Biaryl compound and method for controlling plant diseases
Patent Information
- Application Number
- PCT/JP2024/035367
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2024-04-30
- Filing Date
- 2024-10-03
- Publication Date
- 2025-04-10
AI Technical Summary
The prior art is difficult to provide an effective method of plant disease control.
Plants or culture soil are treated with compounds that represent specific biaryl compounds (Biaryl compounds) to control plant diseases.
This method significantly improves the control effect on plant diseases and provides a new and effective pesticide alternative.
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Figure JP2024035367_10042025_PF_FP_ABST
Abstract
Description
Biaryl compounds and plant disease control methods
[0001] This patent application claims priority under the Paris Convention to and the benefit of Japanese Patent Application No. 2023-172767 (filed October 4, 2023) and Japanese Patent Application No. 2024-073431 (filed April 30, 2024), the entire contents of which are incorporated herein by reference. The present invention relates to biaryl compounds and methods for controlling plant diseases.
[0002] Patent Document 1 describes biaryl compounds as agricultural herbicides.
[0003] EP 0 144 668
[0004] An object of the present invention is to provide an excellent method for controlling plant diseases.
[0005] The present inventors have conducted studies to find an excellent method for controlling plant diseases and have found that a compound represented by the following formula (I) has excellent control activity against plant diseases.
[0006] [1] Formula (I) [In the formula, ring A 6 represents a 6-membered non-aromatic nitrogen-containing heterocycle or a 6-membered aromatic nitrogen-containing heterocycle (provided that ring A 6 In the formula (I), the atom bonded to D is a carbon atom or a nitrogen atom, and ring A is adjacent to the atom bonded to D. 6 at least one of the atoms constituting the group is a nitrogen atom; D represents CR 1 R 2 , C=O, C=S, or C=N-OR 7 n represents 0, 1, 2, or 3; m represents 0, 1, 2, 3, or 4; q represents 0, 1, 2, 3, 4, or 5; R 1 and R 2are the same or different and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A, a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group (the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from Group B), a phenyl group, a 5- to 6-membered aromatic heterocyclic group (the phenyl group and the 5- to 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group C), OR 8 , S.R. 9 , S(O)R 10 , S(O)R 11 , N.R. 12 R 13 , C(O)R 14 , C(R 15 ) = NOR 16 , a cyano group, a nitro group, a halogen atom, or a hydrogen atom; R 1 and R 2 may form, together with the carbon atom to which they are attached, a C3-C8 alicyclic hydrocarbon or a 3- to 8-membered non-aromatic heterocycle (the C3-C8 alicyclic hydrocarbon and the 3- to 8-membered non-aromatic heterocycle may be substituted with one or more substituents selected from Group B); R 3 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group A, a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group (the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group B), a phenyl group, a 5- to 6-membered aromatic heterocyclic group (the phenyl group and the 5- to 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group C), OR 17 , S.R. 18 , S(O)R 19 , S(O)R 20 , N.R. 21 R 22 , C(O)R 23 , C(R 24 ) = NOR 25 , a cyano group, a nitro group, or a halogen atom; R 4represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group A, a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group (the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group B), a phenyl group optionally substituted with one or more substituents selected from group C, OR 26 , N.R. 27 R 28 , C(O)R 29 , C(R 30 ) = NOR 31 , a cyano group, a nitro group, or a halogen atom; R 6 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group A, a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group (the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group B), a phenyl group, a 5- to 6-membered aromatic heterocyclic group (the phenyl group and the 5- to 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group C), OR 32 , S.R. 33 , S(O)R 34 , S(O)R 35 , N.R. 36 R 37 , C(O)R 38 , C(R 39 ) = NOR 40 , a cyano group, a nitro group, or a halogen atom; R 8 , R 12 , R 13 , R 17 , R 21 , R 22 , R 26 , R 27 , R 28 , R 32 , R 36 , and R 37are the same or different and are a C1-C6 chain hydrocarbon group optionally substituted by one or more substituents selected from Group A, a C1-C6 alkylsulfonyl group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a (C2-C8 dialkylamino)carbonyl group {the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C1-C6 alkoxy)carbonyl group, the (C1-C6 alkylamino)carbonyl group, a (C2-C8 dialkylamino)carbonyl group, and the (C2-C8 dialkylamino)carbonyl group may be substituted with one or more halogen atoms}, a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from Group B}, a phenyl group, a 5- to 6-membered aromatic heterocyclic group {the phenyl group and the 5- to 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group C}, or a hydrogen atom; 7 , R 9 , R 16 , R 18 , R 25 , R 31 , R 33 , and R 40 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group (the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from Group B), a phenyl group, a 5-6 membered aromatic heterocyclic group (the phenyl group and the 5-6 membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group C), or a hydrogen atom, R 10 , R 11 , R 19 , R 20 , R 34 , and R 35are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A, a C1-C6 alkylamino group, a C2-C8 dialkylamino group (the C1-C6 alkylamino group and the C2-C8 dialkylamino group are optionally substituted with one or more halogen atoms), a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group (the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group are optionally substituted with one or more substituents selected from Group B), a phenyl group, or a 5- to 6-membered aromatic heterocyclic group (the phenyl group and the 5- to 6-membered aromatic heterocyclic group are optionally substituted with one or more substituents selected from Group C), R 14 , R 23 , R 29 , and R 38 are the same or different and represent a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylamino group, a C2-C8 dialkylamino group (the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylamino group, and the C2-C8 dialkylamino group may be substituted with one or more halogen atoms), or a hydroxy group; R 15 , R 24 , R 30 , and R 39 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group A, or a hydrogen atom; when q is 2, 3, 4, or 5, two adjacent R 6 and R 6may, together with the carbon atoms to which they are bonded, form a C5-C6 alicyclic hydrocarbon, a 5- to 6-membered non-aromatic heterocycle (the C5-C6 alicyclic hydrocarbon and the 5- to 6-membered non-aromatic heterocycle may be substituted with one or more substituents selected from Group B), a benzene ring, or a 5- to 6-membered aromatic heterocycle (the benzene ring and the 5- to 6-membered aromatic heterocycle may be substituted with one or more substituents selected from Group C). Group A: the group consisting of a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group {the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group and the C1-C6 alkylsulfonyl group are optionally substituted with one or more halogen atoms}, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group are optionally substituted with one or more substituents selected from Group B}, a phenyl group, a 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group are optionally substituted with one or more substituents selected from Group C}, a halogen atom, a cyano group, a nitro group, a hydroxy group and a sulfanyl group. Group B: a group consisting of an oxo group, a thioxo group, a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group (the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group, and the C1-C6 alkylsulfonyl group are optionally substituted with one or more halogen atoms), a hydroxy group, a sulfanyl group, a halogen atom, and a cyano group.Group C: a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a C2-C8 dialkylamino group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a (C2-C8 dialkylamino)carbonyl group, a (C1-C6 alkyl)carbonylamino group, a (C1-C6 alkoxy)carbonylamino group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group, the (C1-C6 alkyl)carbonyl group, the C1-C6 alkylsulfonyl group, the C1-C6 alkylamino group, the C2-C8 dialkylamino group, the (C1-C6 alkyl)carbonyl group, the (C1-C6 alkoxy)carbonyl group, the (C1-C6 alkylamino)carbonyl group, the (C2-C8 dialkylamino)carbonyl group, the (C1-C6 alkyl)carbonylamino group and the (C1-C6 alkoxy)carbonylamino group are optionally substituted with one or more halogen atoms}, the group consisting of a C3-C8 alicyclic hydrocarbon group optionally substituted by one or more substituents selected from Group B, an amino group, a nitro group, a cyano group, a hydroxy group, a sulfanyl group, and a halogen atom. [2] A method for controlling plant diseases, which comprises treating a plant or soil in which the plant is grown with a compound represented by the formula (II) (hereinafter referred to as the present compound A), or an N-oxide thereof, or a salt thereof (hereinafter the present compound A, the N-oxide thereof, or a salt thereof will be referred to as the present compound). [In the formula, X 1a is a nitrogen atom or CR 41a represents X 2a is a nitrogen atom or CR 42a represents X 3a is a nitrogen atom or CR 43a represents X 4a is a nitrogen atom or CR 44a (where X 1a , X 2a , X 3a and X 4a The number of nitrogen atoms is 0 or 1. 1a is CR41a and X 2a is CR 42a and X 3a is CR 43a and X 4a is CR 44a When R 41a , R 42a , R 43a and R 44a At least one of these is a hydrogen atom; ma represents 0, 1, 2, or 3; qa represents 0, 1, 2, 3, 4, or 5; R 1a , and R 2a are the same or different, and are group A a a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group, each of which may be substituted by one or more substituents selected from the group consisting of a a phenyl group, a 5- or 6-membered aromatic heterocyclic group {the phenyl group and the 5- or 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from the group C a may be substituted with one or more substituents selected from the group consisting of OR 8a , S.R. 9a , S(O)R 10a , S(O)R 11a , N.R. 12a R 13a , C(O)R 14a , C(R 15a ) = NOR 16a , a cyano group, a nitro group, a halogen atom, or a hydrogen atom; R 1a and R 2a together with the carbon atom to which they are attached, form a C3-C8 alicyclic hydrocarbon or a 3- to 8-membered non-aromatic heterocycle {the C3-C8 alicyclic hydrocarbon and the 3- to 8-membered non-aromatic heterocycle are selected from the group B a may be substituted with one or more substituents selected from the following; 3a and R 5a are the same or different, and are group A aa C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group, each of which may be substituted by one or more substituents selected from the group consisting of a a phenyl group, a 5- or 6-membered aromatic heterocyclic group {the phenyl group and the 5- or 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from the group C a may be substituted with one or more substituents selected from the group consisting of OR 17a , S.R. 18a , S(O)R 19a , S(O)R 20a , N.R. 21a R 22a , C(O)R 23a , C(R 24a ) = NOR 25a , a cyano group, a nitro group, or a halogen atom; R 6a is group A a a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group, each of which may be substituted by one or more substituents selected from the group consisting of a a phenyl group, a 5- or 6-membered aromatic heterocyclic group {the phenyl group and the 5- or 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from the group C a may be substituted with one or more substituents selected from the group consisting of OR 32a , S.R. 33a , S(O)R 34a , S(O)R 35a , N.R. 36a R 37a , C(O)R 38a , C(R 39a ) = NOR 40a , a cyano group, a nitro group, or a halogen atom; R 41a , R 42a , and R 44a are the same or different, and are group D a a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group, each of which may be substituted by one or more substituents selected from the group consisting ofa may be substituted with one or more substituents selected from the group consisting of OR 45a , N.R. 47a R 48a , C(R 49a ) = NOR 50a , a cyano group, a nitro group, a halogen atom, or a hydrogen atom; R 43a is group D a a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group, each of which may be substituted by one or more substituents selected from the group consisting of a may be substituted with one or more substituents selected from the group consisting of OR 46a , N.R. 47a R 48a , C(R 49a ) = NOR 50a , a cyano group, a nitro group, a halogen atom, or a hydrogen atom; R 8a , R 12a , R 13a , R 17a , R 21a , R 22a , R 32a , R 36a , and R 37a are the same or different, and are group A a a C1-C6 chain hydrocarbon group optionally substituted by one or more substituents selected from the group consisting of a C1-C6 alkylsulfonyl group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a (C2-C8 dialkylamino)carbonyl group {the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C1-C6 alkoxy)carbonyl group, the (C1-C6 alkylamino)carbonyl group, and the (C2-C8 dialkylamino)carbonyl group are optionally substituted by one or more halogen atoms}, a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group are selected from the group consisting of a C1-C6 alkylsulfonyl group, a C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, and a ... a a phenyl group, a 5- or 6-membered aromatic heterocyclic group {the phenyl group and the 5- or 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from the group C aor a hydrogen atom, R 9a , R 16a , R 18a , R 25a , R 33a , and R 40a are the same or different, and are group A a a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group, each of which may be substituted by one or more substituents selected from the group consisting of a a phenyl group, a 5- or 6-membered aromatic heterocyclic group {the phenyl group and the 5- or 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from the group C a or a hydrogen atom, R 10a , R 11a , R 19a , R 20a , R 34a , and R 35a are the same or different, and are group A a a C1-C6 chain hydrocarbon group optionally substituted by one or more substituents selected from the group consisting of a C1-C6 alkylamino group, a C2-C8 dialkylamino group (the C1-C6 alkylamino group and the C2-C8 dialkylamino group are optionally substituted by one or more halogen atoms), a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group (the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group are selected from the group consisting of a C1-C6 alkylamino group and a C2-C8 dialkylamino group ... a a phenyl group, or a 5- or 6-membered aromatic heterocyclic group {which may be substituted with one or more substituents selected from the following}, a phenyl group, or a 5- or 6-membered aromatic heterocyclic group {the phenyl group and the 5- or 6-membered aromatic heterocyclic group are selected from the following group C a R may be substituted with one or more substituents selected from the following 23a , and R 38aare the same or different and represent a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylamino group, a C2-C8 dialkylamino group (the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylamino group, and the C2-C8 dialkylamino group may be substituted with one or more halogen atoms), or a hydroxy group; R 15a , R 24a , and R 39a are the same or different, and are group A a R represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from the group consisting of: 45a is group D a a C1-C6 chain hydrocarbon group optionally substituted by one or more substituents selected from the group consisting of a C1-C6 alkylsulfonyl group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a (C2-C8 dialkylamino)carbonyl group {the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C1-C6 alkoxy)carbonyl group, the (C1-C6 alkylamino)carbonyl group, and the (C2-C8 dialkylamino)carbonyl group are optionally substituted by one or more halogen atoms}, a C3-C8 alicyclic hydrocarbon group, or a 3- to 8-membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group are selected from the group consisting of a C1-C6 alkylsulfonyl group, a C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, and a ... a R may be substituted with one or more substituents selected from the following 47a and R 48a are the same or different, and are group D aa C1-C6 chain hydrocarbon group optionally substituted by one or more substituents selected from the group consisting of a C1-C6 alkylsulfonyl group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a (C2-C8 dialkylamino)carbonyl group {the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C1-C6 alkoxy)carbonyl group, the (C1-C6 alkylamino)carbonyl group, and the (C2-C8 dialkylamino)carbonyl group are optionally substituted by one or more halogen atoms}, a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group are selected from the group consisting of a C1-C6 alkylsulfonyl group, a C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, and a ... a or a hydrogen atom, R 50a is group D a a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group, each of which may be substituted by one or more substituents selected from the group consisting of a R may be substituted with one or more substituents selected from the following 49a is group D a R represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from the group consisting of: 14a represents a C1-C6 chain hydrocarbon group, a C1-C6 alkylamino group, a C2-C8 dialkylamino group (the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylamino group, and the C2-C8 dialkylamino group may be substituted with one or more halogen atoms), or a hydroxy group, R 46a is a CFH2 group, a CF2H group, a CF3 group, group D aa C2-C6 chain hydrocarbon group optionally substituted by one or more substituents selected from the group consisting of a C1-C6 alkylsulfonyl group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a (C2-C8 dialkylamino)carbonyl group {the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C1-C6 alkoxy)carbonyl group, the (C1-C6 alkylamino)carbonyl group, and the (C2-C8 dialkylamino)carbonyl group are optionally substituted by one or more halogen atoms}, a C3-C8 alicyclic hydrocarbon group, or a 3- to 8-membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group are selected from the group consisting of a C2-C6 chain hydrocarbon group optionally substituted by one or more substituents selected from the group consisting of a C1-C6 alkylsulfonyl group, a C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, and a (C2-C8 dialkylamino)carbonyl group a and the group A may be substituted with one or more substituents selected from the following. a C1-C6 alkoxy group, C1-C6 alkylsulfanyl group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, {the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group, and the C1-C6 alkylsulfonyl group are optionally substituted with one or more halogen atoms}, C3-C8 alicyclic hydrocarbon group, 3- to 8-membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group are selected from group B a a phenyl group, a 5- or 6-membered aromatic heterocyclic group {the phenyl group and the 5- or 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from the group C a and a group consisting of a halogen atom, a cyano group, a nitro group, a hydroxy group, and a sulfanyl group, each of which may be substituted with one or more substituents selected from the group consisting of: aGroup C: a group consisting of an oxo group, a thioxo group, a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group (the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group, and the C1-C6 alkylsulfonyl group are optionally substituted with one or more halogen atoms), a hydroxy group, a sulfanyl group, a halogen atom, and a cyano group. a C1-C6 chain hydrocarbon group, C1-C6 alkoxy group, C1-C6 alkylsulfanyl group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 alkylamino group, C2-C8 dialkylamino group, (C1-C6 alkyl)carbonyl group, (C1-C6 alkoxy)carbonyl group, (C1-C6 alkylamino)carbonyl group, (C2-C8 dialkylamino)carbonyl group, (C1-C6 alkyl)carbonylamino group, (C1-C6 alkoxy)carbonylamino group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the C1-C6 alkylamino group, the C2-C8 dialkylamino group, the (C1-C6 alkyl)carbonyl group, the (C1-C6 alkoxy)carbonyl group, the (C1-C6 alkylamino)carbonyl group, the (C2-C8 dialkylamino)carbonyl group, the (C1-C6 alkyl)carbonylamino group, and the (C1-C6 alkoxy)carbonylamino group are optionally substituted with one or more halogen atoms}, Group B a Group D: a C3-C8 alicyclic hydrocarbon group optionally substituted with one or more substituents selected from the group consisting of an amino group, a nitro group, a cyano group, a hydroxy group, a sulfanyl group, and a halogen atom. aC1-C6 alkoxy group, C1-C6 alkylsulfanyl group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group {the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group, and the C1-C6 alkylsulfonyl group are optionally substituted with one or more halogen atoms}, C3-C8 alicyclic hydrocarbon group, 3- to 8-membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group are selected from group B a a group consisting of a halogen atom, a cyano group, a nitro group, a hydroxy group, and a sulfanyl group, which may be substituted with one or more substituents selected from the above}, a halogen atom, a cyano group, a nitro group, a hydroxy group, and a sulfanyl group.] (hereinafter referred to as compound A of the present invention) or an N-oxide thereof, or a salt thereof (hereinafter compound A of the present invention, the N-oxide thereof, or a salt thereof will be referred to as the compound of the present invention). [3] A composition containing the compound according to [2], the N-oxide thereof, or a salt thereof, and an inert carrier. [4] A composition containing one or more components selected from the group consisting of group (a), group (b), group (c), and group (d), and the compound according to [2], the N-oxide thereof, or a salt thereof: Group (a): a group consisting of an insecticidal active ingredient, a miticidal active ingredient, and a nematicidal active ingredient; Group (b): a fungicidal active ingredient; Group (c): a plant growth regulator ingredient; Group (d): a repellent ingredient. [5] A method for controlling plant diseases by applying an effective amount of the compound according to [2], its N-oxide, or a salt thereof, or an effective amount of the composition according to [4] to a plant or soil for cultivating a plant. [6] Use of the compound according to [2], its N-oxide, or a salt thereof, or the composition according to [4] for controlling plant diseases. [7] A seed or vegetative reproductive organ bearing an effective amount of the compound according to [2], its N-oxide, or a salt thereof, or an effective amount of the composition according to [4].
[0007] According to the present invention, plant diseases can be controlled.
[0008] Substituents in the present invention will be explained. A halogen atom means a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom. When a substituent is substituted with two or more halogen atoms or substituents, these halogen atoms or substituents may be the same or different. In the present specification, the term "optionally substituted with one or more substituents selected from group X" (X is A, B, C, A a , B a , C a , and D a In the present specification, when two or more substituents selected from group X are present, the substituents may be the same or different. 4 ) n , the notation indicates that when n is 2 or 3, multiple R 4 means that each may be the same or different. 3 ) m , the notation indicates that when m is 2, 3, or 4, multiple R 3 means that each may be the same or different. 6 ) q , the notation indicates that when q is 2, 3, 4, or 5, multiple R 6 means that each may be the same or different. 3a ) ma , the notation means that when ma is 2 or 3, multiple R 3a means that each may be the same or different. 6a ) qa , the notation means that when qa is 2, 3, 4 or 5, multiple R 6ameans that each may be the same or different. In this specification, the notation "CX-CY" means that the number of carbon atoms is X to Y. For example, the notation "C1-C6" means that the number of carbon atoms is 1 to 6. The chain hydrocarbon group represents an alkyl group, an alkenyl group, or an alkynyl group. Examples of alkyl groups include a methyl group, an ethyl group, a propyl group, an isopropyl group, a 1,1-dimethylpropyl group, a 1,2-dimethylpropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group. Examples of alkenyl groups include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-methyl-1-propenyl group, a 1-methyl-2-propenyl group, a 1,2-dimethyl-1-propenyl group, a 3-butenyl group, a 4-pentenyl group, and a 5-hexenyl group. Examples of alkynyl groups include ethynyl, 1-propynyl, 2-propynyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 2-butynyl, 4-pentynyl, and 5-hexynyl groups. Examples of alkoxy groups include methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy, pentyloxy, and hexyloxy groups. Examples of alkylsulfanyl groups include methylsulfanyl, ethylsulfanyl, isopropylsulfanyl, and hexylsulfanyl groups. Examples of alkylsulfinyl groups include methylsulfinyl, ethylsulfinyl, isopropylsulfinyl, and hexylsulfinyl groups. Examples of alkylsulfonyl groups include methanesulfonyl, ethanesulfonyl, isopropanesulfonyl, and hexanesulfonyl groups. Examples of alkylcarbonyl groups include acetyl and propionyl groups. Examples of alkoxycarbonyl groups include methoxycarbonyl, isopropoxycarbonyl, and hexyloxycarbonyl groups. Examples of alicyclic hydrocarbons include cyclobutene, cyclopentene, cyclopentadiene, cyclohexene, cyclohexadiene, and cycloheptene rings.Examples of alicyclic hydrocarbon groups include cycloalkyl groups and cycloalkenyl groups. Examples of cycloalkyl groups include cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, and cyclohexyl groups. Examples of cycloalkenyl groups include cyclopentenyl groups and cyclohexenyl groups. Examples of non-aromatic heterocycles include dihydrofuran rings, dihydrothiophene rings, dihydropyrrole rings, 1,3-dioxole rings, pyran rings, and dihydropyran rings. Examples of aromatic heterocycles include furan rings, thiophene rings, pyrrole rings, pyrazole rings, imidazole rings, oxazole rings, isoxazole rings, thiazole rings, isothiazole rings, triazole rings, oxadiazole rings, thiazole rings, pyridine rings, pyridazine rings, pyrimidine rings, and pyrazine rings. Examples of the aromatic heterocyclic group include 5-membered aromatic heterocyclic groups such as a pyrrolyl group, a furanyl group, a thienyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, and a thiadiazolyl group; and 6-membered aromatic heterocyclic groups such as a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, and a tetrazinyl group. Examples of non-aromatic heterocyclic groups include aziridinyl, oxiranyl, thiiranyl, azetidinyl, oxetanyl, thietanyl, pyrrolidinyl, tetrahydrofuranyl, tetrahydrothienyl, pyrazolinyl, pyrazolidinyl, imidazolinyl, imidazolidinyl, oxazolinyl, thiazolinyl, oxazolidinyl, thiazolidinyl, isoxazolinyl, isoxazolidinyl, isothiazolinyl, isothiazolidinyl, dioxolanyl, dioxanyl, piperidyl, piperazinyl, morpholinyl, thiomorpholinyl, pyranyl, dihydropyranyl, tetrahydropyranyl, tetrahydrothiopyranyl, azepanyl, oxepanyl, and thiepanyl groups.
[0009] Ring A in formula (I) 6 is the formula (A 6 -1) [wherein # represents the bonding site to D], and is a 6-membered non-aromatic nitrogen-containing heterocycle or a 6-membered aromatic nitrogen-containing heterocycle (provided that ring A 6 In the formula (I), the atom bonded to D is a carbon atom or a nitrogen atom, and ring A is adjacent to the atom bonded to D. 6 As described in formula (I), at least one of the atoms constituting ring A is a nitrogen atom. 6 is n R 4 and n R 4 Ring A substituted with 6 is the formula (A 6 -2) (wherein # has the same meaning as above.) 6 -2), n R 4 Ring A substituted with 6 That is, n R 4 a 6-membered non-aromatic nitrogen-containing heterocycle substituted with n R 4 a 6-membered aromatic nitrogen-containing heterocycle substituted with 6 In the formula (I), the atom bonded to D is a carbon atom or a nitrogen atom, and ring A is adjacent to the atom bonded to D. 6 At least one of the atoms constituting the formula (A) is a nitrogen atom. 6 -2) groups represented by the formulae H1, H2, H3, H4 and H5 [wherein the symbols have the same meanings as defined above].
[0010] The N-oxide of the compound represented by formula (I) or formula (II) means a structure in which at least one nitrogen atom contained in the compound represented by formula (I) or formula (II) is substituted with an oxo group.
[0011] The present compound or the compound of the present invention may exist in one or more stereoisomers. Stereoisomers include enantiomers, diastereomers, atropisomers, and geometric isomers. The present invention includes each stereoisomer and a mixture of stereoisomers in any ratio.
[0012] The compound represented by formula (I) or formula (II) or an N-oxide thereof may form an acid addition salt such as a hydrochloride, a sulfate, a nitrate, a phosphate, an acetate, or a benzoate when mixed with an acid such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, or benzoic acid.
[0013] In the present compound, when q is 2, 3, 4, or 5, two adjacent R 6 and R 6 are taken together with the carbon atoms to which they are bonded to form a C5-C6 alicyclic hydrocarbon, a 5- to 6-membered non-aromatic heterocycle (the C5-C6 alicyclic hydrocarbon and the 5- to 6-membered non-aromatic heterocycle may be substituted with one or more substituents selected from Group B), a benzene ring, or a 5- to 6-membered aromatic heterocycle (the benzene ring and the 5- to 6-membered aromatic heterocycle may be substituted with one or more substituents selected from Group C) specifically means a compound represented by the following formula: 1) In the formula, ring A 6 , D.R. 3 , R 4 , m and n have the same meaning as in [1], R 6A , R 6B and R 6C are the same or different, and R in [1] 6 or a hydrogen atom, 6D and R 6E together with the carbon atoms to which they are bonded, form a C5-C6 alicyclic hydrocarbon, a 5- to 6-membered non-aromatic heterocycle (the C5-C6 alicyclic hydrocarbon and the 5- to 6-membered non-aromatic heterocycle may be substituted with one or more substituents selected from Group B), a benzene ring, or a 5- to 6-membered aromatic heterocycle (the benzene ring and the 5- to 6-membered aromatic heterocycle may be substituted with one or more substituents selected from Group C); or 2) a compound in which, in formula (I-A), Ring A 6 , D.R. 3 , R 4 , m and n have the same meaning as in [1], R 6A , R 6B and R 6E are the same or different, and R in [1] 6 or a hydrogen atom, 6C and R 6Dare taken together with the carbon atoms to which they are bonded to form a C5-C6 alicyclic hydrocarbon, a 5- to 6-membered non-aromatic heterocycle (the C5-C6 alicyclic hydrocarbon and the 5- to 6-membered non-aromatic heterocycle may be substituted with one or more substituents selected from Group B), a benzene ring, or a 5- to 6-membered aromatic heterocycle (the benzene ring and the 5- to 6-membered aromatic heterocycle may be substituted with one or more substituents selected from Group C).
[0014] The following compounds are examples of the present compound A: [Aspect A1] In the present compound A, ring A 6 is a 6-membered non-aromatic nitrogen-containing heterocycle. [Aspect A2] In the compound A, ring A 6 is a 6-membered aromatic nitrogen-containing heterocycle. [Aspect A3] Compound A of the present invention, 6 is pyridine, pyrazine, pyrimidine, or pyridazine. [Aspect A4] Compound A of the present invention, 6 [Aspect A5] Compound A, wherein ring A is pyridine. 6 [Aspect A6] Compound A, wherein ring A is pyrazine. 6 [Aspect A7] Compound A, wherein ring A is pyrimidine. 6 [Aspect A8] The compound A, wherein D is CR 1 R 2 [Aspect A9] The compound A, in which D is C=O. [Aspect A10] The compound A, in which R 1 and R 2 are the same or different and are a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom. [Aspect A11] Compound A, wherein R 1 and R 2 are the same or different, OR 8 or a hydrogen atom. [Aspect A12] In the compound A, R 1 and R 2 are the same or different, SR 9 , S(O)R 10 , S(O)R 11 , N.R. 12R 13 or a hydrogen atom. [Aspect A13] In this compound, R 1 and R 2 are the same or different, C(O)R 14 , C(R 15 ) = NOR 16 , a cyano group, a nitro group, or a hydrogen atom. [Aspect A14] In the compound A, R 1 and R 2 are the same or different and are a halogen atom or a hydrogen atom. [Aspect A15] In the compound A, R 1 and R 2 is a hydrogen atom. [Aspect A16] Compound A, 3 is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms. [Aspect A17] Compound A, wherein R 3 is a C3-C8 alicyclic hydrocarbon group or a 3- to 8-membered non-aromatic heterocyclic group (the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from Group B). [Aspect A18] A compound of the present invention, wherein R 3 is a phenyl group or a 5- or 6-membered aromatic heterocyclic group (the phenyl group and the 5- or 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group C). [Aspect A19] A compound of the present invention, wherein R 3 But OR 17 , S.R. 18 , S(O)R 19 , S(O)R 20 , N.R. 21 R 22 , C(O)R 23 , C(R 24 ) = NOR 25 , a cyano group, or a nitro group. [Aspect A20] In the compound A, R 3 is a halogen atom. [Aspect A21] Compound A of the present invention, 4 is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms. [Aspect A22] Compound A of the present invention, 4is a C3-C8 alicyclic hydrocarbon group or a 3- to 8-membered non-aromatic heterocyclic group (the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group may have one or more substituents selected from Group B). [Aspect A23] A compound of the present compound A, wherein R 4 But OR 26 , N.R. 27 R 28 , C(O)R 29 , C(R 30 ) = NOR 31 , a cyano group, or a nitro group. [Aspect A24] In the compound A, R 4 is a halogen atom. [Aspect A25] Compound A, 6 is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms. [Aspect A26] Compound A of the present invention, 6 is a C3-C8 alicyclic hydrocarbon group or a 3- to 8-membered non-aromatic heterocyclic group (the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group may have one or more substituents selected from Group B). [Aspect A27] A compound of the present invention, wherein R 6 is a phenyl group or a 5- or 6-membered aromatic heterocyclic group (the phenyl group and the 5- or 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group C). [Aspect A28] A compound of the present invention, wherein R 6 But OR 32 , S.R. 33 , S(O)R 34 , S(O)R 35 , N.R. 36 R 37 , C(O)R 38 , C(R 39 ) = NOR 40 , a cyano group, or a nitro group. [Aspect A29] In the compound A, R 6is a halogen atom. [Aspect A30] A compound in this compound A wherein n is 0. [Aspect A31] A compound in this compound A wherein n is 1. [Aspect A32] A compound in this compound A wherein n is 2. [Aspect A33] A compound in this compound A wherein n is 3. [Aspect A34] A compound in this compound A wherein m is 0. [Aspect A35] A compound in this compound A wherein m is 1. [Aspect A36] A compound in this compound A wherein m is 2. [Aspect A37] A compound in this compound A wherein m is 3. [Aspect A38] A compound in this compound A wherein m is 4. [Aspect A39] A compound in this compound A wherein q is 0. [Aspect A40] A compound in this compound A wherein q is 1. [Aspect A41] A compound in this compound A wherein q is 2. [Aspect A42] A compound in this compound A wherein q is 3. [Aspect A43] The compound A, wherein q is 4. [Aspect A44] The compound A, wherein q is 5. [Aspect A45] The compound A, wherein two adjacent R 6 and R 6 are taken together with the carbon atoms to which they are attached to form a C5-C6 alicyclic hydrocarbon or a 5- or 6-membered non-aromatic heterocycle (the C5-C6 alicyclic hydrocarbon and the 5- or 6-membered non-aromatic heterocycle may be substituted with one or more halogen atoms). [Aspect A46] In Compound A, when two adjacent R 6 and R 6 are taken together with the carbon atoms to which they are attached to form a benzene ring or a 5- or 6-membered aromatic heterocycle (the benzene ring and the 5- or 6-membered aromatic heterocycle may be substituted with one or more halogen atoms). [Aspect A47] In this compound A, R 1 and R 2 are the same or different, and are C1-C6 chain hydrocarbon groups optionally substituted with one or more halogen atoms, OR 8 or a hydrogen atom. [Aspect A48] In the compound A, R 3 is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a halogen atom. [Aspect A49] Compound A of the present invention, wherein R 4is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a halogen atom. [Aspect A50] Compound A, wherein R 6 is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a halogen atom. [Aspect A51] A compound of the present compound A, wherein m is 1 or 2. [Aspect A52] A compound of the present compound A, wherein ring A 6 is a 6-membered non-aromatic nitrogen-containing heterocycle, and D is CR 1 R 2 and R 1 and R 2 are the same or different, and are C1-C6 chain hydrocarbon groups optionally substituted with one or more halogen atoms, OR 8 or a hydrogen atom, and R 3 is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a halogen atom, and m is 1 or 2. [Aspect A53-1] Compound A of the present invention, wherein ring A 6 is pyridine, pyrazine, pyrimidine, or pyridazine, and D is CR 1 R 2 and R 1 and R 2 are the same or different, and are C1-C6 chain hydrocarbon groups optionally substituted with one or more halogen atoms, OR 8 or a hydrogen atom, and R 3 is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a halogen atom, and m is 1 or 2. [Aspect A53-2] Compound A of the present invention, wherein R 1 and R 2 are the same or different and are a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A, or a hydrogen atom. [Aspect A54] In this compound A, R 3 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A. [Aspect A55] Compound A, wherein R 4 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A. [Aspect A56] Compound A, wherein R6 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A. [Aspect A57] Compound A, wherein R 1 and R 2 together with the carbon atom to which they are bonded to form a C3-C8 alicyclic hydrocarbon or a 3- to 8-membered non-aromatic heterocycle {the C3-C8 alicyclic hydrocarbon and the 3- to 8-membered non-aromatic heterocycle may be substituted with one or more substituents selected from Group B}.
