Phenyl compound and method for controlling plant diseases

Abstract

The present invention provides an excellent method for controlling plant diseases. The compound represented by formula (I) can be used for controlling plant diseases. In formula (I), Z represents a C1-C6 chain hydrocarbon group, etc.; Q represents the group represented by Q1, the group represented by Q2, or the group represented by Q3 (# represents the bonding site to the phenyl group, ● represents the bonding site to the sulfur atom); R 1 , R 2 , R 3 , R 4 and R 5 are the same or different and represent a C1-C6 chain hydrocarbon group, etc.; R 6 , R 7 , R 8 and R 9 are the same or different and represent a hydrogen atom, etc.; n represents 0, 1 or 2.

Description

Technical Field

[0001] This application claims the priority and benefits of Japanese Patent Application No. 2020-075879 filed on April 22, 2020, the entire content of which is incorporated herein by reference.

[0002] The present invention relates to phenyl compounds and methods for controlling plant diseases. Background Art

[0003] In Patent Document 1, phenylpyrazole compounds are described for use as insecticides, acaricides, and nematicides.

[0004] Prior Art Documents

[0005] Patent Documents

[0006] Patent Document 1: Japanese Unexamined Patent Application Publication No. 2007-284387 Summary of the Invention

[0007] Problems to be Solved by the Invention

[0008] An object of the present invention is to provide an excellent method for controlling plant diseases.

[0009] Means for Solving the Problems

[0010] The inventors of the present application conducted research to find an excellent method for controlling plant diseases, and as a result, found that the compound represented by the following formula (I) has excellent control efficacy against plant diseases.

[0011] That is, the present invention is as follows.

[0012] [1] A method for controlling plant diseases, which is carried out by treating a plant or the soil of a cultivated plant with a compound represented by formula (I) (hereinafter, referred to as this compound N) or its N-oxide or a salt thereof (hereinafter, the compound represented by formula (I) or its N-oxide or a salt thereof is referred to as this compound),

[0013] [Chemical Formula 1]

[0014]

[0015] 〔In the formula,

[0016] Z represents a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C6-C10 aryl group, or a 5-10 membered aromatic heterocyclic group which may be substituted with one or more substituents selected from Group A {the C3-C6 cycloalkyl group, the C6-C10 aryl group, and the 5-10 membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group E},

[0017] Q represents the group shown in Q1, the group shown in Q2, or the group shown in Q3 (# represents the bonding site to the phenyl group, ● represents the bonding site to the sulfur atom).

[0018] [Chemical Formula 2]

[0019]

[0020] R 1 、R 2 、R 3 、R 4 and R 5 are the same or different and represent a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C6-C10 aryl group, a 5-10 membered aromatic heterocyclic group {the C3-C6 cycloalkyl group, the C6-C10 aryl group, and the 5-10 membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group E}, a hydrogen atom, a halogen atom, a nitro group, a cyano group, -OR 10 、-S(O) k R 11 、-C(O)R 12 、-CR 13 =N-O-R 14 、-O-N=CR 15 R 16 、-N=N-CR 17 R 18 R 19 、-C(O)NR 20 R 21 、-NR 22 C(O)R 23 、-C(O)N(OR 24 )R 25 、-N(OR 26 )C(O)R 27 、-NR 28 C(O)NR 29 R 30 、-OC(O)NR 31 R 32 、-NR 33 C(O)OR 34 、-NR 35 C(O)C(O)NR 36 R 37 、-CR 38 R 39 NR 40 C(O)C(O)NR 41 R 42 、or -NR 43 C(O)C(O)N(OR 44 )R45 ,

[0021] R 1 and R 2 may together with the carbon atom to which they are attached form a C4-C7 carbocyclic ring or a 5-7 membered heterocyclic ring {the C4-C7 carbocyclic ring and the 5-7 membered heterocyclic ring may be substituted with one or more substituents selected from Group B},

[0022] R 2 and R 3 may together with the carbon atom to which they are attached form a C4-C7 carbocyclic ring or a 5-7 membered heterocyclic ring {the C4-C7 carbocyclic ring and the 5-7 membered heterocyclic ring may be substituted with one or more substituents selected from Group B},

[0023] R 6 , R 7 , R 8 and R 9 which are the same or different and represent a hydrogen atom or a fluorine atom,

[0024] R 10 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 35 , R 36 , R 37 , R 38 , R 39 , R 40 , R 41 , R 42 , R 43 , R 44 , and R 45Same or different, and represents a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C6-C10 aryl group, or a 5-10 membered aromatic heterocyclic group that can be substituted by one or more substituents selected from Group D {the C3-C6 cycloalkyl group, the C6-C10 aryl group, and the 5-10 membered aromatic heterocyclic group can be substituted by one or more substituents selected from Group C} or a hydrogen atom,

[0025] R 34 Represents a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C6-C10 aryl group, or a 5-10 membered aromatic heterocyclic group that can be substituted by one or more substituents selected from Group D {the C3-C6 cycloalkyl group, the C6-C10 aryl group, and the 5-10 membered aromatic heterocyclic group can be substituted by one or more substituents selected from Group C},

[0026] R 11 Represents a C1-C6 chain hydrocarbon group, or a C3-C6 cycloalkyl group that can be substituted by one or more substituents selected from the group consisting of a halogen atom and a cyano group {the C3-C6 cycloalkyl group can be substituted by one or more substituents selected from the group consisting of a halogen atom and a cyano group},

[0027] n represents 0, 1, or 2,

[0028] k represents 0, 1, or 2.

[0029] Group A: A group consisting of a C3-C6 cycloalkyl group, a C1-C3 alkoxy group, a C1-C3 alkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 alkylsulfonyl group {the C3-C6 cycloalkyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group can be substituted by one or more halogen atoms}, a halogen atom, and a cyano group.

[0030] Group B: A group consisting of a C1-C3 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C1-C3 alkoxy group {the C1-C3 chain hydrocarbon group, the C3-C6 cycloalkyl group, and the C1-C3 alkoxy group can be substituted by one or more halogen atoms}, a halogen atom, a nitro group, and a cyano group.

[0031] Group C: A group consisting of a C1-C3 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C1-C3 alkoxy group, a C1-C3 alkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 alkylsulfonyl group {the C1-C3 chain hydrocarbon group, the C3-C6 cycloalkyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group can be substituted by one or more substituents selected from the group consisting of a halogen atom and a cyano group}, a halogen atom, and a cyano group.

[0032] Group D: A group consisting of C1-C3 alkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl {the C1-C3 alkoxy, the C1-C3 alkylthio, the C1-C3 alkylsulfinyl, and the C1-C3 alkylsulfonyl may be substituted with one or more halogen atoms}, C3-C6 cycloalkyl, C6-C10 aryl, 5-10-membered aromatic heterocyclic group {the C3-C6 cycloalkyl, the C6-C10 aryl, and the 5-10-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group C}, halogen atom, and cyano group.

[0033] Group E: A group consisting of C1-C3 chain hydrocarbon group, C3-C6 cycloalkyl, C1-C3 alkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl {the C1-C3 chain hydrocarbon group, the C3-C6 cycloalkyl, the C1-C3 alkoxy, the C1-C3 alkylthio, the C1-C3 alkylsulfinyl, and the C1-C3 alkylsulfonyl may be substituted with one or more halogen atoms}, halogen atom, and cyano group.

[0034] 〔2〕The method according to 〔1〕, wherein the compound represented by formula (I) or its N-oxide or their salts in 〔1〕 are the following compounds or their N-oxides or their salts, and in the said compounds:

[0035] R 1 、R 2 、R 3 、R 4 and R 5 are the same or different and are C1-C6 chain hydrocarbon groups, C3-C6 cycloalkyl, C6-C10 aryl {the C3-C6 cycloalkyl and the C6-C10 aryl may be substituted with one or more substituents selected from Group E}, hydrogen atom, halogen atom, nitro group, cyano group, -OR 10 、-S(O) k R 11 、-C(O)R 12 、-CR 13 =N-O-R 14 、-C(O)NR 20 R 21 、-NR 22 C(O)R 23 、-C(O)N(OR 24 )R 25 、-N(OR 26 )C(O)R 27 、or -NR 33 C(O)OR 34 ,

[0036] R 1 and R 2 together with the carbon atom to which they are attached can form a C4-C7 carbocyclic ring or a 5- to 7-membered heterocyclic ring {the C4-C7 carbocyclic ring and the 5- to 7-membered heterocyclic ring may be substituted with one or more substituents selected from Group B},

[0037] R 2 and R 3 together with the carbon atom to which they are attached can form a C4-C7 carbocyclic ring or a 5- to 7-membered heterocyclic ring {the C4-C7 carbocyclic ring and the 5- to 7-membered heterocyclic ring may be substituted with one or more substituents selected from Group B},

[0038] R 34 is a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group or a C6-C10 aryl group that may be substituted with one or more substituents selected from Group D {the C3-C6 cycloalkyl group and the C6-C10 aryl group may be substituted with one or more substituents selected from Group C},

[0039] R 11 is a C1-C6 chain hydrocarbon group that may be substituted with one or more substituents selected from Group D or a C3-C6 cycloalkyl group {the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}.

[0040] [3] The method according to [1] or [2], wherein the compound of formula (I) or its N-oxide or their salts in [1] are the following compound or its N-oxide or their salts, in the said compound:

[0041] R 6 、R 7 、R 8 and R 9 are each a hydrogen atom.

[0042] [4] The method according to [1] or [2], wherein the compound of formula (I) or its N-oxide or their salts in [1] are the following compound or its N-oxide or their salts, in the said compound:

[0043] Q is a group represented by Q1 or a group represented by Q2,

[0044] R 6 、R 7 and R 8 are each a hydrogen atom.

[0045] [5] The method according to [1] or [2], wherein the compound of formula (I) or its N-oxide or their salts in [1] are the following compound or its N-oxide or their salts, in the said compound:

[0046] Q is the group shown in Q1,

[0047] R 6 and R 7 each represents a hydrogen atom.

[0048] The compound represented by formula (II) (hereinafter, referred to as the compound N of the present invention) or its N-oxide or their salts (hereinafter, the compound represented by formula (II) or its N-oxide or their salts are referred to as the compounds of the present invention),

[0049] [Chemical formula 3]

[0050]

[0051] [In the formula,

[0052] Q A and the combination of m represent:

[0053] Q A is the group shown in Q A 1 or Q A 2 shown groups,

[0054] and m is a combination of 0, 1 or 2; or,

[0055] Q A is the group shown in Q A 3 shown groups,

[0056] and m is a combination of 1 or 2,

[0057] Q A 1 shown group, Q A 2 shown groups, and Q A 3 shown groups each represent the group shown by the following formula (# represents the bonding site to the phenyl group, ● represents the bonding site to the sulfur atom),

[0058] [Chemical formula 4]

[0059]

[0060] R 6A 、R 7A 、R 8A and R 9A are the same or different and represent a hydrogen atom or a fluorine atom,

[0061] Z A represents a C2-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group {the C2-C6 chain hydrocarbon group and the C3-C6 cycloalkyl group may be substituted by one or more halogen atoms}, or may be selected from group E Aa 5- to 10-membered aromatic heterocyclic group substituted with one or more substituents selected from the group consisting of

[0062] R 3A represents a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C6-C10 aryl group, or a 5- to 10-membered aromatic heterocyclic group {the C3-C6 cycloalkyl group, the C6-C10 aryl group, and the 5- to 10-membered aromatic heterocyclic group may be substituted with one or more substituents selected from the group consisting of A}, a hydrogen atom, a halogen atom, a nitro group, a cyano group, -OR A ,-S(O) 10A R p ,-C(O)R 11A ,-CR 12A =N-O-R 13A ,-O-N=CR 14A R 15A ,-N=N-CR 16A R 17A R 18A R 19A ,-C(O)NR 20A R 21A ,-NR 22A C(O)R 23A ,-C(O)N(OR 24A )R 25A ,-N(OR 26A )C(O)R 27A ,-NR 28A C(O)NR 29A R 30A ,-OC(O)NR 31A R 32A ,-NR 33A C(O)OR 34A ,-NR 35A C(O)C(O)NR 36A R 37A ,-CR 38A R 39A NR 40A C(O)C(O)NR 41A R 42A , or -NR 43A C(O)C(O)N(OR 44A )R 45A ,

[0063] R 2A and R 4A are the same or different and represent a group that may be AA C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C6-C10 aryl group, or a 5-10 membered aromatic heterocyclic group substituted with one or more substituents selected from group C A and substituted with one or more substituents selected from group C 10A -C(O)R 12A -CR 13A =N-O-R 14A -O-N=CR 15A R 16A -N=N-CR 17A R 18A R 19A -C(O)NR 20A R 21A -NR 22A C(O)R 23B -C(O)N(OR 24A )R 25A -N(OR 26A )C(O)R 27A -NR 28A C(O)NR 29A R 30A -OC(O)NR 31A R 32A -NR 33A C(O)OR 34A -NR 35A C(O)C(O)NR 36A R 37A -CR 38A R 39A NR 40A C(O)C(O)NR 41A R 42A or -NR 43A C(O)C(O)N(OR 44A )R 45A ,

[0064] R 1A and R 5A are the same or different and represent a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C6-C10 aryl group, or a 5-10 membered aromatic heterocyclic group substituted with one or more substituents selected from group A A and substituted with one or more substituents selected from group C A and substituted with one or more substituents selected from group C 10A -S(O)p R 11A 、 -C(O)R 12A 、 -CR 13A =N - O - R 14A 、 -O - N=CR 15A R 16A 、 -N=N - CR 17A R 18A R 19A 、 -C(O)NR 20A R 21A 、 -NR 22B C(O)R 23A 、 -C(O)N(OR 24A )R 25A 、 -N(OR 26A )C(O)R 27A 、 -NR 28B C(O)NR 29A R 30A 、 -OC(O)NR 31A R 32A 、 -NR 33B C(O)OR 34A 、 -NR 35A C(O)C(O)NR 36A R 37A 、 -CR 38A R 39A NR 40A C(O)C(O)NR 41A R 42A 、 or -NR 43A C(O)C(O)N(OR 44A )R 45A ,

[0065] wherein at least one of R 1A 、 R 2A 、 R 3A 、 R 4A and R 5A is not a hydrogen atom,

[0066] R 1A and R 2A may together with the carbon atom to which they are attached form a C4 - C7 carbocyclic ring or a 5 - 7 - membered heterocyclic ring {the C4 - C7 carbocyclic ring and the 5 - 7 - membered heterocyclic ring may be substituted by one or more substituents selected from Group B A},

[0067] R 2A and R 3A may together with the carbon atom to which they are attached form a C4 - C7 carbocyclic ring or a 5 - 7 - membered heterocyclic ring {the C4 - C7 carbocyclic ring and the 5 - 7 - membered heterocyclic ring may be substituted by one or more substituents selected from Group BA substituted by more than one substituent selected from

[0068] R 10A and R 12A and R 13A and R 14A and R 15A and R 16A and R 17A and R 18A and R 19A and R 20A and R 21A and R 22A and R 23A and R 24A and R 25A and R 26A and R 27A and R 28A and R 29A and R 30A and R 31A and R 32A and R 33A and R 35A and R 36A and R 37A and R 38A and R 39A and R 40A and R 41A and R 42A and R 43A and R 44A and R 45A are the same or different and represent a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C6-C10 aryl group, or a 5-10 membered aromatic heterocyclic group that can be substituted by more than one substituent selected from group D A {the C3-C6 cycloalkyl group, the C6-C10 aryl group, and the 5-10 membered aromatic heterocyclic group can be substituted by more than one substituent selected from group C A} or a hydrogen atom,

[0069] R 34A and R 22B and R 28B and R 33B are the same or different and represent a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C6-C10 aryl group, or a 5-10 membered aromatic heterocyclic group that can be substituted by more than one substituent selected from group D A {the C3-C6 cycloalkyl group, the C6-C10 aryl group, and the 5-10 membered aromatic heterocyclic group can be substituted by more than one substituent selected from group C A},

[0070] R 23B represents a group that can be selected from group DA a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, or a C6-C10 aryl group substituted with one or more substituents selected from Group C A {the C3-C6 cycloalkyl group and the C6-C10 aryl group may be substituted with one or more substituents selected from the group} or a hydrogen atom,

[0071] R 11A represents a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group that may be substituted with one or more substituents selected from Group D A {the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group},

[0072] p represents 0, 1, or 2.

[0073] Group A A : a group consisting of a C3-C6 cycloalkyl group, a C1-C3 alkoxy group, a C1-C3 alkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 alkylsulfonyl group {the C3-C6 cycloalkyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more halogen atoms}, a halogen atom, and a cyano group.

[0074] Group B A : a group consisting of a C1-C3 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C1-C3 alkoxy group {the C1-C3 chain hydrocarbon group, the C3-C6 cycloalkyl group, and the C1-C3 alkoxy group may be substituted with one or more halogen atoms}, a halogen atom, a nitro group, and a cyano group.

[0075] Group C A : a group consisting of a C1-C3 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C1-C3 alkoxy group, a C1-C3 alkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 alkylsulfonyl group {the C1-C3 chain hydrocarbon group, the C3-C6 cycloalkyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}, a halogen atom, and a cyano group.

[0076] Group D A: a group consisting of C1-C3 alkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl {the C1-C3 alkoxy, the C1-C3 alkylthio, the C1-C3 alkylsulfinyl and the C1-C3 alkylsulfonyl may be substituted by one or more halogen atoms}, C3-C6 cycloalkyl, C6-C10 aryl, 5-10 membered aromatic heterocyclic group {the C3-C6 cycloalkyl, the C6-C10 aryl and the 5-10 membered aromatic heterocyclic group may be substituted by one or more substituents selected from the group C A in the above}, halogen atom, and cyano group.

[0077] Group E A : a group consisting of C1-C3 chain hydrocarbon group, C3-C6 cycloalkyl, C1-C3 alkoxy {the C1-C3 chain hydrocarbon group, the C3-C6 cycloalkyl, and the C1-C3 alkoxy may be substituted by one or more halogen atoms}, halogen atom, and cyano group. ].

[0078] [7] The compound according to [6] or its N-oxide or their salts, wherein R 3A is a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, C3-C6 cycloalkyl {the C3-C6 cycloalkyl may be substituted by one or more substituents selected from the group consisting of C1-C3 chain hydrocarbon group and halogen atom}, hydrogen atom, halogen atom, nitro group, cyano group, -OR 10A , -S(O) p R 11A , -C(O)R 12A , -CR 13A =N-O-R 14A , -C(O)NR 20A R 21A , -NR 22A C(O)R 23A , -C(O)N(OR 24A )R 25A , -N(OR 26A )C(O)R 27A or -NR 33A C(O)OR 34A ,

[0079] R 2A and R 4A are the same or different and are a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, C3-C6 cycloalkyl {the C3-C6 cycloalkyl may be substituted by one or more substituents selected from the group consisting of C1-C3 chain hydrocarbon group and halogen atom}, hydrogen atom, halogen atom, nitro group, cyano group, -OR 10A , -C(O)R 12A , -CR13A =NOR 14A 、-C(O)NR 20A R 21A 、-NR 22A C(O)R 23B 、-C(O)N(OR 24A )R 25A 、-N(OR 26A )C(O)R 27A or -NR 33A C(O)OR 34A ,

[0080] R 1A and R 5A the same or different, and are C1-C6 chain hydrocarbon groups which may be substituted with one or more halogen atoms, C3-C6 cycloalkyl groups {the C3-C6 cycloalkyl groups may be substituted with one or more halogen atoms}, hydrogen atoms, halogen atoms, nitro groups, cyano groups, -OR 10A 、-S(O) p R 11A 、-C(O)R 12A , -CR 13A =NOR 14A 、-C(O)NR 20A R 21A 、-NR 22B C(O)R 23A 、-C(O)N(OR 24A )R 25A 、-N(OR 26A )C(O)R 27A or -NR 33B C(O)OR 34A ,

[0081] Among them, R 1A , R 2A , R 3A , R 4A and R 5A At least one of them is not a hydrogen atom,

[0082] R 1A and R 2A Together with the carbon atoms to which they are bonded, they can form a C4-C7 carbocyclic ring, or a 5-7 membered heterocyclic ring {the C4-C7 carbocyclic ring and the 5-7 membered heterocyclic ring can be selected from group B A substituted with one or more substituents in},

[0083] R 2A and R 3A Together with the carbon atoms to which they are bonded, they can form a C4-C7 carbocyclic ring, or a 5-7 membered heterocyclic ring {the C4-C7 carbocyclic ring and the 5-7 membered heterocyclic ring can be selected from group BA substituted by more than one substituent in

[0084] 〔8〕The compound as described in 〔6〕 or 〔7〕, or its N-oxide, or their salts, wherein R 6A , R 7A , R 8A and R 9A are each a hydrogen atom.

[0085] 〔9〕The compound as described in 〔6〕 or 〔7〕, or its N-oxide, or their salts, wherein Q A is the group shown in Q A 1 or the group shown in Q A 2, m is 0, 1 or 2,

[0086] R 6A , R 7A and R 8A are each a hydrogen atom.

[0087] 〔10〕The compound as described in 〔6〕 or 〔7〕, or its N-oxide, or their salts, wherein Q A is the group shown in Q A 1, m is 0, 1 or 2,

[0088] R 6A and R 7A are each a hydrogen atom.

[0089] 〔11〕A plant disease control composition comprising the compound as described in any one of 〔6〕 to 〔10〕, or its N-oxide, or their salts.

[0090] 〔12〕A plant disease control method, which is carried out by treating a plant or the soil of a cultivated plant with an effective amount of the compound as described in any one of 〔6〕 to 〔10〕, or its N-oxide, or their salts.

[0091] 〔13〕Use of the compound as described in any one of 〔6〕 to 〔10〕, or its N-oxide, or their salts for controlling plant diseases.

[0092] 〔14〕A composition comprising one or more components selected from the group consisting of group (a), group (b), group (c) and group (d), and the compound as described in any one of 〔6〕 to 〔10〕, or its N-oxide, or their salts:

[0093] Group (a): the group consisting of an insecticidal active ingredient, a miticidal active ingredient and a nematicidal active ingredient;

[0094] Group (b): a bactericidal active ingredient;

[0095] Group (c): Plant growth regulating ingredient;

[0096] Group (d): Repellent ingredient.

[0097]

[15] A seed or vegetative propagating organ that retains an effective amount of the compound represented by formula (I) or its N-oxide or a salt thereof according to any one of [1] to [5], the compound represented by formula (I) or its N-oxide or a salt thereof according to any one of [6] to

[10] , or the composition according to

[14] .

[0098]

[16] The compound represented by formula (III) (hereinafter referred to as Intermediate A)

[0099] [Chemical formula 5]

[0100]

[0101] [In the formula,

[0102] R 6B and R 7B are the same or different and represent a hydrogen atom or a fluorine atom,

[0103] Z B represents a C3-C6 chain hydrocarbon group or a C4-C6 cycloalkyl group {the C3-C6 chain hydrocarbon group and the C4-C6 cycloalkyl group may be substituted with one or more halogen atoms}.].

[0104] Effects of the invention

[0105] By the present invention, plant diseases can be controlled. Detailed implementation manners

[0106] The substituents in the present invention will be described.

[0107] The halogen atom means a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0108] When the substituent is substituted with two or more halogen atoms or groups, these halogen atoms or groups may be the same or different from each other.

[0109] The expression "CY-CW" in this specification means that the number of carbon atoms is from Y to W. For example, the expression "C1-C6" means that the number of carbon atoms is from 1 to 6.

[0110] The chain hydrocarbon group means an alkyl group, an alkenyl group, or an alkynyl group.

[0111] As the alkyl group, for example, methyl, ethyl, propyl, isopropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, butyl, sec-butyl, tert-butyl, pentyl, and hexyl can be mentioned.

[0112] As the alkenyl group, for example, vinyl, 1-propenyl, 2-propenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 1,2-dimethyl-1-propenyl, 3-butenyl, 4-pentenyl, and 5-hexenyl can be mentioned.

[0113] As the alkynyl group, for example, ethynyl, 1-propynyl, 2-propynyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 2-butynyl, 4-pentynyl, and 5-hexynyl can be mentioned.

[0114] As the cycloalkyl group, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl can be mentioned.

[0115] As the alkoxy group, for example, methoxy, ethoxy, propoxy, and isopropoxy can be mentioned.

[0116] As the alkylthio group, for example, methylthio, ethylthio, propylthio, and isopropylthio can be mentioned.

[0117] As the alkylsulfinyl group, for example, methylsulfinyl, ethylsulfinyl, propylsulfinyl, and isopropylsulfinyl can be mentioned.

[0118] As the alkylsulfonyl group, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, and isopropylsulfonyl can be mentioned.

[0119] As the aryl group, for example, phenyl, indenyl, indanyl, naphthyl, and tetrahydronaphthyl can be mentioned.

[0120] As the 5- to 10-membered aromatic heterocyclic group, for example, 5-membered aromatic heterocyclic group, 6-membered aromatic heterocyclic group, 9-membered aromatic heterocyclic group, and 10-membered aromatic heterocyclic group can be mentioned. As the 5-membered aromatic heterocyclic group, for example, pyrrolyl, furyl, thienyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, and thiadiazolyl can be mentioned. As the 6-membered aromatic heterocyclic group, for example, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, and tetrazinyl can be mentioned. As the 9-membered aromatic heterocyclic group, for example, indolyl, indazolyl, benzimidazolyl, imidazopyridyl group, benzothienyl, and benzofuryl can be mentioned. As the 10-membered aromatic heterocyclic group, for example, quinolinyl, isoquinolinyl, quinazolinyl, and quinoxalinyl can be mentioned.

[0121] As the C4-C7 carbocyclic ring, for example, cyclobutene ring, cyclopentene ring, cyclopentadiene ring, cyclohexene ring, cyclohexadiene ring, benzene ring, and cycloheptene ring can be mentioned.

[0122] As a 5- to 7-membered heterocycle, for example, a furan ring, a dihydrofuran ring, a thiophene ring, a dihydrothiophene ring, a pyrrole ring, a dihydropyrrole ring, a pyrazole ring, an imidazole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, a 1,3-dioxolene ring, a triazole ring, an oxadiazole ring, a thiadiazole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a pyran ring, and a dihydropyran ring can be mentioned.

[0123] "R 1A , R 2A , R 3A , R 4A , and R 5A in at least one of them is not a hydrogen atom" such a description means the same as "not including the case where R 1A , R 2A , R 3A , R 4A , and R 5A are all hydrogen atoms".

[0124] This compound, the compound of the present invention, and Intermediate A sometimes have more than one stereoisomer. As stereoisomers, enantiomers, diastereomers, rotational enantiomers, and cis-trans isomers can be mentioned. The present invention includes each stereoisomer and a mixture of stereoisomers in any ratio.

[0125] This compound or the compound of the present invention sometimes forms acid addition salts such as hydrochloride, sulfate, nitrate, phosphate, acetate, or benzoate by mixing with an acid such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, or benzoic acid.

[0126] As the form of this compound N, the following compounds can be mentioned.

[0127] 〔Form 1〕This compound N, wherein R 1 , R 2 , R 3 , R 4 , and R 5 are the same or different and are a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group {the C1-C6 chain hydrocarbon group and the C3-C6 cycloalkyl group may be substituted with one or more halogen atoms}, a hydrogen atom, a halogen atom, -OR 10 , -C(O)NR 20 R 21 , -NR 22 C(O)R 23 , -C(O)N(OR 24 )R 25 , -N(OR 26 )C(O)R 27 , or -NR 33 C(O)OR 34 .

[0128] 〔Mode 2〕This compound N, wherein R 2 , R 3 , and R 4 are the same or different and are a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group {the C1-C6 chain hydrocarbon group and the C3-C6 cycloalkyl group may be substituted by one or more halogen atoms}, a hydrogen atom, a halogen atom, -OR 10 , -C(O)NR 20 R 21 , -NR 22 C(O)R 23 , -C(O)N(OR 24 )R 25 , -N(OR 26 )C(O)R 27 , or -NR 33 C(O)OR 34 , R 1 and R 5 are the same or different and are a hydrogen atom or a halogen atom.

[0129] 〔Mode 3〕This compound N, wherein R 1 and R 5 are the same or different and are a hydrogen atom or a halogen atom, R 2 and R 4 are the same or different and are a C1-C6 chain hydrocarbon group that may be substituted by one or more halogen atoms, a hydrogen atom, a halogen atom, -OR 10 , or -NR 33 C(O)OR 34 , R 3 is a C1-C6 chain hydrocarbon group that may be substituted by one or more halogen atoms, a C3-C6 cycloalkyl group, a hydrogen atom, a halogen atom, -OR 10 , or -NR 33 C(O)OR 34 .

[0130] 〔Mode 4〕The compound according to Mode 1, wherein R 10 is a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, or a 5-10-membered aromatic heterocyclic group that may be substituted by one or more substituents selected from the group F {the 5-10-membered aromatic heterocyclic group may be substituted by a chain hydrocarbon group that may be substituted by one or more halogen atoms}, R 20 , R 21 , R 22 , R 24 , and R 26 are the same or different and are a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, or a hydrogen atom, R 23 , R 25, and R 27 are the same or different and are a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, or a phenyl group {the phenyl group may be substituted by one or more substituents selected from group G}, R 33 is a C1-C6 chain hydrocarbon group, cyclopropyl, or a hydrogen atom, R 34 is a C1-C6 chain hydrocarbon group that may be substituted by one or more halogen atoms.

[0131] Group F: A group consisting of a C6-C10 aryl group that may be substituted by one or more substituents selected from group G, and a halogen atom.

[0132] Group G: A group consisting of a C1-C3 alkoxy group, a C1-C3 chain hydrocarbon group that may be substituted by one or more halogen atoms, a halogen atom, and a cyano group.

[0133] 〔Mode 5〕The compound according to Mode 1, wherein R 10 is a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, or a 5-10 membered aromatic heterocyclic group that may be substituted by one or more substituents selected from group F {the 5-10 membered aromatic heterocyclic group may be substituted by a chain hydrocarbon group that may be substituted by one or more halogen atoms}, R 20 , R 21 , R 22 , R 24 , and R 26 are the same or different and are a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, or a hydrogen atom, R 23 , R 25 , and R 27 are the same or different and are a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, or a phenyl group {the phenyl group may be substituted by one or more substituents selected from group G}, R 33 is a hydrogen atom, R 34 is a C1-C3 chain hydrocarbon group.

[0134] 〔Mode 6〕The compound according to Mode 3, wherein R 10 is a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, or a 5-10 membered aromatic heterocyclic group that may be substituted by one or more substituents selected from group F {the 5-10 membered aromatic heterocyclic group may be substituted by a chain hydrocarbon group that may be substituted by one or more halogen atoms}, R 20 , R 21 , R 22 , R 24 , and R 26 are the same or different and are a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, or a hydrogen atom, R 23 , R 25 , and R 27identical or different, and is a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, or a phenyl group {the phenyl group may be substituted with one or more substituents selected from group G}, R 33 is a hydrogen atom, R 34 is a C1-C3 chain hydrocarbon group.

[0135] [Mode 7] This compound N, wherein R 1 and R 5 are each a hydrogen atom, R 2 and R 4 are identical or different, and are a hydrogen atom or a halogen atom, R 3 is a C1-C6 chain hydrocarbon group that may be substituted with one or more halogen atoms or a halogen atom.

[0136] [Mode 8] This compound N, wherein Z is a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a phenyl group, or a 6-membered aromatic heterocyclic group that may be substituted with one or more substituents selected from group A.

[0137] [Mode 9] This compound N, wherein Z is a C1-C6 chain hydrocarbon group or a pyridyl group.

[0138] [Mode 10] This compound N, wherein Z is a C1-C6 chain hydrocarbon group.

[0139] [Mode 11] The compound according to Mode 4, wherein Z is a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a phenyl group, or a 6-membered aromatic heterocyclic group that may be substituted with one or more substituents selected from group A.

[0140] [Mode 12] The compound according to Mode 4, wherein Z is a C1-C6 chain hydrocarbon group or a pyridyl group.

[0141] [Mode 13] The compound according to Mode 4, wherein Z is a C1-C6 chain hydrocarbon group.

[0142] [Mode 14] The compound according to Mode 6, wherein Z is a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a phenyl group, or a 6-membered aromatic heterocyclic group that may be substituted with one or more substituents selected from group A.

[0143] [Mode 15] The compound according to Mode 6, wherein Z is a C1-C6 chain hydrocarbon group or a pyridyl group.

[0144] [Mode 16] The compound according to Mode 6, wherein Z is a C1-C6 chain hydrocarbon group.

[0145] [Mode 17] The compound according to Mode 7, wherein Z is a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a phenyl group, or a 6-membered aromatic heterocyclic group that may be substituted with one or more substituents selected from group A.

[0146] 〔Embodiment 18〕The compound according to Embodiment 7, wherein Z is a C1-C6 chain hydrocarbon group or a pyridyl group.

[0147] 〔Embodiment 19〕This compound N, wherein n is 1 or 2.

[0148] 〔Embodiment 20〕This compound N, wherein n is 2.

[0149] 〔Embodiment 21〕The compound according to Embodiment 15, wherein n is 2.

[0150] 〔Embodiment 22〕The compound according to Embodiment 17, wherein n is 2.

[0151] 〔Embodiment 23〕The compound according to Embodiment 18, wherein n is 2.

[0152] 〔Embodiment 24〕The compound according to any one of Embodiments 1 to 23 or this compound N, wherein Q is the group represented by Q1 or the group represented by Q2.

[0153] 〔Embodiment 25〕The compound according to any one of Embodiments 1 to 23 or this compound N, wherein Q is the group represented by Q1.

[0154] 〔Embodiment 26〕The compound according to any one of Embodiments 1 to 23 or this compound N, wherein R 6 and R 7 are each a hydrogen atom.

[0155] 〔Embodiment 27〕The compound according to any one of Embodiments 1 to 23 or this compound N, wherein R 8 is a hydrogen atom.

[0156] 〔Embodiment 28〕The compound according to any one of Embodiments 1 to 23 or this compound N, wherein R 9 is a hydrogen atom.

[0157] 〔Embodiment 29〕The compound according to any one of Embodiments 1 to 23 or this compound N, wherein R 6 , R 7 , R 8 and R 9 are each a hydrogen atom.

[0158] 〔Embodiment 30〕The compound according to any one of Embodiments 1 to 23 or this compound N, wherein Q is the group represented by Q1 or the group represented by Q2, and R 6 , R 7 , and R 8 are each a hydrogen atom.

[0159] 〔Mode 31〕Any compound according to Modes 1 to 23 or Compound N of the present invention, wherein Q is the group represented by Q1, and R 6 and R 7 are each a hydrogen atom.

[0160] 〔Mode 32〕Any compound according to Modes 1 to 18 or Compound N of the present invention, wherein Q is the group represented by Q1 or the group represented by Q3, and n is 0 or 2.

[0161] 〔Mode 33〕Any compound according to Modes 1 to 18 or Compound N of the present invention, wherein Q is the group represented by Q3, and n is 2.

[0162] 〔Mode 34〕Any compound according to Modes 1 to 18 or Compound N of the present invention, wherein Q is the group represented by Q1 or the group represented by Q3, n is 0 or 2, and R 6 , R 7 and R 9 are each a hydrogen atom.

[0163] 〔Mode 35〕Any compound according to Modes 1 to 18 or Compound N of the present invention, wherein Q is the group represented by Q3, n is 2, and R 9 is a hydrogen atom.

[0164] 〔Mode 36〕Compound N of the present invention, wherein Q is the group represented by Q1 or the group represented by Q2, and n is 0 or 2.

[0165] 〔Mode 37〕Compound N of the present invention, wherein Q is the group represented by Q1 or the group represented by Q2, and n is 2.

[0166] 〔Mode 38〕Compound N of the present invention, wherein Q is the group represented by Q1 or the group represented by Q3, and n is 2.

[0167] 〔Mode 39〕Compound N of the present invention, wherein Q is the group represented by Q1, and n is 0 or 2.

[0168] 〔Mode 40〕Compound N of the present invention, wherein Q is the group represented by Q3, and n is 2.

[0169] 〔Mode 41〕Any compound according to Modes 36 to 40 or Compound N of the present invention, wherein Z is a C1-C6 chain hydrocarbon group that can be substituted with one or more halogen atoms, a phenyl group that can be substituted with one or more substituents selected from Group E, or a C3-C6 cycloalkyl group.

[0170] 〔Mode 42〕A compound according to any one of Modes 36 to 40 or this Compound N, wherein Z is a C2-C5 chain hydrocarbon group which may be substituted with one or more halogen atoms, or a phenyl group {the phenyl group may be substituted with one or more substituents selected from the group consisting of a methoxy group and a halogen atom}.

[0171] 〔Mode 43〕A compound according to Mode 41, wherein R 3 is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, -OR 10 , a hydrogen atom, or a halogen atom, and R 10 is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms.

[0172] 〔Mode 44〕A compound according to Mode 41, wherein R 1 and R 5 are each a hydrogen atom, R 2 and R 4 are the same or different and are a hydrogen atom or a halogen atom, and R 3 is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, -OR 10 , a hydrogen atom, or a halogen atom (wherein at least one of R 1 , R 2 , R 3 , R 4 and R 5 is not a hydrogen atom).

[0173] 〔Mode 45〕A compound according to Mode 42, wherein R 3 is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, -OR 10 , a hydrogen atom, or a halogen atom, and R 10 is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms.

[0174] 〔Mode 46〕A compound according to Mode 42, wherein R 1 and R 5 are each a hydrogen atom, R 2 and R 4 are the same or different and are a hydrogen atom or a halogen atom, and R 3 is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, -OR 10 , a hydrogen atom, or a halogen atom (wherein at least one of R 1 , R 2 , R 3 , R 4 and R 5 is not a hydrogen atom).

[0175] [Mode 47] Any one of the compounds according to Modes 36 to 40 or this Compound N, wherein Z is a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group, and R 1 , R 2 , R 3 , R 4 , and R 5 are the same or different and are a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group {the C1-C6 chain hydrocarbon group and the C3-C6 cycloalkyl group may be substituted with one or more halogen atoms}, a hydrogen atom, a halogen atom, -OR 10 , or -NHC(O)OR 34 , and R 10 is a C1-C6 chain hydrocarbon group that may be substituted with one or more substituents selected from Group F2, or a phenyl group that may be substituted with one or more substituents selected from Group G, and R 34 is a C1-C6 chain hydrocarbon group.

[0176] Group F2: A group consisting of a phenyl group that may be substituted with one or more substituents selected from Group G and a halogen atom.

[0177] As a mode of the compound of the present invention N, the following compounds can be cited.

[0178] [Mode A1] The compound of the present invention N, wherein R 1A and R 5A are the same or different and are a C1-C6 chain hydrocarbon group that may be substituted with one or more halogen atoms, a hydrogen atom, a halogen atom, -OR 10A , -C(O)NR 20A R 21A , -NR 22B C(O)R 23A , -C(O)N(OR 24A )R 25A , -N(OR 26A )C(O)R 27A , or -NR 33B C(O)OR 34A (wherein at least one of R 1A , R 2A , R 3A , R 4A , and R 5A is not a hydrogen atom).

[0179] [Mode A2] The compound of the present invention N, wherein R 1A and R 5A are the same or different and are a hydrogen atom or a fluorine atom (wherein R 1A , R 2A , R 3A , R 4Aand R 5A (wherein at least one of them is not a hydrogen atom).

[0180] [Mode A3] Compound N of the present invention, wherein R 1A and R 5A are each a hydrogen atom (wherein at least one of R 1A , R 2A , R 3A , R 4A and R 5A is not a hydrogen atom).

[0181] [Mode A4] Compound N of the present invention, wherein R 2A and R 4A are the same or different and are a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a hydrogen atom, a halogen atom, -OR 10A , -C(O)NR 20A R 21A , -NR 22A C(O)R 23B , -C(O)N(OR 24A )R 25A , -N(OR 26A )C(O)R 27A , or -NR 33A C(O)OR 34A (wherein at least one of R 1A , R 2A , R 3A , R 4A and R 5A is not a hydrogen atom).

[0182] [Mode A5] Compound N of the present invention, wherein R 2A and R 4A are the same or different and are a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a hydrogen atom, a halogen atom, -OR 10A , or -NR 33A C(O)OR 34A (wherein at least one of R 1A , R 2A , R 3A , R 4A and R 5A is not a hydrogen atom).

[0183] [Mode A6] Compound N of the present invention, wherein R 3A is a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group {the C1-C6 chain hydrocarbon group and the C3-C6 cycloalkyl group may be substituted by one or more halogen atoms}, -OR 10A , -C(O)NR20A R 21A 、 -NR 22A C(O)R 23A 、 -C(O)N(OR 24A )R 25A 、 -N(OR 26A )C(O)R 27A 、 or -NR 33A C(O)OR 34A (wherein at least one of R 1A 、 R 2A 、 R 3A 、 R 4A 、 and R 5A is not a hydrogen atom).

[0184] 〔Mode A7〕Compound N of the present invention, wherein R 3A is C3 - C6 cycloalkyl, a C1 - C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a hydrogen atom, a halogen atom, -OR 10A 、 or -NR 33A C(O)OR 34A (wherein at least one of R 1A 、 R 2A 、 R 3A 、 R 4A 、 and R 5A is not a hydrogen atom).

[0185] 〔Mode A8〕Compound N of the present invention, wherein R 1A and R 5A are the same or different and are a C1 - C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a hydrogen atom, a halogen atom, -OR 10A 、 -C(O)NR 20A R 21A 、 -NR 22B C(O)R 23A 、 -C(O)N(OR 24A )R 25A 、 -N(OR 26A )C(O)R 27A 、 or -NR 33B C(O)OR 34A , R 2A and R 4A are the same or different and are a C1 - C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a hydrogen atom, a halogen atom, -OR 10A 、 -C(O)NR 20A R 21A 、 -NR 22A C(O)R 23B 、 -C(O)N(OR 24A)R 25A , -N(OR 26A )C(O)R 27A , or -NR 33A C(O)OR 34A , R 3A is a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group {the C1-C6 chain hydrocarbon group and the C3-C6 cycloalkyl group may be substituted by one or more halogen atoms}, -OR 10A , -C(O)NR 20A R 21A , -NR 22A C(O)R 23A , -C(O)N(OR 24A )R 25A , -N(OR 26A )C(O)R 27A , or -NR 33A C(O)OR 34A (wherein at least one of R 1A , R 2A , R 3A , R 4A and R 5A is not a hydrogen atom).

[0186] [Mode A9] Compound N of the present invention, wherein R 1A and R 5A are the same or different and are a hydrogen atom or a fluorine atom, and R 2A and R 4A are the same or different and are a C1-C6 chain hydrocarbon group that may be substituted by one or more halogen atoms, a hydrogen atom, a halogen atom, -OR 10A , -C(O)NR 20A R 21A , -NR 22A C(O)R 23B , -C(O)N(OR 24A )R 25A , -N(OR 26A )C(O)R 27A , or -NR 33A C(O)OR 34A , R 3A is a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group {the C1-C6 chain hydrocarbon group and the C3-C6 cycloalkyl group may be substituted by one or more halogen atoms}, -OR 10A , -C(O)NR 20A R 21A , -NR 22A C(O)R 23A , -C(O)N(OR 24A )R 25A, -N(OR 26A )C(O)R 27A , or -NR 33A C(O)OR 34A (wherein at least one of R 1A , R 2A , R 3A , R 4A , and R 5A is not a hydrogen atom).

[0187] [Mode A10] Compound N of the present invention, wherein R 1A and R 5A are the same or different and are a hydrogen atom or a fluorine atom, R 2A and R 4A are the same or different and are a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a hydrogen atom, a halogen atom, -OR 10A , or -NR 33A C(O)OR 34A , R 3A is a C3-C6 cycloalkyl group, a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a hydrogen atom, a halogen atom, -OR 10A , or -NR 33A C(O)OR 34A (wherein at least one of R 1A , R 2A , R 3A , R 4A , and R 5A is not a hydrogen atom).

