Pyrazole compound and pest control agent
Novel pyrazole compounds address the issue of drug resistance in pathogenic bacteria by offering excellent fungicidal activity, effectively controlling bacterial growth and preventing resistance development.
Patent Information
- Application Number
- JP2023213413
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Filing Date
- 2023-12-18
- Publication Date
- 2025-06-30
AI Technical Summary
The long-term use of existing fungicides can lead to the development of drug resistance in pathogenic bacteria, necessitating the development of new fungicides with excellent control effects.
The development of novel pyrazole compounds represented by formula (1) and their salts, which exhibit excellent control activity as fungicides, particularly for agricultural and horticultural use.
The pyrazole compounds demonstrate effective control activity against many pathogenic bacteria, providing a useful fungicide solution that helps prevent drug resistance.
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Figure 2025097231000003
Abstract
Description
Technical Field
[0001] The present invention relates to novel pyrazole compounds and salts thereof, production intermediates thereof, and pest control agents containing the compounds and salts thereof as active ingredients.
Background Art
[0002] Patent Documents 1 and 2 disclose certain pyrazole compounds, but do not disclose anything regarding the pyrazole compounds according to the present invention.
[0003] Also, Patent Documents 3 and 4 disclose that certain pyrazole compounds are useful as fungicides, but do not disclose anything regarding the pyrazole compounds according to the present invention.
[0004] Also, Patent Documents 5 to 8 disclose that certain heterocyclic compounds are useful as fungicides, but do not disclose anything regarding the pyrazole compounds according to the present invention.
Prior Art Documents
Patent Documents
[0005]
Patent Document 1
Patent Document 2
Patent Document 3
Patent Document 4
Patent Document 5
Patent Document 6
Patent Document 7
Patent Document 8
Summary of the Invention
Problems to be Solved by the Invention
[0006] However, the long-term use of drugs can cause the acquisition of drug resistance in pathogenic bacteria. Therefore, the development of new drugs with excellent control effects has always been expected.
Means for Solving the Problems
[0007] As a result of intensive research aimed at solving the above problems, the inventors have found that the novel pyrazole compound represented by the following formula (1) according to the present invention exhibits excellent control activity as a fungicide, particularly a fungicide for agricultural and horticultural use, and completed the present invention.
[0008] The pyrazole compound according to the present invention is not disclosed in any literature, and its usefulness as a pest control agent is not known.
[0009] That is, the present invention relates to the following [1]. 〔1〕 Formula (1):
[0010]
Chemical formula
[0011] [In the formula, G represents G-1, G-1 represents a structure represented by the following structural formula,
[0012]
Chemical formula
[0013] G 1 is hydroxy, nitro, cyano, a halogen atom, C1-C6 alkyl, C3-C 10 cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, R bC1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, di(C1-C6 alkyl)amino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C3-C 10 represents cycloalkylaminocarbonyl, di(C1-C6 alkyl)aminocarbonyl or -C(=NOR)R’, G 1 in the relationship with, when m5 represents an integer of 2, 3, 4 or 5, each G 1 may be the same as or different from each other, R b is cyano, C3-C 10 cycloalkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, di(C1-C6 alkyl)aminocarbonyl, phenyl or -C(=NOR)R’, R represents a hydrogen atom or C1-C6 alkyl, R’ represents C1-C6 alkyl, T represents an oxygen atom or a sulfur atom, R X is C1-C6 alkyl, C3-C 10 cycloalkyl, C1-C6 haloalkyl, R c substituted C1-C6 alkyl, benzyl, R X -1, R X -2, R X -3 or R X -4, R X -1 to R X -4 each represent a structure represented by the following structural formula,
[0014]
Chemical formula
[0015] X 1 represents a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl or C1-C6 alkoxy, X1 In the relationship where u5 represents an integer of 2, 3, 4, or 5, each X 1 may be the same as or different from each other, X 1 In the relationship where u4 represents an integer of 2, 3, or 4, each X 1 may be the same as or different from each other, R c represents cyano, C3 - C 10 cycloalkyl, C1 - C6 alkoxy, C1 - C6 alkoxycarbonyl, C1 - C6 alkylaminocarbonyl, di(C1 - C6 alkyl)aminocarbonyl, or -C(=NOR)R’, R Y represents a hydrogen atom, a halogen atom, or C1 - C6 alkyl, R 1 represents a hydrogen atom or C1 - C6 alkyl, R 2 represents a hydrogen atom or C1 - C6 alkyl, R 3 represents a hydrogen atom, a halogen atom, C1 - C6 alkyl, or C1 - C6 alkoxy, R 4 represents a hydrogen atom, a halogen atom, or C1 - C6 alkyl, R a represents a hydrogen atom, C1 - C6 alkyl, R a -1, R a -2, R a -3, R a -4, R a -5, or R a -6, R a -1, R a -2, R a -3, R a -4, R a -5, and R a -6 each represent a structure represented by the following structural formula,
[0016]
Chemical formula
[0017] R 5 represents a hydrogen atom or a C1-C6 alkyl group, R 6 represents a hydrogen atom or a C1-C6 alkyl group, r 1 when represents an integer of 2, two Rs 5 and two Rs 6 may be the same as each other or different from each other, R 7 represents a C1-C6 alkyl group, a C3-C 10 cycloalkyl group, a C1-C6 haloalkyl group or a phenyl group, R 8 represents a hydrogen atom or a C1-C6 alkyl group, R 9 represents a hydrogen atom or a C1-C6 alkyl group, Z represents Z-1 to Z-45 or Z-46, Z-1 to Z-46 each represent a structure represented by the following structural formula,
[0018] [Chemical formula]
[0019] [Chemical formula]
[0020] Note that the substitution position of Z 1 means that it is substituted on the aromatic ring of Z-1 to Z-46, Z 1 is hydroxy, carboxy, amino, nitro, cyano, a halogen atom, a C1-C6 alkyl group, a C3-C 10 cycloalkyl group, a C1-C6 haloalkyl group, a C3-C 10 halocycloalkyl group, a C2-C6 alkenyl group, a C1-C6 alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a C1-C6 alkylcarbonyl group, a C1-C6 alkoxycarbonyl group, R iC1-C6 alkyl replaced by, -OR d , -NHC(O)R e , -NR h C(O)R e , -NHS(O)2R f , -C≡CR g , -SO2NH2, -C(O)NH2, -C(S)NH2, -C(=NOH)NH2, E-1 to E-54, F-1 to F-15 or -C(=NOR)R', Z 1 in relation to, when n7 indicates an integer of 2, 3, 4, 5, 6 or 7, each Z 1 may be the same as or different from each other, Z 1 in relation to, when n6 indicates an integer of 2, 3, 4, 5 or 6, each Z 1 may be the same as or different from each other, Z 1 in relation to, when n5 indicates an integer of 2, 3, 4 or 5, each Z 1 may be the same as or different from each other, Z 1 in relation to, when n4 indicates an integer of 2, 3 or 4, each Z 1 may be the same as or different from each other, Z 1 in relation to, when n3 indicates an integer of 2 or 3, each Z 1 may be the same as or different from each other, Z 1 in relation to, when n2 indicates an integer of 2, each Z 1 may be the same as or different from each other, Z 2 represents C1-C6 alkyl or phenyl, R d is C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, R 10C1-C6 alkyl, C1-C6 alkylcarbonyl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, E-1 to E-54, F-1 to F-15, or C1-C6 alkylaminocarbonyl replaced by R 10 represents C3-C 10 cycloalkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, di(C1-C6 alkyl)aminocarbonyl, E-1 to E-54, F-1 to F-15, or -C(=NOR)R’, R e represents C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C2-C6 alkenyloxy, C1-C6 alkylamino, benzyloxy, E-1 to E-54, F-1 to F-15, or di(C1-C6 alkyl)amino, R f represents C1-C6 alkyl, C1-C6 haloalkyl, E-1 to E-54, F-1 to F-15, or di(C1-C6 alkyl)amino, R g represents a hydrogen atom or tri(C1-C4 alkyl)silyl, R h represents C1-C6 alkyl, R i represents hydroxy or C1-C6 alkoxy, E-1 to E-54 each represent a structure represented by the following structural formula,
[0021]
Chemical formula
[0022]
Chemical formula
[0023] F-1 to F-15 each represent a structure represented by the following structural formula,
[0024]
Chemical formula
[0025] Z a represents a halogen atom, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylcarbonyl or C1-C6 alkoxycarbonyl, Z a in relation to, when v7 indicates an integer of 2, 3, 4, 5, 6 or 7, each Z a may be the same as or different from each other, Z a in relation to, when v6 indicates an integer of 2, 3, 4, 5 or 6, each Z a may be the same as or different from each other, Z a in relation to, when v5 indicates an integer of 2, 3, 4 or 5, each Z a may be the same as or different from each other, Z a in relation to, when v4 indicates an integer of 2, 3 or 4, each Z a may be the same as or different from each other, Z a in relation to, when v3 indicates an integer of 2 or 3, each Z a may be the same as or different from each other, Z a in relation to, when v2 indicates an integer of 2, each Z a may be the same as or different from each other, Z b represents C1-C6 alkyl, m5 represents an integer of 0, 1, 2, 3, 4 or 5, n7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7, n6 represents an integer of 0, 1, 2, 3, 4, 5 or 6, n5 represents an integer of 0, 1, 2, 3, 4 or 5, n4 represents an integer of 0, 1, 2, 3 or 4, n3 represents an integer of 0, 1, 2, or 3, n2 represents an integer of 0, 1, or 2, n1 represents an integer of 0 or 1, u5 represents an integer of 0, 1, 2, 3, 4, or 5, u4 represents an integer of 0, 1, 2, 3, or 4, p represents an integer of 0 or 1, r 1 represents an integer of 1 or 2, r 2 represents an integer of 0 or 1, t represents an integer of 0, 1, or 2, v7 represents an integer of 0, 1, 2, 3, 4, 5, 6, or 7, v6 represents an integer of 0, 1, 2, 3, 4, 5, or 6, v5 represents an integer of 0, 1, 2, 3, 4, or 5, v4 represents an integer of 0, 1, 2, 3, or 4, v3 represents an integer of 0, 1, 2, or 3, v2 represents an integer of 0, 1, or 2, v1 represents an integer of 0 or 1.] A pyrazole compound represented by the formula or a salt thereof.
Effects of the Invention
[0026] The compound of the present invention represented by formula (1) exhibits excellent control activity against many pathogenic bacteria.
[0027] Therefore, the present invention can provide a useful fungicide, particularly a fungicide for agricultural and horticultural use.
Modes for Carrying Out the Invention
[0028] Hereinafter, the present invention will be described in detail.
[0029] In the compounds of the present invention, depending on the type of substituents, geometric isomers of the E-form and Z-form may exist. However, the compounds of the present invention include these E-forms, Z-forms, or mixtures containing the E-form and Z-form in any ratio. In this specification, a compound having geometric isomers is, for example, represented by formula (1-Ra It is represented as a compound having a wavy line bond as shown in (-6).
[0030] [Chemical formula]
[0031] In addition, the compounds of the present invention may have optically active forms due to the presence of one or more asymmetric carbon atoms or asymmetric sulfur atoms, but the compounds of the present invention include all optically active forms or racemates.
[0032] In addition, the compounds of the present invention may have tautomers depending on the type of substituent, but the compounds of the present invention include all tautomers or mixtures of tautomers containing them in any ratio.
[0033] In addition, the compounds of the present invention may exist as one or more rotational isomers due to restricted bond rotation caused by steric hindrance between substituents, but the compounds of the present invention include all rotational isomers or mixtures of diastereomers containing them in any ratio.
[0034] Next, specific examples of each substituent shown in this specification are shown below. Here, n- means normal, i- means iso, s- means secondary, tert- means tertiary, and Ph means phenyl.
[0035] Examples of the "halogen atom" in this specification include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Note that the notation "halo" in this specification also represents these halogen atoms.
[0036] The notation "C a ~C b alkyl" in this specification represents a linear or branched saturated hydrocarbon group having a to b carbon atoms. "C a ~C bExamples of "alkyl" include methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, tert-butyl, n-pentyl, 1,1-dimethylpropyl, and n-hexyl. "C a ~C b "alkyl" is selected within the specified range of the number of carbon atoms.
[0037] In this specification, the notation "C a ~C b "haloalkyl" represents a linear or branched saturated hydrocarbon group having a carbon atom number of a to b, in which the hydrogen atoms bonded to the carbon atoms are arbitrarily substituted by halogen atoms. When substituted by two or more halogen atoms, these halogen atoms may be the same as or different from each other. "C a ~C b Examples of "haloalkyl" include fluoromethyl, chloromethyl, bromomethyl, iodomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, trichloromethyl, bromodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2,2-difluoroethyl, and 2,2,2-trichloroethyl. "C a ~C b "haloalkyl" is selected within the specified range of the number of carbon atoms.
[0038] In this specification, the notation "C a ~C b "alkenyl" represents an unsaturated hydrocarbon having a linear or branched structure with a carbon atom number of a to b and having one or more double bonds in the molecule. "C a ~C b Examples of "alkenyl" include vinyl, 1-propenyl, 2-propenyl (hereinafter also referred to as allyl), 1-methylethenyl, 2-butenyl, 2-methyl-2-propenyl, 3-methyl-2-butenyl, and 1,1-dimethyl-2-propenyl. "C a ~Cb "Alkenyl" is selected within the specified range of carbon atom numbers.
[0039] "C" in this specification a ~C b The notation of "alkynyl" represents a linear or branched unsaturated hydrocarbon having a carbon atom number of a to b and having one or more triple bonds in the molecule. "C" a ~C b Examples of "alkynyl" include ethynyl, propargyl, 2-butynyl, 3-butynyl, 1-pentynyl, and 1-hexynyl. "C" a ~C b "alkynyl" is selected within the specified range of carbon atom numbers.
[0040] "C" in this specification a ~C b The notation of "alkoxy" represents alkyl-O- having a carbon atom number of a to b in the above-mentioned meaning. "C" a ~C b Examples of "alkoxy" include methoxy, ethoxy, n-propyloxy, i-propyloxy, n-butyloxy, i-butyloxy, s-butyloxy, tert-butyloxy, and 2-ethylhexyloxy. "C" a ~C b "alkoxy" is selected within the specified range of carbon atom numbers.
[0041] "C" in this specification a ~C b The notation of "haloalkoxy" represents haloalkyl-O- having a carbon atom number of a to b in the above-mentioned meaning. "C" a ~C b Examples of "haloalkoxy" include difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2,-tetrafluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy, and 1,1,2,3,3,3-hexafluoropropyloxy. "C"a ~C b "Haloalkoxy" is selected within the specified range of carbon atom numbers.
[0042] "C a ~C b The notation "alkenyloxy" represents alkenyl-O- having the above meaning with a to b carbon atoms. "C a ~C b Examples of "alkenyloxy" include vinyloxy, 1-propenyloxy, 2-propenyloxy, 1-methylethenyloxy, 2-butenyloxy, 2-methyl-2-propenyloxy, 3-methyl-2-butenyloxy, 1,1-dimethyl-2-propenyloxy, etc. "C a ~C b "Alkenyloxy" is selected within the specified range of carbon atom numbers.
[0043] "C a ~C b The notation "alkylthio" represents alkyl-S- having the above meaning with a to b carbon atoms. "C a ~C b Examples of "alkylthio" include methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, and tert-butylthio, etc. "C a ~C b "Alkylthio" is selected within the specified range of carbon atom numbers.
[0044] "C a ~C b The notation "alkylsulfinyl" represents alkyl-S(O)- having the above meaning with a to b carbon atoms. "C a ~C b Examples of "alkylsulfinyl" include methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, i-propylsulfinyl, n-butylsulfinyl, i-butylsulfinyl, S-butylsulfinyl, and tert-butylsulfinyl, etc. "Ca ~C b "Alkylsulfinyl" is selected within the specified range of the number of carbon atoms.
[0045] "C a ~C b The notation of "alkylsulfonyl" represents alkyl-SO2- having the above meaning consisting of a to b carbon atoms. "C a ~C b Examples of "alkylsulfonyl" include methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl, n-butylsulfonyl, i-butylsulfonyl, s-butylsulfonyl, and tert-butylsulfonyl. "C a ~C b "Alkylsulfonyl" is selected within the specified range of the number of carbon atoms.
[0046] "C a ~C b The notation of "cycloalkyl" represents a cyclic hydrocarbon group consisting of a to b carbon atoms. "C a ~C b "Cycloalkyl" can form, for example, a monocyclic or polycyclic structure from a 3-membered ring to a 10-membered ring. Also, the hydrogen in each ring may be optionally substituted by alkyl within the specified range of the number of carbon atoms. "C a ~C b Examples of "cycloalkyl" include cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. "C a ~C b "Cycloalkyl" is selected within the specified range of the number of carbon atoms.
[0047] "C a ~C bThe notation "halocycloalkyl" represents a cyclic hydrocarbon group having a to b carbon atoms, in which the hydrogen atoms bonded to the carbon atoms are optionally substituted by halogen atoms. When substituted by two or more halogen atoms, those halogen atoms may be the same as or different from each other. "C a ~C b Examples of "halocycloalkyl" include 2,2-difluorocyclopropyl, 2,2-dichlorocyclopropyl, 2,2-dibromocyclopropyl, 2,2-difluoro-1-methylcyclopropyl, 2,2-dichloro-1-methylcyclopropyl, 2,2-dibromo-1-methylcyclopropyl, and 2,2,3,3-tetrafluorocyclobutyl. "C a ~C b "Halocycloalkyl" is selected within the specified range of the number of carbon atoms.
[0048] In this specification, the notation "C a ~C b alkylamino" represents an amino group in which one of the hydrogen atoms is substituted by an alkyl as defined above having a to b carbon atoms. "C a ~C b Examples of "alkylamino" include methylamino, ethylamino, n-propylamino, i-propylamino, n-butylamino, i-butylamino, and tert-butylamino. "C a ~C b "Alkylamino" is selected within the specified range of the number of carbon atoms.
[0049] In this specification, the notation "di(C a ~C b alkyl)amino" represents an amino group in which both hydrogen atoms are substituted by alkyls as defined above having a to b carbon atoms, which may be the same as or different from each other. "Di(C a ~C bExamples of "(alkyl)amino" include dimethylamino, ethyl(methyl)amino, diethylamino, n-propyl(methyl)amino, i-propyl(methyl)amino, di(n-propyl)amino, di(n-butyl)amino, and the like. "Di(C a ~C b alkyl)amino" Each alkyl is selected within the specified range of carbon atom numbers.
[0050] As used herein, the notation "C a ~C b alkylcarbonyl" represents alkyl-C(O)- having the above meaning with a to b carbon atoms. "C a ~C b alkylcarbonyl" Examples include acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, 2-methylbutanoyl, pivaloyl, hexanoyl, heptanoyl, and the like. "C a ~C b alkylcarbonyl" is selected within the specified range of carbon atom numbers.
[0051] As used herein, the notation "C a ~C b alkoxycarbonyl" represents alkyl-O-C(O)- having the above meaning with a to b carbon atoms. "C a ~C b alkylcarbonyl" Examples include methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, i-propyloxycarbonyl, n-butoxycarbonyl, i-butoxycarbonyl, s-butoxycarbonyl, tert-butoxycarbonyl, 2-ethylhexyloxycarbonyl, and the like. "C a ~C b alkylcarbonyl" is selected within the specified range of carbon atom numbers.
[0052] As used herein, the notation "C a ~C bThe notation "alkylaminocarbonyl" represents carbamoyl in which one of the hydrogen atoms is substituted by alkyl having a carbon atom number of a to b as defined above. "C a ~C b Examples of "alkylaminocarbonyl" include methylcarbamoyl, ethylcarbamoyl, n-propylcarbamoyl, i-propylcarbamoyl, n-butylcarbamoyl, i-butylcarbamoyl, s-butylcarbamoyl, tert-butylcarbamoyl and the like. "C a ~C b "alkylaminocarbonyl" is selected within the specified range of carbon atom numbers.
[0053] In this specification, the notation "C a ~C b cycloalkylaminocarbonyl" represents carbamoyl in which one of the hydrogen atoms is substituted by cycloalkyl having a carbon atom number of a to b as defined above. "C a ~C b Examples of "cycloalkylaminocarbonyl" include cyclopropylcarbamoyl, cyclobutylcarbamoyl, cyclopentylcarbamoyl, cyclohexylcarbamoyl and the like. "C a ~C b "cycloalkylaminocarbonyl" is selected within the specified range of carbon atom numbers.
[0054] In this specification, the notation "di(C a ~C b )alkylaminocarbonyl" represents carbamoyl in which both hydrogen atoms are substituted by alkyl having a carbon atom number of a to b as defined above, which may be the same or different from each other. Examples of "di(C a ~C b )alkylaminocarbonyl" include N,N-dimethylcarbamoyl, N-ethyl-N-methylcarbamoyl, N,N-diethylcarbamoyl, N,N-di(n-propyl)carbamoyl, N,N-di(n-butyl)carbamoyl and the like. "di(C a ~C b) Each alkyl of "alkylaminocarbonyl" is selected within the specified range of the number of carbon atoms.
[0055] As used herein, "tri(C a ~C b )alkylsilyl" denotes silyl substituted by an alkyl having the above meaning and consisting of a to b carbon atoms, which may be the same or different from each other. "Tri(C a ~C b )alkylsilyl" includes, for example, trimethylsilyl, triethylsilyl, tri(n-propyl)silyl, ethyldimethylsilyl, n-propyldimethylsilyl, n-butyldimethylsilyl, i-butyldimethylsilyl, and tert-butyldimethylsilyl. Each alkyl of "tri(C a ~C b )alkylsilyl" is selected within the specified range of the number of carbon atoms.
[0056] As used herein, "C c substituted with R a ~C b alkyl", "C i substituted with R a ~C b alkyl" or "C 10 substituted with R a ~C b alkyl" denotes an alkyl having the above meaning and consisting of a to b carbon atoms, wherein any hydrogen atom bonded to a carbon atom of the alkyl is partially or completely substituted with one or more substituents R c , R i or R 10 . These are each selected within the specified range of the number of carbon atoms. When there are two or more substituents R c , R i or R 10 , the substituents R c , R i or R 10 may be the same as or different from each other.
[0057] As used herein, "C b substituted with Ra ~C b The notation "alkoxy" represents an alkoxy in which any hydrogen atom bonded to a carbon atom is partially or completely substituted by one or more substituents R b and has the meaning described above, consisting of a to b carbon atoms. "R b substituted C a ~C b alkoxy" is selected within the specified range of carbon atom numbers. When two or more substituents R b are present, the substituents R b may be the same or different from each other.
[0058] In this specification, the notation "benzyl" represents -CH2C6H5.
[0059] In this specification, the notation "benzyloxy" represents -О-CH2C6H5.
[0060] Next, a method for producing the compound of the present invention represented by formula (1) will be described. The compound of the present invention represented by formula (1) can be produced, for example, by the following method. Note that the following description is merely illustrative, and the compound of the present invention represented by formula (1) may be produced by other methods. Hereinafter, "the compound of the present invention represented by formula (1)" is also referred to as "compound (1)", and "the compound represented by formula (2)" is also referred to as "compound (2)". The same applies to other compounds.
[0061] (Production Example 1) The compound (1) of the present invention can be produced, for example, by the following production method.
[0062] [Chemical formula]
[0063] [In the formula, G, T, R X , R Y , R 1 , R 2 , R 3 , R 4 , Ra , Z, and p have the same meanings as described above. Compound (1) can be produced by reacting compound (1-1) with compound (1-a) or a salt thereof (for example, hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, para-toluenesulfonate, etc.) and a dehydrating condensing agent in a solvent or without a solvent, optionally in the presence of either one or both of a base and an additive.
[0064] The amount of compound (1-a) or a salt thereof and the dehydrating condensing agent used can be 0.5 to 50 equivalents relative to 1 equivalent of compound (1-1).
[0065] Some of the compounds represented by compound (1-a) are known compounds and can be obtained as commercial products. Also, other compounds represented by compound (1-a) can be produced according to the general known compound synthesis methods described in the literature.
[0066] Examples of the dehydrating condensing agent include 1H-benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, N,N'-dicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, and 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate.
[0067] When using a solvent, the solvent used only needs to be inert to the reaction. Examples of such solvents include water; alcohol solvents such as methanol, ethanol, or tert-butyl alcohol; ether solvents such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane, or diglyme; aromatic hydrocarbon solvents such as benzene, xylene, or toluene; aliphatic hydrocarbon solvents such as n-pentane, n-hexane, or cyclohexane; halogenated hydrocarbon solvents such as dichloromethane, chloroform, or 1,2-dichloroethane; nitrile solvents such as acetonitrile or propionitrile; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, or N,N'-dimethylimidazolidinone; dimethyl sulfoxide; pyridine; or a mixed solvent thereof; and the like.
[0068] The reaction can be carried out in the presence of a base. Examples of the base that can be used include organic bases such as pyridine, 2,6-lutidine, 4-dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, N,N-dimethylaniline, 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), or 1,5-diazabicyclo[4.3.0]-5-nonene (DBN); inorganic bases such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium bicarbonate, potassium carbonate, cesium carbonate, or potassium phosphate; metal alkoxides such as sodium methoxide, sodium ethoxide, or potassium tert-butoxide; The amount of the base used can be 0.1 to 100 equivalents relative to 1 equivalent of the compound (1-1).
[0069] The reaction can be carried out in the presence of an additive. Examples of the additive that can be used include 1-hydroxybenzotriazole, 1-hydroxy-7-azabenzotriazole, or 4-(dimethylamino)pyridine, etc. The amount of the additive used can be 0.005 to 100 equivalents relative to 1 equivalent of the compound (1-1).
[0070] The reaction temperature can be set to any temperature from -78°C to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate or the reaction temperature, but can usually be arbitrarily set within the range of 5 minutes to 100 hours.
[0071] (Production Example 2) The compound (2) of the present invention can be produced, for example, by the following production method.
[0072] [Chemical formula]
[0073] [In the formula, L represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom, C1-C4 alkylsulfonyloxy (for example, methanesulfonyloxy, etc.), halosulfonyloxy (for example, fluorosulfonyloxy, etc.), C1-C4 haloalkylsulfonyloxy (for example, trifluoromethanesulfonyloxy, etc.) or arylsulfonyloxy (for example, paratoluenesulfonyloxy, etc.), and R Xa represents C1-C6 alkyl, C3-C 10 cycloalkyl, C1-C6 haloalkyl, C1-C6 alkyl substituted with R c or benzyl, and G, T, R Y , R 1 , R 2 , R 3 , R 4 , R a , R c , Z and p represent the same meanings as described above.] Compound (2) can be produced by reacting compound (2-1) with compound (D) in a solvent or without a solvent, and optionally in the presence of a base.
[0074] The amount of compound (D) used can be 0.5 to 50 equivalents relative to 1 equivalent of compound (2-1).
[0075] Some of the compounds represented by compound (D) are known compounds and are available as commercial products. The other compounds represented by compound (D) can also be produced according to the general known compound synthesis methods described in the literature.
[0076] When using a solvent, the solvent used may be inert to the reaction, and examples of such solvents include the solvents exemplified in Production Example 1.
[0077] Examples of the base that can be used in this reaction include the bases exemplified in Production Example 1. The amount of the base used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (2-1).
[0078] The reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Production Example 1.
[0079] (Production Example 3) The compound (5) or compound (6) of the present invention can be produced, for example, by the following production method.
[0080]
Chemical formula
[0081] [In the formula, G, T, R X , R Y , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , Z, r 1 and p represent the same meanings as described above.] Compound (5) or compound (6) can be produced by reacting compound (4) of the present invention with an oxidizing agent in a solvent or without a solvent.
[0082] Examples of the oxidizing agent that can be used include hydrogen peroxide, meta-chloroperbenzoic acid, etc. The amount of the oxidizing agent used can be 0.1 to 100 equivalents relative to 1 equivalent of the compound (4).
[0083] When a solvent is used, the solvent used may be inert to the reaction, and examples of the solvent include the solvents exemplified in Production Example 1.
[0084] The reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Production Example 1.
[0085] The compound (4) can be synthesized according to the method of Production Example 1.
[0086] (Production Example 4) The compound (8) of the present invention can be produced, for example, by the following production method.
[0087] [Chemical formula]
[0088] [In the formula, R 1a represents C1-C6 alkyl, and G, L, T, R X , R Y , R 2 , R 3 , R 4 , R a , Z and p represent the same meanings as described above.] The compound (8) can be produced by reacting the compound (7) of the present invention with the compound (D1) in a solvent or without a solvent, and optionally in the presence of a base.
[0089] The amount of the compound (D1) used can be 0.5 to 50 equivalents relative to 1 equivalent of the compound (7).
[0090] Some of the compounds represented by the compound (D1) are known compounds and can be obtained as commercial products. The other compounds represented by the compound (D1) can also be produced according to the general known compound synthesis methods described in the literature.
[0091] When a solvent is used, the solvent used may be inert to the reaction, and examples of the solvent include the solvents exemplified in Production Example 1.
[0092] Examples of the base that can be used in the reaction include the bases exemplified in Production Example 1. The amount of the base used can be 0.1 to 100 equivalents relative to 1 equivalent of the compound (7).
[0093] The reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Production Example 1.
[0094] The compound (7) can be synthesized according to the method of Production Example 1.
[0095] (Production Example 5) The compound (10) of the present invention can be produced, for example, by the following production method.
[0096] [Chemical formula]
[0097] [In the formula, G, R X , R Y , R 1 , R 2 , R 3 , R 4 , R a , Z and p represent the same meanings as described above.] The compound (10) can be produced by reacting the compound (9) of the present invention with 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphospholane 2,4-disulfide (hereinafter also referred to as "Lawesson's reagent") in a solvent or without a solvent, and optionally in the presence of a base.
[0098] The amount of the Lawson's reagent used can be 0.5 to 50 equivalents relative to 1 equivalent of the compound (9).
[0099] When a solvent is used, the solvent used may be inert to the reaction, and examples of the solvent include the solvents exemplified in Production Example 1.
[0100] The reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Production Example 1.
[0101] The compound (9) can be synthesized according to the method of Production Example 1.
[0102] (Production Example 6) The compound (12) of the present invention can be produced, for example, by the following production method.
[0103]
Chemical formula
[0104] [In the formula, R d1 represents C1-C6 alkyl or R d , G, L, T, R X , R Y , R 2 , R 3 , R 4 , R a , R d and p represent the same meanings as described above.] The compound (12) can be produced by reacting the compound (11) of the present invention with the compound (D2) in a solvent or without a solvent, and optionally in the presence of a base.
[0105] The amount of the compound (D2) used can be 0.5 to 50 equivalents relative to 1 equivalent of the compound (11).
[0106] Some of the compounds represented by compound (D2) are known compounds and are available as commercial products. Other compounds represented by compound (D2) can also be produced according to the general known compound synthesis methods described in the literature.
[0107] When using a solvent, the solvent used may be inert to the reaction, and examples of such solvents include the solvents exemplified in Production Example 1.
[0108] Examples of the base that can be used in this reaction include the bases exemplified in Production Example 1. The amount of the base used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (11).
[0109] The reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Production Example 1.
[0110] Compound (11) can be synthesized according to the method of Production Example 1.
[0111] (Production Example 7) The compound (14) of the present invention or the compound (15) of the present invention can be produced, for example, by the following production method.
[0112] [Chemical formula]
[0113] [In the formula, L 1 represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom, or C1-C4 alkylcarbonyloxy (for example, acetoxy, etc.), and L 2 represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom, C1-C4 alkylsulfonyloxy (for example, methanesulfonyloxy, etc.), halosulfonyloxy (for example, fluorosulfonyloxy, etc.), C1-C4 haloalkylsulfonyloxy (for example, trifluoromethanesulfonyloxy, etc.) or arylsulfonyloxy (for example, paratoluenesulfonyloxy, etc.), and G, T, R X , R Y , R2 and R 3 and R 4 and R a and R e and R f and p represent the same meaning as described above. Compound (14) or compound (15) can be produced by reacting compound (13) of the present invention with compound (E) or compound (F) in a solvent or without a solvent, optionally in the presence of a base.
[0114] The amount of compound (E) or compound (F) used can be 0.5 to 50 equivalents relative to 1 equivalent of compound (13).
[0115] Some of the compounds represented by compound (E) are known compounds and can be obtained as commercial products. Also, other compounds represented by compound (E) can be produced according to the general known compound synthesis methods described in the literature.
[0116] Some of the compounds represented by compound (F) are known compounds and can be obtained as commercial products. Also, other compounds represented by compound (F) can be produced according to the general known compound synthesis methods described in the literature.
[0117] When using a solvent, the solvent used may be inert to the reaction, and examples of such solvents include the solvents exemplified in Production Example 1.
[0118] Examples of the base that can be used in this reaction include the bases exemplified in Production Example 1. The amount of the base used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (13).
[0119] The reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Production Example 1.
[0120] Compound (13) can be synthesized according to the method of Production Example 1.
[0121] The compound (1-1) used in Production Example 1 can be produced, for example, according to the production route (reaction pathway) shown in the following Reaction Scheme 1.
[0122] [Reaction Scheme 1]
[0123] [Chemical Formula]
[0124] [In the formula, X represents a halogen atom, and G, T, R X and R Y represent the same meanings as described above.] Compound (1-1) can be obtained by reacting compound (1-2) with compound (A) in a solvent or without a solvent, in the presence of a base, and optionally in the presence of either or both of a copper catalyst and an additive. Alternatively, compound (1-1) can be obtained by reacting compound (1-2) with compound (A) in the presence of a base and optionally in the presence of a palladium catalyst and a ligand.
[0125] Some of the compounds represented by compound (1-2) are known compounds and can be obtained as commercial products. Further, the other compounds represented by compound (1-2) can also be produced according to the general known compound synthesis methods described in the literature.
[0126] The amount of compound (A) used can be 0.5 to 50 equivalents relative to 1 equivalent of compound (1-2).
[0127] Some of the compounds represented by compound (A) are known compounds and can be obtained as commercial products. Further, the other compounds represented by compound (A) can also be produced according to the general known compound synthesis methods described in the literature.
[0128] When using a solvent, the solvent used may be inert to the reaction, and examples of such a solvent include the solvents exemplified in Production Example 1.
[0129] The reaction can be carried out in the presence of a base. Examples of the base that can be used include, for example, the bases exemplified in Production Example 1. The amount of the base used can be 0.1 to 100 equivalents relative to 1 equivalent of the compound (1-2).
[0130] The reaction can be carried out in the presence of a copper catalyst. Examples of the copper catalyst that can be used include, for example, copper(I) iodide, copper(I) trifluoromethanesulfonate benzene complex, copper(I) trifluoromethanesulfonate toluene complex, and the like. The amount of the copper catalyst used can be 0.001 to 50 equivalents relative to 1 equivalent of the compound (1-2).
[0131] The reaction can be carried out in the presence of an additive. Examples of the additive that can be used include, for example, N,N-dimethylglycine, 4-(dimethylamino)pyridine, and the like. The amount of the additive used can be 0.001 to 100 equivalents relative to 1 equivalent of the compound (1-2).
[0132] The reaction can be carried out in the presence of a palladium catalyst. Examples of the palladium catalyst that can be used include, for example, palladium(II)(π-cinnamyl)chloride (dimer), allylpalladium(II) chloride (dimer), and the like. The amount of the palladium catalyst used can be 0.001 to 50 equivalents relative to 1 equivalent of the compound (1-2).
[0133] The reaction can be carried out in the presence of a ligand. Examples of ligands that can be used include 2-di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (tert-butyl-XPhos), tetramethyl-di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (tetramethyldi-tert-butyl-XPhos), 2-di-(tert-butyl)phosphino-2',4',6'-triisopropyl-3-methoxy-6-methylbiphenyl (RockPhos), or 2-(dicyclohexylphosphino)-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl (BrettPhos), etc. The amount of the ligand used can be 0.001 to 50 equivalents relative to 1 equivalent of compound (1-2).
[0134] The reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Production Example 1.
[0135] Among compounds (1-1), a compound (1-1-1) in which T is an oxygen atom and R Y is a hydrogen atom can be produced, for example, according to the production route (reaction pathway) represented by the following reaction formula.
[0136] [Reaction Formula 2]
[0137] [Chemical Formula]
[0138] [In the formula, R 101 represents C1-C6 alkyl, and G and R X represent the same meanings as described above.] Step 1: Compound (1-3) can be obtained by reacting compound (1-4) with compound (B) or a salt thereof (for example, hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, or para-toluenesulfonate, etc.) in a solvent or without a solvent, and optionally in the presence of a base.
[0139] Some of the compounds represented by compound (B) are known compounds and can be obtained as commercial products. The other compounds represented by compound (B) can also be produced according to the general known compound synthesis methods described in the literature.
[0140] The amount of compound (B) or its salt used can be 0.5 to 50 equivalents relative to 1 equivalent of compound (1-4).
[0141] Some of the compounds represented by compound (1-4) are known compounds described in Bioorganic & Medicinal Chemistry Letters 2015, Volume 25, page 4481. The other compounds represented by compound (1-4) can also be synthesized in the same manner as known compounds according to the methods described in the said literature.
[0142] When using a solvent, the solvent used only needs to be inert to the reaction. Examples of such solvents include the solvents exemplified in Production Example 1.
[0143] This reaction can be carried out in the presence of a base. Examples of the base that can be used include the bases exemplified in Production Example 1. The amount of the base used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (1-4).
[0144] The reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Production Example 1.
[0145] Step 2: Compound (1-1-1) can be obtained by reacting compound (1-3) with an oxidizing agent in a solvent or without a solvent.
[0146] Examples of the oxidizing agent that can be used include potassium permanganate, etc. The amount of the oxidizing agent used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (1-3).
[0147] When using a solvent, the solvent used only needs to be inert to the reaction. Examples of such solvents include the solvents exemplified in Production Example 1.
[0148] The reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Production Example 1.
[0149] Among the compounds (1-1), the compound (1-1-1) in which T is an oxygen atom and R Y is a hydrogen atom can be produced, for example, according to the production route (reaction pathway) represented by the following reaction formula.
[0150] [Reaction Formula 3]
[0151]
Chemical Formula
[0152] [In the formula, G and R X represent the same meanings as described above.] Step 1: Compound (1-5) can be obtained by reacting compound (1-6) under the same conditions as in Step 1 of Reaction Formula 2.
[0153] Some of the compounds represented by compound (1-6) are known compounds described in International Publication No. 2003 / 016275, and the other compounds represented by compound (1-6) can also be synthesized in the same manner as known compounds according to the method described in this document.
[0154] Step 2: Compound (1-1-1) can be obtained by reacting compound (1-5) with carbon dioxide in a solvent or without a solvent in the presence of a base.
[0155] Examples of the base that can be used include n-butyllithium, etc. The amount of the base used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (1-5).
[0156] When using a solvent, the solvent used only needs to be inert to the reaction, and examples of such solvents include the solvents exemplified in Production Example 1.
[0157] The reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Production Example 1.
[0158] Among the compound (1-a) or its salts (for example, hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, para-toluenesulfonate, etc.) used in Production Example 1, R a is R a -1, the compound (1-a’) can be produced, for example, according to the production route (reaction pathway) shown in the following Reaction Formula 4.
[0159] [Reaction Formula 4]
[0160] [Chemical Formula]
[0161] [In the formula, L, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , Z, p and r 1 represent the same meanings as described above.] Step 1: The compound (1-a’-2) can be produced by reacting the compound (1-a’-1) with the compound (C1) or the compound (C2) in a solvent or without a solvent, optionally in the presence of a base and, if necessary, in the presence of a phase transfer catalyst.
[0162] A part of the compound represented by the compound (1-a’-1) is a known compound and can be obtained as a commercial product. In addition, other compounds represented by the compound (1-a’-1) can also be produced according to the general known compound synthesis methods described in the literature.
[0163] Part of the compounds represented by compound (C1) or compound (C2) are known compounds and can be obtained as commercial products. The other compounds represented by compound (C1) or compound (C2) can also be produced according to the general known compound synthesis methods described in the literature.
[0164] The amount of compound (C1) or compound (C2) used can be 0.5 to 50 equivalents relative to 1 equivalent of compound (1-a’-1).
[0165] When using a solvent, the solvent used may be inert to the reaction, and examples of such solvents include the solvents exemplified in Production Example 1.
[0166] This reaction can be carried out in the presence of a base. Examples of the base that can be used include the bases exemplified in Production Example 1. The amount of the base used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (1-a’-1).
[0167] This reaction can be carried out in the presence of a phase transfer catalyst. Examples of the phase transfer catalyst that can be used include quaternary ammonium salts such as tetrabutylammonium bromide. The amount of the phase transfer catalyst used can be 0.001 to 10 equivalents relative to 1 equivalent of compound (1-a’-1).
[0168] The reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Production Example 1.
[0169] Step 2: Compound (1-a’) or a salt thereof (for example, hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate or p-toluenesulfonate, etc.) can be produced by reacting compound (1-a’-2) with an acid in a solvent or without a solvent.
[0170] When using a solvent, the solvent used may be inert to the reaction, and examples of such solvents include the solvents exemplified in Production Example 1.
[0171] The reaction can be carried out in the presence of an acid. Examples of the acid that can be used include hydrochloric acid, sulfuric acid, acetic acid, trifluoroacetic acid, and the like. The amount of the acid used can be 0.5 to 1000 equivalents relative to 1 equivalent of the compound (1-a’-2).
[0172] The reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Production Example 1.
[0173] The compound (2-1) used in Production Example 2 can be produced, for example, according to the production route (reaction pathway) shown in the following Reaction Scheme 5.
[0174] [Reaction Scheme 5]
[0175] [Chemical Formula]
[0176] [wherein, G, T, R Y , R 1 , R 2 , R 3 , R 4 , R a , Z and p have the same meanings as described above.] The compound (2-1) can be produced by reacting the compound (3) of the present invention with an acid in a solvent or without a solvent.
[0177] When a solvent is used, the solvent used may be inert to the reaction. Examples of the solvent include the solvents exemplified in Production Example 1.
[0178] Examples of the acid that can be used in this reaction include acids such as hydrochloric acid, sulfuric acid, formic acid, and trifluoroacetic acid. The amount of the acid used can be 0.1 to 100 equivalents relative to 1 equivalent of the compound (3).
[0179] The reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Production Example 1.
[0180] Compound (3) can be synthesized according to the method of Production Method 1.
[0181] Examples of the pyrazole compounds represented by formula (1) included in the present invention that can be produced using these methods include, specifically, the compounds represented in Table 1 and Tables 1-2 to 1-840. However, the compounds represented in Table 1 and Tables 1-2 to 1-840 are for illustrative purposes only, and the pyrazole compounds included in the present invention are not limited to only these.
[0182] In the tables, the substituent described as "Me" represents "methyl", and hereinafter in the same manner, "Et" represents "ethyl", "nPr" represents "normal propyl", "tBu" represents "tertiary butyl", "iPr" represents "isopropyl", "cPr" represents "cyclopropyl", "tAm" represents "1,1-dimethylpropyl", and "Ph" represents "phenyl".
[0183] Also in the tables, for example, the description of "4-" in "4-Me-Ph" represents the substitution position on the phenyl group as described below. For example, "4-Me-Ph" represents 4-methylphenyl, and "2,6-F2-Ph" represents 2,6-difluorophenyl. For example, the description of "4-" in "1-Me-Ph" represents the substitution position on the phenyl group as described below. For example, "4-Me-Ph" represents 4-methylphenyl, and "2,6-F2-Ph" represents 2,6-difluorophenyl.
[0184]
Chemical formula
[0185] Also, the substituents represented by D-1a, D-2a, E-2a, E-3a, E-7a, E-12a, E-14a, E-22a, E-23a, E-24a, E-30a, F-3a, Z-2a, Z-3a, Z-4a, Z-6a, and Z-45a each represent the following structures.
[0186]
Chemical formula
[0187] [Chemical formula]
[0188] [Chemical formula]
[0189] [Chemical formula]
[0190] Note that the numbers described in the above structural formula represent the substitution positions. For example, the description "6-OMe-(E-3a)" in the table represents the following structure. A structural formula without a description of a substituent represents an unsubstituted structure.
