen atom, a C1-C3 alkyl group which may have a halogen atom, and a halogen atom) One or more atoms or substituents selected from the group consisting of C1-C3 alkoxy groups) or a C1-C6 alkyl group having one pyrimidinyl group (wherein The pyrimidinyl group is one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group which may have a halogen atom, and a C1-C3 alkoxy group which may have a halogen atom. It may have a group. A compound which is
In Formula (1-2-2), R ^8b is a C1-C6 alkyl group having one phenyl group (wherein the phenyl group may have a cyano group, a halogen atom, or a halogen atom) (It may have one or more atoms or groups selected from the group consisting of a C1-C3 alkyl group and a C1-C3 alkoxy group optionally having a halogen atom.) One thiazolyl group Having a C1-C6 alkyl group (wherein the thiazolyl group comprises a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, and a C1-C3 alkoxy group optionally having a halogen atom) One or more atoms or groups selected from the group) or a C1-C6 alkyl group having one pyridyl group (wherein the pyridyl group is a halogen atom, a halogen atom). May have one or more atoms or groups selected from the group consisting of a C1-C3 alkyl group which may have a hydrogen atom and a C1-C3 alkoxy group which may have a halogen atom. A compound that is
In the formula (1-1-2), R ^8b is benzyl group, 4-chlorobenzyl group, 3-chlorobenzyl group, 2-chlorobenzyl group, 4-methylbenzyl group, 3-methylbenzyl group, 2-methyl. A compound which is a benzyl group, (2-chlorothiazol-5-yl) -methyl group, (pyridin-3-yl) -methyl group, or (2-chloropyridin-5-yl) -methyl group;

In the formula (1-2-2), compounds wherein A ^1b is ═CR ^9b — and R ^9b is a halogen atom or a hydrogen atom;
In the formula (1-2-2), compounds wherein A ^1b is ═CR ^9b — and R ^9b is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
In the formula (1-2-2), compounds wherein A ^1b is ═CR ^9b — and R ^9b is a fluorine atom or a hydrogen atom;

In the formula (1-3-1), R ^3c is a methyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, an ethyl group, an ethenyl group, an ethynyl group, a fluoromethyl group, a difluoromethyl group, or a trifluoromethyl group. _{, -CF 2 CF 3, -CF 2} CF 2 CF 3, -CF (CF 3) 2, -CF 2 CF 2 CF 2 CF 3, -OCF 3, -OCF 2 CF 3, -SCF 3, -S ( _{O) CF 3, -S (O} ) 2 CF 3, -SCF 2 CF 3, -S (O) CF 2 CF 3, -S (O) 2 CF 2 CF 3, 2- pyridyl group, 5-trifluoromethyl A compound which is a methyl-2-pyridyl group, a 2-pyrimidinyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
In the formula (1-3-1), R ^6c is a C1-C6 haloalkyl group, —OR ^22c (where R ^22c is a C1-C6 haloalkyl group), —S (O) _m R ^23c (wherein , ^{R 23c} is a C1-C6 haloalkyl group, m is 0, 1 or 2), - SF ₅ or the compound is a halogen atom.;
In the formula (1-3-1), R ^6c is a C1-C6 haloalkyl group, —OR ^22c (where R ^22c is a C1-C6 haloalkyl group), —S (O) _m R ^23c (wherein , ^{R 23c} is a C1-C6 haloalkyl group, m is 0, 1 or 2) or compound is -SF _5.;
In the formula (1-3-1), R ^6c is a C1-C6 haloalkyl group, —OR ^22c (where R ^22c is a C1-C6 haloalkyl group), —S (O) _m R ^23c (wherein , R ^23c is a C1-C6 haloalkyl group, and m is 0, 1 or 2.) or a halogen atom;
In Formula (1-3-1), R ^6c is a C1-C6 haloalkyl group, —OR ^22c (where R ^22c is a C1-C6 haloalkyl group) or —S (O) _m R ^23c (wherein , R ^23c is a C1-C6 haloalkyl group, and m is 0, 1 or 2);
In formula (1-3-1), R ^6c is a C1-C6 perfluoroalkyl group, —OR ^22c (where R ^22c is a C1-C6 perfluoroalkyl group) or —S (O) _m R ^A compound wherein R ^23c is a C1-C6 perfluoroalkyl group;
In the formula (1-3-1), R ^6c is a trifluoromethyl group, —CF ₂ CF ₃ , —CF ₂ CF ₂ CF ₃ , —CF (CF ₃ ) ₂ , —OCF ₃ , —OCF ₂ CF ₃ , _{-SCF 3, -S (O) CF} 3, -S (O) 2 CF 3, -SCF 2 CF 3, -S (O) CF 2 CF 3, -S (O) 2 CF 2 CF 3, SF 5 , A fluorine atom, a chlorine atom, a bromine atom or an iodine atom;
In the formula (1-3-1), R ^8c is benzyl group, 4-chlorobenzyl group, 3-chlorobenzyl group, 2-chlorobenzyl group, 4-methylbenzyl group, 3-methylbenzyl group, 2-methylbenzyl. A compound which is a group, (2-chlorothiazol-5-yl) -methyl group, (pyridin-3-yl) -methyl group, or (2-chloropyridin-5-yl) -methyl group;

In the formula (1-3-2), R ^3c is a methyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, an ethyl group, an ethenyl group, an ethynyl group, a fluoromethyl group, a difluoromethyl group, or a trifluoromethyl group. _{, -CF 2 CF 3, -CF 2} CF 2 CF 3, -CF (CF 3) 2, -CF 2 CF 2 CF 2 CF 3, -OCF 3, -OCF 2 CF 3, -SCF 3, -S ( _{O) CF 3, -S (O} ) 2 CF 3, -SCF 2 CF 3, -S (O) CF 2 CF 3, -S (O) 2 CF 2 CF 3, 2- pyridyl group, 5-trifluoromethyl A compound which is a methyl-2-pyridyl group, a 2-pyrimidinyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
In Formula (1-3-2), R ^7c is a C1-C6 haloalkyl group, -OR ^22c (where R ^22c is a C1-C6 haloalkyl group), -S (O) _m R ^23c (wherein , ^{R 23c} is a C1-C6 haloalkyl group, m is 0, 1 or 2), - SF ₅ or the compound is a halogen atom.;
In Formula (1-3-2), R ^7c is a C1-C6 haloalkyl group, -OR ^22c (where R ^22c is a C1-C6 haloalkyl group), -S (O) _m R ^23c (wherein , ^{R 23c} is a C1-C6 haloalkyl group, m is 0, 1 or 2) or compound is -SF _5.;
In Formula (1-3-2), R ^7c is a C1-C6 haloalkyl group, -OR ^22c (where R ^22c is a C1-C6 haloalkyl group), -S (O) _m R ^23c (wherein , R ^23c is a C1-C6 haloalkyl group, and m is 0, 1 or 2.) or a halogen atom;
In Formula (1-3-2), R ^7c is a C1-C6 haloalkyl group, —OR ^22c (where R ^22c is a C1-C6 haloalkyl group) or —S (O) _m R ^23c (wherein , R ^23c is a C1-C6 haloalkyl group, and m is 0, 1 or 2);
In Formula (1-3-2), R ^7c is a C1-C6 perfluoroalkyl group, —OR ^22c (where R ^22c is a C1-C6 perfluoroalkyl group) or —S (O) _m R ^A compound wherein R ^23c is a C1-C6 perfluoroalkyl group;
In Formula (1-3-2), R ^7c is a trifluoromethyl group, —CF ₂ CF ₃ , —CF ₂ CF ₂ CF ₃ , —CF (CF ₃ ) ₂ , —OCF ₃ , —OCF ₂ CF ₃ , _{-SCF 3, -S (O) CF} 3, -S (O) 2 CF 3, -SCF 2 CF 3, -S (O) CF 2 CF 3, -S (O) 2 CF 2 CF 3, SF 5 , A fluorine atom, a chlorine atom, a bromine atom or an iodine atom;
In the formula (1-3-2), R ^8c is benzyl group, 4-chlorobenzyl group, 3-chlorobenzyl group, 2-chlorobenzyl group, 4-methylbenzyl group, 3-methylbenzyl group, 2-methylbenzyl. A compound which is a group, (2-chlorothiazol-5-yl) -methyl group, (pyridin-3-yl) -methyl group, or (2-chloropyridin-5-yl) -methyl group;

In the formula (1-4-1), R ^3d is a methyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, an ethyl group, an ethenyl group, an ethynyl group, a fluoromethyl group, a difluoromethyl group, or a trifluoromethyl group. _{, -CF 2 CF 3, -CF 2} CF 2 CF 3, -CF (CF 3) 2, -CF 2 CF 2 CF 2 CF 3, -OCF 3, -OCF 2 CF 3, -SCF 3, -S ( _{O) CF 3, -S (O} ) 2 CF 3, -SCF 2 CF 3, -S (O) CF 2 CF 3, -S (O) 2 CF 2 CF 3, 2- pyridyl group, 5-trifluoromethyl A compound which is a methyl-2-pyridyl group, a 2-pyrimidinyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
In formula (1-4-1), R ^6d is a C1-C6 haloalkyl group, —OR ^22d (where R ^22d is a C1-C6 haloalkyl group), —S (O) _m R ^23d (wherein , ^{R 23d} is a C1-C6 haloalkyl group, m is 0, 1 or 2), - SF ₅ or the compound is a halogen atom.;
In formula (1-4-1), R ^6d is a C1-C6 haloalkyl group, —OR ^22d (where R ^22d is a C1-C6 haloalkyl group), —S (O) _m R ^23d (wherein , ^{R 23d} is a C1-C6 haloalkyl group, m is 0, 1 or 2) or compound is -SF _5.;
In formula (1-4-1), R ^6d is a C1-C6 haloalkyl group, —OR ^22d (where R ^22d is a C1-C6 haloalkyl group), —S (O) _m R ^23d (wherein , R ^23d is a C1-C6 haloalkyl group, and m is 0, 1 or 2.) or a halogen atom;
In Formula (1-4-1), R ^6d is a C1-C6 haloalkyl group, —OR ^22d (where R ^22d is a C1-C6 haloalkyl group) or —S (O) _m R ^23d (wherein , R ^23d is a C1-C6 haloalkyl group, and m is 0, 1 or 2);
In formula (1-4-1), R ^6d is a C1-C6 perfluoroalkyl group, —OR ^22d (where R ^22d is a C1-C6 perfluoroalkyl group) or —S (O) _m R ^A compound that is ^23d (wherein R ^23d is a C1-C6 perfluoroalkyl group);
In formula (1-4-1), R ^6d is a trifluoromethyl group, —CF ₂ CF ₃ , —CF ₂ CF ₂ CF ₃ , —CF (CF ₃ ) ₂ , —OCF ₃ , —OCF ₂ CF ₃ , _{-SCF 3, -S (O) CF} 3, -S (O) 2 CF 3, -SCF 2 CF 3, -S (O) CF 2 CF 3, -S (O) 2 CF 2 CF 3, SF 5 , A fluorine atom, a chlorine atom, a bromine atom or an iodine atom;
In the formula (1-4-1), R ^8d is benzyl group, 4-chlorobenzyl group, 3-chlorobenzyl group, 2-chlorobenzyl group, 4-methylbenzyl group, 3-methylbenzyl group, 2-methylbenzyl. A compound which is a group, (2-chlorothiazol-5-yl) -methyl group, (pyridin-3-yl) -methyl group, or (2-chloropyridin-5-yl) -methyl group;

In the formula (1-4-2), R ^3d is a methyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, an ethyl group, an ethenyl group, an ethynyl group, a fluoromethyl group, a difluoromethyl group, or a trifluoromethyl group. _{, -CF 2 CF 3, -CF 2} CF 2 CF 3, -CF (CF 3) 2, -CF 2 CF 2 CF 2 CF 3, -OCF 3, -OCF 2 CF 3, -SCF 3, -S ( _{O) CF 3, -S (O} ) 2 CF 3, -SCF 2 CF 3, -S (O) CF 2 CF 3, -S (O) 2 CF 2 CF 3, 2- pyridyl group, 5-trifluoromethyl A compound which is a methyl-2-pyridyl group, a 2-pyrimidinyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
In Formula (1-4-2), R ^7d is a C1-C6 haloalkyl group, —OR ^22d (where R ^22d is a C1-C6 haloalkyl group), —S (O) _m R ^23d (wherein , ^{R 23d} is a C1-C6 haloalkyl group, m is 0, 1 or 2), - SF ₅ or the compound is a halogen atom.;
In Formula (1-4-2), R ^7d is a C1-C6 haloalkyl group, —OR ^22d (where R ^22d is a C1-C6 haloalkyl group), —S (O) _m R ^23d (wherein , ^{R 23d} is a C1-C6 haloalkyl group, m is 0, 1 or 2) or compound is -SF _5.;
In Formula (1-4-2), R ^7d is a C1-C6 haloalkyl group, —OR ^22d (where R ^22d is a C1-C6 haloalkyl group), —S (O) _m R ^23d (wherein , R ^23d is a C1-C6 haloalkyl group, and m is 0, 1 or 2.) or a halogen atom;
In Formula (1-4-2), R ^7d is a C1-C6 haloalkyl group, —OR ^22d (where R ^22d is a C1-C6 haloalkyl group) or —S (O) _m R ^23d (wherein , R ^23d is a C1-C6 haloalkyl group, and m is 0, 1 or 2);
In Formula (1-4-2), R ^7d is a C1-C6 perfluoroalkyl group, —OR ^22d (where R ^22d is a C1-C6 perfluoroalkyl group) or —S (O) _m R ^A compound that is ^23d (wherein R ^23d is a C1-C6 perfluoroalkyl group);
In Formula (1-4-2), R ^7d is a trifluoromethyl group, —CF ₂ CF ₃ , —CF ₂ CF ₂ CF ₃ , —CF (CF ₃ ) ₂ , —OCF ₃ , —OCF ₂ CF ₃ , _{-SCF 3, -S (O) CF} 3, -S (O) 2 CF 3, -SCF 2 CF 3, -S (O) CF 2 CF 3, -S (O) 2 CF 2 CF 3, SF 5 , A fluorine atom, a chlorine atom, a bromine atom or an iodine atom;
In the formula (1-4-2), R ^8d is benzyl group, 4-chlorobenzyl group, 3-chlorobenzyl group, 2-chlorobenzyl group, 4-methylbenzyl group, 3-methylbenzyl group, 2-methylbenzyl. A compound which is a group, (2-chlorothiazol-5-yl) -methyl group, (pyridin-3-yl) -methyl group, or (2-chloropyridin-5-yl) -methyl group;

In the formula (1-5-1), R ^3e is a methyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, an ethyl group, an ethenyl group, an ethynyl group, a fluoromethyl group, a difluoromethyl group, or a trifluoromethyl group. _{, -CF 2 CF 3, -CF 2} CF 2 CF 3, -CF (CF 3) 2, -CF 2 CF 2 CF 2 CF 3, -OCF 3, -OCF 2 CF 3, -SCF 3, -S ( _{O) CF 3, -S (O} ) 2 CF 3, -SCF 2 CF 3, -S (O) CF 2 CF 3, -S (O) 2 CF 2 CF 3, 2- pyridyl group, 5-trifluoromethyl A compound which is a methyl-2-pyridyl group, a 2-pyrimidinyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
In Formula (1-5-1), R ^6e is a C1-C6 haloalkyl group, —OR ^22e (where R ^22e is a C1-C6 haloalkyl group), —S (O) _m R ^23e (wherein , ^{R 23e} is a C1-C6 haloalkyl group, m is 0, 1 or 2), - SF ₅ or the compound is a halogen atom.;
In Formula (1-5-1), R ^6e is a C1-C6 haloalkyl group, —OR ^22e (where R ^22e is a C1-C6 haloalkyl group), —S (O) _m R ^23e (wherein , ^{R 23e} is a C1-C6 haloalkyl group, m is 0, 1 or 2) or compound is -SF _5.;
In Formula (1-5-1), R ^6e is a C1-C6 haloalkyl group, —OR ^22e (where R ^22e is a C1-C6 haloalkyl group), —S (O) _m R ^23e (wherein , R ^23e is a C1-C6 haloalkyl group and m is 0, 1 or 2) or a halogen atom;
In Formula (1-5-1), R ^6e is a C1-C6 haloalkyl group, —OR ^22e (where R ^22e is a C1-C6 haloalkyl group) or —S (O) _m R ^23e (wherein , R ^23e is a C1-C6 haloalkyl group, and m is 0, 1 or 2 .;
In Formula (1-5-1), R ^6e is a C1-C6 perfluoroalkyl group, —OR ^22e (where R ^22e is a C1-C6 perfluoroalkyl group) or —S (O) _m R ^A compound wherein R ^23e is a C1-C6 perfluoroalkyl group;
In formula (1-5-1), R ^6e is a trifluoromethyl group, —CF ₂ CF ₃ , —CF ₂ CF ₂ CF ₃ , —CF (CF ₃ ) ₂ , —OCF ₃ , —OCF ₂ CF ₃ , _{-SCF 3, -S (O) CF} 3, -S (O) 2 CF 3, -SCF 2 CF 3, -S (O) CF 2 CF 3, -S (O) 2 CF 2 CF 3, SF 5 , A fluorine atom, a chlorine atom, a bromine atom or an iodine atom;
In the formula (1-5-1), R ^8e is benzyl group, 4-chlorobenzyl group, 3-chlorobenzyl group, 2-chlorobenzyl group, 4-methylbenzyl group, 3-methylbenzyl group, 2-methylbenzyl. A compound which is a group, (2-chlorothiazol-5-yl) -methyl group, (pyridin-3-yl) -methyl group, or (2-chloropyridin-5-yl) -methyl group;

In the formula (1-5-2), R ^3e is a methyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, an ethyl group, an ethenyl group, an ethynyl group, a fluoromethyl group, a difluoromethyl group, or a trifluoromethyl group. _{, -CF 2 CF 3, -CF 2} CF 2 CF 3, -CF (CF 3) 2, -CF 2 CF 2 CF 2 CF 3, -OCF 3, -OCF 2 CF 3, -SCF 3, -S ( _{O) CF 3, -S (O} ) 2 CF 3, -SCF 2 CF 3, -S (O) CF 2 CF 3, -S (O) 2 CF 2 CF 3, 2- pyridyl group, 5-trifluoromethyl A compound which is a methyl-2-pyridyl group, a 2-pyrimidinyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
In the formula (1-5-2), R ^7e is a C1-C6 haloalkyl group, -OR ^22e (where R ^22e is a C1-C6 haloalkyl group), -S (O) _m R ^23e (wherein , ^{R 23e} is a C1-C6 haloalkyl group, m is 0, 1 or 2), - SF ₅ or the compound is a halogen atom.;
In the formula (1-5-2), R ^7e is a C1-C6 haloalkyl group, -OR ^22e (where R ^22e is a C1-C6 haloalkyl group), -S (O) _m R ^23e (wherein , ^{R 23e} is a C1-C6 haloalkyl group, m is 0, 1 or 2) or compound is -SF _5.;
In the formula (1-5-2), R ^7e is a C1-C6 haloalkyl group, -OR ^22e (where R ^22e is a C1-C6 haloalkyl group), -S (O) _m R ^23e (wherein , R ^23e is a C1-C6 haloalkyl group and m is 0, 1 or 2) or a halogen atom;
In the formula (1-5-2), R ^7e is a C1-C6 haloalkyl group, —OR ^22e (where R ^22e is a C1-C6 haloalkyl group) or —S (O) _m R ^23e (wherein , R ^23e is a C1-C6 haloalkyl group, and m is 0, 1 or 2 .;
In formula (1-5-2), R ^7e is a C1-C6 perfluoroalkyl group, —OR ^22e (where R ^22e is a C1-C6 perfluoroalkyl group) or —S (O) _m R ^A compound wherein R ^23e is a C1-C6 perfluoroalkyl group;
In the formula (1-5-2), R ^7e is a trifluoromethyl group, —CF ₂ CF ₃ , —CF ₂ CF ₂ CF ₃ , —CF (CF ₃ ) ₂ , —OCF ₃ , —OCF ₂ CF ₃ , _{-SCF 3, -S (O) CF} 3, -S (O) 2 CF 3, -SCF 2 CF 3, -S (O) CF 2 CF 3, -S (O) 2 CF 2 CF 3, SF 5 , A fluorine atom, a chlorine atom, a bromine atom or an iodine atom;
In the formula (1-5-2), R ^8e is benzyl group, 4-chlorobenzyl group, 3-chlorobenzyl group, 2-chlorobenzyl group, 4-methylbenzyl group, 3-methylbenzyl group, 2-methylbenzyl. A compound which is a group, (2-chlorothiazol-5-yl) -methyl group, (pyridin-3-yl) -methyl group, or (2-chloropyridin-5-yl) -methyl group;

  As this invention compound, the following compounds are mentioned, for example.

In equation (1),
R ¹ is a C1-C6 alkyl group optionally having one or more halogen atoms,
R ² , R ⁴ and R ⁵ are hydrogen atoms,
R ³ is a C1-C6 alkyl group which may have one or more halogen atoms or a hydrogen atom,
R ⁶ and R ⁷ are each a C1-C6 alkyl group optionally having one or more halogen atoms or a hydrogen atom (provided that any of R ⁶ and R ⁷ is a hydrogen atom, and R ⁶ and R 7 The other of ⁷ is a C1-C6 alkyl group optionally having a halogen atom).
R ⁸ is a C1-C6 alkyl group having one phenyl group (wherein the phenyl group has one or more atoms or groups selected from the group consisting of a C1-C3 alkyl group and a halogen atom). Or a C1-C6 alkyl group having one 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is a C1-C3 alkyl group, and a halogen atom) And may have one or more atoms or groups selected from the group consisting of atoms).
A compound in which n is 0 or 2.

In formula (1-3-1),
R ^1c is a C1-C6 alkyl group optionally having one or more halogen atoms,
R ^3c is a C1-C6 alkyl group optionally having one or more halogen atoms or a hydrogen atom,
R ^6c is a C1-C6 alkyl group ^optionally having one or more halogen atoms,
R ^8c is a C1-C6 alkyl group having one phenyl group (wherein the phenyl group has one or more atoms or groups selected from the group consisting of C1-C3 alkyl groups and halogen atoms). Or a C1-C6 alkyl group having one 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is a C1-C3 alkyl group, and a halogen atom) And may have one or more atoms or groups selected from the group consisting of atoms).
A compound in which n is 0 or 2.

In formula (1-3-1),
R ^1c is a C1-C6 alkyl group optionally having one or more halogen atoms,
R ^3c is a C1-C6 alkyl group optionally having one or more halogen atoms,
R ^6c is a C1-C6 alkyl group ^optionally having one or more halogen atoms,
R ^8c is a C1-C6 alkyl group having one phenyl group (wherein the phenyl group may have one or more halogen atoms), or one 5- or 6-membered aromatic complex. A C1-C6 alkyl group having a cyclic group (wherein the 5- or 6-membered aromatic heterocyclic group may have one or more halogen atoms);
A compound wherein n is 2.

In formula (1-3-1),
R ^1c is an ethyl group,
R ^8c is benzyl group, 2-methylbenzyl group, 3-methylbenzyl group, 4-methylbenzyl group, 2-chlorobenzyl group, 3-chlorobenzyl group, 4-chlorobenzyl group, (2-chloro-thiazole-5 -Yl) -methyl group, (2-chloro-pyridin-5-yl) -methyl group, or (pyridin-3-yl) -methyl group,
R ^3c is a C1-C6 haloalkyl group or a hydrogen atom,
R ^6c is a C1-C6 haloalkyl group,
A compound in which n is 0 or 2.

In the formula (1-4-2),
R ^1d is a C1-C6 alkyl group optionally having one or more halogen atoms,
R ^3d is a C1-C6 alkyl group optionally having one or more halogen atoms or a hydrogen atom,
R ^7d is a C1-C6 alkyl group ^optionally having one or more halogen atoms,
R ^8d is a C1-C6 alkyl group having one phenyl group (wherein the phenyl group represents one or more atoms or groups selected from the group consisting of a cyano group, a C1-C3 alkyl group, and a halogen atom). Or a C1-C6 alkyl group having one 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is a C1-C3 alkyl group) And may have one or more atoms or groups selected from the group consisting of halogen atoms).
A compound in which n is 0 or 2.

In the formula (1-4-2),
R ^1d is a C1-C6 alkyl group optionally having one or more halogen atoms,
R ^3d is a C1-C6 alkyl group optionally having one or more halogen atoms or a hydrogen atom,
R ^7d is a C1-C6 alkyl group ^optionally having one or more halogen atoms,
R ^8d is a C1-C6 alkyl group having one 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group may have one or more halogen atoms). Good)
A compound wherein n is 2.

In the formula (1-4-2),
R ^1d is an ethyl group,
R ^8d is benzyl group, 2-methylbenzyl group, 3-methylbenzyl group, 4-methylbenzyl group, 2-chlorobenzyl group, 3-chlorobenzyl group, 4-chlorobenzyl group, (2-chloro-thiazole-5 -Yl) -methyl group, (2-chloro-pyridin-5-yl) -methyl group, or (pyridin-3-yl) -methyl group,
R ^3d is a C1-C6 haloalkyl group,
R ^6d is a C1-C6 haloalkyl group,
A compound in which n is 0 or 2.

