Aryl tetrahydropyridine compounds and pest control agents
By developing new acyldihydric pesticides, the problem of pest resistance caused by existing pesticides has been solved, and effective insecticidal effects on agricultural pests and mites have been achieved.
Patent Information
- Application Number
- JP2024024109
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2023-12-25
- Filing Date
- 2024-02-20
- Publication Date
- 2025-04-04
AI Technical Summary
The long-term use of existing pesticides has led to increased pest resistance, and new pesticides need to be developed to have excellent insecticidal effects.
Develop a new acyldicycline pesticide, namely the derivative of acyldicycline pesticide, to improve its insecticidal effect on pests through specific chemical structure design.
This new pesticide has significant insecticidal effects on a variety of agricultural pests and mites, delaying the development of pest resistance and providing longer-lasting crop protection.
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Abstract
Description
[Technical field]
[0001] The present invention relates to novel aryltetrahydropyridine compounds and their salts, production intermediates thereof, and pest control agents, agricultural chemicals, control agents, insecticides or acaricides, seed treatment agents and soil treatment agents each containing the compound and / or its salt as an active ingredient. [Background technology]
[0002] Certain aryltetrahydropyridine compounds are known to exhibit pest control activity (eg, Patent Documents 1 and 2). [Prior art documents] [Patent documents]
[0003] [Patent Document 1] International Publication No. 2021 / 261562 [Patent Document 2] International Publication No. 2023 / 127806 Summary of the Invention [Problem to be solved by the invention]
[0004] However, the long-term use of pesticides can cause the emergence of pests and harmful organisms that have acquired resistance to existing insecticides, and therefore there is a constant demand for the development of new pesticides that have excellent pest control effects. [Means for solving the problem]
[0005] As a result of intensive research aimed at solving the above problems, the present inventors have found that a novel aryltetrahydropyridine compound represented by the following formula (1) according to the present invention exhibits excellent pest control activity, particularly excellent insecticidal and acaricidal activity, and have completed the present invention.
[0006] That is, the present invention relates to an aryltetrahydropyridine compound represented by the following formula (1) or a salt thereof.
[0007] Formula (1):
[0008] [ka]
[0009] [In the formula, Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-15, Q-16, Q-17, Q-18, Q-19, Q-20, Q-21, Q-22, Q-23, Q-24, Q-25, Q-26, Q-27, Q-28, Q-2 9, Q-30, Q-31, Q-32, Q-33, Q-34, Q-35, Q-36, Q-37, Q-38, Q-39, Q-40, Q-41, Q-42, Q-43, Q-44, Q-45, Q-46, Q-47, Q-48, Q-49, Q-50, Q-51, Q-52, Q-53, Q-54, Q-55 or Q-56;
[0010] [ka]
[0011] [ka]
[0012] Z 1 is a halogen atom, C 1 ~C 6 Alkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Alkynyl, halo(C 1 ~C 6 ) alkyl, halo(C 2 ~C 6 ) alkenyl, halo(C 2 ~C 6 ) alkynyl, C 1 ~C6 Alkoxy, halo(C 1 ~C 6 ) Alkoxy, C 2 ~C 6 Alkoxy(C 1 ~C 6 ) Alkoxy, C 2 ~C 6 Alkenyloxy, halo(C 2 ~C 6 ) alkenyloxy, C 2 ~C 6 Alkynyloxy, halo(C 2 ~C 6 ) alkynyloxy, C 1 ~C 6 Alkylthio, C 1 ~C 6 Alkylsulfinyl, C 1 ~C 6 Alkyl sulfonyl, halo(C 1 ~C 6 ) Alkylthio, Halo(C 1 ~C 6 ) alkylsulfinyl, halo(C 1 ~C 6 ) Alkyl sulfonyl, C 2 ~C 6 Alkenylthio, C 2 ~C 6 Alkenylsulfinyl, C 2 ~C 6 Alkenylsulfonyl, halo(C 2 ~C 6 ) alkenylthio, halo(C 2 ~C 6 ) alkenylsulfinyl, halo(C 2 ~C 6 ) alkenylsulfonyl, C 2 ~C 6 Alkynylthio, C 2 ~C 6 Alkynylsulfinyl, C 2 ~C 6 Alkynylsulfonyl, halo(C 2 ~C 6 ) Alkynylthio, halo(C 2 ~C 6 ) Alkynylsulfinyl, halo(C 2 ~C6 ) Alkynylsulfonyl, -NH 2 , C 1 ~C 6 Alkylamino, di(C 1 ~C 6 ) alkylamino, halo(C 1 ~C 6 ) Alkylamino, dihalo(C 1 ~C 6 ) Alkylamino, formyl, carboxy, C 1 ~C 6 Alkylcarbonyl, halo(C 1 ~C 6 ) Alkylcarbonyl, C 1 ~C 6 Alkoxycarbonyl, halo(C 1 ~C 6 ) alkoxycarbonyl, C 1 ~C 6 Alkylaminocarbonyl, halo(C 1 ~C 6 ) alkylaminocarbonyl, di(C 1 ~C 6 ) Alkylaminocarbonyl, Hydroxy, C 1 ~C 6 Alkylcarbonyloxy, C 1 ~C 6 Alkoxycarbonyloxy, C 1 ~C 6 Alkyl sulfonyloxy, halo(C 1 ~C 6 ) Alkylsulfonyloxy, -SO 3 H, C 1 ~C 6 Alkylaminosulfonyl, di(C 1 ~C 6 ) alkylaminosulfonyl, -C(=NOR 12 )R 13 , cyano or nitro; R 12 is a hydrogen atom or C 1 ~C 6 represents an alkyl group, R 13 is a hydrogen atom or C 1 ~C 6 represents an alkyl group, Z3 is a hydrogen atom or C 1 ~C 6 represents an alkyl group, J represents J-1 or J-2;
[0013] [ka]
[0014] A 1 represents a nitrogen atom or CH; G stands for G-1, G-2, G-3, G-4, G-5, G-6, G-7, G-8, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G -17, G-18, G-19, G-20, G-21, G-22, G-23, G-24, G-25, G-26, G-27, G-28, G-29, G-30, G-31, G- 32, G-33, G-34, G-35, G-36, G-37, G-38, G-39, G-40, G-41, G-42, G-43, G-44, G-45, G-46, G-4 7, represents G-48, G-49, G-50, G-51, G-52, G-53, G-54, G-55, G-56, G-57, G-58, G-59, G-60 or G-61;
[0015] [ka]
[0016] [ka]
[0017] Z 2 is a halogen atom, C 1 ~C 6 Alkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Alkynyl, halo(C 1 ~C 6 ) alkyl, halo(C 2 ~C 6 ) alkenyl, halo(C2 ~C 6 ) alkynyl, C 1 ~C 6 Alkoxy, halo(C 1 ~C 6 ) Alkoxy, C 1 ~C 6 Alkoxy(C 1 ~C 6 ) Alkoxy, C 2 ~C 6 Alkenyloxy, halo(C 2 ~C 6 ) alkenyloxy, C 2 ~C 6 Alkynyloxy, halo(C 2 ~C 6 ) alkynyloxy, C 1 ~C 6 Alkylthio, C 1 ~C 6 Alkylsulfinyl, C 1 ~C 6 Alkyl sulfonyl, halo(C 1 ~C 6 ) Alkylthio, Halo(C 1 ~C 6 ) alkylsulfinyl, halo(C 1 ~C 6 ) Alkyl sulfonyl, C 2 ~C 6 Alkenylthio, C 2 ~C 6 Alkenylsulfinyl, C 2 ~C 6 Alkenylsulfonyl, halo(C 2 ~C 6 ) alkenylthio, halo(C 2 ~C 6 ) alkenylsulfinyl, halo(C 2 ~C 6 ) alkenylsulfonyl, C 2 ~C 6 Alkynylthio, C 2 ~C 6 Alkynylsulfinyl, C 2 ~C 6 Alkynylsulfonyl, halo(C 2 ~C 6 ) Alkynylthio, halo(C2 ~C 6 ) Alkynylsulfinyl, halo(C 2 ~C 6 ) Alkynylsulfonyl, -NH 2 , C 1 ~C 6 Alkylamino, di(C 1 ~C 6 ) alkylamino, halo(C 1 ~C 6 ) Alkylamino, dihalo(C 1 ~C 6 ) Alkylamino, formyl, carboxy, C 1 ~C 6 Alkylcarbonyl, halo(C 1 ~C 6 ) Alkylcarbonyl, C 1 ~C 6 Alkoxycarbonyl, halo(C 1 ~C 6 ) alkoxycarbonyl, C 1 ~C 6 Alkylaminocarbonyl, halo(C 1 ~C 6 ) alkylaminocarbonyl, di(C 1 ~C 6 ) Alkylaminocarbonyl, Hydroxy, C 1 ~C 6 Alkylcarbonyloxy, C 1 ~C 6 Alkoxycarbonyloxy, C 1 ~C 6 Alkyl sulfonyloxy, halo(C 1 ~C 6 ) Alkylsulfonyloxy, -SO 3 H, C 1 ~C 6 Alkylaminosulfonyl, di(C 1 ~C 6 ) alkylaminosulfonyl, -C(=NOR 14 )R 15 , nitro or cyano; R 14 is a hydrogen atom or C 1 ~C 6 represents an alkyl group, R 15is a hydrogen atom or C 1 ~C 6 represents an alkyl group, Z 4 is C 1 ~C 6 represents an alkyl group, R 1 is a hydrogen atom, a halogen atom, or a halo(C 1 ~C 6 ) Alkyl, C 1 ~C 6 represents alkyl or cyano; R 2 is a hydrogen atom, C 1 ~C 6 Alkyl, halo(C 1 ~C 6 ) Alkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Alkynyl, C 3 ~C 6 Cycloalkyl, -C(O)R 4 , -C(O)OR 5 , D-1, D-2 or D-3;
[0018] [ka]
[0019] R 4 is C 1 ~C 6 Alkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Alkynyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 6 Alkylcarbonyl, di(C 1 ~C 6 ) alkylamino or R 6 Replaced by (C 1 ~C 6 ) alkyl, R 6 is a halogen atom, C 1 ~C 6Alkoxy, cyano, nitro, phenyl or R 8 represents a phenyl substituted with Z 5 is a halogen atom, C 1 ~C 6 Alkyl, C 1 ~C 6 represents alkoxy, cyano or nitro, R 8 is a halogen atom, C 1 ~C 6 Alkyl, C 1 ~C 6 represents alkoxy, cyano or nitro, R 5 is C 1 ~C 6 Alkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Alkynyl, C 3 ~C 6 Cycloalkyl, R 9 Replaced by (C 1 ~C 6 ) alkyl, phenyl or R 10 represents a phenyl substituted with R 9 is a halogen atom, C 1 ~C 6 Alkoxy, cyano, nitro, phenyl or R 11 represents a phenyl substituted with R 10 is a halogen atom, C 1 ~C 6 Alkyl, C 1 ~C 6 represents alkoxy, cyano or nitro, R 11 is a halogen atom, C 1 ~C 6 Alkyl, C 1 ~C 6 represents alkoxy, cyano or nitro, R 3 is a hydrogen atom, C 1 ~C 6 Alkyl, halo(C 1 ~C 6 ) Alkyl, C2 ~C 6 Alkenyl, C 2 ~C 6 Alkynyl, C 3 ~C 6 Cycloalkyl or C 1 ~C 6 represents an alkylcarbonyl; X represents an oxygen atom or a sulfur atom; Y represents an oxygen atom or a sulfur atom; t1 represents an integer of 0 or 1; t2 represents an integer of 0, 1 or 2; t3 represents an integer of 0, 1, 2 or 3; t4 represents an integer of 0, 1, 2, 3 or 4; t5 represents an integer of 0, 1, 2, 3, 4, or 5. t8 represents an integer of 0, 1, 2, 3 or 4. Effect of the Invention
[0020] The compound of the present invention represented by formula (1) exhibits excellent insecticidal and acaricidal activity against many agricultural pests, spider mites, and internal or external parasites of mammals or birds. Therefore, the present invention can provide a novel aryltetrahydropyridine compound or a salt thereof that is useful as a pest control agent, particularly as an insecticide. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
[0021] In the compound according to the present invention represented by formula (1) (hereinafter also referred to as "the compound of the present invention"), the existence of tautomers represented by the following formulas is considered, and the compound of the present invention represented by formula (1) includes all tautomers or a mixture of tautomers containing any ratio.
[0022] [ka]
[0023] The compound of the present invention may have geometric isomers of E- and Z-isomers depending on the type of substituent, and the compound of the present invention includes a mixture containing these E-, Z-, or E- and Z-isomers in any ratio.
[0024] Furthermore, the compound of the present invention may have optically active forms due to the presence of one or more asymmetric carbon atoms or sulfur atoms, and the compound of the present invention includes all optically active forms and racemic forms.
[0025] In addition, the compound of the present invention may have tautomers depending on the type of substituent, and the compound of the present invention includes all tautomers or a mixture of tautomers containing any ratio.
[0026] In addition, the compound 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 compound of the present invention encompasses all rotational isomers or a mixture of diastereomers containing them in any ratio.
[0027] Among the compounds of the present invention, those which can be converted into salts by a conventional method include, for example, salts of hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, and hydroiodic acid; salts of inorganic acids such as nitric acid, sulfuric acid, phosphoric acid, chloric acid, and perchloric acid; salts of sulfonic acids such as methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, and p-toluenesulfonic acid; salts of carboxylic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, oxalic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, and citric acid; salts of amino acids such as glutamic acid and aspartic acid; salts of alkali metals such as lithium, sodium, and potassium; salts of alkaline earth metals such as calcium, barium, and magnesium; aluminum salts; and quaternary ammonium salts such as tetramethylammonium salts, tetrabutylammonium salts, and benzyltrimethylammonium salts.
[0028] Next, specific examples of the substituents shown in this specification are shown below, where n- means normal, i- means iso, s- means secondary, and tert- means tertiary.
[0029] In the present specification, the term "halogen atom" includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. In addition, the term "halo" in the present specification also represents these halogen atoms.
[0030] In this specification, "C a ~C b The term "alkyl" refers to a linear or branched hydrocarbon group having a to b carbon atoms, and specific examples thereof include methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, tert-butyl, n-pentyl, 1,1-dimethylpropyl, and n-hexyl, each of which is selected within the range of the number of carbon atoms specified.
[0031] As used herein, "halo(C a ~C bThe notation of "alkyl" represents a linear or branched hydrocarbon group having a to b carbon atoms in which hydrogen atoms bonded to the carbon atoms are optionally substituted with halogen atoms, and in this case, when the alkyl group is substituted with two or more halogen atoms, the halogen atoms may be the same or different from each other. For example, 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, 2,2,2-trichloroethyl, 2-bromo-2,2-difluoroethyl, 1,1,2,2-tetrafluoroethyl, 2-chloro-1,1,2-trifluoroethyl, 2-chloro-1,1,2,2-tetrafluoroethyl, pentafluoroethyl, 2,2-difluoro Specific examples include propyl, 3,3,3-trifluoropropyl, 3-bromo-3,3-difluoropropyl, 2,2,3,3-tetrafluoropropyl, 2,2,3,3,3-pentafluoropropyl, 1,1,2,3,3,3-hexafluoropropyl, heptafluoropropyl, 2,2,2-trifluoro-1-(methyl)ethyl, 2,2,2-trifluoro-1-(trifluoromethyl)ethyl, 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl, 2,2,3,4,4,4-hexafluorobutyl, 2,2,3,3,4,4,4-heptafluorobutyl, nonafluorobutyl, and the like, and are selected within the range of the number of carbon atoms specified for each.
[0032] In this specification, "C a ~C bThe term "alkenyl" refers to a linear or branched unsaturated hydrocarbon group having a to b carbon atoms and having one or more double bonds in the molecule. Specific examples include vinyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 2-butenyl, 2-methyl-2-propenyl, 3-methyl-2-butenyl, and 1,1-dimethyl-2-propenyl, and are selected within the range of the number of carbon atoms specified for each group.
[0033] As used herein, "halo(C a ~C b The term "alkenyl" refers to a linear or branched unsaturated hydrocarbon group having a to b carbon atoms and one or more double bonds in the molecule, in which hydrogen atoms bonded to carbon atoms are optionally substituted with halogen atoms. In this case, when the alkenyl group is substituted with two or more halogen atoms, the halogen atoms may be the same or different from each other. For example, specific examples include 2,2-dichlorovinyl, 2-fluoro-2-propenyl, 2-chloro-2-propenyl, 3-chloro-2-propenyl, 2-bromo-2-propenyl, 3,3-difluoro-2-propenyl, 2,3-dichloro-2-propenyl, 3,3-dichloro-2-propenyl, 2,3,3-trifluoro-2-propenyl, 2,3,3-trichloro-2-propenyl, 1-(trifluoromethyl)ethenyl, 4,4-difluoro-3-butenyl, 3,4,4-trifluoro-3-butenyl, and 3-chloro-4,4,4-trifluoro-2-butenyl, and the like are selected within the range of the number of carbon atoms specified for each.
[0034] In this specification, "C a ~C b The term "alkynyl" refers to a linear or branched unsaturated hydrocarbon group having a to b carbon atoms and having one or more triple bonds in the molecule, and specific examples thereof include ethynyl, propargyl, 2-butynyl, 3-butynyl, 1-pentynyl, and 1-hexynyl, each of which is selected within the range of the number of carbon atoms specified.
[0035] As used herein, "halo(C a ~C b The expression "alkynyl" refers to an unsaturated hydrocarbon group having a to b carbon atoms, a straight or branched chain, and one or more triple bonds in the molecule, in which hydrogen atoms bonded to the carbon atoms are optionally substituted with halogen atoms. In this case, when the alkynyl group is substituted with two or more halogen atoms, the halogen atoms may be the same or different from each other. For example, 2-chloroethynyl, 2-bromoethynyl, 2-iodoethynyl, 3-chloro-2-propynyl, 3-bromo-2-propynyl, 3-iodo-2-propynyl, etc. are specific examples, and each is selected within the range of the number of carbon atoms specified.
[0036] In this specification, "C a ~C b The term "alkoxy" represents an alkyl-O- group having the above-mentioned meaning and containing a to b carbon atoms, and specific examples thereof include methoxy, ethoxy, n-propyloxy, i-propyloxy, n-butyloxy, i-butyloxy, s-butyloxy, tert-butyloxy, 2-ethylhexyloxy, and the like, and each of the specified ranges of the number of carbon atoms is selected.
[0037] As used herein, "halo(C a ~C b The notation of "alkoxy" represents a haloalkyl-O- group having the above-mentioned meaning and containing a to b carbon atoms, and specific examples thereof include difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy, 1,1,2,3,3,3-hexafluoropropyloxy, and the like, each of which is selected within the range of the specified number of carbon atoms.
[0038] In this specification, "C a ~C b Alkoxy(C d ~C eThe notation "alkoxy" refers to any C a ~C b The alkoxy group represents an alkoxy group having d to e carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted by the alkoxy group. Specific examples thereof include methoxymethoxy and 2-methoxyethoxy, and each of the alkoxy groups is selected within the range of the number of carbon atoms specified.
[0039] In this specification, "C a ~C b The term "alkenyloxy" represents an alkenyl-O- group having the above-mentioned meaning and containing a to b carbon atoms, and specific examples thereof include 2-propenyloxy, 2-butenyloxy, 2-methyl-2-propenyloxy, and 3-methyl-2-butenyloxy, each of which is selected within the range of the number of carbon atoms specified.
[0040] As used herein, "halo(C a ~C b The notation of "alkenyloxy" represents a haloalkenyl-O- group having the above-mentioned meaning and containing a to b carbon atoms, and specific examples thereof include 3,3-difluoroallyloxy and 3,3-dichloroallyloxy, and are selected within the range of the number of carbon atoms specified for each group.
[0041] In this specification, "C a ~C b The term "alkynyloxy" represents an alkynyl-O- group having the above-mentioned meaning and containing a to b carbon atoms, and specific examples thereof include ethynyloxy, propargyloxy, 2-butynyloxy, 1-pentynyloxy, and 1-hexynyloxy, each of which is selected within the range of the number of carbon atoms specified.
[0042] As used herein, "halo(C a ~C bThe notation of "alkynyloxy" represents a haloalkynyl-O- group having the above-mentioned meaning and containing a to b carbon atoms, and specific examples thereof include 3-chloro-2-propynyloxy, 3-bromo-2-propynyloxy, and 3-iodo-2-propynyloxy, and the like, each of which is selected within the range of the number of carbon atoms specified.
[0043] In this specification, "C a ~C b The term "alkylthio" represents an alkyl-S- group having the above-mentioned meaning and containing a to b carbon atoms, and specific examples thereof include methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, tert-butylthio, etc., and each of these is selected within the range of the specified number of carbon atoms.
[0044] As used herein, "halo(C a ~C b The notation of "(trifluoromethyl)thio)" represents a haloalkyl-S- group having the above-mentioned meaning containing a to b carbon atoms, and specific examples thereof include difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, 2,2,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, 2-chloro-1,1,2-trifluoroethylthio, pentafluoroethylthio, 1,1,2,3,3,3-hexafluoropropylthio, heptafluoropropylthio, 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethylthio, nonafluorobutylthio, and the like, and each is selected within the range of the specified number of carbon atoms.
[0045] In this specification, "C a ~C b The term "alkenylthio" represents an alkenyl-S- group having a to b carbon atoms as defined above, and specific examples thereof include 2-propenylthio, 2-butenylthio, 2-methyl-2-propenylthio, and 3-methyl-2-butenylthio, each of which is selected within the range of the number of carbon atoms specified.
[0046] As used herein, "halo(C a ~C b The notation of "(alkenylthio)" represents a haloalkenyl-S- group having the above-mentioned meaning containing a to b carbon atoms, and specific examples thereof include 2-fluoro-2-propenylthio, 2-chloro-2-propenylthio, 3,3-difluoro-2-propenylthio, 3,3-dichloro-2-propenylthio, 2,3,3-trifluoro-2-propenylthio, 4,4-difluoro-3-butenylthio, and 3,4,4-trifluoro-3-butenylthio, and are selected within the range of the number of carbon atoms specified for each group.
[0047] In this specification, "C a ~C b The term "alkynylthio" represents the above-mentioned alkynyl-S- group having a to b carbon atoms, and specific examples thereof include propynylthio, butynylthio, pentynylthio, and hexynylthio, each of which is selected within the range of the number of carbon atoms specified.
[0048] As used herein, "halo(C a ~C b The notation of "alkynylthio" represents a haloalkynyl-S- group having the above-mentioned meaning containing a to b carbon atoms, and specific examples thereof include 3-chloro-2-propynylthio, 3-bromo-2-propynylthio, and 3-iodo-2-propynylthio, and the like, each of which is selected within the range of the specified number of carbon atoms.
[0049] In this specification, "C a ~C b The notation of "alkylsulfinyl" represents the above-mentioned alkyl-S(O)- group having a to b carbon atoms, and specific examples thereof include methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, i-propylsulfinyl, n-butylsulfinyl, i-butylsulfinyl, S-butylsulfinyl, tert-butylsulfinyl, and the like, each selected within the specified range of the number of carbon atoms.
[0050] As used herein, "halo(C a~C b The notation of "(1-(trifluoromethyl)sulfinyl)" represents a haloalkyl-S(O)- group having the above-mentioned meaning containing a to b carbon atoms, and specific examples thereof include difluoromethylsulfinyl, trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethylsulfinyl, nonafluorobutylsulfinyl, and the like, selected within the range of the number of carbon atoms specified for each group.
[0051] In this specification, "C a ~C b The term "alkenylsulfinyl" represents an alkenyl-S(O)- group having a to b carbon atoms as defined above, and specific examples thereof include 2-propenylsulfinyl, 2-butenylsulfinyl, 2-methyl-2-propenylsulfinyl, and 3-methyl-2-butenylsulfinyl, each of which is selected within the range of the number of carbon atoms specified.
[0052] As used herein, "halo(C a ~C b The notation of "haloalkenylsulfinyl" represents a haloalkenyl-S(O)- group having a to b carbon atoms as defined above, and specific examples thereof include 2-fluoro-2-propenylsulfinyl, 2-chloro-2-propenylsulfinyl, 3,3-difluoro-2-propenylsulfinyl, 3,3-dichloro-2-propenylsulfinyl, 4,4-difluoro-3-butenylsulfinyl, and 3,4,4-trifluoro-3-butenylsulfinyl, each of which is selected within the range of the specified number of carbon atoms.
[0053] In this specification, "C a ~C b The term "alkynylsulfinyl" represents an alkynyl-S(O)- group having the above-mentioned meaning and containing a to b carbon atoms, and specific examples thereof include 2-propynylsulfinyl and 2-butynylsulfinyl, each of which is selected within the range of the number of carbon atoms specified.
[0054] As used herein, "halo(C a ~C b The notation of "alkynylsulfinyl" represents a haloalkynyl-S(O)- group having the above-mentioned meaning containing a to b carbon atoms, and specific examples thereof include 3-chloro-2-propynylsulfinyl, 3-bromo-2-propynylsulfinyl, and 3-iodo-2-propynylsulfinyl, and are selected within the range of the number of carbon atoms specified for each group.
[0055] In this specification, "C a ~C b The expression "alkylsulfonyl" means an alkyl-SO 3 having the above-mentioned meaning and containing a to b carbon atoms. 2 - group, and specific examples include methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl, n-butylsulfonyl, i-butylsulfonyl, s-butylsulfonyl, tert-butylsulfonyl, and the like, each of which is selected within the range of the number of carbon atoms specified.
[0056] As used herein, "halo(C a ~C b The expression "alkylsulfonyl" refers to haloalkyl-SO having the above-mentioned meaning and containing a to b carbon atoms. 2 - group, and specific examples thereof include difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 1,1,2,2-tetrafluoroethylsulfonyl, and 2-chloro-1,1,2-trifluoroethylsulfonyl, and each is selected within the range of the number of carbon atoms specified.
[0057] In this specification, "C a ~C b The expression "alkenylsulfonyl" refers to the above-mentioned alkenyl-SO having a to b carbon atoms. 2- group, and specific examples include 2-propenylsulfonyl, 2-butenylsulfonyl, 2-methyl-2-propenylsulfonyl, 3-methyl-2-butenylsulfonyl, etc., each of which is selected within the range of the number of carbon atoms specified.
[0058] As used herein, "halo(C a ~C b The expression "alkenylsulfonyl" refers to the above-mentioned haloalkenyl-SO having a to b carbon atoms. 2 - group, and specific examples thereof include 2-fluoro-2-propenylsulfonyl, 2-chloro-2-propenylsulfonyl, 3,3-difluoro-2-propenylsulfonyl, 3,3-dichloro-2-propenylsulfonyl, 4,4-difluoro-3-butenylsulfonyl, and 3,4,4-trifluoro-3-butenylsulfonyl, each of which is selected within the range of the number of carbon atoms specified.
[0059] In this specification, "C a ~C b The expression "alkynylsulfonyl" refers to the above-mentioned alkynyl-SO having a to b carbon atoms. 2 - group, and specific examples include 2-propynylsulfonyl, 2-butynylsulfonyl, etc., each of which is selected within the range of the number of carbon atoms specified.
[0060] As used herein, "halo(C a ~C b The expression "alkynylsulfonyl" refers to haloalkynyl-SO having the above-mentioned meaning and containing a to b carbon atoms. 2 - group, and specific examples include 3-chloro-2-propynylsulfonyl, 3-bromo-2-propynylsulfonyl, 3-iodo-2-propynylsulfonyl, etc., each of which is selected within the range of the number of carbon atoms specified.
[0061] In this specification, "C a ~C bThe term "alkylamino" refers to an amino group in which one of the hydrogen atoms is substituted with the above-mentioned alkyl having a to b carbon atoms, and specific examples thereof include methylamino, ethylamino, n-propylamino, i-propylamino, n-butylamino, i-butylamino, and tert-butylamino, each of which is selected within the range of the number of carbon atoms specified.
[0062] As used herein, "halo(C a ~C b The term "alkylamino" refers to an amino group in which one of the hydrogen atoms is substituted with haloalkyl having a to b carbon atoms, and specific examples thereof include 2,2,2-trifluoroethylamino, 2-chloro-2,2-difluoroethylamino, and 3,3,3-trifluoropropylamino, each of which is selected within the range of the number of carbon atoms specified.
[0063] In this specification, "di(C a ~C b The expression "alkylamino" represents an amino group in which both hydrogen atoms are substituted with alkyl as defined above, each of which may be the same or different and has a to b carbon atoms. Specific examples include dimethylamino, ethyl(methyl)amino, diethylamino, n-propyl(methyl)amino, i-propyl(methyl)amino, di(n-propyl)amino, di(n-butyl)amino, etc., each of which is selected within the range of the specified number of carbon atoms.
[0064] As used herein, "dihalo(C a ~C b The expression "alkylamino" represents an amino group in which both hydrogen atoms are substituted with haloalkyl having a to b carbon atoms, which may be the same or different, as defined above. Specific examples include bis(2,2,2-trifluoroethyl)amino, and the like, and each is selected within the range of the number of carbon atoms specified.
[0065] In this specification, "C a ~Cb The term "cycloalkyl" refers to a cyclic saturated hydrocarbon group having a to b carbon atoms, which can form a single ring or a composite ring structure having 3 to 10 members. Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms. Specific examples include cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl, each of which is selected within the range of the specified number of carbon atoms.
[0066] In this specification, "C a ~C b The term "alkylcarbonyl" represents the above-mentioned alkyl-C(O)- group having a to b carbon atoms, and specific examples thereof include acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, 2-methylbutanoyl, pivaloyl, hexanoyl, and heptanoyl, each of which is selected within the range of the number of carbon atoms specified.
[0067] As used herein, "halo(C a ~C b The notation of "alkylcarbonyl" represents a haloalkyl-C(O)- group having a to b carbon atoms as defined above, and specific examples thereof include fluoroacetyl, chloroacetyl, difluoroacetyl, dichloroacetyl, trifluoroacetyl, chlorodifluoroacetyl, bromodifluoroacetyl, trichloroacetyl, pentafluoropropionyl, heptafluorobutanoyl, 3-chloro-2,2-dimethylpropanoyl, and the like, each of which is selected within the range of the specified number of carbon atoms.
[0068] In this specification, "C a ~C bThe term "alkoxycarbonyl" represents the above-mentioned alkyl-OC(O)- group having a to b carbon atoms, and specific examples thereof include methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, i-propyloxycarbonyl, n-butoxycarbonyl, i-butoxycarbonyl, s-butoxycarbonyl, tert-butoxycarbonyl, 2-ethylhexyloxycarbonyl, and the like, each of which is selected within the range of the specified number of carbon atoms.
[0069] As used herein, "halo(C a ~C b The notation of "alkoxycarbonyl" represents the above-mentioned haloalkyl-OC(O)- group having a to b carbon atoms, and specific examples thereof include chloromethoxycarbonyl, 2-chloroethoxycarbonyl, 2,2-difluoroethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, and 2,2,2-trichloroethoxycarbonyl, and the like are selected within the range of the number of carbon atoms specified for each group.
[0070] In this specification, "C a ~C b The term "alkylaminocarbonyl" represents a carbamoyl group in which one of the hydrogen atoms is substituted with the above-mentioned alkyl having a to b carbon atoms, and specific examples thereof include methylcarbamoyl, ethylcarbamoyl, n-propylcarbamoyl, i-propylcarbamoyl, n-butylcarbamoyl, i-butylcarbamoyl, s-butylcarbamoyl, and tert-butylcarbamoyl, each of which is selected within the range of the specified number of carbon atoms.
[0071] As used herein, "halo(C a ~C bThe expression "alkylaminocarbonyl" represents a carbamoyl group in which one of the hydrogen atoms is substituted by the above-mentioned haloalkyl having a to b carbon atoms, and specific examples thereof include 2-fluoroethylcarbamoyl, 2-chloroethylcarbamoyl, 2,2-difluoroethylcarbamoyl, and 2,2,2-trifluoroethylcarbamoyl, each of which is selected within the range of the number of carbon atoms specified.
[0072] In this specification, "di(C a ~C b The expression "alkylaminocarbonyl" represents a carbamoyl group in which both hydrogen atoms are substituted with alkyl having a to b carbon atoms, each of which may be the same or different, as defined above. Specific examples include N,N-dimethylcarbamoyl, N-ethyl-N-methylcarbamoyl, N,N-diethylcarbamoyl, N,N-di(n-propyl)carbamoyl, and N,N-di(n-butyl)carbamoyl, each of which is selected within the range of the number of carbon atoms specified.
[0073] In this specification, "C a ~C b The term "alkylcarbonyloxy" refers to an alkyl-C(O)-O- group having the above-mentioned meaning and containing a to b carbon atoms. Specific examples include acetyloxy, propionyloxy, butyryloxy, isobutyryloxy, etc., each of which is selected within the range of the number of carbon atoms specified.