[0015] The following compounds are also examples of the present compound A: [Aspect AA1] Formula (I-1A) [In the formula, X A , X B , X C and X D The combination of A is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is CR Z4 A combination in which: X A is a nitrogen atom, and X B is CR Z2 and X C is CR Z3 and X D is CR Z4 A combination in which: X A is CR Z1 and X B is a nitrogen atom, and X C is CR Z3 and X D is CR Z4 A combination in which: X A is CR Z1 and X B is CR Z2 and X C is a nitrogen atom, and X D is CR Z4 or a combination in which X A is CR Z1 and X B is CR Z2 and X Cis CR Z3 and X D represents a combination of R and R being a nitrogen atom; Z1 , R Z2 , R Z3 , and R Z4 are the same or different and each represents a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, or a 3- to 8-membered non-aromatic heterocyclic group, each of which may be substituted with one or more halogen atoms (the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group may have one or more substituents selected from Group B), OR 26 , N.R. 27 R 28 , C(O)R 29 , C(R 30 ) = NOR 31 , a cyano group, a nitro group, a halogen atom, or a hydrogen atom; D A is CR 1A R 2A or C═O, R 1A and R 2A are the same or different, and are C1-C6 chain hydrocarbon groups optionally substituted with one or more halogen atoms; OR 8 , S.R. 9 , S(O)R 10 , S(O)R 11 , N.R. 12 R 13 , C(O)R 14 , C(R 15 ) = NOR 16 , a cyano group, a nitro group, a halogen atom, or a hydrogen atom; R A2 , R A3 , R A4 , and R A5 are the same or different and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group (the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from Group B), a phenyl group, a 5- to 6-membered aromatic heterocyclic group (the phenyl group and the 5- to 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group C), OR 17 , S.R. 18 , S(O)R 19, S(O)R 20 , N.R. 21 R 22 , C(O)R 23 , C(R 24 ) = NOR 25 , a cyano group, a nitro group, a halogen atom, or a hydrogen atom; R B2 , R B3 , R B4 , R B5 , and R B6 are the same or different and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group (the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group may have one or more substituents selected from Group B), a phenyl group, a 5- to 6-membered aromatic heterocyclic group (the phenyl group and the 5- to 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group C), OR 32 , S.R. 33 , S(O)R 34 , S(O)R 35 , N.R. 36 R 37 , C(O)R 38 , C(R 39 ) = NOR 40 , a cyano group, a nitro group, a halogen atom, or a hydrogen atom; R B5 and R B6 may, together with the carbon atoms to which they are bonded, form a C5-C6 alicyclic hydrocarbon, a 5- to 6-membered non-aromatic heterocycle (the C5-C6 alicyclic hydrocarbon and the 5- to 6-membered non-aromatic heterocycle may be substituted with one or more substituents selected from Group B), a benzene ring, or a 5- to 6-membered aromatic heterocycle (the benzene ring and the 5- to 6-membered aromatic heterocycle may be substituted with one or more substituents selected from Group C), R B4 and R B5may, together with the carbon atoms to which they are bonded, form a C5-C6 alicyclic hydrocarbon, a 5- to 6-membered non-aromatic heterocycle (the C5-C6 alicyclic hydrocarbon and the 5- to 6-membered non-aromatic heterocycle may be substituted with one or more substituents selected from Group B), a benzene ring, or a 5- to 6-membered aromatic heterocycle (the benzene ring and the 5- to 6-membered aromatic heterocycle may be substituted with one or more substituents selected from Group C), and the other symbols have the same meanings as in [1]. [Aspect AA2] A compound represented by the following formula: In Aspect AA1, R B2 , R B3 , R B4 , R B5 , and R B6 are the same or different, and are C1-C4 chain hydrocarbon groups optionally substituted with one or more halogen atoms, OR 32 , S.R. 33 , S(O)R 34 , S(O)R 35 , a cyano group, a halogen atom, or a hydrogen atom; R 32 , R 33 , R 34 , and R 35 are the same or different and are C1-C4 alkyl groups optionally substituted with one or more halogen atoms, R B5 and R B6 together with the carbon atom to which they are bonded form a C5-C6 alicyclic hydrocarbon, a 5- or 6-membered non-aromatic heterocycle {the C5-C6 alicyclic hydrocarbon and the 5- or 6-membered non-aromatic heterocycle are selected from the group B A2 or a 5- or 6-membered aromatic heterocycle {which may be substituted with one or more substituents selected from group B A2 R may be substituted with one or more substituents selected from the group consisting of B4 and R B5 together with the carbon atom to which they are bonded form a C5-C6 alicyclic hydrocarbon, a 5- or 6-membered non-aromatic heterocycle {the C5-C6 alicyclic hydrocarbon and the 5- or 6-membered non-aromatic heterocycle are selected from the group B A2 or a 5- or 6-membered aromatic heterocycle {which may be substituted with one or more substituents selected from group B A2and optionally substituted with one or more substituents selected from the group consisting of: A2 A group consisting of a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a cyano group, and a halogen atom. [Aspect AA3] In aspect AA1, R B2 , R B3 , R B4 , R B5 , and R B6 are the same or different, and are C1-C4 chain hydrocarbon groups optionally substituted with one or more halogen atoms, OR 32 , S.R. 33 , S(O)R 34 , S(O)R 35 , a cyano group, a halogen atom, or a hydrogen atom; R 32 , R 33 , R 34 , and R 35 are the same or different and are C1-C4 alkyl groups optionally substituted with one or more halogen atoms. [Aspect AA4] A compound according to Aspect AA1, wherein R B2 , R B3 , R B4 , R B5 , and R B6 are the same or different and are a C1-C4 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C4 alkoxy group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom, and R B5 and R B6 together with the carbon atom to which they are bonded form a C5-C6 alicyclic hydrocarbon, a 5- or 6-membered non-aromatic heterocycle {the C5-C6 alicyclic hydrocarbon and the 5- or 6-membered non-aromatic heterocycle are selected from the group B A2 or a 5- or 6-membered aromatic heterocycle {which may be substituted with one or more substituents selected from group B A2 R may be substituted with one or more substituents selected from the group consisting of B4 and R B5 together with the carbon atom to which they are bonded form a C5-C6 alicyclic hydrocarbon, a 5- or 6-membered non-aromatic heterocycle {the C5-C6 alicyclic hydrocarbon and the 5- or 6-membered non-aromatic heterocycle are selected from the group B A2or a 5- or 6-membered aromatic heterocycle {which may be substituted with one or more substituents selected from group B A2 [Aspect AA5] In Aspect AA1, R B2 , R B3 , R B4 , R B5 , and R B6 and R are the same or different and are a C1-C4 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C4 alkoxy group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom. [Aspect AA6] A compound in Aspect AA1, wherein R B2 , R B3 , R B4 , R B5 , and R B6 are the same or different and are a halogen atom or a hydrogen atom, R B5 and R B6 together with the carbon atom to which they are bonded form a C5-C6 alicyclic hydrocarbon, a 5- or 6-membered non-aromatic heterocycle {the C5-C6 alicyclic hydrocarbon and the 5- or 6-membered non-aromatic heterocycle are selected from the group B A2 or a 5- or 6-membered aromatic heterocycle {which may be substituted with one or more substituents selected from group B A2 R may be substituted with one or more substituents selected from the group consisting of B4 and R B5 together with the carbon atom to which they are bonded form a C5-C6 alicyclic hydrocarbon, a 5- or 6-membered non-aromatic heterocycle {the C5-C6 alicyclic hydrocarbon and the 5- or 6-membered non-aromatic heterocycle are selected from the group B A2 or a 5- or 6-membered aromatic heterocycle {which may be substituted with one or more substituents selected from group B A2 [Aspect AA7] In Aspect AA1, R B2 , R B3 , R B4 , R B5 , and R B6are the same or different and are a halogen atom or a hydrogen atom. [Aspect AA8] In aspect AA1, R B5 and R B6 together with the carbon atom to which they are bonded form a C5-C6 alicyclic hydrocarbon, a 5- or 6-membered non-aromatic heterocycle {the C5-C6 alicyclic hydrocarbon and the 5- or 6-membered non-aromatic heterocycle are selected from the group B A2 or a 5- or 6-membered aromatic heterocycle {which may be substituted with one or more substituents selected from group B A2 [Aspect AA9] In Aspect AA1, R B4 and R B5 together with the carbon atom to which they are bonded form a C5-C6 alicyclic hydrocarbon, a 5- or 6-membered non-aromatic heterocycle {the C5-C6 alicyclic hydrocarbon and the 5- or 6-membered non-aromatic heterocycle are selected from the group B A2 or a 5- or 6-membered aromatic heterocycle {which may be substituted with one or more substituents selected from group B A2 [Aspect AA10] In Aspect AA1, R A2 , R A3 , R A4 , and R A5 are the same or different and are a halogen atom or a hydrogen atom. [Aspect AA11] In aspect AA2, R A2 , R A3 , R A4 , and R A5 are the same or different and are a halogen atom or a hydrogen atom. [Aspect AA12] In aspect AA3, R A2 , R A3 , R A4 , and R A5 are the same or different and are a halogen atom or a hydrogen atom. [Aspect AA13] In aspect AA4, R A2 , R A3 , R A4 , and R A5 are the same or different and are a halogen atom or a hydrogen atom. [Aspect AA14] In aspect AA5, R A2 , RA3 , R A4 , and R A5 are the same or different and are a halogen atom or a hydrogen atom. [Aspect AA15] In aspect AA6, R A2 , R A3 , R A4 , and R A5 are the same or different and are a halogen atom or a hydrogen atom. [Aspect AA16] In aspect AA7, R A2 , R A3 , R A4 , and R A5 are the same or different and are a halogen atom or a hydrogen atom. [Aspect AA17] In aspect AA8, R A2 , R A3 , R A4 , and R A5 are the same or different and are a halogen atom or a hydrogen atom. [Aspect AA18] In aspect AA9, R A2 , R A3 , R A4 , and R A5 are the same or different and are a halogen atom or a hydrogen atom. [Aspect AA19] In aspect AA1, R A3 and R A4 is a hydrogen atom, and R A2 and R A5 are the same or different and are a halogen atom or a hydrogen atom. [Aspect AA20] In aspect AA2, R A3 and R A4 is a hydrogen atom, and R A2 and R A5 are the same or different and are a halogen atom or a hydrogen atom. [Aspect AA21] In aspect AA3, R A3 and R A4 is a hydrogen atom, and R A2 and R A5 are the same or different and are a halogen atom or a hydrogen atom. [Aspect AA22] In aspect AA4, R A3 and R A4 is a hydrogen atom, and R A2 and R A5are the same or different and are a halogen atom or a hydrogen atom. [Aspect AA23] In Aspect AA5, R A3 and R A4 is a hydrogen atom, and R A2 and R A5 are the same or different and are a halogen atom or a hydrogen atom. [Aspect AA24] In aspect AA6, R A3 and R A4 is a hydrogen atom, and R A2 and R A5 are the same or different and are a halogen atom or a hydrogen atom. [Aspect AA25] In aspect AA7, R A3 and R A4 is a hydrogen atom, and R A2 and R A5 are the same or different and are a halogen atom or a hydrogen atom. [Aspect AA26] In aspect AA8, R A3 and R A4 is a hydrogen atom, and R A2 and R A5 are the same or different and are a halogen atom or a hydrogen atom. [Aspect AA27] In aspect AA9, R A3 and R A4 is a hydrogen atom, and R A2 and R A5 are the same or different and are a halogen atom or a hydrogen atom. [Aspect AA28] In aspect AA1, R A3 and R A4 is a hydrogen atom, and R A2 and R A5 are the same or different and are a fluorine atom or a hydrogen atom. [Aspect AA29] In aspect AA2, R A3 and R A4 is a hydrogen atom, and R A2 and R A5 are the same or different and are a fluorine atom or a hydrogen atom. [Aspect AA30] In aspect AA3, R A3 and R A4 is a hydrogen atom, and R A2 and R A5 are the same or different and are a fluorine atom or a hydrogen atom. [Aspect AA31] A compound in which RA3 and R A4 is a hydrogen atom, and R A2 and R A5 are the same or different and are a fluorine atom or a hydrogen atom. [Aspect AA32] In Aspect AA5, R A3 and R A4 is a hydrogen atom, and R A2 and R A5 are the same or different and are a fluorine atom or a hydrogen atom. [Aspect AA33] In aspect AA6, R A3 and R A4 is a hydrogen atom, and R A2 and R A5 are the same or different and are a fluorine atom or a hydrogen atom. [Aspect AA34] In aspect AA7, R A3 and R A4 is a hydrogen atom, and R A2 and R A5 are the same or different and are a fluorine atom or a hydrogen atom. [Aspect AA35] In aspect AA8, R A3 and R A4 is a hydrogen atom, and R A2 and R A5 are the same or different and are a fluorine atom or a hydrogen atom. [Aspect AA36] In aspect AA9, R A3 and R A4 is a hydrogen atom, and R A2 and R A5 are the same or different and are a fluorine atom or a hydrogen atom. [Aspect AA37] In aspect AA1, R A3 and R A4 is a hydrogen atom, and R A2 and R A5 is a fluorine atom. [Aspect AA38] A compound according to aspect AA2, wherein R A3 and R A4 is a hydrogen atom, and R A2 and R A5 is a fluorine atom. [Aspect AA39] In aspect AA3, R A3 and R A4 is a hydrogen atom, and R A2 and R A5is a fluorine atom. [Aspect AA40] In aspect AA4, R A3 and R A4 is a hydrogen atom, and R A2 and R A5 is a fluorine atom. [Aspect AA41] A compound in aspect AA5, wherein R A3 and R A4 is a hydrogen atom, and R A2 and R A5 is a fluorine atom. [Aspect AA42] A compound according to aspect AA6, wherein R A3 and R A4 is a hydrogen atom, and R A2 and R A5 is a fluorine atom. [Aspect AA43] A compound according to aspect AA7, wherein R A3 and R A4 is a hydrogen atom, and R A2 and R A5 is a fluorine atom. [Aspect AA44] A compound according to aspect AA8, wherein R A3 and R A4 is a hydrogen atom, and R A2 and R A5 is a fluorine atom. [Aspect AA45] A compound according to aspect AA9, wherein R A3 and R A4 is a hydrogen atom, and R A2 and R A5 is a fluorine atom. [Aspect AA46] In any one of Aspects AA1 to AA45, X A is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is a nitrogen atom or CR Z4 [Aspect AA47] In any one of Aspects AA1 to AA45, X A is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is a nitrogen atom or CR Z4 and R Z1 , R Z2 , RZ3 , and R Z4 and are the same or different and are a methyl group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom. [Aspect AA48] In any of Aspects AA1 to AA45, X A is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is a nitrogen atom or CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 is a hydrogen atom. [Aspect AA49] In any one of Aspects AA1 to AA45, X A is a nitrogen atom or CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is CR Z4 [Aspect AA50] In any one of Aspects AA1 to AA45, X A is a nitrogen atom or CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 and are the same or different and are a methyl group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom. [Aspect AA51] In any of Aspects AA1 to AA45, X A is a nitrogen atom or CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is CR Z4 and R Z1 , R Z2 , RZ3 , and R Z4 is a hydrogen atom. [Aspect AA52] In any one of Aspects AA1 to AA45, X A is CR Z1 and X B is CR Z2 and X C is a nitrogen atom or CR Z3 and X D is CR Z4 [Aspect AA53] In any one of Aspects AA1 to AA45, X A is CR Z1 and X B is CR Z2 and X C is a nitrogen atom or CR Z3 and X D is CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 and X are the same or different and are a methyl group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom. [Aspect AA54] In any of Aspects AA1 to AA45, X A is CR Z1 and X B is CR Z2 and X C is a nitrogen atom or CR Z3 and X D is CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 is a hydrogen atom. [Aspect AA55] In any one of Aspects AA1 to AA45, X A is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is CR Z4 [Aspect AA56] In any one of Aspects AA1 to AA45, X A is CR Z1 and X B is CRZ2 and X C is CR Z3 and X D is CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 and are the same or different and are a methyl group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom. [Aspect AA57] In any of Aspects AA1 to AA45, X A is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 is a hydrogen atom. [Aspect AA58] In any one of Aspects AA1 to AA45, D A is CR 1A R 2A and R 1A and R 2A are the same or different, OR 8 or a hydrogen atom, and R 8 is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect AA59] A compound in any one of Aspects AA1 to AA45, wherein D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 or a hydrogen atom, and R 8 is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect AA60] A compound in any of Aspects AA1 to AA45, wherein D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR8 or a hydrogen atom, and R 8 is a hydrogen atom. [Aspect AA61] In any one of Aspects AA1 to AA45, D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 and R 8 is a hydrogen atom. [Aspect AA62] In any one of Aspects AA1 to AA45, D A is CR 1A R 2A and R 1A and R 2A is a hydrogen atom. [Aspect AA63] In any one of Aspects AA1 to AA45, X A is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is a nitrogen atom or CR Z4 and D A is CR 1A R 2A and R 1A and R 2A are the same or different, OR 8 or a hydrogen atom, and R 8 is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect AA64] A compound in any one of Aspects AA1 to AA45, wherein X A is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is a nitrogen atom or CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 are the same or different and are methyl groups optionally substituted with one or more halogen atoms, halogen atoms or hydrogen atoms, and D A is CR1A R 2A and R 1A and R 2A are the same or different, OR 8 or a hydrogen atom, and R 8 is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect AA65] A compound in any one of Aspects AA1 to AA45, wherein X A is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is a nitrogen atom or CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 is a hydrogen atom, and D A is CR 1A R 2A and R 1A and R 2A are the same or different, OR 8 or a hydrogen atom, and R 8 is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect AA66] A compound in any one of Aspects AA1 to AA45, wherein X A is a nitrogen atom or CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is CR Z4 and D A is CR 1A R 2A and R 1A and R 2A are the same or different, OR 8 or a hydrogen atom, and R 8is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect AA67] A compound in any one of Aspects AA1 to AA45, wherein X A is a nitrogen atom or CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 are the same or different and are methyl groups optionally substituted with one or more halogen atoms, halogen atoms or hydrogen atoms, and D A is CR 1A R 2A and R 1A and R 2A are the same or different, OR 8 or a hydrogen atom, and R 8 is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect AA68] A compound in any one of Aspects AA1 to AA45, wherein X A is a nitrogen atom or CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 is a hydrogen atom, and D A is CR 1A R 2A and R 1A and R 2A are the same or different, OR 8 or a hydrogen atom, and R 8is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect AA69] A compound in any one of Aspects AA1 to AA45, wherein X A is CR Z1 and X B is CR Z2 and X C is a nitrogen atom or CR Z3 and X D is CR Z4 and D A is CR 1A R 2A and R 1A and R 2A are the same or different, OR 8 or a hydrogen atom, and R 8 is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect AA70] A compound in any one of Aspects AA1 to AA45, wherein X A is CR Z1 and X B is CR Z2 and X C is a nitrogen atom or CR Z3 and X D is CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 are the same or different and are methyl groups optionally substituted with one or more halogen atoms, halogen atoms or hydrogen atoms, and D A is CR 1A R 2A and R 1A and R 2A are the same or different, OR 8 or a hydrogen atom, and R 8 is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect AA71] A compound in any one of Aspects AA1 to AA45, wherein X A is CR Z1 and X B is CR Z2and X C is a nitrogen atom or CR Z3 and X D is CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 is a hydrogen atom, and D A is CR 1A R 2A and R 1A and R 2A are the same or different, OR 8 or a hydrogen atom, and R 8 is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect AA72] A compound in any one of Aspects AA1 to AA45, wherein X A is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is CR Z4 and D A is CR 1A R 2A and R 1A and R 2A are the same or different, OR 8 or a hydrogen atom, and R 8 is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect AA73] A compound in any one of Aspects AA1 to AA45, wherein X A is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 are the same or different and are methyl groups optionally substituted with one or more halogen atoms, halogen atoms or hydrogen atoms, and D A is CR1A R 2A and R 1A and R 2A are the same or different, OR 8 or a hydrogen atom, and R 8 is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect AA74] A compound in any one of Aspects AA1 to AA45, wherein X A is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 is a hydrogen atom, and D A is CR 1A R 2A and R 1A and R 2A are the same or different, OR 8 or a hydrogen atom, and R 8 is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect AA75] A compound in any one of Aspects AA1 to AA45, wherein X A is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is a nitrogen atom or CR Z4 and D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 or a hydrogen atom, and R 8 is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect AA76] A compound in any one of Aspects AA1 to AA45, wherein XA is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is a nitrogen atom or CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 are the same or different and are methyl groups optionally substituted with one or more halogen atoms, halogen atoms or hydrogen atoms, and D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 or a hydrogen atom, and R 8 is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect AA77] A compound in any one of Aspects AA1 to AA45, wherein X A is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is a nitrogen atom or CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 is a hydrogen atom, and D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 or a hydrogen atom, and R 8 is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect AA78] A compound in any one of Aspects AA1 to AA45, wherein X A is a nitrogen atom or CR Z1 and X B is CR Z2 and X C is CRZ3 and X D is CR Z4 and D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 or a hydrogen atom, and R 8 is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect AA79] A compound in any one of Aspects AA1 to AA45, wherein X A is a nitrogen atom or CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 are the same or different and are methyl groups optionally substituted with one or more halogen atoms, halogen atoms or hydrogen atoms, and D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 or a hydrogen atom, and R 8 is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect AA80] A compound in any one of Aspects AA1 to AA45, wherein X A is a nitrogen atom or CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 is a hydrogen atom, and D A is CR 1A R 2Aand R 1A is a hydrogen atom, and R 2A is OR 8 or a hydrogen atom, and R 8 is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect AA81] A compound in any one of Aspects AA1 to AA45, wherein X A is CR Z1 and X B is CR Z2 and X C is a nitrogen atom or CR Z3 and X D is CR Z4 and D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 or a hydrogen atom, and R 8 is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect AA82] A compound in any one of Aspects AA1 to AA45, wherein X A is CR Z1 and X B is CR Z2 and X C is a nitrogen atom or CR Z3 and X D is CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 are the same or different and are methyl groups optionally substituted with one or more halogen atoms, halogen atoms or hydrogen atoms, and D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 or a hydrogen atom, and R 8is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect AA83] A compound in any one of Aspects AA1 to AA45, wherein X A is CR Z1 and X B is CR Z2 and X C is a nitrogen atom or CR Z3 and X D is CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 is a hydrogen atom, and D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 or a hydrogen atom, and R 8 is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect AA84] A compound in any one of Aspects AA1 to AA45, wherein X A is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is CR Z4 and D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 or a hydrogen atom, and R 8 is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect AA85] A compound in any one of Aspects AA1 to AA45, wherein X A is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is CRZ4 and R Z1 , R Z2 , R Z3 , and R Z4 are the same or different and are methyl groups optionally substituted with one or more halogen atoms, halogen atoms or hydrogen atoms, and D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 or a hydrogen atom, and R 8 is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect AA86] A compound in any one of Aspects AA1 to AA45, wherein X A is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 is a hydrogen atom, and D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 or a hydrogen atom, and R 8 is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect AA87] A compound in any one of Aspects AA1 to AA45, wherein X A is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is a nitrogen atom or CR Z4 and D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2Ais OR 8 or a hydrogen atom, and R 8 is a hydrogen atom. [Aspect AA88] In any one of Aspects AA1 to AA45, X A is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is a nitrogen atom or CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 are the same or different and are methyl groups optionally substituted with one or more halogen atoms, halogen atoms or hydrogen atoms, and D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 or a hydrogen atom, and R 8 is a hydrogen atom. [Aspect AA89] In any one of Aspects AA1 to AA45, X A is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is a nitrogen atom or CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 is a hydrogen atom, and D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 or a hydrogen atom, and R 8 is a hydrogen atom. [Aspect AA90] In any one of Aspects AA1 to AA45, X A is a nitrogen atom or CR Z1 and X B is CR Z2 and X C is CR Z3 and X Dis CR Z4 and D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 or a hydrogen atom, and R 8 is a hydrogen atom. [Aspect AA91] In any one of Aspects AA1 to AA45, X A is a nitrogen atom or CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 are the same or different and are methyl groups optionally substituted with one or more halogen atoms, halogen atoms or hydrogen atoms, and D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 or a hydrogen atom, and R 8 is a hydrogen atom. [Aspect AA92] In any one of Aspects AA1 to AA45, X A is a nitrogen atom or CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 is a hydrogen atom, and D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 or a hydrogen atom, and R 8 is a hydrogen atom. [Aspect AA93] In any one of Aspects AA1 to AA45, X Ais CR Z1 and X B is CR Z2 and X C is a nitrogen atom or CR Z3 and X D is CR Z4 and D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 or a hydrogen atom, and R 8 is a hydrogen atom. [Aspect AA94] In any one of Aspects AA1 to AA45, X A is CR Z1 and X B is CR Z2 and X C is a nitrogen atom or CR Z3 and X D is CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 are the same or different and are methyl groups optionally substituted with one or more halogen atoms, halogen atoms or hydrogen atoms, and D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 or a hydrogen atom, and R 8 is a hydrogen atom. [Aspect AA95] In any one of Aspects AA1 to AA45, X A is CR Z1 and X B is CR Z2 and X C is a nitrogen atom or CR Z3 and X D is CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 is a hydrogen atom, and D A is CR 1A R 2A and R 1A is a hydrogen atom, and R2A is OR 8 or a hydrogen atom, and R 8 is a hydrogen atom. [Aspect AA96] In any one of Aspects AA1 to AA45, X A is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is CR Z4 and D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 or a hydrogen atom, and R 8 is a hydrogen atom. [Aspect AA97] In any one of Aspects AA1 to AA45, X A is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 are the same or different and are methyl groups optionally substituted with one or more halogen atoms, halogen atoms or hydrogen atoms, and D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 or a hydrogen atom, and R 8 is a hydrogen atom. [Aspect AA98] In any one of Aspects AA1 to AA45, X A is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is CR Z4 and R Z1 , R Z2 , R Z3 , and RZ4 is a hydrogen atom, and D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 or a hydrogen atom, and R 8 is a hydrogen atom. [Aspect AA99] In any one of Aspects AA1 to AA45, X A is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is a nitrogen atom or CR Z4 and D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 and R 8 is a hydrogen atom. [Aspect AA100] In any one of Aspects AA1 to AA45, X A is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is a nitrogen atom or CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 are the same or different and are methyl groups optionally substituted with one or more halogen atoms, halogen atoms or hydrogen atoms, and D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 and R 8 is a hydrogen atom. [Aspect AA101] In any one of Aspects AA1 to AA45, X A is CR Z1 and X B is CR Z2 and X C is CRZ3 and X D is a nitrogen atom or CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 is a hydrogen atom, and D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 and R 8 is a hydrogen atom. [Aspect AA102] In any one of Aspects AA1 to AA45, X A is a nitrogen atom or CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is CR Z4 and D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 and R 8 is a hydrogen atom. [Aspect AA103] In any one of Aspects AA1 to AA45, X A is a nitrogen atom or CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 are the same or different and are methyl groups optionally substituted with one or more halogen atoms, halogen atoms or hydrogen atoms, and D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 and R 8is a hydrogen atom. [Aspect AA104] In any one of Aspects AA1 to AA45, X A is a nitrogen atom or CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 is a hydrogen atom, and D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 and R 8 is a hydrogen atom. [Aspect AA105] In any one of Aspects AA1 to AA45, X A is CR Z1 and X B is CR Z2 and X C is a nitrogen atom or CR Z3 and X D is CR Z4 and D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 and R 8 is a hydrogen atom. [Aspect AA106] In any one of Aspects AA1 to AA45, X A is CR Z1 and X B is CR Z2 and X C is a nitrogen atom or CR Z3 and X D is CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 are the same or different and are methyl groups optionally substituted with one or more halogen atoms, halogen atoms or hydrogen atoms, and D A is CR1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 and R 8 is a hydrogen atom. [Aspect AA107] In any one of Aspects AA1 to AA45, X A is CR Z1 and X B is CR Z2 and X C is a nitrogen atom or CR Z3 and X D is CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 is a hydrogen atom, and D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 and R 8 is a hydrogen atom. [Aspect AA108] In any one of Aspects AA1 to AA45, X A is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is CR Z4 and D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 and R 8 is a hydrogen atom. [Aspect AA109] In any one of Aspects AA1 to AA45, X A is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is CR Z4 and R Z1 , R Z2 , R Z3 , and RZ4 are the same or different and are methyl groups optionally substituted with one or more halogen atoms, halogen atoms or hydrogen atoms, and D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 and R 8 is a hydrogen atom. [Aspect AA110] In any one of Aspects AA1 to AA45, X A is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 is a hydrogen atom, and D A is CR 1A R 2A and R 1A is a hydrogen atom, and R 2A is OR 8 and R 8 is a hydrogen atom. [Aspect AA111] In any one of Aspects AA1 to AA45, X A is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is a nitrogen atom or CR Z4 and D A is CR 1A R 2A and R 1A and R 2A is a hydrogen atom. [Aspect AA112] In any one of Aspects AA1 to AA45, X A is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is a nitrogen atom or CR Z4 and RZ1 , R Z2 , R Z3 , and R Z4 are the same or different and are methyl groups optionally substituted with one or more halogen atoms, halogen atoms or hydrogen atoms, and D A is CR 1A R 2A and R 1A and R 2A is a hydrogen atom. [Aspect AA113] In any one of Aspects AA1 to AA45, X A is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is a nitrogen atom or CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 is a hydrogen atom, and D A is CR 1A R 2A and R 1A and R 2A is a hydrogen atom. [Aspect AA114] In any one of Aspects AA1 to AA45, X A is a nitrogen atom or CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is CR Z4 and D A is CR 1A R 2A and R 1A and R 2A is a hydrogen atom. [Aspect AA115] In any one of Aspects AA1 to AA45, X A is a nitrogen atom or CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is CR Z4 and R Z1 , R Z2 , RZ3 , and R Z4 are the same or different and are methyl groups optionally substituted with one or more halogen atoms, halogen atoms or hydrogen atoms, and D A is CR 1A R 2A and R 1A and R 2A is a hydrogen atom. [Aspect AA116] In any one of Aspects AA1 to AA45, X A is a nitrogen atom or CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 is a hydrogen atom, and D A is CR 1A R 2A and R 1A and R 2A is a hydrogen atom. [Aspect AA117] In any one of Aspects AA1 to AA45, X A is CR Z1 and X B is CR Z2 and X C is a nitrogen atom or CR Z3 and X D is CR Z4 and D A is CR 1A R 2A and R 1A and R 2A is a hydrogen atom. [Aspect AA118] In any one of Aspects AA1 to AA45, X A is CR Z1 and X B is CR Z2 and X C is a nitrogen atom or CR Z3 and X D is CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4are the same or different and are methyl groups optionally substituted with one or more halogen atoms, halogen atoms or hydrogen atoms, and D A is CR 1A R 2A and R 1A and R 2A is a hydrogen atom. [Aspect AA119] In any one of Aspects AA1 to AA45, X A is CR Z1 and X B is CR Z2 and X C is a nitrogen atom or CR Z3 and X D is CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 is a hydrogen atom, and D A is CR 1A R 2A and R 1A and R 2A is a hydrogen atom. [Aspect AA120] In any one of Aspects AA1 to AA45, X A is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is CR Z4 and D A is CR 1A R 2A and R 1A and R 2A is a hydrogen atom. [Aspect AA121] In any one of Aspects AA1 to AA45, X A is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4are the same or different and are methyl groups optionally substituted with one or more halogen atoms, halogen atoms or hydrogen atoms, and D A is CR 1A R 2A and R 1A and R 2A is a hydrogen atom. [Aspect AA122] In any one of Aspects AA1 to AA45, X A is CR Z1 and X B is CR Z2 and X C is CR Z3 and X D is CR Z4 and R Z1 , R Z2 , R Z3 , and R Z4 is a hydrogen atom, and D A is CR 1A R 2A and R 1A and R 2A A compound in which is a hydrogen atom.
[0016] The following compounds are also examples of the present compound A: [Aspect AX1] In the present compound A, ring A 6 is a group represented by the formula H1, H2, H3, H4 or H5, and D is CR 1 R 2 , C═O, or C═N—OH, and R 1 and R 2 are the same or different and are a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a phenyl group, a 5- or 6-membered aromatic heterocyclic group, OR 8 , an amino group, a cyano group, a halogen atom, or a hydrogen atom, and R 3 is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, OR 17 or a halogen atom, R 4 is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, OR 26 or a halogen atom, R 6 is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, OR 32 , S.R.33 , S(O)R 34 , S(O)R 35 , a cyano group, or a halogen atom; R 8 But Group B X a C1-C6 chain hydrocarbon group optionally substituted by one or more substituents selected from the group consisting of a (C1-C6 alkyl)carbonyl group, a 5- or 6-membered aromatic heterocyclic group (the 5- or 6-membered aromatic heterocyclic group is selected from the group consisting of X or a hydrogen atom, and R 17 and R 32 are the same or different and are a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom, and R 33 , R 34 , and R 35 are the same or different and are C1-C6 chain hydrocarbon groups optionally substituted with one or more halogen atoms, and when q is 2, 3, 4, or 5, two adjacent R 6 and R 6 together with the carbon atom to which they are bonded form a C5-C6 alicyclic hydrocarbon, a 5- to 6-membered non-aromatic heterocycle, or a 5- to 6-membered aromatic heterocycle {the C5-C6 alicyclic hydrocarbon, the 5- to 6-membered non-aromatic heterocycle, and the 5- to 6-membered aromatic heterocycle are each selected from the group A X and the compound may form a group A, which may be substituted with one or more substituents selected from the following. X Group B: A group consisting of halogen atoms, C1-C4 alkyl groups, C1-C4 haloalkyl groups, C1-C4 alkoxy groups, and C1-C4 haloalkoxy groups. X :Group A X and a halogen atom. 6 is a group represented by the formula H1, H2, H3, H4 or H5, and D is CR 1 R 2 or C═O, and R 1 and R 2 are the same or different, and are C1-C4 chain hydrocarbon groups optionally substituted with one or more halogen atoms, OR 8 , a cyano group, a halogen atom, or a hydrogen atom; R3 is a C1-C4 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C4 alkoxy group, or a halogen atom, and R 4 is a C1-C4 chain hydrocarbon group, a C1-C4 alkoxy group, or a halogen atom, and R 6 is a C1-C4 chain hydrocarbon group, a C1-C4 alkoxy group, a C1-C4 sulfanyl group, a C1-C4 sulfinyl group, a C1-C4 sulfonyl group, a cyano group, a hydroxy group, or a halogen atom, and R 8 But Group B X a C1-C6 chain hydrocarbon group optionally substituted by one or more substituents selected from the group consisting of a (C1-C6 alkyl)carbonyl group, a 5- or 6-membered aromatic heterocyclic group (the 5- or 6-membered aromatic heterocyclic group is selected from the group consisting of X or a hydrogen atom, and when q is 2, 3, 4, or 5, two adjacent R 6 and R 6 may, together with the carbon atom to which they are attached, form a C5-C6 alicyclic hydrocarbon, a 5- or 6-membered non-aromatic heterocycle, or a 5- or 6-membered aromatic heterocycle.
[0017] The following compounds are examples of the compound A of the present invention: [Aspect B1] In the compound A of the present invention, X 1a is CR 41a and X 2a is CR 42a and X 3a is R 43a and X 4a is CR 44a [Aspect B2] In the compound A of the present invention, X 1a is a nitrogen atom, and X 2a is CR 42a and X 3a is R 43a and X 4a is CR 44a [Aspect B3] In the compound A of the present invention, X 1a is CR 41a and X 2a is CR 42a and X 3a is a nitrogen atom, and X 4ais CR 44a [Aspect B4] In the compound A of the present invention, X 1a is CR 41a and X 2a is CR 42a and X 3a is R 43a and X 4a is a nitrogen atom. [Aspect B5] Compound A of the present invention, 1a is CR 41a and X 2a is a nitrogen atom, and X 3a is R 43a and X 4a is CR 44a [Aspect B6] In the compound A of the present invention, X 1a is CR 41a and X 2a is a nitrogen atom, or CR 42a and X 3a is R 43a and X 4a is CR 44a [Aspect B7] In the compound A of the present invention, X 1a is CR 41a and X 2a is CR 42a and X 3a is R 43a and X 4a is a nitrogen atom, or CR 44a [Aspect B8] In the compound A of the present invention, X 1a is CR 41a and X 2a is CR 42a and X 3a is a nitrogen atom, or R 43a and X 4a is CR 44a [Aspect B9] In the compound A of the present invention, R 1a , and R 2a are the same or different, and are in Group A a [Aspect B10] In Compound A of the present invention, R 1a , and R 2aare the same or different and are a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom. [Aspect B11] Compound A of the present invention, 1a , and R 2a are the same or different, OR 8a or a hydrogen atom. [Aspect B12] In Compound A of the present invention, R 1a , and R 2a are the same or different, SR 9a , S(O)R 10a , S(O)R 11a , N.R. 12a R 13a or a hydrogen atom. [Aspect B13] In Compound A of the present invention, R 1a , and R 2a are the same or different, C(O)R 14a , C(R 15a ) = NOR 16a , a cyano group, a nitro group, or a hydrogen atom. [Aspect B14] In Compound A of the present invention, R 1a , and R 2a are the same or different and are a halogen atom or a hydrogen atom. [Aspect B15] In Compound A of the present invention, R 1a , and R 2a is a hydrogen atom. [Aspect B16] Compound A of the present invention, 1a , and R 2a are the same or different, and are C1-C6 chain hydrocarbon groups optionally substituted with one or more halogen atoms, OR 8a , a halogen atom, or a hydrogen atom. [Aspect B17] In Compound A of the present invention, R 1a , and R 2a are the same or different, and are C1-C6 chain hydrocarbon groups optionally substituted with one or more halogen atoms, OR 8a or a hydrogen atom. [Aspect B18] In Compound A of the present invention, R 1a , and R 2a are the same or different and are a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom. [Aspect B19] Compound A of the present invention, wherein R 3aand R 5a are the same or different, and are in Group A a [Aspect B20] In Compound A of the present invention, R 3a and R 5a and R are the same or different and are C1-C6 chain hydrocarbon groups optionally substituted with one or more halogen atoms. 3a and R 5a are the same or different and are a C3-C8 alicyclic hydrocarbon group or a 3- to 8-membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group are selected from the group B a [Aspect B22] In Compound A of the present invention, R 3a and R 5a are the same or different, and each is a phenyl group or a 5- or 6-membered aromatic heterocyclic group {the phenyl group and the 5- or 6-membered aromatic heterocyclic group are selected from the group C a [Aspect B23] In Compound A of the present invention, R 3a and R 5a are the same or different, OR 17a , S.R. 18a , S(O)R 19a , S(O)R 20a , N.R. 21a R 22a , C(O)R 23a , C(R 24a ) = NOR 25a , a cyano group, or a nitro group. [Aspect B24] In Compound A of the present invention, R 3a and R 5a and R are the same or different and are a halogen atom. 3a and R 5a are the same or different and are a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a halogen atom. [Aspect B26] Compound A of the present invention, 41a , R 42a , R 43a , and R44a are the same or different, and are in group D a [Aspect B27] In Compound A of the present invention, R 41a , R 42a , R 43a , and R 44a are the same or different and are a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom. [Aspect B28] Compound A of the present invention, wherein R 41a , R 42a , R 43a , and R 44a are the same or different, and are a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group are selected from the group B a [Aspect B29] In Compound A of the present invention, R 41a , R 42a , and R 44a are the same or different, OR 45a , N.R. 47a R 48a , C(R 49a ) = NOR 50a , a cyano group, a nitro group, or a hydrogen atom; R 43a But OR 46a , N.R. 47a R 48a , C(R 49a ) = NOR 50a , a cyano group, a nitro group, or a hydrogen atom. [Aspect B30] In Compound A of the present invention, R 41a , R 42a , R 43a , and R 44a are the same or different and are a halogen atom or a hydrogen atom. [Aspect B31] In the compound of the present invention, R 41a , R 42a , R 43a , and R 44a is a hydrogen atom. [Aspect B32] Compound A of the present invention, 41a , R 42a , R43a , and R 44a are the same or different and are a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom. [Aspect B33] Compound A of the present invention, wherein R 6a But Group A a [Aspect B34] In Compound A of the present invention, R 6a is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms. [Aspect B35] Compound A of the present invention, wherein R 6a a C3-C8 alicyclic hydrocarbon group or a 3- to 8-membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group are selected from the group B a [Aspect B36] In Compound A of the present invention, R 6a a phenyl group or a 5- or 6-membered aromatic heterocyclic group {the phenyl group and the 5- or 6-membered aromatic heterocyclic group are selected from the group C a [Aspect B37] In Compound A of the present invention, R 6a But OR 32a , S.R. 33a , S(O)R 34a , S(O)R 35a , N.R. 36a R 37a , C(O)R 38a , C(R 39a ) = NOR 40a , a cyano group, or a nitro group. [Aspect B38] In Compound A of the present invention, R 6a is a halogen atom. [Aspect B39] Compound A of the present invention, 6a is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a halogen atom. [Aspect B40] Compound A of the present invention, wherein R 6a is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, OR 32a , S.R. 33a , S(O)R 34a, S(O)R 35a or a halogen atom. [Aspect B41] A compound of the present invention, in which compound A is 0. [Aspect B42] A compound of the present invention, in which compound A is 1. [Aspect B43] A compound of the present invention, in which compound A is 2. [Aspect B44] A compound of the present invention, in which compound A is 3. [Aspect B45] A compound of the present invention, in which compound A is 0 or 1. [Aspect B46] A compound of the present invention, in which compound A is 0. [Aspect B47] A compound of the present invention, in which qa is 1. [Aspect B48] A compound of the present invention, in which qa is 2. [Aspect B49] A compound of the present invention, in which qa is 3. [Aspect B50] A compound of the present invention, in which qa is 4. [Aspect B51] A compound of the present invention, in which qa is 5. [Aspect B52] A compound of the present invention, in which R 1a and R 2a together with the carbon atom to which they are attached, form a C3-C8 alicyclic hydrocarbon or a 3- to 8-membered non-aromatic heterocyclic ring {the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group are selected from the group B a and the compound forms a ring structure in which the ring structure is ...