  Next, the manufacturing method of this invention compound is demonstrated.

  The compound of the present invention and the intermediate compound can be produced, for example, by the following (Production Method 1) to (Production Method 24).

(Production method 1)
The present compound (1)-(n = 1) in which n is 1 in formula (1) or (1)-(n = 2) in which n is 2 represents the present compound (1) in which n is 0 -(N = 0) can be produced by oxidation.
[Wherein the symbols have the same meaning as described above. ]
The present compound (1)-(n = 1) in which n is 1 in the formula (1) is produced by oxidizing the present compound (1)-(n = 0) in which n is 0 with an oxidizing agent. can do.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform, alcohols such as methanol and ethanol, acetic acid, water, and mixtures thereof.
Examples of the oxidizing agent used for the reaction include sodium periodate or m-chloroperbenzoic acid.
In the reaction, the oxidizing agent is usually used in a ratio of 1 to 3 moles relative to 1 mole of the compound (1)-(n = 0) of the present invention. Preferably, the oxidizing agent is used in a ratio of 1 to 1.2 mol with respect to 1 mol of the present compound (1)-(n = 0).
The reaction temperature of the reaction is usually in the range of -20 to 80 ° C. The reaction time is usually in the range of 0.1 to 12 hours.
After completion of the reaction, the reaction mixture is extracted with an organic solvent, and the organic layer is washed with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) or an aqueous solution of a base (for example, sodium bicarbonate) as necessary, dried, By performing post-treatment operations such as concentration, the compound (1)-(n = 1) of the present invention can be isolated. The isolated present compound (1)-(n = 1) can be further purified by chromatography, recrystallization or the like.

The present compound (1)-(n = 2) in which n is 2 in the formula (1) is produced by oxidizing the present compound (1)-(n = 1) in which n is 1 with an oxidizing agent. can do.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform, alcohols such as methanol and ethanol, acetic acid, water, and mixtures thereof.
Examples of the oxidizing agent used in the reaction include m-chloroperbenzoic acid or hydrogen peroxide water.
In the reaction, the oxidizing agent is usually used at a ratio of 1 to 4 moles relative to 1 mole of the compound (1)-(n = 1) of the present invention. Preferably, the oxidizing agent is used in a ratio of 1 to 2 moles relative to 1 mole of the compound (1)-(n = 1) of the present invention.
The reaction temperature of the reaction is usually in the range of -20 to 120 ° C. The reaction time is usually in the range of 0.1 to 12 hours.
After completion of the reaction, the reaction mixture is extracted with an organic solvent, and the organic layer is washed with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) or an aqueous solution of a base (for example, sodium bicarbonate) as necessary, dried, By performing post-treatment operations such as concentration, the compound (1)-(n = 2) of the present invention can be isolated. The compound (1)-(n = 2) of the present invention can be further purified by chromatography, recrystallization and the like.

In addition, the compound (1)-(n = 2) of the present invention in which n is 2 in the formula (1) oxidizes the compound (1)-(n = 0) of the present invention in which n is 0 with an oxidizing agent. Can be produced in a one-step reaction (one pot).
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform, alcohols such as methanol and ethanol, acetic acid, water, and mixtures thereof.
Examples of the oxidizing agent used in the reaction include m-chloroperbenzoic acid or hydrogen peroxide water.
In the reaction, the oxidizing agent is usually used at a ratio of 2 to 5 mol with respect to 1 mol of the present compound (1)-(n = 0). Preferably, the oxidizing agent is used in a ratio of 2 to 3 moles with respect to 1 mole of the present compound (1)-(n = 0).
The reaction temperature of the reaction is usually in the range of 0 to 120 ° C. The reaction time is usually in the range of 0.1 to 12 hours.
After completion of the reaction, the reaction mixture is extracted with an organic solvent, and the organic layer is washed with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) or an aqueous solution of a base (for example, sodium bicarbonate) as necessary, dried, By performing post-treatment operations such as concentration, the compound (1)-(n = 2) of the present invention can be isolated. The isolated present compound (1)-(n = 2) can be further purified by chromatography, recrystallization or the like.

(Production method 2)
The compound (1) of the present invention was prepared by reacting the intermediate compound (M1) with the intermediate compound (M2) or the intermediate compound (M18) to produce the intermediate compound (M3). It can be produced by intramolecular condensation (cyclization) of the compound (M3).
[Wherein the symbols have the same meaning as described above. ]
The intermediate compound (M3) can be produced by reacting the intermediate compound (M1) and the intermediate compound (M2) in the presence of a condensing agent.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include 1,4-dioxane, diethyl ether, tetrahydrofuran (hereinafter referred to as THF), ethers such as tert-butyl methyl ether, dichloromethane, chloroform, carbon tetrachloride, 1,2 -Halogenated hydrocarbons such as dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; N, N-dimethylformamide (hereinafter referred to as DMF) Aprotic polar solvents such as N-methylpyrrolidone (hereinafter referred to as NMP), 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide (hereinafter referred to as DMSO), pyridine, and quinoline And nitrogen-containing aromatic compounds such as .
Examples of the condensing agent used in the reaction include carbodiimides such as 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (hereinafter referred to as WSC) and 1,3-dicyclohexylcarbodiimide.
This reaction can also be performed by adding a catalyst as needed.
Examples of the catalyst used for the reaction include 1-hydroxybenzotriazole (hereinafter referred to as HOBt).
In this reaction, the intermediate compound (M2) is usually in a proportion of 0.5 to 2 mol, the condensing agent is usually in a proportion of 1 to 5 mol, and the catalyst is usually 0 with respect to 1 mol of the intermediate compound (M1). Used in a ratio of 0.01 to 1 mol.
The reaction temperature of the reaction is usually in the range of 0 to 120 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and extracted with an organic solvent and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture. The intermediate compound (M3) can be isolated by collecting the resulting solid by filtration. The isolated intermediate compound (M3) can be further purified by recrystallization, chromatography or the like.

The intermediate compound (M3) can be produced by reacting the intermediate compound (M1) with the intermediate compound (M18).
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatics such as toluene and xylene. Aromatic hydrocarbons, halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, acid amides such as DMF and NMP, sulfoxides such as DMSO, and mixtures thereof It is done.
This reaction can also be performed by adding a base as necessary.
The base used in the reaction includes alkali metal carbonates such as sodium carbonate and potassium carbonate, tertiary amines such as triethylamine and N, N-diisopropylethylamine, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine. And the like.
In the reaction, the intermediate compound (M18) is usually used in a proportion of 1 to 3 mol and the base is usually used in a proportion of 1 to 10 mol with respect to 1 mol of the intermediate compound (M1).
The reaction temperature of the reaction is usually in the range of -20 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the intermediate compound (M3) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. it can. The isolated intermediate compound (M3) can be further purified by chromatography, recrystallization and the like.

The compound (1) of the present invention can be produced by intramolecular condensation of the intermediate compound (M3).
The reaction is usually performed in the presence of a solvent. Examples of the solvent used in the reaction include ethers such as 1,4-dioxane, diethyl ether, THF, tert-butyl methyl ether, and halogenated carbonization such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, and chlorobenzene. Hydrogen, hydrocarbons such as toluene, benzene, xylene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, DMF, NMP, 1,3-dimethyl-2-imidazolidinone, non-DMSO, etc. Examples thereof include protic polar solvents, nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixtures thereof.
In the reaction, a condensing agent, an acid, a base, or a chlorinating agent can be added as necessary.
Examples of the condensing agent used in the reaction include phosphorus oxychloride, acetic anhydride, trifluoroacetic anhydride, WSC, a mixture of triphenylphosphine and base and carbon tetrachloride or carbon tetrabromide, triphenylphosphine and diethyl azodicarboxylate. And the like, and the like.
Examples of the acid used for the reaction include sulfonic acids such as p-toluenesulfonic acid, carboxylic acids such as acetic acid, and polyphosphoric acid.
Examples of the base used in the reaction include pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo [5.4.0] -7-undecene (hereinafter referred to as DBU), 1,5-diazabicyclo [ 4.3.0] Nitrogen-containing heterocyclic compounds such as 5-nonene, tertiary amines such as triethylamine and N, N-diisopropylethylamine, inorganic bases such as tripotassium phosphate, potassium carbonate and sodium hydride. It is done.
Examples of the chlorinating agent used in the reaction include phosphorus oxychloride.
In the reaction, with respect to 1 mol of the intermediate compound (M3), when a condensing agent is used, the ratio of the condensing agent is usually 1 to 5 mol, and when an acid is used, the acid is 0.1 mol to 5 mol. In the case of using a base, the base is used in a proportion of 1 to 5 mol, and in the case of using a chlorinating agent, the chlorinating agent is used in a proportion of 1 to 5 mol.
The reaction temperature of the reaction is usually in the range of 0 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and extracted with an organic solvent and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture. The present compound (1) can be isolated by collecting the obtained solid by filtration. The isolated compound (1) of the present invention can be further purified by recrystallization, chromatography or the like.

The compound (1) of the present invention can be produced by a one-step reaction by reacting the intermediate compound (M1) with the intermediate compound (M2) in the presence of a condensing agent.
The reaction is usually performed in the presence of a solvent. Examples of the solvent used in the reaction include ethers such as 1,4-dioxane, diethyl ether, THF, tert-butyl methyl ether, and halogenations such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, and chlorobenzene. Hydrocarbons, hydrocarbons such as toluene, benzene, xylene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, DMF, NMP, 1,3-dimethyl-2-imidazolidinone, DMSO, etc. Examples thereof include aprotic polar solvents, nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixtures thereof.
Examples of the condensing agent used in the reaction include carbodiimides such as WSC and 1,3-dicyclohexylcarbodiimide.
This reaction can also be performed by adding a catalyst as needed.
Examples of the catalyst used in the reaction include 1-hydroxybenzotriazole.
In the reaction, with respect to 1 mol of the intermediate compound (M1), the intermediate compound (M2) is usually in a proportion of 1 to 2 mol, the condensing agent is usually in a proportion of 1 to 5 mol, and the catalyst is usually 0.01. Used in a proportion of ˜1 mol.
The reaction temperature of the reaction is usually in the range of 0 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and extracted with an organic solvent and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture. The present compound (1) can be isolated by collecting the obtained solid by filtration. The isolated compound (1) of the present invention can be further purified by recrystallization, chromatography or the like.

The compound (1) of the present invention can be produced by a one-step reaction by reacting the intermediate compound (M1) with the intermediate compound (M18).
The reaction is performed in the presence or absence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatics such as toluene and xylene. Aromatic hydrocarbons, halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, acid amides such as DMF and NMP, sulfoxides such as DMSO, and mixtures thereof It is done.
This reaction can also be performed by adding a base as necessary.
The base used in the reaction includes alkali metal carbonates such as sodium carbonate and potassium carbonate, tertiary amines such as triethylamine and N, N-diisopropylethylamine, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine. And the like.
In the reaction, the intermediate compound (M18) is usually used in a proportion of 1 to 3 mol and the base is usually used in a proportion of 1 to 10 mol with respect to 1 mol of the intermediate compound (M1).
The reaction temperature of the reaction is usually in the range of 20 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (1) of the present invention can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. it can. The isolated compound (1) of the present invention can be further purified by chromatography, recrystallization and the like.

(Production method 3)
The compound of the present invention can be produced by reacting the intermediate compound (M1) with the intermediate compound (M4) in the presence of an oxidizing agent.
[Wherein the symbols have the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent. Examples of the solvent used in the reaction include alcohols such as methanol and ethanol, ethers such as 1,4-dioxane, diethyl ether, THF and tert-butyl methyl ether, dichloromethane, chloroform, carbon tetrachloride, 1,2- Halogenated hydrocarbons such as dichloroethane and chlorobenzene, hydrocarbons such as toluene, benzene and xylene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, DMF, NMP, 1,3-dimethyl-2- Examples thereof include aprotic polar solvents such as imidazolidinone and DMSO, nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixtures thereof.
Examples of the oxidizing agent used in the reaction include oxygen, copper (II) chloride, and DDQ.
The reaction can be carried out by adding an acid as necessary.
Examples of the acid used for the reaction include sulfonic acids such as p-toluenesulfonic acid, carboxylic acids such as acetic acid, and polyphosphoric acid.
The reaction can be carried out by adding sulfite as necessary.
Examples of the sulfite used in the reaction include sulfites such as sodium bisulfite and sodium disulfite.
In the reaction, the intermediate compound (M4) is usually used in a proportion of 1 to 2 mol, the oxidizing agent is usually used in a proportion of 1 mol to 5 mol, and an acid is used in the case of using an acid with respect to 1 mol of the intermediate compound (M1). Is usually in a proportion of 0.1 to 2 mol, and when sulfite is used, sulfite is usually used in a proportion of 1 to 5 mol.
The reaction temperature of the reaction is usually in the range of 0 to 200 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and extracted with an organic solvent and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture. The present compound (1) can be isolated by collecting the obtained solid by filtration. The isolated compound (1) of the present invention can be further purified by recrystallization, chromatography or the like.

(Production Method 4)
The present compound (1)-(n = 0) in which n is 0 in the formula (1) can be produced by reacting the intermediate compound (M6) with the compound (M7) in the presence of a base. it can.
[Wherein, V ¹ represents a halogen atom, and other symbols have the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, DMF, Examples thereof include acid amides such as NMP, sulfoxides such as DMSO, and mixtures thereof.
Examples of the base used in the reaction include alkali metal carbonates such as sodium carbonate and potassium carbonate, and alkali metal hydrides such as sodium hydride.
In the reaction, with respect to 1 mol of the intermediate compound (M6), the compound (M7) is usually used in a proportion of 1 to 10 mol, and the base is usually used in a proportion of 1 to 10 mol.
The reaction temperature of the reaction is usually in the range of 0 to 150 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, post-treatment operations such as extraction of the reaction mixture with an organic solvent, drying and concentration of the organic layer, and the like are performed, whereby the compound (1)-(n = 0) of the present invention in which n is 0 are simply obtained. Can be separated. The isolated present compound (1)-(n = 0) in which n is 0 can be further purified by chromatography, recrystallization and the like.
In the reaction, V ¹ is preferably a fluorine atom or a chlorine atom.

(Production method 5)
After the intermediate compound (M1) and the intermediate compound (M19) or the intermediate compound (M39) are reacted to produce the intermediate compound (M20), the intramolecular mixture of the resulting intermediate compound (M20) The intermediate compound (M6) can be produced by condensation.
[Wherein the symbols have the same meaning as described above. ]
The intermediate compound (M20) can be produced according to the method described in Production Method 2 using the intermediate compound (M19) instead of the intermediate compound (M2).
The intermediate compound (M20) can be produced according to the method described in Production Method 2 using the intermediate compound (M39) instead of the intermediate compound (M18).
The intermediate compound (M6) can be produced according to the method described in Production Method 2 using the intermediate compound (M20) instead of the intermediate compound (M3).
Further, the intermediate compound (M6) can be produced by a one-step reaction in accordance with the method described in Production Method 2, using the intermediate compound (M19) instead of the intermediate compound (M2).
In addition, intermediate compound (M6) can be produced in a one-step reaction) using intermediate compound (M39) instead of intermediate compound (M2) and following the method described in Production Method 2.
In the reaction, V ¹ is preferably a fluorine atom or a chlorine atom.

(Production method 6)
By reacting the intermediate compound (M20) and the compound (M7), an intermediate compound (M3)-(n = 0) in which n is 0 in the formula (M3) can be produced. Moreover, this invention compound (1)-(n = 0) whose n is 0 in Formula (1) can be manufactured by intramolecular condensation of the obtained intermediate compound (M3).
[Wherein the symbols have the same meaning as described above]
By using the intermediate compound (M20) instead of the intermediate compound (M6), an intermediate compound (M3)-(n = 0) in which n is 0 can be produced according to the production method 4. .
The intermediate compound (M3)-(n = 0) where n is 0 instead of the intermediate compound (M3), and according to the production method 2, the present compound (1)-wherein n is 0 (N = 0) can be manufactured.
Further, the intermediate compound (M20) is used instead of the intermediate compound (M6), and according to the method of production method 4, the present compound (1)-(n = 0) in which n is 0 is reacted in one step. Can also be manufactured.
In the reaction, V ¹ is preferably a fluorine atom or a chlorine atom.

(Production method 7)
The compound (1)-(n = 0) of the present invention in which n is 0 in the formula (1) is an intermediate compound (M8) or an intermediate compound (M8 ′) that is a disulfide thereof, a compound (M17), Can be prepared by reacting in the presence of a base.
[Wherein, L represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom, a trifluoromethanesulfonyloxy group and a methanesulfonyloxy group, and the other symbols have the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, DMF, Examples include acid amides such as NMP, sulfoxides such as DMSO, and mixtures thereof.
Examples of the base used in the reaction include alkali metal or alkaline earth metal hydrides such as sodium hydride, potassium hydride and calcium hydride, inorganic bases such as sodium carbonate and potassium carbonate, and organic bases such as triethylamine. Can be mentioned.
When the intermediate compound (M8 ′) that is a disulfide is used, it is usually performed in the presence of a reducing agent.
Examples of the reducing agent used in the reaction include sodium hydroxymethanesulfinate (trade name: Rongalite).
In the reaction, with respect to 1 mol of the intermediate compound (M8), the compound (M17) is usually used in a proportion of 1 to 10 mol, and the base is usually used in a proportion of 1 to 10 mol. When the intermediate compound (M8 ′) that is a disulfide is used, the ratio of the compound (M17) is usually 0.5 to 5 mol and the base is usually 0 with respect to 1 mol of the intermediate compound (M8 ′). .5-5 mole ratio, reducing agent is used in 0.5-5 mole ratio.
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, post-treatment operations such as extraction of the reaction mixture with an organic solvent, drying and concentration of the organic layer, and the like are performed, whereby the compound (1)-(n = 0) of the present invention in which n is 0 are simply obtained. Can be separated. The isolated present compound (1)-(n = 0) in which n is 0 can be further purified by chromatography, recrystallization and the like.

(Production method 8)
This invention compound (1)-(n = 0) whose n is 0 in Formula (1) reacts an intermediate compound (M8 '), a compound (M17'-1), or a compound (M17'-2). Can be manufactured.
Wherein, V ² represents a chlorine atom, a bromine atom or an iodine atom, the other symbols have the same meanings as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, DMF, Examples include acid amides such as NMP, sulfoxides such as DMSO, and mixtures thereof.
In the reaction, compound (M17′-1) is usually used at a ratio of 0.5 to 2 mol with respect to 1 mol of intermediate compound (M8 ′). Moreover, when using a compound (M17'-2), a compound (M17'-2) is normally used in the ratio of 0.5-2 mol with respect to 1 mol of intermediate compounds (M8 ').
The reaction temperature of the reaction is usually in the range of -80 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, post-treatment operations such as extraction of the reaction mixture with an organic solvent, drying and concentration of the organic layer, and the like are performed, whereby the compound (1)-(n = 0) of the present invention in which n is 0 are simply obtained. Can be separated. The isolated present compound (1)-(n = 0) in which n is 0 can be further purified by chromatography, recrystallization and the like.

(Production method 9)
An intermediate compound (M8) can be produced by reacting the intermediate compound (M6) with a sulfurizing agent. Further, the intermediate compound (M8 ′), which is a disulfide thereof, can be produced by oxidizing the intermediate compound (M8) with an oxidizing agent.
[Wherein the symbols have the same meaning as described above. ]
The intermediate compound (M8) can be produced according to the production method 4 using a sulfurizing agent such as sodium sulfide, sodium hydrogen sulfide or hydrogen sulfide instead of the compound (M7).
Here, the reaction from the intermediate compound (M8) to the intermediate compound (M8 ′) is likely to occur, and the intermediate compound (M8 ′) may be generated during the synthesis of the intermediate compound (M8).
In the reaction, V ¹ is preferably a fluorine atom or a chlorine atom.

The intermediate compound (M8 ′) can be produced by oxidizing the intermediate compound (M8) with an oxidizing agent.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include water, alcohols such as methanol and ethanol, THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, ethers such as 1,4-dioxane, and aromatic hydrocarbons such as toluene and xylene. Nitriles such as acetonitrile, acid amides such as DMF and NMP, sulfoxides such as DMSO, carboxylic acids such as acetic acid, and mixtures thereof.
Examples of the oxidizing agent used in the reaction include oxygen, iodine, hydrogen peroxide solution, potassium ferricyanide, and the like.
In the reaction, an oxidizing agent is usually used at a ratio of 0.5 to 10 mol with respect to 1 mol of the intermediate compound (M8).
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the intermediate compound (M8 ′) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated intermediate compound (M8 ′) can be further purified by chromatography, recrystallization and the like.

(Production method 10)
The present compound (1) can be produced by reacting the intermediate compound (P2) with the compound (M10) in the presence of a base.
[Wherein the symbols have the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, DMF, Examples include acid amides such as NMP, sulfoxides such as DMSO, and mixtures thereof.
Examples of the base used in the reaction include alkali metal or alkaline earth metal hydrides such as sodium hydride, potassium hydride and calcium hydride, inorganic bases such as sodium carbonate and potassium carbonate, and organic bases such as triethylamine. Is mentioned.
In the reaction, with respect to 1 mol of the present compound (P2), the compound (M10) is usually used in a proportion of 1 to 5 mol, and the base is usually used in a proportion of 1 to 3 mol.
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (1) of the present invention can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound (1) of the present invention can be further purified by chromatography, recrystallization and the like.

(Production method 11)
The intermediate compound (M2) can be produced by hydrolyzing the intermediate compound (M37).
[Wherein the symbols have the same meaning as described above. ]
When hydrolyzing with an acid, the reaction is usually carried out using an aqueous acid solution as a solvent.
Examples of the acid used for the reaction include mineral acids such as hydrochloric acid, nitric acid, phosphoric acid and sulfuric acid, and carboxylic acids such as acetic acid and trifluoroacetic acid.
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the intermediate compound (M2) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated intermediate compound (M2) can be further purified by chromatography, recrystallization and the like.
When hydrolyzing with a base, the reaction is usually carried out in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, alcohols such as methanol and ethanol, water, and a mixture thereof.
Examples of the base used for the reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.
In the reaction, the base is generally used at a ratio of 1 to 10 mol per 1 mol of the intermediate compound (M37).
The reaction temperature of the reaction is usually in the range of 0 to 120 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the intermediate solution (M2) is isolated by acidifying the reaction solution and then performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Can do. The isolated intermediate compound (M2) can be further purified by chromatography, recrystallization and the like.

(Production method 12)
Intermediate compound (M18) can be produced by reacting intermediate compound (M2) in the presence of a chlorinating agent.
[Wherein the symbols have the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, and aliphatic halogens such as dichloromethane and chloroform. Hydrocarbons and mixtures thereof.
Examples of the chlorinating agent used in the reaction include thionyl chloride, oxalyl dichloride, phosphorus oxychloride and the like.
In the reaction, the chlorinating agent is usually used at a ratio of 1 to 5 mol with respect to 1 mol of the intermediate compound (M2).
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the intermediate compound (M18) can be isolated by removing the solvent.

(Production method 13)
Intermediate compound (M2), intermediate compound (M4) or intermediate compound (M37) are respectively intermediate compound (M19), intermediate compound (M22) or intermediate compound (M36) and compound (M7). Can be produced by oxidizing the compound obtained as necessary.
[Wherein the symbols have the same meaning as described above. ]
An intermediate compound (M2)-(n = 0) in which n is 0 can be produced according to the production method 4 using the intermediate compound (M19) instead of the intermediate compound (M6). it can.
An intermediate compound (M4)-(n = 0) in which n is 0 can be produced in accordance with the production method 4 using the intermediate compound (M22) instead of the intermediate compound (M6). it can.
An intermediate compound (M37)-(n = 0) in which n is 0 can be produced according to the production method 4 using the intermediate compound (M36) instead of the intermediate compound (M6). it can.

According to the method of Production Method 1, an intermediate compound in which n is 1 is used instead of the present compound (1)-(n = 0) in which n is 0 and n is an intermediate compound (M2). The intermediate compound (M2)-(n = 1) or the intermediate compound (M2)-(n = 2) in which n is 2 can be produced.
In place of the present compound (1)-(n = 0) where n is 0, an intermediate compound (M4)-(n = 0) where n is 0 is used according to the method of production method 1, Intermediate compound (M4)-(n = 1) where n is 1 or intermediate compound (M4)-(n = 2) where n = 2 can be produced.
In place of the present compound (1)-(n = 0) where n is 0, an intermediate compound (M37)-(n = 0) where n is 0 is used, according to the method of production method 1, Intermediate compound (37)-(n = 1) where n is 1 or intermediate compound (M37)-(n = 2) where n = 2 can be produced.
In the reaction, V ¹ is preferably a fluorine atom or a chlorine atom.