[0074] In this specification, "C a ~C b The term "alkoxycarbonyloxy" represents an alkoxy-C(O)-O- group having the above-mentioned meaning containing a to b carbon atoms, and specific examples thereof include methoxycarbonyloxy, ethoxycarbonyloxy, i-butyloxycarbonyloxy, and tert-butyloxycarbonyloxy, and are selected within the range of the number of carbon atoms specified for each group.
[0075] In this specification, "C a ~C bThe term "alkylsulfonyloxy" represents an alkylsulfonyl-O- group having the above-mentioned meaning and containing a to b carbon atoms, and specific examples thereof include methylsulfonyloxy, ethylsulfonyloxy, n-propylsulfonyloxy, i-propylsulfonyloxy, and the like, and each of these is selected within the range of the specified number of carbon atoms.
[0076] As used herein, "halo(C a ~C b The notation of "alkylsulfonyloxy" represents a haloalkylsulfonyl-O- group having the above-mentioned meaning and containing a to b carbon atoms, and specific examples thereof include difluoromethylsulfonyloxy, trifluoromethylsulfonyloxy, chlorodifluoromethylsulfonyloxy, bromodifluoromethylsulfonyloxy, and the like, and each is selected within the specified range of the number of carbon atoms.
[0077] In this specification, "C a ~C b The term "alkylaminosulfonyl" represents a sulfamoyl group in which one of the hydrogen atoms is substituted with the above-mentioned alkyl having a to b carbon atoms, and specific examples thereof include methylsulfamoyl, ethylsulfamoyl, n-propylsulfamoyl, i-propylsulfamoyl, n-butylsulfamoyl, i-butylsulfamoyl, s-butylsulfamoyl, tert-butylsulfamoyl, and the like, each selected within the range of the specified number of carbon atoms.
[0078] In this specification, "di(C a ~C b The expression "alkylaminosulfonyl" represents a sulfamoyl group in which both hydrogen atoms are substituted by alkyl having a to b carbon atoms, which may be the same or different, as defined above. Specific examples include N,N-dimethylsulfamoyl, N-ethyl-N-methylsulfamoyl, N,N-diethylsulfamoyl, N,N-di(n-propyl)sulfamoyl, N,N-di(n-butyl)sulfamoyl, and the like, selected within the range of the number of carbon atoms specified for each group.
[0079] In this specification, "C a ~C b The term "cycloalkylcarbonyl" represents the above-mentioned cycloalkyl-C(O)- group having a to b carbon atoms, and specific examples thereof include cyclopropylcarbonyl, 2-methylcyclopropylcarbonyl, cyclobutylcarbonyl, and the like, selected within the range of the number of carbon atoms specified for each group.
[0080] As used herein, "halo(C a ~C b The notation of "cycloalkylcarbonyl" represents a halocycloalkyl-C(O)- group having the above-mentioned meaning containing a to b carbon atoms, and specific examples thereof include 2,2-dichlorocyclopropylcarbonyl, 2,2-dichloro-1-methylcyclopropylcarbonyl, and the like, and each is selected within the specified range of the number of carbon atoms.
[0081] In this specification, "R 6 Replaced by (C a ~C b The notation "alkyl" means that any hydrogen atom attached to a carbon atom is substituted with one or more substituents R 6 represents an alkyl group having the above-mentioned meaning, which is partially or completely substituted with a to b carbon atoms, and each of the carbon atoms is selected within the range of the specified number of carbon atoms. 6 When two or more are present, the substituent R 6 may be the same or different from each other.
[0082] In this specification, "R 8 The notation "phenyl substituted with" means that any hydrogen atom attached to a carbon atom is substituted with one or more substituents R 8 In this case, the substituent R 8 When two or more are present, the substituent R 8 may be the same or different from each other.
[0083] In this specification, "R 9 Replaced by (Ca ~C b The notation "alkyl" means that any hydrogen atom attached to a carbon atom is substituted with one or more substituents R 9 represents an alkyl group having the above-mentioned meaning, which is partially or completely substituted with a to b carbon atoms, and each of the carbon atoms is selected within the range of the specified number of carbon atoms. 9 When two or more are present, the substituent R 9 may be the same or different from each other.
[0084] In this specification, "R 10 The notation "phenyl substituted with" means that any hydrogen atom attached to a carbon atom is substituted with one or more substituents R 10 In this case, the substituent R 10 When two or more are present, the substituent R 10 may be the same or different from each other.
[0085] In this specification, "R 11 The notation "phenyl substituted with" means that any hydrogen atom attached to a carbon atom is substituted with one or more substituents R 11 In this case, the substituent R 11 When two or more are present, the substituent R 11 may be the same or different from each other.
[0086] Next, a method for producing the compound of the present invention represented by formula (1) is described below. The compound of the present invention 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 described as "compound of the present invention (1)", and the "compound of formula (2)" is also described as "compound (2)". Other compounds are also described in the same manner.
[0087] [Manufacturing method 1] The compound (1) of the present invention can be produced by reacting a compound (2) with a compound (3).
[0088] [ka]
[0089] (In the formula, Ja represents Ja-1 or Ja-2,
[0090] [ka]
[0091] J, Q, G, X, Y, A 1 ,R 1 ,R 2 and R 3 has the same meaning as above, Ga represents a halogen atom, etc., and Gb represents B(OH) 2 etc.) The compound (1) of the present invention can be produced by reacting the compound (2) with the compound (3) in a solvent or without a solvent.
[0092] When a solvent is used, any solvent may be used as long as it is inert to the reaction, and examples thereof include water, alcohol solvents such as methanol, ethanol, etc., ether solvents such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane, etc., aromatic hydrocarbon solvents such as benzene, xylene, toluene, etc., aliphatic hydrocarbon solvents such as pentane, hexane, cyclohexane, etc., halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichloroethane, etc., nitrile solvents such as acetonitrile, propionitrile, etc., amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N,N'-dimethylimidazolidinone, etc., dimethyl sulfoxide, and mixed solvents thereof.
[0093] The reaction can also be carried out using a base. Examples of bases 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), and 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, and potassium phosphate; and metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide. The amount (equivalent) of the base used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (2).
[0094] The reaction can be carried out in the presence of a palladium catalyst. Examples of the palladium catalyst include [1,1'-bis(diphenylphosphino)ferrocene]palladium(divalent) dichloride dichloromethane adduct. The amount of the palladium catalyst used is 0.005 to 20 equivalents per equivalent of compound (2).
[0095] The reaction can be carried out in the presence of a ligand. Examples of the ligand include 1,1'-bis(diphenylphosphino)ferrocene. The amount of the ligand used is 0.005 to 20 equivalents relative to 1 equivalent of compound (2).
[0096] The reaction temperature can be set at any temperature between -78°C and the reflux temperature of the reaction mixture. The reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but can usually be set at any time within the range of 5 minutes to 100 hours.
[0097] Compound (2) can be produced in accordance with a known method known in the literature, for example, the method described in WO 2021 / 261562.
[0098] Some of the compounds (3) are known compounds, some of which are commercially available, and others can be prepared according to the synthetic methods of known compounds.
[0099] [Manufacturing method 2] The compound (1) of the present invention can be produced by reacting a compound (4) with a compound (5).
[0100] [ka]
[0101] (In the formula, J,Q,X,Y,R 2 and R 3 has the same meaning as above, and Qa is C 1 ~C 6 represents alkoxy. The compound (1) of the present invention can be produced by reacting the compound (4) with the compound (5) in a solvent or without a solvent.
[0102] When a solvent is used, any solvent may be used so long as it is inert to the reaction. For example, the solvents exemplified in Production Method 1 may be used.
[0103] The reaction can also be carried out using a base. Examples of bases that can be used include the bases exemplified in Production Method 1. The amount (equivalent) of the base used is 0.1 to 100 equivalents relative to 1 equivalent of compound (4).
[0104] The reaction temperature can be set at any temperature between -78°C and the reflux temperature of the reaction mixture. The reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but can usually be set at any time within the range of 5 minutes to 100 hours.
[0105] Compound (4) can be produced in accordance with a known method known in the literature, for example, the method described in WO 2021 / 261562.
[0106] Some of the compounds (5) are known compounds, some of which are commercially available, and others can be prepared according to the synthetic methods of known compounds.
[0107] [Manufacturing method 3] Among the compounds (1) of the present invention, compound (1a) in which J represents J-2 can be prepared by reacting compound (6).
[0108] [ka]
[0109] (In the formula, Q, G, X, Y, R 2 and R 3 has the same meaning as above.) Compound (1a) can be produced by reacting compound (6) in a solvent or without a solvent.
[0110] When a solvent is used, any solvent may be used so long as it is inert to the reaction. For example, the solvents exemplified in Production Method 1 may be used.
[0111] The reaction can also be carried out using a base. Examples of the base that can be used include the bases exemplified in Production Method 1. The amount (equivalent) of the base used is 0.1 to 100 equivalents relative to 1 equivalent of compound (6).
[0112] The reaction temperature can be set at any temperature between -78°C and the reflux temperature of the reaction mixture. The reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but can usually be set at any time within the range of 5 minutes to 100 hours.
[0113] The compound (6) used in the production method 3 can be produced according to the following reaction scheme.
[0114] [Reaction Scheme 1]
[0115] [ka]
[0116] (In the formula, Q, G, X, Y, R 2 and R 3 has the same meaning as above, and Jb is C 1 ~C 6 Represents alkyl. [Manufacturing process 1] Compound (9) can be reacted with compound (5) in accordance with a method known in the art, for example, the method described in WO 2016 / 118611, to produce compound (8).
[0117] Some of the compounds (9) are known compounds, some of which are commercially available, and the rest can be prepared according to known methods described in the literature, for example, the method described in The Journal of Organic Chemistry, vol. 69, pages 130-141, 2004.
[0118] [Manufacturing process 2] Compound (7) can be produced by reacting compound (8) according to a known method known in the literature, for example, the method described in The Journal of Organic Chemistry, Vol. 24, pages 9045-9050, 2006.
[0119] [Manufacturing process 3] Compound (7) can be reacted with compound (10) according to a method known in the literature, for example, the method described in Synthetic Communications, 2006, Vol. 36, pages 729-741, to produce compound (6).
[0120] Some of the compounds (10) are known compounds, some of which are commercially available. Others can be prepared according to known methods described in the literature, for example, the method described in Bioorganic & Medicinal Chemistry, 2018, Vol. 26, pp. 1713-1726.
[0121] In the reactions of Production Methods 1 to 3 and Reaction Scheme 1, the reaction mixture after completion of the reaction can be subjected to a typical post-treatment such as direct concentration, dissolving in an organic solvent and washing with water followed by concentration, or pouring into ice water and extracting with an organic solvent followed by concentration, to obtain the target compound of the present invention. When purification is required, the compound can be separated and purified by any purification method such as recrystallization, column chromatography, thin layer chromatography, liquid chromatography fractionation, etc.
[0122] Examples of the compounds of the present invention and intermediates for producing the compounds of the present invention that can be produced by these methods include the compounds shown in Tables 1 to 30.
[0123] In the table, Q-1, Q-2, Q-3, Q-4, Q-6, Q-8, Q-9, Q-10, Q-12a and Q-47a represent the following structures.
[0124] [ka]
[0125] In addition, G-1, G-2, G-3 and G-7 in the table each represent the following structures.
[0126] [ka]
[0127] The numbers in the above structural formula indicate the substituents (Z 1 ) t2 , (Z 1 ) t3 , (Z 1 )t4 , (Z 1 ) t5 , (Z 2 ) t4 Or (Z 2 ) t5 For example, in the table, "Q-1(4-F)" represents "4-fluorophenyl" and "Q-1" represents "phenyl."
[0128] [Table 1]
[0129] [ka]
[0130] -------------------------------------------------- R 1 QG -------------------------------------------------- CHF 2 Q-1(3-F) G-1(4-F) CHF 2 Q-1(3-F) G-3(3-F) CHF 2 Q-1(3-F) G-3(3-Cl) CHF 2 Q-1(3-F) G-3(3-CH 3 ) CHF 2 Q-1(3-F) G-3(3-CF 3 ) CHF 2 Q-1(4-F) G-1(4-F) CHF 2 Q-1(4-F) G-3(3-F) CHF 2 Q-1(4-F) G-3(3-Cl) CHF 2 Q-1(4-F) G-3(3-CH 3 ) CHF 2 Q-1(4-F) G-3(3-CF 3 ) CHF 2 Q-1(4-CN) G-1(4-F) CHF2 Q-1(4-CN) G-3(3-F) CHF 2 Q-1(4-CN) G-3(3-Cl) CHF 2 Q-1(4-CN) G-3(3-CH 3 ) CHF 2 Q-1(4-CN) G-3(3-CF 3 ) CHF 2 Q-1(4-CF 3 ) G-1(4-F) CHF 2 Q-1(4-CF 3 ) G-3(3-F) CHF 2 Q-1(4-CF 3 ) G-3(3-Cl) CHF 2 Q-1(4-CF 3 ) G-3(3-CH 3 ) CHF 2 Q-1(4-CF 3 ) G-3(3-CF 3 ) CHF 2 Q-1(2-F,4-F) G-1(4-F) CHF 2 Q-1(2-F,4-F) G-3(3-F) CHF 2 Q-1(2-F,4-F) G-3(3-Cl) CHF 2 Q-1(2-F,4-F) G-3(3-CH 3 ) CHF 2 Q-1(2-F,4-F) G-3(3-CF 3 ) CHF 2 Q-1(3-F,4-F) G-1(4-F) CHF 2 Q-1(3-F,4-F) G-3(3-F) CHF 2 Q-1(3-F,4-F) G-3(3-Cl) CHF 2Q-1(3-F,4-F) G-3(3-CH 3 ) CHF 2 Q-1(3-F,4-F) G-3(3-CF 3 ) CHF 2 Q-2(4-F) G-1(4-F) CHF 2 Q-2(4-F) G-3(3-F) CHF 2 Q-2(4-F) G-3(3-Cl) CHF 2 Q-2(4-F) G-3(3-CH 3 ) CHF 2 Q-2(4-F) G-3(3-CF 3 ) CHF 2 Q-3 G-1(4-F) CHF 2 Q-3 G-3(3-F) CHF 2 Q-3 G-3(3-Cl) CHF 2 Q-3 G-3(3-CH 3 ) CHF 2 Q-3 G-3(3-CF 3 ) CHF 2 Q-3(4-F) G-1(4-F) CHF 2 Q-3(4-F) G-3(3-F) CHF 2 Q-3(4-F) G-3(3-Cl) CHF 2 Q-3(4-F) G-3(3-CH 3 ) CHF 2 Q-3(4-F) G-3(3-CF 3 ) CHF 2 Q-3(4-Cl) G-1(4-F) CHF 2 Q-3(4-Cl) G-3(3-F) CHF 2 Q-3(4-Cl) G-3(3-Cl) CHF 2 Q-3(4-Cl) G-3(3-CH 3 ) CHF 2 Q-3(4-Cl) G-3(3-CF 3 ) CHF 2 Q-3(4-CH 3 ) G-1(4-F) CHF 2 Q-3(4-CH 3 ) G-3(3-F) CHF 2 Q-3(4-CH 3 ) G-3(3-Cl) CHF 2 Q-3(4-CH 3 ) G-3(3-CH 3 ) CHF 2 Q-3(4-CH 3 ) G-3(3-CF 3 ) CHF 2 Q-3(3-CH 3 ) G-1(4-F) CHF 2 Q-3(3-CH 3 ) G-3(3-F) CHF 2 Q-3(3-CH 3 ) G-3(3-Cl) CHF 2 Q-3(3-CH 3 ) G-3(3-CH 3 ) CHF 2 Q-3(3-CH 3 ) G-3(3-CF 3 ) CHF 2 Q-3(3-OCH 3 ) G-1(4-F) CHF 2 Q-3(3-OCH 3 ) G-3(3-F) CHF 2 Q-3(3-OCH 3 ) G-3(3-Cl) CHF 2 Q-3(3-OCH3 ) G-3(3-CH 3 ) CHF 2 Q-3(3-OCH 3 ) G-3(3-CF 3 ) CHF 2 Q-4 G-1(4-F) CHF 2 Q-4 G-3(3-F) CHF 2 Q-4 G-3(3-Cl) CHF 2 Q-4 G-3(3-CH 3 ) CHF 2 Q-4 G-3(3-CF 3 ) CHF 2 Q-4(4-CH 3 ) G-1(4-F) CHF 2 Q-4(4-CH 3 ) G-3(3-F) CHF 2 Q-4(4-CH 3 ) G-3(3-Cl) CHF 2 Q-4(4-CH 3 ) G-3(3-CH 3 ) CHF 2 Q-4(4-CH 3 ) G-3(3-CF 3 ) CHF 2 Q-4(3-CH 3 ) G-1(4-F) CHF 2 Q-4(3-CH 3 ) G-3(3-F) CHF 2 Q-4(3-CH 3 ) G-3(3-Cl) CHF 2 Q-4(3-CH 3 ) G-3(3-CH 3 ) CHF 2 Q-4(3-CH 3 ) G-3(3-CF 3) CHF 2 Q-9 G-1(4-F) CHF 2 Q-9 G-3(3-F) CHF 2 Q-9 G-3(3-Cl) CHF 2 Q-9 G-3(3-CH 3 ) CHF 2 Q-9 G-3(3-CF 3 ) CHF 2 Q-12a G-1(4-F) CHF 2 Q-12a G-3(3-F) CHF 2 Q-12a G-3(3-Cl) CHF 2 Q-12a G-3(3-CH 3 ) CHF 2 Q-12a G-3(3-CF 3 ) CF 3 Q-1(3-F) G-1(4-F) CF 3 Q-1(3-F) G-3(3-F) CF 3 Q-1(3-F) G-3(3-Cl) CF 3 Q-1(3-F) G-3(3-CH 3 ) CF 3 Q-1(3-F) G-3(3-CF 3 ) CF 3 Q-1(4-F) G-1(4-F) CF 3 Q-1(4-F) G-3(3-F) CF 3 Q-1(4-F) G-3(3-Cl) CF 3 Q-1(4-F) G-3(3-CH 3 ) CF 3 Q-1(4-F) G-3(3-CF 3 ) CF 3 Q-1(4-CN) G-1(4-F) CF 3 Q-1(4-CN) G-3(3-F) CF 3 Q-1(4-CN) G-3(3-Cl) CF 3 Q-1(4-CN) G-3(3-CH 3 ) CF 3 Q-1(4-CN) G-3(3-CF 3 ) CF 3 Q-1(4-CF 3 ) G-1(4-F) CF 3 Q-1(4-CF 3 ) G-3(3-F) CF 3 Q-1(4-CF 3 ) G-3(3-Cl) CF 3 Q-1(4-CF 3 ) G-3(3-CH 3 ) CF 3 Q-1(4-CF 3 ) G-3(3-CF 3 ) CF 3 Q-1(2-F,4-F) G-1(4-F) CF 3 Q-1(2-F,4-F) G-3(3-F) CF 3 Q-1(2-F,4-F) G-3(3-Cl) CF 3 Q-1(2-F,4-F) G-3(3-CH 3 ) CF 3 Q-1(2-F,4-F) G-3(3-CF 3 ) CF 3 Q-1(3-F,4-F) G-1(4-F) CF 3 Q-1(3-F,4-F) G-3(3-F) CF 3 Q-1(3-F,4-F) G-3(3-Cl) CF 3 Q-1(3-F,4-F) G-3(3-CH 3 ) CF 3 Q-1(3-F,4-F) G-3(3-CF 3 ) CF 3 Q-2(4-F) G-1(4-F) CF 3 Q-2(4-F) G-3(3-F) CF 3 Q-2(4-F) G-3(3-Cl) CF 3 Q-2(4-F) G-3(3-CH 3 ) CF 3 Q-2(4-F) G-3(3-CF 3 ) CF 3 Q-3 G-1(4-F) CF 3 Q-3 G-3(3-F) CF 3 Q-3 G-3(3-Cl) CF 3 Q-3 G-3(3-CH 3 ) CF 3 Q-3 G-3(3-CF 3 ) CF 3 Q-3(4-F) G-1(4-F) CF 3 Q-3(4-F) G-3(3-F) CF 3 Q-3(4-F) G-3(3-Cl) CF 3 Q-3(4-F) G-3(3-CH 3 ) CF 3 Q-3(4-F) G-3(3-CF 3 ) CF 3 Q-3(4-Cl) G-1(4-F) CF 3 Q-3(4-Cl) G-3(3-F) CF 3 Q-3(4-Cl) G-3(3-Cl) CF 3 Q-3(4-Cl) G-3(3-CH 3 ) CF 3 Q-3(4-Cl) G-3(3-CF 3 ) CF 3 Q-3(4-CH 3 ) G-1(4-F) CF 3 Q-3(4-CH 3 ) G-3(3-F) CF 3 Q-3(4-CH 3 ) G-3(3-Cl) CF 3 Q-3(4-CH 3 ) G-3(3-CH 3 ) CF 3 Q-3(4-CH 3 ) G-3(3-CF 3 ) CF 3 Q-3(3-CH 3 ) G-1(4-F) CF 3 Q-3(3-CH 3 ) G-3(3-F) CF 3 Q-3(3-CH 3 ) G-3(3-Cl) CF 3 Q-3(3-CH 3 ) G-3(3-CH 3 ) CF 3 Q-3(3-CH 3 ) G-3(3-CF 3 ) CF 3 Q-3(3-OCH 3 ) G-1(4-F) CF 3 Q-3(3-OCH 3 ) G-3(3-F) CF 3 Q-3(3-OCH 3 ) G-3(3-Cl) CF 3 Q-3(3-OCH 3) G-3(3-CH 3 ) CF 3 Q-3(3-OCH 3 ) G-3(3-CF 3 ) CF 3 Q-4 G-1(4-F) CF 3 Q-4 G-3(3-F) CF 3 Q-4 G-3(3-Cl) CF 3 Q-4 G-3(3-CH 3 ) CF 3 Q-4 G-3(3-CF 3 ) CF 3 Q-4(4-CH 3 ) G-1(4-F) CF 3 Q-4(4-CH 3 ) G-3(3-F) CF 3 Q-4(4-CH 3 ) G-3(3-Cl) CF 3 Q-4(4-CH 3 ) G-3(3-CH 3 ) CF 3 Q-4(4-CH 3 ) G-3(3-CF 3 ) CF 3 Q-4(3-CH 3 ) G-1(4-F) CF 3 Q-4(3-CH 3 ) G-3(3-F) CF 3 Q-4(3-CH 3 ) G-3(3-Cl) CF 3 Q-4(3-CH 3 ) G-3(3-CH 3 ) CF 3 Q-4(3-CH 3 ) G-3(3-CF 3 ) CF 3Q-9 G-1(4-F) CF 3 Q-9 G-3(3-F) CF 3 Q-9 G-3(3-Cl) CF 3 Q-9 G-3(3-CH 3 ) CF 3 Q-9 G-3(3-CF 3 ) CF 3 Q-12a G-1(4-F) CF 3 Q-12a G-3(3-F) CF 3 Q-12a G-3(3-Cl) CF 3 Q-12a G-3(3-CH 3 ) CF 3 Q-12a G-3(3-CF 3 ) CF 3 Q-1(4-F) G-1(4-NO 2 ) CF 3 Q-1(4-F) G-1(4-NH 2 ) CF 3 Q-1(4-F) G-1(5-F) CF 3 Q-1(4-F) G-1(5-NO 2 ) CF 3 Q-1(4-F) G-1(5-NH 2 ) CF 3 Q-1(4-F) G-3(3-NO 2 ) CF 3 Q-1(4-F) G-3(3-NH 2 ) CF 3 Q-1(4-CN) G-1(4-NO 2 ) CF 3 Q-1(4-CN) G-1(4-NH 2 ) CF 3Q-1(4-CN) G-1(5-F) CF 3 Q-1(4-CN) G-1(5-NO 2 ) CF 3 Q-1(4-CN) G-1(5-NH 2 ) CF 3 Q-1(4-CN) G-3(3-NO 2 ) CF 3 Q-1(4-CN) G-3(3-NH 2 ) CF 3 Q-2(4-F) G-1(4-NO 2 ) CF 3 Q-2(4-F) G-1(4-NH 2 ) CF 3 Q-2(4-F) G-1(5-F) CF 3 Q-2(4-F) G-1(5-NO 2 ) CF 3 Q-2(4-F) G-1(5-NH 2 ) CF 3 Q-2(4-F) G-3(3-NO 2 ) CF 3 Q-2(4-F) G-3(3-NH 2 ) CF 3 Q-2(4-Cl) G-1(4-F) CF 3 Q-2(4-Cl) G-1(4-NO 2 ) CF 3 Q-2(4-Cl) G-1(4-NH 2 ) CF 3 Q-2(4-Cl) G-1(5-F) CF 3 Q-2(4-Cl) G-1(5-NO 2 ) CF 3 Q-2(4-Cl) G-1(5-NH 2 ) CF 3 Q-2(4-Cl) G-3(3-F) CF 3 Q-2(4-Cl) G-3(3-Cl) CF 3 Q-2(4-Cl) G-3(3-CH 