[0188] [Mode A11] Compound N of the present invention, wherein R 1A and R 5A are each a hydrogen atom, R 2A and R 4A are the same or different and are a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a hydrogen atom, a halogen atom, -OR 10A , or -NR 33A C(O)OR 34A , R 3A is a C3-C6 cycloalkyl group, a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a hydrogen atom, a halogen atom, -OR 10A , or -NR 33A C(O)OR 34A (wherein at least one of R 1A , R 2A , R 3A , R 4A , and R 5A is not a hydrogen atom).

[0189] 〔Mode A12〕Compound N of the present invention, wherein R 1A and R 5A are each a hydrogen atom, R 2A and R 4A are the same or different and are a hydrogen atom or a halogen atom, and R 3A is a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a hydrogen atom, or a halogen atom (wherein at least one of R 1A , R 2A , R 3A , R 4A and R 5A is not a hydrogen atom).

[0190] 〔Mode A13〕The compound according to Mode A8, wherein R 10A is a C3-C6 cycloalkyl group, a C1-C6 chain hydrocarbon group which may be substituted by one or more substituents selected from Group F A , or a 5-10 membered aromatic heterocyclic group {the 5-10 membered aromatic heterocyclic group may be substituted by a chain hydrocarbon group which may be substituted by one or more halogen atoms}, R 20A , R 21A , R 22A , R 24A , and R 26A are the same or different and are a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, or a hydrogen atom, R 22B is a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group, R 23A , R 23B , R 25A , and R 27A are the same or different and are a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, or a phenyl group which may be substituted by one or more substituents selected from Group G A , R 33A is a C1-C6 chain hydrocarbon group, cyclopropyl, or a hydrogen atom, R 33B is a C1-C6 chain hydrocarbon group or cyclopropyl, and R 34A is a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms.

[0191] Group F A : A group consisting of a C6-C10 aryl group which may be substituted by one or more substituents selected from Group G A or a halogen atom.

[0192] Group G A : A group consisting of a C1-C3 alkoxy group, a C1-C3 chain hydrocarbon group which may be substituted by one or more halogen atoms, a halogen atom, and a cyano group.

[0193] 〔Mode A14〕A compound according to Mode A9, wherein R 10A is a C3-C6 cycloalkyl group, a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from Group F A , or a 5-10 membered aromatic heterocyclic group {the 5-10 membered aromatic heterocyclic group may be substituted with a chain hydrocarbon group which may be substituted with one or more halogen atoms}, R 20A , R 21A , R 22A , R 24A , and R 26A are the same or different and are a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, or a hydrogen atom, R 23A , R 23B , R 25A , and R 27A are the same or different and are a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, or a phenyl group which may be substituted with one or more substituents selected from Group G A , R 33A is a C1-C6 chain hydrocarbon group, a cyclopropyl group, or a hydrogen atom, R 34A is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms.

[0194] 〔Mode A15〕A compound according to Mode A10, wherein R 10A is a C3-C6 cycloalkyl group, a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from Group F A , or a 5-10 membered aromatic heterocyclic group {the 5-10 membered aromatic heterocyclic group may be substituted with a chain hydrocarbon group which may be substituted with one or more halogen atoms}, R 33A is a C1-C6 chain hydrocarbon group, a cyclopropyl group, or a hydrogen atom, R 34A is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms.

[0195] 〔Mode A16〕A compound according to Mode A11, wherein R 10A is a C3-C6 cycloalkyl group, a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from Group F A , or a 5-10 membered aromatic heterocyclic group {the 5-10 membered aromatic heterocyclic group may be substituted with a chain hydrocarbon group which may be substituted with one or more halogen atoms}, R 33A is a C1-C6 chain hydrocarbon group, a cyclopropyl group, or a hydrogen atom, R 34A is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms.

[0196] 〔Mode A17〕Compound N of the present invention, wherein Z Ais a C2-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, or a 6-membered aromatic heterocyclic group that can be substituted by one or more substituents selected from Group E A in the above formula.

[0197] 〔Embodiment A18〕Compound N of the present invention, wherein Z A is a C2-C6 chain hydrocarbon group or a pyridyl group.

[0198] 〔Embodiment A19〕The compound according to Embodiment A9, wherein Z A is a C2-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, or a 6-membered aromatic heterocyclic group that can be substituted by one or more substituents selected from Group E A in the above formula.

[0199] 〔Embodiment A20〕The compound according to Embodiment A10, wherein Z A is a C2-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, or a 6-membered aromatic heterocyclic group that can be substituted by one or more substituents selected from Group E A in the above formula.

[0200] 〔Embodiment A21〕The compound according to Embodiment A11, wherein Z A is a C2-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, or a 6-membered aromatic heterocyclic group that can be substituted by one or more substituents selected from Group E A in the above formula.

[0201] 〔Embodiment A22〕The compound according to Embodiment A13, wherein Z A is a C2-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, or a 6-membered aromatic heterocyclic group that can be substituted by one or more substituents selected from Group E A in the above formula.

[0202] 〔Embodiment A23〕The compound according to Embodiment A14, wherein Z A is a C2-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, or a 6-membered aromatic heterocyclic group that can be substituted by one or more substituents selected from Group E A in the above formula.

[0203] 〔Embodiment A24〕The compound according to Embodiment A15, wherein Z A is a C2-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, or a 6-membered aromatic heterocyclic group that can be substituted by one or more substituents selected from Group E A in the above formula.

[0204] 〔Embodiment A25〕The compound according to Embodiment A16, wherein Z Ais a C2-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, or a 6-membered aromatic heterocyclic group that can be substituted by one or more substituents selected from Group E A in the above.

[0205] 〔Mode A26〕The compound according to Mode A15, wherein Z A is a C2-C6 chain hydrocarbon group or a pyridyl group.

[0206] 〔Mode A27〕The compound according to Mode A15, wherein Z A is a C2-C6 chain hydrocarbon group or a pyridyl group, R 33A is a hydrogen atom, and R 34A is a C1-C3 chain hydrocarbon group.

[0207] 〔Mode A28〕The compound according to Mode A12, wherein Z A is a C2-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, or a 6-membered aromatic heterocyclic group that can be substituted by one or more substituents selected from Group E A in the above.

[0208] 〔Mode A29〕The compound according to Mode A12, wherein Z A is a C2-C6 chain hydrocarbon group or a pyridyl group.

[0209] 〔Mode A30〕The compound N of the present invention, wherein m is 1 or 2.

[0210] 〔Mode A31〕The compound N of the present invention, wherein m is 2.

[0211] 〔Mode A32〕The compound according to Mode A28, wherein m is 2.

[0212] 〔Mode A33〕The compound according to Mode A29, wherein m is 2.

[0213] 〔Mode A34〕For any one of the compounds according to Modes A1 to A33 or the compound N of the present invention, wherein Q A is the group shown in Q A 1 or the group shown in Q A 2.

[0214] 〔Mode A35〕For any one of the compounds according to Modes A1 to A33 or the compound N of the present invention, wherein Q A is the group shown in Q A 1.

[0215] 〔Mode A36〕For any one of the compounds according to Modes A1 to A33 or the compound N of the present invention, wherein R 6A and R 7A are each a hydrogen atom.

[0216] 〔Aspect A37〕Any one of the compounds according to Aspect A1 to Aspect A33 or Compound N of the present invention, wherein R 8A is a hydrogen atom.

[0217] 〔Aspect A38〕Any one of the compounds according to Aspect A1 to Aspect A33 or Compound N of the present invention, wherein R 9A is a hydrogen atom.

[0218] 〔Aspect A39〕Any one of the compounds according to Aspect A1 to Aspect A33 or Compound N of the present invention, wherein R 6A , R 7A , R 8A and R 9A are each a hydrogen atom.

[0219] 〔Aspect A40〕Any one of the compounds according to Aspect A1 to Aspect A33 or Compound N of the present invention, wherein Q A is the group shown in Q A 1 or the group shown in Q A 2, and R 6A , R 7A , and R 8A are each a hydrogen atom.

[0220] 〔Aspect A41〕Any one of the compounds according to Aspect A1 to Aspect A33 or Compound N of the present invention, wherein Q A is the group shown in Q A 1, and R 6A and R 7A are each a hydrogen atom.

[0221] 〔Aspect A42〕Any one of the compounds according to Aspect A1 to Aspect A29 or Compound N of the present invention, wherein Q A is the group shown in Q A 1 or the group shown in Q A 3, and m is 1 or 2.

[0222] 〔Aspect A43〕Any one of the compounds according to Aspect A1 to Aspect A29 or Compound N of the present invention, wherein Q A is the group shown in Q A 3, and m is 1 or 2.

[0223] 〔Aspect A44〕Any one of the compounds according to Aspect A1 to Aspect A29 or Compound N of the present invention, wherein Q A is the group shown in Q A 3, and m is 2.

[0224] 〔Mode A45〕Any compound according to Mode A1 to Mode A29 or Compound N of the present invention, wherein Q A is the group shown in Q A 1 or the group shown in Q A 3, m is 1 or 2, and R 6A , R 7A and R 9A are each a hydrogen atom.

[0225] 〔Mode A46〕Any compound according to Mode A1 to Mode A29 or Compound N of the present invention, wherein Q A is the group shown in Q A 3, m is 2, and R 9A is a hydrogen atom.

[0226] 〔Mode A47〕Any compound according to Mode A30, Mode A31, or Compound N of the present invention, wherein Q A is the group shown in Q A 1, R 1A and R 5A are the same or different and are a C1-C6 chain hydrocarbon group that may be substituted with one or more halogen atoms, a hydrogen atom, a halogen atom, or -OR 10A , R 2A and R 4A are the same or different and are a C1-C6 chain hydrocarbon group that may be substituted with one or more halogen atoms, a hydrogen atom, a halogen atom, -OR 10A , or -NHC(O)OR 34A , R 3A is a C1-C6 chain hydrocarbon group that may be substituted with one or more halogen atoms, a halogen atom, or -OR 10A , R 10A is a C1-C6 chain hydrocarbon group that may be substituted with one or more halogen atoms, and R 34A is a C1-C3 chain hydrocarbon group.

[0227] 〔Mode B1〕Compound N of the present invention, wherein Z A is a C2-C6 chain hydrocarbon group that may be substituted with one or more halogen atoms, or a C3-C6 cycloalkyl group.

[0228] 〔Mode B2〕Compound N of the present invention, wherein Z A is a C2-C5 chain hydrocarbon group that may be substituted with one or more halogen atoms.

[0229] 〔Mode B3〕Compound N of the present invention, wherein Q A is the group shown in Q A 1 or the group shown in Q A 2, and m is 0 or 2.

[0230] 〔Mode B4〕Compound N of the present invention, wherein Q A is the group shown in Q A shown in 1 or Q A the group shown in 2, and m is 2.

[0231] 〔Mode B5〕Compound N of the present invention, wherein Q A is the group shown in Q A shown in 1 or Q A the group shown in 3, and m is 2.

[0232] 〔Mode B6〕Compound N of the present invention, wherein Q A is the group shown in Q A shown in 1, and m is 0 or 2.

[0233] 〔Mode B7〕Compound N of the present invention, wherein Q A is the group shown in Q A shown in 3, and m is 2.

[0234] 〔Mode B8〕Compound N of the present invention, wherein Z A is a C2-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, or a C3-C6 cycloalkyl group, and Q A is the group shown in Q A shown in 1 or Q A the group shown in 2, and m is 0 or 2.

[0235] 〔Mode B9〕Compound N of the present invention, wherein Z A is a C2-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, or a C3-C6 cycloalkyl group, and Q A is the group shown in Q A shown in 1 or Q A the group shown in 2, and m is 2.

[0236] 〔Mode B10〕Compound N of the present invention, wherein Z A is a C2-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, or a C3-C6 cycloalkyl group, and Q A is the group shown in Q A shown in 1 or Q A the group shown in 3, and m is 2.

[0237] 〔Mode B11〕Compound N of the present invention, wherein Z A is a C2-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, or a C3-C6 cycloalkyl group, and Q A is the group shown in Q A shown in 1, and m is 0 or 2.

[0238] 〔Mode B12〕Compound N of the present invention, wherein Z A is a C2-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group that can be substituted by one or more halogen atoms, and Q A is the group shown in Q A 3, and m is 2.

[0239] 〔Mode B13〕Compound N of the present invention, wherein Z A is a C2-C5 chain hydrocarbon group that can be substituted by one or more halogen atoms, and Q A is the group shown in Q A 1 or the group shown in Q A 2, and m is 0 or 2.

[0240] 〔Mode B14〕Compound N of the present invention, wherein Z A is a C2-C5 chain hydrocarbon group that can be substituted by one or more halogen atoms, and Q A is the group shown in Q A 1 or the group shown in Q A 2, and m is 2.

[0241] 〔Mode B15〕Compound N of the present invention, wherein Z A is a C2-C5 chain hydrocarbon group that can be substituted by one or more halogen atoms, and Q A is the group shown in Q A 1 or the group shown in Q A 3, and m is 2.

[0242] 〔Mode B16〕Compound N of the present invention, wherein Z A is a C2-C5 chain hydrocarbon group that can be substituted by one or more halogen atoms, and Q A is the group shown in Q A 1, and m is 0 or 2.

[0243] 〔Mode B17〕Compound N of the present invention, wherein Z A is a C2-C5 chain hydrocarbon group that can be substituted by one or more halogen atoms, and Q A is the group shown in Q A 3, and m is 2.

[0244] 〔Mode B18〕According to any one of Modes B1 to B17 or Compound N of the present invention, wherein R 1A and R 5A are each a hydrogen atom, and R 2A and R 4A are the same or different and are a hydrogen atom or a halogen atom.

[0245] [Mode B19] Any compound according to Modes B1 to B17 or Compound N of the present invention, wherein R 3A is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, -OR 10A , a hydrogen atom, or a halogen atom, and R 10A is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms.

[0246] [Mode B20] Any compound according to Modes B1 to B17 or Compound N of the present invention, wherein R 1A and R 5A are each a hydrogen atom, R 2A and R 4A are the same or different and are a hydrogen atom or a halogen atom, and R 3A is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, -OR 10A , a hydrogen atom, or a halogen atom (wherein at least one of R 1A , R 2A , R 3A , R 4A and R 5A is not a hydrogen atom).

[0247] [Mode B21] Any compound according to Modes B1 to B17 or Compound N of the present invention, wherein R 1A , R 3A , R 4A and R 5A are each a hydrogen atom, R 2A is -OR 10A , and R 10A is a methyl group substituted with a phenyl group substituted with one or more substituents selected from Group C A .

[0248] Next, the present compound and the production method of the compound of the present invention will be described.

[0249] Production Method A

[0250] The compound represented by formula (I-b) (hereinafter referred to as compound (I-b)) or the compound represented by formula (I-c) (hereinafter referred to as compound (I-c)) can be produced by reacting the compound represented by formula (I-a) (hereinafter referred to as compound (I-a)) with an oxidizing agent.

[0251] [Chemical formula 6]

[0252]

[0253] [In the formula, the symbols have the same meanings as described above.]

[0254] First, a method for producing compound (I-b) from compound (I-a) is described.

[0255] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include halogenated hydrocarbons such as dichloromethane and chloroform (hereinafter referred to as halogenated hydrocarbons); nitriles such as acetonitrile (hereinafter referred to as nitriles); alcohols such as methanol and ethanol (hereinafter referred to as alcohols); acetic acid; water; and mixtures of two or more of them.

[0256] Examples of the oxidizing agent used in the reaction include sodium periodate, meta-chloroperoxybenzoic acid (hereinafter referred to as mCPBA), and hydrogen peroxide.

[0257] In the reaction, the oxidizing agent is usually used in a ratio of 1 to 1.2 moles per 1 mole of compound (I-a).

[0258] When hydrogen peroxide is used as the oxidizing agent, a base or a catalyst can be added as needed.

[0259] Examples of the base used in the reaction include sodium carbonate. The base is usually used in a ratio of 0.01 to 1 mole per 1 mole of compound (I-a).

[0260] Examples of the catalyst used in the reaction include tungstic acid and sodium tungstate. The catalyst is usually used in a ratio of 0.01 to 0.5 mole per 1 mole of compound (I-a).

[0261] The reaction temperature is usually in the range of -20 to 80 °C. The reaction time is usually in the range of 0.1 to 12 hours.

[0262] After the reaction is completed, water is added to the reaction mixture, extraction is carried out with an organic solvent, and if necessary, the organic layer is washed with an aqueous solution of a reducing agent (such as sodium sulfite, sodium thiosulfate) and an aqueous solution of a base (such as sodium bicarbonate). The organic layer is dried and concentrated, whereby compound (I-b) can be obtained.

[0263] Next, a method for producing compound (I-c) from compound (I-b) is described. Compound (I-c) can be produced by reacting compound (I-b) with an oxidizing agent.

[0264] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include halogenated hydrocarbons, nitriles, alcohols, acetic acid, water, and mixtures of two or more of them.

[0265] Examples of the oxidizing agent used in the reaction include mCPBA and hydrogen peroxide.

[0266] In the reaction, the oxidizing agent is usually used in a proportion of 1 to 2 moles relative to 1 mole of the compound (I-b).

[0267] When using hydrogen peroxide as the oxidizing agent, a base or a catalyst can be added as needed.

[0268] Examples of the base used in the reaction include sodium carbonate. The base is usually used in a proportion of 0.01 to 1 mole relative to 1 mole of the compound (I-b).

[0269] Examples of the catalyst used in the reaction include sodium tungstate. The catalyst is usually used in a proportion of 0.01 to 0.5 mole relative to 1 mole of the compound (I-b).

[0270] The reaction temperature is usually in the range of -20 to 120 °C. The reaction time is usually in the range of 0.1 to 12 hours.

[0271] After the reaction is completed, water is added to the reaction mixture, extraction is carried out using an organic solvent, and the organic layer is washed with an aqueous solution of a reducing agent (such as sodium sulfite, sodium thiosulfate) and an aqueous solution of a base (such as sodium bicarbonate) as needed. The organic layer is dried and concentrated, whereby the compound (I-c) can be obtained.

[0272] In addition, the compound (I-c) can also be produced by reacting the compound (I-a) with an oxidizing agent in a one-step reaction (one-pot).

[0273] For the reaction, the oxidizing agent can be used in a proportion of usually 2 to 5 moles relative to 1 mole of the compound (I-a), and it is carried out according to the method for producing the compound (I-c) from the compound (I-b).

[0274] Production Method B

[0275] The compound represented by the formula (IA-a) (hereinafter, referred to as the compound (IA-a)) can be produced by reacting the compound represented by the formula (M-1) (hereinafter, referred to as the compound (M-1)) with the compound represented by the formula (M-2) (hereinafter, referred to as the compound (M-2)) in the presence of a copper catalyst and a base.

[0276] [Chemical formula 7]

[0277]

[0278] [In the formula, X 1 represents an iodine atom, a bromine atom, a chlorine atom, a trifluoromethanesulfonyloxy group, B(OH)2, or 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl, and the other symbols have the same meanings as described above.

[0279] 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, tetrahydrofuran (hereinafter referred to as THF), and dimethoxyethane (hereinafter referred to as ethers); halogenated hydrocarbons; amides such as N,N-dimethylformamide (hereinafter referred to as DMF) and N-methylpyrrolidone (hereinafter referred to as amides); esters such as methyl acetate and ethyl acetate (hereinafter referred to as esters); nitriles; sulfoxides such as dimethyl sulfoxide (hereinafter referred to as DMSO) (hereinafter referred to as sulfoxides); ketones such as acetone and methyl isobutyl ketone (hereinafter referred to as ketones); alcohols; water; and mixtures of two or more of them.

[0280] Examples of the copper catalyst used in the reaction include copper(I) iodide.

[0281] Examples of the base 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 hydrogencarbonates such as sodium hydrogencarbonate and potassium hydrogencarbonate; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and cesium hydroxide (hereinafter referred to as alkali metal hydroxides); alkali metal alkoxides such as sodium tert-butoxide and potassium tert-butoxide, etc.

[0282] In the reaction, relative to 1 mole of compound (M-1), compound (M-2) is usually used in a ratio of 1 to 10 moles, the base is usually used in a ratio of 1 to 10 moles, and the copper catalyst is usually used in a ratio of 0.01 to 1 mole.

[0283] The reaction temperature is usually in the range of -20 to 150 °C. The reaction time is usually in the range of 0.1 to 120 hours.

[0284] After the reaction is completed, the reaction mixture is mixed with water, and then extracted with an organic solvent. The organic layer is subjected to post-treatment operations such as drying and concentration, whereby compound (IA-a) can be obtained.

[0285] Compound (M-2) is a commercially available compound or can be manufactured using known methods.

[0286] Production Method C

[0287] The compound represented by formula (I-a1) (hereinafter referred to as compound (I-a1)) can be produced by reacting the compound represented by formula (M-3) (hereinafter referred to as compound (M-3)) with the compound represented by formula (R-1) (hereinafter referred to as compound (R-1)) in the presence of a base.

[0288] [Chemical Formula 8]

[0289]

[0290] [In the formula, Z 1 represents a C1-C6 chain hydrocarbon group that may be substituted with one or more substituents selected from Group A, or a C3-C6 cycloalkyl group that may be substituted with one or more substituents selected from Group E, X 2 represents an iodine atom, a bromine atom, a chlorine atom, or a trifluoromethanesulfonyloxy group, and the other symbols have the same meanings as described above.]

[0291] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons; ethers; amides; esters; sulfoxides; ketones; nitriles; and mixtures of two or more of them.

[0292] Examples of the base used in the reaction include organic bases; alkali metal carbonates; alkali metal hydroxides; and alkali metal hydrides such as sodium hydride (hereinafter referred to as alkali metal hydrides).

[0293] In the reaction, relative to 1 mole of compound (M-3), compound (R-1) is usually used in a ratio of 1 to 10 moles, and the base is usually used in a ratio of 1 to 10 moles.

[0294] 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 24 hours.

[0295] In the reaction, sodium iodide, potassium iodide, tetrabutylammonium iodide, etc. can be added as needed, and these compounds are usually used in a ratio of 0.001 to 1.2 moles relative to 1 mole of compound (M-3).

[0296] After the reaction is completed, the reaction mixture is extracted with an organic solvent, and post-treatment operations such as drying and concentration of the organic layer are carried out, whereby compound (I-a1) can be obtained.

[0297] Compound (M-3) can be prepared according to the methods described in International Publication No. 2015 / 147313, J. Med. Chem. 2015, 58, 4462, or the method described in Reference Production Method C.

[0298] Compound (R-1) is a commercially available compound or can be prepared using known methods.

[0299] Production Method D

[0300] Compound (IA-a) can be prepared by reacting a compound represented by formula (M-4) (hereinafter referred to as compound (M-4)) with a compound represented by formula (R-2) (hereinafter referred to as compound (R-2)) in the presence of a base.

[0301] [Chemical Formula 9]

[0302]

[0303] [In the formula, the symbols represent the same meanings as described above.]

[0304] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons; ethers; amides; esters; sulfoxides; ketones; nitriles; and mixtures of two or more of them.

[0305] Examples of the base used in the reaction include organic bases; alkali metal carbonates; alkali metal hydroxides; and alkali metal hydrides.

[0306] In the reaction, relative to 1 mole of the compound (M-4), the compound (R-2) is usually used in a ratio of 1 to 10 moles, and the base is usually used in a ratio of 1 to 10 moles.

[0307] 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 24 hours.

[0308] After the reaction is completed, the reaction mixture is extracted with an organic solvent, and post-treatment operations such as drying and concentration of the organic layer are carried out, whereby the compound (IA-a) can be obtained.

[0309] The compound (M-4) can be manufactured according to the method described in International Publication No. 2015 / 147313.

[0310] The compound (R-2) is a commercially available compound or can be manufactured using known methods.

[0311] Production Method E

[0312] The compound represented by the formula (IA-a2) (hereinafter, referred to as the compound (IA-a2)) can be manufactured by carrying out the following steps: a first step of reacting the compound represented by the formula (IA-a1) (hereinafter, referred to as the compound (IA-a1)) with butyllithium or isopropylmagnesium chloride to obtain the compound represented by the formula (M-5) (hereinafter, referred to as the compound (M-5)); and a second step of reacting the compound (M-5) with a halogenating agent to obtain the compound (IA-a2).

[0313] [Chemical Formula 10]

[0314]

[0315] [In the formula, M 1 represents a lithium atom or MgCl, R 3B represents a halogen atom, and other symbols represent the same meanings as described above.]

[0316] The first step is described. The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons; ethers; and mixtures of two or more of them.

[0317] In the reaction, butyllithium or isopropylmagnesium chloride is usually used in a ratio of 1 to 10 moles relative to 1 mole of the compound (IA-a1).

[0318] The reaction temperature is usually in the range of -78 to 80 °C. The reaction time is usually in the range of 0.1 to 24 hours.

[0319] After the reaction is completed, the obtained compound (M-5) can be used in the second step without performing post-treatment operations.

[0320] The second step is described. The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons; ethers; and mixtures of two or more of them.

[0321] Examples of the halogenating agent used in the reaction include iodine, bromine, N-bromosuccinimide, N-chlorosuccinimide, and N-fluorobis(benzenesulfonyl)amine.

[0322] In the reaction, the halogenating agent is usually used in a ratio of 1 to 10 moles relative to 1 mole of the compound (M-5).

[0323] The reaction temperature is usually in the range of -78 to 150 °C. The reaction time is usually in the range of 0.1 to 24 hours.

[0324] After the reaction is completed, water is added to the reaction mixture, extraction is carried out using an organic solvent, and the organic layer is dried and concentrated, whereby the compound (IA-a2) can be obtained.

[0325] Production method F

[0326] The compound represented by the formula (IB-a) (hereinafter referred to as compound (IB-a)) can be produced by reacting the compound represented by the formula (M-6) (hereinafter referred to as compound (M-6)) with the compound represented by the formula (R-3) (hereinafter referred to as compound (R-3)).

[0327] [Chemical formula 11]

[0328]

[0329] [In the formula, the symbols represent the same meanings as described above.]

[0330] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, ketones, and mixtures of two or more of them.

[0331] In the reaction, compound (R-3) is usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (M-6).

[0332] The reaction temperature is usually in the range of -78 to 80 °C. The reaction time is usually in the range of 0.1 to 24 hours.

[0333] After the reaction is completed, water is added to the reaction mixture, and extraction is carried out using an organic solvent. The organic layer is dried and concentrated, whereby compound (IB-a) can be obtained.

[0334] Compound (M-6) and compound (R-3) are commercially available compounds, or they can be manufactured using known methods.

[0335] Production Method G

[0336] The compound represented by formula (I-d) (hereinafter referred to as compound (I-d)) can be produced by reacting the compound represented by formula (M-13) (hereinafter referred to as compound (M-13)) with the compound represented by formula (R-5) (hereinafter referred to as compound (R-5)).

[0337] [Chemical formula 12]

[0338]

[0339] [In the formula, X 3 represents a chlorine atom, a bromine atom, or -OR 34 , and the other symbols have the same meanings as described above.

[0340] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, ketones, and mixtures of two or more of them.

[0341] In the reaction, compound (R-5) is usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (M-13).

[0342] In the reaction, a base can be used as needed. Examples of the base used in the reaction include organic bases; alkali metal carbonates; and alkali metal hydroxides. These bases are usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (M-13).

[0343] 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 24 hours.

[0344] After the reaction is completed, water is added to the reaction mixture, extraction is carried out using an organic solvent, and the organic layer is dried and concentrated, whereby compound (I-d) can be obtained.

[0345] Compound (M-13) can be produced according to Production Method B, Production Method C, or Production Method D.

[0346] Compound (R-5) is a commercially available compound or can be produced using known methods.

[0347] Production Method H

[0348] The compound represented by formula (I-e) (hereinafter referred to as compound (I-e)) can be produced by reacting the compound represented by formula (M-14) (hereinafter referred to as compound (M-14)) with compound (R-5).

[0349] [Chemical formula 13]

[0350]

[0351] [In the formula, the symbols have the same meanings as described above.]

[0352] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, ketones, and mixtures of two or more of them.

[0353] In the reaction, compound (R-5) is usually used in a ratio of 1 to 10 moles per 1 mole of compound (M-14).

[0354] In the reaction, a base can be used as needed. Examples of the base used in the reaction include organic bases; alkali metal carbonates; and alkali metal hydroxides. These bases are usually used in a ratio of 1 to 10 moles per 1 mole of compound (M-14).

[0355] 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 24 hours.

[0356] After the reaction is completed, water is added to the reaction mixture, extraction is carried out using an organic solvent, and the organic layer is dried and concentrated, whereby compound (I-e) can be obtained.

[0357] Compound (M-14) can be produced according to Production Method B, Production Method C, or Production Method D.

[0358] Compound (R-5) is a commercially available compound or can be produced using known methods.

[0359] Production Method I

[0360] The compound represented by formula (IC-a) (hereinafter referred to as compound (IC-a)) can be produced by reacting the compound represented by formula (M-15) (hereinafter referred to as compound (M-15)) with compound (R-2) in the presence of a base.

[0361] [Chemical formula 14]

[0362]

[0363] [In the formula, the symbols represent the same meanings as described above.]

[0364] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons; ethers; amides; esters; sulfoxides; ketones; nitriles; and mixtures of two or more of them.

[0365] Examples of the base used in the reaction include organic bases; alkali metal carbonates; alkali metal hydroxides; and alkali metal hydrides.

[0366] In the reaction, relative to 1 mole of compound (M-15), compound (R-2) is usually used in a ratio of 1 to 10 moles, and the base is usually used in a ratio of 1 to 10 moles.

[0367] 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 24 hours.

[0368] After the reaction is completed, the reaction mixture is extracted with an organic solvent, and post-treatment operations such as drying and concentration of the organic layer are carried out, whereby compound (IC-a) can be obtained.

[0369] Compound (M-15) can be produced according to the methods described in J.Med.Chem., 2017, 60, 10205. or Org.Lett., 2002, 4, 2485.

[0370] Production Method J

[0371] The compound represented by formula (I-f) (hereinafter referred to as compound (I-f)) can be produced by reacting the compound represented by formula (M-16) (hereinafter referred to as compound (M-16)) with the compound represented by formula (R-6) (hereinafter referred to as compound (R-6)).

[0372] [Chemical formula 15]

[0373]

[0374] [In the formula, X 5represents a chlorine atom, a bromine atom, or -OC(O)R 23 , and other symbols represent the same meanings as described above.

[0375] For the reaction, compound (M-16) can be used in place of compound (M-13), and compound (R-6) can be used in place of compound (R-5), and it can be carried out according to production method G.

[0376] Compound (M-16) can be produced according to production method B, production method C, or production method D.

[0377] Compound (R-6) is a commercially available compound, or it can be produced using known methods.

[0378] Production method K

[0379] The compound represented by formula (I-g) (hereinafter referred to as compound (I-g)) can be produced by reacting the compound represented by formula (M-17) (hereinafter referred to as compound (M-17)) with compound (R-6).

[0380] [Chemical formula 16]

[0381]

[0382] [In the formula, the symbols represent the same meanings as described above.

[0383] For the reaction, compound (M-17) can be used in place of compound (M-13), and compound (R-6) can be used in place of compound (R-5), and it can be carried out according to production method G.

[0384] Compound (M-17) can be produced according to production method B, production method C, or production method D.

[0385] Production method L

[0386] The compound represented by formula (I-h) (hereinafter referred to as compound (I-h)) can be produced by reacting the compound represented by formula (I-i) (hereinafter referred to as compound (I-i)) with the compound represented by formula (R-7) (hereinafter referred to as compound (R-7)).

[0387] [Chemical formula 17]

[0388]

[0389] [In the formula, R 26C represents a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group, and other symbols represent the same meanings as described above.

[0390] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, ketones, and mixtures of two or more of them.

[0391] In the reaction, compound (R-7) is usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (I-i).

[0392] In the reaction, a base can be used as needed. Examples of the base used in the reaction include organic bases; alkali metal carbonates; and alkali metal hydroxides. These bases are usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (I-i).

[0393] 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 24 hours.

[0394] After the reaction is completed, water is added to the reaction mixture, extraction is carried out with an organic solvent, and the organic layer is dried and concentrated, whereby compound (I-h) can be obtained.

[0395] Compound (R-7) is a commercially available compound or can be manufactured using known methods.

[0396] Production method M

[0397] The compound represented by formula (I-j) (hereinafter referred to as compound (I-j)) can be produced by reacting the compound represented by formula (I-o) (hereinafter referred to as compound (I-o)) with compound (R-7).

[0398] [Chemical formula 18]

[0399]

[0400] [In the formula, the symbols represent the same meanings as described above.]

[0401] For the reaction, compound (I-o) can be used instead of compound (I-i), and it can be carried out according to production method L.

[0402] Production method N

[0403] The compound represented by formula (I-k) (hereinafter referred to as compound (I-k)) can be produced by carrying out the following steps: a first step of reacting the compound represented by formula (M-20) (hereinafter referred to as compound (M-20)) with a halogenating agent to obtain the compound represented by formula (M-21) (hereinafter referred to as compound (M-21)); and a second step of reacting compound (M-21) with the compound represented by formula (R-8) (hereinafter referred to as compound (R-8)) to obtain compound (I-k). In addition, compound (I-k) can also be produced by reacting compound (M-20) with compound (R-8) in the presence of a condensing agent.

[0404] [Chemical formula 19]

[0405]

[0406] [In the formula, X 6 represents a chlorine atom or a bromine atom, and the other symbols represent the same meanings as described above.]

[0407] The first step will be described. The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, ketones, and mixtures of two or more of them.

[0408] Examples of the halogenating agent used in the reaction include thionyl chloride and oxalyl chloride.

[0409] In the reaction, the halogenating agent is usually used in a proportion of 1 to 10 moles per 1 mole of compound (M-20).

[0410] In the reaction, a base can be used as needed. Examples of the base used in the reaction include organic bases, alkali metal carbonates, and alkali metal hydroxides. These bases are usually used in a proportion of 1 to 10 moles per 1 mole of compound (M-20).

[0411] The reaction temperature is usually in the range of -78 to 150 °C. The reaction time is usually in the range of 0.1 to 24 hours.

[0412] After the reaction is completed, the obtained compound (M-21) can be used in the second step without performing post-treatment operations.

[0413] The second step will be described. The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, ketones, and mixtures of two or more of them.

[0414] In the reaction, compound (R-8) is usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (M-21).

[0415] In the reaction, a base can be used as needed. Examples of the base used in the reaction include organic bases, alkali metal carbonates, and alkali metal hydroxides. These bases are usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (M-21).

[0416] The reaction temperature is usually in the range of -78 to 150 °C. The reaction time is usually in the range of 0.1 to 24 hours.

[0417] After the reaction is completed, water is added to the reaction mixture, extraction is carried out using an organic solvent, and the organic layer is dried and concentrated, whereby compound (I-k) can be obtained.

[0418] Compound (R-8) is a commercially available compound or can be manufactured using known methods.

[0419] Next, a method for manufacturing compound (I-k) by reacting compound (M-20) with compound (R-8) in the presence of a condensing agent will be described.

[0420] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, ketones, and mixtures of two or more of them.

[0421] Examples of the condensing agent used in the reaction include 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide, N,N'-dicyclohexylcarbodiimide, and N,N'-carbonyldiimidazole.

[0422] In the reaction, the condensing agent is usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (M-20).

[0423] In the reaction, a base can be used as needed. Examples of the base used in the reaction include organic bases, alkali metal carbonates, and alkali metal hydroxides. These bases are usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (M-20).

[0424] The reaction temperature is usually in the range of -78 to 150 °C. The reaction time is usually in the range of 0.1 to 24 hours.

[0425] After the reaction is completed, water is added to the reaction mixture, extraction is carried out using an organic solvent, and the organic layer is dried and concentrated, whereby compound (I-k) can be obtained.

[0426] Production Method O

[0427] The compound represented by the formula (I-m) (hereinafter referred to as compound (I-m)) can be produced by carrying out the following steps: a first step of reacting compound (M-20) with a halogenating agent to obtain compound (M-21); and a second step of reacting compound (M-21) with the compound represented by the formula (R-9) (hereinafter referred to as compound (R-9)) to obtain compound (I-m). In addition, compound (I-m) can also be produced by reacting compound (M-20) with compound (R-9) in the presence of a condensing agent.

[0428] [Chemical formula 20]

[0429]

[0430] [In the formula, the symbols represent the same meanings as described above.]

[0431] For these reactions, compound (R-9) can be used in place of compound (R-8) and carried out according to production method N.

[0432] Compound (R-9) is a commercially available compound or can be produced using known methods.

[0433] Production method P

[0434] The compound represented by the formula (I-n) (hereinafter referred to as compound (I-n)) can be produced by carrying out the following steps: a first step of reacting the compound represented by the formula (M-22) (hereinafter referred to as compound (M-22)) with a halogenating agent to obtain the compound represented by the formula (M-23) (hereinafter referred to as compound (M-23)); and a second step of reacting compound (M-23) with compound (R-8) to obtain compound (I-n). In addition, compound (I-n) can also be produced by reacting compound (M-22) with compound (R-8) in the presence of a condensing agent.

[0435] [Chemical formula 21]

[0436]

[0437] [In the formula, the symbols represent the same meanings as described above.]

[0438] For these reactions, compound (M-22) can be used in place of compound (M-20) and carried out according to production method N.

[0439] Production method Q

[0440] The compound represented by formula (I-p) (hereinafter referred to as compound (I-p)) can be prepared by carrying out the following steps: a first step of reacting compound (M-22) with a halogenating agent to obtain compound (M-23); and a second step of reacting compound (M-23) with compound (R-9) to obtain compound (I-p). In addition, compound (I-p) can also be prepared by reacting compound (M-22) with compound (R-9) in the presence of a condensing agent.

[0441] [Chemical formula 22]

[0442]

[0443] [In the formula, the symbols represent the same meanings as described above.]

[0444] For these reactions, compound (M-22) can be used in place of compound (M-20), and compound (R-9) can be used in place of compound (R-8), and they can be carried out according to production method N.

[0445] The compound represented by formula (IA-a4) (hereinafter referred to as compound (IA-a4)) can be prepared by carrying out the following steps: a first step of reacting the compound represented by formula (IA-a3) (hereinafter referred to as compound (IA-a3)) with butyllithium or isopropylmagnesium chloride to obtain the compound represented by formula (M-24) (hereinafter referred to as compound (M-24)); and a second step of reacting compound (M-24) with a fluorinating agent to obtain compound (IA-a4).

[0446] [Chemical formula 23]

[0447]

[0448] [In the formula, the symbols represent the same meanings as described above.]

[0449] The first step will be described. The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons, ethers, and mixtures of two or more of them.

[0450] In the reaction, butyllithium or isopropylmagnesium chloride is usually used in a ratio of 1 to 10 moles per 1 mole of compound (IA-a3).

[0451] The reaction temperature is usually in the range of -78 to 80 °C. The reaction time is usually in the range of 0.1 to 24 hours.

[0452] After the reaction is completed, the obtained compound (M-24) can be used in the second step without performing post-treatment operations.

[0453] The second process will be described. The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons, ethers, and mixtures of two or more of them.

[0454] Examples of the fluorinating agent used in the reaction include N-fluorobis(benzenesulfonyl)amine.

[0455] In the reaction, the fluorinating agent is usually used in a proportion of 1 to 10 moles relative to 1 mole of the compound (M-24).

[0456] The reaction temperature is usually in the range of -78 to 150 °C. The reaction time is usually in the range of 0.1 to 24 hours.

[0457] After the reaction is completed, water is added to the reaction mixture, extraction is carried out using an organic solvent, and the organic layer is dried and concentrated, whereby the compound (IA-a4) can be obtained.

[0458] The compound (IA-a3) can be produced according to Production Method B, Production Method C, or Production Method D.

[0459] Production Method R

[0460] The compound (I-i) can be produced by reacting the compound represented by the formula (M-25) (hereinafter referred to as the compound (M-25)) with the compound represented by the formula (R-10) (hereinafter referred to as the compound (R-10)).

[0461] [Chemical formula 24]

[0462]

[0463] [In the formula, X 7 represents a chlorine atom, a bromine atom, or -OC(O)R 27 , and the other symbols have the same meanings as described above.

[0464] Regarding the reaction, the compound (M-25) can be used in place of the compound (M-13), and the compound (R-10) can be used in place of the compound (R-5), and the reaction can be carried out according to Production Method G.

[0465] Production Method S

[0466] The compound (I-o) can be produced by reacting the compound represented by the formula (M-26) (hereinafter referred to as the compound (M-26)) with the compound (R-10).

[0467] [Chemical formula 25]

[0468]

[0469] [In the formula, the symbols have the same meanings as described above.]

[0470] Regarding the reaction, compound (M-26) can be used in place of compound (M-13), and compound (R-10) can be used in place of compound (R-5), and it can be carried out according to production method G.

[0471] Production method T

[0472] The N-oxide of the compound represented by formula (I) can be produced by reacting the compound represented by formula (I) with an oxidizing agent. The reaction can be carried out, for example, according to the method described in U.S. Patent Application Publication No. 2018 / 0009778 or International Publication No. 2016 / 121970.

[0473] Next, the production methods of the present compound and the intermediates of the compound of the present invention will be described.

[0474] Reference production method A

[0475] Compound (M-1) can be produced by reacting the compound represented by formula (M-7) (hereinafter referred to as compound (M-7)) with an acid or a base.

[0476] [Chemical formula 26]

[0477]

[0478] [In the formula, R 10 represents methyl or ethyl, and the other symbols have the same meanings as described above.]

[0479] Examples of the acid used in the reaction include hydrochloric acid and trifluoroacetic acid.

[0480] Examples of the base used in the reaction include potassium hydroxide and sodium methoxide.

[0481] The reaction can be carried out according to the method described in J.Med.Chem., 2016, 59, 2760.

[0482] Reference production method B

[0483] Compound (M-7) can be produced by carrying out the following steps: a first step of reacting the compound represented by formula (M-8) (hereinafter referred to as compound (M-8)) with butyllithium or isopropylmagnesium chloride to obtain the compound represented by formula (M-9) (hereinafter referred to as compound (M-9)); and a second step of reacting compound (M-9) with a disulfide or a thiosulfonate to obtain compound (M-7).

[0484] [Chemical formula 27]

[0485]

[0486] [In the formula, the symbols represent the same meanings as described above.]

[0487] The above reaction can be carried out according to the method described in International Publication No. 2008 / 129054.

[0488] Compound (M-8) is a commercially available compound or can be produced according to the method described in J. Med. Chem., 2016, 59, 2760.

[0489] Reference Production Method C

[0490] The compound represented by formula (M-11) (hereinafter referred to as compound (M-11)) can be produced by reacting the compound represented by formula (M-10) (hereinafter referred to as compound (M-10)) with a sulfurizing agent.

[0491] [Chemical formula 28]

[0492]

[0493] [In the formula, the symbols represent the same meanings as described above.]

[0494] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons, amides, nitriles, and mixtures of two or more of them.

[0495] Examples of the sulfurizing agent used in the reaction include phosphorus pentasulfide, Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide), etc.

[0496] In the reaction, the sulfurizing agent is usually used in a proportion of 0.5 to 10 moles per 1 mole of compound (M-10).

[0497] The reaction temperature is usually in the range of 20 to 150 °C. The reaction time is usually in the range of 0.1 to 50 hours.

[0498] After completion of the reaction, water is added to the reaction mixture, extraction is carried out using an organic solvent, and the organic layer is dried and concentrated, whereby compound (M-11) can be obtained.

[0499] Reference Production Method D

[0500] Compound (M-10) can be produced by reacting the compound represented by formula (M-12) (hereinafter referred to as compound (M-12)) with the compound represented by formula (R-4) (hereinafter referred to as compound (R-4)).