[0191] [Chemical formula]
[0192] [Table 1]
[0193] [Chemical formula]
[0194] G is Ph, R X is tBu, R Y is H, R 3 is H, R 4 is H. ――――――――――――――― ――――――――――――――― Z Z ――――――――――――――― ――――――――――――――― 2-F-Ph 2-Cl-4-(E-3a)-Ph 3-F-Ph 2-Cl-4-(6-CN-(E-3a))-Ph 4-F-Ph 2-Cl-4-(6-F-(E-3a))-Ph 2-Cl-Ph 2-Cl-4-(6-Cl-(E-3a))-Ph 3-Cl-Ph 2-Cl-4-(6-CF3-(E-3a))-Ph 4-Cl-Ph 2-Cl-4-(6-OMe-(E-3a))-Ph 2-Br-Ph 2-Cl-4-(E-7a)-Ph 3-Br-Ph 2-Cl-4-(2-F-(E-7a))-Ph 4-Br-Ph 2-Cl-4-(2-Cl-(E-7a))-Ph 2-I-Ph 2-Cl-4-(2-CF3-(E-7a))-Ph 3-I-Ph 2-Cl-4-(2-OMe-(E-7a))-Ph 4-I-Ph 2-Cl-4-(E-22a)-Ph 2-Me-Ph 2-Cl-4-(E-23a)-Ph 3-Me-Ph 2-Cl-4-(E-24a)-Ph 4-Me-Ph 2-Cl-4-(E-12a)-Ph 2-Et-Ph 2-Cl-4-(E-14a)-Ph 3-Et-Ph 2-Cl-4-SMe 4-Et-Ph 2-Cl-4-SOMe 2-cPr-Ph 2-Cl-4-SO2Me 3-cPr-Ph 2-Cl-4-SEt 4-cPr-Ph 2-Cl-4-SOEt 2-CF3-Ph 2-Cl-4-SO2Et 3-CF3-Ph 2-Br-4-nPr-Ph 4-CF3-Ph 2-Br-4-CH2F-Ph 2-CF2H-Ph 2-Br-4-CH2CF3-Ph 3-CF2H-Ph 2-Br-4-CH2CF2H-Ph 4-CF2H-Ph 2-Br-4-CH=CH2-Ph 2-OMe-Ph 2-Br-4-CH=CF2-Ph 3-OMe-Ph 2-Br-4-C≡CH-Ph 4-OMe-Ph 2-Br-4-OH-Ph 2-OEt-Ph 2-Br-4-OnPr-Ph 3-OEt-Ph 2-Br-4-OCH2cPr-Ph 4-OEt-Ph 2-Br-4-OCH2CH=CH2-Ph 2-OCF3-Ph 2-Br-4-OCH2C≡CH-Ph 3-OCF3-Ph 2-Br-4-OCH2CF3-Ph 4-OCF3-Ph 2-Br-4-OCH2CF2H-Ph 2-OCF2H-Ph 2-Br-4-OCH2CF2CF2H-Ph 3-OCF2H-Ph 2-Br-4-OCH2C(=NOMe)Me-Ph 4-OCF2H-Ph 2-Br-4-OCH2C(=NOEt)Me-Ph 2,4-F2-Ph 2-Br-4-OCH2(D-1a)-Ph 2-F-4-Cl-Ph 2-Br-4-OCH2(D-2a)-Ph 2-F-4-Br-Ph 2-Br-4-OCH2(E-2a)-Ph 2-F-4-I-Ph 2-Br-4-OCH2(6-Cl-(E-2a))-Ph 2-F-4-Me-Ph 2-Br-4-OCH2(6-Br-(E-2a))-Ph 2-F-4-Et-Ph 2-Br-4-OCH2(6-Me-(E-2a))-Ph 2-F-4-cPr-Ph 2-Br-4-OCH2(6-OMe-(E-2a))-Ph 2-F-4-CF3-Ph 2-Br-4-OCH2(5-Cl-(E-2a))-Ph 2-F-4-CF2H-Ph 2-Br-4-OCH2(5-Br-(E-2a))-Ph 2-F-4-OMe-Ph 2-Br-4-OCH2(5-Me-(E-2a))-Ph 2-F-4-OEt-Ph 2-Br-4-OCH2(5-OMe-(E-2a))-Ph 2-F-4-OCF3-Ph 2-Br-4-OCH2(E-3a)-Ph 2-F-4-OCF2H-Ph 2-Br-4-OCH2(6-Cl-(E-3a))-Ph 2-Cl-4-F-Ph 2-Br-4-OCH2(6-Br-(E-3a))-Ph 2,4-Cl2-Ph 2-Br-4-OCH2(6-Me-(E-3a))-Ph 2-Cl-4-Br-Ph 2-Br-4-OCH2(6-OMe-(E-3a))-Ph 2-Cl-4-I-Ph 2-Br-4-OCH2(E-30a)-Ph 2-Cl-4-Me-Ph 2-Br-4-OCH2(2-Cl-(E-30a))-Ph 2-Cl-4-Et-Ph 2-Br-4-OCH2(2-Br-(E-30a))-Ph 2-Cl-4-cPr-Ph 2-Br-4-OCH2(2-Me-(E-30a))-Ph 2-Cl-4-CF3-Ph 2-Br-4-OCH2(2-OMe-(E-30a))-Ph 2-Cl-4-CF2H-Ph 2-Br-4-OCH2(F-3a)-Ph 2-Cl-4-OMe-Ph 2-Br-4-NHC(O)OMe 2-Cl-4-OEt-Ph 2-Br-4-NHC(O)OEt 2-Cl-4-OCF3-Ph 2-Br-4-NHC(O)Ph-Ph 2-Cl-4-OCF2H-Ph 2-Br-4-NHC(O)(2-F-Ph)-Ph 2-Br-4-F-Ph 2-Br-4-NHC(O)(2-OMe-Ph)-Ph 2-Br-4-Cl-Ph 2-Br-4-NHC(O)(E-2a)-Ph 2,4-Br2-Ph 2-Br-4-Ph-Ph 2-Br-4-I-Ph 2-Br-4-(4-CN-Ph)-Ph 2-Br-4-Me-Ph 2-Br-4-(4-F-Ph)-Ph 2-Br-4-Et-Ph 2-Br-4-(4-Cl-Ph)-Ph 2-Br-4-cPr-Ph 2-Br-4-(4-CF3-Ph)-Ph 2-Br-4-CF3-Ph 2-Br-4-(4-OMe-Ph)-Ph 2-Br-4-CF2H-Ph 2-Br-4-(E-2a)-Ph 2-Br-4-OMe-Ph 2-Br-4-(5-CN-(E-2a))-Ph 2-Br-4-OEt-Ph 2-Br-4-(5-F-(E-2a))-Ph 2-Br-4-OCF3-Ph 2-Br-4-(5-Cl-(E-2a))-Ph 2-Br-4-OCF2H-Ph 2-Br-4-(5-CF3-(E-2a))-Ph 2-I-4-F-Ph 2-Br-4-(5-OMe-(E-2a))-Ph 2-I-4-Cl-Ph 2-Br-4-(E-3a)-Ph 2-I-4-Br-Ph 2-Br-4-(6-CN-(E-3a))-Ph 2,4-I2-Ph 2-Br-4-(6-F-(E-3a))-Ph 2-I-4-Me-Ph 2-Br-4-(6-Cl-(E-3a))-Ph 2-I-4-Et-Ph 2-Br-4-(6-CF3-(E-3a))-Ph 2-I-4-cPr-Ph 2-Br-4-(6-OMe-(E-3a))-Ph 2-I-4-CF3-Ph 2-Br-4-(E-7a)-Ph 2-I-4-CF2H-Ph 2-Br-4-(2-F-(E-7a))-Ph 2-I-4-OMe-Ph 2-Br-4-(2-Cl-(E-7a))-Ph 2-I-4-OEt-Ph 2-Br-4-(2-CF3-(E-7a))-Ph 2-I-4-OCF3-Ph 2-Br-4-(2-OMe-(E-7a))-Ph 2-I-4-OCF2H-Ph 2-Br-4-(E-22a)-Ph 2-Me-4-F-Ph 2-Br-4-(E-23a)-Ph 2-Me-4-Cl-Ph 2-Br-4-(E-24a)-Ph 2-Me-4-Br-Ph 2-Br-4-(E-12a)-Ph 2-Me-4-I-Ph 2-Br-4-(E-14a)-Ph 2-4-Me2-Ph 2-Br-4-SMe 2-Me-4-Et-Ph 2-Br-4-SOMe 2-Me-4-cPr-Ph 2-Br-4-SO2Me 2-Me-4-CF3-Ph 2-Br-4-SEt 2-Me-4-CF2H-Ph 2-Br-4-SOEt 2-Me-4-OMe-Ph 2-Br-4-SO2Et 2-Me-4-OEt-Ph 2-Me-4-nPr-Ph 2-Me-4-OCF3-Ph 2-Me-4-CH2F-Ph 2-Me-4-OCF2H-Ph 2-Me-4-CH2CF3-Ph 2-Et-4-F-Ph 2-Me-4-CH2CF2H-Ph 2-Et-4-Cl-Ph 2-Me-4-CH=CH2-Ph 2-Et-4-Br-Ph 2-Me-4-CH=CF2-Ph 2-Et-4-I-Ph 2-Me-4-C≡CH-Ph 2-Et-4-Me-Ph 2-Me-4-OH-Ph 2,4-Et2-Ph 2-Me-4-OnPr-Ph 2-Et-4-cPr-Ph 2-Me-4-OCH2cPr-Ph 2-Et-4-CF3-Ph 2-Me-4-OCH2CH=CH2-Ph 2-Et-4-CF2H-Ph 2-Me-4-OCH2C≡CH-Ph 2-Et-4-OMe-Ph 2-Me-4-OCH2CF3-Ph 2-Et-4-OEt-Ph 2-Me-4-OCH2CF2H-Ph 2-Et-4-OCF3-Ph 2-Me-4-OCH2CF2CF2H-Ph 2-Et-4-OCF2H-Ph 2-Me-4-OCH2C(=NOMe)Me-Ph 2-cPr-4-F-Ph 2-Me-4-OCH2C(=NOEt)Me-Ph 2-cPr-4-Cl-Ph 2-Me-4-OCH2(D-1a)-Ph 2-cPr-4-Br-Ph 2-Me-4-OCH2(D-2a)-Ph 2-cPr-4-I-Ph 2-Me-4-OCH2(E-2a)-Ph 2-cPr-4-Me-Ph 2-Me-4-OCH2(6-Cl-(E-2a))-Ph 2-cPr-4-Et-Ph 2-Me-4-OCH2(6-Br-(E-2a))-Ph 2,4-cPr2-Ph 2-Me-4-OCH2(6-Me-(E-2a))-Ph 2-cPr-4-CF3-Ph 2-Me-4-OCH2(6-OMe-(E-2a))-Ph 2-cPr-4-CF2H-Ph 2-Me-4-OCH2(5-Cl-(E-2a))-Ph 2-cPr-4-OMe-Ph 2-Me-4-OCH2(5-Br-(E-2a))-Ph 2-cPr-4-OEt-Ph 2-Me-4-OCH2(5-Me-(E-2a))-Ph 2-cPr-4-OCF3-Ph 2-Me-4-OCH2(5-OMe-(E-2a))-Ph 2-cPr-4-OCF2H-Ph 2-Me-4-OCH2(E-3a)-Ph 2-CF3-4-F-Ph 2-Me-4-OCH2(6-Cl-(E-3a))-Ph 2-CF3-4-Cl-Ph 2-Me-4-OCH2(6-Br-(E-3a))-Ph 2-CF3-4-Br-Ph 2-Me-4-OCH2(6-Me-(E-3a))-Ph 2-CF3-4-I-Ph 2-Me-4-OCH2(6-OMe-(E-3a))-Ph 2-CF3-4-Me-Ph 2-Me-4-OCH2(E-30a)-Ph 2-CF3-4-Et-Ph 2-Me-4-OCH2(2-Cl-(E-30a))-Ph 2-CF3-4-cPr-Ph 2-Me-4-OCH2(2-Br-(E-30a))-Ph 2,4-(CF3)2-Ph 2-Me-4-OCH2(2-Me-(E-30a))-Ph 2-CF3-4-CF2H-Ph 2-Me-4-OCH2(2-OMe-(E-30a))-Ph 2-CF3-4-OMe-Ph 2-Me-4-OCH2(F-3a)-Ph 2-CF3-4-OEt-Ph 2-Me-4-NHC(O)OMe 2-CF3-4-OCF3-Ph 2-Me-4-NHC(O)OEt 2-CF3-4-OCF2H-Ph 2-Me-4-NHC(O)Ph-Ph 2-CF2H-4-F-Ph 2-Me-4-NHC(O)(2-F-Ph)-Ph 2-CF2H-4-Cl-Ph 2-Me-4-NHC(O)(2-OMe-Ph)-Ph 2-CF2H-4-Br-Ph 2-Me-4-NHC(O)(E-2a)-Ph 2-CF2H-4-I-Ph 2-Me-4-Ph-Ph 2-CF2H-4-Me-Ph 2-Me-4-(4-CN-Ph)-Ph 2-CF2H-4-Et-Ph 2-Me-4-(4-F-Ph)-Ph 2-CF2H-4-cPr-Ph 2-Me-4-(4-Cl-Ph)-Ph 2-CF2H-4-CF3-Ph 2-Me-4-(4-CF3-Ph)-Ph 2,4-(CF2H)2-Ph 2-Me-4-(4-OMe-Ph)-Ph 2-CF2H-4-OMe-Ph 2-Me-4-(E-2a)-Ph 2-CF2H-4-OEt-Ph 2-Me-4-(5-CN-(E-2a))-Ph 2-CF2H-4-OCF3-Ph 2-Me-4-(5-F-(E-2a))-Ph 2-CF2H-4-OCF2H-Ph 2-Me-4-(5-Cl-(E-2a))-Ph 2-OMe-4-F-Ph 2-Me-4-(5-CF3-(E-2a))-Ph 2-OMe-4-Cl-Ph 2-Me-4-(5-OMe-(E-2a))-Ph 2-OMe-4-Br-Ph 2-Me-4-(E-3a)-Ph 2-OMe-4-I-Ph 2-Me-4-(6-CN-(E-3a))-Ph 2-OMe-4-Me-Ph 2-Me-4-(6-F-(E-3a))-Ph 2-OMe-4-Et-Ph 2-Me-4-(6-Cl-(E-3a))-Ph 2-OMe-4-cPr-Ph 2-Me-4-(6-CF3-(E-3a))-Ph 2-OMe-4-CF3-Ph 2-Me-4-(6-OMe-(E-3a))-Ph 2-OMe-4-CF2H-Ph 2-Me-4-(E-7a)-Ph 2,4-(OMe)2-Ph 2-Me-4-(2-F-(E-7a))-Ph 2-OMe-4-OEt-Ph 2-Me-4-(2-Cl-(E-7a))-Ph 2-OMe-4-OCF3-Ph 2-Me-4-(2-CF3-(E-7a))-Ph 2-OMe-4-OCF2H-Ph 2-Me-4-(2-OMe-(E-7a))-Ph 2-OEt-4-F-Ph 2-Me-4-(E-22a)-Ph 2-OEt-4-Cl-Ph 2-Me-4-(E-23a)-Ph 2-OEt-4-Br-Ph 2-Me-4-(E-24a)-Ph 2-OEt-4-I-Ph 2-Me-4-(E-12a)-Ph 2-OEt-4-Me-Ph 2-Me-4-(E-14a)-Ph 2-OEt-4-Et-Ph 2-Me-4-SMe 2 - OEt - 4 - cPr - Ph 2 - Me - 4 - SOMe 2 - OEt - 4 - CF3 - Ph 2 - Me - 4 - SO2Me 2 - OEt - 4 - CF2H - Ph 2 - Me - 4 - SEt 2 - OEt - 4 - OMe - Ph 2 - Me - 4 - SOEt 2,4 - (OEt)2 - Ph 2 - Me - 4 - SO2Et 2 - OEt - 4 - OCF3 - Ph 2 - Et - 4 - nPr - Ph 2 - OEt - 4 - OCF2H - Ph 2 - Et - 4 - CH2F - Ph 2 - OCF3 - 4 - F - Ph 2 - Et - 4 - CH2CF3 - Ph 2 - OCF3 - 4 - Cl - Ph 2 - Et - 4 - CH2CF2H - Ph 2 - OCF3 - 4 - Br - Ph 2 - Et - 4 - CH = CH2 - Ph 2 - OCF3 - 4 - I - Ph 2 - Et - 4 - CH = CF2 - Ph 2 - OCF3 - 4 - Me - Ph 2 - Et - 4 - C≡CH - Ph 2 - OCF3 - 4 - Et - Ph 2 - Et - 4 - OH - Ph 2 - OCF3 - 4 - cPr - Ph 2 - Et - 4 - OnPr - Ph 2 - OCF3 - 4 - CF3 - Ph 2 - Et - 4 - OCH2cPr - Ph 2 - OCF3 - 4 - CF2H - Ph 2 - Et - 4 - OCH2CH = CH2 - Ph 2 - OCF3 - 4 - OMe - Ph 2 - Et - 4 - OCH2C≡CH - Ph 2 - OCF3 - 4 - OEt - Ph 2 - Et - 4 - OCH2CF3 - Ph 2,4 - (OCF3)2 - Ph 2 - Et - 4 - OCH2CF2H - Ph 2 - OCF3 - 4 - OCF2H - Ph 2 - Et - 4 - OCH2CF2CF2H - Ph 2 - OCF2H - 4 - F - Ph 2 - Et - 4 - OCH2C(=NOMe)Me - Ph 2 - OCF2H - 4 - Cl - Ph 2 - Et - 4 - OCH2C(=NOEt)Me - Ph 2-OCF2H-4-Br-Ph 2-Et-4-OCH2(D-1a)-Ph 2-OCF2H-4-I-Ph 2-Et-4-OCH2(D-2a)-Ph 2-OCF2H-4-Me-Ph 2-Et-4-OCH2(E-2a)-Ph 2-OCF2H-4-Et-Ph 2-Et-4-OCH2(6-Cl-(E-2a))-Ph 2-OCF2H-4-cPr-Ph 2-Et-4-OCH2(6-Br-(E-2a))-Ph 2-OCF2H-4-CF3-Ph 2-Et-4-OCH2(6-Me-(E-2a))-Ph 2-OCF2H-4-CF2H-Ph 2-Et-4-OCH2(6-OMe-(E-2a))-Ph 2-OCF2H-4-OMe-Ph 2-Et-4-OCH2(5-Cl-(E-2a))-Ph 2-OCF2H-4-OEt-Ph 2-Et-4-OCH2(5-Br-(E-2a))-Ph 2-OCF2H-4-OCF3-Ph 2-Et-4-OCH2(5-Me-(E-2a))-Ph 2,4-(OCF2H)2-Ph 2-Et-4-OCH2(5-OMe-(E-2a))-Ph 4-nPr-Ph 2-Et-4-OCH2(E-3a)-Ph 4-CH2F-Ph 2-Et-4-OCH2(6-Cl-(E-3a))-Ph 4-CH2CF3-Ph 2-Et-4-OCH2(6-Br-(E-3a))-Ph 4-CH2CF2H-Ph 2-Et-4-OCH2(6-Me-(E-3a))-Ph 4-CH=CH2-Ph 2-Et-4-OCH2(6-OMe-(E-3a))-Ph 4-CH=CF2-Ph 2-Et-4-OCH2(E-30a)-Ph 4-C≡CH-Ph 2-Et-4-OCH2(2-Cl-(E-30a))-Ph 4-OH-Ph 2-Et-4-OCH2(2-Br-(E-30a))-Ph 4 - OnPr - Ph 2 - Et - 4 - OCH2(2 - Me - (E - 30a)) - Ph 4 - OCH2cPr - Ph 2 - Et - 4 - OCH2(2 - OMe - (E - 30a)) - Ph 4 - OCH2CH=CH2 - Ph 2 - Et - 4 - OCH2(F - 3a) - Ph 4 - OCH2C≡CH - Ph 2 - Et - 4 - NHC(O)OMe 4 - OCH2CF3 - Ph 2 - Et - 4 - NHC(O)OEt 4 - OCH2CF2H - Ph 2 - Et - 4 - NHC(O)Ph - Ph 4 - OCH2CF2CF2H - Ph 2 - Et - 4 - NHC(O)(2 - F - Ph) - Ph 4 - OCH2C(=NOMe)Me - Ph 2 - Et - 4 - NHC(O)(2 - OMe - Ph) - Ph 4 - OCH2C(=NOEt)Me - Ph 2 - Et - 4 - NHC(O)(E - 2a) - Ph 4 - OCH2(D - 1a) - Ph 2 - Et - 4 - Ph - Ph 4 - OCH2(D - 2a) - Ph 2 - Et - 4 - (4 - CN - Ph) - Ph 4 - OCH2(E - 2a) - Ph 2 - Et - 4 - (4 - F - Ph) - Ph 4 - OCH2(6 - Cl - (E - 2a)) - Ph 2 - Et - 4 - (4 - Cl - Ph) - Ph 4 - OCH2(6 - Br - (E - 2a)) - Ph 2 - Et - 4 - (4 - CF3 - Ph) - Ph 4 - OCH2(6 - Me - (E - 2a)) - Ph 2 - Et - 4 - (4 - OMe - Ph) - Ph 4 - OCH2(6 - OMe - (E - 2a)) - Ph 2 - Et - 4 - (E - 2a) - Ph 4 - OCH2(5 - Cl - (E - 2a)) - Ph 2 - Et - 4 - (5 - CN - (E - 2a)) - Ph 4 - OCH2(5 - Br - (E - 2a)) - Ph 2 - Et - 4 - (5 - F - (E - 2a)) - Ph 4 - OCH2(5 - Me - (E - 2a)) - Ph 2 - Et - 4 - (5 - Cl - (E - 2a)) - Ph 4 - OCH2(5 - OMe - (E - 2a)) - Ph 2 - Et - 4 - (5 - CF3 - (E - 2a)) - Ph 4 - OCH2(E - 3a) - Ph 2 - Et - 4 - (5 - OMe - (E - 2a)) - Ph 4 - OCH2(6 - Cl - (E - 3a)) - Ph 2 - Et - 4 - (E - 3a) - Ph 4 - OCH2(6 - Br - (E - 3a)) - Ph 2 - Et - 4 - (6 - CN - (E - 3a)) - Ph 4 - OCH2(6 - Me - (E - 3a)) - Ph 2 - Et - 4 - (6 - F - (E - 3a)) - Ph 4 - OCH2(6 - OMe - (E - 3a)) - Ph 2 - Et - 4 - (6 - Cl - (E - 3a)) - Ph 4 - OCH2(E - 30a) - Ph 2 - Et - 4 - (6 - CF3 - (E - 3a)) - Ph 4 - OCH2(2 - Cl - (E - 30a)) - Ph 2 - Et - 4 - (6 - OMe - (E - 3a)) - Ph 4 - OCH2(2 - Br - (E - 30a)) - Ph 2 - Et - 4 - (E - 7a) - Ph 4 - OCH2(2 - Me - (E - 30a)) - Ph 2 - Et - 4 - (2 - F - (E - 7a)) - Ph 4 - OCH2(2 - OMe - (E - 30a)) - Ph 2 - Et - 4 - (2 - Cl - (E - 7a)) - Ph 4 - OCH2(F - 3a) - Ph 2 - Et - 4 - (2 - CF3 - (E - 7a)) - Ph 4 - NHC(O)OMe 2 - Et - 4 - (2 - OMe - (E - 7a)) - Ph 4 - NHC(O)OEt 2 - Et - 4 - (E - 22a) - Ph 4 - NHC(O)Ph - Ph 2 - Et - 4 - (E - 23a) - Ph 4 - NHC(O)(2 - F - Ph) - Ph 2 - Et - 4 - (E - 24a) - Ph 4 - NHC(O)(2 - OMe - Ph) - Ph 2 - Et - 4 - (E - 12a) - Ph 4 - NHC(O)(E - 2a) - Ph 2 - Et - 4 - (E - 14a) - Ph 4 - Ph - Ph 2 - Et - 4 - SMe 4-(4-CN-Ph)-Ph 2-Et-4-SOMe 4-(4-F-Ph)-Ph 2-Et-4-SO2Me 4-(4-Cl-Ph)-Ph 2-Et-4-SEt 4-(4-CF3-Ph)-Ph 2-Et-4-SOEt 4-(4-OMe-Ph)-Ph 2-Et-4-SO2Et 4-(E-2a)-Ph 2-OMe-4-nPr-Ph 4-(5-CN-(E-2a))-Ph 2-OMe-4-CH2F-Ph 4-(5-F-(E-2a))-Ph 2-OMe-4-CH2CF3-Ph 4-(5-Cl-(E-2a))-Ph 2-OMe-4-CH2CF2H-Ph 4-(5-CF3-(E-2a))-Ph 2-OMe-4-CH=CH2-Ph 4-(5-OMe-(E-2a))-Ph 2-OMe-4-CH=CF2-Ph 4-(E-3a)-Ph 2-OMe-4-C≡CH-Ph 4-(6-CN-(E-3a))-Ph 2-OMe-4-OH-Ph 4-(6-F-(E-3a))-Ph 2-OMe-4-OnPr-Ph 4-(6-Cl-(E-3a))-Ph 2-OMe-4-OCH2cPr-Ph 4-(6-CF3-(E-3a))-Ph 2-OMe-4-OCH2CH=CH2-Ph 4-(6-OMe-(E-3a))-Ph 2-OMe-4-OCH2C≡CH-Ph 4-(E-7a)-Ph 2-OMe-4-OCH2CF3-Ph 4-(2-F-(E-7a))-Ph 2-OMe-4-OCH2CF2H-Ph 4-(2-Cl-(E-7a))-Ph 2-OMe-4-OCH2CF2CF2H-Ph 4-(2-CF3-(E-7a))-Ph 2-OMe-4-OCH2C(=NOMe)Me-Ph 4-(2-OMe-(E-7a))-Ph 2-OMe-4-OCH2C(=NOEt)Me-Ph 4-(E-22a)-Ph 2-OMe-4-OCH2(D-1a)-Ph 4-(E-23a)-Ph 2-OMe-4-OCH2(D-2a)-Ph 4-(E-24a)-Ph 2-OMe-4-OCH2(E-2a)-Ph 4-(E-12a)-Ph 2-OMe-4-OCH2(6-Cl-(E-2a))-Ph 4-(E-14a)-Ph 2-OMe-4-OCH2(6-Br-(E-2a))-Ph 4-SMe 2-OMe-4-OCH2(6-Me-(E-2a))-Ph 4-SOMe 2-OMe-4-OCH2(6-OMe-(E-2a))-Ph 4-SO2Me 2-OMe-4-OCH2(5-Cl-(E-2a))-Ph 4-SEt 2-OMe-4-OCH2(5-Br-(E-2a))-Ph 4-SOEt 2-OMe-4-OCH2(5-Me-(E-2a))-Ph 4-SO2Et 2-OMe-4-OCH2(5-OMe-(E-2a))-Ph 2-F-4-nPr-Ph 2-OMe-4-OCH2(E-3a)-Ph 2-F-4-CH2F-Ph 2-OMe-4-OCH2(6-Cl-(E-3a))-Ph 2-F-4-CH2CF3-Ph 2-OMe-4-OCH2(6-Br-(E-3a))-Ph 2-F-4-CH2CF2H-Ph 2-OMe-4-OCH2(6-Me-(E-3a))-Ph 2-F-4-CH=CH2-Ph 2-OMe-4-OCH2(6-OMe-(E-3a))-Ph 2-F-4-CH=CF2-Ph 2-OMe-4-OCH2(E-30a)-Ph 2-F-4-C≡CH-Ph 2-OMe-4-OCH2(2-Cl-(E-30a))-Ph 2-F-4-OH-Ph 2-OMe-4-OCH2(2-Br-(E-30a))-Ph 2-F-4-OnPr-Ph 2-OMe-4-OCH2(2-Me-(E-30a))-Ph 2-F-4-OCH2cPr-Ph 2-OMe-4-OCH2(2-OMe-(E-30a))-Ph 2-F-4-OCH2CH=CH2-Ph 2-OMe-4-OCH2(F-3a)-Ph 2-F-4-OCH2C≡CH-Ph 2-OMe-4-NHC(O)OMe 2-F-4-OCH2CF3-Ph 2-OMe-4-NHC(O)OEt 2-F-4-OCH2CF2H-Ph 2-OMe-4-NHC(O)Ph-Ph 2-F-4-OCH2CF2CF2H-Ph 2-OMe-4-NHC(O)(2-F-Ph)-Ph 2-F-4-OCH2C(=NOMe)Me-Ph 2-OMe-4-NHC(O)(2-OMe-Ph)-Ph 2-F-4-OCH2C(=NOEt)Me-Ph 2-OMe-4-NHC(O)(E-2a)-Ph 2-F-4-OCH2(D-1a)-Ph 2-OMe-4-Ph-Ph 2-F-4-OCH2(D-2a)-Ph 2-OMe-4-(4-CN-Ph)-Ph 2-F-4-OCH2(E-2a)-Ph 2-OMe-4-(4-F-Ph)-Ph 2-F-4-OCH2(6-Cl-(E-2a))-Ph 2-OMe-4-(4-Cl-Ph)-Ph 2-F-4-OCH2(6-Br-(E-2a))-Ph 2-OMe-4-(4-CF3-Ph)-Ph 2-F-4-OCH2(6-Me-(E-2a))-Ph 2-OMe-4-(4-OMe-Ph)-Ph 2-F-4-OCH2(6-OMe-(E-2a))-Ph 2-OMe-4-(E-2a)-Ph 2-F-4-OCH2(5-Cl-(E-2a))-Ph 2-OMe-4-(5-CN-(E-2a))-Ph 2-F-4-OCH2(5-Br-(E-2a))-Ph 2-OMe-4-(5-F-(E-2a))-Ph 2-F-4-OCH2(5-Me-(E-2a))-Ph 2-OMe-4-(5-Cl-(E-2a))-Ph 2-F-4-OCH2(5-OMe-(E-2a))-Ph 2-OMe-4-(5-CF3-(E-2a))-Ph 2-F-4-OCH2(E-3a)-Ph 2-OMe-4-(5-OMe-(E-2a))-Ph 2-F-4-OCH2(6-Cl-(E-3a))-Ph 2-OMe-4-(E-3a)-Ph 2-F-4-OCH2(6-Br-(E-3a))-Ph 2-OMe-4-(6-CN-(E-3a))-Ph 2-F-4-OCH2(6-Me-(E-3a))-Ph 2-OMe-4-(6-F-(E-3a))-Ph 2-F-4-OCH2(6-OMe-(E-3a))-Ph 2-OMe-4-(6-Cl-(E-3a))-Ph 2-F-4-OCH2(E-30a)-Ph 2-OMe-4-(6-CF3-(E-3a))-Ph 2-F-4-OCH2(2-Cl-(E-30a))-Ph 2-OMe-4-(6-OMe-(E-3a))-Ph 2-F-4-OCH2(2-Br-(E-30a))-Ph 2-OMe-4-(E-7a)-Ph 2-F-4-OCH2(2-Me-(E-30a))-Ph 2-OMe-4-(2-F-(E-7a))-Ph 2-F-4-OCH2(2-OMe-(E-30a))-Ph 2-OMe-4-(2-Cl-(E-7a))-Ph 2-F-4-OCH2(F-3a)-Ph 2-OMe-4-(2-CF3-(E-7a))-Ph 2-F-4-NHC(O)OMe 2-OMe-4-(2-OMe-(E-7a))-Ph 2-F-4-NHC(O)OEt 2-OMe-4-(E-22a)-Ph 2-F-4-NHC(O)Ph-Ph 2-OMe-4-(E-23a)-Ph 2-F-4-NHC(O)(2-F-Ph)-Ph 2-OMe-4-(E-24a)-Ph 2-F-4-NHC(O)(2-OMe-Ph)-Ph 2-OMe-4-(E-12a)-Ph 2-F-4-NHC(O)(E-2a)-Ph 2-OMe-4-(E-14a)-Ph 2-F-4-Ph-Ph 2-OMe-4-SMe 2-F-4-(4-CN-Ph)-Ph 2-OMe-4-SOMe 2-F-4-(4-F-Ph)-Ph 2-OMe-4-SO2Me 2-F-4-(4-Cl-Ph)-Ph 2-OMe-4-SEt 2-F-4-(4-CF3-Ph)-Ph 2-OMe-4-SOEt 2-F-4-(4-OMe-Ph)-Ph 2-OMe-4-SO2Et 2-F-4-(E-2a)-Ph 2-OEt-4-nPr-Ph 2-F-4-(5-CN-(E-2a))-Ph 2-OEt-4-CH2F-Ph 2-F-4-(5-F-(E-2a))-Ph 2-OEt-4-CH2CF3-Ph 2-F-4-(5-Cl-(E-2a))-Ph 2-OEt-4-CH2CF2H-Ph 2-F-4-(5-CF3-(E-2a))-Ph 2-OEt-4-CH=CH2-Ph 2-F-4-(5-OMe-(E-2a))-Ph 2-OEt-4-CH=CF2-Ph 2-F-4-(E-3a)-Ph 2-OEt-4-C≡CH-Ph 2-F-4-(6-CN-(E-3a))-Ph 2-OEt-4-OH-Ph 2-F-4-(6-F-(E-3a))-Ph 2-OEt-4-OnPr-Ph 2-F-4-(6-Cl-(E-3a))-Ph 2-OEt-4-OCH2cPr-Ph 2-F-4-(6-CF3-(E-3a))-Ph 2-OEt-4-OCH2CH=CH2-Ph 2-F-4-(6-OMe-(E-3a))-Ph 2-OEt-4-OCH2C≡CH-Ph 2-F-4-(E-7a)-Ph 2-OEt-4-OCH2CF3-Ph 2-F-4-(2-F-(E-7a))-Ph 2-OEt-4-OCH2CF2H-Ph 2-F-4-(2-Cl-(E-7a))-Ph 2-OEt-4-OCH2CF2CF2H-Ph 2-F-4-(2-CF3-(E-7a))-Ph 2-OEt-4-OCH2C(=NOMe)Me-Ph 2-F-4-(2-OMe-(E-7a))-Ph 2-OEt-4-OCH2C(=NOEt)Me-Ph 2-F-4-(E-22a)-Ph 2-OEt-4-OCH2(D-1a)-Ph 2-F-4-(E-23a)-Ph 2-OEt-4-OCH2(D-2a)-Ph 2-F-4-(E-24a)-Ph 2-OEt-4-OCH2(E-2a)-Ph 2-F-4-(E-12a)-Ph 2-OEt-4-OCH2(6-Cl-(E-2a))-Ph 2-F-4-(E-14a)-Ph 2-OEt-4-OCH2(6-Br-(E-2a))-Ph 2-F-4-SMe 2-OEt-4-OCH2(6-Me-(E-2a))-Ph 2-F-4-SOMe 2-OEt-4-OCH2(6-OMe-(E-2a))-Ph 2-F-4-SO2Me 2-OEt-4-OCH2(5-Cl-(E-2a))-Ph 2-F-4-SEt 2-OEt-4-OCH2(5-Br-(E-2a))-Ph 2-F-4-SOEt 2-OEt-4-OCH2(5-Me-(E-2a))-Ph 2-F-4-SO2Et 2-OEt-4-OCH2(5-OMe-(E-2a))-Ph 2 - Cl - 4 - nPr - Ph 2 - OEt - 4 - OCH2(E - 3a) - Ph 2 - Cl - 4 - CH2F - Ph 2 - OEt - 4 - OCH2(6 - Cl - (E - 3a)) - Ph 2 - Cl - 4 - CH2CF3 - Ph 2 - OEt - 4 - OCH2(6 - Br - (E - 3a)) - Ph 2 - Cl - 4 - CH2CF2H - Ph 2 - OEt - 4 - OCH2(6 - Me - (E - 3a)) - Ph 2 - Cl - 4 - CH=CH2 - Ph 2 - OEt - 4 - OCH2(6 - OMe - (E - 3a)) - Ph 2 - Cl - 4 - CH=CF2 - Ph 2 - OEt - 4 - OCH2(E - 30a) - Ph 2 - Cl - 4 - C≡CH - Ph 2 - OEt - 4 - OCH2(2 - Cl - (E - 30a)) - Ph 2 - Cl - 4 - OH - Ph 2 - OEt - 4 - OCH2(2 - Br - (E - 30a)) - Ph 2 - Cl - 4 - OnPr - Ph 2 - OEt - 4 - OCH2(2 - Me - (E - 30a)) - Ph 2 - Cl - 4 - OCH2cPr - Ph 2 - OEt - 4 - OCH2(2 - OMe - (E - 30a)) - Ph 2 - Cl - 4 - OCH2CH=CH2 - Ph 2 - OEt - 4 - OCH2(F - 3a) - Ph 2 - Cl - 4 - OCH2C≡CH - Ph 2 - OEt - 4 - NHC(O)OMe 2 - Cl - 4 - OCH2CF3 - Ph 2 - OEt - 4 - NHC(O)OEt 2 - Cl - 4 - OCH2CF2H - Ph 2 - OEt - 4 - NHC(O)Ph - Ph 2 - Cl - 4 - OCH2CF2CF2H - Ph 2 - OEt - 4 - NHC(O)(2 - F - Ph) - Ph 2 - Cl - 4 - OCH2C(=NOMe)Me - Ph 2 - OEt - 4 - NHC(O)(2 - OMe - Ph) - Ph 2 - Cl - 4 - OCH2C(=NOEt)Me - Ph 2 - OEt - 4 - NHC(O)(E - 2a) - Ph 2 - Cl - 4 - OCH2(D - 1a) - Ph 2 - OEt - 4 - Ph - Ph 2-Chloro-4-methoxymethyl-(D-2a)-phenyl 2-ethoxy-4-(4-cyanophenyl)-phenyl 2-Chloro-4-methoxymethyl-(E-2a)-phenyl 2-ethoxy-4-(4-fluorophenyl)-phenyl 2-Chloro-4-methoxymethyl-(6-chloro-(E-2a))-phenyl 2-ethoxy-4-(4-chlorophenyl)-phenyl 2-Chloro-4-methoxymethyl-(6-bromo-(E-2a))-phenyl 2-ethoxy-4-(4-trifluoromethylphenyl)-phenyl 2-Chloro-4-methoxymethyl-(6-methyl-(E-2a))-phenyl 2-ethoxy-4-(4-methoxyphenyl)-phenyl 2-Chloro-4-methoxymethyl-(6-methoxy-(E-2a))-phenyl 2-ethoxy-4-(E-2a)-phenyl 2-Chloro-4-methoxymethyl-(5-chloro-(E-2a))-phenyl 2-ethoxy-4-(5-cyano-(E-2a))-phenyl 2-Chloro-4-methoxymethyl-(5-bromo-(E-2a))-phenyl 2-ethoxy-4-(5-fluoro-(E-2a))-phenyl 2-Chloro-4-methoxymethyl-(5-methyl-(E-2a))-phenyl 2-ethoxy-4-(5-chloro-(E-2a))-phenyl 2-Chloro-4-methoxymethyl-(5-methoxy-(E-2a))-phenyl 2-ethoxy-4-(5-trifluoromethyl-(E-2a))-phenyl 2-Chloro-4-methoxymethyl-(E-3a)-phenyl 2-ethoxy-4-(5-methoxy-(E-2a))-phenyl 2-Chloro-4-methoxymethyl-(6-chloro-(E-3a))-phenyl 2-ethoxy-4-(E-3a)-phenyl 2-Chloro-4-methoxymethyl-(6-bromo-(E-3a))-phenyl 2-ethoxy-4-(6-cyano-(E-3a))-phenyl 2-Chloro-4-methoxymethyl-(6-methyl-(E-3a))-phenyl 2-ethoxy-4-(6-fluoro-(E-3a))-phenyl 2-Chloro-4-methoxymethyl-(6-methoxy-(E-3a))-phenyl 2-ethoxy-4-(6-chloro-(E-3a))-phenyl 2-Chloro-4-methoxymethyl-(E-30a)-phenyl 2-ethoxy-4-(6-trifluoromethyl-(E-3a))-phenyl 2 - Cl - 4 - OCH2(2 - Cl - (E - 30a)) - Ph 2 - OEt - 4 - (6 - OMe - (E - 3a)) - Ph 2 - Cl - 4 - OCH2(2 - Br - (E - 30a)) - Ph 2 - OEt - 4 - (E - 7a) - Ph 2 - Cl - 4 - OCH2(2 - Me - (E - 30a)) - Ph 2 - OEt - 4 - (2 - F - (E - 7a)) - Ph 2 - Cl - 4 - OCH2(2 - OMe - (E - 30a)) - Ph 2 - OEt - 4 - (2 - Cl - (E - 7a)) - Ph 2 - Cl - 4 - OCH2(F - 3a) - Ph 2 - OEt - 4 - (2 - CF3 - (E - 7a)) - Ph 2 - Cl - 4 - NHC(O)OMe 2 - OEt - 4 - (2 - OMe - (E - 7a)) - Ph 2 - Cl - 4 - NHC(O)OEt 2 - OEt - 4 - (E - 22a) - Ph 2 - Cl - 4 - NHC(O)Ph - Ph 2 - OEt - 4 - (E - 23a) - Ph 2 - Cl - 4 - NHC(O)(2 - F - Ph) - Ph 2 - OEt - 4 - (E - 24a) - Ph 2 - Cl - 4 - NHC(O)(2 - OMe - Ph) - Ph 2 - OEt - 4 - (E - 12a) - Ph 2 - Cl - 4 - NHC(O)(E - 2a) - Ph 2 - OEt - 4 - (E - 14a) - Ph 2 - Cl - 4 - Ph - Ph 2 - OEt - 4 - SMe 2 - Cl - 4 - (4 - CN - Ph) - Ph 2 - OEt - 4 - SOMe 2 - Cl - 4 - (4 - F - Ph) - Ph 2 - OEt - 4 - SO2Me 2 - Cl - 4 - (4 - Cl - Ph) - Ph 2 - OEt - 4 - SEt 2 - Cl - 4 - (4 - CF3 - Ph) - Ph 2 - OEt - 4 - SOEt 2 - Cl - 4 - (4 - OMe - Ph) - Ph 2 - OEt - 4 - SO2Et 2 - Cl - 4 - (E - 2a) - Ph Z - 2a 2 - Cl - 4 - (5 - CN - (E - 2a)) - Ph Z - 3a 2-Cl-4-(5-F-(E-2a))-Ph Z-4a 2-Cl-4-(5-Cl-(E-2a))-Ph Z-6a 2-Cl-4-(5-CF3-(E-2a))-Ph Z-45a 2-Cl-4-(5-OMe-(E-2a))-Ph ――――――――――――――― ――――――――――――――― Tables 1-2 are constructed in the same way as Table 1, except that the conditions in Table 1 (i.e., "G is Ph, R X is tBu, R Y is H, R 3 is H, R 4 is H") are replaced by the following conditions (i.e., "G is Ph, R X is tBu, R Y is H, R 3 is F, R 4 is H").