[0018] The following compounds are also examples of the compound A of the present invention: [Aspect BB1] Formula (II-1A) [In the formula, X E , X F , X G and X H The combination of E is CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 (where R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom; E is a nitrogen atom, and X F is CRZ6 and X G is CR Z7 and X H is CR Z8 A combination in which: X E is CR Z5 and X F is a nitrogen atom, and X G is CR Z7 and X H is CR Z8 A combination in which: X E is CR Z5 and X F is CR Z6 and X G is a nitrogen atom, and X H is CR Z8 or a combination in which X E is CR Z5 and X F is CR Z6 and X G is CR Z7 and X H represents a combination of R and R being a nitrogen atom; Z5 , R Z6 , and R Z8 are the same or different, and are C1-C6 chain hydrocarbon groups optionally substituted with one or more halogen atoms; OR 45a , N.R. 47a R 48a , C(R 49a ) = NOR 50a , a cyano group, a nitro group, a halogen atom, or a hydrogen atom; R Z7 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, OR 46a , N.R. 47a R 48a , C(R 49a ) = NOR 50a , a cyano group, a nitro group, a halogen atom, or a hydrogen atom; R 1B and R 2B are the same or different, and are C1-C6 chain hydrocarbon groups optionally substituted with one or more halogen atoms; OR 8a , S.R. 9a , S(O)R 10a , S(O)R 11a , N.R.12a R 13a , C(O)R 14a , C(R 15a ) = NOR 16a , a cyano group, a nitro group, a halogen atom, or a hydrogen atom; R C2 represents a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, or a 3- to 8-membered non-aromatic heterocyclic group, each of which may be substituted with one or more halogen atoms {the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group are each selected from the group B a a phenyl group, a 5- or 6-membered aromatic heterocyclic group {the phenyl group and the 5- or 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from the group C a may be substituted with one or more substituents selected from the group consisting of OR 17a , S.R. 18a , S(O)R 19a , S(O)R 20a , N.R. 21a R 22a , C(O)R 23a , C(R 24a ) = NOR 25a , a cyano group, a nitro group, or a halogen atom; R C3 , R C4 , and R C5 are the same or different and are a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, or a 3- to 8-membered non-aromatic heterocyclic group, each of which may be substituted with one or more halogen atoms {the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group are each selected from the group B a a phenyl group, a 5- or 6-membered aromatic heterocyclic group {the phenyl group and the 5- or 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from the group C a may be substituted with one or more substituents selected from the group consisting of OR 17a , S.R. 18a , S(O)R 19a , S(O)R 20a , N.R. 21a R 22a , C(O)R 23a , C(R 24a ) = NOR 25a , a cyano group, a nitro group, a halogen atom, or a hydrogen atom; R D2 , RD3 , R D4 , R D5 , and R D6 are the same or different and are a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, or a 3- to 8-membered non-aromatic heterocyclic group, each of which may be substituted with one or more halogen atoms {the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group are each selected from the group B a a phenyl group, a 5- or 6-membered aromatic heterocyclic group {the phenyl group and the 5- or 6-membered aromatic heterocyclic group may be selected from the group C a may be substituted with one or more substituents selected from the group consisting of OR 32a , S.R. 33a , S(O)R 34a , S(O)R 35a , N.R. 36a R 37a , C(O)R 38a , C(R 39a ) = NOR 40a , a cyano group, a nitro group, a halogen atom, or a hydrogen atom, and the other symbols have the same meanings as in [2]. [Aspect BB2] A compound represented by the formula: D2 , R D3 , R D4 , R D5 , and R D6 are the same or different, and are C1-C4 chain hydrocarbon groups optionally substituted with one or more halogen atoms, OR 32a , S.R. 33a , S(O)R 34a , S(O)R 35a , a cyano group, a halogen atom, or a hydrogen atom; R 32a , R 33a , R 34a , and R 35a are the same or different and are C1-C4 alkyl groups optionally substituted with one or more halogen atoms. [Aspect BB3] In Aspect BB1, R D2 , R D3 , R D4 , R D5 , and R D6and R are the same or different and are a C1-C4 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C4 alkoxy group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom. [Aspect BB4] A compound according to aspect BB1, wherein R D2 , R D3 , R D4 , R D5 , and R D6 and are the same or different and are a halogen atom or a hydrogen atom. C2 is a halogen atom, and R C3 , R C4 , and R C5 are the same or different and are a halogen atom or a hydrogen atom. [Aspect BB6] In aspect BB2, R C2 is a halogen atom, and R C3 , R C4 , and R C5 are the same or different and are a halogen atom or a hydrogen atom. [Aspect BB7] In aspect BB3, R C2 is a halogen atom, and R C3 , R C4 , and R C5 are the same or different and are a halogen atom or a hydrogen atom. [Aspect BB8] In Aspect BB4, R C2 is a halogen atom, and R C3 , R C4 , and R C5 are the same or different and are a halogen atom or a hydrogen atom. [Aspect BB9] In aspect BB1, R C2 is a halogen atom, and R C3 and R C4 is a hydrogen atom, and R C5 is a halogen atom or a hydrogen atom. [Aspect BB10] In aspect BB2, R C2 is a halogen atom, and R C3 and R C4 is a hydrogen atom, and R C5 is a halogen atom or a hydrogen atom. [Aspect BB11] In aspect BB3, R C2 is a halogen atom, and R C3 and RC4 is a hydrogen atom, and R C5 is a halogen atom or a hydrogen atom. [Aspect BB12] In aspect BB4, R C2 is a halogen atom, and R C3 and R C4 is a hydrogen atom, and R C5 is a halogen atom or a hydrogen atom. [Aspect BB13] In aspect BB1, R C2 and R C5 is a halogen atom, and R C3 and R C4 is a hydrogen atom. [Aspect BB14] In aspect BB2, R C2 and R C5 is a halogen atom, and R C3 and R C4 is a hydrogen atom. [Aspect BB15] In aspect BB3, R C2 and R C5 is a halogen atom, and R C3 and R C4 is a hydrogen atom. [Aspect BB16] In aspect BB4, R C2 and R C5 is a halogen atom, and R C3 and R C4 is a hydrogen atom. [Aspect BB17] In aspect BB1, R C2 is a fluorine atom, and R C3 and R C4 is a hydrogen atom, and R C5 is a fluorine atom or a hydrogen atom. [Aspect BB18] In aspect BB2, R C2 is a fluorine atom, and R C3 and R C4 is a hydrogen atom, and R C5 is a fluorine atom or a hydrogen atom. [Aspect BB19] In aspect BB3, R C2 is a fluorine atom, and R C3 and R C4 is a hydrogen atom, and R C5 is a fluorine atom or a hydrogen atom. [Aspect BB20] In aspect BB4, R C2 is a fluorine atom, and R C3 and R C4is a hydrogen atom, and R C5 is a fluorine atom or a hydrogen atom. [Aspect BB21] In aspect BB1, R C2 and R C5 is a fluorine atom, and R C3 and R C4 is a hydrogen atom. [Aspect BB22] In aspect BB2, R C2 and R C5 is a fluorine atom, and R C3 and R C4 is a hydrogen atom. [Aspect BB23] In aspect BB3, R C2 and R C5 is a fluorine atom, and R C3 and R C4 is a hydrogen atom. [Aspect BB24] In aspect BB4, R C2 and R C5 is a fluorine atom, and R C3 and R C4 is a hydrogen atom. [Aspect BB25] In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is a nitrogen atom or CR Z8 A compound (wherein X H is CR Z8 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom.) [Aspect BB26] In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is a nitrogen atom or CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8are the same or different and are methyl groups optionally substituted with one or more halogen atoms, halogen atoms or hydrogen atoms (provided that X H is CR Z8 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom. (Aspect BB27) In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is a nitrogen atom or CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 is a hydrogen atom. [Aspect BB28] In any one of Aspects BB1 to BB24, X E is a nitrogen atom or CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 A compound (wherein X E is CR Z5 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom. (Aspect BB29) In any one of Aspects BB1 to BB24, X E is a nitrogen atom or CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8are the same or different and are methyl groups optionally substituted with one or more halogen atoms, halogen atoms or hydrogen atoms (provided that X E is CR Z5 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom. [Aspect BB30] In any one of Aspects BB1 to BB24, X E is a nitrogen atom or CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 is a hydrogen atom. [Aspect BB31] In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is a nitrogen atom or CR Z7 and X H is CR Z8 A compound (wherein X G is CR Z7 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom.) [Aspect BB32] In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is a nitrogen atom or CR Z7 and X H is CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8are the same or different and are methyl groups optionally substituted with one or more halogen atoms, halogen atoms or hydrogen atoms (provided that X G is CR Z7 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom. (Aspect BB33) In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is a nitrogen atom or CR Z7 and X H is CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 is a hydrogen atom. [Aspect BB34] In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 (wherein R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom. (Aspect BB35) In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 are the same or different and are methyl groups optionally substituted with one or more halogen atoms, halogen atoms, or hydrogen atoms (provided that R Z5 , R Z6 , RZ7 , and R Z8 At least one of the groups is a hydrogen atom. (Aspect BB36) In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 is a hydrogen atom. [Aspect BB37] In any one of Aspects BB1 to BB24, R 1B and R 2B are the same or different, OR 8a or a hydrogen atom, and R 8a is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect BB38] In any of Aspects BB1 to BB24, R 1B is a hydrogen atom, and R 2B is OR 8a or a hydrogen atom, and R 8a is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect BB39] In any of Aspects BB1 to BB24, R 1B is a hydrogen atom, and R 2B is OR 8a or a hydrogen atom, and R 8a is a hydrogen atom. [Aspect BB40] In any one of Aspects BB1 to BB24, R 1B is a hydrogen atom, and R 2B is OR 8a and R 8a is a hydrogen atom. [Aspect BB41] In any one of Aspects BB1 to BB24, R 1B and R 2B is a hydrogen atom. [Aspect BB42] In any one of Aspects BB1 to BB24, X E is CR Z5 and XF is CR Z6 and X G is CR Z7 and X H is a nitrogen atom or CR Z8 and R 1B and R 2B are the same or different, OR 8a or a hydrogen atom, and R 8a is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom (provided that X H is CR Z8 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom.) [Aspect BB43] In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is a nitrogen atom or CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 are the same or different and are a methyl group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom, and R 1B and R 2B are the same or different, OR 8a or a hydrogen atom, and R 8a is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom (provided that X H is CR Z8 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom. (Aspect BB44) In any one of Aspects BB1 to BB24, X E is CR Z5 and X Fis CR Z6 and X G is CR Z7 and X H is a nitrogen atom or CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 is a hydrogen atom, and R 1B and R 2B are the same or different, OR 8a or a hydrogen atom, and R 8a is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect BB45] In any of Aspects BB1 to BB24, X E is a nitrogen atom or CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 and R 1B and R 2B are the same or different, OR 8a or a hydrogen atom, and R 8a is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom (provided that X E is CR Z5 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom. (Aspect BB46) In any one of Aspects BB1 to BB24, X E is a nitrogen atom or CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8are the same or different and are a methyl group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom, and R 1B and R 2B are the same or different, OR 8a or a hydrogen atom, and R 8a is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom (provided that X E is CR Z5 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom. [Aspect BB47] In any one of Aspects BB1 to BB24, X E is a nitrogen atom or CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 is a hydrogen atom, and R 1B and R 2B are the same or different, OR 8a or a hydrogen atom, and R 8a is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect BB48] In any of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is a nitrogen atom or CR Z7 and X H is CR Z8 and R 1B and R 2B are the same or different, OR 8a or a hydrogen atom, and R 8ais a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom (provided that X G is CR Z7 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom.) [Aspect BB49] In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is a nitrogen atom or CR Z7 and X H is CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 are the same or different and are a methyl group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom, and R 1B and R 2B are the same or different, OR 8a or a hydrogen atom, and R 8a is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom (provided that X G is CR Z7 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom. (Aspect BB50) In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is a nitrogen atom or CR Z7 and X H is CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 is a hydrogen atom, and R 1B and R2B are the same or different, OR 8a or a hydrogen atom, and R 8a is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect BB51] In any of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 and R 1B and R 2B are the same or different, OR 8a or a hydrogen atom, and R 8a is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom (provided that R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom. (Aspect BB52) In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 are the same or different and are a methyl group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom, and R 1B and R 2B are the same or different, OR 8a or a hydrogen atom, and R 8a is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom (provided that R Z5 , R Z6 , R Z7 , and RZ8 At least one of the groups is a hydrogen atom.) [Aspect BB53] In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 is a hydrogen atom, and R 1B and R 2B are the same or different, OR 8a or a hydrogen atom, and R 8a is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect BB54] In any of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is a nitrogen atom or CR Z8 and R 1B is a hydrogen atom, and R 2B is OR 8a or a hydrogen atom, and R 8a is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom (provided that X H is CR Z8 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom.) [Aspect BB55] In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is CR Z7 and X His a nitrogen atom or CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 are the same or different and are a methyl group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom, and R 1B is a hydrogen atom, and R 2B is OR 8a or a hydrogen atom, and R 8a is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom (provided that X H is CR Z8 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom. (Aspect BB56) In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is a nitrogen atom or CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 is a hydrogen atom, and R 1B is a hydrogen atom, and R 2B is OR 8a or a hydrogen atom, and R 8a is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect BB57] In any of Aspects BB1 to BB24, X E is a nitrogen atom or CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 and R 1B is a hydrogen atom, and R 2B is OR8a or a hydrogen atom, and R 8a is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom (provided that X E is CR Z5 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom. (Aspect BB58) In any one of Aspects BB1 to BB24, X E is a nitrogen atom or CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 are the same or different and are a methyl group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom, and R 1B is a hydrogen atom, and R 2B is OR 8a or a hydrogen atom, and R 8a is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom (provided that X E is CR Z5 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of X is a hydrogen atom. E is a nitrogen atom or CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8is a hydrogen atom, and R 1B is a hydrogen atom, and R 2B is OR 8a or a hydrogen atom, and R 8a is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect BB60] In any of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is a nitrogen atom or CR Z7 and X H is CR Z8 and R 1B is a hydrogen atom, and R 2B is OR 8a or a hydrogen atom, and R 8a is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom (provided that X G is CR Z7 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom.) [Aspect BB61] In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is a nitrogen atom or CR Z7 and X H is CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 are the same or different and are a methyl group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom, and R 1B is a hydrogen atom, and R 2B is OR 8a or a hydrogen atom, and R 8ais a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom (provided that X G is CR Z7 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom. (Aspect BB62) In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is a nitrogen atom or CR Z7 and X H is CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 is a hydrogen atom, and R 1B is a hydrogen atom, and R 2B is OR 8a or a hydrogen atom, and R 8a is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect BB63] In any of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 and R 1B is a hydrogen atom, and R 2B is OR 8a or a hydrogen atom, and R 8a is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom (provided that R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom. (Aspect BB64) In any one of Aspects BB1 to BB24, XE is CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 are the same or different and are a methyl group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom, and R 1B is a hydrogen atom, and R 2B is OR 8a or a hydrogen atom, and R 8a is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom (provided that R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom. (Aspect BB65) In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 is a hydrogen atom, and R 1B is a hydrogen atom, and R 2B is OR 8a or a hydrogen atom, and R 8a is a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a (C1-C4 alkyl)carbonyl group, or a hydrogen atom. [Aspect BB66] In any of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is CR Z7 and X His a nitrogen atom or CR Z8 and R 1B is a hydrogen atom, and R 2B is OR 8a or a hydrogen atom, and R 8a is a hydrogen atom (provided that X H is CR Z8 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom. (Aspect BB67) In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is a nitrogen atom or CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 are the same or different and are a methyl group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom, and R 1B is a hydrogen atom, and R 2B is OR 8a or a hydrogen atom, and R 8a is a hydrogen atom (provided that X H is CR Z8 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom. (Aspect BB68) In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is a nitrogen atom or CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 is a hydrogen atom, and R 1B is a hydrogen atom, and R2B is OR 8a or a hydrogen atom, and R 8a is a hydrogen atom. [Aspect BB69] In any one of Aspects BB1 to BB24, X E is a nitrogen atom or CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 and R 1B is a hydrogen atom, and R 2B is OR 8a or a hydrogen atom, and R 8a is a hydrogen atom (provided that X E is CR Z5 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom. (Aspect BB70) In any one of Aspects BB1 to BB24, X E is a nitrogen atom or CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 are the same or different and are a methyl group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom, and R 1B is a hydrogen atom, and R 2B is OR 8a or a hydrogen atom, and R 8a is a hydrogen atom (provided that X E is CR Z5 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of X is a hydrogen atom. E is a nitrogen atom or CRZ5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 is a hydrogen atom, and R 1B is a hydrogen atom, and R 2B is OR 8a or a hydrogen atom, and R 8a is a hydrogen atom. [Aspect BB72] In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is a nitrogen atom or CR Z7 and X H is CR Z8 and R 1B is a hydrogen atom, and R 2B is OR 8a or a hydrogen atom, and R 8a is a hydrogen atom (provided that X G is CR Z7 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom.) [Aspect BB73] In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is a nitrogen atom or CR Z7 and X H is CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 are the same or different and are a methyl group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom, and R 1B is a hydrogen atom, and R 2B is OR 8aor a hydrogen atom, and R 8a is a hydrogen atom (provided that X G is CR Z7 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom. (Aspect BB74) In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is a nitrogen atom or CR Z7 and X H is CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 is a hydrogen atom, and R 1B is a hydrogen atom, and R 2B is OR 8a or a hydrogen atom, and R 8a is a hydrogen atom. [Aspect BB75] In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 and R 1B is a hydrogen atom, and R 2B is OR 8a or a hydrogen atom, and R 8a is a hydrogen atom (provided that R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom. (Aspect BB76) In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 and RZ5 , R Z6 , R Z7 , and R Z8 are the same or different and are a methyl group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom, and R 1B is a hydrogen atom, and R 2B is OR 8a or a hydrogen atom, and R 8a is a hydrogen atom (provided that R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom.) [Aspect BB77] In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 is a hydrogen atom, and R 1B is a hydrogen atom, and R 2B is OR 8a or a hydrogen atom, and R 8a is a hydrogen atom. [Aspect BB78] In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is a nitrogen atom or CR Z8 and R 1B is a hydrogen atom, and R 2B is OR 8a and R 8a is a hydrogen atom (provided that X H is CR Z8 When R Z5 , R Z6 , R Z7 , and R Z8At least one of the groups is a hydrogen atom. (Aspect BB79) In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is a nitrogen atom or CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 are the same or different and are a methyl group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom, and R 1B is a hydrogen atom, and R 2B is OR 8a and R 8a is a hydrogen atom (provided that X H is CR Z8 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom. (Aspect BB80) In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is a nitrogen atom or CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 is a hydrogen atom, and R 1B is a hydrogen atom, and R 2B is OR 8a and R 8a is a hydrogen atom. [Aspect BB81] In any one of Aspects BB1 to BB24, X E is a nitrogen atom or CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CRZ8 and R 1B is a hydrogen atom, and R 2B is OR 8a and R 8a is a hydrogen atom (provided that X E is CR Z5 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom. (Aspect BB82) In any one of Aspects BB1 to BB24, X E is a nitrogen atom or CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 are the same or different and are a methyl group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom, and R 1B is a hydrogen atom, and R 2B is OR 8a and R 8a is a hydrogen atom (provided that X E is CR Z5 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of X is a hydrogen atom. E is a nitrogen atom or CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 is a hydrogen atom, and R 1B is a hydrogen atom, and R 2B is OR 8aand R 8a is a hydrogen atom. [Aspect BB84] In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is a nitrogen atom or CR Z7 and X H is CR Z8 and R 1B is a hydrogen atom, and R 2B is OR 8a and R 8a is a hydrogen atom (provided that X G is CR Z7 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom. (Aspect BB85) In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is a nitrogen atom or CR Z7 and X H is CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 are the same or different and are a methyl group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom, and R 1B is a hydrogen atom, and R 2B is OR 8a and R 8a is a hydrogen atom (provided that X G is CR Z7 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom. (Aspect BB86) In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and XG is a nitrogen atom or CR Z7 and X H is CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 is a hydrogen atom, and R 1B is a hydrogen atom, and R 2B is OR 8a and R 8a is a hydrogen atom. [Aspect BB87] In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 and R 1B is a hydrogen atom, and R 2B is OR 8a and R 8a is a hydrogen atom (provided that R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom. (Aspect BB88) In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 are the same or different and are a methyl group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom, and R 1B is a hydrogen atom, and R 2B is OR 8a and R 8a is a hydrogen atom (provided that R Z5 , R Z6 , R Z7 , and R Z8At least one of the groups is a hydrogen atom. (Aspect BB89) In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 is a hydrogen atom, and R 1B is a hydrogen atom, and R 2B is OR 8a and R 8a is a hydrogen atom. [Aspect BB90] In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is a nitrogen atom or CR Z8 and R 1B and R 2B is a hydrogen atom (provided that X H is CR Z8 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom. (Aspect BB91) In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is a nitrogen atom or CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 are the same or different and are a methyl group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom, and R 1B and R 2Bis a hydrogen atom (provided that X H is CR Z8 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom. (Aspect BB92) In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is a nitrogen atom or CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 is a hydrogen atom, and R 1B and R 2B is a hydrogen atom. [Aspect BB93] In any one of Aspects BB1 to BB24, X E is a nitrogen atom or CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 and R 1B and R 2B is a hydrogen atom (provided that X E is CR Z5 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom. (Aspect BB94) In any one of Aspects BB1 to BB24, X E is a nitrogen atom or CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8are the same or different and are a methyl group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom, and R 1B and R 2B is a hydrogen atom (provided that X E is CR Z5 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of X is a hydrogen atom. E is a nitrogen atom or CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 is a hydrogen atom, and R 1B and R 2B is a hydrogen atom. [Aspect BB96] In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is a nitrogen atom or CR Z7 and X H is CR Z8 and R 1B and R 2B is a hydrogen atom (provided that X G is CR Z7 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom.) [Aspect BB97] In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is a nitrogen atom or CR Z7 and X H is CR Z8and R Z5 , R Z6 , R Z7 , and R Z8 are the same or different and are a methyl group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom, and R 1B and R 2B is a hydrogen atom (provided that X G is CR Z7 When R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom. (Aspect BB98) In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is a nitrogen atom or CR Z7 and X H is CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 is a hydrogen atom, and R 1B and R 2B is a hydrogen atom. [Aspect BB99] In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 and R 1B and R 2B is a hydrogen atom (provided that R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom. (Aspect BB100) In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is CR Z7 and XH is CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 are the same or different and are a methyl group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom, and R 1B and R 2B is a hydrogen atom (provided that R Z5 , R Z6 , R Z7 , and R Z8 At least one of the groups is a hydrogen atom. (Aspect BB101) In any one of Aspects BB1 to BB24, X E is CR Z5 and X F is CR Z6 and X G is CR Z7 and X H is CR Z8 and R Z5 , R Z6 , R Z7 , and R Z8 is a hydrogen atom, and R 1B and R 2B A compound in which is a hydrogen atom.
[0019] The following compounds are also examples of the compound A of the present invention: [Aspect BX1] In the compound A of the present invention, X 1a , X 2a , X 3a and X 4a The combination of 1a is CR 41a and X 2a is CR 42a and X 3a is CR 43a and X 4a is CR 44a (where R 41a , R 42a , R 43a and R 44a At least one of the groups is a hydrogen atom; X 1a is a nitrogen atom, and X 2a is CR 42a and X 3a is CR43a and X 4a is CR 44a A combination in which: X 1a is CR 41a and X 2a is a nitrogen atom, and X 3a is CR 43a and X 4a is CR 44a A combination in which: X 1a is CR 41a and X 2a is CR 42a and X 3a is a nitrogen atom, and X 4a is CR 44a or a combination in which X 1a is CR 41a and X 2a is CR 42a and X 3a is CR 43a and X 4a is a nitrogen atom, and R 1a , and R 2a are the same or different and are a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a phenyl group, a 5- or 6-membered aromatic heterocyclic group, OR 8a , an amino group, a cyano group, a halogen atom, or a hydrogen atom; R 3a and R 5a are the same or different, and are C1-C6 chain hydrocarbon groups optionally substituted with one or more halogen atoms, OR 17a or a halogen atom, R 6a is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, OR 32a , S.R. 33a , S(O)R 34a , S(O)R 35a , a cyano group, or a halogen atom; R 41a , R 42a , and R 44a are the same or different, and are C1-C6 chain hydrocarbon groups optionally substituted with one or more halogen atoms, OR 45a , a halogen atom, or a hydrogen atom; R 43ais a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom, and R 8a But Group B Xa a C1-C6 chain hydrocarbon group optionally substituted by one or more substituents selected from the group consisting of a (C1-C6 alkyl)carbonyl group, a 5- or 6-membered aromatic heterocyclic group (the 5- or 6-membered aromatic heterocyclic group is selected from the group consisting of Xa or a hydrogen atom, and R 17a , R 32a and R 45a are the same or different and are a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom, and R 33a , R 34a , and R 35a are the same or different and are C1-C6 chain hydrocarbon groups optionally substituted with one or more halogen atoms, and when qa is 2, 3, 4, or 5, two adjacent R 6a and R 6a together with the carbon atom to which they are bonded form a C5-C6 alicyclic hydrocarbon, a 5- to 6-membered non-aromatic heterocycle, or a 5- to 6-membered aromatic heterocycle {the C5-C6 alicyclic hydrocarbon, the 5- to 6-membered non-aromatic heterocycle, and the 5- to 6-membered aromatic heterocycle are each selected from the group A Xa and the compound may form a group A, which may be substituted with one or more substituents selected from the following. Xa Group B: A group consisting of halogen atoms, C1-C4 alkyl groups, C1-C4 haloalkyl groups, C1-C4 alkoxy groups, and C1-C4 haloalkoxy groups. Xa :Group A Xa and a halogen atom. [Aspect BX2] In Compound A of the present invention, X 1a , X 2a , X 3a and X 4a The combination of 1a is CR 41a and X 2a is CR 42a and X 3a is CR 43a and X 4a is CR 44a(where R 41a , R 42a , R 43a and R 44a At least one of the groups is a hydrogen atom; X 1a is a nitrogen atom, and X 2a is CR 42a and X 3a is CR 43a and X 4a is CR 44a A combination in which: X 1a is CR 41a and X 2a is a nitrogen atom, and X 3a is CR 43a and X 4a is CR 44a A combination in which: X 1a is CR 41a and X 2a is CR 42a and X 3a is a nitrogen atom, and X 4a is CR 44a or a combination in which X 1a is CR 41a and X 2a is CR 42a and X 3a is CR 43a and X 4a is a nitrogen atom, and R 1a , and R 2a are the same or different and are a C1-C6 chain hydrocarbon group, OR 8a , a cyano group, a halogen atom, or a hydrogen atom; R 3a and R 5a are the same or different and are a C1-C4 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C4 alkoxy group, or a halogen atom, and R 6a is a C1-C4 chain hydrocarbon group, a C1-C4 alkoxy group, a C1-C4 sulfanyl group, a C1-C4 sulfinyl group, a C1-C4 sulfonyl group, a cyano group, a hydroxy group, or a halogen atom, and R 41a , R 42a , and R 44aare the same or different and are a C1-C4 chain hydrocarbon group, a C1-C4 alkoxy group, a halogen atom, or a hydrogen atom, and R 43a is a C1-C4 chain hydrocarbon group, a halogen atom, or a hydrogen atom, and R 8a But Group B Xa a C1-C6 chain hydrocarbon group optionally substituted by one or more substituents selected from the group consisting of a (C1-C6 alkyl)carbonyl group, a 5- or 6-membered aromatic heterocyclic group (the 5- or 6-membered aromatic heterocyclic group is selected from the group consisting of Xa or a hydrogen atom, and when q is 2, 3, 4, or 5, two adjacent R 6a and R 6a may, together with the carbon atom to which they are attached, form a C5-C6 alicyclic hydrocarbon, a 5- or 6-membered non-aromatic heterocycle, or a 5- or 6-membered aromatic heterocycle.
[0020] [Aspect C1] A method for controlling soybean rust fungi by applying the present compound to soybeans or the soil in which soybeans are grown. [Aspect C2] A method for controlling soybean rust fungi by applying the present compound to soybeans or the soil in which soybeans are grown.
[0021] Next, the method for producing the present compound (including the compound of the present invention) will be described.
[0022] Production Method A The compound represented by formula (I) (this compound A) can be produced by reacting a compound represented by formula (B1) (hereinafter referred to as compound (B1)) with a compound represented by formula (M1) (hereinafter referred to as compound (M1)) in the presence of a palladium catalyst and a base. [In the formula, X 51 represents a chlorine atom, a bromine atom, an iodine atom, or a triflyloxy group; Met 51represents B(OH)2 or 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl, and the other symbols have the same meanings as above.] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons such as hexane, toluene, and xylene (hereinafter referred to as hydrocarbons); ethers such as methyl tert-butyl ether (hereinafter referred to as MTBE), tetrahydrofuran (hereinafter referred to as THF), and 1,2-dimethoxyethane (hereinafter referred to as DME) (hereinafter referred to as ethers); halogenated hydrocarbons such as dichloromethane, chloroform, and chlorobenzene (hereinafter referred to as halogenated hydrocarbons); amides such as dimethylformamide (hereinafter referred to as DMF) and N-methylpyrrolidone (hereinafter referred to as NMP) (hereinafter referred to as amides); esters such as methyl acetate and ethyl acetate (hereinafter referred to as esters); nitriles such as acetonitrile and propionitrile (hereinafter referred to as nitriles); dimethyl sulfoxide (hereinafter referred to as DMSO), water, and mixtures of two or more thereof. Examples of palladium catalysts used in the reaction include palladium(II) acetate and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride. Examples of bases used in the reaction include organic bases such as triethylamine and pyridine (hereinafter referred to as organic bases); alkali metal carbonates such as sodium carbonate and potassium carbonate (hereinafter referred to as alkali metal carbonates); alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate (hereinafter referred to as alkali metal bicarbonates); sodium fluoride and tripotassium phosphate. In the reaction, compound (M1) is typically used in a ratio of 0.5 to 2 moles, a palladium catalyst is typically used in a ratio of 0.01 to 0.3 moles, and a base is typically used in a ratio of 1 to 10 moles, relative to 1 mole of compound (B1). The reaction temperature is typically in the range of 0 to 150°C. The reaction time is typically in the range of 0.1 to 120 hours. After the reaction is complete, the compound A can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. Compound (M1) is known or can be produced according to known methods.
[0023] Production Method B The compound represented by formula (I) (the present compound A) can also be produced by reacting a compound represented by formula (B2) (hereinafter referred to as compound (B2)) with a compound represented by formula (M2) (hereinafter referred to as compound (M2)) in the presence of a palladium catalyst and a base. [In the formula, the symbols have the same meanings as defined above.] The reaction can be carried out in accordance with Production Method A, using compound (M2) instead of compound (B1) and compound (B2) instead of compound (M1). Compound (M2) is known or can be produced in accordance with a known method.
[0024] Production Method C The compound represented by formula (I-a) (hereinafter referred to as compound (I-a)) can be produced by reacting a compound represented by formula (B3) (hereinafter referred to as compound (B3)) with a compound represented by formula (M3) (hereinafter referred to as compound (M3)) to produce an organolithium reactant, and then reacting the resulting organolithium reactant with a compound represented by formula (M4) (hereinafter referred to as compound (M4)). [In the formula, X 52 represents a bromine atom or an iodine atom, and X 53 represents a butyl group, a sec-butyl group, or a tert-butyl group, and other symbols have the same meanings as above.] First, a method for producing an organolithium reactant from compound (B3) will be described. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons, ethers, and mixtures of two or more thereof. In the reaction, compound (M3) is usually used in a ratio of 0.5 to 2 moles per mole of compound (B3). The reaction temperature is usually in the range of -78°C to the boiling point of the solvent. The reaction time is usually in the range of 0.1 to 120 hours.
[0025] Next, a method for producing compound (I-a) from an organolithium reactant will be described. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons, ethers, and mixtures of two or more of these. Compound (M4) is usually used in a ratio of 0.5 to 2 moles per mole of organolithium reactant. The reaction temperature is usually in the range of -78°C to the boiling point of the solvent. The reaction time is usually in the range of 0.1 to 120 hours. After completion of the reaction, compound (I-a) can be isolated by post-treatment procedures such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. Compound (B3), compound (M3), and compound (M4) are known or can be produced according to known methods.
[0026] Production Method D Compound (I-a) can also be produced by reacting compound (B3) with a compound represented by formula (M5) (hereinafter referred to as compound (M5)) to produce a Grignard reagent, and then reacting the Grignard reagent with compound (M4). [In the formula, X 54 represents a chlorine atom or a bromine atom, and other symbols have the same meanings as above.] The reaction can be carried out in accordance with Production Method C, except that compound (M5) is used in place of compound (M3). Compound (M5) is a commercially available compound, or can be produced in accordance with known methods.
[0027] Production Method E Compound (I-a) can also be produced by reacting a compound represented by formula (M6) (hereinafter referred to as compound (M6)) with compound (M3) to produce an organolithium reactant, and reacting the resulting organolithium reactant with a compound represented by formula (M7) (hereinafter referred to as compound (M7)). [In the formula, the symbols have the same meanings as defined above.] The reaction can be carried out in accordance with Production Method C, using compound (M6) instead of compound (B3) and compound (M7) instead of compound (M4). Compounds (M6) and (M7) are known or can be produced in accordance with known methods.
[0028] Production Method F Compound (Ia) can also be produced by reacting compound (M6) with compound (M5) to produce a Grignard reagent, which is then reacted with compound (M7). [wherein the symbols have the same meanings as defined above.] The reaction can be carried out in accordance with Production Method C, except that compound (M6) is used in place of compound (B3), compound (M5) is used in place of compound (M3), and compound (M7) is used in place of compound (M4).
[0029] Production Method G The compound represented by formula (Ib) (hereinafter referred to as compound (Ib)) can be produced by dehydroxylating compound (Ia). [In the formula, the symbols have the same meanings as above.] Examples of methods for dehydroxylation include catalytic hydrogen reduction and reaction with phosphorus tribromide. First, catalytic hydrogen reduction will be described. Catalytic hydrogenation can be carried out by reacting compound (I-a) with hydrogen in the presence of a solvent and a catalyst. Examples of solvents used in the reaction include alcohols such as methanol and ethanol (hereinafter referred to as alcohols); esters, acetic acid, and mixtures of two or more thereof. Examples of catalysts used in the reaction include palladium on carbon. The hydrogen pressure in the reaction is usually 1 to 5 atmospheres. The catalyst is usually used in a ratio of 0.01 to 1 mole per mole of compound (I-a). The reaction temperature is usually in the range of 10 to 50°C. The reaction time is usually in the range of 0.1 to 120 hours.
[0030] Next, a method for producing compound (I-b) by reaction with phosphorus tribromide will be described. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons, ethers, and mixtures of two or more of these. In the reaction, phosphorus tribromide is usually used in a ratio of 1 to 10 moles per mole of compound (I-a). The reaction temperature is usually in the range of 0°C to the boiling point of the solvent. The reaction time is usually in the range of 0.1 to 120 hours. After completion of the reaction, water is added to the reaction mixture, and the organic layer is washed with an alkaline aqueous solution (e.g., saturated aqueous sodium bicarbonate solution) as necessary. Compound (I-b) can be isolated by post-treatment procedures such as drying and concentrating the organic layer.
[0031] Production Method H The compound represented by formula (Ic) (hereinafter referred to as compound (Ic)) can be produced by oxidizing compound (Ia). [In the formula, the symbols have the same meanings as defined above.] The oxidation reaction can be carried out according to the method described in Natural Product Reports, 2011, 28, 1722-1754, etc.
[0032] Production Method I Compound (Ia) can also be produced by reducing compound (Ic). [In the formula, the symbols have the same meanings as above.] The reduction reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers, alcohols, and mixtures of two or more of these. Examples of reducing agents used in the reaction include sodium borohydride. In the reaction, the reducing agent is usually used in a ratio of 0.5 to 2 moles per mole of compound (I-c). 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 120 hours. After completion of the reaction, compound (I-a) can be isolated by post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
[0033] Production Method J The compound represented by formula (I-d) (hereinafter referred to as compound (I-d)) can be produced by reacting compound (I-a) with a compound represented by formula (M8) (hereinafter referred to as compound (M8)) in the presence of a base. [In the formula, X 55 represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a mesyloxy group, or a triflyloxy group, and other symbols have the same meanings as above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include alcohols, nitriles, ethers, hydrocarbons, amides, DMSO, water, and mixtures of two or more of these. Examples of bases used in the reaction include alkali metal hydrides, alkali metal carbonates, organic bases, sodium hydride, and tripotassium phosphate. X 55When is a bromine atom, an iodine atom, or a triflyloxy group, the reaction may be carried out by adding a metal catalyst and a ligand, as necessary. Examples of the metal catalyst used in the reaction include palladium catalysts such as palladium(II) acetate and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride; nickel catalysts such as bis(cyclooctadiene)nickel(0) and nickel(II) chloride; and copper catalysts such as copper(I) iodide and copper(I) chloride. When a metal catalyst is used in the reaction, the metal catalyst is usually used in a ratio of 0.01 to 1 mole per mole of compound (I-a). Examples of the ligand used in the reaction include triphenylphosphine, xantphos, 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 1,1'-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 1,2-bis(diphenylphosphino)ethane, 2,2'-bipyridine, 2-aminoethanol, 8-hydroxyquinoline, and 1,10-phenanthroline. When a ligand is used in the reaction, the ligand is typically used in a ratio of 0.01 to 1 mole per mole of compound (I-a). In the reaction, compound (M8) is typically used in a ratio of 1 to 10 moles, and a base is typically used in a ratio of 1 to 10 moles per mole of compound (I-a). The reaction temperature is usually in the range of -20°C to 200°C. The reaction time is usually in the range of 0.1 to 72 hours. After completion of the reaction, compound (I-d) can be obtained by post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. Compound (M8) is known or can be produced according to known methods.
[0034] Reference Production Method A The compound represented by formula (C2) (hereinafter referred to as compound (C2)) can be produced by reacting compound (M6) with compound (M3) to produce an organolithium reactant, and then reacting the resulting organolithium reactant with a compound represented by formula (C1) (hereinafter referred to as compound (C1)). [In the formula, the symbols have the same meanings as defined above.] The reaction can be carried out in accordance with Production Method C, using compound (M6) instead of compound (B3) and compound (C1) instead of compound (M4). Compound (C1) is known or can be produced in accordance with a known method.
[0035] Reference Production Method B Compound (C2) can also be produced by reacting compound (M6) with compound (M5) to produce a Grignard reagent, which is then reacted with compound (C1). [wherein the symbols have the same meanings as defined above.] The reaction can be carried out according to Production Method D, except that compound (M6) is used instead of compound (B3) and compound (C1) is used instead of compound (M4).
[0036] Reference Production Method C The compound represented by formula (C3) (hereinafter referred to as compound (C3)) can be produced by reacting compound (B1) with bis(pinacolato)diboron in the presence of a base and a palladium catalyst. [wherein the symbols have the same meanings as defined above.] The reaction can be carried out according to Production Method A, except that bis(pinacolato)diboron is used in place of Compound (M1).
[0037] Reference Production Method D The compound represented by formula (C5) (hereinafter referred to as compound (C5)) can be produced by oxidizing a compound represented by formula (C4) (hereinafter referred to as compound (C4)). [In the formula, the symbols have the same meanings as defined above.] The oxidation reaction can be carried out in accordance with the method described in Natural Product Reports, 2011, 28, 1722-1754, etc. Compound (C4) can be produced in accordance with Reference Production Method A or Reference Production Method B.
[0038] Reference Production Method E The compound represented by formula (C6) (hereinafter referred to as compound (C6)) can be produced by thiocarbonylating compound (C5). [wherein the symbols have the same meanings as defined above.] The thiocarbonylation reaction can be carried out according to the method described in Tetrahedron, 1985, 41, 5061-5087, etc.
[0039] Reference Production Method F The compound represented by formula (C7) (hereinafter referred to as compound (C7)) can be produced by reacting compound (C5) with a compound represented by formula (M9) (hereinafter referred to as compound (M9)) or a salt of compound (M9). [In the formula, the symbols have the same meanings as defined above.] Examples of salts of compound (M9) include hydrochloride and sulfate. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, alcohols, and mixtures of two or more thereof. A base may be added to the reaction, if necessary. Examples of bases used in the reaction include organic bases; alkali metal carbonates; alkali metal bicarbonates; sodium hydride, and tripotassium phosphate. When a base is used in the reaction, the base is usually used in a ratio of 1 to 10 moles per mole of compound (C5). In the reaction, compound (M9) is usually used in a ratio of 1 to 10 moles per mole of compound (C5). The reaction temperature is usually in the range of 0 to 150°C. The reaction time is usually in the range of 0.1 to 120 hours. After completion of the reaction, compound (C7) can be isolated by post-treatment, such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. The salt of compound (M9) is known or can be prepared according to a known method.
[0040] Reference Production Method G The compound represented by formula (C9) (hereinafter referred to as compound (C9)) can be produced by reacting compound (M6) with a compound represented by formula (M11) (hereinafter referred to as compound (M11)). [In the formula, the symbols have the same meanings as defined above.] The reaction can be carried out in accordance with Production Method A, using compound (M6) instead of compound (B1) and compound (M11) instead of compound (M1). The reaction can also be carried out in accordance with the method described in Angewandte Chemie International Edition, 2020, 59, 22460-22464, etc. Compound (M11) is known or can be produced in accordance with a known method.
[0041] Reference Production Method H The compound represented by formula (B1-1) (hereinafter referred to as compound (B1-1)) can be produced by cyclization reaction of a compound represented by formula (C14) (hereinafter referred to as compound (C14)). [In the formula, R 1v , R 2v , R 3v , R 4v , R 5v , R 6v , R 7v , and R 8v are the same or different and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group A, a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group (the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group B), a phenyl group optionally substituted with one or more substituents selected from group C, OR 26 , N.R. 27 R 28 , C(O)R 29 , C(R 30 ) = NOR 31 , a cyano group, a nitro group, a halogen atom, or a hydrogen atom; R 9v represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group A, a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group (the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group B), a phenyl group optionally substituted with one or more substituents selected from group C, C(O)R 29, or a hydrogen atom, and other symbols have the same meanings as above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include alcohols, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, DMSO, water, and mixtures of two or more of these. A base may be added to the reaction, if necessary. Examples of bases used in the reaction include organic bases, alkali metal carbonates, alkali metal hydrogencarbonates, and phosphazene bases such as 1-tert-butyl-4,4,4-tris(dimethylamino)-2,2-bis[tris(dimethylamino)phosphoranylideneamino]-2λ5,4λ5-catenadi(phosphazene). The base is usually used in a ratio of 0.01 to 10 moles per mole of compound (C14) in the reaction. The reaction temperature is usually in the range of 0 to 150°C. The reaction time is usually in the range of 0.1 to 120 hours. After the reaction is complete, compound (B1-1) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. The reaction can also be carried out in accordance with the methods described in Tetrahedron Letters, 2022, 89, 153599, Org. Lett, 2022, 24, 51, 9447, J. Am. Chem. Soc. 2014, 136, 35, 12217, etc. Compound (C14) can be obtained by known methods, for example, Tetrahedron Letters, 2022, 89, 153599, Org. Lett., 2022, 24, 51, 9447, J. Am. Chem. Soc. 2014, 136, 35, 12217, etc.
[0042] Reference Production Method I The compound represented by formula (B1-2) (hereinafter referred to as compound (B1-2)) can be produced by reacting a compound represented by formula (C15) (hereinafter referred to as compound (C15)) with a compound represented by formula (M1-1) (hereinafter referred to as compound (M1-1)). [In the ceremony, Q v is an oxygen atom, a sulfur atom, or NR 9vand the other symbols have the same meanings as above. ] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include alcohols, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, DMSO, water, and mixtures of two or more of these. A base may be added to the reaction, if necessary. Examples of bases used in the reaction include organic bases, alkali metal carbonates, and alkali metal bicarbonates. In the reaction, compound (M1-1) is usually used in a ratio of 0.5 to 10 moles and a base is usually used in a ratio of 1 to 10 moles per mole of compound (C15). The reaction temperature is usually in the range of 0 to 150°C. The reaction time is usually in the range of 0.1 to 120 hours. After completion of the reaction, compound (B1-2) can be isolated by adding water to the reaction mixture, extracting with an organic solvent, and performing post-treatment such as drying and concentrating the organic layer. The reaction can also be carried out in the same manner as described in J. Chem. Soc., Perkin Trans. 1, 1977, 2328-2332, etc. Compound (C15) is known or can be produced by a known method.
[0043] Reference Production Method J The compound represented by formula (B1-3) (hereinafter referred to as compound (B1-3)) can be produced by reacting a compound represented by formula (C16) (hereinafter referred to as compound (C16)) with a compound represented by formula (M1-2) (hereinafter referred to as compound (M1-2)). [In the formula, the symbols have the same meanings as defined above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include alcohols, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, DMSO, water, and mixtures of two or more of these. A base may be added to the reaction, if necessary. Examples of bases used in the reaction include organic bases, alkali metal carbonates, and alkali metal bicarbonates. In the reaction, compound (M1-2) is usually used in a ratio of 0.5 to 10 moles and a base is usually used in a ratio of 1 to 10 moles per mole of compound (C16). The reaction temperature is usually in the range of 0 to 150°C. The reaction time is usually in the range of 0.1 to 120 hours. After completion of the reaction, compound (B1-3) can be isolated by post-treatment, such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. Compound (C16) is either known or can be produced by a known method.
[0044] The compound of the present invention can be mixed or used in combination with one or more components selected from the group consisting of Group (a), Group (b), Group (c), and Group (d) below (hereinafter referred to as the present component). The term "mixed or used in combination" means that the compound of the present invention and the present component are used simultaneously, separately, or with a time interval. When the compound of the present invention and the present component are used simultaneously, the compound of the present invention and the present component may be contained in separate preparations or in a single preparation. One aspect of the present invention is a composition (hereinafter referred to as Composition A) containing one or more components selected from the group consisting of Group (a), Group (b), Group (c), and Group (d) (i.e., the present component) and the compound of the present invention.
[0045] Group (a) includes acetylcholinesterase inhibitors (e.g., carbamate insecticides, organophosphate insecticides), GABAergic chloride channel blockers (e.g., phenylpyrazole insecticides), sodium channel modulators (e.g., pyrethroid insecticides), nicotinic acetylcholine receptor competitive modulators (e.g., neonicotinoid insecticides), nicotinic acetylcholine receptor allosteric modulators, glutamate-gated chloride channel allosteric modulators (e.g., macrolide insecticides), juvenile hormone mimics, multisite inhibitors, chordotonal organ TRPV channel modulators, mite growth inhibitors, microbial insect midgut membrane disruptors, mitochondrial ATP synthase inhibitors, oxidative phosphorylation uncouplers, nicotinic acetylcholine receptor channel blockers (e.g., nereistoxin insecticides), chitin biosynthesis inhibitors, molting inhibitors, ecdysone receptor agonists, octopamine receptor agonists, mitochondrial electron transport chain complexes I and II, The group consisting of inhibitors of classes III and IV, voltage-dependent sodium channel blockers, acetyl-CoA carboxylase inhibitors, ryanodine receptor modulators (e.g., diamide insecticides), chordotonal organ modulators, microbial insecticides, and other insecticidal, acaricidal, and nematicidal active ingredients, which are described in the IRAC mechanism-based classification.
[0046] Group (b) consists of nucleic acid synthesis inhibitors (e.g., phenylamide fungicides, acylamino acid fungicides), cell division and cytoskeleton inhibitors (e.g., MBC fungicides), respiratory inhibitors (e.g., QoI fungicides, QiI fungicides), amino acid synthesis and protein synthesis inhibitors (e.g., anilinopyrimidine fungicides), signal transduction inhibitors, lipid synthesis and membrane synthesis inhibitors, sterol biosynthesis inhibitors (e.g., DMI fungicides such as triazoles), cell wall biosynthesis inhibitors, melanin synthesis inhibitors, plant defense inducers, multisite contact-active fungicides, microbial fungicides, and other fungicidal active ingredients. These are listed in the FRAC classification based on the mechanism of action.
[0047] Group (c) is a group of plant growth regulators (including mycorrhizal fungi and rhizobia).
[0048] Group (d) is a group of repellent ingredients.
[0049] Examples of combinations of the present ingredient and the compound of the present invention are described below. For example, alanycarb + SX refers to a combination of alanycarb and SX. The abbreviation SX refers to any one of the present compounds selected from the compound group SX1 to SX65. The present ingredients described below are all known ingredients and can be obtained from commercially available preparations or produced by known methods. When the present ingredient is a microorganism, it can also be obtained from a bacterial depository. The number in parentheses indicates the CAS RN (registered trademark).