[0501] [Chemical formula 29]

[0502]

[0503] [In the formula, X 4 represents a C1-C5 chain hydrocarbon group or a C3-C6 cycloalkyl group, and the other symbols represent the same meanings as described above.]

[0504] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, sulfoxides, ketones, nitriles, alcohols, water, and mixtures of two or more of them.

[0505] In the reaction, compound (R-4) is usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (M-12).

[0506] 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 24 hours.

[0507] After the reaction is completed, water is added to the reaction mixture, extraction is carried out using an organic solvent, and the organic layer is dried and concentrated, whereby compound (M-10) can be obtained.

[0508] Compound (M-12) and compound (R-4) are commercially available compounds, or they can be manufactured using known methods.

[0509] Reference Production Method E

[0510] Compound (M-25) can be manufactured by reacting the compound represented by formula (I-q) (hereinafter, referred to as compound (I-q)) with zinc.

[0511] [Chemical Formula 30]

[0512]

[0513] [In the formula, the symbols represent the same meanings as described above.]

[0514] The reaction can be carried out, for example, according to the methods described in Org. Lett. 2017, 19, 3059. or Angew. Chem. Int. Ed. 2014, 53, 14559.

[0515] Compound (I-q) can be manufactured according to Production Method B, Production Method C, or Production Method D.

[0516] Reference Production Method F

[0517] Compound (M-26) can be manufactured by reacting the compound represented by formula (I-r) (hereinafter, referred to as compound (I-r)) with zinc.

[0518] [Chemical Formula 31]

[0519]

[0520] [In the formula, the symbols represent the same meanings as described above.]

[0521] For the reaction, compound (I-r) can be used in place of compound (I-q) and carried out according to the method described in Reference Production Method E.

[0522] Compound (I-r) can be produced according to Production Method B, Production Method C, or Production Method D.

[0523] Reference Production Method G

[0524] Compound (M-20) can be produced by hydrolyzing the compound represented by formula (M-27) (hereinafter referred to as compound (M-27)).

[0525] [Chemical Formula 32]

[0526]

[0527] [In the formula, the symbols represent the same meanings as described above.]

[0528] The reaction can be carried out according to the method described in J. Am. Chem. Soc. 2006, 128, 3536.

[0529] Compound (M-27) can be produced according to Production Method B, Production Method C, or Production Method D.

[0530] Reference Production Method H

[0531] Compound (M-22) can be produced by hydrolyzing the compound represented by formula (M-28) (hereinafter referred to as compound (M-28)).

[0532] [Chemical Formula 33]

[0533]

[0534] [In the formula, the symbols represent the same meanings as described above.]

[0535] The reaction can be carried out according to the method described in J. Am. Chem. Soc. 2006, 128, 3536.

[0536] Compound (M-28) can be produced according to Production Method B, Production Method C, or Production Method D.

[0537] The present compound or the compound of the present invention can be mixed or used in combination with one or more components selected from the group consisting of the following group (a), group (b), group (c) and group (d) (hereinafter referred to as this component).

[0538] The above-mentioned mixing or combined use means that the present compound or the compound of the present invention and this component are used simultaneously, separately or at intervals of time.

[0539] When the present compound or the compound of the present invention and this component are used simultaneously, the present compound or the compound of the present invention and this component can be contained in separate preparations respectively, or can be contained in one preparation.

[0540] One aspect of the present invention is a composition (hereinafter referred to as composition A), which contains: one or more components selected from the group consisting of group (a), group (b), group (c) and group (d); and the present compound or the compound of the present invention.

[0541] Group (a) is a group consisting of acetylcholinesterase inhibitors (such as carbamate insecticides, organophosphorus insecticides), GABA-gated chloride channel blockers (such as phenylpyrazole insecticides), sodium channel modulators (such as pyrethroid insecticides), nicotinic acetylcholine receptor competitive modulators (such as neonicotinoid insecticides), allosteric modulators of nicotinic acetylcholine receptors, allosteric modulators of glutamate-gated chloride channels (such as macrolide insecticides), juvenile hormone mimetics, multi-site inhibitors, chordotonal TRPV channel modulators, mite growth inhibitors, insect midgut intima disruptors from microorganisms, mitochondrial ATP synthase inhibitors, oxidative phosphorylation uncouplers, nicotinic acetylcholine receptor channel blockers (such as nereistoxin insecticides), chitin biosynthesis inhibitors, molting inhibitors, ecdysone receptor agonists, octopamine receptor agonists, mitochondrial complex I, II, III and IV electron transport inhibitors, voltage-dependent sodium channel blockers, acetyl-CoA carboxylase inhibitors, ryanodine receptor modulators (such as diamide insecticides), chordotonal modulators, microbial insecticides, and other insecticidal active ingredients, acaricidal active ingredients and nematicidal active ingredients. These ingredients are listed according to the classification of the mechanism of action based on IRAC.

[0542] Group (b) is a group consisting of nucleic acid synthesis inhibitors (e.g., phenylamide-based fungicides, acyl amino acid-based 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-based fungicides), signal transduction inhibitors, lipid synthesis and membrane synthesis inhibitors, sterol biosynthesis inhibitors (e.g., DMI fungicides such as triazole-based ones), cell wall biosynthesis inhibitors, melanin synthesis inhibitors, plant defense inducers, multi-site contact active fungicides, microbial fungicides, and other fungicidal active ingredients. These ingredients are described according to the classification of the mode of action based on FRAC.

[0543] Group (c) is a group of plant growth regulating components (including mycorrhizal fungi and rhizobia).

[0544] Group (d) is a group of repellent components.

[0545] Hereinafter, examples of the combination of this ingredient and this compound or the compound of the present invention are described. For example, alanycarb + SX represents the combination of alanycarb and SX.

[0546] It should be noted that the abbreviation SX represents any one of the compound groups SX1 to SX42 of the compounds described in the examples, which are either this compound or the compound of the present invention. In addition, all the ingredients described hereinafter are known ingredients, which can be obtained from commercially available preparations or manufactured by known methods. When this ingredient is a microorganism, it can also be obtained from a microorganism preservation institution. It should be noted that the numbers in parentheses represent CAS RN (registered trademark).

[0547] The combination of the ingredient of the above-mentioned group (a) and this compound or the compound of the present invention:

[0548] Abamectin + SX, Acephate + SX, Acequinocyl + SX, Acetamiprid + SX, Acetoprole + SX, Acrinathrin + SX, Acynonapyr + SX, Afidopyropen + SX, Afoxolaner + SX, Alanycarb + SX, Aldicarb + SX, Allethrin + SX, Alpha-cypermethrin + SX, Alpha-endosulfan + SX, Aluminium phosphide + SX, Amitraz + SX, Azadirachtin + SX, Azamethiphos + SX, Azinphos-ethyl + SX, Azinphos-methyl + SX, Azocyclotin + SX, Bark of Celastrus angulatus + SX, Bendiocarb + SX, Benfluthrin + SX, Benfuracarb + SX, Bensultap + SX, Benzoximate + SX, Benzpyrimoxan + SX, Beta-cyfluthrin + SX, Beta-cypermethrin + SX, Bifenazate + SX, Bifenthrin + SX, Bioallethrin + SX, Bioresmethrin + SX, Bistrifluron + SX, Borax + SX, Boric acid + SX, Broflanilide + SX, Bromopropylate + SX, Buprofezin + SX, Butocarboxim + SX, Butoxycarboxim + SX, Cadusafos + SX, Calcium phosphidephosphide)+SX, carbaryl+SX, carbofuran+SX, carbosulfan+SX, cartap hydrochloride+SX, cartap+SX, chinomethionat+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, concanamycinA) +SX, coumaphos+SX, cryolite+SX, cyanophos+SX, cyantraniliprole+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, dicloromezotiaz+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 Dryopterisfilix-mas+SX, emamectin-benzoate+SX, empenthrin+SX, endosulfan+SX, EPN (O-ethyl O-(4-nitrophenyl)phenyl phosphorothioate, O-ethylO-(4-nitrophenyl)phenylphosphonothioate)+SX, ε-methoxybenzylfluthrin +SX, epsilon-momfluorothrin +SX, esfenvalerate +SX, ethiofencarb +SX, ethion +SX, ethiprole +SX, ethoprophos +SX, etofenprox +SX, etoxazole +SX, extract of Artemisia absinthium +SX, extract of Azadirachtaindica +SX, extract of Cassia nigricans +SX, extract of Clitoria ternatea +SX, extract of Symphytum officinale +SX, extract or simulated blend of Chenopodium ambrosioides +SX, extract of Tanacetum vulgare +SX, extract of Urtica dioica +SX, extract of Viscum album +SX, famphur +SX, fenamiphos +SX, fenazaquin +SX, fenbutatin hexoxideoxide)+SX, fenitrothion+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, flucycloxuron+SX, flucythrinate+SX, fluensulfone+SX, flufenoprox+SX, flufenoxuron+SX, flufiprole+SX, flumethrin+SX, flupentiofenox+SX, flupyradifurone+SX, flupyrimin+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 betaacid)+SX, hydramethylnon)+SX, hydroprene)+SX, imicyafos)+SX, imidacloprid)+SX, imidaclothiz)+SX, imiprothrin)+SX, indoxacarb)+SX, isocycloseram+SX, isofenphos)+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, 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, milbemycinoxime)+SX, momfluorothrin+SX, monocrotophos+SX, moxidectin+SX, naled+SX, nicofluprole+SX, nicotine+SX, nicotine-sulfate+SX, nitenpyram+SX, novaluron+SX, noviflumuron+SX, oil of the seeds of Chenopodium anthelminticum+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, pirimicarb+SX, pirimiphos-methyl+SX, prallethrin+SX, profenofos+SX, profluthrin+SX, propargite+SX, propetamphos+SX, propoxur+SX, propyleneglycolalginate)+SX, prothiofos)+SX, pyflubumide+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, spinetoram)+SX, spinosad)+SX, spirodiclofen)+SX, spiromesifen)+SX, spiropidion)+SX, spirotetramat)+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 nearambrosioides)+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, tioxazafen+SX, tolfenpyrad+SX, tralomethrin+SX, transfluthrin+SX, triazamate+SX, triazophos+SX, trichlorfon+SX, triflumezopyrim+SX, triflumuron+SX, trimethacarb+SX, tyclopyrazoflor+SX, vamidothion+SX, wood extract of Quassia amara+SX, XMC (3,5-dimethylphenyl N-methylcarbamate, N-methylamino carbamate of 3,5-dimethylphenyl)+SX, xylylcarb+SX, zeta-cypermethrin+SX, zincphosphide)+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, 2-({2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}imino)-3-(2,2,2-trifluoroethyl)-1,3-thiazolidin-4-one (1445683-71-5)+SX, (2Z)-2-({2-fluoro-4-methyl-5-[(R)-(2,2,2-trifluoroethyl)sulfinyl]phenyl}imino)-3

[0549] -(2,2,2-trifluoroethyl)-1,3-thiazolidin-4-one ((2Z)-2-({2-fluoro-4-methyl-5-[(R)-(2,2,2-trifluoroethyl)sulfinyl]phenyl}imino)-3-(2,2,2-trifluoroethyl)-1,3

[0550] -thiazolidin-4-one)(2377084-09-6)+SX, (3R)-3-(2-chlorothiazol-5-yl)-8-methyl-7-oxo-6-phenyl-2,3-dihydrothiazolo[3,2-a]pyrimidin-4-ium-5-olate)(2249718-27-0)+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, 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]tetradec-11-en-10-one)(907187-07-9)+SX, 3-(4'-fluoro-2,4-dimethyl[1,1'-biphenyl]-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one)(1031385-91-7)+SX, N-[3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl]-2-(methanesulfonyl)propanamide)(2396747-83-2)+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, BT crop protein Cry1Ab + SX, BT crop protein Cry1Ac + SX, BT crop protein Cry1Fa + SX, BT crop protein Cry1A.105 + SX, BT crop protein Cry2Ab + SX, BT crop protein Vip3A + SX, BT crop protein Cry3A + SX, BT crop protein Cry3Ab + SX, BT crop protein Cry3Bb + SX, BT crop protein Cry34Ab1 / Cry35Ab1 + SX, Adoxophyes orana granulosis virus strain BV-0001 + SXAnticarsia gemmatalis multiple nucleopolyhedrovirus (Anticarsia gemmatalis mNPV) + SX, Autographa californica multiple nucleopolyhedrovirus (Autographa californica mNPV) + SX, Cydia pomonella granulovirus V15 strain (Cydia pomonella GV strain V15) + SX, Cydia pomonella granulovirus V22 strain (Cydia pomonella GV strain V22) + SX, Cryptophlebia leucotreta granulovirus (Cryptophlebia leucotreta GV) + SX, Dendrolimus punctatus cypovirus (Dendrolimus punctatus cypovirus) + SX, Helicoverpa armigera nucleopolyhedrovirus BV-0003 strain (Helicoverpa armigera NPV strain BV-0003) + SX, Helicoverpa zea nucleopolyhedrovirus (Helicoverpa zea NPV) + SX, Lymantria dispar nucleopolyhedrovirus (Lymantria dispar NPV) + SX, Mamestra brassicae nucleopolyhedrovirus (Mamestra brassicae NPV) + SX, Mamestra configurata nucleopolyhedrovirus (Mamestra configurata NPV) + SX, Neodiprion abietis nucleopolyhedrovirus (Neodiprion abietis NPV) + SX, Neodiprion lecontei nucleopolyhedrovirus (Neodiprion lecontei NPV) + SX, Neodiprion sertifer nucleopolyhedrovirus (Neodiprion sertifer NPV) + SX, Nosema locustae (Nosema locustae) + SX, Orgyia pseudotsugata nucleopolyhedrovirus (Orgyia pseudotsugata NPV) + SX, Pieris rapae granulovirus (Pieris rapae GV) + SX, Plodia interpunctella granulovirus (Plodia interpunctella GV) + SX, Spodoptera exigua multiple nucleopolyhedrovirus (Spodoptera exigua mNPV) + SX, Spodoptera littoralis multiple nucleopolyhedrovirus (Spodoptera littoralis mNPV) + SX, Spodoptera litura nucleopolyhedrovirus (Spodoptera litura NPV) + SX, Arthrobotrys dactyloides (Arthrobotrys dactyloides) + SX, Bacillus firmus GB-126 strain (Bacillus firmus strain GB-126) + SX, Bacillus firmus I-1582 strain (Bacillus firmus strain I-1582) + SXBacillus megaterium + SX, Bacillus sp. strain AQ175 + SX, Bacillus sp. strain AQ177 + SX, Bacillus sp. strain AQ178 + SX, Bacillus sphaericus strain 2362 + SX, Bacillus sphaericus strain ABTS1743 + SX, Bacillus sphaericus Serotype strain H5a5b + 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 Serotype strain H-7 + SX, Bacillus thuringiensis subsp. Kurstaki strain ABTS351 + SX, Bacillus thuringiensis subsp. Kurstaki strain BMP123 + SXBacillus thuringiensis subsp. Kurstaki strain EG234 + 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 + SXBacillus 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 rinojensis strain A396 + SX, Chromobacterium subtsugae strain PRAA4-1T + SX, Dactyllela ellipsospora + SX, Dectylaria thaumasia + SX, Hirsutella minnesotensis + SX, Hirsutella rhossiliensis + SXHirsutella 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 thoynei + SX, Serratia entomophila + SX, Verticillium chlamydosporium + SX, Verticillium lecanii strain NCIM1312 + SX.、

[0551] Combination of the present component of the above group (b) with the present compound or the compound of the present invention:

[0552] 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, Chinomethionat + SX, Chitin + SX, Chloroinconazide + SX, Chloroneb + SX, Chlorothalonil + SX, Chlozolinate + SX, Colletochlorin B + SX, Copper(II)acetate + SX, Copper(II)hydroxide + SX, Copperoxychloride + 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, Extract of Melaleuca alternifolia + SX, Extract of Reynoutria sachalinensis + SX, Extract of the cotyledons of lupine plantlets ("BLAD") + SX, Extract of Allium sativum + SX, Extract of Equisetum arvense + SX, Extract of Tropaeolum majus + SXFamoxadone + SX, Fenamidone + SX, Fenaminstrobin + SX, Fenarimol + SX, Fenbuconazole + SX, Fenfuram + SX, Fenhexamid + SX, Fenoxanil + SX, Fenpiclonil + SX, Fenpicoxamid + SX, Fenpropidin + SX, Fenpropimorph + SX, Fenpyrazamine + SX, Fentin acetate, Fentin chloride, Fentin hydroxide, Ferbam, Ferimzone, Florylpicoxamid, Fluazinam, Flubeneteram, Fludioxonil, Flufenoxystrobin, Fluindapyr, Flumorph, Fluopicolide, Fluopyram, Fluopimomide, Fluoroimide, Fluoxapiprolin, Fluoxastrobin, Fluquinconazole, Flusilazole, Flusulfamide, Flutianil, Flutolanil, Flutriafol, Fluxapyroxad, Folpet, Fosetyl, Fosetyl - aluminium, Fuberidazole, Furalaxyl, Furametpyr, Guazatine, Hexaconazole, Hymexazole, ImazalilImibenconazole + SX, Iminoctadine + SX, Iminoctadine Triacetate + SX, Inpyrfluxam + SX, Iodocarb + SX, Ipconazole + SX, Ipflentrifluconazole + SX, Ipflufenoquin + SX, Iprobenfos + SX, Iprodione + SX, Iprovalicarb + SX, Isofetamid + SX, Isoflucypram + SX, Isoprothiolane + SX, Isopyrazam + SX, Isotianil + SX, Kasugamycin + SX, Kresoxim - methyl + SX, Laminarin + SX, 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, 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, pyridachlometyl + SX, pyrifenox + SX, pyrimethanil + SX, pyrimorph + SX, pyriofenone + SX, pyrisoxazole + SX, pyroquilon + SX, Quillaja extract + SXquinconazole + SX, quinofumelin + SX, quinoxyfen + SX, quintozene + SX, Saponins of Chenopodium quinoa + 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, triticonazole + SX, validamycin + SX, valifenalate + SX, vinclozolin + SX, yellow mustard powder + SX, thiazole zinc + SX, zineb + SX, ziram + SX, 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) + SXN'-[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, 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one (1616664-98-2) + SX, (2Z)-3-amino-2-cyano-3-phenylacrylate (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)cyclopentane-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 ((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 (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 (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 (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, 4-({6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl]pyridin-3-yl}oxy)benzonitrile (2046300-61-0) + 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) + SXN-(1-benzyl-1,3-dimethylbutyl)-8-fluoroquinoline-3-carboxamide (2132414-04-9) + SX, N-(1-benzyl-3,3,3-trifluoro-1-methylpropyl)-8-fluoroquinoline-3-carboxamide (2132414-00-5) + 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 + SXN-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-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + SX, N-[2-(difluoromethoxy)phenyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + SX, N-[2-(difluoromethoxy)-4-fluorophenyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + SXN-acetyl-2-(ethanesulfonyl)-N-[2-(methoxycarbonyl)-4-(trifluoromethoxy)phenyl]-4-(trifluoromethyl)benzamide (2043675-28-9) + SX, (2S,3S)-3-(2-methylphenyl)butan-2-yl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate (2376210-00-1) + SX, (2S,3S)-3-(4-fluoro-2-methylphenyl)butan-2-yl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (2S,3S)-3-(4-methoxy-2-methylphenyl)butan-2-yl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (2S,3S)-3-(2,4-dimethylphenyl)butan-2-yl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate (2376209-13-9) + SXN-({3-[(2-methylpropanoyl)oxy]-4-methoxypyridin-2-yl}carbonyl)-L-alanine (2S,3S)-3-(2-methylphenyl)butan-2-yl ester ((2S,3S)-3-(2-methylphenyl)butan-2-yl N-({3-[(2-methylpropanoyl)oxy]-4-methoxypyridin-2-yl}carbonyl)-L-alaninate) (2376210-02-3) + SX, N-({3-[(2-methylpropanoyl)oxy]-4-methoxypyridin-2-yl}carbonyl)-L-alanine (2S,3S)-3-(4-fluoro-2-methylphenyl)butan-2-yl ester ((2S,3S)-3-(4-fluoro-2-methylphenyl)butan-2-yl N-({3-[(2-methylpropanoyl)oxy]-4-methoxypyridin-2-yl}carbonyl)-L-alaninate) + SX, N-({3-[(2-methylpropanoyl)oxy]-4-methoxypyridin-2-yl}carbonyl)-L-alanine (2S,3S)-3-(4-methoxy-2-methylphenyl)butan-2-yl ester ((2S,3S)-3-(4-methoxy-2-methylphenyl)butan-2-yl N-({3-[(2-methylpropanoyl)oxy]-4-methoxypyridin-2-yl}carbonyl)-L-alaninate) (2376209-40-2) + SX, N-({3-[(2-methylpropanoyl)oxy]-4-methoxypyridin-2-yl}carbonyl)-L-alanine (2S,3S)-3-(2,4-dimethylphenyl)butan-2-yl ester ((2S,3S)-3-(2,4-dimethylphenyl)butan-2-yl N-({3-[(2-methylpropanoyl)oxy]-4-methoxypyridin-2-yl}carbonyl)-L-alaninate) (2376209-15-1) + SX, N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine (2S,3S)-3-(2-methylphenyl)butan-2-yl ester ((2S,3S)-3-(2-methylphenyl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate) + SX,N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine (2S,3S)-3-(4-fluoro-2-methylphenyl)butan-2-yl ester ((2S,3S)-3-(4-fluoro-2-methylphenyl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate) + SX, N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine (2S,3S)-3-(4-methoxy-2-methylphenyl)butan-2-yl ester ((2S,3S)-3-(4-methoxy-2-methylphenyl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate) + SX, N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine (2S,3S)-3-(2,4-dimethylphenyl)butan-2-yl ester ((2S,3S)-3-(2,4-dimethylphenyl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate) + SX, N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine (2S,3S)-3-(4-fluoro-2-methylphenyl)-4-methylpentan-2-yl ester ((2S,3S)-3-(4-fluoro-2-methylphenyl)-4-methylpentan-2-yl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate) + SX, N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine (2S,3S)-3-(2-fluoro-4-methylphenyl)-4-methylpentan-2-yl ester ((2S,3S)-3-(2-fluoro-4-methylphenyl)-4-methylpentan-2-yl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate) + SX,N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine (2S,3S)-3-(2,4-difluorophenyl)-4-methylpentan-2-yl ester ((2S,3S)-3-(2,4-difluorophenyl)-4-methylpentan-2-yl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate) + SX, N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine (2S,3S)-3-(2,4-dimethylphenyl)-4-methylpentan-2-yl ester ((2S,3S)-3-(2,4-dimethylphenyl)-4-methylpentan-2-yl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate) + SX, N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine (2S,3S)-3-(4-fluoro-2-methoxylphenyl)-4-methylpentan-2-yl ester ((2S,3S)-3-(4-fluoro-2-methoxylphenyl)-4-methylpentan-2-yl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate) + SX, N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alanine (2S,3S)-3-(4-fluoro-2-methylphenyl)-4-methylpentan-2-yl ester ((2S,3S)-3-(4-fluoro-2-methylphenyl)-4-methylpentan-2-yl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate) + SX, N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alanine (2S,3S)-3-(2-fluoro-4-methylphenyl)-4-methylpentan-2-yl ester ((2S,3S)-3-(2-fluoro-4-methylphenyl)-4-methylpentan-2-yl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate) + SX,N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alanine (2S,3S)-3-(2,4-difluorophenyl)-4-methylpentan-2-yl ester ((2S,3S)-3-(2,4-difluorophenyl)-4-methylpentan-2-yl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate) + SX, N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alanine (2S,3S)-3-(2,4-dimethylphenyl)-4-methylpentan-2-yl ester ((2S,3S)-3-(2,4-dimethylphenyl)-4-methylpentan-2-yl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate) + SX, N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alanine (2S,3S)-3-(4-fluoro-2-methoxylphenyl)-4-methylpentan-2-yl ester ((2S,3S)-3-(4-fluoro-2-methoxylphenyl)-4-methylpentan-2-yl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate) + SX, N-({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)-L-alanine (2S,3S)-3-(4-fluoro-2-methylphenyl)-4-methylpentan-2-yl ester ((2S,3S)-3-(4-fluoro-2-methylphenyl)-4-methylpentan-2-yl N-({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)-L-alaninate) + SX, N-({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)-L-alanine (2S,3S)-3-(2-fluor-4-methylphenyl)-4-methylpentan-2-yl ester ((2S,3S)-3,

[0553] -(2-fluoro-4-methylphenyl)-4-methylpentan-2-yl N-({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)-L-alaninate)+SX, N-({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)-L-alanine (2S,3S)-3-(2,4-difluorophenyl)-4-methylpentan-2-yl ester ((2S,3S)-3-(2,4-difluorophenyl)-4-methylpentan-2-yl N-({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)-L-alaninate)+SX, N-({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)-L-alanine (2S,3S)-3-(2,4-dimethylphenyl)-4-methylpentan-2-yl ester ((2S,3S)-3-(2,4-dimethylphenyl)-4-methylpentan-2-yl N-({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)-L-alaninate)+SX, N-({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)-L-alanine (2S,3S)-3-(4-fluoro-2-methoxylphenyl)-4-methylpentan-2-yl ester ((2S,3S)-3-(4-fluoro-2-methoxylphenyl)-4-methylpentan-2-yl N-({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)-L-alaninate)+SX, N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine (2S,3S)-3-(4-fluoro-2-methylphenyl)-4-methylpentan-2-yl ester ((2S,3S)-3-(4-fluoro-2-methylphenyl)-4-methylpentan-2-ylN-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate)+SX, N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine (2S,3S)-3-(2-fluoro-4-methylphenyl)-4-methylpentan-2-yl ester ((2S,3S)-3-(2-fluoro-4-methylphenyl)-4-methylpentan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate)+SX, N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine (2S,3S)-3-(2,4-difluorophenyl)-4-methylpentan-2-yl ester ((2S,3S)-3-(2,4-difluorophenyl)-4-methylpentan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate)+SX, N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine (2S,3S)-3-(2,4-dimethylphenyl)-4-methylpentan-2-yl ester ((2S,3S)-3-(2,4-dimethylphenyl)-4-methylpentan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate)+SX, N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine (2S,3S)-3-(4-fluoro-2-methoxylphenyl)-4-methylpentan-2-yl ester ((2S,3S)-3-(4-fluoro-2-methoxylphenyl)-4-methylpentan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate)+SX, N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine 3-(4-bromo-7-fluoroindol-1-yl)butan-2-yl ester (3-(4-bromo-7-fluoroindol-1-yl)butan-2-ylN-[(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-alaninateN-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate)+SX, N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl ester ((1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate)+SX, N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alanine (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl ester ((1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate)+SX, Agrobacterium radiobactor strain K1026+SX, Agrobacterium radiobactor strain K84+SX, Bacillus amyloliquefaciens (Aveo (trademark) 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 strainBacillus 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 D747D747)+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 CGMCC8325 strain (Coniothyriumminitans 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-02CAB-02)+SX, Pseudomonas syringae strain 742RS)+SX, Pseudomonas syringae strain MA-4)+SX, Pseudozyma flocculosa PF-A22UL strain+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 IMI206040)+SX, Trichoderma atroviride strain IMI206040)+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 IMI206039IMI206039)+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.

[0554] The combination of the present component of group (c) with the present compound or the compounds of the present invention:

[0555] 1-methylcyclopropene + SX, 1,3-diphenylurea + SX, 2,3,5-triiodobenzoic acid + SX, IAA ((1H-indol-3-yl)acetic acid) + SX, IBA (4-(1H-indol-3-yl)butyric acid) + SX, MCPA (2-(4-chloro-2-methylphenoxy)acetic acid) + SX, MCPB (4-(4-chloro-2-methylphenoxy)butyric acid) + SX, 4-CPA (4-chlorophenoxyacetic acid) + SX, 5-aminolevulinic acid hydrochloride + SX, 6-benzylaminopurine + SX, abscisic acid + SX, AVG (aminoethoxyvinylglycine) + 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, cholinechloride)+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, maleichydrazide)+SX, mefluidide)+SX, mepiquat-chloride)+SX, oxidized glutathione)+SX, pacrobutrazol)+SX, pendimethalin)+SX, prohexandione-calcium)+SX, prohydrojasmon)+SX, pyraflufen-ethyl)+SX, sintofen)+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, Claroideoglomusetunicatum)+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 strain RTI-801+SX, Rhizophagus irregularis strain DAOM 197198+SX, Azorhizobium caulinodans)+SX, Azospirillum amazonense)+SX, Azospirillum brasilense strain XOH+SX, Azospirillum brasilense Ab-V5 strain+SX, Azospirillum brasilense Ab-V6 strain+SX, Azospirillum caulinodans+SX, Azospirillum halopraeferens)+SX, Azospirillum irakense)+SX, Azospirillum lipoferum)+SX, Bradyrhizobium elkanii strain SEMIA 587+SX, Bradyrhizobium elkanii strain SEMIA 5019+SX, Bradyrhizobium japonicum strain TA-11+SX, Bradyrhizobium japonicum strain USDA 110+SX, Bradyrhizobium liaoningense)+SX, Bradyrhizobium lupini)+SX, Delftia acidovorans strain RAY209+SX, Mesorhizobium ciceri)+SX, Mesorhizobium huakuiiHuakii)+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.

[0556] The combination of the component of the above group (d) with the present compound or the compound of the present invention:

[0557] Anthraquinone)+SX, Deet)+SX, Icaridin)+SX.

[0558] The ratio of the present compound or the compound of the present invention to the present component is not particularly limited. In terms of weight ratio (the present compound or the compound of the present invention: the present component), examples include 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, etc.

[0559] The present compound or the compound of the present invention can be mixed or used in combination with chemical fertilizers (such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.).

[0560] The present compound, the compound of the present invention or composition A can control plant diseases caused by phytopathogenic microorganisms such as fungi, oomycetes, Phytomyxea, bacteria, etc. As fungi, for example, Ascomycota, Basidiomycota, Blastocladiomycota, Chytridiomycota, Mucoromycota and Olpidiomycota can be mentioned. Specifically, for example, the following examples can be given. The scientific names of the phytopathogenic microorganisms causing each disease are shown in parentheses.

[0561] Diseases of rice: blast (Pyricularia oryzae), brown spot (Cochliobolus miyabeanus), sheath blight (Rhizoctonia solani), bakanae disease (Gibberella fujikuroi), yellowing and atrophy disease (Sclerophthora macrospora), false blast and panicle blight (Epicoccum nigrum), seedling blight (Trichoderma viride, Rhizopus oryzae);

[0562] Diseases of wheat: powdery mildew (Blumeria graminis), head blight (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), yellow rust (Puccinia striiformis), black rust (Puccinia graminis), brown rust (Puccinia recondita), pink snow mold (Microdochium nivale, Microdochium majus), snow scab (Typhula incarnata, Typhula ishikariensis), loose smut (Ustilago tritici), covered smut (Tilletia caries, Tilletia controversa), eyespot (Pseudocercosporella herpotrichoides), leaf blotch (Septoria tritici), glume blotch (Stagonospora nodorum), tan spot (Pyrenophora tritici-repentis), seedling blight caused by Rhizoctonia spp. (Rhizoctonia solani), take-all (Gaeumannomyces graminis), blast (Pyricularia graminis-tritici);

[0563] Diseases of barley: powdery mildew (Blumeria graminis), scab (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), yellow rust (Puccinia striiformis), black rust (Puccinia graminis), stripe rust (Puccinia hordei), loose smut (Ustilago nuda), Rhynchosporium leaf blotch (Rhynchosporium secalis), net blotch (Pyrenophora teres), spot blotch (Cochliobolus sativus), leaf stripe (Pyrenophora graminea), Ramularia leaf spot (Ramularia collo-cygni), seedling blight caused by Rhizoctonia spp. (Rhizoctonia solani);

[0564] Diseases of maize: rust (Puccinia sorghi), southern rust (Puccinia polysora), northern leaf blight (Setosphaeria turcica), tropical rust (Physopella zeae), Bipolaris leaf spot (Cochliobolus heterostrophus), anthracnose (Colletotrichum graminicola), gray leaf spot (Cercospora zeae-maydis), brown spot (Kabatiella zeae), Phaeosphaeria leaf spot (Phaeosphaeria maydis), Diplodia ear rot (Stenocarpella maydis, Stenocarpella macrospora), stalk rot (Fusarium graminearum, Fusarium verticillioides, Colletotrichum graminicola), common smut (Ustilago maydis), Physoderma stalk rot (Physoderma maydis);

[0565] Diseases of cotton: anthracnose (Colletotrichum gossypii), white mold (Ramularia areola), black spot (Alternaria macrospora, Alternaria gossypii), black root rot (Thielaviopsis basicola);

[0566] Diseases of coffee: rust (Hemileia vastatrix), leaf spot (Cercospora coffeicola);

[0567] Diseases of rapeseed: sclerotinia rot (Sclerotinia sclerotiorum), black spot (Alternaria brassicae), root rot (Phoma lingam), light leaf spot (Pyrenopeziza brassicae);

[0568] Diseases of sugarcane: rust (Puccinia melanocephala, Puccinia kuehnii), smut (Ustilago scitaminea);

[0569] Diseases of sunflower: rust (Puccinia helianthi), downy mildew (Plasmopara halstedii);

[0570] Diseases of citrus: melanosis (Diaporthe citri), scab (Elsinoe fawcetti), green mold rot (Penicillium digitatum), blue mold (Penicillium italicum), phytophthora blight (Phytophthora parasitica, Phytophthora citrophthora), aspergillosis (Aspergillus niger);

[0571] Diseases of apples: blossom blight (Monilinia mali), canker (Valsa ceratosperma), powdery mildew (Podosphaera leucotricha), Alternaria leaf spot (Alternaria alternata apple pathotype), scab (Venturia inaequalis), anthracnose (Glomerella cingulata, Colletotrichum acutatum), brown spot (Diplocarpon mali), ring rot (Botryosphaeria berengeriana), phytophthora blight (Phytophthora cactorum), rust (Gymnosporangium juniperi-virginianae, Gymnosporangium yamadae);

[0572] Diseases of pears: scab (Venturia nashicola, Venturia pirina), black spot (Alternaria alternata Japanese pear pathotype), rust (Gymnosporangium haraeanum);

[0573] Diseases of peaches: gray spot (Monilinia fructicola), scab (Cladosporium carpophilum), brown blotch (Phomopsis rot) (Phomopsis sp.), leaf curl (Taphrina deformans);

[0574] Diseases of grapes: anthracnose (Elsinoe ampelina), late rot (Glomerella cingulata, Colletotrichum acutatum), powdery mildew (Uncinula necator), rust (Phakopsora ampelopsidis), black rot (Guignardia bidwellii), downy mildew (Plasmoparaviticola);

[0575] Diseases of persimmons: anthracnose (Gloeosporium kaki, Colletotrichum acutatum), leaf fall disease (Cercospora kaki, Mycosphaerella nawae);

[0576] Diseases of figs: rust (Phakopsora nishidana);

[0577] Diseases of cucurbits: anthracnose (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea), gummy stem blight (Didymella bryoniae), brown spot (Corynespora cassiicola), fusarium wilt (Fusarium oxysporum), downy mildew (Pseudoperonospora cubensis), phytophthora blight (Phytophthora capsici), damping-off (Pythium sp.);

[0578] Diseases of tomatoes: bacterial ring rot (Alternaria solani), leaf mold (Cladosporium fulvum), target spot (Pseudocercospora fuligena), late blight (Phytophthora infestans), powdery mildew (Leveillula taurica);

[0579] Diseases of eggplant: Phomopsis vexans, Erysiphe cichoracearum;

[0580] Diseases of cruciferous vegetables: Alternaria japonica, Cercosporella brassicae, Plasmodiophora brassicae, Peronospora parasitica, Albugo candida;

[0581] Disease of scallions: Puccinia allii;

[0582] Diseases of soybeans: Cercospora kikuchii, Elsinoe glycines, Diaporthe phaseolorum var. sojae, Phakopsora pachyrhizi, Corynespora cassiicola, Colletotrichum glycines, Colletotrichum truncatum, Rhizoctonia solani, Septoria glycines, Cercospora sojina, Sclerotinia sclerotiorum, Microsphaera diffusa, Phytophthora sojae, Peronospora manshurica, Fusarium virguliforme, Calonectria ilicicola, Diaporthe / Phomopsis complex (Diaporthe longicolla);

[0583] Diseases of kidney beans: Sclerotinia rot (Sclerotinia sclerotiorum), rust (Uromyces appendiculatus), angular leaf spot (Phaeoisariopsis griseola), anthracnose (Colletotrichum lindemuthianum), root rot (Fusarium solani);

[0584] Diseases of peanuts: black leaf spot (Cercospora personata), brown leaf spot (Cercospora arachidicola), southern blight (Sclerotium rolfsii), red crown rot (Calonectria ilicicola);

[0585] Diseases of peas: powdery mildew (Erysiphe pisi), root rot (Fusarium solani);

[0586] Diseases of potatoes: early blight (Alternaria solani), late blight (Phytophthora infestans), pink rot (Phytophthora erythroseptica), powdery scab (Spongospora subterranea f.sp. subterranea), Verticillium wilt (Verticillium albo - atrum, Verticillium dahliae, Verticillium nigrescens), dry rot (Fusarium solani), potato wart disease (Synchytrium endobioticum);

[0587] Diseases of strawberries: powdery mildew (Sphaerotheca humuli));

[0588] Diseases of tea: net blotch (Exobasidium reticulatum), white star blight (Elsinoe leucospila), gray blight (Pestalotiopsis sp.), anthracnose (Colletotrichum theae-sinensis);

[0589] Diseases of tobacco: brown spot (Alternaria longipes), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), phytophthora blight (Phytophthora nicotianae);

[0590] Diseases of sugar beet: leaf spot (Cercospora beticola), leaf blight (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris), black root rot (aphanomyces root rot) (Aphanomyces cochlioides), rust (Uromyces betae);

[0591] Diseases of rose: black spot (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa);

[0592] Diseases of chrysanthemum: leaf spot (Septoria chrysanthemi-indici), white rust (Puccinia horiana);

[0593] Diseases of onion: botrytis leaf blight (Botrytis cinerea, Botrytis byssoidea, Botrytis squamosa), gray rot (Botrytis allii), sclerotial neck rot (Botrytis squamosa);

[0594] Diseases of various crops: Gray mold (Botrytis cinerea), Sclerotinia rot (Sclerotinia sclerotiorum), Seedling damping-off (Pythium aphanidermatum, Pythium irregulare, Pythium ultimum);

[0595] Diseases of radish: Alternaria leaf spot (Alternaria brassicicola);

[0596] Diseases of turfgrass: Dollar spot (Sclerotinia homoeocarpa), Brown patch, Large patch (Rhizoctonia solani), Pythium blight (Pythium aphanidermatum);

[0597] Diseases of banana: Sigatoka disease (Mycosphaerella fijiensis, Mycosphaerella musicola);

[0598] Diseases of lentil: Ascochyta disease (Ascochyta lentis);

[0599] Diseases of chickpea: Ascochyta blight (Ascochyta rabiei));

[0600] Diseases of green pepper: Anthracnose (Colletotrichum scovillei));

[0601] Diseases of mango: Anthracnose (Colletotrichum acutatum));

[0602] Diseases of fruit trees: White root rot (Rosellinia necatrix), Purple root rot (Helicobasidium mompa);

[0603] Diseases of harvested fruits such as apples and pears: Mucor rot diseases (Mucor piriformis);

[0604] Seed diseases or diseases in the early growth stage caused by Aspergillus, Penicillium, Fusarium, Gibberella, Tricoderma, Thielaviopsis, Rhizopus, Mucor, Corticium, Phoma, Rhizoctonia, Diplodia, etc.;

[0605] Viral diseases: The big vein disease of lettuce mediated by Olpidium brassicae, and viral diseases of various crops mediated by Polymyxa (e.g., Polymyxa betae and Polymyxa graminis);

[0606] Diseases caused by bacteria: Bacterial seedling blight of rice (Burkholderia plantarii), bacterial angular leaf spot of cucumber (Pseudomonas syringae pv. lachrymans), bacterial wilt of eggplant (Ralstonia solanacearum), citrus canker (Xanthomonas citri), soft rot of Chinese cabbage (Erwinia carotovora), potato scab (Streptomyces scabiei), Stewart's wilt of corn (Clavibacter michiganensis), crown gall of grape, olive, peach, etc. (Xylella fastidiosa), root nodule disease of Rosaceae plants such as apple, peach, cherry, etc. (Agrobacterium tumefaciens).

[0607] As the method for controlling plant diseases of the present invention, it is implemented by treating plants or the soil of cultivated plants with an effective amount of this compound, the compound of the present invention or composition A. As treatment methods, for example, foliar treatment, soil treatment and seed treatment can be cited.

[0608] This compound, the compound of the present invention or composition A is usually mixed with an inert carrier such as a solid carrier or a liquid carrier, and surfactants and other formulation adjuvants are added as needed, and formulated into emulsions, oils, powders, granules, wettable powders, granular wettable powders, flowables, dry flowables, microcapsules, etc. for use. These formulations contain the compound, the compound of the present invention or composition A in an amount usually of 0.1 to 99% by weight.

[0609] Examples of the solid carrier include fine powders and granular materials such as clays (kaolin clay, diatomaceous earth, bentonite, acid clay, etc.), dry silica, wet silica, talc, ceramics, other inorganic minerals (sericite, quartz, sulfur, activated carbon, calcium carbonate, etc.), chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.), and synthetic resins (polypropylene, polyacrylonitrile, polymethyl methacrylate, polyester resins such as polyethylene terephthalate, nylon resins such as nylon-6, nylon-11, nylon-66, polyamide resins, polyvinyl chloride, polyvinylidene chloride, vinyl chloride-propylene copolymers, etc.).

[0610] Examples of the liquid carrier include water, alcohols (methanol, ethanol, isopropanol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), aromatic hydrocarbons (toluene, xylene, ethylbenzene, dodecylbenzene, phenylxyleneethylbenzene, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil, etc.), esters (ethyl acetate, butyl acetate, isopropyl myristate, ethyl oleate, isopropyl adipate, diisobutyl adipate, propylene glycol monomethyl ether acetate, etc.), nitriles (acetonitrile, isobutyronitrile, etc.), ethers (diisopropyl ether, 1,4-dioxane, 1,2-dimethoxyethane, diethylene glycol dimethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, 3-methoxy-3-methyl-1-butanol, etc.), amides (DMF, N,N-dimethylacetamide, etc.), sulfoxides (DMSO, etc.), propylene carbonate, and vegetable oils (soybean oil, cottonseed oil, etc.).

[0611] As surfactants, nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, and polyethylene glycol fatty acid esters, and anionic surfactants such as alkyl sulfonates, alkyl benzene sulfonates, and alkyl sulfates can be mentioned. Specifically, Nimbus (registered trademark), Assist (registered trademark), Aureo (registered trademark), Iharol (registered trademark), Silwet L-77 (registered trademark), BreakThru (registered trademark), SundanceII (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 (registered trademark) X45, AGRAL 90 (registered trademark), AGROTIN (registered trademark), ARPON (registered trademark), EnSpray N (registered trademark), and BANOLE (registered trademark) etc. can be mentioned.

[0612] As other preparation adjuvants, fixatives, dispersants, colorants, stabilizers, etc. can be mentioned. Specifically, there are casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), isopropyl acid phosphate, 2,6-di-tert-butyl-4-methylphenol, BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).

[0613] In the present invention, plants include the whole plant and specific parts of the plant. As specific parts of the plant, for example, stems and leaves, flowers, spikes, fruits, trunks, branches, crowns, seeds, vegetative propagation organs, and seedlings can be mentioned.