[0195] Therefore, the first item in Tables 1-2 is a compound of formula (1) where G is Ph, R X is tBu, R Y is H, R 3 is F, R 4 is H. Tables 1-3 to 1-840 are constructed in the same way. [Table 1-2] G is Ph, R X is tBu, R Y is H, R 3 is F, R 4 is H. [Table 1-3] G is Ph, R X is tBu, R Y is H, R 3 is F, R 4 is F. [Table 1-4] G is Ph, R X is tBu, R Y is H, R 3 is Me, R 4 is H. [Table 1-5] G is Ph, and R X is tBu, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-6] G is Ph, and R X is tBu, and R Y is F, and R 3 is H, and R 4 is H. [Table 1-7] G is Ph, and R X is tBu, and R Y is F, and R 3 is F, and R 4 is H. [Table 1-8] G is Ph, and R X is tBu, and R Y is F, and R 3 is F, and R 4 is F. [Table 1-9] G is Ph, and R X is tBu, and R Y is F, and R 3 is Me, and R 4 is H. [Table 1-10] G is Ph, and R X is tBu, and R Y is F, and R 3 is Me, and R 4 is Me. [Table 1-11] G is Ph, and R X is tBu, and R Y is Cl, and R 3 is H, and R 4 is H. [Table 1-12] G is Ph, and R X is tBu, and R Y is Cl, and R 3 is F, and R 4 is H. [Table 1-13] G is Ph, R X is tBu, R Y is Cl, R 3 is F, R 4 is F. [Table 1-14] G is Ph, R X is tBu, R Y is Cl, R 3 is Me, R 4 is H. [Table 1-15] G is Ph, R X is tBu, R Y is Cl, R 3 is Me, R 4 is Me. [Table 1-16] G is Ph, R X is tBu, R Y is Br, R 3 is H, R 4 is H. [Table 1-17] G is Ph, R X is tBu, R Y is Br, R 3 is F, R 4 is H. [Table 1-18] G is Ph, R X is tBu, R Y is Br, R 3 is F, R 4 is F. [Table 1-19] G is Ph, R X is tBu, R Y is Br, R 3 is Me, R 4 is H. [Table 1-20] G is Ph, R X is tBu, R Y is Br, R 3 is Me, R 4It is Me. [Table 1-21] G is Ph, and R X is tAm, and R Y is H, and R 3 is H, and R 4 is H. [Table 1-22] G is Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is H. [Table 1-23] G is Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is F. [Table 1-24] G is Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is H. [Table 1-25] G is Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-26] G is Ph, and R X is tAm, and R Y is F, and R 3 is H, and R 4 is H. [Table 1-27] G is Ph, and R X is tAm, and R Y is F, and R 3 is F, and R 4 is H. [Table 1-28] G is Ph, and R X is tAm, and R Y is F, and R 3 is F, and R 4It is F. [Table 1-29] G is Ph, and R X is tAm, and R Y is F, and R 3 is Me, and R 4 is H. [Table 1-30] G is Ph, and R X is tAm, and R Y is F, and R 3 is Me, and R 4 is Me. [Table 1-31] G is Ph, and R X is tAm, and R Y is Cl, and R 3 is H, and R 4 is H. [Table 1-32] G is Ph, and R X is tAm, and R Y is Cl, and R 3 is F, and R 4 is H. [Table 1-33] G is Ph, and R X is tAm, and R Y is Cl, and R 3 is F, and R 4 is F. [Table 1-34] G is Ph, and R X is tAm, and R Y is Cl, and R 3 is Me, and R 4 is H. [Table 1-35] G is Ph, and R X is tAm, and R Y is Cl, and R 3 is Me, and R 4 is Me. [Table 1-36] G is Ph, and R X is tAm, and R Y is Br, and R 3 is H, and R4 is H. [Table 1-37] G is Ph, and R X is tAm, and R Y is Br, and R 3 is F, and R 4 is H. [Table 1-38] G is Ph, and R X is tAm, and R Y is Br, and R 3 is F, and R 4 is F. [Table 1-39] G is Ph, and R X is tAm, and R Y is Br, and R 3 is Me, and R 4 is H. [Table 1-40] G is Ph, and R X is tAm, and R Y is Br, and R 3 is Me, and R 4 is Me. [Table 1-41] G is 3-F-Ph, and R X is tBu, and R Y is H, and R 3 is H, and R 4 is H. [Table 1-42] G is 3-F-Ph, and R X is tBu, and R Y is H, and R 3 is F, and R 4 is H. [Table 1-43] G is 3-F-Ph, and R X is tBu, and R Y is H, and R 3 is F, and R 4 is F. [Table 1-44] G is 3-F-Ph, and R X is tBu, and R Y is H, and R3 is Me, and R 4 is H. [Table 1-45] G is 3-F-Ph, and R X is tBu, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-46] G is 3-F-Ph, and R X is tBu, and R Y is F, and R 3 is H, and R 4 is H. [Table 1-47] G is 3-F-Ph, and R X is tBu, and R Y is F, and R 3 is F, and R 4 is H. [Table 1-48] G is 3-F-Ph, and R X is tBu, and R Y is F, and R 3 is F, and R 4 is F. [Table 1-49] G is 3-F-Ph, and R X is tBu, and R Y is F, and R 3 is Me, and R 4 is H. [Table 1-50] G is 3-F-Ph, and R X is tBu, and R Y is F, and R 3 is Me, and R 4 is Me. [Table 1-51] G is 3-F-Ph, and R X is tBu, and R Y is Cl, and R 3 is H, and R 4 is H. [Table 1-52] G is 3-F-Ph, and R Xis tBu, and R Y is Cl, and R 3 is F, and R 4 is H. [Table 1-53] G is 3-F-Ph, and R X is tBu, and R Y is Cl, and R 3 is F, and R 4 is F. [Table 1-54] G is 3-F-Ph, and R X is tBu, and R Y is Cl, and R 3 is Me, and R 4 is H. [Table 1-55] G is 3-F-Ph, and R X is tBu, and R Y is Cl, and R 3 is Me, and R 4 is Me. [Table 1-56] G is 3-F-Ph, and R X is tBu, and R Y is Br, and R 3 is H, and R 4 is H. [Table 1-57] G is 3-F-Ph, and R X is tBu, and R Y is Br, and R 3 is F, and R 4 is H. [Table 1-58] G is 3-F-Ph, and R X is tBu, and R Y is Br, and R 3 is F, and R 4 is F. [Table 1-59] G is 3-F-Ph, and R X is tBu, and R Y is Br, and R 3 is Me, and R 4 is H. [Table 1-60] G is 3-F-Ph, and R X is tBu, and R Y is Br, and R 3 is Me, and R 4 is Me. [Table 1-61] G is 3-F-Ph, and R X is tAm, and R Y is H, and R 3 is H, and R 4 is H. [Table 1-62] G is 3-F-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is H. [Table 1-63] G is 3-F-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is F. [Table 1-64] G is 3-F-Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is H. [Table 1-65] G is 3-F-Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-66] G is 3-F-Ph, and R X is tAm, and R Y is F, and R 3 is H, and R 4 is H. [Table 1-67] G is 3-F-Ph, and R X is tAm, and R Y is F, and R 3 is F, and R 4It is H. [Table 1-68] G is 3-F-Ph, and R X is tAm, and R Y is F, and R 3 is F, and R 4 is F. [Table 1-69] G is 3-F-Ph, and R X is tAm, and R Y is F, and R 3 is Me, and R 4 is H. [Table 1-70] G is 3-F-Ph, and R X is tAm, and R Y is F, and R 3 is Me, and R 4 is Me. [Table 1-71] G is 3-F-Ph, and R X is tAm, and R Y is Cl, and R 3 is H, and R 4 is H. [Table 1-72] G is 3-F-Ph, and R X is tAm, and R Y is Cl, and R 3 is F, and R 4 is H. [Table 1-73] G is 3-F-Ph, and R X is tAm, and R Y is Cl, and R 3 is F, and R 4 is F. [Table 1-74] G is 3-F-Ph, and R X is tAm, and R Y is Cl, and R 3 is Me, and R 4 is H. [Table 1-75] G is 3-F-Ph, and R X is tAm, and R Y is Cl, and R3 is Me, and R 4 is Me. [Table 1-76] G is 3-F-Ph, and R X is tAm, and R Y is Br, and R 3 is H, and R 4 is H. [Table 1-77] G is 3-F-Ph, and R X is tAm, and R Y is Br, and R 3 is F, and R 4 is H. [Table 1-78] G is 3-F-Ph, and R X is tAm, and R Y is Br, and R 3 is F, and R 4 is F. [Table 1-79] G is 3-F-Ph, and R X is tAm, and R Y is Br, and R 3 is Me, and R 4 is H. [Table 1-80] G is 3-F-Ph, and R X is tAm, and R Y is Br, and R 3 is Me, and R 4 is Me. [Table 1-81] G is 3-Cl-Ph, and R X is tBu, and R Y is H, and R 3 is H, and R 4 is H. [Table 1-82] G is 3-Cl-Ph, and R X is tBu, and R Y is H, and R 3 is F, and R 4 is H. [Table 1-83] G is 3-Cl-Ph, and RX is tBu, and R Y is H, and R 3 is F, and R 4 is F. [Table 1-84] G is 3-Cl-Ph, and R X is tBu, and R Y is H, and R 3 is Me, and R 4 is H. [Table 1-85] G is 3-Cl-Ph, and R X is tBu, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-86] G is 3-Cl-Ph, and R X is tBu, and R Y is F, and R 3 is H, and R 4 is H. [Table 1-87] G is 3-Cl-Ph, and R X is tBu, and R Y is F, and R 3 is F, and R 4 is H. [Table 1-88] G is 3-Cl-Ph, and R X is tBu, and R Y is F, and R 3 is F, and R 4 is F. [Table 1-89] G is 3-Cl-Ph, and R X is tBu, and R Y is F, and R 3 is Me, and R 4 is H. [Table 1-90] G is 3-Cl-Ph, and R X is tBu, and R Y is F, and R 3 is Me, and R 4 is Me. [Table 1-91] G is 3-Cl-Ph, and R X is tBu, and R Y is Cl, and R 3 is H, and R 4 is H. [Table 1-92] G is 3-Cl-Ph, and R X is tBu, and R Y is Cl, and R 3 is F, and R 4 is H. [Table 1-93] G is 3-Cl-Ph, and R X is tBu, and R Y is Cl, and R 3 is F, and R 4 is F. [Table 1-94] G is 3-Cl-Ph, and R X is tBu, and R Y is Cl, and R 3 is Me, and R 4 is H. [Table 1-95] G is 3-Cl-Ph, and R X is tBu, and R Y is Cl, and R 3 is Me, and R 4 is Me. [Table 1-96] G is 3-Cl-Ph, and R X is tBu, and R Y is Br, and R 3 is H, and R 4 is H. [Table 1-97] G is 3-Cl-Ph, and R X is tBu, and R Y is Br, and R 3 is F, and R 4 is H. [Table 1-98] G is 3-Cl-Ph, and R X is tBu, and R Y is Br,3 is F, and R 4 is F. [Table 1-99] G is 3-Cl-Ph, and R X is tBu, and R Y is Br, and R 3 is Me, and R 4 is H. [Table 1-100] G is 3-Cl-Ph, and R X is tBu, and R Y is Br, and R 3 is Me, and R 4 is Me. [Table 1-101] G is 3-Cl-Ph, and R X is tAm, and R Y is H, and R 3 is H, and R 4 is H. [Table 1-102] G is 3-Cl-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is H. [Table 1-103] G is 3-Cl-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is F. [Table 1-104] G is 3-Cl-Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is H. [Table 1-105] G is 3-Cl-Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-106] G is 3-Cl-Ph, R X is tAm, R Y is F, R 3 is H, R 4 is H. [Table 1-107] G is 3-Cl-Ph, R X is tAm, R Y is F, R 3 is F, R 4 is H. [Table 1-108] G is 3-Cl-Ph, R X is tAm, R Y is F, R 3 is F, R 4 is F. [Table 1-109] G is 3-Cl-Ph, R X is tAm, R Y is F, R 3 is Me, R 4 is H. [Table 1-110] G is 3-Cl-Ph, R X is tAm, R Y is F, R 3 is Me, R 4 is Me. [Table 1-111] G is 3-Cl-Ph, R X is tAm, R Y is Cl, R 3 is H, R 4 is H. [Table 1-112] G is 3-Cl-Ph, R X is tAm, R Y is Cl, R 3 is F, R 4 is H. [Table 1-113] G is 3-Cl-Ph, R X is tAm, R Y is Cl, R 3 is F, R4 is F. [Table 1-114] G is 3-Cl-Ph, R X is tAm, R Y is Cl, R 3 is Me, R 4 is H. [Table 1-115] G is 3-Cl-Ph, R X is tAm, R Y is Cl, R 3 is Me, R 4 is Me. [Table 1-116] G is 3-Cl-Ph, R X is tAm, R Y is Br, R 3 is H, R 4 is H. [Table 1-117] G is 3-Cl-Ph, R X is tAm, R Y is Br, R 3 is F, R 4 is H. [Table 1-118] G is 3-Cl-Ph, R X is tAm, R Y is Br, R 3 is F, R 4 is F. [Table 1-119] G is 3-Cl-Ph, R X is tAm, R Y is Br, R 3 is Me, R 4 is H. [Table 1-120] G is 3-Cl-Ph, R X is tAm, R Y is Br, R 3 is Me, R 4 is Me. [Table 1-121] G is 3-Br-Ph, R Xis tBu, and R Y is H, and R 3 is H, and R 4 is H. [Table 1-122] G is 3-Br-Ph, and R X is tBu, and R Y is H, and R 3 is F, and R 4 is H. [Table 1-123] G is 3-Br-Ph, and R X is tBu, and R Y is H, and R 3 is F, and R 4 is F. [Table 1-124] G is 3-Br-Ph, and R X is tBu, and R Y is H, and R 3 is Me, and R 4 is H. [Table 1-125] G is 3-Br-Ph, and R X is tBu, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-126] G is 3-Br-Ph, and R X is tBu, and R Y is F, and R 3 is H, and R 4 is H. [Table 1-127] G is 3-Br-Ph, and R X is tBu, and R Y is F, and R 3 is F, and R 4 is H. [Table 1-128] G is 3-Br-Ph, and R X is tBu, and R Y is F, and R 3 is F, and R 4 is F. [Table 1-129] G is 3-Br-Ph, and R X is tBu, and R Y is F, and R 3 is Me, and R 4 is H. [Table 1-130] G is 3-Br-Ph, and R X is tBu, and R Y is F, and R 3 is Me, and R 4 is Me. [Table 1-131] G is 3-Br-Ph, and R X is tBu, and R Y is Cl, and R 3 is H, and R 4 is H. [Table 1-132] G is 3-Br-Ph, and R X is tBu, and R Y is Cl, and R 3 is F, and R 4 is H. [Table 1-133] G is 3-Br-Ph, and R X is tBu, and R Y is Cl, and R 3 is F, and R 4 is F. [Table 1-134] G is 3-Br-Ph, and R X is tBu, and R Y is Cl, and R 3 is Me, and R 4 is H. [Table 1-135] G is 3-Br-Ph, and R X is tBu, and R Y is Cl, and R 3 is Me, and R 4 is Me. [Table 1-136] G is 3-Br-Ph, and R X is tBu, and R Y is Br, and R3 is H, and R 4 is H. [Table 1-137] G is 3-Br-Ph, and R X is tBu, and R Y is Br, and R 3 is F, and R 4 is H. [Table 1-138] G is 3-Br-Ph, and R X is tBu, and R Y is Br, and R 3 is F, and R 4 is F. [Table 1-139] G is 3-Br-Ph, and R X is tBu, and R Y is Br, and R 3 is Me, and R 4 is H. [Table 1-140] G is 3-Br-Ph, and R X is tBu, and R Y is Br, and R 3 is Me, and R 4 is Me. [Table 1-141] G is 3-Br-Ph, and R X is tAm, and R Y is H, and R 3 is H, and R 4 is H. [Table 1-142] G is 3-Br-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is H. [Table 1-143] G is 3-Br-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is F. [Table 1-144] G is 3-Br-Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is H. [Table 1-145] G is 3-Br-Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-146] G is 3-Br-Ph, and R X is tAm, and R Y is F, and R 3 is H, and R 4 is H. [Table 1-147] G is 3-Br-Ph, and R X is tAm, and R Y is F, and R 3 is F, and R 4 is H. [Table 1-148] G is 3-Br-Ph, and R X is tAm, and R Y is F, and R 3 is F, and R 4 is F. [Table 1-149] G is 3-Br-Ph, and R X is tAm, and R Y is F, and R 3 is Me, and R 4 is H. [Table 1-150] G is 3-Br-Ph, and R X is tAm, and R Y is F, and R 3 is Me, and R 4 is Me. [Table 1-151] G is 3-Br-Ph, and R X is tAm, and R Y is Cl, and R 3 is H, and R4 is H. [Table 1-152] G is 3-Br-Ph, and R X is tAm, and R Y is Cl, and R 3 is F, and R 4 is H. [Table 1-153] G is 3-Br-Ph, and R X is tAm, and R Y is Cl, and R 3 is F, and R 4 is F. [Table 1-154] G is 3-Br-Ph, and R X is tAm, and R Y is Cl, and R 3 is Me, and R 4 is H. [Table 1-155] G is 3-Br-Ph, and R X is tAm, and R Y is Cl, and R 3 is Me, and R 4 is Me. [Table 1-156] G is 3-Br-Ph, and R X is tAm, and R Y is Br, and R 3 is H, and R 4 is H. [Table 1-157] G is 3-Br-Ph, and R X is tAm, and R Y is Br, and R 3 is F, and R 4 is H. [Table 1-158] G is 3-Br-Ph, and R X is tAm, and R Y is Br, and R 3 is F, and R 4 is F. [Table 1-159] G is 3-Br-Ph, and R Xis tAm, R Y is Br, R 3 is Me, R 4 is H. [Table 1-160] G is 3-Br-Ph, R X is tAm, R Y is Br, R 3 is Me, R 4 is Me. [Table 1-161] G is 3-I-Ph, R X is tBu, R Y is H, R 3 is H, R 4 is H. [Table 1-162] G is 3-I-Ph, R X is tBu, R Y is H, R 3 is F, R 4 is H. [Table 1-163] G is 3-I-Ph, R X is tBu, R Y is H, R 3 is F, R 4 is F. [Table 1-164] G is 3-I-Ph, R X is tBu, R Y is H, R 3 is Me, R 4 is H. [Table 1-165] G is 3-I-Ph, R X is tBu, R Y is H, R 3 is Me, R 4 is Me. [Table 1-166] G is 3-I-Ph, R X is tBu, R Y is F, R 3 is H, R 4 is H. [Table 1-167] G is 3-I-Ph, and R X is tBu, and R Y is F, and R 3 is F, and R 4 is H. [Table 1-168] G is 3-I-Ph, and R X is tBu, and R Y is F, and R 3 is F, and R 4 is F. [Table 1-169] G is 3-I-Ph, and R X is tBu, and R Y is F, and R 3 is Me, and R 4 is H. [Table 1-170] G is 3-I-Ph, and R X is tBu, and R Y is F, and R 3 is Me, and R 4 is Me. [Table 1-171] G is 3-I-Ph, and R X is tBu, and R Y is Cl, and R 3 is H, and R 4 is H. [Table 1-172] G is 3-I-Ph, and R X is tBu, and R Y is Cl, and R 3 is F, and R 4 is H. [Table 1-173] G is 3-I-Ph, and R X is tBu, and R Y is Cl, and R 3 is F, and R 4 is F. [Table 1-174] G is 3-I-Ph, and R X is tBu, and R Y is Cl, and R 3is Me, and R 4 is H. [Table 1-175] G is 3-I-Ph, and R X is tBu, and R Y is Cl, and R 3 is Me, and R 4 is Me. [Table 1-176] G is 3-I-Ph, and R X is tBu, and R Y is Br, and R 3 is H, and R 4 is H. [Table 1-177] G is 3-I-Ph, and R X is tBu, and R Y is Br, and R 3 is F, and R 4 is H. [Table 1-178] G is 3-I-Ph, and R X is tBu, and R Y is Br, and R 3 is F, and R 4 is F. [Table 1-179] G is 3-I-Ph, and R X is tBu, and R Y is Br, and R 3 is Me, and R 4 is H. [Table 1-180] G is 3-I-Ph, and R X is tBu, and R Y is Br, and R 3 is Me, and R 4 is Me. [Table 1-181] G is 3-I-Ph, and R X is tAm, and R Y is H, and R 3 is H, and R 4 is H. [Table 1-182] G is 3-I-Ph, and R Xis tAm, R Y is H, R 3 is F, R 4 is H. [Table 1-183] G is 3-I-Ph, R X is tAm, R Y is H, R 3 is F, R 4 is F. [Table 1-184] G is 3-I-Ph, R X is tAm, R Y is H, R 3 is Me, R 4 is H. [Table 1-185] G is 3-I-Ph, R X is tAm, R Y is H, R 3 is Me, R 4 is Me. [Table 1-186] G is 3-I-Ph, R X is tAm, R Y is F, R 3 is H, R 4 is H. [Table 1-187] G is 3-I-Ph, R X is tAm, R Y is F, R 3 is F, R 4 is H. [Table 1-188] G is 3-I-Ph, R X is tAm, R Y is F, R 3 is F, R 4 is F. [Table 1-189] G is 3-I-Ph, R X is tAm, R Y is F, R 3 is Me, R 4 is H. [Table 1-190] G is 3-I-Ph, and R X is tAm, and R Y is F, and R 3 is Me, and R 4 is Me. [Table 1-191] G is 3-I-Ph, and R X is tAm, and R Y is Cl, and R 3 is H, and R 4 is H. [Table 1-192] G is 3-I-Ph, and R X is tAm, and R Y is Cl, and R 3 is F, and R 4 is H. [Table 1-193] G is 3-I-Ph, and R X is tAm, and R Y is Cl, and R 3 is F, and R 4 is F. [Table 1-194] G is 3-I-Ph, and R X is tAm, and R Y is Cl, and R 3 is Me, and R 4 is H. [Table 1-195] G is 3-I-Ph, and R X is tAm, and R Y is Cl, and R 3 is Me, and R 4 is Me. [Table 1-196] G is 3-I-Ph, and R X is tAm, and R Y is Br, and R 3 is H, and R 4 is H. [Table 1-197] G is 3-I-Ph, and R X is tAm, and R Y is Br, and R 3 is F, and R4 is H. [Table 1-198] G is 3-I-Ph, and R X is tAm, and R Y is Br, and R 3 is F, and R 4 is F. [Table 1-199] G is 3-I-Ph, and R X is tAm, and R Y is Br, and R 3 is Me, and R 4 is H. [Table 1-200] G is 3-I-Ph, and R X is tAm, and R Y is Br, and R 3 is Me, and R 4 is Me. [Table 1-201] G is 3-Me-Ph, and R X is tBu, and R Y is H, and R 3 is H, and R 4 is H. [Table 1-202] G is 3-Me-Ph, and R X is tBu, and R Y is H, and R 3 is F, and R 4 is H. [Table 1-203] G is 3-Me-Ph, and R X is tBu, and R Y is H, and R 3 is F, and R 4 is F. [Table 1-204] G is 3-Me-Ph, and R X is tBu, and R Y is H, and R 3 is Me, and R 4 is H. [Table 1-205] G is 3-Me-Ph, and R Xis tBu, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-206] G is 3-Me-Ph, and R X is tBu, and R Y is F, and R 3 is H, and R 4 is H. [Table 1-207] G is 3-Me-Ph, and R X is tBu, and R Y is F, and R 3 is F, and R 4 is H. [Table 1-208] G is 3-Me-Ph, and R X is tBu, and R Y is F, and R 3 is F, and R 4 is F. [Table 1-209] G is 3-Me-Ph, and R X is tBu, and R Y is F, and R 3 is Me, and R 4 is H. [Table 1-210] G is 3-Me-Ph, and R X is tBu, and R Y is F, and R 3 is Me, and R 4 is Me. [Table 1-211] G is 3-Me-Ph, and R X is tBu, and R Y is Cl, and R 3 is H, and R 4 is H. [Table 1-212] G is 3-Me-Ph, and R X is tBu, and R Y is Cl, and R 3 is F, and R 4 is H. [Table 1-213] G is 3-Me-Ph, and R X is tBu, and R Y is Cl, and R 3 is F, and R 4 is F. [Table 1-214] G is 3-Me-Ph, and R X is tBu, and R Y is Cl, and R 3 is Me, and R 4 is H. [Table 1-215] G is 3-Me-Ph, and R X is tBu, and R Y is Cl, and R 3 is Me, and R 4 is Me. [Table 1-216] G is 3-Me-Ph, and R X is tBu, and R Y is Br, and R 3 is H, and R 4 is H. [Table 1-217] G is 3-Me-Ph, and R X is tBu, and R Y is Br, and R 3 is F, and R 4 is H. [Table 1-218] G is 3-Me-Ph, and R X is tBu, and R Y is Br, and R 3 is F, and R 4 is F. [Table 1-219] G is 3-Me-Ph, and R X is tBu, and R Y is Br, and R 3 is Me, and R 4 is H. [Table 1-220] G is 3-Me-Ph, and R X is tBu, and R Y is Br, and R3 is Me, and R 4 is Me. [Table 1-221] G is 3-Me-Ph, and R X is tAm, and R Y is H, and R 3 is H, and R 4 is H. [Table 1-222] G is 3-Me-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is H. [Table 1-223] G is 3-Me-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is F. [Table 1-224] G is 3-Me-Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is H. [Table 1-225] G is 3-Me-Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-226] G is 3-Me-Ph, and R X is tAm, and R Y is F, and R 3 is H, and R 4 is H. [Table 1-227] G is 3-Me-Ph, and R X is tAm, and R Y is F, and R 3 is F, and R 4 is H. [Table 1-228] G is 3-Me-Ph, and RX is tAm, R Y is F, R 3 is F, R 4 is F. [Table 1-229] G is 3-Me-Ph, R X is tAm, R Y is F, R 3 is Me, R 4 is H. [Table 1-230] G is 3-Me-Ph, R X is tAm, R Y is F, R 3 is Me, R 4 is Me. [Table 1-231] G is 3-Me-Ph, R X is tAm, R Y is Cl, R 3 is H, R 4 is H. [Table 1-232] G is 3-Me-Ph, R X is tAm, R Y is Cl, R 3 is F, R 4 is H. [Table 1-233] G is 3-Me-Ph, R X is tAm, R Y is Cl, R 3 is F, R 4 is F. [Table 1-234] G is 3-Me-Ph, R X is tAm, R Y is Cl, R 3 is Me, R 4 is H. [Table 1-235] G is 3-Me-Ph, R X is tAm, R Y is Cl, R 3 is Me, R 4 is Me. [Table 1-236] G is 3-Me-Ph, R X is tAm, R Y is Br, R 3 is H, R 4 is H. [Table 1-237] G is 3-Me-Ph, R X is tAm, R Y is Br, R 3 is F, R 4 is H. [Table 1-238] G is 3-Me-Ph, R X is tAm, R Y is Br, R 3 is F, R 4 is F. [Table 1-239] G is 3-Me-Ph, R X is tAm, R Y is Br, R 3 is Me, R 4 is H. [Table 1-240] G is 3-Me-Ph, R X is tAm, R Y is Br, R 3 is Me, R 4 is Me. [Table 1-241] G is 3-cPr-Ph, R X is tBu, R Y is H, R 3 is H, R 4 is H. [Table 1-242] G is 3-cPr-Ph, R X is tBu, R Y is H, R 3 is F, R 4 is H. [Table 1-243] G is 3-cPr-Ph, R X is tBu, R Yis H, R 3 is F, R 4 is F. [Table 1-244] G is 3-cPr-Ph, R X is tBu, R Y is H, R 3 is Me, R 4 is H. [Table 1-245] G is 3-cPr-Ph, R X is tBu, R Y is H, R 3 is Me, R 4 is Me. [Table 1-246] G is 3-cPr-Ph, R X is tBu, R Y is F, R 3 is H, R 4 is H. [Table 1-247] G is 3-cPr-Ph, R X is tBu, R Y is F, R 3 is F, R 4 is H. [Table 1-248] G is 3-cPr-Ph, R X is tBu, R Y is F, R 3 is F, R 4 is F. [Table 1-249] G is 3-cPr-Ph, R X is tBu, R Y is F, R 3 is Me, R 4 is H. [Table 1-250] G is 3-cPr-Ph, R X is tBu, R Y is F, R 3 is Me, R 4 is Me. [Table 1-251] G is 3-cPr-Ph, and R X is tBu, and R Y is Cl, and R 3 is H, and R 4 is H. [Table 1-252] G is 3-cPr-Ph, and R X is tBu, and R Y is Cl, and R 3 is F, and R 4 is H. [Table 1-253] G is 3-cPr-Ph, and R X is tBu, and R Y is Cl, and R 3 is F, and R 4 is F. [Table 1-254] G is 3-cPr-Ph, and R X is tBu, and R Y is Cl, and R 3 is Me, and R 4 is H. [Table 1-255] G is 3-cPr-Ph, and R X is tBu, and R Y is Cl, and R 3 is Me, and R 4 is Me. [Table 1-256] G is 3-cPr-Ph, and R X is tBu, and R Y is Br, and R 3 is H, and R 4 is H. [Table 1-257] G is 3-cPr-Ph, and R X is tBu, and R Y is Br, and R 3 is F, and R 4 is H. [Table 1-258] G is 3-cPr-Ph, and R X is tBu, and R Y is Br, and R3 is F, and R 4 is F. [Table 1-259] G is 3-cPr-Ph, and R X is tBu, and R Y is Br, and R 3 is Me, and R 4 is H. [Table 1-260] G is 3-cPr-Ph, and R X is tBu, and R Y is Br, and R 3 is Me, and R 4 is Me. [Table 1-261] G is 3-cPr-Ph, and R X is tAm, and R Y is H, and R 3 is H, and R 4 is H. [Table 1-262] G is 3-cPr-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is H. [Table 1-263] G is 3-cPr-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is F. [Table 1-264] G is 3-cPr-Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is H. [Table 1-265] G is 3-cPr-Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-266] G is 3-cPr-Ph, R X is tAm, R Y is F, R 3 is H, R 4 is H. [Table 1-267] G is 3-cPr-Ph, R X is tAm, R Y is F, R 3 is F, R 4 is H. [Table 1-268] G is 3-cPr-Ph, R X is tAm, R Y is F, R 3 is F, R 4 is F. [Table 1-269] G is 3-cPr-Ph, R X is tAm, R Y is F, R 3 is Me, R 4 is H. [Table 1-270] G is 3-cPr-Ph, R X is tAm, R Y is F, R 3 is Me, R 4 is Me. [Table 1-271] G is 3-cPr-Ph, R X is tAm, R Y is Cl, R 3 is H, R 4 is H. [Table 1-272] G is 3-cPr-Ph, R X is tAm, R Y is Cl, R 3 is F, R 4 is H. [Table 1-273] G is 3-cPr-Ph, R X is tAm, R Y is Cl, R 3 is F, R4 is F. [Table 1-274] G is 3-cPr-Ph, and R X is tAm, and R Y is Cl, and R 3 is Me, and R 4 is H. [Table 1-275] G is 3-cPr-Ph, and R X is tAm, and R Y is Cl, and R 3 is Me, and R 4 is Me. [Table 1-276] G is 3-cPr-Ph, and R X is tAm, and R Y is Br, and R 3 is H, and R 4 is H. [Table 1-277] G is 3-cPr-Ph, and R X is tAm, and R Y is Br, and R 3 is F, and R 4 is H. [Table 1-278] G is 3-cPr-Ph, and R X is tAm, and R Y is Br, and R 3 is F, and R 4 is F. [Table 1-279] G is 3-cPr-Ph, and R X is tAm, and R Y is Br, and R 3 is Me, and R 4 is H. [Table 1-280] G is 3-cPr-Ph, and R X is tAm, and R Y is Br, and R 3 is Me, and R 4 is Me. [Table 1-281] G is 3-CF3-Ph, and RX is tBu, and R Y is H, and R 3 is H, and R 4 is H. [Table 1-282] G is 3-CF3-Ph, and R X is tBu, and R Y is H, and R 3 is F, and R 4 is H. [Table 1-283] G is 3-CF3-Ph, and R X is tBu, and R Y is H, and R 3 is F, and R 4 is F. [Table 1-284] G is 3-CF3-Ph, and R X is tBu, and R Y is H, and R 3 is Me, and R 4 is H. [Table 1-285] G is 3-CF3-Ph, and R X is tBu, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-286] G is 3-CF3-Ph, and R X is tBu, and R Y is F, and R 3 is H, and R 4 is H. [Table 1-287] G is 3-CF3-Ph, and R X is tBu, and R Y is F, and R 3 is F, and R 4 is H. [Table 1-288] G is 3-CF3-Ph, and R X is tBu, and R Y is F, and R 3 is F, and R 4 is F. [Table 1-289] G is 3-CF3-Ph, and R X is tBu, and R Y is F, and R 3 is Me, and R 4 is H. [Table 1-290] G is 3-CF3-Ph, and R X is tBu, and R Y is F, and R 3 is Me, and R 4 is Me. [Table 1-291] G is 3-CF3-Ph, and R X is tBu, and R Y is Cl, and R 3 is H, and R 4 is H. [Table 1-292] G is 3-CF3-Ph, and R X is tBu, and R Y is Cl, and R 3 is F, and R 4 is H. [Table 1-293] G is 3-CF3-Ph, and R X is tBu, and R Y is Cl, and R 3 is F, and R 4 is F. [Table 1-294] G is 3-CF3-Ph, and R X is tBu, and R Y is Cl, and R 3 is Me, and R 4 is H. [Table 1-295] G is 3-CF3-Ph, and R X is tBu, and R Y is Cl, and R 3 is Me, and R 4 is Me. [Table 1-296] G is 3-CF3-Ph, and R X is tBu, and RY is Br, and R 3 is H, and R 4 is H. [Table 1-297] G is 3-CF3-Ph, and R X is tBu, and R Y is Br, and R 3 is F, and R 4 is H. [Table 1-298] G is 3-CF3-Ph, and R X is tBu, and R Y is Br, and R 3 is F, and R 4 is F. [Table 1-299] G is 3-CF3-Ph, and R X is tBu, and R Y is Br, and R 3 is Me, and R 4 is H. [Table 1-300] G is 3-CF3-Ph, and R X is tBu, and R Y is Br, and R 3 is Me, and R 4 is Me. [Table 1-301] G is 3-CF3-Ph, and R X is tAm, and R Y is H, and R 3 is H, and R 4 is H. [Table 1-302] G is 3-CF3-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is H. [Table 1-303] G is 3-CF3-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is F. [Table 1-304] G is 3-CF3-Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is H. [Table 1-305] G is 3-CF3-Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-306] G is 3-CF3-Ph, and R X is tAm, and R Y is F, and R 3 is H, and R 4 is H. [Table 1-307] G is 3-CF3-Ph, and R X is tAm, and R Y is F, and R 3 is F, and R 4 is H. [Table 1-308] G is 3-CF3-Ph, and R X is tAm, and R Y is F, and R 3 is F, and R 4 is F. [Table 1-309] G is 3-CF3-Ph, and R X is tAm, and R Y is F, and R 3 is Me, and R 4 is H. [Table 1-310] G is 3-CF3-Ph, and R X is tAm, and R Y is F, and R 3 is Me, and R 4 is Me. [Table 1-311] G is 3-CF3-Ph, and R X is tAm, and R Yis Cl, and R 3 is H, and R 4 is H. [Table 1-312] G is 3-CF3-Ph, and R X is tAm, and R Y is Cl, and R 3 is F, and R 4 is H. [Table 1-313] G is 3-CF3-Ph, and R X is tAm, and R Y is Cl, and R 3 is F, and R 4 is F. [Table 1-314] G is 3-CF3-Ph, and R X is tAm, and R Y is Cl, and R 3 is Me, and R 4 is H. [Table 1-315] G is 3-CF3-Ph, and R X is tAm, and R Y is Cl, and R 3 is Me, and R 4 is Me. [Table 1-316] G is 3-CF3-Ph, and R X is tAm, and R Y is Br, and R 3 is H, and R 4 is H. [Table 1-317] G is 3-CF3-Ph, and R X is tAm, and R Y is Br, and R 3 is F, and R 4 is H. [Table 1-318] G is 3-CF3-Ph, and R X is tAm, and R Y is Br, and R 3 is F, and R 4 is F. [Table 1-319] G is 3-CF3-Ph, and R X is tAm, and R Y is Br, and R 3 is Me, and R 4 is H. [Table 1-320] G is 3-CF3-Ph, and R X is tAm, and R Y is Br, and R 3 is Me, and R 4 is Me. [Table 1-321] G is 3-CF2H-Ph, and R X is tBu, and R Y is H, and R 3 is H, and R 4 is H. [Table 1-322] G is 3-CF2H-Ph, and R X is tBu, and R Y is H, and R 3 is F, and R 4 is H. [Table 1-323] G is 3-CF2H-Ph, and R X is tBu, and R Y is H, and R 3 is F, and R 4 is F. [Table 1-324] G is 3-CF2H-Ph, and R X is tBu, and R Y is H, and R 3 is Me, and R 4 is H. [Table 1-325] G is 3-CF2H-Ph, and R X is tBu, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-326] G is 3-CF2H-Ph, and R X is tBu, and R Y is F, and R3 is H, and R 4 is H. [Table 1-327] G is 3-CF2H-Ph, and R X is tBu, and R Y is F, and R 3 is F, and R 4 is H. [Table 1-328] G is 3-CF2H-Ph, and R X is tBu, and R Y is F, and R 3 is F, and R 4 is F. [Table 1-329] G is 3-CF2H-Ph, and R X is tBu, and R Y is F, and R 3 is Me, and R 4 is H. [Table 1-330] G is 3-CF2H-Ph, and R X is tBu, and R Y is F, and R 3 is Me, and R 4 is Me. [Table 1-331] G is 3-CF2H-Ph, and R X is tBu, and R Y is Cl, and R 3 is H, and R 4 is H. [Table 1-332] G is 3-CF2H-Ph, and R X is tBu, and R Y is Cl, and R 3 is F, and R 4 is H. [Table 1-333] G is 3-CF2H-Ph, and R X is tBu, and R Y is Cl, and R 3 is F, and R 4 is F. [Table 1-334] G is 3-CF2H-Ph, and R X is tBu, and R Y is Cl, and R 3 is Me, and R 4 is H. [Table 1-335] G is 3-CF2H-Ph, and R X is tBu, and R Y is Cl, and R 3 is Me, and R 4 is Me. [Table 1-336] G is 3-CF2H-Ph, and R X is tBu, and R Y is Br, and R 3 is H, and R 4 is H. [Table 1-337] G is 3-CF2H-Ph, and R X is tBu, and R Y is Br, and R 3 is F, and R 4 is H. [Table 1-338] G is 3-CF2H-Ph, and R X is tBu, and R Y is Br, and R 3 is F, and R 4 is F. [Table 1-339] G is 3-CF2H-Ph, and R X is tBu, and R Y is Br, and R 3 is Me, and R 4 is H. [Table 1-340] G is 3-CF2H-Ph, and R X is tBu, and R Y is Br, and R 3 is Me, and R 4 is Me. [Table 1-341] G is 3-CF2H-Ph, and R X is tAm, and R Y is H, and R3 is H, and R 4 is H. [Table 1-342] G is 3-CF2H-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is H. [Table 1-343] G is 3-CF2H-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is F. [Table 1-344] G is 3-CF2H-Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is H. [Table 1-345] G is 3-CF2H-Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-346] G is 3-CF2H-Ph, and R X is tAm, and R Y is F, and R 3 is H, and R 4 is H. [Table 1-347] G is 3-CF2H-Ph, and R X is tAm, and R Y is F, and R 3 is F, and R 4 is H. [Table 1-348] G is 3-CF2H-Ph, and R X is tAm, and R Y is F, and R 3 is F, and R 4 is F. [Table 1-349] G is 3-CF2H-Ph, and R X is tAm, and R Y is F, and R 3 is Me, and R 4 is H. [Table 1-350] G is 3-CF2H-Ph, and R X is tAm, and R Y is F, and R 3 is Me, and R 4 is Me. [Table 1-351] G is 3-CF2H-Ph, and R X is tAm, and R Y is Cl, and R 3 is H, and R 4 is H. [Table 1-352] G is 3-CF2H-Ph, and R X is tAm, and R Y is Cl, and R 3 is F, and R 4 is H. [Table 1-353] G is 3-CF2H-Ph, and R X is tAm, and R Y is Cl, and R 3 is F, and R 4 is F. [Table 1-354] G is 3-CF2H-Ph, and R X is tAm, and R Y is Cl, and R 3 is Me, and R 4 is H. [Table 1-355] G is 3-CF2H-Ph, and R X is tAm, and R Y is Cl, and R 3 is Me, and R 4 is Me. [Table 1-356] G is 3-CF2H-Ph, and R X is tAm, and R Y is Br, and R3 is H, R 4 is H. [Table 1-357] G is 3-CF2H-Ph, R X is tAm, R Y is Br, R 3 is F, R 4 is H. [Table 1-358] G is 3-CF2H-Ph, R X is tAm, R Y is Br, R 3 is F, R 4 is F. [Table 1-359] G is 3-CF2H-Ph, R X is tAm, R Y is Br, R 3 is Me, R 4 is H. [Table 1-360] G is 3-CF2H-Ph, R X is tAm, R Y is Br, R 3 is Me, R 4 is Me. [Table 1-361] G is 3-OMe-Ph, R X is tBu, R Y is H, R 3 is H, R 4 is H. [Table 1-362] G is 3-OMe-Ph, R X is tBu, R Y is H, R 3 is F, R 4 is H. [Table 1-363] G is 3-OMe-Ph, R X is tBu, R Y is H, R 3 is F, R 4 is F. [Table 1-364] G is 3-OMe-Ph, R X is tBu, R Y is H, R 3 is Me, R 4 is H. [Table 1-365] G is 3-OMe-Ph, R X is tBu, R Y is H, R 3 is Me, R 4 is Me. [Table 1-366] G is 3-OMe-Ph, R X is tBu, R Y is F, R 3 is H, R 4 is H. [Table 1-367] G is 3-OMe-Ph, R X is tBu, R Y is F, R 3 is F, R 4 is H. [Table 1-368] G is 3-OMe-Ph, R X is tBu, R Y is F, R 3 is F, R 4 is F. [Table 1-369] G is 3-OMe-Ph, R X is tBu, R Y is F, R 3 is Me, R 4 is H. [Table 1-370] G is 3-OMe-Ph, R X is tBu, R Y is F, R 3 is Me, R 4 is Me. [Table 1-371] G is 3-OMe-Ph, R X is tBu, R Y is Cl, R 3 is H, R4 is H. [Table 1-372] G is 3-OMe-Ph, and R X is tBu, and R Y is Cl, and R 3 is F, and R 4 is H. [Table 1-373] G is 3-OMe-Ph, and R X is tBu, and R Y is Cl, and R 3 is F, and R 4 is F. [Table 1-374] G is 3-OMe-Ph, and R X is tBu, and R Y is Cl, and R 3 is Me, and R 4 is H. [Table 1-375] G is 3-OMe-Ph, and R X is tBu, and R Y is Cl, and R 3 is Me, and R 4 is Me. [Table 1-376] G is 3-OMe-Ph, and R X is tBu, and R Y is Br, and R 3 is H, and R 4 is H. [Table 1-377] G is 3-OMe-Ph, and R X is tBu, and R Y is Br, and R 3 is F, and R 4 is H. [Table 1-378] G is 3-OMe-Ph, and R X is tBu, and R Y is Br, and R 3 is F, and R 4 is F. [Table 1-379] G is 3-OMe-Ph, and RX is tBu, and R Y is Br, and R 3 is Me, and R 4 is H. [Table 1-380] G is 3-OMe-Ph, and R X is tBu, and R Y is Br, and R 3 is Me, and R 4 is Me. [Table 1-381] G is 3-OMe-Ph, and R X is tAm, and R Y is H, and R 3 is H, and R 4 is H. [Table 1-382] G is 3-OMe-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is H. [Table 1-383] G is 3-OMe-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is F. [Table 1-384] G is 3-OMe-Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is H. [Table 1-385] G is 3-OMe-Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-386] G is 3-OMe-Ph, and R X is tAm, and R Y is F, and R 3 is H, and R 4 4It is H. [Table 1-387] G is 3-OMe-Ph, and R X is tAm, and R Y is F, and R 3 is F, and R 4 is H. [Table 1-388] G is 3-OMe-Ph, and R X is tAm, and R Y is F, and R 3 is F, and R 4 is F. [Table 1-389] G is 3-OMe-Ph, and R X is tAm, and R Y is F, and R 3 is Me, and R 4 is H. [Table 1-390] G is 3-OMe-Ph, and R X is tAm, and R Y is F, and R 3 is Me, and R 4 is Me. [Table 1-391] G is 3-OMe-Ph, and R X is tAm, and R Y is Cl, and R 3 is H, and R 4 is H. [Table 1-392] G is 3-OMe-Ph, and R X is tAm, and R Y is Cl, and R 3 is F, and R 4 is H. [Table 1-393] G is 3-OMe-Ph, and R X is tAm, and R Y is Cl, and R 3 is F, and R 4 is F. [Table 1-394] G is 3-OMe-Ph, and R X is tAm, and RY is Cl, and R 3 is Me, and R 4 is H. [Table 1-395] G is 3-OMe-Ph, and R X is tAm, and R Y is Cl, and R 3 is Me, and R 4 is Me. [Table 1-396] G is 3-OMe-Ph, and R X is tAm, and R Y is Br, and R 3 is H, and R 4 is H. [Table 1-397] G is 3-OMe-Ph, and R X is tAm, and R Y is Br, and R 3 is F, and R 4 is H. [Table 1-398] G is 3-OMe-Ph, and R X is tAm, and R Y is Br, and R 3 is F, and R 4 is F. [Table 1-399] G is 3-OMe-Ph, and R X is tAm, and R Y is Br, and R 3 is Me, and R 4 is H. [Table 1-400] G is 3-OMe-Ph, and R X is tAm, and R Y is Br, and R 3 is Me, and R 4 is Me. [Table 1-401] G is 3-OCF3-Ph, and R X is tBu, and R Y is H, and R 3 is H, and R 4 is H. [Table 1-402] G is 3-OCF3-Ph, and R X is tBu, and R Y is H, and R 3 is F, and R 4 is H. [Table 1-403] G is 3-OCF3-Ph, and R X is tBu, and R Y is H, and R 3 is F, and R 4 is F. [Table 1-404] G is 3-OCF3-Ph, and R X is tBu, and R Y is H, and R 3 is Me, and R 4 is H. [Table 1-405] G is 3-OCF3-Ph, and R X is tBu, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-406] G is 3-OCF3-Ph, and R X is tBu, and R Y is F, and R 3 is H, and R 4 is H. [Table 1-407] G is 3-OCF3-Ph, and R X is tBu, and R Y is F, and R 3 is F, and R 4 is H. [Table 1-408] G is 3-OCF3-Ph, and R X is tBu, and R Y is F, and R 3 is F, and R 4 is F. [Table 1-409] G is 3-OCF3-Ph, and R X is tBu, and R Yis F, and R 3 is Me, and R 4 is H. [Table 1-410] G is 3-OCF3-Ph, and R X is tBu, and R Y is F, and R 3 is Me, and R 4 is Me. [Table 1-411] G is 3-OCF3-Ph, and R X is tBu, and R Y is Cl, and R 3 is H, and R 4 is H. [Table 1-412] G is 3-OCF3-Ph, and R X is tBu, and R Y is Cl, and R 3 is F, and R 4 is H. [Table 1-413] G is 3-OCF3-Ph, and R X is tBu, and R Y is Cl, and R 3 is F, and R 4 is F. [Table 1-414] G is 3-OCF3-Ph, and R X is tBu, and R Y is Cl, and R 3 is Me, and R 4 is H. [Table 1-415] G is 3-OCF3-Ph, and R X is tBu, and R Y is Cl, and R 3 is Me, and R 4 is Me. [Table 1-416] G is 3-OCF3-Ph, and R X is tBu, and R Y is Br, and R 3 is H, and R 4 is H. [Table 1-417] G is 3-OCF3-Ph, and R X is tBu, and R Y is Br, and R 3 is F, and R 4 is H. [Table 1-418] G is 3-OCF3-Ph, and R X is tBu, and R Y is Br, and R 3 is F, and R 4 is F. [Table 1-419] G is 3-OCF3-Ph, and R X is tBu, and R Y is Br, and R 3 is Me, and R 4 is H. [Table 1-420] G is 3-OCF3-Ph, and R X is tBu, and R Y is Br, and R 3 is Me, and R 4 is Me. [Table 1-421] G is 3-OCF3-Ph, and R X is tAm, and R Y is H, and R 3 is H, and R 4 is H. [Table 1-422] G is 3-OCF3-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is H. [Table 1-423] G is 3-OCF3-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is F. [Table 1-424] G is 3-OCF3-Ph, and R X is tAm, and RY is H, and R 3 is Me, and R 4 is H. [Table 1-425] G is 3-OCF3-Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-426] G is 3-OCF3-Ph, and R X is tAm, and R Y is F, and R 3 is H, and R 4 is H. [Table 1-427] G is 3-OCF3-Ph, and R X is tAm, and R Y is F, and R 3 is F, and R 4 is H. [Table 1-428] G is 3-OCF3-Ph, and R X is tAm, and R Y is F, and R 3 is F, and R 4 is F. [Table 1-429] G is 3-OCF3-Ph, and R X is tAm, and R Y is F, and R 3 is Me, and R 4 is H. [Table 1-430] G is 3-OCF3-Ph, and R X is tAm, and R Y is F, and R 3 is Me, and R 4 is Me. [Table 1-431] G is 3-OCF3-Ph, and R X is tAm, and R Y is Cl, and R 3 is H, and R 4 is H. [Table 1-432] G is 3-OCF3-Ph, and R X is tAm, and R Y is Cl, and R 3 is F, and R 4 is H. [Table 1-433] G is 3-OCF3-Ph, and R X is tAm, and R Y is Cl, and R 3 is F, and R 4 is F. [Table 1-434] G is 3-OCF3-Ph, and R X is tAm, and R Y is Cl, and R 3 is Me, and R 4 is H. [Table 1-435] G is 3-OCF3-Ph, and R X is tAm, and R Y is Cl, and R 3 is Me, and R 4 is Me. [Table 1-436] G is 3-OCF3-Ph, and R X is tAm, and R Y is Br, and R 3 is H, and R 4 is H. [Table 1-437] G is 3-OCF3-Ph, and R X is tAm, and R Y is Br, and R 3 is F, and R 4 is H. [Table 1-438] G is 3-OCF3-Ph, and R X is tAm, and R Y is Br, and R 3 is F, and R 4 is F. [Table 1-439] G is 3-OCF3-Ph, and R X is tAm, and RY is Br, and R 3 is Me, and R 4 is H. [Table 1-440] G is 3-OCF3-Ph, and R X is tAm, and R Y is Br, and R 3 is Me, and R 4 is Me. [Table 1-441] G is 3-OCF2H-Ph, and R X is tBu, and R Y is H, and R 3 is H, and R 4 is H. [Table 1-442] G is 3-OCF2H-Ph, and R X is tBu, and R Y is H, and R 3 is F, and R 4 is H. [Table 1-443] G is 3-OCF2H-Ph, and R X is tBu, and R Y is H, and R 3 is F, and R 4 is F. [Table 1-444] G is 3-OCF2H-Ph, and R X is tBu, and R Y is H, and R 3 is Me, and R 4 is H. [Table 1-445] G is 3-OCF2H-Ph, and R X is tBu, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-446] G is 3-OCF2H-Ph, and R X is tBu, and R Y is F, and R 3 is H, and R 4 is H. [Table 1-447] G is 3-OCF2H-Ph, R X is tBu, R Y is F, R 3 is F, R 4 is H. [Table 1-448] G is 3-OCF2H-Ph, R X is tBu, R Y is F, R 3 is F, R 4 is F. [Table 1-449] G is 3-OCF2H-Ph, R X is tBu, R Y is F, R 3 is Me, R 4 is H. [Table 1-450] G is 3-OCF2H-Ph, R X is tBu, R Y is F, R 3 is Me, R 4 is Me. [Table 1-451] G is 3-OCF2H-Ph, R X is tBu, R Y is Cl, R 3 is H, R 4 is H. [Table 1-452] G is 3-OCF2H-Ph, R X is tBu, R Y is Cl, R 3 is F, R 4 is H. [Table 1-453] G is 3-OCF2H-Ph, R X is tBu, R Y is Cl, R 3 is F, R 4 is F. [Table 1-454] G is 3-OCF2H-Ph, R Xis tBu, and R Y is Cl, and R 3 is Me, and R 4 is H. [Table 1-455] G is 3-OCF2H-Ph, and R X is tBu, and R Y is Cl, and R 3 is Me, and R 4 is Me. [Table 1-456] G is 3-OCF2H-Ph, and R X is tBu, and R Y is Br, and R 3 is H, and R 4 is H. [Table 1-457] G is 3-OCF2H-Ph, and R X is tBu, and R Y is Br, and R 3 is F, and R 4 is H. [Table 1-458] G is 3-OCF2H-Ph, and R X is tBu, and R Y is Br, and R 3 is F, and R 4 is F. [Table 1-459] G is 3-OCF2H-Ph, and R X is tBu, and R Y is Br, and R 3 is Me, and R 4 is H. [Table 1-460] G is 3-OCF2H-Ph, and R X is tBu, and R Y is Br, and R 3 is Me, and R 4 is Me. [Table 1-461] G is 3-OCF2H-Ph, and R X is tAm, and R Y is H, and R 3 is H, and R4 is H. [Table 1-462] G is 3-OCF2H-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is H. [Table 1-463] G is 3-OCF2H-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is F. [Table 1-464] G is 3-OCF2H-Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is H. [Table 1-465] G is 3-OCF2H-Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-466] G is 3-OCF2H-Ph, and R X is tAm, and R Y is F, and R 3 is H, and R 4 is H. [Table 1-467] G is 3-OCF2H-Ph, and R X is tAm, and R Y is F, and R 3 is F, and R 4 is H. [Table 1-468] G is 3-OCF2H-Ph, and R X is tAm, and R Y is F, and R 3 is F, and R 4 is F. [Table 1-469] G is 3-OCF2H-Ph, and R X is tAm, and R Y is F, and R 3 is Me, and R 4 is H. [Table 1-470] G is 3-OCF2H-Ph, and R X is tAm, and R Y is F, and R 3 is Me, and R 4 is Me. [Table 1-471] G is 3-OCF2H-Ph, and R X is tAm, and R Y is Cl, and R 3 is H, and R 4 is H. [Table 1-472] G is 3-OCF2H-Ph, and R X is tAm, and R Y is Cl, and R 3 is F, and R 4 is H. [Table 1-473] G is 3-OCF2H-Ph, and R X is tAm, and R Y is Cl, and R 3 is F, and R 4 is F. [Table 1-474] G is 3-OCF2H-Ph, and R X is tAm, and R Y is Cl, and R 3 is Me, and R 4 is H. [Table 1-475] G is 3-OCF2H-Ph, and R X is tAm, and R Y is Cl, and R 3 is Me, and R 4 is Me. [Table 1-476] G is 3-OCF2H-Ph, and R X is tAm, and R Yis Br, and R 3 is H, and R 4 is H. [Table 1-477] G is 3-OCF2H-Ph, and R X is tAm, and R Y is Br, and R 3 is F, and R 4 is H. [Table 1-478] G is 3-OCF2H-Ph, and R X is tAm, and R Y is Br, and R 3 is F, and R 4 is F. [Table 1-479] G is 3-OCF2H-Ph, and R X is tAm, and R Y is Br, and R 3 is Me, and R 4 is H. [Table 1-480] G is 3-OCF2H-Ph, and R X is tAm, and R Y is Br, and R 3 is Me, and R 4 is Me. [Table 1-481] G is 2-F-Ph, and R X is tBu, and R Y is H, and R 3 is H, and R 4 is H. [Table 1-482] G is 2-F-Ph, and R X is tBu, and R Y is H, and R 3 is F, and R 4 is H. [Table 1-483] G is 2-F-Ph, and R X is tBu, and R Y is H, and R 3 is F, and R 4 is F. [Table 1-484] G is 2-F-Ph, and R X is tBu, and R Y is H, and R 3 is Me, and R 4 is H. [Table 1-485] G is 2-F-Ph, and R X is tBu, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-486] G is 2-F-Ph, and R X is tBu, and R Y is F, and R 3 is H, and R 4 is H. [Table 1-487] G is 2-F-Ph, and R X is tBu, and R Y is F, and R 3 is F, and R 4 is H. [Table 1-488] G is 2-F-Ph, and R X is tBu, and R Y is F, and R 3 is F, and R 4 is F. [Table 1-489] G is 2-F-Ph, and R X is tBu, and R Y is F, and R 3 is Me, and R 4 is H. [Table 1-490] G is 2-F-Ph, and R X is tBu, and R Y is F, and R 3 is Me, and R 4 is Me. [Table 1-491] G is 2-F-Ph, and R X is tBu, and R Y is Cl, and R 3 is H, and R4 is H. [Table 1-492] G is 2-F-Ph, R X is tBu, R Y is Cl, R 3 is F, R 4 is H. [Table 1-493] G is 2-F-Ph, R X is tBu, R Y is Cl, R 3 is F, R 4 is F. [Table 1-494] G is 2-F-Ph, R X is tBu, R Y is Cl, R 3 is Me, R 4 is H. [Table 1-495] G is 2-F-Ph, R X is tBu, R Y is Cl, R 3 is Me, R 4 is Me. [Table 1-496] G is 2-F-Ph, R X is tBu, R Y is Br, R 3 is H, R 4 is H. [Table 1-497] G is 2-F-Ph, R X is tBu, R Y is Br, R 3 is F, R 4 is H. [Table 1-498] G is 2-F-Ph, R X is tBu, R Y is Br, R 3 is F, R 4 is F. [Table 1-499] G is 2-F-Ph, R X is tBu, RY is Br, and R 3 is Me, and R 4 is H. [Table 1-500] G is 2-F-Ph, and R X is tBu, and R Y is Br, and R 3 is Me, and R 4 is Me. [Table 1-501] G is 2-F-Ph, and R X is tAm, and R Y is H, and R 3 is H, and R 4 is H. [Table 1-502] G is 2-F-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is H. [Table 1-503] G is 2-F-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is F. [Table 1-504] G is 2-F-Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is H. [Table 1-505] G is 2-F-Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-506] G is 2-F-Ph, and R X is tAm, and R Y is F, and R 3 is H, and R 4 is H. [Table 1-507] G is 2-F-Ph, and R X is tAm, and R Y is F, and R 3 is F, and R 4 is H. [Table 1-508] G is 2-F-Ph, and R X is tAm, and R Y is F, and R 3 is F, and R 4 is F. [Table 1-509] G is 2-F-Ph, and R X is tAm, and R Y is F, and R 3 is Me, and R 4 is H. [Table 1-510] G is 2-F-Ph, and R X is tAm, and R Y is F, and R 3 is Me, and R 4 is Me. [Table 1-511] G is 2-F-Ph, and R X is tAm, and R Y is Cl, and R 3 is H, and R 4 is H. [Table 1-512] G is 2-F-Ph, and R X is tAm, and R Y is Cl, and R 3 is F, and R 4 is H. [Table 1-513] G is 2-F-Ph, and R X is tAm, and R Y is Cl, and R 3 is F, and R 4 is F. [Table 1-514] G is 2-F-Ph, and R X is tAm, and R Y is Cl, and R 3 is Me, and R 4It is H. [Table 1-515] G is 2-F-Ph, and R X is tAm, and R Y is Cl, and R 3 is Me, and R 4 is Me. [Table 1-516] G is 2-F-Ph, and R X is tAm, and R Y is Br, and R 3 is H, and R 4 is H. [Table 1-517] G is 2-F-Ph, and R X is tAm, and R Y