[0050] Combinations of the present ingredient of the above group (a) with the compound of the present invention: abamectin + SX, acephate + SX, acequinocyl + SX, acetamiprid + SX, acetoprole + SX, acrinathrin + SX, acinonapyr + SX, afidopyropen + SX, afoxolaner + SX, alanycarb + SX, aldicarb + SX, allethrin + SX, alpha-cypermethrin + SX, alpha-endosulfan + SX, aluminum phosphide + SX, Amitraz + SX, azadirachtin + SX, azamethiphos + SX, azinphos-ethyl + SX, azinphos-methyl + SX, azocyclotin + SX, Celastrus angulatus bark + SX, bendiocarb + SX, benfluthrin + SX, benfuracarb + SX, bensultap + SX, bentiofluorin + SX, benzoximate + SX, benzpyrimoxan + SX, beta-cyfluthrin + SX SX, beta-cypermethrin + SX, bifenazate + SX, bifenthrin + SX,Bioallethrin + SX, bioresmethrin + SX, bistrifluron + SX, bisulfufen + SX, borax + SX, boric acid + SX, broflanilide + SX, bromopropylate + SX, buprofezin + SX, butocarboxim + SX, butoxycarboxim + SX, cadusafos + SX, calcium phosphide + SX, carbaryl + SX, carbofuran + SX, carbosulfan + SX, Cartap hydrochloride + SX, cartap + SX, chinomethionate + SX, chlorantraniliprole + SX, chlordane + SX, chlorethoxyfos + SX, chlorfenapyr + SX, chlorfenvinphos + SX, chlorfluazuron + SX, chlormephos + SX, chloropicrin + SX, chlorpyrifos + SX, chlorpyrifos-methyl + SX, chromafenozide + SX, clofentezine + SX, clothianidin + SX, concanamycin A + SX, coumaphos + SX, cryolite + SX,Cyanophos + SX, cyantraniliprole + SX, cybenzoxasulfyl + SX, cyclaniliprole + SX, cyclobutrifluram + SX, cycloprothrin + SX, cycloxaprid + SX, cyenopyrafen + SX, cyetpyrafen + SX, cyflumetofen + SX, cyfluthrin + SX, cyhalodiamide + SX, cyhalothrin + SX, cyhexatin + SX, cypermethrin + SX, Cyphenothrin + SX, cyproflanilide + SX, cyromazine + SX, dazomet + SX, deltamethrin + SX, demeton-S-methyl + SX, diafenthiuron + SX, diazinon + SX, dichlorvos + SX, dichloromezotiaz + SX, dicofol + SX, dicrotophos + SX, diflovidazin + SX, diflubenzuron + SX, dimefluthrin + SX, Dimethoate + SX, dimethylvinphos + SX, dimpropyridaz + SX, dinotefuran + SX, disodium octaborate + SX,Disulfoton + SX, DNOC (2-methyl-4,6-dinitrophenol) + SX, doramectin + SX, dried leaves of Dryopteris filix (mas) + SX, emamectin benzoate + SX, empenthrin + SX, endosulfan + SX, EPN (O-ethyl O-(4-nitrophenyl) phenylphosphonothioate) + SX, epsilon-metofluthrin + SX, epsilon-momfluorothrin + SX, esfenvalerate + SX, ethiofencarb + SX, ethion + SX, Ethiprole + SX, ethoprophos + SX, etofenprox + SX, etoxazole + SX, Artemisia absinthium extract + SX, Azadirachta indica extract + SX, Cassia nigricans extract + SX, Clitoria ternatea extract + SX, Symphytum officinale extract + SX, Chenopodium ambrosioides extract + SX, Tansy extract + SX, Urtica dioica extract + SX, Mistletoe extract (extract of Viscum album) + SX,Famphur + SX, fenamiphos + SX, fenazaquin + SX, fenbutatin oxide + SX, fenitrothion + SX, fenmezoditiaz + SX, fenobucarb + SX, fenoxycarb + SX, fenpropathrin + SX, fenpyroximate + SX, fenthion + SX, fenvalerate + SX, fipronil + SX, flometoquin + SX, flonicamid + SX, Fluacrypyrim + SX, fluazaindolizine + SX, fluazuron + SX, flubendiamide + SX, fluchlordiniliprole + SX, flucycloxuron + SX, flucythrinate + SX, fluensulfone + SX, flufenprox + SX, flufenoxuron + SX, flufiprole + SX, flumethrin + SX, flupentiofenox + SX, flupyradifurone + SX, flupyrimin + SX, flupyroxystrobin + SX, fluralaner + SX, fluvalinate + SX, fluxametamide + SX,Formetanate + SX, fosthiazate + SX, furamethrin + SX, furathiocarb + SX, gamma-cyhalothrin + SX, GS-omega / kappa HXTX-Hv1a peptide + SX, halfenprox + SX, halofenozide + SX, heptafluthrin + SX, heptenophos + SX, hexaflumuron + SX, hexythiazox + SX, potassium salt of hop beta acid + SX, hydramethylnon + SX, hydroprene + SX, imicyafos + SX, imidacloprid + SX, imidaclothiz + SX, imiprothrin + SX, indazapyroxamet + SX, indoxacarb + SX, isocycloseram + SX, isofenphos + SX, isoflualanam + SX, isoprocarb + SX, isopropyl-O-(methoxyaminothiophosphoryl) salicylate + SX, Isoxathion + SX, Ivermectin + SX, Kadethrin + SX, Kappa-tefluthrin + SX,Kappa-bifenthrin + SX, kinoprene + SX, lambda-cyhalothrin + SX, ledprona + SX, lenoremycin + SX, lepimectin + SX, lime sulfur + SX, lotilaner + SX, lufenuron + SX, machine oil + SX, malathion + SX, mecarbam + SX, meperfluthrin + SX, metaflumizone + SX, metam + SX, methamidophos + SX, Methidathion + SX, methiocarb + SX, methomyl + SX, methoprene + SX, methoxychlor + SX, methoxyfenozide + SX, methyl bromide + SX, metofluthrin + SX, metolcarb + SX, metoxadiazone + SX, mevinphos + SX, milbemectin + SX, milbemycin oxime + SX, mivorilaner + SX, modoflaner + SX, momfluorothrin + SX Monocrotophos + SX, moxidectin + SX, naled + SX, nicofluprole + SX, nicotine + SX,Nicotine sulfate + SX, nitenpyram + SX, novaluron + SX, noviflumuron + SX, Chenopodium anthelminticum seed oil + SX, omethoate + SX, oxamyl + SX, oxazosulfyl + SX, oxydemeton-methyl + SX, parathion + SX, parathion-methyl + SX, permethrin + SX, phenothrin + SX, phenthoate + SX, phorate + SX, phosalone + SX, phosmet + SX, phosphamidon + SX, phosphine + SX, phoxim + SX, pioxaniliprole + SX, piperflanilide + SX, pirimicarb + SX, pirimiphos-methyl + SX, prallethrin + SX, profenofos + SX, profluthrin + SX, propargite + SX, propetamphos + SX, propoxur + SX, propylene glycol alginate + SX, prothiofos + SX, Piflubumide + SX, pymetrozine + SX, pyraclofos + SX,Pyrethrins + SX, pyridaben + SX, pyridalyl + SX, pyridaphenthion + SX, pyrifluquinazone + SX, pyrimidifen + SX, pyriminostrobin + SX, pyriprole + SX, pyriproxyfen + SX, quinalphos + SX, resmethrin + SX, rotenone + SX, ryanodine + SX, sarolaner + SX, selamectin + SX, sigma-cypermethrin + SX, silafluofen + SX, sodium borate + SX, sodium metaborate + SX, spidoxamat + SX, spinetoram + SX, spinosad + SX, spirobudifen + SX, spirodiclofen + SX, spiromesifen + SX, spiropidione + SX, spirotetramat + SX, sulfiflumin + SX, sulfluramid + SX, sulfotep + SX, sulfoxaflor + SX, sulfur + SX, sulfuryl fluoride + SX, tartar emetic + SX, tau-fluvalinate + SX, tebufenozide + SX,Tebufenpyrad + SX, tebupirimfos + SX, teflubenzuron + SX, tefluthrin + SX, temephos + SX, terbufos + SX, terpene constituents of the extract of Chenopodium ambrosioides near ambrosioides + SX, tetrachlorantraniliprole + SX, tetrachlorvinphos + SX, tetradifon + SX, tetramethrin + SX, tetramethylfluthrin + SX, tetraniliprole + SX, Theta-cypermethrin + SX, thiacloprid + SX, thiamethoxam + SX, thiocyclam + SX, thiodicarb + SX, thiofanox + SX, thiometon + SX, thiosultap disodium + SX, thiosultap monosodium + SX, thiapyrachlor + SX, tigolaner + SX, thioantraniliprole + SX, tioxazafen + SX, tolfenpyrad + SX, tralomethrin + SX, transfluthrin + SX, triazamate + SX,Triazophos + SX, trichlorfon + SX, trifluenfuronate + SX, triflumezopyrim + SX, triflumuron + SX, trimethacarb + SX, tyclopyrazoflor + SX, umifoxolaner + SX, vadescana + SX, vamidothion + SX, Quassia amara wood extract + SX, 3,5-dimethylphenyl N-methylcarbamate (XMC) + SX, xylylcarb + SX, zeta-cypermethrin + SX, Zinc phosphide + SX, 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide (1241050-20-3) + SX, 3-methoxy-N-(5-{5-(trifluoromethyl)-5-[3-(trifluoromethyl)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}indan-1-yl)propanamide (1118626-57-5) + SX, N-{4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl}-1-methyl-4-(methanesulfonyl)-3-(1,1,2,2,2-pentafluoroethyl)-1H-pyrazole-3-carboxamide (1400768-21-9) + SX,N-[3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl]-2-(methanesulfonyl)propanamide (2396747-83-2) + SX, N-[4-chloro-2-(pyridin-3-yl)-1,3-thiazol-5-yl]-N-ethyl-3-(methanesulfonyl)propanamide + SX, 1,4-dimethyl-2-[2-(pyridin-3-yl)-2H-indazol-5-yl]-1,2,4-triazolidine-3,5-dione (2171099-09-3) + SX, 2-isopropyl-5-[(3,4,4-trifluoro-3-buten-1-yl)sulfonyl]-1,3,4-thiadiazole (2058052-95-0) + SX, N-({2-fluoro-4-[(2S,3S)-2-hydroxy-3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]phenyl}methyl)cyclopropanecarboxamide + SX, 7-fluoro-N-[1-(methylsulfanyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 7-fluoro-N-[1-(methanesulfinyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 7-fluoro-N-[1-(methanesulfonyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, N-[1-(difluoromethyl)cyclopropyl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 2,9-dihydro-9-(methoxymethyl)-2-(pyridin-3-yl)-10H-pyrazolo[3,4-f]pyrido[2,3-b][1,4]oxazepin-10-one (2607927-97-7) + SX, Cry1Ab protein from Bacillus thuringiensis (Bacillus thuringiensis Cry1Ab protein) + SX, Cry1Ac protein from Bacillus thuringiensis (Bacillus thuringiensis Cry1Ac protein) + SX, Cry1Fa protein from Bacillus thuringiensis (Bacillus thuringiensis Cry1Fa protein) + SX, Cry1A.105 protein from Bacillus thuringiensis (Bacillus thuringiensis Cry1A.105 protein) + SX, Cry2Ab protein from Bacillus thuringiensis (Bacillus thuringiensis Cry2Ab protein) + SX, Vip3A protein from Bacillus thuringiensis (Bacillus thuringiensis Vip3A protein + SX, mCry3A protein from Bacillus thuringiensis (Bacillus thuringiensis mCry3A protein) + SX, Cry3Ab protein from Bacillus thuringiensis (Bacillus thuringiensis Cry3Ab protein) + SX, Cry3Bb protein from Bacillus thuringiensis (Bacillus thuringiensis Cry3Bb protein) + SX, Cry34Ab1 / Cry35Ab1 protein from Bacillus thuringiensis (Bacillus thuringiensis Cry34Ab1 / Cry35Ab1 protein) + SX, Adoxophyes orana granulosis virus strain BV-0001 + SX,Anticarsia gemmatalis nuclear polyhedrosis virus (mNPV) + SX, Autographa californica nuclear polyhedrosis virus (mNPV) + SX, Cydia pomonella GV strain V15 + SX, Cydia pomonella GV strain V22 + SX, Cryptophlebia leucotreta GV + SX, Dendrolimus punctatus cypovirus + SX, Helicoverpa armigera NPV strain BV-0003 + SX Helicoverpa zea nucleopolyhedrosis virus (NPV) + SX, Lymantria dispar nucleopolyhedrosis virus (NPV) + SX, Mamestra brassicae nucleopolyhedrosis virus (NPV) + SX, Mamestra configurata nucleopolyhedrosis virus (NPV) + SX, Neodiprion abietis nucleopolyhedrosis virus (NPV) + SX, Neodiprion lecontei nucleopolyhedrosis virus (NPV) + SX, Neodiprion sertifer nucleopolyhedrosis virus (NPV) + SX, Nosema locustae + SX, Orgyia pseudotsugata nuclear polyhedrosis virus (NPV) + SX, Pieris rapae granulosis virus (GV) + SX, Plodia interpunctella granulosis virus (GV) + SX,Spodoptera exigua mNPV (Spodoptera exigua mNPV) + SX, 1999; Spodoptera littoralis mNPV (Spodoptera littoralis mNPV) + SX, 1999; Spinach squid (Spodoptera litura NPV) + SX, Arthrobotrys dactyloides + SX, Bacillus firmus strain GB-126 + SX, Bacillus firmus strain I-1582 + SX, Bacillus firmus strain NCIM2637 + SX, Bacillus megaterium + SX, Bacillus sp. strain AQ175 + SX, Bacillus sp. strain AQ177 + SX, Bacillus sp. strain AQ178 + SX, Bacillus sphaericus strain 2362 serotype H5a5b + SX, Bacillus sphaericus strain ABTS1743 + SX, Bacillus thuringiensis strain AQ52 + SX, Bacillus thuringiensis strain BD#32 + SX, Bacillus thuringiensis strain CR-371 + SX, Bacillus thuringiensis subsp. Aizawai strain ABTS-1857 + SX, Bacillus thuringiensis subsp. Aizawai strain AM65-52 + SX, Bacillus thuringiensis subsp. Aizawai strain GC-91 + SX, Bacillus thuringiensis subsp. Aizawai strain NB200 + SX, Bacillus thuringiensis subsp. Aizawai Serotype strain H-7 + SX, Bacillus thuringiensis subsp. Kurstaki strain ABTS351 + SX,Bacillus thuringiensis subsp. Kurstaki strain BMP123 + SX, Bacillus thuringiensis subsp. Kurstaki strain CCT1306) + SX, Bacillus thuringiensis subsp. Kurstaki strain EG2348 + SX, Bacillus thuringiensis subsp. Kurstaki strain EG7841 + SX, Bacillus thuringiensis subsp. Kurstaki strain EVB113-19 + SX, Bacillus thuringiensis subsp. Kurstaki strain F810 + SX, Bacillus thuringiensis subsp. Kurstaki strain HD-1 + SX, Bacillus thuringiensis subsp. Kurstaki strain PB54 + SX, Bacillus thuringiensis subsp. Kurstaki strain SA-11 + SX, Bacillus thuringiensis subsp. Kurstaki strain SA-12 + SX, Bacillus thuringiensis subsp. Tenebriosis strain NB176 + SX, Bacillus thuringiensis subsp. Thuringiensis strain MPPL002 + SX, Bacillus thuringiensis subsp. morrisoni + SX, Bacillus thuringiensis var. colmeri + SX, Bacillus thuringiensis var. darmstadiensis strain 24-91 + SX, Bacillus thuringiensis var. dendrolimus + SX, Bacillus thuringiensis var. galleriae + SX,Bacillus thuringiensis var. israelensis strain BMP144 + SX, Bacillus thuringiensis var. israelensis serotype strain H-14 + SX, Bacillus thuringiensis var. japonensis strain buibui + SX, Bacillus thuringiensis var. san diego strain M-7 + SX, Bacillus thuringiensis var. 7216 + SX, Bacillus thuringiensis var. aegypti + SX, Bacillus thuringiensis var. T36 + SX, Beauveria bassiana strain ANT-03 + SX, Beauveria bassiana strain ATCC74040 + SX, Beauveria bassiana strain GHA + SX, Beauveria brongniartii + SX, Burkholderia rinogensis strain A396 + SX, Chromobacterium subtsugae strain PRAA4-1T + SX, Dactyllela ellipsospora + SX, Dactylaria thaumasia + SX, Hirsutella minnesotensis + SX, Hirsutella rhossiliensis + SX, Hirsutella thompsonii + SX, Lagenidium giganteum + SX, Lecanicillium lecanii strain KV01 + SX, Lecanicillium lecanii conidia of strain DAOM198499 + SX, Lecanicillium lecanii conidia of strain DAOM216596 + SX, Lecanicillium muscarium strain Ve6 + SX,Metarhizium anisopliae strain F52 + SX, Metarhizium anisopliae var. acridum + SX, Metarhizium anisopliae var. anisopliae BIPESCO 5 / F52 + SX, Metarhizium flavoviride + SX, Monacrosporium phymatopagum + SX, Paecilomyces fumosoroseus Apopka strain 97 + SX, Paecilomyces lilacinus strain 251 + SX, Paecilomyces tenuipes strain T1 + SX, Paenibacillus popilliae + SX, Pasteuria nishizawae strain Pn1 + SX, Pasteuria penetrans + SX, Pasteuria usgae + SX, Pasteuria thornei + SX, Serratia entomophila + SX, Verticillium chlamydosporium + SX, Verticillium lecani strain NCIM1312 + SX, Wolbachia pipientis + SX。,
[0051] Combinations of the present ingredient of the above group (b) with the compound of the present invention: acibenzolar-S-methyl + SX, aldimorph + SX, ametoctradin + SX, aminopyrifen + SX, amisulbrom + SX, anilazine + SX, azaconazole + SX, azoxystrobin + SX, basic copper sulfate + SX, benalaxyl + SX, benalaxyl-M + SX, benodanil + SX, benomyl + SX, benthiavalicarb + SX, Benthiavalicarb-isopropyl + SX, benzovindiflupyr + SX, binapacryl + SX, biphenyl + SX, bitertanol + SX, bixafen + SX, blasticidin S + SX, Bordeaux mixture + SX, boscalid + SX, bromothalonil + SX, bromuconazole + SX, bupirimate + SX, captafol + SX, captan + SX, carbendazim + SX, carboxin + SX, carpropamid + SX, chinomethionate + SX, chitin + SX, chloroinconazide + SX, chloroneb + SX,Chlorothalonil + SX, chlozolinate + SX, colletochlorin B + SX, copper(II) acetate + SX, copper(II) hydroxide + SX, copper oxychloride + SX, copper(II) sulfate + SX, coumoxystrobin + SX, cyazofamid + SX, cyflufenamid + SX, cymoxanil + SX, cyproconazole + SX, cyprodinil + SX, dichlobentiazox + SX, Dichlofluanid + SX, diclocymet + SX, diclomezine + SX, dicloran + SX, diethofencarb + SX, difenoconazole + SX, diflumetorim + SX, dimethachlone + SX, dimethirimol + SX, dimethomorph + SX, dimoxystrobin + SX, diniconazole + SX, diniconazole-M + SX, dinocap + SX, dipotassium hydrogenphosphite + SX, dipymetitrone + SX, dithianon + SX,Dodecylbenzenesulphonic acid bisethylenediamine copper(II) salt + SX, dodemorph + SX, dodine + SX, edifenphos + SX, enoxastrobin + SX, epoxiconazole + SX, etaconazole + SX, ethaboxam + SX, ethirimol + SX, etridiazole + SX, tea tree extract (Melaleuca alternifolia) + SX, extract of Reynoutria sachalinensis (Japanese knotweed) + SX, extract of the cotyledons of lupine plantlets ("BLAD") + SX, garlic extract (extract of Allium sativum) + SX, horsetail extract (extract of Equisetum arvense) + SX, nasturtium extract (extract of Tropaeolum majus) + SX, famoxadone + SX, fenamidone + SX, fenaminstrobin + SX, fenarimol + SX, fenbuconazole + SX, feneptamidoquin + SX, fenfuram + SX, fenhexamid + SX, fenopyramide + SX, fenoxanil + SX, Fenpiclonil + SX, fenpicoxamid + SX,Fenpropidin + SX, fenpropimorph + SX, fenpyrazamine + SX, triphenyltin acetate + SX, triphenyltin chloride + SX, fentin hydroxide + SX, ferbam + SX, ferimzone + SX, florylpicoxamid + SX, fluazinam + SX, flubeneteram + SX, fludioxonil + SX, flufenoxadiazam + SX, flufenoxystrobin + SX, fluindapyr + SX, flumetylsulforim + SX, flumorph + SX, fluopicolide + SX, fluopyram + SX, fluopimomide + SX, fluoroimide + SX, fluoxapiprolin + SX, fluoxastrobin + SX, fluoxytioconazole + SX, fluquinconazole + SX, flusilazole + SX, flusulfamide + SX, flutianil + SX, flutolanil + SX, flutriafol + SX, Fluxapyroxad + SX, Folpet + SX, Fosetyl + SX, Fosetyl-aluminum + SX,Fuberidazole + SX, furalaxyl + SX, furametpyr + SX, galquin + SX, guazatine + SX, hexaconazole + SX, hymexazole + SX, imazalil + SX, imibenconazole + SX, iminoctadine + SX, iminoctadine triacetate + SX, inpyrfluxam + SX, iodocarb + SX, ipconazole + SX, ipfentrifluconazole + SX Ipflufenoquin + SX, iprobenfos + SX, iprodione + SX, iprovalicarb + SX, isofetamide + SX, isofleucine + SX, isoflucipram + SX, isoprothiolane + SX, isopyrazam + SX, isotianil + SX, kasugamycin + SX, kresoxim-methyl + SX, laminarin + SX, oak leaves and bark of quercus + SX, mancozeb + SX, mandestrobin + SX, Mandipropamid + SX, maneb + SX, mefentrifluconazole + SX, mepanipyrim + SX, mepronil + SX,Meptyldinocap + SX, metalaxyl + SX, metalaxyl-M + SX, metarylpicoxamid + SX, metconazole + SX, methasulfocarb + SX, metiram + SX, metominostrobin + SX, metrafenone + SX, metyltetraprole + SX, myclobutanil + SX, naftifine + SX, nuarimol + SX, octhilinone + SX, ofurace + SX Orysastrobin + SX, oxadixyl + SX, oxathiapiprolin + SX, oxine-copper + SX, oxolinic acid + SX, oxpoconazole + SX, oxpoconazole fumarate + SX, oxycarboxin + SX, oxytetracycline + SX, pefurazoate + SX, penconazole + SX, pencycuron + SX, penflufen + SX, penthiopyrad + SX, phenamacril + SX, phosphorous acid + SX, Phthalide + SX, picarbutrazox + SX, picoxystrobin + SX, piperalin + SX,Polyoxins + SX, potassium hydrogencarbonate + SX, potassium dihydrogenphosphite + SX, probenazole + SX, prochloraz + SX, procymidone + SX, propamidine + SX, propamocarb + SX, propiconazole + SX, propineb + SX, proquinazid + SX, prothiocarb + SX, prothioconazole + SX, pydiflumetofen + SX, pyraclostrobin + SX, pyrametostrobin + SX, Pyraoxystrobin + SX, pyrapropoyne + SX, pyraziflumid + SX, pyrazophos + SX, pyribencarb + SX, pyributicarb + SX, pyridaclomethyl + SX, pyrifenox + SX, pyrimethanil + SX, pyrimorph + SX, pyriophenone + SX, pyrisoxazole + SX, pyroquilon + SX, Quillaja extract + SX, quinconazole + SX, Quinofumelin + SX, quinoxyfen + SX, quintozene + SX,Quinoa saponins (Chenopodiaceae) + SX, seboctylamine + SX, sedaxane + SX, silthiofam + SX, simeconazole + SX, sodium hydrogencarbonate + SX, spiroxamine + SX, streptomycin + SX, sulfur + SX, tebuconazole + SX, tebufloquin + SX, teclofthalam + SX, tecnazene + SX, terbinafine + SX, tetraconazole + SX Thiabendazole + SX, thifluzamide + SX, thiophanate + SX, thiophanate-methyl + SX, thiram + SX, thymol + SX, tiadinil + SX, tolclofos-methyl + SX, tolfenpyrad + SX, tolprocarb + SX, tolylfluanid + SX, triadimefon + SX, triadimenol + SX, triazoxide + SX, triclopyricarb + SX, tricyclazole + SX, Tridemorph + SX, trifloxystrobin + SX, triflumizole + SX, triforine + SX,トリチコナゾール(triticonazole) + SX, バリダマイシン(validamycin) + SX, バリフェナレート(valifenalate) + SX, ビンクロゾリン(vinclozolin) + SX, マスタードパウダー(yellow mustard powder) + SX, zinc thiazole + SX, ジネブ(zineb) + SX, ジラム(ziram) + SX, ゾキサミド(zoxamide) + SX, N'-[4-({3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl}oxy)-2,5-dimethylphenyl]-N-ethyl-N-methylmethanimidamide (1202781-91-6) + SX, N'-{4-[(4,5-dichlorothiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylmethanimidamide (929908-57-6) + SX, N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylmethanimidamide (1052688-31-9) + SX, N'-[5-chloro-4-(2-fluorophenoxy)-2-methylphenyl]-N-ethyl-N-methylmethanimidamide (2055589-28-9) + SX, N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylmethanimidamide (2055756-21-1) + SX, N'-(2-chloro-4-phenoxy-5-methylphenyl)-N-ethyl-N-methylmethanimidamide (2062599-39-5) + SX, N'-[4-(1-hydroxy-1-phenyl-2,2,2-trifluoroethyl)-2-methyl-5-methoxyphenyl]-N-isopropyl-N-methylmethanimidamide (2101814-55-3) + SX,N'-[5-bromo-6-(1-methyl-2-propoxyethoxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylmethanimidamide (1817828-69-5) + SX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine (1362477-26-6) + SX, 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline (1257056-97-5) + SX, ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate (39491-78-6) + SX, N-[(2-chlorothiazol-5-yl)methyl]-N-ethyl-6-methoxy-3-nitropyridin-2-amine (1446247-98-8) + SX, 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-11-4) + SX, (1R, 2S, 5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-06-2) + SX, (1S, 2R, 5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-07-3) + SX, 2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-13-6) + SX, (1R, 2S,5S)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-08-4) + SX, (1S, 2R, 5R)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-09-5) + SX, methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-carboxylate (1791398-02-1) + SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-bromo-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-86-0) + SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-chloro-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-84-8) + SX, 1-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018316-13-5) + SX, 1-[2-(1-chlorocyclopropyl)-3-(2,3-difluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018317-25-2) + SX, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082661-43-4) + SX,2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082660-27-1) + SX, methyl ({2-methyl-5-[1-(4-methoxy-2-methylphenyl)-1H-pyrazol-3-yl]phenyl}methyl)carbamate (1605879-98-8) + SX, 2-(difluoromethyl)-N-[1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1616239-21-4) + SX, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-02-9) + SX, 2-(difluoromethyl)-N-[3-propyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-05-2) + SX, (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-27-0) + SX, (2E,3Z)-5-{[1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-54-3) + SX, 5-chloro-4-({2-[6-(4-chlorophenoxy)pyridin-3-yl]ethyl}amino)-6-methylpyrimidine (1605340-92-8) + SX, 4,4-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one (2098918-25-1) + SX, 5,5-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one (2098918-26-2) + SX, N-ethyl-2-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N,2-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide + SX, N-methoxy-N'-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N'-ethyl-N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N,N'-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N-acetyl-2-(ethanesulfonyl)-N-[2-(methoxycarbonyl)-4-(trifluoromethoxy)phenyl]-4-(trifluoromethyl)benzamide (2043675-28-9) + SX, 3-(4-bromo-7-fluoroindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX,3-(7-bromoindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(7-bromo-4-fluoroindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(3,5-dichloropyridin-2-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(3,5-dichloropyridin-2-yl)butan-2-yl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate + SX, N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide + SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)acetamide + SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({2-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)butanamide + SX, N-methoxy-N-methyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N,N-diethyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N-methyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one + SX,4-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)morpholin-3-one + SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one + SX, 3,3-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one + SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1,2-oxazinan-3-one + SX, 1-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)azepan-2-one + SX, 4,4-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, 5-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, ethyl 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxylate + SX, N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-propyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-methoxy-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-methoxy-N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N,N-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-1,2,4-triazol-3-amine + SX, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + SX, methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + SX, ethyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + SX, methyl 2-[2-(trifluoromethyl)-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + SX, 1-(2,3-dimethylpyridin-5-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-[2-(difluoromethyl)-3-methylpyridin-5-yl]-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 2,2-difluoro-N-[6-({[1-(1-methyl-1H-tetrazol-5-yl)benzimidazol-2-yl]oxy}methyl)pyridin-2-yl]-2-phenoxyacetamide + SX,1-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile + SX, ethyl 1-[(4-{[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy}phenyl)methyl]-1H-pyrazole-4-carboxylate + SX, ethyl 1-[(4-{[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy}phenyl)methyl]-1H-pyrazole-4-carboxylate + SX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide + SX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide + SX, 6-chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-(3-cyclopropyl-2-fluorophenoxy)-5-methylpyridazine-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(spiro[3.4]octan-1-yl)-5-methylthiazole-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-hexyl-5-methylthiazole-4-carboxamide + SX, 2-[acetyl(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2-methoxyacetyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2-methylpropanoyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-{[(oxetan-3-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-{[(oxolan-3-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-{[(oxan-4-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)ethyl]pyrimidin-2-amine + SX,5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(3,5-difluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(6-chloropyridin-3-yl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluoro-3-methoxyphenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-2-{[1-(2,6-difluorophenyl)cyclopropyl]oxy}pyrimidine + SX, 3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5S)-3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX,3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(4-bromo-2-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, 3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5R)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}-3-methylbutan-2-yl)-2-methylpropanamide + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}-3-methylbutan-2-yl)-2,2-dimethylpropanamide + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX, N-((2S)-1-{3-[2-(2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-(2-cyanoethoxy)ethyl]-5-[1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX, methyl ({5-[1-(2,6-difluoro-4-isopropylphenyl)-1H-pyrazol-3-yl]-2-methylphenyl}methyl)carbamate + SX, methyl ({5-[1-(2,6-difluoro-4-cyclopropylphenyl)-1H-pyrazol-3-yl]-2-methylphenyl}methyl)carbamate + SX, methyl ({5-[1-(2,6-difluoro-4-methoxyphenyl)-1H-pyrazol-3-yl]-2-methylphenyl}methyl)carbamate + SX, methyl (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxyprop-2-enoate + SX, methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxyprop-2-enoate + SX, methyl (Z)-2-[(3-isopropyl-1H-pyrazol-1-yl)-2-methylphenoxy]-3-methoxyprop-2-enoate + SX, 1-(4,5-dimethyl-1H-benzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-(4,5-dimethyl-1H-benzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-(pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-6-fluoro-3,3-dimethylisoquinolin-4(3H)-one + SX, methyl (2Z)-3-methoxy-2-[(4-methyl[1,1'-biphenyl]-3-yl)oxy]prop-2-enoate + SX, Agrobacterium radiobactor strain K1026 + SX, Agrobacterium radiobactor strain K84 + SX, Bacillus amyloliquefaciens strain PTA-4838 (Aveo™ EZ Nematicide) + SX, Bacillus amyloliquefaciens strain AT332 + SX, Bacillus amyloliquefaciens strain B3 + SX, Bacillus amyloliquefaciens strain D747 + SX, Bacillus amyloliquefaciens strain DB101 + SX, Bacillus amyloliquefaciens strain DB102 + SX, Bacillus amyloliquefaciens strain GB03 + SX, Bacillus amyloliquefaciens strain FZB24 + SX, Bacillus amyloliquefaciens strain FZB42 + SX, Bacillus amyloliquefaciens strain IN937a + SX,Bacillus amyloliquefaciens strain MBI600 + SX, Bacillus amyloliquefaciens strain QST713 + SX, Bacillus amyloliquefaciens isolate strain B246 + SX, Bacillus amyloliquefaciens strain F727 + SX, Bacillus amyloliquefaciens subsp. plantarum strain D747 + SX, Bacillus licheniformis strain HB-2 + SX, Bacillus licheniformis strain SB3086 + SX, Bacillus pumilus strain AQ717 + SX, Bacillus pumilus strain BUF-33 + SX, Bacillus pumilus strain GB34 + SX, Bacillus pumilus strain QST2808 + SX, Bacillus simplex strain CGF2856 + SX, Bacillus subtilis strain AQ153 + SX, Bacillus subtilis strain AQ743 + SX, Bacillus subtilis strain BU1814 + SX, Bacillus subtilis strain D747 + SX, Bacillus subtilis strain DB101 + SX, Bacillus subtilis strain FZB24 + SX, Bacillus subtilis strain GB03 + SX, Bacillus subtilis strain HAI0404 + SX, Bacillus subtilis strain IAB / BS03 + SX, Bacillus subtilis strain MBI600 + SX, Bacillus subtilis strain QST30002 / AQ30002 + SX, Bacillus subtilis strain QST30004 / AQ30004 + SX,Bacillus subtilis strain QST713 + SX, Bacillus subtilis strain QST714 + SX, Bacillus subtilis var. Amyloliquefaciens strain FZB24 + SX, Bacillus subtilis strain Y1336 + SX, Burkholderia cepacia + SX, Burkholderia cepacia type Wisconsin strain J82 + SX, Burkholderia cepacia type Wisconsin strain M54 + SX, Candida oleophila strain O + SX, Candida saitoana + SX, Chaetomium cupreum + SX, Clonostachys rosea + SX, Coniothyrium minitans strain CGMCC8325 + SX, Coniothyrium minitans strain CON / M / 91-8 + SX, cryptococcus albidus + SX, Erwinia carotovora subsp. carotovora strain CGE234M403 + SX, Fusarium oxysporum strain Fo47 + SX, Gliocladium catenulatum strain J1446 + SX, Paenibacillus polymyxa strain AC-1 + SX, Paenibacillus polymyxa strain BS-0105 + SX, Pantoea agglomerans strain E325 + SX, Phlebiopsis gigantea strain VRA1992 + SX, Pseudomonas aureofaciens strain TX-1 + SX, Pseudomonas chlororaphis strain 63-28 + SX, Pseudomonas chlororaphis strain AFS009 + SX,Pseudomonas chlororaphis strain MA342 + SX, Pseudomonas fluorescens strain 1629RS + SX, Pseudomonas fluorescens strain A506 + SX, Pseudomonas fluorescens strain CL145A + SX, Pseudomonas fluorescens strain G7090 + SX, Pseudomonas sp. strain CAB-02 + SX, Pseudomonas syringae strain 742RS + SX, Pseudomonas syringae strain MA-4 + SX, Pseudozyma flocculosa strain PF-A22UL + SX, Pseudomonas rhodesiae strain HAI-0804 + SX, Pythium oligandrum strain DV74 + SX, Pythium oligandrum strain M1 + SX, Streptomyces griseoviridis strain K61 + SX, Streptomyces lydicus strain WYCD108US + SX, Streptomyces lydicus strain WYEC108 + SX, Talaromyces flavus strain SAY-Y-94-01 + SX, Talaromyces flavus strain V117b + SX, Trichoderma asperellum strain ICC012 + SX, Trichoderma asperellum SKT-1 + SX, Trichoderma asperellum strain T25 + SX, Trichoderma asperellum strain T34 + SX, Trichoderma asperellum strain TV1 + SX, Trichoderma atroviride strain CNCM 1-1237 + SX, Trichoderma atroviride strain LC52 + SX,Trichoderma atroviride strain IMI 206040 + SX, Trichoderma atroviride strain SC1 + SX, Trichoderma atroviride strain SKT-1 + SX, Trichoderma atroviride strain T11 + SX, Trichoderma gamsii strain ICC080 + SX, Trichoderma harzianum strain 21 + SX, Trichoderma harzianum strain DB104 + SX, Trichoderma harzianum strain DSM 14944 + SX, Trichoderma harzianum strain ESALQ-1303 + SX, Trichoderma harzianum strain ESALQ-1306 + SX, Trichoderma harzianum strain IIHR-Th-2 + SX, Trichoderma harzianum strain ITEM908 + SX, Trichoderma harzianum strain kd + SX, Trichoderma harzianum strain MO1 + SX, Trichoderma harzianum strain SF + SX, Trichoderma harzianum strain T22 + SX, Trichoderma harzianum strain T39 + SX, Trichoderma harzianum strain T78 + SX, Trichoderma harzianum strain TH35 + SX, Trichoderma polysporum strain IMI206039 + SX, trichoderma stromaticum + SX, Trichoderma virens strain G-41 + SX, Trichoderma virens strain GL-21 + SX, Trichoderma viride + SX,Variovorax paradoxus strain CGF4526 + SX, Harpin protein + SX。,
[0052] Combinations of the present ingredient in group (c) above with the compound of the present invention: 1-methylcyclopropene + SX, 1,3-diphenylurea + SX, 2,3,5-triiodobenzoic acid + SX, (1H-indol-3-yl)acetic acid (IAA) + SX, 4-(1H-indol-3-yl)butyric acid (IBA) + SX, 2-(4-chloro-2-methylphenoxy)acetic acid (MCPA) + SX, 4-(4-chloro-2-methylphenoxy)butyric acid (MCPB) + SX, 4-chlorophenoxyacetic acid (4-CPA) + SX, 5-aminolevulinic acid hydrochloride + SX, 6-benzylaminopurine + SX, abscisic acid + SX, AVG (aminoethoxyvinylglycine) + SX, anisiflupurin + SX, ancymidol + SX, butralin + SX, calcium carbonate + SX, calcium chloride + SX, calcium formate + SX, calcium peroxide + SX, calcium polysulfide + SX, calcium sulfate + SX, chlormequat chloride + SX, chlorpropham + SX, choline chloride + SX, cloprop + SX, cyanamide + SX, Cyclanilide + SX,Daminozide + SX, decan-1-ol + SX, dichlorprop + SX, dikegulac + SX, dimethipin + SX, diquat + SX, ethephon + SX, ethychlozate + SX, flumetralin + SX, flurprimidol + SX, forchlorfenuron + SX, formononetin + SX, gibberellin A + SX, gibberellin A3 + SX, inabenfide + SX, Kinetin + SX, lipochitooligosaccharide SP104 + SX, maleic hydrazide + SX, mefluidide + SX, mepiquat chloride + SX, oxidized glutathione + SX, paclobutrazol + SX, pendimethalin + SX, prohexadione calcium + SX, prohydrojasmon + SX, pyraflufen-ethyl + SX, sintophen + SX, sodium 1-naphthaleneacetate + SX, sodium cyanate + SX, Thidiazuron + SX, triapenthenol + SX, tribufos + SX, trinexapac-ethyl + SX,Uniconazole-P + SX, 2-(naphthalen-1-yl)acetamide + SX, [4-oxo-4-(2-phenylethyl)amino]butyric acid + SX, Methyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate + SX, 3-[(6-chloro-4-phenylquinazolin-2-yl)amino]propan-1-ol + SX, Claroideoglomus etunicatum + SX, Claroideoglomus claroideum + SX, Funneliformis mosseae + SX, Gigaspora margarita + SX, Gigaspora rosea + SX, Glomus aggregatum + SX, Glomus deserticola + SX, Glomus monosporum + SX, Paraglomus brasillianum + SX, Rhizophagus clarus + SX, Rhizophagus intraradices RTI-801 + SX, Rhizophagus irregularis DAOM 197198 + SX, Azorhizobium caulinodans + SX, Azospirillum amazonense + SX, Azospirillum brasilense XOH + SX, Azospirillum brasilense Ab-V5 + SX, Azospirillum brasilense Ab-V6 + SX, Azospirillum caulinodans + SX, Azospirillum halopraeferens + SX, Azospirillum irakense + SX, Azospirillum lipoferum + SX, Bradyrhizobium elkanii SEMIA 587 + SX, Bradyrhizobium elkanii SEMIA 5019 + SX, Bradyrhizobium japonicum TA-11 + SX,Bradyrhizobium japonicum USDA 110 + SX, Bradyrhizobium liaoningense + SX, Bradyrhizobium lupini + SX, Delftia acidovorans RAY209 + SX, Mesorhizobium ciceri + SX, Mesorhizobium huakii + SX, Mesorhizobium loti + SX, Rhizobium etli + SX, Rhizobium galegae + SX, Rhizobium leguminosarum bv. Phaseoli + SX, Rhizobium leguminosarum bv. Trifolii + SX, Rhizobium leguminosarum bv. Viciae + SX, Rhizobium trifolii + SX, Rhizobium tropici + SX, Sinorhizobium fredii + SX, Sinorhizobium meliloti + SX, Zucchini Yellow Mosaik Virus weak strain + SX. ,
[0053] Combinations of the present component of the above group (d) with the compound of the present invention: anthraquinone + SX, deet + SX, icaridin + SX.
[0054] The ratio of the compound of the present invention to the present component is not particularly limited, and examples thereof include a weight ratio (compound of the present invention:present component) of 1000:1 to 1:1000, 500:1 to 1:500, 100:1 to 1:100, 50:1, 20:1, 10:1, 9:1, 8:1, 7:1, 6:1, 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:20, 1:50, and the like.
[0055] The present compound, the compound of the present invention, or Composition A can control plant diseases caused by plant pathogenic microorganisms such as fungi, oomycetes, Phytomyxea, and bacteria. Examples of fungi include Ascomycota, Basidiomycota, Blastocladiomycota, Chytridiomycota, Mucoromycota, and Olpidiomycota. Specific examples include the following: The scientific name of the plant pathogenic microorganism that causes each disease is shown in parentheses.