3 ) CF 3 Q-2(4-Cl) G-3(3-CF 3 ) CF 3 Q-2(4-Cl) G-3(3-NO 2 ) CF 3 Q-2(4-Cl) G-3(3-NH 2 ) CF 3 Q-2(4-CN) G-1(4-F) CF 3 Q-2(4-CN) G-1(4-NO 2 ) CF 3 Q-2(4-CN) G-1(4-NH 2 ) CF 3 Q-2(4-CN) G-1(5-F) CF 3 Q-2(4-CN) G-1(5-NO 2 ) CF 3 Q-2(4-CN) G-1(5-NH 2 ) CF 3 Q-2(4-CN) G-3(3-F) CF 3 Q-2(4-CN) G-3(3-Cl) CF 3 Q-2(4-CN) G-3(3-CH 3 ) CF 3 Q-2(4-CN) G-3(3-CF 3 ) CF 3 Q-2(4-CN) G-3(3-NO 2 ) CF 3 Q-2(4-CN) G-3(3-NH 2 ) CF3 Q-3 G-1(4-NO 2 ) CF 3 Q-3 G-1(4-NH 2 ) CF 3 Q-3 G-1(5-F) CF 3 Q-3 G-1(5-NO 2 ) CF 3 Q-3 G-1(5-NH 2 ) CF 3 Q-3 G-3(3-NO 2 ) CF 3 Q-3 G-3(3-NH 2 ) CF 3 Q-3(3-CH 3 ) G-1(4-NO 2 ) CF 3 Q-3(3-CH 3 ) G-1(4-NH 2 ) CF 3 Q-3(3-CH 3 ) G-1(5-F) CF 3 Q-3(3-CH 3 ) G-1(5-NO 2 ) CF 3 Q-3(3-CH 3 ) G-1(5-NH 2 ) CF 3 Q-3(3-CH 3 ) G-3(3-NO 2 ) CF 3 Q-3(3-CH 3 ) G-3(3-NH 2 ) CF 3 Q-3(3-Cl) G-1(4-F) CF 3 Q-3(3-Cl) G-1(4-NO 2 ) CF 3 Q-3(3-Cl) G-1(4-NH2 ) CF 3 Q-3(3-Cl) G-1(5-F) CF 3 Q-3(3-Cl) G-1(5-NO 2 ) CF 3 Q-3(3-Cl) G-1(5-NH 2 ) CF 3 Q-3(3-Cl) G-3(3-F) CF 3 Q-3(3-Cl) G-3(3-Cl) CF 3 Q-3(3-Cl) G-3(3-CH 3 ) CF 3 Q-3(3-Cl) G-3(3-CF 3 ) CF 3 Q-3(3-Cl) G-3(3-NO 2 ) CF 3 Q-3(3-Cl) G-3(3-NH 2 ) CF 3 Q-3(3-F) G-1(4-F) CF 3 Q-3(3-F) G-1(4-NO 2 ) CF 3 Q-3(3-F) G-1(4-NH 2 ) CF 3 Q-3(3-F) G-1(5-F) CF 3 Q-3(3-F) G-1(5-NO 2 ) CF 3 Q-3(3-F) G-1(5-NH 2 ) CF 3 Q-3(3-F) G-3(3-F) CF 3 Q-3(3-F) G-3(3-Cl) CF 3 Q-3(3-F) G-3(3-CH 3 ) CF 3 Q-3(3-F) G-3(3-CF 3 ) CF 3 Q-3(3-F) G-3(3-NO 2 ) CF 3 Q-3(3-F) G-3(3-NH 2 ) CF 3 Q-3(4-Br) G-1(4-F) CF 3 Q-3(4-Br) G-1(4-NO 2 ) CF 3 Q-3(4-Br) G-1(4-NH 2 ) CF 3 Q-3(4-Br) G-1(5-F) CF 3 Q-3(4-Br) G-1(5-NO 2 ) CF 3 Q-3(4-Br) G-1(5-NH 2 ) CF 3 Q-3(4-Br) G-3(3-F) CF 3 Q-3(4-Br) G-3(3-Cl) CF 3 Q-3(4-Br) G-3(3-CH 3 ) CF 3 Q-3(4-Br) G-3(3-CF 3 ) CF 3 Q-3(4-Br) G-3(3-NO 2 ) CF 3 Q-3(4-Br) G-3(3-NH 2 ) CF 3 Q-3(4-CH 3 ) G-1(4-NO 2 ) CF 3 Q-3(4-CH 3 ) G-1(4-NH 2 ) CF 3Q-3(4-CH 3 ) G-1(5-F) CF 3 Q-3(4-CH 3 ) G-1(5-NO 2 ) CF 3 Q-3(4-CH 3 ) G-1(5-NH 2 ) CF 3 Q-3(4-CH 3 ) G-3(3-NO 2 ) CF 3 Q-3(4-CH 3 ) G-3(3-NH 2 ) CF 3 Q-3(4-Cl) G-1(4-NO 2 ) CF 3 Q-3(4-Cl) G-1(4-NH 2 ) CF 3 Q-3(4-Cl) G-1(5-F) CF 3 Q-3(4-Cl) G-1(5-NO 2 ) CF 3 Q-3(4-Cl) G-1(5-NH 2 ) CF 3 Q-3(4-Cl) G-3(3-NO 2 ) CF 3 Q-3(4-Cl) G-3(3-NH 2 ) CF 3 Q-3(4-CN) G-1(4-F) CF 3 Q-3(4-CN) G-1(4-NO 2 ) CF 3 Q-3(4-CN) G-1(4-NH 2 ) CF 3 Q-3(4-CN) G-1(5-F) CF 3 Q-3(4-CN) G-1(5-NO 2 ) CF 3 Q-3(4-CN) G-1(5-NH 2 ) CF 3 Q-3(4-CN) G-3(3-F) CF 3 Q-3(4-CN) G-3(3-Cl) CF 3 Q-3(4-CN) G-3(3-CH 3 ) CF 3 Q-3(4-CN) G-3(3-CF 3 ) CF 3 Q-3(4-CN) G-3(3-NO 2 ) CF 3 Q-3(4-CN) G-3(3-NH 2 ) CF 3 Q-3(4-F) G-1(4-NO 2 ) CF 3 Q-3(4-F) G-1(4-NH 2 ) CF 3 Q-3(4-F) G-1(5-F) CF 3 Q-3(4-F) G-1(5-NO 2 ) CF 3 Q-3(4-F) G-1(5-NH 2 ) CF 3 Q-3(4-F) G-3(3-NO 2 ) CF 3 Q-3(4-F) G-3(3-NH 2 ) CF 3 Q-3(6-F) G-1(4-F) CF 3 Q-3(6-F) G-1(4-NO 2 ) CF 3 Q-3(6-F) G-1(4-NH 2 ) CF 3 Q-3(6-F) G-1(5-F) CF 3 Q-3(6-F) G-1(5-NO 2 ) CF 3 Q-3(6-F) G-1(5-NH 2 ) CF 3 Q-3(6-F) G-3(3-F) CF 3 Q-3(6-F) G-3(3-Cl) CF 3 Q-3(6-F) G-3(3-CH 3 ) CF 3 Q-3(6-F) G-3(3-CF 3 ) CF 3 Q-3(6-F) G-3(3-NO 2 ) CF 3 Q-3(6-F) G-3(3-NH 2 ) CF 3 Q-4 G-1(4-NO 2 ) CF 3 Q-4 G-1(4-NH 2 ) CF 3 Q-4 G-1(5-F) CF 3 Q-4 G-1(5-NO 2 ) CF 3 Q-4 G-1(5-NH 2 ) CF 3 Q-4 G-3(3-NO 2 ) CF 3 Q-4 G-3(3-NH 2 ) CF 3 Q-4(3-CH 3 ) G-1(4-NO 2 ) CF 3 Q-4(3-CH 3 ) G-1(4-NH 2 ) CF 3 Q-4(3-CH 3) G-1(5-F) CF 3 Q-4(3-CH 3 ) G-1(5-NO 2 ) CF 3 Q-4(3-CH 3 ) G-1(5-NH 2 ) CF 3 Q-4(3-CH 3 ) G-3(3-NO 2 ) CF 3 Q-4(3-CH 3 ) G-3(3-NH 2 ) CF 3 Q-4(3-Cl) G-1(4-F) CF 3 Q-4(3-Cl) G-1(4-NO 2 ) CF 3 Q-4(3-Cl) G-1(4-NH 2 ) CF 3 Q-4(3-Cl) G-1(5-F) CF 3 Q-4(3-Cl) G-1(5-NO 2 ) CF 3 Q-4(3-Cl) G-1(5-NH 2 ) CF 3 Q-4(3-Cl) G-3(3-F) CF 3 Q-4(3-Cl) G-3(3-Cl) CF 3 Q-4(3-Cl) G-3(3-CH 3 ) CF 3 Q-4(3-Cl) G-3(3-CF 3 ) CF 3 Q-4(3-Cl) G-3(3-NO 2 ) CF 3 Q-4(3-Cl) G-3(3-NH 2 ) CF 3Q-4(4-Br) G-1(4-F) CF 3 Q-4(4-Br) G-1(4-NO 2 ) CF 3 Q-4(4-Br) G-1(4-NH 2 ) CF 3 Q-4(4-Br) G-1(5-F) CF 3 Q-4(4-Br) G-1(5-NO 2 ) CF 3 Q-4(4-Br) G-1(5-NH 2 ) CF 3 Q-4(4-Br) G-3(3-F) CF 3 Q-4(4-Br) G-3(3-Cl) CF 3 Q-4(4-Br) G-3(3-CH 3 ) CF 3 Q-4(4-Br) G-3(3-CF 3 ) CF 3 Q-4(4-Br) G-3(3-NO 2 ) CF 3 Q-4(4-Br) G-3(3-NH 2 ) CF 3 Q-4(4-Cl) G-1(4-F) CF 3 Q-4(4-Cl) G-1(4-NO 2 ) CF 3 Q-4(4-Cl) G-1(4-NH 2 ) CF 3 Q-4(4-Cl) G-1(5-F) CF 3 Q-4(4-Cl) G-1(5-NO 2 ) CF 3 Q-4(4-Cl) G-1(5-NH 2 ) CF 3Q-4(4-Cl) G-3(3-F) CF 3 Q-4(4-Cl) G-3(3-Cl) CF 3 Q-4(4-Cl) G-3(3-CH 3 ) CF 3 Q-4(4-Cl) G-3(3-CF 3 ) CF 3 Q-4(4-Cl) G-3(3-NO 2 ) CF 3 Q-4(4-Cl) G-3(3-NH 2 ) CF 3 Q-9 G-1(4-NO 2 ) CF 3 Q-9 G-1(4-NH 2 ) CF 3 Q-9 G-1(5-F) CF 3 Q-9 G-1(5-NO 2 ) CF 3 Q-9 G-1(5-NH 2 ) CF 3 Q-9 G-3(3-NO 2 ) CF 3 Q-9 G-3(3-NH 2 ) CF 3 Q-12a G-1(4-NO 2 ) CF 3 Q-12a G-1(4-NH 2 ) CF 3 Q-12a G-1(5-F) CF 3 Q-12a G-1(5-NO 2 ) CF 3 Q-12a G-1(5-NH 2 ) CF 3 Q-12a G-3(3-NO 2 ) CF 3 Q-12a G-3(3-NH 2 ) Cl Q-1(4-F) G-1(4-F) Cl Q-1(4-F) G-1(4-NO 2 ) Cl Q-1(4-F) G-1(4-NH 2 ) Cl Q-1(4-F) G-1(5-F) Cl Q-1(4-F) G-1(5-NO 2 ) Cl Q-1(4-F) G-1(5-NH 2 ) Cl Q-1(4-F) G-3(3-F) Cl Q-1(4-F) G-3(3-Cl) Cl Q-1(4-F) G-3(3-CH 3 ) Cl Q-1(4-F) G-3(3-CF 3 ) Cl Q-1(4-F) G-3(3-NO 2 ) Cl Q-1(4-F) G-3(3-NH 2 ) Cl Q-1(4-CN) G-1(4-F) Cl Q-1(4-CN) G-1(4-NO 2 ) Cl Q-1(4-CN) G-1(4-NH 2 ) Cl Q-1(4-CN) G-1(5-F) Cl Q-1(4-CN) G-1(5-NO 2 ) Cl Q-1(4-CN) G-1(5-NH 2 ) Cl Q-1(4-CN) G-3(3-F) Cl Q-1(4-CN) G-3(3-Cl) Cl Q-1(4-CN) G-3(3-CH 3 ) Cl Q-1(4-CN) G-3(3-CF 3 ) Cl Q-1(4-CN) G-3(3-NO 2 ) Cl Q-1(4-CN) G-3(3-NH 2 ) Cl Q-2(4-F) G-1(4-F) Cl Q-2(4-F) G-1(4-NO 2 ) Cl Q-2(4-F) G-1(4-NH 2 ) Cl Q-2(4-F) G-1(5-F) Cl Q-2(4-F) G-1(5-NO 2 ) Cl Q-2(4-F) G-1(5-NH 2 ) Cl Q-2(4-F) G-3(3-F) Cl Q-2(4-F) G-3(3-Cl) Cl Q-2(4-F) G-3(3-CH 3 ) Cl Q-2(4-F) G-3(3-CF 3 ) Cl Q-2(4-F) G-3(3-NO 2 ) Cl Q-2(4-F) G-3(3-NH 2 ) Cl Q-2(4-Cl) G-1(4-F) Cl Q-2(4-Cl) G-1(4-NO 2 ) Cl Q-2(4-Cl) G-1(4-NH 2 ) Cl Q-2(4-Cl) G-1(5-F) Cl Q-2(4-Cl) G-1(5-NO 2 ) Cl Q-2(4-Cl) G-1(5-NH 2 ) Cl Q-2(4-Cl) G-3(3-F) Cl Q-2(4-Cl) G-3(3-Cl) Cl Q-2(4-Cl) G-3(3-CH 3 ) Cl Q-2(4-Cl) G-3(3-CF 3 ) Cl Q-2(4-Cl) G-3(3-NO 2 ) Cl Q-2(4-Cl) G-3(3-NH 2 ) Cl Q-2(4-CN) G-1(4-F) Cl Q-2(4-CN) G-1(4-NO 2 ) Cl Q-2(4-CN) G-1(4-NH 2 ) Cl Q-2(4-CN) G-1(5-F) Cl Q-2(4-CN) G-1(5-NO 2 ) Cl Q-2(4-CN) G-1(5-NH 2 ) Cl Q-2(4-CN) G-3(3-F) Cl Q-2(4-CN) G-3(3-Cl) Cl Q-2(4-CN) G-3(3-CH 3 ) Cl Q-2(4-CN) G-3(3-CF 3 ) Cl Q-2(4-CN) G-3(3-NO 2 ) Cl Q-2(4-CN) G-3(3-NH 2 ) Cl Q-3 G-1(4-F) Cl Q-3 G-1(4-NO 2 ) Cl Q-3 G-1(4-NH 2 ) Cl Q-3 G-1(5-F) Cl Q-3 G-1(5-NO 2 ) Cl Q-3 G-1(5-NH 2 ) Cl Q-3 G-3(3-F) Cl Q-3 G-3(3-Cl) Cl Q-3 G-3(3-CH 3 ) Cl Q-3 G-3(3-CF 3 ) Cl Q-3 G-3(3-NO 2 ) Cl Q-3 G-3(3-NH 2 ) Cl Q-3(3-CH 3 ) G-1(4-F) Cl Q-3(3-CH 3 ) G-1(4-NO 2 ) Cl Q-3(3-CH 3 ) G-1(4-NH 2 ) Cl Q-3(3-CH 3 ) G-1(5-F) Cl Q-3(3-CH 3 ) G-1(5-NO 2 ) Cl Q-3(3-CH 3 ) G-1(5-NH 2 ) Cl Q-3(3-CH 3 ) G-3(3-F) Cl Q-3(3-CH 3 ) G-3(3-Cl) Cl Q-3(3-CH 3 ) G-3(3-CH 3 ) Cl Q-3(3-CH 3 ) G-3(3-CF 3 ) Cl Q-3(3-CH 3 ) G-3(3-NO 2 ) Cl Q-3(3-CH 3 ) G-3(3-NH 2 ) Cl Q-3(3-Cl) G-1(4-F) Cl Q-3(3-Cl) G-1(4-NO 2 ) Cl Q-3(3-Cl) G-1(4-NH 2 ) Cl Q-3(3-Cl) G-1(5-F) Cl Q-3(3-Cl) G-1(5-NO 2) Cl Q-3(3-Cl) G-1(5-NH 2 ) Cl Q-3(3-Cl) G-3(3-F) Cl Q-3(3-Cl) G-3(3-Cl) Cl Q-3(3-Cl) G-3(3-CH 3 ) Cl Q-3(3-Cl) G-3(3-CF 3 ) Cl Q-3(3-Cl) G-3(3-NO 2 ) Cl Q-3(3-Cl) G-3(3-NH 2 ) Cl Q-3(3-F) G-1(4-F) Cl Q-3(3-F) G-1(4-NO 2 ) Cl Q-3(3-F) G-1(4-NH 2 ) Cl Q-3(3-F) G-1(5-F) Cl Q-3(3-F) G-1(5-NO 2 ) Cl Q-3(3-F) G-1(5-NH 2 ) Cl Q-3(3-F) G-3(3-F) Cl Q-3(3-F) G-3(3-Cl) Cl Q-3(3-F) G-3(3-CH 3 ) Cl Q-3(3-F) G-3(3-CF 3 ) Cl Q-3(3-F) G-3(3-NO 2 ) Cl Q-3(3-F) G-3(3-NH 2 ) Cl Q-3(4-Br) G-1(4-F) Cl Q-3(4-Br) G-1(4-NO 2 ) Cl Q-3(4-Br) G-1(4-NH 2 ) Cl Q-3(4-Br) G-1(5-F) Cl Q-3(4-Br) G-1(5-NO 2 ) Cl Q-3(4-Br) G-1(5-NH 2 ) Cl Q-3(4-Br) G-3(3-F) Cl Q-3(4-Br) G-3(3-Cl) Cl Q-3(4-Br) G-3(3-CH 3 ) Cl Q-3(4-Br) G-3(3-CF 3 ) Cl Q-3(4-Br) G-3(3-NO 2 ) Cl Q-3(4-Br) G-3(3-NH 2 ) Cl Q-3(4-CH 3 ) G-1(4-F) Cl Q-3(4-CH 3 ) G-1(4-NO 2 ) Cl Q-3(4-CH 3 ) G-1(4-NH 2 ) Cl Q-3(4-CH 3 ) G-1(5-F) Cl Q-3(4-CH 3 ) G-1(5-NO 2 ) Cl Q-3(4-CH 3 ) G-1(5-NH 2 ) Cl Q-3(4-CH 3 ) G-3(3-F) Cl Q-3(4-CH 3 ) G-3(3-Cl) Cl Q-3(4-CH 3 ) G-3(3-CH 3 ) Cl Q-3(4-CH 3 ) G-3(3-CF 3 ) Cl Q-3(4-CH 3 ) G-3(3-NO 2 ) Cl Q-3(4-CH 3) G-3(3-NH 2 ) Cl Q-3(4-Cl) G-1(4-F) Cl Q-3(4-Cl) G-1(4-NO 2 ) Cl Q-3(4-Cl) G-1(4-NH 2 ) Cl Q-3(4-Cl) G-1(5-F) Cl Q-3(4-Cl) G-1(5-NO 2 ) Cl Q-3(4-Cl) G-1(5-NH 2 ) Cl Q-3(4-Cl) G-3(3-F) Cl Q-3(4-Cl) G-3(3-Cl) Cl Q-3(4-Cl) G-3(3-CH 3 ) Cl Q-3(4-Cl) G-3(3-CF 3 ) Cl Q-3(4-Cl) G-3(3-NO 2 ) Cl Q-3(4-Cl) G-3(3-NH 2 ) Cl Q-3(4-CN) G-1(4-F) Cl Q-3(4-CN) G-1(4-NO 2 ) Cl Q-3(4-CN) G-1(4-NH 2 ) Cl Q-3(4-CN) G-1(5-F) Cl Q-3(4-CN) G-1(5-NO 2 ) Cl Q-3(4-CN) G-1(5-NH 2 ) Cl Q-3(4-CN) G-3(3-F) Cl Q-3(4-CN) G-3(3-Cl) Cl Q-3(4-CN) G-3(3-CH 3 ) Cl Q-3(4-CN) G-3(3-CF 3 ) Cl Q-3(4-CN) G-3(3-NO 2 ) Cl Q-3(4-CN) G-3(3-NH 2 ) Cl Q-3(4-F) G-1(4-F) Cl Q-3(4-F) G-1(4-NO 2 ) Cl Q-3(4-F) G-1(4-NH 2 ) Cl Q-3(4-F) G-1(5-F) Cl Q-3(4-F) G-1(5-NO 2 ) Cl Q-3(4-F) G-1(5-NH 2 ) Cl Q-3(4-F) G-3(3-F) Cl Q-3(4-F) G-3(3-Cl) Cl Q-3(4-F) G-3(3-CH 3 ) Cl Q-3(4-F) G-3(3-CF 3 ) Cl Q-3(4-F) G-3(3-NO 2 ) Cl Q-3(4-F) G-3(3-NH 2 ) Cl Q-3(6-F) G-1(4-F) Cl Q-3(6-F) G-1(4-NO 2 ) Cl Q-3(6-F) G-1(4-NH 2 ) Cl Q-3(6-F) G-1(5-F) Cl Q-3(6-F) G-1(5-NO 2 ) Cl Q-3(6-F) G-1(5-NH 2 ) Cl Q-3(6-F) G-3(3-F) Cl Q-3(6-F) G-3(3-Cl) Cl Q-3(6-F) G-3(3-CH 3 ) Cl Q-3(6-F) G-3(3-CF3 ) Cl Q-3(6-F) G-3(3-NO 2 ) Cl Q-3(6-F) G-3(3-NH 2 ) Cl Q-4 G-1(4-F) Cl Q-4 G-1(4-NO 2 ) Cl Q-4 G-1(4-NH 2 ) Cl Q-4 G-1(5-F) Cl Q-4 G-1(5-NO 2 ) Cl Q-4 G-1(5-NH 2 ) Cl Q-4 G-3(3-F) Cl Q-4 G-3(3-Cl) Cl Q-4 G-3(3-CH 3 ) Cl Q-4 G-3(3-CF 3 ) Cl Q-4 G-3(3-NO 2 ) Cl Q-4 G-3(3-NH 2 ) Cl Q-4(3-CH 3 ) G-1(4-F) Cl Q-4(3-CH 3 ) G-1(4-NO 2 ) Cl Q-4(3-CH 3 ) G-1(4-NH 2 ) Cl Q-4(3-CH 3 ) G-1(5-F) Cl Q-4(3-CH 3 ) G-1(5-NO 2 ) Cl Q-4(3-CH 3 ) G-1(5-NH 2 ) Cl Q-4(3-CH 3 ) G-3(3-F) Cl Q-4(3-CH 3 ) G-3(3-Cl) Cl Q-4(3-CH 3 ) G-3(3-CH 3 ) Cl Q-4(3-CH 3 ) G-3(3-CF 3 ) Cl Q-4(3-CH 3 ) G-3(3-NO 2 ) Cl Q-4(3-CH 3 ) G-3(3-NH 2 ) Cl Q-4(3-Cl) G-1(4-F) Cl Q-4(3-Cl) G-1(4-NO 2 ) Cl Q-4(3-Cl) G-1(4-NH 2 ) Cl Q-4(3-Cl) G-1(5-F) Cl Q-4(3-Cl) G-1(5-NO 2 ) Cl Q-4(3-Cl) G-1(5-NH 2 ) Cl Q-4(3-Cl) G-3(3-F) Cl Q-4(3-Cl) G-3(3-Cl) Cl Q-4(3-Cl) G-3(3-CH 3 ) Cl Q-4(3-Cl) G-3(3-CF 3 ) Cl Q-4(3-Cl) G-3(3-NO 2 ) Cl Q-4(3-Cl) G-3(3-NH 2 ) Cl Q-4(4-Br) G-1(4-F) Cl Q-4(4-Br) G-1(4-NO 2 ) Cl Q-4(4-Br) G-1(4-NH 2 ) Cl Q-4(4-Br) G-1(5-F) Cl Q-4(4-Br) G-1(5-NO 2 ) Cl Q-4(4-Br) G-1(5-NH2 ) Cl Q-4(4-Br) G-3(3-F) Cl Q-4(4-Br) G-3(3-Cl) Cl Q-4(4-Br) G-3(3-CH 3 ) Cl Q-4(4-Br) G-3(3-CF 3 ) Cl Q-4(4-Br) G-3(3-NO 2 ) Cl Q-4(4-Br) G-3(3-NH 2 ) Cl Q-4(4-Cl) G-1(4-F) Cl Q-4(4-Cl) G-1(4-NO 2 ) Cl Q-4(4-Cl) G-1(4-NH 2 ) Cl Q-4(4-Cl) G-1(5-F) Cl Q-4(4-Cl) G-1(5-NO 2 ) Cl Q-4(4-Cl) G-1(5-NH 2 ) Cl Q-4(4-Cl) G-3(3-F) Cl Q-4(4-Cl) G-3(3-Cl) Cl Q-4(4-Cl) G-3(3-CH 3 ) Cl Q-4(4-Cl) G-3(3-CF 3 ) Cl Q-4(4-Cl) G-3(3-NO 2 ) Cl Q-4(4-Cl) G-3(3-NH 2 ) Cl Q-9 G-1(4-F) Cl Q-9 G-1(4-NO 2 ) Cl Q-9 G-1(4-NH 2 ) Cl Q-9 G-1(5-F) Cl Q-9 G-1(5-NO 2 ) Cl Q-9 G-1(5-NH 2 ) Cl Q-9 G-3(3-F) Cl Q-9 G-3(3-Cl) Cl Q-9 G-3(3-CH 3 ) Cl Q-9 G-3(3-CF 3 ) Cl Q-9 G-3(3-NO 2 ) Cl Q-9 G-3(3-NH 2 ) Cl Q-12a G-1(4-F) Cl Q-12a G-1(4-NO 2 ) Cl Q-12a G-1(4-NH 2 ) Cl Q-12a G-1(5-F) Cl Q-12a G-1(5-NO 2 ) Cl Q-12a G-1(5-NH 2 ) Cl Q-12a G-3(3-F) Cl Q-12a G-3(3-Cl) Cl Q-12a G-3(3-CH 3 ) Cl Q-12a G-3(3-CF 3 ) Cl Q-12a G-3(3-NO 2 ) Cl Q-12a G-3(3-NH 2 ) ―――――――――――――――― [Table 2]
[0131]
Chem.
[0132] ――――――――――― Q G ――――――――――― Q-3(3-Cl) G-1(4-F) Q-3(3-Cl) G-1(2-F) Q-3(3-Cl) G-1(2-Cl) Q-3(3-Cl) G-3(3-F) Q-3(3-Cl) G-3(3-Cl) Q-3(3-Cl) G-3(3-CH 3 ) Q-3(3-Cl) G-3(3-CF 3 ) Q-3(3-CH 3 ) G-1(4-F) Q-3(3-CH 3 ) G-1(2-F) Q-3(3-CH 3 ) G-1(2-Cl) Q-3(3-CH 3 ) G-3(3-F) Q-3(3-CH 3 ) G-3(3-Cl) Q-3(3-CH 3 ) G-3(3-CH 3 ) Q-3(3-CH 3 ) G-3(3-CF 3 ) Q-4(3-Cl) G-1(4-F) Q-4(3-Cl) G-1(2-F) Q-4(3-Cl) G-1(2-Cl) Q-4(3-Cl) G-3(3-F) Q-4(3-Cl) G-3(3-Cl) Q-4(3-Cl) G-3(3-CH 3 ) Q-4(3-Cl) G-3(3-CF 3 ) Q-4(3-CH 3 ) G-1(4-F) Q-4(3-CH 3 ) G-1(2-F) Q-4(3-CH 3 ) G-1(2-Cl) Q-4(3-CH 3 ) G-3(3-F) Q-4(3-CH 3) G-3(3-Cl) Q-4(3-CH 3 ) G-3(3-CH 3 ) Q-4(3-CH 3 ) G-3(3-CF 3 ) Q-4(4-CH 3 ) G-1(4-F) Q-4(4-CH 3 ) G-1(2-F) Q-4(4-CH 3 ) G-1(2-Cl) Q-4(4-CH 3 ) G-3(3-F) Q-4(4-CH 3 ) G-3(3-Cl) Q-4(4-CH 3 ) G-3(3-CH 3 ) Q-4(4-CH 3 ) G-3(3-CF 3 ) Q-4(3-Br) G-1(4-F) Q-4(3-Br) G-1(2-F) Q-4(3-Br) G-1(2-Cl) Q-4(3-Br) G-3(3-F) Q-4(3-Br) G-3(3-Cl) Q-4(3-Br) G-3(3-CH 3 ) Q-4(3-Br) G-3(3-CF 3 ) Q-10(3-CH 3 ) G-1(4-F) Q-10(3-CH 3 ) G-1(2-F) Q-10(3-CH 3 ) G-1(2-Cl) Q-10(3-CH 3 ) G-3(3-F) Q-10(3-CH 3 ) G-3(3-Cl) Q-10(3-CH 3 ) G-3(3-CH 3 ) Q-10(3-CH 3 ) G-3(3-CF 3 ) Q-12a G-1(4-F) Q-12a G-1(2-F) Q-12a G-1(2-Cl) Q-12a G-3(3-F) Q-12a G-3(3-Cl) Q-12a G-3(3-CH 3 ) Q-12a G-3(3-CF 3 ) Q-47a G-1(4-F) Q-47a G-1(2-F) Q-47a G-1(2-Cl) Q-47a G-3(3-F) Q-47a G-3(3-Cl) Q-47a G-3(3-CH 3 ) Q-47a G-3(3-CF 3 ) Q-3(4-CN) G-1(4-F) Q-3(4-CN) G-1(2-F) Q-3(4-CN) G-1(2-Cl) Q-3(4-CN) G-3(3-F) Q-3(4-CN) G-3(3-Cl) Q-3(4-CN) G-3(3-CH 3 ) Q-3(4-CN) G-3(3-CF 3 ) Q-2(4-CN) G-1(4-F) Q-2(4-CN) G-1(2-F) Q-2(4-CN) G-1(2-Cl) Q-2(4-CN) G-3(3-F) Q-2(4-CN) G-3(3-Cl) Q-2(4-CN) G-3(3-CH 3 ) Q-2(4-CN) G-3(3-CF 3 ) Q-3(5-Cl) G-1(4-F) Q-3(5-Cl) G-1(2-F) Q-3(5-Cl) G-1(2-Cl) Q-3(5-Cl) G-3(3-F) Q-3(5-Cl) G-3(3-Cl) Q-3(5-Cl) G-3(3-CH 3 ) Q-3(5-Cl) G-3(3-CF 3 ) Q-3(5-CH 3 ) G-1(4-F) Q-3(5-CH 3 ) G-1(2-F) Q-3(5-CH 3 ) G-1(2-Cl) Q-3(5-CH 3 ) G-3(3-F) Q-3(5-CH 3 ) G-3(3-Cl) Q-3(5-CH 3 ) G-3(3-CH 3 ) Q-3(5-CH 3 ) G-3(3-CF 3 ) Q-6(3-CH 3 ) G-1(4-F) Q-6(3-CH 3 ) G-1(2-F) Q-6(3-CH 3 ) G-1(2-Cl) Q-6(3-CH 3 ) G-3(3-F) Q-6(3-CH 3 ) G-3(3-Cl) Q-6(3-CH 3 ) G-3(3-CH 3 ) Q-6(3-CH 3 ) G-3(3-CF 3 ) Q-6(3-Cl) G-1(4-F) Q-6(3-Cl) G-1(2-F) Q-6(3-Cl) G-1(2-Cl) Q-6(3-Cl) G-3(3-F) Q-6(3-Cl) G-3(3-Cl) Q-6(3-Cl) G-3(3-CH 3 ) Q-6(3-Cl) G-3(3-CF 3 ) Q-3(4-I) G-1(4-F) Q-3(4-I) G-1(2-F) Q-3(4-I) G-1(2-Cl) Q-3(4-I) G-3(3-F) Q-3(4-I) G-3(3-Cl) Q-3(4-I) G-3(3-CH 3 ) Q-3(4-I) G-3(3-CF 3 ) Q-10 G-1(4-F) Q-10 G-1(2-F) Q-10 G-1(2-Cl) Q-10 G-3(3-F) Q-10 G-3(3-Cl) Q-10 G-3(3-CH 3 ) Q-10 G-3(3-CF 3 ) Q-3(5-Br) G-1(4-F) Q-3(5-Br) G-1(2-F) Q-3(5-Br) G-1(2-Cl) Q-3(5-Br) G-3(3-F) Q-3(5-Br) G-3(3-Cl) Q-3(5-Br) G-3(3-CH 3 ) Q-3(5-Br) G-3(3-CF 3 ) Q-3(3-Br) G-1(4-F) Q-3(3-Br) G-1(2-F) Q-3(3-Br) G-1(2-Cl) Q-3(3-Br) G-3(3-F) Q-3(3-Br) G-3(3-Cl) Q-3(3-Br) G-3(3-CH 3 ) Q-3(3-Br) G-3(3-CF 3 ) Q-3(4-CF 3 ) G-1(4-F) Q-3(4-CF 3 ) G-1(2-F) Q-3(4-CF 3 ) G-1(2-Cl) Q-3(4-CF 3 ) G-3(3-F) Q-3(4-CF 3 ) G-3(3-Cl) Q-3(4-CF 3 ) G-3(3-CH 3 ) Q-3(4-CF 3 ) G-3(3-CF 3 ) Q-8(3-CH 3 ) G-1(4-F) Q-8(3-CH 3 ) G-1(2-F) Q-8(3-CH 3 ) G-1(2-Cl) Q-8(3-CH 3 ) G-3(3-F) Q-8(3-CH 3 ) G-3(3-Cl) Q-8(3-CH 3 ) G-3(3-CH 3 ) Q-8(3-CH 3 ) G-3(3-CF 3 ) Q-8(3-Cl) G-1(4-F) Q-8(3-Cl) G-1(2-F) Q-8(3-Cl) G-1(2-Cl) Q-8(3-Cl) G-3(3-F) Q-8(3-Cl) G-3(3-Cl) Q-8(3-Cl) G-3(3-CH 3 ) Q-8(3-Cl) G-3(3-CF 3 ) Q-1(4-F) G-1(4-F) Q-1(4-F) G-1(5-F) Q-1(4-F) G-3(3-F) Q-1(4-F) G-3(3-Cl) Q-1(4-F) G-3(3-CH 3 ) Q-1(4-F) G-3(3-CF 3 ) Q-1(4-CN) G-1(4-F) Q-1(4-CN) G-1(5-F) Q-1(4-CN) G-3(3-F) Q-1(4-CN) G-3(3-Cl) Q-1(4-CN) G-3(3-CH 3 ) Q-1(4-CN) G-3(3-CF 3 ) Q-2(4-F) G-1(4-F) Q-2(4-F) G-1(5-F) Q-2(4-F) G-3(3-F) Q-2(4-F) G-3(3-Cl) Q-2(4-F) G-3(3-CH 3 ) Q-2(4-F) G-3(3-CF 3 ) Q-2(4-Cl) G-1(4-F) Q-2(4-Cl) G-1(5-F) Q-2(4-Cl) G-3(3-F) Q-2(4-Cl) G-3(3-Cl) Q-2(4-Cl) G-3(3-CH 3 ) Q-2(4-Cl) G-3(3-CF 3 ) Q-2(4-CN) G-1(5-F) Q-3 G-1(4-F) Q-3 G-1(5-F) Q-3 G-3(3-F) Q-3 G-3(3-Cl) Q-3 G-3(3-CH 3 ) Q-3 G-3(3-CF 3 ) Q-3(3-CH 3 ) G-1(5-F) Q-3(3-Cl) G-1(5-F) Q-3(3-F) G-1(4-F) Q-3(3-F) G-1(5-F) Q-3(3-F) G-3(3-F) Q-3(3-F) G-3(3-Cl) Q-3(3-F) G-3(3-CH 3 ) Q-3(3-F) G-3(3-CF 3 ) Q-3(4-Br) G-1(4-F) Q-3(4-Br) G-1(5-F) Q-3(4-Br) G-3(3-F) Q-3(4-Br) G-3(3-Cl) Q-3(4-Br) G-3(3-CH 3 ) Q-3(4-Br) G-3(3-CF 3 ) Q-3(4-CF 3 ) G-1(5-F) Q-3(4-CH 3 ) G-1(4-F) Q-3(4-CH 3 ) G-1(5-F) Q-3(4-CH 3 ) G-3(3-F) Q-3(4-CH 3 ) G-3(3-Cl) Q-3(4-CH 3 ) G-3(3-CH 3 ) Q-3(4-CH 3 ) G-3(3-CF 3 ) Q-3(4-Cl) G-1(4-F) Q-3(4-Cl) G-1(5-F) Q-3(4-Cl) G-3(3-F) Q-3(4-Cl) G-3(3-Cl) Q-3(4-Cl) G-3(3-CH 3 ) Q-3(4-Cl) G-3(3-CF 3 ) Q-3(4-CN) G-1(5-F) Q-3(4-F) G-1(4-F) Q-3(4-F) G-1(5-F) Q-3(4-F) G-3(3-F) Q-3(4-F) G-3(3-Cl) Q-3(4-F) G-3(3-CH 3 ) Q-3(4-F) G-3(3-CF 3 ) Q-3(6-F) G-1(4-F) Q-3(6-F) G-1(5-F) Q-3(6-F) G-3(3-F) Q-3(6-F) G-3(3-Cl) Q-3(6-F) G-3(3-CH 3 ) Q-3(6-F) G-3(3-CF 3 ) Q-4 G-1(4-F) Q-4 G-1(5-F) Q-4 G-3(3-F) Q-4 G-3(3-Cl) Q-4 G-3(3-CH 3 ) Q-4 G-3(3-CF 3 ) Q-4(3-CH 3 ) G-1(5-F) Q-4(3-Cl) G-1(5-F) Q-4(4-Br) G-1(4-F) Q-4(4-Br) G-1(5-F) Q-4(4-Br) G-3(3-F) Q-4(4-Br) G-3(3-Cl) Q-4(4-Br) G-3(3-CH 3 ) Q-4(4-Br) G-3(3-CF 3 ) Q-4(4-Cl) G-1(4-F) Q-4(4-Cl) G-1(5-F) Q-4(4-Cl) G-3(3-F) Q-4(4-Cl) G-3(3-Cl) Q-4(4-Cl) G-3(3-CH 3 ) Q-4(4-Cl) G-3(3-CF 3 ) Q-6(4-Cl) G-1(4-F) Q-6(4-Cl) G-1(5-F) Q-6(4-Cl) G-3(3-F) Q-6(4-Cl) G-3(3-Cl) Q-6(4-Cl) G-3(3-CH 3 ) Q-6(4-Cl) G-3(3-CF 3 ) Q-9 G-1(4-F) Q-9 G-1(5-F) Q-9 G-3(3-F) Q-9 G-3(3-Cl) Q-9 G-3(3-CH 3 ) Q-9 G-3(3-CF 3 ) Q-12a G-1(5-F) ――――――――――― [Table 3]
[0133] [Chemical Structure]
[0134] ―――――― Q ―――――― Q-1 Q-1(4-F) Q-1(4-Cl) Q-1(4-Br) Q-1(4-I) Q-1(4-CN) Q-1(4-CH 3 ) Q-1(4-CF 3 ) Q-2 Q-2(4-F) Q-2(4-Cl) Q-2(4-Br) Q-2(4-I) Q-2(4-CN) Q-2(4-CH 3 ) Q-2(4-CF 3 ) Q-3 Q-3(4-F) Q-3(4-Cl) Q-3(4-Br) Q-3(4-I) Q-3(4-CN) Q-3(4-CH 3 ) Q-3(4-CF 3 ) Q-4 Q-4(4-F) Q-4(4-Cl) Q-4(4-Br) Q-4(4-I) Q-4(4-CN) Q-4(4-CH 3 ) Q-4(4-CF 3 ) Q-6 Q-6(4-F) Q-6(4-Cl) Q-6(4-Br) Q-6(4-I) Q-6(4-CN) Q-6(4-CH 3 ) Q-6(4-CF 3 ) Q-9 Q-9(4-F) Q-9(4-Cl) Q-9(4-Br) Q-9(4-I) Q-9(4-CN) Q-9(4-CH 3 ) Q-9(4-CF 3 ) Q-10 Q-10(3-F) Q-10(3-Cl) Q-10(3-Br) Q-10(3-I) Q-10(3-CN) Q-10(3-CH 3 ) Q-10(3-CF 3 ) Q-12a Q-12a(4-F) Q-12a(4-Cl) Q-12a(4-Br) Q-12a(4-I) Q-12a(4-CN) Q-12a(4-CH 3 ) Q-12a(4-CF 3 ) Q-1(3-F) Q-1(3-Cl) Q-1(3-Br) Q-1(3-I) Q-1(3-CN) Q-1(3-CH 3 ) Q-1(3-CF 3 ) Q-1(2-F) Q-1(2-Cl) Q-1(2-Br) Q-1(2-I) Q-1(2-CN) Q-1(2-CH 3 ) Q-1(2-CF 3 ) Q-3(3-F) Q-3(3-Cl) Q-3(3-Br) Q-3(3-I) Q-3(3-CN) Q-3(3-CH 3 ) Q-3(3-CF 3 ) Q-3(5-F) Q-3(5-Cl) Q-3(5-Br) Q-3(5-I) Q-3(5-CN) Q-3(5-CH 3 ) Q-3(5-CF 3 ) Q-3(6-F) Q-3(6-Cl) Q-3(6-Br) Q-3(6-I) Q-3(6-CN) Q-3(6-CH 3 ) Q-3(6-CF 3 ) Q-4(3-F) Q-4(3-Cl) Q-4(3-Br) Q-4(3-I) Q-4(3-CN) Q-4(3-CH 3 ) Q-4(3-CF 3 ) Q-6(3-F) Q-6(3-Cl) Q-6(3-Br) Q-6(3-I) Q-6(3-CN) Q-6(3-CH 3 ) Q-6(3-CF 3 ) Q-9(3-F) Q-9(3-Cl) Q-9(3-Br) Q-9(3-I) Q-9(3-CN) Q-9(3-CH 3 ) Q-9(3-CF 3 ) ―――――― [Table 4]
[0135] [Chemical]
[0136] —————— Q —————— Q - 1 Q - 1(4 - F) Q - 1(4 - Cl) Q - 1(4 - Br) Q - 1(4 - I) Q - 1(4 - CN) Q - 1(4 - CH 3 ) Q - 1(4 - CF 3 ) Q - 2 Q - 2(4 - F) Q - 2(4 - Cl) Q - 2(4 - Br) Q - 2(4 - I) Q - 2(4 - CN) Q - 2(4 - CH 3 ) Q - 2(4 - CF 3 ) Q - 3 Q - 3(4 - F) Q - 3(4 - Cl) Q - 3(4 - Br) Q - 3(4 - I) Q - 3(4 - CN) Q - 3(4 - CH 3 ) Q - 3(4 - CF 3 ) Q - 4 Q - 4(4 - F) Q - 4(4 - Cl) Q - 4(4 - Br) Q - 4(4 - I) Q - 4(4 - CN) Q - 4(4 - CH 3 ) Q - 4(4 - CF 3 ) Q - 6 Q - 6(4 - F) Q - 6(4 - Cl) Q - 6(4 - Br) Q-6(4-I) Q-6(4-CN) Q-6(4-CH 3 ) Q-6(4-CF 3 ) Q-9 Q-9(4-F) Q-9(4-Cl) Q-9(4-Br) Q-9(4-I) Q-9(4-CN) Q-9(4-CH 3 ) Q-9(4-CF 3 ) Q-10 Q-10(3-F) Q-10(3-Cl) Q-10(3-Br) Q-10(3-I) Q-10(3-CN) Q-10(3-CH 3 ) Q-10(3-CF 3 ) Q-12a Q-12a(4-F) Q-12a(4-Cl) Q-12a(4-Br) Q-12a(4-I) Q-12a(4-CN) Q-12a(4-CH 3 ) Q-12a(4-CF 3 ) Q-1(3-F) Q-1(3-Cl) Q-1(3-Br) Q-1(3-I) Q-1(3-CN) Q-1(3-CH 3 ) Q-1(3-CF 3 ) Q-1(2-F) Q-1(2-Cl) Q-1(2-Br) Q-1(2-I) Q-1(2-CN) Q-1(2-CH 3 ) Q-1(2-CF 3 ) Q-3(3-F) Q-3(3-Cl) Q-3(3-Br) Q-3(3-I) Q-3(3-CN) Q-3(3-CH 3 ) Q-3(3-CF 3 ) Q-3(5-F) Q-3(5-Cl) Q-3(5-Br) Q-3(5-I) Q-3(5-CN) Q-3(5-CH 3 ) Q-3(5-CF 3 ) Q-3(6-F) Q-3(6-Cl) Q-3(6-Br) Q-3(6-I) Q-3(6-CN) Q-3(6-CH 3 ) Q-3(6-CF 3 ) Q-4(3-F) Q-4(3-Cl) Q-4(3-Br) Q-4(3-I) Q-4(3-CN) Q-4(3-CH 3 ) Q-4(3-CF 3 ) Q-6(3-F) Q-6(3-Cl) Q-6(3-Br) Q-6(3-I) Q-6(3-CN) Q-6(3-CH 3 ) Q-6(3-CF 3 ) Q-9(3-F) Q-9(3-Cl) Q-9(3-Br) Q-9(3-I) Q-9(3-CN) Q-9(3-CH 3 ) Q-9(3-CF 3 ) —————— [Table 5]
[0137]
Chem.