is Br, and R 3 is F, and R 4 is H. [Table 1-518] G is 2-F-Ph, and R X is tAm, and R Y is Br, and R 3 is F, and R 4 is F. [Table 1-519] G is 2-F-Ph, and R X is tAm, and R Y is Br, and R 3 is Me, and R 4 is H. [Table 1-520] G is 2-F-Ph, and R X is tAm, and R Y is Br, and R 3 is Me, and R 4 is Me. [Table 1-521] G is 2,3-F2-Ph, and R X is tBu, and R Y is H, and R 3 is H, and R 4 is H. [Table 1-522] G is 2,3-F2-Ph, and R X is tBu, and RY is H, and R 3 is F, and R 4 is H. [Table 1-523] G is 2,3-F2-Ph, and R X is tBu, and R Y is H, and R 3 is F, and R 4 is F. [Table 1-524] G is 2,3-F2-Ph, and R X is tBu, and R Y is H, and R 3 is Me, and R 4 is H. [Table 1-525] G is 2,3-F2-Ph, and R X is tBu, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-526] G is 2,3-F2-Ph, and R X is tBu, and R Y is F, and R 3 is H, and R 4 is H. [Table 1-527] G is 2,3-F2-Ph, and R X is tBu, and R Y is F, and R 3 is F, and R 4 is H. [Table 1-528] G is 2,3-F2-Ph, and R X is tBu, and R Y is F, and R 3 is F, and R 4 is F. [Table 1-529] G is 2,3-F2-Ph, and R X is tBu, and R Y is F, and R 3 is Me, and R 4 is H. [Table 1-530] G is 2,3-F2-Ph, and R X is tBu, and R Y is F, and R 3 is Me, and R 4 is Me. [Table 1-531] G is 2,3-F2-Ph, and R X is tBu, and R Y is Cl, and R 3 is H, and R 4 is H. [Table 1-532] G is 2,3-F2-Ph, and R X is tBu, and R Y is Cl, and R 3 is F, and R 4 is H. [Table 1-533] G is 2,3-F2-Ph, and R X is tBu, and R Y is Cl, and R 3 is F, and R 4 is F. [Table 1-534] G is 2,3-F2-Ph, and R X is tBu, and R Y is Cl, and R 3 is Me, and R 4 is H. [Table 1-535] G is 2,3-F2-Ph, and R X is tBu, and R Y is Cl, and R 3 is Me, and R 4 is Me. [Table 1-536] G is 2,3-F2-Ph, and R X is tBu, and R Y is Br, and R 3 is H, and R 4 is H. [Table 1-537] G is 2,3-F2-Ph, and R X is tBu, and RY is Br, and R 3 is F, and R 4 is H. [Table 1-538] G is 2,3-F2-Ph, and R X is tBu, and R Y is Br, and R 3 is F, and R 4 is F. [Table 1-539] G is 2,3-F2-Ph, and R X is tBu, and R Y is Br, and R 3 is Me, and R 4 is H. [Table 1-540] G is 2,3-F2-Ph, and R X is tBu, and R Y is Br, and R 3 is Me, and R 4 is Me. [Table 1-541] G is 2,3-F2-Ph, and R X is tAm, and R Y is H, and R 3 is H, and R 4 is H. [Table 1-542] G is 2,3-F2-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is H. [Table 1-543] G is 2,3-F2-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is F. [Table 1-544] G is 2,3-F2-Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is H. [Table 1-545] G is 2,3-F2-Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-546] G is 2,3-F2-Ph, and R X is tAm, and R Y is F, and R 3 is H, and R 4 is H. [Table 1-547] G is 2,3-F2-Ph, and R X is tAm, and R Y is F, and R 3 is F, and R 4 is H. [Table 1-548] G is 2,3-F2-Ph, and R X is tAm, and R Y is F, and R 3 is F, and R 4 is F. [Table 1-549] G is 2,3-F2-Ph, and R X is tAm, and R Y is F, and R 3 is Me, and R 4 is H. [Table 1-550] G is 2,3-F2-Ph, and R X is tAm, and R Y is F, and R 3 is Me, and R 4 is Me. [Table 1-551] G is 2,3-F2-Ph, and R X is tAm, and R Y is Cl, and R 3 is H, and R 4 is H. [Table 1-552] G is 2,3-F2-Ph, and R X is tAm, and R Yis Cl, and R 3 is F, and R 4 is H. [Table 1-553] G is 2,3-F2-Ph, and R X is tAm, and R Y is Cl, and R 3 is F, and R 4 is F. [Table 1-554] G is 2,3-F2-Ph, and R X is tAm, and R Y is Cl, and R 3 is Me, and R 4 is H. [Table 1-555] G is 2,3-F2-Ph, and R X is tAm, and R Y is Cl, and R 3 is Me, and R 4 is Me. [Table 1-556] G is 2,3-F2-Ph, and R X is tAm, and R Y is Br, and R 3 is H, and R 4 is H. [Table 1-557] G is 2,3-F2-Ph, and R X is tAm, and R Y is Br, and R 3 is F, and R 4 is H. [Table 1-558] G is 2,3-F2-Ph, and R X is tAm, and R Y is Br, and R 3 is F, and R 4 is F. [Table 1-559] G is 2,3-F2-Ph, and R X is tAm, and R Y is Br, and R 3 is Me, and R 4 is H. [Table 1-560] G is 2,3-F2-Ph, and R X is tAm, and R Y is Br, and R 3 is Me, and R 4 is Me. [Table 1-561] G is 2-F-3-Cl-Ph, and R X is tBu, and R Y is H, and R 3 is H, and R 4 is H. [Table 1-562] G is 2-F-3-Cl-Ph, and R X is tBu, and R Y is H, and R 3 is F, and R 4 is H. [Table 1-563] G is 2-F-3-Cl-Ph, and R X is tBu, and R Y is H, and R 3 is F, and R 4 is F. [Table 1-564] G is 2-F-3-Cl-Ph, and R X is tBu, and R Y is H, and R 3 is Me, and R 4 is H. [Table 1-565] G is 2-F-3-Cl-Ph, and R X is tBu, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-566] G is 2-F-3-Cl-Ph, and R X is tBu, and R Y is F, and R 3 is H, and R 4 is H. [Table 1-567] G is 2-F-3-Cl-Ph, and R Xis tBu, and R Y is F, and R 3 is F, and R 4 is H. [Table 1-568] G is 2-F-3-Cl-Ph, and R X is tBu, and R Y is F, and R 3 is F, and R 4 is F. [Table 1-569] G is 2-F-3-Cl-Ph, and R X is tBu, and R Y is F, and R 3 is Me, and R 4 is H. [Table 1-570] G is 2-F-3-Cl-Ph, and R X is tBu, and R Y is F, and R 3 is Me, and R 4 is Me. [Table 1-571] G is 2-F-3-Cl-Ph, and R X is tBu, and R Y is Cl, and R 3 is H, and R 4 is H. [Table 1-572] G is 2-F-3-Cl-Ph, and R X is tBu, and R Y is Cl, and R 3 is F, and R 4 is H. [Table 1-573] G is 2-F-3-Cl-Ph, and R X is tBu, and R Y is Cl, and R 3 is F, and R 4 is F. [Table 1-574] G is 2-F-3-Cl-Ph, and R X is tBu, and R Y is Cl, and R 3 is Me, and R4 is H. [Table 1-575] G is 2-F-3-Cl-Ph, and R X is tBu, and R Y is Cl, and R 3 is Me, and R 4 is Me. [Table 1-576] G is 2-F-3-Cl-Ph, and R X is tBu, and R Y is Br, and R 3 is H, and R 4 is H. [Table 1-577] G is 2-F-3-Cl-Ph, and R X is tBu, and R Y is Br, and R 3 is F, and R 4 is H. [Table 1-578] G is 2-F-3-Cl-Ph, and R X is tBu, and R Y is Br, and R 3 is F, and R 4 is F. [Table 1-579] G is 2-F-3-Cl-Ph, and R X is tBu, and R Y is Br, and R 3 is Me, and R 4 is H. [Table 1-580] G is 2-F-3-Cl-Ph, and R X is tBu, and R Y is Br, and R 3 is Me, and R 4 is Me. [Table 1-581] G is 2-F-3-Cl-Ph, and R X is tAm, and R Y is H, and R 3 is H, and R 4 is H. [Table 1-582] G is 2-F-3-Cl-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is H. [Table 1-583] G is 2-F-3-Cl-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is F. [Table 1-584] G is 2-F-3-Cl-Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is H. [Table 1-585] G is 2-F-3-Cl-Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-586] G is 2-F-3-Cl-Ph, and R X is tAm, and R Y is F, and R 3 is H, and R 4 is H. [Table 1-587] G is 2-F-3-Cl-Ph, and R X is tAm, and R Y is F, and R 3 is F, and R 4 is H. [Table 1-588] G is 2-F-3-Cl-Ph, and R X is tAm, and R Y is F, and R 3 is F, and R 4 is F. [Table 1-589] G is 2-F-3-Cl-Ph, and R X is tAm, and R Y is F, and R3 is Me, and R 4 is H. [Table 1-590] G is 2-F-3-Cl-Ph, and R X is tAm, and R Y is F, and R 3 is Me, and R 4 is Me. [Table 1-591] G is 2-F-3-Cl-Ph, and R X is tAm, and R Y is Cl, and R 3 is H, and R 4 is H. [Table 1-592] G is 2-F-3-Cl-Ph, and R X is tAm, and R Y is Cl, and R 3 is F, and R 4 is H. [Table 1-593] G is 2-F-3-Cl-Ph, and R X is tAm, and R Y is Cl, and R 3 is F, and R 4 is F. [Table 1-594] G is 2-F-3-Cl-Ph, and R X is tAm, and R Y is Cl, and R 3 is Me, and R 4 is H. [Table 1-595] G is 2-F-3-Cl-Ph, and R X is tAm, and R Y is Cl, and R 3 is Me, and R 4 is Me. [Table 1-596] G is 2-F-3-Cl-Ph, and R X is tAm, and R Y is Br, and R 3 is H, and R 4 is H. [Table 1-597] G is 2-F-3-Cl-Ph, and R X is tAm, and R Y is Br, and R 3 is F, and R 4 is H. [Table 1-598] G is 2-F-3-Cl-Ph, and R X is tAm, and R Y is Br, and R 3 is F, and R 4 is F. [Table 1-599] G is 2-F-3-Cl-Ph, and R X is tAm, and R Y is Br, and R 3 is Me, and R 4 is H. [Table 1-600] G is 2-F-3-Cl-Ph, and R X is tAm, and R Y is Br, and R 3 is Me, and R 4 is Me. [Table 1-601] G is 2-F-3-Br-Ph, and R X is tBu, and R Y is H, and R 3 is H, and R 4 is H. [Table 1-602] G is 2-F-3-Br-Ph, and R X is tBu, and R Y is H, and R 3 is F, and R 4 is H. [Table 1-603] G is 2-F-3-Br-Ph, and R X is tBu, and R Y is H, and R 3 is F, and R 4 is F. [Table 1-604] G is 2-F-3-Br-Ph, and R Xis tBu, and R Y is H, and R 3 is Me, and R 4 is H. [Table 1-605] G is 2-F-3-Br-Ph, and R X is tBu, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-606] G is 2-F-3-Br-Ph, and R X is tBu, and R Y is F, and R 3 is H, and R 4 is H. [Table 1-607] G is 2-F-3-Br-Ph, and R X is tBu, and R Y is F, and R 3 is F, and R 4 is H. [Table 1-608] G is 2-F-3-Br-Ph, and R X is tBu, and R Y is F, and R 3 is F, and R 4 is F. [Table 1-609] G is 2-F-3-Br-Ph, and R X is tBu, and R Y is F, and R 3 is Me, and R 4 is H. [Table 1-610] G is 2-F-3-Br-Ph, and R X is tBu, and R Y is F, and R 3 is Me, and R 4 is Me. [Table 1-611] G is 2-F-3-Br-Ph, and R X is tBu, and R Y is Cl, and R 3 is H, and R4 is H. [Table 1-612] G is 2-F-3-Br-Ph, and R X is tBu, and R Y is Cl, and R 3 is F, and R 4 is H. [Table 1-613] G is 2-F-3-Br-Ph, and R X is tBu, and R Y is Cl, and R 3 is F, and R 4 is F. [Table 1-614] G is 2-F-3-Br-Ph, and R X is tBu, and R Y is Cl, and R 3 is Me, and R 4 is H. [Table 1-615] G is 2-F-3-Br-Ph, and R X is tBu, and R Y is Cl, and R 3 is Me, and R 4 is Me. [Table 1-616] G is 2-F-3-Br-Ph, and R X is tBu, and R Y is Br, and R 3 is H, and R 4 is H. [Table 1-617] G is 2-F-3-Br-Ph, and R X is tBu, and R Y is Br, and R 3 is F, and R 4 is H. [Table 1-618] G is 2-F-3-Br-Ph, and R X is tBu, and R Y is Br, and R 3 is F, and R 4 is F. [Table 1-619] G is 2-F-3-Br-Ph, and R X is tBu, and R Y is Br, and R 3 is Me, and R 4 is H. [Table 1-620] G is 2-F-3-Br-Ph, and R X is tBu, and R Y is Br, and R 3 is Me, and R 4 is Me. [Table 1-621] G is 2-F-3-Br-Ph, and R X is tAm, and R Y is H, and R 3 is H, and R 4 is H. [Table 1-622] G is 2-F-3-Br-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is H. [Table 1-623] G is 2-F-3-Br-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is F. [Table 1-624] G is 2-F-3-Br-Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is H. [Table 1-625] G is 2-F-3-Br-Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-626] G is 2-F-3-Br-Ph, and R X is tAm, and R Yis F, R 3 is H, R 4 is H. [Table 1-627] G is 2-F-3-Br-Ph, R X is tAm, R Y is F, R 3 is F, R 4 is H. [Table 1-628] G is 2-F-3-Br-Ph, R X is tAm, R Y is F, R 3 is F, R 4 is F. [Table 1-629] G is 2-F-3-Br-Ph, R X is tAm, R Y is F, R 3 is Me, R 4 is H. [Table 1-630] G is 2-F-3-Br-Ph, R X is tAm, R Y is F, R 3 is Me, R 4 is Me. [Table 1-631] G is 2-F-3-Br-Ph, R X is tAm, R Y is Cl, R 3 is H, R 4 is H. [Table 1-632] G is 2-F-3-Br-Ph, R X is tAm, R Y is Cl, R 3 is F, R 4 is H. [Table 1-633] G is 2-F-3-Br-Ph, R X is tAm, R Y is Cl, R 3 is F, R 4 is F. [Table 1-634] G is 2-F-3-Br-Ph, and R X is tAm, and R Y is Cl, and R 3 is Me, and R 4 is H. [Table 1-635] G is 2-F-3-Br-Ph, and R X is tAm, and R Y is Cl, and R 3 is Me, and R 4 is Me. [Table 1-636] G is 2-F-3-Br-Ph, and R X is tAm, and R Y is Br, and R 3 is H, and R 4 is H. [Table 1-637] G is 2-F-3-Br-Ph, and R X is tAm, and R Y is Br, and R 3 is F, and R 4 is H. [Table 1-638] G is 2-F-3-Br-Ph, and R X is tAm, and R Y is Br, and R 3 is F, and R 4 is F. [Table 1-639] G is 2-F-3-Br-Ph, and R X is tAm, and R Y is Br, and R 3 is Me, and R 4 is H. [Table 1-640] G is 2-F-3-Br-Ph, and R X is tAm, and R Y is Br, and R 3 is Me, and R 4 is Me. [Table 1-641] G is 2-F-3-Me-Ph, and RX is tBu, and R Y is H, and R 3 is H, and R 4 is H. [Table 1-642] G is 2-F-3-Me-Ph, and R X is tBu, and R Y is H, and R 3 is F, and R 4 is H. [Table 1-643] G is 2-F-3-Me-Ph, and R X is tBu, and R Y is H, and R 3 is F, and R 4 is F. [Table 1-644] G is 2-F-3-Me-Ph, and R X is tBu, and R Y is H, and R 3 is Me, and R 4 is H. [Table 1-645] G is 2-F-3-Me-Ph, and R X is tBu, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-646] G is 2-F-3-Me-Ph, and R X is tBu, and R Y is F, and R 3 is H, and R 4 is H. [Table 1-647] G is 2-F-3-Me-Ph, and R X is tBu, and R Y is F, and R 3 is F, and R 4 is H. [Table 1-648] G is 2-F-3-Me-Ph, and R X is tBu, and R Y is F, and R 3 is F, and R4 is F. [Table 1-649] G is 2-F-3-Me-Ph, and R X is tBu, and R Y is F, and R 3 is Me, and R 4 is H. [Table 1-650] G is 2-F-3-Me-Ph, and R X is tBu, and R Y is F, and R 3 is Me, and R 4 is Me. [Table 1-651] G is 2-F-3-Me-Ph, and R X is tBu, and R Y is Cl, and R 3 is H, and R 4 is H. [Table 1-652] G is 2-F-3-Me-Ph, and R X is tBu, and R Y is Cl, and R 3 is F, and R 4 is H. [Table 1-653] G is 2-F-3-Me-Ph, and R X is tBu, and R Y is Cl, and R 3 is F, and R 4 is F. [Table 1-654] G is 2-F-3-Me-Ph, and R X is tBu, and R Y is Cl, and R 3 is Me, and R 4 is H. [Table 1-655] G is 2-F-3-Me-Ph, and R X is tBu, and R Y is Cl, and R 3 is Me, and R 4 is Me. [Table 1-656] G is 2-F-3-Me-Ph, R X is tBu, R Y is Br, R 3 is H, R 4 is H. [Table 1-657] G is 2-F-3-Me-Ph, R X is tBu, R Y is Br, R 3 is F, R 4 is H. [Table 1-658] G is 2-F-3-Me-Ph, R X is tBu, R Y is Br, R 3 is F, R 4 is F. [Table 1-659] G is 2-F-3-Me-Ph, R X is tBu, R Y is Br, R 3 is Me, R 4 is H. [Table 1-660] G is 2-F-3-Me-Ph, R X is tBu, R Y is Br, R 3 is Me, R 4 is Me. [Table 1-661] G is 2-F-3-Me-Ph, R X is tAm, R Y is H, R 3 is H, R 4 is H. [Table 1-662] G is 2-F-3-Me-Ph, R X is tAm, R Y is H, R 3 is F, R 4 is H. [Table 1-663] G is 2-F-3-Me-Ph, R X is tAm, R Yis H, R 3 is F, R 4 is F. [Table 1-664] G is 2-F-3-Me-Ph, R X is tAm, R Y is H, R 3 is Me, R 4 is H. [Table 1-665] G is 2-F-3-Me-Ph, R X is tAm, R Y is H, R 3 is Me, R 4 is Me. [Table 1-666] G is 2-F-3-Me-Ph, R X is tAm, R Y is F, R 3 is H, R 4 is H. [Table 1-667] G is 2-F-3-Me-Ph, R X is tAm, R Y is F, R 3 is F, R 4 is H. [Table 1-668] G is 2-F-3-Me-Ph, R X is tAm, R Y is F, R 3 is F, R 4 is F. [Table 1-669] G is 2-F-3-Me-Ph, R X is tAm, R Y is F, R 3 is Me, R 4 is H. [Table 1-670] G is 2-F-3-Me-Ph, R X is tAm, R Y is F, R 3 is Me, R 4 is Me. [Table 1-671] G is 2-F-3-Me-Ph, and R X is tAm, and R Y is Cl, and R 3 is H, and R 4 is H. [Table 1-672] G is 2-F-3-Me-Ph, and R X is tAm, and R Y is Cl, and R 3 is F, and R 4 is H. [Table 1-673] G is 2-F-3-Me-Ph, and R X is tAm, and R Y is Cl, and R 3 is F, and R 4 is F. [Table 1-674] G is 2-F-3-Me-Ph, and R X is tAm, and R Y is Cl, and R 3 is Me, and R 4 is H. [Table 1-675] G is 2-F-3-Me-Ph, and R X is tAm, and R Y is Cl, and R 3 is Me, and R 4 is Me. [Table 1-676] G is 2-F-3-Me-Ph, and R X is tAm, and R Y is Br, and R 3 is H, and R 4 is H. [Table 1-677] G is 2-F-3-Me-Ph, and R X is tAm, and R Y is Br, and R 3 is F, and R 4 is H. [Table 1-678] G is 2-F-3-Me-Ph, and R Xis tAm, R Y is Br, R 3 is F, R 4 is F. [Table 1-679] G is 2-F-3-Me-Ph, R X is tAm, R Y is Br, R 3 is Me, R 4 is H. [Table 1-680] G is 2-F-3-Me-Ph, R X is tAm, R Y is Br, R 3 is Me, R 4 is Me. [Table 1-681] G is 2-F-3-cPr-Ph, R X is tBu, R Y is H, R 3 is H, R 4 is H. [Table 1-682] G is 2-F-3-cPr-Ph, R X is tBu, R Y is H, R 3 is F, R 4 is H. [Table 1-683] G is 2-F-3-cPr-Ph, R X is tBu, R Y is H, R 3 is F, R 4 is F. [Table 1-684] G is 2-F-3-cPr-Ph, R X is tBu, R Y is H, R 3 is Me, R 4 is H. [Table 1-685] G is 2-F-3-cPr-Ph, R X is tBu, R Y is H, R 3 is Me, R4 It is Me. [Table 1-686] G is 2-F-3-cPr-Ph, and R X is tBu, and R Y is F, and R 3 is H, and R 4 is H. [Table 1-687] G is 2-F-3-cPr-Ph, and R X is tBu, and R Y is F, and R 3 is F, and R 4 is H. [Table 1-688] G is 2-F-3-cPr-Ph, and R X is tBu, and R Y is F, and R 3 is F, and R 4 is F. [Table 1-689] G is 2-F-3-cPr-Ph, and R X is tBu, and R Y is F, and R 3 is Me, and R 4 is H. [Table 1-690] G is 2-F-3-cPr-Ph, and R X is tBu, and R Y is F, and R 3 is Me, and R 4 is Me. [Table 1-691] G is 2-F-3-cPr-Ph, and R X is tBu, and R Y is Cl, and R 3 is H, and R 4 is H. [Table 1-692] G is 2-F-3-cPr-Ph, and R X is tBu, and R Y is Cl, and R 3 is F, and R 4 is H. [Table 1-693] G is 2-F-3-cPr-Ph, R X is tBu, R Y is Cl, R 3 is F, R 4 is F. [Table 1-694] G is 2-F-3-cPr-Ph, R X is tBu, R Y is Cl, R 3 is Me, R 4 is H. [Table 1-695] G is 2-F-3-cPr-Ph, R X is tBu, R Y is Cl, R 3 is Me, R 4 is Me. [Table 1-696] G is 2-F-3-cPr-Ph, R X is tBu, R Y is Br, R 3 is H, R 4 is H. [Table 1-697] G is 2-F-3-cPr-Ph, R X is tBu, R Y is Br, R 3 is F, R 4 is H. [Table 1-698] G is 2-F-3-cPr-Ph, R X is tBu, R Y is Br, R 3 is F, R 4 is F. [Table 1-699] G is 2-F-3-cPr-Ph, R X is tBu, R Y is Br, R 3 is Me, R 4 is H. [Table 1-700] G is 2-F-3-cPr-Ph, R X is tBu, RY is Br, and R 3 is Me, and R 4 is Me. [Table 1-701] G is 2-F-3-cPr-Ph, and R X is tAm, and R Y is H, and R 3 is H, and R 4 is H. [Table 1-702] G is 2-F-3-cPr-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is H. [Table 1-703] G is 2-F-3-cPr-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is F. [Table 1-704] G is 2-F-3-cPr-Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is H. [Table 1-705] G is 2-F-3-cPr-Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-706] G is 2-F-3-cPr-Ph, and R X is tAm, and R Y is F, and R 3 is H, and R 4 is H. [Table 1-707] G is 2-F-3-cPr-Ph, and R X is tAm, and R Y is F, and R 3 is F, and R 4It is H. [Table 1-708] G is 2-F-3-cPr-Ph, and R X is tAm, and R Y is F, and R 3 is F, and R 4 is F. [Table 1-709] G is 2-F-3-cPr-Ph, and R X is tAm, and R Y is F, and R 3 is Me, and R 4 is H. [Table 1-710] G is 2-F-3-cPr-Ph, and R X is tAm, and R Y is F, and R 3 is Me, and R 4 is Me. [Table 1-711] G is 2-F-3-cPr-Ph, and R X is tAm, and R Y is Cl, and R 3 is H, and R 4 is H. [Table 1-712] G is 2-F-3-cPr-Ph, and R X is tAm, and R Y is Cl, and R 3 is F, and R 4 is H. [Table 1-713] G is 2-F-3-cPr-Ph, and R X is tAm, and R Y is Cl, and R 3 is F, and R 4 is F. [Table 1-714] G is 2-F-3-cPr-Ph, and R X is tAm, and R Y is Cl, and R 3 is Me, and R 4 is H. [Table 1-715] G is 2-F-3-cPr-Ph, and R X is tAm, and R Y is Cl, and R 3 is Me, and R 4 is Me. [Table 1-716] G is 2-F-3-cPr-Ph, and R X is tAm, and R Y is Br, and R 3 is H, and R 4 is H. [Table 1-717] G is 2-F-3-cPr-Ph, and R X is tAm, and R Y is Br, and R 3 is F, and R 4 is H. [Table 1-718] G is 2-F-3-cPr-Ph, and R X is tAm, and R Y is Br, and R 3 is F, and R 4 is F. [Table 1-719] G is 2-F-3-cPr-Ph, and R X is tAm, and R Y is Br, and R 3 is Me, and R 4 is H. [Table 1-720] G is 2-F-3-cPr-Ph, and R X is tAm, and R Y is Br, and R 3 is Me, and R 4 is Me. [Table 1-721] G is 2-F-3-CF3-Ph, and R X is tBu, and R Y is H, and R 3 is H, and R 4 is H. [Table 1-722] G is 2-F-3-CF3-Ph, and R X is tBu, and RY is H, and R 3 is F, and R 4 is H. [Table 1-723] G is 2-F-3-CF3-Ph, and R X is tBu, and R Y is H, and R 3 is F, and R 4 is F. [Table 1-724] G is 2-F-3-CF3-Ph, and R X is tBu, and R Y is H, and R 3 is Me, and R 4 is H. [Table 1-725] G is 2-F-3-CF3-Ph, and R X is tBu, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-726] G is 2-F-3-CF3-Ph, and R X is tBu, and R Y is F, and R 3 is H, and R 4 is H. [Table 1-727] G is 2-F-3-CF3-Ph, and R X is tBu, and R Y is F, and R 3 is F, and R 4 is H. [Table 1-728] G is 2-F-3-CF3-Ph, and R X is tBu, and R Y is F, and R 3 is F, and R 4 is F. [Table 1-729] G is 2-F-3-CF3-Ph, and R X is tBu, and R Y is F, and R 3 is Me, and R 4It is H. [Table 1-730] G is 2-F-3-CF3-Ph, and R X is tBu, and R Y is F, and R 3 is Me, and R 4 is Me. [Table 1-731] G is 2-F-3-CF3-Ph, and R X is tBu, and R Y is Cl, and R 3 is H, and R 4 is H. [Table 1-732] G is 2-F-3-CF3-Ph, and R X is tBu, and R Y is Cl, and R 3 is F, and R 4 is H. [Table 1-733] G is 2-F-3-CF3-Ph, and R X is tBu, and R Y is Cl, and R 3 is F, and R 4 is F. [Table 1-734] G is 2-F-3-CF3-Ph, and R X is tBu, and R Y is Cl, and R 3 is Me, and R 4 is H. [Table 1-735] G is 2-F-3-CF3-Ph, and R X is tBu, and R Y is Cl, and R 3 is Me, and R 4 is Me. [Table 1-736] G is 2-F-3-CF3-Ph, and R X is tBu, and R Y is Br, and R 3 is H, and R 4 is H. [Table 1-737] G is 2-F-3-CF3-Ph, and R X is tBu, and R Y is Br, and R 3 is F, and R 4 is H. [Table 1-738] G is 2-F-3-CF3-Ph, and R X is tBu, and R Y is Br, and R 3 is F, and R 4 is F. [Table 1-739] G is 2-F-3-CF3-Ph, and R X is tBu, and R Y is Br, and R 3 is Me, and R 4 is H. [Table 1-740] G is 2-F-3-CF3-Ph, and R X is tBu, and R Y is Br, and R 3 is Me, and R 4 is Me. [Table 1-741] G is 2-F-3-CF3-Ph, and R X is tAm, and R Y is H, and R 3 is H, and R 4 is H. [Table 1-742] G is 2-F-3-CF3-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is H. [Table 1-743] G is 2-F-3-CF3-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is F. [Table 1-744] G is 2-F-3-CF3-Ph, and R X is tAm, and RY is H, and R 3 is Me, and R 4 is H. [Table 1-745] G is 2-F-3-CF3-Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-746] G is 2-F-3-CF3-Ph, and R X is tAm, and R Y is F, and R 3 is H, and R 4 is H. [Table 1-747] G is 2-F-3-CF3-Ph, and R X is tAm, and R Y is F, and R 3 is F, and R 4 is H. [Table 1-748] G is 2-F-3-CF3-Ph, and R X is tAm, and R Y is F, and R 3 is F, and R 4 is F. [Table 1-749] G is 2-F-3-CF3-Ph, and R X is tAm, and R Y is F, and R 3 is Me, and R 4 is H. [Table 1-750] G is 2-F-3-CF3-Ph, and R X is tAm, and R Y is F, and R 3 is Me, and R 4 is Me. [Table 1-751] G is 2-F-3-CF3-Ph, and R X is tAm, and R Y is Cl, and R 3 is H, and R 4It is H. [Table 1-752] G is 2-F-3-CF3-Ph, and R X is tAm, and R Y is Cl, and R 3 is F, and R 4 is H. [Table 1-753] G is 2-F-3-CF3-Ph, and R X is tAm, and R Y is Cl, and R 3 is F, and R 4 is F. [Table 1-754] G is 2-F-3-CF3-Ph, and R X is tAm, and R Y is Cl, and R 3 is Me, and R 4 is H. [Table 1-755] G is 2-F-3-CF3-Ph, and R X is tAm, and R Y is Cl, and R 3 is Me, and R 4 is Me. [Table 1-756] G is 2-F-3-CF3-Ph, and R X is tAm, and R Y is Br, and R 3 is H, and R 4 is H. [Table 1-757] G is 2-F-3-CF3-Ph, and R X is tAm, and R Y is Br, and R 3 is F, and R 4 is H. [Table 1-758] G is 2-F-3-CF3-Ph, and R X is tAm, and R Y is Br, and R 3 is F, and R 4 is F. [Table 1-759] G is 2-F-3-CF3-Ph, and R X is tAm, and R Y is Br, and R 3 is Me, and R 4 is H. [Table 1-760] G is 2-F-3-CF3-Ph, and R X is tAm, and R Y is Br, and R 3 is Me, and R 4 is Me. [Table 1-761] G is 2-F-3-OMe-Ph, and R X is tBu, and R Y is H, and R 3 is H, and R 4 is H. [Table 1-762] G is 2-F-3-OMe-Ph, and R X is tBu, and R Y is H, and R 3 is F, and R 4 is H. [Table 1-763] G is 2-F-3-OMe-Ph, and R X is tBu, and R Y is H, and R 3 is F, and R 4 is F. [Table 1-764] G is 2-F-3-OMe-Ph, and R X is tBu, and R Y is H, and R 3 is Me, and R 4 is H. [Table 1-765] G is 2-F-3-OMe-Ph, and R X is tBu, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-766] G is 2-F-3-OMe-Ph, and R X is tBu, and RY is F, R 3 is H, R 4 is H. [Table 1-767] G is 2-F-3-OMe-Ph, R X is tBu, R Y is F, R 3 is F, R 4 is H. [Table 1-768] G is 2-F-3-OMe-Ph, R X is tBu, R Y is F, R 3 is F, R 4 is F. [Table 1-769] G is 2-F-3-OMe-Ph, R X is tBu, R Y is F, R 3 is Me, R 4 is H. [Table 1-770] G is 2-F-3-OMe-Ph, R X is tBu, R Y is F, R 3 is Me, R 4 is Me. [Table 1-771] G is 2-F-3-OMe-Ph, R X is tBu, R Y is Cl, R 3 is H, R 4 is H. [Table 1-772] G is 2-F-3-OMe-Ph, R X is tBu, R Y is Cl, R 3 is F, R 4 is H. [Table 1-773] G is 2-F-3-OMe-Ph, R X is tBu, R Y is Cl, R 3 is F, R 4It is F. [Table 1-774] G is 2-F-3-OMe-Ph, and R X is tBu, and R Y is Cl, and R 3 is Me, and R 4 is H. [Table 1-775] G is 2-F-3-OMe-Ph, and R X is tBu, and R Y is Cl, and R 3 is Me, and R 4 is Me. [Table 1-776] G is 2-F-3-OMe-Ph, and R X is tBu, and R Y is Br, and R 3 is H, and R 4 is H. [Table 1-777] G is 2-F-3-OMe-Ph, and R X is tBu, and R Y is Br, and R 3 is F, and R 4 is H. [Table 1-778] G is 2-F-3-OMe-Ph, and R X is tBu, and R Y is Br, and R 3 is F, and R 4 is F. [Table 1-779] G is 2-F-3-OMe-Ph, and R X is tBu, and R Y is Br, and R 3 is Me, and R 4 is H. [Table 1-780] G is 2-F-3-OMe-Ph, and R X is tBu, and R Y is Br, and R 3 is Me, and R 4 is Me. [Table 1-781] G is 2-F-3-OMe-Ph, and R X is tAm, and R Y is H, and R 3 is H, and R 4 is H. [Table 1-782] G is 2-F-3-OMe-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is H. [Table 1-783] G is 2-F-3-OMe-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is F. [Table 1-784] G is 2-F-3-OMe-Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is H. [Table 1-785] G is 2-F-3-OMe-Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-786] G is 2-F-3-OMe-Ph, and R X is tAm, and R Y is F, and R 3 is H, and R 4 is H. [Table 1-787] G is 2-F-3-OMe-Ph, and R X is tAm, and R Y is F, and R 3 is F, and R 4 is H. [Table 1-788] G is 2-F-3-OMe-Ph, and R X is tAm, and R Yis F, R 3 is F, R 4 is F. [Table 1-789] G is 2-F-3-OMe-Ph, R X is tAm, R Y is F, R 3 is Me, R 4 is H. [Table 1-790] G is 2-F-3-OMe-Ph, R X is tAm, R Y is F, R 3 is Me, R 4 is Me. [Table 1-791] G is 2-F-3-OMe-Ph, R X is tAm, R Y is Cl, R 3 is H, R 4 is H. [Table 1-792] G is 2-F-3-OMe-Ph, R X is tAm, R Y is Cl, R 3 is F, R 4 is H. [Table 1-793] G is 2-F-3-OMe-Ph, R X is tAm, R Y is Cl, R 3 is F, R 4 is F. [Table 1-794] G is 2-F-3-OMe-Ph, R X is tAm, R Y is Cl, R 3 is Me, R 4 is H. [Table 1-795] G is 2-F-3-OMe-Ph, R X is tAm, R Y is Cl, R 3 is Me, R 4It is me. [Table 1-796] G is 2-F-3-OMe-Ph, and R X is tAm, and R Y is Br, and R 3 is H, and R 4 is H. [Table 1-797] G is 2-F-3-OMe-Ph, and R X is tAm, and R Y is Br, and R 3 is F, and R 4 is H. [Table 1-798] G is 2-F-3-OMe-Ph, and R X is tAm, and R Y is Br, and R 3 is F, and R 4 is F. [Table 1-799] G is 2-F-3-OMe-Ph, and R X is tAm, and R Y is Br, and R 3 is Me, and R 4 is H. [Table 1-800] G is 2-F-3-OMe-Ph, and R X is tAm, and R Y is Br, and R 3 is Me, and R 4 is Me. [Table 1-801] G is 2-F-3-OCF3-Ph, and R X is tBu, and R Y is H, and R 3 is H, and R 4 is H. [Table 1-802] G is 2-F-3-OCF3-Ph, and R X is tBu, and R Y is H, and R 3 is F, and R 4 is H. [Table 1-803] G is 2-F-3-OCF3-Ph, R X is tBu, R Y is H, R 3 is F, R 4 is F. [Table 1-804] G is 2-F-3-OCF3-Ph, R X is tBu, R Y is H, R 3 is Me, R 4 is H. [Table 1-805] G is 2-F-3-OCF3-Ph, R X is tBu, R Y is H, R 3 is Me, R 4 is Me. [Table 1-806] G is 2-F-3-OCF3-Ph, R X is tBu, R Y is F, R 3 is H, R 4 is H. [Table 1-807] G is 2-F-3-OCF3-Ph, R X is tBu, R Y is F, R 3 is F, R 4 is H. [Table 1-808] G is 2-F-3-OCF3-Ph, R X is tBu, R Y is F, R 3 is F, R 4 is F. [Table 1-809] G is 2-F-3-OCF3-Ph, R X is tBu, R Y is F, R 3 is Me, R 4 is H. [Table 1-810] G is 2-F-3-OCF3-Ph, R X is tBu, RY is F, and R 3 is Me, and R 4 is Me. [Table 1-811] G is 2-F-3-OCF3-Ph, and R X is tBu, and R Y is Cl, and R 3 is H, and R 4 is H. [Table 1-812] G is 2-F-3-OCF3-Ph, and R X is tBu, and R Y is Cl, and R 3 is F, and R 4 is H. [Table 1-813] G is 2-F-3-OCF3-Ph, and R X is tBu, and R Y is Cl, and R 3 is F, and R 4 is F. [Table 1-814] G is 2-F-3-OCF3-Ph, and R X is tBu, and R Y is Cl, and R 3 is Me, and R 4 is H. [Table 1-815] G is 2-F-3-OCF3-Ph, and R X is tBu, and R Y is Cl, and R 3 is Me, and R 4 is Me. [Table 1-816] G is 2-F-3-OCF3-Ph, and R X is tBu, and R Y is Br, and R 3 is H, and R 4 is H. [Table 1-817] G is 2-F-3-OCF3-Ph, and R X is tBu, and R Y is Br, and R 3is F, and R 4 is H. [Table 1-818] G is 2-F-3-OCF3-Ph, and R X is tBu, and R Y is Br, and R 3 is F, and R 4 is F. [Table 1-819] G is 2-F-3-OCF3-Ph, and R X is tBu, and R Y is Br, and R 3 is Me, and R 4 is H. [Table 1-820] G is 2-F-3-OCF3-Ph, and R X is tBu, and R Y is Br, and R 3 is Me, and R 4 is Me. [Table 1-821] G is 2-F-3-OCF3-Ph, and R X is tAm, and R Y is H, and R 3 is H, and R 4 is H. [Table 1-822] G is 2-F-3-OCF3-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is H. [Table 1-823] G is 2-F-3-OCF3-Ph, and R X is tAm, and R Y is H, and R 3 is F, and R 4 is F. [Table 1-824] G is 2-F-3-OCF3-Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is H. [Table 1-825] G is 2-F-3-OCF3-Ph, and R X is tAm, and R Y is H, and R 3 is Me, and R 4 is Me. [Table 1-826] G is 2-F-3-OCF3-Ph, and R X is tAm, and R Y is F, and R 3 is H, and R 4 is H. [Table 1-827] G is 2-F-3-OCF3-Ph, and R X is tAm, and R Y is F, and R 3 is F, and R 4 is H. [Table 1-828] G is 2-F-3-OCF3-Ph, and R X is tAm, and R Y is F, and R 3 is F, and R 4 is F. [Table 1-829] G is 2-F-3-OCF3-Ph, and R X is tAm, and R Y is F, and R 3 is Me, and R 4 is H. [Table 1-830] G is 2-F-3-OCF3-Ph, and R X is tAm, and R Y is F, and R 3 is Me, and R 4 is Me. [Table 1-831] G is 2-F-3-OCF3-Ph, and R X is tAm, and R Y is Cl, and R 3 is H, and R 4 is H. [Table 1-832] G is 2-F-3-OCF3-Ph, and RX is tAm, R Y is Cl, R 3 is F, R 4 is H. [Table 1-833] G is 2-F-3-OCF3-Ph, R X is tAm, R Y is Cl, R 3 is F, R 4 is F. [Table 1-834] G is 2-F-3-OCF3-Ph, R X is tAm, R Y is Cl, R 3 is Me, R 4 is H. [Table 1-835] G is 2-F-3-OCF3-Ph, R X is tAm, R Y is Cl, R 3 is Me, R 4 is Me. [Table 1-836] G is 2-F-3-OCF3-Ph, R X is tAm, R Y is Br, R 3 is H, R 4 is H. [Table 1-837] G is 2-F-3-OCF3-Ph, R X is tAm, R Y is Br, R 3 is F, R 4 is H. [Table 1-838] G is 2-F-3-OCF3-Ph, R X is tAm, R Y is Br, R 3 is F, R 4 is F. [Table 1-839] G is 2-F-3-OCF3-Ph, R X is tAm, R Yis Br, and R 3 is Me, and R 4 is H. [Table 1-840] G is 2-F-3-OCF3-Ph, and R X is tAm, and R Y is Br, and R 3 is Me, and R 4 is Me.
[0196] The compounds of the present invention can generally be used as fungicides and bactericides for agricultural and horticultural purposes against various diseases caused by powdery mildews, oomycetes, zygomycetes, ascomycetes, basidiomycetes, imperfect fungi, bacteria or viruses.
[0197] "Pathogenic bacteria" means microorganisms that cause plant diseases. Specifically, the following microorganisms are included, but not limited to these. Taphrina spp. (e.g., Taphrina deformans, T. pruni, etc.), Pneumocystis spp., Geotrichum spp., Candida spp. (e.g., Candida albicans, C. sorbosa, etc.), Pichia spp. (e.g., Pichia kluyveri, etc.), Capnodium spp., Fumago spp., Hypocapnodium spp., Cercospora spp. (e.g., Cercospora apii, C. asparagi, C. beticola, C. capsici, C. carotae, C. kaki, C. kikuchii, C. zonata, etc.), Cercosporidium spp., Cladosporium spp. (e.g., Cladosporium colocasiae, C. cucumerinum, C. variabile, etc.), Davidiella spp., Didymosporium spp., Heterosporium spp. (e.g., Heterosporium allii, etc.), Mycosphaerella spp. (e.g., Mycosphaerella arachidis, M. berkeleyi, M. cerasella, M. fijiensis, M. fragariae, M. graminicola, M. nawae, M. pinodes, M. pomi, M. zingiberis, etc.), Mycovellosiella spp. (e.g., Mycovellosiella fulva, M. nattrassii, etc.), Paracercospora spp. (e.g., Paracercospora egenula, etc.), Phaeoisariopsis spp., Phaeoramularia spp., Pseudocercospora spp. (e.g., Pseudocercospora abelmoschi, P. fuligena, P. vitis, etc.), Pseudocercosporella spp. (e.g., Pseudocercosporella capsellae, etc.), Ramichloridium spp., Ramularia spp., Septogloeum spp., Septoria spp. (e.g., Septoria albopunctata, S. apiicola, S. chrysanthemella, S. helianthi, S. obesa, etc.), Sphaerulina spp., Aureobasidium spp., Kabatiella spp., Plowrightia spp., Stigmina spp., Elsinoe spp. (e.g., Elsinoe ampelina, E. araliae, E. fawcettii, etc.), Sphaceloma spp. (e.g., Sphaceloma caricae, etc.), Ascochyta spp. (e.g., Ascochyta pisi, etc.), Corynespora spp. (e.g., Corynespora cassiicola, etc.), Leptosphaeria spp. (e.g., Leptosphaeria coniothyrium, L. maculans, etc.), Saccharicola spp., Phaeosphaeria spp. (e.g., Phaeosphaeria nodorum, etc.), Ophiosphaerella spp., Setophoma spp., Helminthosporium spp., Alternaria spp. (e.g., Alternaria alternata, A. brassicae, A. brassicicola, A. citri, A. dauci, A. helianthi, A. japonica, A. kikuchiana, A. mali, A. panax, A. porri, A. radicina, A. solani, etc.), Bipolaris spp. (e.g., Bipolaris sorghicola, etc.), Cochliobolus spp. (e.g., Cochliobolus heterostrophus, C. lunatus, C. miyabeanus, etc.), Curvularia spp. (e.g., Curvularia geniculata, C. verruculosa, etc.), Drechslera spp., Pleospora spp. (e.g., Pleospora herbarum, etc.), Pyrenophora spp.(e.g., Pyrenophora graminea, P. teres, etc.), Setosphaeria spp. (e.g., Setosphaeria turcica, etc.), Stemphylium spp. (e.g., Stemphylium botryosum, S. lycopersici, S. solani, S. vesicarium, etc.), Fusicladium spp., Venturia spp. (e.g., Venturia carpophila, V. Inaequalis, V. nashicola, V. pirina, etc.), Didymella spp. (e.g., Didymella bryoniae, D. fabae, etc.), Hendersonia spp., Phoma spp. (e.g., Phoma erratica var. mikan, P. exigua var. exigua, P. wasabiae, etc.), Pyrenochaeta spp. (e.g., Pyrenochaeta lycopersici, etc.), Stagonospora spp. (e.g., Stagonospora sacchari, etc.), Botryosphaeria spp. (e.g., Botryosphaeria berengeriana f. sp. piricola, B. dothidea, etc.), Dothiorella spp., Fusicoccum spp., Guignardia spp., Lasiodiplodia spp. (e.g., Lasiodiplodia theobromae, etc.), Macrophoma spp., Macrophomina spp., Neofusicoccum spp., Phyllosticta spp. (e.g., Phyllosticta zingiberis, etc.), Schizothyrium spp. (e.g., Schizothyrium pomi, etc.), Acrospermum spp., Leptosphaerulina spp., Aspergillus spp., Penicillium spp. (e.g., Penicillium digitatum, P. italicum, P. sclerotigenum, etc.), Microsporum spp., Trichophyton spp.(e.g., Trichophyton mentagrophytes, T. rubrum, etc.), Histoplasma spp., Blumeria spp. (e.g., Blumeria graminis f. sp. hordei, B. g. f. sp. tritici, etc.), Erysiphe spp. (e.g., Erysiphe betae, E. cichoracearum, E. c. var. cichoracearum, E. heraclei, E. pisi, etc.), Golovinomyces spp. (e.g., Golovinomyces cichoracearum var. latisporus, etc.), Leveillula spp. (e.g., Leveillula taurica, etc.), Microsphaera spp., Oidium spp. (e.g., Oidium neolycopersici, etc.), Phyllactinia spp. (e.g., Phyllactinia kakicola, P. mali, P. moricola, etc.), Podosphaera spp. (e.g., Podosphaera fusca, P. leucotricha, P. pannosa, P. tridactyla var. tridactyla, P. xanthii, etc.), Sphaerotheca spp. (e.g., Sphaerotheca aphanis var. aphanis, S. fuliginea, etc.), Uncinula spp. (e.g., Uncinula necator, U. n. var. necator, etc.), Uncinuliella spp. (e.g., Uncinuliella simulans var. simulans, U. s. var. tandae, etc.), Blumeriella spp. (e.g., Blumeriella jaapii, etc.), Cylindrosporium spp., Diplocarpon spp. (e.g., Diplocarpon mali, D. mespili, D. rosae, etc.), Gloeosporium spp. (e.g., Gloeosporium minus, etc.), Marssonina spp., Tapesia spp. (e.g., Tapesia acuformis, T.yallundae, etc., Lachnum spp., Scleromitrula spp., Botryotinia spp. (e.g., Botryotinia fuckeliana, etc.), Botrytis spp. (e.g., Botrytis allii, B. byssoidea, B. cinerea, B. elliptica, B. fabae, B. squamosa, etc.), Ciborinia spp., Grovesinia spp., Monilia mumecola, Monilinia spp. (e.g., Monilinia fructicola, M. fructigena, M. laxa, M. mali, M. vaccinii-corymbosi, etc.), Sclerotinia spp. (e.g., Sclerotinia borealis, S. homoeocarpa, S. minor, S. sclerotiorum, etc.), Valdensia spp. (e.g., Valdensia heterodoxa, etc.), Claviceps spp. (e.g., Claviceps sorghi, C. sorghicola, etc.), Epichloe spp., Ephelis japonica, Villosiclava virens, Hypomyces spp. (e.g., Hypomyces solani f. sp. mori, H. s. f. sp. pisi, etc.), Trichoderma spp. (e.g., Trichoderma viride, etc.), Calonectria spp. (e.g., Calonectria ilicicola, etc.), Candelospora spp., Cylindrocarpon spp., Cylindrocladium spp., Fusarium spp. (e.g., Fusarium arthrosporioides, F. crookwellense, F. culmorum, F. cuneirostrum, F. oxysporum, F. o. f. sp. adzukicola, F. o. f. sp. allii, F. o. f. sp. asparagi, F. o. f. sp. batatas, F. o. f. sp. cepae, F. o. f. sp.Colocasiae, F. o. f. sp. conglutinans, F. o. f. sp. cubense, F. o. f. sp. cucumerinum, F. o. f. sp. fabae, F. o. f. sp. fragariae, F. o. f. sp. lactucae, F. o. f. sp. lagenariae, F. o. f. sp. lycopersici, F. o. f. sp. melongenae, F. o. f. sp. melonis, F. o. f. sp. nelumbinicola, F. o. f. sp. niveum, F. o. f. sp. radicis-lycopersici, F. o. f. sp. raphani, F. o. f. sp. spinaciae, F. sporotrichioides, F. solani, F. s. f. sp. cucurbitae, F. s. f. sp. eumartii, F. s. f. sp. glycines, F. s. f. sp. pisi, F. s. f. sp. Radicicola, F. virguliforme, etc.), Gibberella spp. (e.g., Gibberella avenacea, G. baccata, G. fujikuroi, G. zeae, etc.), Haematonectria spp., Nectria spp., Ophionectria spp., Caldariomyces spp., Myrothecium spp., Trichothecium spp., Verticillium spp. (e.g., Verticillium albo-atrum, V. dahliae, V. longisporum, etc.), Ceratocystis spp. (e.g., Ceratocystis ficicola, C. fimbriata, etc.), Thielaviopsis spp. (e.g., Thielaviopsis basicola, etc.), Adisciso spp., Monochaetia spp., Pestalotia spp. (e.g., Pestalotia eriobotrifolia, etc.), Pestalotiopsis spp.(e.g., Pestalotiopsis funerea, P. longiseta, P. neglecta, P. theae, etc.), Physalospora spp., Nemania spp., Nodulisporium spp., Rosellinia spp. (e.g., Rosellinia necatrix, etc.), Monographella spp. (e.g., Monographella nivalis, etc.), Ophiostoma spp., Cryphonectria spp. (e.g., Cryphonectria parasitica, etc.), Diaporthe spp. (e.g., Diaporthe citri, D. kyushuensis, D. nomurai, D. tanakae, etc.), Diaporthopsis spp., Phomopsis spp. (e.g., Phomopsis asparagi, P. fukushii, P. obscurans, P. vexans, etc.), Cryptosporella spp., Discula spp. (e.g., Discula theae-sinensis, etc.), Gnomonia spp., Coniella spp., Coryneum spp., Greeneria spp., Melanconis spp., Cytospora spp., Leucostoma spp., Valsa spp. (e.g., Valsa ceratosperma, etc.), Tubakia spp., Monosporascus spp., Clasterosporium spp., Gaeumannomyces spp. (e.g., Gaeumannomyces graminis, etc.), Magnaporthe spp. (e.g., Magnaporthe grisea, etc.), Pyricularia spp. (e.g., Pyricularia zingiberis, etc.), Monilochaetes infuscans, Colletotrichum spp. (e.g., Colletotrichum acutatum, C. capsici, C. cereale, C. destructivum, C. fragariae, C. lindemuthianum, C. nigrum, C. orbiculare, C.Fungi of the phylum Ascomycota such as Spinaciae (e.g., Spinacia oleracea), Glomerella spp. (e.g., Glomerella cingulata), Khuskia oryzae, Phyllachora spp. (e.g., Phyllachora pomigena), Ellisembia spp., Briosia spp., Cephalosporium spp. (e.g., Cephalosporium gramineum), Epicoccum spp., Gloeocercospora sorghi, Mycocentrospora spp., Peltaster spp. (e.g., Peltaster fructicola), Phaeocytostroma spp., Phialophora spp. (e.g., Phialophora gregata), Pseudophloeosporella dioscoreae, Pseudoseptoria spp., Rhynchosporium spp. (e.g., Rhynchosporium secalis), Sarocladium spp., Coleophoma spp., Helicoceras oryzae, etc. Septobasidium spp. (e.g., Septobasidium bogoriense, S. tanakae), Helicobasidium spp. (e.g., Helicobasidium longisporum), Coleosporium spp. (e.g., Coleosporium plectranthi), Cronartium spp., Phakopsora spp. (e.g., Phakopsora artemisiae, P. nishidana, P. pachyrhizi), Physopella spp. (e.g., Physopella ampelopsidis), Kuehneola spp. (e.g., Kuehneola japonica), Phragmidium spp. (e.g., Phragmidium fusiforme, P. mucronatum, P. rosae - multiflorae), Gymnosporangium spp.(e.g., Gymnosporangium asiaticum, G. yamadae, etc.), Puccinia spp. (e.g., Puccinia allii, P. brachypodii var. poae-nemoralis, P. coronata, P. c. var. coronata, P. cynodontis, P. graminis, P. g. subsp. graminicola, P. hordei, P. horiana, P. kuehnii, P. melanocephala, P. recondita, P. striiformis var. striiformis, P. tanaceti var. tanaceti, P. tokyensis, P. zoysiae, etc.), Uromyces spp. (e.g., Uromyces phaseoli var. azukicola, U. p. var. phaseoli, Uromyces viciae-fabae var. viciae-fabae, etc.), Naohidemyces vaccinii, Nyssopsora spp., Leucotelium spp., Tranzschelia spp. (e.g., Tranzschelia discolor, etc.), Aecidium spp., Blastospora spp. (e.g., Blastospora smilacis, etc.), Uredo spp., Sphacelotheca spp., Urocystis spp., Sporisorium spp. (e.g., Sporisorium scitamineum, etc.), Ustilago spp. (e.g., Ustilago maydis, U. nuda, etc.), Entyloma spp., Exobasidium spp. (e.g., Exobasidium reticulatum, E. vexans, etc.), Microstroma spp., Tilletia spp. (e.g., Tilletia caries, T. controversa, T. laevis, etc.), Itersonilia spp. (e.g., Itersonilia perplexans, etc.), Cryptococcus spp., Bovista spp.(e.g., Bovista dermoxantha, etc.), Lycoperdon spp. (e.g., Lycoperdon curtisii, L. perlatum, etc.), Conocybe spp. (e.g., Conocybe apala, etc.), Marasmius spp. (e.g., Marasmius oreades, etc.), Armillaria spp., Helotium spp., Lepista spp. (e.g., Lepista subnuda, etc.), Sclerotium. Fungi of the phylum Basidiomycota such as spp. (e.g., Sclerotium cepivorum, etc.), Typhula spp. (e.g., Typhula incarnata, T. ishikariensis var. ishikariensis, etc.), Athelia spp. (e.g., Athelia rolfsii, etc.), Ceratobasidium spp. (e.g., Ceratobasidium cornigerum, etc.), Ceratorhiza spp., Rhizoctonia spp. (e.g., Rhizoctonia solani, etc.), Thanatephorus spp. (e.g., Thanatephorus cucumeris, etc.), Laetisaria spp., Waitea spp., Fomitiporia spp., Ganoderma spp., Chondrostereum purpureum, Phanerochaete spp., etc. Fungi of the phylum Chitridiomycota such as Olpidium spp. Fungi of the phylum Blastocladiomycota such as Physoderma spp. Fungi of the subphylum Mucoromycotina such as Choanephora spp., Choanephoroidea cucurbitae, Mucor spp. (e.g., Mucor fragilis, etc.), Rhizopus spp. (e.g., Rhizopus arrhizus, R. chinensis, R. oryzae, R. stolonifer var. stolonifer, etc.). Protists of the phylum Cercozoa such as Plasmodiophora spp. (e.g., Plasmodiophora brassicae, etc.), Spongospora subterranea f. sp. Subterranea. Oomycetes such as Aphanomyces spp. (e.g., Aphanomyces cochlioides, A. raphani, etc.), Albugo spp. (e.g., Albugo macrospora, A. wasabiae, etc.), Bremia spp. (e.g., Bremia lactucae, etc.), Hyaloperonospora spp., Peronosclerospora spp., Peronospora spp. (e.g., Peronospora alliariae - wasabi, P. chrysanthemi - coronarii, P. destructor, P. farinosa f. sp. spinaciae, P. manshurica, P. parasitica, P. sparsa, etc.), Plasmopara spp. (e.g., Plasmopara halstedii, P. nivea, P. viticola, etc.), Pseudoperonospora spp. (e.g., Pseudoperonospora cubensis, etc.), Sclerophthora spp., Phytophthora spp. (e.g., Phytophthora cactorum, P. capsici, P. citricola, P. citrophthora, P. cryptogea, P. fragariae, P. infestans, P. melonis, P. nicotianae, P. palmivora, P. porri, P. sojae, P. syringae, P. vignae f. sp. adzukicola, etc.), Pythium spp. (e.g., Pythium afertile, P. aphanidermatum, P. apleroticum, P. aristosporum, P. arrhenomanes, P. buismaniae, P. debaryanum, P. graminicola, P. horinouchiense, P. irregulare, P. iwayamai, P. myriotylum, P. okanoganense, P. paddicum, P. paroecandrum, P. periplocum, P. spinosum, P. sulcatum, P. sylvaticum, P. ultimum var. ultimum, P. vanterpoolii, P. vexans, P. volutum, etc.), etc., oomycetes of the Heterokontophyta. Clavibacter spp. (e.g., Clavibacter michiganensis subsp.Gram-positive bacteria of the phylum Actinobacteria such as *michiganensis*, Curtobacterium spp., Leifsonia spp. (e.g., *Leifsonia xyli subsp. xyli*), Streptomyces spp. (e.g., *Streptomyces ipomoeae*). Gram-positive bacteria of the phylum Firmicutes such as Clostridium sp. Gram-positive bacteria of the phylum Tenericutes such as Phytoplasma. Rhizobium spp. (e.g., *Rhizobium radiobacter*), Acetobacter spp., Burkholderia spp. (e.g., *Burkholderia andropogonis*, B. cepacia, B. gladioli, B. glumae, B. plantarii), Acidovorax spp. (e.g., *Acidovorax avenae subsp. avenae*, A. a. subsp. citrulli, A. konjaci), Herbaspirillum spp., Ralstonia spp. (e.g., *Ralstonia solanacearum*), Xanthomonas spp. (e.g., *Xanthomonas albilineans*, X. arboricola pv. pruni, X. axonopodis pv. vitians, X. campestris pv. campestris, X. c. pv. cucurbitae, X. c. pv. glycines, X. c. pv. mangiferaeindicae, X. c. pv. nigromaculans, X. c. pv. vesicatoria, X. citri subsp. citri, X. oryzae pv. oryzae), Pseudomonas spp. (e.g., *Pseudomonas cichorii*, P. fluorescens, P. marginalis, P. m. pv. marginalis, P. savastanoi pv. glycinea, P. syringae, P. s. pv. actinidiae, P. s. pv.Gram-negative bacteria of the phylum Proteobacteria such as eriobotryae, P. s. pv. helianthi, P. s. pv. lachrymans, P. s. pv. maculicola, P. s. pv. mori, P. s. pv. morsprunorum, P. s. pv. spinaciae, P. s. pv. syringae, P. s. pv. theae, P. viridiflava, etc., Rhizobacter spp., Brenneria spp. (e.g., Brenneria nigrifluens, etc.), Dickeya spp. (e.g., Dickeya dianthicola, D. zeae, etc.), Erwinia spp. (e.g., Erwinia amylovora, E. rhapontici, etc.), Pantoea spp., Pectobacterium spp. (e.g., Pectobacterium atrosepticum, P. carotovorum, P. wasabiae, etc.).