(Production method 14)
The intermediate compound (M30) can be produced by reacting the intermediate compound (M33) with the compound (M28) or by nitrating the intermediate compound (M29). The intermediate compound (M1) can be produced by reducing the intermediate compound (M30) obtained here.
[Wherein the symbols have the same meaning as described above. ]

Intermediate compound (M30) can be produced by reacting intermediate compound (M33) with compound (M28) in the presence of a base.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, DMF, Examples thereof include acid amides such as NMP, sulfoxides such as DMSO, and mixtures thereof.
Examples of the base used in the reaction include alkali metal hydrides such as sodium hydride, alkali metal carbonates such as sodium carbonate and potassium carbonate, tertiary amines such as triethylamine and N, N-diisopropylethylamine, and pyridine, Examples thereof include nitrogen-containing aromatic compounds such as 4-dimethylaminopyridine.
In the reaction, with respect to 1 mol of the intermediate compound (M33), the compound (M28) is usually used in a proportion of 1 to 10 mol, and the base is usually used in a proportion of 0 to 10 mol.
The reaction temperature of the reaction is usually in the range of 0 to 150 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the intermediate compound (M30) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated intermediate compound (M30) can be further purified by chromatography, recrystallization and the like.

Intermediate compound (M30) can be produced by reacting intermediate compound (M29) in the presence of a nitrating agent.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform, acetic acid, concentrated sulfuric acid, concentrated nitric acid, water, and mixtures thereof.
An example of the nitrating agent used in the reaction is concentrated nitric acid.
In the reaction, the nitrating agent is usually used at a ratio of 1 to 3 moles relative to 1 mole of the intermediate compound (M29).
The reaction temperature of the reaction is usually in the range of -10 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the intermediate compound (M30) can be isolated by performing post-treatment operations such as pouring the reaction mixture into water, extraction with an organic solvent, and drying and concentration of the organic layer. . The isolated intermediate compound (M30) can be further purified by chromatography, recrystallization and the like.

The intermediate compound (M1) can be produced by reacting the intermediate compound (M30) with hydrogen in the presence of a hydrogenation catalyst.
The reaction is usually performed in a hydrogen atmosphere at 1 to 100 atm, usually in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, esters such as ethyl acetate and butyl acetate, alcohols such as methanol and ethanol, water And mixtures thereof.
Examples of the hydrogenation catalyst used in the reaction include transition metal compounds such as palladium carbon, palladium hydroxide, Raney nickel, and platinum oxide.
In the reaction, hydrogen is usually used in a proportion of 3 mol and a hydrogenation catalyst is usually used in a proportion of 0.001 to 0.5 mol with respect to 1 mol of the intermediate compound (M30).
This reaction can also be performed by adding an acid, a base or the like, if necessary.
Examples of the acid used for the reaction include acetic acid and hydrochloric acid, and examples of the base used for the reaction include tertiary amines such as triethylamine, magnesium oxide and the like.
The reaction temperature of the reaction is usually in the range of -20 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the intermediate compound (M1) can be isolated by performing post-treatment operations such as filtration of the reaction mixture, extraction with an organic solvent as necessary, and drying and concentration of the organic layer. it can. The isolated intermediate compound (M1) can be further purified by chromatography, recrystallization and the like.

The intermediate compound (M1) can be produced by subjecting the intermediate compound (M30) to a reduction reaction.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, esters such as ethyl acetate and butyl acetate, alcohols such as methanol and ethanol, Examples thereof include acid amides such as DMF and NMP, and mixtures thereof.
Examples of the reducing agent used in the reaction include reducing agents such as iron powder and zinc powder.
The reaction can be carried out by adding an acid such as hydrochloric acid or acetic acid and water as necessary.
In the reaction, the reducing agent is usually used in a proportion of 3 to 10 mol and the acid is usually used in a proportion of 0.1 to 10 mol with respect to 1 mol of the intermediate compound (M30).
The reaction temperature is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is filtered, water is added to the filtrate, extraction is performed with an organic solvent, and post-treatment operations such as drying and concentration of the organic layer are performed to obtain the intermediate compound (M1). It can be isolated. The isolated intermediate compound (M1) can also be purified by chromatography, recrystallization and the like.

The intermediate compound (M30) is prepared by acetylating the intermediate compound (M29) to produce the intermediate compound (M29 ′), and then nitration of the obtained intermediate compound (M29 ′). It can also be produced by producing ') and hydrolyzing the obtained intermediate compound (M30').
[Wherein the symbols have the same meaning as described above. ]
The intermediate compound (M29 ′) can be produced by reacting the intermediate compound (M29) in the presence of an acetylating agent.
The reaction is usually performed in the presence of a solvent or using an acylating agent as a solvent.
Examples of the solvent used in the reaction include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform, ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, and aromatics such as toluene and xylene. Group hydrocarbons, nitriles such as acetonitrile, acid amides such as DMF and NMP, sulfoxides such as DMSO, acetic anhydride, and mixtures thereof.
Examples of the acetylating agent used in the reaction include acetic anhydride and p-acetoxynitrobenzene.
This reaction can also be performed by adding a base as necessary.
Examples of the base used in the reaction include tertiary amines such as triethylamine and N, N-diisopropylethylamine, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
In the reaction, the acetylating agent is usually used in a proportion of 1 mol or more and the base is usually used in a proportion of 0 to 10 mol with respect to 1 mol of the intermediate compound (M29).
The reaction temperature of the reaction is usually in the range of 0 to 150 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the intermediate compound (M29 ′) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated intermediate compound (M29 ′) can be further purified by chromatography, recrystallization and the like.

  In place of the intermediate compound (M29), the intermediate compound (M29 ′) was used, and the intermediate compound (M29) was nitrated in the production method 14 to produce the intermediate compound (M30). Body compound (M30 ′) can be produced.

  The intermediate compound (M30) can be produced by hydrolyzing the intermediate compound (M30 ′) in the presence of an acid or a base.

When hydrolyzing with an acid, the reaction is usually carried out using an aqueous acid solution as a solvent.
Examples of the acid used in the reaction include mineral acids such as hydrochloric acid and sulfuric acid, and carboxylic acids such as acetic acid and trifluoroacetic acid.
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the intermediate compound (M30) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated intermediate compound (M30) can be further purified by chromatography, recrystallization and the like.

When hydrolyzing with a base, the reaction is usually carried out in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, alcohols such as methanol and ethanol, water, and a mixture thereof.
Examples of the base used in the reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, hydrazine and the like.
In the reaction, the base is usually used at a ratio of 1 to 10 mol with respect to 1 mol of the intermediate compound (M30 ′).
The reaction temperature of the reaction is usually in the range of 0 to 120 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the intermediate solution (M30) is isolated by performing post-treatment operations such as acidification of the reaction solution, extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Can do. The isolated intermediate compound (M30) can be further purified by chromatography, recrystallization and the like.

(Production method 15)
The intermediate compound (M35) can be produced by brominating the intermediate compound (M29), and then the intermediate compound (M35) is aminated to produce the intermediate compound (M1). it can.
[Wherein the symbols have the same meaning as described above. ]
Intermediate compound (M35) can be produced by reacting intermediate compound (M29) with a brominating agent.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as 1,4-dioxane, diethyl ether, and THF, esters such as ethyl acetate and butyl acetate, and halogens such as dichloromethane, chloroform, carbon tetrachloride, and 1,2-dichloroethane. Hydrocarbons, nitriles such as acetonitrile, aprotic polar solvents such as DMF and NMP, water, acetic acid, and mixtures thereof.
Examples of the brominating agent used in the reaction include N-bromosuccinimide and bromine.
The brominating agent is usually used at a ratio of 1 to 3 moles relative to 1 mole of the intermediate compound (M29).
The reaction temperature of the reaction is usually in the range of −10 to 100 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and extracted with an organic solvent and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture. The intermediate compound (M35) can be isolated by collecting the resulting solid by filtration. The isolated intermediate compound (M35) can be further purified by recrystallization, chromatography or the like.

Intermediate compound (M1) can be produced by reacting intermediate compound (M35) with an aminating agent in the presence of a copper compound.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include water, alcohols such as methanol and ethanol, ethers such as 1,4-dioxane, diethyl ether and THF, esters such as ethyl acetate and butyl acetate, dichloromethane, chloroform and tetrachloride. Carbon, halogenated hydrocarbons such as 1,2-dichloroethane, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP and DMSO, nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixtures thereof Can be mentioned.
Examples of the aminating agent used in the reaction include ammonia, aqueous ammonia, and lithium amide.
Examples of the copper compound used in the reaction include copper, copper (I) iodide, copper (I) oxide, copper (II) oxide, acetylacetone copper (II), copper acetate (II), copper sulfate (II) and the like. Can be mentioned.
In the reaction, a ligand can be added as necessary.
Examples of the ligand used in the reaction include acetylacetone, salen, phenanthroline, and the like.
This reaction can also be performed by adding a base as necessary.
Examples of the base used in the reaction include pyridine, picoline, 2,6-lutidine, DBU, nitrogen-containing heterocyclic compounds such as 1,5-diazabicyclo [4.3.0] -5-nonene, triethylamine, N, N -Inorganic bases such as tertiary amines such as diisopropylethylamine, tripotassium phosphate, potassium carbonate, cesium carbonate, sodium hydroxide.
The aminating agent is usually used at a ratio of 1 to 5 moles, and the copper compound is usually used at a ratio of 0.02 to 0.5 moles per 1 mole of the intermediate compound (M35). The ligand is used in a proportion of 0.02 to 2 mol, and the base is used in a proportion of 1 to 5 mol if necessary.
The reaction temperature of the reaction is usually in the range of 30 to 200 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and extracted with an organic solvent and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture. The intermediate compound (M1) can be isolated by collecting the resulting solid by filtration. The isolated intermediate compound (M1) can be further purified by recrystallization, chromatography or the like.

(Production Method 16)
After intermediate compound (M32) is produced by nitration of intermediate compound (M31), intermediate compound (M33) can be produced by reducing the obtained intermediate compound (M32). .
[Wherein the symbols have the same meaning as described above. ]

  The intermediate compound (M32) can be produced according to the production method 14, using the intermediate compound (M31) instead of the intermediate compound (M29).

Intermediate compound (M33) can be produced by reacting intermediate compound (M32) in the presence of a chlorinating agent.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, and aliphatic halogens such as dichloromethane and chloroform. Hydrocarbons and mixtures thereof.
Examples of the chlorinating agent used in the reaction include thionyl chloride, oxalyl dichloride, phosphorus oxychloride and the like.
In the reaction, the chlorinating agent is usually used at a ratio of 1 to 100 mol with respect to 1 mol of the intermediate compound (M32).
The reaction temperature of the reaction is usually in the range of 0 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and extracted with an organic solvent and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture. The intermediate compound (M33) can be isolated by collecting the resulting solid by filtration. The isolated intermediate compound (M33) can be further purified by recrystallization, chromatography or the like.

(Production Method 17)
After intermediate compound (M40) is produced by nitration of intermediate compound (M34), intermediate compound (M40) is reacted with intermediate compound (M10) to obtain intermediate compound (M40). M30) can be manufactured.
[Wherein the symbols have the same meaning as described above. ]
Intermediate compound (M40) can be produced according to the method of production method 14, using intermediate compound (M34) instead of intermediate compound (M29).
The intermediate compound (30) can be produced according to the production method 10 using the intermediate compound (M40) instead of the intermediate compound (P2).

(Production method 18)
After the intermediate compound (M38) is produced by reducing the intermediate compound (M40), the obtained intermediate compound (M38) is reacted with the intermediate compound (M2), (M18) or (M4). Thus, the intermediate compound (P2) can be produced.
[Wherein the symbols have the same meaning as described above. ]
The intermediate compound (M38) can be produced according to the production method 14, using the intermediate compound (M40) instead of the intermediate compound (M30).
The intermediate compound (P2) can be produced according to the production method 2, using the intermediate compound (M38) instead of the intermediate compound (M1). Alternatively, the intermediate compound (P2) can be produced according to the production method 3, using the intermediate compound (M38) instead of the intermediate compound (M1).

(Production Method 19)
The compound (P7) of the present invention in which R ⁶ is a C1-C6 perfluoroalkyl group in the formula (1), the compound (P4) of the present invention in which R ⁶ is a halogen atom in the formula (1), the compound (M11) or The compound (M11 ′) can be produced by reacting in the presence of a copper compound.
[Wherein, Rf represents a C1-C6 perfluoroalkyl group, and other symbols have the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include aromatic hydrocarbons such as toluene and xylene, acid amides such as DMF and NMP, and mixtures thereof.
Examples of the copper compound used for the reaction include copper and copper (I) iodide.
When using the compound (M11) in the reaction, the compound (M11) is usually used in a proportion of 1 to 10 mol and the copper compound is usually used in a proportion of 0.5 to 10 mol with respect to 1 mol of the compound (P4) of the present invention. The reaction temperature of the reaction is usually in the range of 100 to 200 ° C. The reaction time is usually in the range of 0.5 to 48 hours.
When the intermediate compound (M11 ′) is used in the reaction, potassium fluoride may be added. The compound (M11 ′) is usually in a proportion of 1 to 10 mol, the copper compound is usually in a proportion of 0.1 to 10 mol, and the potassium fluoride is usually in a proportion of 0.1 to 5 mol with respect to 1 mol of the compound (P4) of the present invention. The reaction temperature of the reaction is usually in the range of 0 to 150 ° C. The reaction time is usually in the range of 0.5 to 48 hours.
After completion of the reaction, the compound of the present invention (P7) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound (P7) of the present invention can be further purified by chromatography, recrystallization and the like.
In the reaction, V ¹ is preferably a bromine atom or an iodine atom.

(Production method 20)
By reacting the present compound (P4) with a sulfurizing agent, the present compound (P9) in which R ⁶ is —SH in the formula (1) can be produced. Moreover, the intermediate compound (P9 ') which is the disulfide body can be manufactured by oxidizing this invention compound (P9).
[Wherein, V ¹ represents a halogen atom, and other symbols have the same meaning as described above. ]
The compound (P9) of the present invention can be produced by reacting the compound (P4) of the present invention in the presence of a sulfurizing agent and a catalyst.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include aromatic hydrocarbons such as toluene and xylene, acid amides such as DMF and NMP, sulfoxides such as DMSO, and mixtures thereof.
Examples of the sulfurizing agent used in the reaction include sodium sulfide, sodium sulfide nonahydrate, and thiourea.
Examples of the catalyst used in the reaction include copper (I) chloride, copper (I) bromide, and copper (I) iodide.
This reaction can also be performed by adding a ligand as necessary.
Examples of the ligand used in the reaction include acetylacetone, salen, phenanthroline, and the like.
This reaction can also be performed in presence of a base as needed.
Examples of the base used in the reaction include potassium carbonate, cesium carbonate, tripotassium phosphate, and triethylamine.
In this reaction, the ratio of the sulfurizing agent is usually 1 to 10 moles, the catalyst is usually 0.1 to 5 moles, and the ligand is usually 0.1 to 5 moles with respect to 1 mole of the compound (P4) of the present invention. The mole ratio, base is usually used in a ratio of 1 mole to 2 moles.
The reaction temperature of the reaction is usually in the range of 50 to 200 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the compound of the present invention (P9) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound (P9) of the present invention can be further purified by chromatography, recrystallization and the like.
In the reaction, V ¹ is preferably a bromine atom or an iodine atom.
Here, the reaction from the compound (P9) of the present invention to the intermediate compound (P9 ′) is likely to occur, and the intermediate compound (P9 ′) may be generated during the synthesis of the compound (P9) of the present invention.

The intermediate compound (P9 ′) can be produced by oxidizing the compound (P9) of the present invention with an oxidizing agent.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include water, alcohols such as methanol and ethanol, THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, ethers such as 1,4-dioxane, and aromatic hydrocarbons such as toluene and xylene. Nitriles such as acetonitrile, acid amides such as DMF and NMP, sulfoxides such as DMSO, carboxylic acids such as acetic acid, and mixtures thereof.
Examples of the oxidizing agent used in the reaction include oxygen, iodine, hydrogen peroxide solution, potassium ferricyanide, and the like.
In the reaction, an oxidizing agent is usually used at a ratio of 0.5 to 10 moles with respect to 1 mole of the compound (P9) of the present invention.
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the intermediate compound (P9 ′) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated intermediate compound (P9 ′) can be further purified by chromatography, recrystallization and the like.

The compound (P9) of the present invention is produced by thioesterifying the compound (P4) of the present invention to produce an intermediate compound (P9-1) and then hydrolyzing the obtained intermediate compound (P9-1). can do.
[Wherein, R ^{15 ′} represents a chain hydrocarbon group which may have one or more halogen atoms or a phenyl group which may have one or more halogen atoms; Represents the same meaning as above. ]
The intermediate compound (P9-1) can be produced by reacting the compound (P4) of the present invention in the presence of a thioesterifying agent and a catalyst.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include aromatic hydrocarbons such as toluene and xylene, acid amides such as DMF and NMP, sulfoxides such as DMSO, and mixtures thereof.
Examples of the thioesterification agent used in the reaction include thioacetic acid and thiobenzoic acid.
Examples of the catalyst used in the reaction include copper (I) chloride, copper (I) bromide, and copper (I) iodide.
This reaction can also be performed by adding a ligand as necessary.
Examples of the ligand used in the reaction include acetylacetone, salen, phenanthroline, and the like.
This reaction can also be performed in presence of a base as needed.
Examples of the base used in the reaction include potassium carbonate, cesium carbonate, tripotassium phosphate, and triethylamine.
In the reaction, with respect to 1 mol of the present compound (P4), the proportion of the thioesterifying agent is usually 1 to 10 mol, the proportion of the catalyst is usually 0.1 to 5 mol, and the ligand is usually 0.1 to 0.1 mol. The base is usually used at a ratio of 5 moles and 1 mole to 2 moles.
The reaction temperature of the reaction is usually in the range of 50 to 200 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the intermediate compound (P9-1) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated intermediate compound (P9-1) can be further purified by chromatography, recrystallization and the like.
In the reaction, V ¹ is preferably a bromine atom or an iodine atom.

The compound (P9) of the present invention can be produced by hydrolyzing the intermediate compound (P9-1).
When hydrolyzing with an acid, the reaction is usually carried out using an aqueous acid solution as a solvent.
Examples of the acid used for the reaction include mineral acids such as hydrochloric acid, nitric acid, phosphoric acid and sulfuric acid, and carboxylic acids such as acetic acid and trifluoroacetic acid.
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound of the present invention (P9) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound (P9) of the present invention can be further purified by chromatography, recrystallization and the like.
When hydrolyzing with a base, the reaction is usually carried out in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, alcohols such as methanol and ethanol, water, and a mixture thereof.
Examples of the base used for the reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.
In the reaction, the base is usually used at a ratio of 1 to 10 mol per 1 mol of the intermediate compound (P9-1).
The reaction temperature of the reaction is usually in the range of 0 to 120 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound of the present invention (P9) is isolated by post-treatment such as acidification of the reaction solution, extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Can do. The isolated compound (P9) of the present invention can be further purified by chromatography, recrystallization and the like.
Here, the reaction from the compound (P9) of the present invention to the intermediate compound (P9 ′) is likely to occur, and the intermediate compound (P9 ′) may be generated during the synthesis of the compound (P9) of the present invention.

(Production method 21)
The present compound (P9) or an intermediate compound (P9 ′) which is a disulfide thereof and the compound (M13) are reacted in the presence of a base, and R ⁶ is —S (O) _m R ¹¹ ′, This invention compound (P10)-(m = 0) whose m is 0 can be manufactured. By oxidizing the compound (P10)-(m = 0) of the present invention in which m is 0, the present invention in which R ⁶ is —S (O) _m R ¹¹ ′ and m is 1 in the formula (1) This invention compound (P10)-(m = 2) which is compound (P10)-(m = 1) or 2 can be manufactured.
[Wherein, R11 ′ represents a chain hydrocarbon group which may have one or more halogen atoms, and other symbols represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, DMF, Examples include acid amides such as NMP, sulfoxides such as DMSO, and mixtures thereof.
Examples of the base used in the reaction include alkali metal or alkaline earth metal hydrides such as sodium hydride, potassium hydride and calcium hydride, inorganic bases such as sodium carbonate and potassium carbonate, and organic bases such as triethylamine. Can be mentioned.
When an intermediate compound (P9 ′) that is a disulfide is used, it is usually carried out in the presence of a reducing agent.
Examples of the reducing agent used in the reaction include sodium hydroxymethanesulfinate (trade name: Rongalite).
In the reaction, with respect to 1 mol of the present compound (P9), the compound (M13) is usually used in a proportion of 1 to 10 mol, and the base is usually used in a proportion of 1 to 10 mol.
When the intermediate compound (P9 ′) that is a disulfide is used, the ratio of the compound (M13) is usually 0.5 to 5 mol and the base is usually 0 with respect to 1 mol of the intermediate compound (P9 ′). .5-5 mole ratio, reducing agent is used in 0.5-5 mole ratio.
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (P10)-(m = 0) of the present invention in which m is 0 is obtained simply by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Can be separated. The isolated compound (P10)-(m = 0) of the present invention in which m is 0 can be further purified by chromatography, recrystallization and the like.

Among the compounds (P10)-(m = 0) of the present invention in which m is 0, the compound in which R ¹¹ ′ is C1-C6 perfluoroalkyl is an intermediate compound (P9 ′), perfluoroalkyl iodide. And it can manufacture by making it react with a reducing agent.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, DMF, Examples include acid amides such as NMP, sulfoxides such as DMSO, and mixtures thereof.
Examples of the reducing agent used in the reaction include tetrakis (dimethylamino) ethylene.
Examples of perfluoroalkyl iodide include trifluoromethane iodide, pentafluoroethane iodide, heptafluoro-2-iodopropane, and the like.
In the reaction, perfluoroalkyl iodide is usually used in a proportion of 1 to 10 mol and a reducing agent in a proportion of 0.5 to 5 mol with respect to 1 mol of the intermediate compound (P9 ′).
The reaction temperature of the reaction is usually in the range of -80 to 50 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (P10)-(m = 0) of the present invention in which m is 0 is obtained simply by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Can be separated. The isolated compound (P10)-(m = 0) of the present invention in which m is 0 can be further purified by chromatography, recrystallization and the like.

In the present compound (P10), the present compound (P10)-(m = 1) or the present compound (P10)-(m = 2) in which m is 1 represents the present invention in which m is 0. It can be produced by oxidizing compound (P10)-(m = 0) with an oxidizing agent.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform, alcohols such as methanol and ethanol, acetic acid, water, and mixtures thereof.
Examples of the oxidizing agent used in the reaction include m-chloroperbenzoic acid and aqueous hydrogen peroxide.
The reaction can be carried out in the presence of a catalyst as necessary.
Examples of the catalyst used in the reaction include sodium tungstate.
In the reaction, with respect to the compound (P10)-(m = 0) of the present invention in which 1 mol of m is 0, the ratio of the oxidizing agent is usually 1 to 5 mol, and the catalyst is usually 0.01 to 0.5. Used in molar proportions.
In the compound in which m is 1, the oxidizing agent is usually used in a proportion of 0.8 to 1.2 mol with respect to the compound (P10)-(m = 0) of the present invention in which 1 mol of m is 0, In the compound in which m is 2, the oxidizing agent is usually used at a ratio of 1.8 to 5 mol with respect to the compound (P10)-(m = 0) of the present invention in which 1 mol of m is 0.
The reaction temperature of the reaction is usually in the range of -20 to 120 ° C. The reaction time is usually in the range of 0.1 to 12 hours.
After completion of the reaction, the reaction mixture is extracted with an organic solvent, and the organic layer is washed with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) or an aqueous solution of a base (for example, sodium bicarbonate) as necessary, dried, The present compound (P10)-(m = 1) or the present compound (P10)-(m = 2) wherein m is 1 is isolated by performing post-treatment operations such as concentration. Can do. The present compound (P10)-(m = 1) or the present compound (P10)-(m = 2) wherein m is 1 is further purified by chromatography, recrystallization, etc. You can also.

(Production method 22)
This invention compound (P11) whose R < ⁶ > is -OH in Formula (1) can be manufactured through intermediate compound (P11 ') from this invention compound (P4).
[Wherein the symbols have the same meaning as described above. ]
The intermediate compound (P11 ′) can be produced by reacting the compound (P4) of the present invention with benzyl alcohol in the presence of a base.
The reaction is usually performed in the presence of a solvent or benzyl alcohol as a solvent.
Examples of the solvent used in the reaction include aromatic hydrocarbons such as toluene and xylene, acid amides such as DMF and NMP, sulfoxides such as DMSO, and mixtures thereof.
This reaction can also be performed by adding a catalyst as needed.
Examples of the catalyst used in the reaction include copper (I) chloride, copper (I) bromide, and copper (I) iodide.
This reaction can also be performed by adding a ligand as necessary.
Examples of the ligand used in the reaction include acetylacetone, salen, phenanthroline, and the like.
The reaction is usually performed in the presence of a base.
Examples of the base used in the reaction include potassium carbonate, cesium carbonate, and tripotassium phosphate.
In the reaction, with respect to 1 mole of the compound (P4) of the present invention, the proportion of benzyl alcohol is usually 1 to 10 moles, the catalyst is usually 0.1 to 5 moles, and the ligand is usually 0.1 to 5 moles. The mole ratio, base is usually used in a ratio of 1 mole to 2 moles.
The reaction temperature of the reaction is usually in the range of 50 to 200 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the intermediate compound (P11 ′) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated intermediate compound (P11 ′) can be further purified by chromatography, recrystallization and the like.
In the reaction, V ¹ is preferably a bromine atom or an iodine atom.