[0138] —————— R 1 G 51 —————— HCl HBr HI FCl FBr FI ClCl ClBr ClI CHF 2 Cl CHF 2 Br CHF 2 I CF 3 Cl CF 3 Br CF 3 I —————— [Table 6]
[0139]
Chem.
[0140] —————— G 51 —————— Cl Br I —————— [Table 7]
[0141] [Chem.]
[0142] ――――――――――― R 1 G ――――――――――― Cl G-7 Cl G-1 Cl G-3 Cl G-2 Cl G-7(3-F) Cl G-7(4-F) Cl G-7(5-F) Cl G-7(6-F) Cl G-1(2-F) Cl G-1(4-F) Cl G-1(5-F) Cl G-1(6-F) Cl G-3(2-F) Cl G-3(3-F) Cl G-2(2-F) Cl G-2(3-F) Cl G-2(4-F) Cl G-2(2-F,4-F) Cl G-2(2-F,5-F) Cl G-7(3-Cl) Cl G-7(4-Cl) Cl G-7(5-Cl) Cl G-7(6-Cl) Cl G-1(2-Cl) Cl G-1(4-Cl) Cl G-1(5-Cl) Cl G-1(6-Cl) Cl G-3(2-Cl) Cl G-3(3-Cl) Cl G-2(2-Cl) Cl G-2(3-Cl) Cl G-2(4-Cl) Cl G-2(2-Cl,4-Cl) Cl G-2(2-Cl,5-Cl) Cl G-7(3-CH 3 ) Cl G-7(4-CH 3 ) Cl G-7(5-CH 3 ) Cl G-7(6-CH 3 ) Cl G-1(2-CH 3 ) Cl G-1(4-CH 3 ) Cl G-1(5-CH 3 ) Cl G-1(6-CH 3 ) Cl G-3(2-CH 3 ) Cl G-3(3-CH 3 ) Cl G-2(2-CH 3 ) Cl G-2(3-CH 3 ) Cl G-2(4-CH 3 ) Cl G-2(2-CH 3 ,4-CH 3 ) Cl G-2(2-CH 3 ,5-CH 3 ) Cl G-7(3-CF 3 ) Cl G-7(4-CF 3 ) Cl G-7(5-CF 3 ) Cl G-7(6-CF 3 ) Cl G-1(2-CF 3 ) Cl G-1(4-CF 3 ) Cl G-1(5-CF 3 ) Cl G-1(6-CF 3 ) Cl G-3(2-CF 3 ) Cl G-3(3-CF3 ) Cl G-2(2-CF 3 ) Cl G-2(3-CF 3 ) Cl G-2(4-CF 3 ) Cl G-2(2-CF 3 ,4-CF 3 ) Cl G-2(2-CF 3 ,5-CF 3 ) Cl G-1(4-NO 2 ) Cl G-1(4-NH 2 ) Cl G-1(5-NO 2 ) Cl G-1(5-NH 2 ) Cl G-3(3-NO 2 ) Cl G-3(3-NH 2 ) CF 3 G-7 CF 3 G-1 CF 3 G-3 CF 3 G-2 CF 3 G-7(3-F) CF 3 G-7(4-F) CF 3 G-7(5-F) CF 3 G-7(6-F) CF 3 G-1(2-F) CF 3 G-1(4-F) CF 3 G-1(5-F) CF 3 G-1(6-F) CF 3 G-3(2-F) CF 3 G-3(3-F) CF 3 G-2(2-F) CF3 G-2(3-F) CF 3 G-2(4-F) CF 3 G-2(2-F,4-F) CF 3 G-2(2-F,5-F) CF 3 G-7(3-Cl) CF 3 G-7(4-Cl) CF 3 G-7(5-Cl) CF 3 G-7(6-Cl) CF 3 G-1(2-Cl) CF 3 G-1(4-Cl) CF 3 G-1(5-Cl) CF 3 G-1(6-Cl) CF 3 G-3(2-Cl) CF 3 G-3(3-Cl) CF 3 G-2(2-Cl) CF 3 G-2(3-Cl) CF 3 G-2(4-Cl) CF 3 G-2(2-Cl,4-Cl) CF 3 G-2(2-Cl,5-Cl) CF 3 G-7(3-CH 3 ) CF 3 G-7(4-CH 3 ) CF 3 G-7(5-CH 3 ) CF 3 G-7(6-CH 3 ) CF 3 G-1(2-CH 3 ) CF 3 G-1(4-CH 3 ) CF 3 G-1(5-CH 3 ) CF 3 G-1(6-CH 3 ) CF 3 G-3(2-CH 3 ) CF 3 G-3(3-CH 3 ) CF 3 G-2(2-CH 3 ) CF 3 G-2(3-CH 3 ) CF 3 G-2(4-CH 3 ) CF 3 G-2(2-CH 3 ,4-CH 3 ) CF 3 G-2(2-CH 3 ,5-CH 3 ) CF 3 G-7(3-CF 3 ) CF 3 G-7(4-CF 3 ) CF 3 G-7(5-CF 3 ) CF 3 G-7(6-CF 3 ) CF 3 G-1(2-CF 3 ) CF 3 G-1(4-CF 3 ) CF 3 G-1(5-CF 3 ) CF 3 G-1(6-CF 3 ) CF 3 G-3(2-CF 3 ) CF 3 G-3(3-CF 3 ) CF3 G-2(2-CF 3 ) CF 3 G-2(3-CF 3 ) CF 3 G-2(4-CF 3 ) CF 3 G-2(2-CF 3 ,4-CF 3 ) CF 3 G-2(2-CF 3 ,5-CF 3 ) CF 3 G-1(4-NO 2 ) CF 3 G-1(4-NH 2 ) CF 3 G-1(5-NO 2 ) CF 3 G-1(5-NH 2 ) CF 3 G-3(3-NO 2 ) CF 3 G-3(3-NH 2 ) CHF 2 G-7 CHF 2 G-1 CHF 2 G-3 CHF 2 G-2 CHF 2 G-7(3-F) CHF 2 G-7(4-F) CHF 2 G-7(5-F) CHF 2 G-7(6-F) CHF 2 G-1(2-F) CHF 2 G-1(4-F) CHF 2 G-1(5-F) CHF 2 G-1(6-F) CHF 2 G-3(2-F) CHF 2 G-3(3-F) CHF 2 G-2(2-F) CHF 2 G-2(3-F) CHF 2 G-2(4-F) CHF 2 G-2(2-F,4-F) CHF 2 G-2(2-F,5-F) CHF 2 G-7(3-Cl) CHF 2 G-7(4-Cl) CHF 2 G-7(5-Cl) CHF 2 G-7(6-Cl) CHF 2 G-1(2-Cl) CHF 2 G-1(4-Cl) CHF 2 G-1(5-Cl) CHF 2 G-1(6-Cl) CHF 2 G-3(2-Cl) CHF 2 G-3(3-Cl) CHF 2 G-2(2-Cl) CHF 2 G-2(3-Cl) CHF 2 G-2(4-Cl) CHF 2 G-2(2-Cl,4-Cl) CHF 2 G-2(2-Cl,5-Cl) CHF 2 G-7(3-CH 3 ) CHF 2 G-7(4-CH 3 ) CHF 2 G-7(5-CH 3 ) CHF 2 G-7(6-CH 3 ) CHF 2 G-1(2-CH 3 ) CHF 2 G-1(4-CH 3 ) CHF 2 G-1(5-CH 3 ) CHF 2 G-1(6-CH 3 ) CHF 2 G-3(2-CH 3 ) CHF 2 G-3(3-CH 3 ) CHF 2 G-2(2-CH 3 ) CHF 2 G-2(3-CH 3 ) CHF 2 G-2(4-CH 3 ) CHF 2 G-2(2-CH 3 ,4-CH 3 ) CHF 2 G-2(2-CH 3 ,5-CH 3 ) CHF 2 G-7(3-CF 3 ) CHF 2 G-7(4-CF 3 ) CHF 2 G-7(5-CF 3 ) CHF 2 G-7(6-CF 3 ) CHF 2 G-1(2-CF 3 ) CHF 2 G-1(4-CF 3 ) CHF 2 G-1(5-CF 3) CHF 2 G-1(6-CF 3 ) CHF 2 G-3(2-CF 3 ) CHF 2 G-3(3-CF 3 ) CHF 2 G-2(2-CF 3 ) CHF 2 G-2(3-CF 3 ) CHF 2 G-2(4-CF 3 ) CHF 2 G-2(2-CF 3 ,4-CF 3 ) CHF 2 G-2(2-CF 3 ,5-CF 3 ) ――――――――――― [Table 8]
[0143]
Chem.
[0144] ―――――――― G ―――――――― G-7 G-1 G-3 G-2 G-7(3-F) G-7(4-F) G-7(5-F) G-7(6-F) G-1(2-F) G-1(4-F) G-1(5-F) G-1(6-F) G-3(2-F) G-3(3-F) G-2(2-F) G-2(3-F) G-2(4-F) G-2(2-F,4-F) G-2(2-F,5-F) G-7(3-Cl) G-7(4-Cl) G-7(5-Cl) G-7(6-Cl) G-1(2-Cl) G-1(4-Cl) G-1(5-Cl) G-1(6-Cl) G-3(2-Cl) G-3(3-Cl) G-2(2-Cl) G-2(3-Cl) G-2(4-Cl) G-2(2-Cl,4-Cl) G-2(2-Cl,5-Cl) G-7(3-CH 3 ) G-7(4-CH 3 ) G-7(5-CH 3 ) G-7(6-CH 3 ) G-1(2-CH 3 ) G-1(4-CH 3 ) G-1(5-CH 3 ) G-1(6-CH 3 ) G-3(2-CH 3 ) G-3(3-CH 3 ) G-2(2-CH 3 ) G-2(3-CH 3 ) G-2(4-CH 3 ) G-2(2-CH 3 ,4-CH 3 ) G-2(2-CH 3 ,5-CH 3 ) G-7(3-CF 3 ) G-7(4-CF 3 ) G-7(5-CF 3 ) G-7(6-CF 3 ) G-1(2-CF 3 ) G-1(4-CF 3 ) G-1(5-CF 3 ) G-1(6-CF 3 ) G-3(2-CF 3 ) G-3(3-CF 3 ) G-2(2-CF 3 ) G-2(3-CF 3 ) G-2(4-CF 3 ) G-2(2-CF 3 ,4-CF 3 ) G-2(2-CF 3 ,5-CF 3 ) G-1(4-NO 2 ) G-1(4-NH 2 ) G-1(5-NO 2 ) G-1(5-NH 2 ) G-3(3-NO 2 ) G-3(3-NH 2 ) ―――――――― [Table 9]
[0145]
Chem.
[0146] ――――――――――― Q G ――――――――――― Q-3(3-Cl) G-1(4-F) Q-3(3-Cl) G-1(2-F) Q-3(3-Cl) G-1(2-Cl) Q-3(3-Cl) G-3(3-F) Q-3(3-Cl) G-3(3-Cl) Q-3(3-Cl) G-3(3-CH 3 ) Q-3(3-Cl) G-3(3-CF 3 ) Q-3(3-CH 3 ) G-1(4-F) Q-3(3-CH 3 ) G-1(2-F) Q-3(3-CH 3 ) G-1(2-Cl) Q-3(3-CH 3 ) G-3(3-F) Q-3(3-CH 3 ) G-3(3-Cl) Q-3(3-CH 3 ) G-3(3-CH 3 ) Q-3(3-CH 3 ) G-3(3-CF 3 ) Q-4(3-Cl) G-1(4-F) Q-4(3-Cl) G-1(2-F) Q-4(3-Cl) G-1(2-Cl) Q-4(3-Cl) G-3(3-F) Q-4(3-Cl) G-3(3-Cl) Q-4(3-Cl) G-3(3-CH 3 ) Q-4(3-Cl) G-3(3-CF 3 ) Q-4(3-CH 3 ) G-1(4-F) Q-4(3-CH 3 ) G-1(2-F) Q-4(3-CH 3 ) G-1(2-Cl) Q-4(3-CH 3 ) G-3(3-F) Q-4(3-CH 3) G-3(3-Cl) Q-4(3-CH 3 ) G-3(3-CH 3 ) Q-4(3-CH 3 ) G-3(3-CF 3 ) Q-4(4-CH 3 ) G-1(4-F) Q-4(4-CH 3 ) G-1(2-F) Q-4(4-CH 3 ) G-1(2-Cl) Q-4(4-CH 3 ) G-3(3-F) Q-4(4-CH 3 ) G-3(3-Cl) Q-4(4-CH 3 ) G-3(3-CH 3 ) Q-4(4-CH 3 ) G-3(3-CF 3 ) Q-4(3-Br) G-1(4-F) Q-4(3-Br) G-1(2-F) Q-4(3-Br) G-1(2-Cl) Q-4(3-Br) G-3(3-F) Q-4(3-Br) G-3(3-Cl) Q-4(3-Br) G-3(3-CH 3 ) Q-4(3-Br) G-3(3-CF 3 ) Q-10(3-CH 3 ) G-1(4-F) Q-10(3-CH 3 ) G-1(2-F) Q-10(3-CH 3 ) G-1(2-Cl) Q-10(3-CH 3 ) G-3(3-F) Q-10(3-CH 3 ) G-3(3-Cl) Q-10(3-CH 3 ) G-3(3-CH 3 ) Q-10(3-CH 3 ) G-3(3-CF 3 ) Q-12a G-1(4-F) Q-12a G-1(2-F) Q-12a G-1(2-Cl) Q-12a G-3(3-F) Q-12a G-3(3-Cl) Q-12a G-3(3-CH 3 ) Q-12a G-3(3-CF 3 ) Q-47a G-1(4-F) Q-47a G-1(2-F) Q-47a G-1(2-Cl) Q-47a G-3(3-F) Q-47a G-3(3-Cl) Q-47a G-3(3-CH 3 ) Q-47a G-3(3-CF 3 ) Q-3(4-CN) G-1(4-F) Q-3(4-CN) G-1(2-F) Q-3(4-CN) G-1(2-Cl) Q-3(4-CN) G-3(3-F) Q-3(4-CN) G-3(3-Cl) Q-3(4-CN) G-3(3-CH 3 ) Q-3(4-CN) G-3(3-CF 3 ) Q-2(4-CN) G-1(4-F) Q-2(4-CN) G-1(2-F) Q-2(4-CN) G-1(2-Cl) Q-2(4-CN) G-3(3-F) Q-2(4-CN) G-3(3-Cl) Q-2(4-CN) G-3(3-CH 3 ) Q-2(4-CN) G-3(3-CF 3 ) Q-3(5-Cl) G-1(4-F) Q-3(5-Cl) G-1(2-F) Q-3(5-Cl) G-1(2-Cl) Q-3(5-Cl) G-3(3-F) Q-3(5-Cl) G-3(3-Cl) Q-3(5-Cl) G-3(3-CH 3 ) Q-3(5-Cl) G-3(3-CF 3 ) Q-3(5-CH 3 ) G-1(4-F) Q-3(5-CH 3 ) G-1(2-F) Q-3(5-CH 3 ) G-1(2-Cl) Q-3(5-CH 3 ) G-3(3-F) Q-3(5-CH 3 ) G-3(3-Cl) Q-3(5-CH 3 ) G-3(3-CH 3 ) Q-3(5-CH 3 ) G-3(3-CF 3 ) Q-6(3-CH 3 ) G-1(4-F) Q-6(3-CH 3 ) G-1(2-F) Q-6(3-CH 3 ) G-1(2-Cl) Q-6(3-CH 3 ) G-3(3-F) Q-6(3-CH 3 ) G-3(3-Cl) Q-6(3-CH 3 ) G-3(3-CH 3 ) Q-6(3-CH 3 ) G-3(3-CF 3 ) Q-6(3-Cl) G-1(4-F) Q-6(3-Cl) G-1(2-F) Q-6(3-Cl) G-1(2-Cl) Q-6(3-Cl) G-3(3-F) Q-6(3-Cl) G-3(3-Cl) Q-6(3-Cl) G-3(3-CH 3 ) Q-6(3-Cl) G-3(3-CF 3 ) Q-3(4-I) G-1(4-F) Q-3(4-I) G-1(2-F) Q-3(4-I) G-1(2-Cl) Q-3(4-I) G-3(3-F) Q-3(4-I) G-3(3-Cl) Q-3(4-I) G-3(3-CH 3 ) Q-3(4-I) G-3(3-CF 3 ) Q-10 G-1(4-F) Q-10 G-1(2-F) Q-10 G-1(2-Cl) Q-10 G-3(3-F) Q-10 G-3(3-Cl) Q-10 G-3(3-CH 3 ) Q-10 G-3(3-CF 3 ) Q-3(5-Br) G-1(4-F) Q-3(5-Br) G-1(2-F) Q-3(5-Br) G-1(2-Cl) Q-3(5-Br) G-3(3-F) Q-3(5-Br) G-3(3-Cl) Q-3(5-Br) G-3(3-CH 3 ) Q-3(5-Br) G-3(3-CF 3 ) Q-3(3-Br) G-1(4-F) Q-3(3-Br) G-1(2-F) Q-3(3-Br) G-1(2-Cl) Q-3(3-Br) G-3(3-F) Q-3(3-Br) G-3(3-Cl) Q-3(3-Br) G-3(3-CH 3 ) Q-3(3-Br) G-3(3-CF 3 ) Q-3(4-CF 3 ) G-1(4-F) Q-3(4-CF 3 ) G-1(2-F) Q-3(4-CF 3 ) G-1(2-Cl) Q-3(4-CF 3 ) G-3(3-F) Q-3(4-CF 3 ) G-3(3-Cl) Q-3(4-CF 3 ) G-3(3-CH 3 ) Q-3(4-CF 3 ) G-3(3-CF 3 ) Q-8(3-CH 3 ) G-1(4-F) Q-8(3-CH 3 ) G-1(2-F) Q-8(3-CH 3 ) G-1(2-Cl) Q-8(3-CH 3 ) G-3(3-F) Q-8(3-CH 3 ) G-3(3-Cl) Q-8(3-CH 3 ) G-3(3-CH 3 ) Q-8(3-CH 3 ) G-3(3-CF 3 ) Q-8(3-Cl) G-1(4-F) Q-8(3-Cl) G-1(2-F) Q-8(3-Cl) G-1(2-Cl) Q-8(3-Cl) G-3(3-F) Q-8(3-Cl) G-3(3-Cl) Q-8(3-Cl) G-3(3-CH 3 ) Q-8(3-Cl) G-3(3-CF 3 ) Q-1(4-F) G-1(4-F) Q-1(4-F) G-1(5-F) Q-1(4-F) G-3(3-F) Q-1(4-F) G-3(3-Cl) Q-1(4-F) G-3(3-CH 3 ) Q-1(4-F) G-3(3-CF 3 ) Q-1(4-CN) G-1(4-F) Q-1(4-CN) G-1(5-F) Q-1(4-CN) G-3(3-F) Q-1(4-CN) G-3(3-Cl) Q-1(4-CN) G-3(3-CH 3 ) Q-1(4-CN) G-3(3-CF 3 ) Q-2(4-F) G-1(4-F) Q-2(4-F) G-1(5-F) Q-2(4-F) G-3(3-F) Q-2(4-F) G-3(3-Cl) Q-2(4-F) G-3(3-CH 3 ) Q-2(4-F) G-3(3-CF 3 ) Q-2(4-Cl) G-1(4-F) Q-2(4-Cl) G-1(5-F) Q-2(4-Cl) G-3(3-F) Q-2(4-Cl) G-3(3-Cl) Q-2(4-Cl) G-3(3-CH 3 ) Q-2(4-Cl) G-3(3-CF 3 ) Q-2(4-CN) G-1(5-F) Q-3 G-1(4-F) Q-3 G-1(5-F) Q-3 G-3(3-F) Q-3 G-3(3-Cl) Q-3 G-3(3-CH 3 ) Q-3 G-3(3-CF 3 ) Q-3(3-CH 3 ) G-1(5-F) Q-3(3-Cl) G-1(5-F) Q-3(3-F) G-1(4-F) Q-3(3-F) G-1(5-F) Q-3(3-F) G-3(3-F) Q-3(3-F) G-3(3-Cl) Q-3(3-F) G-3(3-CH 3 ) Q-3(3-F) G-3(3-CF 3 ) Q-3(4-Br) G-1(4-F) Q-3(4-Br) G-1(5-F) Q-3(4-Br) G-3(3-F) Q-3(4-Br) G-3(3-Cl) Q-3(4-Br) G-3(3-CH 3 ) Q-3(4-Br) G-3(3-CF 3 ) Q-3(4-CF 3 ) G-1(5-F) Q-3(4-CH 3 ) G-1(4-F) Q-3(4-CH 3 ) G-1(5-F) Q-3(4-CH 3 ) G-3(3-F) Q-3(4-CH 3 ) G-3(3-Cl) Q-3(4-CH 3 ) G-3(3-CH 3 ) Q-3(4-CH 3 ) G-3(3-CF 3 ) Q-3(4-Cl) G-1(4-F) Q-3(4-Cl) G-1(5-F) Q-3(4-Cl) G-3(3-F) Q-3(4-Cl) G-3(3-Cl) Q-3(4-Cl) G-3(3-CH 3 ) Q-3(4-Cl) G-3(3-CF 3 ) Q-3(4-CN) G-1(5-F) Q-3(4-F) G-1(4-F) Q-3(4-F) G-1(5-F) Q-3(4-F) G-3(3-F) Q-3(4-F) G-3(3-Cl) Q-3(4-F) G-3(3-CH 3 ) Q-3(4-F) G-3(3-CF 3 ) Q-3(6-F) G-1(4-F) Q-3(6-F) G-1(5-F) Q-3(6-F) G-3(3-F) Q-3(6-F) G-3(3-Cl) Q-3(6-F) G-3(3-CH 3 ) Q-3(6-F) G-3(3-CF 3 ) Q-4 G-1(4-F) Q-4 G-1(5-F) Q-4 G-3(3-F) Q-4 G-3(3-Cl) Q-4 G-3(3-CH 3 ) Q-4 G-3(3-CF 3 ) Q-4(3-CH 3 ) G-1(5-F) Q-4(3-Cl) G-1(5-F) Q-4(4-Br) G-1(4-F) Q-4(4-Br) G-1(5-F) Q-4(4-Br) G-3(3-F) Q-4(4-Br) G-3(3-Cl) Q-4(4-Br) G-3(3-CH 3 ) Q-4(4-Br) G-3(3-CF 3 ) Q-4(4-Cl) G-1(4-F) Q-4(4-Cl) G-1(5-F) Q-4(4-Cl) G-3(3-F) Q-4(4-Cl) G-3(3-Cl) Q-4(4-Cl) G-3(3-CH 3 ) Q-4(4-Cl) G-3(3-CF 3 ) Q-6(4-Cl) G-1(4-F) Q-6(4-Cl) G-1(5-F) Q-6(4-Cl) G-3(3-F) Q-6(4-Cl) G-3(3-Cl) Q-6(4-Cl) G-3(3-CH 3 ) Q-6(4-Cl) G-3(3-CF 3 ) Q-9 G-1(4-F) Q-9 G-1(5-F) Q-9 G-3(3-F) Q-9 G-3(3-Cl) Q-9 G-3(3-CH 3 ) Q-9 G-3(3-CF 3 ) Q-12a G-1(5-F) ――――――――――― [Table 10]
[0147] [Chemistry]
[0148] ――――――――――― Q G ――――――――――― Q-3(3-Cl) G-1(4-F) Q-3(3-Cl) G-1(2-F) Q-3(3-Cl) G-1(2-Cl) Q-3(3-Cl) G-3(3-F) Q-3(3-Cl) G-3(3-Cl) Q-3(3-Cl) G-3(3-CH 3 ) Q-3(3-Cl) G-3(3-CF 3 ) Q-3(3-CH 3 ) G-1(4-F) Q-3(3-CH 3 ) G-1(2-F) Q-3(3-CH 3 ) G-1(2-Cl) Q-3(3-CH 3 ) G-3(3-F) Q-3(3-CH 3 ) G-3(3-Cl) Q-3(3-CH 3 ) G-3(3-CH 3 ) Q-3(3-CH 3 ) G-3(3-CF 3 ) Q-4(3-Cl) G-1(4-F) Q-4(3-Cl) G-1(2-F) Q-4(3-Cl) G-1(2-Cl) Q-4(3-Cl) G-3(3-F) Q-4(3-Cl) G-3(3-Cl) Q-4(3-Cl) G-3(3-CH 3 ) Q-4(3-Cl) G-3(3-CF 3 ) Q-4(3-CH 3 ) G-1(4-F) Q-4(3-CH 3 ) G-1(2-F) Q-4(3-CH 3 ) G-1(2-Cl) Q-4(3-CH 3 ) G-3(3-F) Q-4(3-CH 3) G-3(3-Cl) Q-4(3-CH 3 ) G-3(3-CH 3 ) Q-4(3-CH 3 ) G-3(3-CF 3 ) Q-4(4-CH 3 ) G-1(4-F) Q-4(4-CH 3 ) G-1(2-F) Q-4(4-CH 3 ) G-1(2-Cl) Q-4(4-CH 3 ) G-3(3-F) Q-4(4-CH 3 ) G-3(3-Cl) Q-4(4-CH 3 ) G-3(3-CH 3 ) Q-4(4-CH 3 ) G-3(3-CF 3 ) Q-4(3-Br) G-1(4-F) Q-4(3-Br) G-1(2-F) Q-4(3-Br) G-1(2-Cl) Q-4(3-Br) G-3(3-F) Q-4(3-Br) G-3(3-Cl) Q-4(3-Br) G-3(3-CH 3 ) Q-4(3-Br) G-3(3-CF 3 ) Q-10(3-CH 3 ) G-1(4-F) Q-10(3-CH 3 ) G-1(2-F) Q-10(3-CH 3 ) G-1(2-Cl) Q-10(3-CH 3 ) G-3(3-F) Q-10(3-CH 3 ) G-3(3-Cl) Q-10(3-CH 3 ) G-3(3-CH 3 ) Q-10(3-CH 3 ) G-3(3-CF 3 ) Q-12a G-1(4-F) Q-12a G-1(2-F) Q-12a G-1(2-Cl) Q-12a G-3(3-F) Q-12a G-3(3-Cl) Q-12a G-3(3-CH 3 ) Q-12a G-3(3-CF 3 ) Q-47a G-1(4-F) Q-47a G-1(2-F) Q-47a G-1(2-Cl) Q-47a G-3(3-F) Q-47a G-3(3-Cl) Q-47a G-3(3-CH 3 ) Q-47a G-3(3-CF 3 ) Q-3(4-CN) G-1(4-F) Q-3(4-CN) G-1(2-F) Q-3(4-CN) G-1(2-Cl) Q-3(4-CN) G-3(3-F) Q-3(4-CN) G-3(3-Cl) Q-3(4-CN) G-3(3-CH 3 ) Q-3(4-CN) G-3(3-CF 3 ) Q-2(4-CN) G-1(4-F) Q-2(4-CN) G-1(2-F) Q-2(4-CN) G-1(2-Cl) Q-2(4-CN) G-3(3-F) Q-2(4-CN) G-3(3-Cl) Q-2(4-CN) G-3(3-CH 3 ) Q-2(4-CN) G-3(3-CF 3 ) Q-3(5-Cl) G-1(4-F) Q-3(5-Cl) G-1(2-F) Q-3(5-Cl) G-1(2-Cl) Q-3(5-Cl) G-3(3-F) Q-3(5-Cl) G-3(3-Cl) Q-3(5-Cl) G-3(3-CH 3 ) Q-3(5-Cl) G-3(3-CF 3 ) Q-3(5-CH 3 ) G-1(4-F) Q-3(5-CH 3 ) G-1(2-F) Q-3(5-CH 3 ) G-1(2-Cl) Q-3(5-CH 3 ) G-3(3-F) Q-3(5-CH 3 ) G-3(3-Cl) Q-3(5-CH 3 ) G-3(3-CH 3 ) Q-3(5-CH 3 ) G-3(3-CF 3 ) Q-6(3-CH 3 ) G-1(4-F) Q-6(3-CH 3 ) G-1(2-F) Q-6(3-CH 3 ) G-1(2-Cl) Q-6(3-CH 3 ) G-3(3-F) Q-6(3-CH 3 ) G-3(3-Cl) Q-6(3-CH 3 ) G-3(3-CH 3 ) Q-6(3-CH 3 ) G-3(3-CF 3 ) Q-6(3-Cl) G-1(4-F) Q-6(3-Cl) G-1(2-F) Q-6(3-Cl) G-1(2-Cl) Q-6(3-Cl) G-3(3-F) Q-6(3-Cl) G-3(3-Cl) Q-6(3-Cl) G-3(3-CH 3 ) Q-6(3-Cl) G-3(3-CF 3 ) Q-3(4-I) G-1(4-F) Q-3(4-I) G-1(2-F) Q-3(4-I) G-1(2-Cl) Q-3(4-I) G-3(3-F) Q-3(4-I) G-3(3-Cl) Q-3(4-I) G-3(3-CH 3 ) Q-3(4-I) G-3(3-CF 3 ) Q-10 G-1(4-F) Q-10 G-1(2-F) Q-10 G-1(2-Cl) Q-10 G-3(3-F) Q-10 G-3(3-Cl) Q-10 G-3(3-CH 3 ) Q-10 G-3(3-CF 3 ) Q-3(5-Br) G-1(4-F) Q-3(5-Br) G-1(2-F) Q-3(5-Br) G-1(2-Cl) Q-3(5-Br) G-3(3-F) Q-3(5-Br) G-3(3-Cl) Q-3(5-Br) G-3(3-CH 3 ) Q-3(5-Br) G-3(3-CF 3 ) Q-3(3-Br) G-1(4-F) Q-3(3-Br) G-1(2-F) Q-3(3-Br) G-1(2-Cl) Q-3(3-Br) G-3(3-F) Q-3(3-Br) G-3(3-Cl) Q-3(3-Br) G-3(3-CH 3 ) Q-3(3-Br) G-3(3-CF 3 ) Q-3(4-CF 3 ) G-1(4-F) Q-3(4-CF 3 ) G-1(2-F) Q-3(4-CF 3 ) G-1(2-Cl) Q-3(4-CF 3 ) G-3(3-F) Q-3(4-CF 3 ) G-3(3-Cl) Q-3(4-CF 3 ) G-3(3-CH 3 ) Q-3(4-CF 3 ) G-3(3-CF 3 ) Q-8(3-CH 3 ) G-1(4-F) Q-8(3-CH 3 ) G-1(2-F) Q-8(3-CH 3 ) G-1(2-Cl) Q-8(3-CH 3 ) G-3(3-F) Q-8(3-CH 3 ) G-3(3-Cl) Q-8(3-CH 3 ) G-3(3-CH 3 ) Q-8(3-CH 3 ) G-3(3-CF 3 ) Q-8(3-Cl) G-1(4-F) Q-8(3-Cl) G-1(2-F) Q-8(3-Cl) G-1(2-Cl) Q-8(3-Cl) G-3(3-F) Q-8(3-Cl) G-3(3-Cl) Q-8(3-Cl) G-3(3-CH 3 ) Q-8(3-Cl) G-3(3-CF 3 ) Q-1(4-F) G-1(4-F) Q-1(4-F) G-1(5-F) Q-1(4-F) G-3(3-F) Q-1(4-F) G-3(3-Cl) Q-1(4-F) G-3(3-CH 3 ) Q-1(4-F) G-3(3-CF 3 ) Q-1(4-CN) G-1(4-F) Q-1(4-CN) G-1(5-F) Q-1(4-CN) G-3(3-F) Q-1(4-CN) G-3(3-Cl) Q-1(4-CN) G-3(3-CH 3 ) Q-1(4-CN) G-3(3-CF 3 ) Q-2(4-F) G-1(4-F) Q-2(4-F) G-1(5-F) Q-2(4-F) G-3(3-F) Q-2(4-F) G-3(3-Cl) Q-2(4-F) G-3(3-CH 3 ) Q-2(4-F) G-3(3-CF 3 ) Q-2(4-Cl) G-1(4-F) Q-2(4-Cl) G-1(5-F) Q-2(4-Cl) G-3(3-F) Q-2(4-Cl) G-3(3-Cl) Q-2(4-Cl) G-3(3-CH 3 ) Q-2(4-Cl) G-3(3-CF 3 ) Q-2(4-CN) G-1(5-F) Q-3 G-1(4-F) Q-3 G-1(5-F) Q-3 G-3(3-F) Q-3 G-3(3-Cl) Q-3 G-3(3-CH 3 ) Q-3 G-3(3-CF 3 ) Q-3(3-CH 3 ) G-1(5-F) Q-3(3-Cl) G-1(5-F) Q-3(3-F) G-1(4-F) Q-3(3-F) G-1(5-F) Q-3(3-F) G-3(3-F) Q-3(3-F) G-3(3-Cl) Q-3(3-F) G-3(3-CH 3 ) Q-3(3-F) G-3(3-CF 3 ) Q-3(4-Br) G-1(4-F) Q-3(4-Br) G-1(5-F) Q-3(4-Br) G-3(3-F) Q-3(4-Br) G-3(3-Cl) Q-3(4-Br) G-3(3-CH 3 ) Q-3(4-Br) G-3(3-CF 3 ) Q-3(4-CF 3 ) G-1(5-F) Q-3(4-CH 3 ) G-1(4-F) Q-3(4-CH 3 ) G-1(5-F) Q-3(4-CH 3 ) G-3(3-F) Q-3(4-CH 3 ) G-3(3-Cl) Q-3(4-CH 3 ) G-3(3-CH 3 ) Q-3(4-CH 3 ) G-3(3-CF 3 ) Q-3(4-Cl) G-1(4-F) Q-3(4-Cl) G-1(5-F) Q-3(4-Cl) G-3(3-F) Q-3(4-Cl) G-3(3-Cl) Q-3(4-Cl) G-3(3-CH 3 ) Q-3(4-Cl) G-3(3-CF 3 ) Q-3(4-CN) G-1(5-F) Q-3(4-F) G-1(4-F) Q-3(4-F) G-1(5-F) Q-3(4-F) G-3(3-F) Q-3(4-F) G-3(3-Cl) Q-3(4-F) G-3(3-CH 3 ) Q-3(4-F) G-3(3-CF 3 ) Q-3(6-F) G-1(4-F) Q-3(6-F) G-1(5-F) Q-3(6-F) G-3(3-F) Q-3(6-F) G-3(3-Cl) Q-3(6-F) G-3(3-CH 3 ) Q-3(6-F) G-3(3-CF 3 ) Q-4 G-1(4-F) Q-4 G-1(5-F) Q-4 G-3(3-F) Q-4 G-3(3-Cl) Q-4 G-3(3-CH 3 ) Q-4 G-3(3-CF 3 ) Q-4(3-CH 3 ) G-1(5-F) Q-4(3-Cl) G-1(5-F) Q-4(4-Br) G-1(4-F) Q-4(4-Br) G-1(5-F) Q-4(4-Br) G-3(3-F) Q-4(4-Br) G-3(3-Cl) Q-4(4-Br) G-3(3-CH 3 ) Q-4(4-Br) G-3(3-CF 3 ) Q-4(4-Cl) G-1(4-F) Q-4(4-Cl) G-1(5-F) Q-4(4-Cl) G-3(3-F) Q-4(4-Cl) G-3(3-Cl) Q-4(4-Cl) G-3(3-CH 3 ) Q-4(4-Cl) G-3(3-CF 3 ) Q-6(4-Cl) G-1(4-F) Q-6(4-Cl) G-1(5-F) Q-6(4-Cl) G-3(3-F) Q-6(4-Cl) G-3(3-Cl) Q-6(4-Cl) G-3(3-CH 3 ) Q-6(4-Cl) G-3(3-CF 3 ) Q-9 G-1(4-F) Q-9 G-1(5-F) Q-9 G-3(3-F) Q-9 G-3(3-Cl) Q-9 G-3(3-CH 3 ) Q-9 G-3(3-CF 3 ) Q-12a G-1(5-F) ――――――――――― [Table 11]
[0149] [Chem.]