[0198] Specific examples of plant diseases caused by the infection and growth of these pathogens include, but are not limited to, the following plant diseases. Peach leaf curl (Taphrina deformans), Plum pockets (Taphrina pruni), Asparagus leaf spot (Cercospora asparagi), Sugar beet leaf spot (Cercospora beticola), Pepper frogeye leaf spot (Cercospora capsici), Persimmon angular leaf spot (Cercospora kaki), Soybean purple stain (Cercospora kikuchii), Peanut brown leaf spot (Mycosphaerella arachidis), Cherry cylindrosporium leaf spot (Mycosphaerella cerasella, Blumeriella jaapii), Black sigatoka (Mycosphaerella fijiensis), Yellow sigatoka (Mycosphaerell musicola), Wheat speckled leaf blotch (Mycosphaerella graminicola), Persimmon circular leaf spot (Mycosphaerella nawae), Pea mycosphaerella blight (Mycosphaerella pinodes), Ginger leaf spot (Mycosphaerella zingiberis), Tomato leaf mold (Mycovellosiella fulva), Eggplant leaf mold (Mycovellosiella nattrassii), Tomato cercospora leaf mold (Pseudocercospora fuligena), Grape isariopsis leaf spot (Pseudocercospora vitis), Chinese cabbage leaf spot (Pseudocercosporella capsellae), Chrysanthemum leaf spot (Septoriachrysanthemella), Chrysanthemum leaf blight (Septoria obesa), Grape anthracnose (Elsinoe ampelina), Aralia spot anthracnose (Elsinoe araliae), Citrus scab (Elsinoe fawcettii), Pea leaf spot (Ascochyta pisi), Cucumber Corynespora leaf spot (Corynespora cassiicola), Rose stem canker (Leptosphaeria coniothyrium), Wheat glume blotch (Leptosphaeria nodorum), Rose leaf spot (Alternaria alternata), Cabbage Alternaria leaf spot (Alternaria brassicae), Carrot leaf blight (Alternaria dauci), Pear black spot (Alternaria kikuchiana), Apple Alternaria blotch (Alternaria mali), Leek Alternaria leaf spot (Alternaria porri), Sorghum target spot (Bipolaris sorghicola), Maize southern leaf blight (Cochliobolus heterostrophus), Rice brown spot (Cochliobolus miyabeanus), Garlic tip blight (Pleospora herbarum), Barley stripe (Pyrenophora graminea), Barley net blotch (Pyrenophora teres), Sorghum leaf blight (Setosphaeria turcica), Maize northern leaf blight (Setosphaeria turcica), Asparagus leaf spot (StemphyliumBotryosum), Scab (Venturia carpophila) of the Prunoideae subfamily of the Rosaceae family, Scab (Venturia Inaequalis) of apples, Scab (Venturia nashicola) of Japanese pears, Gummy stem blight (Didymella bryoniae) of the Cucurbitaceae family, Leaf spot (Phoma exigua var. exigua) of burdock, Streak (Phoma wasabiae) of Japanese horseradish, Ring rot (Botryosphaeria berengeriana f. sp. piricola) of the Pomoideae subfamily of the Rosaceae family, Soft rot (Botryosphaeria dothidea, Lasiodiplodia theobromae, Diaporthe sp.) of kiwifruit, Common green mold (Penicillium digitatum) of citrus fruits, Blue mold (Penicillium italicum) of citrus fruits, Powdery mildew occurring in various crops, Powdery mildew of barley (Blumeria graminis f. sp. hordei), Powdery mildew of wheat (Blumeria graminis f. sp. tritici), Powdery mildew of cucumbers (Erysiphe betae, Leveillula taurica, Oidium sp., Podosphaera xanthii), Powdery mildew of eggplants (Erysiphe cichoracearum, Leveillula taurica, Sphaerotheca fuliginea), Powdery mildew of carrots and parsley (Erysiphe heraclei), Powdery mildew of peas (Erysiphe pisi), Powdery mildew of tomatoes (Leveillula taurica, Oidium neolycopersici, Oidium sp.), Powdery mildew of bell peppers (Leveillula taurica), Powdery mildew of pumpkins (Oidium sp., Podosphaera xanthii), Powdery mildew of bitter gourds (Oidium sp.), Powdery mildew of persimmons (Phyllactiniakakicola), powdery mildew of burdock (Podosphaera fusca), powdery mildew of apple (Podosphaera leucotricha), powdery mildew of rose (Podosphaera pannosa, Uncinuliella simulans var. simulans, U. s. var. tandae), powdery mildew of zucchini and wax gourd (Podosphaera xanthii), powdery mildew of strawberry (Sphaerotheca aphanis var. aphanis), powdery mildew of watermelon and melon (Sphaerotheca fuliginea), powdery mildew of grape (Uncinula necator, U. n. var. necator), apple blotch (Diplocarpon mali), black spot of rose (Diplocarpon rosae), gray mold neck rot of onion (Botrytis allii), gray mold, Botrytis blight (Botrytis cinerea), leaf blight of garlic (Botrytis cinerea, B. byssoidea, B. squamosa), chocolate spot of broad bean (Botrytis cinerea, B. elliptica, B. fabae), brown rot of Rosaceae (Monilinia fructicola, M. fructigena, M. laxa), blossom blight of apple (Monilinia mali), dollar spot (Sclerotinia homoeocarpa), cottony rot, sclerotinia rot, stem rot (Sclerotinia sclerotiorum), false smut of rice (Villosiclava virens), root necrosis of soybean (Calonectria ilicicola), fusarium blight of wheat (Fusarium crookwellense, F. culmorum, Gibberella avenacea, G. zeae,Monographella nivalis), barley scab (Fusarium blight (Fusarium culmorum, Gibberella avenacea, G. zeae)), konjac dry rot (Dry rot (Fusarium oxysporum, F. solani f. sp. radicicola)), yam brown rot (Brown rot (Fusarium oxysporum, F. solani f. sp. pisi, F. s. f. sp. radicicola)), adzuki bean wilt (Fusarium wilt (Fusarium oxysporum f. sp. adzukicola)), Chinese chive dry rot (Fusarium basal rot (Fusarium oxysporum f. sp. allii, F. solani f. sp. radicicola)), sweet potato stem rot (Stem rot (Fusarium oxysporum f. sp. batatas, F. solani)), taro dry rot (Dry rot (Fusarium oxysporum f. sp. colocasiae)), cabbage and komatsuna yellows (Yellows (Fusarium oxysporum f. sp. conglutinans)), banana Panama disease (Panama disease (Fusarium oxysporum f. sp. cubense)), strawberry wilt (Fusarium wilt (Fusarium oxysporum f. sp. fragariae)), lettuce root rot (Root rot (Fusarium oxysporum f. sp. lactucae)), watermelon stem rot (Fusarium wilt (Fusarium oxysporum f. sp. lagenariae, F. o. f. sp. niveum)), tomato wilt (Fusarium wilt (Fusarium oxysporum f. sp. lycopersici)), melon stem rot (Fusarium wilt (Fusarium oxysporum f. sp. melonis)), radish yellows (Yellows (Fusarium oxysporum f. sp.raphani), spinach Fusarium wilt (Fusarium oxysporum f. sp. spinaciae), soybean sudden death syndrome (Fusarium solani f. sp. Glycines, Fusarium virguliforme), rice bakanae disease (Gibberella fujikuroi), radish Verticillium black spot (Verticillium albo - atrum, V. dahliae), tomato, eggplant, and cucumber Verticillium wilt (Verticillium dahliae), fig Ceratocystis canker (Ceratocystis ficicola), sweet potato black rot (Ceratocystis fimbriata), tea gray blight (Pestalotiopsis longiseta, P. theae), chestnut Endothia canker (Cryphonectria parasitica), citrus melanose (Diaporthe citri), asparagus stem blight (Phomopsis asparagi), pear Phomopsis canker (Phomopsis fukushii), eggplant brown spot (Phomopsis vexans), tea anthracnose (Discula theae - sinensis), apple Valsa canker (Valsa ceratosperma), rice blast (Magnaporthe grisea), strawberry crown rot (Colletotrichum acutatum, C. fragariae, Glomerella cingulata), apple bitter rot (Colletotrichum acutatum, Glomerella cingulata), oat anthracnose (Colletotrichum acutatum, Glomerellacingulata), Apple anthracnose (Colletotrichum acutatum), Grape ripe rot (Colletotrichum acutatum, Glomerella cingulata), Chrysanthemum anthracnose (Colletotrichum acutatum), Common bean anthracnose (Colletotrichum lindemuthianum), Cucurbit anthracnose (Colletotrichum orbiculare), Yam anthracnose (Glomerella cingulata), Chestnut anthracnose (Glomerella cingulata), Persimmon anthracnose (Glomerella cingulata), Azuki bean brown stem rot (Phialophora gregata), Yam leaf spot (Pseudophloeosporella dioscoreae), Barley scald (Rhynchosporium secalis), Wheat brown rust (Puccinia recondita), Wheat stripe rust (Puccinia striiformis), Rust diseases occurring in various crops, Fig rust (Phakopsora nishidana), Soybean rust (Phakopsora pachyrhizi), Rose rust (Kuehneola japonica, Phragmidium fusiforme, P. mucronatum, P. rosae-multiflorae), Pear rust (Gymnosporangium asiaticum), Apple rust (Gymnosporangium yamadae), Onion rust (Puccinia allii), Chrysanthemum white rust (Puccinia horiana), Chrysanthemum black rust (Puccinia tanaceti var. tanaceti), Broad bean rust (Uromyces viciae-fabae var. viciae-fabae), Sugarcane smut (Sporisoriumscitamineum), corn smut (Ustilago maydis), loose smut of barley (Ustilago nuda), net blister blight of tea (Exobasidium reticulatum), blister blight of tea (Exobasidium vexans), southern blight (Athelia rolfsii), root and stem rot of chrysanthemum (Ceratobasidium cornigerum, Rhizoctonia solani), sheath blight of ginger (Rhizoctonia solani), damping-off of cabbage seedlings (Rhizoctonia solani), damping-off of clover seedlings (Rhizoctonia solani), bottom rot of lettuce (Rhizoctonia solani), brown patch, large patch of turfgrass (Rhizoctonia solani), sheath blight of rice (Thanatephorus cucumeris), root rot of sugar beet (Thanatephorus cucumeris), leaf blight of sugar beet (Thanatephorus cucumeris), rhizopus rot of fig (Rhizopus stolonifer var. stolonifer), clubroot of cruciferous vegetables (Plasmodiophora brassicae), aphanomyces root rot of sugar beet (Aphanomyces cochlioides), white rust of crucifers (Albugo macrospora), downy mildew occurring on various crops, downy mildew of lettuce (Bremia lactucae), downy mildew of chrysanthemum (Peronospora chrysanthemi-coronarii), downy mildew of onion and Welsh onion (Peronospora destructor), downy mildew of spinach (Peronospora farinosa f. sp. spinaciae), downy mildew of soybean (Peronosporamanshurica), downy mildew of the Brassicaceae family (Peronospora parasitica), downy mildew of roses (Peronospora sparsa), downy mildew of sunflowers (Plasmopara halstedii), downy mildew of clovers (Plasmopara nivea), downy mildew of grapes (Plasmopara viticola), downy mildew of cucurbits (Pseudoperonospora cubensis), Phytophthora root rot of tara no ki (Phytophthora cactorum), Brown rot of watermelon (Phytophthora capsici), Phytophthora rot of pumpkin (Phytophthora capsici), Phytophthora blight of pepper (Phytophthora capsici), Phytophthora rot of watermelon (Phytophthora cryptogea), Late blight of tomato and potato (Phytophthora infestans), Blight of fig Wh Colletotrichum gloeosporioides, Phytophthora palmivora, Leaf blight (Phytophthora porri), Phytophthora root and stem rot (Phytophthora sojae), Phytophthora stem rot (Phytophthora vignae f. sp. adzukicola), Damping-off (Pythium aphanidermatum, P. myriotylum, P. paroecandrum, P. ultimum var. ultimum), Root rot (Pythium aristosporum), Browning root rot (Pythium arrhenomanes, P. graminicola), Damping-off (Pythium buismaniae, P. myriotylum), Root rot (Pythium myriotylum), Root rot (Pythium myriotylum, P. ultimum var. ultimum), Brown blotted root rot (Pythium sulcatum), Bacterial canker (Clavibacter michiganensis subsp. michiganensis), Scab (Streptomyces spp.), Crown gall (Rhizobium radiobacter), Bacterial stripe (Burkholderia andropogonis), Soft rot (Burkholderia cepacia, Pseudomonas marginalis pv. marginalis, Erwinia rhapontici), Bacterial grain rot (Burkholderia gladioli, B.Glumae), Bacterial fruit blotch (Acidovorax avenae subsp. citrulli), Bacterial leaf blight (Acidovorax konjaci), Bacterial wilt (Ralstonia solanacearum), Bacterial shot hole (Xanthomonas arboricola pv. pruni, Pseudomonas syringae pv. syringae, Brenneria nigrifluens), Bacterial leaf spot (Xanthomonas arboricola pv. pruni), Bacterial spot (Xanthomonas axonopodis pv. vitians), Black rot of Brassicaceae (Xanthomonas campestris pv. campestris), Bacterial pustule (Xanthomonas campestris pv. glycines), Bacterial spot (Xanthomonas campestris pv. nigromaculans), Bacterial spot (Xanthomonas campestris pv. vesicatoria), Citrus canker (Xanthomonas citri subsp. citri), Garlic spring rot (Pseudomonas cichorii, P. marginalis pv. marginalis, Erwinia sp.), Bacterial rot of lettuce (Pseudomonas cichorii, P. marginalis pv. marginalis, P. viridiflava), Bacterial blossom blight of kiwifruit (Pseudomonas marginalis pv. marginalis, P. syringae pv. syringae, P.viridiflava), kiwifruit canker (Pseudomonas syringae pv. actinidiae), loquat canker (Pseudomonas syringae pv. eriobotryae), cucurbit bacterial spot (Pseudomonas syringae pv. lachrymans), brassica bacterial black spot (Pseudomonas syringae pv. maculicola), plum canker (Pseudomonas syringae pv. morsprunorum, Erwinia sp.), tea bacterial shoot blight (Pseudomonas syringae pv. theae), scallion bacterial soft rot (Dickeya sp., Pectobacterium carotovorum), rosaceous pome fire blight (Erwinia amylovora), konjac soft rot (Pectobacterium carotovorum), bacterial soft rot (Pectobacterium carotovorum).
[0199] The development of control agents against diseases of agricultural and horticultural crops has progressed, and a variety of agents have been put into practical use to date. However, due to the long-term use of such agents, in recent years, pathogenic bacteria have acquired drug resistance, and there has been an increasing number of situations where it has become difficult to control them with existing fungicides that have been conventionally used. In addition, some of the existing agents are highly toxic, and some have the problem of disturbing the ecosystem by remaining in the environment for a long time, and this problem is becoming apparent. Under such circumstances, the compound of the present invention has excellent control activity against many pathogenic bacteria and has high safety for the target crops. In addition, the compound of the present invention can exhibit a sufficient control effect even against pathogenic bacteria that have acquired resistance to existing fungicides. Furthermore, the compound of the present invention does not cause phytotoxicity to the target crops, has almost no adverse effects on mammals, fish, and beneficial insects, has low residual properties, and has a low environmental load.
[0200] In addition to being used as an agricultural and horticultural fungicide, the compound of the present invention can also be used as a medical antibacterial agent and an animal antibacterial agent used as an antifungal agent or an internal parasite control agent, an antibacterial and antifungal agent for wood, paper / pulp, adhesives / paints, fibers, leather, etc., and an industrial fungicide for cooling water channels in manufacturing factories, etc.
[0201] Examples of pathogenic bacteria targeted as medical antibacterial agents or animal antibacterial agents include, but are not limited to, dermatophytes such as Trichophyton rubrum and Trichophyton mentagrophytes, Candida fungi such as Candida albicans, Aspergillus fungi such as Aspergillus fumigatus, Cryptococcus fungi such as Cryptococcus neoformas, gram-negative bacteria such as Escherichia coli, Pseudomonas aeruginosa, and Haemophilus influenzae, and gram-positive bacteria such as Staphylococcus aureus and Streptococcus pyogenes.
[0202] Examples of the strains targeted as antibacterial and antifungal agents include, but are not limited to, wood-decaying fungi such as Tyromyces palustris and Coriolus versicolor, and deterioration microorganisms of materials such as Aspergillus niger, Aspergillus terreus, Eurotium tonophilum, Penicillium citrinum, Penicillium funiculosum, Rhizopus oryzae, Cladosporium cladosporioides, Aureobasidium pullulans, Gliocladium virens, Chaetomium globosum, Fusarium moniliforme, and Myrothecium verrucaria.
[0203] Examples of the strains targeted as industrial bactericides include, but are not limited to, slime bacteria such as Sphaerotilis natans and Zoogloea ramigera.
[0204] In addition to use as a fungicide for agricultural and horticultural purposes, the compound of the present invention can also be used as an internal parasite control agent for livestock, poultry, or pets.
[0205] Specific examples of the internal parasites targeted include, but are not limited to, the following. Nematodes such as Haemonchus, Trichostrongylus, Ostertagia, Nematodirus, Cooperia, Ascaris, Bunostomum, Oesophagostomum, Chabertia, Trichuris, Storongylus, Trichonema, Dictyocaulus, Capillaria, Heterakis, Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria, Toxascaris, Parascaris, etc.; Filariidae nematodes such as Wuchereria, Brugia, Onchoceca, Dirofilaria, Loa, etc.; Dracunculidae nematodes such as Deacunculus, etc.; Cestodes such as Dipylidium caninum, Taenia taeniaeformis, Taenia solium, Taenia saginata, Hymenolepis diminuta, Moniezia benedeni, Diphyllobothrium latum, Diphyllobothrium erinacei, Echinococcus granulosus, Echinococcus multilocularis, etc.; Trematodes such as Fasciola hepatica, F. gigantica, Paragonimus westermanii, Fasciolopsic bruski, Eurytrema pancreaticum, E. coelomaticum, Clonorchis sinensis, Schistosoma japonicum, Schistosoma haematobium, Schistosoma mansoni; Eimeria spp. such as Eimeria tenella, Eimeria acervulina, Eimeria brunetti, Eimeria maxima, Eimeria necatrix, Eimeria bovis, Eimeria ovinoidalis; Trypanosomsa cruzi, Leishmania spp., Plasmodium spp., Babesis spp., Trichomonadidae spp., Histomanas spp., Giardia spp., Toxoplasma spp., Entamoeba histolytica, Theileria spp., etc.
[0206] In addition to being used as an agricultural and horticultural fungicide, the compound of the present invention can also be used as an antifungal agent.
[0207] Specific examples of pathogenic bacteria targeted as antifungal agents include, but are not limited to, the following. Dermatophytes such as Trichophyton rubrum and Trichophyton mentagrophytes, Candida fungi such as Candida albicans, Aspergillus fungi such as Aspergillus fumigatus, Cryptococcus fungi such as Cryptococcus neoformas, etc.
[0208] When applying the compound of the present invention as a plant disease and plant pest control agent, usually, the compound of the present invention is mixed with a suitable solid carrier or liquid carrier, and further, if desired, a surfactant, a penetrant, a spreading agent, a thickening agent, an antifreezing agent, a binder, an anti-caking agent, a disintegrant or a decomposition inhibitor, etc. are added to prepare a formulation in any dosage form such as a soluble concentrate, an emulsifiable concentrate, a wettable powder, a water soluble powder, a water dispersible granule, a water soluble granule, a suspension concentrate, a concentrated emulsion, a suspoemulsion, a microemulsion, a dustable powder, a granule or a gel, etc. for practical use. Further, from the viewpoints of labor saving and safety improvement, the formulation in any of the above dosage forms can also be enclosed in a water-soluble package and provided.
[0209] Examples of the solid carrier include natural minerals such as quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite or diatomaceous earth; inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate or potassium chloride; synthetic silicic acid; or synthetic silicate; etc.
[0210] Examples of the liquid carrier include alcohols such as ethylene glycol, propylene glycol or isopropanol; aromatic hydrocarbons such as xylene, alkylbenzene or alkylnaphthalene; ethers such as butyl cellosolve; ketones such as cyclohexanone; esters such as γ-butyrolactone; acid amides such as N-methylpyrrolidone or N-octylpyrrolidone; vegetable oils such as soybean oil, rapeseed oil, cottonseed oil or castor oil; or water; and the like. These solid and liquid carriers may be used alone or in combination of two or more.
[0211] Examples of the surfactant include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene styryl phenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene fatty acid ester, sorbitan fatty acid ester or polyoxyethylene sorbitan fatty acid ester; anionic surfactants such as alkyl sulfate, alkylbenzene sulfonate, lignin sulfonate, alkyl sulfosuccinate, naphthalene sulfonate, alkylnaphthalene sulfonate, salt of formalin condensate of naphthalene sulfonate, salt of formalin condensate of alkylnaphthalene sulfonate, polyoxyethylene alkyl aryl ether sulfate or phosphate, polyoxyethylene styryl phenyl ether sulfate or phosphate, polycarboxylate or polystyrene sulfonate; cationic surfactants such as alkylamine salt or alkyl quaternary ammonium salt; or amphoteric surfactants such as amino acid type or betaine type; and the like.
[0212] The content of these surfactants is not particularly limited, but is usually preferably in the range of 0.05 to 20 parts by weight with respect to 100 parts by weight of the preparation of the present invention. These surfactants may be used alone or in combination of two or more.
[0213] When the compound of the present invention is used as an agricultural chemical, if necessary, it may be mixed and applied with other types of herbicides, various insecticides, acaricides, nematicides, fungicides, plant growth regulators, synergists, fertilizers, soil conditioners, etc. at the time of formulation or spraying.
[0214] In particular, by mixing and applying with other agricultural chemicals or plant hormones, cost reduction due to a decrease in the application dose, expansion of the bactericidal and insecticidal spectrum due to the synergistic effect of the mixed agent, or a higher pest control effect can be expected. At this time, it is also possible to combine with a plurality of known agricultural chemicals at the same time.
[0215] In one aspect, examples of the types of agricultural chemicals to be mixed and used with the compound of the present invention include compounds described in The Pesticide Manual, 18th Edition, 2018. Specific examples of their common names are as follows. However, the agricultural chemicals to be mixed and used are not necessarily limited to these. Fungicides: acibenzolar-S-methyl, acypetacs, aldimorph, allyl alcohol, ametoctradin, aminopyrifen, amisulbrom, amobam, ampropylfos, anilazine, azaconazole, azithiram, azoxystrobin, barium polysulfide, benalaxyl, benalaxyl-M, benodanil, benomyl, benquinox, bentaluron, benthiavalicarb-isopropyl, benthiazole, benzamacril, benzamorf, benzovindiflupyr, binapacryl, biphenyl, bitertanol, bixafen, blasticidin-S, bordeaux mixture, boscalid, bromoconazole, bupirimate, buthiobate, butylamine, calcium polysulfide, captafol, captan, carbamorph, carbendazim, carboxin, carpropamid, carvone, cheshunt mixture, chinomethionat,chlobenthiazone, chloraniformethane, chloranil, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlorquinox, chlozolinate, climbazole, copper acetate, copper carbonate, basic, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper sulfate, copper sulfate, basic, copper zinc chromate, coumoxystrobin, cresol, cufraneb, cuprobam, cyazofamid, cyclafuramid, cycloheximide, cyflufenamid, cymoxanil, cypendazole, cyproconazole, cyprodinil, cyprofuram, dazomet, debacarb, decafentin, dehydroacetic acid, dichlobentiazox, dichlofluanid, dichlone, dichlorophen, dichlozoline, diclobutrazol, diclocymet, diclomezinedicloran, diethofencarb, difenoconazole, diflumetorim, dimethirimol, dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dinobuton, dinocap, dinocap-4, dinocap-6, dinocton, dinosulfon, dinoterbon, diphenylamine, dipymetitrone, dipyrithione, disulfiram, ditalimfos, dithianon, DNOC, dodemorph, dodine, drazoxolon, edifenphos, enestrobin, enoxastrobin, epoxiconazole, ethaboxam, etaconazole, etem, ethirimol, ethoxyquin, etridiazole, famoxadone, fenamidone, fenaminosulf, fenaminstrobin, fenapanil, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenitropan, fenoxanil, fenpiclonil, fenpicoxamidfenpropidin, fenpropimorph, fenpyrazamine, fentin, ferbam, ferimzone, florylpicoxamid, fluazinam, fludioxonil, flufenoxystrobin, fluindapyr, flumetover, flumorph, fluopicolide, fluopimomide, fluopyram, fluoroimide, fluotrimazole, fluoxapiprolin, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutolanil, flutianil, flutriafol, fluxapyroxad, folpet, fosetyl-aluminium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbanil, furconazole, furconazole-cis, furmecyclox, furophanate, glyodin, griseofulvin, guazatine, halacrinate, hexachlorobenzene, hexaconazole, hexylthiofos8-hydroxyquinoline sulfate, hymexazol, imazalil, imibenconazole, iminoctadine-albesilate, iminoctadine-triacetate, inpyrfluxam, iodocarb, ipconazole, ipfentrifluconazole, ipflufenoquin, iprobenfos, iprodione, iprovalicarb, isofetamid, isoflucypram, isotianil, isoprothiolane, isopyrazam, isovaledione, kasugamycin, kresoxim-methyl, laminarin, mancopper, mancozeb, mandestrobin, mandipropamid, maneb, mebenil, mecarbinzid, mefentrifluconazole, mepanipyrim, mepronil, meptyldinocap, metalaxyl, metalaxyl-M, metam, metazoxolon, metconazole, methasulfocarb, methfuroxam, metyltetraprole, metiram, metominostrobin,Metrafenone, Metsulfovax, Milneb, Myclobutanil, Myclozolin, Nabam, Naftifine, Natamycin, Nickel bis (dimethyldithiocarbamate), Nitrostyrene, Nitrothal-isopropyl, Nuarimol, Octhilinone, Ofurace, Orysastrobin, Oxadixyl, Oxathiapiprolin, Oxine copper, Oxpoconazole fumarate, Oxycarboxin, Pefurazoate, Penconazole, Pencycuron, Penflufen, Pentachlorophenol, Penthiopyrad, 2-Phenylphenol, Phosdiphen, Phthalide, Picarbutrazox, Picoxystrobin, Piperalin, Polycarbamate, Polyoxins, Polyoxorim, Potassium azide, Potassium hydrogen carbonate, Probenazole, Prochloraz, Procymidone, Propamocarb hydrochloride, Propiconazole, Propinebproquinazid, prothiocarb, pyrazophos, pyribencarb, pyrifenox, pyrimethanil, pyriminostrobin, pyroquilon, prothiocarb, prothioconazole, pydiflumetofen, pyracarbolid, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyrapropoyne, pyraziflumid, pyridachlometyl, pyridinitril, pyriofenone, pyrisoxazole, pyroxychlor, pyroxyfur, quinacetol - sulfate, quinazamid, quinconazole, quinoxyfen, quinofumelin, quintozene, rabenzazole, salicylanilide, sedaxane, silthiofam, simeconazole, sodium hydrogen carbonate, sodium hypochlorite, spiroxamine, sulfur, tebuconazole, tebufloquin, tecloftalam, tecnazene, tecoram, tetraconazole, thiabendazoleThiadifluor, thicyofen, thifluzamide, thiochlor, Thiochlorfenphim, thiophanate, thiophanate-methyl, thiram, tiadinil, tioxymid, tolclofos-methyl, tolprocarb, tolylfluanid, triadimefon, triadimenol, triamiphos, triarimol, triazbutil, triazoxide, tributyltin oxide, trichlamide, triclopyricarb, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, validamycin, valifenalate, vinclozolin, zarilamid, zinc naphthenate, zinc sulfate, zineb, ziram, zoxamide, shiitake mycelium extract, shiitake fruiting body extract, etc. Insecticides: abamectin, acephate, acequinocyl, acetamiprid, acrinathrin, acynonapyr, afidopyropen, afoxolaner, alanycarb, aldicarb, allethrin, alpha-cypermethrin, alpha-endosulfan, amidoflumet, amitraz, azamethiphos, azinphos-ethyl, azinphos-methyl, azocyclotin, bacillus thuringiensis, bendiocarb, benfluthrin, benfuracarb, bensultap, benzoximate, benzpyrimoxan, beta-cyfluthrin, beta-cypermethrin, bifenazate, bifenthrin, bioallethrin, biresmethrin, bistrifluron, broflanilide, bromopropylate, buprofezin, butocarboxim, carbaryl, carbofuran, carbosulfan, cartap, chinomethionat, chlorantraniliprole, chlorethxyfos,chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, chlorobezilate, chloroprallethrin, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clofentezine, clothianidin, cyanophos, cyantraniliprole, cyclaniliprole, cycloprothrin, cyenopyrafen, cyetpyrafen, cyflumetofen, cyfluthrin, cyhalodiamide, cyhalothrin, cyhexatine, cypermethrin, cyphenothrin, cyproflanilide, cyromazine, deltamethrin, diacloden, diafenthiuron, diazinon, dichlorvos, dicloromezotiaz, dicofol, dienochlor, diflovidazin, diflubenzuron, dimefluthrin, dimethoate, dimethylvinphos, dimpropyridaz, dinotefuran, diofenolan, disulfoton, DNOCd-T-80-phthalthrin (d-tetramethrin), emamectin benzoate, empenthrin, endosulfan, EPN, epsilon-metofluthrin, epsilon-momfluorothrin, esfenvalerate, ethiofencarb, ethiprole, etofenprox, etoxazole, etrimfos, Febantel, fenazaquin, fenbutatin oxide, fenitrothion, fenmezoditiaz, fenobucarb, fenothiocarb, fenoxycarb, fenpropathrin, fenpyroximate, fenthion, fenvalerate, fipronil, flometoquin, flonicamid, fluacrypyrim, fluazuron, flubendiamide, fluchlordiniliprole, flucycloxuron, flucythrinate, flufenerim, flufenoxuron, flufenprox, flufiprole, fluhexafon, flumethrin, flupentiofenox, flupyradifurone, flupyriminfluralaner, fluvalinate, fluxametamide, fonophos, formetanate, formothion, furathiocarb, gamma-cyhalothrin, halfenprox, halofenozide, heptafluthrin, hexaflumuron, hexythiazox, hydramethylnon, imidacloprid, imiprothrin, indazapyroxamet, indoxacarb, indoxacarb-MP, isocycloseram, isofenphos, isoprocarb, isoxathion, kappa-bifenthrin, kappa-tefluthrin, lambda-cyhalothrin, lepimectin, lufenuron, malathion, meperfluthrin, metaflumizone, metalcarb, metaldehyde, methacrifos, methamidophos, methidathion, methomyl, methoprene, methoxychlor, methoxyfenozide, methyl bromide, metofluthrin, milbemectin, momfluorothrin,Monocrotophos, Muscalure, Nicofluprole, Nitenpyram, Novaluron, Noviflumuron, Omethoate, Oxazosulfyl, Oxydemeton-methyl, Oxydeprofos, Parathion, Parathion-methyl, Pentachlorophenol, Permethrin, Phenothrin, Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos-methyl, Praziquantel, Profenofos, Profluthrin, Propaphos, Propargite, Prothiofos, Protrifenbute, Pyflubumide, Pymetrozine, Pyraclofos, Pyrafluprole, Pyrethrins, Pyridaben, Pyridalyl, Pyrifluquinazon, Pyrimidifen, Pyriprole, Pyriproxyfen, Resmethrin, Rotenone, Silafluofen, Spidoxamat, Spinetoram, Spinosad, SpirodiclofenSpiromesifen, spiropidion, spirotetramat, spyromesifen, sulfotep, sulfoxaflor, sulprofos, tau-fluvalinate, tebufenozide, tebufenpyrad, teflubenzuron, tefluthorin, terbufos, tetrachlorantraniliprole, tetrachlorvinphos, tetramethrin, tetramethylfluthrin, tetraniliprole, thiacloprid, thiamethoxam, thiocyclam, thiodicarb, thiofanox, thiometon, tolfenpyrad, tralomethrin, transfluthrin, triazamate, triazuron, trichlorfon, triflumezopyrim, triflumuron, tyclopyrazoflor, vamidothion, zeta-cypermethrin, etc. Antiparasitic drugs: esfenvalerate, fenpropathrin, fenvalerate, cypermethrin, bifenthrin, cypermethrin, deltamethrin, etofenprox, lambda-cyhalothrin, permethrin, tefluthrin, zeta-cypermethrin, acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiamethoxam, chromafenozide, fenoxycarb, lufenuron, methoprene, pyriproxyfen, triflumuron, chlorpyrifos, chlorpyrifos-methyl, diazinon, dichlorvos, fenitrothion, fenthion, malathion, pirimiphos-methyl, tetrachlorvinphos, ethiprole, fipronil, propoxur, carbaryl, bendiocarb, metoxadiazone, fenobucarb, carbofuran, afoxolaner, fluralaner, fluxametamide, sarolaner, lotilaner,tigolaner, esafoxolaner, modoflaner, umifoxolaner, mivorilaner, avermectin, ivermectin, doramectin, eprinomectin, maduramycin, milbemycin, milbemycin oxime, moxidectin, selamectin, indoxacarb, amitraz, bistrifluron, spinosad, albendazole, atovaquone, bithionol, cambendazole, carnidazole, chloroquine, clazuril, clorsulon, closantel, coumaphos, dichlorophen, diethylcarbamazine, diminazene, dinitolmide, dithiazanine iodide, emodepside, epsiprantel, febantel, fenbendazole, flubendazole, glycalpyramide, imidocarb, levamisole, mebendazole, mefloquine hydrochloride, melarsamine hydrochloride, metronidazole, metyridine,Monepantel, morantel tartrate, niclosamide, oxantel pamoate, oxantel tartrate, oxibendazole, oxyclozanide, piperazine adipate, piperazine citrate, piperazine phosphate, praziquantel, pyrantel pamoate, rafoxanide, tetramisole hydrochloride, thiabendazole, triclabendazole, etc. Antifungal agents: ketoconazole, miconazole nitrate, etc. Antibacterial agents: amoxicillin, ampicillin, bethoxazin, bithionol, bronopol, cefapirin, cefazolin, cefquinome, ceftiofur, chlortetracycline, clavulanic acid, danofloxacin, difloxacin, dinitolmide, enrofloxacin, florfenicol, lincomycin, lomefloxacin, marbofloxacin, miloxacin, mirosamycin, nitrapyrin, norfloxacin, octhilinone, ofloxacin, orbifloxacin, oxolinic acid, oxytetracycline, penicillin, streptomycin, thiamphenicol, tiamulin fumarate, tilmicosin phosphate, acetylisovaleryltylosin, tylosin phosphate, tulathromycin, valnemulin, calcined oyster shell (calcium oxide), Talaromyces spp., Trichoderma spp., and Uniochitrium spp., etc.
[0216] Although the application dosage of the compound of the present invention may vary depending on the application scenario, application time, application method, cultivated crop, etc., generally, 0.005 to 50 kg per hectare (ha) as the active ingredient amount is appropriate, and 0.01 to 1 kg is preferred.
[0217] Next, formulation examples of the preparation when using the compound of the present invention are shown. However, the formulation examples of the present invention are not limited to these only. In the following formulation examples, "parts" means parts by weight.
[0218] [Wettable powder] Compound of the present invention 0.1 - 80 parts Solid carrier 5 - 98.9 parts Surfactant 1 - 10 parts Others 0 - 5 parts Examples of others include, for example, anti-caking agents or anti-decomposition agents, etc.
[0219] [Emulsion] Compound of the present invention 0.1 - 30 parts Liquid carrier 45 - 95 parts Surfactant 4.9 - 15 parts Others 0 - 10 parts Examples of others include, for example, spreading agents or anti-decomposition agents, etc.
[0220] [Suspension concentrate] Compound of the present invention 0.1 - 70 parts Liquid carrier 15 - 98.89 parts Surfactant 1 - 12 parts Others 0.01 - 30 parts Examples of others include, for example, anti-freezing agents or thickening agents, etc.
[0221] [Granular wettable powder] Compound of the present invention 0.1 - 90 parts Solid carrier 0 - 98.9 parts Surfactant 1 - 20 parts Others 0 - 10 parts Examples of others include, for example, binders or anti-decomposition agents, etc.
[0222] 〔Liquid formulation〕 0.01 - 70 parts of the compound of the present invention 20 - 99.99 parts of liquid carrier 0 - 10 parts of others Examples of others include antifreezing agents or spreading agents, etc.
[0223] 〔Granule formulation〕 0.01 - 80 parts of the compound of the present invention 10 - 99.99 parts of solid carrier 0 - 10 parts of others Examples of others include binders or decomposition inhibitors, etc.
[0224] 〔Powder formulation〕 0.01 - 30 parts of the compound of the present invention 65 - 99.99 parts of solid carrier 0 - 5 parts of others Examples of others include drift inhibitors or decomposition inhibitors, etc.
[0225] In use, the above formulations are diluted 1 - 10,000 times, preferably 100 - 10,000 times with water, or sprayed without dilution.
[0226] Next, formulation examples of agricultural and horticultural fungicides containing the compound of the present invention as an active ingredient are specifically shown. However, the formulations of the present invention are not limited only to these, including the compound of the present invention. In the following formulation examples, "parts" means parts by weight.
[0227] 〔Formulation Example 1〕Emulsion 20 parts of Compound No.1 - 001 of the present invention 55 parts of methylnaphthalene 20 parts of cyclohexanone 5 parts of Solpol 2680 (Mixture of non - ionic surfactant and anionic surfactant: manufactured by Toho Chemical Industry Co., Ltd., trade name) Mix the above components uniformly to form an emulsion. When in use, dilute the above emulsion 50 to 20,000 times with water and spray it so that the amount of the active ingredient is 0.005 to 50 kg per hectare.
[0228] [Formulation Example 2] Wettable powder 25 parts of Compound No. 1-001 of the present invention 66 parts of pyrophyllite 4 parts of Solpol 5039 (Anionic surfactant: manufactured by Toho Chemical Industry Co., Ltd., trade name) 3 parts of Carplex #80D (White carbon: manufactured by Shionogi & Co., Ltd., trade name) 2 parts of calcium lignin sulfonate Mix and grind the above components uniformly to form a wettable powder. When in use, dilute the above wettable powder 50 to 20,000 times with water and spray it so that the amount of the active ingredient is 0.005 to 50 kg per hectare.
[0229] [Formulation Example 3] Dust 3 parts of Compound No. 1-001 of the present invention 0.5 part of Carplex #80D (White carbon: manufactured by Shionogi & Co., Ltd., trade name) 95 parts of kaolinite 1.5 parts of diisopropyl phosphate Mix and grind the above components uniformly to form a dust. When in use, spray the above dust so that the amount of the active ingredient is 0.005 to 50 kg per hectare.
[0230] [Formulation Example 4] Granule 5 parts of Compound No. 1-001 of the present invention 30 parts of bentonite 64 parts of talc 1 part of calcium lignin sulfonate Mix and grind the above components uniformly, add a small amount of water, stir and mix, granulate with an extrusion granulator, and dry to form granules. When in use, spray the above granules so that the amount of the active ingredient is 0.005 to 50 kg per hectare.
[0231] [Formulation Example 5] Suspension 25 parts of Compound No. 1-001 of the present invention 5 parts of Solpol 3353 (Nonionic surfactant: manufactured by Toho Chemical Industry Co., Ltd., trade name) 0.5 part of Lunox 1000C (Anionic surfactant: manufactured by Toho Chemical Industry Co., Ltd., trade name) 0.2 part of xanthan gum (natural polymer) 0.4 part of sodium benzoate 10 parts of propylene glycol 58.9 parts of water The above components excluding the active ingredient (the compound of the present invention) were uniformly dissolved, then the compound of the present invention was added and stirred well, and then wet pulverized with a sand mill to obtain a flowable agent. When in use, the flowable agent is diluted 50 to 20,000 times with water and sprayed so that the amount of the active ingredient becomes 0.005 to 50 kg per hectare.
[0232] [Formulation Example 6] Granular wettable powder 75 parts of Compound No. 1-001 of the present invention 5 parts of Hitenol NE-15 (Anionic surfactant: manufactured by Daiichi Kogyo Seiyaku Co., Ltd., trade name) 10 parts of Vanirex N (Anionic surfactant: manufactured by Nippon Paper Industries Co., Ltd., trade name) 10 parts of Carplex #80D (White carbon: manufactured by Shionogi & Co., Ltd., trade name) The above components were uniformly mixed and finely pulverized, a small amount of water was added and stirred and mixed, granulated with an extrusion granulator, and dried to obtain a dry flowable agent. When in use, it is diluted 50 to 20,000 times with water and sprayed so that the active ingredient becomes 0.005 to 50 kg per hectare.
[0233] As the application method of the compound of the present invention, foliar spraying, soil treatment, seed disinfection, etc. can be mentioned, and it is also effective in general methods commonly used by those skilled in the art.
[0234] 〔Summary〕 As described above, the present invention relates to the following [1] to [9]. 〔1〕 Formula (1):
[0235]
Chem.
[0236] [In the formula, G represents G-1, G-1 represents a structure represented by the following structural formula,
[0237]
Chem.
[0238] G 1 is hydroxy, nitro, cyano, a halogen atom, C1-C6 alkyl, C3-C 10 cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, R b substituted C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, di(C1-C6 alkyl)amino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C3-C 10 cycloalkylaminocarbonyl, di(C1-C6 alkyl)aminocarbonyl or -C(=NOR)R', G 1 in the relationship with, when m5 represents an integer of 2, 3, 4 or 5, each G 1 may be the same as or different from each other, R b is cyano, C3-C 10 cycloalkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, di(C1-C6 alkyl)aminocarbonyl, phenyl or -C(=NOR)R', R represents a hydrogen atom or C1-C6 alkyl, R’ represents C1-C6 alkyl, T represents an oxygen atom or a sulfur atom, R X is C1-C6 alkyl, C3-C 10 cycloalkyl, C1-C6 haloalkyl, C1-C6 alkyl substituted by R c -1, C1-C6 alkyl substituted by R X -2, C1-C6 alkyl substituted by R X -3 or C1-C6 alkyl substituted by R X -4, and X represents R X -1 to R X -4 each represent a structure represented by the following structural formula,
[0239] [Chemical formula]
[0240] X 1 represents a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl or C1-C6 alkoxy, X 1 In the relationship with, when u5 indicates an integer of 2, 3, 4 or 5, each X 1 may be the same as or different from each other, X 1 In the relationship with, when u4 indicates an integer of 2, 3 or 4, each X 1 may be the same as or different from each other, R c is cyano, C3-C 10 cycloalkyl, C1-C6 alkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, di(C1-C6 alkyl)aminocarbonyl or -C(=NOR)R’, R Y represents a hydrogen atom, a halogen atom or C1-C6 alkyl, R 1 represents a hydrogen atom or C1-C6 alkyl, R 2 represents a hydrogen atom or C1-C6 alkyl, R3 represents a hydrogen atom, a halogen atom, C1-C6 alkyl or C1-C6 alkoxy, R 4 represents a hydrogen atom, a halogen atom or C1-C6 alkyl, R a represents a hydrogen atom, C1-C6 alkyl, R a -1, R a -2, R a -3, R a -4, R a -5 or R a -6, R a -1, R a -2, R a -3, R a -4, R a -5 and R a -6 each represent a structure represented by the following structural formula,
[0241]
Chemical formula
[0242] R 5 represents a hydrogen atom or C1-C6 alkyl, R 6 represents a hydrogen atom or C1-C6 alkyl, r 1 When r represents an integer of 2, two Rs 5 and two Rs 6 may be the same as or different from each other, R 7 represents C1-C6 alkyl, C3-C 10 cycloalkyl, C1-C6 haloalkyl or phenyl, R 8 represents a hydrogen atom or C1-C6 alkyl, R 9 represents a hydrogen atom or C1-C6 alkyl, Z represents Z-1 to Z-45 or Z-46, Z-1 to Z-46 each represent a structure represented by the following structural formula,
[0243] [Chem.]
[0244] [Chem.]