[0614] The vegetative propagation organs refer to the parts among the roots, stems, leaves, etc. of a plant that have the ability to grow when this part is detached from the main body and placed in the soil. Examples of vegetative propagation organs include, for example, tuberous roots, creeping roots, bulbs, corms (or solid bulbs), tubers, rhizomes, stolons, rhizophores, cane cuttings, propagules, and vine cuttings. It should be noted that stolons are sometimes also called runners, and propagules are also called bulbils, which are divided into broad buds and bulbils. Vine cuttings refer to the slender parts (collective term for leaves and stems, shoots without roots) of sweet potatoes, Japanese yams, etc. Bulbs, corms, tubers, rhizomes, cane cuttings, rhizophores, or tuberous roots are also collectively called bulbs. The cultivation of potatoes starts by implanting tubers into the soil, but the tubers used are usually called seed potatoes.

[0615] As seed treatment, for example, there can be mentioned the treatment of seeds or vegetative propagation organs with this compound, the compound of the present invention, or composition A. Specifically, for example, there can be mentioned the spraying treatment of atomizing the suspension of this compound, the compound of the present invention, or composition A and spraying it onto the surface of seeds or vegetative propagation organs; the coating treatment of coating this compound, the compound of the present invention, or composition A onto seeds or vegetative propagation organs; the immersion treatment of immersing seeds in the liquid medicine of this compound, the compound of the present invention, or composition A for a specified time; the method of coating seeds or vegetative propagation organs with a carrier containing this compound, the compound of the present invention, or composition A (coating treatment, pellet coating treatment, etc.). As the above-mentioned vegetative propagation organs, seed potatoes can be particularly mentioned.

[0616] When treating seeds or vegetative propagation organs with composition A, composition A can be made into a single preparation for treating seeds or vegetative propagation organs, or composition A can be made into different multiple preparations and treated on seeds or vegetative propagation organs in several times. As a method of making composition A into different multiple preparations and treating it in several times, there can be mentioned: for example, treating with a preparation containing only this compound or the compound of the present invention as the active ingredient, allowing the seeds or vegetative propagation organs to air-dry, and then treating with a preparation containing this ingredient; and treating with a preparation containing this compound and this ingredient or containing the compound of the present invention and this ingredient as the active ingredient, allowing the seeds or vegetative propagation organs to air-dry, and then treating with a preparation containing this ingredient other than the already treated this ingredient.

[0617] The seeds or vegetative propagation organs that retain the compound, the compound of the present invention, or Composition A in the present invention refer to seeds or vegetative propagation organs in a state where the compound, the compound of the present invention, or Composition A is attached to the surface of the seeds or vegetative propagation organs. For the seeds or vegetative propagation organs that retain the above-mentioned compound, the compound of the present invention, or Composition A, materials other than the compound, the compound of the present invention, or Composition A may be attached before or after attaching the compound, the compound of the present invention, or Composition A to the seeds or vegetative propagation organs.

[0618] In addition, when Composition A forms a layer and adheres to the surface of the seeds or vegetative propagation organs, the layer is composed of one or more layers. In addition, when composed of multiple layers, each layer is a layer containing one or more active ingredients, or is composed of a layer containing one or more active ingredients and a layer containing no active ingredients.

[0619] The seeds or vegetative propagation organs that retain the compound, the compound of the present invention, or Composition A can be obtained, for example, by applying a preparation containing the compound, the compound of the present invention, or Composition A to the seeds or vegetative propagation organs using the aforementioned seed treatment method.

[0620] The application amount of the compound, the compound of the present invention, or Composition A varies depending on meteorological conditions, formulation form, application period, application method, application site, target disease, target crop, etc. In the case of foliar treatment or soil treatment, per 1000 m 2 it is usually 1 to 500 g. In the case of seed treatment, based on 1 Kg of seeds, the amount of the compound, the compound of the present invention, or Composition A is usually 0.001 to 100 g. When formulating the compound, the compound of the present invention, or Composition A into an emulsion, aqueous solution, suspension, etc., it is usually diluted with water so that the active ingredient concentration becomes 0.01 to 10,000 ppm and then applied, and powders, granules, etc. are usually applied directly.

[0621] The compound, the compound of the present invention, or Composition A can be used as a fungicide for plant diseases in agricultural fields such as upland fields, paddy fields, lawns, and orchards. Examples of plants include the following plants.

[0622] Maize (dent corn, flint corn, soft corn, pop corn, waxy corn, sweet corn, forage corn), rice (long grain rice, short grain rice, medium grain rice, japonica rice, tropical japonica rice, indica rice, javanica rice, paddy rice, upland rice, floating rice, direct seeding, transplantation, glutinous rice), wheat (bread wheat (hard, soft, medium, red wheat, white wheat), durum wheat, spelt wheat, club wheat, their respective winter wheat types, spring wheat types), barley (two-row barley (= barley for brewing), six-row barley, hull-less barley, pearl barley, their respective winter barley types, spring barley types), rye (winter rye type, spring rye type), triticale (winter triticale type, spring triticale type), oats (winter oat type, spring oat type), sorghum, cotton (upland cotton, pima cotton), soybean (cultivars for harvesting mature seeds, edamame cultivars, forage cultivars, their respective indeterminate growth types, determinate growth types, semi-determinate growth types), peanut, buckwheat, sugar beet (for sugar production, forage, root vegetable, leaf vegetable, fuel), rapeseed (winter rapeseed type, spring rapeseed type), canola (winter canola type, spring canola type), sunflower (for oil extraction, edible, ornamental), sugarcane, tobacco, tea, mulberry, solanaceous vegetables (eggplant, tomato, green pepper, chili pepper, potato, etc.), cucurbitaceous vegetables (cucumber, pumpkin, zucchini, watermelon, melon, etc.), cruciferous vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, mustard, broccoli, cauliflower, etc.), asteraceous vegetables (burdock, spring chrysanthemum, artichoke, lettuce, etc.), liliaceous vegetables (scallion, onion, garlic, asparagus, etc.), umbelliferous vegetables (carrot, parsley, celery, parsnip, etc.), chenopodiaceous vegetables (spinach, chard, etc.), labiatae vegetables (perilla, mint, basil, etc.), strawberry, sweet potato, Japanese yam, taro, pome fruits (apple, European pear, Japanese pear, white pear, Chinese flowering quince, quince, etc.), stone fruits (peach, plum, nectarine, Japanese apricot (Prunus mume), cherry, apricot, prune, etc.), citrus fruits (Satsuma mandarin, orange, lemon, lime, grapefruit, etc.), nuts (chestnut, walnut, hazelnut, almond, pistachio, cashew nut, macadamia nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, persimmon, fig, olive, loquat, banana, coffee, date palm, coconut, ornamental plants, forest plants, turf grasses, forage grasses, etc.

[0623] The above-mentioned plants only need to be commonly cultivated varieties, without any particular limitation. The above-mentioned plants also include: plants that can be created by natural cross-breeding; plants that can be generated by mutation; F1 hybrid plants; and genetically modified crops. As genetically modified crops, for example, plants that have been given tolerance to herbicides such as HPPD (4-hydroxyphenylpyruvate dioxygenase) inhibitors like isoxaflutole, ALS (acetolactate synthase) inhibitors like imazethapyr and thifensulfuron-methyl, EPSP (5-enolpyruvylshikimate-3-phosphate synthase) inhibitors, glutamine synthetase inhibitors, PPO (protoporphyrinogen oxidase) inhibitors, bromoxynil, or dicamba; plants that can synthesize selective toxins known in the genus Bacillus such as Bacillus thuringiensis; plants that can confer specific insecticidal activity by inducing gene silencing (RNAi; RNA interference) in the target harmful insects by synthesizing gene fragments that are partially identical to the endogenous genes from harmful insects.

[0624] Examples

[0625] Hereinafter, production examples, reference production examples, formulation examples, and test examples are shown to more specifically illustrate the present invention, but the present invention is not limited to these examples. In this specification, Me represents methyl, Et represents ethyl, Pr represents propyl, i-Pr represents isopropyl, c-Pr represents cyclopropyl, Bu represents butyl, i-Bu represents isobutyl, s-Bu represents sec-butyl, t-Bu represents tert-butyl, c-Bu represents cyclobutyl, Pen represents pentyl, i-Pen represents isopentyl, neo-Pen represents neopentyl, c-Hex represents cyclohexyl, Allyl represents allyl, Ph represents phenyl, 2-Py represents 2-pyridyl, 3-Py represents 3-pyridyl, 4-Py represents 4-pyridyl. When the phenyl or pyridyl group has a substituent, the substituent and the substitution position are described together before the symbol. For example, 2-CN-Ph represents 2-cyanophenyl, 3,4-F2-Ph represents 3,4-difluorophenyl, and 4-(OMe)-Ph represents 4-methoxyphenyl.

[0626] Production examples of the present compound and the compounds of the present invention are shown.

[0627] Reference Production Example 1

[0628] To a mixture of 2.2 g of dimethylaminosulfonylpyrazole and 20 mL of THF, 5.3 mL of butyllithium (2.6 M, hexane solution) was added dropwise at -78 °C, and the mixture was stirred at -78 °C for 30 minutes. 1.8 g of diethyl disulfide was added to the resulting mixture, and the mixture was stirred at room temperature for 4 hours. An aqueous ammonium chloride solution was added to the resulting mixture, and extraction was carried out with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 3.0 g of intermediate MA1-1 represented by the following formula.

[0629] [Chemical formula 34]

[0630]

[0631] Intermediate MA1-1: 1 H-NMR(CDCl3)δ: 7.62(1H, d), 6.18(1H, d), 3.02(6H, s), 2.96(2H, q), 1.38(3H, t).

[0632] Reference Production Example 1-1

[0633] The compounds produced according to Reference Production Example 1 and their physical property values are shown below.

[0634] In the compound represented by formula (MA1), R 6 , R 7 , and the combination of Z are compounds in any of the combinations described in [Table MA1].

[0635] [Chemical formula 35]

[0636]

[0637] [Table 1]

[0638] [Table MA1]

[0639] Intermediate <![CDATA[R 6 > <![CDATA[R 7 > Z MA1-2 H H Pr MA1-3 H H Me MA1-4 H H i-Pr MA1-5 H H Bu MA1-6 H H i-Bu MA1-7 H H Pen MA1-8 H H i-Pen MA1-9 H H c-Hex MA1-10 H H Allyl MA1-11 H H Ph MA1-12 H H 4-(OMe)-Ph MA1-13 H H 4-Cl-Ph MA1-14 H H 2-(OMe)-Ph MA1-15 H H 2-Cl-Ph MA1-16 H H 4-Py MA1-17 H H 2-Py MA1-18 H F Pr

[0640] Intermediate MA1-2: 1 H-NMR(CDCl3)δ: 7.61(1H, d), 6.16(1H, d), 3.02(6H, s), 2.91(2H, dd), 1.74(2H, m), 1.06(3H, t).

[0641] Intermediate MA1-3: 1 H-NMR(CDCl3)δ: 7.63(1H, d), 6.09(1H, d), 3.01(6H, s), 2.49(3H, s).

[0642] Intermediate MA1-4: 1 H-NMR(CDCl3)δ: 7.62(1H, d), 6.28(1H, d), 3.45(1H, m), 3.03(6H, s), 1.36(6H, d).

[0643] Intermediate MA1-5: 1 H-NMR(CDCl3)δ: 7.62(1H, d), 6.16(1H, d), 3.02(6H, s), 2.93(2H, dd), 1.70(2H, m), 1.48(2H, m), 0.94(3H, t).

[0644] Intermediate MA1-6: 1 H-NMR(CDCl3)δ: 7.61(1H, d), 6.14(1H, d), 3.02(6H, s), 2.81(2H, d), 1.96(1H, m), 1.06(6H, d).

[0645] Intermediate MA1-7: 1 H-NMR(CDCl3)δ: 7.61(1H, d), 6.16(1H, d), 3.02(6H, s), 2.92(2H, dd), 1.71(2H, m), 1.47 - 1.29(4H, m), 0.91(3H, t).

[0646] Intermediate MA1-8: 1 H-NMR(CDCl3)δ: 7.62(1H, d), 6.16(1H, d), 3.02(6H, s), 2.93(2H, m), 1.74(1H, m), 1.63 - 1.57(2H, m), 0.93(6H, d).

[0647] Intermediate MA1-9: 1 H-NMR(CDCl3)δ: 7.61(1H, d), 6.26(1H, d), 3.20(1H, m), 3.03(6H, s), 2.07 - 2.00(2H, m), 1.83 - 1.76(2H, m), 1.65 - 1.26(6H, m).

[0648] Intermediate MA1-10: 1 H-NMR(CDCl3)δ: 7.61(1H, d), 6.23(1H, d), 5.88(1H, m), 5.24(1H, m), 5.17(1H, m), 3.58(2H, m), 3.02(6H, s).

[0649] Intermediate MA1-11: 11H-NMR (CDCl3) δ: 7.57 - 7.51 (3H, m), 7.42 - 7.37 (3H, m), 5.78 (1H, d), 3.04 (6H, s).

[0650] Intermediate MA1-12: 1 1H-NMR (CDCl3) δ: 7.52 (2H, m), 7.47 (1H, d), 6.94 (2H, m), 5.56 (1H, d), 3.84 (3H, s), 3.04 (6H, s).

[0651] Intermediate MA1-13: 1 1H-NMR (CDCl3) δ: 7.54 (1H, d), 7.45 (2H, m), 7.36 (2H, m), 5.85 (1H, d), 3.05 (6H, s).

[0652] Intermediate MA1-14: 1 1H-NMR (CDCl3) δ: 7.52 (1H, d), 7.42 - 7.36 (2H, m), 6.98 - 6.94 (2H, m), 5.74 (1H, d), 3.84 (3H, s), 3.04 (6H, s).

[0653] Intermediate MA1-15: 1 1H-NMR (CDCl3) δ: 7.59 (1H, d), 7.48 (1H, m), 7.40 (1H, m), 7.32 (1H, m), 7.26 (1H, m), 5.89 (1H, d), 3.05 (6H, s).

[0654] Intermediate MA1-16: 1 1H-NMR (CDCl3) δ: 8.46 (2H, m), 7.75 (1H, d), 7.05 (2H, m), 6.57 (1H, d), 3.07 (6H, s).

[0655] Intermediate MA1-17: 1 1H-NMR (CDCl3) δ: 8.45 (1H, m), 7.73 (1H, d), 7.57 (1H, m), 7.12 - 7.08 (2H, m), 6.60 (1H, d), 3.04 (6H, s).

[0656] Intermediate MA1-18: 1 1H-NMR (CDCl3) δ: 7.56 (1H, d), 3.08 (6H, s), 2.90 (2H, t), 1.62 (2H, m), 1.01 (3H, t).

[0657] Reference Production Example 2

[0658] A mixture of 3.0 g of intermediate MA1-1 and 30 mL of trifluoroacetic acid was stirred at 50 °C for 2 hours. Water was added to the resulting mixture, and the mixture was extracted with chloroform. The obtained organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.9 g of intermediate MA2-1 represented by the following formula.

[0659] [Chemical formula 36]

[0660]

[0661] Intermediate MA2-1: 1 1H-NMR (CDCl3) δ: 7.62 (1H, d), 6.37 (1H, d), 2.90 (2H, q), 1.30 (3H, t).

[0662] Reference Production Example 2-1

[0663] The compounds produced according to Reference Production Example 2 and their physical property values are shown below.

[0664] In the compound represented by formula (MA2), R 6 , R 7 , and the combination of Z are any of the combinations described in [Table MA2].

[0665] [Chemical formula 37]

[0666]

[0667] [Table 2]

[0668] [Table MA2]

[0669] Intermediate <![CDATA[R 6 > <![CDATA[R 7 > Z MA2-2 H H Pr MA2-3 H H Me MA2-4 H H i-Pr MA2-5 H H Bu MA2-6 H H i.Bu MA2-7 H H Pen MA2-8 H H i-Pen MA2-9 H H c-Hex MA2-10 H H Allyl MA2-11 H H Ph MA2-12 H H 4-(OMe)-Ph MA2-13 H H 4-Cl-Ph MA2-14 H H 2-(OMe)-Ph MA2-15 H H 2-Cl-Ph MA2-16 H H 4-Py MA2-17 H H 2-Py MA2-18 H F Pr

[0670] Intermediate MA2-2: 1 1H-NMR (CDCl3) δ: 7.62 (1H, d), 6.35 (1H, d), 2.86 (2H, dd), 1.65 (2H, m), 1.00 (3H, t).

[0671] Intermediate MA2-3: 1 1H-NMR (CDCl3) δ: 7.60 (1H, d), 6.31 (1H, d), 2.51 (3H, s).

[0672] Intermediate MA2-4: 11H-NMR (CDCl3) δ: 7.65 (1H, d), 6.41 (1H, d), 3.28 (1H, m), 1.29 (6H, d).

[0673] Intermediate MA2-5: 1 1H-NMR (CDCl3) δ: 7.59 (1H, d), 6.35 (1H, d), 2.88 (2H, dd), 1.62 (2H, m), 1.42 (2H, m), 0.90 (3H, t).

[0674] Intermediate MA2-6: 1 1H-NMR (CDCl3) δ: 7.65 (1H, br s), 6.37 (1H, br s), 2.83 (2H, d), 1.86 (1H, m), 1.02 (6H, d).

[0675] Intermediate MA2-7: 1 1H-NMR (CDCl3) δ: 7.58 (1H, d), 6.34 (1H, d), 2.88 (2H, dd), 1.64 (2H, m), 1.43 - 1.26 (4H, m), 0.88 (3H, t).

[0676] Intermediate MA2-8: 1 1H-NMR (CDCl3) δ: 7.59 (1H, d), 6.34 (1H, d), 2.89 (2H, dd), 1.70 (1H, m), 1.52 (2H, m), 0.89 (6H, d).

[0677] Intermediate MA2-9: 1 1H-NMR (CDCl3) δ: 7.60 (1H, d), 6.39 (1H, d), 3.03 - 2.94 (1H, m), 2.01 - 1.93 (2H, m), 1.79 - 1.71 (2H, m), 1.63 - 1.55 (1H, m), 1.41 - 1.18 (5H, m).

[0678] Intermediate MA2-10: 1 1H-NMR (CDCl3) δ: 7.62 (1H, br s), 6.38 (1H, br s), 5.89 (1H, m), 5.11 - 5.03 (2H, m), 3.50 (2H, m).

[0679] Intermediate MA2-11: 1 1H-NMR (CDCl3) δ: 7.54 (1H, d), 7.28 - 7.14 (5H, m), 6.43 (1H, d).

[0680] Intermediate MA2-12: 1 H-NMR(CDCl3) δ: 7.54(1H, br s), 7.34(2H, m), 6.83(2H, m), 6.31(1H, br s), 3.78(3H, s).

[0681] Intermediate MA2-13: 1 H-NMR(CDCl3) δ: 7.60(1H, d), 7.26 - 7.15(4H, m), 6.44(1H, d).

[0682] Intermediate MA2-14: 1 H-NMR(CDCl3) δ: 7.63(1H, d), 7.19(1H, m), 6.96(1H, m), 6.90 - 6.81(2H, m), 6.48(1H, d), 3.92(3H, s).

[0683] Intermediate MA2-15: 1 H-NMR(CDCl3) δ: 7.67(1H, d), 7.38 - 7.33(1H, m), 7.12 - 7.05(2H, m), 6.89 - 6.84(1H, m), 6.55(1H, d).

[0684] Intermediate MA2-16: 1 H-NMR(CDCl3) δ: 8.37(2H, m), 7.74(1H, d), 6.89(2H, m), 6.60(1H, d).

[0685] Intermediate MA2-17: 1 H-NMR(CDCl3) δ: 8.44(1H, d), 7.70(1H, m), 7.50(1H, m), 7.07 - 6.98(2H, m), 6.56(1H, d).

[0686] Intermediate MA2-18: 1 H-NMR(CDCl3) δ: 10.56(1H, br s), 7.48(1H, d), 2.79(2H, t), 1.62(2H, m), 1.00(3H, t).

[0687] Reference Production Example 3

[0688] To a mixture of 3.0 g of 1-(4-chlorophenyl)-1H-pyrazol-3-ol and 6.0 mL of pyridine, 5.0 g of trifluoromethanesulfonic anhydride was added dropwise at 0 °C, and the mixture was stirred at 0 °C for 2 hours. To the resulting mixture, an aqueous sodium bicarbonate solution was added, and extraction was carried out with ethyl acetate. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain 5.3 g of Intermediate MA3-1 represented by the following formula.

[0689] [Chemical Formula 38]

[0690]

[0691] Intermediate MA3-1

[0692] Reference Production Example 4

[0693] A mixture of 1.4 g of Intermediate MA2-2, 2.6 g of 3-iodoaniline, 1.5 g of copper(I) iodide, 1.4 g of trans-N,N'-dimethylcyclohexane-1,2-diamine, 2.8 g of potassium carbonate, and 25 mL of DMF was stirred at 80 °C for 10 hours. Water was added to the resulting mixture, and filtration was carried out. After extraction of the filtrate with ethyl acetate, the obtained organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 70:30) to obtain 2.2 g of Intermediate MA4-1 represented by the following formula.

[0694] [Chemical Formula 39]

[0695]

[0696] Intermediate MA4-1: 1 H-NMR(CDCl3)δ:7.82(1H,d),7.18(1H,t),7.09(1H,t),6.97(1H,m),6.57(1H,m),6.38(1H,d),3.81(2H,br s),2.99(2H,m),1.74(2H,m),1.04(3H,t).

[0697] Reference Production Example 4-1

[0698] The compounds produced according to Reference Production Example 4 and their physical property values are shown below.

[0699] In the compound represented by formula (MA4), R 1 , R 2 , R 3 , R 4 , and R 5 are combined in any one of the combinations described in [Table MA4].

[0700] [Chemical Formula 40]

[0701]

[0702] [Table 3]

[0703] [Table MA4]

[0704] Intermediate <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 5 > MA4-2 H H <![CDATA[NH2]]> H H MA4-3 H F <![CDATA[NH2]]> H H MA4-4 H H C(O)OEt H H MA4-5 H C(O)OEt H H H

[0705] Intermediate MA4-2: 1 H-NMR(CDCl3) δ: 7.72(1H, d), 7.42(2H, m), 6.72(2H, m), 6.37(1H, d), 3.72(2H, br s), 2.97(2H, m), 1.73(2H, m), 1.03(3H, t).

[0706] Intermediate MA4-3: 1 H-NMR(CDCl3) δ: 7.72(1H, d), 7.37(1H, m), 7.21(1H, m), 6.81(1H, t), 6.37(1H, d), 3.76(2H, br s), 2.98(2H, t), 1.74(2H, m), 1.03(3H, t).

[0707] Intermediate MA4-4: 1 H-NMR(CDCl3) δ: 8.12(2H, m), 7.95(1H, d), 7.74(2H, m), 6.44(1H, d), 4.39(2H, q), 3.05(2H, t), 1.77(2H, m), 1.41(3H, t), 1.06(3H, t).

[0708] Intermediate MA4-5: 1 H-NMR(CDCl3) δ: 8.27(1H, m), 7.95 - 7.92(3H, m), 7.52(1H, t), 6.44(1H, d), 4.42(2H, q), 3.04(2H, t), 1.77(2H, m), 1.42(3H, t), 1.05(3H, t).

[0709] Reference Production Example 5

[0710] A mixture of 7.8 g of Intermediate MA4-5, 2.9 g of potassium hydroxide, 40 mL of ethanol, and 20 mL of water was stirred at 50 °C for 4 hours. 30 mL of 2.0 M hydrochloric acid was added to the resulting mixture, and the mixture was stirred for 1 hour. The resulting mixture was filtered, and the obtained solid was dried under reduced pressure to obtain 5.8 g of Intermediate MA5-1 represented by the following formula.

[0711] [Chemical Formula 41]

[0712]

[0713] Intermediate MA5-1: 1 H-NMR (CDCl3) δ: 8.31 (1H, m), 8.02 - 7.99 (2H, m), 7.96 (1H, d), 7.56 (1H, t), 6.45 (1H, d), 3.05 (2H, t), 1.77 (2H, m), 1.06 (3H, t).

[0714] Reference Production Example 5-1

[0715] Using Intermediate MA4-4 in place of Intermediate MA4-5, according to Reference Production Example 5, Intermediate MA5-2 shown by the following formula was obtained.

[0716] [Chemical Formula 42]

[0717]

[0718] Intermediate MA5-2: 1 H-NMR (DMSO-d6) δ: 8.57 (1H, m), 8.03 (2H, m), 7.85 (2H, m), 6.58 (1H, m), 3.01 (2H, t), 1.65 (2H, m), 0.97 (3H, t).

[0719] Reference Production Example 6

[0720] A mixture of 4.2 g of Compound IIA-150 of the present invention, 0.8 g of ammonium chloride, 2.8 g of zinc, 20 mL of THF, and 10 mL of water was stirred at 0 °C for 2 hours. After filtering the resulting mixture, the obtained filtrate was extracted with MTBE. The obtained organic layer was dried with magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 2.8 g of Intermediate MA6-1 shown by the following formula.

[0721] [Chemical Formula 43]

[0722]

[0723] Intermediate MA6-1: 1 H-NMR (CDCl3) δ: 7.85 (1H, d), 7.38 (1H, m), 7.30 (1H, t), 7.21 - 7.18 (1H, m), 6.88 - 6.84 (2H, m), 6.40 (1H, d), 5.64 (1H, br s), 3.00 (2H, t), 1.74 (2H, m), 1.04 (3H, t).

[0724] Reference Production Example 6-1

[0725] Instead of using Compound IIA-150 of the present invention, Compound IIA-149 of the present invention was used, and according to Reference Production Example 6, Intermediate MA6-2 represented by the following formula was obtained.

[0726] [Chemical Formula 44]

[0727]

[0728] Intermediate MA6-2: 1 H-NMR(CDCl3)δ: 7.78(1H, d), 7.55(2H, m), 7.03(2H, m), 6.83(1H, brs), 6.39(1H, d), 5.58(1H, br s), 2.99(2H, t), 1.74(2H, m), 1.04(3H, t).

[0729] Production Example 1

[0730] A mixture of 0.38 g of Intermediate MA2-1, 0.78 g of 4-iodotoluene, 0.46 g of copper(I) iodide, 0.43 g of trans-N,N'-dimethylcyclohexane-1,2-diamine, 0.87 g of potassium carbonate, and 10 mL of DMF was stirred at 80 °C for 4 hours. Water was added to the resulting mixture, and it was filtered. The filtrate was extracted with ethyl acetate. The obtained organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 20:1) to obtain 0.61 g of Compound IIA-1 of the present invention represented by the following formula.

[0731] [Chemical Formula 45]

[0732]

[0733] Compound IIA-1 of the present invention: 1 H-NMR(CDCl3)δ: 7.83(1H, d), 7.55(2H, m), 7.22(2H, m), 6.40(1H, d), 3.03(2H, q), 2.37(3H, s), 1.38(3H, t).

[0734] Production Example 1-1

[0735] The compounds produced according to Production Example 1 and their physical property values are shown below.

[0736] In the compound represented by formula (A1), Z, R 1 , R 2 , R 3 , R 4 , R 5 , R6 and R 7 The combination of and is a compound of any one of the combinations described in [Table IIA1-1], [Table IIA1-2] and [Table IA1].

[0737] [Chemical formula 46]

[0738]

[0739] [Table 4]

[0740] [Table IIA1-1]

[0741]

[0742] Compound IIA-2 of the present invention: 1 H-NMR(CDCl3)δ: 7.93(1H, d), 7.80(2H, m), 7.69(2H, m), 6.45(1H, d), 3.08(2H, q), 1.41(3H, t).

[0743] Compound IIA-3 of the present invention: 1 H-NMR(CDCl3)δ: 7.77(1H, d), 7.57(2H, m), 6.95(2H, m), 6.40(1H, d), 3.83(3H, s), 3.02(2H, q), 1.37(3H, t).

[0744] Compound IIA-4 of the present invention: 1 H-NMR(CDCl3)δ: 7.87(1H, d), 7.67(2H, m), 7.43(2H, m), 7.26(1H, m), 6.42(1H, d), 3.05(2H, q), 1.39(3H, t).

[0745] Compound IIA-5 of the present invention: 1 H-NMR(CDCl3)δ: 7.81(1H, d), 7.66 - 7.60(2H, m), 7.16 - 7.09(2H, m), 6.41(1H, d), 3.04(2H, q), 1.38(3H, t).

[0746] Compound IIA-6 of the present invention: 1 H-NMR(CDCl3)δ: 7.93(1H, d), 7.82 - 7.71(4H, m), 6.45(1H, d), 3.10(2H, q), 1.41(3H, t).

[0747] Compound IIA-7 of the present invention: 11H-NMR (CDCl3) δ: 7.85 (1H, d), 7.70 (2H, m), 7.29 (2H, m), 6.43 (1H, d), 3.06 (2H, q), 1.39 (3H, t).

[0748] Compound IIA-8 of the present invention: 1 1H-NMR (CDCl3) δ: 7.84 (1H, d), 7.58 - 7.52 (4H, m), 6.42 (1H, d), 3.05 (2H, q), 1.39 (3H, t).

[0749] Compound IIA-9 of the present invention: 1 1H-NMR (CDCl3) δ: 7.84 (1H, d), 7.73 (2H, m), 7.44 (2H, m), 6.42 (1H, d), 3.05 (2H, q), 1.39 (3H, t).

[0750] Compound IIA-10 of the present invention: 1 1H-NMR (CDCl3) δ: 7.85 (1H, d), 7.73 (1H, t), 7.56 - 7.52 (1H, ddd), 7.35 (1H, t), 7.24 - 7.21 (1H, m), 6.42 (1H, d), 3.06 (2H, q), 1.39 (3H, t).

[0751] Compound IIA-11 of the present invention: 1 1H-NMR (CDCl3) δ: 7.86 (1H, d), 7.34 - 7.28 (2H, m), 7.20 (1H, m), 6.81 (1H, m), 6.41 (1H, d), 3.86 (3H, s), 3.05 (2H, q), 1.39 (3H, t).

[0752] Compound IIA-12 of the present invention: 1 1H-NMR (CDCl3) δ: 7.85 (1H, d), 7.61 (1H, m), 7.50 (1H, m), 7.39 - 7.28 (2H, m), 6.42 (1H, d), 3.04 (2H, q), 1.38 (3H, t).

[0753] Compound IIA-13 of the present invention: 1 1H-NMR (CDCl3) δ: 8.03 (1H, d), 7.77 (1H, m), 7.27 (1H, m), 7.07 - 7.01 (2H, m), 6.38 (1H, d), 3.88 (3H, s), 3.03 (2H, q), 1.38 (3H, t).

[0754] Compound IIA-14 of the present invention: 1 H-NMR (CDCl3) δ: 7.86 (1H, d), 7.48 - 7.35 (3H, m), 6.96 (1H, m), 6.42 (1H, d), 3.07 (2H, q), 1.40 (3H, t).

[0755] Compound IIA-15 of the present invention: 1 H-NMR (CDCl3) δ: 7.84 - 7.82 (2H, m), 7.52 - 7.46 (2H, m), 6.42 (1H, d), 3.06 (2H, q), 1.39 (3H, t).

[0756] Compound IIA-16 of the present invention: 1 H-NMR (CDCl3) δ: 8.00 - 7.90 (2H, m), 7.27 - 7.17 (3H, m), 6.42 (1H, d), 3.06 (2H, q), 1.39 (3H, t).

[0757] Compound IIA-17 of the present invention: 1 H-NMR (CDCl3) δ: 7.83 (1H, d), 7.59 (2H, d), 7.23 (1H, t), 6.42 (1H, d), 3.07 (2H, q), 1.40 (3H, t).

[0758] Compound IIA-18 of the present invention: 1 H-NMR (CDCl3) δ: 7.53 (1H, d), 7.35 (2H, m), 7.28 (2H, m), 6.39 (1H, d), 3.02 (2H, q), 2.60 (2H, q), 1.36 (3H, t), 1.11 (3H, t).

[0759] Compound IIA-19 of the present invention: 1 H-NMR (CDCl3) δ: 7.94 (1H, d), 7.91 - 7.91 (1H, m), 7.65 - 7.33 (8H, m), 6.45 (1H, d), 3.06 (2H, q), 1.40 (3H, t).

[0760] Compound IIA-20 of the present invention: 1 H-NMR (CDCl3) δ: 7.40 (1H, d), 7.23 (1H, m), 7.12 (2H, m), 6.43 (1H, d), 3.00 (2H, q), 2.04 (6H, s), 1.34 (3H, t).

[0761] Compound IIA-21 of the present invention: 11H-NMR (CDCl3) δ: 7.84 (1H, d), 7.56 (1H, m), 7.40 (1H, m), 7.38 (1H, m), 7.42 (1H, d), 3.07 (2H, q), 1.40 (3H, t).

[0762] Compound IIA-22 of the present invention: 1 1H-NMR (CDCl3) δ: 7.84 (1H, d), 7.58 (1H, m), 7.54 (1H, m), 7.33 (1H, m), 7.42 (1H, d), 3.07 (2H, q), 1.40 (3H, t).

[0763] Compound IIA-23 of the present invention: 1 1H-NMR (CDCl3) δ: 7.92 (1H, t), 7.77 (1H, t), 7.05 - 6.99 (2H, m), 6.41 (1H, d), 3.04 (2H, q), 2.38 (3H, s), 1.38 (3H, t).

[0764] Compound IIA-24 of the present invention: 1 1H-NMR (CDCl3) δ: 7.86 (1H, d), 7.76 (1H, m), 7.48 (1H, m), 7.23 (1H, m), 7.42 (1H, d), 3.07 (2H, q), 1.40 (3H, t).

[0765] Compound IIA-25 of the present invention: 1 1H-NMR (CDCl3) δ: 7.96 - 7.88 (2H, m), 7.26 - 7.21 (2H, m), 6.42 (1H, d), 3.06 (2H, q), 1.39 (3H, t).

[0766] Compound IIA-26 of the present invention: 1 1H-NMR (CDCl3) δ: 7.84 (1H, d), 7.58 (2H, d), 7.28 (2H, d), 6.41 (1H, d), 3.04 (2H, m), 2.99 - 2.89 (1H, m), 1.38 (3H, t), 1.27 (6H, d).

[0767] Compound IIA-27 of the present invention: 1 1H-NMR (CDCl3) δ: 7.85 (1H, d), 7.56 (2H, d), 7.18 (2H, d), 6.41 (1H, d), 3.04 (2H, q), 2.51 (2H, s), 1.38 (3H, t), 1.34 (9H, s).

[0768] Compound IIA-29 of the present invention: 1 H-NMR (CDCl3) δ: 7.80 (1H, d), 7.31 (1H, d), 7.08 (1H, dd), 6.89 (1H, d), 6.42 (1H, d), 3.95 (3H, s), 3.91 (3H, s), 3.02 (2H, q), 1.38 (3H, t).

[0769] Compound IIA-30 of the present invention: 1 H-NMR (CDCl3) δ: 7.76 (1H, d), 7.45 (1H, m), 7.40 (1H, m), 6.84 (1H, d), 6.39 (1H, d), 3.85 (3H, s), 3.01 (2H, q), 2.26 (3H, s), 1.37 (3H, t).

[0770] [Table 5]

[0771] [Table IIA1-2]

[0772]

[0773] Compound IIA-31 of the present invention: 1 H-NMR (CDCl3) δ: 7.82 (1H, d), 7.39 (1H, m), 7.32 (1H, m), 7.21 (1H, m), 6.40 (1H, d), 3.05 (2H, q), 2.29 (3H, d), 1.39 (3H, t).

[0774] Compound IIA-32 of the present invention: 1 H-NMR (CDCl3) δ: 7.77 (1H, d), 7.47 (1H, m), 7.35 (1H, m), 7.00 (1H, m), 6.38 (1H, d), 3.92 (3H, s), 3.03 (2H, q), 1.38 (3H, t).

[0775] Compound IIA-33 of the present invention: 1 H-NMR (CDCl3) δ: 8.07 (1H, d), 7.76 (1H, m), 7.70 (1H, m), 7.63 (1H, m), 7.06 (1H, d), 3.37 (2H, q), 1.41 (3H, t).

[0776] Compound IIA-34 of the present invention: 1 H-NMR (CDCl3) δ: 7.78 (1H, d), 7.34 (2H, m), 6.42 (1H, d), 3.07 (2H, q), 1.40 (3H, t).

[0777] Compound IIA-35 of the present invention: 1 H-NMR(CDCl3)δ: 7.81(1H, d), 7.35(2H, m), 6.41(1H, d), 3.08(2H, q), 1.40(3H, t).

[0778] Compound IIA-36 of the present invention: 1 H-NMR(CDCl3)δ: 7.80(1H, d), 7.20(2H, m), 6.40(1H, d), 3.06(2H, q), 2.19(3H, t), 1.40(3H, t).

[0779] Compound IIA-37 of the present invention: 1 H-NMR(CDCl3)δ: 7.83(1H, d), 7.24(2H, m), 6.96(1H, m), 6.42(1H, d), 3.08(2H, q), 1.40(3H, t).

[0780] Compound IIA-38 of the present invention: 1 H-NMR(CDCl3)δ: 7.86(1H, d), 7.34(2H, m), 6.44(1H, d), 3.11(2H, q), 1.42(3H, t).

[0781] Compound IIA-39 of the present invention: 1 H-NMR(CDCl3)δ: 7.76(1H, d), 7.26(2H, m), 6.40(1H, d), 4.00(3H, m), 3.06(2H, q), 1.39(3H, t).

[0782] Compound IIA-40 of the present invention: 1 H-NMR(CDCl3)δ: 7.83(1H, d), 7.60(2H, m), 7.39(2H, m), 6.40(1H, d), 3.01(2H, t), 1.75(2H, m), 1.04(3H, t).

[0783] Compound IIA-41 of the present invention: 1 H-NMR(CDCl3)δ: 7.82(1H, d), 7.54(2H, m), 7.23(2H, m), 6.39(1H, d), 3.00(2H, t), 2.37(3H, s), 1.79 - 1.70(2H, m), 1.04(3H, t).

[0784] Compound IIA-42 of the present invention: 11H-NMR (CDCl3) δ: 7.83 (1H, d), 7.58 (2H, m), 7.44 (2H, m), 6.39 (1H, d), 3.00 (2H, dd), 1.75 (2H, m), 1.34 (9H, s), 1.04 (3H, t).

[0785] Compound IIA-43 of the present invention: 1 1H-NMR (CDCl3) δ: 7.81 (1H, d), 7.39 (1H, dd), 7.31 (1H, dd), 7.24 - 7.19 (1H, m), 6.39 (1H, d), 3.01 (2H, t), 2.29 (3H, s), 1.80 - 1.71 (2H, m), 1.04 (3H, t).

[0786] Compound IIA-44 of the present invention: 1 1H-NMR (CDCl3) δ: 7.83 (1H, d), 7.55 (1H, m), 7.47 - 7.36 (2H, m), 6.41 (1H, d), 3.03 (2H, dd), 1.76 (2H, m), 1.05 (3H, t).

[0787] Compound IIA-45 of the present invention: 1 1H-NMR (CDCl3) δ: 7.90 (1H, d), 7.65 (1H, m), 7.60 (1H, m), 7.50 (1H, m), 6.43 (1H, d), 3.07 (2H, dd), 1.78 (2H, m), 1.06 (3H, t).

[0788] Compound IIA-46 of the present invention: 1 1H-NMR (CDCl3) δ: 7.79 (1H, d), 7.19 (2H, m), 6.39 (1H, d), 3.03 (2H, t), 2.19 (3H, s), 1.76 (2H, m), 1.05 (3H, t).

[0789] Compound IIA-47 of the present invention: 1 1H-NMR (CDCl3) δ: 7.81 (1H, d), 7.34 (2H, m), 6.41 (1H, d), 3.05 (2H, t), 1.77 (2H, m), 1.05 (3H, t).

[0790] Compound IIA-48 of the present invention: 1 1H-NMR (CDCl3) δ: 7.85 (1H, d), 7.34 (2H, m), 6.44 (1H, d), 3.08 (2H, t), 1.78 (2H, m), 1.06 (3H, t).

[0791] Compound IIA-49 of the present invention: 1 H-NMR(CDCl3)δ: 7.93(1H, d), 7.79(2H, d), 7.69(2H, d), 6.44(1H, d), 3.05(2H, t), 1.77(2H, m), 1.05(3H, t).

[0792] Compound IIA-50 of the present invention: 1 H-NMR(CDCl3)δ: 7.85(1H, d), 7.63(2H, m), 7.40(2H, m), 6.46(1H, d), 3.52(1H, m), 1.37(6H, d).

[0793] Compound IIA-51 of the present invention: 1 H-NMR(CDCl3)δ: 7.83(1H, d), 7.61(2H, m), 7.40(2H, m), 6.41(1H, d), 3.04(2H, t), 1.71(2H, m), 1.48(2H, m), 0.94(3H, t).

[0794] Compound IIA-52 of the present invention: 1 H-NMR(CDCl3)δ: 7.83(1H, d), 7.61(2H, m), 7.40(2H, m), 6.39(1H, d), 2.95(2H, d), 1.97(1H, m), 1.05(6H, d).

[0795] Compound IIA-53 of the present invention: 1 H-NMR(CDCl3)δ: 7.83(1H, d), 7.61(2H, m), 7.40(2H, m), 6.41(1H, d), 3.03(2H, t), 1.73(2H, m), 1.47 - 1.30(4H, m), 0.90(3H, t).

[0796] Compound IIA-54 of the present invention: 1 H-NMR(CDCl3)δ: 7.84(1H, d), 7.61(2H, m), 7.40(2H, m), 6.40(1H, d), 3.05(2H, m), 1.75(1H, m), 1.61(2H, m), 0.93(6H, d).

[0797] Compound IIA-55 of the present invention: 1H-NMR(CDCl3) δ: 7.84 (1H, d), 7.63 (2H, m), 7.41 (2H, m), 6.45 (1H, d), 3.26 (1H, m), 2.69 (2H, m), 1.79 (2H, m), 1.61 - 1.24 (6H, m).

[0798] Compound IIA-56 of the present invention: 1 H-NMR(CDCl3) δ: 7.83 (1H, d), 7.61 (2H, m), 7.40 (2H, m), 6.43 (1H, d), 5.98 (1H, m), 5.20 (1H, m), 5.10 (1H, m), 3.67 (2H, m).

[0799] Compound IIA-57 of the present invention: 1 H-NMR(CDCl3) δ: 8.44 (1H, m), 8.00 (1H, d), 7.69 (2H, m), 7.50 (1H, m), 7.44 (2H, m), 7.12 (1H, d), 7.03 (1H, m), 6.72 (1H, d).

[0800] Compound IIA-58 of the present invention: 1 H-NMR(CDCl3) δ: 8.39 (2H, m), 8.02 (1H, d), 7.69 (2H, m), 7.46 (2H, m), 7.10 (2H, m), 6.68 (1H, d).

[0801] Compound IIA-59 of the present invention: 1 H-NMR(DMSO-D6) δ: 8.52 (1H, d), 7.49 - 7.32 (8H, m), 6.96 - 6.92 (1H, m), 6.55 (1H, d), 5.18 (2H, s), 3.00 (2H, t), 1.71 - 1.62 (2H, m), 0.98 (3H, t).

[0802] Compound IIA-149 of the present invention: 1 H-NMR(CDCl3) δ: 8.32 (2H, m), 7.97 (1H, d), 7.83 (2H, m), 6.46 (1H, d), 3.08 (2H, t), 1.79 (2H, m), 1.07 (3H, t).

[0803] Compound IIA-150 of the present invention: 11H-NMR (CDCl3) δ: 8.51 (1H, m), 8.10 (1H, m), 8.05 (1H, m), 7.97 (1H, d), 7.62 (1H, t), 6.46 (1H, d), 3.07 (2H, t), 1.78 (2H, m), 1.07 (3H, t).