[0056] Rice diseases: blast (Pyricularia oryzae), sesame leaf blight (Cochliobolus miyabeanus), sheath blight (Rhizoctonia solani), bakanae disease (Gibberella fujikuroi), yellowing and withering disease (Sclerophthora macrospora), false blast and ear blight (Epicoccum nigrum), seedling blight (Trichoderma viride, Rhizopus oryzae), suspected sheath blight (red sclerotium pathogen (Waitea circinata), brown sclerotium pathogen (Ceratobasidium setariae), brown sheath blight pathogen (Thanatephorus cucumeris)), false smut (Ustilaginoidea virens), black kernel smut (Tilletia horrida, Tilletia barclayana);Wheat diseases: Powdery mildew (Blumeria graminis), head blight (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), yellow rust (Puccinia striiformis), black rust (Puccinia graminis), red rust (Puccinia recondita), pink snow blight (Microdochium nivale, Microdochium majus), small snow blight (Typhula incarnata, Typhula ishikariensis), large snow blight (Sclerotinia borealis), brown snow blight (Pythium spp.), naked smut (Ustilago tritici), grass smut (Tilletia caries, Tilletia controversa), eyespot (Pseudocercosporella herpotrichoides), leaf blight (Septoria tritici), rotten blight (Stagonospora nodorum), yellow spot (Pyrenophora tritici-repentis), seedling damping off caused by Rhizoctonia fungi (Rhizoctonia solani), damping off (Gaeumannomyces graminis), rice blast (Pyricularia graminis-tritici);Barley diseases: powdery mildew (Blumeria graminis), head blight (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), yellow rust (Puccinia striiformis), black rust (Puccinia graminis), small rust (Puccinia hordei), ear bunt (Ustilago nuda), scald (Rhynchosporium secalis), net blotch (Pyrenophora teres), leaf spot (Cochliobolus sativus), leaf spot (Pyrenophora graminea), leaf spot (Ramularia collo-cygni), seedling damping-off (Rhizoctonia solani); corn diseases: rust (Puccinia sorghi), southern rust (Puccinia polysora), sooty blight (Setosphaeria turcica), tropical rust (Physopella zeae), southern leaf blight (Cochliobolus heterostrophus), anthracnose (Colletotrichum graminicola), gray leaf spot (Cercospora zeae-maydis), brown spot (Kabatiella zeae), Phaeosphaeria leaf spot (Phaeosphaeria maydis), Diplodia disease (Stenocarpella maydis, Stenocarpella macrospora), stalk rot (Fusarium graminearum, Fusarium verticilioides, Colletotrichum graminicola), smut (Ustilago maydis), Physoderma maydis, tar spot (Phyllachora maydis);Cotton diseases: anthracnose (Colletotrichum gossypii), white mold (Ramularia areola), black spot (Alternaria macrospora, Alternaria gossypii), black root rot (Thielaviopsis basicola); coffee diseases: rust (Hemileia vastatrix), leaf spot (Cercospora coffeicola); rapeseed diseases: sclerotinia sclerotiorum, black spot (Alternaria brassicae), root rot (Phoma lingam), light leaf spot (Pyrenopeziza brassicae); sugarcane diseases: rust (Puccinia melanocephela, Puccinia kuehnii), smut (Ustilago scitaminea); sunflower diseases: rust (Puccinia helianthi), downy mildew (Plasmopara Citrus diseases: black spot (Diaporthe citri), scab (Elsinoe fawcetti), green mold (Penicillium digitatum), blue mold (Penicillium italicum), late blight (Phytophthora parasitica, Phytophthora citrophthora), aspergillus niger;Apple diseases: Monilinia mali, canker (Valsa ceratosperma), powdery mildew (Podosphaera leucotricha), leaf spot (Alternaria alternata apple pathotype), black spot (Venturia inaequalis), anthracnose (Glomerella cingulata, Colletotrichum acutatum), brown spot (Diplocarpon mali), ring spot (Botryosphaeria berengeriana), late blight (Phytophtora cactorum), red spot (Gymnosporangium juniperi-virginianae, Gymnosporangium yamadae); Pear diseases: black spot (Venturia nashicola, Venturia pirina), black spot (Alternaria alternata Japanese pear pathotype), red spot (Gymnosporangium haraeanum); Peach diseases: brown rot (Monilinia fructicola), black scab (Cladosporium carpophilum), phomopsis rot (Phomopsis sp.), leaf crinkle (Taphrina deformans), powdery mildew (Podosphaera leucotricha); grape diseases: black rot (Elsinoe ampelina), late rot (Glomerella cingulata, Colletotrichum acutatum), powdery mildew (Uncinula necator), rust (Neophysopella sp.), black rot (Guignardia bidwellii), downy mildew (Plasmopara viticola), brown spot (Pseudocercospora vitis), white rot (Coniella castaneicola); persimmon diseases: anthracnose (Gloeosporium kaki, Colletotrichum acutatum), leaf drop (Cercospora kaki, Mycosphaerella nawae), powdery mildew (Phyllactinia kakicola);Fig diseases: Rust (Phakopsora nishidana); Cucurbit diseases: Anthracnose (Colletotrichum lagenarium), Powdery mildew (Sphaerotheca fuliginea), Blight (Didymella bryoniae), Brown spot (Corynespora cassiicola), Blight (Fusarium oxysporum), Downy mildew (Pseudoperonospora cubensis), Late blight (Phytophthora capsici), Damping-off (Pythium sp.), Root rot (Phomopsis sp.); Tomato diseases: Ring spot (Alternaria solani), Leaf mold (Cladosporium fulvum), Leaf mold (Pseudocercospora fuligena), Late blight (Phytophthora infestans), Powdery mildew (Leveillula taurica); Diseases of eggplant: brown spot (Phomopsis vexans), powdery mildew (Erysiphe cichoracearum), black blight (Corynespora melongenae), sooty mold (Mycovellosiella nattrassii), brown spot (Thanatephorus cucumeris); diseases of cruciferous vegetables: black spot (Alternaria japonica), white spot (Cercosporella brassicae), clubroot (Plasmodiophora brassicae), downy mildew (Peronospora parasitica), white rust (Albugo candida), sooty mold (Alternaria brassicicola); diseases of leeks: rust (Puccinia allii), black spot (Alternaria porri), black rot (Sclerotium cepivorum), small sclerotial rot (Botrytis squamosa), leaf blight (Stemphylium vesicarium, Stempphylium botryosum), white silk disease (Sclerotium rolfsii), white spot leaf blight (Botrytis squamosa);Soybean diseases: Purple spot (Cercospora kikuchii), black rot (Elsinoe glycines), black spot (Diaporthe phaseolorum var. sojae), rust (Phakopsora pachyrhizi), brown ring spot (Corynespora cassiicola), anthracnose (Colletotrichum glycines, Colletotrichum truncatum), leaf rot (Rhizoctonia solani), brown spot (Septoria glycines), leaf spot (Cercospora sojina), sclerotinia sclerotiorum, powdery mildew (Microsphaera diffusa), stem rot (Phytophthora sojae), downy mildew (Peronospora manshurica), sudden death (Fusarium virguliforme), black root rot (Calonectria ilicicola), Diaporthe / Phomopsis Diseases of soybeans include: complex (Diaporthe longicolla, Diaporthe phaseolorum, Phomopsis longicolla), pod anomalies of soybeans caused by various pathogenic fungi; diseases of common beans: Sclerotinia sclerotiorum, rust (Uromyces appendiculatus), angular spot (Phaeoisariopsis griseola), anthracnose (Colletotrichum lindemuthianum), root rot (Fusarium solani); diseases of peanuts: black spot (Cercospora personata), brown spot (Cercospora arachidicola), southern blight (Sclerotium rolfsii), black root rot (Calonectria ilicicola); diseases of peas: powdery mildew (Erysiphe pisi), root rot (Fusarium solani);Potato diseases: summer blight (Alternaria solani), late blight (Phytophthora infestans), scarlet rot (Phytophthora erythroseptica), powdery scab (Spongospora subterranea f. sp. subterranea), verticillium wilt (Verticillium albo-atrum, Verticillium dahliae, Verticillium nigrescens), dry rot (Fusarium solani), canker (Synchytrium endobioticum); strawberry diseases: powdery mildew (Sphaerotheca humuli), anthracnose (Glomerella cingulata, Colletotrichum acutatum); tea diseases: net blight (Exobasidium reticulatum), white spot (Elsinoe leucospila), ring spot (Pestalotiopsis Diseases of tobacco: red spot (Alternaria longipes), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), late blight (Phytophthora nicotianae); Diseases of sugar beet: brown spot (Cercospora beticola), leaf rot (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris), black root rot (Aphanomyces cochlioides), rust (Uromyces betae); Diseases of rose: black spot (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa); Diseases of chrysanthemum: brown spot (Septoria chrysanthemi indici), white rust (Puccinia horiana); Onion diseases: white spotted leaf blight (Botrytis cinerea, Botrytis byssoidea, Botrytis squamosa), gray rot (Botrytis allii), small sclerotial rot (Botrytis squamosa);Diseases of various crops: gray mold (Botrytis cinerea), sclerotinia sclerotiorum, black rot (Sclerotium cepivorum), southern blight (Sclerotium rolfsii), damping-off (Pythium aphanidermatum, Pythium irregulare, Pythium ultimum); diseases of radish: black spot (Alternaria brassicicola); diseases of sweet potato: fusarium wilt (Fusarium oxysporum f. sp. batatas), root rot (Diaporthe destruens), black spot (Ceratocystis fimbriata); diseases of turfgrass: dollar spot (Sclerotinia homoeocarpa), brown patch, large patch (Rhizoctonia solani), red blight (Pythium aphanidermatum), anthracnose (Colletotrichum caudatum); Banana diseases: Sigatoka (Mycosphaerella fijiensis, Mycosphaerella musicola); Lentil diseases: Ascochyta (Ascochyta lentis); Chickpea diseases: Ascochyta (Ascochyta rabiei); Bell pepper diseases: Anthracnose (Colletotrichum scovillei), Powdery mildew (Leveillula taurica), Southern blight (Sclerotium rolfsii); Mango diseases: Anthracnose (Colletotrichum acutatum); Cocoa diseases: Witches' broom (Moniliophthora perniciosa), Frosty pod rot (Moniliophthora roreri); Pecan diseases: Black spot (Venturia effusa); Diseases of lychee: downy mildew (Peronophythora litchii), anthracnose (Colletotrichum siemense); Diseases of fruit trees: white root rot (Rosellinia necatrix), purple root rot (Helicobasidium mompa);Diseases of fruits such as apples and pears after harvest: Mucorrot (Mucor piriformis); seed diseases or diseases in the early stages of growth caused by species of the genera Aspergillus, Penicillium, Fusarium, Gibberella, Tricoderma, Thielaviopsis, Rhizopus, Mucor, Corticium, Phoma, Rhizoctonia, Diplodia, etc.; viral diseases: big vein disease of lettuce transmitted by Olpidium brassicae, viral diseases of various crops transmitted by species of the Polymyxa genus (e.g., Polymyxa betae and Polymyxa graminis); diseases caused by bacteria: bacterial seedling blight of rice (Burkholderia plantarii), brown leach disease of rice (Pantoea ananatis), bacterial leaf blight of rice (Xanthomonas oryzae pv. oryzae.), cucumber bacterial spot (Pseudomonas syringae pv. lachrymans), eggplant bacterial wilt (Ralstonia solanacearum), citrus canker (Xanthomonas citri), Chinese cabbage soft rot (Erwinia carotovora), potato scab (Streptomyces scabiei), potato black leg (Pectobacterium carotovorum, Dickeia sp.), peach bacterial bore (Pseudomona syringae, Erwinia nigrifluens, Xanthomonas campestris), plum canker (Pseudomonas syringae pv. morsprunorum, Erwinia sp.), corn Goss's wilt (Clavibacter michiganensis), and grape, olive, and peach Pierce's disease (Xylella fastidiosa), and crown gall of Rosaceae plants such as apples, peaches, and cherries (Agrobacterium tumefaciens);
[0057] The soybean rust fungus with the F129L amino acid substitution in the mitochondrial cytochrome b protein is a soybean rust fungus (scientific name: Phakopsora pachyrhizi) that has a mutation in the mitochondrial cytochrome b gene that encodes the mitochondrial cytochrome protein, resulting in the F129L amino acid substitution, and is therefore resistant to QoI fungicides.
[0058] One embodiment of the method for controlling plant diseases of the present invention is a method for controlling soybean rust fungi, which comprises treating soybeans or the soil in which soybeans are grown with the present compound.
[0059] The method for controlling plant diseases of the present invention is carried out by applying an effective amount of the present compound, the compound of the present invention, or Composition A to plants or the soil in which the plants are grown. Examples of the treatment method include foliage treatment, soil treatment, and seed treatment.
[0060] The present compound, the compound of the present invention, or Composition A is typically formulated into an aqueous suspension, oil suspension, oil concentrate, emulsifiable concentrate, emulsion, microemulsion, microcapsule, wettable powder, water dispersible granule, dust, granule, or other formulation by mixing an inert carrier such as a solid carrier or a liquid carrier with a surfactant, and optionally adding formulation adjuvants such as a binder, dispersant, or stabilizer. In addition to these formulations, the present compound, the compound of the present invention, or Composition A can also be formulated into a dosage form described in "Manual on development and use of FAO and WHO Specifications for pesticides," FAO Plant Production and Protection Papers-271 to 276, prepared by the FAO / WHO Joint Meeting on Pesticide Specifications, 2016, ISSN:0259-2517. These formulations typically contain 0.0001 to 99% by weight of the present compound, the compound of the present invention, or Composition A.
[0061] Examples of solid carriers include clay (pyrophyllite clay, kaolin clay, etc.), talc, calcium carbonate, diatomaceous earth, zeolite, bentonite, acid clay, attapulgite, white carbon, ammonium sulfate, vermiculite, perlite, pumice, silica sand, fine powder and granular chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.), and resins (polyethylene, polypropylene, polyester, polyurethane, polyamide, polyvinyl chloride, etc.).
[0062] Examples of liquid carriers include water, alcohols (ethanol, cyclohexanol, benzyl alcohol, propylene glycol, polyethylene glycol, etc.), ketones (acetone, cyclohexanone, etc.), aromatic hydrocarbons (xylene, phenylxylylethane, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, etc.), esters (ethyl acetate, methyl oleate, propylene carbonate, etc.), nitriles (acetonitrile, etc.), ethers (ethylene glycol dimethyl ether, etc.), amides (N,N-dimethylformamide, N,N-dimethyloctanamide, etc.), sulfoxides (dimethyl sulfoxide, etc.), lactams (N-methylpyrrolidone, N-octylpyrrolidone, etc.), fatty acids (oleic acid, etc.), and vegetable oils (soybean oil, etc.).
[0063] Examples of surfactants include nonionic surfactants (polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyethylene glycol fatty acid esters, etc.) and anionic surfactants (alkyl sulfonates, alkylaryl sulfonates, alkyl sulfates, etc.).
[0064] Other formulation adjuvants include binders, dispersants, colorants, stabilizers, etc., and specific examples include polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), acid isopropyl phosphate, and dibutylhydroxytoluene.
[0065] Furthermore, an adjuvant can be used as a component that enhances or supports the efficacy of the present compound, the compound of the present invention, or Composition A. Specific examples include Nimbus (registered trademark), Assist (registered trademark), Aureo (registered trademark), Iharol (registered trademark), Silwet L-77 (registered trademark), BreakThru (registered trademark), Sundance II (registered trademark), Induce (registered trademark), Penetrator (registered trademark), AgriDex (registered trademark), Lutensol A8 (registered trademark), NP-7 (registered trademark), Triton (registered trademark), Nufilm (registered trademark), Emulgator NP7 (registered trademark), Emulad (registered trademark), TRITON X 45 (registered trademark), AGRAL 90 (registered trademark), AGROTIN (registered trademark), ARPON (registered trademark), EnSpray N (registered trademark), and BANOLE (registered trademark).
[0066] In the present invention, plants include whole plants and specific parts of plants, such as stems, leaves, flowers, spikes, fruits, trunks, branches, crowns, seeds, vegetative reproductive organs, and seedlings.
[0067] Vegetative reproductive organs refer to plant roots, stems, leaves, and other parts that can grow when separated from the main body and placed in soil. Examples of vegetative reproductive organs include tuberous roots, creeping roots, bulbs, corms (or solid bulbs), tubers, rhizomes, stolons, rhizophores, cane cuttings, propagules, and vine cuttings. Stolons are sometimes called runners, and propagules are also called bulbils and are divided into broad buds and bulbils. Vines refer to shoots (a collective term for leaves and stems) of plants such as sweet potatoes and Japanese yams. Bulbs, corms, tubers, rhizomes, stem fragments, rhizophores, and tuberous roots are collectively called bulbils. Potato cultivation begins by planting tubers in the soil, and the tubers used are generally called seed potatoes.
[0068] Seedlings include seedlings and saplings.
[0069] Examples of methods for controlling plant diseases by applying an effective amount of the present compound, the compound of the present invention, or Composition A to soil include methods of applying an effective amount of the present compound, the compound of the present invention, or Composition A to soil before or after planting a plant. More specifically, for example, planting hole treatment (spraying in planting holes, mixing in planting hole treatment soil), plant base treatment (spraying in planting holes, mixing in plant base soil, plant base irrigation, plant base treatment in the latter half of the seedling raising period), planting furrow treatment (spraying in planting furrows, mixing in planting furrow soil), row treatment (row spraying, row soil mixing, row spraying in the growing season), row treatment at sowing (row spraying at sowing, mixing in row soil at sowing), overall treatment (overall soil spraying, overall soil mixing), side row treatment, water surface treatment (water surface application, water surface application after flooding), other soil spray treatments (foliar spraying of granules during the growing season, spraying under the crown or around the main trunk, soil surface spraying, soil surface mixing, seeding hole spraying, furrow surface spraying, spraying between plants), and others. Other irrigation treatments include soil irrigation, seedling irrigation, chemical injection treatment, ground level irrigation, chemical drip irrigation, chemigation), seedling tray treatments (seedling tray spraying, seedling tray irrigation, seedling tray flooding), seedling tray treatments (seedling tray spraying, seedling tray irrigation, seedling tray flooding), seedling bed treatments (seedling bed spraying, seedling bed irrigation, water seedling bed spraying, seedling immersion), bed soil mixing treatments (bed soil mixing, bed soil mixing before sowing, spraying before soil covering at sowing, spraying after soil covering at sowing, covering soil mixing), and other treatments (hilling soil mixing, plowing in, topsoil mixing, rain-drop soil mixing, planting position treatment, granular inflorescence spraying, paste fertilizer mixing).
[0070] Seed treatments include, for example, treatment of seeds or vegetative reproductive organs with the present compound, the compound of the present invention, or Composition A. More specifically, examples include spray treatments in which a suspension of the present compound, the compound of the present invention, or Composition A is sprayed onto the surface of seeds or vegetative reproductive organs; smear treatments in which the present compound, the compound of the present invention, or Composition A is applied to seeds or vegetative reproductive organs; immersion treatments in which seeds or vegetative reproductive organs are immersed in a solution of the present compound, the compound of the present invention, or Composition A for a certain period of time; and methods of coating seeds or vegetative reproductive organs with a carrier containing the present compound, the compound of the present invention, or Composition A (film coating treatment, pellet coating treatment, etc.). The above-mentioned vegetative reproductive organs particularly include seed potatoes. In the present invention, the term "seeds or vegetative reproductive organs carrying the present compound, the compound of the present invention, or Composition A" refers to seeds or vegetative reproductive organs in which the present compound, the compound of the present invention, or Composition A is attached to the surface of the seeds or vegetative reproductive organs. The above-mentioned seeds or vegetative reproductive organs carrying the present compound, the compound of the present invention, or Composition A may have materials other than the present compound, the compound of the present invention, or Composition A attached to them before or after the application of the present compound, the compound of the present invention, or Composition A to the seeds or vegetative reproductive organs. Furthermore, when composition A is attached to the surface of a seed or vegetative reproductive organ in the form of a layer, the layer may consist of one layer or multiple layers. Furthermore, when it consists of multiple layers, each layer may contain one or more active ingredients, or may consist of a layer containing one or more active ingredients and a layer containing no active ingredients. Seeds or vegetative reproductive organs bearing the present compound, the compound of the present invention, or composition A can be obtained, for example, by applying a formulation containing the present compound, the compound of the present invention, or composition A to seeds or vegetative reproductive organs by the seed treatment method described above.
[0071] The application rate of the present compound, the compound of the present invention or Composition A varies depending on weather conditions, formulation type, application time, application method, application location, target disease, target crop, etc., but in the case of foliar application or soil application, the application rate is 1000 ml 2In the case of seed treatment, the amount of the present compound, the compound of the present invention, or Composition A is usually 0.001 to 100 g per kg of seeds. When the present compound, the compound of the present invention, or Composition A is formulated as an emulsifiable concentrate, wettable powder, flowable concentrate, or the like, it is usually applied after being diluted with water to an active ingredient concentration of 0.01 to 10,000 ppm, and dusts, granules, and the like are usually applied as they are.
[0072] The present compound, the compound of the present invention or Composition A can be used as an agent for controlling plant diseases in agricultural lands such as fields, paddy fields, lawns, orchards, etc. Examples of plants include the following.
[0073] Corn (horse-tooth, hard grain, soft grain, explosive, glutinous, sweet, field corn), rice (long grain, short grain, medium grain, japonica, tropical japonica, indica, javanica, paddy rice, upland rice, floating rice, direct-seeded rice, transplanted rice, glutinous rice), wheat (bread wheat (hard, soft, medium, red wheat, white wheat), durum wheat, spelt wheat, club wheat, each winter wheat type, spring wheat type), barley (two-row barley (= beer barley), six-row barley, naked barley, waxy barley, each winter barley type, spring barley type), rye (winter rye type, spring rye type), triticale (winter triticale type, spring triticale type), oats (winter oat type, spring oat type), sorghum, cotton (upland type, pima type), soybean (fully harvested seed varieties, edamame varieties, green-harvested varieties, indeterminate, determinate, semi-determinate types), peanuts, buckwheat, sugar beet (sugar production, animal feed, root vegetable, leafy vegetable, fuel), rapeseed (winter rapeseed type, spring rapeseed type), canola (winter canola type, spring canola type), sunflower (oil production, food, ornamental), sugarcane, tobacco, tea plant, mulberry, solanaceous vegetables (eggplant, tomato, bell pepper, chili pepper) , potatoes, etc.), Cucurbitaceae vegetables (cucumber, pumpkin, zucchini, watermelon, melon, etc.), Cruciferous vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, mustard greens, broccoli, cauliflower, etc.), Asteraceae vegetables (burdock, garland chrysanthemum, artichoke, lettuce, etc.), Liliaceae vegetables (leeks, onions, garlic, asparagus, etc.), Umbelliferae vegetables (carrots, parsley, celery, parsley, etc.), Chenopodiaceae vegetables (spinach, Swiss chard, etc.), Lamiaceae vegetables (perilla, mint, basil, etc.), strawberries, sweet potatoes, yams, scallions, Sweet potatoes, pome fruits (apples, European pears, Japanese pears, Chinese pears, quince, quince, etc.), stone fruits (peaches, plums, nectarines, plums, cherries, apricots, prunes, etc.), citrus fruits (Satsuma mandarins, oranges, lemons, limes, grapefruits, etc.), nuts (chestnuts, walnuts, hazelnuts, almonds, pistachios, cashew nuts, macadamia nuts, etc.), berries (blueberries, cranberries, blackberries, raspberries, etc.), grapes, persimmons, figs, olives, loquats, bananas, coffee, dates, coconuts, ornamental plants, forest plants,Turfgrass, pasture grass,
[0074] The above-mentioned plants are not particularly limited as long as they are varieties that are commonly cultivated, and include plants that can be produced by natural crossbreeding, plants that can be generated by mutation, F1 hybrid plants, and genetically modified crops. Examples of genetically modified crops include plants that have been conferred resistance to herbicides such as HPPD (4-hydroxyphenylpyruvate dioxygenase enzyme) inhibitors such as isoxaflutole, ALS (acetolactate synthase) inhibitors such as imazethapyr and thifensulfuron methyl, EPSP (5-enolpyruvylshikimate-3-phosphate synthase) inhibitors, glutamine synthetase inhibitors, PPO (protoporphyrinogen oxidase) inhibitors, bromoxynil, or dicamba; plants that are capable of synthesizing selective toxins known to be found in the genus Bacillus, such as Bacillus thuringiensis; and plants that can be conferred specific insecticidal activity by synthesizing gene fragments that partially match endogenous genes derived from harmful insects and inducing gene silencing (RNAi; RNA interference) in the target harmful insect.
[0075] The present invention will be explained in more detail below by showing Production Examples, Reference Production Examples, Formulation Examples and Test Examples, but the present invention is not limited to these examples.
[0076] In this specification, Me represents a methyl group, Et represents an ethyl group, Pr represents a propyl group, i-Pr represents an isopropyl group, cPr represents a cyclopropyl group, Bu represents a butyl group, i-Bu represents an isobutyl group, s-Bu represents a sec-butyl group, Ph represents a phenyl group, Bn represents a benzyl group, and 2-Py represents a pyridin-2-yl group. When Ph is substituted with a substituent, the substituent and the substitution position are written before the symbol. For example, 4-OMe-Ph represents a 4-methoxyphenyl group, and 2,6-Cl2-Ph represents a 2,6-dichlorophenyl group.
[0077] When the physical properties of a compound are measured by liquid chromatography / mass spectrometry (hereinafter referred to as LC / MS), the measured molecular ion value [M+H] +, [M+H+MeCN] + or [M-H] - The time and retention time (hereinafter referred to as RT) are also recorded. The conditions for liquid chromatography (hereinafter referred to as LC) and mass spectrometry (hereinafter referred to as MS) are as follows. [LC conditions] Column: L-column2 ODS, inner diameter 4.6 mm, length 30 mm, particle size 3 μm (Chemicals Evaluation and Research Institute, Japan) UV measurement wavelength: 254 nm Mobile phase: Solution A: 0.1% formic acid aqueous solution, Solution B: 0.1% formic acid acetonitrile Flow rate: 2.0 mL / min Pump: Two LC-20AD pumps (Shimadzu Corporation) (high-pressure gradient) Gradient conditions: Solution was delivered at the concentration gradient shown in [Table LC1].
[0078] [MS conditions] Detector: LCMS-2020 (manufactured by Shimadzu Corporation) Ionization method: DUIS method (ESI, APCI)
[0079] First, examples of the preparation of the present compounds (including the compounds of the present invention) will be shown.
[0080] Production Example 1: Under a nitrogen atmosphere, 6.3 mL of isopropylmagnesium chloride lithium chloride complex (THF solution, 1.3 M) was added dropwise to a mixture of 2 g of 4-bromo-3,5-difluoro-1,1'-biphenyl and 18 mL of THF at 0°C, and the mixture was stirred at room temperature for 2 hours. 6 mL of the resulting mixture was transferred to another reaction vessel, and a THF solution (5 mL) of 0.25 g of 3-pyridazinecarbaldehyde was added, followed by stirring at room temperature for 2.5 hours. Aqueous ammonium chloride solution was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 4:1 to 1:19) to obtain 0.18 g of Compound 1 represented by the following formula: This compound 1: 1 H-NMR (CDCl3) δ: 9.17 (1H, d), 7.56-7.38 (7H, m), 7.16-7.09 (2H, m), 6.44 (1H, d), 4.98 (1H, d).
[0081] Preparation Example 1-1 The compound prepared in accordance with Preparation Example 1 and its physical properties are shown below. Formula (IA-1) In the compound represented by the formula (hereinafter referred to as compound (IA-1)), R 1a , R 2a , X 1a , X 2a , X 3a , X 4a , R 5A , R 5B , R 5C , R 5D and a compound in which the combination of E is any of the combinations described in [Table A-1].
[0082]
[0083] This compound 2: 1 H-NMR (CDCl3) δ: 8.67 (1H, s), 8.58-8.53 (2H, m), 7.56-7.51 (2H, m), 7.49-7.37 (3H, m), 7.17-7.10 (2H, m), 6.33 (1H, d), 4.58 (1H, d). Compound 3: 1 H-NMR (CDCl3) δ: 8.62 (1H, d), 7.71-7.65 (1H, m), 7.56-7.50 (2H, m), 7.49-7.36 (3H, m), 7.29-7.19 (2H, m), 7.14-7.07 (2H, m), 6.23 (1H, d), 5.47 (1H, d). Compound 4: 1 H-NMR (CDCl3) δ: 8.79 (2H, d), 7.54-7.50 (2H, m), 7.47-7.35 (3H, m), 7.28 (1H, t), 7.14-7.07 (2H, m), 6.28 (1H, d), 5.11 (1H, d). This compound 5: 1 H-NMR (CDCl3) δ: 8.46 (1H, d), 7.55-7.51 (2H, m), 7.47-7.38 (4H, m), 7.30-7.26 (1H, m), 7.14-7.09 (2H, m), 6.23 (1H, d), 4.97 (1H, d). Compound 44: 1H-NMR (CDCl3) δ: 8.60-8.58 (1H, m), 7.65 (1H, td), 7.58-7.55 (4H, m), 7.46-7.40 (4H, m), 7.33 (1H, tt), 7.23-7.19 (2H, m), 5.80 (1H, d), 5.29 (1H, d). Compound 45: LC / MS: 312 [M+H] + , RT = 1.569 Compound 46: LC / MS: 312 [M+H] + , RT = 1.499 min Compound 47: LC / MS: 312 [M+H] + , RT = 1.363 Compound 48: LC / MS: 312 [M+H] + , RT = 1.335 min Compound 49: LC / MS: 316 [M+H] + , RT = 1.985 points for compound 50: 1 H-NMR (CDCl3) δ: 8.60-8.59 (1H, m), 7.65 (1H, td), 7.61 (1H, br s), 7.56-7.53 (2H, m), 7.45-7.41 (4H, m), 7.37-7.35 (1H, m), 7.31 (1H, d), 7.23 (1H, dd), 6.30 (1H, d), 5.49 (1H, d). Compound 51: 1 H-NMR (CDCl3) δ: 8.62 (1H, d), 7.65 (1H, td), 7.54 (4H, d), 7.47-7.39 (3H, m), 7.27-7.23 (1H, m), 7.13-7.11 (1H, m), 6.64 (1H, d), 5.63 (1H, d). Compound 52: 1 H-NMR (CDCl3) δ: 8.63 (1H, d), 7.89 (1H, d), 7.70-7.68 (1H, br m), 7.64 (1H, td), 7.58-7.56 (2H, m), 7.46-7.44 (3H, m), 7.40-7.37 (1H, m), 7.27-7.24 (1H, m), 7.09 (1H, d), 6.21 (1H, d), 5.73 (1H, d). Compound 53:1 H-NMR (CDCl3) δ: 8.60 (1H, d), 7.71 (1H, td), 7.45-7.42 (4H, m), 7.40-7.36 (1H, m), 7.32-7.27 (1H, m), 7.26-7.24 (1H, m), 7.05 (2H, d), 5.75 (1H, d), 5.34 (1H, d). Compound 54: 1 H-NMR (CDCl3) δ: 8.63 (1H, d), 7.73 (1H, td), 7.51-7.43 (5H, m), 7.31-7.28 (1H, m), 7.25-7.24 (1H, m), 6.26 (1H, d), 5.58 (1H, d). Compound 55: 1 H-NMR (CDCl3) δ: 8.62 (1H, d), 7.64 (1H, t), 7.58 (2H, d), 7.43-7.40 (4H, m), 7.35-7.28 (2H, m), 7.24-7.22 (1H, m), 7.09 (1H, d), 6.01 (1H, d), 5.15 (1H, d), 2.42 (3H, s). Compound 56: 1 H-NMR (CDCl3) δ: 8.62-8.61 (1H, m), 7.63-7.56 (3H, m), 7.44-7.40 (2H, m), 7.35-7.30 (1H, m), 7.24 (2H, s), 7.23-7.20 (1H, m), 6.96 (1H, dd), 6.26 (1H, s), 5.47 (1H, br s), 2.29 (6H, s). Compound 57: 1 H-NMR (CDCl3) δ: 8.58 (1H, d), 7.67 (1H, td), 7.55-7.54 (2H, m), 7.45-7.43 (3H, m), 7.37-7.34 (2H, m), 7.30-7.28 (2H, m), 7.23 (1H, dd), 6.15 (1H, d), 5.43 (1H, d). Compound 58: 1H-NMR (CDCl3) δ: 8.79 (2H, d), 7.40-7.33 (1H, m), 7.29 (1H, t), 7.08-7.01 (2H, m), 6.99-6.88 (2H, m), 6.28 (1H, d), 5.13 (1H, d). Compound 59: 1 H-NMR (CDCl3) δ: 8.60 (1H, d), 7.67 (1H, td), 7.42-7.38 (2H, m), 7.35-7.28 (4H, m), 7.24-7.20 (4H, m), 5.77 (1H, s), 5.25 (1H, br s), 2.25 (3H, s). This compound 60: 1 H-NMR (CDCl3) δ: 8.60 (1H, d), 7.67 (1H, td), 7.40 (2H, t), 7.33-7.31 (1H, m), 7.29-7.27 (1H, m), 7.23 (1H, dd), 7.11-7.10 (4H, m), 5.73 (1H, s), 5.20 (1H, br s), 1.99 (6H, s). Compound 61: 1 H-NMR (CDCl3) δ: 8.62-8.61 (1H, m), 7.69-7.63 (1H, m), 7.54-7.51 (2H, m), 7.47-7.42 (3H, m), 7.40-7.38 (1H, m), 7.26-7.24 (1H, m), 7.20-7.16 (2H, m), 6.40 (1H, d), 5.57 (1H, d). This compound 80: 1 H-NMR (CDCl3) δ: 8.57-8.56 (1H, m), 7.68 (1H, td), 7.54-7.50 (2H, m), 7.45-7.42 (2H, m), 7.40-7.36 (1H, m), 7.29 (1H, d), 7.25-7.22 (1H, m), 7.06 (2H, d), 5.91 (1H, s), 2.02 (3H, t). Compound 93: 1H-NMR (CDCl3) δ: 9.24 (1H, d), 8.73 (1H, d), 7.38 (1H, d), 7.24-7.10 (5H, m), 6.22 (1H, d), 4.71 (1H, d). Compound 94: 1 H-NMR (CDCl3) δ: 8.28 (1H, d), 7.56-7.49 (2H, m), 7.47-7.37 (3H, m), 7.23-7.13 (2H, m), 7.13-7.06 (2H, m), 6.19 (1H, d), 5.21 (1H, d), 3.87 (3H, s). Compound 95: 1 H-NMR (CDCl3) δ: 8.61-8.57 (1H, m), 7.65-7.59 (1H, m), 7.54-7.49 (4H, m), 7.47-7.41 (2H, m), 7.41-7.29 (4H, m), 7.27-7.22 (1H, m), 7.17-7.13 (1H, m), 7.09-7.01 (2H, m), 6.52 (1H, s). Compound 96: 1 H-NMR (CDCl3) δ: 8.55 (2H, dq), 7.86 (2H, dt), 7.71-7.65 (2H, m), 7.54-7.48 (2H, m), 7.45-7.34 (4H, m), 7.21 (2H, ddd), 7.06-6.97 (2H, m).
[0084] Preparation Example 2: To a mixture of 0.16 g of Compound 1 and 5 mL of THF, 0.25 mL of phosphorus tribromide was added at room temperature and stirred under reflux for 3 hours. 1 M aqueous sodium hydroxide solution was added to the resulting mixture, and the mixture was extracted with chloroform. The resulting organic layer was washed with saturated brine and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 4:1 to 1:10) to obtain 0.05 g of Compound 6, which is represented by the following formula: This compound 6: 1 H-NMR (CDCl3) δ: 9.09 (1H, dd), 7.57-7.52 (2H, m), 7.49-7.34 (5H, m), 7.20-7.12 (2H, m), 4.46 (2H, s).
[0085] Preparation Example 2-1 Compounds prepared according to Preparation Example 2 and their physical properties are shown below. In compound (IA-1), R 1a , R 2a , X 1a , X 2a , X 3a , X 4a , R 5A , R 5B , R 5C , R 5D and a compound in which the combination of E is any of the combinations described in [Table A-2].
[0086]
[0087] Compound 7: LC / MS: 324 [M+H+MeCN] + , RT = 1.932 min Compound 7: 1 H-NMR (CDCl3) δ: 8.58-8.55 (1H, m), 8.52-8.49 (1H, m), 8.43 (1H, d), 7.56-7.52 (2H, m), 7.48-7.42 (2H, m), 7.41-7.35 (1H, m), 7.19-7.13 (2H, m), 4.27 (2H, s). Compound 8: 1 H-NMR (CDCl3) δ: 8.55 (1H, dd), 7.60 (1H, td), 7.56-7.52 (2H, m), 7.47-7.41 (2H, m), 7.40-7.35 (1H, m), 7.20-7.09 (4H, m), 4.25 (2H, s). Compound 9: LC / MS: 324 [M+H+MeCN] + , RT = 1.972 min Compound 9: 1 H-NMR (CDCl3) δ: 8.69 (2H, d), 7.58-7.54 (2H, m), 7.47-7.42 (2H, m), 7.41-7.35 (1H, m), 7.20-7.13 (3H, m), 4.44 (2H, s). Compound 10: LC / MS: 300 [M+H] + , RT = 2.171 min Compound 10: 1H-NMR (CDCl3) δ: 8.40 (1H, d), 7.56-7.52 (2H, m), 7.47-7.42 (2H, m), 7.42-7.37 (1H, m), 7.34-7.29 (1H, m), 7.22-7.18 (1H, m), 7.17-7.13 (2H, m), 4.23 (2H, s). Compound 64: 1 H-NMR (CDCl3) δ: 7.57-7.54 (2H, m), 7.49-7.43 (3H, m), 7.41-7.36 (1H, m), 7.18-7.12 (2H, m), 6.99 (1H, d), 6.86 (1H, d), 4.23 (2H, s), 2.55 (3H, s). Compound 65: 1 H-NMR (CDCl3) δ: 8.39-8.37 (1H, m), 7.57-7.51 (2H, m), 7.47-7.35 (4H, m), 7.17-7.11 (2H, m), 7.08 (1H, d), 4.21 (2H, s), 2.29 (3H, s). Compound 66: 1 H-NMR (CDCl3) δ: 8.41 (1H, d), 7.57-7.53 (2H, m), 7.47-7.42 (2H, m), 7.41-7.35 (1H, m), 7.18-7.12 (2H, m), 6.99 (1H, s), 6.95 (1H, d), 4.21 (2H, s), 2.30 (3H, d). Compound 67: 1 H-NMR (CDCl3) δ: 8.38-8.34 (1H, m), 7.57-7.53 (2H, m), 7.47-7.34 (4H, m), 7.17-7.10 (2H, m), 7.05 (1H, dd), 4.19 (2H, s), 2.41 (3H, s). Compound 68: 1 H-NMR (CDCl3) δ: 8.36-8.32 (1H, m), 7.57-7.52 (2H, m), 7.47-7.41 (2H, m), 7.40-7.34 (2H, m), 7.20-7.11 (3H, m), 4.29 (2H, s). Compound 69: 1H-NMR (CDCl3) δ: 8.40 (1H, d), 7.55-7.52 (2H, m), 7.46-7.43 (2H, m), 7.40-7.37 (1H, m), 7.34-7.30 (1H, m), 7.20 (1H, dd), 7.17-7.13 (2H, m), 4.23 (2H, s). Compound 70: 1 H-NMR (CDCl3) δ: 8.69 (2H, d), 7.44-7.37 (1H, m), 7.16 (1H, t), 7.13-7.07 (2H, m), 6.99-6.90 (2H, m), 4.44 (2H, s). Compound 71: 1 H-NMR (CDCl3) δ: 8.58-8.57 (1H, m), 7.62-7.53 (5H, m), 7.42 (2H, t), 7.35-7.31 (3H, m), 7.16-7.13 (2H, m), 4.20 (2H, s). Compound 72: 1 H-NMR (CDCl3) δ: 8.58 (1H, d), 7.63-7.59 (2H, m), 7.57-7.55 (2H, m), 7.46-7.42 (3H, m), 7.38-7.34 (2H, m), 7.17-7.13 (2H, m), 4.34 (2H, s). Compound 73: 1 H-NMR (CDCl3) δ: 8.58 (1H, d), 7.59-7.57 (5H, m), 7.48-7.46 (2H, m), 7.34-7.30 (1H, m), 7.14 (1H, dd), 6.99 (1H, d), 4.57 (2H, s). Compound 74: 1 H-NMR (CDCl3) δ: 8.59 (1H, d), 7.89 (1H, s), 7.68 (1H, d), 7.61-7.59 (3H, m), 7.48-7.36 (4H, m), 7.16 (1H, dd), 7.09 (1H, d), 4.40 (2H, s). Compound 75: 1H-NMR (CDCl3) δ: 8.60-8.58 (1H, m), 7.65 (1H, td), 7.43 (4H, d), 7.40-7.36 (1H, m), 7.20-7.17 (2H, m), 6.89 (2H, d), 4.15 (2H, s). Compound 76: 1 H-NMR (CDCl3) δ: 8.56 (1H, t), 7.65 (1H, td), 7.49-7.45 (6H, m), 7.17 (1H, dd), 4.31 (2H, s). Compound 77: 1 H-NMR (CDCl3) δ: 8.57 (1H, d), 7.58-7.57 (3H, m), 7.43-7.41 (4H, m), 7.33-7.32 (1H, m), 7.25-7.22 (1H, br m), 7.12 (1H, dd), 7.03 (1H, d), 4.22 (2H, s), 2.32 (3H, s). Compound 78: 1 H-NMR (CDCl3) δ: 8.58-8.56 (1H, m), 7.62-7.59 (2H, m), 7.52 (1H, td), 7.44-7.42 (2H, m), 7.33-7.32 (3H, m), 7.11-7.09 (1H, m), 6.81 (1H, d), 4.28 (2H, s), 2.32 (6H, s). Compound 79: 1 H-NMR (CDCl3) δ: 8.57-8.56 (1H, m), 7.62 (1H, td), 7.57-7.55 (2H, m), 7.45-7.41 (2H, m), 7.36-7.33 (3H, m), 7.29 (1H, d), 7.20 (1H, d), 7.14 (1H, dd), 4.23 (2H, s). This compound 81+92 (this compound 81 is a mixture of this compound 92 and this compound 92 is a mixture of 1:1 (モルratio)): 1H-NMR (CDCl3) δ: 8.62-8.61 (1H, m), 8.58-8.57 (1H, m), 7.68-7.63 (2H, m), 7.60-7.57 (2H, m), 7.54-7.51 (2H, m), 7.49-7.37 (6H, m), 7.31 (2H, dd), 7.21-7.19 (3H, m), 7.14-7.12 (1H, m), 7.10-7.09 (2H, m), 6.55 (1H, d), 5.70 (1H, s), 4.75 (1H, q), 1.81 (3H, d). Compound 82: 1 H-NMR (CDCl3) δ: 8.58 (1H, d), 7.61 (1H, td), 7.41-7.37 (2H, m), 7.34-7.28 (3H, m), 7.19-7.17 (3H, m), 7.14-7.12 (2H, m), 4.16 (2H, s), 2.24 (3H, s). Compound 83: 1 H-NMR (CDCl3) δ: 8.58 (1H, dq), 7.62 (1H, td), 7.41-7.39 (2H, m), 7.32-7.31 (1H, m), 7.22 (1H, d), 7.15-7.12 (3H, m), 7.01 (2H, s), 4.12 (2H, s), 1.99 (6H, s). Compound 89: LC / MS: 298 [M+H] + , RT = 2.005 points Compound 90: 1 H-NMR (CDCl3) δ: 8.57 (1H, d), 7.61-7.58 (2H, m), 7.56 (1H, td), 7.53 (1H, d) 7.45-7.43 (2H, m), 7.41-7.38 (1H, m), 7.35-7.33 (1H, m), 7.27 (1H, d), 7.11 (1H, dd), 7.01 (1H, d), 4.28 (2H, s), 3.25-3.18 (1H, m), 1.17 (6H, d).