The compound (P11) of the present invention can be produced by reacting the intermediate compound (P11 ′) with hydrogen in the presence of a hydrogenation catalyst.
The reaction is usually performed in a hydrogen atmosphere at 1 to 100 atm, usually in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, esters such as ethyl acetate and butyl acetate, alcohols such as methanol and ethanol, water And mixtures thereof.
Examples of the hydrogenation catalyst used in the reaction include transition metal compounds such as palladium carbon, palladium hydroxide, Raney nickel, and platinum oxide.
In the reaction, with respect to 1 mol of the intermediate compound (P11 ′), hydrogen is usually used in an excess ratio of 3 mol or more, and a hydrogenation catalyst is usually used in a ratio of 0.001 to 0.5 mol.
This reaction can also be performed by adding an acid, a base or the like, if necessary.
Examples of the acid used for the reaction include acetic acid and hydrochloric acid, and examples of the base used for the reaction include tertiary amines such as triethylamine, magnesium oxide and the like.
The reaction temperature of the reaction is usually in the range of -20 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (P11) of the present invention can be isolated by performing post-treatment operations such as filtration of the reaction mixture, extraction with an organic solvent as necessary, and drying and concentration of the organic layer. it can. The isolated compound (P11) of the present invention can be further purified by chromatography, recrystallization and the like.

(Production Method 23)
This invention compound (P12) whose R < ⁶ > is -OR < ¹¹ '> in Formula (1) can be manufactured by making this invention compound (P11) and a compound (M13) react.
[Wherein the symbols have the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, DMF, Examples include acid amides such as NMP, sulfoxides such as DMSO, and mixtures thereof.
Examples of the base used in the reaction include alkali metal or alkaline earth metal hydrides such as sodium hydride, potassium hydride and calcium hydride, inorganic bases such as sodium carbonate and potassium carbonate, and organic bases such as triethylamine. Can be mentioned.
In the reaction, with respect to 1 mol of the present compound (P11), the compound (M13) is usually used in a proportion of 1 to 10 mol, and the base is usually used in a proportion of 1 to 10 mol.
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound of the present invention (P12) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound (P12) of the present invention can be further purified by chromatography, recrystallization and the like.

In addition, among the present compound ^(P12), 'the compound of the present invention is a trifluoromethyl group ^{(P12) - (R 11'} R 11 = CF 3) can be produced by the following production method.
[Wherein the symbols have the same meaning as described above. ]
The intermediate compound (P11 ″) can be produced by reacting the compound (P11) of the present invention with a base, carbon disulfide and a methylating agent.
The reaction is performed in the presence of a solvent.
Examples of the solvent used in the reaction include acid amides such as DMF and NMP, and sulfoxides such as DMSO.
Examples of the base used for the reaction include alkali metal hydrides such as sodium hydride.
Examples of the methylating agent used in the reaction include methyl iodide.
In the reaction, the base is usually in a proportion of 1 to 2 mol, the carbon disulfide is usually in a proportion of 1 to 10 mol, and the methylating agent is usually in a proportion of 1 to 10 mol, relative to 1 mol of the compound (P11) of the present invention. Used in
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the intermediate compound (P11 ″) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The intermediate compound (P11 ″) can be further purified by chromatography, recrystallization and the like.

Among the compounds of the present invention (P12), the compound (P12)-(R ^{11 ′} = CF ₃ ) of the present invention wherein R ¹¹ ′ is a trifluoromethyl group oxidizes the intermediate compound (P11 ″) and the fluorinating agent. It can manufacture by making it react in presence of an agent.
The reaction is performed in the presence of a solvent.
Examples of the solvent used in the reaction include halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, and 1,2-dichloroethane.
Examples of the oxidizing agent used in the reaction include 1,3-dibromo-5,5-dimethylhydantoin.
Examples of the fluorinating agent used in the reaction include tetra-n-butylammonium fluoride and a hydrogen fluoride pyridine complex.
In the reaction, with respect to 1 mol of the intermediate compound (P11 ″), the oxidizing agent is usually used in a proportion of 1 to 10 mol, and the fluorinating agent is usually used in a proportion of 1 to 10 mol.
The reaction temperature of the reaction is usually in the range of -80 to 50 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the compound of the present invention (P12)-(R12) in which R ¹¹ ′ is a trifluoromethyl group is obtained by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, drying and concentration of the organic layer. ^{11 ′} = CF ₃ ) can be isolated. The compound (P12)-(R ^{11 ′} = CF ₃ ) of the present invention, in which the isolated R ¹¹ ′ is a trifluoromethyl group, can be further purified by chromatography, recrystallization, and the like.

(Production method 24)
Among the compounds of the present invention and the intermediate compound described above, N is a compound in which the nitrogen atom is optionally oxidized by reacting a compound having a nitrogen-containing heterocyclic group having a lone pair on the nitrogen atom with an oxidizing agent. Oxides can be produced.
Examples of the nitrogen-containing heterocyclic group include a pyridine ring.
The reaction can be carried out by a known method, for example, in a solvent such as halogenated hydrocarbons such as dichloromethane, chloroform and chlorobenzene, alcohols such as methanol and ethanol, acetic acid, water and a mixture thereof. It is carried out using an oxidizing agent such as chloroperbenzoic acid or hydrogen peroxide.

Next, specific examples of the compound of the present invention are shown below.
Formula (A)
R ² , R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethyl group, and R ¹ , R ⁸ , A ² and n are represented by [Table 1] to [Table 180]. The compound of the present invention which is a combination described in 1.

In the above [Table 1] to [Table 180], Me represents a methyl group, Et represents an ethyl group, Pr represents an n-propyl group, iPr represents an isopropyl group, tBu represents a tert-butyl group. CycPr represents a cyclopropyl group.

In the formula (A), R ² is a fluorine atom, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a fluorine atom, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a fluorine atom, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethyl group, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a fluorine atom, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a trifluoromethyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ² is a chlorine atom, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a chlorine atom, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethyl group, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a chlorine atom, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a chlorine atom, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a trifluoromethyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ² is a bromine atom, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethyl group, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a bromine atom, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethyl group, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a bromine atom, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethyl group, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a bromine atom, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a trifluoromethyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ² is a methyl group, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a methyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a methyl group, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a methyl group, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a trifluoromethyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ² is a trifluoromethyl group, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethyl group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ³ is a trifluoromethyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethyl group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ⁴ is a trifluoromethyl group, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethyl group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ⁵ is a trifluoromethyl group, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a trifluoromethyl group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ³ is a pentafluoroethyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethyl group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ³ is a trifluoromethoxy group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethyl group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ³ is a ² -pyridyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethyl group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ³ is a 3-chloro-2-pyridyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethyl group, R ¹ , R ⁸ , A compound in which A ² and n are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ³ is a 2-pyrimidinyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethyl group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ³ is —SF ₅ , R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].

In the formula (A), R ² , R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a pentafluoroethyl group, and R ¹ , R ⁸ , A ² and n are [Table 1] to The compound which is a combination described in [Table 180].
In the formula (A), R ² is a fluorine atom, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a pentafluoroethyl group, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a fluorine atom, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a pentafluoroethyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a fluorine atom, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a pentafluoroethyl group, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a fluorine atom, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a pentafluoroethyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ² is a chlorine atom, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a pentafluoroethyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a chlorine atom, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a pentafluoroethyl group, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a chlorine atom, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a pentafluoroethyl group, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a chlorine atom, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a pentafluoroethyl group, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ² is a bromine atom, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a pentafluoroethyl group, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a bromine atom, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a pentafluoroethyl group, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a bromine atom, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a pentafluoroethyl group, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a bromine atom, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a pentafluoroethyl group, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ² is a methyl group, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a pentafluoroethyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a methyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a pentafluoroethyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a methyl group, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a pentafluoroethyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a methyl group, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a pentafluoroethyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ² is a trifluoromethyl group, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a pentafluoroethyl group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ³ is a trifluoromethyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a pentafluoroethyl group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ⁴ is a trifluoromethyl group, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a pentafluoroethyl group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ⁵ is a trifluoromethyl group, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a pentafluoroethyl group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ³ is a pentafluoroethyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a pentafluoroethyl group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ³ is a trifluoromethoxy group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a pentafluoroethyl group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ³ is a 2-pyridyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a pentafluoroethyl group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ³ is a 3-chloro-2-pyridyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a pentafluoroethyl group, R ¹ , R ⁸ , A compound in which A ² and n are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ³ is a 2-pyrimidinyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a pentafluoroethyl group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ³ is —SF ₅ , R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a pentafluoroethyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].

In the formula (A), R ² , R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a heptafluoroisopropyl group, and R ¹ , R ⁸ , A ² and n are from [Table 1] to The compound which is a combination described in [Table 180].
In the formula (A), R ² is a fluorine atom, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a heptafluoroisopropyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a fluorine atom, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a heptafluoroisopropyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a fluorine atom, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a heptafluoroisopropyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a fluorine atom, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a heptafluoroisopropyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ² is a chlorine atom, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a heptafluoroisopropyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a chlorine atom, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a heptafluoroisopropyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a chlorine atom, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a heptafluoroisopropyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a chlorine atom, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a heptafluoroisopropyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ² is a bromine atom, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a heptafluoroisopropyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a bromine atom, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a heptafluoroisopropyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a bromine atom, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a heptafluoroisopropyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a bromine atom, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a heptafluoroisopropyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ² is a methyl group, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a heptafluoroisopropyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a methyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a heptafluoroisopropyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a methyl group, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a heptafluoroisopropyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a methyl group, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a heptafluoroisopropyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ² is a trifluoromethyl group, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a heptafluoroisopropyl group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ³ is a trifluoromethyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a heptafluoroisopropyl group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ⁴ is a trifluoromethyl group, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a heptafluoroisopropyl group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ⁵ is a trifluoromethyl group, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a heptafluoroisopropyl group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ³ is a pentafluoroethyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a heptafluoroisopropyl group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ³ is a trifluoromethoxy group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a heptafluoroisopropyl group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ³ is a 2-pyridyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a heptafluoroisopropyl group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ³ is a 3-chloro-2-pyridyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a heptafluoroisopropyl group, R ¹ , R ⁸ , A compound in which A ² and n are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ³ is a 2-pyrimidinyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a heptafluoroisopropyl group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ³ is —SF ₅ , R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a heptafluoroisopropyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].

In the formula (A), R ² , R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethoxy group, and R ¹ , R ⁸ , A ² and n are [Table 1] to The compound which is a combination described in [Table 180].
In the formula (A), R ² is a fluorine atom, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethoxy group, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a fluorine atom, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethoxy group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a fluorine atom, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethoxy group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a fluorine atom, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a trifluoromethoxy group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ² is a chlorine atom, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethoxy group, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a chlorine atom, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethoxy group, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a chlorine atom, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethoxy group, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a chlorine atom, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a trifluoromethoxy group, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ² is a bromine atom, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethoxy group, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a bromine atom, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethoxy group, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a bromine atom, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethoxy group, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a bromine atom, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a trifluoromethoxy group, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ² is a methyl group, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethoxy group, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a methyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethoxy group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a methyl group, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethoxy group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a methyl group, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a trifluoromethoxy group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ² is a trifluoromethyl group, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethoxy group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ³ is a trifluoromethyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethoxy group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ⁴ is a trifluoromethyl group, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethoxy group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ⁵ is a trifluoromethyl group, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a trifluoromethoxy group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ³ is a pentafluoroethyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethoxy group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ³ is a trifluoromethoxy group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethoxy group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ³ is a 2-pyridyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethoxy group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ³ is a 3-chloro-2-pyridyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethoxy group, R ¹ , R ⁸ , A compound in which A ² and n are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ³ is a 2-pyrimidinyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethoxy group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].
In the formula (A), R ³ is —SF ₅ , R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethoxy group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].

In the formula (A), R ² , R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfanyl group, and R ¹ , R ⁸ , A ² and n are [Table 1] -The compound which is a combination as described in [Table 180].
In the formula (A), R ² is a fluorine atom, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfanyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a fluorine atom, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfanyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a fluorine atom, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfanyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a fluorine atom, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a trifluoromethylsulfanyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ² is a chlorine atom, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfanyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a chlorine atom, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfanyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a chlorine atom, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfanyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a chlorine atom, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a trifluoromethylsulfanyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ² is a bromine atom, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfanyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a bromine atom, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfanyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a bromine atom, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfanyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a bromine atom, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a trifluoromethylsulfanyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ² is a methyl group, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfanyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a methyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfanyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a methyl group, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfanyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a methyl group, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a trifluoromethylsulfanyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ² is a trifluoromethyl group, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfanyl group, R ¹ , R ⁸ , A ² and n is a combination described in [Table 1] to [Table 180].
In the formula (A), R ³ is a trifluoromethyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfanyl group, R ¹ , R ⁸ , A ² and n is a combination described in [Table 1] to [Table 180].
In the formula (A), R ⁴ is a trifluoromethyl group, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfanyl group, R ¹ , R ⁸ , A ² and n is a combination described in [Table 1] to [Table 180].
In the formula (A), R ⁵ is a trifluoromethyl group, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a trifluoromethylsulfanyl group, R ¹ , R ⁸ , A ² and n is a combination described in [Table 1] to [Table 180].
In the formula (A), R ³ is a pentafluoroethyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfanyl group, R ¹ , R ⁸ , A ² and n is a combination described in [Table 1] to [Table 180].
In the formula (A), R ³ is a trifluoromethoxy group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfanyl group, R ¹ , R ⁸ , A ² and n is a combination described in [Table 1] to [Table 180].
In the formula (A), R ³ is a 2-pyridyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfanyl group, R ¹ , R ⁸ , A ² and n is a combination described in [Table 1] to [Table 180].
In the formula (A), R ³ is a 3-chloro-2-pyridyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfanyl group, R ¹ , R ⁸ , A ² and n are the compounds described in [Table 1] to [Table 180].
In the formula (A), R ³ is a 2-pyrimidinyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfanyl group, R ¹ , R ⁸ , A ² and n is a combination described in [Table 1] to [Table 180].
In the formula (A), R ³ is —SF ₅ , R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfanyl group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].

In the formula (A), R ² , R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfinyl group, and R ¹ , R ⁸ , A ² and n are [Table 1] -The compound which is a combination as described in [Table 180].
In the formula (A), R ² is a fluorine atom, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfinyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a fluorine atom, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfinyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a fluorine atom, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfinyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a fluorine atom, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a trifluoromethylsulfinyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ² is a chlorine atom, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfinyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a chlorine atom, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfinyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a chlorine atom, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfinyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a chlorine atom, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a trifluoromethylsulfinyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ² is a bromine atom, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfinyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a bromine atom, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfinyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a bromine atom, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfinyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a bromine atom, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a trifluoromethylsulfinyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ² is a methyl group, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfinyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a methyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfinyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a methyl group, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfinyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a methyl group, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a trifluoromethylsulfinyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ² is a trifluoromethyl group, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfinyl group, R ¹ , R ⁸ , A ² and n is a combination described in [Table 1] to [Table 180].
In the formula (A), R ³ is a trifluoromethyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfinyl group, R ¹ , R ⁸ , A ² and n is a combination described in [Table 1] to [Table 180].
In the formula (A), R ⁴ is a trifluoromethyl group, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfinyl group, R ¹ , R ⁸ , A ² and n is a combination described in [Table 1] to [Table 180].
In the formula (A), R ⁵ is a trifluoromethyl group, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a trifluoromethylsulfinyl group, R ¹ , R ⁸ , A ² and n is a combination described in [Table 1] to [Table 180].
In the formula (A), R ³ is a pentafluoroethyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfinyl group, R ¹ , R ⁸ , A ² and n is a combination described in [Table 1] to [Table 180].
In the formula (A), R ³ is a trifluoromethoxy group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfinyl group, R ¹ , R ⁸ , A ² and n is a combination described in [Table 1] to [Table 180].
In the formula (A), R ³ is a 2-pyridyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfinyl group, R ¹ , R ⁸ , A ² and n is a combination described in [Table 1] to [Table 180].
In the formula (A), R ³ is a 3-chloro-2-pyridyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfinyl group, R ¹ , R ⁸ , A ² and n are the compounds described in [Table 1] to [Table 180].
In the formula (A), R ³ is a 2-pyrimidinyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfinyl group, R ¹ , R ⁸ , A ² and n is a combination described in [Table 1] to [Table 180].
In the formula (A), R ³ is —SF ₅ , R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfinyl group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].

In the formula (A), R ² , R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfonyl group, and R ¹ , R ⁸ , A ² and n are [Table 1] -The compound which is a combination as described in [Table 180].
In the formula (A), R ² is a fluorine atom, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfonyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a fluorine atom, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfonyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a fluorine atom, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfonyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a fluorine atom, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a trifluoromethylsulfonyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ² is a chlorine atom, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfonyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a chlorine atom, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfonyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a chlorine atom, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfonyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a chlorine atom, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a trifluoromethylsulfonyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ² is a bromine atom, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfonyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a bromine atom, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfonyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a bromine atom, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfonyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a bromine atom, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a trifluoromethylsulfonyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ² is a methyl group, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfonyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a methyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfonyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a methyl group, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfonyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a methyl group, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a trifluoromethylsulfonyl group, and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ² is a trifluoromethyl group, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfonyl group, R ¹ , R ⁸ , A ² and n is a combination described in [Table 1] to [Table 180].
In the formula (A), R ³ is a trifluoromethyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfonyl group, R ¹ , R ⁸ , A ² and n is a combination described in [Table 1] to [Table 180].
In the formula (A), R ⁴ is a trifluoromethyl group, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfonyl group, R ¹ , R ⁸ , A ² and n is a combination described in [Table 1] to [Table 180].
In the formula (A), R ⁵ is a trifluoromethyl group, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a trifluoromethylsulfonyl group, R ¹ , R ⁸ , A ² and n is a combination described in [Table 1] to [Table 180].
In the formula (A), R ³ is a pentafluoroethyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfonyl group, R ¹ , R ⁸ , A ² and n is a combination described in [Table 1] to [Table 180].
In the formula (A), R ³ is a trifluoromethoxy group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfonyl group, R ¹ , R ⁸ , A ² and n is a combination described in [Table 1] to [Table 180].
In the formula (A), R ³ is a 2-pyridyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfonyl group, R ¹ , R ⁸ , A ² and n is a combination described in [Table 1] to [Table 180].
In the formula (A), R ³ is a 3-chloro-2-pyridyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfonyl group, R ¹ , R ⁸ , A ² and n are the compounds described in [Table 1] to [Table 180].
In the formula (A), R ³ is a 2-pyrimidinyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfonyl group, R ¹ , R ⁸ , A ² and n is a combination described in [Table 1] to [Table 180].
In the formula (A), R ³ is —SF ₅ , R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a trifluoromethylsulfonyl group, R ¹ , R ⁸ , A ² and n Are the combinations described in [Table 1] to [Table 180].

In the formula (A), R ² , R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a bromine atom, and R ¹ , R ⁸ , A ² and n are [Table 1] to [Table 1]. 180].
In the formula (A), R ² is a fluorine atom, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a bromine atom, and R ¹ , R ⁸ , A ² and n are [1] to [Table 180].
In the formula (A), R ³ is a fluorine atom, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a bromine atom, and R ¹ , R ⁸ , A ² and n are [1] to [Table 180].
In the formula (A), R ⁴ is a fluorine atom, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a bromine atom, and R ¹ , R ⁸ , A ² and n are [1] to [Table 180].
In the formula (A), R ⁵ is a fluorine atom, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a bromine atom, and R ¹ , R ⁸ , A ² and n are [1] to [Table 180].
In the formula (A), R ² is a chlorine atom, R ³ , R ⁴ and R ⁵ are hydrogen atoms, RR ⁶ is a bromine atom, and R ¹ , R ⁸ , A ² and n are [1] to [Table 180].
In the formula (A), R ³ is a chlorine atom, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a bromine atom, and R ¹ , R ⁸ , A ² and n are [1] to [Table 180].
In the formula (A), R ⁴ is a chlorine atom, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a bromine atom, and R ¹ , R ⁸ , A ² and n are [1] to [Table 180].
In the formula (A), R ⁵ is a chlorine atom, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a bromine atom, and R ¹ , R ⁸ , A ² and n are [1] to [Table 180].
In the formula (A), R ² is a bromine atom, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a bromine atom, and R ¹ , R ⁸ , A ² and n are [1] to [Table 180].
In the formula (A), R ³ is a bromine atom, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a bromine atom, and R ¹ , R ⁸ , A ² and n are [1] to [Table 180].
In the formula (A), R ⁴ is a bromine atom, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a bromine atom, and R ¹ , R ⁸ , A ² and n are [1] to [Table 180].
In the formula (A), R ⁵ is a bromine atom, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a bromine atom, and R ¹ , R ⁸ , A ² and n are [1] to [Table 180].
In the formula (A), R ² is a methyl group, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a bromine atom, and R ¹ , R ⁸ , A ² and n are [1] to [Table 180].
In the formula (A), R ³ is a methyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a bromine atom, R ¹ , R ⁸ , A ² and n are [1] to [Table 180].
In the formula (A), R ⁴ is a methyl group, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a bromine atom, and R ¹ , R ⁸ , A ² and n are [1] to [Table 180].
In the formula (A), R ⁵ is a methyl group, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a bromine atom, and R ¹ , R ⁸ , A ² and n are [1] to [Table 180].
In the formula (A), R ² is a trifluoromethyl group, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a bromine atom, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a trifluoromethyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a bromine atom, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a trifluoromethyl group, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is a bromine atom, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a trifluoromethyl group, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is a bromine atom, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a pentafluoroethyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a bromine atom, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a trifluoromethoxy group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a bromine atom, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a 2-pyridyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a bromine atom, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a 3-chloro-2-pyridyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a bromine atom, R ¹ , R ⁸ , A ² And n is a combination described in [Table 1] to [Table 180].
In the formula (A), R ³ is a 2-pyrimidinyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a bromine atom, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is —SF ₅ , R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is a bromine atom, R ¹ , R ⁸ , A ² and n are [ The compound which is a combination as described in [Table 1]-[Table 180].

In the formula (A), R ² , R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is an iodine atom, and R ¹ , R ⁸ , A ² and n are [Table 1] to [Table 1]. 180].
In the formula (A), R ² is a fluorine atom, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is an iodine atom, and R ¹ , R ⁸ , A ² and n are [1] to [Table 180].
In the formula (A), R ³ is a fluorine atom, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is an iodine atom, and R ¹ , R ⁸ , A ² and n are [1] to [Table 180].
In the formula (A), R ⁴ is a fluorine atom, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is an iodine atom, and R ¹ , R ⁸ , A ² and n are [1] to [Table 180].
In the formula (A), R ⁵ is a fluorine atom, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is an iodine atom, and R ¹ , R ⁸ , A ² and n are [1] to [Table 180].
In the formula (A), R ² is a chlorine atom, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is an iodine atom, and R ¹ , R ⁸ , A ² and n are [1] to [Table 180].
In the formula (A), R ³ is a chlorine atom, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is an iodine atom, and R ¹ , R ⁸ , A ² and n are [1] to [Table 180].
In the formula (A), R ⁴ is a chlorine atom, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is an iodine atom, R ¹ , R ⁸ , A ² and n are [1] to [Table 180].
In the formula (A), R ⁵ is a chlorine atom, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is an iodine atom, R ¹ , R ⁸ , A ² and n are [1] to [Table 180].
In the formula (A), R ² is a bromine atom, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is an iodine atom, and R ¹ , R ⁸ , A ² and n are [1] to [Table 180].
In the formula (A), R ³ is a bromine atom, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is an iodine atom, and R ¹ , R ⁸ , A ² and n are [1] to [Table 180].
In the formula (A), R ⁴ is a bromine atom, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is an iodine atom, R ¹ , R ⁸ , A ² and n are [1] to [Table 180].
In the formula (A), R ⁵ is a bromine atom, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is an iodine atom, and R ¹ , R ⁸ , A ² and n are [1] to [Table 180].
In the formula (A), R ² is a methyl group, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is an iodine atom, and R ¹ , R ⁸ , A ² and n are [1] to [Table 180].
In the formula (A), R ³ is a methyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is an iodine atom, and R ¹ , R ⁸ , A ² and n are [1] to [Table 180].
In the formula (A), R ⁴ is a methyl group, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is an iodine atom, R ¹ , R ⁸ , A ² and n are [1] to [Table 180].
In the formula (A), R ⁵ is a methyl group, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is an iodine atom, R ¹ , R ⁸ , A ² and n are [1] to [Table 180].
In the formula (A), R ² is a trifluoromethyl group, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is an iodine atom, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a trifluoromethyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is an iodine atom, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a trifluoromethyl group, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is an iodine atom, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a trifluoromethyl group, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is an iodine atom, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a pentafluoroethyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is an iodine atom, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a trifluoromethoxy group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is an iodine atom, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a 2-pyridyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is an iodine atom, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a 3-chloro-2-pyridyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is an iodine atom, R ¹ , R ⁸ , A ² And n is a combination described in [Table 1] to [Table 180].
In the formula (A), R ³ is a 2-pyrimidinyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is an iodine atom, R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is —SF ₅ , R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is an iodine atom, R ¹ , R ⁸ , A ² and n are [ The compound which is a combination as described in [Table 1]-[Table 180].