[0804] Compound IIA-151 of the present invention: 1 1H-NMR (CDCl3) δ: 7.76 (1H, d), 7.56 (2H, m), 7.41 (2H, m), 2.97 (2H, t), 1.72 (2H, m), 1.04 (3H, t).

[0805] [Table 6]

[0806] [Table IA1]

[0807] This compound Z <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 5 > <![CDATA[R 6 > <![CDATA[R 7 > IA-1 Me H H Cl H H H H IA-2 Ph H H Cl H H H H IA-3 Ph H F Cl H H H H IA-4 Ph H H OMe H H H H IA-5 4-(OMe)-Ph H H Cl H H H H IA-6 4-Cl-Ph H H Cl H H H H IA-7 2-(OMe)-Ph H H Cl H H H H IA-8 2-Cl-Ph H H Cl H H H H

[0808] This compound IA-1: 1 1H-NMR (CDCl3) δ: 7.84 (1H, d), 7.61 (2H, m), 7.40 (2H, m), 6.39 (1H, d), 2.59 (3H, s).

[0809] This compound IA-2: 1 1H-NMR (CDCl3) δ: 7.88 (1H, d), 7.65 (2H, m), 7.44 - 7.39 (4H, m), 7.31 - 7.20 (3H, m), 6.45 (1H, d).

[0810] This compound IA-3: 1 1H-NMR (CDCl3) δ: 7.88 (1H, d), 7.58 (1H, m), 7.49 - 7.40 (4H, m), 7.33 - 7.23 (3H, m), 6.43 (1H, d).

[0811] This compound IA-4: 1 1H-NMR (CDCl3) δ: 7.84 (1H, d), 7.61 (2H, m), 7.38 (2H, m), 7.27 (2H, m), 7.19 (1H, m), 6.97 (2H, m), 6.46 (1H, d), 3.85 (3H, s).

[0812] This compound IA-5: 11H-NMR (CDCl3) δ: 7.81 (1H, d), 7.62 (2H, m), 7.47 (2H, m), 7.40 (2H, m), 6.87 (2H, m), 6.27 (1H, d), 3.81 (3H, s).

[0813] This compound IA-6: 1 1H-NMR (CDCl3) δ: 7.90 (1H, d), 7.64 (2H, m), 7.43 (2H, m), 7.33 (2H, m), 7.26 (2H, m), 6.46 (1H, d).

[0814] This compound IA-7: 1 1H-NMR (CDCl3) δ: 7.90 (1H, d), 7.66 (2H, m), 7.41 (2H, m), 7.26 - 7.14 (2H, m), 6.90 - 6.83 (2H, m), 6.48 (1H, d), 3.90 (3H, s).

[0815] This compound IA-8: 1 1H-NMR (CDCl3) δ: 7.97 (1H, d), 7.67 (2H, m), 7.43 (2H, m), 7.37 (1H, m), 7.14 - 7.07 (3H, m), 6.58 (1H, d).

[0816] Production Example 2

[0817] A mixture of 1.0 g of intermediate MA3-1, 1.0 g of sodium ethanethiolate, and 10 mL of DMF was stirred at 120 °C for 5 hours. An aqueous sodium bicarbonate solution was added to the resulting mixture, and extraction was performed with ethyl acetate. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain 1.3 g of a crude product of the compound IIA-60 of the present invention represented by the following formula.

[0818] [Chemical formula 47]

[0819]

[0820] The compound IIA-60 of the present invention: 1 1H-NMR (CDCl3) δ: 7.84 (1H, d), 7.61 (2H, m), 7.40 (2H, m), 6.42 (1H, d), 3.05 (2H, q), 1.39 (3H, t).

[0821] Production Example 3

[0822] To a mixture of 0.27 g of Compound IIA-37 of the present invention and 10 mL of THF, 0.58 mL of butyllithium (2.6 M, hexane solution) was added dropwise at -78 °C, and the mixture was stirred at -78 °C for 30 minutes. To the resulting mixture, 0.65 g of 1,2-dibromo-1,1,2,2-tetrachloroethane was added, and after stirring for 30 minutes, the mixture was stirred at room temperature for 4 hours. An aqueous ammonium chloride solution was added to the resulting mixture, and extraction was carried out with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 98:2) to obtain 0.16 g of Compound IIA-61 of the present invention represented by the following formula.

[0823] [Chemical formula 48]

[0824]

[0825] Compound IIA-61 of the present invention: 1 H-NMR (CDCl3) δ: 7.83 (1H, d), 7.33 (2H, m), 6.42 (1H, d), 3.08 (2H, q), 1.41 (3H, t).

[0826] Production Example 4

[0827] To a mixture of 0.22 g of Compound IIA-1 of the present invention and 5 mL of chloroform, 0.25 g of mCPBA (purity 75%, 25% water-containing) was added at 0 °C, and the mixture was stirred at 0 °C for 2 hours. An aqueous sodium sulfite solution was added to the resulting mixture, and extraction was carried out with chloroform. The obtained organic layer was washed with an aqueous sodium bicarbonate solution, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 50:50) to obtain 0.21 g of Compound IIA-62 of the present invention represented by the following formula.

[0828] [Chemical formula 49]

[0829]

[0830] Compound IIA-62 of the present invention: 1 H-NMR (CDCl3) δ: 7.97 (1H, d), 7.56 (2H, m), 7.27 (2H, m), 6.93 (1H, d), 3.21 - 3.06 (2H, m), 2.40 (3H, s), 1.33 (3H, t).

[0831] Production Example 4-1

[0832] The compounds produced according to Production Example 4 and their physical property values are shown below.

[0833] In the compound represented by formula (A2), Z, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are combined as any one of the combinations described in [Table IIA2] and [Table IA2].

[0834] [Chemical formula 50]

[0835]

[0836] [Table 7]

[0837] [Table IIA2]

[0838] The compound of the present invention Z <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 5 > <![CDATA[R 6 > <![CDATA[R 7 > IIA-63 Et H H <![CDATA[CF3]]> H H H H IIA-64 Et F H H H H H H

[0839] Compound IIA-63 of the present invention: 1 H-NMR(CDCl3)δ: 8.10(1H, d), 7.84(2H, m), 7.75(2H, m), 7.01(1H, d), 3.15(2H, m), 1.35(3H, t).

[0840] Compound IIA-64 of the present invention: 1 H-NMR(CDCl3)δ: 8.02(1H, d), 7.51 - 7.40(3H, m), 7.10 - 7.02(1H, m), 6.98(1H, d), 3.14(2H, m), 1.34(3H, t).

[0841] [Table 8]

[0842] [Table IA2]

[0843] This compound Z <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 5 > <![CDATA[R 6 > <![CDATA[R 7 > IA-9 2-(OMe)-Ph H H Cl H H H H IA-10 2-Cl-Ph H H Cl H H H H

[0844] This compound IA-9: 1 H-NMR(CDCl3)δ: 8.20(1H, m), 7.92(1H, d), 7.64 - 7.55(3H, m), 7.41(2H, m), 7.15 - 7.90(2H, m), 6.96(1H, d), 3.85(3H, s).

[0845] This compound IA-10: 1 H-NMR(CDCl3)δ: 8.18(1H, m), 7.87(1H, d), 7.65 - 7.56(3H, m), 7.50 - 7.38(4H, m), 6.47(1H, d).

[0846] Production Example 5

[0847] To a mixture of 0.22 g of Compound IIA-1 of the present invention and 5 mL of chloroform, 0.54 g of mCPBA (purity 75%, containing 25% water) was added at 0 °C, and the mixture was stirred at room temperature for 4 hours. An aqueous sodium sulfite solution was added to the resulting mixture, and extraction was carried out with chloroform. The obtained organic layer was washed with an aqueous sodium bicarbonate solution, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 80:20) to obtain 0.25 g of Compound IIA-65 of the present invention represented by the following formula.

[0848] [Chemical Formula 51]

[0849]

[0850] Compound IIA-65 of the present invention: 1 H-NMR(CDCl3)δ:7.95(1H,d),7.60(2H,m),7.29(2H,m),6.98(1H,d),3.35(2H,q),2.41(3H,s),1.39(3H,t).

[0851] Production Example 5-1

[0852] The compounds produced according to Production Example 5 and their physical property values are shown below.

[0853] In the compound represented by formula (A3), the combinations of Z, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are any of the combinations described in [Table IIA3-1], [Table IIA3-2], [Table IIA3-3], [Table IIA3-4], [Table IIA3-5] and [Table IA3].

[0854] [Chemical Formula 52]

[0855]

[0856] [Table 9]

[0857] [Table IIA3-1]

[0858]

[0859] Compound IIA-66 of the present invention: 11H-NMR (CDCl3) δ: 8.10 (1H, d), 7.89 (2H, m), 7.72 (2H, m), 7.04 (1H, d), 3.37 (2H, q), 1.41 (3H, t).

[0860] Compound IIA-67 of the present invention: 1 1H-NMR (CDCl3) δ: 7.90 (1H, d), 7.62 (2H, m), 7.01 - 6.95 (3H, m), 3.86 (3H, s), 3.34 (2H, q), 1.39 (3H, t).

[0861] Compound IIA-68 of the present invention: 1 1H-NMR (CDCl3) δ: 8.01 (1H, d), 7.73 (2H, m), 7.51 (2H, m), 7.41 (1H, m), 7.00 (1H, d), 3.36 (2H, q), 1.40 (3H, t).

[0862] Compound IIA-69 of the present invention: 1 1H-NMR (CDCl3) δ: 7.96 (1H, d), 7.71 (2H, m), 7.20 (2H, m), 6.99 (1H, d), 3.35 (2H, q), 1.40 (3H, t).

[0863] Compound IIA-70 of the present invention: 1 1H-NMR (CDCl3) δ: 8.09 (1H, d), 7.90 (2H, m), 7.82 (2H, m), 7.06 (1H, d), 3.37 (2H, q), 1.41 (3H, t).

[0864] Compound IIA-71 of the present invention: 1 1H-NMR (CDCl3) δ: 8.00 (1H, d), 7.78 (2H, m), 7.36 (2H, m), 7.02 (1H, d), 3.36 (2H, q), 1.40 (3H, t).

[0865] Compound IIA-72 of the present invention: 1 1H-NMR (CDCl3) δ: 7.98 (1H, d), 7.63 (4H, s), 7.01 (1H, d), 3.35 (2H, q), 1.40 (3H, t).

[0866] Compound IIA-73 of the present invention: 11H-NMR (CDCl3) δ: 7.99 (1H, d), 7.82 (2H, m), 7.49 (2H, m), 7.00 (1H, d), 3.35 (2H, q), 1.40 (3H, t).

[0867] Compound IIA-74 of the present invention: 1 1H-NMR (CDCl3) δ: δ: 8.01 (1H, d), 7.81 (1H, m), 7.62 (1H, m), 7.44 (1H, m), 7.38 (1H, m), 7.01 (1H, d), 3.36 (2H, q), 1.40 (3H, t).

[0868] Compound IIA-75 of the present invention: 1 1H-NMR (CDCl3) δ: 7.99 (1H, d), 7.39 (1H, t), 7.31 (1H, m), 7.26 (1H, m), 6.99 (1H, d), 6.94 (1H, m), 3.89 (3H, s), 3.36 (2H, q), 1.40 (3H, t).

[0869] Compound IIA-76 of the present invention: 1 1H-NMR (CDCl3) δ: 7.92 (1H, d), 7.63 - 7.54 (2H, m), 7.47 - 7.41 (2H, m), 6.99 (1H, d), 3.36 (2H, q), 1.40 (3H, t).

[0870] Compound IIA-77 of the present invention: 1 1H-NMR (CDCl3) δ: 8.11 (1H, d), 7.75 (1H, m), 7.39 (1H, m), 7.09 (2H, m), 6.94 (1H, d), 3.91 (3H, s), 3.35 (2H, q), 1.39 (3H, t).

[0871] Compound IIA-78 of the present invention: 1 1H-NMR (CDCl3) δ: 8.00 (1H, d), 7.51 (3H, m), 7.11 (1H, m), 7.01 (1H, d), 3.36 (2H, q), 1.41 (3H, t).

[0872] Compound IIA-79 of the present invention: 1 1H-NMR (CDCl3) δ: 7.99 (1H, d), 7.91 (1H, m), 7.59 (2H, m), 7.02 (1H, d), 3.36 (2H, q), 1.40 (3H, t).

[0873] Compound IIA-80 of the present invention:1 H-NMR (CDCl3) δ: 8.08 (1H, t), 7.91 (1H, m), 7.40 (1H, m), 7.33 - 7.25 (2H, m), 7.00 (1H, d), 3.36 (2H, q), 1.40 (3H, t).

[0874] Compound IIA-81 of the present invention: 1 H-NMR (CDCl3) δ: 8.00 (1H, d), 7.68 (2H, d), 7.39 (1H, t), 7.02 (1H, d), 3.36 (2H, q), 1.40 (3H, t).

[0875] Compound IIA-82 of the present invention: 1 H-NMR (CDCl3) δ: 1 H-NMR (CDCl3) δ: 7.68 (1H, d), 7.46 - 7.38 (2H, m), 7.32 - 7.31 (2H, m), 6.98 (1H, d), 3.35 (2H, q), 2.53 (2H, q), 1.39 (3H, t), 1.11 (3H, t).

[0876] Compound IIA-83 of the present invention: 1 H-NMR (CDCl3) δ: 8.06 (1H, d), 7.95 (1H, m), 7.70 - 7.39 (8H, m), 7.02 (1H, d), 3.38 (2H, q), 1.41 (3H, t).

[0877] Compound IIA-84 of the present invention: 1 H-NMR (CDCl3) δ: 1 H-NMR (CDCl3) δ: 7.58 (1H, d), 7.30 (1H, t), 7.16 (2H, d), 7.01 (1H, d), 3.34 (2H, q), 2.02 (6H, s), 1.37 (3H, t).

[0878] Compound IIA-85 of the present invention: 1 H-NMR (CDCl3) δ: 7.99 (1H, d), 7.63 (1H, m), 7.54 (1H, m), 7.48 (1H, m), 7.02 (1H, d), 3.36 (2H, q), 1.40 (3H, t).

[0879] Compound IIA-86 of the present invention: 11H-NMR (CDCl3) δ: 8.00 (1H, d), 7.69 (1H, dd), 7.61 (1H, dd), 7.43 (1H, m), 7.02 (1H, m), 3.60 (2H, q), 1.41 (3H, t).

[0880] Compound IIA-87 of the present invention: 1 1H-NMR (CDCl3) δ: 8.02 (1H, t), 7.76 (1H, m), 7.11 - 7.06 (2H, m), 6.98 (1H, d), 3.35 (2H, q), 2.42 (3H, s), 1.40 (3H, t).

[0881] Compound IIA-88 of the present invention: 1 1H-NMR (CDCl3) δ: 8.00 (1H, d), 7.87 (1H, dd), 7.54 (1H, dd), 7.32 (1H, dd), 7.02 (1H, d), 3.36 (2H, q), 1.40 (3H, t).

[0882] Compound IIA-89 of the present invention: 1 1H-NMR (CDCl3) δ: 8.06 (1H, t), 7.89 (1H, m), 7.35 - 7.28 (2H, m), 7.01 (1H, d), 3.35 (2H, q), 1.40 (3H, t).

[0883] Compound IIA-90 of the present invention: 1 1H-NMR (CDCl3) δ: 7.96 (1H, d), 7.63 (2H, m), 7.35 (2H, m), 6.98 (1H, d), 3.35 (2H, q), 3.01 - 2.94 (1H, m), 1.39 (3H, t), 1.28 (6H, d).

[0884] Compound IIA-91 of the present invention: 1 1H-NMR (CDCl3) δ: 7.97 (1H, d), 7.61 (2H, m), 7.24 (2H, m), 6.98 (1H, d), 3.36 (2H, q), 2.55 (2H, s), 1.40 (3H, t), 0.92 (9H, s).

[0885] Compound IIA-92 of the present invention: 11H-NMR (CDCl3) δ: 7.93 (1H, d), 7.59 (2H, m), 7.17 (2H, m), 6.96 (1H, d), 3.30 (2H, m), 1.99 - 1.83 (3H, m), 1.09 - 1.01 (5H, m), 0.75 - 0.71 (2H, m).

[0886] Compound IIA-93 of the present invention: 1 1H-NMR (CDCl3) δ: 7.93 (1H, d), 7.31 (1H, d), 7.16 (1H, m), 6.97 (1H, d), 6.93 (1H, d), 3.97 (3H, s), 3.94 (3H, s), 3.35 (2H, q), 1.40 (3H, t).

[0887] Compound IIA-94 of the present invention: 1 1H-NMR (CDCl3) δ: 7.89 (1H, d), 7.50 (1H, m), 7.46 (1H, m), 6.95 (1H, d), 6.88 (1H, d), 3.88 (3H, s), 3.34 (2H, q), 2.28 (3H, s), 1.39 (3H, t).

[0888] [Table 10]

[0889] [Table IIA3-2]

[0890]

[0891] Compound IIA-95 of the present invention: 1 1H-NMR (CDCl3) δ: 8.01 (1H, d), 7.45 (1H, m), 7.39 (1H, m), 7.29 (1H, m), 6.97 (1H, m), 3.35 (2H, q), 2.31 (3H, s), 1.40 (3H, t).

[0892] Compound IIA-96 of the present invention: 1 1H-NMR (CDCl3) δ: 7.92 (1H, d), 7.52 (1H, m), 7.43 (1H, m), 7.05 (1H, t), 6.98 (1H, d), 2.95 (3H, s), 3.35 (2H, q), 1.40 (3H, t).

[0893] Compound IIA-97 of the present invention: 11H-NMR (CDCl3) δ: 8.07 (1H, d), 7.76 (1H, m), 7.70 (1H, m), 7.63 (1H, m), 7.06 (1H, d), 3.37 (2H, q), 1.41 (3H, t).

[0894] Compound IIA-98 of the present invention: 1 1H-NMR (CDCl3) δ: 7.95 (1H, d), 7.44 (2H, m), 7.02 (1H, d), 3.35 (2H, q), 1.40 (3H, t).

[0895] Compound IIA-99 of the present invention: 1 1H-NMR (CDCl3) δ: 7.99 (1H, d), 7.46 (2H, m), 7.03 (1H, d), 3.36 (2H, q), 1.41 (3H, t).

[0896] Compound IIA-100 of the present invention: 1 1H-NMR (CDCl3) δ: 7.95 (1H, d), 7.29 (2H, m), 7.00 (1H, d), 3.51 (2H, q), 2.24 (3H, t), 1.40 (3H, t).

[0897] Compound IIA-101 of the present invention: 1 1H-NMR (CDCl3) δ: 8.00 (1H, d), 7.33 (2H, m), 7.02 (1H, d), 6.86 (1H, m), 3.36 (2H, q), 1.41 (3H, t).

[0898] Compound IIA-102 of the present invention: 1 1H-NMR (CDCl3) δ: 8.05 (1H, d), 7.48 (2H, m), 7.07 (1H, d), 3.37 (2H, q), 1.41 (3H, t).

[0899] Compound IIA-103 of the present invention: 1 1H-NMR (CDCl3) δ: 7.92 (1H, d), 7.34 (2H, m), 7.00 (1H, d), 4.05 (3H, t), 3.35 (2H, q), 1.40 (3H, t).

[0900] Compound IIA-104 of the present invention: 1 1H-NMR (CDCl3) δ: 7.97 (1H, d), 7.68 (2H, m), 7.48 (2H, m), 7.00 (1H, d), 3.30 (2H, m), 1.89 (2H, m), 1.06 (3H, t).

[0901] Compound IIA-105 of the present invention: 1 H-NMR(CDCl3)δ: 7.94(1H,d), 7.60(2H,m), 7.30 - 7.28(2H,m), 6.97(1H,d), 3.31(2H,m), 2.41(3H,s), 1.89(2H,m), 1.04(3H,t).

[0902] Compound IIA-106 of the present invention: 1 H-NMR(CDCl3)δ: 7.95(1H,d), 7.64(2H,m), 7.50(2H,m), 6.97(1H,d), 3.31(2H,m), 1.88(2H,m), 1.36(9H,s), 1.05(3H,t).

[0903] Compound IIA-107 of the present invention: 1 H-NMR(CDCl3)δ: 7.95(1H,d), 7.45(1H,m), 7.39(1H,m), 7.30(1H,m), 6.98(1H,d), 3.31(2H,m), 2.33(3H,s), 1.89(2H,m), 1.06(3H,t).

[0904] Compound IIA-108 of the present invention: 1 H-NMR(CDCl3)δ: 7.98(1H,d), 7.63(1H,m), 7.56 - 7.46(2H,m), 7.01(1H,d), 3.31(2H,m), 1.89(2H,m), 1.07(3H,t).

[0905] Compound IIA-109 of the present invention: 1 H-NMR(CDCl3)δ: 8.07(1H,d), 7.76(1H,m), 7.70(1H,m), 7.63(1H,m), 7.04(1H,d), 3.32(2H,m), 1.90(2H,m), 1.07(3H,t).

[0906] Compound IIA-110 of the present invention: 1 H-NMR(CDCl3)δ: 7.94(1H,d), 7.29(2H,m), 6.99(1H,d), 3.31(2H,m), 2.24(3H,t), 1.89(2H,m), 1.06(3H,t).

[0907] Compound IIA-111 of the present invention: 11H-NMR (CDCl3) δ: 7.99 (1H, d), 7.46 (2H, m), 7.02 (1H, d), 3.31 (2H, m), 1.89 (2H, m), 1.07 (3H, t).

[0908] Compound IIA-112 of the present invention: 1 1H-NMR (CDCl3) δ: 8.04 (1H, d), 7.48 (2H, m), 7.06 (1H, d), 3.32 (2H, m), 1.89 (2H, m), 1.08 (3H, t).

[0909] Compound IIA-113 of the present invention: 1 1H-NMR (CDCl3) δ: 8.07 (1H, d), 7.89 (2H, m), 7.78 (2H, m), 7.40 (1H, d), 3.32 (2H, m), 8.90 (2H, m), 1.07 (3H, t).

[0910] Compound IIA-114 of the present invention: 1 1H-NMR (CDCl3) δ: 7.99 (1H, d), 7.69 (2H, m), 7.47 (2H, m), 7.00 (1H, d), 3.45 (1H, m), 1.41 (6H, d).

[0911] Compound IIA-115 of the present invention: 1 1H-NMR (CDCl3) δ: 7.97 (1H, d), 7.68 (2H, m), 7.48 (2H, m), 7.00 (1H, d), 3.33 (2H, m), 1.83 (2H, m), 1.46 (2H, m), 0.93 (3H, t).

[0912] Compound IIA-116 of the present invention: 1 1H-NMR (CDCl3) δ: 7.96 (1H, d), 7.68 (2H, m), 7.48 (2H, m), 7.00 (1H, d), 3.25 (2H, d), 2.39 (1H, m), 1.11 (6H, d).

[0913] Compound IIA-117 of the present invention: 1 1H-NMR (CDCl3) δ: 7.97 (1H, d), 7.68 (2H, m), 7.48 (2H, m), 7.00 (1H, d), 3.32 (2H, m), 1.85 (2H, m), 1.44 - 1.28 (4H, m), 0.89 (3H, t).

[0914] Compound IIA-118 of the present invention: 11H-NMR (CDCl3) δ: 7.97 (1H, d), 7.68 (2H, m), 7.48 (2H, m), 7.00 (1H, d), 3.33 (2H, m), 1.77 - 1.66 (3H, m), 0.92 (6H, d).

[0915] Compound IIA-119 of the present invention: 1 1H-NMR (CDCl3) δ: 7.97 (1H, d), 7.69 (2H, m), 7.48 (2H, m), 6.98 (1H, d), 3.17 (1H, m), 2.18 (2H, m), 1.90 (2H, m), 1.73 - 1.13 (6H, m).

[0916] Compound IIA-120 of the present invention: 1 1H-NMR (CDCl3) δ: 7.96 (1H, d), 7.68 (2H, m), 7.48 (2H, m), 6.97 (1H, d), 5.90 (1H, m), 5.41 (1H, dd), 5.32 (1H, d), 4.05 (2H, d).

[0917] Compound IIA-121 of the present invention: 1 1H-NMR (CDCl3) δ: 8.88 (2H, m), 7.95 - 7.91 (3H, m), 7.62 (2H, m), 7.45 (2H, m), 7.05 (1H, d).

[0918] Compound IIA-122 of the present invention: 1 1H-NMR (CDCl3) δ: 8.72 (1H, m), 8.31 (1H, d), 8.00 - 7.95 (2H, m), 7.63 (2H, m), 7.51 (1H, m), 7.43 (2H, m), 7.19 (1H, d).

[0919] Compound IIA-123 of the present invention: 1 1H-NMR (CDCl3) δ: 7.98 (1H, d), 7.68 (2H, m), 7.48 (2H, m), 7.01 (1H, d), 3.35 (2H, q), 1.40 (3H, t).

[0920] Compound IIA-124 of the present invention: 1 1H-NMR (CDCl3) δ: 8.01 (1H, d), 7.43 (2H, m), 7.03 (1H, d), 3.36 (2H, q), 1.41 (3H, t).

[0921] [Table 11]

[0922] [Table IIA3-3]

[0923]

[0924] Compound IIA-125 of the present invention: 1 H-NMR(DMSO-D6)δ: 8.78(1H, d), 7.56 - 7.33(8H, m), 7.12 - 7.07(2H, m), 5.21(2H, s), 3.41 - 3.37(2H, m), 1.73 - 1.64(2H, m), 0.96(3H, t).

[0925] Compound IIA-126 of the present invention: 1 H-NMR(DMSO-D6)δ: 8.77(1H, d), 7.54 - 7.53(1H, m), 7.48 - 7.47(2H, m), 7.37(2H, d), 7.21(2H, d), 7.09 - 7.06(2H, m), 5.16(2H, s), 3.40 - 3.37(2H, m), 2.31(3H, s), 1.73 - 1.64(2H, m), 0.96(3H, t).

[0926] Compound IIA-127 of the present invention: 1 H-NMR(DMSO-D6)δ: 8.77(1H, d), 7.55 - 7.55(1H, m), 7.49 - 7.47(2H, m), 7.30 - 7.26(3H, m), 7.16(1H, d), 7.10 - 7.07(2H, m), 5.16(2H, s), 3.40 - 3.35(2H, m), 2.33(3H, s), 1.73 - 1.64(2H, m), 0.96(3H, t).

[0927] Compound IIA-128 of the present invention: 1 H-NMR(DMSO-D6)δ: 8.78(1H, d), 7.58 - 7.57(1H, m), 7.50 - 7.49(2H, m), 7.45(1H, d), 7.29 - 7.20(3H, m), 7.14 - 7.11(1H, m), 7.08(1H, d), 5.19(2H, s), 3.41 - 3.35(2H, m), 2.36(3H, s), 1.73 - 1.64(2H, m), 0.96(3H, t).

[0928] Compound IIA-129 of the present invention: 11H-NMR (DMSO-D6) δ: 8.79 (1H, d), 8.17 (1H, t), 7.85 - 7.82 (2H, m), 7.70 - 7.63 (2H, m), 7.43 (1H, d), 7.31 - 7.28 (1H, m), 7.09 (1H, d), 3.39 - 3.33 (2H, m), 1.72 - 1.63 (2H, m), 0.95 (3H, t).

[0929] Compound IIA-130 of the present invention: 1 1H-NMR (DMSO-D6) δ: 8.79 (1H, d), 8.60 - 8.59 (1H, m), 8.29 (1H, dd), 7.85 - 7.81 (2H, m), 7.66 (1H, t), 7.35 (1H, d), 7.32 - 7.29 (1H, m), 7.09 (1H, d), 3.40 - 3.32 (2H, m), 1.72 - 1.63 (2H, m), 0.95 (3H, t).

[0930] Compound IIA-132 of the present invention: 1 1H-NMR (CDCl3) δ: 7.98 (1H, d), 7.74 (1H, s), 7.63 (2H, t), 7.54 (1H, t), 7.44 - 7.40 (2H, m), 7.31 - 7.29 (1H, m), 7.02 - 6.98 (2H, m), 5.19 (2H, s), 3.33 - 3.29 (2H, m), 1.94 - 1.84 (2H, m), 1.06 (3H, t).

[0931] Compound IIA-133 of the present invention: 1 1H-NMR (CDCl3) δ: 7.99 (1H, d), 7.78 (1H, br s), 7.70 - 7.64 (2H, m), 7.53 (1H, t), 7.44 - 7.40 (2H, m), 7.32 - 7.29 (1H, m), 7.00 - 6.97 (2H, m), 5.17 (2H, s), 3.33 - 3.29 (2H, m), 1.94 - 1.84 (2H, m), 1.06 (3H, t).

[0932] Compound IIA-134 of the present invention: 11H-NMR (CDCl3) δ: 7.96 (1H, d), 7.41 - 7.37 (2H, m), 7.32 (1H, t), 7.29 - 7.26 (1H, m), 7.04 - 6.97 (4H, m), 6.89 (1H, dd), 5.12 (2H, s), 3.83 (3H, s), 3.33 - 3.29 (2H, m), 1.93 - 1.84 (2H, m), 1.06 (3H, t).

[0933] Compound IIA-135 of the present invention: 1 1H-NMR (CDCl3) δ: 7.95 (1H, d), 7.45 - 7.36 (5H, m), 7.20 - 7.15 (1H, m), 7.08 - 7.05 (2H, m), 7.01 - 6.99 (1H, m), 6.97 (1H, d), 3.32 - 3.28 (2H, m), 1.92 - 1.83 (2H, m), 1.05 (3H, t).

[0934] Compound IIA-136 of the present invention: 1 1H-NMR (CDCl3) δ: 7.95 (1H, d), 7.36 (1H, t), 7.26 - 7.23 (1H, m), 7.20 (1H, t), 6.97 (1H, d), 6.84 - 6.82 (1H, m), 4.75 - 4.68 (1H, m), 3.33 - 3.29 (2H, m), 2.52 - 2.45 (2H, m), 2.24 - 2.14 (2H, m), 1.94 - 1.84 (3H, m), 1.78 - 1.66 (1H, m), 1.05 (3H, t).

[0935] [Table 12]

[0936] [Table IIA3-4]

[0937]

[0938] Compound IIA-143 of the present invention: 1 1H-NMR (CDCl3) δ: 8.01 (1H, d), 7.92 (1H, br s), 7.43 - 7.35 (3H, m), 6.97 (1H, d), 6.92 (1H, br s), 3.81 (3H, s), 3.31 (2H, m), 1.88 (2H, m), 1.06 (3H, t).

[0939] Compound IIA-144 of the present invention: 11H-NMR (CDCl3) δ: 8.01 (1H, d), 7.94 (1H, br), 7.43 - 7.34 (3H, m), 6.97 (1H, d), 6.86 (1H, br), 4.25 (2H, q), 3.31 (2H, m), 1.88 (2H, m), 1.33 (3H, t), 1.05 (3H, t).

[0940] Compound IIA-145 of the present invention: 1 1H-NMR (CDCl3) δ: 8.01 (1H, d), 7.95 (1H, br s), 7.43 - 7.38 (2H, m), 7.32 (1H, m), 6.97 (1H, d), 6.75 (1H, br s), 5.03 (1H, m), 3.30 (2H, m), 1.88 (2H, m), 1.32 (6H, d), 1.06 (3H, t).

[0941] Compound IIA-146 of the present invention: 1 1H-NMR (CDCl3) δ: 7.93 (1H, d), 7.65 (2H, m), 7.54 (2H, m), 6.97 (1H, d), 6.81 (1H, br s), 3.81 (3H, s), 3.30 (2H, m), 1.89 (2H, m), 1.05 (3H, t).

[0942] Compound IIA-147 of the present invention: 1 1H-NMR (CDCl3) δ: 7.93 (1H, d), 7.65 (2H, m), 7.53 (2H, m), 6.97 (1H, d), 6.76 (1H, br s), 4.25 (2H, q), 3.30 (2H, m), 1.89 (2H, m), 1.33 (3H, t), 1.05 (3H, t).

[0943] Compound IIA-148 of the present invention: 1 1H-NMR (CDCl3) δ: 7.93 (1H, d), 7.65 (2H, m), 7.53 (2H, m), 6.97 (1H, d), 6.78 (1H, br s), 5.04 (1H, m), 3.30 (2H, m), 1.89 (2H, m), 1.32 (6H, d), 1.05 (3H, t).

[0944] [Table 13]

[0945] [Table IIA3-5]

[0946]

[0947] Compound IIA-152 of the present invention: 1 H-NMR (CDCl3) δ: 8.40 (2H, m), 8.13 (1H, d), 7.96 (2H, m), 7.07 (1H, d), 3.33 (2H, m), 1.91 (2H, m), 1.08 (3H, t).

[0948] Compound IIA-153 of the present invention: 1 H-NMR (CDCl3) δ: 8.61 (1H, t), 8.27 (1H, m), 8.17 - 8.13 (2H, m), 7.73 (1H, t), 7.06 (1H, d), 3.34 (2H, m), 1.90 (2H, m), 1.08 (3H, t).

[0949] Compound IIA-154 of the present invention: 1 H-NMR (CDCl3) δ: 7.88 (1H, d), 7.63 (2H, m), 7.48 (2H, m), 3.31 (2H, m), 1.92 (2H, m), 1.08 (3H, t).

[0950] Compound IIA-155 of the present invention: 1 H-NMR (CDCl3) δ: 8.51 (1H, t), 7.96 (1H, d), 7.62 (1H, m), 7.45 - 7.41 (2H, m), 6.99 (1H, d), 3.30 (2H, m), 2.27 (3H, s), 1.89 (2H, m), 1.06 (3H, t).

[0951] Compound IIA-156 of the present invention: 1 H-NMR (CDCl3) δ: 8.51 (1H, m), 7.96 (1H, d), 7.67 - 7.60 (2H, m), 7.41 (1H, m), 6.98 (1H, d), 3.30 (2H, m), 1.89 (2H, m), 1.60 (1H, m), 1.14 (2H, m), 1.06 (3H, t), 0.94 (2H, m).

[0952] Compound IIA-157 of the present invention: 1 H-NMR (CDCl3) δ: 8.53 (1H, t), 7.96 (1H, d), 7.62 (1H, m), 7.45 - 7.39 (2H, m), 6.98 (1H, d), 3.30 (2H, m), 2.45 (2H, t), 1.89 (2H, m), 1.75 (2H, m), 1.43 (2H, m), 1.06 (3H, t), 0.97 (3H, t).

[0953] Compound IIA-158 of the present invention: 1 H-NMR(CDCl3)δ:8.66(1H,t),8.07(1H,br s),7.99(1H,d),7.88(2H,m),7.67(1H,m),7.49(1H,m),7.04-6.99(3H,m),3.90(3H,s),3.31(2H,m),1.89(2H,m),1.07(3H,t).

[0954] Compound IIA-159 of the present invention: 1 H-NMR(CDCl3)δ:8.63(1H,t),8.09(1H,br s),8.00(1H,d),7.86(2H,m),7.69(1H,m),7.53-7.48(3H,m),7.00(1H,d),3.31(2H,m),1.89(2H,m),1.07(3H,t).

[0955] Compound IIA-160 of the present invention: 1 H-NMR(CDCl3)δ:8.60(1H,t),8.00-7.96(2H,m),7.70-7.66(2H,m),7.63(1H,m),7.49(1H,m),7.18(1H,m),7.00(1H,d),3.31(2H,m),1.89(2H,m),1.07(3H,t).

[0956] Compound IIA-161 of the present invention: 1 H-NMR(CDCl3)δ:8.25(1H,br s),8.10(1H,m),8.01(1H,d),7.88(2H,m),7.70(1H,m),7.50-7.44(4H,m),6.95(1H,d),3.27(2H,m),1.86(2H,m),1.04(3H,t).

[0957] Compound IIA-162 of the present invention: 1 H-NMR(CDCl3)δ:8.08(1H,m),8.00(1H,m),7.77-7.66(1H,br s),7.49-7.37(3H,m),6.96(1H,m),3.30(2H,m),1.87(2H,m),1.56(1H,m),1.11(2H,m),1.05(3H,t),0.90(2H,m).

[0958] Compound IIA-163 of the present invention: 11H-NMR (CDCl3) δ: 8.11 - 7.99 (2H, m), 7.52 - 7.34 (4H, m), 6.95 (1H, m), 3.29 (2H, m), 2.45 (2H, m), 1.88 (2H, m), 1.27 (3H, m), 1.05 (3H, m).

[0959] Compound IIA-164 of the present invention: 1 1H-NMR (CDCl3) δ: 8.21 (1H, m), 8.10 (1H, br s), 8.05 (1H, d), 7.89 - 7.86 (2H, m), 7.62 - 7.54 (3H, m), 7.18 (2H, m), 6.97 (1H, d), 3.30 (2H, m), 2.35 (3H, s), 1.87 (2H, m), 1.05 (3H, t).

[0960] Compound IIA-165 of the present invention: 1 1H-NMR (CDCl3) δ: 8.23 (1H, m), 8.07 (1H, d), 8.02 (1H, br s), 7.91 - 7.87 (2H, m), 7.63 - 7.56 (3H, m), 6.99 (1H, d), 6.92 (2H, m), 3.83 (3H, s), 3.30 (2H, m), 1.88 (2H, m), 1.06 (3H, t).

[0961] Compound IIA-166 of the present invention: 1 1H-NMR (CDCl3) δ: 8.21 (1H, m), 8.17 (1H, br s), 8.06 (1H, d), 7.90 - 7.87 (2H, m), 7.66 - 7.60 (3H, m), 7.35 (2H, m), 6.98 (1H, d), 3.29 (2H, m), 1.87 (2H, m), 1.05 (3H, t).

[0962] Compound IIA-167 of the present invention: 1 1H-NMR (CDCl3) δ: 8.29 (1H, br s), 8.19 (1H, m), 8.05 (1H, d), 7.90 - 7.85 (2H, m), 7.82 (1H, m), 7.60 (1H, t), 7.55 (1H, m), 7.30 (1H, t), 7.17 - 7.14 (1H, m), 6.96 (1H, d), 3.29 (2H, m), 1.87 (2H, m), 1.05 (3H, t).

[0963] Compound IIA-168 of the present invention: 1 1H-NMR (CDCl3) δ:1 H-NMR (CDCl3) δ: 7.79 (1H, d), 7.71 - 7.70 (1H, m), 7.67 - 7.65 (1H, m), 7.29 - 7.17 (5H, m), 7.09 (2H, d), 6.94 (1H, d), 3.54 (3H, s), 3.31 - 3.27 (2H, m), 1.91 - 1.82 (2H, m), 1.06 (3H, t).

[0964] Compound IIA-169 of the present invention: 1 H-NMR (CDCl3) δ: 8.10 (1H, m), 8.05 (1H, d), 7.84 (1H, m), 7.76 (1H, m), 7.55 (1H, t), 6.97 (1H, m), 6.58 (1H, br s), 3.30 (2H, m), 2.95 (1H, m), 1.88 (2H, m), 1.06 (3H, t), 0.91 (2H, m), 0.70 (2H, m).

[0965] Compound IIA-170 of the present invention: 1 H-NMR (CDCl3) δ: 8.15 (1H, m), 8.07 (1H, d), 7.87 (1H, m), 7.78 (1H, m), 7.56 (1H, t), 6.99 (1H, m), 6.41 (1H, br s), 3.46 (2H, q), 3.31 (2H, m), 1.88 (2H, m), 1.68 (2H, m), 1.06 (3H, t), 1.01 (3H, t).

[0966] Compound IIA-171 of the present invention: 1 H-NMR (CDCl3) δ: 8.05 - 8.03 (2H, m), 7.87 (1H, m), 7.73 (1H, m), 7.56 (1H, t), 7.01 (1H, d), 3.58 (3H, s), 3.41 (3H, s), 3.32 (2H, m), 1.89 (2H, m), 1.06 (3H, t).

[0967] Compound IIA-172 of the present invention: 1 H-NMR (CDCl3) δ: 8.08 (1H, m), 8.03 (2H, m), 7.90 - 7.85 (3H, m), 7.67 (2H, m), 7.41 (2H, m), 7.19 (1H, m), 7.02 (1H, m), 3.33 (2H, m), 1.90 (2H, m), 1.07 (3H, t).

[0968] Compound IIA-173 of the present invention: 11H-NMR (CDCl3) δ: 8.05 (1H, d), 7.89 (2H, m), 7.79 (2H, m), 7.00 (1H, m), 6.34 (1H, br s), 3.31 (2H, m), 2.93 (1H, m), 1.89 (2H, m), 1.06 (3H, t), 0.90 (2H, m), 0.67 (2H, m).

[0969] Compound IIA-174 of the present invention: 1 1H-NMR (CDCl3) δ: 8.08 (1H, d), 7.87 (2H, m), 7.80 (2H, m), 7.01 (1H, d), 3.56 (3H, s), 3.40 (3H, s), 3.32 (2H, m), 1.90 (2H, m), 1.07 (3H, t).

[0970] Compound IIA-175 of the present invention: 1 1H-NMR (CDCl3) δ: 8.04 (1H, m), 8.01 (1H, d), 7.74 - 7.71 (2H, m), 7.64 - 7.57 (2H, m), 7.54 - 7.48 (2H, m), 7.46 - 7.41 (2H, m), 6.99 (1H, d), 3.67 (3H, s), 3.32 (2H, m), 1.89 (2H, m), 1.07 (3H, t).

[0971] Compound IIA-176 of the present invention: 1 1H-NMR (CDCl3) δ: 8.00 (1H, d), 7.75 (2H, m), 7.71 - 7.68 (4H, m), 7.49 (1H, m), 7.42 (2H, m), 7.00 (1H, d), 3.68 (3H, s), 3.31 (2H, m), 1.89 (2H, m), 1.06 (3H, t).

[0972] Compound IIA-177 of the present invention: 1 1H-NMR (CDCl3) δ: 7.63 (2H, m), 7.50 (2H, m), 6.50 (1H, d), 3.29 (2H, m), 1.90 (2H, m), 1.07 (3H, t).

[0973] Compound IIA-178 of the present invention: 1 1H-NMR (CDCl3) δ: 7.61 (2H, m), 7.51 (2H, m), 3.30 (2H, m), 1.92 (2H, m), 1.09 (3H, t).

[0974] [Table 14]

[0975] [Table I A3]

[0976] This compound Z <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 5 > <![CDATA[R 6 > <![CDATA[R 7 > IA-11 Me H H Cl H H H H IA-12 Ph H H Cl H H H H IA-13 Ph H F Cl H H H H IA-14 Ph H H OMe H H H H IA-15 4-(OMe)-Ph H H Cl H H H H IA-16 4-Cl-Ph H H Cl H H H H IA-17 2-(OMe)-Ph H H Cl H H H H IA-18 2-Cl-Ph H H Cl H H H H

[0977] This compound IA-11: 1 H-NMR(CDCl3)δ: 7.97(1H, d), 7.68(2H, m), 7.48(2H, m), 7.00(1H, d), 3.27(3H, s).

[0978] This compound IA-12: 1 H-NMR(CDCl3)δ: 8.10 - 8.08(2H, m), 7.90(1H, d), 7.62(3H, m), 7.55(2H, m), 7.43(2H, m), 7.00(1H, d).

[0979] This compound IA-13: 1 H-NMR(CDCl3)δ: 8.09(2H, m), 7.91(1H, d), 7.63(1H, m), 7.58 - 7.53(3H, m), 7.49(1H, m), 7.41(1H, m), 7.01(1H, d).

[0980] This compound IA-14: 1 H-NMR(CDCl3)δ: 8.09(2H, m), 7.82(1H, d), 7.62 - 7.51(5H, m), 6.97 - 6.94(3H, m), 3.84(3H, s).

[0981] This compound IA-15: 1 H-NMR(CDCl3)δ: 8.01(2H, m), 7.88(1H, d), 7.61(2H, m), 7.43(2H, m), 7.00(2H, m), 6.96(1H, d), 3.86(3H, s).