[0088] Preparation Example 3: Under a nitrogen atmosphere, 0.30 g of the present compound 3 was added to a mixture of 0.05 g of sodium hydride (oil, 60%) and 5 mL of THF, and the mixture was stirred at room temperature for 30 minutes. 0.075 mL of methyl iodide was added to the resulting mixture, and the mixture was stirred at room temperature for 4.5 hours. Saturated aqueous sodium bicarbonate was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate=3:2) to obtain 0.26 g of the present compound 11 represented by the following formula: This compound 11: 1 H-NMR (CDCl3) δ: 8.55-8.51 (1H, m), 7.81-7.70 (2H, m), 7.55-7.50 (2H, m), 7.48-7.34 (3H, m), 7.20-7.15 (1H, m), 7.15-7.07 (2H, m), 5.85 (1H, s), 3.54 (3H, s).
[0089] Preparation Example 3-1 Compounds prepared according to Preparation Example 3 and their physical properties are shown below. In compound (IA-1), R 1a , R 2a , X 1a , X 2a , X 3a , X 4a , R 5A , R 5B , R 5C , R 5D and a compound in which the combination of E is any of the combinations described in [Table A-3].
[0090] This compound 12: 1 H-NMR (CDCl3) δ: 8.51 (1H, d), 7.83 (1H, d), 7.78-7.72 (1H, m), 7.55-7.50 (2H, m), 7.47-7.35 (3H, m), 7.20-7.14 (1H, m), 7.13-7.05 (2H, m), 5.93 (1H, s), 3.68-3.56 (2H, m), 1.72-1.64 (2H, m), 1.50-1.39 (2H, m), 0.92 (3H, t). Compound 13: 1H-NMR (CDCl3) δ: 8.51 (1H, dt), 7.90 (1H, d), 7.75 (1H, td), 7.56-7.50 (2H, m), 7.46-7.27 (8H, m), 7.20-7.15 (1H, m), 7.14-7.08 (2H, m), 6.05 (1H, s), 4.70 (2H, dd). Compound 14: 1 H-NMR (CDCl3) δ: 8.60-8.55 (1H, m), 7.78-7.69 (2H, m), 7.53-7.49 (3H, m), 7.46-7.35 (3H, m), 7.24-7.18 (1H, m), 7.16-7.09 (3H, m), 6.71 (1H, d).
[0091] Production Example 4: Under a nitrogen atmosphere, 0.30 g of this compound 3, 0.2 mL of acetic anhydride was added to a mixture of 12 mg of 4-dimethylaminopyridine, 0.42 mL of triethylamine, and 5 mL of chloroform, and the mixture was stirred at room temperature for 4 hours. Saturated aqueous sodium bicarbonate was added to the resulting mixture, and the mixture was extracted with chloroform. The resulting organic layer was washed with saturated brine and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate=3:2) to obtain 0.33 g of this compound 15 represented by the following formula: This compound 15: 1 H-NMR (CDCl3) δ: 8.57 (1H, d), 7.76-7.70 (1H, m), 7.59-7.49 (3H, m), 7.47-7.35 (3H, m), 7.29 (1H, s), 7.23-7.17 (1H, m), 7.15-7.08 (2H, m), 2.24 (3H, s).
[0092] Preparation Example 5: To a mixture of 0.077 g of this compound 3 and 5 mL of chloroform, 0.165 g of Dess-Martin periodinane was added at room temperature, and the mixture was stirred at room temperature for 4 hours. 5 mL of saturated aqueous sodium thiosulfate solution and 5 mL of saturated aqueous sodium bicarbonate solution were added sequentially to the resulting mixture, and the mixture was stirred for 1 hour, followed by extraction with chloroform. The resulting organic layer was washed with saturated brine and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain 0.072 g of this compound 16, which is represented by the following formula: This compound 16: 1 H-NMR (CDCl3) δ: 8.71 (1H, d), 8.19 (1H, d), 7.96-7.89 (1H, m), 7.62-7.56 (2H, m), 7.54-7.41 (4H, m), 7.25-7.18 (2H, m).
[0093] Preparation Example 6: A mixture of 0.28 g of intermediate 2,4-chlorophenylboronic acid (0.16 g), {1,1'-bis(diphenylphosphino)ferrocene}dichloropalladium(II) (0.02 g), tripotassium phosphate (0.43 g), DME (5 mL), and water (0.5 mL) was stirred under reflux for 5 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was concentrated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain 0.30 g of Compound 17, which is represented by the following formula: This compound 17: 1 H-NMR (CDCl3) δ: 8.56-8.55 (1H, m), 7.61 (1H, td), 7.51-7.39 (4H, m), 7.22-7.06 (4H, m), 4.25 (2H, s).
[0094] Preparation Example 6-1 Compounds prepared according to Preparation Example 6 and their physical properties are shown below. In compound (IA-1), R 1a , R 2a , X 1a , X 2a , X 3a , X 4a , R 5A , R 5B , R5C , R 5D , and びEのcombination せが [Table A-4] are recorded のいずれかのcombination せである compounds.
[0095] This compound 18: 1 H-NMR (CDCl3) δ: 8.57 (1H, d), 7.62 (1H, td), 7.50-7.45 (1H, m), 7.33-7.30 (3H, m), 7.21 (1H, d), 7.17-7.11 (1H, m), 7.06-6.99 (2H, m), 4.27 (2H, s). Compound 19: 1 H-NMR (CDCl3) δ: 8.55 (1H, d), 7.61 (1H, td), 7.53 (1H, s), 7.44-7.33 (3H, m), 7.19 (1H, d), 7.15-7.09 (3H, m), 4.25 (2H, s). This compound 20: 1 H-NMR (CDCl3) δ: 8.56 (1H, m), 7.61 (1H, m), 7.44-7.35 (2H, m), 7.24-7.13 (6H, m), 4.26 (2H, s) Compound 21: 1 H-NMR (CDCl3) δ: 8.56-8.55 (1H, m), 7.63-7.59 (1H, m), 7.44-7.05 (8H, m), 4.25 (2H, s) Compound 22: 1 H-NMR (CDCl3) δ: 8.56-8.55 (1H, m), 7.63-7.58 (1H, m), 7.52-7.49 (2H, m), 7.20-7.08 (6H, m), 4.25 (2H, s) Compound 23: 1 H-NMR (CDCl3) δ: 8.56-8.55 (1H, m), 7.64-7.59 (1H, m), 7.21-7.12 (7H, m), 4.27 (2H, s) Compound 24: 1H-NMR (CDCl3) δ: 8.56-8.55 (1H, m), 7.63-7.59 (1H, m), 7.42-7.36 (1H, m), 7.20-7.07 (4H, m), 6.99-6.90 (2H, m), 4.26 (2H, s) Compound 25: 1 H-NMR (CDCl3) δ: 8.56-8.55 (1H, m), 7.63-7.59 (1H, m), 7.21-7.02 (7H, m), 4.26 (2H, s) Compound 26: 1 H-NMR (CDCl3) δ: 8.55-8.59 (1H, m), 7.57-7.67 (1H, m), 7.28-7.40 (1H, m), 6.95-7.22 (6H, m), 4.28 (2H, s) Compound 27: 1 H-NMR (CDCl3) δ: 8.55-8.54 (m, 1H), 7.63-7.59 (m, 1H), 7.37-7.32 (m, 1H), 7.26-7.05 (m, 6H), 4.25 (s, 2H) Compound 28: 1 H-NMR (CDCl3) δ: 8.55-8.54 (m, 1H), 7.63-7.59 (m, 1H), 7.20-7.05 (m, 6H), 6.86-6.81 (m, 1H), 4.25 (s, 2H) Compound 29: LC / MS: 356 [M+H] + , RT = 2.233 points for compound 30: 1 H-NMR (CDCl3) δ: 8.57 (1H, d), 7.64-7.58 (1H, m), 7.27-7.11 (5H, m), 7.03-6.97 (2H, m), 4.25 (2H, s), 2.97 (4H, t), 2.11-2.01 (2H, m). Compound 31: 1 H-NMR (CDCl3) δ: 8.57-8.54 (1H, m), 7.63-7.57 (1H, m), 7.37-7.32 (3H, m), 7.22-7.11 (5H, m), 4.25 (2H, s), 2.42 (3H, s). Compound 32: 1H-NMR (CDCl3) δ: 8.55 (1H, d), 7.62-7.57 (1H, m), 7.46-7.42 (2H, m), 7.25 (2H, d), 7.18 (1H, d), 7.15-7.09 (3H, m), 4.24 (2H, s), 2.39 (3H, s). Compound 33: 1 H-NMR (CDCl3) δ: 8.58-8.55 (1H, m), 7.63-7.57 (1H, m), 7.37-7.32 (1H, m), 7.30 (1H, dd), 7.20 (1H, d), 7.15-7.09 (3H, m), 7.05-7.00 (1H, m), 6.99 (1H, d), 4.25 (2H, s), 3.83 (3H, s). Compound 34: LC / MS: 312 [M+H] + , RT = 1.821 min Compound 35: LC / MS: 312 [M+H] + , RT = 1.781 min Compound 36: LC / MS: 307 [M+H] + , RT = 1.614 Compound 37: LC / MS: 362 [M+H] + , RT = 2.061 % Compound 38: LC / MS: 323 [M+H] + , RT = 1.525 min Compound 39: LC / MS: 296 [M+H] + , RT = 1.940 Compound 40: LC / MS: 413 [M+H+MeCN] + , RT = 1.495 min Compound 41: LC / MS: 388 [M+H] + , RT = 1.660 Compound 42: LC / MS: 325 [M+H] + , RT = 1.107 for compound 43: 1 H-NMR (CDCl3) δ: 8.55 (1H, d), 7.62 (1H, td), 7.23-7.07 (6H, m), 4.25 (2H, s). Compound 62: 1H-NMR (CDCl3) δ: 8.71 (2H, d), 7.47-7.43 (4H, m), 7.40-7.35 (1H, m), 7.16 (1H, t), 6.95-6.87 (2H, m), 4.34 (2H, s). Compound 63: 1 H-NMR (CDCl3) δ: 8.72 (2H, d), 7.47-7.38 (5H, m), 7.33-7.24 (3H, m), 7.16 (1H, t), 4.36 (2H, s). Compound 85: LC / MS: 282 [M+H] + , RT = 1.645 for compound 85: 1 H-NMR (CDCl3) δ: 8.57 (1H, dd), 7.64-7.58 (1H, m), 7.44-7.39 (1H, m), 7.36-7.27 (4H, m), 7.23-7.19 (2H, m), 7.15-7.11 (2H, m), 4.23 (2H, s). Compound 86: LC / MS: 300 [M+H] + , RT = 1.711 Compound 86: 1 H-NMR (CDCl3) δ: 8.57 (1H, dd), 7.65-7.59 (1H, m), 7.37-7.32 (1H, m), 7.30-7.24 (2H, m), 7.23-7.19 (1H, m), 7.19-7.11 (4H, m), 4.23 (2H, s). Compound 87: LC / MS: 283 [M+H] + , RT = 1.905 for compound 87: 1 H-NMR (CDCl3) δ: 8.71 (2H, d), 7.45-7.27 (5H, m), 7.22-7.11 (3H, m), 4.40 (2H, s). Compound 88: LC / MS: 301 [M+H] + , RT = 1.934 for compound 98: 1H-NMR (CDCl3) δ: 8.70 (2H, d), 7.29-7.23 (2H, m), 7.18 (1H, t), 7.13-7.06 (2H, m), 7.01-6.94 (2H, m), 5.45 (1H, br s), 4.45 (2H, s).
[0096] Preparation Example 7: To a mixture of 0.51 g of 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride and 2.0 mL of chloroform was added 0.30 g of the present compound 3, and the mixture was stirred at room temperature for 3 hours. To the resulting mixture was added an aqueous potassium hydroxide solution (1 M), and the mixture was allowed to stand overnight, followed by extraction with chloroform. The resulting organic layer was concentrated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain 0.27 g of the present compound 91 represented by the following formula. This compound 91: 1 H-NMR (CDCl3) δ: 8.55 (1H, d), 7.85-7.73 (2H, m), 7.56-7.51 (2H, m), 7.48-7.37 (3H, m), 7.25-7.21 (1H, m), 7.14 (2H, d), 6.91 (1H, d).
[0097] Production Example 8: Under an argon atmosphere, 2.0 mL of bis(2,2,6,6-tetramethylpiperidinyl)zinc (toluene solution, 0.5 M) was added to a mixture of 0.20 mL of 2-methylpyridine and 7.0 mL of toluene, and the mixture was stirred at 50°C for 17 hours. 0.53 g of 1-bromo-2-methoxy-4-phenylbenzene, 0.05 g of tris(dibenzylideneacetone)dipalladium, and 0.03 mL of MTBE were added to the resulting mixture, and the mixture was stirred at room temperature for 24 hours. Water was added to the resulting mixture, and the mixture was extracted with MTBE. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain 0.07 g of Compound 84, which is represented by the following formula: This compound 84: 1H-NMR (CDCl3) δ: 8.55 (1H, d), 7.60-7.54 (3H, m), 7.43 (2H, t), 7.35-7.33 (1H, m), 7.25 (1H, d), 7.12 (4H, m), 4.20 (2H, s), 3.87 (3H, s).
[0098] Production Example 9: To a mixture of 0.50 g of 3-fluoro-[1,1'-biphenyl]-4-acetonitrile, 0.25 mL of chloropyrazine, and 8.0 mL of DMF, 0.53 g of potassium tert-butoxide was added at 0°C, and the mixture was stirred at room temperature for 1 hour. Water was added to the resulting mixture, and the mixture was extracted with MTBE. The resulting organic layer was washed with saturated brine and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain 0.51 g of Compound 97 represented by the following formula: This compound 97: 1 H-NMR (CDCl3) δ: 8.74 (1H, s), 8.62-8.58 (2H, m), 7.67 (1H, t), 7.58-7.53 (2H, m), 7.49-7.37 (4H, m), 7.35 (1H, dd), 5.66 (1H, s).
[0099] Reference Production Example 1 Under a nitrogen atmosphere, a THF solution (8.0 mL) of 3.8 g of 2-bromopyridine was added dropwise to 6.3 mL of isopropyl magnesium chloride lithium chloride complex (THF solution, 1.3 M) at −15° C., and the mixture was stirred at room temperature for 1 hour. The resulting mixture was added dropwise to a THF solution (20 mL) of 5.0 g of 4-bromo-2,6-difluorobenzaldehyde at 0° C., and the mixture was stirred at room temperature for 20 hours. Aqueous ammonium chloride solution was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate=2:3) to obtain 5.27 g of Intermediate 1 represented by the following formula: Intermediate 1: 1H-NMR (CDCl3) δ: 8.59 (1H, dt), 7.69-7.64 (1H, m), 7.27-7.23 (1H, m), 7.13 (1H, d), 7.10-7.04 (2H, m), 6.14 (1H, d), 5.47 (1H, d).
[0100] Reference Production Example 1-1 Compounds produced according to Reference Production Example 1 and their physical properties are shown below. 1a , R 2a , X 1a , X 2a , X 3a , X 4a , R 5A , R 5B , R 5C , R 5D and a compound in which the combination of E is a combination described in [Table B-1].
[0101] Intermediate 3: 1 H-NMR (CDCl3) δ: 8.56 (1H, d), 7.66 (1H, td), 7.33-7.21 (5H, m), 6.06 (1H, s), 5.44 (1H, s).
[0102] Reference Preparation Example 2: To a mixture of 5.1 g of Intermediate 1 and 34 mL of THF, 3.2 mL of phosphorus tribromide was added at 0°C and stirred under reflux for 2 hours. A 1 M aqueous solution of sodium hydroxide was added to the resulting mixture, and the mixture was extracted with MTBE. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate=7:3) to obtain 3.1 g of Intermediate 2 represented by the following formula: Intermediate 2: 1 H-NMR (CDCl3) δ: 8.54-8.51 (1H, m), 7.59 (1H, td), 7.16-7.07 (4H, m), 4.16 (2H, s).
[0103] Reference Production Example 2-1 Compounds prepared according to Reference Production Example 2 and their physical properties are shown below. 1a , R 2a , X1a , X 2a , X 3a , X 4a , R 5A , R 5B , R 5C , R 5D and a compound in which the combination of E is any of the combinations described in [Table B-2].
[0104] Intermediate 4: 1 H-NMR (CDCl3) δ: 8.55-8.53 (1H, m), 7.60 (1H, td), 7.25-7.21 (2H, m), 7.16-7.12 (3H, m), 4.13 (2H, s). Intermediate 5: 1 H-NMR (CDCl3) δ: 8.68 (2H, d), 7.28-7.13 (4H, m), 4.31 (2H, s). Intermediate 6: 1 H-NMR (CDCl3) δ: 8.66 (2H, d), 7.17-7.09 (3H, m), 4.35 (2H, s).
[0105] Examples of the compounds (including the compounds of the present invention) produced according to the above production methods and production examples are shown below. In the compound represented by the formula (hereinafter referred to as compound (A-1)), Z is a pyridin-2-yl group, and R 1X , R 2X , R 3X , R 4X , R 5X , R 6X , and E 1X The combination of the above is any one of the combinations described in Combination A (hereinafter referred to as compound group SX1).
[0106] Combination A consists of substituent numbers A1 to A2288. Substituent numbers A1 to A2288 are the substituents R 1X , R 2X , R 3X , R 4X , R 5X , R 6X , and E 1X The following represents a combination of [Substituent Number; R 1X ,R 2X,R 3X ,R 4X ,R 5X ,R 6X ,E 1X For example, the substituent number A3 is R 1X , R 2X , R 4X , R 5X , and R 6X are each a hydrogen atom, and R 3X is a methyl group, and E 1X represents a combination in which the aryl group is a phenyl group.
[0107] Combination A: [A1; H, H, F, H, H, H, Ph], [A2; H, H, Cl, H, H, H, Ph], [A3; H, H, Me, H, H, H, Ph], [A4; H, H, CN, H, H, H, Ph], [A5; H, H, OH, H, H, H, Ph], [A6; H, H, cPr, H, H, H, Ph], [A7; H, H, F, F, H, H, Ph], [A8; H, H, F, H, F, H, Ph], [A9; H, H, F, H, H, F, Ph], [A10; H, H, Cl, H, H, Cl, Ph], [A11; H, H, Me, H, H, Me, Ph], [A12; H, H, F, F, F, F, Ph], [A13; F, H, F, H, H, H, Ph], [A14; F, H, Cl, H, H, H, Ph], [A15; F, H, Me, H, H, H, Ph], [A16; F, H, CN, H, H, H, Ph], [A17; F, H, OH, H, H, H, Ph], [A18; F, H, cPr, H, H, H, Ph], [A19; F, H, F, F, H, H, Ph], [A20; F, H, F, H, F, H, Ph], [A21; F, H, F, H, H, F, Ph], [A22; F, H, Cl, H, H, Cl, Ph], [A23; F, H, Me, H, H, Me, Ph], [A24; F, H, F, F, F, F, Ph], [A25; Me, H, F, H, H, H, Ph], [A26; Me, H, Cl, H, H, H, Ph], [A27; Me, H, Me, H, H, H, Ph], [A28; Me, H, CN, H, H, H, Ph], [A29; Me, H, OH, H, H, H, Ph], [A30; Me, H, cPr, H, H, H, Ph], [A31; Me, H, F, F, H, H, Ph], [A32; Me, H, F, H, F, H, Ph], [A33; Me, H, F, H, H, F, Ph], [A34; Me, H, Cl, H, H, Cl, Ph], [A35; Me, H, Me, H, H, Me, Ph], [A36; Me, H, F, F, F, F, Ph], [A37; OMe, H, F, H, H, H, Ph], [A38; OMe, H, Cl, H, H, H, Ph], [A39; OMe, H, Me, H, H, H, Ph], [A40; OMe, H, CN, H, H, H, Ph], [A41; OMe, H, OH, H, H, H, Ph], [A42; OMe, H, cPr, H, H, H, Ph], [A43; OMe, H, F, F, H, H, Ph], [A44; OMe, H, F, H, F, H, Ph], [A45;OMe,H,F,H,H,F,Ph]、[A46;OMe,H,Cl,H,H,Cl,Ph]、[A47;OMe,H,Me,H,H,Me,Ph]、[A48;OMe,H,F,F,F,F,Ph]、[A49;OH,H,F,H,H,H,Ph]、[A50;OH,H,Cl,H,H,H,Ph]、[A51;OH,H,Me,H,H,H,Ph]、[A52;OH,H,CN,H,H,H,Ph]、[A53;OH,H,OH,H,H,H,Ph]、[A54;OH,H,cPr,H,H,H,Ph]、[A55;OH,H,F,F,H,H,Ph]、[A56;OH,H,F,H,F,H,Ph]、[A57;OH,H,F,H,H,F,Ph]、[A58;OH,H,Cl,H,H,Cl,Ph]、[A59;OH,H,Me,H,H,Me,Ph]、[A60;OH,H,F,F,F,F,Ph]、[A61;Me,Me,F,H,H,H,Ph]、[A62;Me,Me,Cl,H,H,H,Ph]、[A63;Me,Me,Me,H,H,H,Ph]、[A64;Me,Me,CN,H,H,H,Ph]、[A65;Me,Me,OH,H,H,H,Ph]、[A66;Me,Me,cPr,H,H,H,Ph]、[A67;Me,Me,F,F,H,H,Ph]、[A68;Me,Me,F,H,F,H,Ph]、[A69;Me,Me,F,H,H,F,Ph]、[A70;Me,Me,Cl,H,H,Cl,Ph]、[A71;Me,Me,Me,H,H,Me,Ph]、[A72;Me,Me,F,F,F,F,Ph]、[A73;F,F,F,H,H,H,Ph]、[A74;F,F,Cl,H,H,H,Ph]、[A75;F,F,Me,H,H,H,Ph]、[A76;F,F,CN,H,H,H,Ph]、[A77;F,F,OH,H,H,H,Ph]、[A78;F,F,cPr,H,H,H,Ph]、[A79;F,F,F,F,H,H,Ph]、[A80;F,F,F,H,F,H,Ph]、[A81;F,F,F,H,H,F,Ph]、[A82;F,F,Cl,H,H,Cl,Ph]、[A83;F,F,Me,H,H,Me,Ph]、[A84;F,F,F,F,F,F,Ph]、[A85;OH,Me,F,H,H,H,Ph]、[A86;OH,Me,Cl,H,H,H,Ph]、[A87;OH,Me,Me,H,H,H,Ph]、[A88;OH,Me,CN,H,H,H,Ph]、[A89;OH,Me,OH,H,H,H,Ph]、[A90;OH,Me,cPr,H,H,H,Ph]、[A91;OH,Me,F,F,H,H,Ph]、[A92;OH,Me,F,H,F,H,Ph]、[A93;OH,Me,F,H,H,F,Ph]、[A94;OH,Me,Cl,H,H,Cl,Ph]、[A95;OH,Me,Me,H,H,Me,Ph]、[A96;OH,Me,F,F,F,F,Ph]、[A97;H,H,F,H,H,H,2-F-Ph]、[A98;H,H,Cl,H,H,H,2-F-Ph]、[A99;H,H,Me,H,H,H,2-F-Ph]、[A100;H,H,CN,H,H,H,2-F-Ph]、 [A101;H,H,OH,H,H,H,2-F-Ph]、[A102;H,H,cPr,H,H,H,2-F-Ph]、[A103;H,H,F,F,H,H,2-F-Ph]、[A104;H,H,F,H,F,H,2-F-Ph]、[A105;H,H,F,H,H,F,2-F-Ph]、[A106;H,H,Cl,H,H,Cl,2-F-Ph]、[A107;H,H,Me,H,H,Me,2-F-Ph]、[A108;H,H,F,F,F,F,2-F-Ph]、[A109;F,H,F,H,H,H,2-F-Ph]、[A110;F,H,Cl,H,H,H,2-F-Ph]、[A111;F,H,Me,H,H,H,2-F-Ph]、[A112;F,H,CN,H,H,H,2-F-Ph]、[A113;F,H,OH,H,H,H,2-F-Ph]、[A114;F,H,cPr,H,H,H,2-F-Ph]、[A115;F,H,F,F,H,H,2-F-Ph]、[A116;F,H,F,H,F,H,2-F-Ph]、[A117;F,H,F,H,H,F,2-F-Ph]、[A118;F,H,Cl,H,H,Cl,2-F-Ph]、[A119;F,H,Me,H,H,Me,2-F-Ph]、[A120;F,H,F,F,F,F,2-F-Ph]、[A121;Me,H,F,H,H,H,2-F-Ph]、[A122;Me,H,Cl,H,H,H,2-F-Ph]、[A123;Me,H,Me,H,H,H,2-F-Ph]、[A124;Me,H,CN,H,H,H,2-F-Ph]、[A125;Me,H,OH,H,H,H,2-F-Ph]、[A126;Me,H,cPr,H,H,H,2-F-Ph]、 [A127;Me,H,F,F,H,H,2-F-Ph]、[A128;Me,H,F,H,F,H,2-F-Ph]、[A129;Me,H,F,H,H,F,2-F-Ph]、[A130;Me,H,Cl,H,H,Cl,2-F-Ph]、[A131;Me,H,Me,H,H,Me,2-F-Ph]、[A132;Me,H,F,F,F,F,2-F-Ph]、[A133;OMe,H,F,H,H,H,2-F-Ph]、[A134;OMe,H,Cl,H,H,H,2-F-Ph]、[A135;OMe,H,Me,H,H,H,2-F-Ph]、[A136;OMe,H,CN,H,H,H,2-F-Ph]、[A137;OMe,H,OH,H,H,H,2-F-Ph]、[A138;OMe,H,cPr,H,H,H,2-F-Ph]、[A139;OMe,H,F,F,H,H,2-F-Ph]、[A140;OMe,H,F,H,F,H,2-F-Ph]、[A141;OMe,H,F,H,H,F,2-F-Ph]、[A142;OMe,H,Cl,H,H,Cl,2-F-Ph]、[A143;OMe,H,Me,H,H,Me,2-F-Ph]、[A144;OMe,H,F,F,F,F,2-F-Ph]、[A145;OH,H,F,H,H,H,2-F-Ph]、[A146;OH,H,Cl,H,H,H,2-F-Ph]、[A147;OH,H,Me,H,H,H,2-F-Ph]、[A148;OH,H,CN,H,H,H,2-F-Ph]、[A149;OH,H,OH,H,H,H,2-F-Ph]、[A150;OH,H,cPr,H,H,H,2-F-Ph]、[A151;OH,H,F,F,H,H,2-F-Ph]、[A152;OH,H,F,H,F,H,2-F-Ph]、[A153;OH,H,F,H,H,F,2-F-Ph]、[A154;OH,H,Cl,H,H,Cl,2-F-Ph]、[A155;OH,H,Me,H,H,Me,2-F-Ph]、[A156;OH,H,F,F,F,F,2-F-Ph]、[A157;Me,Me,F,H,H,H,2-F-Ph]、[A158;Me,Me,Cl,H,H,H,2-F-Ph]、[A159;Me,Me,Me,H,H,H,2-F-Ph]、[A160;Me,Me,CN,H,H,H,2-F-Ph]、[A161;Me,Me,OH,H,H,H,2-F-Ph]、[A162;Me,Me,cPr,H,H,H,2-F-Ph]、[A163;Me,Me,F,F,H,H,2-F-Ph]、[A164;Me,Me,F,H,F,H,2-F-Ph]、[A165;Me,Me,F,H,H,F,2-F-Ph]、[A166;Me,Me,Cl,H,H,Cl,2-F-Ph]、[A167;Me,Me,Me,H,H,Me,2-F-Ph]、[A168;Me,Me,F,F,F,F,2-F-Ph]、[A169;F,F,F,H,H,H,2-F-Ph]、[A170;F,F,Cl,H,H,H,2-F-Ph]、[A171;F,F,Me,H,H,H,2-F-Ph]、[A172;F,F,CN,H,H,H,2-F-Ph]、[A173;F,F,OH,H,H,H,2-F-Ph]、[A174;F,F,cPr,H,H,H,2-F-Ph]、[A175;F,F,F,F,H,H,2-F-Ph]、[A176;F,F,F,H,F,H,2-F-Ph]、[A177;F,F,F,H,H,F,2-F-Ph]、[A178;F,F,Cl,H,H,Cl,2-F-Ph]、[A179;F,F,Me,H,H,Me,2-F-Ph]、[A180;F,F,F,F,F,F,2-F-Ph]、[A181;OH,Me,F,H,H,H,2-F-Ph]、[A182;OH,Me,Cl,H,H,H,2-F-Ph]、[A183;OH,Me,Me,H,H,H,2-F-Ph]、[A184;OH,Me,CN,H,H,H,2-F-Ph]、[A185;OH,Me,OH,H,H,H,2-F-Ph]、[A186;OH,Me,cPr,H,H,H,2-F-Ph]、[A187;OH,Me,F,F,H,H,2-F-Ph]、[A188;OH,Me,F,H,F,H,2-F-Ph]、[A189;OH,Me,F,H,H,F,2-F-Ph]、[A190;OH,Me,Cl,H,H,Cl,2-F-Ph]、[A191;OH,Me,Me,H,H,Me,2-F-Ph]、[A192;OH,Me,F,F,F,F,2-F-Ph]、[A193;H,H,F,H,H,H,3-F-Ph]、[A194;H,H,Cl,H,H,H,3-F-Ph]、[A195;H,H,Me,H,H,H,3-F-Ph]、[A196;H,H,CN,H,H,H,3-F-Ph]、[A197;H,H,OH,H,H,H,3-F-Ph]、[A198;H,H,cPr,H,H,H,3-F-Ph]、[A199;H,H,F,F,H,H,3-F-Ph]、[A200;H,H,F,H,F,H,3-F-Ph]、 [A201;H,H,F,H,H,F,3-F-Ph]、[A202;H,H,Cl,H,H,Cl,3-F-Ph]、[A203;H,H,Me,H,H,Me,3-F-Ph]、[A204;H,H,F,F,F,F,3-F-Ph]、[A205;F,H,F,H,H,H,3-F-Ph]、[A206;F,H,Cl,H,H,H,3-F-Ph]、[A207;F,H,Me,H,H,H,3-F-Ph]、[A208;F,H,CN,H,H,H,3-F-Ph]、[A209;F,H,OH,H,H,H,3-F-Ph]、[A210;F,H,cPr,H,H,H,3-F-Ph]、[A211;F,H,F,F,H,H,3-F-Ph]、[A212;F,H,F,H,F,H,3-F-Ph]、[A213;F,H,F,H,H,F,3-F-Ph]、[A214;F,H,Cl,H,H,Cl,3-F-Ph]、[A215;F,H,Me,H,H,Me,3-F-Ph]、[A216;F,H,F,F,F,F,3-F-Ph]、[A217;Me,H,F,H,H,H,3-F-Ph]、[A218;Me,H,Cl,H,H,H,3-F-Ph]、[A219;Me,H,Me,H,H,H,3-F-Ph]、[A220;Me,H,CN,H,H,H,3-F-Ph]、[A221;Me,H,OH,H,H,H,3-F-Ph]、[A222;Me,H,cPr,H,H,H,3-F-Ph]、[A223;Me,H,F,F,H,H,3-F-Ph]、[A224;Me,H,F,H,F,H,3-F-Ph]、[A225;Me,H,F,H,H,F,3-F-Ph]、[A226;Me,H,Cl,H,H,Cl,3-F-Ph]、[A227;Me,H,Me,H,H,Me,3-F-Ph]、[A228;Me,H,F,F,F,F,3-F-Ph]、[A229;OMe,H,F,H,H,H,3-F-Ph]、[A230;OMe,H,Cl,H,H,H,3-F-Ph]、[A231;OMe,H,Me,H,H,H,3-F-Ph]、[A232;OMe,H,CN,H,H,H,3-F-Ph]、[A233;OMe,H,OH,H,H,H,3-F-Ph]、[A234;OMe,H,cPr,H,H,H,3-F-Ph]、[A235;OMe,H,F,F,H,H,3-F-Ph]、[A236;OMe,H,F,H,F,H,3-F-Ph]、[A237;OMe,H,F,H,H,F,3-F-Ph]、[A238;OMe,H,Cl,H,H,Cl,3-F-Ph]、[A239;OMe,H,Me,H,H,Me,3-F-Ph]、[A240;OMe,H,F,F,F,F,3-F-Ph]、[A241;OH,H,F,H,H,H,3-F-Ph]、[A242;OH,H,Cl,H,H,H,3-F-Ph]、[A243;OH,H,Me,H,H,H,3-F-Ph]、[A244;OH,H,CN,H,H,H,3-F-Ph]、[A245;OH,H,OH,H,H,H,3-F-Ph]、[A246;OH,H,cPr,H,H,H,3-F-Ph]、[A247;OH,H,F,F,H,H,3-F-Ph]、[A248;OH,H,F,H,F,H,3-F-Ph]、[A249;OH,H,F,H,H,F,3-F-Ph]、[A250;OH,H,Cl,H,H,Cl,3-F-Ph]、[A251;OH,H,Me,H,H,Me,3-F-Ph]、[A252;OH,H,F,F,F,F,3-F-Ph]、[A253;Me,Me,F,H,H,H,3-F-Ph]、[A254;Me,Me,Cl,H,H,H,3-F-Ph]、[A255;Me,Me,Me,H,H,H,3-F-Ph]、 [A256;Me,Me,CN,H,H,H,3-F-Ph]、[A257;Me,Me,OH,H,H,H,3-F-Ph]、[A258;Me,Me,cPr,H,H,H,3-F-Ph]、[A259;Me,Me,F,F,H,H,3-F-Ph]、[A260;Me,Me,F,H,F,H,3-F-Ph]、[A261;Me,Me,F,H,H,F,3-F-Ph]、[A262;Me,Me,Cl,H,H,Cl,3-F-Ph]、[A263;Me,Me,Me,H,H,Me,3-F-Ph]、[A264;Me,Me,F,F,F,F,3-F-Ph]、[A265;F,F,F,H,H,H,3-F-Ph]、[A266;F,F,Cl,H,H,H,3-F-Ph]、[A267;F,F,Me,H,H,H,3-F-Ph]、[A268;F,F,CN,H,H,H,3-F-Ph]、[A269;F,F,OH,H,H,H,3-F-Ph]、[A270;F,F,cPr,H,H,H,3-F-Ph]、[A271;F,F,F,F,H,H,3-F-Ph]、[A272;F,F,F,H,F,H,3-F-Ph]、[A273;F,F,F,H,H,F,3-F-Ph]、[A274;F,F,Cl,H,H,Cl,3-F-Ph]、[A275;F,F,Me,H,H,Me,3-F-Ph]、[A276;F,F,F,F,F,F,3-F-Ph]、[A277;OH,Me,F,H,H,H,3-F-Ph]、[A278;OH,Me,Cl,H,H,H,3-F-Ph]、[A279;OH,Me,Me,H,H,H,3-F-Ph]、[A280;OH,Me,CN,H,H,H,3-F-Ph]、[A281;OH,Me,OH,H,H,H,3-F-Ph]、[A282;OH,Me,cPr,H,H,H,3-F-Ph]、[A283;OH,Me,F,F,H,H,3-F-Ph]、[A284;OH,Me,F,H,F,H,3-F-Ph]、[A285;OH,Me,F,H,H,F,3-F-Ph]、[A286;OH,Me,Cl,H,H,Cl,3-F-Ph]、[A287;OH,Me,Me,H,H,Me,3-F-Ph]、[A288;OH,Me,F,F,F,F,3-F-Ph]、[A289;H,H,F,H,H,H,4-F-Ph]、[A290;H,H,Cl,H,H,H,4-F-Ph]、[A291;H,H,Me,H,H,H,4-F-Ph]、[A292;H,H,CN,H,H,H,4-F-Ph]、[A293;H,H,OH,H,H,H,4-F-Ph]、[A294;H,H,cPr,H,H,H,4-F-Ph]、[A295;H,H,F,F,H,H,4-F-Ph]、[A296;H,H,F,H,F,H,4-F-Ph]、[A297;H,H,F,H,H,F,4-F-Ph]、[A298;H,H,Cl,H,H,Cl,4-F-Ph]、[A299;H,H,Me,H,H,Me,4-F-Ph]、[A300;H,H,F,F,F,F,4-F-Ph]、 [A301;F,H,F,H,H,H,4-F-Ph]、[A302;F,H,Cl,H,H,H,4-F-Ph]、[A303;F,H,Me,H,H,H,4-F-Ph]、[A304;F,H,CN,H,H,H,4-F-Ph]、[A305;F,H,OH,H,H,H,4-F-Ph]、[A306;F,H,cPr,H,H,H,4-F-Ph]、[A307;F,H,F,F,H,H,4-F-Ph]、[A308;F,H,F,H,F,H,4-F-Ph]、[A309;F,H,F,H,H,F,4-F-Ph]、[A310;F,H,Cl,H,H,Cl,4-F-Ph]、[A311;F,H,Me,H,H,Me,4-F-Ph]、[A312;F,H,F,F,F,F,4-F-Ph]、[A313;Me,H,F,H,H,H,4-F-Ph]、[A314;Me,H,Cl,H,H,H,4-F-Ph]、[A315;Me,H,Me,H,H,H,4-F-Ph]、[A316;Me,H,CN,H,H,H,4-F-Ph]、[A317;Me,H,OH,H,H,H,4-F-Ph]、[A318;Me,H,cPr,H,H,H,4-F-Ph]、[A319;Me,H,F,F,H,H,4-F-Ph]、[A320;Me,H,F,H,F,H,4-F-Ph]、[A321;Me,H,F,H,H,F,4-F-Ph]、[A322;Me,H,Cl,H,H,Cl,4-F-Ph]、[A323;Me,H,Me,H,H,Me,4-F-Ph]、[A324;Me,H,F,F,F,F,4-F-Ph]、[A325;OMe,H,F,H,H,H,4-F-Ph]、[A326;OMe,H,Cl,H,H,H,4-F-Ph]、[A327;OMe,H,Me,H,H,H,4-F-Ph]、[A328;OMe,H,CN,H,H,H,4-F-Ph]、[A329;OMe,H,OH,H,H,H,4-F-Ph]、[A330;OMe,H,cPr,H,H,H,4-F-Ph]、[A331;OMe,H,F,F,H,H,4-F-Ph]、[A332;OMe,H,F,H,F,H,4-F-Ph]、[A333;OMe,H,F,H,H,F,4-F-Ph]、[A334;OMe,H,Cl,H,H,Cl,4-F-Ph]、[A335;OMe,H,Me,H,H,Me,4-F-Ph]、[A336;OMe,H,F,F,F,F,4-F-Ph]、[A337;OH,H,F,H,H,H,4-F-Ph]、[A338;OH,H,Cl,H,H,H,4-F-Ph]、[A339;OH,H,Me,H,H,H,4-F-Ph]、[A340;OH,H,CN,H,H,H,4-F-Ph]、[A341;OH,H,OH,H,H,H,4-F-Ph]、[A342;OH,H,cPr,H,H,H,4-F-Ph]、[A343;OH,H,F,F,H,H,4-F-Ph]、[A344;OH,H,F,H,F,H,4-F-Ph]、[A345;OH,H,F,H,H,F,4-F-Ph]、[A346;OH,H,Cl,H,H,Cl,4-F-Ph]、[A347;OH,H,Me,H,H,Me,4-F-Ph]、[A348;OH,H,F,F,F,F,4-F-Ph]、[A349;Me,Me,F,H,H,H,4-F-Ph]、[A350;Me,Me,Cl,H,H,H,4-F-Ph]、[A351;Me,Me,Me,H,H,H,4-F-Ph]、[A352;Me,Me,CN,H,H,H,4-F-Ph]、[A353;Me,Me,OH,H,H,H,4-F-Ph]、[A354;Me,Me,cPr,H,H,H,4-F-Ph]、[A355;Me,Me,F,F,H,H,4-F-Ph]、[A356;Me,Me,F,H,F,H,4-F-Ph]、[A357;Me,Me,F,H,H,F,4-F-Ph]、[A358;Me,Me,Cl,H,H,Cl,4-F-Ph]、[A359;Me,Me,Me,H,H,Me,4-F-Ph]、[A360;Me,Me,F,F,F,F,4-F-Ph]、[A361;F,F,F,H,H,H,4-F-Ph]、[A362;F,F,Cl,H,H,H,4-F-Ph]、[A363;F,F,Me,H,H,H,4-F-Ph]、[A364;F,F,CN,H,H,H,4-F-Ph]、[A365;F,F,OH,H,H,H,4-F-Ph]、[A366;F,F,cPr,H,H,H,4-F-Ph]、[A367;F,F,F,F,H,H,4-F-Ph]、[A368;F,F,F,H,F,H,4-F-Ph]、[A369;F,F,F,H,H,F,4-F-Ph]、[A370;F,F,Cl,H,H,Cl,4-F-Ph]、[A371;F,F,Me,H,H,Me,4-F-Ph]、[A372;F,F,F,F,F,F,4-F-Ph]、[A373;OH,Me,F,H,H,H,4-F-Ph]、[A374;OH,Me,Cl,H,H,H,4-F-Ph]、[A375;OH,Me,Me,H,H,H,4-F-Ph]、[A376;OH,Me,CN,H,H,H,4-F-Ph]、[A377;OH,Me,OH,H,H,H,4-F-Ph]、[A378;OH,Me,cPr,H,H,H,4-F-Ph]、[A379;OH,Me,F,F,H,H,4-F-Ph]、[A380;OH,Me,F,H,F,H,4-F-Ph]、[A381;OH,Me,F,H,H,F,4-F-Ph]、[A382;OH,Me,Cl,H,H,Cl,4-F-Ph]、[A383;OH,Me,Me,H,H,Me,4-F-Ph]、 [A384;OH,Me,F,F,F,F,4-F-Ph]、[A385;H,H,F,H,H,H,2-Cl-Ph]、[A386;H,H,Cl,H,H,H,2-Cl-Ph]、[A387;H,H,Me,H,H,H,2-Cl-Ph]、[A388;H,H,CN,H,H,H,2-Cl-Ph]、[A389;H,H,OH,H,H,H,2-Cl-Ph]、[A390;H,H,cPr,H,H,H,2-Cl-Ph]、[A391;H,H,F,F,H,H,2-Cl-Ph]、[A392;H,H,F,H,F,H,2-Cl-Ph]、[A393;H,H,F,H,H,F,2-Cl-Ph]、[A394;H,H,Cl,H,H,Cl,2-Cl-Ph]、[A395;H,H,Me,H,H,Me,2-Cl-Ph]、[A396;H,H,F,F,F,F,2-Cl-Ph]、[A397;F,H,F,H,H,H,2-Cl-Ph]、[A398;F,H,Cl,H,H,H,2-Cl-Ph]、[A399;F,H,Me,H,H,H,2-Cl-Ph]、[A400;F,H,CN,H,H,H,2-Cl-Ph]、 [A401;F,H,OH,H,H,H,2-Cl-Ph]、[A402;F,H,cPr,H,H,H,2-Cl-Ph]、[A403;F,H,F,F,H,H,2-Cl-Ph]、[A404;F,H,F,H,F,H,2-Cl-Ph]、[A405;F,H,F,H,H,F,2-Cl-Ph]、[A406;F,H,Cl,H,H,Cl,2-Cl-Ph]、[A407;F,H,Me,H,H,Me,2-Cl-Ph]、[A408;F,H,F,F,F,F,2-Cl-Ph]、[A409;Me,H,F,H,H,H,2-Cl-Ph]、[A410;Me,H,Cl,H,H,H,2-Cl-Ph]、[A411;Me,H,Me,H,H,H,2-Cl-Ph]、[A412;Me,H,CN,H,H,H,2-Cl-Ph]、[A413;Me,H,OH,H,H,H,2-Cl-Ph]、[A414;Me,H,cPr,H,H,H,2-Cl-Ph]、[A415;Me,H,F,F,H,H,2-Cl-Ph]、[A416;Me,H,F,H,F,H,2-Cl-Ph]、[A417;Me,H,F,H,H,F,2-Cl-Ph]、[A418;Me,H,Cl,H,H,Cl,2-Cl-Ph]、[A419;Me,H,Me,H,H,Me,2-Cl-Ph]、[A420;Me,H,F,F,F,F,2-Cl-Ph]、[A421;OMe,H,F,H,H,H,2-Cl-Ph]、[A422;OMe,H,Cl,H,H,H,2-Cl-Ph]、[A423;OMe,H,Me,H,H,H,2-Cl-Ph]、[A424;OMe,H,CN,H,H,H,2-Cl-Ph]、[A425;OMe,H,OH,H,H,H,2-Cl-Ph]、[A426;OMe,H,cPr,H,H,H,2-Cl-Ph]、[A427;OMe,H,F,F,H,H,2-Cl-Ph]、[A428;OMe,H,F,H,F,H,2-Cl-Ph]、[A429;OMe,H,F,H,H,F,2-Cl-Ph]、[A430;OMe,H,Cl,H,H,Cl,2-Cl-Ph]、[A431;OMe,H,Me,H,H,Me,2-Cl-Ph]、[A432;OMe,H,F,F,F,F,2-Cl-Ph]、[A433;OH,H,F,H,H,H,2-Cl-Ph]、[A434;OH,H,Cl,H,H,H,2-Cl-Ph]、[A435;OH,H,Me,H,H,H,2-Cl-Ph]、[A436;OH,H,CN,H,H,H,2-Cl-Ph]、[A437;OH,H,OH,H,H,H,2-Cl-Ph]、[A438;OH,H,cPr,H,H,H,2-Cl-Ph]、[A439;OH,H,F,F,H,H,2-Cl-Ph]、[A440;OH,H,F,H,F,H,2-Cl-Ph]、[A441;OH,H,F,H,H,F,2-Cl-Ph]、[A442;OH,H,Cl,H,H,Cl,2-Cl-Ph]、[A443;OH,H,Me,H,H,Me,2-Cl-Ph]、[A444;OH,H,F,F,F,F,2-Cl-Ph]、[A445;Me,Me,F,H,H,H,2-Cl-Ph]、[A446;Me,Me,Cl,H,H,H,2-Cl-Ph]、[A447;Me,Me,Me,H,H,H,2-Cl-Ph]、[A448;Me,Me,CN,H,H,H,2-Cl-Ph]、[A449;Me,Me,OH,H,H,H,2-Cl-Ph]、[A450;Me,Me,cPr,H,H,H,2-Cl-Ph]、[A451;Me,Me,F,F,H,H,2-Cl-Ph]、[A452;Me,Me,F,H,F,H,2-Cl-Ph]、[A453;Me,Me,F,H,H,F,2-Cl-Ph]、[A454;Me,Me,Cl,H,H,Cl,2-Cl-Ph]、[A455;Me,Me,Me,H,H,Me,2-Cl-Ph]、[A456;Me,Me,F,F,F,F,2-Cl-Ph]、[A457;F,F,F,H,H,H,2-Cl-Ph]、[A458;F,F,Cl,H,H,H,2-Cl-Ph]、[A459;F,F,Me,H,H,H,2-Cl-Ph]、[A460;F,F,CN,H,H,H,2-Cl-Ph]、[A461;F,F,OH,H,H,H,2-Cl-Ph]、[A462;F,F,cPr,H,H,H,2-Cl-Ph]、[A463;F,F,F,F,H,H,2-Cl-Ph]、[A464;F,F,F,H,F,H,2-Cl-Ph]、[A465;F,F,F,H,H,F,2-Cl-Ph]、[A466;F,F,Cl,H,H,Cl,2-Cl-Ph]、[A467;F,F,Me,H,H,Me,2-Cl-Ph]、[A468;F,F,F,F,F,F,2-Cl-Ph]、[A469;OH,Me,F,H,H,H,2-Cl-Ph]、[A470;OH,Me,Cl,H,H,H,2-Cl-Ph]、[A471;OH,Me,Me,H,H,H,2-Cl-Ph]、[A472;OH,Me,CN,H,H,H,2-Cl-Ph]、[A473;OH,Me,OH,H,H,H,2-Cl-Ph]、[A474;OH,Me,cPr,H,H,H,2-Cl-Ph]、[A475;OH,Me,F,F,H,H,2-Cl-Ph]、[A476;OH,Me,F,H,F,H,2-Cl-Ph]、[A477;OH,Me,F,H,H,F,2-Cl-Ph]、[A478;OH,Me,Cl,H,H,Cl,2-Cl-Ph]、[A479;OH,Me,Me,H,H,Me,2-Cl-Ph]、[A480;OH,Me,F,F,F,F,2-Cl-Ph]、[A481;H,H,F,H,H,H,3-Cl-Ph]、[A482;H,H,Cl,H,H,H,3-Cl-Ph]、[A483;H,H,Me,H,H,H,3-Cl-Ph]、[A484;H,H,CN,H,H,H,3-Cl-Ph]、[A485;H,H,OH,H,H,H,3-Cl-Ph]、[A486;H,H,cPr,H,H,H,3-Cl-Ph]、[A487;H,H,F,F,H,H,3-Cl-Ph]、[A488;H,H,F,H,F,H,3-Cl-Ph]、[A489;H,H,F,H,H,F,3-Cl-Ph]、[A490;H,H,Cl,H,H,Cl,3-Cl-Ph]、[A491;H,H,Me,H,H,Me,3-Cl-Ph]、[A492;H,H,F,F,F,F,3-Cl-Ph]、[A493;F,H,F,H,H,H,3-Cl-Ph]、[A494;F,H,Cl,H,H,H,3-Cl-Ph]、[A495;F,H,Me,H,H,H,3-Cl-Ph]、[A496;F,H,CN,H,H,H,3-Cl-Ph]、[A497;F,H,OH,H,H,H,3-Cl-Ph]、[A498;F,H,cPr,H,H,H,3-Cl-Ph]、[A499;F,H,F,F,H,H,3-Cl-Ph]、[A500;F,H,F,H,F,H,3-Cl-Ph]、 [A501;F,H,F,H,H,F,3-Cl-Ph]、[A502;F,H,Cl,H,H,Cl,3-Cl-Ph]、[A503;F,H,Me,H,H,Me,3-Cl-Ph]、[A504;F,H,F,F,F,F,3-Cl-Ph]、[A505;Me,H,F,H,H,H,3-Cl-Ph]、[A506;Me,H,Cl,H,H,H,3-Cl-Ph]、[A507;Me,H,Me,H,H,H,3-Cl-Ph]、[A508;Me,H,CN,H,H,H,3-Cl-Ph]、[A509;Me,H,OH,H,H,H,3-Cl-Ph]、[A510;Me,H,cPr,H,H,H,3-Cl-Ph]、[A511;Me,H,F,F,H,H,3-Cl-Ph]、[A512;Me,H,F,H,F,H,3-Cl-Ph]、[A513;Me,H,F,H,H,F,3-Cl-Ph]、[A514;Me,H,Cl,H,H,Cl,3-Cl-Ph]、[A515;Me,H,Me,H,H,Me,3-Cl-Ph]、[A516;Me,H,F,F,F,F,3-Cl-Ph]、[A517;OMe,H,F,H,H,H,3-Cl-Ph]、[A518;OMe,H,Cl,H,H,H,3-Cl-Ph]、[A519;OMe,H,Me,H,H,H,3-Cl-Ph]、[A520;OMe,H,CN,H,H,H,3-Cl-Ph]、[A521;OMe,H,OH,H,H,H,3-Cl-Ph]、[A522;OMe,H,cPr,H,H,H,3-Cl-Ph]、[A523;OMe,H,F,F,H,H,3-Cl-Ph]、[A524;OMe,H,F,H,F,H,3-Cl-Ph]、[A525;OMe,H,F,H,H,F,3-Cl-Ph]、[A526;OMe,H,Cl,H,H,Cl,3-Cl-Ph]、[A527;OMe,H,Me,H,H,Me,3-Cl-Ph]、[A528;OMe,H,F,F,F,F,3-Cl-Ph]、[A529;OH,H,F,H,H,H,3-Cl-Ph]、[A530;OH,H,Cl,H,H,H,3-Cl-Ph]、[A531;OH,H,Me,H,H,H,3-Cl-Ph]、[A532;OH,H,CN,H,H,H,3-Cl-Ph]、[A533;OH,H,OH,H,H,H,3-Cl-Ph]、[A534;OH,H,cPr,H,H,H,3-Cl-Ph]、[A535;OH,H,F,F,H,H,3-Cl-Ph]、[A536;OH,H,F,H,F,H,3-Cl-Ph]、[A537;OH,H,F,H,H,F,3-Cl-Ph]、[A538;OH,H,Cl,H,H,Cl,3-Cl-Ph]、[A539;OH,H,Me,H,H,Me,3-Cl-Ph]、[A540;OH,H,F,F,F,F,3-Cl-Ph]、[A541;Me,Me,F,H,H,H,3-Cl-Ph]、[A542;Me,Me,Cl,H,H,H,3-Cl-Ph]、[A543;Me,Me,Me,H,H,H,3-Cl-Ph]、[A544;Me,Me,CN,H,H,H,3-Cl-Ph]、[A545;Me,Me,OH,H,H,H,3-Cl-Ph]、[A546;Me,Me,cPr,H,H,H,3-Cl-Ph]、[A547;Me,Me,F,F,H,H,3-Cl-Ph]、[A548;Me,Me,F,H,F,H,3-Cl-Ph]、[A549;Me,Me,F,H,H,F,3-Cl-Ph]、[A550;Me,Me,Cl,H,H,Cl,3-Cl-Ph]、[A551;Me,Me,Me,H,H,Me,3-Cl-Ph]、[A552;Me,Me,F,F,F,F,3-Cl-Ph]、[A553;F,F,F,H,H,H,3-Cl-Ph]、[A554;F,F,Cl,H,H,H,3-Cl-Ph]、[A555;F,F,Me,H,H,H,3-Cl-Ph]、[A556;F,F,CN,H,H,H,3-Cl-Ph]、[A557;F,F,OH,H,H,H,3-Cl-Ph]、[A558;F,F,cPr,H,H,H,3-Cl-Ph]、[A559;F,F,F,F,H,H,3-Cl-Ph]、[A560;F,F,F,H,F,H,3-Cl-Ph]、[A561;F,F,F,H,H,F,3-Cl-Ph]、[A562;F,F,Cl,H,H,Cl,3-Cl-Ph]、[A563;F,F,Me,H,H,Me,3-Cl-Ph]、[A564;F,F,F,F,F,F,3-Cl-Ph]、[A565;OH,Me,F,H,H,H,3-Cl-Ph]、[A566;OH,Me,Cl,H,H,H,3-Cl-Ph]、[A567;OH,Me,Me,H,H,H,3-Cl-Ph]、[A568;OH,Me,CN,H,H,H,3-Cl-Ph]、[A569;OH,Me,OH,H,H,H,3-Cl-Ph]、[A570;OH,Me,cPr,H,H,H,3-Cl-Ph]、[A571;OH,Me,F,F,H,H,3-Cl-Ph]、[A572;OH,Me,F,H,F,H,3-Cl-Ph]、[A573;OH,Me,F,H,H,F,3-Cl-Ph]、[A574;OH,Me,Cl,H,H,Cl,3-Cl-Ph]、[A575;OH,Me,Me,H,H,Me,3-Cl-Ph]、[A576;OH,Me,F,F,F,F,3-Cl-Ph]、[A577;H,H,F,H,H,H,4-Cl-Ph]、[A578;H,H,Cl,H,H,H,4-Cl-Ph]、[A579;H,H,Me,H,H,H,4-Cl-Ph]、[A580;H,H,CN,H,H,H,4-Cl-Ph]、[A581;H,H,OH,H,H,H,4-Cl-Ph]、[A582;H,H,cPr,H,H,H,4-Cl-Ph]、[A583;H,H,F,F,H,H,4-Cl-Ph]、[A584;H,H,F,H,F,H,4-Cl-Ph]、[A585;H,H,F,H,H,F,4-Cl-Ph]、[A586;H,H,Cl,H,H,Cl,4-Cl-Ph]、[A587;H,H,Me,H,H,Me,4-Cl-Ph]、[A588;H,H,F,F,F,F,4-Cl-Ph]、[A589;F,H,F,H,H,H,4-Cl-Ph]、[A590;F,H,Cl,H,H,H,4-Cl-Ph]、[A591;F,H,Me,H,H,H,4-Cl-Ph]、[A592;F,H,CN,H,H,H,4-Cl-Ph]、[A593;F,H,OH,H,H,H,4-Cl-Ph]、[A594;F,H,cPr,H,H,H,4-Cl-Ph]、[A595;F,H,F,F,H,H,4-Cl-Ph]、[A596;F,H,F,H,F,H,4-Cl-Ph]、[A597;F,H,F,H,H,F,4-Cl-Ph]、[A598;F,H,Cl,H,H,Cl,4-Cl-Ph]、[A599;F,H,Me,H,H,Me,4-Cl-Ph]、[A600;F,H,F,F,F,F,4-Cl-Ph]、 [A601;Me,H,F,H,H,H,4-Cl-Ph]、[A602;Me,H,Cl,H,H,H,4-Cl-Ph]、[A603;Me,H,Me,H,H,H,4-Cl-Ph]、[A604;Me,H,CN,H,H,H,4-Cl-Ph]、[A605;Me,H,OH,H,H,H,4-Cl-Ph]、[A606;Me,H,cPr,H,H,H,4-Cl-Ph]、[A607;Me,H,F,F,H,H,4-Cl-Ph]、[A608;Me,H,F,H,F,H,4-Cl-Ph]、[A609;Me,H,F,H,H,F,4-Cl-Ph]、[A610;Me,H,Cl,H,H,Cl,4-Cl-Ph]、[A611;Me,H,Me,H,H,Me,4-Cl-Ph]、[A612;Me,H,F,F,F,F,4-Cl-Ph]、[A613;OMe,H,F,H,H,H,4-Cl-Ph]、[A614;OMe,H,Cl,H,H,H,4-Cl-Ph]、[A615;OMe,H,Me,H,H,H,4-Cl-Ph]、[A616;OMe,H,CN,H,H,H,4-Cl-Ph]、[A617;OMe,H,OH,H,H,H,4-Cl-Ph]、[A618;OMe,H,cPr,H,H,H,4-Cl-Ph]、[A619;OMe,H,F,F,H,H,4-Cl-Ph]、[A620;OMe,H,F,H,F,H,4-Cl-Ph]、[A621;OMe,H,F,H,H,F,4-Cl-Ph]、[A622;OMe,H,Cl,H,H,Cl,4-Cl-Ph]、[A623;OMe,H,Me,H,H,Me,4-Cl-Ph]、[A624;OMe,H,F,F,F,F,4-Cl-Ph]、[A625;OH,H,F,H,H,H,4-Cl-Ph]、[A626;OH,H,Cl,H,H,H,4-Cl-Ph]、[A627;OH,H,Me,H,H,H,4-Cl-Ph]、[A628;OH,H,CN,H,H,H,4-Cl-Ph]、[A629;OH,H,OH,H,H,H,4-Cl-Ph]、[A630;OH,H,cPr,H,H,H,4-Cl-Ph]、[A631;OH,H,F,F,H,H,4-Cl-Ph]、[A632;OH,H,F,H,F,H,4-Cl-Ph]、[A633;OH,H,F,H,H,F,4-Cl-Ph]、[A634;OH,H,Cl,H,H,Cl,4-Cl-Ph]、[A635;OH,H,Me,H,H,Me,4-Cl-Ph]、[A636;OH,H,F,F,F,F,4-Cl-Ph]、[A637;Me,Me,F,H,H,H,4-Cl-Ph]、[A638;Me,Me,Cl,H,H,H,4-Cl-Ph]、[A639;Me,Me,Me,H,H,H,4-Cl-Ph]、[A640;Me,Me,CN,H,H,H,4-Cl-Ph]、[A641;Me,Me,OH,H,H,H,4-Cl-Ph]、[A642;Me,Me,cPr,H,H,H,4-Cl-Ph]、[A643;Me,Me,F,F,H,H,4-Cl-Ph]、[A644;Me,Me,F,H,F,H,4-Cl-Ph]、[A645;Me,Me,F,H,H,F,4-Cl-Ph]、[A646;Me,Me,Cl,H,H,Cl,4-Cl-Ph]、[A647;Me,Me,Me,H,H,Me,4-Cl-Ph]、[A648;Me,Me,F,F,F,F,4-Cl-Ph]、[A649;F,F,F,H,H,H,4-Cl-Ph]、[A650;F,F,Cl,H,H,H,4-Cl-Ph]、[A651;F,F,Me,H,H,H,4-Cl-Ph]、[A652;F,F,CN,H,H,H,4-Cl-Ph]、[A653;F,F,OH,H,H,H,4-Cl-Ph]、[A654;F,F,cPr,H,H,H,4-Cl-Ph]、[A655;F,F,F,F,H,H,4-Cl-Ph]、[A656;F,F,F,H,F,H,4-Cl-Ph]、[A657;F,F,F,H,H,F,4-Cl-Ph]、[A658;F,F,Cl,H,H,Cl,4-Cl-Ph]、[A659;F,F,Me,H,H,Me,4-Cl-Ph]、[A660;F,F,F,F,F,F,4-Cl-Ph]、[A661;OH,Me,F,H,H,H,4-Cl-Ph]、[A662;OH,Me,Cl,H,H,H,4-Cl-Ph]、[A663;OH,Me,Me,H,H,H,4-Cl-Ph]、[A664;OH,Me,CN,H,H,H,4-Cl-Ph]、[A665;OH,Me,OH,H,H,H,4-Cl-Ph]、[A666;OH,Me,cPr,H,H,H,4-Cl-Ph]、[A667;OH,Me,F,F,H,H,4-Cl-Ph]、[A668;OH,Me,F,H,F,H,4-Cl-Ph]、[A669;OH,Me,F,H,H,F,4-Cl-Ph]、[A670;OH,Me,Cl,H,H,Cl,4-Cl-Ph]、[A671;OH,Me,Me,H,H,Me,4-Cl-Ph]、[A672;OH,Me,F,F,F,F,4-Cl-Ph]、[A673;H,H,F,H,H,H,2-Me-Ph]、[A674;H,H,Cl,H,H,H,2-Me-Ph]、[A675;H,H,Me,H,H,H,2-Me-Ph]、[A676;H,H,CN,H,H,H,2-Me-Ph]、[A677;H,H,OH,H,H,H,2-Me-Ph]、[A678;H,H,cPr,H,H,H,2-Me-Ph]、[A679;H,H,F,F,H,H,2-Me-Ph]、[A680;H,H,F,H,F,H,2-Me-Ph]、[A681;H,H,F,H,H,F,2-Me-Ph]、[A682;H,H,Cl,H,H,Cl,2-Me-Ph]、[A683;H,H,Me,H,H,Me,2-Me-Ph]、[A684;H,H,F,F,F,F,2-Me-Ph]、[A685;F,H,F,H,H,H,2-Me-Ph]、[A686;F,H,Cl,H,H,H,2-Me-Ph]、[A687;F,H,Me,H,H,H,2-Me-Ph]、[A688;F,H,CN,H,H,H,2-Me-Ph]、[A689;F,H,OH,H,H,H,2-Me-Ph]、[A690;F,H,cPr,H,H,H,2-Me-Ph]、[A691;F,H,F,F,H,H,2-Me-Ph]、[A692;F,H,F,H,F,H,2-Me-Ph]、[A693;F,H,F,H,H,F,2-Me-Ph]、[A694;F,H,Cl,H,H,Cl,2-Me-Ph]、[A695;F,H,Me,H,H,Me,2-Me-Ph]、[A696;F,H,F,F,F,F,2-Me-Ph]、[A697;Me,H,F,H,H,H,2-Me-Ph]、[A698;Me,H,Cl,H,H,H,2-Me-Ph]、[A699;Me,H,Me,H,H,H,2-Me-Ph]、[A700;Me,H,CN,H,H,H,2-Me-Ph]、 [A701;Me,H,OH,H,H,H,2-Me-Ph]、[A702;Me,H,cPr,H,H,H,2-Me-Ph]、[A703;Me,H,F,F,H,H,2-Me-Ph]、[A704;Me,H,F,H,F,H,2-Me-Ph]、[A705;Me,H,F,H,H,F,2-Me-Ph]、[A706;Me,H,Cl,H,H,Cl,2-Me-Ph]、[A707;Me,H,Me,H,H,Me,2-Me-Ph]、[A708;Me,H,F,F,F,F,2-Me-Ph]、[A709;OMe,H,F,H,H,H,2-Me-Ph]、[A710;OMe,H,Cl,H,H,H,2-Me-Ph]、[A711;OMe,H,Me,H,H,H,2-Me-Ph]、[A712;OMe,H,CN,H,H,H,2-Me-Ph]、[A713;OMe,H,OH,H,H,H,2-Me-Ph]、[A714;OMe,H,cPr,H,H,H,2-Me-Ph]、[A715;OMe,H,F,F,H,H,2-Me-Ph]、[A716;OMe,H,F,H,F,H,2-Me-Ph]、[A717;OMe,H,F,H,H,F,2-Me-Ph]、[A718;OMe,H,Cl,H,H,Cl,2-Me-Ph]、[A719;OMe,H,Me,H,H,Me,2-Me-Ph]、[A720;OMe,H,F,F,F,F,2-Me-Ph]、[A721;OH,H,F,H,H,H,2-Me-Ph]、[A722;OH,H,Cl,H,H,H,2-Me-Ph]、[A723;OH,H,Me,H,H,H,2-Me-Ph]、[A724;OH,H,CN,H,H,H,2-Me-Ph]、[A725;OH,H,OH,H,H,H,2-Me-Ph]、[A726;OH,H,cPr,H,H,H,2-Me-Ph]、[A727;OH,H,F,F,H,H,2-Me-Ph]、[A728;OH,H,F,H,F,H,2-Me-Ph]、[A729;OH,H,F,H,H,F,2-Me-Ph]、[A730;OH,H,Cl,H,H,Cl,2-Me-Ph]、[A731;OH,H,Me,H,H,Me,2-Me-Ph]、[A732;OH,H,F,F,F,F,2-Me-Ph]、[A733;Me,Me,F,H,H,H,2-Me-Ph]、[A734;Me,Me,Cl,H,H,H,2-Me-Ph]、[A735;Me,Me,Me,H,H,H,2-Me-Ph]、[A736;Me,Me,CN,H,H,H,2-Me-Ph]、[A737;Me,Me,OH,H,H,H,2-Me-Ph]、[A738;Me,Me,cPr,H,H,H,2-Me-Ph]、[A739;Me,Me,F,F,H,H,2-Me-Ph]、[A740;Me,Me,F,H,F,H,2-Me-Ph]、[A741;Me,Me,F,H,H,F,2-Me-Ph]、[A742;Me,Me,Cl,H,H,Cl,2-Me-Ph]、[A743;Me,Me,Me,H,H,Me,2-Me-Ph]、[A744;Me,Me,F,F,F,F,2-Me-Ph]、[A745;F,F,F,H,H,H,2-Me-Ph]、[A746;F,F,Cl,H,H,H,2-Me-Ph]、[A747;F,F,Me,H,H,H,2-Me-Ph]、[A748;F,F,CN,H,H,H,2-Me-Ph]、[A749;F,F,OH,H,H,H,2-Me-Ph]、[A750;F,F,cPr,H,H,H,2-Me-Ph]、[A751;F,F,F,F,H,H,2-Me-Ph]、[A752;F,F,F,H,F,H,2-Me-Ph]、[A753;F,F,F,H,H,F,2-Me-Ph]、[A754;F,F,Cl,H,H,Cl,2-Me-Ph]、[A755;F,F,Me,H,H,Me,2-Me-Ph]、[A756;F,F,F,F,F,F,2-Me-Ph]、[A757;OH,Me,F,H,H,H,2-Me-Ph]、[A758;OH,Me,Cl,H,H,H,2-Me-Ph]、[A759;OH,Me,Me,H,H,H,2-Me-Ph]、[A760;OH,Me,CN,H,H,H,2-Me-Ph]、[A761;OH,Me,OH,H,H,H,2-Me-Ph]、[A762;OH,Me,cPr,H,H,H,2-Me-Ph]、[A763;OH,Me,F,F,H,H,2-Me-Ph]、[A764;OH,Me,F,H,F,H,2-Me-Ph]、[A765;OH,Me,F,H,H,F,2-Me-Ph]、[A766;OH,Me,Cl,H,H,Cl,2-Me-Ph]、[A767;OH,Me,Me,H,H,Me,2-Me-Ph]、[A768;OH,Me,F,F,F,F,2-Me-Ph]、[A769;H,H,F,H,H,H,3-Me-Ph]、[A770;H,H,Cl,H,H,H,3-Me-Ph]、[A771;H,H,Me,H,H,H,3-Me-Ph]、[A772;H,H,CN,H,H,H,3-Me-Ph]、[A773;H,H,OH,H,H,H,3-Me-Ph]、[A774;H,H,cPr,H,H,H,3-Me-Ph]、[A775;H,H,F,F,H,H,3-Me-Ph]、[A776;H,H,F,H,F,H,3-Me-Ph]、[A777;H,H,F,H,H,F,3-Me-Ph]、[A778;H,H,Cl,H,H,Cl,3-Me-Ph]、[A779;H,H,Me,H,H,Me,3-Me-Ph]、[A780;H,H,F,F,F,F,3-Me-Ph]、[A781;F,H,F,H,H,H,3-Me-Ph]、[A782;F,H,Cl,H,H,H,3-Me-Ph]、[A783;F,H,Me,H,H,H,3-Me-Ph]、[A784;F,H,CN,H,H,H,3-Me-Ph]、[A785;F,H,OH,H,H,H,3-Me-Ph]、[A786;F,H,cPr,H,H,H,3-Me-Ph]、[A787;F,H,F,F,H,H,3-Me-Ph]、[A788;F,H,F,H,F,H,3-Me-Ph]、[A789;F,H,F,H,H,F,3-Me-Ph]、[A790;F,H,Cl,H,H,Cl,3-Me-Ph]、[A791;F,H,Me,H,H,Me,3-Me-Ph]、[A792;F,H,F,F,F,F,3-Me-Ph]、[A793;Me,H,F,H,H,H,3-Me-Ph]、[A794;Me,H,Cl,H,H,H,3-Me-Ph]、[A795;Me,H,Me,H,H,H,3-Me-Ph]、[A796;Me,H,CN,H,H,H,3-Me-Ph]、[A797;Me,H,OH,H,H,H,3-Me-Ph]、[A798;Me,H,cPr,H,H,H,3-Me-Ph]、[A799;Me,H,F,F,H,H,3-Me-Ph]、[A800;Me,H,F,H,F,H,3-Me-Ph]、 [A801;Me,H,F,H,H,F,3-Me-Ph]、[A802;Me,H,Cl,H,H,Cl,3-Me-Ph]、[A803;Me,H,Me,H,H,Me,3-Me-Ph]、[A804;Me,H,F,F,F,F,3-Me-Ph]、[A805;OMe,H,F,H,H,H,3-Me-Ph]、[A806;OMe,H,Cl,H,H,H,3-Me-Ph]、[A807;OMe,H,Me,H,H,H,3-Me-Ph]、[A808;OMe,H,CN,H,H,H,3-Me-Ph]、[A809;OMe,H,OH,H,H,H,3-Me-Ph]、[A810;OMe,H,cPr,H,H,H,3-Me-Ph]、[A811;OMe,H,F,F,H,H,3-Me-Ph]、[A812;OMe,H,F,H,F,H,3-Me-Ph]、[A813;OMe,H,F,H,H,F,3-Me-Ph]、[A814;OMe,H,Cl,H,H,Cl,3-Me-Ph]、[A815;OMe,H,Me,H,H,Me,3-Me-Ph]、[A816;OMe,H,F,F,F,F,3-Me-Ph]、[A817;OH,H,F,H,H,H,3-Me-Ph]、[A818;OH,H,Cl,H,H,H,3-Me-Ph]、[A819;OH,H,Me,H,H,H,3-Me-Ph]、[A820;OH,H,CN,H,H,H,3-Me-Ph]、[A821;OH,H,OH,H,H,H,3-Me-Ph]、[A822;OH,H,cPr,H,H,H,3-Me-Ph]、[A823;OH,H,F,F,H,H,3-Me-Ph]、[A824;OH,H,F,H,F,H,3-Me-Ph]、[A825;OH,H,F,H,H,F,3-Me-Ph]、[A826;OH,H,Cl,H,H,Cl,3-Me-Ph]、[A827;OH,H,Me,H,H,Me,3-Me-Ph]、[A828;OH,H,F,F,F,F,3-Me-Ph]、[A829;Me,Me,F,H,H,H,3-Me-Ph]、[A830;Me,Me,Cl,H,H,H,3-Me-Ph]、[A831;Me,Me,Me,H,H,H,3-Me-Ph]、[A832;Me,Me,CN,H,H,H,3-Me-Ph]、[A833;Me,Me,OH,H,H,H,3-Me-Ph]、[A834;Me,Me,cPr,H,H,H,3-Me-Ph]、[A835;Me,Me,F,F,H,H,3-Me-Ph]、[A836;Me,Me,F,H,F,H,3-Me-Ph]、[A837;Me,Me,F,H,H,F,3-Me-Ph]、[A838;Me,Me,Cl,H,H,Cl,3-Me-Ph]、[A839;Me,Me,Me,H,H,Me,3-Me-Ph]、[A840;Me,Me,F,F,F,F,3-Me-Ph]、[A841;F,F,F,H,H,H,3-Me-Ph]、[A842;F,F,Cl,H,H,H,3-Me-Ph]、[A843;F,F,Me,H,H,H,3-Me-Ph]、[A844;F,F,CN,H,H,H,3-Me-Ph]、[A845;F,F,OH,H,H,H,3-Me-Ph]、[A846;F,F,cPr,H,H,H,3-Me-Ph]、[A847;F,F,F,F,H,H,3-Me-Ph]、[A848;F,F,F,H,F,H,3-Me-Ph]、[A849;F,F,F,H,H,F,3-Me-Ph]、[A850;F,F,Cl,H,H,Cl,3-Me-Ph]、[A851;F,F,Me,H,H,Me,3-Me-Ph]、[A852;F,F,F,F,F,F,3-Me-Ph]、[A853;OH,Me,F,H,H,H,3-Me-Ph]、[A854;OH,Me,Cl,H,H,H,3-Me-Ph]、[A855;OH,Me,Me,H,H,H,3-Me-Ph]、[A856;OH,Me,CN,H,H,H,3-Me-Ph]、[A857;OH,Me,OH,H,H,H,3-Me-Ph]、[A858;OH,Me,cPr,H,H,H,3-Me-Ph]、[A859;OH,Me,F,F,H,H,3-Me-Ph]、[A860;OH,Me,F,H,F,H,3-Me-Ph]、[A861;OH,Me,F,H,H,F,3-Me-Ph]、[A862;OH,Me,Cl,H,H,Cl,3-Me-Ph]、[A863;OH,Me,Me,H,H,Me,3-Me-Ph]、[A864;OH,Me,F,F,F,F,3-Me-Ph]、[A865;H,H,F,H,H,H,4-Me-Ph]、[A866;H,H,Cl,H,H,H,4-Me-Ph]、[A867;H,H,Me,H,H,H,4-Me-Ph]、[A868;H,H,CN,H,H,H,4-Me-Ph]、[A869;H,H,OH,H,H,H,4-Me-Ph]、[A870;H,H,cPr,H,H,H,4-Me-Ph]、[A871;H,H,F,F,H,H,4-Me-Ph]、[A872;H,H,F,H,F,H,4-Me-Ph]、[A873;H,H,F,H,H,F,4-Me-Ph]、[A874;H,H,Cl,H,H,Cl,4-Me-Ph]、[A875;H,H,Me,H,H,Me,4-Me-Ph]、[A876;H,H,F,F,F,F,4-Me-Ph]、[A877;F,H,F,H,H,H,4-Me-Ph]、[A878;F,H,Cl,H,H,H,4-Me-Ph]、[A879;F,H,Me,H,H,H,4-Me-Ph]、[A880;F,H,CN,H,H,H,4-Me-Ph]、[A881;F,H,OH,H,H,H,4-Me-Ph]、[A882;F,H,cPr,H,H,H,4-Me-Ph]、[A883;F,H,F,F,H,H,4-Me-Ph]、[A884;F,H,F,H,F,H,4-Me-Ph]、[A885;F,H,F,H,H,F,4-Me-Ph]、[A886;F,H,Cl,H,H,Cl,4-Me-Ph]、[A887;F,H,Me,H,H,Me,4-Me-Ph]、[A888;F,H,F,F,F,F,4-Me-Ph]、[A889;Me,H,F,H,H,H,4-Me-Ph]、[A890;Me,H,Cl,H,H,H,4-Me-Ph]、[A891;Me,H,Me,H,H,H,4-Me-Ph]、[A892;Me,H,CN,H,H,H,4-Me-Ph]、[A893;Me,H,OH,H,H,H,4-Me-Ph]、[A894;Me,H,cPr,H,H,H,4-Me-Ph]、[A895;Me,H,F,F,H,H,4-Me-Ph]、[A896;Me,H,F,H,F,H,4-Me-Ph]、[A897;Me,H,F,H,H,F,4-Me-Ph]、[A898;Me,H,Cl,H,H,Cl,4-Me-Ph]、[A899;Me,H,Me,H,H,Me,4-Me-Ph]、[A900;Me,H,F,F,F,F,4-Me-Ph]、 [A901;OMe,H,F,H,H,H,4-Me-Ph]、[A902;OMe,H,Cl,H,H,H,4-Me-Ph]、[A903;OMe,H,Me,H,H,H,4-Me-Ph]、[A904;OMe,H,CN,H,H,H,4-Me-Ph]、[A905;OMe,H,OH,H,H,H,4-Me-Ph]、[A906;OMe,H,cPr,H,H,H,4-Me-Ph]、[A907;OMe,H,F,F,H,H,4-Me-Ph]、[A908;OMe,H,F,H,F,H,4-Me-Ph]、[A909;OMe,H,F,H,H,F,4-Me-Ph]、[A910;OMe,H,Cl,H,H,Cl,4-Me-Ph]、[A911;OMe,H,Me,H,H,Me,4-Me-Ph]、[A912;OMe,H,F,F,F,F,4-Me-Ph]、[A913;OH,H,F,H,H,H,4-Me-Ph]、[A914;OH,H,Cl,H,H,H,4-Me-Ph]、[A915;OH,H,Me,H,H,H,4-Me-Ph]、[A916;OH,H,CN,H,H,H,4-Me-Ph]、[A917;OH,H,OH,H,H,H,4-Me-Ph]、[A918;OH,H,cPr,H,H,H,4-Me-Ph]、[A919;OH,H,F,F,H,H,4-Me-Ph]、[A920;OH,H,F,H,F,H,4-Me-Ph]、 [A921;OH,H,F,H,H,F,4-Me-Ph]、[A922;OH,H,Cl,H,H,Cl,4-Me-Ph]、[A923;OH,H,Me,H,H,Me,4-Me-Ph]、[A924;OH,H,F,F,F,F,4-Me-Ph]、[A925;Me,Me,F,H,H,H,4-Me-Ph]、[A926;Me,Me,Cl,H,H,H,4-Me-Ph]、[A927;Me,Me,Me,H,H,H,4-Me-Ph]、[A928;Me,Me,CN,H,H,H,4-Me-Ph]、[A929;Me,Me,OH,H,H,H,4-Me-Ph]、[A930;Me,Me,cPr,H,H,H,4-Me-Ph]、[A931;Me,Me,F,F,H,H,4-Me-Ph]、[A932;Me,Me,F,H,F,H,4-Me-Ph]、[A933;Me,Me,F,H,H,F,4-Me-Ph]、[A934;Me,Me,Cl,H,H,Cl,4-Me-Ph]、[A935;Me,Me,Me,H,H,Me,4-Me-Ph]、[A936;Me,Me,F,F,F,F,4-Me-Ph]、[A937;F,F,F,H,H,H,4-Me-Ph]、[A938;F,F,Cl,H,H,H,4-Me-Ph]、[A939;F,F,Me,H,H,H,4-Me-Ph]、[A940;F,F,CN,H,H,H,4-Me-Ph]、[A941;F,F,OH,H,H,H,4-Me-Ph]、[A942;F,F,cPr,H,H,H,4-Me-Ph]、[A943;F,F,F,F,H,H,4-Me-Ph]、[A944;F,F,F,H,F,H,4-Me-Ph]、[A945;F,F,F,H,H,F,4-Me-Ph]、[A946;F,F,Cl,H,H,Cl,4-Me-Ph]、[A947;F,F,Me,H,H,Me,4-Me-Ph]、[A948;F,F,F,F,F,F,4-Me-Ph]、[A949;OH,Me,F,H,H,H,4-Me-Ph]、[A950;OH,Me,Cl,H,H,H,4-Me-Ph]、[A951;OH,Me,Me,H,H,H,4-Me-Ph]、[A952;OH,Me,CN,H,H,H,4-Me-Ph]、[A953;OH,Me,OH,H,H,H,4-Me-Ph]、[A954;OH,Me,cPr,H,H,H,4-Me-Ph]、[A955;OH,Me,F,F,H,H,4-Me-Ph]、[A956;OH,Me,F,H,F,H,4-Me-Ph]、[A957;OH,Me,F,H,H,F,4-Me-Ph]、[A958;OH,Me,Cl,H,H,Cl,4-Me-Ph]、[A959;OH,Me,Me,H,H,Me,4-Me-Ph]、[A960;OH,Me,F,F,F,F,4-Me-Ph]、[A961;H,H,F,H,H,H,2-OMe-Ph]、[A962;H,H,Cl,H,H,H,2-OMe-Ph]、[A963;H,H,Me,H,H,H,2-OMe-Ph]、[A964;H,H,CN,H,H,H,2-OMe-Ph]、[A965;H,H,OH,H,H,H,2-OMe-Ph]、[A966;H,H,cPr,H,H,H,2-OMe-Ph]、[A967;H,H,F,F,H,H,2-OMe-Ph]、[A968;H,H,F,H,F,H,2-OMe-Ph]、[A969;H,H,F,H,H,F,2-OMe-Ph]、[A970;H,H,Cl,H,H,Cl,2-OMe-Ph]、[A971;H,H,Me,H,H,Me,2-OMe-Ph]、[A972;H,H,F,F,F,F,2-OMe-Ph]、[A973;F,H,F,H,H,H,2-OMe-Ph]、[A974;F,H,Cl,H,H,H,2-OMe-Ph]、[A975;F,H,Me,H,H,H,2-OMe-Ph]、[A976;F,H,CN,H,H,H,2-OMe-Ph]、[A977;F,H,OH,H,H,H,2-OMe-Ph]、[A978;F,H,cPr,H,H,H,2-OMe-Ph]、[A979;F,H,F,F,H,H,2-OMe-Ph]、[A980;F,H,F,H,F,H,2-OMe-Ph]、[A981;F,H,F,H,H,F,2-OMe-Ph]、[A982;F,H,Cl,H,H,Cl,2-OMe-Ph]、[A983;F,H,Me,H,H,Me,2-OMe-Ph]、[A984;F,H,F,F,F,F,2-OMe-Ph]、[A985;Me,H,F,H,H,H,2-OMe-Ph]、[A986;Me,H,Cl,H,H,H,2-OMe-Ph]、[A987;Me,H,Me,H,H,H,2-OMe-Ph]、[A988;Me,H,CN,H,H,H,2-OMe-Ph]、[A989;Me,H,OH,H,H,H,2-OMe-Ph]、[A990;Me,H,cPr,H,H,H,2-OMe-Ph]、[A991;Me,H,F,F,H,H,2-OMe-Ph]、[A992;Me,H,F,H,F,H,2-OMe-Ph]、[A993;Me,H,F,H,H,F,2-OMe-Ph]、[A994;Me,H,Cl,H,H,Cl,2-OMe-Ph]、[A995;Me,H,Me,H,H,Me,2-OMe-Ph]、[A996;Me,H,F,F,F,F,2-OMe-Ph]、[A997;OMe,H,F,H,H,H,2-OMe-Ph]、[A998;OMe,H,Cl,H,H,H,2-OMe-Ph]、[A999;OMe,H,Me,H,H,H,2-OMe-Ph]、[A1000;OMe,H,CN,H,H,H,2-OMe-Ph]、 [A1001;OMe,H,OH,H,H,H,2-OMe-Ph]、[A1002;OMe,H,cPr,H,H,H,2-OMe-Ph]、[A1003;OMe,H,F,F,H,H,2-OMe-Ph]、[A1004;OMe,H,F,H,F,H,2-OMe-Ph]、[A1005;OMe,H,F,H,H,F,2-OMe-Ph]、[A1006;OMe,H,Cl,H,H,Cl,2-OMe-Ph]、[A1007;OMe,H,Me,H,H,Me,2-OMe-Ph]、[A1008;OMe,H,F,F,F,F,2-OMe-Ph]、[A1009;OH,H,F,H,H,H,2-OMe-Ph]、[A1010;OH,H,Cl,H,H,H,2-OMe-Ph]、[A1011;OH,H,Me,H,H,H,2-OMe-Ph]、[A1012;OH,H,CN,H,H,H,2-OMe-Ph]、[A1013;OH,H,OH,H,H,H,2-OMe-Ph]、[A1014;OH,H,cPr,H,H,H,2-OMe-Ph]、[A1015;OH,H,F,F,H,H,2-OMe-Ph]、[A1016;OH,H,F,H,F,H,2-OMe-Ph]、[A1017;OH,H,F,H,H,F,2-OMe-Ph]、[A1018;OH,H,Cl,H,H,Cl,2-OMe-Ph]、[A1019;OH,H,Me,H,H,Me,2-OMe-Ph]、[A1020;OH,H,F,F,F,F,2-OMe-Ph]、[A1021;Me,Me,F,H,H,H,2-OMe-Ph]、[A1022;Me,Me,Cl,H,H,H,2-OMe-Ph]、[A1023;Me,Me,Me,H,H,H,2-OMe-Ph]、[A1024;Me,Me,CN,H,H,H,2-OMe-Ph]、[A1025;Me,Me,OH,H,H,H,2-OMe-Ph]、[A1026;Me,Me,cPr,H,H,H,2-OMe-Ph]、[A1027;Me,Me,F,F,H,H,2-OMe-Ph]、[A1028;Me,Me,F,H,F,H,2-OMe-Ph]、[A1029;Me,Me,F,H,H,F,2-OMe-Ph]、[A1030;Me,Me,Cl,H,H,Cl,2-OMe-Ph]、[A1031;Me,Me,Me,H,H,Me,2-OMe-Ph]、[A1032;Me,Me,F,F,F,F,2-OMe-Ph]、[A1033;F,F,F,H,H,H,2-OMe-Ph]、[A1034;F,F,Cl,H,H,H,2-OMe-Ph]、[A1035;F,F,Me,H,H,H,2-OMe-Ph]、[A1036;F,F,CN,H,H,H,2-OMe-Ph]、[A1037;F,F,OH,H,H,H,2-OMe-Ph]、[A1038;F,F,cPr,H,H,H,2-OMe-Ph]、[A1039;F,F,F,F,H,H,2-OMe-Ph]、[A1040;F,F,F,H,F,H,2-OMe-Ph]、[A1041;F,F,F,H,H,F,2-OMe-Ph]、[A1042;F,F,Cl,H,H,Cl,2-OMe-Ph]、[A1043;F,F,Me,H,H,Me,2-OMe-Ph]、[A1044;F,F,F,F,F,F,2-OMe-Ph]、[A1045;OH,Me,F,H,H,H,2-OMe-Ph]、[A1046;OH,Me,Cl,H,H,H,2-OMe-Ph]、[A1047;OH,Me,Me,H,H,H,2-OMe-Ph]、[A1048;OH,Me,CN,H,H,H,2-OMe-Ph]、[A1049;OH,Me,OH,H,H,H,2-OMe-Ph]、[A1050;OH,Me,cPr,H,H,H,2-OMe-Ph]、[A1051;OH,Me,F,F,H,H,2-OMe-Ph]、[A1052;OH,Me,F,H,F,H,2-OMe-Ph]、[A1053;OH,Me,F,H,H,F,2-OMe-Ph]、[A1054;OH,Me,Cl,H,H,Cl,2-OMe-Ph]、[A1055;OH,Me,Me,H,H,Me,2-OMe-Ph]、[A1056;OH,Me,F,F,F,F,2-OMe-Ph]、[A1057;H,H,F,H,H,H,3-OMe-Ph]、[A1058;H,H,Cl,H,H,H,3-OMe-Ph]、[A1059;H,H,Me,H,H,H,3-OMe-Ph]、[A1060;H,H,CN,H,H,H,3-OMe-Ph]、[A1061;H,H,OH,H,H,H,3-OMe-Ph]、[A1062;H,H,cPr,H,H,H,3-OMe-Ph]、[A1063;H,H,F,F,H,H,3-OMe-Ph]、[A1064;H,H,F,H,F,H,3-OMe-Ph]、[A1065;H,H,F,H,H,F,3-OMe-Ph]、[A1066;H,H,Cl,H,H,Cl,3-OMe-Ph]、[A1067;H,H,Me,H,H,Me,3-OMe-Ph]、[A1068;H,H,F,F,F,F,3-OMe-Ph]、[A1069;F,H,F,H,H,H,3-OMe-Ph]、[A1070;F,H,Cl,H,H,H,3-OMe-Ph]、[A1071;F,H,Me,H,H,H,3-OMe-Ph]、[A1072;F,H,CN,H,H,H,3-OMe-Ph]、[A1073;F,H,OH,H,H,H,3-OMe-Ph]、[A1074;F,H,cPr,H,H,H,3-OMe-Ph]、[A1075;F,H,F,F,H,H,3-OMe-Ph]、[A1076;F,H,F,H,F,H,3-OMe-Ph]、[A1077;F,H,F,H,H,F,3-OMe-Ph]、[A1078;F,H,Cl,H,H,Cl,3-OMe-Ph]、[A1079;F,H,Me,H,H,Me,3-OMe-Ph]、[A1080;F,H,F,F,F,F,3-OMe-Ph]、[A1081;Me,H,F,H,H,H,3-OMe-Ph]、[A1082;Me,H,Cl,H,H,H,3-OMe-Ph]、[A1083;Me,H,Me,H,H,H,3-OMe-Ph]、[A1084;Me,H,CN,H,H,H,3-OMe-Ph]、[A1085;Me,H,OH,H,H,H,3-OMe-Ph]、[A1086;Me,H,cPr,H,H,H,3-OMe-Ph]、[A1087;Me,H,F,F,H,H,3-OMe-Ph]、[A1088;Me,H,F,H,F,H,3-OMe-Ph]、[A1089;Me,H,F,H,H,F,3-OMe-Ph]、[A1090;Me,H,Cl,H,H,Cl,3-OMe-Ph]、[A1091;Me,H,Me,H,H,Me,3-OMe-Ph]、[A1092;Me,H,F,F,F,F,3-OMe-Ph]、[A1093;OMe,H,F,H,H,H,3-OMe-Ph]、[A1094;OMe,H,Cl,H,H,H,3-OMe-Ph]、[A1095;OMe,H,Me,H,H,H,3-OMe-Ph]、[A1096;OMe,H,CN,H,H,H,3-OMe-Ph]、[A1097;OMe,H,OH,H,H,H,3-OMe-Ph]、[A1098;OMe,H,cPr,H,H,H,3-OMe-Ph]、[A1099;OMe,H,F,F,H,H,3-OMe-Ph]、[A1100;OMe,H,F,H,F,H,3-OMe-Ph]、 [A1101;OMe,H,F,H,H,F,3-OMe-Ph]、[A1102;OMe,H,Cl,H,H,Cl,3-OMe-Ph]、[A1103;OMe,H,Me,H,H,Me,3-OMe-Ph]、[A1104;OMe,H,F,F,F,F,3-OMe-Ph]、[A1105;OH,H,F,H,H,H,3-OMe-Ph]、[A1106;OH,H,Cl,H,H,H,3-OMe-Ph]、[A1107;OH,H,Me,H,H,H,3-OMe-Ph]、[A1108;OH,H,CN,H,H,H,3-OMe-Ph]、[A1109;OH,H,OH,H,H,H,3-OMe-Ph]、[A1110;OH,H,cPr,H,H,H,3-OMe-Ph]、[A1111;OH,H,F,F,H,H,3-OMe-Ph]、[A1112;OH,H,F,H,F,H,3-OMe-Ph]、[A1113;OH,H,F,H,H,F,3-OMe-Ph]、[A1114;OH,H,Cl,H,H,Cl,3-OMe-Ph]、[A1115;OH,H,Me,H,H,Me,3-OMe-Ph]、[A1116;OH,H,F,F,F,F,3-OMe-Ph]、[A1117;Me,Me,F,H,H,H,3-OMe-Ph]、[A1118;Me,Me,Cl,H,H,H,3-OMe-Ph]、[A1119;Me,Me,Me,H,H,H,3-OMe-Ph]、[A1120;Me,Me,CN,H,H,H,3-OMe-Ph]、[A1121;Me,Me,OH,H,H,H,3-OMe-Ph]、[A1122;Me,Me,cPr,H,H,H,3-OMe-Ph]、[A1123;Me,Me,F,F,H,H,3-OMe-Ph]、[A1124;Me,Me,F,H,F,H,3-OMe-Ph]、[A1125;Me,Me,F,H,H,F,3-OMe-Ph]、[A1126;Me,Me,Cl,H,H,Cl,3-OMe-Ph]、[A1127;Me,Me,Me,H,H,Me,3-OMe-Ph]、[A1128;Me,Me,F,F,F,F,3-OMe-Ph]、[A1129;F,F,F,H,H,H,3-OMe-Ph]、[A1130;F,F,Cl,H,H,H,3-OMe-Ph]、[A1131;F,F,Me,H,H,H,3-OMe-Ph]、[A1132;F,F,CN,H,H,H,3-OMe-Ph]、[A1133;F,F,OH,H,H,H,3-OMe-Ph]、[A1134;F,F,cPr,H,H,H,3-OMe-Ph]、[A1135;F,F,F,F,H,H,3-OMe-Ph]、[A1136;F,F,F,H,F,H,3-OMe-Ph]、[A1137;F,F,F,H,H,F,3-OMe-Ph]、[A1138;F,F,Cl,H,H,Cl,3-OMe-Ph]、[A1139;F,F,Me,H,H,Me,3-OMe-Ph]、[A1140;F,F,F,F,F,F,3-OMe-Ph]、[A1141;OH,Me,F,H,H,H,3-OMe-Ph]、[A1142;OH,Me,Cl,H,H,H,3-OMe-Ph]、[A1143;OH,Me,Me,H,H,H,3-OMe-Ph]、[A1144;OH,Me,CN,H,H,H,3-OMe-Ph]、[A1145;OH,Me,OH,H,H,H,3-OMe-Ph]、[A1146;OH,Me,cPr,H,H,H,3-OMe-Ph]、[A1147;OH,Me,F,F,H,H,3-OMe-Ph]、[A1148;OH,Me,F,H,F,H,3-OMe-Ph]、[A1149;OH,Me,F,H,H,F,3-OMe-Ph]、[A1150;OH,Me,Cl,H,H,Cl,3-OMe-Ph]、[A1151;OH,Me,Me,H,H,Me,3-OMe-Ph]、[A1152;OH,Me,F,F,F,F,3-OMe-Ph]、[A1153;H,H,F,H,H,H,4-OMe-Ph]、[A1154;H,H,Cl,H,H,H,4-OMe-Ph]、[A1155;H,H,Me,H,H,H,4-OMe-Ph]、[A1156;H,H,CN,H,H,H,4-OMe-Ph]、[A1157;H,H,OH,H,H,H,4-OMe-Ph]、[A1158;H,H,cPr,H,H,H,4-OMe-Ph]、[A1159;H,H,F,F,H,H,4-OMe-Ph]、[A1160;H,H,F,H,F,H,4-OMe-Ph]、 [A1161;H,H,F,H,H,F,4-OMe-Ph]、[A1162;H,H,Cl,H,H,Cl,4-OMe-Ph]、[A1163;H,H,Me,H,H,Me,4-OMe-Ph]、[A1164;H,H,F,F,F,F,4-OMe-Ph]、[A1165;F,H,F,H,H,H,4-OMe-Ph]、[A1166;F,H,Cl,H,H,H,4-OMe-Ph]、[A1167;F,H,Me,H,H,H,4-OMe-Ph]、[A1168;F,H,CN,H,H,H,4-OMe-Ph]、[A1169;F,H,OH,H,H,H,4-OMe-Ph]、[A1170;F,H,cPr,H,H,H,4-OMe-Ph]、[A1171;F,H,F,F,H,H,4-OMe-Ph]、[A1172;F,H,F,H,F,H,4-OMe-Ph]、[A1173;F,H,F,H,H,F,4-OMe-Ph]、[A1174;F,H,Cl,H,H,Cl,4-OMe-Ph]、[A1175;F,H,Me,H,H,Me,4-OMe-Ph]、[A1176;F,H,F,F,F,F,4-OMe-Ph]、[A1177;Me,H,F,H,H,H,4-OMe-Ph]、[A1178;Me,H,Cl,H,H,H,4-OMe-Ph]、[A1179;Me,H,Me,H,H,H,4-OMe-Ph]、[A1180;Me,H,CN,H,H,H,4-OMe-Ph]、[A1181;Me,H,OH,H,H,H,4-OMe-Ph]、[A1182;Me,H,cPr,H,H,H,4-OMe-Ph]、[A1183;Me,H,F,F,H,H,4-OMe-Ph]、[A1184;Me,H,F,H,F,H,4-OMe-Ph]、[A1185;Me,H,F,H,H,F,4-OMe-Ph]、[A1186;Me,H,Cl,H,H,Cl,4-OMe-Ph]、[A1187;Me,H,Me,H,H,Me,4-OMe-Ph]、[A1188;Me,H,F,F,F,F,4-OMe-Ph]、[A1189;OMe,H,F,H,H,H,4-OMe-Ph]、[A1190;OMe,H,Cl,H,H,H,4-OMe-Ph]、[A1191;OMe,H,Me,H,H,H,4-OMe-Ph]、[A1192;OMe,H,CN,H,H,H,4-OMe-Ph]、[A1193;OMe,H,OH,H,H,H,4-OMe-Ph]、[A1194;OMe,H,cPr,H,H,H,4-OMe-Ph]、[A1195;OMe,H,F,F,H,H,4-OMe-Ph]、[A1196;OMe,H,F,H,F,H,4-OMe-Ph]、[A1197;OMe,H,F,H,H,F,4-OMe-Ph]、[A1198;OMe,H,Cl,H,H,Cl,4-OMe-Ph]、[A1199;OMe,H,Me,H,H,Me,4-OMe-Ph]、[A1200;OMe,H,F,F,F,F,4-OMe-Ph]、 [A1201;OH,H,F,H,H,H,4-OMe-Ph]、[A1202;OH,H,Cl,H,H,H,4-OMe-Ph]、[A1203;OH,H,Me,H,H,H,4-OMe-Ph]、[A1204;OH,H,CN,H,H,H,4-OMe-Ph]、[A1205;OH,H,OH,H,H,H,4-OMe-Ph]、[A1206;OH,H,cPr,H,H,H,4-OMe-Ph]、[A1207;OH,H,F,F,H,H,4-OMe-Ph]、[A1208;OH,H,F,H,F,H,4-OMe-Ph]、[A1209;OH,H,F,H,H,F,4-OMe-Ph]、[A1210;OH,H,Cl,H,H,Cl,4-OMe-Ph]、[A1211;OH,H,Me,H,H,Me,4-OMe-Ph]、[A1212;OH,H,F,F,F,F,4-OMe-Ph]、[A1213;Me,Me,F,H,H,H,4-OMe-Ph]、[A1214;Me,Me,Cl,H,H,H,4-OMe-Ph]、[A1215;Me,Me,Me,H,H,H,4-OMe-Ph]、[A1216;Me,Me,CN,H,H,H,4-OMe-Ph]、[A1217;Me,Me,OH,H,H,H,4-OMe-Ph]、[A1218;Me,Me,cPr,H,H,H,4-OMe-Ph]、[A1219;Me,Me,F,F,H,H,4-OMe-Ph]、[A1220;Me,Me,F,H,F,H,4-OMe-Ph]、[A1221;Me,Me,F,H,H,F,4-OMe-Ph]、[A1222;Me,Me,Cl,H,H,Cl,4-OMe-Ph]、[A1223;Me,Me,Me,H,H,Me,4-OMe-Ph]、[A1224;Me,Me,F,F,F,F,4-OMe-Ph]、[A1225;F,F,F,H,H,H,4-OMe-Ph]、[A1226;F,F,Cl,H,H,H,4-OMe-Ph]、[A1227;F,F,Me,H,H,H,4-OMe-Ph]、[A1228;F,F,CN,H,H,H,4-OMe-Ph]、[A1229;F,F,OH,H,H,H,4-OMe-Ph]、[A1230;F,F,cPr,H,H,H,4-OMe-Ph]、[A1231;F,F,F,F,H,H,4-OMe-Ph]、[A1232;F,F,F,H,F,H,4-OMe-Ph]、[A1233;F,F,F,H,H,F,4-OMe-Ph]、[A1234;F,F,Cl,H,H,Cl,4-OMe-Ph]、[A1235;F,F,Me,H,H,Me,4-OMe-Ph]、[A1236;F,F,F,F,F,F,4-OMe-Ph]、[A1237;OH,Me,F,H,H,H,4-OMe-Ph]、[A1238;OH,Me,Cl,H,H,H,4-OMe-Ph]、[A1239;OH,Me,Me,H,H,H,4-OMe-Ph]、[A1240;OH,Me,CN,H,H,H,4-OMe-Ph]、[A1241;OH,Me,OH,H,H,H,4-OMe-Ph]、[A1242;OH,Me,cPr,H,H,H,4-OMe-Ph]、[A1243;OH,Me,F,F,H,H,4-OMe-Ph]、[A1244;OH,Me,F,H,F,H,4-OMe-Ph]、[A1245;OH,Me,F,H,H,F,4-OMe-Ph]、[A1246;OH,Me,Cl,H,H,Cl,4-OMe-Ph]、[A1247;OH,Me,Me,H,H,Me,4-OMe-Ph]、[A1248;OH,Me,F,F,F,F,4-OMe-Ph]、[A1249;H,H,F,H,H,H,2-cPr-Ph]、[A1250;H,H,Cl,H,H,H,2-cPr-Ph]、[A1251;H,H,Me,H,H,H,2-cPr-Ph]、[A1252;H,H,CN,H,H,H,2-cPr-Ph]、[A1253;H,H,OH,H,H,H,2-cPr-Ph]、[A1254;H,H,cPr,H,H,H,2-cPr-Ph]、[A1255;H,H,F,F,H,H,2-cPr-Ph]、[A1256;H,H,F,H,F,H,2-cPr-Ph]、[A1257;H,H,F,H,H,F,2-cPr-Ph]、[A1258;H,H,Cl,H,H,Cl,2-cPr-Ph]、[A1259;H,H,Me,H,H,Me,2-cPr-Ph]、[A1260;H,H,F,F,F,F,2-cPr-Ph]、[A1261;F,H,F,H,H,H,2-cPr-Ph]、[A1262;F,H,Cl,H,H,H,2-cPr-Ph]、[A1263;F,H,Me,H,H,H,2-cPr-Ph]、[A1264;F,H,CN,H,H,H,2-cPr-Ph]、[A1265;F,H,OH,H,H,H,2-cPr-Ph]、[A1266;F,H,cPr,H,H,H,2-cPr-Ph]、[A1267;F,H,F,F,H,H,2-cPr-Ph]、[A1268;F,H,F,H,F,H,2-cPr-Ph]、[A1269;F,H,F,H,H,F,2-cPr-Ph]、[A1270;F,H,Cl,H,H,Cl,2-cPr-Ph]、[A1271;F,H,Me,H,H,Me,2-cPr-Ph]、[A1272;F,H,F,F,F,F,2-cPr-Ph]、[A1273;Me,H,F,H,H,H,2-cPr...