[0245] Note that the substitution position of Z 1 represents that it is substituted on the aromatic ring of Z-1 to Z-46, Z 1 is hydroxy, carboxy, amino, nitro, cyano, halogen atom, C1-C6 alkyl, C3-C 10 cycloalkyl, C1-C6 haloalkyl, C3-C 10 halocycloalkyl, C2-C6 alkenyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylamino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkyl substituted by R i , -OR d , -NHC(О)R e , -NR h C(О)R e , -NHSО2R f , -C≡CR g , -SО2NH2, -C(О)NH2, -C(S)NH2, -C(=NOH)NH2, E-1 to E-54, F-1 to F-15 or -C(=NOR)R’, Z 1 In relation to, when n7 indicates an integer of 2, 3, 4, 5, 6 or 7, each Z 1 may be the same as or different from each other, Z 1 In relation to, when n6 indicates an integer of 2, 3, 4, 5 or 6, each Z 1 may be the same as or different from each other, Z 1 In relation to, when n5 indicates an integer of 2, 3, 4 or 5, each Z 1may be the same as or different from each other, Z 1 in relation to, when n4 represents an integer of 2, 3 or 4, each Z 1 may be the same as or different from each other, Z 1 in relation to, when n3 represents an integer of 2 or 3, each Z 1 may be the same as or different from each other, Z 1 in relation to, when n2 represents an integer of 2, each Z 1 may be the same as or different from each other, Z 2 represents C1-C6 alkyl or phenyl, R d represents C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C1-C6 alkyl substituted with R 10 C1-C6 alkylcarbonyl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, E-1 to E-54, F-1 to F-15 or C1-C6 alkylaminocarbonyl, R 10 R represents C3-C 10 cycloalkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, di(C1-C6 alkyl)aminocarbonyl, E-1 to E-54, F-1 to F-15 or -C(=NOR)R', R e represents C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C2-C6 alkenyloxy, C1-C6 alkylamino, benzyloxy, E-1 to E-54, F-1 to F-15 or di(C1-C6 alkyl)amino, R f represents C1-C6 alkyl, C1-C6 haloalkyl, E-1 to E-54, F-1 to F-15 or di(C1-C6 alkyl)amino, R g represents a hydrogen atom or tri(C1-C4 alkyl)silyl, R hrepresents C1-C6 alkyl, R i represents hydroxy or C1-C6 alkoxy, E-1 to E-54 each represent a structure represented by the following structural formula,
[0246]
Chemical formula
[0247]
Chemical formula
[0248] F-1 to F-15 each represent a structure represented by the following structural formula,
[0249]
Chemical formula
[0250] Z a represents a halogen atom, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylcarbonyl or C1-C6 alkoxycarbonyl, Z a In relation to, when v7 indicates an integer of 2, 3, 4, 5, 6 or 7, each Z a may be the same as or different from each other, Z a In relation to, when v6 indicates an integer of 2, 3, 4, 5 or 6, each Z a may be the same as or different from each other, Z a In relation to, when v5 indicates an integer of 2, 3, 4 or 5, each Z a may be the same as or different from each other, Z a In relation to, when v4 indicates an integer of 2, 3 or 4, each Z amay be identical to or different from each other, Z a in the relationship with, when v3 represents an integer of 2 or 3, each Z a may be identical to or different from each other, Z a in the relationship with, when v2 represents an integer of 2, each Z a may be identical to or different from each other, Z b represents C1 - C6 alkyl, m5 represents an integer of 0, 1, 2, 3, 4 or 5, n7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7, n6 represents an integer of 0, 1, 2, 3, 4, 5 or 6, n5 represents an integer of 0, 1, 2, 3, 4 or 5, n4 represents an integer of 0, 1, 2, 3 or 4, n3 represents an integer of 0, 1, 2 or 3, n2 represents an integer of 0, 1 or 2, n1 represents an integer of 0 or 1, u5 represents an integer of 0, 1, 2, 3, 4 or 5, u4 represents an integer of 0, 1, 2, 3 or 4, p represents an integer of 0 or 1, r 1 represents an integer of 1 or 2, r 2 represents an integer of 0 or 1, t represents an integer of 0, 1 or 2, v7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7, v6 represents an integer of 0, 1, 2, 3, 4, 5 or 6, v5 represents an integer of 0, 1, 2, 3, 4 or 5, v4 represents an integer of 0, 1, 2, 3 or 4, v3 represents an integer of 0, 1, 2 or 3, v2 represents an integer of 0, 1 or 2, v1 represents an integer of 0 or 1.] A pyrazole compound represented by the formula or a salt thereof. [2] R b represents cyano or phenyl, X 1 represents a halogen atom, R c represents cyano, C3-C 10 cycloalkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, di(C1-C6 alkyl)aminocarbonyl or -C(=NOR)R’, R Y represents a hydrogen atom or a halogen atom, R a represents a hydrogen atom, C1-C6 alkyl, R a -1 or R a -4, R 5 represents a hydrogen atom, R 6 represents a hydrogen atom, R 7 represents C1-C6 alkyl, Z represents Z-1, Z-2, Z-3, Z-4, Z-6, Z-8, Z-9, Z-10, Z-11, Z-14, Z-17, Z-19, Z-20, Z-24, Z-27, Z-39, Z-41 or Z-46, Z 1 represents hydroxy, carboxy, amino, nitro, cyano, halogen atom, C1-C6 alkyl, C3-C 10 cycloalkyl, C1-C6 haloalkyl, C3-C 10 halocycloalkyl, C2-C6 alkenyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkylamino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkyl substituted with R i , -OR d , -NHC(О)R e , -NR h C(О)R e , -NHSО2R f , -C≡CR g, -SO2NH2, -C(O)NH2, -C(S)NH2, -C(=NOH)NH2, -C(=NOR)R’, E-1, E-2, E-3, E-7, E-12, E-14, E-21, E-23, E-24, E-31, F-10 or F-11, Z 2 represents C1-C6 alkyl, R d represents C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C1-C6 alkyl substituted with R 10 , C1-C6 alkylcarbonyl, C1-C6 alkylaminocarbonyl or E-1, R 10 represents C3-C 10 cycloalkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, di(C1-C6)alkylaminocarbonyl, -C(=NOR)R’, tetrahydrofuran-3-yl, E-1, E-2, E-3, E-5, E-22, E-30, E-41 or F-3, R e represents C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C2-C6 alkenyloxy, C1-C6 alkylamino, di(C1-C6)alkylamino, benzyloxy, E-1, E-2, E-3, E-4, E-8, E-11, E-13, E-14 or E-23, R f represents C1-C6 alkyl, C1-C6 haloalkyl, di(C1-C6 alkyl)amino or E-1, m5 represents an integer of 0, 1 or 2, n7 represents an integer of 0, n5 represents an integer of 0, 1, 2 or 3, n4 represents an integer of 0, 1 or 2, n3 represents an integer of 0, 1 or 2, n2 represents an integer of 0 or 2, n1 represents an integer of 1, u5 represents an integer of 0 or 1, u4 represents an integer of 0 or 1, r 1 represents an integer of 1, v6 represents an integer of 0, v5 represents an integer of 0, 1 or 2, v4 represents an integer of 0, 1, 2 or 3, v3 represents an integer of 0, 1 or 2, v2 represents an integer of 0 or 1, v1 is the pyrazole compound or a salt thereof according to the above [1] representing an integer of 1. [3] Z is the pyrazole compound or a salt thereof according to the above [1] representing Z-8 to Z-44 or Z-46. [4] G 1 represents a halogen atom, C1-C6 alkyl or C1-C6 haloalkyl, T represents an oxygen atom, R X represents C1-C6 alkyl, R Y represents a hydrogen atom, R 1 represents a hydrogen atom, R 2 represents a hydrogen atom, R 3 represents a hydrogen atom, R 4 represents a hydrogen atom, Z represents Z-8, Z-9, Z-10, Z-11, Z-14, Z-17, Z-19, Z-20, Z-24, Z-27, Z-39, Z-41 or Z-46. Z 1 represents cyano, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, E-3 or E-7, Z 2 represents C1-C6 alkyl, Z a represents a halogen atom or C1-C6 alkoxy, m5 represents an integer of 0 or 1, n4 represents an integer of 0, 1 or 2, n3 represents an integer of 0, 1 or 2, n2 represents an integer of 0 or 2, n1 represents an integer of 1, p represents an integer of 1, v4 represents an integer of 1, v3 is the pyrazole compound or a salt thereof according to the above [3] that represents an integer of 1. [5] An agricultural chemical containing, as an active ingredient, one or more selected from the pyrazole compounds and salts thereof according to any one of the above [1] to [4]. [6] A fungicide containing, as an active ingredient, one or more selected from the pyrazole compounds and salts thereof according to any one of the above [1] to [4]. [7] A fungicide for agricultural and horticultural use containing, as an active ingredient, one or more selected from the pyrazole compounds and salts thereof according to any one of the above [1] to [4]. [8] An antifungal agent containing, as an active ingredient, one or more selected from the pyrazole compounds and salts thereof according to any one of the above [1] to [4]. [9] An endoparasite control agent containing, as an active ingredient, one or more selected from the pyrazole compounds and salts thereof according to any one of the above [1] to [4].
[0251] [Example] The present invention will be described in more detail below by presenting synthesis examples and test examples of the compounds of the present invention as examples, but the present invention is not limited thereto.
[0252] For the medium-pressure preparative liquid chromatography described in the synthesis examples, a medium-pressure preparative apparatus of Yamazen Corporation; YFLC-Wprep (flow rate 18 ml / min, column of silica gel 40 μm) was used.
[0253] Also, the chemical shift values of the proton nuclear magnetic resonance spectra (hereinafter, 1 described as 1H-NMR) described below were measured at 300 MHz (model; JNM-ECX300 or JNM-ECP300, manufactured by JEOL Ltd.) or 400 MHz (model; JNM-ECZ400S, manufactured by JEOL Ltd.) using Me4Si (tetramethylsilane) as a reference substance. Incidentally, 1The symbols in the chemical shift values of 1H-NMR represent the following meanings. s: singlet, d: doublet, dd: double doublet, t: triplet, dt: double triplet, q: quartet, sep: septet, m: multiplet, br: broad singlet.
[0254] [Synthesis Example] [Synthesis Example 1] Synthesis of N-(2-(2,4-dimethylphenyl)-2,2-difluoroethyl)-1-phenyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide (Compound No. 2-001) [Step 1] Synthesis of 1-phenyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid To a mixed solution of 1.0 g of 4-iodo-1-phenyl-1H-pyrazole-5-carboxylic acid and 5 ml of xylene, 0.42 ml of 3-(trifluoromethyl)phenol, 1.6 g of cesium carbonate, 19 mg of 4-(dimethylamino)pyridine, and 33 mg of copper(I) trifluoromethanesulfonate toluene complex were sequentially added at room temperature. After nitrogen substitution, the mixture was stirred at reflux temperature for 8 hours. After completion of the reaction, 10 ml of water was added to the reaction mixture, and the aqueous layer was washed with 10 ml of diethyl ether. To the obtained aqueous layer, 35% by mass hydrochloric acid aqueous solution was added until the pH reached 1, and the mixture was extracted with 20 ml of ethyl acetate. The obtained organic layer was dehydrated and dried over saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 566 mg of the target product as a brown solid.
[0255] [Step 2] Synthesis of N-(2-(2,4-dimethylphenyl)-2,2-difluoroethyl)-1-phenyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide (Compound No. 2-001) To a mixed solution of 173 mg of 1-phenyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid obtained in Step 1 and 4 ml of dichloromethane, 226 mg of 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazol[4,5-b]pyridinium 3-oxide hexafluorophosphate, 0.17 ml of N,N-diisopropylethylamine, and 92 mg of 2-(2,4-dimethylphenyl)-2,2-difluoroethan-1-amine were added at room temperature, and the mixture was stirred at the same temperature for 3 hours. After completion of the reaction, 5 ml of 1 mol / l aqueous hydrochloric acid solution was added to the reaction mixture, and the mixture was extracted with 5 ml of dichloromethane. The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography using n-hexane:ethyl acetate [gradient from 9:1 to 1:9 (volume ratio, the same hereinafter)] as an eluent to obtain 62 mg of the target product as a yellow solid. Melting point: 82 - 85 °C.
[0256] Synthesis Example 2: Synthesis of N-(2,4-dimethylphenethyl)-1-ethyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide (Compound No. 2-159) To a mixed solution of 500 mg of N-(2,4-dimethylphenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide, 332 mg of potassium carbonate, and 5 ml of dimethylformamide, 0.19 ml of ethyl iodide was added at room temperature, and the mixture was stirred at 50 °C for 1 hour. After completion of the reaction, 5 ml of saturated aqueous ammonium chloride solution was added at room temperature, and the mixture was extracted with diisopropyl ether (5 ml × 2 times). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 9:1 to 1:9) as an eluent to obtain 66 mg of the target product as a colorless oil. 11H-NMR (CDCl3, Me4Si, 300 MHz): δ 7.51 - 7.34 (m, 2H), 7.28 - 7.04 (m, 3H), 6.97 - 6.65 (m, 4H), 4.67 (q, J = 7.2 Hz, 2H), 3.69 - 3.52 (m, 2H), 2.80 (t, J = 6.8 Hz, 2H), 2.23 (s, 3H), 2.21 (s, 3H), 1.46 (t, J = 7.2 Hz, 3H).
[0257] Synthesis Example 3: Synthesis of 1-(tert-butyl)-N-(1-(2,4-dimethylphenyl)-3-(methylsulfonyl)propan-2-yl)-4-phenoxy-1H-pyrazole-5-carboxamide (Compound No. 3-011) To a mixed solution of 289 mg of 1-(tert-butyl)-N-(1-(2,4-dimethylphenyl)-3-(methylthio)propan-2-yl)-4-phenoxy-1H-pyrazole-5-carboxamide and 5 ml of dichloromethane, 158 mg of meta-chloroperbenzoic acid (containing 30% by mass of water) was added under ice-cooling, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, 5 ml of a saturated aqueous sodium sulfite solution was added at room temperature, and the mixture was extracted with chloroform (5 ml × 1 time). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 9:1 to 1:9) as the eluent to obtain 61 mg of the target product as a solid. Melting point 131 - 133 °C.
[0258] Synthesis Example 4: Synthesis of 1-(tert-butyl)-N-(2,4-dimethylphenethyl)-N-methyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide (Compound No. 5-001) To a mixed solution of 92 mg of 1-(tert-butyl)-N-(2,4-dimethylphenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide and 1 ml of N,N-dimethylformamide, 16 mg of 63% by mass sodium hydride (dispersed in mineral oil) and 25 μl of methyl iodide were sequentially added under ice cooling, and the mixture was stirred at room temperature for 4 hours. After completion of the reaction, 3 ml of a saturated aqueous ammonium chloride solution was added at room temperature, and the mixture was extracted with diisopropyl ether (3 ml × 2 times). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 9:1 to 1:9) as the eluent to obtain 65 mg of the target product as a colorless oily substance. 1 H-NMR (CDCl3, Me4Si, 400 MHz): δ 7.43 - 7.35 (m, 1H), 7.32 - 7.27 (m, 2H), 7.20 - 7.12 (m, 1H), 7.03 - 6.90 (m, 3H), 6.89 - 6.83 (m, 1H), 3.80 - 3.28 (m, 2H), 3.10 - 2.55 (m, 5H), 2.30 - 2.16 (m, 6H), 1.68 - 1.59 (m, 9H).
[0259] Synthesis Example 5: Synthesis of 1-isopropyl-N-(4-methylphenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carbothioamide (Compound No. 6-002) To a mixed solution of 300 mg of 1-isopropyl-N-(4-methylphenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide and 4 ml of xylene, 340 mg of Lawesson's reagent was added at room temperature, and the mixture was stirred at 120 °C for 2 hours. After completion of the reaction, 5 ml of n-hexane was added at room temperature, and the insoluble matter was filtered off. The obtained filtrate was concentrated under reduced pressure to remove the solvent. The obtained residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 9:1 to 1:9) as the eluent to obtain 311 mg of the target product as a resinous substance. 1 1H-NMR (CDCl3, Me4Si, 400 MHz): δ 8.05 - 7.92 (m, 1H), 7.45 - 7.32 (m, 2H), 7.20 (s, 1H), 7.18 - 7.14 (m, 1H), 7.07 - 6.98 (m, 5H), 5.87 (sep, J = 6.5 Hz, 1H), 4.02 - 3.93 (m, 2H), 2.87 (t, J = 6.8 Hz, 2H), 2.26 (s, 3H), 1.48 (d, J = 6.5 Hz, 6H).
[0260] Synthesis Example 6: Synthesis of 1-(tert-Butyl)-N-(4-ethoxyphenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide (Compound No. 2-092) To a mixed solution of 80 mg of 1-(tert-butyl)-N-(4-hydroxyphenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide and 3 ml of N,N-dimethylformamide, 62 mg of potassium carbonate and 36 μl of ethyl iodide were sequentially added at room temperature, and the mixture was stirred at 60 °C for 3 hours. After completion of the reaction, 3 ml of a saturated aqueous ammonium chloride solution was added at room temperature, and the mixture was extracted with diisopropyl ether (3 ml × 2 times). The obtained organic layer was washed with water, dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 74 mg of the target product as a pale yellow solid. Melting point 74 - 77 °C.
[0261] Synthesis Example 7: Synthesis of N-(4-acetamidophenethyl)-1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide (Compound No. 4-001) To a mixed solution of 200 mg of N-(4-aminophenethyl)-1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide and 2 ml of dichloromethane, 91 mg of acetic anhydride was added at room temperature, and the mixture was stirred at the same temperature for 1 hour. After completion of the reaction, 3 ml of water was added at room temperature, and the mixture was extracted with dichloromethane (3 ml × 2 times). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (2:1) as an eluent to obtain 120 mg of the target product as a resinous substance. 1 H-NMR (CDCl3, Me4Si, 400 MHz): δ 7.47 - 7.39 (m, 1H), 7.38 - 7.29 (m, 3H), 7.23 - 7.16 (m, 1H), 7.14 (s, 1H), 7.12 - 6.99 (m, 4H), 6.50 - 6.35 (m, 1H), 3.66 - 3.56 (m, 2H), 2.76 (t, J = 6.8 Hz, 2H), 2.17 (s, 3H), 1.72 (s, 9H).
[0262] [Reference Example] The following shows the production method of the production intermediate of the compound of the present invention as a reference example.
[0263] Reference Example 1: Synthesis of 4-iodo-1-phenyl-1H-pyrazole-5-carboxylic acid To a mixed solution of 2.0 g of 1-phenyl-1H-pyrazole-5-carboxylic acid and 10 ml of acetic acid, 2.5 g of N-iodosuccinimide was added at room temperature, and the mixture was stirred at 80 °C for 30 minutes. After completion of the reaction, 50 ml of water was added at room temperature, and the precipitated solid was collected by filtration. The obtained solid was dried under reduced pressure to obtain 2.69 g of the target product as a peach-colored solid. Melting point 191 - 193 °C.
[0264] Reference Example 2: Synthesis of 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid Project 1: Synthesis of 4-(dimethylamino)-3-(3-(trifluoromethyl)phenoxy)but-3-en-2-one A mixed solution of 4.7 g of 1-(3-(trifluoromethyl)phenoxy)propan-2-one and 2.9 g of N,N-dimethylformamide dimethylacetal was stirred at 80 °C for 16 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography using ethyl acetate as the eluent. 10 ml of diisopropyl ether and 10 ml of n-hexane were added to the obtained oily substance, and the precipitated solid was collected by filtration. The obtained solid was dried under reduced pressure to obtain 2.36 g of the target product as a light brown solid. Melting point 112 - 114 °C.
[0265] Project 2: Synthesis of 1-(tert-butyl)-5-methyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole A mixed solution of 2.4 g of 4-(dimethylamino)-3-(3-(trifluoromethyl)phenoxy)but-3-en-2-one, 1.64 g of tert-butylhydrazine hydrochloride and 25 ml of 1,4-dioxane was stirred at 100 °C for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. 20 ml of water was added to the obtained residue, and extraction was carried out with n-hexane (20 ml × 2 times). The obtained organic layer was dehydrated and dried with saturated brine and then anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (5:1) as the eluent to obtain 2.51 g of the target product as a pale yellow oily substance. 1 1H-NMR (CDCl3, Me4Si, 300 MHz): δ 7.42 - 7.32 (m, 1H), 7.28 (s, 1H), 7.28 - 7.22 (m, 1H), 7.21 - 7.14 (m, 1H), 7.12 - 7.04 (m, 1H), 2.29 (s, 3H), 1.66 (s, 9H).
[0266] Step 3: Synthesis of 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid To a mixed solution of 930 mg of 1-(tert-butyl)-5-methyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole, 8.5 ml of tert-butyl alcohol and 4.3 ml of water, 1.48 g of potassium permanganate was added at room temperature, and the mixture was stirred at 100 °C for 2 hours. After completion of stirring, 1.48 g of potassium permanganate was added to the reaction mixture at the same temperature, and the mixture was stirred at the same temperature for 2 hours. After completion of the reaction, the reaction mixture was filtered through celite, and the celite was washed with 20 ml of water. The aqueous layer of the obtained filtrate was washed with chloroform (20 ml × 2 times), then 1 mol / l hydrochloric acid aqueous solution was added until the pH reached 1, and the mixture was extracted with chloroform (20 ml × 2 times). The obtained organic layer was washed with water, then with saturated brine, and then dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained solid was washed with 5 ml of n-hexane and then dried under reduced pressure to obtain 209 mg of the target product as a white solid. Melting point: 120 - 124 °C.
[0267] Reference Example 3: Synthesis of 1-benzyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid Step 1: Synthesis of 3-(dimethylamino)-2-(3-(trifluoromethyl)phenoxy)acrolein To 15 ml of N,N-dimethylformamide, 5.6 ml of phosphorus oxychloride was added under ice-cooling, and the mixture was stirred at the same temperature for 15 minutes. After completion of stirring, a solution of 5.0 g of 1-(2,2-dimethoxyethoxy)-3-(trifluoromethyl)benzene in 5 ml of N,N-dimethylformamide was added to the reaction mixture under ice-cooling, and the mixture was stirred at 70 °C for 30 minutes. After completion of the reaction, the reaction mixture was added to a mixed solution of 28 g of potassium carbonate, 50 ml of water and 5 ml of ethanol, and the mixture was stirred at room temperature for 1 hour. After completion of stirring, the reaction mixture was extracted with toluene (40 ml × 2 times). The obtained organic layer was washed with water, then with saturated brine, and then dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 4.40 g of the target product as a brown oil. 1 1H-NMR (CDCl3, Me4Si, 400 MHz): δ 8.82 (s, 1H), 7.52 - 7.03 (m, 3H), 7.03 - 6.95 (m, 1H), 6.62 (s, 1H), 3.12 (br, 6H).
[0268] Step 2: Synthesis of 1-benzyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole A mixed solution of 2.0 g of 3-(dimethylamino)-2-(3-(trifluoromethyl)phenoxy)acrolein, 2.4 g of benzylhydrazine hydrochloride, 2.1 ml of triethylamine and 25 ml of 1,4-dioxane was stirred at 100 °C for 3 hours. After completion of the reaction, 20 ml of 1 mol / l hydrochloric acid aqueous solution was added to the reaction mixture at room temperature, and the mixture was extracted with chloroform (30 ml × 2 times). The obtained organic layer was washed with water, then with saturated brine, and then dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 9:1 to 1:9) as the eluent, and 400 mg of the target product was obtained as a red oily substance. 1 1H-NMR (CDCl3, Me4Si, 400 MHz): δ 7.46 - 7.20 (m, 7H), 7.20 - 7.14 (m, 2H), 7.10 - 7.06 (m, 1H), 7.03 - 6.96 (m, 1H), 5.29 (s, 2H) Step 3: Synthesis of 1-benzyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid Under a nitrogen atmosphere, 0.85 ml of a 1.6 mol / l n-hexane solution of n-butyllithium was added dropwise to a 10 ml solution of 360 mg of 1-benzyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole in tetrahydrofuran at -78°C, and the mixture was stirred at the same temperature for 10 minutes. After completion of the stirring, 1.0 g of dry ice was added to the reaction mixture at -78°C, and the mixture was stirred at the same temperature for 5 minutes. After completion of the reaction, 10 ml of a 1 mol / l aqueous hydrochloric acid solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate (10 ml × 2 times). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography using n-hexane:ethyl acetate:acetic acid (gradient from 74:25:1 to 39:60:1) as the eluent to obtain 45 mg of the target product as a colorless solid. Melting point 124 - 126°C.
[0269] Reference Example 4: Synthesis of 1-(2,4-dimethylphenyl)-3-ethoxypropan-2-amine Step 1: Synthesis of tert-butyl (1-(2,4-dimethylphenyl)-3-hydroxypropan-2-yl)carbamate 2.7 g of sodium borohydride was added to a 110 ml tetrahydrofuran solution of 11.5 g of ethyl 2-((tert-butoxycarbonyl)amino)-3-(2,4-dimethylphenyl)propanoate at room temperature. After completion of the addition, 22 ml of methanol was added dropwise at 65°C, and the mixture was stirred at the same temperature for 2 hours. After completion of the reaction, water was added to the reaction mixture at room temperature, and the solvent was distilled off under reduced pressure. Saturated brine was added to the obtained residue, and the mixture was extracted with ethyl acetate (50 ml × 2 times). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 9.76 g of a crude product of the target product as a colorless solid. This was used in the next step as it was without further purification. 1H-NMR (CDCl3, Me4Si, 300 MHz) δ 7.07 - 6.91 (m, 3H), 4.89 - 4.64 (m, 1H), 3.93 - 3.74 (m, 1H), 3.74 - 3.49 (m, 2H), 2.89 - 2.72 (m, 2H), 2.43 (br, 1H), 2.33 (s, 3H), 2.29 (s, 3H), 1.42 (s, 9H).
[0270] Step 2: Synthesis of tert-Butyl (1-(2,4-Dimethylphenyl)-3-ethoxypropan-2-yl)carbamate (1-(2,4-Dimethylphenyl)-3-hydroxypropan-2-yl)carbamate (1.0 g) and 20 ml of n-hexane were mixed, and 2 ml of 50% by mass aqueous sodium hydroxide solution, 12 mg of tetrabutylammonium bromide, and 828 mg of diethyl sulfate were sequentially added at room temperature, followed by stirring at 65°C for 5 hours. After completion of stirring, the mixture was stirred at room temperature for 14 hours and then at 65°C for 8 hours. After completion of the reaction, 20 ml of water was added at room temperature, and the mixture was extracted with 10 ml of ethyl acetate. The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography using ethyl acetate as the eluent to obtain 1.04 g of the target product as a colorless oily substance. 1 H-NMR (CDCl3, Me4Si, 300 MHz) δ 7.06 - 6.99 (m, 1H), 6.98 - 6.88 (m, 2H), 5.02 - 4.87 (m, 1H), 3.94 - 3.76 (m, 1H), 3.52 - 3.38 (m, 2H), 3.36 - 3.23 (m, 2H), 2.90 - 2.75 (m, 2H), 2.33 (s, 3H), 2.28 (s, 3H), 1.42 (s, 9H), 1.21 (t, J = 6.9 Hz, 3H).
[0271] Step 3: Synthesis of 1-(2,4-Dimethylphenyl)-3-ethoxypropan-2-amine To a mixed solution of 1.04 g of tert-butyl (1-(2,4-dimethylphenyl)-3-ethoxypropan-2-yl)carbamate and 15 ml of 1,4-dioxane, 5 ml of a 35% by mass aqueous hydrochloric acid solution was added at room temperature, and the mixture was stirred at the same temperature for 18 hours. After completion of the reaction, the solvent of the reaction mixture was distilled off under reduced pressure. To the obtained residue, 10 ml of water was added, and the residue was washed with a mixed solution of 10 ml of n-hexane and 10 ml of ethyl acetate. To the obtained aqueous layer, a 1 mol / l aqueous sodium hydroxide solution was added to adjust the pH to 10, and then the mixture was extracted with 20 ml of ethyl acetate. The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 657 mg of the target product as a colorless oily substance. 1 1H-NMR (CDCl3, Me4Si, 300 MHz) δ 7.06 - 6.90 (m, 3H), 3.56 - 3.39 (m, 3H), 3.31 - 3.15 (m, 2H), 2.80 - 2.69 (m, 1H), 2.57 - 2.46 (m, 1H), 2.29 (s, 6H), 1.21 (t, J = 6.9 Hz, 3H) (the proton peak of NH2 could not be observed).
[0272] Reference Example 5: Synthesis of N-(2,4-dimethylphenyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide To a mixed solution of 459 mg of 1-(tert-butyl)-N-(2,4-dimethylphenyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide and 5 ml of dichloromethane, 1 ml of trifluoroacetic acid was added at room temperature, and the mixture was stirred at the same temperature for 2 hours and 30 minutes. After completion of the reaction, the solvent of the reaction mixture was distilled off under reduced pressure. To the obtained residue, 10 ml of toluene was added, and the solvent was distilled off again under reduced pressure. The obtained residue was washed with 3 ml of diisopropyl ether to obtain 131 mg of the target product as a white solid. Melting point 132 - 134 °C.
[0273] Reference Example 6: Synthesis of 1-(2,4-dimethylphenyl)-3-(methylthio)propan-2-amine Project 1: Synthesis of 2-((tert-Butoxycarbonyl)amino)-3-(2,4-dimethylphenyl)propyl 4-methylbenzenesulfonate (1-(2,4-Dimethylphenyl)-3-hydroxypropan-2-yl)carbamic acid tert-butyl (5.00 g), N-methylimidazole (1.76 g), triethylamine (2.17 g) and toluene (30 ml) were mixed, and p-toluenesulfonyl chloride (4.09 g) was added thereto at room temperature. The mixture was stirred at the same temperature for 2 hours. After completion of the reaction, water (30 ml) was added at room temperature, and the mixture was extracted with ethyl acetate (30 ml × 1 time). The obtained organic layer was washed with 1 mol / l hydrochloric acid, then with saturated brine, and then dehydrated and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography using ethyl acetate as an eluent. The obtained solid was washed with 20 ml of diisopropyl ether to obtain 5.20 g of the target product as a white solid. Melting point: 90 - 93°C.
[0274] Project 2: Synthesis of S-(2-((tert-Butoxycarbonyl)amino)-3-(2,4-dimethylphenyl)propyl) ethanethioate Potassium thioacetate (0.75 g) was added to a mixed solution of 2-((tert-Butoxycarbonyl)amino)-3-(2,4-dimethylphenyl)propyl 4-methylbenzenesulfonate (1.90 g) and N,N-dimethylformamide (9 ml) at room temperature. The mixture was stirred at the same temperature for 2 hours and 30 minutes. After completion of the reaction, water (20 ml) was added at room temperature, and the mixture was extracted with ethyl acetate (20 ml × 1 time). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 1.51 g of the target product as a yellow solid. Melting point: 92 - 94°C.
[0275] Project 3: Synthesis of (1-(2,4-Dimethylphenyl)-3-(methylthio)propan-2-yl)carbamic acid tert-butyl To a mixed solution of 1.51 g of S-(2-((tert-butoxycarbonyl)amino)-3-(2,4-dimethylphenyl)propyl) ethanethioate, 1.21 g of potassium carbonate and 8 ml of methanol, 0.93 g of methyl iodide was added at room temperature, and the mixture was stirred at the same temperature for 1 hour and 30 minutes. After completion of the reaction, the solvent was distilled off under reduced pressure. 10 ml of water was added to the obtained residue, and the mixture was extracted with ethyl acetate (10 ml × 1 time). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 1.28 g of the target product as a white solid. Melting point 70 - 72 °C.
[0276] Step 4: Synthesis of 1-(2,4-dimethylphenyl)-3-(methylthio)propan-2-amine To a mixed solution of 1.28 g of tert-butyl (1-(2,4-dimethylphenyl)-3-(methylthio)propan-2-yl)carbamate and 10 ml of 1,4-dioxane, 3 ml of 35% by mass hydrochloric acid was added at room temperature, and the mixture was stirred at the same temperature for 3 hours and 30 minutes. After completion of the reaction, the solvent was distilled off under reduced pressure. The obtained aqueous layer was washed with a mixed solution of n-hexane:ethyl acetate = 1:1 (volume ratio) (100 ml × 2 times). To the obtained aqueous layer, 1 mol / l aqueous sodium hydroxide solution was added until the pH reached 13, and the mixture was extracted with ethyl acetate (10 ml × 1 time). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 0.61 g of the target product as an oily substance. 1 1H-NMR (CDCl3, Me4Si, 400 MHz) δ 7.07 - 6.89 (m, 3H), 3.21 - 3.28 (m, 1H), 2.92 - 2.39 (m, 4H), 2.29 (s, 6H), 2.11 (s, 3H). The NH2 proton was not observed.
[0277] Reference Example 7: Synthesis of 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylic acid (Compound No. i-036) Step 1: Synthesis of methyl 4-(3-bromophenoxy)-1-(tert-butyl)-1H-pyrazole-5-carboxylate (Compound No. ii-004) (4-(3-Bromophenoxy)-1-(tert-butyl)-1H-pyrazole-5-carboxylic acid (1.00 g) and 10 ml of acetone were mixed, and 0.49 g of potassium carbonate and 0.67 g of dimethyl sulfate were sequentially added thereto at room temperature, followed by stirring at the same temperature for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. 20 ml of water was added to the obtained residue, and the mixture was extracted with ethyl acetate (20 ml × 2 times). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 0.90 g of the target product as a yellow solid. Melting point: 69 - 71 °C.
[0278] Step 2: Synthesis of methyl 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylate (Compound No. ii-005) Under a nitrogen atmosphere, 0.10 g of [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride was added to a mixed solution of 0.50 g of methyl 4-(3-bromophenoxy)-1-(tert-butyl)-1H-pyrazole-5-carboxylate, 0.89 g of trimethylboroxine, 0.92 g of cesium carbonate, and 10 ml of 1,4-dioxane at room temperature, and the mixture was stirred at 100 °C for 16 hours. After completion of the reaction, 20 ml of water was added to the reaction mixture, and the mixture was extracted with ethyl acetate (20 ml × 3 times). After dehydration and drying with saturated brine and then anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 10:0 to 9:1) as the eluent to obtain 0.30 g of the target product as a yellow oil. 1 1H-NMR (CDCl3, Me4Si, 400 MHz) δ 7.24 (s, 1H), 7.20 - 7.13 (m, 1H), 6.90 - 6.85 (m, 1H), 6.84 - 6.76 (m, 2H), 3.77 (s, 3H), 2.33 (s, 3H), 1.72 (s, 3H).
[0279] Process 3: Synthesis of 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylic acid (Compound No. i-036) (To a mixed solution of 39.0 g of methyl 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylate and 100 ml of methanol, a mixed solution of 27.1 g of sodium hydroxide and 100 ml of water was added at room temperature, and the mixture was stirred at 45 °C for 16 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. After adding 50 ml of water to the obtained residue, an aqueous 35% by mass hydrochloric acid solution was added until the pH reached 2, and the precipitated solid was collected by filtration. The obtained solid was dried under reduced pressure and then washed with 100 ml of n-hexane to obtain 37.0 g of the target product as a white solid.) Melting point: 116 - 118 °C.
[0280] Reference Example 8: Synthesis of 1-(tert-butyl)-3-chloro-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid (Compound No. i-039) Process 1: Synthesis of 1-(tert-butyl)-3-chloro-5-(dichloromethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole (To a mixed solution of 5.00 g of 1-(tert-butyl)-5-methyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole and 17 ml of N,N-dimethylformamide, 11.4 g of 1,3-dichloro-5,5-dimethylhydantoin was added portionwise at 70 °C, and the mixture was stirred at 100 °C for 1 hour. After completion of the reaction, an aqueous saturated sodium thiosulfate solution was added to the reaction mixture under ice cooling, and extraction was carried out with a mixed solution of n-hexane:ethyl acetate = 1:1 (30 ml × 1 time). The obtained organic layer was washed with water and saturated aqueous sodium bicarbonate, then with saturated brine, and then dehydrated and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 7.29 g of the target product as a brown oil.) 1 1H-NMR (CDCl3, Me4Si, 300 MHz): δ 7.46 - 7.37 (m, 1H), 7.35 - 7.29 (m, 1H), 7.25 - 7.21 (m, 1H), 7.15 - 7.06 (m, 2H), 1.71 (s, 9H).
[0281] Step 2: Synthesis of 1-(tert-butyl)-3-chloro-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carbaldehyde To a mixed solution of 7.29 g of 1-(tert-butyl)-3-chloro-5-(dichloromethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole, 16 ml of N,N-dimethylformamide and 8 ml of water, 5.04 g of calcium carbonate was added at room temperature, and the mixture was stirred at 100 °C for 5 hours. After completion of stirring, 1.68 g of calcium carbonate and 4 ml of water were added to the reaction mixture at 100 °C, and the mixture was stirred at the same temperature for 19 hours. After completion of stirring, 1.68 g of calcium carbonate was added to the reaction mixture at 100 °C, and the mixture was stirred at the same temperature for 24 hours. After completion of the reaction, the reaction mixture was filtered through celite, and the celite was washed with 20 ml of ethyl acetate. The obtained filtrate was extracted with a mixed solution of n-hexane:ethyl acetate = 1:1 (20 ml × 1 time). The obtained organic layer was washed with water, dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 5.56 g of the target product as a brown oily substance. 1 H-NMR (CDCl3, Me4Si, 300 MHz): δ 9.74 (s, 1H), 7.49 - 7.42 (m, 1H), 7.40 - 7.33 (m, 1H), 7.25 - 7.21 (m, 1H), 7.14 - 7.06 (m, 1H), 1.70 (s, 9H).
[0282] Step 3: Synthesis of 1-(tert-butyl)-3-chloro-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid To a mixed solution of 4.00 g of 1-(tert-butyl)-3-chloro-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carbaldehyde, 8.06 g of 2-methyl-2-butene, 30 ml of tert-butanol and 10 ml of water, 3.60 g of sodium dihydrogen phosphate dihydrate and 2.61 g of sodium chlorite (purity: 80% by mass) were added under ice-cooling, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure. 20 ml of diisopropyl ether was added to the obtained residue, and back extraction was carried out with 1 mol / l aqueous sodium hydroxide solution (20 ml × 1 time). 35% by mass hydrochloric acid was added to the obtained aqueous layer until the pH reached 1, and extraction was carried out with chloroform (20 ml × 1 time). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained solid was washed with 10 ml of n-hexane and then dried under reduced pressure to obtain 2.38 g of the target product as a pale yellow solid. Melting point 105 - 107 °C.
[0283] The compounds of the present invention can be synthesized according to the above-mentioned Synthesis Examples and Reference Examples. Examples of the compounds of the present invention prepared in the same manner as in Synthesis Examples 1 to 7 are shown in Tables 2 to 13, and examples of the production intermediates prepared in the same manner as in Reference Examples 1 to 6 are shown in Tables 14 to 15. However, the compounds of the present invention and the production intermediates are not limited thereto.
[0284] In the tables, the substituent described as "Me" represents "methyl", and similarly hereinafter, "Et" represents "ethyl", "nPr" represents "normal propyl", "nBu" represents "normal butyl", "tBu" represents "tertiary butyl", "iBu" represents "isobutyl", "iPr" represents "isopropyl", "cPr" represents "cyclopropyl", "cHx" represents "cyclohexyl", "Ph" represents "phenyl", and "Bn" represents "benzyl". Also, the notation of "*" indicates that the compound is an oily substance or a resinous compound without a melting point, "**" indicates that the compound decomposed when measuring the melting point, and "m.p." represents the melting point (unit: °C). Further, ">" in the tables represents a higher temperature. For example, ">300" in the tables means that the compound whose melting point was measured did not melt at 300 °C.
[0285] In the table, for example, the description of "4-" in "4-Me-Ph" represents the substitution position on the phenyl group as described below. For example, "4-Me-Ph" represents 4-methylphenyl, and "2,6-F2-Ph" represents 2,6-difluorophenyl. For example, the description of "4-" in "1-Me-Ph" represents the substitution position on the phenyl group as described below. For example, "4-Me-Ph" represents 4-methylphenyl, and "2,6-F2-Ph" represents 2,6-difluorophenyl.
[0286]
Chemical Structure
[0287] Also, the substituents represented by D-1a, E-2a, E-2b, E-2c, E-3a, E-4a, E-5a, E-7a, E-11a, E-12a, E-13a, E-14a, E-21a, E-22a, E-23a, E-24a, E-30a, E-31a, E-41a, F-3a, F-10a, F-11a, L-1 to L-4, Z-1a, Z-1b, Z-1c, Z-1d, Z-2a, Z-3a, Z-4a, Z-4b, Z-6a, Z-8a, Z-9a, Z-10a, Z-11a, Z-14a, Z-17a, Z-19a, Z-20a, Z-24a, Z-27a, Z-39a, and Z-41a each represent the following structures.
[0288]
Chemical Structure
[0289]
Chemical Structure
[0290]
Chemical Structure
[0291]
Chemical Structure
[0292]
Chem.
[0293] In addition, the numbers described in the above structural formulas are numbers representing substitution positions. For example, the description "6-OMe-(E-3a)" in the table represents the following structure. A structural formula without a description of a substituent represents an unsubstituted structure.
[0294]
Chem.
[0295] [Table 2]
[0296]
Chem.