[0982] This compound IA-16: 1 H-NMR(CDCl3)δ: 8.02(2H, m), 7.91(1H, d), 7.61(2H, m), 7.51(2H, m), 7.44(2H, m), 7.00(1H, d).

[0983] This compound IA-17: 1H-NMR(CDCl3)δ: 8.04(1H, m), 7.84(1H, d), 7.64(2H, m), 7.49(1H, m), 7.43(2H, m), 7.23(1H, m), 6.91(1H, d), 6.45(1H, d). 3.78(3H, s).

[0984] Production Example 6

[0985] A mixture of 1.03 g of 4-chlorothiobenzamide, 0.92 g of S-ethyl 2-bromothioacetate, and 15 mL of ethanol was stirred at 80 °C for 8 hours. The resulting mixture was concentrated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 98:2) to obtain 0.42 g of the compound IIB-1 of the present invention represented by the following formula.

[0986] [Chemical Formula 53]

[0987]

[0988] Compound IIB-1 of the present invention: 1 H-NMR(CDCl3)δ: 7.89(2H, m), 7.40(2H, m), 7.04(1H, s), 3.09(2H, q), 1.37(3H, t).

[0989] Production Example 6-1

[0990] The compounds produced according to Production Example 6 and their physical property values are shown below.

[0991] In the compound represented by the formula (B1), Z, R 1 , R 2 , R 3 , R 4 , R 5 , and R 8 are combined as the compounds described in [Table IIB1].

[0992] [Chemical Formula 54]

[0993]

[0994] [Table 15]

[0995] [Table IIB1]

[0996] The compound of the present invention Z <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 5 > <![CDATA[R 8 > IIB-2 Pr H H Cl H H H

[0997] Compound IIB-2 of the present invention: 11H-NMR (CDCl3) δ: 7.84 (2H, m), 7.23 (2H, m), 6.98 (1H, s), 3.05 (2H, m), 1.73 (2H, m), 1.04 (3H, t).

[0998] Production Example 7

[0999] To a mixture of 0.42 g of Compound IIB-1 of the present invention and 5 mL of chloroform, 1.2 g of mCPBA (purity 75%, containing 25% water) was added at 0 °C, and the mixture was stirred at room temperature for 2 hours. An aqueous sodium sulfite solution was added to the resulting mixture, and extraction was performed with chloroform. The obtained organic layer was washed with an aqueous sodium bicarbonate solution, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 80:20) to obtain 93 mg of Compound IIB-3 of the present invention represented by the following formula.

[1000] [Chemical Formula 55]

[1001]

[1002] Compound IIB-3 of the present invention: 1 1H-NMR (CDCl3) δ: 8.12 (1H, s), 7.93 (2H, m), 7.46 (2H, m), 3.40 (2H, q), 1.37 (3H, t).

[1003] Production Example 7-1

[1004] The compounds produced according to Production Example 7 and their physical property values are shown below.

[1005] In the compound represented by the formula (B3), Z, R 1 , R 2 , R 3 , R 4 , R 5 , and R 8 are combined as the combinations described in [Table IIB3].

[1006] [Chemical Formula 56]

[1007]

[1008] [Table 16]

[1009] [Table IIB3]

[1010] The compound of the present invention Z <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 5 > <![CDATA[R 6 > IIB-4 Pr H H Cl H H H

[1011] Compound IIB-4 of the present invention: 11H-NMR (CDCl3) δ: 8.16 (1H, s), 7.93 (2H, m), 7.46 (2H, m), 3.35 (2H, m), 1.87 (2H, m), 1.06 (3H, t).

[1012] Reference Production Example 7

[1013] A mixture of 1.35 g of 4-fluoro-3-(trifluoromethyl)benzoylmethyl bromide, 0.5 g of O-ethyl thiocarbamate, and 5 mL of ethanol was stirred at 85 °C for 5 hours. The resulting mixture was concentrated under reduced pressure. To the resulting residue, 5 mL of toluene and 0.73 g of Lawesson's reagent were successively added, and the mixture was stirred at 110 °C for 8 hours. Saturated brine was added to the resulting mixture, and extraction was performed with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 0.34 g of Intermediate MC1-1 represented by the following formula.

[1014] [Chemical Formula 57]

[1015]

[1016] Intermediate MC1-1: 1 1H-NMR (CDCl3) δ: 7.76 - 7.73 (1H, m), 7.71 - 7.67 (1H, m), 7.37 - 7.32 (1H, m), 6.73 (1H, s).

[1017] Reference Production Example 7-1

[1018] Using 4-fluoro-3-bromobenzoylmethyl bromide instead of 4-fluoro-3-(trifluoromethyl)benzoylmethyl bromide, Intermediate MC1-2 was obtained according to Reference Production Example 7.

[1019] [Chemical Formula 58]

[1020]

[1021] Intermediate MC1-2: 1 1H-NMR (CDCl3) δ: 7.66 (1H, dd), 7.28 - 7.25 (1H, m), 7.17 (1H, dd), 6.75 (1H, s).

[1022] Production Example 8

[1023] A mixture of 0.34 g of intermediate MC1-1, 0.14 mL of 1-iodopropane, 0.25 g of potassium carbonate, and 5 mL of acetone was stirred at 80 °C for 5 hours. The resulting mixture was concentrated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 40:60) to obtain 0.38 g of the present compound IC-1 represented by the following formula.

[1024] [Chemical formula 59]

[1025]

[1026] This compound IC-1: 1 1H-NMR (CDCl3) δ: 8.13 - 8.11 (1H, m), 8.06 - 8.03 (1H, m), 7.35 (1H, s), 7.26 - 7.21 (1H, m), 3.26 (2H, t), 1.90 - 1.81 (2H, m), 1.11 - 1.07 (3H, m).

[1027] Production Example 8-1

[1028] The compounds produced according to Production Example 8 and their physical property values are shown below.

[1029] In the compound represented by formula (C1), Z, R 1 , R 2 , R 3 , R 4 and R 5 are combined in any one of the combinations described in [Table IC1].

[1030] [Chemical formula 60]

[1031]

[1032] [Table 17]

[1033] [Table IC1]

[1034] This compound Z <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 5 > IC-2 s-Bu H H Cl H H IC-3 i-Pr H H Cl H H IC-4 Pr H H OMe H H IC-5 Pr H H Me H H IC-6 Et H H <![CDATA[OCF3]]> H H IC-7 Pr H H Br H H IC-8 Et H Cl Cl H H IC-9 Pr H H Bu H H IC-10 Pr Br H H H H IC-11 Pr Me H H H H IC-12 Pr H H <![CDATA[CF3]]> H H IC-13 Pr H H t-Bu H H IC-14 Pr H H F H H IC-15 Pr H Br H H H IC-16 Et H F H H H IC-17 Pr H F H H H IC-18 Et H F Me H H IC-19 Pr H F Me H H IC-20 <![CDATA[CH2CH2CF=CF2]]> H F H H H IC-21 Et H H I H H IC-22 Et H H Br H H IC-23 Et H F Br H H IC-24 Pr H F Br H H IC-25 Me H H H H H IC-26 Et H H Cl H H IC-27 Me H H Cl H H IC-28 Pr H H Cl H H IC-29 Bu H H Cl H H IC-30 Pr H H H H H

[1035] This compound IC-2: 1 1H-NMR (CDCl3) δ: 7.83 (2H, dt), 7.38 (2H, dt), 7.35 (1H, s), 3.77 - 3.69 (1H, m), 1.88 - 1.68 (2H, m), 1.47 (3H, d), 1.06 (3H, t).

[1036] This compound IC-3: 11H-NMR (CDCl3) δ: 7.85 - 7.81 (2H, m), 7.40 - 7.36 (2H, m), 7.36 (1H, s), 3.95 - 3.84 (1H, m), 1.48 (6H, d).

[1037] This compound IC-4: 1 1H-NMR (CDCl3) δ: 7.82 (2H, dt), 7.20 (1H, s), 6.94 (2H, dt), 3.85 (3H, s), 3.24 (2H, t), 1.89 - 1.80 (2H, m), 1.08 (3H, t).

[1038] This compound IC-5: 1 1H-NMR (CDCl3) δ: 7.79 - 7.76 (2H, m), 7.28 (1H, s), 7.22 - 7.20 (2H, m), 3.24 (2H, t), 2.38 (3H, s), 1.89 - 1.80 (2H, m), 1.08 (3H, t).

[1039] This compound IC-6: 1 1H-NMR (CDCl3) δ: 7.93 - 7.89 (2H, m), 7.34 (1H, s), 7.26 - 7.24 (2H, m), 3.29 (2H, q), 1.48 (3H, t).

[1040] This compound IC-7: 1 1H-NMR (CDCl3) δ: 7.78 - 7.74 (2H, m), 7.55 - 7.51 (2H, m), 7.34 (1H, s), 3.25 (2H, t), 1.89 - 1.80 (2H, m), 1.08 (3H, t).

[1041] This compound IC-8: 1 1H-NMR (CDCl3) δ: 8.00 (1H, s), 7.70 (1H, d), 7.46 (1H, d), 7.36 (1H, s), 3.29 (2H, q), 1.48 (3H, t).

[1042] This compound IC-9: 1 1H-NMR (CDCl3) δ: 7.79 (2H, d), 7.28 (1H, s), 7.22 (2H, d), 3.24 (2H, t), 2.63 (2H, t), 1.89 - 1.80 (2H, m), 1.65 - 1.58 (2H, m), 1.41 - 1.32 (2H, m), 1.07 (3H, t), 0.93 (3H, t).

[1043] This compound IC-10: 1 H-NMR(CDCl3) δ: 7.80(1H, dd), 7.66(1H, d), 7.62(1H, s), 7.37(1H, t), 7.19(1H, td), 3.24(2H, t), 1.89 - 1.80(2H, m), 1.07(3H, t).

[1044] This compound IC-11: 1 H-NMR(CDCl3) δ: 7.57(1H, d), 7.27 - 7.21(3H, m), 7.12(1H, s), 3.24(2H, t), 2.45(3H, s), 1.88 - 1.79(2H, m), 1.06(3H, t).

[1045] This compound IC-12: 1 H-NMR(CDCl3) δ: 8.00(2H, d), 7.66(2H, d), 7.45(1H, d), 3.27(2H, t), 1.91 - 1.82(2H, m), 1.09(3H, t).

[1046] This compound IC-13: 1 H-NMR(CDCl3) δ: 7.81(2H, d), 7.43(2H, d), 7.29(1H, s), 3.25(2H, t), 1.89 - 1.80(2H, m), 1.35(9H, s), 1.07(3H, t).

[1047] This compound IC-14: 1 H-NMR(CDCl3) δ: 7.88 - 7.83(2H, m), 7.27(1H, s), 7.12 - 7.06(2H, m), 3.25(2H, t), 1.90 - 1.80(2H, m), 1.08(3H, t).

[1048] This compound IC-15: 1H-NMR(CDCl3) δ: 8.05(1H, s), 7.80(1H, d), 7.45(1H, d), 7.36(1H, s), 7.27(1H, t), 3.26(2H, t), 1.90 - 1.80(2H, m), 1.08(3H, t).

[1049] This compound IC-16: 1 H-NMR(CDCl3) δ: 7.66 - 7.60(2H, m), 7.39 - 7.34(2H, m), 7.04 - 6.99(1H, m), 3.30(2H, q), 1.48(3H, t).

[1050] This compound IC-17: 1 H-NMR(CDCl3)δ: 7.66 - 7.59(2H, m), 7.41 - 7.34(2H, m), 7.04 - 6.99(1H, m), 3.26(2H, t), 1.90 - 1.81(2H, m), 1.08(3H, t).

[1051] This compound IC-19: 1 H-NMR(CDCl3)δ: 7.56 - 7.53(2H, m), 7.30(1H, s), 7.22 - 7.18(1H, m), 3.25(2H, t), 2.30(3H, s), 1.90 - 1.80(2H, m), 1.08(3H, t).

[1052] This compound IC-20: 1 H-NMR(CDCl3)δ: 7.65 - 7.59(2H, m), 7.40 - 7.35(2H, m), 7.06 - 7.01(1H, m), 3.48(2H, t), 2.95 - 2.83(2H, m).

[1053] This compound IC-21: 1H-NMR(CDCl3)δ: 7.74(2H, dt), 7.63(2H, dt), 7.36(1H, s), 3.28(2H, q), 1.48(3H, t).

[1054] This compound IC-22: 1H-NMR(CDCl3)δ: 7.76(2H, dt), 7.53(2H, dt), 7.35(1H, s), 3.28(2H, q), 1.48(3H, t).

[1055] This compound IC-23: 1 H-NMR(CDCl3)δ: 7.68(1H, dd), 7.59 - 7.52(2H, m), 7.38(1H, s), 3.29(2H, q), 1.48(3H, t).

[1056] This compound IC-24: 1 H-NMR(CDCl3)δ: 7.68(1H, dd), 7.59 - 7.51(2H, m), 7.37(1H, s), 3.26(2H, t), 1.90 - 1.81(2H, m), 1.08(3H, t).

[1057] Production Example 9

[1058] To a mixture of 0.2 g of this compound IC-26 and 5 mL of chloroform, 0.4 g of mCPBA (purity 75%, containing 25% water) was added at 0 °C, and the mixture was stirred at room temperature for 3 hours. 10 mL of a saturated aqueous sodium thiosulfate solution was added to the resulting mixture, and after stirring for 1 hour, extraction was performed with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 80:20) to obtain 0.2 g of the compound IIC-1 of the present invention represented by the following formula.

[1059] [Chemical formula 61]

[1060]

[1061] Compound IIC-1 of the present invention: 1 H-NMR (CDCl3) δ: 7.87 (2H, d), 7.82 (1H, s), 7.44 (2H, d), 3.51 (2H, q), 1.44 (3H, t).

[1062] Production Example 9-1

[1063] The compounds produced according to Production Example 9 and their physical property values are shown below.

[1064] In the compound represented by formula (C3), Z, R 1 , R 2 , R 3 , R 4 , and R 5 are compounds in which the combination is any of the combinations described in [Table IIC3] and [Table IC3].

[1065] [Chemical formula 62]

[1066]

[1067] [Table 18]

[1068] [Table IIC3]

[1069] The compound of the present invention Z <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 5 > IIC-2 s-Bu H H Cl H H IIC-3 i-Pr H H Cl H H IIC-4 Pr H H Cl H H IIC-5 Bu H H Cl H H IIC-6 Pr H H OMe H H IIC-7 Pr H H Me H H IIC-8 Et H H <![CDATA[OCF3]]> H H IIC-9 Pr H H Br H H IIC-10 Et H Cl Cl H H IIC-11 Pr H H Bu H H IlC-12 Pr Br H H H H IIC-13 Pr H <![CDATA[CF3]]> F H H lIC-14 Pr Me H H H H lIC-15 Pr H H <![CDATA[CF3]]> H H IIC-16 Pr H H t-Bu H H IIC-17 Pr H H F H H lIC-18 Pr H Br H H H IIC-19 Et H F H H H lIC-20 Pr H F H H H IIC-21 Et H F Me H H IIC-22 Pr H F Me H H IIC-23 <![CDATA[CH2CH2CF=CF2]]> H F H H H IIC-24 Et H H I H H IIC-25 Et H H Br H H IIC-26 Et H F Br H H IIC-27 Pr H F Br H H

[1070] Compound IIC-2 of the present invention: 1 H-NMR (CDCl3) δ: 7.89 - 7.86 (2H, m), 7.84 - 7.83 (1H, m), 7.45 - 7.42 (2H, m), 3.48 - 3.46 (1H, m), 2.17 - 2.14 (1H, m), 1.70 - 1.63 (1H, m), 1.45 (3H, d), 1.06 (3H, t).

[1071] Compound IIC-3 of the present invention: 1 H-NMR (CDCl3) δ: 7.87 (2H, d), 7.84 (1H, s), 7.45 - 7.41 (2H, m), 3.73 - 3.66 (1H, m), 1.47 (6H, d).

[1072] Compound IIC-4 of the present invention: 1 H-NMR (CDCl3) δ: 7.87 (2H, dt), 7.82 (1H, s), 7.44 (2H, dt), 3.48 - 3.44 (2H, m), 1.97 - 1.87 (2H, m), 1.08 (3H, t).

[1073] Compound IIC-5 of the present invention: 1 H-NMR (CDCl3) δ: 7.87 (2H, dt), 7.82 (1H, s), 7.44 (2H, dt), 3.50 - 3.46 (2H, m), 1.90 - 1.82 (2H, m), 1.53 - 1.43 (2H, m), 0.94 (3H, t).

[1074] Compound IIC-6 of the present invention: 1 H-NMR (CDCl3) δ: 7.86 (2H, dt), 7.68 (1H, s), 6.98 (2H, dt), 3.87 (3H, s), 3.47 - 3.43 (2H, m), 1.96 - 1.87 (2H, m), 1.08 (3H, t).

[1075] Compound IIC-7 of the present invention: 1 H-NMR (CDCl3) δ: 7.82 (2H, d), 7.76 (1H, s), 7.45 - 7.41 (2H, m), 3.48 - 3.44 (2H, m), 2.40 (3H, s), 1.96 - 1.87 (2H, m), 1.08 (3H, t).

[1076] Compound IIC-8 of the present invention: 1 H-NMR (CDCl3) δ: 7.96 (2H, dt), 7.84 (1H, s), 7.31 (2H, d), 3.51 (2H, q), 1.44 (3H, t).

[1077] Compound IIC-9 of the present invention: 1 H-NMR (CDCl3) δ: 7.83 (1H, s), 7.80 (2H, dt), 7.43 (2H, t), 3.48 - 3.44 (2H, m), 1.97 - 1.87 (2H, m), 1.08 (3H, t).

[1078] Compound IIC-10 of the present invention: 1 H-NMR(CDCl3)δ: 8.05(1H, d), 7.86(1H, s), 7.75(1H, dd), 7.53(1H, d), 3.52(2H, q), 1.45(3H, t).

[1079] Compound IIC-11 of the present invention: 1 H-NMR(CDCl3)δ: 7.83(2H, d), 7.76(1H, s), 7.30 - 7.28(2H, m), 3.48 - 3.44(2H, m), 2.66(2H, t), 1.96 - 1.86(2H, m), 1.66 - 1.59(2H, m), 1.42 - 1.33(2H, m), 1.07(3H, t), 0.94(3H, t).

[1080] Compound IIC-12 of the present invention: 1 H-NMR(CDCl3)δ: 8.13(1H, s), 7.80(1H, d), 7.70(1H, d), 7.44 - 7.40(1H, m), 7.29 - 7.27(1H, m), 3.48 - 3.45(2H, m), 1.97 - 1.88(2H, m), 1.08(3H, t).

[1081] Compound IIC-13 of the present invention: 1 H-NMR(CDCl3)δ: 8.17(1H, dd), 8.11(1H, m), 7.86(1H, s), 7.31(1H, t), 3.49 - 3.45(2H, m), 1.97 - 1.88(2H, m), 1.10(3H, t).

[1082] Compound IIC-14 of the present invention: 1 H-NMR(CDCl3)δ: 8.08(1H, t), 7.64(1H, s), 7.59 - 7.56(1H, m), 7.43(1H, t), 7.36 - 7.28(1H, m), 3.48 - 3.44(2H, m), 2.46(3H, s), 1.96 - 1.87(2H, m), 1.07(3H, t).

[1083] Compound IIC-15 of the present invention: 1 H-NMR(CDCl3)δ: 8.05(2H, d), 7.94(1H, s), 7.72(2H, d), 3.49 - 3.45(2H, m), 1.98 - 1.88(2H, m), 1.09(3H, t).

[1084] Compound IIC-16 of the present invention: 1 H-NMR(CDCl3)δ:7.85(2H,dt),7.77(1H,s),7.48(2H,dt),3.48-3.44(2H,m),1.95-1.86(2H,m),1.36(9H,s),1.07(3H,t).

[1085] Compound IIC-17 of the present invention: 1 H-NMR(CDCl3)δ:7.93-7.90(2H,m),7.77(1H,s),7.18-7.13(2H,m),3.48-3.44(2H,m),1.97-1.88(2H,m),1.09(3H,t).

[1086] Compound IIC-18 of the present invention: 1 H-NMR(CDCl3)δ:8.10(1H,s),7.85(1H,s),7.84(1H,d),7.54(1H,d),7.34(1H,t),3.49-3.45(2H,m),1.97-1.87(2H,m),1.09(3H,t).

[1087] Compound IIC-19 of the present invention: 1 H-NMR(CDCl3)δ:7.66-7.60(2H,m),7.39-7.34(2H,m),7.04-6.99(1H,m),3.30(2H,q),1.48(3H,t).

[1088] Compound IIC-20 of the present invention: 1 H-NMR(CDCl3)δ:7.66-7.59(2H,m),7.39-7.34(2H,m),7.04-6.99(1H,m),3.26(2H,t),1.90-1.81(2H,m),1.08(3H,t).

[1089] Compound IIC-21 of the present invention: 1 H-NMR(CDCl3)δ:7.79(1H,s),7.60-7.57(2H,m),7.28-7.24(1H,m),3.51(2H,q),2.32(3H,s),1.44(3H,t,).

[1090] Compound IIC-22 of the present invention: 11H-NMR (CDCl3) δ: 7.78 (1H, s), 7.61 - 7.57 (2H, m), 7.28 - 7.24 (1H, m), 3.48 - 3.44 (2H, m), 2.33 (3H, s), 1.97 - 1.87 (2H, m), 1.08 (3H, t).

[1091] Compound IIC-23 of the present invention: 1 1H-NMR (CDCl3) δ: 7.81 (1H, s), 7.66 - 7.63 (1H, m), 7.62 - 7.58 (1H, m), 7.45 - 7.39 (1H, m), 7.12 - 7.06 (1H, m), 3.52 - 3.35 (2H, m), 3.04 - 2.61 (2H, m).

[1092] Compound IIC-24 of the present invention: 1 1H-NMR (CDCl3) δ: 7.84 (1H, s), 7.80 (2H, d), 7.66 (2H, d), 3.51 (2H, q), 1.44 (3H, t).

[1093] Compound IIC-25 of the present invention: 1 1H-NMR (CDCl3) δ: 7.84 (1H, s), 7.80 (2H, d), 7.59 (2H, d), 3.51 (2H, q), 1.44 (3H, t).

[1094] Compound IIC-26 of the present invention: 1 1H-NMR (CDCl3) δ: 7.87 (1H, s), 7.72 (1H, dd), 7.64 (1H, dd), 7.58 (1H, dd), 3.52 (2H, q), 1.45 (3H, t).

[1095] Compound IIC-27 of the present invention: 1 1H-NMR (CDCl3) δ: 7.86 (1H, s), 7.72 (1H, dd), 7.64 (1H, dd), 7.58 (1H, dd), 3.48 - 3.44 (2H, m), 1.95 - 1.89 (2H, m), 1.09 (3H, t).

[1096] [Table 19]

[1097] [Table IC3]

[1098] This compound Z <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 5 > IC-31 Pr H H H H H IC-32 Me H H H H H IC-33 Me H H Cl H H

[1099] This compound IC-31: 11H-NMR (CDCl3) δ: 7.94 - 7.92 (2H, m), 7.83 (1H, s), 7.48 - 7.41 (3H, m), 3.49 - 3.45 (2H, m), 1.97 - 1.88 (2H, m), 1.08 (3H, t).

[1100] This compound IC-32: 1 1H-NMR (CDCl3) δ: 7.94 - 7.91 (2H, m), 7.82 (1H, s), 7.49 - 7.39 (3H, m), 3.39 (3H, s).

[1101] Production Example 10

[1102] To a mixture of 0.30 g of Intermediate MA4-1, 0.16 mL of pyridine and 10 mL of chloroform, 0.18 g of ethyl chloroformate was added at 0 °C, and the mixture was stirred at room temperature for 4 hours. Water was added to the resulting mixture, and the mixture was extracted with chloroform. The obtained organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 60:40) to obtain 0.25 g of the compound IIA-137 of the present invention represented by the following formula.

[1103] [Chemical formula 63]

[1104]

[1105] The compound IIA-137 of the present invention: 1 1H-NMR (CDCl3) δ: 7.88 (1H, d), 7.78 (1H, br s), 7.38 - 7.26 (3H, m), 6.70 (1H, br s), 6.40 (1H, d), 3.80 (3H, s), 3.01 (2H, m), 1.75 (2H, m), 1.04 (3H, t).

[1106] Production Example 10-1

[1107] The compounds produced according to Production Example 10 and their physical property values are shown below.

[1108] In the compound represented by the formula (A1), Z, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are combined as any one of the combinations described in [Table IIA1-3].

[1109] [Chemical formula 64]

[1110]

[1111] [Table 20]

[1112] [Table IIA1-3]

[1113]

[1114] Compound IIA-138 of the present invention: 1 H-NMR(CDCl3)δ: 7.88(1H,d), 7.79(1H,br s), 7.38 - 7.26(3H,m), 6.68(1H,br s), 6.39(1H,d), 4.24(2H,q), 3.01(2H,m), 1.75(2H,m), 1.33(3H,t), 1.04(3H,t).

[1115] Compound IIA-139 of the present invention: 1 H-NMR(CDCl3)δ: 7.88(1H,d), 7.80(1H,br s), 7.38 - 7.26(3H,m), 6.64(1H,br s), 6.39(1H,d), 5.03(1H,m), 3.01(2H,m), 1.75(2H,m), 1.31(6H,d), 1.04(3H,t).

[1116] Compound IIA-140 of the present invention: 1 H-NMR(CDCl3)δ: 7.81(1H,d), 7.61(2H,m), 7.45(2H,m), 6.65(1H,br s), 6.40(1H,d), 3.79(3H,s), 3.00(2H,m), 1.75(2H,m), 1.04(3H,t).

[1117] Compound IIA-141 of the present invention: 1 H-NMR(CDCl3)δ: 7.81(1H,d), 7.60(2H,m), 7.45(2H,m), 6.62(1H,br s), 6.39(1H,d), 4.24(2H,q), 3.00(2H,m), 1.75(2H,m), 1.32(3H,t), 1.04(3H,t).

[1118] Compound IIA-142 of the present invention: 11H-NMR (CDCl3) δ: 7.81 (1H, d), 7.60 (2H, m), 7.45 (2H, m), 6.58 (1H, br s), 6.40 (1H, d), 5.03 (1H, m), 3.00 (2H, m), 1.75 (2H, m), 1.31 (6H, d), 1.04 (3H, t).

[1119] Production Example 11

[1120] To a mixture of 0.5 g of Intermediate MA4-3, 0.32 mL of pyridine and 10 mL of chloroform, 0.24 g of acetyl chloride was added at 0 °C, and the mixture was stirred at room temperature for 4 hours. Water was added to the resulting mixture, and the mixture was extracted with chloroform. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 2:1) to obtain 0.47 g of Compound IIA-179 of the present invention represented by the following formula.

[1121] [Chemical Formula 65]

[1122]

[1123] Compound IIA-179 of the present invention: 1 1H-NMR (CDCl3) δ: 8.38 (1H, t), 7.82 (1H, d), 7.55 (1H, m), 7.40 - 7.33 (2H, m), 6.40 (1H, d), 3.01 (2H, t), 2.24 (3H, s), 1.45 (2H, m), 1.04 (3H, t).

[1124] Production Example 11-1

[1125] The compounds produced according to Production Example 11 and their physical property values are shown below.

[1126] In the compound represented by formula (A1), Z, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are combined as any one of the combinations described in [Table IIA1-4].

[1127] [Chemical Formula 66]

[1128]

[1129] [Table 21]

[1130] [Table IIA1-4]

[1131]

[1132] Compound IIA-180 of the present invention: 1 H-NMR(CDCl3) δ: 8.39(1H, m), 7.81(1H, d), 7.60 - 7.53(2H, m), 7.33(1H, m), 6.40(1H, d), 3.01(2H, t), 1.75(2H, m), 1.58(1H, m), 1.13(2H, m), 1.04(3H, t), 0.91(2H, m).

[1133] Compound IIA-181 of the present invention: 1 H-NMR(CDCl3) δ: 8.42(1H, t), 7.82(1H, d), 7.55(1H, m), 7.36 - 7.30(2H, m), 6.40(1H, d), 3.01(2H, t), 2.43(2H, t), 1.80 - 1.69(4H, m), 1.43(2H, m), 1.04(3H, t), 0.97(3H, t).

[1134] Compound IIA-182 of the present invention: 1 H-NMR(CDCl3) δ: 8.55(1H, t), 7.99(1H, br s), 7.89 - 7.84(3H, m), 7.61(1H, m), 7.41(1H, m), 7.01(2H, m), 6.41(1H, d), 3.89(3H, s), 3.03(2H, t), 1.77(2H, m), 1.05(3H, t).

[1135] Compound IIA-183 of the present invention: 1 H-NMR(CDCl3) δ: 8.52(1H, t), 7.99(1H, br s), 7.86 - 7.83(3H, m), 7.62(1H, m), 7.50(2H, m), 7.42(1H, m), 6.42(1H, d), 3.03(2H, t), 1.77(2H, m), 1.06(3H, t).

[1136] Compound IIA-184 of the present invention: 1 H-NMR(CDCl3) δ: 8.49(1H, t), 7.91(1H, br s), 7.85(1H, d), 7.60(1H, m), 7.64 - 7.59(2H, m), 7.40(1H, m), 7.16(1H, m), 6.42(1H, d), 3.03(2H, t), 1.77(2H, m), 1.05(3H, t).

[1137] Compound IIA-185 of the present invention: 1 H-NMR(CDCl3)δ: 8.05(1H,m), 7.93(1H,d), 7.90(1H,brs), 7.78(2H,m), 7.60(1H,m), 7.46 - 7.40(2H,m), 7.31(2H,m), 6.42(1H,d), 3.01(2H,t), 2.44(3H,s), 1.76(2H,m), 1.05(3H,t).

[1138] Compound IIA-186 of the present invention: 1 H-NMR(CDCl3)δ: 8.02(1H,m), 7.92 - 7.89(2H,m), 7.82(2H,m), 7.60(1H,m), 7.05 - 7.40(4H,m), 6.42(1H,d), 3.01(2H,t), 1.75(2H,m), 1.04(3H,t).

[1139] Compound IIA-187 of the present invention: 1 H-NMR(CDCl3)δ: 7.96(1H,br s), 7.89(1H,d), 7.43 - 7.34(4H,m), 6.39(1H,d), 3.01(2H,t), 1.75(2H,m), 1.52(1H,m), 1.11(2H,m), 1.04(3H,t), 0.89(2H,m).

[1140] Compound IIA-188 of the present invention: 1 H-NMR(CDCl3)δ: 7.95 - 7.88(2H,m), 7.43 - 7.23(4H,m), 6.42(1H,m), 3.01(2H,m), 2.43(2H,m), 1.76(2H,m), 1.27(3H,m), 0.05(3H,m).

[1141] Production Example 12

[1142] A mixture of 0.26 g of Intermediate MA5-2, 0.16 g of p-toluidine, 0.38 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 0.24 g of 4-dimethylaminopyridine, and 10 mL of chloroform was stirred at room temperature for 6 hours. Water was added to the resulting mixture, and extraction was performed with chloroform. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 3:1) to obtain 0.29 g of Compound IIA-189 of the present invention represented by the following formula.

[1143] [Chemical Formula 67]

[1144]

[1145] Compound IIA-189 of the present invention: 1 H-NMR(CDCl3) δ: 8.05(1H, m), 7.93(1H, d), 7.90(1H, brs), 7.78(2H, m), 7.60(1H, m), 7.46 - 7.40(2H, m), 7.31(2H, m), 6.42(1H, d), 3.01(2H, t), 2.44(3H, s), 1.76(2H, m), 1.05(3H, t).

[1146] Production Example 12-1

[1147] The compounds produced according to Production Example 12 and their physical property values are shown below.

[1148] In the compound represented by formula (A1), Z, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are combined as any one of the combinations described in [Table IIA1-5].

[1149] [Chemical Formula 68]

[1150]

[1151] [Table 22]

[1152] [Table IIA1-5]

[1153]

[1154] Compound IIA-190 of the present invention: 1 H-NMR(CDCl3) δ: 8.18(1H, m), 8.96(1H, d), 7.90(1H, brs), 7.83(1H, m), 7.75(1H, m), 7.58 - 7.53(3H, m), 6.93(2H, m), 6.45(1H, d), 3.83(3H, s), 3.03(2H, t), 1.76(2H, m), 1.05(3H, t).

[1155] Compound IIA-191 of the present invention: 11H-NMR (CDCl3) δ: 8.20 (1H, m), 7.98 (1H, br s), 7.96 (1H, d), 7.84 (1H, m), 7.76 (1H, m), 7.64 (2H, m), 7.57 (1H, t), 7.36 (2H, m), 6.47 (1H, d), 3.03 (2H, t), 1.76 (2H, m), 1.05 (3H, t).

[1156] Compound IIA-192 of the present invention: 1 1H-NMR (CDCl3) δ: 8.18 (1H, m), 8.97 - 8.92 (2H, m), 7.87 - 7.81 (2H, m), 7.74 (1H, m), 7.56 (1H, t), 7.50 (1H, m), 7.31 (1H, t), 7.16 (1H, m), 6.46 (1H, d), 3.03 (2H, t), 1.76 (2H, m), 1.05 (3H, t).

[1157] Compound IIA-193 of the present invention: 1 1H-NMR (CDCl3) δ: 7.66 (1H, d), 7.63 - 7.60 (2H, m), 7.27 - 7.07 (7H, m), 6.35 (1H, d), 3.52 (3H, s), 3.00 (2H, t), 1.74 (2H, m), 1.04 (3H, t).

[1158] Compound IIA-194 of the present invention: 1 1H-NMR (CDCl3) δ: 8.05 (1H, m), 7.94 (1H, d), 7.80 (1H, m), 7.63 (1H, m), 7.49 (1H, t), 6.44 (1H, d), 6.36 (1H, br s), 3.01 (2H, t), 2.93 (1H, m), 1.75 (2H, m), 1.05 (3H, t), 0.90 (2H, m), 0.66 (2H, m).

[1159] Compound IIA-195 of the present invention: 1 1H-NMR (CDCl3) δ: 8.08 (1H, m), 7.95 (1H, d), 7.81 (1H, m), 7.64 (1H, m), 7.50 (1H, t), 6.44 (1H, d), 6.23 (1H, br s), 3.45 (2H, m), 3.02 (2H, t), 1.76 (2H, m), 1.67 (2H, m), 1.05 (3H, t), 1.01 (3H, t).

[1160] Compound IIA-196 of the present invention: 11H-NMR (CDCl3) δ: 7.95 (1H, m), 7.90 (1H, d), 7.81 (1H, m), 7.57 (1H, m), 7.48 (1H, t), 6.42 (1H, d), 3.58 (3H, s), 3.39 (3H, s), 3.03 (2H, t), 1.76 (2H, m), 1.05 (3H, t).

[1161] Compound IIA-197 of the present invention: 1 1H-NMR (CDCl3) δ: 7.97 - 7.93 (3H, m), 7.83 (1H, br s), 7.80 (2H, m), 7.65 (2H, m), 7.39 (2H, m), 7.17 (1H, m), 6.45 (1H, d), 3.05 (2H, t), 1.78 (2H, m), 1.06 (3H, t).

[1162] Compound IIA-198 of the present invention: 1 1H-NMR (CDCl3) δ: 7.92 (1H, d), 7.82 (2H, m), 7.72 (2H, m), 6.43 (1H, d), 6.27 (1H, br s), 3.03 (2H, t), 2.92 (1H, m), 1.77 (2H, m), 1.05 (3H, t), 0.89 (2H, m), 0.65 (2H, m).

[1163] Compound IIA-199 of the present invention: 1 1H-NMR (CDCl3) δ: 7.92 (1H, d), 7.82 (2H, m), 7.71 (2H, m), 6.43 (1H, d), 3.56 (3H, s), 3.39 (3H, s), 3.04 (2H, t), 1.77 (2H, m), 1.05 (3H, t).

[1164] Production Example 13

[1165] To a mixture of 2.5 g of Intermediate MA6-1, 0.8 mL of pyridine, and 30 mL of chloroform, 1.1 mL of benzoyl chloride was added dropwise at 0 °C, and the mixture was stirred at 0 °C for 2 hours. Water was added to the resulting mixture, and extraction was performed with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 1.3 g of Compound IIA-203 of the present invention represented by the following formula.

[1166] [Chemical Formula 69]

[1167]

[1168] Compound IIA-203 of the present invention:1 1H-NMR (CDCl3) δ: 7.71 (1H, d), 7.60 (1H, m), 7.57 (1H, m), 7.50 - 7.46 (2H, m), 7.41 (1H, m), 7.33 - 7.28 (3H, m), 7.01 (1H, m), 6.38 (1H, d), 3.0 (2H, t), 1.74 (2H, m), 1.04 (3H, t).

[1169] Production Example 13-1

[1170] Using intermediate MA6-2 in place of intermediate MA6-1, according to Production Example 13, the compound IIA-204 of the present invention represented by the following formula was obtained.

[1171] [Chemical formula 70]

[1172]

[1173] Compound IIA-204 of the present invention: 1 1H-NMR (CDCl3) δ: 7.83 (1H, d), 7.59 (2H, m), 7.45 (2H, m), 7.39 (1H, m), 7.30 - 7.26 (4H, m), 6.40 (1H, d), 3.00 (2H, t), 1.74 (2H, m), 1.03 (3H, t).

[1174] Production Example 14

[1175] To a mixture of 1.1 g of compound IIA-203 of the present invention, 0.6 g of potassium carbonate, and 15 mL of DMF, 0.6 g of methyl iodide was added at 0 °C, and the mixture was stirred at room temperature for 4 hours. Water was added to the resulting mixture, and extraction was performed with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 4:1) to obtain 1.1 g of compound IIA-200 of the present invention represented by the following formula.

[1176] [Chemical formula 71]

[1177]

[1178] Compound IIA-200 of the present invention: 1 1H-NMR (CDCl3) δ: 7.88 (1H, m), 7.84 (1H, d), 7.69 - 7.66 (2H, m), 7.56 (1H, m), 7.49 - 7.36 (5H, m), 6.41 (1H, d), 3.70 (3H, s), 3.02 (2H, t), 1.76 (2H, m), 1.05 (3H, t).

[1179] Production Example 14-1

[1180] Using Compound IIA-204 of the present invention in place of Compound IIA-203 of the present invention, according to Production Example 14, Compound IIA-201 of the present invention represented by the following formula was obtained.

[1181] [Chemical Formula 72]

[1182]

[1183] Compound IIA-201 of the present invention: 1 H-NMR (CDCl3) δ: 7.86 (1H, d), 7.69 - 7.63 (4H, m), 7.53 (2H, m), 7.44 (1H, m), 7.37 (2H, m), 6.41 (1H, d), 3.71 (3H, s), 3.02 (2H, t), 1.76 (2H, m), 1.05 (3H, t).

[1184] Production Example 15

[1185] To a mixture of 2.0 g of Compound IIA-40 of the present invention and 20 mL of THF, 3.2 mL of butyllithium (2.8 M, hexane solution) was added dropwise at -78°C, and the mixture was stirred at -78°C for 30 minutes. To the resulting mixture, a mixture of 3.1 g of N-fluorobis(benzenesulfonyl)amine and 20 mL of THF was added at -78°C, and the mixture was stirred at room temperature for 4 hours. Water was added to the resulting mixture, and extraction was performed with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 20:1) to obtain 1.2 g of Compound IIA-202 of the present invention represented by the following formula.

[1186] [Chemical Formula 73]

[1187]

[1188] Compound IIA-202 of the present invention: 1 H-NMR (CDCl3) δ: 7.58 (2H, m), 7.41 (2H, m), 5.90 (1H, d), 3.00 (2H, t), 1.75 (2H, m), 1.04 (3H, t).

[1189] Examples of the present compound and the compound of the present invention produced according to the above production methods and production examples are shown below.

[1190] In the compound represented by formula (L-1), Q is the group represented by Q1, n is 0, R 6 and R 7 are each a hydrogen atom, R1C , R 2C , R 3C , R 4C , R 5C and Z C The combination of and Z is a compound of any one of the combinations described in combination A (hereinafter, referred to as compound group SX1).

[1191] [Chemical formula 74]

[1192]

[1193] Combination A contains substituent numbers A1 to A2717. The substituent numbers A1 to A2717 represent, in the compound represented by formula (L-1), the R 1C , R 2C , R 3C , R 4C , R 5C and Z C combination, hereinafter, referred to as [substituent number; R 1C , R 2C , R 3C , R 4C , R 5C , Z C .

[1194] For example, the so-called substituent number A5 means that R 1C , R 2C , R 4C and R 5C are each a hydrogen atom, R 3C is a methyl group, and Z C is an ethyl group combination.