[0150] ―――――――――――――――― R 1 Q G ―――――――――――――――― CHF 2Q-1(3-F) G-1(4-F) CHF 2 Q-1(3-F) G-3(3-F) CHF 2 Q-1(3-F) G-3(3-Cl) CHF 2 Q-1(3-F) G-3(3-CH 3 ) CHF 2 Q-1(3-F) G-3(3-CF 3 ) CHF 2 Q-1(4-F) G-1(4-F) CHF 2 Q-1(4-F) G-3(3-F) CHF 2 Q-1(4-F) G-3(3-Cl) CHF 2 Q-1(4-F) G-3(3-CH 3 ) CHF 2 Q-1(4-F) G-3(3-CF 3 ) CHF 2 Q-1(4-CN) G-1(4-F) CHF 2 Q-1(4-CN) G-3(3-F) CHF 2 Q-1(4-CN) G-3(3-Cl) CHF 2 Q-1(4-CN) G-3(3-CH 3 ) CHF 2 Q-1(4-CN) G-3(3-CF 3 ) CHF 2 Q-1(4-CF 3 ) G-1(4-F) CHF 2 Q-1(4-CF 3 ) G-3(3-F) CHF 2 Q-1(4-CF 3 ) G-3(3-Cl) CHF 2 Q-1(4-CF 3 ) G-3(3-CH3 ) CHF 2 Q-1(4-CF 3 ) G-3(3-CF 3 ) CHF 2 Q-1(2-F,4-F) G-1(4-F) CHF 2 Q-1(2-F,4-F) G-3(3-F) CHF 2 Q-1(2-F,4-F) G-3(3-Cl) CHF 2 Q-1(2-F,4-F) G-3(3-CH 3 ) CHF 2 Q-1(2-F,4-F) G-3(3-CF 3 ) CHF 2 Q-1(3-F,4-F) G-1(4-F) CHF 2 Q-1(3-F,4-F) G-3(3-F) CHF 2 Q-1(3-F,4-F) G-3(3-Cl) CHF 2 Q-1(3-F,4-F) G-3(3-CH 3 ) CHF 2 Q-1(3-F,4-F) G-3(3-CF 3 ) CHF 2 Q-2(4-F) G-1(4-F) CHF 2 Q-2(4-F) G-3(3-F) CHF 2 Q-2(4-F) G-3(3-Cl) CHF 2 Q-2(4-F) G-3(3-CH 3 ) CHF 2 Q-2(4-F) G-3(3-CF 3 ) CHF 2 Q-3 G-1(4-F) CHF 2 Q-3 G-3(3-F) CHF2 Q-3 G-3(3-Cl) CHF 2 Q-3 G-3(3-CH 3 ) CHF 2 Q-3 G-3(3-CF 3 ) CHF 2 Q-3(4-F) G-1(4-F) CHF 2 Q-3(4-F) G-3(3-F) CHF 2 Q-3(4-F) G-3(3-Cl) CHF 2 Q-3(4-F) G-3(3-CH 3 ) CHF 2 Q-3(4-F) G-3(3-CF 3 ) CHF 2 Q-3(4-Cl) G-1(4-F) CHF 2 Q-3(4-Cl) G-3(3-F) CHF 2 Q-3(4-Cl) G-3(3-Cl) CHF 2 Q-3(4-Cl) G-3(3-CH 3 ) CHF 2 Q-3(4-Cl) G-3(3-CF 3 ) CHF 2 Q-3(4-CH 3 ) G-1(4-F) CHF 2 Q-3(4-CH 3 ) G-3(3-F) CHF 2 Q-3(4-CH 3 ) G-3(3-Cl) CHF 2 Q-3(4-CH 3 ) G-3(3-CH 3 ) CHF 2 Q-3(4-CH 3 ) G-3(3-CF 3 ) CHF 2 Q-3(3-CH 3 ) G-1(4-F) CHF 2 Q-3(3-CH 3 ) G-3(3-F) CHF 2 Q-3(3-CH 3 ) G-3(3-Cl) CHF 2 Q-3(3-CH 3 ) G-3(3-CH 3 ) CHF 2 Q-3(3-CH 3 ) G-3(3-CF 3 ) CHF 2 Q-3(3-OCH 3 ) G-1(4-F) CHF 2 Q-3(3-OCH 3 ) G-3(3-F) CHF 2 Q-3(3-OCH 3 ) G-3(3-Cl) CHF 2 Q-3(3-OCH 3 ) G-3(3-CH 3 ) CHF 2 Q-3(3-OCH 3 ) G-3(3-CF 3 ) CHF 2 Q-4 G-1(4-F) CHF 2 Q-4 G-3(3-F) CHF 2 Q-4 G-3(3-Cl) CHF 2 Q-4 G-3(3-CH 3 ) CHF 2 Q-4 G-3(3-CF 3 ) CHF 2 Q-4(4-CH 3 ) G-1(4-F) CHF 2 Q-4(4-CH 3) G-3(3-F) CHF 2 Q-4(4-CH 3 ) G-3(3-Cl) CHF 2 Q-4(4-CH 3 ) G-3(3-CH 3 ) CHF 2 Q-4(4-CH 3 ) G-3(3-CF 3 ) CHF 2 Q-4(3-CH 3 ) G-1(4-F) CHF 2 Q-4(3-CH 3 ) G-3(3-F) CHF 2 Q-4(3-CH 3 ) G-3(3-Cl) CHF 2 Q-4(3-CH 3 ) G-3(3-CH 3 ) CHF 2 Q-4(3-CH 3 ) G-3(3-CF 3 ) CHF 2 Q-9 G-1(4-F) CHF 2 Q-9 G-3(3-F) CHF 2 Q-9 G-3(3-Cl) CHF 2 Q-9 G-3(3-CH 3 ) CHF 2 Q-9 G-3(3-CF 3 ) CHF 2 Q-12a G-1(4-F) CHF 2 Q-12a G-3(3-F) CHF 2 Q-12a G-3(3-Cl) CHF 2 Q-12a G-3(3-CH 3 ) CHF 2Q-12a G-3(3-CF 3 ) CF 3 Q-1(3-F) G-1(4-F) CF 3 Q-1(3-F) G-3(3-F) CF 3 Q-1(3-F) G-3(3-Cl) CF 3 Q-1(3-F) G-3(3-CH 3 ) CF 3 Q-1(3-F) G-3(3-CF 3 ) CF 3 Q-1(4-F) G-1(4-F) CF 3 Q-1(4-F) G-3(3-F) CF 3 Q-1(4-F) G-3(3-Cl) CF 3 Q-1(4-F) G-3(3-CH 3 ) CF 3 Q-1(4-F) G-3(3-CF 3 ) CF 3 Q-1(4-CN) G-1(4-F) CF 3 Q-1(4-CN) G-3(3-F) CF 3 Q-1(4-CN) G-3(3-Cl) CF 3 Q-1(4-CN) G-3(3-CH 3 ) CF 3 Q-1(4-CN) G-3(3-CF 3 ) CF 3 Q-1(4-CF 3 ) G-1(4-F) CF 3 Q-1(4-CF 3 ) G-3(3-F) CF 3 Q-1(4-CF 3 ) G-3(3-Cl) CF 3Q-1(4-CF 3 ) G-3(3-CH 3 ) CF 3 Q-1(4-CF 3 ) G-3(3-CF 3 ) CF 3 Q-1(2-F,4-F) G-1(4-F) CF 3 Q-1(2-F,4-F) G-3(3-F) CF 3 Q-1(2-F,4-F) G-3(3-Cl) CF 3 Q-1(2-F,4-F) G-3(3-CH 3 ) CF 3 Q-1(2-F,4-F) G-3(3-CF 3 ) CF 3 Q-1(3-F,4-F) G-1(4-F) CF 3 Q-1(3-F,4-F) G-3(3-F) CF 3 Q-1(3-F,4-F) G-3(3-Cl) CF 3 Q-1(3-F,4-F) G-3(3-CH 3 ) CF 3 Q-1(3-F,4-F) G-3(3-CF 3 ) CF 3 Q-2(4-F) G-1(4-F) CF 3 Q-2(4-F) G-3(3-F) CF 3 Q-2(4-F) G-3(3-Cl) CF 3 Q-2(4-F) G-3(3-CH 3 ) CF 3 Q-2(4-F) G-3(3-CF 3 ) CF 3 Q-3 G-1(4-F) CF 3 Q-3 G-3(3-F) CF 3 Q-3 G-3(3-Cl) CF 3 Q-3 G-3(3-CH 3 ) CF 3 Q-3 G-3(3-CF 3 ) CF 3 Q-3(4-F) G-1(4-F) CF 3 Q-3(4-F) G-3(3-F) CF 3 Q-3(4-F) G-3(3-Cl) CF 3 Q-3(4-F) G-3(3-CH 3 ) CF 3 Q-3(4-F) G-3(3-CF 3 ) CF 3 Q-3(4-Cl) G-1(4-F) CF 3 Q-3(4-Cl) G-3(3-F) CF 3 Q-3(4-Cl) G-3(3-Cl) CF 3 Q-3(4-Cl) G-3(3-CH 3 ) CF 3 Q-3(4-Cl) G-3(3-CF 3 ) CF 3 Q-3(4-CH 3 ) G-1(4-F) CF 3 Q-3(4-CH 3 ) G-3(3-F) CF 3 Q-3(4-CH 3 ) G-3(3-Cl) CF 3 Q-3(4-CH 3 ) G-3(3-CH 3 ) CF 3 Q-3(4-CH 3 ) G-3(3-CF 3 ) CF3 Q-3(3-CH 3 ) G-1(4-F) CF 3 Q-3(3-CH 3 ) G-3(3-F) CF 3 Q-3(3-CH 3 ) G-3(3-Cl) CF 3 Q-3(3-CH 3 ) G-3(3-CH 3 ) CF 3 Q-3(3-CH 3 ) G-3(3-CF 3 ) CF 3 Q-3(3-OCH 3 ) G-1(4-F) CF 3 Q-3(3-OCH 3 ) G-3(3-F) CF 3 Q-3(3-OCH 3 ) G-3(3-Cl) CF 3 Q-3(3-OCH 3 ) G-3(3-CH 3 ) CF 3 Q-3(3-OCH 3 ) G-3(3-CF 3 ) CF 3 Q-4 G-1(4-F) CF 3 Q-4 G-3(3-F) CF 3 Q-4 G-3(3-Cl) CF 3 Q-4 G-3(3-CH 3 ) CF 3 Q-4 G-3(3-CF 3 ) CF 3 Q-4(4-CH 3 ) G-1(4-F) CF 3 Q-4(4-CH 3 ) G-3(3-F) CF3 Q-4(4-CH 3 ) G-3(3-Cl) CF 3 Q-4(4-CH 3 ) G-3(3-CH 3 ) CF 3 Q-4(4-CH 3 ) G-3(3-CF 3 ) CF 3 Q-4(3-CH 3 ) G-1(4-F) CF 3 Q-4(3-CH 3 ) G-3(3-F) CF 3 Q-4(3-CH 3 ) G-3(3-Cl) CF 3 Q-4(3-CH 3 ) G-3(3-CH 3 ) CF 3 Q-4(3-CH 3 ) G-3(3-CF 3 ) CF 3 Q-9 G-1(4-F) CF 3 Q-9 G-3(3-F) CF 3 Q-9 G-3(3-Cl) CF 3 Q-9 G-3(3-CH 3 ) CF 3 Q-9 G-3(3-CF 3 ) CF 3 Q-12a G-1(4-F) CF 3 Q-12a G-3(3-F) CF 3 Q-12a G-3(3-Cl) CF 3 Q-12a G-3(3-CH 3 ) CF 3 Q-12a G-3(3-CF 3 ) CF3 Q-1(4-F) G-1(4-NO 2 ) CF 3 Q-1(4-F) G-1(4-NH 2 ) CF 3 Q-1(4-F) G-1(5-F) CF 3 Q-1(4-F) G-1(5-NO 2 ) CF 3 Q-1(4-F) G-1(5-NH 2 ) CF 3 Q-1(4-F) G-3(3-NO 2 ) CF 3 Q-1(4-F) G-3(3-NH 2 ) CF 3 Q-1(4-CN) G-1(4-NO 2 ) CF 3 Q-1(4-CN) G-1(4-NH 2 ) CF 3 Q-1(4-CN) G-1(5-F) CF 3 Q-1(4-CN) G-1(5-NO 2 ) CF 3 Q-1(4-CN) G-1(5-NH 2 ) CF 3 Q-1(4-CN) G-3(3-NO 2 ) CF 3 Q-1(4-CN) G-3(3-NH 2 ) CF 3 Q-2(4-F) G-1(4-NO 2 ) CF 3 Q-2(4-F) G-1(4-NH 2 ) CF 3 Q-2(4-F) G-1(5-F) CF 3 Q-2(4-F) G-1(5-NO2 ) CF 3 Q-2(4-F) G-1(5-NH 2 ) CF 3 Q-2(4-F) G-3(3-NO 2 ) CF 3 Q-2(4-F) G-3(3-NH 2 ) CF 3 Q-2(4-Cl) G-1(4-F) CF 3 Q-2(4-Cl) G-1(4-NO 2 ) CF 3 Q-2(4-Cl) G-1(4-NH 2 ) CF 3 Q-2(4-Cl) G-1(5-F) CF 3 Q-2(4-Cl) G-1(5-NO 2 ) CF 3 Q-2(4-Cl) G-1(5-NH 2 ) CF 3 Q-2(4-Cl) G-3(3-F) CF 3 Q-2(4-Cl) G-3(3-Cl) CF 3 Q-2(4-Cl) G-3(3-CH 3 ) CF 3 Q-2(4-Cl) G-3(3-CF 3 ) CF 3 Q-2(4-Cl) G-3(3-NO 2 ) CF 3 Q-2(4-Cl) G-3(3-NH 2 ) CF 3 Q-2(4-CN) G-1(4-F) CF 3 Q-2(4-CN) G-1(4-NO 2 ) CF 3Q-2(4-CN) G-1(4-NH 2 ) CF 3 Q-2(4-CN) G-1(5-F) CF 3 Q-2(4-CN) G-1(5-NO 2 ) CF 3 Q-2(4-CN) G-1(5-NH 2 ) CF 3 Q-2(4-CN) G-3(3-F) CF 3 Q-2(4-CN) G-3(3-Cl) CF 3 Q-2(4-CN) G-3(3-CH 3 ) CF 3 Q-2(4-CN) G-3(3-CF 3 ) CF 3 Q-2(4-CN) G-3(3-NO 2 ) CF 3 Q-2(4-CN) G-3(3-NH 2 ) CF 3 Q-3 G-1(4-NO 2 ) CF 3 Q-3 G-1(4-NH 2 ) CF 3 Q-3 G-1(5-F) CF 3 Q-3 G-1(5-NO 2 ) CF 3 Q-3 G-1(5-NH 2 ) CF 3 Q-3 G-3(3-NO 2 ) CF 3 Q-3 G-3(3-NH 2 ) CF 3 Q-3(3-CH 3 ) G-1(4-NO 2 ) CF 3Q-3(3-CH 3 ) G-1(4-NH 2 ) CF 3 Q-3(3-CH 3 ) G-1(5-F) CF 3 Q-3(3-CH 3 ) G-1(5-NO 2 ) CF 3 Q-3(3-CH 3 ) G-1(5-NH 2 ) CF 3 Q-3(3-CH 3 ) G-3(3-NO 2 ) CF 3 Q-3(3-CH 3 ) G-3(3-NH 2 ) CF 3 Q-3(3-Cl) G-1(4-F) CF 3 Q-3(3-Cl) G-1(4-NO 2 ) CF 3 Q-3(3-Cl) G-1(4-NH 2 ) CF 3 Q-3(3-Cl) G-1(5-F) CF 3 Q-3(3-Cl) G-1(5-NO 2 ) CF 3 Q-3(3-Cl) G-1(5-NH 2 ) CF 3 Q-3(3-Cl) G-3(3-F) CF 3 Q-3(3-Cl) G-3(3-Cl) CF 3 Q-3(3-Cl) G-3(3-CH 3 ) CF 3 Q-3(3-Cl) G-3(3-CF 3 ) CF 3 Q-3(3-Cl) G-3(3-NO 2 ) CF 3 Q-3(3-Cl) G-3(3-NH 2 ) CF 3 Q-3(3-F) G-1(4-F) CF 3 Q-3(3-F) G-1(4-NO 2 ) CF 3 Q-3(3-F) G-1(4-NH 2 ) CF 3 Q-3(3-F) G-1(5-F) CF 3 Q-3(3-F) G-1(5-NO 2 ) CF 3 Q-3(3-F) G-1(5-NH 2 ) CF 3 Q-3(3-F) G-3(3-F) CF 3 Q-3(3-F) G-3(3-Cl) CF 3 Q-3(3-F) G-3(3-CH 3 ) CF 3 Q-3(3-F) G-3(3-CF 3 ) CF 3 Q-3(3-F) G-3(3-NO 2 ) CF 3 Q-3(3-F) G-3(3-NH 2 ) CF 3 Q-3(4-Br) G-1(4-F) CF 3 Q-3(4-Br) G-1(4-NO 2 ) CF 3 Q-3(4-Br) G-1(4-NH 2 ) CF 3 Q-3(4-Br) G-1(5-F) CF 3 Q-3(4-Br) G-1(5-NO 2 ) CF3 Q-3(4-Br) G-1(5-NH 2 ) CF 3 Q-3(4-Br) G-3(3-F) CF 3 Q-3(4-Br) G-3(3-Cl) CF 3 Q-3(4-Br) G-3(3-CH 3 ) CF 3 Q-3(4-Br) G-3(3-CF 3 ) CF 3 Q-3(4-Br) G-3(3-NO 2 ) CF 3 Q-3(4-Br) G-3(3-NH 2 ) CF 3 Q-3(4-CH 3 ) G-1(4-NO 2 ) CF 3 Q-3(4-CH 3 ) G-1(4-NH 2 ) CF 3 Q-3(4-CH 3 ) G-1(5-F) CF 3 Q-3(4-CH 3 ) G-1(5-NO 2 ) CF 3 Q-3(4-CH 3 ) G-1(5-NH 2 ) CF 3 Q-3(4-CH 3 ) G-3(3-NO 2 ) CF 3 Q-3(4-CH 3 ) G-3(3-NH 2 ) CF 3 Q-3(4-Cl) G-1(4-NO 2 ) CF 3 Q-3(4-Cl) G-1(4-NH 2 ) CF 3 Q-3(4-Cl) G-1(5-F) CF 3 Q-3(4-Cl) G-1(5-NO 2 ) CF 3 Q-3(4-Cl) G-1(5-NH 2 ) CF 3 Q-3(4-Cl) G-3(3-NO 2 ) CF 3 Q-3(4-Cl) G-3(3-NH 2 ) CF 3 Q-3(4-CN) G-1(4-F) CF 3 Q-3(4-CN) G-1(4-NO 2 ) CF 3 Q-3(4-CN) G-1(4-NH 2 ) CF 3 Q-3(4-CN) G-1(5-F) CF 3 Q-3(4-CN) G-1(5-NO 2 ) CF 3 Q-3(4-CN) G-1(5-NH 2 ) CF 3 Q-3(4-CN) G-3(3-F) CF 3 Q-3(4-CN) G-3(3-Cl) CF 3 Q-3(4-CN) G-3(3-CH 3 ) CF 3 Q-3(4-CN) G-3(3-CF 3 ) CF 3 Q-3(4-CN) G-3(3-NO 2 ) CF 3 Q-3(4-CN) G-3(3-NH 2 ) CF 3 Q-3(4-F) G-1(4-NO2 ) CF 3 Q-3(4-F) G-1(4-NH 2 ) CF 3 Q-3(4-F) G-1(5-F) CF 3 Q-3(4-F) G-1(5-NO 2 ) CF 3 Q-3(4-F) G-1(5-NH 2 ) CF 3 Q-3(4-F) G-3(3-NO 2 ) CF 3 Q-3(4-F) G-3(3-NH 2 ) CF 3 Q-3(6-F) G-1(4-F) CF 3 Q-3(6-F) G-1(4-NO 2 ) CF 3 Q-3(6-F) G-1(4-NH 2 ) CF 3 Q-3(6-F) G-1(5-F) CF 3 Q-3(6-F) G-1(5-NO 2 ) CF 3 Q-3(6-F) G-1(5-NH 2 ) CF 3 Q-3(6-F) G-3(3-F) CF 3 Q-3(6-F) G-3(3-Cl) CF 3 Q-3(6-F) G-3(3-CH 3 ) CF 3 Q-3(6-F) G-3(3-CF 3 ) CF 3 Q-3(6-F) G-3(3-NO 2 ) CF 3 Q-3(6-F) G-3(3-NH2 ) CF 3 Q-4 G-1(4-NO 2 ) CF 3 Q-4 G-1(4-NH 2 ) CF 3 Q-4 G-1(5-F) CF 3 Q-4 G-1(5-NO 2 ) CF 3 Q-4 G-1(5-NH 2 ) CF 3 Q-4 G-3(3-NO 2 ) CF 3 Q-4 G-3(3-NH 2 ) CF 3 Q-4(3-CH 3 ) G-1(4-NO 2 ) CF 3 Q-4(3-CH 3 ) G-1(4-NH 2 ) CF 3 Q-4(3-CH 3 ) G-1(5-F) CF 3 Q-4(3-CH 3 ) G-1(5-NO 2 ) CF 3 Q-4(3-CH 3 ) G-1(5-NH 2 ) CF 3 Q-4(3-CH 3 ) G-3(3-NO 2 ) CF 3 Q-4(3-CH 3 ) G-3(3-NH 2 ) CF 3 Q-4(3-Cl) G-1(4-F) CF 3 Q-4(3-Cl) G-1(4-NO 2 ) CF3 Q-4(3-Cl) G-1(4-NH 2 ) CF 3 Q-4(3-Cl) G-1(5-F) CF 3 Q-4(3-Cl) G-1(5-NO 2 ) CF 3 Q-4(3-Cl) G-1(5-NH 2 ) CF 3 Q-4(3-Cl) G-3(3-F) CF 3 Q-4(3-Cl) G-3(3-Cl) CF 3 Q-4(3-Cl) G-3(3-CH 3 ) CF 3 Q-4(3-Cl) G-3(3-CF 3 ) CF 3 Q-4(3-Cl) G-3(3-NO 2 ) CF 3 Q-4(3-Cl) G-3(3-NH 2 ) CF 3 Q-4(4-Br) G-1(4-F) CF 3 Q-4(4-Br) G-1(4-NO 2 ) CF 3 Q-4(4-Br) G-1(4-NH 2 ) CF 3 Q-4(4-Br) G-1(5-F) CF 3 Q-4(4-Br) G-1(5-NO 2 ) CF 3 Q-4(4-Br) G-1(5-NH 2 ) CF 3 Q-4(4-Br) G-3(3-F) CF 3 Q-4(4-Br) G-3(3-Cl) CF 3Q-4(4-Br) G-3(3-CH 3 ) CF 3 Q-4(4-Br) G-3(3-CF 3 ) CF 3 Q-4(4-Br) G-3(3-NO 2 ) CF 3 Q-4(4-Br) G-3(3-NH 2 ) CF 3 Q-4(4-Cl) G-1(4-F) CF 3 Q-4(4-Cl) G-1(4-NO 2 ) CF 3 Q-4(4-Cl) G-1(4-NH 2 ) CF 3 Q-4(4-Cl) G-1(5-F) CF 3 Q-4(4-Cl) G-1(5-NO 2 ) CF 3 Q-4(4-Cl) G-1(5-NH 2 ) CF 3 Q-4(4-Cl) G-3(3-F) CF 3 Q-4(4-Cl) G-3(3-Cl) CF 3 Q-4(4-Cl) G-3(3-CH 3 ) CF 3 Q-4(4-Cl) G-3(3-CF 3 ) CF 3 Q-4(4-Cl) G-3(3-NO 2 ) CF 3 Q-4(4-Cl) G-3(3-NH 2 ) CF 3 Q-9 G-1(4-NO 2 ) CF 3 Q-9 G-1(4-NH 2 ) CF3 Q-9 G-1(5-F) CF 3 Q-9 G-1(5-NO 2 ) CF 3 Q-9 G-1(5-NH 2 ) CF 3 Q-9 G-3(3-NO 2 ) CF 3 Q-9 G-3(3-NH 2 ) CF 3 Q-12a G-1(4-NO 2 ) CF 3 Q-12a G-1(4-NH 2 ) CF 3 Q-12a G-1(5-F) CF 3 Q-12a G-1(5-NO 2 ) CF 3 Q-12a G-1(5-NH 2 ) CF 3 Q-12a G-3(3-NO 2 ) CF 3 Q-12a G-3(3-NH 2 ) Cl Q-1(4-F) G-1(4-F) Cl Q-1(4-F) G-1(4-NO 2 ) Cl Q-1(4-F) G-1(4-NH 2 ) Cl Q-1(4-F) G-1(5-F) Cl Q-1(4-F) G-1(5-NO 2 ) Cl Q-1(4-F) G-1(5-NH 2 ) Cl Q-1(4-F) G-3(3-F) Cl Q-1(4-F) G-3(3-Cl) Cl Q-1(4-F) G-3(3-CH 3 ) Cl Q-1(4-F) G-3(3-CF 3 ) Cl Q-1(4-F) G-3(3-NO 2 ) Cl Q-1(4-F) G-3(3-NH 2 ) Cl Q-1(4-CN) G-1(4-F) Cl Q-1(4-CN) G-1(4-NO 2 ) Cl Q-1(4-CN) G-1(4-NH 2 ) Cl Q-1(4-CN) G-1(5-F) Cl Q-1(4-CN) G-1(5-NO 2 ) Cl Q-1(4-CN) G-1(5-NH 2 ) Cl Q-1(4-CN) G-3(3-F) Cl Q-1(4-CN) G-3(3-Cl) Cl Q-1(4-CN) G-3(3-CH 3 ) Cl Q-1(4-CN) G-3(3-CF 3 ) Cl Q-1(4-CN) G-3(3-NO 2 ) Cl Q-1(4-CN) G-3(3-NH 2 ) Cl Q-2(4-F) G-1(4-F) Cl Q-2(4-F) G-1(4-NO 2 ) Cl Q-2(4-F) G-1(4-NH 2 ) Cl Q-2(4-F) G-1(5-F) Cl Q-2(4-F) G-1(5-NO 2 ) Cl Q-2(4-F) G-1(5-NH 2 ) Cl Q-2(4-F) G-3(3-F) Cl Q-2(4-F) G-3(3-Cl) Cl Q-2(4-F) G-3(3-CH 3 ) Cl Q-2(4-F) G-3(3-CF 3 ) Cl Q-2(4-F) G-3(3-NO 2 ) Cl Q-2(4-F) G-3(3-NH 2 ) Cl Q-2(4-Cl) G-1(4-F) Cl Q-2(4-Cl) G-1(4-NO 2 ) Cl Q-2(4-Cl) G-1(4-NH 2 ) Cl Q-2(4-Cl) G-1(5-F) Cl Q-2(4-Cl) G-1(5-NO 2 ) Cl Q-2(4-Cl) G-1(5-NH 2 ) Cl Q-2(4-Cl) G-3(3-F) Cl Q-2(4-Cl) G-3(3-Cl) Cl Q-2(4-Cl) G-3(3-CH 3 ) Cl Q-2(4-Cl) G-3(3-CF 3 ) Cl Q-2(4-Cl) G-3(3-NO 2 ) Cl Q-2(4-Cl) G-3(3-NH 2 ) Cl Q-2(4-CN) G-1(4-F) Cl Q-2(4-CN) G-1(4-NO 2 ) Cl Q-2(4-CN) G-1(4-NH 2 ) Cl Q-2(4-CN) G-1(5-F) Cl Q-2(4-CN) G-1(5-NO 2 ) Cl Q-2(4-CN) G-1(5-NH 2 ) Cl Q-2(4-CN) G-3(3-F) Cl Q-2(4-CN) G-3(3-Cl) Cl Q-2(4-CN) G-3(3-CH 3 ) Cl Q-2(4-CN) G-3(3-CF 3 ) Cl Q-2(4-CN) G-3(3-NO 2 ) Cl Q-2(4-CN) G-3(3-NH 2 ) Cl Q-3 G-1(4-F) Cl Q-3 G-1(4-NO 2 ) Cl Q-3 G-1(4-NH 2 ) Cl Q-3 G-1(5-F) Cl Q-3 G-1(5-NO 2 ) Cl Q-3 G-1(5-NH 2 ) Cl Q-3 G-3(3-F) Cl Q-3 G-3(3-Cl) Cl Q-3 G-3(3-CH 3 ) Cl Q-3 G-3(3-CF 3 ) Cl Q-3 G-3(3-NO 2 ) Cl Q-3 G-3(3-NH 2 ) Cl Q-3(3-CH 3 ) G-1(4-F) Cl Q-3(3-CH 3 ) G-1(4-NO 2 ) Cl Q-3(3-CH 3 ) G-1(4-NH 2 ) Cl Q-3(3-CH 3 ) G-1(5-F) Cl Q-3(3-CH 3 ) G-1(5-NO 2 ) Cl Q-3(3-CH 3 ) G-1(5-NH 2 ) Cl Q-3(3-CH 3 ) G-3(3-F) Cl Q-3(3-CH 3 ) G-3(3-Cl) Cl Q-3(3-CH 3 ) G-3(3-CH 3 ) Cl Q-3(3-CH 3 ) G-3(3-CF 3 ) Cl Q-3(3-CH 3 ) G-3(3-NO 2 ) Cl Q-3(3-CH 3 ) G-3(3-NH 2 ) Cl Q-3(3-Cl) G-1(4-F) Cl Q-3(3-Cl) G-1(4-NO 2 ) Cl Q-3(3-Cl) G-1(4-NH 2 ) Cl Q-3(3-Cl) G-1(5-F) Cl Q-3(3-Cl) G-1(5-NO 2 ) Cl Q-3(3-Cl) G-1(5-NH 2 ) Cl Q-3(3-Cl) G-3(3-F) Cl Q-3(3-Cl) G-3(3-Cl) Cl Q-3(3-Cl) G-3(3-CH 3 ) Cl Q-3(3-Cl) G-3(3-CF 3 ) Cl Q-3(3-Cl) G-3(3-NO 2 ) Cl Q-3(3-Cl) G-3(3-NH 2 ) Cl Q-3(3-F) G-1(4-F) Cl Q-3(3-F) G-1(4-NO 2 ) Cl Q-3(3-F) G-1(4-NH 2 ) Cl Q-3(3-F) G-1(5-F) Cl Q-3(3-F) G-1(5-NO 2 ) Cl Q-3(3-F) G-1(5-NH 2 ) Cl Q-3(3-F) G-3(3-F) Cl Q-3(3-F) G-3(3-Cl) Cl Q-3(3-F) G-3(3-CH 3 ) Cl Q-3(3-F) G-3(3-CF 3 ) Cl Q-3(3-F) G-3(3-NO 2 ) Cl Q-3(3-F) G-3(3-NH 2 ) Cl Q-3(4-Br) G-1(4-F) Cl Q-3(4-Br) G-1(4-NO 2 ) Cl Q-3(4-Br) G-1(4-NH 2 ) Cl Q-3(4-Br) G-1(5-F) Cl Q-3(4-Br) G-1(5-NO 2 ) Cl Q-3(4-Br) G-1(5-NH 2 ) Cl Q-3(4-Br) G-3(3-F) Cl Q-3(4-Br) G-3(3-Cl) Cl Q-3(4-Br) G-3(3-CH 3 ) Cl Q-3(4-Br) G-3(3-CF 3 ) Cl Q-3(4-Br) G-3(3-NO 2 ) Cl Q-3(4-Br) G-3(3-NH 2 ) Cl Q-3(4-CH 3 ) G-1(4-F) Cl Q-3(4-CH 3 ) G-1(4-NO 2 ) Cl Q-3(4-CH 3 ) G-1(4-NH 2 ) Cl Q-3(4-CH 3 ) G-1(5-F) Cl Q-3(4-CH 3 ) G-1(5-NO 2 ) Cl Q-3(4-CH 3 ) G-1(5-NH 2 ) Cl Q-3(4-CH 3 ) G-3(3-F) Cl Q-3(4-CH 3 ) G-3(3-Cl) Cl Q-3(4-CH 3 ) G-3(3-CH 3 ) Cl Q-3(4-CH 3 ) G-3(3-CF 3 ) Cl Q-3(4-CH 3 ) G-3(3-NO 2 ) Cl Q-3(4-CH 3 ) G-3(3-NH 2 ) Cl Q-3(4-Cl) G-1(4-F) Cl Q-3(4-Cl) G-1(4-NO 2 ) Cl Q-3(4-Cl) G-1(4-NH 2 ) Cl Q-3(4-Cl) G-1(5-F) Cl Q-3(4-Cl) G-1(5-NO 2 ) Cl Q-3(4-Cl) G-1(5-NH 2 ) Cl Q-3(4-Cl) G-3(3-F) Cl Q-3(4-Cl) G-3(3-Cl) Cl Q-3(4-Cl) G-3(3-CH 3 ) Cl Q-3(4-Cl) G-3(3-CF 3 ) Cl Q-3(4-Cl) G-3(3-NO 2 ) Cl Q-3(4-Cl) G-3(3-NH 2 ) Cl Q-3(4-CN) G-1(4-F) Cl Q-3(4-CN) G-1(4-NO 2 ) Cl Q-3(4-CN) G-1(4-NH 2 ) Cl Q-3(4-CN) G-1(5-F) Cl Q-3(4-CN) G-1(5-NO 2 ) Cl Q-3(4-CN) G-1(5-NH 2 ) Cl Q-3(4-CN) G-3(3-F) Cl Q-3(4-CN) G-3(3-Cl) Cl Q-3(4-CN) G-3(3-CH 3 ) Cl Q-3(4-CN) G-3(3-CF 3 ) Cl Q-3(4-CN) G-3(3-NO 2 ) Cl Q-3(4-CN) G-3(3-NH 2 ) Cl Q-3(4-F) G-1(4-F) Cl Q-3(4-F) G-1(4-NO 2 ) Cl Q-3(4-F) G-1(4-NH 2 ) Cl Q-3(4-F) G-1(5-F) Cl Q-3(4-F) G-1(5-NO 2 ) Cl Q-3(4-F) G-1(5-NH 2 ) Cl Q-3(4-F) G-3(3-F) Cl Q-3(4-F) G-3(3-Cl) Cl Q-3(4-F) G-3(3-CH 3 ) Cl Q-3(4-F) G-3(3-CF 3 ) Cl Q-3(4-F) G-3(3-NO 2 ) Cl Q-3(4-F) G-3(3-NH 2 ) Cl Q-3(6-F) G-1(4-F) Cl Q-3(6-F) G-1(4-NO 2 ) Cl Q-3(6-F) G-1(4-NH 2 ) Cl Q-3(6-F) G-1(5-F) Cl Q-3(6-F) G-1(5-NO 2 ) Cl Q-3(6-F) G-1(5-NH 2 ) Cl Q-3(6-F) G-3(3-F) Cl Q-3(6-F) G-3(3-Cl) Cl Q-3(6-F) G-3(3-CH 3 ) Cl Q-3(6-F) G-3(3-CF 3 ) Cl Q-3(6-F) G-3(3-NO 2 ) Cl Q-3(6-F) G-3(3-NH 2 ) Cl Q-4 G-1(4-F) Cl Q-4 G-1(4-NO 2 ) Cl Q-4 G-1(4-NH 2 ) Cl Q-4 G-1(5-F) Cl Q-4 G-1(5-NO 2 ) Cl Q-4 G-1(5-NH 2 ) Cl Q-4 G-3(3-F) Cl Q-4 G-3(3-Cl) Cl Q-4 G-3(3-CH 3 ) Cl Q-4 G-3(3-CF 3) Cl Q-4 G-3(3-NO 2 ) Cl Q-4 G-3(3-NH 2 ) Cl Q-4(3-CH 3 ) G-1(4-F) Cl Q-4(3-CH 3 ) G-1(4-NO 2 ) Cl Q-4(3-CH 3 ) G-1(4-NH 2 ) Cl Q-4(3-CH 3 ) G-1(5-F) Cl Q-4(3-CH 3 ) G-1(5-NO 2 ) Cl Q-4(3-CH 3 ) G-1(5-NH 2 ) Cl Q-4(3-CH 3 ) G-3(3-F) Cl Q-4(3-CH 3 ) G-3(3-Cl) Cl Q-4(3-CH 3 ) G-3(3-CH 3 ) Cl Q-4(3-CH 3 ) G-3(3-CF 3 ) Cl Q-4(3-CH 3 ) G-3(3-NO 2 ) Cl Q-4(3-CH 3 ) G-3(3-NH 2 ) Cl Q-4(3-Cl) G-1(4-F) Cl Q-4(3-Cl) G-1(4-NO 2 ) Cl Q-4(3-Cl) G-1(4-NH 2 ) Cl Q-4(3-Cl) G-1(5-F) Cl Q-4(3-Cl) G-1(5-NO 2 ) Cl Q-4(3-Cl) G-1(5-NH 2 ) Cl Q-4(3-Cl) G-3(3-F) Cl Q-4(3-Cl) G-3(3-Cl) Cl Q-4(3-Cl) G-3(3-CH 3 ) Cl Q-4(3-Cl) G-3(3-CF 3 ) Cl Q-4(3-Cl) G-3(3-NO 2 ) Cl Q-4(3-Cl) G-3(3-NH 2 ) Cl Q-4(4-Br) G-1(4-F) Cl Q-4(4-Br) G-1(4-NO 2 ) Cl Q-4(4-Br) G-1(4-NH 2 ) Cl Q-4(4-Br) G-1(5-F) Cl Q-4(4-Br) G-1(5-NO 2 ) Cl Q-4(4-Br) G-1(5-NH 2 ) Cl Q-4(4-Br) G-3(3-F) Cl Q-4(4-Br) G-3(3-Cl) Cl Q-4(4-Br) G-3(3-CH 3 ) Cl Q-4(4-Br) G-3(3-CF 3 ) Cl Q-4(4-Br) G-3(3-NO 2 ) Cl Q-4(4-Br) G-3(3-NH 2 ) Cl Q-4(4-Cl) G-1(4-F) Cl Q-4(4-Cl) G-1(4-NO 2 ) Cl Q-4(4-Cl) G-1(4-NH 2 ) Cl Q-4(4-Cl) G-1(5-F) Cl Q-4(4-Cl) G-1(5-NO 2 ) Cl Q-4(4-Cl) G-1(5-NH 2 ) Cl Q-4(4-Cl) G-3(3-F) Cl Q-4(4-Cl) G-3(3-Cl) Cl Q-4(4-Cl) G-3(3-CH 3 ) Cl Q-4(4-Cl) G-3(3-CF 3 ) Cl Q-4(4-Cl) G-3(3-NO 2 ) Cl Q-4(4-Cl) G-3(3-NH 2 ) Cl Q-9 G-1(4-F) Cl Q-9 G-1(4-NO 2 ) Cl Q-9 G-1(4-NH 2 ) Cl Q-9 G-1(5-F) Cl Q-9 G-1(5-NO 2 ) Cl Q-9 G-1(5-NH 2 ) Cl Q-9 G-3(3-F) Cl Q-9 G-3(3-Cl) Cl Q-9 G-3(3-CH 3 ) Cl Q-9 G-3(3-CF 3 ) Cl Q-9 G-3(3-NO 2 ) Cl Q-9 G-3(3-NH 2 ) Cl Q-12a G-1(4-F) Cl Q-12a G-1(4-NO 2 ) Cl Q-12a G-1(4-NH 2 ) Cl Q-12a G-1(5-F) Cl Q-12a G-1(5-NO 2 ) Cl Q-12a G-1(5-NH 2 ) Cl Q-12a G-3(3-F) Cl Q-12a G-3(3-Cl) Cl Q-12a G-3(3-CH 3 ) Cl Q-12a G-3(3-CF 3 ) Cl Q-12a G-3(3-NO 2 ) Cl Q-12a G-3(3-NH 2 ) ―――――――――――――――― [Table 12]
[0151]
Chem.
[0152] ――――――――――― Q G ――――――――――― Q-3(3-Cl) G-1(4-F) Q-3(3-Cl) G-1(2-F) Q-3(3-Cl) G-1(2-Cl) Q-3(3-Cl) G-3(3-F) Q-3(3-Cl) G-3(3-Cl) Q-3(3-Cl) G-3(3-CH 3 ) Q-3(3-Cl) G-3(3-CF 3 ) Q-3(3-CH 3 ) G-1(4-F) Q-3(3-CH 3 ) G-1(2-F) Q-3(3-CH 3 ) G-1(2-Cl) Q-3(3-CH 3 ) G-3(3-F) Q-3(3-CH 3 ) G-3(3-Cl) Q-3(3-CH 3) G-3(3-CH 3 ) Q-3(3-CH 3 ) G-3(3-CF 3 ) Q-4(3-Cl) G-1(4-F) Q-4(3-Cl) G-1(2-F) Q-4(3-Cl) G-1(2-Cl) Q-4(3-Cl) G-3(3-F) Q-4(3-Cl) G-3(3-Cl) Q-4(3-Cl) G-3(3-CH 3 ) Q-4(3-Cl) G-3(3-CF 3 ) Q-4(3-CH 3 ) G-1(4-F) Q-4(3-CH 3 ) G-1(2-F) Q-4(3-CH 3 ) G-1(2-Cl) Q-4(3-CH 3 ) G-3(3-F) Q-4(3-CH 3 ) G-3(3-Cl) Q-4(3-CH 3 ) G-3(3-CH 3 ) Q-4(3-CH 3 ) G-3(3-CF 3 ) Q-4(4-CH 3 ) G-1(4-F) Q-4(4-CH 3 ) G-1(2-F) Q-4(4-CH 3 ) G-1(2-Cl) Q-4(4-CH 3 ) G-3(3-F) Q-4(4-CH 3 ) G-3(3-Cl) Q-4(4-CH 3 ) G-3(3-CH 3 ) Q-4(4-CH 3 ) G-3(3-CF3 ) Q-4(3-Br) G-1(4-F) Q-4(3-Br) G-1(2-F) Q-4(3-Br) G-1(2-Cl) Q-4(3-Br) G-3(3-F) Q-4(3-Br) G-3(3-Cl) Q-4(3-Br) G-3(3-CH 3 ) Q-4(3-Br) G-3(3-CF 3 ) Q-10(3-CH 3 ) G-1(4-F) Q-10(3-CH 3 ) G-1(2-F) Q-10(3-CH 3 ) G-1(2-Cl) Q-10(3-CH 3 ) G-3(3-F) Q-10(3-CH 3 ) G-3(3-Cl) Q-10(3-CH 3 ) G-3(3-CH 3 ) Q-10(3-CH 3 ) G-3(3-CF 3 ) Q-12a G-1(4-F) Q-12a G-1(2-F) Q-12a G-1(2-Cl) Q-12a G-3(3-F) Q-12a G-3(3-Cl) Q-12a G-3(3-CH 3 ) Q-12a G-3(3-CF 3 ) Q-47a G-1(4-F) Q-47a G-1(2-F) Q-47a G-1(2-Cl) Q-47a G-3(3-F) Q-47a G-3(3-Cl) Q-47a G-3(3-CH 3 ) Q-47a G-3(3-CF 3 ) Q-3(4-CN) G-1(4-F) Q-3(4-CN) G-1(2-F) Q-3(4-CN) G-1(2-Cl) Q-3(4-CN) G-3(3-F) Q-3(4-CN) G-3(3-Cl) Q-3(4-CN) G-3(3-CH 3 ) Q-3(4-CN) G-3(3-CF 3 ) Q-2(4-CN) G-1(4-F) Q-2(4-CN) G-1(2-F) Q-2(4-CN) G-1(2-Cl) Q-2(4-CN) G-3(3-F) Q-2(4-CN) G-3(3-Cl) Q-2(4-CN) G-3(3-CH 3 ) Q-2(4-CN) G-3(3-CF 3 ) Q-3(5-Cl) G-1(4-F) Q-3(5-Cl) G-1(2-F) Q-3(5-Cl) G-1(2-Cl) Q-3(5-Cl) G-3(3-F) Q-3(5-Cl) G-3(3-Cl) Q-3(5-Cl) G-3(3-CH 3 ) Q-3(5-Cl) G-3(3-CF 3 ) Q-3(5-CH 3 ) G-1(4-F) Q-3(5-CH 3 ) G-1(2-F) Q-3(5-CH 3 ) G-1(2-Cl) Q-3(5-CH 3 ) G-3(3-F) Q-3(5-CH 3) G-3(3-Cl) Q-3(5-CH 3 ) G-3(3-CH 3 ) Q-3(5-CH 3 ) G-3(3-CF 3 ) Q-6(3-CH 3 ) G-1(4-F) Q-6(3-CH 3 ) G-1(2-F) Q-6(3-CH 3 ) G-1(2-Cl) Q-6(3-CH 3 ) G-3(3-F) Q-6(3-CH 3 ) G-3(3-Cl) Q-6(3-CH 3 ) G-3(3-CH 3 ) Q-6(3-CH 3 ) G-3(3-CF 3 ) Q-6(3-Cl) G-1(4-F) Q-6(3-Cl) G-1(2-F) Q-6(3-Cl) G-1(2-Cl) Q-6(3-Cl) G-3(3-F) Q-6(3-Cl) G-3(3-Cl) Q-6(3-Cl) G-3(3-CH 3 ) Q-6(3-Cl) G-3(3-CF 3 ) Q-3(4-I) G-1(4-F) Q-3(4-I) G-1(2-F) Q-3(4-I) G-1(2-Cl) Q-3(4-I) G-3(3-F) Q-3(4-I) G-3(3-Cl) Q-3(4-I) G-3(3-CH 3 ) Q-3(4-I) G-3(3-CF 3 ) Q-10 G-1(4-F) Q-10 G-1(2-F) Q-10 G-1(2-Cl) Q-10 G-3(3-F) Q-10 G-3(3-Cl) Q-10 G-3(3-CH 3 ) Q-10 G-3(3-CF 3 ) Q-3(5-Br) G-1(4-F) Q-3(5-Br) G-1(2-F) Q-3(5-Br) G-1(2-Cl) Q-3(5-Br) G-3(3-F) Q-3(5-Br) G-3(3-Cl) Q-3(5-Br) G-3(3-CH 3 ) Q-3(5-Br) G-3(3-CF 3 ) Q-3(3-Br) G-1(4-F) Q-3(3-Br) G-1(2-F) Q-3(3-Br) G-1(2-Cl) Q-3(3-Br) G-3(3-F) Q-3(3-Br) G-3(3-Cl) Q-3(3-Br) G-3(3-CH 3 ) Q-3(3-Br) G-3(3-CF 3 ) Q-3(4-CF 3 ) G-1(4-F) Q-3(4-CF 3 ) G-1(2-F) Q-3(4-CF 3 ) G-1(2-Cl) Q-3(4-CF 3 ) G-3(3-F) Q-3(4-CF 3 ) G-3(3-Cl) Q-3(4-CF 3 ) G-3(3-CH 3 ) Q-3(4-CF 3 ) G-3(3-CF3 ) Q-8(3-CH 3 ) G-1(4-F) Q-8(3-CH 3 ) G-1(2-F) Q-8(3-CH 3 ) G-1(2-Cl) Q-8(3-CH 3 ) G-3(3-F) Q-8(3-CH 3 ) G-3(3-Cl) Q-8(3-CH 3 ) G-3(3-CH 3 ) Q-8(3-CH 3 ) G-3(3-CF 3 ) Q-8(3-Cl) G-1(4-F) Q-8(3-Cl) G-1(2-F) Q-8(3-Cl) G-1(2-Cl) Q-8(3-Cl) G-3(3-F) Q-8(3-Cl) G-3(3-Cl) Q-8(3-Cl) G-3(3-CH 3 ) Q-8(3-Cl) G-3(3-CF 3 ) Q-1(4-F) G-1(4-F) Q-1(4-F) G-1(5-F) Q-1(4-F) G-3(3-F) Q-1(4-F) G-3(3-Cl) Q-1(4-F) G-3(3-CH 3 ) Q-1(4-F) G-3(3-CF 3 ) Q-1(4-CN) G-1(4-F) Q-1(4-CN) G-1(5-F) Q-1(4-CN) G-3(3-F) Q-1(4-CN) G-3(3-Cl) Q-1(4-CN) G-3(3-CH 3 ) Q-1(4-CN) G-3(3-CF 3 ) Q-2(4-F) G-1(4-F) Q-2(4-F) G-1(5-F) Q-2(4-F) G-3(3-F) Q-2(4-F) G-3(3-Cl) Q-2(4-F) G-3(3-CH 3 ) Q-2(4-F) G-3(3-CF 3 ) Q-2(4-Cl) G-1(4-F) Q-2(4-Cl) G-1(5-F) Q-2(4-Cl) G-3(3-F) Q-2(4-Cl) G-3(3-Cl) Q-2(4-Cl) G-3(3-CH 3 ) Q-2(4-Cl) G-3(3-CF 3 ) Q-2(4-CN) G-1(5-F) Q-3 G-1(4-F) Q-3 G-1(5-F) Q-3 G-3(3-F) Q-3 G-3(3-Cl) Q-3 G-3(3-CH 3 ) Q-3 G-3(3-CF 3 ) Q-3(3-CH 3 ) G-1(5-F) Q-3(3-Cl) G-1(5-F) Q-3(3-F) G-1(4-F) Q-3(3-F) G-1(5-F) Q-3(3-F) G-3(3-F) Q-3(3-F) G-3(3-Cl) Q-3(3-F) G-3(3-CH 3 ) Q-3(3-F) G-3(3-CF 3 ) Q-3(4-Br) G-1(4-F) Q-3(4-Br) G-1(5-F) Q-3(4-Br) G-3(3-F) Q-3(4-Br) G-3(3-Cl) Q-3(4-Br) G-3(3-CH 3 ) Q-3(4-Br) G-3(3-CF 3 ) Q-3(4-CF 3 ) G-1(5-F) Q-3(4-CH 3 ) G-1(4-F) Q-3(4-CH 3 ) G-1(5-F) Q-3(4-CH 3 ) G-3(3-F) Q-3(4-CH 3 ) G-3(3-Cl) Q-3(4-CH 3 ) G-3(3-CH 3 ) Q-3(4-CH 3 ) G-3(3-CF 3 ) Q-3(4-Cl) G-1(4-F) Q-3(4-Cl) G-1(5-F) Q-3(4-Cl) G-3(3-F) Q-3(4-Cl) G-3(3-Cl) Q-3(4-Cl) G-3(3-CH 3 ) Q-3(4-Cl) G-3(3-CF 3 ) Q-3(4-CN) G-1(5-F) Q-3(4-F) G-1(4-F) Q-3(4-F) G-1(5-F) Q-3(4-F) G-3(3-F) Q-3(4-F) G-3(3-Cl) Q-3(4-F) G-3(3-CH 3 ) Q-3(4-F) G-3(3-CF 3 ) Q-3(6-F) G-1(4-F) Q-3(6-F) G-1(5-F) Q-3(6-F) G-3(3-F) Q-3(6-F) G-3(3-Cl) Q-3(6-F) G-3(3-CH 3 ) Q-3(6-F) G-3(3-CF 3 ) Q-4 G-1(4-F) Q-4 G-1(5-F) Q-4 G-3(3-F) Q-4 G-3(3-Cl) Q-4 G-3(3-CH 3 ) Q-4 G-3(3-CF 3 ) Q-4(3-CH 3 ) G-1(5-F) Q-4(3-Cl) G-1(5-F) Q-4(4-Br) G-1(4-F) Q-4(4-Br) G-1(5-F) Q-4(4-Br) G-3(3-F) Q-4(4-Br) G-3(3-Cl) Q-4(4-Br) G-3(3-CH 3 ) Q-4(4-Br) G-3(3-CF 3 ) Q-4(4-Cl) G-1(4-F) Q-4(4-Cl) G-1(5-F) Q-4(4-Cl) G-3(3-F) Q-4(4-Cl) G-3(3-Cl) Q-4(4-Cl) G-3(3-CH 3 ) Q-4(4-Cl) G-3(3-CF 3 ) Q-6(4-Cl) G-1(4-F) Q-6(4-Cl) G-1(5-F) Q-6(4-Cl) G-3(3-F) Q-6(4-Cl) G-3(3-Cl) Q-6(4-Cl) G-3(3-CH 3 ) Q-6(4-Cl) G-3(3-CF 3 ) Q-9 G-1(4-F) Q-9 G-1(5-F) Q-9 G-3(3-F) Q-9 G-3(3-Cl) Q-9 G-3(3-CH 3 ) Q-9 G-3(3-CF 3 ) Q-12a G-1(5-F) ――――――――――― [Table 13]
[0153]
Chem.
[0154] ―――――― Q ―――――― Q-1 Q-1(4-F) Q-1(4-Cl) Q-1(4-Br) Q-1(4-I) Q-1(4-CN) Q-1(4-CH 3 ) Q-1(4-CF 3 ) Q-2 Q-2(4-F) Q-2(4-Cl) Q-2(4-Br) Q-2(4-I) Q-2(4-CN) Q-2(4-CH 3 ) Q-2(4-CF 3 ) Q-3 Q-3(4-F) Q-3(4-Cl) Q-3(4-Br) Q-3(4-I) Q-3(4-CN) Q-3(4-CH 3 ) Q-3(4-CF 3 ) Q-4 Q-4(4-F) Q-4(4-Cl) Q-4(4-Br) Q-4(4-I) Q-4(4-CN) Q-4(4-CH 3 ) Q-4(4-CF 3 ) Q-6 Q-6(4-F) Q-6(4-Cl) Q-6(4-Br) Q-6(4-I) Q-6(4-CN) Q-6(4-CH 3 ) Q-6(4-CF 3 ) Q-9 Q-9(4-F) Q-9(4-Cl) Q-9(4-Br) Q-9(4-I) Q-9(4-CN) Q-9(4-CH 3 ) Q-9(4-CF 3 ) Q-10 Q-10(3-F) Q-10(3-Cl) Q-10(3-Br) Q-10(3-I) Q-10(3-CN) Q-10(3-CH 3 ) Q-10(3-CF 3 ) Q-12a Q-12a(4-F) Q-12a(4-Cl) Q-12a(4-Br) Q-12a(4-I) Q-12a(4-CN) Q-12a(4-CH 3 ) Q-12a(4-CF 3 ) Q-1(3-F) Q-1(3-Cl) Q-1(3-Br) Q-1(3-I) Q-1(3-CN) Q-1(3-CH 3 ) Q-1(3-CF 3 ) Q-1(2-F) Q-1(2-Cl) Q-1(2-Br) Q-1(2-I) Q-1(2-CN) Q-1(2-CH 3 ) Q-1(2-CF 3 ) Q-3(3-F) Q-3(3-Cl) Q-3(3-Br) Q-3(3-I) Q-3(3-CN) Q-3(3-CH 3 ) Q-3(3-CF 3 ) Q-3(5-F) Q-3(5-Cl) Q-3(5-Br) Q-3(5-I) Q-3(5-CN) Q-3(5-CH 3 ) Q-3(5-CF 3 ) Q-3(6-F) Q-3(6-Cl) Q-3(6-Br) Q-3(6-I) Q-3(6-CN) Q-3(6-CH 3 ) Q-3(6-CF 3 ) Q-4(3-F) Q-4(3-Cl) Q-4(3-Br) Q-4(3-I) Q-4(3-CN) Q-4(3-CH 3 ) Q-4(3-CF 3 ) Q-6(3-F) Q-6(3-Cl) Q-6(3-Br) Q-6(3-I) Q-6(3-CN) Q-6(3-CH 3 ) Q-6(3-CF 3 ) Q-9(3-F) Q-9(3-Cl) Q-9(3-Br) Q-9(3-I) Q-9(3-CN) Q-9(3-CH 3 ) Q-9(3-CF 3 ) ―――――― [Table 14]
[0155]
Chem.