Claims
1. Formula (I) [In the formula, ring A 6 is a 6-membered non-aromatic nitrogen-containing heterocycle or a 6-membered aromatic nitrogen-containing heterocycle (provided that ring A 6 In the formula (I), the atom bonded to D is a carbon atom or a nitrogen atom, and a ring A is adjacent to the atom bonded to D. 6 at least one of the atoms constituting the ring is a nitrogen atom; D represents CR 1 R 2 , C=O, C=S, or C=N-OR 7 n represents 0, 1, 2, or 3; m represents 0, 1, 2, 3, or 4; q represents 0, 1, 2, 3, 4, or 5; R 1 and R 2 are the same or different and each represents a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group A, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group B}, a phenyl group, a 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group may be substituted with one or more substituents selected from group C}, OR 8 , S.R. 9 , S(O)R 10 , S(O)R 11 , N.R. 12 R 13 , C(O)R 14 , C(R 15 ) = NOR 16 , a cyano group, a nitro group, a halogen atom, or a hydrogen atom; R 1 and R 2 may form, together with the carbon atom to which they are bonded, a C3-C8 alicyclic hydrocarbon or a 3- to 8-membered non-aromatic heterocycle {the C3-C8 alicyclic hydrocarbon and the 3- to 8-membered non-aromatic heterocycle may be substituted with one or more substituents selected from group B}, R 3 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group A, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group B}, a phenyl group, a 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group may be substituted with one or more substituents selected from group C}, OR 17 , S.R. 18 , S(O)R 19 , S(O)R 20 , N.R. 21 R 22 , C(O)R 23 , C(R 24 ) = NOR 25 , a cyano group, a nitro group, or a halogen atom; R 4 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group A, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group B}, a phenyl group optionally substituted with one or more substituents selected from group C, OR 26 , N.R. 27 R 28 , C(O)R 29 , C(R 30 ) = NOR 31 , a cyano group, a nitro group, or a halogen atom; R 6 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group A, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group B}, a phenyl group, a 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group may be substituted with one or more substituents selected from group C}, OR 32 , S.R. 33 , S(O)R 34 , S(O)R 35 , N.R. 36 R 37 , C(O)R 38 , C(R 39 ) = NOR 40 , a cyano group, a nitro group, or a halogen atom; R 8 , R 12 , R 13 , R 17 , R 21 , R 22 , R 26 , R 27 , R 28 , R 32 , R 36 , and R 37 are the same or different and each is a C1-C6 chain hydrocarbon group, a C1-C6 alkylsulfonyl group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a (C2-C8 dialkylamino)carbonyl group {the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C1-C6 alkoxy)carbonyl group, the (C1-C6 alkylamino)carbonyl group, the (C2-C8 dialkylamino)carbonyl group, each of which may be substituted by one or more substituents selected from group A. a carbonyl group, and the (C2-C8 dialkylamino)carbonyl group are optionally substituted with one or more halogen atoms}, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group are optionally substituted with one or more substituents selected from group B}, a phenyl group, a 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group are optionally substituted with one or more substituents selected from group C}, or a hydrogen atom; 7 , R 9 , R 16 , R 18 , R 25 , R 31 , R 33 , and R 40 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group A, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group B}, a phenyl group, a 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group may be substituted with one or more substituents selected from group C}, or a hydrogen atom, R 10 , R 11 , R 19 , R 20 , R 34 , and R 35 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group A, a C1-C6 alkylamino group, a C2-C8 dialkylamino group {the C1-C6 alkylamino group and the C2-C8 dialkylamino group may be substituted with one or more halogen atoms}, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group B}, a phenyl group, or a 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group may be substituted with one or more substituents selected from group C}, R 14 , R 23 , R 29 , and R 38 are the same or different and represent a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylamino group, a C2-C8 dialkylamino group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylamino group, and the C2-C8 dialkylamino group may be substituted with one or more halogen atoms}, or a hydroxy group, R 15 , R 24 , R 30 , and R 39 are the same or different and each represents a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group A, or a hydrogen atom; when q is 2, 3, 4, or 5, adjacent two R 6 and R 6 may form, together with the carbon atom to which they are bonded, a C5-C6 alicyclic hydrocarbon, a 5- to 6-membered non-aromatic heterocycle {the C5-C6 alicyclic hydrocarbon and the 5- to 6-membered non-aromatic heterocycle may be substituted with one or more substituents selected from group B}, a benzene ring, or a 5- to 6-membered aromatic heterocycle {the benzene ring and the 5- to 6-membered aromatic heterocycle may be substituted with one or more substituents selected from group C}. Group A: the group consisting of a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group {the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group and the C1-C6 alkylsulfonyl group may be substituted with one or more halogen atoms}, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from Group B}, a phenyl group, a 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group C}, a halogen atom, a cyano group, a nitro group, a hydroxy group, and a sulfanyl group. Group B: a group consisting of an oxo group, a thioxo group, a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group and the C1-C6 alkylsulfonyl group are optionally substituted with one or more halogen atoms}, a hydroxy group, a sulfanyl group, a halogen atom, and a cyano group.Group C: a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a C2-C8 dialkylamino group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a (C2-C8 dialkylamino)carbonyl group, a (C1-C6 alkyl)carbonylamino group, a (C1-C6 alkoxy)carbonylamino group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group, the (C1-C6 alkyl)carbonyl group, the C1-C6 alkylsulfonyl group, the C1-C6 alkylamino group, the C2-C8 dialkylamino group, the (C1-C6 alkyl)carbonyl group, the (C1-C6 alkoxy)carbonyl group, the (C1-C6 alkylamino)carbonyl group, the (C2-C8 dialkylamino)carbonyl group, the (C1-C6 alkyl)carbonylamino group and the (C1-C6 alkoxy)carbonylamino group are optionally substituted with one or more halogen atoms}, the group consisting of a C3-C8 alicyclic hydrocarbon group optionally substituted with one or more substituents selected from group B, an amino group, a nitro group, a cyano group, a hydroxy group, a sulfanyl group, and a halogen atom. ], or an N-oxide or a salt thereof to a plant or the soil in which the plant is grown.
2. Formula (II) [In the formula, X 1a is a nitrogen atom, or CR 41a represents 2a is a nitrogen atom, or CR 42a represents 3a is a nitrogen atom, or CR 43a represents 4a is a nitrogen atom, or CR 44a (wherein X 1a , X 2a , X 3a and X 4a The number of nitrogen atoms is 0 or 1. 1a is CR 41a And X 2a is CR 42a And X 3a is CR 43a And X 4a is CR 44a When R 41a , R 42a , R 43a and R 44a At least one of the groups is a hydrogen atom; m represents 0, 1, 2, or 3; q represents 0, 1, 2, 3, 4, or 5; R 1a , and R 2a are the same or different, and are group A a a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group, each of which may be substituted by one or more substituents selected from the group consisting of the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group, each of which may be substituted by one or more substituents selected from the group consisting of the C1-C6 chain hydrocarbon group, the C3-C8 alicyclic hydrocarbon group, and the 3- to 8-membered non-aromatic heterocyclic group a a phenyl group, a 5- or 6-membered aromatic heterocyclic group {the phenyl group and the 5- or 6-membered aromatic heterocyclic group are each selected from group C a may be substituted with one or more substituents selected from the following: OR 8a , S.R. 9a , S(O)R 10a , S(O)R 11a , N.R. 12a R 13a , C(O)R 14a , C(R 15a ) = NOR 16a , a cyano group, a nitro group, a halogen atom, or a hydrogen atom; R 1a and R 2a together with the carbon atom to which they are attached, a C3-C8 alicyclic hydrocarbon or a 3- to 8-membered non-aromatic heterocycle {the C3-C8 alicyclic hydrocarbon and the 3- to 8-membered non-aromatic heterocycle are each selected from the group B a R may be substituted with one or more substituents selected from the following 3a and R 5a are the same or different, and are group A a a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group, each of which may be substituted by one or more substituents selected from the group consisting of the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group, each of which may be substituted by one or more substituents selected from the group consisting of the C1-C6 chain hydrocarbon group, the C3-C8 alicyclic hydrocarbon group, and the 3- to 8-membered non-aromatic heterocyclic group a a phenyl group, a 5- or 6-membered aromatic heterocyclic group {the phenyl group and the 5- or 6-membered aromatic heterocyclic group are each selected from group C a may be substituted with one or more substituents selected from the following: OR 17a , S.R. 18a , S(O)R 19a , S(O)R 20a , N.R. 21a R 22a , C(O)R 23a , C(R 24a ) = NOR 25a , a cyano group, a nitro group, or a halogen atom; R 6a Group A a a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group, each of which may be substituted by one or more substituents selected from the group consisting of the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group, each of which may be substituted by one or more substituents selected from the group consisting of the C1-C6 chain hydrocarbon group, the C3-C8 alicyclic hydrocarbon group, and the 3- to 8-membered non-aromatic heterocyclic group a a phenyl group, a 5- or 6-membered aromatic heterocyclic group {the phenyl group and the 5- or 6-membered aromatic heterocyclic group are each selected from group C a may be substituted with one or more substituents selected from the following: OR 32a , S.R. 33a , S(O)R 34a , S(O)R 35a , N.R. 36a R 37a , C(O)R 38a , C(R 39a ) = NOR 40a , a cyano group, a nitro group, or a halogen atom; R 41a , R 42a , and R 44a are the same or different, and are group D a a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group, each of which may be substituted by one or more substituents selected from the group consisting of the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group, each of which may be substituted by one or more substituents selected from the group consisting of the C1-C6 chain hydrocarbon group, the C3-C8 alicyclic hydrocarbon group, and the 3- to 8-membered non-aromatic heterocyclic group a may be substituted with one or more substituents selected from the following: OR 45a , N.R. 47a R 48a , C(R 49a ) = NOR 50a , a cyano group, a nitro group, a halogen atom, or a hydrogen atom; R 43a is group D a a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group, each of which may be substituted by one or more substituents selected from the group consisting of the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group, each of which may be substituted by one or more substituents selected from the group consisting of the C1-C6 chain hydrocarbon group, the C3-C8 alicyclic hydrocarbon group, and the 3- to 8-membered non-aromatic heterocyclic group a may be substituted with one or more substituents selected from the following: OR 46a , N.R. 47a R 48a , C(R 49a ) = NOR 50a , a cyano group, a nitro group, a halogen atom, or a hydrogen atom; R 8a , R 12a , R 13a , R 17a , R 21a , R 22a , R 32a , R 36a , and R 37a are the same or different, and are group A a a C1-C6 chain hydrocarbon group optionally substituted by one or more substituents selected from the group consisting of a C1-C6 alkylsulfonyl group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a (C2-C8 dialkylamino)carbonyl group {the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C1-C6 alkoxy)carbonyl group, the (C1-C6 alkylamino)carbonyl group, and the (C2-C8 dialkylamino)carbonyl group are optionally substituted by one or more halogen atoms}, a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group, and the 3- to 8-membered non-aromatic heterocyclic group are each selected from the group consisting of a C1-C6 alkylsulfonyl group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, and a (C2-C8 dialkylamino)carbonyl group are optionally substituted by one or more halogen atoms}, a a phenyl group, a 5- or 6-membered aromatic heterocyclic group {the phenyl group and the 5- or 6-membered aromatic heterocyclic group are each selected from group C a or a hydrogen atom; R 9a , R 16a , R 18a , R 25a , R 33a , and R 40a are the same or different, and are group A a a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group, each of which may be substituted by one or more substituents selected from the group consisting of the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group, each of which may be substituted by one or more substituents selected from the group consisting of the C1-C6 chain hydrocarbon group, the C3-C8 alicyclic hydrocarbon group, and the 3- to 8-membered non-aromatic heterocyclic group a a phenyl group, a 5- or 6-membered aromatic heterocyclic group {the phenyl group and the 5- or 6-membered aromatic heterocyclic group are each selected from group C a or a hydrogen atom; R 10a , R 11a , R 19a , R 20a , R 34a , and R 35a are the same or different, and are group A a a C1-C6 chain hydrocarbon group optionally substituted by one or more substituents selected from the group consisting of a C1-C6 alkylamino group, a C2-C8 dialkylamino group (the C1-C6 alkylamino group and the C2-C8 dialkylamino group are optionally substituted by one or more halogen atoms), a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group (the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group are selected from the group consisting of ... alkylamino group, a C1-C6 alkylamino group, a C2-C8 dialkylamino group, a a phenyl group, or a 5- or 6-membered aromatic heterocyclic group {the phenyl group and the 5- or 6-membered aromatic heterocyclic group are each selected from group C a R may be substituted with one or more substituents selected from 23a , and R 38a are the same or different and represent a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylamino group, a C2-C8 dialkylamino group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylamino group, and the C2-C8 dialkylamino group may be substituted with one or more halogen atoms}, or a hydroxy group, R 15a , R 24a , and R 39a are the same or different, and are group A a R represents a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from the following, or a hydrogen atom; 45a is group D a a C1-C6 chain hydrocarbon group, a C1-C6 alkylsulfonyl group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a (C2-C8 dialkylamino)carbonyl group {the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C1-C6 alkoxy)carbonyl group, the (C1-C6 alkylamino)carbonyl group, and the (C2-C8 dialkylamino)carbonyl group are optionally substituted with one or more halogen atoms}, a C3-C8 alicyclic hydrocarbon group, or a 3- to 8-membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group are each selected from group B a R may be substituted with one or more substituents selected from 47a and R 48a are the same or different, and are group D a a C1-C6 chain hydrocarbon group optionally substituted by one or more substituents selected from the group consisting of a C1-C6 alkylsulfonyl group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a (C2-C8 dialkylamino)carbonyl group {the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C1-C6 alkoxy)carbonyl group, the (C1-C6 alkylamino)carbonyl group, and the (C2-C8 dialkylamino)carbonyl group are optionally substituted by one or more halogen atoms}, a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group, and the 3- to 8-membered non-aromatic heterocyclic group are each selected from the group consisting of a C1-C6 alkylsulfonyl group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, and a (C2-C8 dialkylamino)carbonyl group are optionally substituted by one or more halogen atoms}, a or a hydrogen atom; R 50a is group D a a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group, each of which may be substituted by one or more substituents selected from the group consisting of the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group, each of which may be substituted by one or more substituents selected from the group consisting of the C1-C6 chain hydrocarbon group, the C3-C8 alicyclic hydrocarbon group, and the 3- to 8-membered non-aromatic heterocyclic group a R may be substituted with one or more substituents selected from 49a is group D a R represents a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from the following, or a hydrogen atom; 14a represents a C1-C6 chain hydrocarbon group, a C1-C6 alkylamino group, a C2-C8 dialkylamino group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylamino group, and the C2-C8 dialkylamino group may be substituted with one or more halogen atoms}, or a hydroxy group, R 46a is a CFH group, a CFH group, a CF3 group, group D a a C2-C6 chain hydrocarbon group optionally substituted by one or more substituents selected from the group consisting of a C1-C6 alkylsulfonyl group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a (C2-C8 dialkylamino)carbonyl group {the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C1-C6 alkoxy)carbonyl group, the (C1-C6 alkylamino)carbonyl group, and the (C2-C8 dialkylamino)carbonyl group are optionally substituted by one or more halogen atoms}, a C3-C8 alicyclic hydrocarbon group, or a 3- to 8-membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group are each selected from the group consisting of a C2-C6 chain hydrocarbon group optionally substituted by one or more substituents selected from the group consisting of a C1-C6 alkylsulfonyl group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, and a (C2-C8 dialkylamino)carbonyl group a may be substituted with one or more substituents selected from the following. a C1-C6 alkoxy group, C1-C6 alkylsulfanyl group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, {the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group, and the C1-C6 alkylsulfonyl group may be substituted with one or more halogen atoms}, a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group, and the 3- to 8-membered non-aromatic heterocyclic group are group B a a phenyl group, a 5- or 6-membered aromatic heterocyclic group {the phenyl group and the 5- or 6-membered aromatic heterocyclic group are each selected from group C a Group B is a group consisting of a halogen atom, a cyano group, a nitro group, a hydroxyl group, and a sulfanyl group, and may be substituted with one or more substituents selected from the group consisting of a halogen atom, a cyano group, a nitro group, a hydroxyl group, and a sulfanyl group. a Group C: the group consisting of an oxo group, a thioxo group, a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group, and the C1-C6 alkylsulfonyl group may be substituted with one or more halogen atoms}, a hydroxy group, a sulfanyl group, a halogen atom, and a cyano group. a : a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a C2-C8 dialkylamino group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a (C2-C8 dialkylamino)carbonyl group, a (C1-C6 alkyl)carbonylamino group, a (C1-C6 alkoxy)carbonylamino group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the C1-C6 alkylamino group, the C2-C8 dialkylamino group, the (C1-C6 alkyl)carbonyl group, the (C1-C6 alkoxy)carbonyl group, the (C1-C6 alkylamino)carbonyl group, the (C2-C8 dialkylamino)carbonyl group, the (C1-C6 alkyl)carbonylamino group and the (C1-C6 alkoxy)carbonylamino group are optionally substituted with one or more halogen atoms}, Group B a Group D consisting of a C3-C8 alicyclic hydrocarbon group optionally substituted with one or more substituents selected from the group consisting of an amino group, a nitro group, a cyano group, a hydroxy group, a sulfanyl group, and a halogen atom. a C1-C6 alkoxy group, C1-C6 alkylsulfanyl group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group {the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group, and the C1-C6 alkylsulfonyl group may be substituted with one or more halogen atoms}, a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group, and the 3- to 8-membered non-aromatic heterocyclic group are each selected from group B a The compound represented by the formula (I) may be substituted with one or more substituents selected from the group consisting of a halogen atom, a cyano group, a nitro group, a hydroxy group, and a sulfanyl group, or an N-oxide thereof, or a salt thereof.
3. A composition comprising the compound according to claim 2 or its N-oxide or a salt thereof and an inert carrier.
4. A composition containing one or more components selected from the group consisting of groups (a), (b), (c) and (d), and the compound described in claim 2 or its N-oxide or a salt thereof: Group (a): a group consisting of insecticidal active components, acaricidal active components and nematicidal active components; Group (b): fungicidal active components; Group (c): plant growth regulator components; Group (d): repellent components.
5. A method for controlling plant diseases which comprises applying an effective amount of the compound or N-oxide or salt thereof according to claim 2, or an effective amount of the composition according to claim 4 to a plant or the soil in which the plant is grown.
6. Use of a compound or an N-oxide or a salt thereof according to claim 2, or a composition according to claim 4, for controlling plant diseases.
7. A seed or vegetative reproductive organ bearing an effective amount of a compound or N-oxide or salt thereof according to claim 2, or an effective amount of a composition according to claim 4.
Citation Information
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