In the formula (A), R ² , R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is —SF ₅ , and R ¹ , R ⁸ , A ² and n are [Table 1] to [Table 1] Table 180].
In the formula (A), R ² is a fluorine atom, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is —SF ₅ , and R ¹ , R ⁸ , A ² and n are [ The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a fluorine atom, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is —SF ₅ , and R ¹ , R ⁸ , A ² and n are [ The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a fluorine atom, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is —SF ₅ , and R ¹ , R ⁸ , A ² and n are [ The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a fluorine atom, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is —SF ₅ , and R ¹ , R ⁸ , A ² and n are [ The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ² is a chlorine atom, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is —SF ₅ , R ¹ , R ⁸ , A ² and n are [ The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a chlorine atom, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is —SF ₅ , and R ¹ , R ⁸ , A ² and n are [ The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a chlorine atom, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is —SF ₅ , and R ¹ , R ⁸ , A ² and n are [ The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a chlorine atom, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is —SF ₅ , and R ¹ , R ⁸ , A ² and n are [ The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ² is a bromine atom, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is —SF ₅ , R ¹ , R ⁸ , A ² and n are [ The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a bromine atom, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is —SF ₅ , and R ¹ , R ⁸ , A ² and n are [ The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a bromine atom, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is —SF ₅ , R ¹ , R ⁸ , A ² and n are [ The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a bromine atom, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is —SF ₅ , and R ¹ , R ⁸ , A ² and n are [ The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ² is a methyl group, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is —SF ₅ , R ¹ , R ⁸ , A ² and n are [ The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a methyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is —SF ₅ , R ¹ , R ⁸ , A ² and n are [ The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a methyl group, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is —SF ₅ , R ¹ , R ⁸ , A ² and n are [ The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a methyl group, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is —SF ₅ , R ¹ , R ⁸ , A ² and n are [ The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ² is a trifluoromethyl group, R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is —SF ₅ , and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a trifluoromethyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is —SF ₅ , and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁴ is a trifluoromethyl group, R ² , R ³ and R ⁵ are hydrogen atoms, R ⁶ is —SF ₅ , and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ⁵ is a trifluoromethyl group, R ² , R ³ and R ⁴ are hydrogen atoms, R ⁶ is —SF ₅ , and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a pentafluoroethyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is —SF ₅ , and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a trifluoromethoxy group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is —SF ₅ , and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a 2-pyridyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is —SF ₅ , and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is a 3-chloro-2-pyridyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is —SF ₅ , R ¹ , R ⁸ , A ² and n are compounds according to the combinations described in [Table 1] to [Table 180].
In the formula (A), R ³ is a 2-pyrimidinyl group, R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is —SF ₅ , and R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].
In the formula (A), R ³ is —SF ₅ , R ² , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is —SF ₅ , R ¹ , R ⁸ , A ² and n are The compound which is a combination as described in [Table 1]-[Table 180].

  Examples of pests for which the compounds of the present invention are effective include harmful arthropods and nematodes such as harmful insects and harmful mites. Specific examples of such pests include the following.

  Hemiptera: small brown planthopper (Laodelphax striatellus), brown planthopper (Nilaparvata lugens), planthoppers such as Sejirounka (Sogatella furcifera), green rice leafhopper (Nephotettix cincticeps), Taiwan green rice leafhopper (Nephotettix virescens), tea Roh green leafhopper (Empoasca onukii) such as Leafhoppers, cotton aphids (Aphis gossypii), peach aphids (Myzus persicae), radish aphids (Brevicoryne brassicae), snowy aphids (Aphis spiraecola), tulip beetle aphids rosiphum euphorbiae), potato beetle aphids (Aulacorthum solani), barley aphids (Rhopalosiphum padi), citrus aphids (Toxoptera citricidus), peach beetles, Stink bugs such as stink bugs (Riptortus clavetus), spider helicopter bugs (Leptocorina chinensis), bark beetle bugs (Eysarcoris parvus), stag beetle (Haryomorpha mista) whitefly (Ariocanthus spiniferus), redfly worms (Aonurosanthus spiraferus) ), Ruby Beetles (Ceroplastes rubens), Icerya purchasi, Fujino scale (Pranococcus kraunhiae), Pseudococcus longispinis, Pseudococcus longispinis Scale insects such as Igaramushi (Pseudaulacaspis pentagona), tingidae acids, bedbugs such as bed bugs (Cimex lectularius), and Psyllidae such.

  Lepidoptera: rice stem borer (Chilo suppressalis), Sankameiga (Tryporyza incertulas), leaf roller (Cnaphalocrocis medinalis), Watanomeiga (Notarcha derogata), Indian meal moth (Plodia interpunctella), the European corn borer (Ostrinia furnacalis), high Madara Roh moth (Hellula undalis), Japanese medusa such as Shibatatsuga (Pediasia teterrellus), Spodoptera litura, Spodoptera exigua, Ayuyoto (Pseudaletia septata), Atoga ras genus such as ra brassicae, Agrotis ipsilon, Tamanaginiwaba (Prusia nigrisigna), Trichopulsia, Heliotis, Helicoberpa, etc. (Leguminivora glycinivolora), Azusa yamushiga (Matsusumuraeses azukivivora), Apple wolfberry (Adoxophyces orana famonata) Species of the genus, such as Archops fuscocuppreanus, Cydia pomonella, the genus Cypnotia, the genus moss of the genus P. , Genus Euprocutis, etc., Suga, such as Plutella xylostella, Cotton moth, such as Pectinophora gossypiella, Phthorimaea operculella, etc .; Riga acids, and clothes moth (Tinea translucens), Hirozukoga such as webbing clothes moth (Tineola bisselliella).

  Thrips pests: Frankliniella occidentalis, Thrips parmi, Scitotrips dorsalis, and Thrips thrips

  Diptera: Culex (Culex pipiens pallens), Culex (Culex tritaeniorhynchus), Culex such as Culex quinquefasciatus (Culex quinquefasciatus), Aedes aegypti (Aedes aegypti), Aedes albopictus (Aedes albopictus) Aedes genus such as Anopheles sinensis (Anopheles sinensis), etc. Genus Anopheles, chironomid, housefly (Musca domestica), housefly (Muscina stabulans) and other species of houseflies, fly flies, sphagnum flies, fly flies, leaf fly (Delia platura), leaf flies D (Agromyza oryzae), rice Hime leafminer (Hydrellia griseola), tomato leafminer, (Liriomyza sativae), legume leafminer (Liriomyza trifolii), leafminer such as the pea (Chromatomyia horticola), chloropidae such as Inekimoguribae (Chlorops oryzae), melon fly (Dacus cucurbitae), fruit flies such as Ceratitis capitata, fruit flies such as Drosophila and flea flies, Megaseria spiracularis, Clogmial butterflies, etc. Kinokobae acids, blackfly acids, Abu such as gadfly (Tabanus trigonus), keds acids and stable flies such.

Coleoptera pests: Western Corn Rootworm (Diabrotica virgifera virgifera), corn rootworm such as southern corn rootworm (Diabrotica undecimpunctata howardi), cupreous chafer (Anomala cuprea), rufocuprea (Anomala rufocuprea), chafers such as Japanese beetle (Popillia japonica) , Weevil (Sitophilus zeamais), Rice weevil (Lissohoprus oryzophilus), Azuki beetle (Callosobrchuchus chiensis), Echonocnemus squatium (Echinocnemus quail) onomus grandis), weevils such as grass reed weevil (Sphenophorus venatus), Chai Loco Meno mealworm (Tenebrio molitor), mealworm such as red flour beetle (Tribolium castaneum),
Inedorooimushi (Oulema oryzae), cucurbit leaf beetle (Aulacophora femoralis), Kisujinomihamushi (Phyllotreta striolata), beetles such as Colorado potato beetle (Leptinotarsa decemlineata), varied carpet beetle (Anthrenus verbasci), carpet beetle such as Hara Giro beetle (Dermestes maculates), cigarette beetle (Lasiderma serricorne) and the like, Epilachna vigintioctopuncta and other epilacunas, Lyctus brunneus and pine beetle (Pompicus) erda), bark beetles, leopard beetles, longhorn beetles (Anoprophora malasiaca), longhorn beetles (Agriotes spp.), and blue scallops (ed) p.

  Diptera: Locusta migratoria, Kelly (Gryllotalpa africana), Oxya yezoensis, Oyana japonica, and crickets.

  Lepidoptera: Cat fleas (Ctenocephalides felis), Dog fleas (Ctenocephalides canis), Human fleas (Pulex irritans), Xenopsilla cheopes, etc.

  Anoplura: body louse (Pediculus humanus corporis), head lice (Pediculus humanus humanus), crab louse (Phthirus pubis), Ushijirami (Haematopinus eurysternus), Hitsujijirami (Dalmalinia ovis), Butajirami (Haematopinus suis), Inujirami (Linognathus setosus) and the like.

  White-eye pests: sheep lice (Dalmalinia ovis), cattle lice (Dalmalinia bovis), chicken lice (Menopon gallinae), dog lice (Trichodictes canis), feline larvae

  Hymenoptera: Monomorium phalaosis, Formica fusca japonica, Ochellelus glove, pistomrme puns, pol. Spr. Ants such as Argentine ants (Linepithema humile), wasps such as wasps, scallops, and wasps such as wasp (Athalia rosae) and Japanese bee (Athalia japonica).

  Nematodes: rice Shin Galle nematode (Aphelenchoides besseyi), strawberry menu nematode (Nothotylenchus acris), sweet potato root-knot nematode (Meloidogyne incognita), northern root-knot nematode (Meloidogyne hapla), Java root-knot nematode (Meloidogyne javanica), soybean cyst nematode (Heterodera glycines), Potato cyst nematodes (Globodera rostochiensis), Southern nematode crested peas (Pratylenchus coffeae), Barley nestle nematode (Pratylenchus neglectus).

  Cockroach insects: German cockroaches (Blatella germanica), Black cockroaches (Periplaneta furiginosa), American cockroaches (Periplaneta americana), Japanese cockroaches (Periplaneta brunet)

  Termite insect pests: Reticulites speratus, Cypterterms worm, Incitermes munus, Cyptotermes domesticus Glypoptermes satsumensis), Glypoptermes nakajii, Gyptotermes fuscus, Glyptotermes kodamai, Kushimoto Roari (Glyptotermes kushimensis), giant termite (Hodotermopsis japonica), Kou Shu Ye termite (Coptotermes guangzhoensis), Amami termites (Reticulitermes miyatakei), R. flavipes (Reticulitermes flaviceps amamianus), Kang Mont termites (Reticulitermes sp.), Takasago termite (Nasutitermes takasagoensis) , Nitrobe termites (Pericapritermes nitobei), Musya termites (Sinocapritermes mushae) and the like.

Mite order pests: Taninychus urticae, Kantawa spider mite (Tetranychus kanzawai), citrus spider mite (Panonychus citri), mite spider mite (Pananycos ulmi), spider mite pistula mite (Panthonychus urmi), spider mite pistula mite (Panthonychus urmi), spider mite pistula mite (Panthonychus urmi); Tomato rust mites (Aculops lycopersici), Chinese radish mites (Calacarus carinatus), Chinese radish mites (Acaphylla theavagrans), Green rust mites (Eriophys chibaensis), Apple rust ticles Fushidani such, dust mite such as Chanohokoridani (Polyphagotarsonemus latus), southern Hime Himehadani such as spider mites (Brevipalpus phoenicis), Kenagahadani such, longicornis (Haemaphysalis longicornis), Yamatochimadani (Haemaphysalis flava), Taiwan Kaku ticks (Dermacentor taiwanicus), American Catfish tick (Dermacentor variabilis), Yamato tick (Ixodes ovatus), Schulz tick (Ixodes perulcatus), Black legged tick (Ixodes scapularis), American thorny tick (Amblyomama amamma) ricanum), Boophilus microplus (Boophilus microplus), ticks such as Rhipicephalus sanguineus (Rhipicephalus sanguineus), Tyrophagus (Tyrophagus putrescentiae), grain mites such as Tyrophagus (Tyrophagus similis), farinae (Dermatophagoides farinae), D. pteronyssinus (Dermatophagoides ptrenyssnus) Leopard ticks, such as Cheyletus eruditus, Scarlet ticks (Cheyletus malacensis), Scarlet ticks (Cheyletus mooreii), Tiger ticks (Cheyletie) tick mites such as ll. Ornithonysus sylvairum, duck spider (Dermanysussus gallinae), etc .;
Lip and limb class: Geeu (Thereunema hilgendorfi), Tobizukade (Scorpendra subspinipes) and the like.
Double leg class: Oxidus gracilis, Nedyopus tambanus, etc.
Isopods: Armadillium vulgare, etc.
Gastropoda: Limax marginatus, Limax flavus, etc.

The pest control agent of the present invention contains the compound of the present invention and an inert carrier. The pest control agent of the present invention is usually a mixture of the compound of the present invention and an inert carrier such as a solid carrier, a liquid carrier, a gaseous carrier, etc., and a surfactant or other formulation adjuvant is added as necessary. Emulsions, oils, powders, granules, wettable powders, flowables, microcapsules, aerosols, smokers, poisonous baits, resin formulations, shampoos, pastes, foams, carbon dioxide formulations, It is formulated into tablets. These preparations may be used after being processed into mosquito coils, electric mosquito mats, liquid mosquito traps, fumigants, fumigants, sheet preparations, spot-on agents, or oral treatments.
The pest control agent of the present invention usually contains 0.01 to 95% by weight of the compound of the present invention.

  Examples of solid carriers used for formulation include clays (kaolin clay, diatomaceous earth, bentonite, fusami clay, acidic clay), synthetic hydrous silicon oxide, talc, ceramics, and other inorganic minerals (sericite, quartz, sulfur). , Activated carbon, calcium carbonate, hydrated silica, etc.), fine powders and granules of chemical fertilizers (ammonium sulfate, phosphorous acid, ammonium nitrate, urea, ammonium chloride, etc.), and synthetic resins (polypropylene, polyacrylonitrile, polymethyl methacrylate) Polyester resins such as polyethylene terephthalate, nylon resins such as nylon-6, nylon-11, and nylon-66, polyamide resins, polyvinyl chloride, polyvinylidene chloride, and vinyl chloride-propylene copolymers).

  Examples of the liquid carrier include water, alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), aromatic hydrocarbons (Toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil, etc.), esters (ethyl acetate, butyl acetate, isopropyl myristate, Ethyl oleate, diisopropyl adipate, diisobutyl adipate, propylene glycol monomethyl ether acetate, etc.), nitriles (acetonitrile, isobutyro Tolyl), ethers (diisopropyl ether, 1,4-dioxane, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, 3-methoxy-3-methyl-1-butanol, etc. ), Acid amides (N, N-dimethylformamide, N, N-dimethylacetamide, etc.), halogenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride, etc.), sulfoxides (dimethylsulfoxide, etc.), propylene carbonate and vegetable oil (Soybean oil, cottonseed oil, etc.).

  Examples of the gaseous carrier include fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether, and carbon dioxide gas.

  Examples of the surfactant include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, and polyethylene glycol fatty acid ester, and anions such as alkyl sulfonate, alkyl benzene sulfonate, and alkyl sulfate. Surfactant is mentioned.

  Examples of other adjuvants for preparation include fixing agents, dispersants, colorants and stabilizers, such as casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, Synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert- And a mixture of butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).

Examples of the base material of the resin preparation include vinyl chloride polymers, polyurethanes, etc., and these base materials include phthalic acid esters (dimethyl phthalate, dioctyl phthalate, etc.) and adipic acid esters as necessary. Further, a plasticizer such as stearic acid may be added. The resin formulation is obtained by kneading the compound in the base material using a normal kneading apparatus, and then molding by injection molding, extrusion molding, press molding, etc., and if necessary, through steps such as molding, cutting, It can be processed into resin preparations such as plate, film, tape, net, and string. These resin preparations are processed, for example, as animal collars, animal ear tags, sheet preparations, attracting strings, or gardening supports.
Examples of the bait base include cereal flour, vegetable oil, sugar, crystalline cellulose and the like, and if necessary, antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid, and preservatives such as dehydroacetic acid. Additives for preventing accidental eating by children and pets such as pepper powder, pests such as cheese flavor, onion flavor and peanut oil are added.

  The pest control method of the present invention is carried out by applying an effective amount of the compound of the present invention to pests directly and / or to pest habitats (plants, soil, households, animal bodies, etc.). The pest control method of the present invention is usually used in the form of the pest control agent of the present invention.

When the pest control agent of the present invention is used for pest control in the agricultural field, the application amount is usually 1 to 10,000 g in terms of the amount of the compound of the present invention per 10,000 m ² . When the pest control agent of the present invention is formulated into an emulsion, a wettable powder, a flowable agent, etc., it is usually diluted with water so that the active ingredient concentration is 0.01 to 10000 ppm. Agents, powders, etc. are usually applied as they are.

  These preparations and water dilutions of the preparations may be sprayed directly on pests or plants such as crops to be protected from pests, and in order to control pests that inhabit cultivated soil. You may process to soil.

  Moreover, it can also process by the method of wrapping the resin formulation processed into the sheet form or the string form around the crop, stretching over the crop vicinity, and laying on the stock soil.

When the pest control agent of the present invention is used for controlling pests living in the house, the amount applied is the amount of the compound of the present invention per 1 m ² treated area when treated on the surface, usually 0.01. The amount of the compound of the present invention per 1 m ³ of the treatment space is usually 0.01 to 500 mg. When the pest control agent of the present invention is formulated into an emulsion, a wettable powder, a flowable agent, etc., it is usually diluted with water so that the active ingredient concentration is 0.1 to 10,000 ppm. Apply aerosols, smoke, poisonous bait, etc. as they are.

  When the harmful arthropod control agent of the present invention is used to control ectoparasites of cattle, horses, pigs, sheep, goats, chickens, small animals such as dogs, cats, rats, mice, etc., it is well known in veterinary medicine. Can be used on animals. As a specific method of use, for the purpose of systemic suppression, for example, administration by tablet, feed mixing, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.) is intended for non-systemic suppression. In this case, for example, an oil agent or an aqueous liquid is sprayed, a pour-on treatment or a spot-on treatment is performed, the animal is washed with a shampoo preparation, or a resin preparation is attached to the animal with a collar or ear tag. The amount of the compound of the present invention when administered to an animal body is usually in the range of 0.1 to 1000 mg per 1 kg body weight of the animal.

The pest control agent of the present invention can be used in farmland where the following “crop” is cultivated.
Agricultural crops: corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, etc.
Vegetables: Solanum vegetables (eggplants, tomatoes, peppers, peppers, potatoes, etc.), Cucurbitaceae vegetables (cucumbers, pumpkins, zucchini, watermelons, melons, etc.), Brassicaceae vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage) , Mustard, broccoli, cauliflower, etc.), asteraceae vegetables (burdock, shungiku, artichokes, lettuce, etc.), liliaceae vegetables (leek, onion, garlic, asparagus), celery family vegetables (carrot, parsley, celery, American scallop, etc.) ), Red crustacean vegetables (spinach, chard, etc.);
Fruit trees: berries (apples, pears, Japanese pears, quince, quince, etc.), nuclear fruits (peaches, plums, nectarines, ume, sweet cherry, apricots, prunes, etc.), citrus (satsuma mandarin, orange, lemon, lime, grapefruit) ), Nuts (chestnut, walnut, hazel, almond, pistachio, cashew nut, macadamia nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, oyster, olive, loquat, banana, coffee, Date palm, coconut palm, oil palm etc.
Trees other than fruit trees: tea, mulberry, flowering trees (Satsuki, camellia, hydrangea, sasanqua, shikimi, sakura, yurinoki, crape myrtle, snapdragon, etc.), roadside trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak) , Poplar, redwood, fu, sycamore, zelkova, blackfish, Japanese amberjack, moths, pine, pine, spruce, yew, elm, Japanese cypress, etc.), coral jug, dogwood, cedar, cypress, croton, masaki, kanamochi, etc.
Lawn: Shiba (Nasis, Pleurotus, etc.), Bermudagrass (Neurodonidae, etc.), Bentgrass (Oleoptera, Hykonukagusa, Odonoptera, etc.), Bluegrass (Nagahagusa, Oosuzunokatabira, etc.), Fescue (Oonishi nokegusa, Drosophila, etc.) , Grass, etc.), ryegrass (rat, wheat, etc.), anemonefish, and blue whale.
Other: Flowers (Rose, Carnation, Chrysanthemum, Eustoma, Gypsophila, Gerbera, Marigold, Salvia, Petunia, Verbena, Tulip, Aster, Gentian, Lily, Pansy, Cyclamen, Orchid, Lily of the valley, Lavender, Stock, Habutton, Primula, Poinsettia, gladiolus, cattleya, daisy, symbidium, begonia, etc.), biofuel plants (Jatropha, Curcas, safflower, Amanazuna, switchgrass, Miscanthus, Kusanoshi, Danchiku, Kenaf, cassava, willow, algae, etc.), ornamental plants, etc. .

  “Crop” also includes genetically modified crops.

  The pest control agent of the present invention can be mixed or used in combination with other insecticides, acaricides, nematicides, fungicides, plant growth regulators, herbicides and synergists. Examples of active ingredients of such insecticides, acaricides, nematicides, fungicides, plant growth regulators, herbicides and synergists are shown below.

Active Ingredients of Insecticides (1) Organophosphorus Compounds Acephate, Aluminum Phosphide, Butathiofos, Cadosafos, Chlorethoxyfos, Chlorfenvinphos, Chlorfenvinphos (Chlorpyrifos), Chlorpyrifos-methyl (Chlorpyrifos-methyl), Cyanophos (Cyanophos: CYAP), Diazinon (Diazinon), DCIP (Dichlorodiisopropylene ether), Diclofenthion (V: D) ), Dimethoate, dimethylvinphos, disulfoton, EPN, etion, ethoprofos, etrimfos, fention (MPP), EP, Phosthiazate, formothion, hydrogen phosphide, isofenphos, isoxathion, malathion, methulfenfos, methulfenfos, methulfenfos MTP), monocrotophos, nared (BRP), oxydeprofos (ESP), parathion, fosarone, phosmet (PMP), pirimiphosmethyl (pirimithiopimethiopimethiopimethiopimethiopimethiopimethiopimethiopimethypisonepimethypisonepimethypisonepimethypisonepimethypisonepimethypisonepimethypisonepimethypisonepimethypisone (Pyridafenthion), quinalphos, phentoate (PAP), profenofos, propopafos, prothiofos, pyraclofos, phosphite, sulthio Tebupirimfos, temefos, tetrachlorbinphos (tetrach1orvinphos), terbufos, thiomethon, trichlorfon (DEP), bamidithios (vamidothionate, vamidothionate) .
(2) Carbamate compounds alaniccarb, bendiocarb, benfuracarb, BPMC, carbaryl (carbary1), carbofuran, carbothofen, loecarb , Fenobucarb, phenothiocarb, phenoxycarb, furathiocarb, isoprocarb (MIPC), methocarb (metolcarb) hiocarb), NAC, oxamyl (oxamyl), pirimicarb (pirimicarb), propoxur (propoxur: PHC), XMC, thiodicarb (thiodicarb), xylylcarb (xylylcarb), and aldicarb (aldicarb).

(3) Pyrethroid compounds acrinathrin, allethrin, benfluthrin, beta-cyfluthrin, bifenthrin, cycloprotorin, fluprothrin , Cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucitrate lucytrinate, flufenprox, flumethrin, fluvalinate, halfenprox, imiprothrin, permethrin, praretrin, praretrin resmethrin), sigma-cypermethrin, silaflufen, tefluthrin, tralomethrin, transfluthrin, tetramethrin. ethrin), phenothrin, cyphenothrin, alpha-permethrin, zeta-cypermethrin, lambda cihalothrin (lambda-halothrin) ), Furamethrin, tau-fluvalinate, methfluthrin, profluthrin, dimethylfluthrin, 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl EZ)-(1RS, 3RS; 1RS, 3S ) -2,2-dimethyl-3-prop-1-enylcyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4-methylbenzyl (EZ)-(1RS, 3RS; 1RS, 3SR) -2 , 2-dimethyl-3-prop-1-enylcyclopropanecarboxylate, and 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl (1RS, 3RS; 1RS, 3SR) -2,2- Dimethyl-3- (2-methyl-1-propenyl) cyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl (EZ)-(1RS, 3RS; 1RS, 3SR)- 2,2-Dimethyl-3- (2-cyano-1-propenyl) cyclopropanecarboxylate.
(4) Nereistoxin compounds Cartap, bensultap, thiocyclam, monosultap, and bisultap.

(5) Neonicotinoid compounds imidacloprid (imidac1oprid), nitenpyram (nitenpyram), acetamiprid (acetamipride), thiamethoxam, thiacloprid (thiacloprid), dinoteurin (dinothurine)
(6) Benzoylurea compound Chlorfluazuron, bistrifluron, diafenthiuron, diflubenzuron, fluazuron, flucycloxuron, flucyclolone (Flufenoxuron), hexaflumuron, lufenuron, novaluron, novifluuron, teflubenzuron, triflumuron, and triflumuron.
(7) Phenylpyrazole compounds Acetoprole, etiprole, fipronil, vaniliprole, pyriprole, and pyrafluprole.
(8) Bt toxin Live spores and produced crystal toxins derived from Bacillus thuringiensis, and mixtures thereof;
(9) Hydrazine compounds Chromafenozide, halofenozide, methoxyphenozide, and tebufenozide.
(10) Organochlorine compounds Aldrin, dieldrin, dienochlor, endosulfan, and methoxychlor.