[0156] ―――――― Q ―――――― Q-1 Q-1(4-F) Q-1(4-Cl) Q-1(4-Br) Q-1(4-I) Q-1(4-CN) Q-1(4-CH 3 ) Q-1(4-CF 3 ) Q-2 Q-2(4-F) Q-2(4-Cl) Q-2(4-Br) Q-2(4-I) Q-2(4-CN) Q-2(4-CH 3 ) Q-2(4-CF 3 ) Q-3 Q-3(4-F) Q-3(4-Cl) Q-3(4-Br) Q-3(4-I) Q-3(4-CN) Q-3(4-CH 3 ) Q-3(4-CF 3 ) Q-4 Q-4(4-F) Q-4(4-Cl) Q-4(4-Br) Q-4(4-I) Q-4(4-CN) Q-4(4-CH 3 ) Q-4(4-CF 3 ) Q-6 Q-6(4-F) Q-6(4-Cl) Q-6(4-Br) Q-6(4-I) Q-6(4-CN) Q-6(4-CH 3 ) Q-6(4-CF 3 ) Q-9 Q-9(4-F) Q-9(4-Cl) Q-9(4-Br) Q-9(4-I) Q-9(4-CN) Q-9(4-CH 3 ) Q-9(4-CF 3 ) Q-10 Q-10(3-F) Q-10(3-Cl) Q-10(3-Br) Q-10(3-I) Q-10(3-CN) Q-10(3-CH 3 ) Q-10(3-CF 3 ) Q-12a Q-12a(4-F) Q-12a(4-Cl) Q-12a(4-Br) Q-12a(4-I) Q-12a(4-CN) Q-12a(4-CH 3 ) Q-12a(4-CF 3 ) Q-1(3-F) Q-1(3-Cl) Q-1(3-Br) Q-1(3-I) Q-1(3-CN) Q-1(3-CH 3 ) Q-1(3-CF 3 ) Q-1(2-F) Q-1(2-Cl) Q-1(2-Br) Q-1(2-I) Q-1(2-CN) Q-1(2-CH 3 ) Q-1(2-CF 3 ) Q-3(3-F) Q-3(3-Cl) Q-3(3-Br) Q-3(3-I) Q-3(3-CN) Q-3(3-CH 3 ) Q-3(3-CF 3 ) Q-3(5-F) Q-3(5-Cl) Q-3(5-Br) Q-3(5-I) Q-3(5-CN) Q-3(5-CH 3 ) Q-3(5-CF 3) Q-3(6-F) Q-3(6-Cl) Q-3(6-Br) Q-3(6-I) Q-3(6-CN) Q-3(6-CH 3 ) Q-3(6-CF 3 ) Q-4(3-F) Q-4(3-Cl) Q-4(3-Br) Q-4(3-I) Q-4(3-CN) Q-4(3-CH 3 ) Q-4(3-CF 3 ) Q-6(3-F) Q-6(3-Cl) Q-6(3-Br) Q-6(3-I) Q-6(3-CN) Q-6(3-CH 3 ) Q-6(3-CF 3 ) Q-9(3-F) Q-9(3-Cl) Q-9(3-Br) Q-9(3-I) Q-9(3-CN) Q-9(3-CH 3 ) Q-9(3-CF 3 ) ―――――― [Table 15]
[0157] [Chem.]
[0158] ―――――― R 1 G 51 ―――――― H Cl H Br H I F Cl F Br F I Cl Cl Cl Br Cl I CHF 2 Cl CHF 2 Br CHF 2 I CF 3 Cl CF 3 Br CF 3 I ―――――― [Table 16]
[0159]
Chem.
[0160] ―――――― G 51 ―――――― Cl Br I ―――――― [Table 17]
[0161]
Chem.
[0162] ――――――――――― R 1 G ――――――――――― Cl G-7 Cl G-1 Cl G-3 Cl G-2 Cl G-7(3-F) Cl G-7(4-F) Cl G-7(5-F) Cl G-7(6-F) Cl G-1(2-F) Cl G-1(4-F) Cl G-1(5-F) Cl G-1(6-F) Cl G-3(2-F) Cl G-3(3-F) Cl G-2(2-F) Cl G-2(3-F) Cl G-2(4-F) Cl G-2(2-F,4-F) Cl G-2(2-F,5-F) Cl G-7(3-Cl) Cl G-7(4-Cl) Cl G-7(5-Cl) Cl G-7(6-Cl) Cl G-1(2-Cl) Cl G-1(4-Cl) Cl G-1(5-Cl) Cl G-1(6-Cl) Cl G-3(2-Cl) Cl G-3(3-Cl) Cl G-2(2-Cl) Cl G-2(3-Cl) Cl G-2(4-Cl) Cl G-2(2-Cl,4-Cl) Cl G-2(2-Cl,5-Cl) Cl G-7(3-CH 3 ) Cl G-7(4-CH 3 ) Cl G-7(5-CH 3 ) Cl G-7(6-CH 3 ) Cl G-1(2-CH 3 ) Cl G-1(4-CH 3 ) Cl G-1(5-CH 3 ) Cl G-1(6-CH 3 ) Cl G-3(2-CH 3 ) Cl G-3(3-CH 3 ) Cl G-2(2-CH 3 ) Cl G-2(3-CH 3 ) Cl G-2(4-CH 3 ) Cl G-2(2-CH 3 ,4-CH 3 ) Cl G-2(2-CH 3 ,5-CH 3 ) Cl G-7(3-CF 3 ) Cl G-7(4-CF 3 ) Cl G-7(5-CF 3 ) Cl G-7(6-CF 3 ) Cl G-1(2-CF 3 ) Cl G-1(4-CF 3 ) Cl G-1(5-CF 3 ) Cl G-1(6-CF 3 ) Cl G-3(2-CF 3 ) Cl G-3(3-CF 3 ) Cl G-2(2-CF 3 ) Cl G-2(3-CF 3 ) Cl G-2(4-CF 3 ) Cl G-2(2-CF 3 ,4-CF 3 ) Cl G-2(2-CF 3 ,5-CF 3 ) Cl G-1(4-NO 2 ) Cl G-1(4-NH 2 ) Cl G-1(5-NO 2 ) Cl G-1(5-NH 2 ) Cl G-3(3-NO 2 ) Cl G-3(3-NH 2 ) CF 3 G-7 CF 3 G-1 CF 3 G-3 CF 3 G-2 CF 3 G-7(3-F) CF 3 G-7(4-F) CF 3 G-7(5-F) CF 3 G-7(6-F) CF 3 G-1(2-F) CF 3 G-1(4-F) CF 3 G-1(5-F) CF 3 G-1(6-F) CF 3 G-3(2-F) CF 3 G-3(3-F) CF 3 G-2(2-F) CF 3 G-2(3-F) CF 3 G-2(4-F) CF 3 G-2(2-F,4-F) CF 3 G-2(2-F,5-F) CF 3 G-7(3-Cl) CF 3 G-7(4-Cl) CF 3 G-7(5-Cl) CF 3 G-7(6-Cl) CF 3 G-1(2-Cl) CF 3 G-1(4-Cl) CF 3 G-1(5-Cl) CF 3 G-1(6-Cl) CF 3 G-3(2-Cl) CF 3 G-3(3-Cl) CF 3 G-2(2-Cl) CF 3 G-2(3-Cl) CF 3 G-2(4-Cl) CF 3 G-2(2-Cl,4-Cl) CF 3 G-2(2-Cl,5-Cl) CF 3 G-7(3-CH 3 ) CF 3 G-7(4-CH 3 ) CF 3 G-7(5-CH 3 ) CF 3 G-7(6-CH 3 ) CF 3 G-1(2-CH 3 ) CF 3 G-1(4-CH 3 ) CF 3 G-1(5-CH 3 ) CF 3 G-1(6-CH 3 ) CF 3 G-3(2-CH 3 ) CF 3 G-3(3-CH 3 ) CF 3 G-2(2-CH 3 ) CF 3 G-2(3-CH 3 ) CF 3 G-2(4-CH 3 ) CF 3 G-2(2-CH 3,4-CH 3 ) CF 3 G-2(2-CH 3 ,5-CH 3 ) CF 3 G-7(3-CF 3 ) CF 3 G-7(4-CF 3 ) CF 3 G-7(5-CF 3 ) CF 3 G-7(6-CF 3 ) CF 3 G-1(2-CF 3 ) CF 3 G-1(4-CF 3 ) CF 3 G-1(5-CF 3 ) CF 3 G-1(6-CF 3 ) CF 3 G-3(2-CF 3 ) CF 3 G-3(3-CF 3 ) CF 3 G-2(2-CF 3 ) CF 3 G-2(3-CF 3 ) CF 3 G-2(4-CF 3 ) CF 3 G-2(2-CF 3 ,4-CF 3 ) CF 3 G-2(2-CF 3 ,5-CF 3 ) CF 3 G-1(4-NO 2 ) CF 3 G-1(4-NH 2 ) CF 3G-1(5-NO 2 ) CF 3 G-1(5-NH 2 ) CF 3 G-3(3-NO 2 ) CF 3 G-3(3-NH 2 ) CHF 2 G-7 CHF 2 G-1 CHF 2 G-3 CHF 2 G-2 CHF 2 G-7(3-F) CHF 2 G-7(4-F) CHF 2 G-7(5-F) CHF 2 G-7(6-F) CHF 2 G-1(2-F) CHF 2 G-1(4-F) CHF 2 G-1(5-F) CHF 2 G-1(6-F) CHF 2 G-3(2-F) CHF 2 G-3(3-F) CHF 2 G-2(2-F) CHF 2 G-2(3-F) CHF 2 G-2(4-F) CHF 2 G-2(2-F,4-F) CHF 2 G-2(2-F,5-F) CHF 2 G-7(3-Cl) CHF 2 G-7(4-Cl) CHF 2 G-7(5-Cl) CHF2 G-7(6-Cl) CHF 2 G-1(2-Cl) CHF 2 G-1(4-Cl) CHF 2 G-1(5-Cl) CHF 2 G-1(6-Cl) CHF 2 G-3(2-Cl) CHF 2 G-3(3-Cl) CHF 2 G-2(2-Cl) CHF 2 G-2(3-Cl) CHF 2 G-2(4-Cl) CHF 2 G-2(2-Cl,4-Cl) CHF 2 G-2(2-Cl,5-Cl) CHF 2 G-7(3-CH 3 ) CHF 2 G-7(4-CH 3 ) CHF 2 G-7(5-CH 3 ) CHF 2 G-7(6-CH 3 ) CHF 2 G-1(2-CH 3 ) CHF 2 G-1(4-CH 3 ) CHF 2 G-1(5-CH 3 ) CHF 2 G-1(6-CH 3 ) CHF 2 G-3(2-CH 3 ) CHF 2 G-3(3-CH 3 ) CHF 2 G-2(2-CH3 ) CHF 2 G-2(3-CH 3 ) CHF 2 G-2(4-CH 3 ) CHF 2 G-2(2-CH 3 ,4-CH 3 ) CHF 2 G-2(2-CH 3 ,5-CH 3 ) CHF 2 G-7(3-CF 3 ) CHF 2 G-7(4-CF 3 ) CHF 2 G-7(5-CF 3 ) CHF 2 G-7(6-CF 3 ) CHF 2 G-1(2-CF 3 ) CHF 2 G-1(4-CF 3 ) CHF 2 G-1(5-CF 3 ) CHF 2 G-1(6-CF 3 ) CHF 2 G-3(2-CF 3 ) CHF 2 G-3(3-CF 3 ) CHF 2 G-2(2-CF 3 ) CHF 2 G-2(3-CF 3 ) CHF 2 G-2(4-CF 3 ) CHF 2 G-2(2-CF 3 ,4-CF 3 ) CHF2 G-2(2-CF 3 ,5-CF 3 ) ――――――――――― [Table 18]
[0163]
Chemical
[0164] ―――――――― G ―――――――― G-7 G-1 G-3 G-2 G-7(3-F) G-7(4-F) G-7(5-F) G-7(6-F) G-1(2-F) G-1(4-F) G-1(5-F) G-1(6-F) G-3(2-F) G-3(3-F) G-2(2-F) G-2(3-F) G-2(4-F) G-2(2-F,4-F) G-2(2-F,5-F) G-7(3-Cl) G-7(4-Cl) G-7(5-Cl) G-7(6-Cl) G-1(2-Cl) G-1(4-Cl) G-1(5-Cl) G-1(6-Cl) G-3(2-Cl) G-3(3-Cl) G-2(2-Cl) G-2(3-Cl) G-2(4-Cl) G-2(2-Cl,4-Cl) G-2(2-Cl,5-Cl) G-7(3-CH 3 ) G-7(4-CH 3 ) G-7(5-CH 3 ) G-7(6-CH 3 ) G-1(2-CH 3 ) G-1(4-CH 3 ) G-1(5-CH 3 ) G-1(6-CH 3 ) G-3(2-CH 3 ) G-3(3-CH 3 ) G-2(2-CH 3 ) G-2(3-CH 3 ) G-2(4-CH 3 ) G-2(2-CH 3 ,4-CH 3 ) G-2(2-CH 3 ,5-CH 3 ) G-7(3-CF 3 ) G-7(4-CF 3 ) G-7(5-CF 3 ) G-7(6-CF 3 ) G-1(2-CF 3 ) G-1(4-CF 3 ) G-1(5-CF 3 ) G-1(6-CF 3 ) G-3(2-CF 3 ) G-3(3-CF 3 ) G-2(2-CF 3 ) G-2(3-CF 3 ) G-2(4-CF3 ) G-2(2-CF 3 ,4-CF 3 ) G-2(2-CF 3 ,5-CF 3 ) G-1(4-NO 2 ) G-1(4-NH 2 ) G-1(5-NO 2 ) G-1(5-NH 2 ) G-3(3-NO 2 ) G-3(3-NH 2 ) ―――――――― [Table 19]
[0165] [Chem.]
[0166] ――――――――――― Q G ――――――――――― Q-3(3-Cl) G-1(4-F) Q-3(3-Cl) G-1(2-F) Q-3(3-Cl) G-1(2-Cl) Q-3(3-Cl) G-3(3-F) Q-3(3-Cl) G-3(3-Cl) Q-3(3-Cl) G-3(3-CH 3 ) Q-3(3-Cl) G-3(3-CF 3 ) Q-3(3-CH 3 ) G-1(4-F) Q-3(3-CH 3 ) G-1(2-F) Q-3(3-CH 3 ) G-1(2-Cl) Q-3(3-CH 3 ) G-3(3-F) Q-3(3-CH3 ) G-3(3-Cl) Q-3(3-CH 3 ) G-3(3-CH 3 ) Q-3(3-CH 3 ) G-3(3-CF 3 ) Q-4(3-Cl) G-1(4-F) Q-4(3-Cl) G-1(2-F) Q-4(3-Cl) G-1(2-Cl) Q-4(3-Cl) G-3(3-F) Q-4(3-Cl) G-3(3-Cl) Q-4(3-Cl) G-3(3-CH 3 ) Q-4(3-Cl) G-3(3-CF 3 ) Q-4(3-CH 3 ) G-1(4-F) Q-4(3-CH 3 ) G-1(2-F) Q-4(3-CH 3 ) G-1(2-Cl) Q-4(3-CH 3 ) G-3(3-F) Q-4(3-CH 3 ) G-3(3-Cl) Q-4(3-CH 3 ) G-3(3-CH 3 ) Q-4(3-CH 3 ) G-3(3-CF 3 ) Q-4(4-CH 3 ) G-1(4-F) Q-4(4-CH 3 ) G-1(2-F) Q-4(4-CH 3 ) G-1(2-Cl) Q-4(4-CH 3 ) G-3(3-F) Q-4(4-CH 3 ) G-3(3-Cl) Q-4(4-CH 3 ) G-3(3-CH 3) Q-4(4-CH 3 ) G-3(3-CF 3 ) Q-4(3-Br) G-1(4-F) Q-4(3-Br) G-1(2-F) Q-4(3-Br) G-1(2-Cl) Q-4(3-Br) G-3(3-F) Q-4(3-Br) G-3(3-Cl) Q-4(3-Br) G-3(3-CH 3 ) Q-4(3-Br) G-3(3-CF 3 ) Q-10(3-CH 3 ) G-1(4-F) Q-10(3-CH 3 ) G-1(2-F) Q-10(3-CH 3 ) G-1(2-Cl) Q-10(3-CH 3 ) G-3(3-F) Q-10(3-CH 3 ) G-3(3-Cl) Q-10(3-CH 3 ) G-3(3-CH 3 ) Q-10(3-CH 3 ) G-3(3-CF 3 ) Q-12a G-1(4-F) Q-12a G-1(2-F) Q-12a G-1(2-Cl) Q-12a G-3(3-F) Q-12a G-3(3-Cl) Q-12a G-3(3-CH 3 ) Q-12a G-3(3-CF 3 ) Q-47a G-1(4-F) Q-47a G-1(2-F) Q-47a G-1(2-Cl) Q-47a G-3(3-F) Q-47a G-3(3-Cl) Q-47a G-3(3-CH 3 ) Q-47a G-3(3-CF 3 ) Q-3(4-CN) G-1(4-F) Q-3(4-CN) G-1(2-F) Q-3(4-CN) G-1(2-Cl) Q-3(4-CN) G-3(3-F) Q-3(4-CN) G-3(3-Cl) Q-3(4-CN) G-3(3-CH 3 ) Q-3(4-CN) G-3(3-CF 3 ) Q-2(4-CN) G-1(4-F) Q-2(4-CN) G-1(2-F) Q-2(4-CN) G-1(2-Cl) Q-2(4-CN) G-3(3-F) Q-2(4-CN) G-3(3-Cl) Q-2(4-CN) G-3(3-CH 3 ) Q-2(4-CN) G-3(3-CF 3 ) Q-3(5-Cl) G-1(4-F) Q-3(5-Cl) G-1(2-F) Q-3(5-Cl) G-1(2-Cl) Q-3(5-Cl) G-3(3-F) Q-3(5-Cl) G-3(3-Cl) Q-3(5-Cl) G-3(3-CH 3 ) Q-3(5-Cl) G-3(3-CF 3 ) Q-3(5-CH 3 ) G-1(4-F) Q-3(5-CH 3 ) G-1(2-F) Q-3(5-CH 3 ) G-1(2-Cl) Q-3(5-CH3 ) G-3(3-F) Q-3(5-CH 3 ) G-3(3-Cl) Q-3(5-CH 3 ) G-3(3-CH 3 ) Q-3(5-CH 3 ) G-3(3-CF 3 ) Q-6(3-CH 3 ) G-1(4-F) Q-6(3-CH 3 ) G-1(2-F) Q-6(3-CH 3 ) G-1(2-Cl) Q-6(3-CH 3 ) G-3(3-F) Q-6(3-CH 3 ) G-3(3-Cl) Q-6(3-CH 3 ) G-3(3-CH 3 ) Q-6(3-CH 3 ) G-3(3-CF 3 ) Q-6(3-Cl) G-1(4-F) Q-6(3-Cl) G-1(2-F) Q-6(3-Cl) G-1(2-Cl) Q-6(3-Cl) G-3(3-F) Q-6(3-Cl) G-3(3-Cl) Q-6(3-Cl) G-3(3-CH 3 ) Q-6(3-Cl) G-3(3-CF 3 ) Q-3(4-I) G-1(4-F) Q-3(4-I) G-1(2-F) Q-3(4-I) G-1(2-Cl) Q-3(4-I) G-3(3-F) Q-3(4-I) G-3(3-Cl) Q-3(4-I) G-3(3-CH 3 ) Q-3(4-I) G-3(3-CF3 ) Q-10 G-1(4-F) Q-10 G-1(2-F) Q-10 G-1(2-Cl) Q-10 G-3(3-F) Q-10 G-3(3-Cl) Q-10 G-3(3-CH 3 ) Q-10 G-3(3-CF 3 ) Q-3(5-Br) G-1(4-F) Q-3(5-Br) G-1(2-F) Q-3(5-Br) G-1(2-Cl) Q-3(5-Br) G-3(3-F) Q-3(5-Br) G-3(3-Cl) Q-3(5-Br) G-3(3-CH 3 ) Q-3(5-Br) G-3(3-CF 3 ) Q-3(3-Br) G-1(4-F) Q-3(3-Br) G-1(2-F) Q-3(3-Br) G-1(2-Cl) Q-3(3-Br) G-3(3-F) Q-3(3-Br) G-3(3-Cl) Q-3(3-Br) G-3(3-CH 3 ) Q-3(3-Br) G-3(3-CF 3 ) Q-3(4-CF 3 ) G-1(4-F) Q-3(4-CF 3 ) G-1(2-F) Q-3(4-CF 3 ) G-1(2-Cl) Q-3(4-CF 3 ) G-3(3-F) Q-3(4-CF 3 ) G-3(3-Cl) Q-3(4-CF 3 ) G-3(3-CH 3 ) Q-3(4-CF 3 ) G-3(3-CF 3 ) Q-8(3-CH 3 ) G-1(4-F) Q-8(3-CH 3 ) G-1(2-F) Q-8(3-CH 3 ) G-1(2-Cl) Q-8(3-CH 3 ) G-3(3-F) Q-8(3-CH 3 ) G-3(3-Cl) Q-8(3-CH 3 ) G-3(3-CH 3 ) Q-8(3-CH 3 ) G-3(3-CF 3 ) Q-8(3-Cl) G-1(4-F) Q-8(3-Cl) G-1(2-F) Q-8(3-Cl) G-1(2-Cl) Q-8(3-Cl) G-3(3-F) Q-8(3-Cl) G-3(3-Cl) Q-8(3-Cl) G-3(3-CH 3 ) Q-8(3-Cl) G-3(3-CF 3 ) Q-1(4-F) G-1(4-F) Q-1(4-F) G-1(5-F) Q-1(4-F) G-3(3-F) Q-1(4-F) G-3(3-Cl) Q-1(4-F) G-3(3-CH 3 ) Q-1(4-F) G-3(3-CF 3 ) Q-1(4-CN) G-1(4-F) Q-1(4-CN) G-1(5-F) Q-1(4-CN) G-3(3-F) Q-1(4-CN) G-3(3-Cl) Q-1(4-CN) G-3(3-CH 3 ) Q-1(4-CN) G-3(3-CF 3 ) Q-2(4-F) G-1(4-F) Q-2(4-F) G-1(5-F) Q-2(4-F) G-3(3-F) Q-2(4-F) G-3(3-Cl) Q-2(4-F) G-3(3-CH 3 ) Q-2(4-F) G-3(3-CF 3 ) Q-2(4-Cl) G-1(4-F) Q-2(4-Cl) G-1(5-F) Q-2(4-Cl) G-3(3-F) Q-2(4-Cl) G-3(3-Cl) Q-2(4-Cl) G-3(3-CH 3 ) Q-2(4-Cl) G-3(3-CF 3 ) Q-2(4-CN) G-1(5-F) Q-3 G-1(4-F) Q-3 G-1(5-F) Q-3 G-3(3-F) Q-3 G-3(3-Cl) Q-3 G-3(3-CH 3 ) Q-3 G-3(3-CF 3 ) Q-3(3-CH 3 ) G-1(5-F) Q-3(3-Cl) G-1(5-F) Q-3(3-F) G-1(4-F) Q-3(3-F) G-1(5-F) Q-3(3-F) G-3(3-F) Q-3(3-F) G-3(3-Cl) Q-3(3-F) G-3(3-CH 3 ) Q-3(3-F) G-3(3-CF 3 ) Q-3(4-Br) G-1(4-F) Q-3(4-Br) G-1(5-F) Q-3(4-Br) G-3(3-F) Q-3(4-Br) G-3(3-Cl) Q-3(4-Br) G-3(3-CH 3 ) Q-3(4-Br) G-3(3-CF 3 ) Q-3(4-CF 3 ) G-1(5-F) Q-3(4-CH 3 ) G-1(4-F) Q-3(4-CH 3 ) G-1(5-F) Q-3(4-CH 3 ) G-3(3-F) Q-3(4-CH 3 ) G-3(3-Cl) Q-3(4-CH 3 ) G-3(3-CH 3 ) Q-3(4-CH 3 ) G-3(3-CF 3 ) Q-3(4-Cl) G-1(4-F) Q-3(4-Cl) G-1(5-F) Q-3(4-Cl) G-3(3-F) Q-3(4-Cl) G-3(3-Cl) Q-3(4-Cl) G-3(3-CH 3 ) Q-3(4-Cl) G-3(3-CF 3 ) Q-3(4-CN) G-1(5-F) Q-3(4-F) G-1(4-F) Q-3(4-F) G-1(5-F) Q-3(4-F) G-3(3-F) Q-3(4-F) G-3(3-Cl) Q-3(4-F) G-3(3-CH 3 ) Q-3(4-F) G-3(3-CF3 ) Q-3(6-F) G-1(4-F) Q-3(6-F) G-1(5-F) Q-3(6-F) G-3(3-F) Q-3(6-F) G-3(3-Cl) Q-3(6-F) G-3(3-CH 3 ) Q-3(6-F) G-3(3-CF 3 ) Q-4 G-1(4-F) Q-4 G-1(5-F) Q-4 G-3(3-F) Q-4 G-3(3-Cl) Q-4 G-3(3-CH 3 ) Q-4 G-3(3-CF 3 ) Q-4(3-CH 3 ) G-1(5-F) Q-4(3-Cl) G-1(5-F) Q-4(4-Br) G-1(4-F) Q-4(4-Br) G-1(5-F) Q-4(4-Br) G-3(3-F) Q-4(4-Br) G-3(3-Cl) Q-4(4-Br) G-3(3-CH 3 ) Q-4(4-Br) G-3(3-CF 3 ) Q-4(4-Cl) G-1(4-F) Q-4(4-Cl) G-1(5-F) Q-4(4-Cl) G-3(3-F) Q-4(4-Cl) G-3(3-Cl) Q-4(4-Cl) G-3(3-CH 3 ) Q-4(4-Cl) G-3(3-CF 3 ) Q-6(4-Cl) G-1(4-F) Q-6(4-Cl) G-1(5-F) Q-6(4-Cl) G-3(3-F) Q-6(4-Cl) G-3(3-Cl) Q-6(4-Cl) G-3(3-CH 3 ) Q-6(4-Cl) G-3(3-CF 3 ) Q-9 G-1(4-F) Q-9 G-1(5-F) Q-9 G-3(3-F) Q-9 G-3(3-Cl) Q-9 G-3(3-CH 3 ) Q-9 G-3(3-CF 3 ) Q-12a G-1(5-F) ――――――――――― [Table 20]
[0167]
Chem.