[1195] Combination A

[1196] [Substituent number; R 1C , R 2C , R 3C , R 4C , R 5C , Z C :

[1197] [A1; H, H, F, H, H, Et], [A2; H, H, Cl, H, H, Et], [A3; H, H, Br, H, H, Et], [A4; H, H, I, H, H, Et], [A5; H, H, Me, H, H, Et], [A6; H, H, OMe, H, H, Et], [A7; H, H, CF3, H, H, Et], [A8; H, H, CHF2, H, H, Et], [A9; H, H, NO2, H, H, Et], [A10; H, H, F, H, H, Pr], [A11; H, H, Cl, H, H, Pr], [A12; H, H, Br, H, H, Pr], [A13; H, H, I, H, H, Pr], [A14; H, H, Me, H, H, Pr], [A15; H, H, OMe, H, H, Pr], [A16; H, H, CF3, H, H, Pr], [A17; H, H, CHF2, H, H, Pr], [A18; H, H, NO2, H, H, Pr], [A19; H, H, F, H, H, i-Pr], [A20; H, H, Cl, H, H, i-Pr], [A21; H, H, Br, H, H, i-Pr], [A22; H, H, I, H, H, i-Pr], [A23; H, H, Me, H, H, i-Pr], [A24; H, H, OMe, H, H, i-Pr], [A25; H, H, CF3, H, H, i-Pr], [A26; H, H, CHF2, H, H, i-Pr], [A27; H, H, NO2, H, H, i-Pr], [A28; H, H, F, H, H, c-Pr], [A29; H, H, Cl, H, H, c-Pr], [A30; H, H, Br, H, H, c-Pr], [A31; H, H, I, H, H, c-Pr], [A32; H, H, Me, H, H, c-Pr], [A33; H, H, OMe, H, H, c-Pr], [A34; H, H, CF3, H, H, c-Pr], [A35; H, H, CHF2, H, H, c-Pr], [A36; H, H, NO2, H, H, c-Pr], [A37; H, H, F, H, H, Bu], [A38; H, H, Cl, H, H, Bu], [A39; H, H, Br, H, H, Bu], [A40; H, H, I, H, H, Bu], [A41; H, H, Me, H, H, Bu], [A42; H, H, OMe, H, H, Bu], [A43; H, H, CF3, H, H, Bu], [A44; H, H, CHF2, H, H, Bu], [A45; H, H, NO2, H, H, Bu], [A46; H, H, F, H, H, i-Bu], [A47; H, H, Cl, H, H, i-Bu], [A48;H,H,Br,H,H,i-Bu],[A49; H,H,I,H,H,i-Bu],[A50; H,H,Me,H,H,i-Bu],[A51; H,H,OMe,H,H,i-Bu],[A52; H,H,CF3,H,H,i-Bu],[A53; H,H,CHF2,H,H,i-Bu],[A54; H,H,NO2,H,H,i-Bu],[A55; H,H,F,H,H,CH2CF3],[A56; H,H,Cl,H,H,CH2CF3],[A57; H,H,Br,H,H,CH2CF3],[A58; H,H,I,H,H,CH2CF3],[A59; H,H,Me,H,H,CH2CF3],[A60; H,H,OMe,H,H,CH2CF3],[A61; H,H,CF3,H,H,CH2CF3],[A62; H,H,CHF2,H,H,CH2CF3],[A63; H,H,NO2,H,H,CH2CF3],[A64; H,H,F,H,H,CF2CH3],[A65; H,H,Cl,H,H,CF2CH3],[A66; H,H,Br,H,H,CF2CH3],[A67; H,H,I,H,H,CF2CH3],[A68; H,H,Me,H,H,CF2CH3],[A69; H,H,OMe,H,H,CF2CH3],[A70; H,H,CF3,H,H,CF2CH3],[A71; H,H,CHF2,H,H,CF2CH3],[A72; H,H,NO2,H,H,CF2CH3],[A73; H,H,F,H,H,2-Py],[A74; H,H,Cl,H,H,2-Py],[A75; H,H,Br,H,H,2-Py],[A76; H,H,I,H,H,2-Py],[A77; H,H,Me,H,H,2-Py],[A78; H,H,OMe,H,H,2-Py],[A79; H,H,CF3,H,H,2-Py],[A80; H,H,CHF2,H,H,2-Py],[A81; H,H,NO2,H,H,2-Py],[A82; H,H,F,H,H,3-Py],[A83; H,H,Cl,H,H,3-Py],[A84; H,H,Br,H,H,3-Py],[A85; H,H,I,H,H,3-Py],[A86; H,H,Me,H,H,3-Py],[A87; H,H,OMe,H,H,3-Py],[A88; H,H,CF3,H,H,3-Py],[A89; H,H,CHF2,H,H,3-Py],[A90; H,H,NO2,H,H,3-Py],[A91;H,H,F,H,H,4-Py],[A92; H,H,Cl,H,H,4-Py],[A93; H,H,Br,H,H,4-Py],[A94; H,H,I,H,H,4-Py],[A95; H,H,Me,H,H,4-Py],[A96; H,H,OMe,H,H,4-Py],[A97; H,H,CF3,H,H,4-Py],[A98; H,H,CHF2,H,H,4-Py],[A99; H,H,NO2,H,H,4-Py],[A100; H,F,H,H,H,Et],;

[1198] [A101; H, F, F, H, H, Et], [A102; H, F, Cl, H, H, Et], [A103; H, F, Br, H, H, Et], [A104; H, F, I, H, H, Et], [A105; H, F, Me, H, H, Et], [A106; H, F, OMe, H, H, Et], [A107; H, F, CF3, H, H, Et], [A108; H, F, CHF2, H, H, Et], [A109; H, F, NO2, H, H, Et], [A110; H, F, H, H, H, Pr], [A111; H, F, F, H, H, Pr], [A112; H, F, Cl, H, H, Pr], [A113; H, F, Br, H, H, Pr], [A114; H, F, I, H, H, Pr], [A115; H, F, Me, H, H, Pr], [A116; H, F, OMe, H, H, Pr], [A117; H, F, CF3, H, H, Pr], [A118; H, F, CHF2, H, H, Pr], [A119; H, F, NO2, H, H, Pr], [A120; H, F, H, H, H, i-Pr], [A121; H, F, F, H, H, i-Pr], [A122; H, F, Cl, H, H, i-Pr], [A123; H, F, Br, H, H, i-Pr], [A124; H, F, I, H, H, i-Pr], [A125; H, F, Me, H, H, i-Pr], [A126; H, F, OMe, H, H, i-Pr], [A127; H, F, CF3, H, H, i-Pr], [A128; H, F, CHF2, H, H, i-Pr], [A129; H, F, NO2, H, H, i-Pr], [A130; H, F, H, H, H, c-Pr], [A131; H, F, F, H, H, c-Pr], [A132; H, F, Cl, H, H, c-Pr], [A133; H, F, Br, H, H, c-Pr], [A134; H, F, I, H, H, c-Pr], [A135; H, F, Me, H, H, c-Pr], [A136; H, F, OMe, H, H, c-Pr], [A137; H, F, CF3, H, H, c-Pr], [A138; H, F, CHF2, H, H, c-Pr], [A139; H, F, NO2, H, H, c-Pr], [A140; H, F, H, H, H, Bu], [A141; H, F, F, H, H, Bu], [A142; H, F, Cl, H, H, Bu], [A143; H, F, Br, H, H, Bu], [A144; H, F, I, H, H, Bu], [A145; H, F, Me, H, H, Bu], [A146;[H, F, OMe, H, H, Bu], [A147; H, F, CF3, H, H, Bu], [A148; H, F, CHF2, H, H, Bu], [A149; H, F, NO2, H, H, Bu], [A150; H, F, H, H, H, i - Bu], [A151; H, F, F, H, H, i - Bu], [A152; H, F, Cl, H, H, i - Bu], [A153; H, F, Br, H, H, i - Bu], [A154; H, F, I, H, H, i - Bu], [A155; H, F, Me, H, H, i - Bu], [A156; H, F, OMe, H, H, i - Bu], [A157; H, F, CF3, H, H, i - Bu], [A158; H, F, CHF2, H, H, i - Bu], [A159; H, F, NO2, H, H, i - Bu], [A160; H, F, H, H, H, CH2CF3], [A161; H, F, F, H, H, CH2CF3], [A162; H, F, Cl, H, H, CH2CF3], [A163; H, F, Br, H, H, CH2CF3], [A164; H, F, I, H, H, CH2CF3], [A165; H, F, Me, H, H, CH2CF3], [A166; H, F, OMe, H, H, CH2CF3], [A167; H, F, CF3, H, H, CH2CF3], [A168; H, F, CHF2, H, H, CH2CF3], [A169; H, F, NO2, H, H, CH2CF3], [A170; H, F, H, H, H, CF2CH3], [A171; H, F, F, H, H, CF2CH3], [A172; H, F, Cl, H, H, CF2CH3], [A173; H, F, Br, H, H, CF2CH3], [A174; H, F, I, H, H, CF2CH3], [A175; H, F, Me, H, H, CF2CH3], [A176; H, F, OMe, H, H, CF2CH3], [A177; H, F, CF3, H, H, CF2CH3], [A178; H, F, CHF2, H, H, CF2CH3], [A179; H, F, NO2, H, H, CF2CH3], [A180; H, F, H, H, H, 2 - Py], [A181; H, F, F, H, H, 2 - Py], [A182; H, F, Cl, H, H, 2 - Py], [A183; H, F, Br, H, H, 2 - Py], [A184; H, F, I, H, H, 2 - Py], [A185; H, F, Me, H, H, 2 - Py], [A186; H, F, OMe, H, H, 2 - Py], [A187;H,F,CF3,H,H,2-Py],[A188; H,F,CHF2,H,H,2-Py],[A189; H,F,NO2,H,H,2-Py],[A190; H,F,H,H,H,3-Py],[A191; H,F,F,H,H,3-Py],[A192; H,F,Cl,H,H,3-Py],[A193; H,F,Br,H,H,3-Py],[A194; H,F,I,H,H,3-Py],[A195; H,F,Me,H,H,3-Py],[A196; H,F,OMe,H,H,3-Py],[A197; H,F,CF3,H,H,3-Py],[A198; H,F,CHF2,H,H,3-Py],[A199; H,F,NO2,H,H,3-Py],[A200; H,F,H,H,H,4-Py],[A201; H,F,F,H,H,4-Py],[A202; H,F,Cl,H,H,4-Py],[A203; H,F,Br,H,H,4-Py],[A204; H,F,I,H,H,4-Py],[A205; H,F,Me,H,H,4-Py],[A206; H,F,OMe,H,H,4-Py],[A207; H,F,CF3,H,H,4-Py],[A208; H,F,CHF2,H,H,4-Py],[A209; H,F,NO2,H,H,4-Py],[A210; H,Cl,H,H,H,Et],[A211; H,Cl,F,H,H,Et],;

[1199] [A212; H, Cl, Cl, H, H, Et], [A213; H, Cl, Br, H, H, Et], [A214; H, Cl, I, H, H, Et], [A215; H, Cl, Me, H, H, Et], [A216; H, Cl, OMe, H, H, Et], [A217; H, Cl, CF3, H, H, Et], [A218; H, Cl, CHF2, H, H, Et], [A219; H, Cl, NO2, H, H, Et], [A220; H, Cl, H, H, H, Pr], [A221; H, Cl, F, H, H, Pr], [A222; H, Cl, Cl, H, H, Pr], [A223; H, Cl, Br, H, H, Pr], [A224; H, Cl, I, H, H, Pr], [A225; H, Cl, Me, H, H, Pr], [A226; H, Cl, OMe, H, H, Pr], [A227; H, Cl, CF3, H, H, Pr], [A228; H, Cl, CHF2, H, H, Pr], [A229; H, Cl, NO2, H, H, Pr], [A230; H, Cl, H, H, H, i-Pr], [A231; H, Cl, F, H, H, i-Pr], [A232; H, Cl, Cl, H, H, i-Pr], [A233; H, Cl, Br, H, H, i-Pr], [A234; H, Cl, I, H, H, i-Pr], [A235; H, Cl, Me, H, H, i-Pr], [A236; H, Cl, OMe, H, H, i-Pr], [A237; H, Cl, CF3, H, H, i-Pr], [A238; H, Cl, CHF2, H, H, i-Pr], [A239; H, Cl, NO2, H, H, i-Pr], [A240; H, Cl, H, H, H, c-Pr], [A241; H, Cl, F, H, H, c-Pr], [A242; H, Cl, Cl, H, H, c-Pr], [A243; H, Cl, Br, H, H, c-Pr], [A244; H, Cl, I, H, H, c-Pr], [A245; H, Cl, Me, H, H, c-Pr], [A246; H, Cl, OMe, H, H, c-Pr], [A247; H, Cl, CF3, H, H, c-Pr], [A248; H, Cl, CHF2, H, H, c-Pr], [A249; H, Cl, NO2, H, H, c-Pr], [A250; H, Cl, H, H, H, Bu], [A251; H, Cl, F, H, H, Bu], [A252; H, Cl, Cl, H, H, Bu], [A253; H, Cl, Br, H, H, Bu], [A254; H, Cl, I, H, H, Bu], [A255;H, Cl, Me, H, H, Bu], [A256; H, Cl, OMe, H, H, Bu], [A257; H, Cl, CF3, H, H, Bu], [A258; H, Cl, CHF2, H, H, Bu], [A259; H, Cl, NO2, H, H, Bu], [A260; H, Cl, H, H, H, i - Bu], [A261; H, Cl, F, H, H, i - Bu], [A262; H, Cl, Cl, H, H, i - Bu], [A263; H, Cl, Br, H, H, i - Bu], [A264; H, Cl, I, H, H, i - Bu], [A265; H, Cl, Me, H, H, i - Bu], [A266; H, Cl, OMe, H, H, i - Bu], [A267; H, Cl, CF3, H, H, i - Bu], [A268; H, Cl, CHF2, H, H, i - Bu], [A269; H, Cl, NO2, H, H, i - Bu], [A270; H, Cl, H, H, H, CH2CF3], [A271; H, Cl, F, H, H, CH2CF3], [A272; H, Cl, Cl, H, H, CH2CF3], [A273; H, Cl, Br, H, H, CH2CF3], [A274; H, Cl, I, H, H, CH2CF3], [A275; H, Cl, Me, H, H, CH2CF3], [A276; H, Cl, OMe, H, H, CH2CF3], [A277; H, Cl, CF3, H, H, CH2CF3], [A278; H, Cl, CHF2, H, H, CH2CF3], [A279; H, Cl, NO2, H, H, CH2CF3], [A280; H, Cl, H, H, H, CF2CH3], [A281; H, Cl, F, H, H, CF2CH3], [A282; H, Cl, Cl, H, H, CF2CH3], [A283; H, Cl, Br, H, H, CF2CH3], [A284; H, Cl, I, H, H, CF2CH3], [A285; H, Cl, Me, H, H, CF2CH3], [A286; H, Cl, OMe, H, H, CF2CH3], [A287; H, Cl, CF3, H, H, CF2CH3], [A288; H, Cl, CHF2, H, H, CF2CH3], [A289; H, Cl, NO2, H, H, CF2CH3], [A290; H, Cl, H, H, H, 2 - Py], [A291; H, Cl, F, H, H, 2 - Py], [A292; H, Cl, Cl, H, H, 2 - Py], [A293; H, Cl, Br, H, H, 2 - Py], [A294; H, Cl, I, H, H, 2 - Py], [A295;H, Cl, Me, H, H, 2-Py], [A296; H, Cl, OMe, H, H, 2-Py], [A297; H, Cl, CF3, H, H, 2-Py], [A298; H, Cl, CHF2, H, H, 2-Py], [A299; H, Cl, NO2, H, H, 2-Py], [A300; H, Cl, H, H, H, 3-Py], [A301; H, Cl, F, H, H, 3-Py], [A302; H, Cl, Cl, H, H, 3-Py], [A303; H, Cl, Br, H, H, 3-Py], [A304; H, Cl, I, H, H, 3-Py], [A305; H, Cl, Me, H, H, 3-Py], [A306; H, Cl, OMe, H, H, 3-Py], [A307; H, Cl, CF3, H, H, 3-Py], [A308; H, Cl, CHF2, H, H, 3-Py], [A309; H, Cl, NO2, H, H, 3-Py], [A310; H, Cl, H, H, H, 4-Py], [A311; H, Cl, F, H, H, 4-Py], [A312; H, Cl, Cl, H, H, 4-Py], [A313; H, Cl, Br, H, H, 4-Py], [A314; H, Cl, I, H, H, 4-Py], [A315; H, Cl, Me, H, H, 4-Py], [A316; H, Cl, OMe, H, H, 4-Py], [A317; H, Cl, CF3, H, H, 4-Py], [A318; H, Cl, CHF2, H, H, 4-Py], [A319; H, Cl, NO2, H, H, 4-Py], [A320; H, Br, H, H, H, Et], [A321; H, Br, F, H, H, Et], [A322; H, Br, Cl, H, H, Et], [A323; H, Br, Br, H, H, Et], [A324; H, Br, I, H, H, Et], [A325; H, Br, Me, H, H, Et], [A326; H, Br, OMe, H, H, Et], [A327; H, Br, CF3, H, H, Et], [A328; H, Br, CHF2, H, H, Et], [A329; H, Br, NO2, H, H, Et], [A330; H, Br, H, H, H, Pr], [A331; H, Br, F, H, H, Pr], [A332; H, Br, Cl, H, H, Pr], [A333; H, Br, Br, H, H, Pr], [A334; H, Br, I, H, H, Pr], [A335; H, Br, Me, H, H, Pr], [A336; H, Br, OMe, H, H, Pr], [A337;[[H, Br, CF3, H, H, Pr], [A338; H, Br, CHF2, H, H, Pr], [A339; H, Br, NO2, H, H, Pr], [A340; H, Br, H, H, H, i-Pr], [A341; H, Br, F, H, H, i-Pr], [A342; H, Br, Cl, H, H, i-Pr], ;

[1200] [A343; H, Br, Br, H, H, i-Pr], [A344; H, Br, I, H, H, i-Pr], [A345; H, Br, Me, H, H, i-Pr], [A346; H, Br, OMe, H, H, i-Pr], [A347; H, Br, CF3, H, H, i-Pr], [A348; H, Br, CHF2, H, H, i-Pr], [A349; H, Br, NO2, H, H, i-Pr], [A350; H, Br, H, H, H, c-Pr], [A351; H, Br, F, H, H, c-Pr], [A352; H, Br, Cl, H, H, c-Pr], [A353; H, Br, Br, H, H, c-Pr], [A354; H, Br, I, H, H, c-Pr], [A355; H, Br, Me, H, H, c-Pr], [A356; H, Br, OMe, H, H, c-Pr], [A357; H, Br, CF3, H, H, c-Pr], [A358; H, Br, CHF2, H, H, c-Pr], [A359; H, Br, NO2, H, H, c-Pr], [A360; H, Br, H, H, H, Bu], [A361; H, Br, F, H, H, Bu], [A362; H, Br, Cl, H, H, Bu], [A363; H, Br, Br, H, H, Bu], [A364; H, Br, I, H, H, Bu], [A365; H, Br, Me, H, H, Bu], [A366; H, Br, OMe, H, H, Bu], [A367; H, Br, CF3, H, H, Bu], [A368; H, Br, CHF2, H, H, Bu], [A369; H, Br, NO2, H, H, Bu], [A370; H, Br, H, H, H, i-Bu], [A371; H, Br, F, H, H, i-Bu], [A372; H, Br, Cl, H, H, i-Bu], [A373; H, Br, Br, H, H, i-Bu], [A374; H, Br, I, H, H, i-Bu], [A375; H, Br, Me, H, H, i-Bu], [A376; H, Br, OMe, H, H, i-Bu], [A377; H, Br, CF3, H, H, i-Bu], [A378; H, Br, CHF2, H, H, i-Bu], [A379; H, Br, NO2, H, H, i-Bu], [A380; H, Br, H, H, H, CH2CF3], [A381; H, Br, F, H, H, CH2CF3], [A382; H, Br, Cl, H, H, CH2CF3], [A383; H, Br, Br, H, H, CH2CF3], [A384;H, Br, I, H, H, CH2CF3], [A385; H, Br, Me, H, H, CH2CF3], [A386; H, Br, OMe, H, H, CH2CF3], [A387; H, Br, CF3, H, H, CH2CF3], [A388; H, Br, CHF2, H, H, CH2CF3], [A389; H, Br, NO2, H, H, CH2CF3], [A390; H, Br, H, H, H, CF2CH3], [A391; H, Br, F, H, H, CF2CH3], [A392; H, Br, Cl, H, H, CF2CH3], [A393; H, Br, Br, H, H, CF2CH3], [A394; H, Br, I, H, H, CF2CH3], [A395; H, Br, Me, H, H, CF2CH3], [A396; H, Br, OMe, H, H, CF2CH3], [A397; H, Br, CF3, H, H, CF2CH3], [A398; H, Br, CHF2, H, H, CF2CH3], [A399; H, Br, NO2, H, H, CF2CH3], [A400; H, Br, H, H, H, 2-Py], [A401; H, Br, F, H, H, 2-Py], [A402; H, Br, Cl, H, H, 2-Py], [A403; H, Br, Br, H, H, 2-Py], [A404; H, Br, I, H, H, 2-Py], [A405; H, Br, Me, H, H, 2-Py], [A406; H, Br, OMe, H, H, 2-Py], [A407; H, Br, CF3, H, H, 2-Py], [A408; H, Br, CHF2, H, H, 2-Py], [A409; H, Br, NO2, H, H, 2-Py], [A410; H, Br, H, H, H, 3-Py], [A411; H, Br, F, H, H, 3-Py], [A412; H, Br, Cl, H, H, 3-Py], [A413; H, Br, Br, H, H, 3-Py], [A414; H, Br, I, H, H, 3-Py], [A415; H, Br, Me, H, H, 3-Py], [A416; H, Br, OMe, H, H, 3-Py], [A417; H, Br, CF3, H, H, 3-Py], [A418; H, Br, CHF2, H, H, 3-Py], [A419; H, Br, NO2, H, H, 3-Py], [A420; H, Br, H, H, H, 4-Py], [A421; H, Br, F, H, H, 4-Py], [A422; H, Br, Cl, H, H, 4-Py], [A423; H, Br, Br, H, H, 4-Py], [A424;H, Br, I, H, H, 4-Py], [A425; H, Br, Me, H, H, 4-Py], [A426; H, Br, OMe, H, H, 4-Py], [A427; H, Br, CF3, H, H, 4-Py], [A428; H, Br, CHF2, H, H, 4-Py], [A429; H, Br, NO2, H, H, 4-Py], [A430; H, CF3, H, H, H, Et], [A431; H, CF3, F, H, H, Et], [A432; H, CF3, Cl, H, H, Et], [A433; H, CF3, Br, H, H, Et], [A434; H, CF3, I, H, H, Et], [A435; H, CF3, Me, H, H, Et], [A436; H, CF3, OMe, H, H, Et], [A437; H, CF3, CF3, H, H, Et], [A438; H, CF3, CHF2, H, H, Et], [A439; H, CF3, NO2, H, H, Et], [A440; H, CF3, H, H, H, Pr], [A441; H, CF3, F, H, H, Pr], [A442; H, CF3, Cl, H, H, Pr], [A443; H, CF3, Br, H, H, Pr], [A444; H, CF3, I, H, H, Pr], [A445; H, CF3, Me, H, H, Pr], [A446; H, CF3, OMe, H, H, Pr], [A447; H, CF3, CF3, H, H, Pr], [A448; H, CF3, CHF2, H, H, Pr], [A449; H, CF3, NO2, H, H, Pr], [A450; H, CF3, H, H, H, i-Pr], [A451; H, CF3, F, H, H, i-Pr], [A452; H, CF3, Cl, H, H, i-Pr], [A453; H, CF3, Br, H, H, i-Pr], [A454; H, CF3, I, H, H, i-Pr], [A455; H, CF3, Me, H, H, i-Pr], [A456; H, CF3, OMe, H, H, i-Pr], [A457; H, CF3, CF3, H, H, i-Pr], [A458; H, CF3, CHF2, H, H, i-Pr], [A459; H, CF3, NO2, H, H, i-Pr], [A460; H, CF3, H, H, H, c-Pr], [A461; H, CF3, F, H, H, c-Pr], [A462; H, CF3, Cl, H, H, c-Pr], [A463; H, CF3, Br, H, H, c-Pr], [A464; H, CF3, I, H, H, c-Pr], [A465;H, CF3, Me, H, H, c-Pr, [A466]; H, CF3, OMe, H, H, c-Pr, [A467]; H, CF3, CF3, H, H, c-Pr, [A468]; H, CF3, CHF2, H, H, c-Pr, [A469]; H, CF3, NO2, H, H, c-Pr, [A470]; H, CF3, H, H, H, Bu, [A471]; H, CF3, F, H, H, Bu, [A472]; H, CF3, Cl, H, H, Bu, [A473]; H, CF3, Br, H, H, Bu, [A474]; H, CF3, I, H, H, Bu, [A475]; H, CF3, Me, H, H, Bu, [A476]; H, CF3, OMe, H, H, Bu, [A477]; H, CF3, CF3, H, H, Bu, [A478]; H, CF3, CHF2, H, H, Bu, [A479]; H, CF3, NO2, H, H, Bu, [A480]; H, CF3, H, H, H, i-Bu, [A481]; H, CF3, F, H, H, i-Bu, [A482]; H, CF3, Cl, H, H, i-Bu, [A483]; H, CF3, Br, H, H, i-Bu, [A484]; H, CF3, I, H, H, i-Bu, [A485]; H, CF3, Me, H, H, i-Bu, [A486]; H, CF3, OMe, H, H, i-Bu, [A487]; H, CF3, CF3, H, H, i-Bu, [A488]; H, CF3, CHF2, H, H, i-Bu, [A489]; H, CF3, NO2, H, H, i-Bu, [A490]; H, CF3, H, H, H, CH2CF3, [A491]; H, CF3, F, H, H, CH2CF3, [A492]; H, CF3, Cl, H, H, CH2CF3, [A493]; H, CF3, Br, H, H, CH2CF3],;

[1201] [A494; H, CF3, I, H, H, CH2CF3], [A495; H, CF3, Me, H, H, CH2CF3], [A496; H, CF3, OMe, H, H, CH2CF3], [A497; H, CF3, CF3, H, H, CH2CF3], [A498; H, CF3, CHF2, H, H, CH2CF3], [A499; H, CF3, NO2, H, H, CH2CF3], [A500; H, CF3, H, H, H, CF2CH3], [A501; H, CF3, F, H, H, CF2CH3], [A502; H, CF3, Cl, H, H, CF2CH3], [A503; H, CF3, Br, H, H, CF2CH3], [A504; H, CF3, I, H, H, CF2CH3], [A505; H, CF3, Me, H, H, CF2CH3], [A506; H, CF3, OMe, H, H, CF2CH3], [A507; H, CF3, CF3, H, H, CF2CH3], [A508; H, CF3, CHF2, H, H, CF2CH3], [A509; H, CF3, NO2, H, H, CF2CH3], [A510; H, CF3, H, H, H, 2-Py], [A511; H, CF3, F, H, H, 2-Py], [A512; H, CF3, Cl, H, H, 2-Py], [A513; H, CF3, Br, H, H, 2-Py], [A514; H, CF3, I, H, H, 2-Py], [A515; H, CF3, Me, H, H, 2-Py], [A516; H, CF3, OMe, H, H, 2-Py], [A517; H, CF3, CF3, H, H, 2-Py], [A518; H, CF3, CHF2, H, H, 2-Py], [A519; H, CF3, NO2, H, H, 2-Py], [A520; H, CF3, H, H, H, 3-Py], [A521; H, CF3, F, H, H, 3-Py], [A522; H, CF3, Cl, H, H, 3-Py], [A523; H, CF3, Br, H, H, 3-Py], [A524; H, CF3, I, H, H, 3-Py], [A525; H, CF3, Me, H, H, 3-Py], [A526; H, CF3, OMe, H, H, 3-Py], [A527; H, CF3, CF3, H, H, 3-Py], [A528; H, CF3, CHF2, H, H, 3-Py], [A529; H, CF3, NO2, H, H, 3-Py], [A530; H, CF3, H, H, H, 4-Py], [A531; H, CF3, F, H, H, 4-Py], [A532;H, CF3, Cl, H, H, 4-Py], [A533; H, CF3, Br, H, H, 4-Py], [A534; H, CF3, I, H, H, 4-Py], [A535; H, CF3, Me, H, H, 4-Py], [A536; H, CF3, OMe, H, H, 4-Py], [A537; H, CF3, CF3, H, H, 4-Py], [A538; H, CF3, CHF2, H, H, 4-Py], [A539; H, CF3, NO2, H, H, 4-Py], [A540; H, NO2, H, H, H, Et], [A541; H, NO2, F, H, H, Et], [A542; H, NO2, Cl, H, H, Et], [A543; H, NO2, Br, H, H, Et], [A544; H, NO2, I, H, H, Et], [A545; H, NO2, Me, H, H, Et], [A546; H, NO2, OMe, H, H, Et], [A547; H, NO2, CF3, H, H, Et], [A548; H, NO2, CHF2, H, H, Et], [A549; H, NO2, NO2, H, H, Et], [A550; H, NO2, H, H, H, Pr], [A551; H, NO2, F, H, H, Pr], [A552; H, NO2, Cl, H, H, Pr], [A553; H, NO2, Br, H, H, Pr], [A554; H, NO2, I, H, H, Pr], [A555; H, NO2, Me, H, H, Pr], [A556; H, NO2, OMe, H, H, Pr], [A557; H, NO2, CF3, H, H, Pr], [A558; H, NO2, CHF2, H, H, Pr], [A559; H, NO2, NO2, H, H, Pr], [A560; H, NO2, H, H, H, i-Pr], [A561; H, NO2, F, H, H, i-Pr], [A562; H, NO2, Cl, H, H, i-Pr], [A563; H, NO2, Br, H, H, i-Pr], [A564; H, NO2, I, H, H, i-Pr], [A565; H, NO2, Me, H, H, i-Pr], [A566; H, NO2, OMe, H, H, i-Pr], [A567; H, NO2, CF3, H, H, i-Pr], [A568; H, NO2, CHF2, H, H, i-Pr], [A569; H, NO2, NO2, H, H, i-Pr], [A570; H, NO2, H, H, H, c-Pr], [A571; H, NO2, F, H, H, c-Pr], [A572; H, NO2, Cl, H, H, c-Pr], [A573;H, NO2, Br, H, H, c-Pr], [A574; H, NO2, I, H, H, c-Pr], [A575; H, NO2, Me, H, H, c-Pr], [A576; H, NO2, OMe, H, H, c-Pr], [A577; H, NO2, CF3, H, H, c-Pr], [A578; H, NO2, CHF2, H, H, c-Pr], [A579; H, NO2, NO2, H, H, c-Pr], [A580; H, NO2, H, H, H, Bu], [A581; H, NO2, F, H, H, Bu], [A582; H, NO2, Cl, H, H, Bu], [A583; H, NO2, Br, H, H, Bu], [A584; H, NO2, I, H, H, Bu], [A585; H, NO2, Me, H, H, Bu], [A586; H, NO2, OMe, H, H, Bu], [A587; H, NO2, CF3, H, H, Bu], [A588; H, NO2, CHF2, H, H, Bu], [A589; H, NO2, NO2, H, H, Bu], [A590; H, NO2, H, H, H, i-Bu], [A591; H, NO2, F, H, H, i-Bu], [A592; H, NO2, Cl, H, H, i-Bu], [A593; H, NO2, Br, H, H, i-Bu], [A594; H, NO2, I, H, H, i-Bu], [A595; H, NO2, Me, H, H, i-Bu], [A596; H, NO2, OMe, H, H, i-Bu], [A597; H, NO2, CF3, H, H, i-Bu], [A598; H, NO2, CHF2, H, H, i-Bu], [A599; H, NO2, NO2, H, H, i-Bu], [A600; H, NO2, H, H, H, CH2CF3], [A601; H, NO2, F, H, H, CH2CF3], [A602; H, NO2, Cl, H, H, CH2CF3], [A603; H, NO2, Br, H, H, CH2CF3], [A604; H, NO2, I, H, H, CH2CF3], [A605; H, NO2, Me, H, H, CH2CF3], [A606; H, NO2, OMe, H, H, CH2CF3], [A607; H, NO2, CF3, H, H, CH2CF3], [A608; H, NO2, CHF2, H, H, CH2CF3], [A609; H, NO2, NO2, H, H, CH2CF3], [A610; H, NO2, H, H, H, CF2CH3], [A611; H, NO2, F, H, H, CF2CH3], [A612;[H, NO2, Cl, H, H, CF2CH3],;

[1202] [A613; H, NO2, Br, H, H, CF2CH3], [A614; H, NO2, I, H, H, CF2CH3], [A615; H, NO2, Me, H, H, CF2CH3], [A616; H, NO2, OMe, H, H, CF2CH3], [A617; H, NO2, CF3, H, H, CF2CH3], [A618; H, NO2, CHF2, H, H, CF2CH3], [A619; H, NO2, NO2, H, H, CF2CH3], [A620; H, NO2, H, H, H, 2-Py], [A621; H, NO2, F, H, H, 2-Py], [A622; H, NO2, Cl, H, H, 2-Py], [A623; H, NO2, Br, H, H, 2-Py], [A624; H, NO2, I, H, H, 2-Py], [A625; H, NO2, Me, H, H, 2-Py], [A626; H, NO2, OMe, H, H, 2-Py], [A627; H, NO2, CF3, H, H, 2-Py], [A628; H, NO2, CHF2, H, H, 2-Py], [A629; H, NO2, NO2, H, H, 2-Py], [A630; H, NO2, H, H, H, 3-Py], [A631; H, NO2, F, H, H, 3-Py], [A632; H, NO2, Cl, H, H, 3-Py], [A633; H, NO2, Br, H, H, 3-Py], [A634; H, NO2, I, H, H, 3-Py], [A635; H, NO2, Me, H, H, 3-Py], [A636; H, NO2, OMe, H, H, 3-Py], [A637; H, NO2, CF3, H, H, 3-Py], [A638; H, NO2, CHF2, H, H, 3-Py], [A639; H, NO2, NO2, H, H, 3-Py], [A640; H, NO2, H, H, H, 4-Py], [A641; H, NO2, F, H, H, 4-Py], [A642; H, NO2, Cl, H, H, 4-Py], [A643; H, NO2, Br, H, H, 4-Py], [A644; H, NO2, I, H, H, 4-Py], [A645; H, NO2, Me, H, H, 4-Py], [A646; H, NO2, OMe, H, H, 4-Py], [A647; H, NO2, CF3, H, H, 4-Py], [A648; H, NO2, CHF2, H, H, 4-Py], [A649; H, NO2, NO2, H, H, 4-Py], [A650; H, OCH2Ph, H, H, H, Et], [A651;[H, OCH2Ph, F, H, H, Et], [A652; H, OCH2Ph, Cl, H, H, Et], [A653; H, OCH2Ph, Br, H, H, Et], [A654; H, OCH2Ph, I, H, H, Et], [A655; H, OCH2Ph, Me, H, H, Et], [A656; H, OCH2Ph, OMe, H, H, Et], [A657; H, OCH2Ph, CF3, H, H, Et], [A658; H, OCH2Ph, CHF2, H, H, Et], [A659; H, OCH2Ph, NO2, H, H, Et], [A660; H, OCH2Ph, H, H, H, Pr], [A661; H, OCH2Ph, F, H, H, Pr], [A662; H, OCH2Ph, Cl, H, H, Pr], [A663; H, OCH2Ph, Br, H, H, Pr], [A664; H, OCH2Ph, I, H, H, Pr], [A665; H, OCH2Ph, Me, H, H, Pr], [A666; H, OCH2Ph, OMe, H, H, Pr], [A667; H, OCH2Ph, CF3, H, H, Pr], [A668; H, OCH2Ph, CHF2, H, H, Pr], [A669; H, OCH2Ph, NO2, H, H, Pr], [A670; H, OCH2Ph, H, H, H, i-Pr], [A671; H, OCH2Ph, F, H, H, i-Pr], [A672; H, OCH2Ph, Cl, H, H, i-Pr], [A673; H, OCH2Ph, Br, H, H, i-Pr], [A674; H, OCH2Ph, I, H, H, i-Pr], [A675; H, OCH2Ph, Me, H, H, i-Pr], [A676; H, OCH2Ph, OMe, H, H, i-Pr], [A677; H, OCH2Ph, CF3, H, H, i-Pr], [A678; H, OCH2Ph, CHF2, H, H, i-Pr], [A679; H, OCH2Ph, NO2, H, H, i-Pr], [A680; H, OCH2Ph, H, H, H, c-Pr], [A681; H, OCH2Ph, F, H, H, c-Pr], [A682; H, OCH2Ph, Cl, H, H, c-Pr], [A683; H, OCH2Ph, Br, H, H, c-Pr], [A684; H, OCH2Ph, I, H, H, c-Pr], [A685; H, OCH2Ph, Me, H, H, c-Pr], [A686; H, OCH2Ph, OMe, H, H, c-Pr], [A687;[H, OCH2Ph, CF3, H, H, c-Pr], [A688]; [H, OCH2Ph, CHF2, H, H, c-Pr], [A689]; [H, OCH2Ph, NO2, H, H, c-Pr], [A690]; [H, OCH2Ph, H, H, H, Bu], [A691]; [H, OCH2Ph, F, H, H, Bu], [A692]; [H, OCH2Ph, Cl, H, H, Bu], [A693]; [H, OCH2Ph, Br, H, H, Bu], [A694]; [H, OCH2Ph, I, H, H, Bu], [A695]; [H, OCH2Ph, Me, H, H, Bu], [A696]; [H, OCH2Ph, OMe, H, H, Bu], [A697]; [H, OCH2Ph, CF3, H, H, Bu], [A698]; [H, OCH2Ph, CHF2, H, H, Bu], [A699]; [H, OCH2Ph, NO2, H, H, Bu], [A700]; [H, OCH2Ph, H, H, H, i-Bu], [A701]; [H, OCH2Ph, F, H, H, i-Bu], [A702]; [H, OCH2Ph, Cl, H, H, i-Bu], [A703]; [H, OCH2Ph, Br, H, H, i-Bu], [A704]; [H, OCH2Ph, I, H, H, i-Bu], [A705]; [H, OCH2Ph, Me, H, H, i-Bu], [A706]; [H, OCH2Ph, OMe, H, H, i-Bu], [A707]; [H, OCH2Ph, CF3, H, H, i-Bu], [A708]; [H, OCH2Ph, CHF2, H, H, i-Bu], [A709]; [H, OCH2Ph, NO2, H, H, i-Bu], [A710]; [H, OCH2Ph, H, H, H, CH2CF3], [A711]; [H, OCH2Ph, F, H, H, CH2CF3], [A712]; [H, OCH2Ph, Cl, H, H, CH2CF3], [A713]; [H, OCH2Ph, Br, H, H, CH2CF3], [A714]; [H, OCH2Ph, I, H, H, CH2CF3], [A715]; [H, OCH2Ph, Me, H, H, CH2CF3], [A716]; [H, OCH2Ph, OMe, H, H, CH2CF3], [A717]; [H, OCH2Ph, CF3, H, H, CH2CF3], [A718]; [H, OCH2Ph, CHF2, H, H, CH2CF3], [A719]; [H, OCH2Ph, NO2, H, H, CH2CF3], [A720]; [H, OCH2Ph, H, H, H, CF2CH3], [A721]; [H, OCH2Ph, F, H, H, CF2CH3], [A722;[H, OCH2Ph, Cl, H, H, CF2CH3], [A723; H, OCH2Ph, Br, H, H, CF2CH3], [A724; H, OCH2Ph, I, H, H, CF2CH3], [A725; H, OCH2Ph, Me, H, H, CF2CH3], [A726; H, OCH2Ph, OMe, H, H, CF2CH3], [A727; H, OCH2Ph, CF3, H, H, CF2CH3], [A728; H, OCH2Ph, CHF2, H, H, CF2CH3], [A729; H, OCH2Ph, NO2, H, H, CF2CH3], [A730; H, OCH2Ph, H, H, H, 2-Py], [A731; H, OCH2Ph, F, H, H, 2-Py], [A732; H, OCH2Ph, Cl, H, H, 2-Py], [A733; H, OCH2Ph, Br, H, H, 2-Py], [A734; H, OCH2Ph, I, H, H, 2-Py], [A735; H, OCH2Ph, Me, H, H, 2-Py], [A736; H, OCH2Ph, OMe, H, H, 2-Py], [A737; H, OCH2Ph, CF3, H, H, 2-Py], [A738; H, OCH2Ph, CHF2, H, H, 2-Py], [A739; H, OCH2Ph, NO2, H, H, 2-Py], [A740; H, OCH2Ph, H, H, H, 3-Py], [A741; H, OCH2Ph, F, H, H, 3-Py], [A742; H, OCH2Ph, Cl, H, H, 3-Py], ;

[1203] [A743; H, OCH2Ph, Br, H, H, 3-Py], [A744; H, OCH2Ph, I, H, H, 3-Py], [A745; H, OCH2Ph, Me, H, H, 3-Py], [A746; H, OCH2Ph, OMe, H, H, 3-Py], [A747; H, OCH2Ph, CF3, H, H, 3-Py], [A748; H, OCH2Ph, CHF2, H, H, 3-Py], [A749; H, OCH2Ph, NO2, H, H, 3-Py], [A750; H, OCH2Ph, H, H, H, 4-Py], [A751; H, OCH2Ph, F, H, H, 4-Py], [A752; H, OCH2Ph, Cl, H, H, 4-Py], [A753; H, OCH2Ph, Br, H, H, 4-Py], [A754; H, OCH2Ph, I, H, H, 4-Py], [A755; H, OCH2Ph, Me, H, H, 4-Py], [A756; H, OCH2Ph, OMe, H, H, 4-Py], [A757; H, OCH2Ph, CF3, H, H, 4-Py], [A758; H, OCH2Ph, CHF2, H, H, 4-Py], [A759; H, OCH2Ph, NO2, H, H, 4-Py], [A760; H, F, H, F, H, Et], [A761; H, F, F, F, H, Et], [A762; H, F, Cl, F, H, Et], [A763; H, F, Br, F, H, Et], [A764; H, F, I, F, H, Et], [A765; H, F, Me, F, H, Et], [A766; H, F, OMe, F, H, Et], [A767; H, F, CF3, F, H, Et], [A768; H, F, CHF2, F, H, Et], [A769; H, F, NO2, F, H, Et], [A770; H, F, H, F, H, Pr], [A771; H, F, F, F, H, Pr], [A772; H, F, Cl, F, H, Pr], [A773; H, F, Br, F, H, Pr], [A774; H, F, I, F, H, Pr], [A775; H, F, Me, F, H, Pr], [A776; H, F, OMe, F, H, Pr], [A777; H, F, CF3, F, H, Pr], [A778; H, F, CHF2, F, H, Pr], [A779; H, F, NO2, F, H, Pr], [A780; H, F, H, F, H, i-Pr], [A781; H, F, F, F, H, i-Pr], [A782; H, F, Cl, F, H, i-Pr], [A783;H,F,Br,F,H,i-Pr],[A784; H,F,I,F,H,i-Pr],[A785; H,F,Me,F,H,i-Pr],[A786; H,F,OMe,F,H,i-Pr],[A787; H,F,CF3,F,H,i-Pr],[A788; H,F,CHF2,F,H,i-Pr],[A789; H,F,NO2,F,H,i-Pr],[A790; H,F,H,F,H,c-Pr],[A791; H,F,F,F,H,c-Pr],[A792; H,F,Cl,F,H,c-Pr],[A793; H,F,Br,F,H,c-Pr],[A794; H,F,I,F,H,c-Pr],[A795; H,F,Me,F,H,c-Pr],[A796; H,F,OMe,F,H,c-Pr],[A797; H,F,CF3,F,H,c-Pr],[A798; H,F,CHF2,F,H,c-Pr],[A799; H,F,NO2,F,H,c-Pr],[A800; H,F,H,F,H,Bu],[A801; H,F,F,F,H,Bu],[A802; H,F,Cl,F,H,Bu],[A803; H,F,Br,F,H,Bu],[A804; H,F,I,F,H,Bu],[A805; H,F,Me,F,H,Bu],[A806; H,F,OMe,F,H,Bu],[A807; H,F,CF3,F,H,Bu],[A808; H,F,CHF2,F,H,Bu],[A809; H,F,NO2,F,H,Bu],[A810; H,F,H,F,H,i-Bu],[A811; H,F,F,F,H,i-Bu],[A812; H,F,Cl,F,H,i-Bu],[A813; H,F,Br,F,H,i-Bu],[A814; H,F,I,F,H,i-Bu],[A815; H,F,Me,F,H,i-Bu],[A816; H,F,OMe,F,H,i-Bu],[A817; H,F,CF3,F,H,i-Bu],[A818; H,F,CHF2,F,H,i-Bu],[A819; H,F,NO2,F,H,i-Bu],[A820; H,F,H,F,H,CH2CF3],[A821; H,F,F,F,H,CH2CF3],[A822; H,F,Cl,F,H,CH2CF3],[A823; H,F,Br,F,H,CH2CF3],[A824; H,F,I,F,H,CH2CF3],[A825; H,F,Me,F,H,CH2CF3],[A826;[H,F,OMe,F,H,CH2CF3],[A827; H,F,CF3,F,H,CH2CF3],[A828; H,F,CHF2,F,H,CH2CF3],[A829; H,F,NO2,F,H,CH2CF3],[A830; H,F,H,F,H,CF2CH3],[A831; H,F,F,F,H,CF2CH3],[A832; H,F,Cl,F,H,CF2CH3],[A833; H,F,Br,F,H,CF2CH3],[A834; H,F,I,F,H,CF2CH3],[A835; H,F,Me,F,H,CF2CH3],[A836; H,F,OMe,F,H,CF2CH3],[A837; H,F,CF3,F,H,CF2CH3],[A838; H,F,CHF2,F,H,CF2CH3],[A839; H,F,NO2,F,H,CF2CH3],[A840; H,F,H,F,H,2-Py],[A841; H,F,F,F,H,2-Py],[A842; H,F,Cl,F,H,2-Py],[A843; H,F,Br,F,H,2-Py],[A844; H,F,I,F,H,2-Py],[A845; H,F,Me,F,H,2-Py],[A846; H,F,OMe,F,H,2-Py],[A847; H,F,CF3,F,H,2-Py],[A848; H,F,CHF2,F,H,2-Py],[A849; H,F,NO2,F,H,2-Py],[A850; H,F,H,F,H,3-Py],[A851; H,F,F,F,H,3-Py],[A852; H,F,Cl,F,H,3-Py],[A853; H,F,Br,F,H,3-Py],[A854; H,F,I,F,H,3-Py],[A855; H,F,Me,F,H,3-Py],[A856; H,F,OMe,F,H,3-Py],[A857; H,F,CF3,F,H,3-Py],[A858; H,F,CHF2,F,H,3-Py],[A859; H,F,NO2,F,H,3-Py],[A860; H,F,H,F,H,4-Py],[A861; H,F,F,F,H,4-Py],[A862; H,F,Cl,F,H,4-Py],[A863; H,F,Br,F,H,4-Py],[A864; H,F,I,F,H,4-Py],[A865; H,F,Me,F,H,4-Py],[A866; H,F,OMe,F,H,4-Py],[A867;H,F,CF3,F,H,4-Py],[A868; H,F,CHF2,F,H,4-Py],[A869; H,F,NO2,F,H,4-Py],;