(11) Other insecticide active ingredients Machine oil (nicotine-sulfate); avermectin (avermectin-B), bromopropyrate, buprofezin, chlorphenapyr Ritranol, cyromazine, DD (1,3-Dichloropropene), emamectin benzoate, fenazaquin, flupyrazolep , Indoxacarb, methoxadiazone, milbemycin-A, pymetrozine, pyridalyl, pyriprosul, spiromidol, spinomidol tolfenpyrad, triazamate, flubendiamide, repimectin, arsenous acid, benclothiaz, lime nitrogen calcium lime ulfide, chlordane, DDT, DSP, flufenerium, flonicamid, flurimfen, formatenate, metam-ammonium, metam-ammonium sodium, methyl bromide, potassium oleate, protrifenbute, spiromesifen, sulfoxafluor, sulfur, metafluon, sulfur ), Spirotetramat (sp rotetramat), pyrifluquinazon (pyrifluquinazone), spinetoram (spinetoram), chlorantraniliprole (chlorantraniliprole), Toraropiriru (tralopyril), cyan tiger Niri Prowl (cyantraniliprole),
Following formula (K)
[Where,
R ¹⁰⁰ represents a chlorine, bromine or trifluoromethyl group,
R ²⁰⁰ represents a chlorine, bromine or methyl group,
R ³⁰⁰ represents chlorine, bromine or a cyano group. ]
And a compound represented by the following formula (L)
[Where,
R ¹⁰⁰⁰ represents chlorine, bromine or iodine. ]
A compound represented by

Active ingredients of acaricides: acequinocyl, amitraz, benzoximate, bifenaate, phenisobromolate (BS), chinomethionate (BS), chinomethionate (BS) chlorfenson, clofentezine, cyflumetofene, kelsen (dicofol), etoxazole, fenbutatin oxide (fenbutafen), fenothiocarbene roximate, fluacrylpyrim, fluproxyfen, hexythiazox, propargite (BPPS), polynactin complex (pyridene), pyridaben (pyriben) (Tetradifon), spirodiclofen, spiromesifen, spirotetramat, amidoflumet, and cenopyrafen.

Active ingredients of nematicides DCIP, fostiazate, levamisole hydrochloride, methylisothiocyanate, morantel tartrate, and imiciafos.

Active ingredients of fungicides Propiconazole, Prothioconazole, Triadimenol, Prochloraz, Penconazole, Tebuconazole, Tebuconazole, Tebuconazole , Bromuconazole, epoxiconazole, difenoconazole, cyproconazole, metconazole, triflumazole, triflumizole Tetraconazole, microbutanil, fenbuconazole, hexaconazole, fluquinconazole, triticonazole, triticonazole, tericonazole, triticonazole, triticonazole Azole fungicidal compounds such as flutriafol;
Cyclic amine bactericidal compounds such as fenpropimorph, tridemorph, fenpropidin;
Benzimidazolic fungicidal compounds such as carbendezim, benomyl, thiabendazole, thiophanate-methyl;
Procymidone; cyprodinil; pyrimethanil; dietofencarb; thiuram; fluazilonyl; Captan; mepanipyrim; fenpiclonil; fludioxonil; diclofluraned; folppet; cresoxime- azoxystrobin; trifloxystrobin; fluoxastrobin; picoxystrobin; pyracrostrobin; dimoxystrobin; dimoxystrobin; dimoxystrobin; Pyribencarb; spiroxamine; quinoxyfen; fenhexamid; famoxadone; fenamidone; samamide; samamide; samamide; iprovalicarb; benthiavaricarb; cyazofamid; mandipropamid; boscaliden; (Bifafen); cyflufenamide; proquinazid; isotianil and thiadinil.

Active ingredient of herbicide (1) Phenoxy fatty acid herbicidal compound 2,4-PA, MCP, MCPB, phenthiol (phenothio1), mecoprop, fluroxypyr, triclopyr, clomeprop Naproanilide.
(2) Benzoic acid herbicidal compound 2,3,6-TBA, dicamba, clopyralid, picloram, aminopyralid, quinclorac, and quinmerac.
(3) Urea herbicidal compounds diuron, linuron, chlortoluron, isoproturon, fluometuron, isouron, tebuthiuron, tebuthiuron, metabenthuron , Cumyluron, daimuron, and methyl-daimuron.
(4) Triazine herbicidal compounds atrazine, ametrine, cyanazine, simazine, propazine, simetrin, dimethamethrin (dimethymetrine) ), Triaziflam, and indaziflam.
(5) Bipyridinium herbicidal compound paraquat and diquat.

(6) Hydroxybenzonitrile herbicidal compounds bromoxynil and ioxynil.
(7) Dinitroaniline herbicidal compounds pendimethalin, prodiamine, and trifluralin.
(8) Organic phosphorus herbicidal compounds amiprofos-methyl, butamifos, bensulide, piperophos, anilofos, glyphosate, glufosinate, glufosinate, glufosinate P (glufosinate-P), and bialaphos.
(9) Carbamate herbicidal compounds di-allate, tri-allate, EPTC, butyrate, beniocarb, esprocarb, molinate, dimipeperate (Swep), chlorpropham, phenmedifam, phenisopham, piributicarb, and asuram.
(10) Acid amide herbicidal compounds propanil, propyzamide, bromobutide, and etobanzanide.

(11) Chloroacetanilide herbicidal compounds acetochlor, acechlor, butachlor, dimethenamide, propachlor, metazachlor, metrachlor or totrachlor pretilachlor), tenylchlor (theny1ch1or), and petoxamide.
(12) Diphenyl ether herbicidal compounds aciflufen-sodium, bifenox, oxyfluorfen, lactofen, fomesafen, clomethoxythonifen, and clomethoxythonipheni.
(13) Cyclic imide herbicidal compounds oxadiazon, cinidone-ethyl, carfentrazone-ethyl, sulfentrazone, full-microlac-pentyl, flumi-lacyl-pentyl Oxazine (flumioxazin), pyraflufen-ethyl, oxadiargyl (oxadiargy1), pentoxazone (pentoxazone), fluthiacet-methyl (butafenzilben) zone), and saflufenacil (saflufenacil).
(14) Pyrazole herbicidal compounds benzofenap, pyrazolate, pyrazoxifene, topramzone, and pyrasulfotole.
(15) Triketone herbicidal compounds isoxaflutole, benzobicyclon, sulcotrione, mesotrione, tembotrione, and tefriltrione.
(16) Aryloxyphenoxypropionic acid herbicidal compound clodinafop-propargyl, cyhalofop-butyl, diclohop-methyl, phenoxaprop-ethyl, fenoxaprop-propyl Fluazifop-butyl, haloxyhop-methyl, and quizalofop-ethyl, metamihop.
(17) Trionoxime herbicidal compounds alloxydim-sodium, cetoxydim, butoxydim, crestodim, cloxydimim, cycloxidim, texydimym (Traxydim), and profoxydim.

(18) sulfonylurea herbicidal compounds chlorsulfuron, sulfomethuron-methyl, metsulfuron-methyl, chlorimuron-ethyl, tribenuron methyl (18) tribenuron-methyl, triasulfuron, bensulfuron-methyl, thifensulfuron-methyl, pyrazosulfuron-methyl, urmisyl Nicosulfuron (nico) ulfuron, amidosulfuron, cinosulfuron, imazosulfuron, rimsulfuron, halosulfuron (th), thulfuron (thulsulfuron), prosulfuron (thulsulfuron) , Triflusulfuron-methyl, flazasulfuron, cyclosulfamuron, flupirsulfuron, sulfosulfurium, sulfosulfurium Azulsulfuron, ethoxysulfuron, oxasulfuron, iodosulfuron-methyl-sodium, foramsulfuron, mesosulfuron, mesulfuron methyl Trisulfursulfuron, tritosulfuron, orthosulfamuron, flucetosulfuron, and propyrisulfuron.
(19) Imidazolinone herbicidal compounds imazametabenz-methyl, imazamethapyr, imazamox, imazapyr, and imazakin (p), imazaquin (p)
(20) Sulfonamide herbicidal compounds flumetslam, metosulam, dicloslam, floraslam, chloransrammethyl, penoxsulox, penoxsulox, and penoxsulox.
(21) Pyrimidinyloxybenzoic acid herbicidal compound pyrithiobac-sodium, bispyribac-sodium, pyriminobac-methy1, pyribenzoximid, pyrifalidomid And pyrimisulfan.
(22) Other herbicidal compounds bentazon, bromacil, terbacil, chlorthiamid, isoxaben, dinoseb, amitrole, cinmethyline, cinmethyline (cinthyl) tripiphane, dalapon (da1apon), diflufenzopyr sodium (diflufenzopyr-sodium), dithiopyr (dithiopyr), thiazopyr (thiazopyr), sodium flucarbazone (proflubazone) Nasset (mefenacet), flufenacet (flufenacet), fentrazamide (fentrazamide), caffenstrole (cafenstrom), indanophan (indanofan), oxadichromemephone (oxaneclomefone), fidarate (benduresate) (Norflurazon), flurtamon, diflufenican, picolinafen, beflubutamide, clomazone, amicarbazone , Pinoxaden (pinoxaden), pyraclonil (pyraclonil), pyroxasulfone (pyroxasulfone), thien-carbazone methyl (thiencarbazone-methyl), amino cyclo Pila crawl (aminocyclopyrachlor), type phen carbazone (ipfencarbazone), and Mechiozorin (methiozolin).

Active ingredients of plant growth regulators: hymexazole, paclobutrazol, uniconazole-P, inabenfide, prohexadione-calcium, ibiglycin -Naphthylacetamide, abscisic acid, indolebutyric acid, ethiclozate, etephon, cloxymecpro, cloxymecpro rprop), gibberellins, prohydrojasmon, benzylaminopurine, forchlorfenuron, maleic hydrazide, c-peroxide, c Chloride (mepiquat-chloride) and 4-CPA (4-chlorophenoacetic acid).

Active ingredient of synergist piperonyl butoxide, sesamex, sulfoxide, N- (2-ethylhexyl) -8,9,10-trinorborn-5-ene-2,3-di Carboximide (MGK 264), N-decrimimidazole (N-decylimidazole), WARF-anti-resistant (TBRF-antiresistant), TBPT, TPP, IBP, PSCP, methyl iodide (CH ₃ I), t-phenyl butyl Tenon (t-phenylbutone), diethyl maleate, DMC, FDMC, ETP, and ETN.

Hereinafter, although this invention is demonstrated in more detail by a manufacture example, a reference manufacture example, a formulation example, a test example, etc., this invention is not limited only to these examples.
First, a manufacture example is shown about manufacture of this invention compound.

Production Example 001
A mixture of 10 g of 5-trifluoromethylpyridin-2-ol and 52 mL of sulfuric acid was heated and stirred at 95 ° C., a mixture of 8 mL of fuming nitric acid and 10 mL of sulfuric acid was added dropwise, and the mixture was heated and stirred for 4 hours. The reaction mixture cooled to room temperature was poured into ice, saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 7.4 g of 3-nitro-5-trifluoromethylpyridine-2-ol.

¹ H-NMR (DMSO-d ₆ ) δ: 13.54 (1H, brs), 8.67 (1H, d), 8.46 (1H, d)

Production Example 002
To a mixture of 3.2 g of 3-nitro-5-trifluoromethylpyridine-2-ol and 1 drop of DMF, 8.2 mL of phosphorus oxychloride was added at room temperature. The mixture was heated to 105 ° C. and stirred for 24 hours. After cooling the reaction mixture to room temperature, the reaction mixture was poured into ice and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain 2.5 g of 2-chloro-3-nitro-5-trifluoromethylpyridine.

Production Example 003
To a mixture of 2.5 g of 2-chloro-3-nitro-5-trifluoromethylpyridine and 5 mL of ethanol was added 5 mL of 28% aqueous ammonia solution under ice cooling. The mixture was warmed to room temperature and stirred for 5 hours. After cooling the reaction mixture to room temperature, the reaction mixture was poured into ice and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and then concentrated under reduced pressure to obtain 2.2 g of 2-amino-3-nitro-5-trifluoromethylpyridine.

Production Example 004
To a mixture of 890 mg of iron powder, 30 mL of ethanol, 20 mL of water, and 1.4 g of ammonium chloride, a mixture of 2.2 g of 2-amino-3-nitro-5-trifluoromethylpyridine and 15 mL of THF was added at 40 ° C. Stir at 4 ° C. for 4 hours. The reaction mixture allowed to cool was filtered, and the filtrate was concentrated under reduced pressure. Ethyl acetate and water were added to the resulting residue for liquid separation. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure to obtain 1.8 g of 5-trifluoromethyl-pyridine-2,3-diamine.

¹ H-NMR (CDCl ₃ ) δ: 7.93 (1H, d), 7.04 (1H, d), 4.71 (2H, brs), 3.46 (2H, brs).

Production Example 005
To a mixture of 65 g of 5-trifluoromethyl-pyridin-2-ylamine and 100 mL of chloroform, 71 g of N-bromosuccinimide was added in 5 portions under cooling with ice water. After heating up to room temperature and stirring for 1 hour, it heated to 80 degreeC and heated and stirred for 30 minutes. After cooling to room temperature, a saturated aqueous sodium thiosulfate solution and a saturated aqueous sodium hydrogen carbonate solution were added, and the mixture was extracted with chloroform. The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 96 g of 3-bromo-5-trifluoromethyl-pyridin-2-ylamine.

¹ H-NMR (CDCl ₃ ) δ: 8.27 (1H, d), 7.86 (1H, d), 5.38 (2H, brs).

Production Example 006
3-Bromo-5-trifluoromethyl-pyridin-2-ylamine 40 g, acetylacetone copper (II) 2.2 g, acetylacetone 6.6 g, cesium carbonate 59 g, and NMP 105 mL were added to an autoclave reactor, and 28% aqueous ammonia solution was cooled with ice. 25 mL was added. After sealing, the temperature was raised to 110 ° C. and heated and stirred for 12 hours. After cooling to room temperature with ice, the reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 15 g of 5-trifluoromethyl-pyridine-2,3-diamine.

¹ H-NMR (CDCl ₃ ) δ: 7.93 (1H, d), 7.04 (1H, d), 4.71 (2H, brs), 3.46 (2H, brs).

Production Example 007
7.4 g of sodium ethanethiolate (90%) was added to a mixture of 15.1 g of 2-fluoro-4-trifluoromethylbenzaldehyde and 61 mL of DMF, and the mixture was stirred at room temperature for 6 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 12 g of 2-formyl-5-trifluoromethylphenylethyl sulfide.

¹ H-NMR (CDCl ₃ ) δ: 10.41 (1H, s), 7.94 (1H, d), 7.63 (1H, s), 7.53 (1H, d), 3.04 ( 2H, q), 1.41 (3H, t).

Production Example 008
To a mixture of 2.2 g of C- (2-chloro-thiazol-5-yl) -methylamine, 2.3 g of N, N-diisopropylethylamine and 15 mL of N-methyl-2-pyrrolidone, 6.0 g of chloro-3-nitro-5-trifluoromethylpyridine was added dropwise. The reaction mixture was stirred for 1 hour under ice cooling. A 10% aqueous citric acid solution was poured into the obtained reaction mixture, and the mixture was extracted with ethyl acetate. The combined organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure to give (2-chloro-thiazol-5-ylmethyl)-(3-nitro-5-trifluoromethylpyridine-2- Yl) 4.1 g of amine was obtained.

¹ H-NMR (CDCl ₃ ) δ: 8.75-8.68 (3H, m), 7.53 (1H, s), 4.97 (2H, d).

Production Example 009
To a mixture of 8.1 g of iron powder, 20 mL of ethanol, 6 mL of water and a few drops of acetic acid, (2-chloro-thiazol-5-ylmethyl)-(3-nitro-5-trifluoromethylpyridin-2-yl) amine was added. After adding a mixture of 4.0 g and 20 mL of ethanol at 70 ° C., the mixture was stirred at 70 ° C. for 1 hour. The reaction mixture allowed to cool was filtered, and the filtrate was concentrated under reduced pressure. Ethyl acetate and water were added to the resulting residue for liquid separation. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure, ^{N 2} - (2-chloro - thiazole --5-ylmethyl) -5-trifluoromethyl - pyridin-2,3-diamine 3. 5 g was obtained.

¹ H-NMR (CDCl ₃ ) δ: 8.07 (1H, s), 7.45 (1H, s), 7.05 (1H, d), 4.91 (1H, brs), 4.78 ( 2H, d), 3.31 (2H, brs).

Production Example 010
N ² - (2-chloro - thiazole --5-ylmethyl) -5-trifluoromethyl - pyridin-2,3-diamine 0.3 g, 2-ethylsulfanyl-benzoic acid 0.2g, WSC0.2g, HOBt14mg and A mixture of 1 mL of pyridine was stirred at room temperature for 3 hours. To this reaction mixture was poured 10% aqueous citric acid solution, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with water, dried over sodium sulfate, concentrated under reduced pressure, and N- {2- [2-chloro-thiazol-5-ylmethyl] -amino] -5-trifluoromethyl-pyridine-3- 0.4 g of yl} -2-ethylsulfanyl-benzamide was obtained.

¹ H-NMR (CDCl ₃ ) δ: 8.41 (2H, brs), 7.86-7.77 (2H, m), 7.54-7.34 (4H, m), 6.07 (1H , T), 4.81 (2H, d), 2.94 (2H, q), 1.26 (3H, t).

Production Example 011
0.4 g N- {2- [2-chloro-thiazol-5-ylmethyl] -amino] -5-trifluoromethyl-pyridin-3-yl} -2-ethylsulfanyl-benzamide, p-toluenesulfonic acid A mixture of 0.4 g of hydrate, 10 mL of N-methyl-2-pyrrolidone and 10 mL of xylene was heated to reflux for 8 hours while dehydrating using a Dean-Stark apparatus. The reaction mixture was allowed to cool, water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and 3- (2-chloro-thiazol-5-ylmethyl) -2- (2-ethylsulfanyl-phenyl) -6-trifluoromethyl-3H-imidazo [4, 0.2 g of 5-b] pyridine (hereinafter referred to as the present compound 001) was obtained.

Production Example 012
Mixture of 0.2 g 3- (2-chloro-thiazol-5-ylmethyl) -2- (2-ethylsulfanyl-phenyl) -6-trifluoromethyl-3H-imidazo [4,5-b] pyridine and 2 mL chloroform Under ice cooling, 0.2 g of m-chloroperbenzoic acid (69-75%) was added, and the mixture was warmed to room temperature and stirred for 1 hour. To this reaction mixture, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium thiosulfate solution were added, and the mixture was extracted with chloroform. The combined organic layers were washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 3- (2-chloro-thiazol-5-ylmethyl) -2- (2-ethanesulfonyl-phenyl) -6-trifluoromethyl-3H-imidazo [4 5-b] pyridine (hereinafter referred to as the present compound 002) 0.18 g was obtained.

Production Example 013
A mixture of 5.8 g of 5-trifluoromethyl-pyridine-2,3-diamine, 4.6 g of 2-ethylsulfanylbenzoic acid, 4.9 g of WSC and 10 mL of pyridine was stirred at room temperature for 3 hours. To this reaction mixture was poured 10% aqueous citric acid solution, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with water, dried over sodium sulfate, and concentrated under reduced pressure to obtain 4.7 g of N- (2-amino-5-trifluoromethylpyridin-3-yl) -2-ethylsulfanyl-benzamide. It was.

¹ H-NMR (DMSO-d ₆ ) δ: 9.75 (1H, s), 8.17 (1H, s), 8.09 (1H, s), 7.64 (1H, d), 7. 53-7.45 (2H, m), 7.34-7.28 (1H, m), 6.71 (2H, s), 2.97 (2H, q), 1.22 (3H, t)

Production Example 014
A mixture of 200 mg of N- (2-amino-5-trifluoromethylpyridin-3-yl) -2-ethylsulfanyl-benzamide, 1 mL of tert-butyl alcohol and 9 mL of THF was heated and stirred at 80 ° C., and 60% 56 mg of sodium hydride (oily) was added. The mixture was heated and stirred at 80 ° C. for 2 hours, and 56 mg of 60% sodium hydride (oily) was added. Furthermore, after stirring with heating at the same temperature for 2 hours, 56 mg of 60% sodium hydride (oily) was added, and the mixture was heated with stirring at the same temperature for 2 hours. The reaction mixture was cooled to room temperature, the solvent was evaporated, saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 132 mg of 2- (2-ethylsulfanylphenyl) -6-trifluoromethyl-3H-imidazo [4,5-b] pyridine.

¹ H-NMR (CDCl ₃ ) δ: 8.67 (1H, d), 8.51-8.48 (1H, m), 8.33 (1H, d), 7.66-7.61 (1H M), 7.51-7.46 (2H, m), 2.93 (2H, q), 1.27 (3H, t)

Production Example 015
To a mixture of 2.3 g of 2- (2-ethylsulfanylphenyl) -6-trifluoromethyl-3H-imidazo [4,5-b] pyridine and 20 mL of chloroform was added 69-75% 3-chloroperbenzoic acid under ice cooling. 8.0 g was added. The mixture was warmed to room temperature and stirred for 0.5 hour, and then a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium thiosulfate solution were added, and the mixture was extracted with chloroform. The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and the resulting crystals were washed with hexane to give 2- (2-ethylsulfonyl-phenyl) -6-trifluoromethyl-3H-imidazo [4,5-b] pyridine. 2.5 g was obtained.

¹ H-NMR (CDCl ₃ ) δ: 8.63 (1H, s), 8.35 (1H, s), 8.24 (1H, d), 8.09 (1H, d), 7.83 ( 1H, t), 7.76 (1H, t), 3.33 (2H, q), 0.88 (3H, t).

Production Example 016
To a mixture of 8.6 g of 5-trifluoromethyl-pyridine-2,3-diamine, 11 g of 2-formyl-5-trifluoromethylphenylethyl sulfide, and 67 mL of DMF, 6.1 g of sodium bisulfite was added at room temperature. . After heating and stirring at 100 ° C. for 3 hours, 1 g of copper (II) chloride dihydrate was added, and the mixture was further heated and stirred at 100 ° C. for 1 hour. After cooling to room temperature, the reaction mixture was added to water and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain a yellow powdered solid. This was washed with hot hexane to obtain 12 g of 2- (2-ethylsulfanyl-4-trifluoromethyl-phenyl) -6-trifluoromethyl-3H-imidazo [4,5-b] pyridine.

¹ H-NMR (CDCl ₃ ) δ: 12.79 (1H, brs), 8.72 (1H, brs), 8.49-8.34 (2H, m), 7.79 (1H, s), 7.64 (1H, d), 3.00 (2H, q), 1.31 (3H, t).

Production Example 017
To a mixture of 12 g of 2- (2-ethylsulfanyl-4-trifluoromethyl-phenyl) -6-trifluoromethyl-3H-imidazo [4,5-b] pyridine and 111 mL of chloroform was added m-chloroperoxide under ice-cooling. 8.0 g of benzoic acid (69-75%) was added. The mixture was warmed to room temperature and stirred for 0.5 hour, and then a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium thiosulfate solution were added, and the mixture was extracted with chloroform. The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 9.1 g of 2- (2-ethanesulfonyl-4-trifluoromethyl-phenyl) -6-trifluoromethyl-3H-imidazo [4,5-b] pyridine. .

¹ H-NMR (DMSO-d ₆ ) δ: 14.15 (1H, brs), 8.83 (1H, s), 8.58 (1H, s), 8.41 (1H, d), 8. 37 (1H, s), 8.19 (1H, d), 3.97 (2H, q), 1.23 (3H, t).

Production Example 018
To a mixture of 2- (2-ethanesulfonyl-4-trifluoromethyl-phenyl) -6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (200 mg) and DMF (1 mL) was added sodium hydride (oil, 60%) 19 mg was added and stirred at room temperature for 30 minutes. To this mixture, a mixture of 70 mg of 4-methylbenzyl chloride and 1 mL of DMF was added under ice cooling, and the mixture was warmed to room temperature and stirred for 3 hours. Thereafter, the temperature was raised to 50 ° C., and the mixture was heated and stirred for 3 hours. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to give 2- (2-ethanesulfonyl-4-trifluoromethyl-phenyl) -3- (4-methyl-benzyl) -6-trifluoromethyl-3H-imidazo [4,5- b] 57 mg of pyridine (hereinafter referred to as the present compound 009) and 2- (2-ethanesulfonyl-4-trifluoromethyl-phenyl) -1- (4-methyl-benzyl) -6-trifluoromethyl- 21 mg of 1H-imidazo [4,5-b] pyridine (hereinafter referred to as the present compound 018) was obtained.