[0297] ―――――――――――――――――――――――――――――――――― No. G Z R X R a R 2 m.p.(°C) ―――――――――――――――――――――――――――――――――― 1-001 3-CF3-Ph 4-Me-Ph Ph Me Me 152-154 1-002 3-CF3-Ph 4-Me-Ph tBu Me Me 139-141 1-003 3-CF3-Ph 4-Me-Ph Bn Me Me * 1-004 3-CF3-Ph Z-2a Ph H H 148-150 1-005 3-Br-Ph 4-Me-Ph tBu Me Me 121-122 1-006 3-CF3-Ph Z-3a tBu H H * 1-007 3-CF3-Ph Z-2a tBu H H 126-128 1-008 Ph 4-Me-Ph tBu Me Me 96-98 1-009 Ph Z-2a tBu H H * 1-010 Ph Z-3a tBu H H * 1-011 3-CF3-Ph 2,4-Me2-Ph tBu H H * 1-012 3-CF3-Ph 2,4-Cl2-Ph tBu Me H 129-131 1-013 3-CF3-Ph 2-Cl-Ph tBu Me H 102-104 1-014 3-CF3-Ph 3-Cl-Ph tBu Me H 82-84 1-015 3-CF3-Ph 4-Cl-Ph tBu Me H 129-131 1-016 3-CF3-Ph 4-Me-Ph tBu Me H 101-103 1-017 3-CF3-Ph Ph tBu Me Me 104-106 1-018 3-CF3-Ph 3-Cl-Ph tBu Me Me 122-124 1-019 3-CF3-Ph 4-Cl-Ph tBu Me Me 147-149 1-020 3-CF3-Ph 4-OMe-Ph tBu Me Me 139-141 1-021 2,4-Cl2-Ph 4-Me-Ph tBu Me Me * 1-022 Ph 2,4-Me2-Ph tBu CH2OMe H 102-104 1-023 3-CF3-Ph 2,4-Me2-Ph tBu CH2OMe H 127-129 1-024 3-Cl-Ph 4-Me-Ph tBu Me Me 109-111 1-025 4-Cl-Ph 4-Me-Ph tBu Me Me 122-124 1-026 3-OMe-Ph 4-Me-Ph tBu Me Me 88-89 1-027 3-OCF3-Ph 4-Me-Ph tBu Me Me 116-117 1-028 2,3-Cl2-Ph 4-Me-Ph tBu Me Me 147-149 1-029 2-Cl-Ph 4-Me-Ph tBu Me Me * 1-030 3,4-Cl2-Ph 4-Me-Ph tBu Me Me * 1-031 3-CF3-Ph 2-F-Ph tBu Me Me 104-106 1-032 3-CF3-Ph 2-Cl-Ph tBu Me Me 110-112 1-033 3-CF3-Ph 2-Br-Ph tBu Me Me 102-104 1-034 3-CF3-Ph 3-F-Ph tBu Me Me 98-100 1-035 3-CF3-Ph 3-Br-Ph tBu Me Me 134-136 1-036 3-CF3-Ph 4-F-Ph tBu Me Me 111-113 1-037 3-CF3-Ph 4-Br-Ph tBu Me Me 161-163 1-038 3-CF3-Ph 4-Me-Ph E-2a Me Me 173-175 ―――――――――――――――――――――――――――――――――― [Table 3]
[0298] [Chemical formula]
[0299] ―――――――――――――――――――――――――――――――――― No. G Z R X R 3 R 4 m.p.(℃) ―――――――――――――――――――――――――――――――――― 2-001 3-CF3-Ph 2,4-Me2-Ph Ph F F 82-85 2-002 3-CF3-Ph 2,4-Me2-Ph Me F F 88-91 2-003 3-CF3-Ph 2,4-Me2-Ph 2-Cl-Ph F F * 2-004 3-CF3-Ph 2,4-Me2-Ph tBu F F * 2-005 3-CF3-Ph 2,4-Me2-Ph Bn F F * 2-006 3-CF3-Ph 2,4-Me2-Ph 3-Cl-Ph F F 82-84 2-007 3-CF3-Ph 2,4-Me2-Ph 4-Cl-Ph F F 109-111 2-008 2-F-3-cPr-Ph 2,4-Me2-Ph Ph F F * 2-009 3-CF3-Ph 2,4-Cl2-Ph tBu H H * 2-010 3-CF3-Ph 2,4-Me2-Ph tBu H H 76-78 2-011 3-CF3-Ph 2,4-Cl2-Ph Ph H H 98-100 2-012 3-Br-Ph 2,4-Me2-Ph tBu H H * 2-013 3-Br-Ph 2,4-Me2-Ph tBu F F * 2-014 3-Br-Ph 2,4-Cl2-Ph tBu H H * 2-015 2-F-3-Cl-Ph 2,4-Me2-Ph tBu H H * 2-016 3-CF3-Ph 2,4-Me2-Ph iPr H H * 2-017 3-CF3-Ph 2,4-Me2-Ph cHx H H * 2-018 Ph 2,4-Me2-Ph tBu H H * 2-019 Ph 2,4-Cl2-Ph tBu H H * 2-020 2-F-3-Cl-Ph 2,4-Me2-Ph tBu F F * 2-021 2-F-3-Cl-Ph 2,4-Cl2-Ph tBu H H * 2-022 3-CF3-Ph 2,4-Me2-Ph tBu F H * 2-023 3-CF3-Ph Ph tBu H H * 2-024 3-CF3-Ph 2-Me-Ph tBu H H * 2-025 3-CF3-Ph 3-Me-Ph tBu H H 99-101 2-026 3-CF3-Ph 4-Me-Ph tBu H H 72-74 2-027 3-CF3-Ph 3,4-Cl2-Ph tBu H H * 2-028 3-CF3-Ph 2,6-Cl2-Ph tBu H H * 2-029 3-CF3-Ph 2,4-Me2-Ph C(Me)2Et H H * 2-030 Ph 2,4-Me2-Ph tBu F F * 2-031 3-CF3-Ph 2,4-Me2-Ph L-1 H H * 2-032 3-CF3-Ph 2,4-Me2-Ph CH(Me)Et H H * 2-033 3-cPr-Ph 2,4-Me2-Ph tBu H H * 2-034 3-CF3-Ph 2,4-Me2-Ph L-2 H H 126-128 2-035 3-CF3-Ph 2,4-Me2-Ph L-3 H H * 2-036 3-Me-Ph 2,4-Me2-Ph tBu H H * 2-037 3-CF3-Ph 4-NH2-Ph tBu H H * 2-038 3-CF3-Ph 4-OH-Ph tBu H H 99-102 2-039 3-C(O)NHiPr-Ph 2,4-Me2-Ph tBu H H 149-151 2-040 3-CF3-Ph 2-Me-4-Cl-Ph tBu H H * 2-041 3-C(O)Me-Ph 2,4-Me2-Ph tBu H H * 2-042 3-OH-Ph 2,4-Me2-Ph tBu H H * 2-043 3-C(=NOMe)Me-Ph 2,4-Me2-Ph tBu H H * 2-044 3-OMe-Ph 2,4-Me2-Ph tBu H H * 2-045 3-OiPr-Ph 2,4-Me2-Ph tBu H H * 2-046 3-OBn-Ph 2,4-Me2-Ph tBu H H * 2-047 3-OCH2CN-Ph 2,4-Me2-Ph tBu H H * 2-048 Ph 2,4-Me2-Ph tBu F H * 2-049 Ph Ph tBu H H * 2-050 Ph 4-Me-Ph tBu H H * 2-051 Ph 3-Me-Ph tBu H H * 2-052 Ph 2-Me-Ph tBu H H * 2-053 3-C(=NOiPr)Me-Ph 2,4-Me2-Ph tBu H H * 2-054 3-C(=NOtBu)Me-Ph 2,4-Me2-Ph tBu H H * 2-055 3-C(=NOH)Me-Ph 2,4-Me2-Ph tBu H H * 2-056 2-F-3-Cl-Ph 4-Me-Ph tBu H H * 2-057 3-CF3-Ph 2-OMe-Ph tBu H H 99-100 2-058 3-CF3-Ph 3-OMe-Ph tBu H H 109-111 2-059 3-CF3-Ph 4-OMe-Ph tBu H H * 2-060 3-CF3-Ph 3,4-(OMe)2-Ph tBu H H 100-102 2-061 3-CF3-Ph 2-Cl-Ph tBu H H * 2-062 3-CF3-Ph 3-Cl-Ph tBu H H * 2-063 3-CF3-Ph 4-Cl-Ph tBu H H 96-98 2-064 3-CF3-Ph 3-Br-Ph tBu H H 85-87 2-065 3-CF3-Ph 2-F-Ph tBu H H * 2-066 3-CF3-Ph 3-F-Ph tBu H H * 2-067 3-CF3-Ph 4-F-Ph tBu H H * 2-068 3-CF3-Ph 2-CF3-Ph tBu H H * 2-069 3-CF3-Ph 3-CF3-Ph tBu H H 107-108 2-070 3-CF3-Ph 4-CF3-Ph tBu H H 118-119 2-071 3-CF3-Ph 4-NO2-Ph tBu H H * 2-072 3-CF3-Ph 4-C(O)OMe-Ph tBu H H * 2-073 3-CF3-Ph 4-SO2Me-Ph tBu H H 168-170 2-074 3-CF3-Ph 4-SO2NH2-Ph tBu H H 154-156 2-075 3-CF3-Ph 4-CN-Ph tBu H H 124-125 2-076 3-CF3-Ph 2,4,6-Me3-Ph tBu H H * 2-077 3-CF3-Ph 2,4-Me2-Ph C(Me)2CN H H * 2-078 3-CF3-Ph 4-Br-Ph tBu H H 106-108 2-079 Ph 4-SO2Me-Ph tBu H H 119-121 2-080 Ph 4-CN-Ph tBu H H * 2-081 3-CF3-Ph 2-Br-Ph tBu H H * 2-082 3-C(O)OMe-Ph 2,4-Me2-Ph tBu H H * 2-083 4-NO2-Ph 2,4-Me2-Ph tBu H H 152-155 2-084 3-C(O)NHtBu-Ph 2,4-Me2-Ph tBu H H * 2-085 3-C(O)NHcHx-Ph 2,4-Me2-Ph tBu H H * 2-086 3-C(O)NMe2-Ph 2,4-Me2-Ph tBu H H * 2-087 3-CF3-Ph Ph tBu Me H * 2-088 3-CF3-Ph 2-Cl-4-Br-Ph tBu F F * 2-089 3-CF3-Ph Ph tBu Me Me * 2-090 Ph Ph tBu Me H * 2-091 3-CN-Ph 2,4-Me2-Ph tBu H H * 2-092 3-CF3-Ph 4-OEt-Ph tBu H H 74-77 2-093 3-Cl-Ph 2,4-Me2-Ph tBu H H * 2-094 Ph 4-Br-Ph tBu H H 100-102 2-095 3-F-Ph 2,4-Me2-Ph tBu H H * 2-096 3-I-Ph 2,4-Me2-Ph tBu H H * 2-097 4-Cl-Ph 2,4-Me2-Ph tBu H H * 2-098 2-Cl-Ph 2,4-Me2-Ph tBu H H * 2-099 3,4-Cl2-Ph 2,4-Me2-Ph tBu H H * 2-100 2,4-Cl2-Ph 2,4-Me2-Ph tBu H H * 2-101 Ph 2-OMe-Ph tBu H H * 2-102 Ph 3-OMe-Ph tBu H H * 2-103 Ph 4-OMe-Ph tBu H H * 2-104 Ph 3,4-(OMe)2-Ph tBu H H * 2-105 Ph 2-Cl-Ph tBu H H * 2-106 Ph 3-Cl-Ph tBu H H * 2-107 Ph 4-Cl-Ph tBu H H * 2-108 Ph 2-Br-Ph tBu H H * 2-109 Ph 2-F-Ph tBu H H * 2-110 Ph 3-F-Ph tBu H H * 2-111 Ph 4-F-Ph tBu H H * 2-112 Ph 2-CF3-Ph tBu H H * 2-113 Ph 3-CF3-Ph tBu H H * 2-114 Ph 4-CF3-Ph tBu H H 104-106 2-115 Ph 4-NO2-Ph tBu H H * 2-116 Ph 4-C(O)OMe-Ph tBu H H * 2-117 Ph 2,4,6-Me3-Ph tBu H H * 2-118 3-CF3-Ph Z-1a tBu H H * 2-119 3-CF3-Ph 3-Br-4-OMe-Ph tBu H H * 2-120 2,3-Cl2-Ph 2,4-Me2-Ph tBu H H * 2-121 3-Cl-Ph 4-Me-Ph tBu H H * 2-122 3-Cl-Ph 2,4-Cl2-Ph tBu H H * 2-123 3-OCF3-Ph 2,4-Me2-Ph tBu H H * 2-124 3-CF3-Ph 4-Me-Ph nBu H H * 2-125 3-CF3-Ph 4-Me-Ph CH2CF3H H * 2-126 3-CF3-Ph 4-Me-Ph CH2CH2tBu H H * 2-127 3-CF3-Ph 4-Me-Ph CH2cPr H H * 2-128 3-CF3-Ph 4-Me-Ph L-4 H H * 2-129 3-CF3-Ph 4-OnPr-Ph tBu H H 82-84 2-130 3-CF3-Ph 4-OiPr-Ph tBu H H 97-98 2-131 3-CF3-Ph 4-Et-Ph tBu H H * 2-132 3-CF3-Ph 4-SMe-Ph tBu H H 79-81 2-133 3-CF3-Ph Z-3a tBu H H * 2-134 3-CF3-Ph Z-2a tBu H H * 2-135 3-CF3-Ph 3,4-Me2-Ph tBu H H * 2-136 3-CF3-Ph 3-Cl-4-OMe-Ph tBu H H 104-106 2-137 3-CF3-Ph 3,4-(OEt)2-Ph tBu H H * 2-138 3-CF3-Ph 3-OMe-4-OEt-Ph tBu H H * 2-139 3-CF3-Ph 4-tBu-Ph tBu H H * 2-140 3-CF3-Ph Z-4a tBu H H * 2-141 Ph 4-OnPr-Ph tBu H H * 2-142 Ph 4-OiPr-Ph tBu H H * 2-143 Ph 4-OEt-Ph tBu H H * 2-144 Ph 4-Et-Ph tBu H H 67-69 2-145 Ph 4-tBu-Ph tBu H H * 2-146 Ph 4-SMe-Ph tBu H H * 2-147 Ph Z-3a tBu H H * 2-148 Ph Z-2a tBu H H * 2-149 Ph 3,4-Me2-Ph tBu H H * 2-150 Ph 3-Cl-4-OMe-Ph tBu H H * 2-151 Ph Z-4a tBu H H * 2-152 4-Cl-Ph 4-Me-Ph tBu H H * 2-153 4-Cl-Ph 2,4-Cl2-Ph tBu H H * 2-154 3-OMe-Ph 4-Me-Ph tBu H H * 2-155 3-OCF3-Ph 4-Me-Ph tBu H H * 2-156 2,4-Cl2-Ph 4-Me-Ph tBu H H * 2-157 3-F-Ph 4-Me-Ph tBu H H * 2-158 3-F-Ph 2,4-Cl2-Ph tBu H H * 2-159 3-CF3-Ph 2,4-Me2-Ph Et H H * 2-160 3-CF3-Ph 4-NHMe-Ph tBu H H * 2-161 3-CF3-Ph 4-Me-Ph tBu Cl H 86-88 2-162 4-CF3-Ph 4-Me-Ph tBu H H * 2-163 2-CF3-Ph 4-Me-Ph tBu H H 134-136 2-164 Ph 4-C(O)Me-Ph tBu H H 96-99 2-165 3-CF3-Ph 2-Cl-4-Me-Ph tBu H H * 2-166 3-CF3-Ph 2-Br-4-Me-Ph tBu H H 102-104 2-167 Ph 2-Cl-4-Me-Ph tBu H H * 2-168 Ph 2-Br-4-Me-Ph tBu H H * 2-169 3-CF3-Ph 3,4-(OH)2-Ph tBu H H * 2-170 3-CF3-Ph 2-Br-4-Me-Ph tBu OMe H * 2-171 3-CF3-Ph Z-6a tBu H H * 2-172 3-CF3-Ph 4-Me-Ph iPr H H 93-95 2-173 3-CF3-Ph 4-Me-Ph Ph H H * 2-174 Ph 4-CH(OH)Me-Ph tBu H H * 2-175 Ph 4-C(O)OEt-Ph tBu H H 90-92 2-176 Ph 4-C(O)OH-Ph tBu H H 73-76 2-177 3-CF3-Ph 2-Me-4-NO2-Ph tBu H H 74-76 2-178 Ph 2-Me-4-Cl-Ph tBu H H * 2-179 3-CF3-Ph 2,4-Br2-Ph tBu H H * 2-180 Ph 2,4-Br2-Ph tBu H H * 2-181 3-Me-Ph 2,4-Br2-Ph tBu H H * 2-182 3-CF3-Ph 2-F-4-Me-Ph tBu H H * 2-183 3-CF3-Ph 2-F-4-Cl-Ph tBu H H * 2-184 3-CF3-Ph 2-Br-4-Cl-Ph tBu H H * 2-185 3-CF3-Ph 2-Me-4-Br-Ph tBu H H * 2-186 3-CF3-Ph 4-Me-Ph tBu Me Me * 2-187 3-Me-Ph 2-F-4-Me-Ph tBu H H * 2-188 3-Me-Ph 2-F-4-Cl-Ph tBu H H * 2-189 3-Me-Ph 2-Br-4-Cl-Ph tBu H H * 2-190 3-Me-Ph 2-Me-4-Br-Ph tBu H H * 2-191 3-Methylphenyl 4-Methylphenyl tert-Butyl Methyl Methyl * 2-192 3-Methylphenyl 2-Chloro-4-Methylphenyl tert-Butyl Hydrogen Hydrogen * 2-193 3-Methylphenyl 2-Bromo-4-Methylphenyl tert-Butyl Hydrogen Hydrogen * 2-194 3-Methylphenyl 2-Methyl-4-Chlorophenyl tert-Butyl Hydrogen Hydrogen * 2-195 3-Methylphenyl 2,4-Dichlorophenyl tert-Butyl Hydrogen Hydrogen * 2-196 Phenyl 2-Fluoro-4-Methylphenyl tert-Butyl Hydrogen Hydrogen * 2-197 Phenyl 2-Fluoro-4-Chlorophenyl tert-Butyl Hydrogen Hydrogen * 2-198 Phenyl 2-Bromo-4-Chlorophenyl tert-Butyl Hydrogen Hydrogen * 2-199 Phenyl 2-Methyl-4-Bromophenyl tert-Butyl Hydrogen Hydrogen * 2-200 Phenyl 4-Methylphenyl tert-Butyl Methyl Methyl * 2-201 3-Chlorophenyl 2,4-Dibromophenyl tert-Butyl Hydrogen Hydrogen * 2-202 3-Bromophenyl 2,4-Dibromophenyl tert-Butyl Hydrogen Hydrogen * 2-203 3-Trifluoromethylphenyl 2,4-Dimethylphenyl E-2a Hydrogen Hydrogen * 2-204 3-Trifluoromethylphenyl 3-Methyl-4-Nitrophenyl tert-Butyl Hydrogen Hydrogen * 2-205 3-Trifluoromethylphenyl 4-Isobutylphenyl tert-Butyl Hydrogen Hydrogen * 2-206 3-Trifluoromethylphenyl 4-Isopropylphenyl tert-Butyl Hydrogen Hydrogen * 2-207 3-Trifluoromethylphenyl 4-Cyclopropylphenyl tert-Butyl Hydrogen Hydrogen * 2-208 3-Trifluoromethylphenyl 4-Vinylphenyl tert-Butyl Hydrogen Hydrogen * 2-209 Phenyl 2-Methyl-4-Fluorophenyl tert-Butyl Hydrogen Hydrogen * 2-210 3-Methylphenyl 2-Methyl-4-Fluorophenyl tert-Butyl Hydrogen Hydrogen * 2-211 3-Trifluoromethylphenyl 2-Methyl-4-Fluorophenyl tert-Butyl Hydrogen Hydrogen 77 - 79 2-212 Ph 2-Br-4-F-Ph tBu H H * 2-213 3-Me-Ph 2-Br-4-F-Ph tBu H H * 2-214 3-CF3-Ph 2-Br-4-F-Ph tBu H H * 2-215 Ph 2-OMe-4-F-Ph tBu H H * 2-216 3-Me-Ph 2-OMe-4-F-Ph tBu H H * 2-217 3-CF3-Ph 2-OMe-4-F-Ph tBu H H * 2-218 3-CF3-Ph 2-Cl-4-Br-Ph tBu H H * 2-219 Ph 2-Cl-4-Br-Ph tBu H H * 2-220 3-Me-Ph 2-Cl-4-Br-Ph tBu H H 66-68 2-221 3-CF3-Ph 2-Cl-4-OMe-Ph tBu H H * 2-222 Ph 2-Cl-4-OMe-Ph tBu H H * 2-223 3-Me-Ph 2-Cl-4-OMe-Ph tBu H H * 2-224 3-CF3-Ph Z-1b tBu H H * 2-225 Ph Z-1b tBu H H * 2-226 3-Me-Ph Z-1b tBu H H * 2-227 3-CF3-Ph 2-F-4-Br-Ph tBu H H 84-86 2-228 Ph 2-F-4-Br-Ph tBu H H * 2-229 3-Me-Ph 2-F-4-Br-Ph tBu H H 79-81 2-230 3-CF3-Ph 2-Me-4-OMe-Ph tBu H H 102-104 2-231 Ph 2-Me-4-OMe-Ph tBu H H * 2-232 3-Me-Ph 2-Me-4-OMe-Ph tBu H H * 2-233 3-CF3-Ph 2-F-4-OMe-Ph tBu H H 66-68 2-234 Ph 2-F-4-OMe-Ph tBu H H * 2-235 3-Me-Ph 2-F-4-OMe-Ph tBu H H * 2-236 3-Cl-Ph 2,4-Me2-Ph tBu F F * 2-237 3-Cl-Ph 2,4-Me2-Ph tBu F H * 2-238 3-Cl-Ph 4-Cl-Ph tBu H H 76-78 2-239 3-Cl-Ph 4-Br-Ph tBu H H 92-94 2-240 3-Cl-Ph 4-OMe-Ph tBu H H 91-93 2-241 3-Cl-Ph 3,4-(OMe)2-Ph tBu H H 94-96 2-242 3-Cl-Ph Z-4a tBu H H 122-124 2-243 3-Cl-Ph 4-Me-Ph tBu Me Me * 2-244 Ph 4-iPr-Ph tBu H H * 2-245 Ph Z-1c tBu H H * 2-246 3-Me-Ph Z-1c tBu H H * 2-247 3-CF3-Ph Z-1c tBu H H * 2-248 Ph 2,4,5-Me3-Ph tBu H H * 2-249 3-Me-Ph 2,4,5-Me3-Ph tBu H H * 2-250 3-CF3-Ph 2,4,5-Me3-Ph tBu H H * 2-251 3-CF3-Ph 3-Br-4-Me-Ph tBu H H * 2-252 3-SMe-Ph 2,4-Cl2-Ph tBu H H 104-106 2-253 Ph 2-OH-4-Me-Ph tBu H H * 2-254 Ph 2-OH-4-OMe-Ph tBu H H * 2-255 Ph 4-iBu-Ph tBu H H * 2-256 Ph 2-Br-4-OMe-Ph tBu H H * 2-257 3-CF3-Ph Z-4b tBu H H * 2-258 Ph Z-4b tBu H H * 2-259 3-Me-Ph Z-4b tBu H H * 2-260 Ph 3-Br-4-Me-Ph tBu H H * 2-261 3-Me-Ph 3-Br-4-Me-Ph tBu H H * 2-262 3-CF3-Ph 2-OH-4-Me-Ph tBu H H * 2-263 3-CF3-Ph 2-OH-4-OMe-Ph tBu H H * 2-264 3-Me-Ph 4-iPr-Ph tBu H H * 2-265 3-Me-Ph 2-OH-4-Me-Ph tBu H H * 2-266 3-Me-Ph 2-OH-4-OMe-Ph tBu H H * 2-267 3-SMe-Ph 4-Me-Ph tBu H H 102-104 2-268 3-SOMe-Ph 2,4-Cl2-Ph tBu H H * 2-269 3-SO2Me-Ph 2,4-Cl2-Ph tBu H H 147-149 2-270 3-Me-Ph 2,4-Me2-Ph tBu F F * 2-271 3-Me-Ph 2,4-Me2-Ph tBu F H * 2-272 3-Me-Ph 4-Cl-Ph tBu H H 81-83 2-273 3-Me-Ph 4-Br-Ph tBu H H 84-86 2-274 3-Me-Ph 4-OMe-Ph tBu H H 56-58 2-275 3-Methylphenyl 3,4-dimethoxyphenyl tert-butyl hydrogen hydrogen * 2-276 3-Methylphenyl Z-4a tert-butyl hydrogen hydrogen 91-93 2-277 3-Methylphenyl 4-methylphenyl tert-butyl hydrogen hydrogen 74-76 2-278 3-Chlorophenyl 2-fluoro-4-methylphenyl tert-butyl hydrogen hydrogen * 2-279 3-Chlorophenyl 2-fluoro-4-chlorophenyl tert-butyl hydrogen hydrogen * 2-280 3-Chlorophenyl 2-bromo-4-chlorophenyl tert-butyl hydrogen hydrogen 87-89 2-281 3-Chlorophenyl 2-methyl-4-bromophenyl tert-butyl hydrogen hydrogen * 2-282 3-Chlorophenyl Z-1c tert-butyl hydrogen hydrogen * 2-283 3-Chlorophenyl 2-chloro-4-methylphenyl tert-butyl hydrogen hydrogen * 2-284 3-Chlorophenyl 2-bromo-4-methylphenyl tert-butyl hydrogen hydrogen * 2-285 3-Chlorophenyl 2-methyl-4-chlorophenyl tert-butyl hydrogen hydrogen * 2-286 3-Bromophenyl 2-fluoro-4-methylphenyl tert-butyl hydrogen hydrogen * 2-287 3-Bromophenyl 2-fluoro-4-chlorophenyl tert-butyl hydrogen hydrogen 91-93 2-288 3-Bromophenyl 2-bromo-4-chlorophenyl tert-butyl hydrogen hydrogen * 2-289 3-Bromophenyl 2-methyl-4-bromophenyl tert-butyl hydrogen hydrogen * 2-290 3-Bromophenyl 4-methylphenyl tert-butyl methyl methyl * 2-291 3-Bromophenyl 2-chloro-4-methylphenyl tert-butyl hydrogen hydrogen * 2-292 3-Bromophenyl 2-bromo-4-methylphenyl tert-butyl hydrogen hydrogen 91-93 2-293 3-Bromophenyl 2-methyl-4-chlorophenyl tert-butyl hydrogen hydrogen 91-93 2-294 Phenyl 2,4-difluorophenyl tert-butyl hydrogen hydrogen * 2-295 3-Methylphenyl 2,4-difluorophenyl tert-butyl hydrogen hydrogen 76 - 78 2-296 3-Trifluoromethylphenyl 2,4-difluorophenyl tert-butyl hydrogen hydrogen 82 - 84 2-297 Phenyl 2,4-dimethoxyphenyl tert-butyl hydrogen hydrogen * 2-298 3-Methylphenyl 2,4-dimethoxyphenyl tert-butyl hydrogen hydrogen * 2-299 3-Trifluoromethylphenyl 2,4-dimethoxyphenyl tert-butyl hydrogen hydrogen * 2-300 3-Trifluoromethylphenyl 4-carboxyphenyl tert-butyl hydrogen hydrogen 160 - 163 2-301 3-Trifluoromethylphenyl 2-nitro-4-methylphenyl tert-butyl hydrogen hydrogen * 2-302 3-Chlorophenyl 2,4-dimethoxyphenyl tert-butyl hydrogen hydrogen * 2-303 3-Bromophenyl 2,4-dimethoxyphenyl tert-butyl hydrogen hydrogen * 2-304 3-Bromophenyl 2-chloro-4-methoxyphenyl tert-butyl hydrogen hydrogen * 2-305 3-Chlorophenyl 2-chloro-4-methoxyphenyl tert-butyl hydrogen hydrogen 82 - 84 2-306 3-Chlorophenyl 2-chloro-4-bromophenyl tert-butyl hydrogen hydrogen * 2-307 3-Methylsulfanylphenyl 4-methoxyphenyl tert-butyl hydrogen hydrogen 79 - 81 2-308 3-Trifluoromethylphenyl Z-1d tert-butyl hydrogen hydrogen * 2-309 3-Bromophenyl 2-chloro-4-bromophenyl tert-butyl hydrogen hydrogen * 2-310 3-Dimethylaminophenyl 4-methylphenyl tert-butyl hydrogen hydrogen * 2-311 3-Methylphenyl 2-bromo-4-methoxyphenyl tert-butyl hydrogen hydrogen * 2-312 3-Methylphenyl 4-isobutylphenyl tert-butyl hydrogen hydrogen * 2-313 3-Bromophenyl 2,4-dimethylphenyl tert-butyl fluorine hydrogen * 2-314 3-Bromophenyl 4-chlorophenyl tert-butyl hydrogen hydrogen 82 - 84 2-315 3-Bromo-phenyl 4-Bromo-phenyl tert-butyl H H 87-89 2-316 3-Bromo-phenyl 4-Methoxy-phenyl tert-butyl H H 89-91 2-317 3-Bromo-phenyl 3,4-(Methoxy)2-phenyl tert-butyl H H * 2-318 3-Bromo-phenyl Z-4a tert-butyl H H 136-138 2-319 3-Trifluoromethyl-phenyl 4-Hydroxymethyl-phenyl tert-butyl H H * 2-320 3-Trifluoromethyl-phenyl 2-Methoxy-4-methyl-phenyl tert-butyl H H * 2-321 3-Trifluoromethyl-phenyl 2-Ethoxy-4-methyl-phenyl tert-butyl H H 82-84 2-322 3-Trifluoromethyl-phenyl 2-Isopropoxy-4-methyl-phenyl tert-butyl H H 70-72 2-323 3-Trifluoromethyl-phenyl 4-Methyl-phenyl E-4a H H 105-107 2-324 3-Methyl-phenyl 2-Methoxy-4-methyl-phenyl tert-butyl H H * 2-325 3-Methyl-phenyl 2-Ethoxy-4-methyl-phenyl tert-butyl H H * 2-326 3-Methyl-phenyl 2-Isopropoxy-4-methyl-phenyl tert-butyl H H * 2-327 3-Chloro-phenyl 2-Fluoro-4-bromo-phenyl tert-butyl H H * 2-328 3-Chloro-phenyl 2-Methyl-4-methoxy-phenyl tert-butyl H H * 2-329 3-Chloro-phenyl 2-Fluoro-4-methoxy-phenyl tert-butyl H H * 2-330 3-Chloro-phenyl 2-Bromo-4-methoxy-phenyl tert-butyl H H * 2-331 3-Chloro-phenyl 2-Hydroxy-4-chloro-phenyl tert-butyl H H * 2-332 3-Bromo-phenyl 2-Fluoro-4-bromo-phenyl tert-butyl H H * 2-333 3-Bromo-phenyl 2-Methyl-4-methoxy-phenyl tert-butyl H H * 2-334 3-Bromo-phenyl 2-Fluoro-4-methoxy-phenyl tert-butyl H H * 2-335 3-Bromo-phenyl 2-Bromo-4-methoxy-phenyl tert-butyl H H * 2-336 3-Bromo-phenyl 2-Hydroxy-4-chloro-phenyl tert-butyl H H * 2-337 3-Bromo-phenyl Z-1b tert-butyl H H * 2-338 3-Bromo-phenyl Z-4b tert-butyl H H * 2-339 3-Bromo-phenyl 3-Bromo-4-methyl-phenyl tert-butyl H H * 2-340 3-Bromo-phenyl 2-Hydroxy-phenyl tert-butyl H H * 2-341 3-Chloro-phenyl Z-1b tert-butyl H H * 2-342 3-Chloro-phenyl Z-4b tert-butyl H H * 2-343 3-Chloro-phenyl 3-Bromo-4-methyl-phenyl tert-butyl H H * 2-344 3-Chloro-phenyl 2-Hydroxy-phenyl tert-butyl H H * 2-345 3-Chloro-phenyl 2-Methoxy-4-fluoro-phenyl tert-butyl H H * 2-346 3-Trifluoromethyl-phenyl 2,4-Dimethyl-phenyl E-3a H H * 2-347 Phenyl 2,4-Dimethyl-phenyl E-2a H H * 2-348 Phenyl 4-Methyl-phenyl E-2a H H * 2-349 Phenyl 2,4-Dimethyl-phenyl E-3a H H * 2-350 Phenyl 4-Methyl-phenyl E-3a H H * 2-351 3-Chloro-phenyl 2-Methyl-4-fluoro-phenyl tert-butyl H H * 2-352 3-Chloro-phenyl 2-Bromo-4-fluoro-phenyl tert-butyl H H * 2-353 3-Bromo-phenyl 2-Methyl-4-fluoro-phenyl tert-butyl H H 82-84 2-354 3-Trifluoromethyl-phenyl 2-Hydroxy-phenyl tert-butyl H H * 2-355 Phenyl 2-Hydroxy-phenyl tert-butyl H H * 2-356 3-Methyl-phenyl 2-Hydroxy-phenyl tert-butyl H H * 2-357 2,6-difluoro-phenyl 4-methyl-phenyl tert-butyl hydrogen hydrogen * 2-358 3-trifluoromethyl-phenyl 2-hydroxy-4-chloro-phenyl tert-butyl hydrogen hydrogen * 2-359 phenyl 2-hydroxy-4-chloro-phenyl tert-butyl hydrogen hydrogen * 2-360 3-methyl-phenyl 2-hydroxy-4-chloro-phenyl tert-butyl hydrogen hydrogen * 2-361 3-trifluoromethyl-phenyl 2-bromo-4-methoxy-phenyl tert-butyl hydrogen hydrogen * 2-362 3-bromo-phenyl 4-methyl-phenyl tert-butyl hydrogen hydrogen * 2-363 3-trifluoromethyl-phenyl 4-methyl-phenyl (E)-2a hydrogen hydrogen 81-83 2-364 3-trifluoromethyl-phenyl 4-chloro-phenyl (E)-2a hydrogen hydrogen 96-98 2-365 3-trifluoromethyl-phenyl 4-bromo-phenyl (E)-2a hydrogen hydrogen 76-78 2-366 3-trifluoromethyl-phenyl 4-methoxy-phenyl (E)-2a hydrogen hydrogen * 2-367 3-trifluoromethyl-phenyl 3,4-dimethoxy-phenyl (E)-2a hydrogen hydrogen * 2-368 3-trifluoromethyl-phenyl 4-methyl-phenyl (E)-2a methyl methyl * 2-369 3-trifluoromethyl-phenyl 2-fluoro-4-methyl-phenyl (E)-2a hydrogen hydrogen 69-71 2-370 3-trifluoromethyl-phenyl 2-chloro-4-methyl-phenyl (E)-2a hydrogen hydrogen 96-98 2-371 3-trifluoromethyl-phenyl 2-bromo-4-methyl-phenyl (E)-2a hydrogen hydrogen * 2-372 3-trifluoromethyl-phenyl 2-bromo-4-chloro-phenyl (E)-2a hydrogen hydrogen * 2-373 3-trifluoromethyl-phenyl 2-methyl-4-bromo-phenyl (E)-2a hydrogen hydrogen * 2-374 3-trifluoromethyl-phenyl 2,4-dibromo-phenyl (E)-2a hydrogen hydrogen * 2-375 3-trifluoromethyl-phenyl 2-fluoro-4-chloro-phenyl (E)-2a hydrogen hydrogen 107-109 2-376 3-trifluoromethyl-phenyl 4-methoxy-phenyl tert-butyl methyl hydrogen * 2-377 3-Methylphenyl 4-Methoxyphenyl tert-Butyl Methyl Hydrogen * 2-378 2-Fluorophenyl 4-Methylphenyl tert-Butyl Hydrogen Hydrogen * 2-379 2,3-Difluorophenyl 4-Methylphenyl tert-Butyl Hydrogen Hydrogen 102 - 104 2-380 2-Fluoro-3-Methoxyphenyl 4-Methylphenyl tert-Butyl Hydrogen Hydrogen * 2-381 2-Fluoro-3-Bromophenyl 4-Methylphenyl tert-Butyl Hydrogen Hydrogen 89 - 91 2-382 3-(Trifluoromethyl)phenyl 4-Methylphenyl (E)-2b Hydrogen Hydrogen 120 - 121 2-383 3-(Trifluoromethyl)phenyl 4-Methylphenyl (E)-2c Hydrogen Hydrogen 151 - 152 2-384 3-Methylphenyl 4-Methylphenyl tert-Butyl Methyl Hydrogen * 2-385 3-(Trifluoromethyl)phenyl 4-Methylphenyl tert-Butyl Methyl Hydrogen * 2-386 3-(Trifluoromethyl)phenyl 4-(Carboxamido)phenyl tert-Butyl Hydrogen Hydrogen 176 - 178 2-387 Phenyl 2-Methyl-4-Ethoxyphenyl tert-Butyl Hydrogen Hydrogen * 2-388 3-Methylphenyl 2-Methyl-4-Ethoxyphenyl tert-Butyl Hydrogen Hydrogen * 2-389 3-(Trifluoromethyl)phenyl 2-Methyl-4-Ethoxyphenyl tert-Butyl Hydrogen Hydrogen * 2-390 3-(Trifluoromethyl)phenyl 2-Methoxy-4-Chlorophenyl tert-Butyl Hydrogen Hydrogen 79 - 82 2-391 3-(Trifluoromethyl)phenyl 2-Ethoxy-4-Chlorophenyl tert-Butyl Hydrogen Hydrogen 106 - 108 2-392 Phenyl 2-Methoxy-4-Chlorophenyl tert-Butyl Hydrogen Hydrogen * 2-393 3-Methylphenyl 2-Methoxy-4-Chlorophenyl tert-Butyl Hydrogen Hydrogen * 2-394 2,3-Difluorophenyl 4-Methoxyphenyl tert-Butyl Hydrogen Hydrogen 94 - 96 2-395 2,3-Difluorophenyl 4-Chlorophenyl tert-Butyl Hydrogen Hydrogen 89 - 91 2-396 2,3-Difluorophenyl 4-Bromophenyl tert-Butyl Hydrogen Hydrogen * 2-397 2,3-difluoro-phenyl 2-methyl-4-methoxy-phenyl tert-butyl H H * 2-398 2,3-difluoro-phenyl 2-fluoro-4-methoxy-phenyl tert-butyl H H * 2-399 2,3-difluoro-phenyl 2-methoxy-4-methyl-phenyl tert-butyl H H * 2-400 2-fluoro-phenyl 4-methoxy-phenyl tert-butyl H H * 2-401 2-fluoro-phenyl 4-chloro-phenyl tert-butyl H H * 2-402 2-fluoro-phenyl 4-bromo-phenyl tert-butyl H H * 2-403 2-fluoro-phenyl 2-methyl-4-methoxy-phenyl tert-butyl H H * 2-404 2-fluoro-phenyl 2-fluoro-4-methoxy-phenyl tert-butyl H H * 2-405 2-fluoro-phenyl 2-methoxy-4-methyl-phenyl tert-butyl H H * 2-406 2-fluoro-3-methoxy-phenyl 4-methoxy-phenyl tert-butyl H H * 2-407 2-fluoro-3-methoxy-phenyl 4-chloro-phenyl tert-butyl H H * 2-408 2-fluoro-3-methoxy-phenyl 4-bromo-phenyl tert-butyl H H * 2-409 2-fluoro-3-methoxy-phenyl 2-methyl-4-methoxy-phenyl tert-butyl H H * 2-410 2-fluoro-3-methoxy-phenyl 2-fluoro-4-methoxy-phenyl tert-butyl H H * 2-411 2-fluoro-3-methoxy-phenyl 2-methoxy-4-methyl-phenyl tert-butyl H H * 2-412 3-trifluoromethyl-phenyl 2-chloro-4-ethoxy-phenyl tert-butyl H H * 2-413 phenyl 2-chloro-4-ethoxy-phenyl tert-butyl H H 81-83 2-414 3-methyl-phenyl 2-chloro-4-ethoxy-phenyl tert-butyl H H * 2-415 3-trifluoromethyl-phenyl 2-methoxy-4-bromo-phenyl tert-butyl H H * 2-416 3-methyl-phenyl 2-methoxy-4-bromo-phenyl tert-butyl H H * 2-417 3-Chloro-phenyl 2-methoxy-4-bromo-phenyl tert-butyl H H * 2-418 Phenyl 2-methoxy-4-bromo-phenyl tert-butyl H H 110 - 112 2-419 3-Chloro-phenyl 2-methoxy-4-methyl-phenyl tert-butyl H H * 2-420 Phenyl 2-methoxy-4-methyl-phenyl tert-butyl H H * 2-421 3-Trifluoromethyl-phenyl 4-(hydroxy-difluoromethyl)-phenyl tert-butyl H H * 2-422 3-Chloro-phenyl 2-methoxy-4-chloro-phenyl tert-butyl H H * 2-423 3-Trifluoromethyl-phenyl 4-(thiocarbamoyl)-phenyl tert-butyl H H 164 - 166 2-424 3-Methyl-phenyl 4-(methoxycarbonyl)-phenyl tert-butyl H H * 2-425 3-Methyl-phenyl 4-(carboxy)-phenyl tert-butyl H H 143 - 143 2-426 3-Methyl-phenyl 4-cyano-phenyl tert-butyl H H 85 - 87 ―――――――――――――――――――――――――――――――――― [Table 4]
[0300] [Chemical formula]
[0301] ―――――――――――――――――――――――――――――――――― No. G Z R X R a R 2 m.p.(°C) ―――――――――――――――――――――――――――――――――― 3-001 3-Trifluoromethyl-phenyl 2,4-dimethyl-phenyl tert-butyl CH2OEt H * 3-002 3-Bromo-phenyl 2,4-dimethyl-phenyl tert-butyl CH2OMe H * 3-003 3-Trifluoromethyl-phenyl 2,4-dimethyl-phenyl tert-butyl CH2OMe H * 3-004 Ph 2,4-Dimethylphenyl tert-Butyl Methoxymethyl Hydrogen * 3-005 Ph 2,4-Dimethylphenyl tert-Butyl Methylthiomethyl 111 - 114 3-006 3-Trifluoromethylphenyl 2,4-Dimethylphenyl tert-Butyl Methylthiomethyl 98 - 101 3-007 3-Trifluoromethylphenyl 2-Chloro-4-Bromophenyl tert-Butyl Methyl Hydrogen * 3-008 Ph 2-Chloro-4-Bromophenyl tert-Butyl Methyl Hydrogen * 3-009 3-Trifluoromethylphenyl 2,4-Dimethylphenyl tert-Butyl Methylsulfonylmethyl 152 - 154 3-010 3-Trifluoromethylphenyl 2,4-Dimethylphenyl tert-Butyl Methylsulfoxymethyl 136 - 138 3-011 Ph 2,4-Dimethylphenyl tert-Butyl Methylsulfonylmethyl 131 - 133 3-012 Ph 2,4-Dimethylphenyl tert-Butyl Methylsulfoxymethyl 159 - 161 ―――――――――――――――――――――――――――――――――― [Table 5]
[0302] [Chemical Structure]
[0303] ―――――――――――――――――――――――――――――――――― No. G Z 1 R X Melting Point (°C) ―――――――――――――――――――――――――――――――――― 4-001 3-Trifluoromethylphenyl N-Methylcarbamoyl tert-Butyl * 4-002 3-Trifluoromethylphenyl Methoxycarbonyl tert-Butyl * 4-003 3-Trifluoromethylphenyl Phenyl tert-Butyl 95 - 97 4-004 3-Trifluoromethylphenyl N-Methylsulfamoyl tert-Butyl * 4-005 3-CF3-Ph 6-OMe-(E-3a) tBu * 4-006 3-CF3-Ph NHC(O)NHEt tBu 164 - 166 4-007 3-CF3-Ph NHC(O)CF3tBu 146 - 148 4-008 3-CF3-Ph NHC(O)Ph tBu 192 - 194 4-009 3-CF3-Ph NHC(O)(5-Cl-(E-23a)) tBu 179 - 181 4-010 3-CF3-Ph NHC(O)(E-2a) tBu 129 - 131 4-011 3-CF3-Ph NHC(O)(E-4a) tBu 239 - 241 4-012 3-CF3-Ph NHSO2(4-Me-Ph) tBu 96 - 98 4-013 3-CF3-Ph NHSO2CF3tBu 129 - 131 4-014 3-CF3-Ph NHC(O)NMe2tBu 154 - 156 4-015 3-CF3-Ph NHSO2NMe2tBu 112 - 114 4-016 3-CF3-Ph NHC(O)OMe tBu 129 - 131 4-017 3-CF3-Ph OC(O)NHEt tBu 140 - 142 4-018 3-CF3-Ph E-21a tBu * 4-019 3-CF3-Ph E-31a tBu * 4-020 3-CF3-Ph E-3a tBu * 4-021 3-CF3-Ph 6-Cl-(E-3a) tBu 144 - 146 4-022 3-CF3-Ph E-7a tBu 129 - 131 4-023 3-CF3-Ph E-23a tBu 127 - 129 4-024 3-CF3-Ph E-14a tBu 117 - 119 4-025 3-CF3-Ph E-12a tBu * 4-026 3-CF3-Ph E-24a tBu * 4-027 3-CF3-Ph Ph tBu 147-149 4-028 Ph C≡CSiMe3tBu 101-103 4-029 Ph C≡CH tBu 115-117 4-030 3-CF3-Ph OCH2CH=CH2tBu 77-79 4-031 3-CF3-Ph OCH2C≡CH tBu * 4-032 3-CF3-Ph OCH2CF3tBu 72-74 4-033 3-CF3-Ph OCH2C(O)Me tBu * 4-034 3-CF3-Ph OCH2C(O)OMe tBu * 4-035 3-CF3-Ph OCH2C(O)NMe2tBu 108-109 4-036 3-CF3-Ph OCH2C(=NOMe)Me tBu * 4-037 3-CF3-Ph OBn tBu 115-117 4-038 3-CF3-Ph OCH2(E-2a) tBu 150-152 4-039 Ph OCH2cPr tBu * 4-040 Ph OCH2CH=CH2tBu * 4-041 Ph OCH2C≡CH tBu * 4-042 Ph OCH2CF3tBu 89-90 4-043 Ph OCH2C(O)Me tBu * 4-044 Ph OCH2C(O)OMe tBu * 4-045 Ph OCH2C(O)NMe2tBu * 4-046 Ph OCH2C(=NOMe)Me tBu * 4-047 Ph OBn tBu * 4-048 3-CF3-Ph NMeC(O)Me tBu 127-129 4-049 3-CF3-Ph NMeC(O)CF3tBu 92-94 4-050 3-CF3-Ph NMeC(O)OMe tBu * 4-051 3-CF3-Ph NMeC(O)NMe2tBu 76 - 78 4-052 3-CF3-Ph NMeC(O)(E-2a) tBu * 4-053 3-CF3-Ph 4-CN-Ph tBu 92 - 94 4-054 3-CF3-Ph 4-C(O)Me-Ph tBu 130 - 132 4-055 3-CF3-Ph 4-Me-Ph tBu 161 - 162 4-056 3-CF3-Ph 4-OMe-Ph tBu ** 4-057 3-CF3-Ph 4-C(O)OMe-Ph tBu 123 - 124 4-058 3-CF3-Ph 6-CF3-(E-3a) tBu 150 - 152 4-059 3-CF3-Ph 6-CN-(E-3a) tBu 130 - 131 4-060 3-CF3-Ph 6-F-(E-3a) tBu 114 - 115 4-061 3-CF3-Ph 6-OEt-(E-3a) tBu 97 - 99 4-062 3-CF3-Ph F-10a tBu 134 - 136 4-063 3-CF3-Ph F-11a tBu 119 - 120 4-064 Ph C(=NOMe)Me tBu * 4-065 3-CF3-Ph NHCO(E-3a) tBu 203 - 205 4-066 3-CF3-Ph NHCO(2-Cl-(E-3a)) tBu * 4-067 3-CF3-Ph NHCO(6-Cl-(E-3a)) tBu * 4-068 3-CF3-Ph NHCO(6-CF3-(E-3a)) tBu 197 - 199 4-069 3-CF3-Ph NHCO(E-8a) tBu 186 - 188 4-070 3-CF3-Ph NHCO(2-F-Ph) tBu 130 - 132 4-071 3-CF3-Ph NHCO(2-OMe-Ph) tBu 71 - 73 4-072 3-CF3-Ph NHCO(3-Me-(E-13a)) tBu 114 - 116 4-073 3-CF3-Ph NHCO(E-11a) tBu 178 - 180 4-074 3-CF3-Ph NHCO(E-14a) tBu 195 - 197 4-075 Ph CH(OMe)Me tBu * 4-076 3-Cl-Ph E-2a tBu * 4-077 3-CF3-Ph OCH2(6-OMe-(E-2a)) tBu 132 - 134 4-078 3-CF3-Ph OCH2(6-Me-(E-2a)) tBu * 4-079 3-CF3-Ph OCH2(F-3a) tBu * 4-080 3-CF3-Ph OCH2(3,5-Me2-4-OMe-(E-2a)) tBu * 4-081 3-CF3-Ph OCH2(3-Me-4-OCH2CF3-(E-2a)) tBu * 4-082 3-CF3-Ph OCH2(4,6-(OMe)2-(E-5a)) tBu * 4-083 3-CF3-Ph OCH2(4-C(O)OMe-(E-22a)) tBu * 4-084 3-CF3-Ph OCH2(6-Cl-(E-3a)) tBu * 4-085 3-CF3-Ph OCH2(2-Cl-(E-30a)) tBu * 4-086 3-CF3-Ph OCH2(2-CN-Ph) tBu 124 - 126 4-087 3-CF3-Ph OCH2(5-Me-(E-41a)) tBu 99 - 101 4-088 3-CF3-Ph OCH2(3,4-(OMe)2-(E-2a)) tBu * 4-089 3-CF3-Ph OCH2(6-Cl-(E-2a)) tBu 130-131 4-090 3-CF3-Ph OCH2(6-Br-(E-2a)) tBu 120-121 4-091 Ph OCH2(6-OMe-(E-2a)) tBu * 4-092 Ph OCH2(6-Cl-(E-2a)) tBu * 4-093 3-CF3-Ph E-2a tBu 112-114 4-094 3-Me-Ph E-2a tBu * 4-095 Ph E-2a tBu 117-119 4-096 Ph OCH2(6-Br-(E-2a)) tBu * 4-097 Ph OCH2(6-Cl-(E-3a)) tBu * 4-098 Ph OCH2(2-Cl-(E-30a)) tBu * 4-099 3-CF3-Ph NHC(O)OEt tBu 300> 4-100 3-CF3-Ph NHC(O)OiPr tBu 141-143 4-101 3-CF3-Ph NHC(O)OiBu tBu 146-148 4-102 3-CF3-Ph NHC(O)OCH2CH=CH2tBu 134-136 4-103 3-CF3-Ph NHC(O)OBn tBu 117-119 4-104 3-CF3-Ph OCH2(D-1a) tBu 123-124 4-105 3-CF3-Ph CH2OMe tBu * 4-106 3-Me-Ph C(=NOH)NH2tBu 129-131 ―――――――――――――――――――――――――――――――――― [Table 6]
[0304] [Chemical Structure]
[0305] ―――――――――――――――――――――――――――――――――― No. G Z R X R 1 R 3 R 4 m.p.(℃) ―――――――――――――――――――――――――――――――――― 5-001 3-CF3-Ph 2,4-Me2-Ph tBu Me H H * 5-002 Ph 4-CH(OMe)Me-Ph tBu Me H H * ―――――――――――――――――――――――――――――――――― [Table 7]
[0306]
Chem.
[0307] ―――――――――――――――――――――――――――――――――― No. G Z R X R 3 R 4 m.p.(℃) ―――――――――――――――――――――――――――――――――― 6-001 3-CF3-Ph 2,4-Me2-Ph tBu H H 132-134 6-002 3-CF3-Ph 4-Me-Ph iPr H H * 6-003 3-CF3-Ph 4-Me-Ph Ph H H 129-128 ―――――――――――――――――――――――――――――――――― [Table 8]
[0308]
Chem.
[0309] ———————————————————————————————————————————————————————————————————— No. G Z 1 Z 1’ R X m.p.(℃) ———————————————————————————————————————————————————————————————————— 7 - 001 3 - CF3 - Ph NHC(O)OMe Me tBu 121 - 123 7 - 002 3 - CF3 - Ph NHC(O)(E - 2a) Me tBu * 7 - 003 3 - CF3 - Ph NHC(O)(2 - F - Ph) Me tBu * 7 - 004 3 - CF3 - Ph NHC(O)(2 - OMe - Ph) Me tBu * 7 - 005 3 - CF3 - Ph NHC(O)(2 - CF3 - Ph) Me tBu 162 - 164 7 - 006 3 - CF3 - Ph NHC(O)(2,4 - Cl2 - Ph) Me tBu 147 - 149 7 - 007 3 - CF3 - Ph Me OCH2CF3tBu * 7 - 008 3 - CF3 - Ph C(O)OMe OMe tBu * 7 - 009 3 - CF3 - Ph C(O)OH OMe tBu 136 - 138 ———————————————————————————————————————————————————————————————————— [Table 9]
[0310]
Chem.
[0311] ———————————————————————————————————————————————————————————————————— No. G Z 1 Z 1’ R X m.p.(℃) ———————————————————————————————————————————————————————————————————— 8-001 3-CF3-Ph NHC(O)(E-2a) Me tBu * 8-002 3-CF3-Ph NHC(O)(2-F-Ph) Me tBu 132-134 8-003 3-CF3-Ph NHC(O)(2-OMe-Ph) Me tBu * 8-004 3-CF3-Ph NHC(O)(2-CF3-Ph) Me tBu * 8-005 3-CF3-Ph NHC(O)(2,4-Cl2-Ph) Me tBu * ―――――――――――――――――――――――――――――――――― [Table 10]
[0312] [Chemistry]
[0313] ―――――――――――――――――――――――――――――――――― No. G Z R X R Y R 3 R 4 m.p.(℃) ―――――――――――――――――――――――――――――――――― 9-001 Ph 4-Me-Ph tBu Br H H 110-112 9-002 Ph 2,4-Me2-Ph tBu Br H H * 9-003 3-CF3-Ph 4-Cl-Ph tBu Br H H 105-107 9-004 3-CF3-Ph 4-Br-Ph tBu Br H H 98-100 9-005 3-CF3-Ph 4-OMe-Ph tBu Br H H * 9-006 3-CF3-Ph Z-4a tBu Br H H * 9-007 3-CF3-Ph 4-Me-Ph tBu Cl H H * 9-008 3-CF3-Ph 4-OEt-Ph tBu Br H H * 9-009 3-CF3-Ph 4-OMe-Ph tBu Cl H H * 9-010 3-CF3-Ph 2,4-Me2-Ph tBu Cl F F * 9-011 3-CF3-Ph 4-OEt-Ph tBu Cl H H * 9-012 3-CF3-Ph 4-Cl-Ph tBu Cl H H 96-98 9-013 3-CF3-Ph 4-Br-Ph tBu Cl H H * 9-014 3-CF3-Ph 2-Me-4-OMe-Ph tBu Cl H H * 9-015 3-CF3-Ph 2-OMe-4-Me-Ph tBu Cl H H * 9-016 3-CF3-Ph 4-OH-Ph tBu Cl H H * 9-017 3-CF3-Ph 4-OiPr-Ph tBu Cl H H * 9-018 3-CF3-Ph 4-OCH2CF3-Ph tBu Cl H H 119-121 9-019 3-CF3-Ph 4-OCH2CF2H-Ph tBu Cl H H * 9-020 3-CF3-Ph 4-OCH2CF2CF2H-Ph tBu Cl H H 101-103 ―――――――――――――――――――――――――――――――――― [Table 11]
[0314] [Chemical formula]
[0315] ―――――――――――――――――――――――――――――――――― No. G Z 1 R X R Y R 3 R 4 m.p.(℃) ―――――――――――――――――――――――――――――――――― 10-001 3-CF3-Ph OCH2(6-Cl-(E-3a)) tBu Cl H H * 10-002 3-CF3-Ph OCH2(2-Cl-(E-30a)) tBu Cl H H * ―――――――――――――――――――――――――――――――――― [Table 12]
[0316] [Chemical formula]
[0317] ―――――――――――――――――――――――――――――――――― No. G Z R X R 3 R 4 m.p.(°C) ―――――――――――――――――――――――――――――――――― 11-001 3-CF3-Ph Z-9a tBu H H * 11-002 3-CF3-Ph Z-10a tBu H H * 11-003 Ph Z-9a tBu H H * 11-004 Ph Z-8a tBu H H * 11-005 Ph Z-27a tBu H H * 11-006 3-CF3-Ph 3-Me-(Z-39a) tBu H H 139-140 11-007 3-CF3-Ph 3,5-Me2-(Z-24a) tBu H H * 11-008 3-CF3-Ph Z-8a tBu H H * 11-009 3-CF3-Ph Z-19a tBu H H * 11-010 3-CF3-Ph 6-Me-(Z-8a) tBu H H * 11-011 3-CF3-Ph Z-14a tBu H H 92-94 11-012 3-CF3-Ph Z-20a tBu H H * 11-013 3-CF3-Ph 5-Me-(Z-41a) tBu H H * 11-014 3-CF3-Ph 5-Me-(Z-14a) tBu H H * 11-015 3-CF3-Ph 6-Me-(Z-14a) tBu H H * 11-016 3-CF3-Ph 5-Me-(Z-11a) tBu H H * 11-017 3-CF3-Ph 3,5-Me2-(Z-8a) tBu H H * 11-018 3-CF3-Ph 4-Cl-6-CF3-(Z-9a) tBu H H * 11-019 3-CF3-Ph 5-Me-(Z-17a) tBu H H * 11-020 3-CF3-Ph 5-Me-(Z-19a) tBu H H * 11-021 3-CF3-Ph 3-Br-5-Me-(Z-8a) tBu H H * 11-022 3-CF3-Ph 3-Me-5-Br-(Z-8a) tBu H H * 11-023 3-CF3-Ph 3,5-Cl2-(Z-8a) tBu H H * 11-024 3-CF3-Ph 3-Cl-5-Br-(Z-8a) tBu H H * 11-025 3-CF3-Ph 6-Cl-(Z-9a) tBu H H * 11-026 3-Me-Ph 6-Cl-(Z-9a) tBu H H * 11-027 3-Cl-Ph 6-Cl-(Z-9a) tBu H H * 11-028 Ph 6-Cl-(Z-9a) tBu H H * 11-029 3-CF3-Ph 6-CN-(Z-9a) tBu H H 129-131 11-030 3-CF3-Ph 6-OMe-(Z-9a) tBu H H * 11-031 3-Me-Ph 6-OMe-(Z-9a) tBu H H * 11-032 3-Cl-Ph 6-OMe-(Z-9a) tBu H H * 11-033 Ph 6-OMe-(Z-9a) tBu H H * ―――――――――――――――――――――――――――――――――― [Table 13]
[0318] [Chemical formula]
[0319] ―――――――――――――――――――――――――――――――――― No. G Z 1 Z 1a Z 1b R X m.p.(℃) ―――――――――――――――――――――――――――――――――― 12-001 3-CF3-Ph H H H tBu 82-84 12-002 3-CF3-Ph Me H Me tBu * 12-003 3-CF3-Ph H Me H tBu * 12-004 3-CF3-Ph H Cl H tBu 107-108 12-005 3-CF3-Ph H Br H tBu 113-114 12-006 3-CF3-Ph H 2-OMe-(E-7a) H tBu * 12-007 3-CF3-Ph H 6-Cl-(E-3a) H tBu * ―――――――――――――――――――――――――――――――――― [Table 14]
[0320] [Chemical formula]
[0321] ――――――――――――――――――――――――――――― No. G R X R Y m.p.(℃) ――――――――――――――――――――――――――――― i-001 3-CF3-Ph Ph H 177-179 i-002 3-CF3-Ph tBu H 120-124 i-003 3-CF3-Ph Bn H 124-126 i-004 3-CF3-Ph Me H i-005 3-CF3-Ph 2-Cl-Ph H i-006 3-CF3-Ph 3-Cl-Ph H 177-180 i-007 3-CF3-Ph 4-Cl-Ph H i-008 2-F-3-cPr-Ph Ph H i-009 3-Br-Ph tBu H 95-102 i-010 2-F-3-Cl-Ph tBu H 153-155 i-011 Ph tBu H 142-144 i-012 2-CF3-Ph tBu H 139-141 i-013 4-CF3-Ph tBu H 131-133 i-014 3-F-Ph tBu H 154-156 i-015 2-Cl-Ph tBu H 166-168 i-016 3-Cl-Ph tBu H 122-124 i-017 4-Cl-Ph tBu H 119-121 i-018 2,3-Cl2-Ph tBu H 160-162 i-019 2,4-Cl2-Ph tBu H 143-145 i-020 3,4-Cl2-Ph tBu H 143-145 i-021 3-I-Ph tBu H 121-123 i-022 3-OMe-Ph tBu H 145-147 i-023 3-OCF3-Ph tBu H 112-114 i-024 3-NMe2-Ph tBu H 126-130 i-025 3-CF3-Ph iPr H 177-179 i-026 Ph iPr H 142-144 i-027 Ph Ph H 176-178 i-028 2-F-3-Br-Ph tBu H i-029 2-F-3-cPr-Ph tBu H i-030 3-CF3-Ph E-2a H 115-117 i-031 3-CF3-Ph E-3a H 191-193 i-032 3-CF3-Ph E-4a H 166-168 i-033 Ph E-2a H 121-123 i-034 Ph E-3a H 187-189 i-035 Ph E-4a H 153-155 i-036 3-Me-Ph tBu H 116-118 i-037 3-SMe-Ph tBu H 117-119 i-038 3-CF3-Ph tBu Br 126-128 i-039 3-Me-Ph tBu Cl 105-107 i-040 2-F-Ph tBu H 118-120 i-041 2,3-F2-Ph tBu H 129-131 i-042 2-F-3-OMe-Ph tBu H 171-174 ――――――――――――――――――――――――――――― [Table 15]
[0322] [Chem.]