[1204] [A870; H, Cl, H, F, H, Et], [A871; H, Cl, F, F, H, Et], [A872; H, Cl, Cl, F, H, Et], [A873; H, Cl, Br, F, H, Et], [A874; H, Cl, I, F, H, Et], [A875; H, Cl, Me, F, H, Et], [A876; H, Cl, OMe, F, H, Et], [A877; H, Cl, CF3, F, H, Et], [A878; H, Cl, CHF2, F, H, Et], [A879; H, Cl, NO2, F, H, Et], [A880; H, Cl, H, F, H, Pr], [A881; H, Cl, F, F, H, Pr], [A882; H, Cl, Cl, F, H, Pr], [A883; H, Cl, Br, F, H, Pr], [A884; H, Cl, I, F, H, Pr], [A885; H, Cl, Me, F, H, Pr], [A886; H, Cl, OMe, F, H, Pr], [A887; H, Cl, CF3, F, H, Pr], [A888; H, Cl, CHF2, F, H, Pr], [A889; H, Cl, NO2, F, H, Pr], [A890; H, Cl, H, F, H, i-Pr], [A891; H, Cl, F, F, H, i-Pr], [A892; H, Cl, Cl, F, H, i-Pr], [A893; H, Cl, Br, F, H, i-Pr], [A894; H, Cl, I, F, H, i-Pr], [A895; H, Cl, Me, F, H, i-Pr], [A896; H, Cl, OMe, F, H, i-Pr], [A897; H, Cl, CF3, F, H, i-Pr], [A898; H, Cl, CHF2, F, H, i-Pr], [A899; H, Cl, NO2, F, H, i-Pr], [A900; H, Cl, H, F, H, c-Pr], [A901; H, Cl, F, F, H, c-Pr], [A902; H, Cl, Cl, F, H, c-Pr], [A903; H, Cl, Br, F, H, c-Pr], [A904; H, Cl, I, F, H, c-Pr], [A905; H, Cl, Me, F, H, c-Pr], [A906; H, Cl, OMe, F, H, c-Pr], [A907; H, Cl, CF3, F, H, c-Pr], [A908; H, Cl, CHF2, F, H, c-Pr], [A909; H, Cl, NO2, F, H, c-Pr], [A910; H, Cl, H, F, H, Bu], [A911; H, Cl, F, F, H, Bu], [A912; H, Cl, Cl, F, H, Bu], [A913;H, Cl, Br, F, H, Bu], [A914; H, Cl, I, F, H, Bu], [A915; H, Cl, Me, F, H, Bu], [A916; H, Cl, OMe, F, H, Bu], [A917; H, Cl, CF3, F, H, Bu], [A918; H, Cl, CHF2, F, H, Bu], [A919; H, Cl, NO2, F, H, Bu], [A920; H, Cl, H, F, H, i - Bu], [A921; H, Cl, F, F, H, i - Bu], [A922; H, Cl, Cl, F, H, i - Bu], [A923; H, Cl, Br, F, H, i - Bu], [A924; H, Cl, I, F, H, i - Bu], [A925; H, Cl, Me, F, H, i - Bu], [A926; H, Cl, OMe, F, H, i - Bu], [A927; H, Cl, CF3, F, H, i - Bu], [A928; H, Cl, CHF2, F, H, i - Bu], [A929; H, Cl, NO2, F, H, i - Bu], [A930; H, Cl, H, F, H, CH2CF3], [A931; H, Cl, F, F, H, CH2CF3], [A932; H, Cl, Cl, F, H, CH2CF3], [A933; H, Cl, Br, F, H, CH2CF3], [A934; H, Cl, I, F, H, CH2CF3], [A935; H, Cl, Me, F, H, CH2CF3], [A936; H, Cl, OMe, F, H, CH2CF3], [A937; H, Cl, CF3, F, H, CH2CF3], [A938; H, Cl, CHF2, F, H, CH2CF3], [A939; H, Cl, NO2, F, H, CH2CF3], [A940; H, Cl, H, F, H, CF2CH3], [A941; H, Cl, F, F, H, CF2CH3], [A942; H, Cl, Cl, F, H, CF2CH3], [A943; H, Cl, Br, F, H, CF2CH3], [A944; H, Cl, I, F, H, CF2CH3], [A945; H, Cl, Me, F, H, CF2CH3], [A946; H, Cl, OMe, F, H, CF2CH3], [A947; H, Cl, CF3, F, H, CF2CH3], [A948; H, Cl, CHF2, F, H, CF2CH3], [A949; H, Cl, NO2, F, H, CF2CH3], [A950; H, Cl, H, F, H, 2 - Py], [A951; H, Cl, F, F, H, 2 - Py], [A952; H, Cl, Cl, F, H, 2 - Py], [A953;H, Cl, Br, F, H, 2-Py], [A954; H, Cl, I, F, H, 2-Py], [A955; H, Cl, Me, F, H, 2-Py], [A956; H, Cl, OMe, F, H, 2-Py], [A957; H, Cl, CF3, F, H, 2-Py], [A958; H, Cl, CHF2, F, H, 2-Py], [A959; H, Cl, NO2, F, H, 2-Py], [A960; H, Cl, H, F, H, 3-Py], [A961; H, Cl, F, F, H, 3-Py], [A962; H, Cl, Cl, F, H, 3-Py], [A963; H, Cl, Br, F, H, 3-Py], [A964; H, Cl, I, F, H, 3-Py], [A965; H, Cl, Me, F, H, 3-Py], [A966; H, Cl, OMe, F, H, 3-Py], [A967; H, Cl, CF3, F, H, 3-Py], [A968; H, Cl, CHF2, F, H, 3-Py], [A969; H, Cl, NO2, F, H, 3-Py], [A970; H, Cl, H, F, H, 4-Py], [A971; H, Cl, F, F, H, 4-Py], [A972; H, Cl, Cl, F, H, 4-Py], [A973; H, Cl, Br, F, H, 4-Py], [A974; H, Cl, I, F, H, 4-Py], [A975; H, Cl, Me, F, H, 4-Py], [A976; H, Cl, OMe, F, H, 4-Py], [A977; H, Cl, CF3, F, H, 4-Py], [A978; H, Cl, CHF2, F, H, 4-Py], [A979; H, Cl, NO2, F, H, 4-Py], ;

[1205] [A980; H, Br, H, F, H, Et], [A981; H, Br, F, F, H, Et], [A982; H, Br, Cl, F, H, Et], [A983; H, Br, Br, F, H, Et], [A984; H, Br, I, F, H, Et], [A985; H, Br, Me, F, H, Et], [A986; H, Br, OMe, F, H, Et], [A987; H, Br, CF3, F, H, Et], [A988; H, Br, CHF2, F, H, Et], [A989; H, Br, NO2, F, H, Et], [A990; H, Br, H, F, H, Pr], [A991; H, Br, F, F, H, Pr], [A992; H, Br, Cl, F, H, Pr], [A993; H, Br, Br, F, H, Pr], [A994; H, Br, I, F, H, Pr], [A995; H, Br, Me, F, H, Pr], [A996; H, Br, OMe, F, H, Pr], [A997; H, Br, CF3, F, H, Pr], [A998; H, Br, CHF2, F, H, Pr], [A999; H, Br, NO2, F, H, Pr], [A1000; H, Br, H, F, H, i-Pr], [A1001; H, Br, F, F, H, i-Pr], [A1002; H, Br, Cl, F, H, i-Pr], [A1003; H, Br, Br, F, H, i-Pr], [A1004; H, Br, I, F, H, i-Pr], [A1005; H, Br, Me, F, H, i-Pr], [A1006; H, Br, OMe, F, H, i-Pr], [A1007; H, Br, CF3, F, H, i-Pr], [A1008; H, Br, CHF2, F, H, i-Pr], [A1009; H, Br, NO2, F, H, i-Pr], [A1010; H, Br, H, F, H, c-Pr], [A1011; H, Br, F, F, H, c-Pr], [A1012; H, Br, Cl, F, H, c-Pr], [A1013; H, Br, Br, F, H, c-Pr], [A1014; H, Br, I, F, H, c-Pr], [A1015; H, Br, Me, F, H, c-Pr], [A1016; H, Br, OMe, F, H, c-Pr], [A1017; H, Br, CF3, F, H, c-Pr], [A1018; H, Br, CHF2, F, H, c-Pr], [A1019; H, Br, NO2, F, H, c-Pr], [A1020; H, Br, H, F, H, Bu], [A1021; H, Br, F, F, H, Bu], [A1022;H, Br, Cl, F, H, Bu], [A1023; H, Br, Br, F, H, Bu], [A1024; H, Br, I, F, H, Bu], [A1025; H, Br, Me, F, H, Bu], [A1026; H, Br, OMe, F, H, Bu], [A1027; H, Br, CF3, F, H, Bu], [A1028; H, Br, CHF2, F, H, Bu], [A1029; H, Br, NO2, F, H, Bu], [A1030; H, Br, H, F, H, i - Bu], [A1031; H, Br, F, F, H, i - Bu], [A1032; H, Br, Cl, F, H, i - Bu], [A1033; H, Br, Br, F, H, i - Bu], [A1034; H, Br, I, F, H, i - Bu], [A1035; H, Br, Me, F, H, i - Bu], [A1036; H, Br, OMe, F, H, i - Bu], [A1037; H, Br, CF3, F, H, i - Bu], [A1038; H, Br, CHF2, F, H, i - Bu], [A1039; H, Br, NO2, F, H, i - Bu], [A1040; H, Br, H, F, H, CH2CF3], [A1041; H, Br, F, F, H, CH2CF3], [A1042; H, Br, Cl, F, H, CH2CF3], [A1043; H, Br, Br, F, H, CH2CF3], [A1044; H, Br, I, F, H, CH2CF3], [A1045; H, Br, Me, F, H, CH2CF3], [A1046; H, Br, OMe, F, H, CH2CF3], [A1047; H, Br, CF3, F, H, CH2CF3], [A1048; H, Br, CHF2, F, H, CH2CF3], [A1049; H, Br, NO2, F, H, CH2CF3], [A1050; H, Br, H, F, H, CF2CH3], [A1051; H, Br, F, F, H, CF2CH3], [A1052; H, Br, Cl, F, H, CF2CH3], [A1053; H, Br, Br, F, H, CF2CH3], [A1054; H, Br, I, F, H, CF2CH3], [A1055; H, Br, Me, F, H, CF2CH3], [A1056; H, Br, OMe, F, H, CF2CH3], [A1057; H, Br, CF3, F, H, CF2CH3], [A1058; H, Br, CHF2, F, H, CF2CH3], [A1059; H, Br, NO2, F, H, CF2CH3], [A1060;H, Br, H, F, H, 2-Py], [A1061; H, Br, F, F, H, 2-Py], [A1062; H, Br, Cl, F, H, 2-Py], [A1063; H, Br, Br, F, H, 2-Py], [A1064; H, Br, I, F, H, 2-Py], [A1065; H, Br, Me, F, H, 2-Py], [A1066; H, Br, OMe, F, H, 2-Py], [A1067; H, Br, CF3, F, H, 2-Py], [A1068; H, Br, CHF2, F, H, 2-Py], [A1069; H, Br, NO2, F, H, 2-Py], [A1070; H, Br, H, F, H, 3-Py], [A1071; H, Br, F, F, H, 3-Py], [A1072; H, Br, Cl, F, H, 3-Py], [A1073; H, Br, Br, F, H, 3-Py], [A1074; H, Br, I, F, H, 3-Py], [A1075; H, Br, Me, F, H, 3-Py], [A1076; H, Br, OMe, F, H, 3-Py], [A1077; H, Br, CF3, F, H, 3-Py], [A1078; H, Br, CHF2, F, H, 3-Py], [A1079; H, Br, NO2, F, H, 3-Py], [A1080; H, Br, H, F, H, 4-Py], [A1081; H, Br, F, F, H, 4-Py], [A1082; H, Br, Cl, F, H, 4-Py], [A1083; H, Br, Br, F, H, 4-Py], [A1084; H, Br, I, F, H, 4-Py], [A1085; H, Br, Me, F, H, 4-Py], [A1086; H, Br, OMe, F, H, 4-Py], [A1087; H, Br, CF3, F, H, 4-Py], [A1088; H, Br, CHF2, F, H, 4-Py], [A1089; H, Br, NO2, F, H, 4-Py], ;

[1206] [A1090; H, CF3, H, F, H, Et], [A1091; H, CF3, F, F, H, Et], [A1092; H, CF3, Cl, F, H, Et], [A1093; H, CF3, Br, F, H, Et], [A1094; H, CF3, I, F, H, Et], [A1095; H, CF3, Me, F, H, Et], [A1096; H, CF3, OMe, F, H, Et], [A1097; H, CF3, CF3, F, H, Et], [A1098; H, CF3, CHF2, F, H, Et], [A1099; H, CF3, NO2, F, H, Et], [A1100; H, CF3, H, F, H, Pr], [A1101; H, CF3, F, F, H, Pr], [A1102; H, CF3, Cl, F, H, Pr], [A1103; H, CF3, Br, F, H, Pr], [A1104; H, CF3, I, F, H, Pr], [A1105; H, CF3, Me, F, H, Pr], [A1106; H, CF3, OMe, F, H, Pr], [A1107; H, CF3, CF3, F, H, Pr], [A1108; H, CF3, CHF2, F, H, Pr], [A1109; H, CF3, NO2, F, H, Pr], [A1110; H, CF3, H, F, H, i-Pr], [A1111; H, CF3, F, F, H, i-Pr], [A1112; H, CF3, Cl, F, H, i-Pr], [A1113; H, CF3, Br, F, H, i-Pr], [A1114; H, CF3, I, F, H, i-Pr], [A1115; H, CF3, Me, F, H, i-Pr], [A1116; H, CF3, OMe, F, H, i-Pr], [A1117; H, CF3, CF3, F, H, i-Pr], [A1118; H, CF3, CHF2, F, H, i-Pr], [A1119; H, CF3, NO2, F, H, i-Pr], [A1120; H, CF3, H, F, H, c-Pr], [A1121; H, CF3, F, F, H, c-Pr], [A1122; H, CF3, Cl, F, H, c-Pr], [A1123; H, CF3, Br, F, H, c-Pr], [A1124; H, CF3, I, F, H, c-Pr], [A1125; H, CF3, Me, F, H, c-Pr], [A1126; H, CF3, OMe, F, H, c-Pr], [A1127; H, CF3, CF3, F, H, c-Pr], [A1128; H, CF3, CHF2, F, H, c-Pr], [A1129;H, CF3, NO2, F, H, c-Pr], [A1130; H, CF3, H, F, H, Bu], [A1131; H, CF3, F, F, H, Bu], [A1132; H, CF3, Cl, F, H, Bu], [A1133; H, CF3, Br, F, H, Bu], [A1134; H, CF3, I, F, H, Bu], [A1135; H, CF3, Me, F, H, Bu], [A1136; H, CF3, OMe, F, H, Bu], [A1137; H, CF3, CF3, F, H, Bu], [A1138; H, CF3, CHF2, F, H, Bu], [A1139; H, CF3, NO2, F, H, Bu], [A1140; H, CF3, H, F, H, i-Bu], [A1141; H, CF3, F, F, H, i-Bu], [A1142; H, CF3, Cl, F, H, i-Bu], [A1143; H, CF3, Br, F, H, i-Bu], [A1144; H, CF3, I, F, H, i-Bu], [A1145; H, CF3, Me, F, H, i-Bu], [A1146; H, CF3, OMe, F, H, i-Bu], [A1147; H, CF3, CF3, F, H, i-Bu], [A1148; H, CF3, CHF2, F, H, i-Bu], [A1149; H, CF3, NO2, F, H, i-Bu], [A1150; H, CF3, H, F, H, CH2CF3], [A1151; H, CF3, F, F, H, CH2CF3], [A1152; H, CF3, Cl, F, H, CH2CF3], [A1153; H, CF3, Br, F, H, CH2CF3], [A1154; H, CF3, I, F, H, CH2CF3], [A1155; H, CF3, Me, F, H, CH2CF3], [A1156; H, CF3, OMe, F, H, CH2CF3], [A1157; H, CF3, CF3, F, H, CH2CF3], [A1158; H, CF3, CHF2, F, H, CH2CF3], [A1159; H, CF3, NO2, F, H, CH2CF3], [A1160; H, CF3, H, F, H, CF2CH3], [A1161; H, CF3, F, F, H, CF2CH3], [A1162; H, CF3, Cl, F, H, CF2CH3], [A1163; H, CF3, Br, F, H, CF2CH3], [A1164; H, CF3, I, F, H, CF2CH3], [A1165; H, CF3, Me, F, H, CF2CH3], [A1166;H, CF3, OMe, F, H, CF2CH3], [A1167; H, CF3, CF3, F, H, CF2CH3], [A1168; H, CF3, CHF2, F, H, CF2CH3], [A1169; H, CF3, NO2, F, H, CF2CH3], [A1170; H, CF3, H, F, H, 2-Py], [A1171; H, CF3, F, F, H, 2-Py], [A1172; H, CF3, Cl, F, H, 2-Py], [A1173; H, CF3, Br, F, H, 2-Py], [A1174; H, CF3, I, F, H, 2-Py], [A1175; H, CF3, Me, F, H, 2-Py], [A1176; H, CF3, OMe, F, H, 2-Py], [A1177; H, CF3, CF3, F, H, 2-Py], [A1178; H, CF3, CHF2, F, H, 2-Py], [A1179; H, CF3, NO2, F, H, 2-Py], [A1180; H, CF3, H, F, H, 3-Py], [A1181; H, CF3, F, F, H, 3-Py], [A1182; H, CF3, Cl, F, H, 3-Py], [A1183; H, CF3, Br, F, H, 3-Py], [A1184; H, CF3, I, F, H, 3-Py], [A1185; H, CF3, Me, F, H, 3-Py], [A1186; H, CF3, OMe, F, H, 3-Py], [A1187; H, CF3, CF3, F, H, 3-Py], [A1188; H, CF3, CHF2, F, H, 3-Py], [A1189; H, CF3, NO2, F, H, 3-Py], [A1190; H, CF3, H, F, H, 4-Py], [A1191; H, CF3, F, F, H, 4-Py], [A1192; H, CF3, Cl, F, H, 4-Py], [A1193; H, CF3, Br, F, H, 4-Py], [A1194; H, CF3, I, F, H, 4-Py], [A1195; H, CF3, Me, F, H, 4-Py], [A1196; H, CF3, OMe, F, H, 4-Py], [A1197; H, CF3, CF3, F, H, 4-Py], [A1198; H, CF3, CHF2, F, H, 4-Py], [A1199; H, CF3, NO2, F, H, 4-Py], ;

[1207] [A1200; H, NO2, H, F, H, Et], [A1201; H, NO2, F, F, H, Et], [A1202; H, NO2, Cl, F, H, Et], [A1203; H, NO2, Br, F, H, Et], [A1204; H, NO2, I, F, H, Et], [A1205; H, NO2, Me, F, H, Et], [A1206; H, NO2, OMe, F, H, Et], [A1207; H, NO2, CF3, F, H, Et], [A1208; H, NO2, CHF2, F, H, Et], [A1209; H, NO2, NO2, F, H, Et], [A1210; H, NO2, H, F, H, Pr], [A1211; H, NO2, F, F, H, Pr], [A1212; H, NO2, Cl, F, H, Pr], [A1213; H, NO2, Br, F, H, Pr], [A1214; H, NO2, I, F, H, Pr], [A1215; H, NO2, Me, F, H, Pr], [A1216; H, NO2, OMe, F, H, Pr], [A1217; H, NO2, CF3, F, H, Pr], [A1218; H, NO2, CHF2, F, H, Pr], [A1219; H, NO2, NO2, F, H, Pr], [A1220; H, NO2, H, F, H, i-Pr], [A1221; H, NO2, F, F, H, i-Pr], [A1222; H, NO2, Cl, F, H, i-Pr], [A1223; H, NO2, Br, F, H, i-Pr], [A1224; H, NO2, I, F, H, i-Pr], [A1225; H, NO2, Me, F, H, i-Pr], [A1226; H, NO2, OMe, F, H, i-Pr], [A1227; H, NO2, CF3, F, H, i-Pr], [A1228; H, NO2, CHF2, F, H, i-Pr], [A1229; H, NO2, NO2, F, H, i-Pr], [A1230; H, NO2, H, F, H, c-Pr], [A1231; H, NO2, F, F, H, c-Pr], [A1232; H, NO2, Cl, F, H, c-Pr], [A1233; H, NO2, Br, F, H, c-Pr], [A1234; H, NO2, I, F, H, c-Pr], [A1235; H, NO2, Me, F, H, c-Pr], [A1236; H, NO2, OMe, F, H, c-Pr], [A1237; H, NO2, CF3, F, H, c-Pr], [A1238; H, NO2, CHF2, F, H, c-Pr], [A1239;H, NO2, NO2, F, H, c-Pr], [A1240; H, NO2, H, F, H, Bu], [A1241; H, NO2, F, F, H, Bu], [A1242; H, NO2, Cl, F, H, Bu], [A1243; H, NO2, Br, F, H, Bu], [A1244; H, NO2, I, F, H, Bu], [A1245; H, NO2, Me, F, H, Bu], [A1246; H, NO2, OMe, F, H, Bu], [A1247; H, NO2, CF3, F, H, Bu], [A1248; H, NO2, CHF2, F, H, Bu], [A1249; H, NO2, NO2, F, H, Bu], [A1250; H, NO2, H, F, H, i-Bu], [A1251; H, NO2, F, F, H, i-Bu], [A1252; H, NO2, Cl, F, H, i-Bu], [A1253; H, NO2, Br, F, H, i-Bu], [A1254; H, NO2, I, F, H, i-Bu], [A1255; H, NO2, Me, F, H, i-Bu], [A1256; H, NO2, OMe, F, H, i-Bu], [A1257; H, NO2, CF3, F, H, i-Bu], [A1258; H, NO2, CHF2, F, H, i-Bu], [A1259; H, NO2, NO2, F, H, i-Bu], [A1260; H, NO2, H, F, H, CH2CF3], [A1261; H, NO2, F, F, H, CH2CF3], [A1262; H, NO2, Cl, F, H, CH2CF3], [A1263; H, NO2, Br, F, H, CH2CF3], [A1264; H, NO2, I, F, H, CH2CF3], [A1265; H, NO2, Me, F, H, CH2CF3], [A1266; H, NO2, OMe, F, H, CH2CF3], [A1267; H, NO2, CF3, F, H, CH2CF3], [A1268; H, NO2, CHF2, F, H, CH2CF3], [A1269; H, NO2, NO2, F, H, CH2CF3], [A1270; H, NO2, H, F, H, CF2CH3], [A1271; H, NO2, F, F, H, CF2CH3], [A1272; H, NO2, Cl, F, H, CF2CH3], [A1273; H, NO2, Br, F, H, CF2CH3], [A1274; H, NO2, I, F, H, CF2CH3], [A1275; H, NO2, Me, F, H, CF2CH3], [A1276;H, NO2, OMe, F, H, CF2CH3, [A1277]; H, NO2, CF3, F, H, CF2CH3, [A1278]; H, NO2, CHF2, F, H, CF2CH3, [A1279]; H, NO2, NO2, F, H, CF2CH3, [A1280]; H, NO2, H, F, H, 2-Py, [A1281]; H, NO2, F, F, H, 2-Py, [A1282]; H, NO2, Cl, F, H, 2-Py, [A1283]; H, NO2, Br, F, H, 2-Py, [A1284]; H, NO2, I, F, H, 2-Py, [A1285]; H, NO2, Me, F, H, 2-Py, [A1286]; H, NO2, OMe, F, H, 2-Py, [A1287]; H, NO2, CF3, F, H, 2-Py, [A1288]; H, NO2, CHF2, F, H, 2-Py, [A1289]; H, NO2, NO2, F, H, 2-Py, [A1290]; H, NO2, H, F, H, 3-Py, [A1291]; H, NO2, F, F, H, 3-Py, [A1292]; H, NO2, Cl, F, H, 3-Py, [A1293]; H, NO2, Br, F, H, 3-Py, [A1294]; H, NO2, I, F, H, 3-Py, [A1295]; H, NO2, Me, F, H, 3-Py, [A1296]; H, NO2, OMe, F, H, 3-Py, [A1297]; H, NO2, CF3, F, H, 3-Py, [A1298]; H, NO2, CHF2, F, H, 3-Py, [A1299]; H, NO2, NO2, F, H, 3-Py, [A1300]; H, NO2, H, F, H, 4-Py, [A1301]; H, NO2, F, F, H, 4-Py, [A1302]; H, NO2, Cl, F, H, 4-Py, [A1303]; H, NO2, Br, F, H, 4-Py, [A1304]; H, NO2, I, F, H, 4-Py, [A1305]; H, NO2, Me, F, H, 4-Py, [A1306]; H, NO2, OMe, F, H, 4-Py, [A1307]; H, NO2, CF3, F, H, 4-Py, [A1308]; H, NO2, CHF2, F, H, 4-Py, [A1309]; H, NO2, NO2, F, H, 4-Py, ;

[1208] [A1310; H, OCH2Ph, H, F, H, Et], [A1311; H, OCH2Ph, F, F, H, Et], [A1312; H, OCH2Ph, Cl, F, H, Et], [A1313; H, OCH2Ph, Br, F, H, Et], [A1314; H, OCH2Ph, I, F, H, Et], [A1315; H, OCH2Ph, Me, F, H, Et], [A1316; H, OCH2Ph, OMe, F, H, Et], [A1317; H, OCH2Ph, CF3, F, H, Et], [A1318; H, OCH2Ph, CHF...

Claims

1. A method for controlling plant diseases, which is carried out by treating a plant or the soil of a cultivated plant with a compound represented by formula (I) or a salt thereof. In formula (I), Z represents: methyl substituted with one or more substituents selected from Group A; a C2-C6 chain hydrocarbon group, which may be substituted with one or more substituents selected from Group A; a C3-C6 cycloalkyl group, a C6-C10 aryl group, or a 5-10 membered aromatic heterocyclic group, which may be substituted with one or more substituents selected from Group E; Q represents the group shown in Q1, wherein, # represents the bonding site to the phenyl group, and ● represents the bonding site to the sulfur atom; R 1 , R 2 , R 3 , R 4 and R 5 are the same or different, representing a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C6-C10 aryl group, a 5-10 membered aromatic heterocyclic group, a hydrogen atom, a halogen atom, a nitro group, a cyano group, -OR 10 、-S(O) k R 11 、-C(O)R 12 , -CR 13 =NOR 14 、-ON=CR 15 R 16 、-N=N-CR 17 R 18 R 19 、-C(O)NR 20 R 21 、-NR 22 C(O)R 23 、-C(O)N(OR 24 )R 25 、-N(OR 26 )C(O)R 27 、-NR 28 C(O)NR 29 R 30 、-OC(O)NR 31 R 32 、-NR 33 C(O)OR 34 、-NR 35 C(O)C(O)NR 36 R 37 , -CR 38 R 39 NR 40 C(O)C(O)NR 41 R 42 , or -NR 43 C(O)C(O)N(OR 44 )R 45 , the C1-C6 chain hydrocarbon group may be substituted by one or more substituents selected from group D, the C3-C6 cycloalkyl group, the C6-C10 aryl group, and the 5-10 membered aromatic heterocyclic group may be substituted by one or more substituents selected from group E, R 1 and R 2 may together with the carbon atoms to which they are bonded form a C4-C7 carbocyclic ring, or a 5-7 membered heterocyclic ring, and the C4-C7 carbocyclic ring and the 5-7 membered heterocyclic ring may be substituted with one or more substituents selected from Group B R 2 and R 3 may together with the carbon atoms to which they are bonded form a C4-C7 carbocyclic ring or a 5-7 membered heterocyclic ring, and the C4-C7 carbocyclic ring and the 5-7 membered heterocyclic ring may be substituted with one or more substituents selected from Group B R 6 and R 7 each represents a hydrogen atom, R 10 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 19 、R 20 、R 21 、R 22 、R 23 、R 24 、R 25 、R 26 、R 27 、R 28 、R 29 、R 30 、R 31 、R 32 、R 33 、R 35 、R 36 、R 37 、R 38 、R 39 、R 40 、R 41 、R 42 、R 43 、R 44 、 and R 45 are the same or different and represent a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C6-C10 aryl group, a 5-10 membered aromatic heterocyclic group or a hydrogen atom, where the C1-C6 chain hydrocarbon group may be substituted by one or more substituents selected from group D, and the C3-C6 cycloalkyl group, the C6-C10 aryl group, and the 5-10 membered aromatic heterocyclic group may be substituted by one or more substituents selected from group C. R 34 represents a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C6-C10 aryl group, or a 5-10 membered aromatic heterocyclic group, the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group D, and the C3-C6 cycloalkyl group, the C6-C10 aryl group, and the 5-10 membered aromatic heterocyclic group may be substituted with one or more substituents selected from group C. R 11 represents a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group, the C1-C6 chain hydrocarbon group may be substituted by one or more substituents selected from Group D, and the C3-C6 cycloalkyl group may be substituted by one or more substituents selected from the group consisting of a halogen atom and a cyano group. n represents 2; k represents 0, 1, or 2; Group A: a group consisting of a C3-C6 cycloalkyl group, a C1-C3 alkoxy group, a C1-C3 alkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 alkylsulfonyl group, a halogen atom, and a cyano group, and the C3-C6 cycloalkyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more halogen atoms; Group B: a group consisting of a C1-C3 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C1-C3 alkoxy group, a halogen atom, a nitro group, and a cyano group, and the C1-C3 chain hydrocarbon group, the C3-C6 cycloalkyl group, and the C1-C3 alkoxy group may be substituted with one or more halogen atoms; Group C: a group consisting of a C1-C3 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C1-C3 alkoxy group, a C1-C3 alkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 alkylsulfonyl group, a halogen atom, and a cyano group, and the C1-C3 chain hydrocarbon group, the C3-C6 cycloalkyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group; Group D: a group consisting of a C1-C3 alkoxy group, a C1-C3 alkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C3-C6 cycloalkyl group, a C6-C10 aryl group, a 5-10 membered aromatic heterocyclic group, a halogen atom, and a cyano group, and the C1-C3 alkoxy group, the C1-C3 alkylthio group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more halogen atoms, and the C3-C6 cycloalkyl group, the C6-C10 aryl group, and the 5-10 membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group C; Group E: a group consisting of a C1-C3 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C1-C3 alkoxy group, a C1-C3 alkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 alkylsulfonyl group, a halogen atom, and a cyano group, wherein the C1-C3 chain hydrocarbon group, the C3-C6 cycloalkyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted by one or more halogen atoms.

2. The method according to claim 1, wherein the compound represented by formula (I) in claim 1 or a salt thereof is the following compound or a salt thereof, and in the compound: R 1 、R 2 、R 3 、R 4 and R 5 are the same or different and are C1-C6 chain alkyl, C3-C6 cycloalkyl, C6-C10 aryl, hydrogen atom, halogen atom, nitro group, cyano group, -OR 10 、-S(O) k R 11 、-C(O)R 12 、-CR 13 =N-O-R 14 、-C(O)NR 20 R 21 、-NR 22 C(O)R 23 、-C(O)N(OR 24 )R 25 、-N(OR 26 )C(O)R 27 、or -NR 33 C(O)OR 34 , the C1-C6 chain alkyl may be substituted with one or more substituents selected from group D, and the C3-C6 cycloalkyl and the C6-C10 aryl may be substituted with one or more substituents selected from group E. R 1 and R 2 may together with the carbon atoms to which they are bonded form a C4-C7 carbocyclic ring or a 5- to 7-membered heterocyclic ring, and the C4-C7 carbocyclic ring and the 5- to 7-membered heterocyclic ring may be substituted with one or more substituents selected from Group B R 2 and R 3 may together with the carbon atoms to which they are bonded form a C4-C7 carbocyclic ring, or a 5-7 membered heterocyclic ring, which C4-C7 carbocyclic ring and which 5-7 membered heterocyclic ring may be substituted by one or more substituents selected from Group B, R 34 is a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group or a C6-C10 aryl group. The C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group D, and the C3-C6 cycloalkyl group and the C6-C10 aryl group may be substituted with one or more substituents selected from group C. R 11 is a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group. The C1-C6 chain hydrocarbon group may be substituted by one or more substituents selected from Group D, and the C3-C6 cycloalkyl group may be substituted by one or more substituents selected from the group consisting of a halogen atom and a cyano group.

3. The compound represented by formula (II) or a salt thereof, in formula (II), Q A represented by the combination of and m: Q A is Q A the group shown in 1, and the combination where m is 2, Q A The group shown in 1 represents the group shown by the following formula, where # represents the bonding site to the phenyl group, ● represents the bonding site to the sulfur atom, R 6A and R 7A each represents a hydrogen atom, Z A represents a C2-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, or a 5-10 membered aromatic heterocyclic group, the C2-C6 chain hydrocarbon group and the C3-C6 cycloalkyl group may be substituted by one or more halogen atoms, and the 5-10 membered aromatic heterocyclic group may be substituted by one or more substituents selected from Group E A above, R 3A represents a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C6-C10 aryl group, a 5-10 membered aromatic heterocyclic group, a hydrogen atom, a halogen atom, a nitro group, a cyano group, -OR 10A , -S(O) p R 11A , -C(O)R 12A , -CR 13A =N-O-R 14A , -O-N=CR 15A R 16A , -N=N-CR 17A R 18A R 19A , -C(O)NR 20A R 21A , -NR 22A C(O)R 23A , -C(O)N(OR 24A )R 25A , -N(OR 26A )C(O)R 27A , -NR 28A C(O)NR 29A R 30A , -OC(O)NR 31A R 32A , -NR 33A C(O)OR 34A , -NR 35A C(O)C(O)NR 36A R 37A , -CR 38A R 39A NR 40A C(O)C(O)NR 41A R 42A , or -NR 43A C(O)C(O)N(OR 44A )R 45A , the C1-C6 chain hydrocarbon group may be substituted by one or more substituents selected from group A A , the C3-C6 cycloalkyl group, the C6-C10 aryl group, and the 5-10 membered aromatic heterocyclic group may be substituted by one or more substituents selected from group C A , R 2A and R 4A are the same or different and represent a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C6-C10 aryl group, a 5-10 membered aromatic heterocyclic group, a hydrogen atom, a halogen atom, a nitro group, a cyano group, -OR 10A , -C(O)R 12A , -CR 13A =N-O-R 14A , -O-N=CR 15A R 16A , -N=N-CR 17A R 18A R 19A , -C(O)NR 20A R 21A , -NR 22A C(O)R 23B , -C(O)N(OR 24A )R 25A , -N(OR 26A )C(O)R 27A , -NR 28A C(O)NR 29A R 30A , -OC(O)NR 31A R 32A , -NR 33A C(O)OR 34A , -NR 35A C(O)C(O)NR 36A R 37A , -CR 38A R 39A NR 40A C(O)C(O)NR 41A R 42A , or -NR 43A C(O)C(O)N(OR 44A )R 45A , the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from Group A A , the C3-C6 cycloalkyl group, the C6-C10 aryl group, and the 5-10 membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group C A . R 1A and R 5A which are the same or different and represent a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C6-C10 aryl group, a 5-10 membered aromatic heterocyclic group, a hydrogen atom, a halogen atom, a nitro group, a cyano group, -OR 10A , -S(O) p R 11A , -C(O)R 12A , -CR 13A =N-O-R 14A , -O-N=CR 15A R 16A , -N=N-CR 17A R 18A R 19A , -C(O)NR 20A R 21A , -NR 22B C(O)R 23A , -C(O)N(OR 24A )R 25A , -N(OR 26A )C(O)R 27A , -NR 28B C(O)NR 29A R 30A , -OC(O)NR 31A R 32A , -NR 33B C(O)OR 34A , -NR 35A C(O)C(O)NR 36A R 37A , -CR 38A R 39A NR 40A C(O)C(O)NR 41A R 42A , or -NR 43A C(O)C(O)N(OR 44A )R 45A , where the C1-C6 chain hydrocarbon group may be substituted by one or more substituents selected from Group A A , and the C3-C6 cycloalkyl group, the C6-C10 aryl group, and the 5-10 membered aromatic heterocyclic group may be substituted by one or more substituents selected from Group C A . wherein at least one of R 1A , R 2A , R 3A , R 4A , and R 5A is not a hydrogen atom R 1A and R 2A may together with the carbon atoms to which they are bonded form a C4-C7 carbocyclic ring or a 5- to 7-membered heterocyclic ring, and the C4-C7 carbocyclic ring and the 5- to 7-membered heterocyclic ring may be substituted with one or more substituents selected from Group B A below R 2A and R 3A may together with the carbon atoms to which they are bonded form a C4-C7 carbocyclic ring or a 5-7 membered heterocyclic ring, and the C4-C7 carbocyclic ring and the 5-7 membered heterocyclic ring may be substituted with one or more substituents selected from Group B A above, R 10A 、R 12A 、R 13A 、R 14A 、R 15A 、R 16A 、R 17A 、R 18A 、R 19A 、R 20A 、R 21A 、R 22A 、R 23A 、R 24A 、R 25A 、R 26A 、R 27A 、R 28A 、R 29A 、R 30A 、R 31A 、R 32A 、R 33A 、R 35A 、R 36A 、R 37A 、R 38A 、R 39A 、R 40A 、R 41A 、R 42A 、R 43A 、R 44A 、and R 45A are the same or different and represent a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C6-C10 aryl group, a 5-10 membered aromatic heterocyclic group or a hydrogen atom, and the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group D A and the C3-C6 cycloalkyl group, the C6-C10 aryl group, and the 5-10 membered aromatic heterocyclic group may be substituted with one or more substituents selected from group C A ​ R 34A 、R 22B 、R 28B 、and R 33B which are the same or different and represent a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C6-C10 aryl group, or a 5-10 membered aromatic heterocyclic group, wherein the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from group D A and the C3-C6 cycloalkyl group, the C6-C10 aryl group, and the 5-10 membered aromatic heterocyclic group may be substituted with one or more substituents selected from group C A . R 23B represents a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, or a C6-C10 aryl group or a hydrogen atom, and the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from Group D A and the C3-C6 cycloalkyl group and the C6-C10 aryl group may be substituted with one or more substituents selected from Group C A and is substituted with one or more substituents selected from Group C R 11A represents a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group, and the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from Group D A and the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group p represents 0, 1, or 2; Group A A : a group consisting of a C3-C6 cycloalkyl group, a C1-C3 alkoxy group, a C1-C3 alkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 alkylsulfonyl group, a halogen atom, and a cyano group, where the C3-C6 cycloalkyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more halogen atoms; Group B A : a group consisting of a C1-C3 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C1-C3 alkoxy group, a halogen atom, a nitro group, and a cyano group, wherein the C1-C3 chain hydrocarbon group, the C3-C6 cycloalkyl group, and the C1-C3 alkoxy group may be substituted by one or more halogen atoms; Group C A : a group consisting of a C1-C3 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C1-C3 alkoxy group, a C1-C3 alkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 alkylsulfonyl group, a halogen atom, and a cyano group, where the C1-C3 chain hydrocarbon group, the C3-C6 cycloalkyl group, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group; Group D A : a group consisting of a C1-C3 alkoxy group, a C1-C3 alkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C3-C6 cycloalkyl group, a C6-C10 aryl group, a 5-10 membered aromatic heterocyclic group, a halogen atom, and a cyano group, wherein the C1-C3 alkoxy group, the C1-C3 alkylthio group, the C1-C3 alkylsulfinyl group, and the C1-C3 alkylsulfonyl group may be substituted with one or more halogen atoms, and the C3-C6 cycloalkyl group, the C6-C10 aryl group, and the 5-10 membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group C A ; Group E A : a group consisting of a C1-C3 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C1-C3 alkoxy group, a halogen atom, and a cyano group, wherein the C1-C3 chain hydrocarbon group, the C3-C6 cycloalkyl group, and the C1-C3 alkoxy group may be substituted by one or more halogen atoms.

4. The compound or a salt thereof according to claim 3, wherein R 3A is a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a hydrogen atom, a halogen atom, a nitro group, a cyano group, -OR 10A , -S(O) p R 11A , -C(O)R 12A , -CR 13A =N-O-R 14A , -C(O)NR 20A R 21A , -NR 22A C(O)R 23A , -C(O)N(OR 24A )R 25A , -N(OR 26A )C(O)R 27A or -NR 33A C(O)OR 34A , the C1-C6 chain hydrocarbon group may be substituted by one or more halogen atoms, and the C3-C6 cycloalkyl group may be substituted by one or more substituents selected from the group consisting of a C1-C3 chain hydrocarbon group and a halogen atom. R 2A and R 4A are the same or different and are a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a hydrogen atom, a halogen atom, a nitro group, a cyano group, -OR 10A , -C(O)R 12A , -CR 13A =N-O-R 14A , -C(O)NR 20A R 21A , -NR 22A C(O)R 23B , -C(O)N(OR 24A )R 25A , -N(OR 26A )C(O)R 27A or -NR 33A C(O)OR 34A , the C1-C6 chain hydrocarbon group may be substituted by one or more halogen atoms, and the C3-C6 cycloalkyl group may be substituted by one or more substituents selected from the group consisting of a C1-C3 chain hydrocarbon group and a halogen atom. R 1A and R 5A are the same or different and are C1-C6 chain alkyl, C3-C6 cycloalkyl, hydrogen atom, halogen atom, nitro, cyano, -OR 10A , -S(O) p R 11A , -C(O)R 12A , -CR 13A =N-O-R 14A , -C(O)NR 20A R 21A , -NR 22B C(O)R 23A , -C(O)N(OR 24A )R 25A , -N(OR 26A )C(O)R 27A or -NR 33B C(O)OR 34A , the C1-C6 chain alkyl may be substituted by one or more halogen atoms, and the C3-C6 cycloalkyl may be substituted by one or more halogen atoms, wherein at least one of R 1A , R 2A , R 3A , R 4A , and R 5A is not a hydrogen atom R 1A and R 2A can together with the carbon atoms to which they are bonded form a C4-C7 carbocyclic ring or a 5-7 membered heterocyclic ring, and the C4-C7 carbocyclic ring and the 5-7 membered heterocyclic ring may be substituted with one or more substituents selected from Group B A below. R 2A and R 3A may together with the carbon atoms to which they are bonded form a C4-C7 carbocyclic ring or a 5-7 membered heterocyclic ring, and the C4-C7 carbocyclic ring and the 5-7 membered heterocyclic ring may be substituted with one or more substituents selected from Group B A below.

5. A plant disease control composition comprising the compound or a salt thereof according to claim 3 or 4.

6. A plant disease control method, which is carried out by treating a plant or the soil of a cultivated plant with an effective amount of the compound or a salt thereof according to claim 3 or 4.

7. Use of the compound or a salt thereof according to claim 3 or 4 for controlling plant diseases.

8. A composition comprising: one or more components selected from the group consisting of group (a), group (b), group (c), and group (d); and the compound or a salt thereof according to claim 3 or 4, Group (a): a group consisting of an insecticidal active ingredient, a miticidal active ingredient, and a nematicidal active ingredient; Group (b): a bactericidal active ingredient; Group (c): a plant growth regulating ingredient; Group (d): a repellent ingredient.

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