Production Example 019
Mixture of 2- (2-ethylsulfonyl-4-trifluoromethyl-phenyl) -6-trifluoromethyl-3H-imidazo [4,5-b] pyridine 200 mg, 4-dimethylamino-pyridine 6 mg, triethylamine 58 mg, DMF 1 mL Under ice cooling, 84 mg of 2-chlorobenzyl chloride was added, and the mixture was warmed to room temperature and stirred for 3 hours. Then, it heated up to 80 degreeC and heated and stirred for 3 hours. Saturated aqueous ammonium chloride solution was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was chromatographed on silica gel to give 3- (2-chloro-benzyl) -2- (2-ethanesulfonyl-4-trifluoromethyl-phenyl) -6-trifluoromethyl-3H-imidazo [4,5- b] 64 mg of pyridine (hereinafter referred to as the present compound 004) and 1- (2-chloro-benzyl) -2- (2-ethanesulfonyl-4-trifluoromethyl-phenyl) -6-trifluoromethyl-1H -18 mg of imidazo [4,5-b] pyridine (hereinafter referred to as the present compound 014) was obtained.

  The compound of the present invention produced in the same manner as the compound of the present invention and the production method is shown in the table.

Compound represented by formula (1-3).
In the formula, R ^1c , R ^3c , R ^6c , R ^8c , A ^2c and n represent the combinations described in the following [Table 45].

Compound represented by formula (1-4).
R ¹ , R ³ , R ⁷ , R ⁸ , R ¹⁰ , A ¹ and n in the formula represent the combinations described in [Table 46] below.

The ¹ H-NMR data of the compounds of the present invention described in [Table 45] and [Table 46] are shown below.

Compound 002 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 8.79 (1H, d), 8.31 (1H, d), 8.26 (1H, dd), 7.90-7.78 (2H, m), 7.40 (1H, dd), 7.14 (1H, s), 5.79-5.02 (2H, brm), 3.48-3.24 (2H, brm), 1.24 (3H, t).

Compound 003 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 8.81 (1H, d), 8.44 (1H, d), 8.33 (1H, d), 7.74 (1H, dd), 7.25- 7.19 (3H, m), 7.13 (1H, d), 7.00-6.96 (2H, m), 5.39 (2H, brs), 3.43 (2H, q), 1 .26 (3H, t).

Compound 004 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 8.81 (1H, d), 8.40 (1H, d), 8.35 (1H, d), 7.70 (1H, dd), 7.29- 7.26 (1H, m), 7.19 (1H, td), 7.13 (1H, d), 7.05 (1H, td), 6.93 (1H, dd), 5.57 (2H) , Brs), 3.42 (2H, q), 1.26 (3H, t).

Compound 005 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 8.80 (1H, d), 8.38 (1H, d), 8.35 (1H, d), 7.60 (1H, dd), 7.14 ( 1H, td), 7.07 (1H, d), 6.98 (1H, d), 6.90 (1H, t), 6.62 (1H, d), 5.45 (2H, brs), 3.40 (2H, q), 2.01 (3H, s), 1.28-1.23 (3H, m).

Compound 006 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 8.81 (1H, d), 8.46 (1H, d), 8.34 (1H, d), 7.83 (1H, dd), 7.25- 7.14 (3H, m), 6.96-6.94 (1H, m), 6.91-6.87 (1H, m), 5.35 (2H, brs), 3.42 (2H, q), 1.27 (3H, t).

Compound 007 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 8.81 (1H, d), 8.44 (1H, d), 8.33 (1H, d), 7.73 (1H, dd), 7.12- 7.04 (3H, m), 6.77-6.72 (2H, m), 5.35 (2H, brs), 3.42 (2H, q), 2.21 (3H, s), 1 .26 (3H, t).

Compound 008 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 8.80 (1H, d), 8.46 (1H, d), 8.34 (1H, d), 7.84 (1H, dd), 7.23- 7.19 (3H, m), 6.98-6.94 (2H, m), 5.36 (2H, brs), 3.43 (2H, q), 1.27 (3H, t).

Compound 009 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 8.81 (1H, d), 8.44 (1H, d), 8.32 (1H, d), 7.75 (1H, dd), 7.15 ( 1H, d), 7.01 (2H, d), 6.87 (2H, d), 5.35 (2H, brs), 3.43 (2H, q), 2.30 (3H, s), 1.26 (3H, t).

Compound 010 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 8.81 (1H, d), 8.63-8.50 (1H, brm), 8.48 (1H, d), 8.34 (1H, d), 8.32-8.20 (1H, brm), 7.91 (1H, dd), 7.53 (1H, d), 7.32 (1H, d), 7.25-7.17 (1H, brm), 5.86-5.12 (2H, brm), 3.74-2.46 (2H, m), 1.35-1.25 (3H, brm).

Compound 011 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 8.82 (1H, d), 8.51 (1H, d), 8.33 (1H, d), 8.07 (1H, dd), 7.56 ( 1H, d), 7.20 (1H, s), 5.42 (2H, brs), 3.40 (2H, brs), 1.30-1.24 (3H, m).

The present compound 012
¹ H-NMR (CDCl ₃ ) δ: 8.78 (1H, s), 8.48 (1H, s), 8.32 (1H, d), 8.05 (1H, d), 7.96 ( 1H, d), 7.54 (1H, dd), 7.39 (1H, d), 7.21 (1H, d), 5.34 (2H, brs), 3.42 (2H, q), 1.26 (3H, t).

The present compound 013
¹ H-NMR (CDCl ₃ ) δ: 8.88 (1H, d), 8.47 (1H, d), 7.90 (1H, dd), 7.76 (1H, d), 7.49 ( 1H, d), 7.36-7.31 (3H, m), 7.10-7.05 (2H, m), 5.25 (2H, brs), 4.15-4.03 (2H, m), 1.40-1.24 (3H, m).

Compound 014 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 8.90 (1H, d), 8.45 (1H, d), 7.84 (1H, dd), 7.81 (1H, d), 7.44- 7.39 (2H, m), 7.29 (1H, td), 7.14 (1H, td), 6.88 (1H, dd), 5.36 (2H, brs), 3.52 (2H) , Brs), 1.27 (3H, t).

Compound 015 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 8.89 (1H, d), 8.45 (1H, d), 7.81 (1H, dd), 7.73 (1H, d), 7.42- 7.07 (4H, m), 6.73 (1H, d), 5.20 (2H, brs), 3.55 (2H, brs), 2.17 (3H, s), 1.40-1 .24 (3H, m).

Compound 016 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 8.88 (1H, d), 8.47 (1H, d), 7.89 (1H, dd), 7.79 (1H, d), 7.46 ( 1H, d), 7.20 (1H, d), 7.14 (1H, d), 6.84 (2H, brs), 5.20 (2H, brs), 3.55 (2H, brs), 2.28 (3H, s), 1.41-1.21 (3H, m).

Compound 017 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 8.89 (1H, d), 8.48 (1H, d), 7.94 (1H, dd), 7.75 (1H, d), 7.50 ( 1H, d), 7.34-7.29 (2H, m), 7.05-7.01 (2H, m), 5.39-5.04 (2H, m), 3.74-3. 39 (2H, m), 1.42-1.24 (3H, m).

Compound 018 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 8.87 (1H, d), 8.47 (1H, d), 7.90 (1H, dd), 7.77 (1H, d), 7.50 ( 1H, d), 7.13 (2H, d), 6.95 (2H, d), 5.19 (2H, brs), 3.57 (2H, brs), 2.34 (3H, s), 1.30-1.24 (3H, m).

The present compound 019
¹ H-NMR (CDCl ₃ ) δ: 8.92 (1H, d), 8.50 (1H, d), 8.08 (1H, dd), 7.93 (1H, d), 7.67 ( 1H, d), 7.38 (1H, s), 5.49-5.19 (2H, brm), 3.60-3.31 (2H, brm), 1.30-1.24 (3H, m).

Compound 020 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 8.90 (1H, s), 8.48 (1H, s), 8.19 (1H, d), 7.99 (1H, d), 7.76 ( 1H, s), 7.55 (1H, d), 7.42 (1H, dd), 7.28 (1H, d), 5.25 (2H, brs), 3.53 (2H, brs), 1.28 (3H, t).

  Next, the formulation example of this invention compound is shown. In addition, a part represents a weight part.

Formulation Example 1
10 parts of any one of the compounds of the present invention 001 to 020 are dissolved in a mixture of 35 parts of xylene and 35 parts of N, N-dimethylformamide, and 14 parts of polyoxyethylene styryl phenyl ether and 6 parts of calcium dodecylbenzenesulfonate. And mix to obtain each emulsion.

Formulation Example 2
4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic silicon hydroxide fine powder and 54 parts of diatomaceous earth are mixed, and 20 parts of any one of the compounds 001 to 020 of the present invention are added and mixed, respectively. Get a wettable powder.

Formulation Example 3
1 part of the synthetic silicon hydrous fine powder, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay are mixed with 2 parts of any one of the compounds 001 to 020 of the present invention. Next, an appropriate amount of water is added to the mixture, and the mixture is further stirred, granulated by a granulator, and dried by ventilation to obtain each granule.

Formulation Example 4
One part of any one of the compounds of the present invention 001 to 020 is dissolved in an appropriate amount of acetone, and 5 parts of a synthetic silicon hydroxide fine powder, 0.3 part of PAP and 93.7 parts of fusami clay are added, and the mixture is sufficiently stirred and mixed. Acetone is removed by evaporation to obtain each powder.

Formulation Example 5
35 parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and white carbon (weight ratio 1: 1), 10 parts of any one of the compounds 001 to 020 of the present invention, and 55 parts of water are mixed, and wet pulverization method Each flowable agent is obtained by finely pulverizing with.

Formulation Example 6
0.1 part of any one of the compounds of the present invention 001 to 020 is dissolved in 5 parts of xylene and 5 parts of trichloroethane, and this is mixed with 89.9 parts of deodorized kerosene to obtain each oil agent.

Formulation Example 7
10 mg of any one of the compounds 001 to 020 of the present invention is dissolved in 0.5 mL of acetone, and this solution is treated with 5 g of animal solid feed powder (solid feed powder CE-2 for breeding breeding, a product of Nippon Claire Co., Ltd.). And mix evenly. Then acetone is evaporated to dryness to obtain each poisonous bait.

Formulation Example 8
0.1 part of any one of the compounds of the present invention 001 to 020, 49.9 parts of neothiozole (Chuo Kasei Co., Ltd.) are placed in an aerosol can, and after mounting an aerosol valve, 25 parts of dimethyl ether and 25 parts of LPG are filled and shaken. Finally, an oil aerosol is obtained by mounting the actuator.

Formulation Example 9
0.6 part of any one of the compounds of the present invention 001 to 020, 0.01 part of BHT (2,6-di-tert-butyl-4-methylphenol), 5 parts of xylene, 3.39 parts of deodorized kerosene and emulsifier {Rheidol MO-60 (registered trademark)} 1 part mixed and dissolved and 50 parts distilled water are filled into an aerosol container, and after the valve is mounted, 40 parts of propellant (LPG) is pressurized through the valve. Fill to obtain an aqueous aerosol.

Formulation Example 10
0.1 g of any one of the present compounds 001 to 020 is dissolved in 2 mL of propylene glycol and impregnated into a porous ceramic plate of 4.0 × 4.0 cm and a thickness of 1.2 cm to obtain a heating smoke. .

Formulation Example 11
Any 5 parts of the present compounds 001 to 020 and 95 parts of an ethylene-methyl methacrylate copolymer (ratio of methyl methacrylate in the copolymer: 10% by weight, ACRIFT WD301, manufactured by Sumitomo Chemical Co., Ltd.) A kneader (manufactured by Moriyama Seisakusho) is melt-kneaded, and the obtained kneaded product is extruded from an extruder through a molding die to obtain a rod-shaped molded body having a length of 15 cm and a diameter of 3 mm.

Formulation Example 12
Melting and kneading 5 parts of any of the compounds 001 to 020 of the present invention and 95 parts of a soft vinyl chloride resin with a closed pressure kneader (manufactured by Moriyama Seisakusho) A rod-shaped molded body having a length of 15 cm and a diameter of 3 mm is obtained.

Formulation Example 13
100 mg of any of the compounds 001 to 020 of the present invention, 68.75 mg lactose, 237.5 mg corn starch, 43.75 mg microcrystalline cellulose, 18.75 mg polyvinylpyrrolidone, 28.75 mg sodium carboxymethyl starch, and magnesium stearate 5 mg is mixed and the resulting mixture is compressed to an appropriate size to obtain tablets.

Formulation Example 14
25 mg of any of the compounds of the present invention 001 to 020, lactose 60 mg, corn starch 25 mg, carmellose calcium 6 mg, and 5% hydroxypropylmethylcellulose are mixed in an appropriate amount, and the resulting mixture is filled into a hard shell gelatin capsule or hydroxypropylmethylcellulose capsule And a capsule is obtained.

Formulation Example 15
Any one of the present compounds 001 to 020, fumaric acid 500 mg, sodium chloride 2000 mg, methylparaben 150 mg, propylparaben 50 mg, granule sugar 25000 mg, sorbitol (70% solution) 13000 mg, Veegum K (Vanderbilt Co.) 100 mg, flavor 35 mg, and coloring Distilled water is added to 500 mg of the preparation so that the final volume becomes 100 mL, and mixed to obtain a suspension for oral administration.

Formulation Example 16
Any 5% by weight of the compounds 001 to 020 of the present invention is dissolved in 5% by weight of polysorbate 85, 3% by weight of benzyl alcohol, and 30% by weight of propylene glycol, and the pH of this solution becomes 6.0 to 6.5. After adding a phosphate buffer solution as described above, water is added until the final volume is reached to obtain a solution for oral administration.

Formulation Example 17
5% by weight of aluminum distearate is dispersed by heating in 57% by weight of fractionated coconut oil and 3% by weight of polysorbate 85. This is cooled to room temperature and 25% by weight of saccharin in the oil vehicle is dispersed. To this, 10% by weight of any one of the compounds 001 to 020 of the present invention is allocated to obtain a paste preparation for oral administration.

Formulation Example 18
Any 5% by weight of the compounds 001 to 020 of the present invention is mixed with 95% by weight of limestone powder, and granules for oral administration are obtained using the wet granulation method.

Formulation Example 19
Any 5 parts of the compounds of the present invention 001 to 020 are dissolved in 80 parts of diethylene glycol monoethyl ether, and 15 parts of propylene carbonate are mixed with this to obtain a spot-on solution.

Formulation Example 20
Any 10 parts of the compounds 001 to 020 of the present invention are dissolved in 70 parts of diethylene glycol monoethyl ether, and 20 parts of 2-octyldodecanol is mixed with this to obtain a pour-on solution.

Formulation Example 21
Add 0.5 parts of the present compounds 001 to 020 to 60 parts of Nikkor TEALS-42 (42% aqueous solution of Nikko Chemicals lauryl sulfate triethanolamine) and 20 parts of propylene glycol. After stirring and mixing, 19.5 parts of water is added and further stirred and mixed to obtain a shampoo agent of a uniform solution.

Formulation Example 22
Any of the present compounds 001 to 020 0.15% by weight, animal feed 95% by weight, and 4.85% by weight of a mixture composed of dicalcium phosphate, diatomaceous earth, Aerosil, and carbonate (or chalk) are sufficiently stirred and mixed. Obtain a premix for animal feed.

Formulation Example 23
7.2 g of any one of the present compounds 001 to 020 and 92.8 g of Phosco S-55 (manufactured by Maruishi Pharmaceutical Co., Ltd.) are dissolved and mixed at 100 ° C., poured into a suppository form, cooled and solidified, and suppository. Get.

  Next, the pest control effect of the compound of the present invention is shown by test examples.

Test example 1
The preparations of the compounds 002 and 011 of the present invention obtained in Formulation Example 5 were diluted with water so that the active ingredient concentration was 500 ppm to prepare a test drug solution.
Meanwhile, about 30 Aphis gossypi (all stages) were inoculated into cucumber seedlings (first true leaf development stage) planted in plastic cups and left for 1 day. The seedlings were sprayed with 20 ml of the test chemical solution.
Six days after spraying, the number of live cotton aphids that parasitized on the leaves of the cucumber was examined, and the control value was determined by the following formula.
Control value (%) = {1− (Cb × Tai) / (Cai × Tb)} × 100
In addition, the character in a formula represents the following meaning.
Cb: number of insects before treatment in the untreated group Cai: number of insects at the time of observation in the untreated group Tb: number of insects before the treatment in the treated group Tai: number of insects at the time of observation in the treated group In Formulation Example 5, it means a group in which a preparation containing no compound of the present invention was sprayed with a test chemical diluted with the same amount of water as the treatment group.
As a result, the treatment group using the test chemical solutions of the compounds 002 and 011 of the present invention showed a control value of 90% or more.

Test example 2
Each preparation of the compound of the present invention obtained in Formulation Example 5 is diluted with water so that the active ingredient concentration is 500 ppm to prepare a test drug solution.
On the other hand, cucumber seedlings planted in plastic cups (second true leaf development stage) are irrigated with 5 ml of the test chemical and stored in a greenhouse at 25 ° C. for 7 days. After inoculating about 30 Aphis gossypi (all stages) on the cucumber leaf surface and keeping it in the greenhouse for another 6 days, the number of live aphids on the cucumber leaf was investigated. The control value is obtained by the following formula.
Control value (%) = {1− (Cb × Tai) / (Cai × Tb)} × 100
In addition, the character in a formula represents the following meaning.
Cb: number of insects before treatment in the untreated group Cai: number of insects at the time of observation in the untreated group Tb: number of insects before the treatment in the treated group Tai: number of insects at the time of observation in the treated group In Formulation Example 5, it means a group in which a preparation containing no compound of the present invention was sprayed with a test chemical diluted with the same amount of water as the treatment group.

Test example 3
Each preparation of the compound of the present invention obtained in Formulation Example 5 is diluted with water so that the active ingredient concentration is 500 ppm to prepare a test drug solution.
10 ml of the test chemical solution is sprayed on rice seedlings in the second leaf development stage planted in a polyethylene cup. After air-drying, 20 3-4 instar larvae of Nilaparvata lugens are released and stored in a greenhouse at 25 ° C. Six days later, the number of brown planthopper infested with rice is investigated, and the control value is obtained by the following formula.
Control value (%) = {1− (Cb × Tai) / (Cai × Tb)} × 100
In addition, the character in a formula represents the following meaning.
Cb: number of insects before treatment in the untreated group Cai: number of insects at the time of observation in the untreated group Tb: number of insects before the treatment in the treated group Tai: number of insects at the time of observation in the treated group In Formulation Example 5, it means a group in which a preparation containing no compound of the present invention was sprayed with a test chemical diluted with the same amount of water as the treatment group.

Test example 4
Each preparation of the compound of the present invention obtained in Formulation Example 5 is diluted with water so that the active ingredient concentration is 500 ppm to prepare a test drug solution.
On the other hand, 5 ml of the test drug solution is irrigated to rice seedlings planted in plastic cups (2 weeks after sowing, in the second leaf development stage) and stored in a 25 ° C. greenhouse for 7 days. After releasing 20 3-4 instar larvae of the green planthopper (Nilaparvata lugens) and keeping it in the greenhouse for another 6 days, the number of surviving insects parasitized on the rice leaves was investigated, and the control value was calculated by the following formula: Ask for.
Control value (%) = {1− (Cb × Tai) / (Cai × Tb)} × 100
In addition, the character in a formula represents the following meaning.
Cb: number of insects before treatment in the untreated group Cai: number of insects at the time of observation in the untreated group Tb: number of insects before the treatment in the treated group Tai: number of insects at the time of observation in the treated group In Formulation Example 5, it means a group in which a preparation containing no compound of the present invention was sprayed with a test chemical diluted with the same amount of water as the treatment group.

Test Example 5
Each preparation of the compound of the present invention obtained in Formulation Example 5 is diluted with water so that the active ingredient concentration is 500 ppm to prepare a test drug solution.
On the other hand, adult tobacco whitefly (Bemisia tabaci) is released on tomato seedlings (third true leaf development stage) planted in a polyethylene cup and allowed to lay eggs for about 72 hours. The tomato seedlings are kept in a greenhouse for 8 days, and the test chemical is sprayed at a rate of 20 ml / cup to the place where the larva has hatched from the delivered eggs, and kept in the greenhouse at 25 ° C. After 7 days, the number of surviving larvae on the tomato leaves is examined, and the control value is obtained by the following formula.
Control value (%) = {1− (Cb × Tai) / (Cai × Tb)} × 100
In addition, the character in a formula represents the following meaning.
Cb: number of insects before treatment in the untreated group Cai: number of insects at the time of observation in the untreated group Tb: number of insects before the treatment in the treated group Tai: number of insects at the time of observation in the treated group In Formulation Example 5, it means a group in which a preparation containing no compound of the present invention was sprayed with a test chemical diluted with the same amount of water as the treatment group.

Test Example 6
The preparations of the compounds 002 and 011 of the present invention obtained in Formulation Example 5 were diluted with water so that the active ingredient concentration was 500 ppm to prepare a test drug solution.
On the other hand, the test chemical solution was sprayed at a rate of 20 mL / cup on a three-leaf cabbage planted in a polyethylene cup. After the drug solution was dried, the stems and leaves were cut out and accommodated in a 50 mL cup, and 5 second-instar larvae of Plutella xylostella were released and capped. After storing at 25 ° C., the number of live insects was counted after 5 days, and the death rate was calculated from the following formula.
Death rate (%) = (Number of dead insects / number of test insects) × 100
As a result, the treatment group using the test chemical solutions of the present compounds 002 and 011 showed a death rate of 80% or more.

Test Example 7
Formulations of the present compounds 002, 008, 011, 012 and 020 obtained in Formulation Example 5 were diluted with water so that the active ingredient concentration was 200 ppm to prepare a test spray solution.
On the other hand, apples were planted in plastic cups and grown until the seventh and eighth true leaves developed. The apple was sprayed with the test chemical at a rate of 20 mL / cup. After the chemical solution was dried, 60 first-instar larvae of Adoxophys orana fascita were released, the bottom was hollowed out, and the plastic cup with filter paper attached was put upside down. Seven days later, the number of surviving insects was counted, and the death rate was calculated from the following formula.
Death rate (%) = (Number of dead insects / number of test insects) × 100
As a result, the treatment group of the test chemical solutions of the compounds 002, 008, 011, 012 and 020 of the present invention showed a death rate of 90% or more.

Test Example 8
Each pharmaceutical compound of the present invention obtained in Formulation Example 5 is diluted with water so that the active ingredient concentration is 500 ppm to prepare a test drug solution.
A filter paper of the same size was laid on the bottom of a polyethylene cup having a diameter of 5.5 cm, 0.7 ml of the test chemical solution was dropped onto the filter paper, and 30 mg of sucrose was uniformly added as a bait. Ten female fly (Musca domestica) females were released into the polyethylene cup and capped. After 24 hours, the life of the house fly is examined to determine the death rate.

Test Example 9
Each formulation of the compound of the present invention obtained in Formulation Example 5 is diluted with water so that the active ingredient concentration is 500 ppm to prepare a test drug solution.
A filter paper of the same size was laid on the bottom of a polyethylene cup having a diameter of 5.5 cm, 0.7 ml of the test chemical solution was dropped onto the filter paper, and 30 mg of sucrose was uniformly added as a bait. Two adult male German cockroaches (Blatella germanica) are released into the polyethylene cup and covered. After 6 days, investigate the life and death of German cockroaches and determine the death rate.

Test Example 10
The preparation of Compound 011 of the present invention obtained in Formulation Example 5 was diluted with water so that the active ingredient concentration was 500 ppm to prepare a test drug solution.
0.7 ml of the test chemical solution was added to 100 ml of ion-exchanged water (active ingredient concentration: 3.5 ppm). Twenty dead larvae of Culex pipiens parallels were released into the liquid, and the viability was investigated one day later to determine the mortality rate.
As a result, the treatment with Compound 011 of the present invention showed a death rate of 95% or more.

Test Example 11
2 mg of the compound of the present invention is weighed into a screw tube (Marum No. 5; 27 × 55 mm), 0.2 mL of acetone is added, and the lid is covered and dissolved. The screw tube is rotated and inverted to coat the chemical solution so that the entire inner wall is uniform. After removing the lid and allowing it to air dry for about 2 hours, 5 groups of non-blood-sucking young ticks (Haemaphysalis longicornis) are released and covered. Two days later, the number of lethals is investigated, and the death rate is calculated using the following formula.
Death rate (%) = 100 x (number of dead ticks / number of test ticks)

  The compound of the present invention has a control effect against pests and is useful as an active ingredient of a pest control agent.