[0323] ――――――――――――――――――――――――――――― No. G R X R Y R 101 m.p.(℃) ――――――――――――――――――――――――――――― ii-001 3-CF3-Ph tBu H Me ii-002 2-F-3-Br-Ph tBu H Me ii-003 2-F-3-cPr-Ph tBu H Me ii-004 3-Br-Ph tBu H Me 69 - 71 ii-005 3-Me-Ph tBu H Me * ――――――――――――――――――――――――――――― Among the compounds of the present invention shown in Tables 2 to 13, the 1 1H-NMR data of the compounds without melting point description are shown in Table 16. The following data were measured in deuterated chloroform. The notation "#1" indicates that the measurement was performed at 300 MHz (model: JNM-ECX300 or JNM-ECP300, manufactured by JEOL Ltd.), and similarly, "#2" indicates that the measurement was performed at 400 MHz (model: JNM-ECZ400S, manufactured by JEOL Ltd.).
[0324] [Table 16] ―――――――――――――――――――――――――――――――――― No. 1 1H-NMR (CDCl3, Me4Si) ―――――――――――――――――――――――――――――――――― 1-003(#2): δ7.57 - 6.87 (m, 15H), 5.76 (s, 2H), 2.28 (s, 3H), 1.62 (s, 6H). 1-006(#1): δ 7.81 - 7.74 (m, 1H), 7.72 - 7.58 (m, 3H), 7.50 - 7.40 (m, 2H), 7.34 - 7.17 (m, 5H), 7.07 - 6.98 (m, 1H), 6.80 - 6.69 (m, 1H), 4.69 (d, J = 5.8 Hz, 2H), 1.77 (s, 9H). 1-009(#1): δ 7.96 - 7.89 (m, 1H), 7.87 - 7.81 (m, 1H), 7.80 - 7.74 (m, 1H), 7.53 - 7.28 (m, 4H), 7.22 - 7.13 (m, 3H), 7.06 - 6.95 (m, 1H), 6.88 - 6.70 (m, 3H), 4.98 (d, J = 5.4 Hz, 2H), 1.78 (s, 9H). 1-010(#1): δ 7.82 - 7.75 (m, 1H), 7.74 - 7.67 (m, 1H), 7.66 - 7.57 (m, 2H), 7.50 - 7.39 (m, 2H), 7.31 - 7.19 (m, 4H), 7.11 - 7.01 (m, 1H), 7.00 - 6.88 (m, 3H), 4.70 (d, J = 5.4 Hz, 2H), 1.77 (s, 9H). 1-011(#2): δ 7.42 - 7.29 (m, 2H), 7.23 (s, 1H), 7.18 - 7.13 (m, 1H), 7.06 - 6.97 (m, 2H), 6.95 - 6.85 (m, 2H), 6.47 - 6.37 (m, 1H), 4.47 (d, J = 5.5 Hz, 2H), 2.28 (s, 3H), 2.15 (s, 3H), 1.76 (s, 9H). 1-021(#2): δ 7.48 - 7.46 (m, 1H), 7.25 (s, 1H), 7.19 - 7.13 (m, 3H), 7.04 - 6.98 (m, 2H), 6.88 - 6.82 (m, 1H), 6.56 (br, 1H), 2.28 (s, 3H), 1.67 (s, 9H), 1.64 (s, 6H). 1-029(#1): δ 7.48 - 7.43 (m, 1H), 7.25 (s, 1H), 7.23 - 7.12 (m, 3H), 7.08 - 6.96 (m, 3H), 6.95 - 6.90 (m, 1H), 6.65 (br s, 1H), 2.27 (s, 3H), 1.68 (s, 9H), 1.62 (s, 6H). 1-030(#1): δ 7.36 (d, J = 8.9 Hz, 1H), 7.25 (s, 1H), 7.17 - 7.09 (m, 3H), 7.06 - 6.99 (m, 2H), 6.82 (dd, J = 8.9, 2.7 Hz, 1H), 6.37 (br s, 1H), 2.30 (s, 3H), 1.68 (s, 9H), 1.64 (s, 6H). 2-003(#2): δ 7.57 - 7.38 (m, 8H), 7.36 - 7.30 (m, 1H), 7.20 - 7.15 (m, 1H), 7.09 - 6.95 (m, 2H), 6.90 - 6.84 (m, 1H), 4.04 - 3.96 (m, 2H), 2.36 (s, 3H), 2.27 (s, 3H). 2-004(#2): δ 7.48 - 7.40 (m, 1H), 7.39 - 7.34 (m, 1H), 7.29 - 7.25 (m, 1H), 7.25 - 7.22 (m, 1H), 7.20 (s, 1H), 7.19 - 7.12 (m, 1H), 7.02 - 6.97 (m, 1H), 6.92 - 6.86 (m, 1H), 6.84 - 6.74 (m, 1H), 4.11 - 4.00 (m, 2H), 2.45 - 2.41 (m, 3H), 2.28 (s, 3H), 1.68 (s, 9H). 2-005(#2): δ 7.58 - 6.97 (m, 12H), 6.94 - 6.70 (m, 2H), 5.82 (s, 2H), 4.15 - 4.00 (m, 2H), 2.43 - 2.39 (m, 3H), 2.27 (s, 3H). 2-008(#2): δ 7.47 - 7.38 (m, 3H), 7.37 - 7.27 (m, 4H), 7.25 - 7.18 (m, 1H), 7.07 - 6.96 (m, 3H), 6.95 - 6.88 (m, 1H), 6.80 - 6.69 (m, 1H), 4.14 - 4.02 (m, 2H), 2.48 - 2.39 (m, 3H), 2.29 (s, 3H), 2.20 - 2.12 (m, 1H), 1.11 - 1.03 (m, 2H), 0.85 - 0.73 (m, 2H). 2-009(#2): δ 7.47 - 7.41 (m, 1H), 7.40 - 7.35 (m, 1H), 7.29 - 7.27 (m, 1H), 7.25 - 7.23 (m, 1H), 7.16 (s, 1H), 7.13 - 7.05 (m, 2H), 7.03 - 6.97 (m, 1H), 6.54 - 6.40 (m, 1H), 3.69 - 3.58 (m, 2H), 2.90 (t, J = 7.0 Hz, 2H), 1.72 (s, 9H). 2-012(#2): δ 7.24 - 7.20 (m, 1H), 7.18 - 7.13 (m, 2H), 7.08 (t, J = 2.2 Hz, 1H), 6.96 - 6.92 (m, 2H), 6.86 - 6.82 (m, 2H), 6.50 - 6.42 (m, 1H), 3.57 (q, J = 7.0 Hz, 2H), 2.74 (t, J = 7.0 Hz, 2H), 2.27 (s, 3H), 2.24 (s, 3H), 1.73 (s, 9H). 2-013(#2): δ 7.25 - 7.22 (m, 2H), 7.20 - 7.17 (m, 2H), 7.16 - 7.14 (m, 1H), 7.02 - 7.00 (m, 1H), 6.95 - 6.88 (m, 2H), 6.83 - 6.76 (m, 1H), 4.12 - 4.00 (m, 2H), 2.46 - 2.42 (m, 3H), 2.29 (s, 3H), 1.67 (s, 9H). 2-014(#2): δ 7.31 - 7.29 (m, 1H), 7.26 - 7.23 (m, 1H), 7.20 - 7.15 (m, 2H), 7.13 - 7.11 (m, 1H), 7.08 - 7.05 (m, 1H), 7.03 - 7.00 (m, 1H), 6.88 - 6.84 (m, 1H), 6.53 - 6.45 (m, 1H), 3.66 - 3.60 (m, 2H), 2.91 (t, J = 6.8 Hz, 2H), 1.72 (s, 9H). 2-015(#1): δ 7.18 - 7.09 (m, 2H), 7.04 - 6.79 (m, 5H), 6.60 - 6.43 (m, 1H), 3.64 - 3.54 (m, 2H), 2.77 (t, J = 7.2 Hz, 2H), 2.25 (s, 3H), 2.23 (s, 3H), 1.71 (s, 9H). 2-016(#2): δ 7.50 - 7.38 (m, 2H), 7.25 - 7.21 (m, 1H), 7.18 (s, 1H), 7.16 - 7.10 (m, 1H), 6.96 - 6.91 (m, 1H), 6.91 - 6.88 (m, 1H), 6.88 - 6.81 (m, 1H), 6.79 - 6.73 (m, 1H), 5.77 (sep, J = 6.9 Hz, 1H), 3.67 - 3.58 (m, 2H), 2.80 (t, J = 6.8 Hz, 2H), 2.24 (s, 3H), 2.21 (s, 3H), 1.50 (d, J = 6.9 Hz, 6H). 2-017(#2): δ 7.49 - 7.38 (m, 2H), 7.24 - 7.20 (m, 1H), 7.16 (s, 1H), 7.15 - 7.10 (m, 1H), 6.95 - 6.91 (m, 1H), 6.91 - 6.88 (m, 1H), 6.88 - 6.80 (m, 1H), 6.78 - 6.73 (m, 1H), 5.43 - 5.30 (m, 1H), 3.68 - 3.58 (m, 2H), 2.80 (t, J = 6.8 Hz, 2H), 2.23 (s, 3H), 2.21 (s, 3H), 2.10 - 1.99 (m, 2H), 1.96 - 1.80 (m, 4H), 1.78 - 1.67 (m, 1H), 1.56 - 1.39 (m, 3H). 2-018(#1): δ 7.34 - 7.26 (m, 2H), 7.14 (s, 1H), 7.12 - 7.05 (m, 1H), 6.97 - 6.89 (m, 4H), 6.85 - 6.78 (m, 1H), 6.70 - 6.55 (m, 1H), 3.54 (q, J = 7.2 Hz, 2H), 2.71 (t, J = 7.2 Hz, 2H), 2.24 (s, 3H), 2.23 (s, 3H), 1.73 (s, 9H). 2-019(#1): δ 7.36 - 7.27 (m, 3H), 7.13 (s, 1H), 7.12 - 7.03 (m, 2H), 6.99 - 6.91 (m, 3H), 6.70 - 6.60 (m, 1H), 3.62 (q, J = 6.6 Hz, 2H), 2.89 (t, J = 6.6 Hz, 2H), 1.72 (s, 9H). 2-020(#2): δ 7.31 - 7.26 (m, 1H), 7.17 - 7.12 (m, 2H), 7.04 - 6.96 (m, 2H), 6.94 - 6.88 (m, 2H), 6.86 - 6.79 (m, 1H), 4.14 - 4.03 (m, 2H), 2.47 - 2.42 (m, 3H), 2.28 (s, 3H), 1.66 (s, 9H). 2-021(#2): δ 7.31 - 7.29 (m, 1H), 7.19 - 7.10 (m, 3H), 7.06 - 6.97 (m, 2H), 6.93 - 6.87 (m, 1H), 6.64 - 6.50 (m, 1H), 3.71 - 3.61 (m, 2H), 2.94 (t, J = 7.0 Hz, 2H), 1.70 (s, 9H). 2-022(#1): δ 7.47 - 7.38 (m, 1H), 7.38 - 7.32 (m, 1H), 7.32 - 7.27 (m, 1H), 7.24 - 7.13 (m, 3H), 7.02 - 6.92 (m, 2H), 6.91 - 6.78 (m, 1H), 5.72 - 5.42 (m, 1H), 4.09 - 3.86 (m, 1H), 3.57 - 3.37 (m, 1H), 2.31 - 2.24 (m, 6H), 1.73 (s, 9H). 2-023(#1): δ 7.45 - 7.31 (m, 2H), 7.24 - 7.02 (m, 8H), 6.49 - 6.36 (m, 1H), 3.71 - 3.58 (m, 2H), 2.79 (t, J = 6.8 Hz, 2H), 1.72 (s, 9H). 2-024(#1): δ 7.48 - 7.29 (m, 2H), 7.23 - 7.13 (m, 2H), 7.12 - 6.96 (m, 5H), 6.55 - 6.37 (m, 1H), 3.65 - 3.53 (m, 2H), 2.77 (t, J = 7.0 Hz, 2H), 2.26 (s, 3H), 1.73 (s, 9H). 2-027(#1): δ 7.50 - 7.32 (m, 2H), 7.28 - 7.18 (m, 3H), 7.14 (s, 1H), 7.11 - 7.02 (m, 1H), 7.00 - 6.91 (m, 1H), 6.54 - 6.38 (m, 1H), 3.68 - 3.55 (m, 2H), 2.76 (t, J = 7.0 Hz, 2H), 1.72 (s, 9H). 2-028(#1): δ 7.48 - 7.30 (m, 2H), 7.25 - 7.21 (m, 1H), 7.20 - 7.09 (m, 4H), 7.05 - 6.96 (m, 1H), 6.63 - 6.46 (m, 1H), 3.73 - 3.59 (m, 2H), 3.15 (t, J = 6.8 Hz, 2H), 1.71 (s, 9H). 2-029(#1): δ 7.45 - 7.30 (m, 2H), 7.22 - 7.15 (m, 2H), 7.10 - 7.01 (m, 1H), 6.97 - 6.88 (m, 2H), 6.87 - 6.78 (m, 1H), 6.43 - 6.30 (m, 1H), 3.62 - 3.48 (m, 2H), 2.72 (t, J = 7.0 Hz, 2H), 2.24 (s, 3H), 2.22 (s, 3H), 2.16 (q, J = 7.5 Hz, 2H), 1.68 (s, 6H), 0.75 (t, J = 7.5 Hz, 3H). 2-030(#1): δ 7.37 - 7.28 (m, 2H), 7.26 - 7.22 (m, 1H), 7.15 (s, 1H), 7.14 - 7.07 (m, 1H), 7.05 - 6.94 (m, 4H), 6.93 - 6.86 (m, 1H), 4.12 - 3.97 (m, 2H), 2.46 - 2.42 (m, 3H), 2.28 (s, 3H), 1.67 (s, 9H). 2-031(#2): δ 7.50 - 7.40 (m, 2H), 7.25 - 7.22 (m, 1H), 7.18 - 7.11 (m, 1H), 7.18 (s, 1H), 6.95 - 6.80 (m, 3H), 6.78 - 6.71 (m, 1H), 4.21 (q, J = 7.1 Hz, 2H), 3.63 - 3.54 (m, 2H), 2.76 (t, J = 6.8 Hz, 2H), 2.23 - 2.16 (m, 6H), 1.88 (s, 6H), 1.29 - 1.20 (m, 3H). 2-032(#2): δ 7.50 - 7.38 (m, 2H), 7.25 - 7.17 (m, 2H), 7.16 - 7.08 (m, 1H), 6.98 - 6.80 (m, 3H), 6.80 - 6.73 (m, 1H), 5.67 - 5.53 (m, 1H), 3.72 - 3.53 (m, 2H), 2.80 (t, J = 7.0 Hz, 2H), 2.23 (s, 3H), 2.22 (s, 3H), 2.05 - 1.92 (m, 1H), 1.85 - 1.72 (m, 1H), 1.49 (d, J = 6.6 Hz, 3H), 0.82 (dd, J = 7.5, 7.5 Hz, 3H). 2-033(#2): δ 7.20 - 7.11 (m, 2H), 6.97 - 6.90 (m, 2H), 6.85 - 6.77 (m, 2H), 6.74 - 6.63 (m, 3H), 3.58 - 3.52 (m, 2H), 2.72 (t, J = 7.2 Hz, 2H), 2.26 - 2.22 (m, 6H), 1.90 - 1.80 (m, 1H), 1.73 (s, 9H), 1.00 - 0.93 (m, 2H), 0.69 - 0.64 (m, 2H). 2-035(#2): δ 7.51 - 7.39 (m, 2H), 7.24 (s, 1H), 7.21 - 7.14 (m, 1H), 7.12 - 7.06 (m, 1H), 7.05 - 6.85 (m, 2H), 6.80 - 6.73 (m, 1H), 6.71 - 6.62 (m, 1H), 3.67 - 3.58 (m, 2H), 3.00 - 2.84 (m, 3H), 2.75 (t, J = 6.8 Hz, 2H), 2.51 - 2.33 (m, 3H), 2.24 - 2.17 (m, 6H), 1.88 (s, 6H). 2-036(#2): δ 7.21 - 7.13 (m, 2H), 6.97 - 6.88 (m, 3H), 6.85 - 6.62 (m, 4H), 3.59 - 3.51 (m, 2H), 2.73 (t, J = 7.2 Hz, 2H), 2.32 (s, 3H), 2.26 - 2.21 (m, 6H), 1.74 (s, 9H). 2-037(#2): δ 7.46 - 7.39 (m, 1H), 7.39 - 7.33 (m, 1H), 7.24 - 7.20 (m, 1H), 7.15 (s, 1H), 7.13 - 7.05 (m, 1H), 6.94 - 6.87 (m, 2H), 6.56 - 6.49 (m, 2H), 6.46 - 6.34 (m, 1H), 3.65 - 3.47 (m, 4H), 2.67 (t, J = 6.8 Hz, 2H), 1.72 (s, 9H). 2-040(#2): δ 7.47 - 7.40 (m, 1H), 7.40 - 7.34 (m, 1H), 7.25 - 7.21 (m, 1H), 7.17 (s, 1H), 7.11 - 7.04 (m, 2H), 7.00 - 6.95 (m, 2H), 6.51 - 6.40 (m, 1H), 3.62 - 3.53 (m, 2H), 2.74 (t, J = 7.2 Hz, 2H), 2.23 (s, 3H), 1.73 (s, 9H). 2-041(#2): δ 7.70 - 7.66 (m, 1H), 7.57 - 7.54 (m, 1H), 7.43 - 7.38 (m, 1H), 7.16 - 7.10 (m, 2H), 6.96 - 6.89 (m, 2H), 6.84 - 6.78 (m, 1H), 6.56 - 6.50 (m, 1H), 3.60 - 3.52 (m, 2H), 2.73 (t, J = 7.2 Hz, 2H), 2.58 (s, 3H), 2.23 (d, J = 3.7 Hz, 6H), 1.73 (s, 9H). 2-042(#2): δ 7.48 (s, 1H), 7.20 - 7.08 (m, 2H), 6.97 - 6.89 (m, 2H), 6.87 - 6.81 (m, 1H), 6.69 - 6.54 (m, 2H), 6.52 - 6.46 (m, 1H), 6.44 - 6.40 (m, 1H), 3.58 - 3.49 (m, 2H), 2.70 (t, J = 7.2 Hz, 2H), 2.27 - 2.17 (m, 6H), 1.68 (d, J = 1.1 Hz, 9H). 2-043(#2): δ 7.40 - 7.35 (m, 1H), 7.33 - 7.27 (m, 2H), 7.13 (s, 1H), 6.98 - 6.90 (m, 3H), 6.85 - 6.80 (m, 1H), 6.66 - 6.59 (m, 1H), 3.99 (s, 3H), 3.61 - 3.52 (m, 2H), 2.74 (t, J = 7.2 Hz, 2H), 2.24 (s, 6H), 2.19 (s, 3H), 1.73 (s, 9H). 2-044(#2): δ 7.22 - 7.16 (m, 2H), 6.96 - 6.91 (m, 2H), 6.85 - 6.81 (m, 1H), 6.66 - 6.61 (m, 2H), 6.55 - 6.50 (m, 2H), 3.76 (s, 3H), 3.58 - 3.51 (m, 2H), 2.72 (t, J = 7.2 Hz, 2H), 2.25 - 2.22 (m, 6H), 1.73 (s, 9H). 2-045(#2): δ 7.20 - 7.14 (m, 2H), 6.97 - 6.91 (m, 2H), 6.85 - 6.81 (m, 1H), 6.65 - 6.59 (m, 2H), 6.52 - 6.47 (m, 2H), 4.53 - 4.45 (m, 1H), 3.59 - 3.50 (m, 2H), 2.72 (t, J = 7.3 Hz, 2H), 2.26 - 2.23 (m, 6H), 1.73 (s, 9H), 1.32 (d, J = 5.9 Hz, 6H). 2-046(#2): δ 7.42 - 7.28 (m, 5H), 7.25 - 7.14 (m, 2H), 6.96 - 6.90 (m, 2H), 6.85 - 6.80 (m, 1H), 6.73 - 6.68 (m, 1H), 6.61 - 6.51 (m, 3H), 5.01 (s, 2H), 3.58 - 3.49 (m, 2H), 2.71 (t, J = 7.2 Hz, 2H), 2.26 - 2.20 (m, 6H), 1.79 - 1.70 (m, 9H). 2-047(#2): δ 7.30 - 7.14 (m, 2H), 6.97 - 6.82 (m, 3H), 6.72 - 6.63 (m, 2H), 6.58 - 6.55 (m, 1H), 6.53 - 6.46 (m, 1H), 4.72 (s, 2H), 3.58 - 3.50 (m, 2H), 2.71 (t, J = 7.2 Hz, 2H), 2.28 - 2.21 (m, 6H), 1.72 (s, 9H). 2-048(#1): δ 7.38 - 7.27 (m, 2H), 7.24 - 7.17 (m, 2H), 7.13 - 6.90 (m, 6H), 5.72 - 5.43 (m, 1H), 4.07 - 3.84 (m, 1H), 3.57 - 3.36 (m, 1H), 2.29 (s, 3H), 2.27 (s, 3H), 1.73 (s, 9H). 2-049(#1): δ 7.37 - 7.25 (m, 2H), 7.24 - 7.05 (m, 7H), 6.98 - 6.89 (m, 2H), 6.71 - 6.53 (m, 1H), 3.67 - 3.55 (m, 2H), 2.77 (t, J = 6.8 Hz, 2H), 1.72 (s, 9H). 2-050(#1): δ 7.38 - 7.23 (m, 2H), 7.16 - 6.88 (m, 8H), 6.68 - 6.50 (m, 1H), 3.66 - 3.53 (m, 2H), 2.73 (t, J = 6.8 Hz, 2H), 2.27 (s, 3H), 1.72 (s, 9H). 2-051(#1): δ 7.36 - 7.24 (m, 2H), 7.15 - 7.04 (m, 3H), 7.02 - 6.88 (m, 5H), 6.71 - 6.52 (m, 1H), 3.66 - 3.55 (m, 2H), 2.73 (t, J = 7.2 Hz, 2H), 2.26 (s, 3H), 1.72 (s, 9H). 2-052(#1): δ 7.36 - 7.25 (m, 2H), 7.15 (s, 1H), 7.14 - 6.98 (m, 5H), 6.97 - 6.90 (m, 2H), 6.68 - 6.55 (m, 1H), 3.63 - 3.51 (m, 2H), 2.75 (t, J = 7.2 Hz, 2H), 2.26 (s, 3H), 1.73 (s, 9H). 2-053(#1): δ 7.42 - 7.27 (m, 3H), 7.13 (s, 1H), 6.99 - 6.79 (m, 4H), 6.68 - 6.58 (m, 1H), 4.49 - 4.40 (m, 1H), 3.61 - 3.51 (m, 2H), 2.73 (t, J = 7.2 Hz, 2H), 2.26 - 2.15 (m, 9H), 1.73 (s, 9H), 1.30 (d, J = 6.5 Hz, 6H). 2-054(#1): δ 7.43 - 7.26 (m, 3H), 7.14 (s, 1H), 6.97 - 6.78 (m, 4H), 6.67 - 6.57 (m, 1H), 3.60 - 3.50 (m, 2H), 2.72 (t, J = 7.2 Hz, 2H), 2.26 - 2.13 (m, 9H), 1.73 (s, 9H), 1.34 (s, 9H). 2-055(#1): δ 7.83 - 7.55 (m, 1H), 7.40 - 7.27 (m, 3H), 7.15 (s, 1H), 6.97 - 6.89 (m, 3H), 6.84 - 6.78 (m, 1H), 6.64 - 6.55 (m, 1H), 3.61 - 3.51 (m, 2H), 2.73 (t, J = 7.2 Hz, 2H), 2.27 - 2.21 (m, 9H), 1.73 (s, 9H). 2-056(#1): δ 7.17 - 7.08 (m, 2H), 7.07 - 6.93 (m, 5H), 6.92 - 6.82 (m, 1H), 6.57 - 6.42 (m, 1H), 3.63 (dt, J = 5.7, 7.2 Hz, 2H), 2.78 (t, J = 7.2 Hz, 2H), 2.25 (s, 3H), 1.70 (s, 9H). 2-059(#2): δ 7.46 - 7.33 (m, 2H), 7.24 - 7.21 (m, 1H), 7.15 (s, 1H), 7.11 - 7.00 (m, 3H), 6.78 - 6.70 (m, 2H), 6.48 - 6.37 (m, 1H), 3.74 (s, 3H), 3.65 - 3.55 (m, 2H), 2.73 (t, J = 6.8 Hz, 2H), 1.72 (s, 9H). 2-061(#2): δ 7.46 - 7.33 (m, 2H), 7.30 - 7.26 (m, 1H), 7.24 - 7.19 (m, 1H), 7.16 (s, 1H), 7.16 - 7.00 (m, 4H), 6.53 - 6.42 (m, 1H), 3.70 - 3.62 (m, 2H), 2.94 (t, J = 7.2 Hz, 2H), 1.72 (s, 9H). 2-062(#2): δ 7.46 - 7.33 (m, 2H), 7.25 - 7.19 (m, 1H), 7.18 - 7.06 (m, 5H), 7.03 - 6.98 (m, 1H), 6.51 - 6.40 (m, 1H), 3.68 - 3.59 (m, 2H), 2.78 (t, J = 6.8 Hz, 2H), 1.72 (s, 9H). 2-065(#2): δ 7.46 - 7.39 (m, 1H), 7.39 - 7.33 (m, 1H), 7.23 - 7.18 (m, 1H), 7.18 - 7.07 (m, 4H), 6.98 - 6.89 (m, 2H), 6.54 - 6.42 (m, 1H), 3.68 - 3.60 (m, 2H), 2.85 (t, J = 6.8 Hz, 2H), 1.72 (s, 9H). 2-066(#2): δ 7.47 - 7.39 (m, 1H), 7.39 - 7.33 (m, 1H), 7.23 - 7.18 (m, 1H), 7.17 - 7.05 (m, 3H), 6.93 - 6.79 (m, 3H), 6.52 - 6.40 (m, 1H), 3.69 - 3.60 (m, 2H), 2.80 (t, J = 6.8 Hz, 2H), 1.72 (s, 9H). 2-067(#2): δ 7.46 - 7.34 (m, 2H), 7.23 - 7.18 (m, 1H), 7.16 (s, 1H), 7.12 - 7.04 (m, 3H), 6.91 - 6.82 (m, 2H), 6.49 - 6.37 (m, 1H), 3.66 - 3.57 (m, 2H), 2.77 (t, J = 6.8 Hz, 2H), 1.72 (s, 9H). 2-068(#2): δ 7.58 - 7.53 (m, 1H), 7.46 - 7.39 (m, 2H), 7.39 - 7.31 (m, 3H), 7.22 - 7.16 (m, 2H), 7.13 - 7.07 (m, 1H), 6.56 - 6.44 (m, 1H), 3.69 - 3.60 (m, 2H), 2.96 (t, J = 7.2 Hz, 2H), 1.72 (s, 9H). 2-071(#2): δ 8.05 - 7.99 (m, 2H), 7.47 - 7.34 (m, 2H), 7.31 - 7.26 (m, 2H), 7.23 - 7.19 (m, 1H), 7.15 (s, 1H), 7.09 - 7.03 (m, 1H), 6.56 - 6.46 (m, 1H), 3.74 - 3.65 (m, 2H), 2.92 (t, J = 6.8 Hz, 2H), 1.72 (s, 9H). 2-072(#1): δ 7.88 - 7.81 (m, 2H), 7.45 - 7.30 (m, 2H), 7.23 - 7.16 (m, 3H), 7.13 (s, 1H), 7.10 - 7.00 (m, 1H), 6.52 - 6.39 (m, 1H), 3.89 (s, 3H), 3.73 - 3.61 (m, 2H), 2.86 (t, J = 6.8 Hz, 2H), 1.72 (s, 9H). 2-076(#1): δ 7.47 - 7.29 (m, 2H), 7.27 - 7.23 (m, 1H), 7.20 (s, 1H), 7.15 - 7.06 (m, 1H), 6.77 (s, 2H), 6.51 - 6.39 (m, 1H), 3.48 - 3.36 (m, 2H), 2.77 - 2.65 (m, 2H), 2.24 (s, 6H), 2.21 (s, 3H), 1.74 (s, 9H). 2-077(#2): δ 7.53 - 7.43 (m, 2H), 7.26 - 7.22 (m, 1H), 7.17 (s, 1H), 7.16 - 7.10 (m, 1H), 6.96 - 6.92 (m, 1H), 6.91 - 6.87 (m, 1H), 6.86 - 6.78 (m, 1H), 6.77 - 6.72 (m, 1H), 3.72 - 3.64 (m, 2H), 2.82 (t, J = 6.8 Hz, 2H), 2.23 (s, 3H), 2.20 (s, 3H), 2.14 (s, 6H). 2-080(#1): δ 7.46 - 7.28 (m, 4H), 7.24 - 7.13 (m, 3H), 7.11 (s, 1H), 6.96 - 6.87 (m, 2H), 6.76 - 6.60 (m, 1H), 3.71 - 3.59 (m, 2H), 2.85 (t, J = 6.8 Hz, 2H), 1.72 (s, 9H). 2-081(#2): δ 7.51 - 7.32 (m, 3H), 7.24 - 7.19 (m, 1H), 7.19 - 6.97 (m, 5H), 6.54 - 6.40 (m, 1H), 3.71 - 3.60 (m, 2H), 2.95 (t, J = 6.8 Hz, 2H), 1.72 (s, 9H). 2-082(#2): δ 7.82 - 7.74 (m, 1H), 7.68 - 7.59 (m, 1H), 7.42 - 7.33 (m, 1H), 7.17 - 7.06 (m, 2H), 6.97 - 6.87 (m, 2H), 6.84 - 6.76 (m, 1H), 6.59 - 6.47 (m, 1H), 3.92 (s, 3H), 3.60 - 3.51 (m, 2H), 2.74 (t, J = 7.2 Hz, 2H), 2.34 - 2.15 (m, 6H), 1.73 (s, 9H). 2-084(#1): δ 7.43 - 7.27 (m, 3H), 7.17 (s, 1H), 7.07 - 7.01 (m, 1H), 6.95 - 6.90 (m, 2H), 6.86 - 6.80 (m, 1H), 6.54 - 6.46 (m, 1H), 6.03 (s, 1H), 3.52 - 3.43 (m, 2H), 2.63 (t, J = 7.2 Hz, 2H), 2.27 - 2.19 (m, 6H), 1.72 (s, 9H), 1.46 (s, 9H). 2-085(#1): δ 7.46 - 7.27 (m, 3H), 7.17 (s, 1H), 7.07 - 7.02 (m, 1H), 6.95 - 6.90 (m, 2H), 6.86 - 6.80 (m, 1H), 6.55 - 6.46 (m, 1H), 6.14 - 6.04 (m, 1H), 4.02 - 3.87 (m, 1H), 3.54 - 3.42 (m, 2H), 2.63 (t, J = 7.2 Hz, 2H), 2.27 - 2.17 (m, 6H), 2.08 - 1.96 (m, 2H), 1.83 - 1.59 (m, 11H), 1.52 - 1.11 (m, 6H). 2-086(#1): δ 7.33 (t, J = 7.8 Hz, 1H), 7.18 - 7.10 (m, 2H), 7.03 - 6.92 (m, 4H), 6.89 - 6.83 (m, 1H), 6.59 - 6.51 (m, 1H), 3.59 - 3.50 (m, 2H), 3.13 - 2.90 (m, 6H), 2.74 (t, J = 7.2 Hz, 2H), 2.29 - 2.23 (m, 6H), 1.72 (s, 9H). 2-087(#1): δ 7.44 - 7.27 (m, 3H), 7.24 - 7.07 (m, 6H), 7.05 - 6.97 (m, 1H), 6.42 - 6.22 (m, 1H), 3.79 - 3.66 (m, 1H), 3.47 - 3.33 (m, 1H), 3.03 - 2.82 (m, 1H), 1.70 (s, 9H), 1.24 (d, J = 7.2 Hz, 3H). 2-088(#2): δ 7.62 - 7.57 (m, 1H), 7.51 - 7.36 (m, 3H), 7.34 - 7.27 (m, 2H), 7.21 - 7.13 (m, 2H), 6.84 - 6.72 (m, 1H), 4.32 - 4.18 (m, 2H), 1.65 (s, 9H). 2-089(#1): δ 7.43 - 7.30 (m, 3H), 7.29 - 7.12 (m, 4H), 7.10 - 7.06 (m, 2H), 7.02 - 6.94 (m, 1H), 6.23 - 6.10 (m, 1H), 3.60 (d, J = 5.8 Hz, 2H), 1.69 (s, 9H), 1.29 (s, 6H). 2-090(#1): δ 7.37 - 7.04 (m, 9H), 6.93 - 6.83 (m, 2H), 6.58 - 6.42 (m, 1H), 3.74 - 3.61 (m, 1H), 3.48 - 3.35 (m, 1H), 3.01 - 2.85 (m, 1H), 1.70 (s, 9H), 1.28 - 1.20 (m, 3H). 2-091(#1): δ 7.42 - 7.32 (m, 2H), 7.18 (s, 1H), 7.14 - 7.08 (m, 2H), 6.97 - 6.91 (m, 2H), 6.88 - 6.82 (m, 1H), 6.40 - 6.30 (m, 1H), 3.63 - 3.51 (m, 2H), 2.77 - 2.70 (m, 2H), 2.29 - 2.20 (m, 6H), 1.73 (s, 9H). 2-093(#2): δ 7.24 - 7.19 (m, 1H), 7.17 (s, 1H), 7.10 - 7.04 (m, 1H), 6.97 - 6.93 (m, 2H), 6.92 - 6.91 (m, 1H), 6.87 - 6.82 (m, 1H), 6.82 - 6.78 (m, 1H), 6.53 - 6.41 (m, 1H), 3.57 (dt, J = 5.6, 7.2 Hz, 2H), 2.74 (t, J = 7.2 Hz, 2H), 2.26 (s, 3H), 2.23 (s, 3H), 1.73 (s, 9H). 2-095(#2): δ 7.28 - 7.21 (m, 1H), 7.19 (s, 1H), 6.97 - 6.92 (m, 2H), 6.87 - 6.83 (m, 1H), 6.82 - 6.76 (m, 1H), 6.72 - 6.67 (m, 1H), 6.64 - 6.59 (m, 1H), 6.50 - 6.42 (m, 1H), 3.56 (dt, J = 5.6, 7.2 Hz, 2H), 2.72 (t, J = 7.2 Hz, 2H), 2.26 (s, 3H), 2.23 (s, 3H), 1.73 (s, 9H). 2-096(#2): δ 7.45 - 7.41 (m, 1H), 7.31 - 7.28 (m, 1H), 7.15 (s, 1H), 7.04 - 6.98 (m, 1H), 6.97 - 6.92 (m, 2H), 6.90 - 6.82 (m, 2H), 6.54 - 6.43 (m, 1H), 3.57 (dt, J = 6.0, 7.2 Hz, 2H), 2.74 (t, J = 7.2 Hz, 2H), 2.27 (s, 3H), 2.24 (s, 3H), 1.73 (s, 9H). 2-097(#2): δ 7.28 - 7.22 (m, 2H), 7.14 (s, 1H), 6.97 - 6.91 (m, 2H), 6.88 - 6.81 (m, 3H), 6.55 - 6.44 (m, 1H), 3.57 (dt, J = 6.0, 7.2 Hz, 2H), 2.74 (t, J = 7.2 Hz, 2H), 2.26 (s, 3H), 2.23 (s, 3H), 1.72 (s, 9H). 2-098(#2): δ 7.44 - 7.37 (m, 1H), 7.23 - 7.17 (m, 2H), 7.07 - 7.02 (m, 1H), 7.00 - 6.95 (m, 2H), 6.93 - 6.90 (m, 1H), 6.86 - 6.80 (m, 1H), 6.77 - 6.67 (m, 1H), 3.55 (dt, J = 6.4, 7.2 Hz, 2H), 2.73 (t, J = 7.2 Hz, 2H), 2.25 (s, 3H), 2.23 (s, 3H), 1.73 (s, 9H). 2-099(#2): δ 7.33 (d, J = 9.2 Hz, 1H), 7.16 (s, 1H), 7.00 (d, J = 2.8 Hz, 1H), 6.97 - 6.92 (m, 2H), 6.88 - 6.82 (m, 1H), 6.75 (dd, J = 9.2, 2.8 Hz, 1H), 6.44 - 6.33 (m, 1H), 3.59 (dt, J = 6.0, ...
Claims
1. Formula (1): 【Chemical Formula 1】 [wherein, G represents G-1, G-1 represents a structure represented by the following structural formula, [Chemical 2] G 1 represents hydroxy, nitro, cyano, a halogen atom, C 1 to C 6 alkyl, C 3 to C 10 cycloalkyl, C 1 to C 6 haloalkyl, C 1 to C 6 alkoxy, C b substituted by R 1 to C 6 alkoxy, C 1 to C 6 haloalkoxy, C 1 to C 6 alkylthio, C 1 to C 6 alkylsulfinyl, C 1 to C 6 alkylsulfonyl, di(C 1 to C 6 alkyl)amino, C 1 to C 6 alkylcarbonyl, C 1 to C 6 alkoxycarbonyl, C 1 to C 6 alkylaminocarbonyl, C 3 to C 10 cycloalkylaminocarbonyl, di(C 1 to C 6 alkyl)aminocarbonyl or -C(=NOR)R', and G 1 In relation to G, when m5 indicates an integer of 2, 3, 4, or 5, each G 1 may be the same as or different from each other, R b represents cyano, C 3 to C 10 cycloalkyl, C 1 to C 6 alkoxycarbonyl, C 1 to C 6 alkylaminocarbonyl, di(C 1 to C 6 alkyl)aminocarbonyl, phenyl or -C(=NOR)R', R represents a hydrogen atom or C 1 ~C 6 alkyl, and R' is C 1 ~C 6 represents alkyl, T represents an oxygen atom or a sulfur atom, R X is C 1 to C 6 alkyl, C 3 to C 10 cycloalkyl, C 1 to C 6 haloalkyl, R c substituted C 1 to C 6 alkyl, benzyl, R X -1, R X -2, R X -3 or R X -4, and represents R X -1 to R X -4 each represent a structure represented by the following structural formula, 【Chemical Formula 3】 X 1 represents a halogen atom, C 1 to C 6 alkyl, C 1 to C 6 haloalkyl or C 1 to C 6 alkoxy, X 1 in relation to u5 indicating an integer of 2, 3, 4 or 5, each X 1 may be the same as or different from each other, X 1 In the relationship with, when u4 indicates an integer of 2, 3, or 4, each X 1 may be the same as each other or different from each other, R c represents cyano, C 3 to C 10 cycloalkyl, C 1 to C 6 alkoxy, C 1 to C 6 alkoxycarbonyl, C 1 to C 6 alkylaminocarbonyl, di(C 1 to C 6 alkyl)aminocarbonyl or -C(=NOR)R', R Y represents a hydrogen atom, a halogen atom or C 1 to C 6 alkyl, and R 1 represents a hydrogen atom or C 1 to C 6 alkyl, R 2 represents a hydrogen atom or C 1 to C 6 alkyl, and R 3 represents a hydrogen atom, a halogen atom, C 1 to C 6 alkyl or C 1 to C 6 alkoxy, and R 4 represents a hydrogen atom, a halogen atom or C 1 to C 6 alkyl, and R a represents a hydrogen atom, C 1 to C 6 alkyl, R a -1, R a -2, R a -3, R a -4, R a -5 or R a -6, and R a -1, R a -2, R a -3, R a -4, R a -5 and R a -6 each represent a structure represented by the following structural formula, 【Chemical Formula 4】 R 5 represents a hydrogen atom or C 1 to C 6 alkyl, and R 6 represents a hydrogen atom or C 1 to C 6 alkyl, r 1 When r represents an integer of 2, the two Rs 5 and the two Rs 6 may be identical to each other or different from each other, R 7 represents C 1 to C 6 alkyl, C 3 to C 10 cycloalkyl, C 1 to C 6 haloalkyl or phenyl, and R 8 represents a hydrogen atom or C 1 to C 6 alkyl, R 9 represents a hydrogen atom or C 1 to C 6 alkyl, Z represents Z-1 to Z-45 or Z-46, Z-1 to Z-46 each represent a structure represented by the following structural formula, 【Chemical Formula 5】 【Chemical Formula 6】 Incidentally, Z 1 The substitution position indicates that it is substituted on the aromatic ring of Z-1 to Z-46, Z 1 is hydroxy, carboxy, amino, nitro, cyano, a halogen atom, C 1 to C 6 alkyl, C 3 to C 10 cycloalkyl, C 1 to C 6 haloalkyl, C 3 to C 10 halocycloalkyl, C 2 to C 6 alkenyl, C 1 to C 6 alkoxy, C 1 to C 6 alkylthio, C 1 to C 6 alkylsulfinyl, C 1 to C 6 alkylsulfonyl, C 1 to C 6 alkylamino, C 1 to C 6 alkylcarbonyl, C 1 to C 6 alkoxycarbonyl, R i substituted C 1 to C 6 alkyl, -OR d , -NHC(O)R e , -NR h C(O)R e , -NHSO 2 R f , -C≡CR g , -SO 2 NH 2 , -C(O)NH 2 , -C(S)NH 2 , -C(=NOH)NH 2 represents E-1 to E-54, F-1 to F-15 or -C(=NOR)R', Z 1 in relation to, when n7 represents an integer of 2, 3, 4, 5, 6 or 7, each Z 1 may be the same as each other or may be different from each other, Z 1 in relation to, when n6 represents an integer of 2, 3, 4, 5 or 6, each Z 1 may be identical to each other or different from each other, Z 1 in relation to, when n5 represents an integer of 2, 3, 4 or 5, each Z 1 may be the same as each other or different from each other, Z 1 In relation to Z, when n4 represents an integer of 2, 3, or 4, each Z 1 may be identical to or different from each other, Z 1 in relation to, when n3 represents an integer of 2 or 3, each Z 1 may be identical to each other or different from each other, Z 1 In relation to, when n2 represents an integer of 2, each Z 1 may be identical to each other or may be different from each other, Z 2 represents C 1 to C 6 alkyl or phenyl, and R d is C 2 to C 6 alkenyl, C 2 to C 6 alkynyl, C 1 to C 6 haloalkyl, R 10 substituted C 1 to C 6 alkyl, C 1 to C 6 alkylcarbonyl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, E-1 to E-54, F-1 to F-15 or C 1 to C 6 alkylaminocarbonyl, and represents R 10 represents C 3 to C 10 cycloalkyl, C 1 to C 6 alkylcarbonyl, C 1 to C 6 alkoxycarbonyl, di(C 1 to C 6 alkyl)aminocarbonyl, E-1 to E-54, F-1 to F-15 or -C(=NOR)R', R e represents C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 1 to C 6 alkoxy, C 2 to C 6 alkenyloxy, C 1 to C 6 alkylamino, benzyloxy, E-1 to E-54, F-1 to F-15 or di(C 1 to C 6 alkyl)amino, R f represents C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, E-1 to E-54, F-1 to F-15 or di(C 1 to C 6 alkyl)amino, R g represents a hydrogen atom or tri(C 1 ~C 4 alkyl)silyl, R h represents C 1 to C 6 alkyl, and R i represents hydroxy or C 1 to C 6 alkoxy, and E-1 to E-54 each represent a structure represented by the following structural formula, 【Chemical Formula 7】 【Chemical Formula 8】 F-1 to F-15 each represent a structure represented by the following structural formula, 【Chemical Formula 9】 Z a represents a halogen atom, cyano, C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 1 to C 6 alkoxy, C 1 to C 6 haloalkoxy, C 1 to C 6 alkylcarbonyl or C 1 to C 6 alkoxycarbonyl, Z a In relation to, when v7 indicates an integer of 2, 3, 4, 5, 6 or 7, each Z a may be the same as each other or different from each other, Z a in relation to, when v6 represents an integer of 2, 3, 4, 5 or 6, each Z a may be identical to each other or may be different from each other, Z a in relation to, when v5 indicates an integer of 2, 3, 4 or 5, each Z a may be identical to each other or may be different from each other, Z a In the relationship with, when v4 indicates an integer of 2, 3, or 4, each Z a may be the same as each other or different from each other, Z a In relation to, when v3 indicates an integer of 2 or 3, each Z a may be the same as or different from each other, Z a In the relationship with, when v2 indicates an integer of 2, each Z a may be identical to each other or different from each other, Z b represents C 1 to C 6 alkyl, and m5 represents an integer of 0, 1, 2, 3, 4 or 5, n7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7, n6 represents an integer of 0, 1, 2, 3, 4, 5 or 6, n5 represents an integer of 0, 1, 2, 3, 4 or 5, n4 represents an integer of 0, 1, 2, 3 or 4, n3 represents an integer of 0, 1, 2 or 3, n2 represents an integer of 0, 1 or 2, n1 represents an integer of 0 or 1, u5 represents an integer of 0, 1, 2, 3, 4 or 5, u4 represents an integer of 0, 1, 2, 3 or 4, p represents an integer of 0 or 1, r 1 represents an integer of 1 or 2, r 2 represents an integer of 0 or 1, t represents an integer of 0, 1 or 2, v7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7, v6 represents an integer of 0, 1, 2, 3, 4, 5 or 6, v5 represents an integer of 0, 1, 2, 3, 4 or 5, v4 represents an integer of 0, 1, 2, 3 or 4, v3 represents an integer of 0, 1, 2 or 3, v2 represents an integer of 0, 1 or 2, v1 represents an integer of 0 or 1. ] A pyrazole compound represented by or a salt thereof.
2. R b represents cyano or phenyl, X 1 represents a halogen atom, and R c represents cyano, C 3 -C 10 -cycloalkyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylaminocarbonyl, di(C 1 -C 6 -alkyl)aminocarbonyl or -C(=NOR)R', R Y represents a hydrogen atom or a halogen atom, R a represents a hydrogen atom, C 1 to C 6 alkyl, R a -1 or R a -4, and R 5 represents a hydrogen atom, and R 6 represents a hydrogen atom, and R 7 represents C 1 to C 6 alkyl, and Z represents Z-1, Z-2, Z-3, Z-4, Z-6, Z-8, Z-9, Z-10, Z-11, Z-14, Z-17, Z-19, Z-20, Z-24, Z-27, Z-39, Z-41 or Z-46, Z 1 represents hydroxy, carboxy, amino, nitro, cyano, a halogen atom, C 1 to C 6 alkyl, C 3 to C 10 cycloalkyl, C 1 to C 6 haloalkyl, C 3 to C 10 halocycloalkyl, C 2 to C 6 alkenyl, C 1 to C 6 alkoxy, C 1 to C 6 alkylthio, C 1 to C 6 alkylsulfonyl, C 1 to C 6 alkylamino, C 1 to C 6 alkylcarbonyl, C 1 to C 6 alkoxycarbonyl, R i substituted C 1 to C 6 alkyl, -OR d , -NHC(O)R e , -NR h C(O)R e , -NHSO 2 R f , -C≡CR g , -SO 2 NH 2 , -C(O)NH 2 , -C(S)NH 2 , -C(=NOH)NH 2 , -C(=NOR)R', E-1, E-2, E-3, E-7, E-12, E-14, E-21, E-23, E-24, E-31, F-10 or F-11, Z 2 represents C 1 to C 6 alkyl, and R d represents C 2 to C 6 alkenyl, C 2 to C 6 alkynyl, C 1 to C 6 haloalkyl, R 10 substituted C 1 to C 6 alkyl, C 1 to C 6 alkylcarbonyl, C 1 to C 6 alkylaminocarbonyl or E-1, R 10 represents C 3 to C 10 cycloalkyl, C 1 to C 6 alkylcarbonyl, C 1 to C 6 alkoxycarbonyl, di(C 1 to C 6 )alkylaminocarbonyl, -C(=NOR)R', tetrahydrofuran-3-yl, E-1, E-2, E-3, E-5, E-22, E-30, E-41 or F-3, R e represents C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 1 to C 6 alkoxy, C 2 to C 6 alkenyloxy, C 1 to C 6 alkylamino, di(C 1 to C 6 )alkylamino, benzyloxy, E-1, E-2, E-3, E-4, E-8, E-11, E-13, E-14 or E-23, R f represents C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, di(C 1 to C 6 alkyl)amino or E-1, m5 represents an integer of 0, 1 or 2, n7 represents an integer of 0, n5 represents an integer of 0, 1, 2 or 3, n4 represents an integer of 0, 1 or 2, n3 represents an integer of 0, 1 or 2, n2 represents an integer of 0 or 2, n1 represents an integer of 1, u5 represents an integer of 0 or 1, u4 represents an integer of 0 or 1, r 1 represents an integer of 1, v6 represents an integer of 0, v5 represents an integer of 0, 1 or 2, v4 represents an integer of 0, 1, 2 or 3, v3 represents an integer of 0, 1 or 2, v2 represents an integer of 0 or 1, v1 represents an integer of 1. The pyrazole compound or a salt thereof according to Claim 1.
3. The pyrazole compound or a salt thereof according to Claim 1, wherein Z represents Z-8 to Z-44 or Z-46.
4. G 1 represents a halogen atom, C 1 to C 6 alkyl or C 1 to C 6 haloalkyl, T represents an oxygen atom, R X represents C 1 to C 6 alkyl, and R Y represents a hydrogen atom, and R 1 represents a hydrogen atom, and R 2 represents a hydrogen atom, and R 3 represents a hydrogen atom, and R 4 represents a hydrogen atom, Z represents Z-8, Z-9, Z-10, Z-11, Z-14, Z-17, Z-19, Z-20, Z-24, Z-27, Z-39, Z-41 or Z-46, Z 1 represents cyano, a halogen atom, C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, E-3 or E-7, Z 2 represents C 1 to C 6 alkyl, and Z a represents a halogen atom or C 1 to C 6 alkoxy, and m5 represents an integer of 0 or 1, n4 represents an integer of 0, 1 or 2, n3 represents an integer of 0, 1 or 2, n2 represents an integer of 0 or 2, n1 represents an integer of 1, p represents an integer of 1, v4 represents an integer of 1, The pyrazole compound according to claim 3, or a salt thereof, wherein v3 represents an integer of 1.
5. A pesticide containing, as an active ingredient, one or more selected from the pyrazole compounds according to any one of claims 1 to 4 and salts thereof.
6. A fungicide containing, as an active ingredient, one or more selected from the pyrazole compounds according to any one of claims 1 to 4 and salts thereof.
7. A fungicide for agricultural and horticultural use containing, as an active ingredient, one or more selected from the pyrazole compounds according to any one of claims 1 to 4 and salts thereof.
8. An antifungal agent containing, as an active ingredient, one or more selected from the pyrazole compounds according to any one of claims 1 to 4 and salts thereof.
9. An agent for controlling internal parasites containing, as an active ingredient, one or more selected from the pyrazole compounds according to any one of claims 1 to 4 and salts thereof.
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