Claims (16)

Formula (1)
[Where:
A ¹ represents a nitrogen atom or = CR ⁹ - represents,
A ² represents a nitrogen atom or = CR ^10- ,
R ¹ may have a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from group X, or one or more atoms or groups selected from group Y. Represents a C3-C6 alicyclic hydrocarbon group,
R ² , R ³ , R ⁴ and R ⁵ are the same or different and are selected from the group Z and a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from the group X. one or more atoms or phenyl group which may have a group, one or more atoms 5 or or may have a group 6-membered heterocyclic group selected from the group Z, -OR ^11, -S (O) _m R ¹¹ , —S (O) ₂ NR ¹¹ R ¹² , —NR ¹¹ R ¹² , —NR ¹¹ CO ₂ R ¹² , —NR ¹¹ C (O) R ¹² , —CO ₂ R ¹¹ , —C (O) represents R ¹² , —C (O) NR ¹¹ R ¹² , —SF ₅ , a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R ⁶ and R ⁷ are the same or different and are each a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from group X, one or more atoms selected from group Z, or A phenyl group which may have a group, a 5- or 6-membered heterocyclic group which may have one or more atoms or groups selected from group Z, —OR ¹¹ , —S (O) _m R ¹¹ , —S (O) ₂ NR ¹¹ R ¹² , —NR ¹¹ R ¹² , —NR ¹¹ CO ₂ R ¹² , —NR ¹¹ C (O) R ¹² , —CO ₂ R ¹¹ , —C (O) R ¹¹ , a cyano group, a nitro group, a halogen atom, -SF ₅ or a hydrogen atom,
R ⁸ is a C1-C6 chain hydrocarbon group having one phenyl group (wherein the phenyl group may have one or more atoms or groups selected from group Z), or 1 C1-C6 chain hydrocarbon group having a 5- or 6-membered heterocyclic group (wherein the 5- or 6-membered heterocyclic group has one or more atoms or groups selected from group Z) Represents)
R ⁹ and R ¹⁰ are the same or different and are a C1-C6 chain hydrocarbon group which may have one or more halogen atoms, —OR ¹¹ , —S (O) _m R ¹¹ , —NR ¹¹ R _{^{12, -CO 2 R 11, -C}} (O) R 11, a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R ¹¹ and R ¹² are the same or different and each represents a C1-C6 chain hydrocarbon group or hydrogen atom which may have one or more halogen atoms,
m represents 0, 1 or 2, and n represents 0, 1 or 2.
Here, R ⁶ and R ⁷ do not simultaneously represent a hydrogen atom, and in —S (O) _m R ¹¹ , when m is 1 or 2, R ¹¹ does not represent a hydrogen atom.
Group X: C3-C6 cycloalkyl group optionally having one or more halogen atoms or one or more C1-C3 alkyl groups, C1-C6 alkoxy optionally having one or more halogen atoms A group, a C2-C6 alkenyloxy group optionally having one or more halogen atoms, a C2-C6 alkynyloxy group optionally having one or more halogen atoms, and having one or more halogen atoms. A C1-C6 alkylsulfanyl group which may have one or more, a C1-C6 alkylsulfinyl group which may have one or more halogen atoms, a C1-C6 alkylsulfonyl which may have one or more halogen atoms A C2-C6 alkylcarbonyl group which may have one or more halogen atoms, a C2-C6 alkoxy group which may have one or more halogen atoms Boniru group, cyano group, hydroxy group and the group consisting of halogen atoms.
Group Y: C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, C1-C6 alkoxy group optionally having one or more halogen atoms, one or more halogen atoms A group consisting of a C2-C6 alkenyloxy group optionally having one, a C2-C6 alkynyloxy group optionally having one or more halogen atoms, a hydroxy group and a halogen atom.
Group Z: C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, C1-C6 alkoxy group optionally having one or more halogen atoms, one or more halogen atoms A C1-C6 alkylsulfanyl group optionally having one or more, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6 optionally having one or more halogen atoms Alkylsulfonyl group, C2-C6 alkylcarbonyl group optionally having one or more halogen atoms, C2-C6 alkoxycarbonyl group optionally having one or more halogen atoms, one or more halogen atoms A C1-C6 alkylamino group optionally having one or more, a C2-C8 dialkylamino group optionally having one or more halogen atoms, a halogen atom, a cyano group, and The group consisting of Toro group. ]
Or a N-oxide thereof (hereinafter referred to as the present compound). R ² , R ³ , R ⁴ and R ⁵ are the same or different and are selected from group Z, a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from group X one or more atoms or phenyl group which may have a group, one or more atoms 5 or or may have a group 6-membered heterocyclic group selected from the group Z, -OR ^11, -S (O) _m R ¹¹ , —SF ₅ , a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R ⁶ and R ⁷ are the same or different and may have one or more atoms or groups selected from group X, a C1-C6 chain hydrocarbon group, —OR ¹¹ , —S (O) _m R ¹¹ , —SF ₅ , a halogen atom or a hydrogen atom,
R ⁹ and R ¹⁰ are each a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, -OR ¹¹ , -S (O) _m R ¹¹ , a halogen atom or a hydrogen atom. 1. The compound according to 1. R ¹ is a C1-C6 alkyl group optionally having one or more atoms or groups selected from the group consisting of halogen atoms and cyclopropyl groups (wherein the cyclopropyl group is one or more halogen atoms) Or may have one or more C1-C3 alkyl groups), may have one or more halogen atoms, may have C2-C6 alkenyl groups, or may have one or more halogen atoms. A good C2-C6 alkynyl group, or a cyclopropyl group optionally having one or more halogen atoms,
R ² , R ⁴ and R ⁵ are the same or different and are a halogen atom or a hydrogen atom,
R ³ has a C1-C6 alkyl group optionally having one or more halogen atoms, a C2-C6 alkenyl group optionally having one or more halogen atoms, and one or more halogen atoms. An optionally substituted C2-C6 alkynyl group, a 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is a C1-C3 alkyl group optionally having a halogen atom, One or more atoms or groups selected from the group consisting of a C1-C3 alkoxy group which may have a halogen atom and a halogen atom may be present.), —OR ¹¹ , —S (O) _m R ¹¹ , a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R ⁶ is a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ¹¹ , —S (O) _m R ¹¹ , —SF ₅ or a halogen atom;
R ⁷ is a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ¹¹ , —S (O) _m R ¹¹ , a halogen atom or a hydrogen atom;
R ¹¹ is a C1-C6 alkyl group optionally having one or more halogen atoms,
R ⁸ is a C1-C6 alkyl group having one phenyl group (wherein the phenyl group may be a cyano group, a C1-C3 alkyl group optionally having a halogen atom, or a halogen atom). A C1-C3 alkoxy group, and one or more atoms or groups selected from the group consisting of halogen atoms.) C1-C6 having one 5- or 6-membered aromatic heterocyclic group An alkyl group (wherein the 5- or 6-membered aromatic heterocyclic group is a C1-C3 alkyl group optionally having a halogen atom, a C1-C3 alkoxy group optionally having a halogen atom, and a halogen atom); Which may have one or more atoms or groups selected from the group consisting of atoms), or a C1-C6 alkyl group having one tetrahydrofuryl group (wherein the tetrahydrofuryl group). Has one or more atoms or groups selected from the group consisting of a C1-C3 alkyl group optionally having a halogen atom, a C1-C3 alkoxy group optionally having a halogen atom, and a halogen atom. You may have)
The R ⁹ and R ¹⁰ are each a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ¹¹ , —S (O) _m R ¹¹ , a halogen atom, or a hydrogen atom. Compound. A ¹ is = CR ⁹ - and it claims 1 to 3 A compound according to one or. Compounds according to one or claims 1 to 3 A ¹ is a nitrogen atom. The compound according to any one of claims 1 to 3, wherein A ¹ is = CR ⁹ -and A ² is a nitrogen atom. A ¹ is nitrogen atom, ^{A 2} is = ^{CR 10} - and is claims 1 to 3 A compound according to one or. The compound according to any one of claims 1 to 3, wherein A ¹ is = CR ⁹ -and A ² is = CR ^10- . A ¹ is = CH-
R ⁷ is a hydrogen atom,
R ¹ is a C1-C6 alkyl group optionally having one or more atoms or groups selected from the group consisting of halogen atoms and cyclopropyl groups (wherein the cyclopropyl group is one or more halogen atoms) Or may have one or more C1-C3 alkyl groups), may have one or more halogen atoms, may have C2-C6 alkenyl groups, or may have one or more halogen atoms. A good C2-C6 alkynyl group, or a cyclopropyl group optionally having one or more halogen atoms,
R ² , R ⁴ and R ⁵ are the same or different and are a halogen atom or a hydrogen atom,
R ³ has a C1-C6 alkyl group that may have one or more halogen atoms, a C2-C6 alkenyl group that may have one or more halogen atoms, and one or more halogen atoms An optionally substituted C2-C6 alkynyl group, a 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is a C1-C3 alkyl group optionally having a halogen atom, a halogen One or more atoms or groups selected from the group consisting of a C1-C3 alkoxy group which may have an atom, and a halogen atom; and -OR ²⁰ (wherein R ²⁰ represents Represents a C1-C6 alkyl group optionally having one or more halogen atoms.), -S (O) _m R ²¹ (wherein R ²¹ may have one or more halogen atoms). Represents a good C1-C6 alkyl group m represents 0, 1 or 2.), a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R ⁶ may be a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ²² (wherein R ²² is a C1-C6 alkyl group optionally having one or more halogen atoms) -S (O) _m R ²³ (wherein R ²³ represents a C1-C6 alkyl group optionally having one or more halogen atoms, and m represents 0, 1 or 2). .), - a SF ₅ or halogen atom,
R ⁸ is a C1-C6 alkyl group having one phenyl group (wherein the phenyl group may be a cyano group, a C1-C3 alkyl group optionally having a halogen atom, or a halogen atom). A C1-C3 alkoxy group, and one or more atoms or groups selected from the group consisting of halogen atoms.) C1-C6 having one 5- or 6-membered aromatic heterocyclic group An alkyl group (wherein the 5- or 6-membered aromatic heterocyclic group is a C1-C3 alkyl group optionally having a halogen atom, a C1-C3 alkoxy group optionally having a halogen atom, and a halogen atom); Which may have one or more atoms or groups selected from the group consisting of atoms), or a C1-C6 alkyl group having one tetrahydrofuryl group (wherein the tetrahydrofuryl group). Has one or more atoms or groups selected from the group consisting of a C1-C3 alkyl group optionally having a halogen atom, a C1-C3 alkoxy group optionally having a halogen atom, and a halogen atom. You may have)
R ¹⁰ may be a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ²⁴ (wherein R ²⁴ is a C1-C6 alkyl group optionally having one or more halogen atoms) ), —S (O) _m R ²⁵ (wherein R ²⁵ represents a C1-C6 alkyl group optionally having one or more halogen atoms, and m represents 0, 1 or 2). ), A halogen atom or a hydrogen atom,
The compound according to claim 1, wherein n is 0, 1 or 2. A ¹ is = CH-
R ⁷ is a hydrogen atom,
R ¹ is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a cyclopropyl group optionally having one or more halogen atoms, or a C1-C6 alkyl group having a cyclopropyl group (wherein the cyclo The propyl group may have one or more halogen atoms or one or more C1-C3 alkyl groups).
R ² , R ⁴ and R ⁵ are hydrogen atoms,
R ³ has a C1-C6 alkyl group that may have one or more halogen atoms, a C2-C6 alkenyl group that may have one or more halogen atoms, and one or more halogen atoms An optionally substituted C2-C6 alkynyl group, a pyridyl group (wherein the pyridyl group is a C1-C3 alkyl group optionally having a halogen atom, a C1-C3 alkoxy group optionally having a halogen atom, And a pyrimidinyl group (wherein the pyrimidinyl group is a C1-C3 alkyl group optionally having a halogen atom). it may have optionally C1-C3 may be alkoxy groups having a halogen atom, and one or more atoms or groups selected from the group consisting of halogen atom), -. oR ² , ^{(Wherein, R 20} is one or more halogen atoms optionally may C1-C6 alkyl group which may have ^{_{a.) - S (O) m}} R 21 ( ^wherein halogen ^{R 21} is 1 or more An optionally substituted C1-C6 alkyl group, and m is 0, 1 or 2.), a halogen atom or a hydrogen atom,
R ⁶ is a C1-C6 haloalkyl group, —OR ²² (wherein R ²² is a C1-C6 haloalkyl group), —S (O) _m R ²³ (wherein R ²³ is a C1-C6 haloalkyl group) There, m is 0, 1 or 2), -. a SF ₅ or halogen atom,
R ⁸ is a C1-C6 alkyl group having one phenyl group (wherein the phenyl group may have a cyano group, a C1-C3 alkyl group optionally having a halogen atom, or a halogen atom). A C1-C3 alkoxy group, which may have one or more atoms or groups selected from the group consisting of halogen atoms.) A C1-C6 alkyl group having one thiazolyl group (wherein the thiazolyl group) Has one or more atoms or groups selected from the group consisting of a C1-C3 alkyl group optionally having a halogen atom, a C1-C3 alkoxy group optionally having a halogen atom, and a halogen atom. A C1-C6 alkyl group having one pyridyl group (wherein the pyridyl group is a C1-C3 alkyl group optionally having a halogen atom, a halogen atom). A C1-C3 alkoxy group optionally having one or more atoms and one or more atoms or groups selected from the group consisting of halogen atoms), or a C1-C6 having a tetrahydrofuryl group An alkyl group (wherein the tetrahydrofuryl group is selected from the group consisting of a C1-C3 alkyl group optionally having a halogen atom, a C1-C3 alkoxy group optionally having a halogen atom, and a halogen atom); Which may have one or more atoms or groups).
The compound according to claim 1, wherein R ¹⁰ is a hydrogen atom or a halogen atom. A ² is = CH-
R ⁶ is a hydrogen atom,
R ¹ is a C1-C6 alkyl group optionally having one or more atoms or groups selected from the group consisting of halogen atoms and cyclopropyl groups (wherein the cyclopropyl group is
May have one or more halogen atoms or one or more C1-C3 alkyl groups),
A C2-C6 alkenyl group which may have one or more halogen atoms, a C2-C6 alkynyl group which may have one or more halogen atoms, or one or more halogen atoms A good cyclopropyl group,
R ² , R ⁴ and R ⁵ are the same or different and are a halogen atom or a hydrogen atom,
R ³ has a C1-C6 alkyl group that may have one or more halogen atoms, a C2-C6 alkenyl group that may have one or more halogen atoms, and one or more halogen atoms An optionally substituted C2-C6 alkynyl group, a 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is a C1-C3 alkyl group optionally having a halogen atom, a halogen One or more atoms or groups selected from the group consisting of a C1-C3 alkoxy group which may have an atom, and a halogen atom; and -OR ²⁰ (wherein R ²⁰ represents Represents a C1-C6 alkyl group optionally having one or more halogen atoms.), -S (O) _m R ²¹ (wherein R ²¹ may have one or more halogen atoms). Represents a good C1-C6 alkyl group m represents 0, 1 or 2.), a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R ⁷ may be a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ²² (wherein R ²² is a C1-C6 alkyl group optionally having one or more halogen atoms) -S (O) _m R ²³ (wherein R ²³ represents a C1-C6 alkyl group optionally having one or more halogen atoms, and m represents 0, 1 or 2). .), - a SF ₅ or halogen atom,
R ⁸ is a C1-C6 alkyl group having one phenyl group (wherein the phenyl group may be a cyano group, a C1-C3 alkyl group optionally having a halogen atom, or a halogen atom). A C1-C3 alkoxy group, and one or more atoms or groups selected from the group consisting of halogen atoms.
A C1-C6 alkyl group having one 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group may be a C1-C3 alkyl group optionally having a halogen atom, A C1-C3 alkoxy group optionally having a halogen atom, and one or more atoms or groups selected from the group consisting of halogen atoms), or a C1-C6 having a tetrahydrofuryl group An alkyl group (wherein the tetrahydrofuryl group is selected from the group consisting of a C1-C3 alkyl group optionally having a halogen atom, a C1-C3 alkoxy group optionally having a halogen atom, and a halogen atom); One or more atoms or groups may be present).
R ⁹ is a C1-C6 alkyl group which may have one or more halogen atoms, —OR ²⁴ (wherein R ²⁴ is a C1-C6 alkyl group which may have one or more halogen atoms). ), —S (O) _m R ²⁵ (wherein R ²⁵ represents a C1-C6 alkyl group optionally having one or more halogen atoms, and m represents 0, 1 or 2). ), A halogen atom or a hydrogen atom,
2. The compound according to claim 1, wherein n is 0, 1 or 2. A ² is ═CH—, R ⁶ is a hydrogen atom,
R ¹ is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a cyclopropyl group optionally having one or more halogen atoms, or a C1-C6 alkyl group having a cyclopropyl group (wherein the cyclo The propyl group may have one or more halogen atoms or one or more C1-C3 alkyl groups).
R ² , R ⁴ and R ⁵ are hydrogen atoms,
R ³ has a C1-C6 alkyl group that may have one or more halogen atoms, a C2-C6 alkenyl group that may have one or more halogen atoms, and one or more halogen atoms An optionally substituted C2-C6 alkynyl group, a pyridyl group (wherein the pyridyl group is a halogen atom, a C1-C3 alkyl group which may have a halogen atom, and a C1- which may have a halogen atom) 1 or more atoms or groups selected from the group consisting of C3 alkoxy groups, and a pyrimidinyl group (wherein the pyrimidinyl group may have a halogen atom or a halogen atom) C3 alkyl group, and a halogen atom may have one or more atoms or groups selected from the group consisting of may also be C1-C3 alkoxy group which the have), -. oR ² , ^{(Wherein, R 20} is one or more halogen atoms optionally may C1-C6 alkyl group which may have ^{_{a.) - S (O) m}} R 21 ( ^wherein halogen ^{R 21} is 1 or more An optionally substituted C1-C6 alkyl group, and m is 0, 1 or 2.), a halogen atom or a hydrogen atom,
R ⁷ is a C1-C6 haloalkyl group, —OR ²² (wherein R ²² is a C1-C6 haloalkyl group), —S (O) _m R ²³ (wherein R ²³ is a C1-C6 haloalkyl group) There, m is 0, 1 or 2), -. a SF ₅ or halogen atom,
R ⁸ is a C1-C6 alkyl group having one phenyl group (wherein the phenyl group may have a cyano group, a C1-C3 alkyl group optionally having a halogen atom, or a halogen atom). One or more atoms or groups selected from the group consisting of C1-C3 alkoxy groups and halogen atoms may be present).
A C1-C6 alkyl group having one thiazolyl group (wherein the thiazolyl group is a C1-C3 alkyl group optionally having a halogen atom, a C1-C3 alkoxy group optionally having a halogen atom, And may have one or more atoms or groups selected from the group consisting of halogen atoms).
A C1-C6 alkyl group having one pyridyl group (wherein the pyridyl group is a C1-C3 alkyl group optionally having a halogen atom, a C1-C3 alkoxy group optionally having a halogen atom, And one or more atoms or groups selected from the group consisting of halogen atoms), or a C1-C6 alkyl group having one tetrahydrofuryl group (wherein the tetrahydrofuryl group is a halogen atom) A C1-C3 alkyl group which may have an atom, a C1-C3 alkoxy group which may have a halogen atom, and one or more atoms or groups selected from the group consisting of a halogen atom; Is good.)
The compound according to claim 1, wherein R ⁹ is a hydrogen atom or a halogen atom. A ¹ is ═CH—, R ² , R ⁴ , R ⁵ , and R ⁷ are hydrogen atoms,
A ² is a nitrogen atom or = CR ^10- (wherein R ¹⁰ represents a halogen atom or a hydrogen atom);
R ¹ is an ethyl group, a cyclopropyl group, or a cyclopropylmethyl group;
R ⁸ is benzyl group, 2-methylbenzyl group, 3-methylbenzyl group, 4-methylbenzyl group, 2-chlorobenzyl group, 3-chlorobenzyl group, 4-chlorobenzyl group, 2-cyanobenzyl group, 3- Cyanobenzyl group, 4-cyanobenzyl group, 2-fluorobenzyl group, 3-fluorobenzyl group, 4-fluorobenzyl group, phenyl-ethyl group, (2-chloro-phenyl) -ethyl group, (3-chloro-phenyl) ) -Ethyl group, (4-chloro-phenyl) -ethyl group, (2-methyl-phenyl) -ethyl group, (3-methyl-phenyl) -ethyl group, (4-methyl-phenyl) -ethyl group, ( 2-chloro-thiazol-5-yl) -methyl group, (thiazol-5-yl) -methyl group, (2-bromo-thiazol-5-yl) -methyl group, (2-methyl) Ru-thiazol-5-yl) -methyl group, (2-trifluoromethyl-thiazol-5-yl) -methyl group, (2-chloro-thiazol-5-yl) -ethyl group, (thiazol-5-yl) ) -Ethyl group, (2-chloro-pyridin-5-yl) -methyl group, (pyridin-3-yl) -methyl group, (pyridin-2-yl) -methyl group, (pyridin-4-yl)- Methyl group, (6-fluoro-pyridin-3-yl) -methyl group, (6-bromo-pyridin-3-yl) -methyl group, (6-trifluoromethyl-pyridin-3-yl) -methyl group, (6-methyl-pyridin-3-yl) -methyl group, (6-chloro-5-fluoro-pyridin-3-yl) -methyl group, (5,6-dichloro-pyridin-3-yl) -methyl group , (Pyridin-3-yl) -e Group, (6-chloro-pyridin-3-yl) -ethyl group, (pyrimidin-5-yl) -methyl group, (2-chloro-pyrimidin-5-yl) -methyl group, (2-methyl-pyrimidine) -5-yl) -methyl group, (5-chloro-pyrazin-2-yl) -methyl group, (tetrahydro-furan-3-yl) -methyl group, or (tetrahydro-furan-3-yl) -ethyl group And
R ³ is a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ²⁰ (wherein R ²⁰ is a C1-C6 alkyl optionally having one or more halogen atoms) -S (O) _m R ²¹ (wherein R ²¹ represents a C1-C6 alkyl group optionally having one or more halogen atoms, and m represents 0, 1, or 2). Represents a halogen atom or a hydrogen atom,
R ⁶ is a C1-C6 haloalkyl group, —OR ²² (wherein R ²² represents a C1-C6 haloalkyl group), —S (O) _m R ²³ (wherein R ²³ is a C1-C6 haloalkyl group). the stands, m represents 0, 1 or 2), -. a SF ₅ or halogen atom,
2. The compound according to claim 1, wherein n is 0, 1 or 2. A ² is ═CH—, R ² , R ⁴ , R ⁵ , and R ⁶ are hydrogen atoms,
A ¹ is nitrogen atom or = CR ⁹ - (wherein, ^{R 9} represents a hydrogen atom or a halogen atom.), And
R ¹ is an ethyl group, a cyclopropyl group, or a cyclopropylmethyl group;
R ⁸ is benzyl group, 2-methylbenzyl group, 3-methylbenzyl group, 4-methylbenzyl group, 2-chlorobenzyl group, 3-chlorobenzyl group, 4-chlorobenzyl group, 2-cyanobenzyl group, 3- Cyanobenzyl group, 4-cyanobenzyl group, 2-fluorobenzyl group, 3-fluorobenzyl group, 4-fluorobenzyl group, phenyl-ethyl group, (2-chloro-phenyl) -ethyl group, (3-chloro-phenyl) ) -Ethyl group, (4-chloro-phenyl) -ethyl group, (2-methyl-phenyl) -ethyl group, (3-methyl-phenyl) -ethyl group, (4-methyl-phenyl) -ethyl group, ( 2-chloro-thiazol-5-yl) -methyl group, (thiazol-5-yl) -methyl group, (2-bromo-thiazol-5-yl) -methyl group, (2-methyl) Ru-thiazol-5-yl) -methyl group, (2-trifluoromethyl-thiazol-5-yl) -methyl group, (2-chloro-thiazol-5-yl) -ethyl group, (thiazol-5-yl) ) -Ethyl group, (2-chloro-pyridin-5-yl) -methyl group, (pyridin-3-yl) -methyl group, (pyridin-2-yl) -methyl group, (pyridin-4-yl)- Methyl group, (6-fluoro-pyridin-3-yl) -methyl group, (6-bromo-pyridin-3-yl) -methyl group, (6-trifluoromethyl-pyridin-3-yl) -methyl group, (6-methyl-pyridin-3-yl) -methyl group, (6-chloro-5-fluoro-pyridin-3-yl) -methyl group, (5,6-dichloro-pyridin-3-yl) -methyl group , (Pyridin-3-yl) -e Group, (6-chloro-pyridin-3-yl) -ethyl group, (pyrimidin-5-yl) -methyl group, (2-chloro-pyrimidin-5-yl) -methyl group, (2-methyl-pyrimidine) -5-yl) -methyl group, (5-chloro-pyrazin-2-yl) -methyl group, (tetrahydro-furan-3-yl) -methyl group, or (tetrahydro-furan-3-yl) -ethyl group And
R ³ is a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ²⁰ (wherein R ²⁰ is a C1-C6 alkyl optionally having one or more halogen atoms) -S (O) _m R ²¹ (wherein R ²¹ represents a C1-C6 alkyl group optionally having one or more halogen atoms, and m represents 0, 1, or 2). And R ⁷ is a C1-C6 haloalkyl group, —OR ²² (wherein R ²² represents a C1-C6 haloalkyl group), —S (O) _m R ^23. (Wherein R ²³ represents a C1-C6 haloalkyl group, m represents 0, 1 or 2), —SF ₅ or a halogen atom;
2. The compound according to claim 1, wherein n is 0, 1 or 2. A pest control composition comprising the compound according to any one of claims 1 to 14 and an inert carrier. A method for controlling pests, which comprises applying an effective amount of the compound according to any one of claims 1 to 14 to pests or habitats of pests.