[0168] ――――――――――― Q G ――――――――――― Q-3(3-Cl) G-1(4-F) Q-3(3-Cl) G-1(2-F) Q-3(3-Cl) G-1(2-Cl) Q-3(3-Cl) G-3(3-F) Q-3(3-Cl) G-3(3-Cl) Q-3(3-Cl) G-3(3-CH 3 ) Q-3(3-Cl) G-3(3-CF 3 ) Q-3(3-CH 3 ) G-1(4-F) Q-3(3-CH 3 ) G-1(2-F) Q-3(3-CH 3 ) G-1(2-Cl) Q-3(3-CH 3 ) G-3(3-F) Q-3(3-CH3 ) G-3(3-Cl) Q-3(3-CH 3 ) G-3(3-CH 3 ) Q-3(3-CH 3 ) G-3(3-CF 3 ) Q-4(3-Cl) G-1(4-F) Q-4(3-Cl) G-1(2-F) Q-4(3-Cl) G-1(2-Cl) Q-4(3-Cl) G-3(3-F) Q-4(3-Cl) G-3(3-Cl) Q-4(3-Cl) G-3(3-CH 3 ) Q-4(3-Cl) G-3(3-CF 3 ) Q-4(3-CH 3 ) G-1(4-F) Q-4(3-CH 3 ) G-1(2-F) Q-4(3-CH 3 ) G-1(2-Cl) Q-4(3-CH 3 ) G-3(3-F) Q-4(3-CH 3 ) G-3(3-Cl) Q-4(3-CH 3 ) G-3(3-CH 3 ) Q-4(3-CH 3 ) G-3(3-CF 3 ) Q-4(4-CH 3 ) G-1(4-F) Q-4(4-CH 3 ) G-1(2-F) Q-4(4-CH 3 ) G-1(2-Cl) Q-4(4-CH 3 ) G-3(3-F) Q-4(4-CH 3 ) G-3(3-Cl) Q-4(4-CH 3 ) G-3(3-CH 3) Q-4(4-CH 3 ) G-3(3-CF 3 ) Q-4(3-Br) G-1(4-F) Q-4(3-Br) G-1(2-F) Q-4(3-Br) G-1(2-Cl) Q-4(3-Br) G-3(3-F) Q-4(3-Br) G-3(3-Cl) Q-4(3-Br) G-3(3-CH 3 ) Q-4(3-Br) G-3(3-CF 3 ) Q-10(3-CH 3 ) G-1(4-F) Q-10(3-CH 3 ) G-1(2-F) Q-10(3-CH 3 ) G-1(2-Cl) Q-10(3-CH 3 ) G-3(3-F) Q-10(3-CH 3 ) G-3(3-Cl) Q-10(3-CH 3 ) G-3(3-CH 3 ) Q-10(3-CH 3 ) G-3(3-CF 3 ) Q-12a G-1(4-F) Q-12a G-1(2-F) Q-12a G-1(2-Cl) Q-12a G-3(3-F) Q-12a G-3(3-Cl) Q-12a G-3(3-CH 3 ) Q-12a G-3(3-CF 3 ) Q-47a G-1(4-F) Q-47a G-1(2-F) Q-47a G-1(2-Cl) Q-47a G-3(3-F) Q-47a G-3(3-Cl) Q-47a G-3(3-CH 3 ) Q-47a G-3(3-CF 3 ) Q-3(4-CN) G-1(4-F) Q-3(4-CN) G-1(2-F) Q-3(4-CN) G-1(2-Cl) Q-3(4-CN) G-3(3-F) Q-3(4-CN) G-3(3-Cl) Q-3(4-CN) G-3(3-CH 3 ) Q-3(4-CN) G-3(3-CF 3 ) Q-2(4-CN) G-1(4-F) Q-2(4-CN) G-1(2-F) Q-2(4-CN) G-1(2-Cl) Q-2(4-CN) G-3(3-F) Q-2(4-CN) G-3(3-Cl) Q-2(4-CN) G-3(3-CH 3 ) Q-2(4-CN) G-3(3-CF 3 ) Q-3(5-Cl) G-1(4-F) Q-3(5-Cl) G-1(2-F) Q-3(5-Cl) G-1(2-Cl) Q-3(5-Cl) G-3(3-F) Q-3(5-Cl) G-3(3-Cl) Q-3(5-Cl) G-3(3-CH 3 ) Q-3(5-Cl) G-3(3-CF 3 ) Q-3(5-CH 3 ) G-1(4-F) Q-3(5-CH 3 ) G-1(2-F) Q-3(5-CH 3 ) G-1(2-Cl) Q-3(5-CH3 ) G-3(3-F) Q-3(5-CH 3 ) G-3(3-Cl) Q-3(5-CH 3 ) G-3(3-CH 3 ) Q-3(5-CH 3 ) G-3(3-CF 3 ) Q-6(3-CH 3 ) G-1(4-F) Q-6(3-CH 3 ) G-1(2-F) Q-6(3-CH 3 ) G-1(2-Cl) Q-6(3-CH 3 ) G-3(3-F) Q-6(3-CH 3 ) G-3(3-Cl) Q-6(3-CH 3 ) G-3(3-CH 3 ) Q-6(3-CH 3 ) G-3(3-CF 3 ) Q-6(3-Cl) G-1(4-F) Q-6(3-Cl) G-1(2-F) Q-6(3-Cl) G-1(2-Cl) Q-6(3-Cl) G-3(3-F) Q-6(3-Cl) G-3(3-Cl) Q-6(3-Cl) G-3(3-CH 3 ) Q-6(3-Cl) G-3(3-CF 3 ) Q-3(4-I) G-1(4-F) Q-3(4-I) G-1(2-F) Q-3(4-I) G-1(2-Cl) Q-3(4-I) G-3(3-F) Q-3(4-I) G-3(3-Cl) Q-3(4-I) G-3(3-CH 3 ) Q-3(4-I) G-3(3-CF3 ) Q-10 G-1(4-F) Q-10 G-1(2-F) Q-10 G-1(2-Cl) Q-10 G-3(3-F) Q-10 G-3(3-Cl) Q-10 G-3(3-CH 3 ) Q-10 G-3(3-CF 3 ) Q-3(5-Br) G-1(4-F) Q-3(5-Br) G-1(2-F) Q-3(5-Br) G-1(2-Cl) Q-3(5-Br) G-3(3-F) Q-3(5-Br) G-3(3-Cl) Q-3(5-Br) G-3(3-CH 3 ) Q-3(5-Br) G-3(3-CF 3 ) Q-3(3-Br) G-1(4-F) Q-3(3-Br) G-1(2-F) Q-3(3-Br) G-1(2-Cl) Q-3(3-Br) G-3(3-F) Q-3(3-Br) G-3(3-Cl) Q-3(3-Br) G-3(3-CH 3 ) Q-3(3-Br) G-3(3-CF 3 ) Q-3(4-CF 3 ) G-1(4-F) Q-3(4-CF 3 ) G-1(2-F) Q-3(4-CF 3 ) G-1(2-Cl) Q-3(4-CF 3 ) G-3(3-F) Q-3(4-CF 3 ) G-3(3-Cl) Q-3(4-CF 3 ) G-3(3-CH 3 ) Q-3(4-CF 3 ) G-3(3-CF 3 ) Q-8(3-CH 3 ) G-1(4-F) Q-8(3-CH 3 ) G-1(2-F) Q-8(3-CH 3 ) G-1(2-Cl) Q-8(3-CH 3 ) G-3(3-F) Q-8(3-CH 3 ) G-3(3-Cl) Q-8(3-CH 3 ) G-3(3-CH 3 ) Q-8(3-CH 3 ) G-3(3-CF 3 ) Q-8(3-Cl) G-1(4-F) Q-8(3-Cl) G-1(2-F) Q-8(3-Cl) G-1(2-Cl) Q-8(3-Cl) G-3(3-F) Q-8(3-Cl) G-3(3-Cl) Q-8(3-Cl) G-3(3-CH 3 ) Q-8(3-Cl) G-3(3-CF 3 ) Q-1(4-F) G-1(4-F) Q-1(4-F) G-1(5-F) Q-1(4-F) G-3(3-F) Q-1(4-F) G-3(3-Cl) Q-1(4-F) G-3(3-CH 3 ) Q-1(4-F) G-3(3-CF 3 ) Q-1(4-CN) G-1(4-F) Q-1(4-CN) G-1(5-F) Q-1(4-CN) G-3(3-F) Q-1(4-CN) G-3(3-Cl) Q-1(4-CN) G-3(3-CH 3 ) Q-1(4-CN) G-3(3-CF 3 ) Q-2(4-F) G-1(4-F) Q-2(4-F) G-1(5-F) Q-2(4-F) G-3(3-F) Q-2(4-F) G-3(3-Cl) Q-2(4-F) G-3(3-CH 3 ) Q-2(4-F) G-3(3-CF 3 ) Q-2(4-Cl) G-1(4-F) Q-2(4-Cl) G-1(5-F) Q-2(4-Cl) G-3(3-F) Q-2(4-Cl) G-3(3-Cl) Q-2(4-Cl) G-3(3-CH 3 ) Q-2(4-Cl) G-3(3-CF 3 ) Q-2(4-CN) G-1(5-F) Q-3 G-1(4-F) Q-3 G-1(5-F) Q-3 G-3(3-F) Q-3 G-3(3-Cl) Q-3 G-3(3-CH 3 ) Q-3 G-3(3-CF 3 ) Q-3(3-CH 3 ) G-1(5-F) Q-3(3-Cl) G-1(5-F) Q-3(3-F) G-1(4-F) Q-3(3-F) G-1(5-F) Q-3(3-F) G-3(3-F) Q-3(3-F) G-3(3-Cl) Q-3(3-F) G-3(3-CH 3 ) Q-3(3-F) G-3(3-CF 3 ) Q-3(4-Br) G-1(4-F) Q-3(4-Br) G-1(5-F) Q-3(4-Br) G-3(3-F) Q-3(4-Br) G-3(3-Cl) Q-3(4-Br) G-3(3-CH 3 ) Q-3(4-Br) G-3(3-CF 3 ) Q-3(4-CF 3 ) G-1(5-F) Q-3(4-CH 3 ) G-1(4-F) Q-3(4-CH 3 ) G-1(5-F) Q-3(4-CH 3 ) G-3(3-F) Q-3(4-CH 3 ) G-3(3-Cl) Q-3(4-CH 3 ) G-3(3-CH 3 ) Q-3(4-CH 3 ) G-3(3-CF 3 ) Q-3(4-Cl) G-1(4-F) Q-3(4-Cl) G-1(5-F) Q-3(4-Cl) G-3(3-F) Q-3(4-Cl) G-3(3-Cl) Q-3(4-Cl) G-3(3-CH 3 ) Q-3(4-Cl) G-3(3-CF 3 ) Q-3(4-CN) G-1(5-F) Q-3(4-F) G-1(4-F) Q-3(4-F) G-1(5-F) Q-3(4-F) G-3(3-F) Q-3(4-F) G-3(3-Cl) Q-3(4-F) G-3(3-CH 3 ) Q-3(4-F) G-3(3-CF3 ) Q-3(6-F) G-1(4-F) Q-3(6-F) G-1(5-F) Q-3(6-F) G-3(3-F) Q-3(6-F) G-3(3-Cl) Q-3(6-F) G-3(3-CH 3 ) Q-3(6-F) G-3(3-CF 3 ) Q-4 G-1(4-F) Q-4 G-1(5-F) Q-4 G-3(3-F) Q-4 G-3(3-Cl) Q-4 G-3(3-CH 3 ) Q-4 G-3(3-CF 3 ) Q-4(3-CH 3 ) G-1(5-F) Q-4(3-Cl) G-1(5-F) Q-4(4-Br) G-1(4-F) Q-4(4-Br) G-1(5-F) Q-4(4-Br) G-3(3-F) Q-4(4-Br) G-3(3-Cl) Q-4(4-Br) G-3(3-CH 3 ) Q-4(4-Br) G-3(3-CF 3 ) Q-4(4-Cl) G-1(4-F) Q-4(4-Cl) G-1(5-F) Q-4(4-Cl) G-3(3-F) Q-4(4-Cl) G-3(3-Cl) Q-4(4-Cl) G-3(3-CH 3 ) Q-4(4-Cl) G-3(3-CF 3 ) Q-6(4-Cl) G-1(4-F) Q-6(4-Cl) G-1(5-F) Q-6(4-Cl) G-3(3-F) Q-6(4-Cl) G-3(3-Cl) Q-6(4-Cl) G-3(3-CH 3 ) Q-6(4-Cl) G-3(3-CF 3 ) Q-9 G-1(4-F) Q-9 G-1(5-F) Q-9 G-3(3-F) Q-9 G-3(3-Cl) Q-9 G-3(3-CH 3 ) Q-9 G-3(3-CF 3 ) Q-12a G-1(5-F) ――――――――――― [Table 21]
[0169]
Chemical Structure
[0170] ―――――――――――――――― R 1 Q G ―――――――――――――――― CHF 2 Q-1(3-F) G-1(4-F) CHF 2 Q-1(3-F) G-3(3-F) CHF 2 Q-1(3-F) G-3(3-Cl) CHF 2 Q-1(3-F) G-3(3-CH 3 ) CHF 2 Q-1(3-F) G-3(3-CF 3 ) CHF 2 Q-1(4-F) G-1(4-F) CHF 2 Q-1(4-F) G-3(3-F) CHF 2 Q-1(4-F) G-3(3-Cl) CHF2 Q-1(4-F) G-3(3-CH 3 ) CHF 2 Q-1(4-F) G-3(3-CF 3 ) CHF 2 Q-1(4-CN) G-1(4-F) CHF 2 Q-1(4-CN) G-3(3-F) CHF 2 Q-1(4-CN) G-3(3-Cl) CHF 2 Q-1(4-CN) G-3(3-CH 3 ) CHF 2 Q-1(4-CN) G-3(3-CF 3 ) CHF 2 Q-1(4-CF 3 ) G-1(4-F) CHF 2 Q-1(4-CF 3 ) G-3(3-F) CHF 2 Q-1(4-CF 3 ) G-3(3-Cl) CHF 2 Q-1(4-CF 3 ) G-3(3-CH 3 ) CHF 2 Q-1(4-CF 3 ) G-3(3-CF 3 ) CHF 2 Q-1(2-F,4-F) G-1(4-F) CHF 2 Q-1(2-F,4-F) G-3(3-F) CHF 2 Q-1(2-F,4-F) G-3(3-Cl) CHF 2 Q-1(2-F,4-F) G-3(3-CH 3 ) CHF 2 Q-1(2-F,4-F) G-3(3-CF 3 ) CHF 2Q-1(3-F,4-F) G-1(4-F) CHF 2 Q-1(3-F,4-F) G-3(3-F) CHF 2 Q-1(3-F,4-F) G-3(3-Cl) CHF 2 Q-1(3-F,4-F) G-3(3-CH 3 ) CHF 2 Q-1(3-F,4-F) G-3(3-CF 3 ) CHF 2 Q-2(4-F) G-1(4-F) CHF 2 Q-2(4-F) G-3(3-F) CHF 2 Q-2(4-F) G-3(3-Cl) CHF 2 Q-2(4-F) G-3(3-CH 3 ) CHF 2 Q-2(4-F) G-3(3-CF 3 ) CHF 2 Q-3 G-1(4-F) CHF 2 Q-3 G-3(3-F) CHF 2 Q-3 G-3(3-Cl) CHF 2 Q-3 G-3(3-CH 3 ) CHF 2 Q-3 G-3(3-CF 3 ) CHF 2 Q-3(4-F) G-1(4-F) CHF 2 Q-3(4-F) G-3(3-F) CHF 2 Q-3(4-F) G-3(3-Cl) CHF 2 Q-3(4-F) G-3(3-CH 3 ) CHF 2 Q-3(4-F) G-3(3-CF 3) CHF 2 Q-3(4-Cl) G-1(4-F) CHF 2 Q-3(4-Cl) G-3(3-F) CHF 2 Q-3(4-Cl) G-3(3-Cl) CHF 2 Q-3(4-Cl) G-3(3-CH 3 ) CHF 2 Q-3(4-Cl) G-3(3-CF 3 ) CHF 2 Q-3(4-CH 3 ) G-1(4-F) CHF 2 Q-3(4-CH 3 ) G-3(3-F) CHF 2 Q-3(4-CH 3 ) G-3(3-Cl) CHF 2 Q-3(4-CH 3 ) G-3(3-CH 3 ) CHF 2 Q-3(4-CH 3 ) G-3(3-CF 3 ) CHF 2 Q-3(3-CH 3 ) G-1(4-F) CHF 2 Q-3(3-CH 3 ) G-3(3-F) CHF 2 Q-3(3-CH 3 ) G-3(3-Cl) CHF 2 Q-3(3-CH 3 ) G-3(3-CH 3 ) CHF 2 Q-3(3-CH 3 ) G-3(3-CF 3 ) CHF 2 Q-3(3-OCH 3 ) G-1(4-F) CHF2 Q-3(3-OCH 3 ) G-3(3-F) CHF 2 Q-3(3-OCH 3 ) G-3(3-Cl) CHF 2 Q-3(3-OCH 3 ) G-3(3-CH 3 ) CHF 2 Q-3(3-OCH 3 ) G-3(3-CF 3 ) CHF 2 Q-4 G-1(4-F) CHF 2 Q-4 G-3(3-F) CHF 2 Q-4 G-3(3-Cl) CHF 2 Q-4 G-3(3-CH 3 ) CHF 2 Q-4 G-3(3-CF 3 ) CHF 2 Q-4(4-CH 3 ) G-1(4-F) CHF 2 Q-4(4-CH 3 ) G-3(3-F) CHF 2 Q-4(4-CH 3 ) G-3(3-Cl) CHF 2 Q-4(4-CH 3 ) G-3(3-CH 3 ) CHF 2 Q-4(4-CH 3 ) G-3(3-CF 3 ) CHF 2 Q-4(3-CH 3 ) G-1(4-F) CHF 2 Q-4(3-CH 3 ) G-3(3-F) CHF 2 Q-4(3-CH 3 ) G-3(3-Cl) CHF 2 Q-4(3-CH 3 ) G-3(3-CH 3 ) CHF 2 Q-4(3-CH 3 ) G-3(3-CF 3 ) CHF 2 Q-9 G-1(4-F) CHF 2 Q-9 G-3(3-F) CHF 2 Q-9 G-3(3-Cl) CHF 2 Q-9 G-3(3-CH 3 ) CHF 2 Q-9 G-3(3-CF 3 ) CHF 2 Q-12a G-1(4-F) CHF 2 Q-12a G-3(3-F) CHF 2 Q-12a G-3(3-Cl) CHF 2 Q-12a G-3(3-CH 3 ) CHF 2 Q-12a G-3(3-CF 3 ) CF 3 Q-1(3-F) G-1(4-F) CF 3 Q-1(3-F) G-3(3-F) CF 3 Q-1(3-F) G-3(3-Cl) CF 3 Q-1(3-F) G-3(3-CH 3 ) CF 3 Q-1(3-F) G-3(3-CF 3 ) CF 3 Q-1(4-F) G-1(4-F) CF 3 Q-1(4-F) G-3(3-F) CF 3Q-1(4-F) G-3(3-Cl) CF 3 Q-1(4-F) G-3(3-CH 3 ) CF 3 Q-1(4-F) G-3(3-CF 3 ) CF 3 Q-1(4-CN) G-1(4-F) CF 3 Q-1(4-CN) G-3(3-F) CF 3 Q-1(4-CN) G-3(3-Cl) CF 3 Q-1(4-CN) G-3(3-CH 3 ) CF 3 Q-1(4-CN) G-3(3-CF 3 ) CF 3 Q-1(4-CF 3 ) G-1(4-F) CF 3 Q-1(4-CF 3 ) G-3(3-F) CF 3 Q-1(4-CF 3 ) G-3(3-Cl) CF 3 Q-1(4-CF 3 ) G-3(3-CH 3 ) CF 3 Q-1(4-CF 3 ) G-3(3-CF 3 ) CF 3 Q-1(2-F,4-F) G-1(4-F) CF 3 Q-1(2-F,4-F) G-3(3-F) CF 3 Q-1(2-F,4-F) G-3(3-Cl) CF 3 Q-1(2-F,4-F) G-3(3-CH 3 ) CF 3 Q-1(2-F,4-F) G-3(3-CF 3 ) CF 3 Q-1(3-F,4-F) G-1(4-F) CF 3 Q-1(3-F,4-F) G-3(3-F) CF 3 Q-1(3-F,4-F) G-3(3-Cl) CF 3 Q-1(3-F,4-F) G-3(3-CH 3 ) CF 3 Q-1(3-F,4-F) G-3(3-CF 3 ) CF 3 Q-2(4-F) G-1(4-F) CF 3 Q-2(4-F) G-3(3-F) CF 3 Q-2(4-F) G-3(3-Cl) CF 3 Q-2(4-F) G-3(3-CH 3 ) CF 3 Q-2(4-F) G-3(3-CF 3 ) CF 3 Q-3 G-1(4-F) CF 3 Q-3 G-3(3-F) CF 3 Q-3 G-3(3-Cl) CF 3 Q-3 G-3(3-CH 3 ) CF 3 Q-3 G-3(3-CF 3 ) CF 3 Q-3(4-F) G-1(4-F) CF 3 Q-3(4-F) G-3(3-F) CF 3 Q-3(4-F) G-3(3-Cl) CF 3 Q-3(4-F) G-3(3-CH 3 ) CF 3 Q-3(4-F) G-3(3-CF3 ) CF 3 Q-3(4-Cl) G-1(4-F) CF 3 Q-3(4-Cl) G-3(3-F) CF 3 Q-3(4-Cl) G-3(3-Cl) CF 3 Q-3(4-Cl) G-3(3-CH 3 ) CF 3 Q-3(4-Cl) G-3(3-CF 3 ) CF 3 Q-3(4-CH 3 ) G-1(4-F) CF 3 Q-3(4-CH 3 ) G-3(3-F) CF 3 Q-3(4-CH 3 ) G-3(3-Cl) CF 3 Q-3(4-CH 3 ) G-3(3-CH 3 ) CF 3 Q-3(4-CH 3 ) G-3(3-CF 3 ) CF 3 Q-3(3-CH 3 ) G-1(4-F) CF 3 Q-3(3-CH 3 ) G-3(3-F) CF 3 Q-3(3-CH 3 ) G-3(3-Cl) CF 3 Q-3(3-CH 3 ) G-3(3-CH 3 ) CF 3 Q-3(3-CH 3 ) G-3(3-CF 3 ) CF 3 Q-3(3-OCH 3 ) G-1(4-F) CF3 Q-3(3-OCH 3 ) G-3(3-F) CF 3 Q-3(3-OCH 3 ) G-3(3-Cl) CF 3 Q-3(3-OCH 3 ) G-3(3-CH 3 ) CF 3 Q-3(3-OCH 3 ) G-3(3-CF 3 ) CF 3 Q-4 G-1(4-F) CF 3 Q-4 G-3(3-F) CF 3 Q-4 G-3(3-Cl) CF 3 Q-4 G-3(3-CH 3 ) CF 3 Q-4 G-3(3-CF 3 ) CF 3 Q-4(4-CH 3 ) G-1(4-F) CF 3 Q-4(4-CH 3 ) G-3(3-F) CF 3 Q-4(4-CH 3 ) G-3(3-Cl) CF 3 Q-4(4-CH 3 ) G-3(3-CH 3 ) CF 3 Q-4(4-CH 3 ) G-3(3-CF 3 ) CF 3 Q-4(3-CH 3 ) G-1(4-F) CF 3 Q-4(3-CH 3 ) G-3(3-F) CF 3 Q-4(3-CH 3 ) G-3(3-Cl) CF3 Q-4(3-CH 3 ) G-3(3-CH 3 ) CF 3 Q-4(3-CH 3 ) G-3(3-CF 3 ) CF 3 Q-9 G-1(4-F) CF 3 Q-9 G-3(3-F) CF 3 Q-9 G-3(3-Cl) CF 3 Q-9 G-3(3-CH 3 ) CF 3 Q-9 G-3(3-CF 3 ) CF 3 Q-12a G-1(4-F) CF 3 Q-12a G-3(3-F) CF 3 Q-12a G-3(3-Cl) CF 3 Q-12a G-3(3-CH 3 ) CF 3 Q-12a G-3(3-CF 3 ) CF 3 Q-1(4-F) G-1(4-NO 2 ) CF 3 Q-1(4-F) G-1(4-NH 2 ) CF 3 Q-1(4-F) G-1(5-F) CF 3 Q-1(4-F) G-1(5-NO 2 ) CF 3 Q-1(4-F) G-1(5-NH 2 ) CF 3 Q-1(4-F) G-3(3-NO 2 ) CF 3 Q-1(4-F) G-3(3-NH 2 ) CF 3 Q-1(4-CN) G-1(4-NO 2 ) CF 3 Q-1(4-CN) G-1(4-NH 2 ) CF 3 Q-1(4-CN) G-1(5-F) CF 3 Q-1(4-CN) G-1(5-NO 2 ) CF 3 Q-1(4-CN) G-1(5-NH 2 ) CF 3 Q-1(4-CN) G-3(3-NO 2 ) CF 3 Q-1(4-CN) G-3(3-NH 2 ) CF 3 Q-2(4-F) G-1(4-NO 2 ) CF 3 Q-2(4-F) G-1(4-NH 2 ) CF 3 Q-2(4-F) G-1(5-F) CF 3 Q-2(4-F) G-1(5-NO 2 ) CF 3 Q-2(4-F) G-1(5-NH 2 ) CF 3 Q-2(4-F) G-3(3-NO 2 ) CF 3 Q-2(4-F) G-3(3-NH 2 ) CF 3 Q-2(4-Cl) G-1(4-F) CF 3 Q-2(4-Cl) G-1(4-NO 2 ) CF 3 Q-2(4-Cl) G-1(4-NH 2 ) CF 3Q-2(4-Cl) G-1(5-F) CF 3 Q-2(4-Cl) G-1(5-NO 2 ) CF 3 Q-2(4-Cl) G-1(5-NH 2 ) CF 3 Q-2(4-Cl) G-3(3-F) CF 3 Q-2(4-Cl) G-3(3-Cl) CF 3 Q-2(4-Cl) G-3(3-CH 3 ) CF 3 Q-2(4-Cl) G-3(3-CF 3 ) CF 3 Q-2(4-Cl) G-3(3-NO 2 ) CF 3 Q-2(4-Cl) G-3(3-NH 2 ) CF 3 Q-2(4-CN) G-1(4-F) CF 3 Q-2(4-CN) G-1(4-NO 2 ) CF 3 Q-2(4-CN) G-1(4-NH 2 ) CF 3 Q-2(4-CN) G-1(5-F) CF 3 Q-2(4-CN) G-1(5-NO 2 ) CF 3 Q-2(4-CN) G-1(5-NH 2 ) CF 3 Q-2(4-CN) G-3(3-F) CF 3 Q-2(4-CN) G-3(3-Cl) CF 3 Q-2(4-CN) G-3(3-CH 3 ) CF 3Q-2(4-CN) G-3(3-CF 3 ) CF 3 Q-2(4-CN) G-3(3-NO 2 ) CF 3 Q-2(4-CN) G-3(3-NH 2 ) CF 3 Q-3 G-1(4-NO 2 ) CF 3 Q-3 G-1(4-NH 2 ) CF 3 Q-3 G-1(5-F) CF 3 Q-3 G-1(5-NO 2 ) CF 3 Q-3 G-1(5-NH 2 ) CF 3 Q-3 G-3(3-NO 2 ) CF 3 Q-3 G-3(3-NH 2 ) CF 3 Q-3(3-CH 3 ) G-1(4-NO 2 ) CF 3 Q-3(3-CH 3 ) G-1(4-NH 2 ) CF 3 Q-3(3-CH 3 ) G-1(5-F) CF 3 Q-3(3-CH 3 ) G-1(5-NO 2 ) CF 3 Q-3(3-CH 3 ) G-1(5-NH 2 ) CF 3 Q-3(3-CH 3 ) G-3(3-NO 2 ) CF 3 Q-3(3-CH 3 ) G-3(3-NH2 ) CF 3 Q-3(3-Cl) G-1(4-F) CF 3 Q-3(3-Cl) G-1(4-NO 2 ) CF 3 Q-3(3-Cl) G-1(4-NH 2 ) CF 3 Q-3(3-Cl) G-1(5-F) CF 3 Q-3(3-Cl) G-1(5-NO 2 ) CF 3 Q-3(3-Cl) G-1(5-NH 2 ) CF 3 Q-3(3-Cl) G-3(3-F) CF 3 Q-3(3-Cl) G-3(3-Cl) CF 3 Q-3(3-Cl) G-3(3-CH 3 ) CF 3 Q-3(3-Cl) G-3(3-CF 3 ) CF 3 Q-3(3-Cl) G-3(3-NO 2 ) CF 3 Q-3(3-Cl) G-3(3-NH 2 ) CF 3 Q-3(3-F) G-1(4-F) CF 3 Q-3(3-F) G-1(4-NO 2 ) CF 3 Q-3(3-F) G-1(4-NH 2 ) CF 3 Q-3(3-F) G-1(5-F) CF 3 Q-3(3-F) G-1(5-NO 2 ) CF 3 Q-3(3-F) G-1(5-NH 2) CF 3 Q-3(3-F) G-3(3-F) CF 3 Q-3(3-F) G-3(3-Cl) CF 3 Q-3(3-F) G-3(3-CH 3 ) CF 3 Q-3(3-F) G-3(3-CF 3 ) CF 3 Q-3(3-F) G-3(3-NO 2 ) CF 3 Q-3(3-F) G-3(3-NH 2 ) CF 3 Q-3(4-Br) G-1(4-F) CF 3 Q-3(4-Br) G-1(4-NO 2 ) CF 3 Q-3(4-Br) G-1(4-NH 2 ) CF 3 Q-3(4-Br) G-1(5-F) CF 3 Q-3(4-Br) G-1(5-NO 2 ) CF 3 Q-3(4-Br) G-1(5-NH 2 ) CF 3 Q-3(4-Br) G-3(3-F) CF 3 Q-3(4-Br) G-3(3-Cl) CF 3 Q-3(4-Br) G-3(3-CH 3 ) CF 3 Q-3(4-Br) G-3(3-CF 3 ) CF 3 Q-3(4-Br) G-3(3-NO 2 ) CF 3 Q-3(4-Br) G-3(3-NH 2 ) CF 3 Q-3(4-CH 3 ) G-1(4-NO 2 ) CF 3 Q-3(4-CH 3 ) G-1(4-NH 2 ) CF 3 Q-3(4-CH 3 ) G-1(5-F) CF 3 Q-3(4-CH 3 ) G-1(5-NO 2 ) CF 3 Q-3(4-CH 3 ) G-1(5-NH 2 ) CF 3 Q-3(4-CH 3 ) G-3(3-NO 2 ) CF 3 Q-3(4-CH 3 ) G-3(3-NH 2 ) CF 3 Q-3(4-Cl) G-1(4-NO 2 ) CF 3 Q-3(4-Cl) G-1(4-NH 2 ) CF 3 Q-3(4-Cl) G-1(5-F) CF 3 Q-3(4-Cl) G-1(5-NO 2 ) CF 3 Q-3(4-Cl) G-1(5-NH 2 ) CF 3 Q-3(4-Cl) G-3(3-NO 2 ) CF 3 Q-3(4-Cl) G-3(3-NH 2 ) CF 3 Q-3(4-CN) G-1(4-F) CF 3 Q-3(4-CN) G-1(4-NO2 ) CF 3 Q-3(4-CN) G-1(4-NH 2 ) CF 3 Q-3(4-CN) G-1(5-F) CF 3 Q-3(4-CN) G-1(5-NO 2 ) CF 3 Q-3(4-CN) G-1(5-NH 2 ) CF 3 Q-3(4-CN) G-3(3-F) CF 3 Q-3(4-CN) G-3(3-Cl) CF 3 Q-3(4-CN) G-3(3-CH 3 ) CF 3 Q-3(4-CN) G-3(3-CF 3 ) CF 3 Q-3(4-CN) G-3(3-NO 2 ) CF 3 Q-3(4-CN) G-3(3-NH 2 ) CF 3 Q-3(4-F) G-1(4-NO 2 ) CF 3 Q-3(4-F) G-1(4-NH 2 ) CF 3 Q-3(4-F) G-1(5-F) CF 3 Q-3(4-F) G-1(5-NO 2 ) CF 3 Q-3(4-F) G-1(5-NH 2 ) CF 3 Q-3(4-F) G-3(3-NO 2 ) CF 3 Q-3(4-F) G-3(3-NH 2 ) CF 3Q-3(6-F) G-1(4-F) CF 3 Q-3(6-F) G-1(4-NO 2 ) CF 3 Q-3(6-F) G-1(4-NH 2 ) CF 3 Q-3(6-F) G-1(5-F) CF 3 Q-3(6-F) G-1(5-NO 2 ) CF 3 Q-3(6-F) G-1(5-NH 2 ) CF 3 Q-3(6-F) G-3(3-F) CF 3 Q-3(6-F) G-3(3-Cl) CF 3 Q-3(6-F) G-3(3-CH 3 ) CF 3 Q-3(6-F) G-3(3-CF 3 ) CF 3 Q-3(6-F) G-3(3-NO 2 ) CF 3 Q-3(6-F) G-3(3-NH 2 ) CF 3 Q-4 G-1(4-NO 2 ) CF 3 Q-4 G-1(4-NH 2 ) CF 3 Q-4 G-1(5-F) CF 3 Q-4 G-1(5-NO 2 ) CF 3 Q-4 G-1(5-NH 2 ) CF 3 Q-4 G-3(3-NO 2 ) CF 3 Q-4 G-3(3-NH 2 ) CF 3 Q-4(3-CH 3 ) G-1(4-NO 2 ) CF 3 Q-4(3-CH 3 ) G-1(4-NH 2 ) CF 3 Q-4(3-CH 3 ) G-1(5-F) CF 3 Q-4(3-CH 3 ) G-1(5-NO 2 ) CF 3 Q-4(3-CH 3 ) G-1(5-NH 2 ) CF 3 Q-4(3-CH 3 ) G-3(3-NO 2 ) CF 3 Q-4(3-CH 3 ) G-3(3-NH 2 ) CF 3 Q-4(3-Cl) G-1(4-F) CF 3 Q-4(3-Cl) G-1(4-NO 2 ) CF 3 Q-4(3-Cl) G-1(4-NH 2 ) CF 3 Q-4(3-Cl) G-1(5-F) CF 3 Q-4(3-Cl) G-1(5-NO 2 ) CF 3 Q-4(3-Cl) G-1(5-NH 2 ) CF 3 Q-4(3-Cl) G-3(3-F) CF 3 Q-4(3-Cl) G-3(3-Cl) CF 3 Q-4(3-Cl) G-3(3-CH 3 ) CF 3Q-4(3-Cl) G-3(3-CF 3 ) CF 3 Q-4(3-Cl) G-3(3-NO 2 ) CF 3 Q-4(3-Cl) G-3(3-NH 2 ) CF 3 Q-4(4-Br) G-1(4-F) CF 3 Q-4(4-Br) G-1(4-NO 2 ) CF 3 Q-4(4-Br) G-1(4-NH 2 ) CF 3 Q-4(4-Br) G-1(5-F) CF 3 Q-4(4-Br) G-1(5-NO 2 ) CF 3 Q-4(4-Br) G-1(5-NH 2 ) CF 3 Q-4(4-Br) G-3(3-F) CF 3 Q-4(4-Br) G-3(3-Cl) CF 3 Q-4(4-Br) G-3(3-CH 3 ) CF 3 Q-4(4-Br) G-3(3-CF 3 ) CF 3 Q-4(4-Br) G-3(3-NO 2 ) CF 3 Q-4(4-Br) G-3(3-NH 2 ) CF 3 Q-4(4-Cl) G-1(4-F) CF 3 Q-4(4-Cl) G-1(4-NO 2 ) CF 3 Q-4(4-Cl) G-1(4-NH 2 ) CF3 Q-4(4-Cl) G-1(5-F) CF 3 Q-4(4-Cl) G-1(5-NO 2 ) CF 3 Q-4(4-Cl) G-1(5-NH 2 ) CF 3 Q-4(4-Cl) G-3(3-F) CF 3 Q-4(4-Cl) G-3(3-Cl) CF 3 Q-4(4-Cl) G-3(3-CH 3 ) CF 3 Q-4(4-Cl) G-3(3-CF 3 ) CF 3 Q-4(4-Cl) G-3(3-NO 2 ) CF 3 Q-4(4-Cl) G-3(3-NH 2 ) CF 3 Q-9 G-1(4-NO 2 ) CF 3 Q-9 G-1(4-NH 2 ) CF 3 Q-9 G-1(5-F) CF 3 Q-9 G-1(5-NO 2 ) CF 3 Q-9 G-1(5-NH 2 ) CF 3 Q-9 G-3(3-NO 2 ) CF 3 Q-9 G-3(3-NH 2 ) CF 3 Q-12a G-1(4-NO 2 ) CF 3 Q-12a G-1(4-NH 2 ) CF 3 Q-12a G-1(5-F) CF 3 Q-12a G-1(5-NO 2 ) CF 3 Q-12a G-1(5-NH 2 ) CF 3 Q-12a G-3(3-NO 2 ) CF 3 Q-12a G-3(3-NH 2 ) Cl Q-1(4-F) G-1(4-F) Cl Q-1(4-F) G-1(4-NO 2 ) Cl Q-1(4-F) G-1(4-NH 2 ) Cl Q-1(4-F) G-1(5-F) Cl Q-1(4-F) G-1(5-NO 2 ) Cl Q-1(4-F) G-1(5-NH 2 ) Cl Q-1(4-F) G-3(3-F) Cl Q-1(4-F) G-3(3-Cl) Cl Q-1(4-F) G-3(3-CH 3 ) Cl Q-1(4-F) G-3(3-CF 3 ) Cl Q-1(4-F) G-3(3-NO 2 ) Cl Q-1(4-F) G-3(3-NH 2 ) Cl Q-1(4-CN) G-1(4-F) Cl Q-1(4-CN) G-1(4-NO 2 ) Cl Q-1(4-CN) G-1(4-NH 2 ) Cl Q-1(4-CN) G-1(5-F) Cl Q-1(4-CN) G-1(5-NO 2 ) Cl Q-1(4-CN) G-1(5-NH 2 ) Cl Q-1(4-CN) G-3(3-F) Cl Q-1(4-CN) G-3(3-Cl) Cl Q-1(4-CN) G-3(3-CH 3 ) Cl Q-1(4-CN) G-3(3-CF 3 ) Cl Q-1(4-CN) G-3(3-NO 2 ) Cl Q-1(4-CN) G-3(3-NH 2 ) Cl Q-2(4-F) G-1(4-F) Cl Q-2(4-F) G-1(4-NO 2 ) Cl Q-2(4-F) G-1(4-NH 2 ) Cl Q-2(4-F) G-1(5-F) Cl Q-2(4-F) G-1(5-NO 2 ) Cl Q-2(4-F) G-1(5-NH 2 ) Cl Q-2(4-F) G-3(3-F) Cl Q-2(4-F) G-3(3-Cl) Cl Q-2(4-F) G-3(3-CH 3 ) Cl Q-2(4-F) G-3(3-CF 3 ) Cl Q-2(4-F) G-3(3-NO 2 ) Cl Q-2(4-F) G-3(3-NH 2 ) Cl Q-2(4-Cl) G-1(4-F) Cl Q-2(4-Cl) G-1(4-NO 2 ) Cl Q-2(4-Cl) G-1(4-NH 2 ) Cl Q-2(4-Cl) G-1(5-F) Cl Q-2(4-Cl) G-1(5-NO 2 ) Cl Q-2(4-Cl) G-1(5-NH 2 ) Cl Q-2(4-Cl) G-3(3-F) Cl Q-2(4-Cl) G-3(3-Cl) Cl Q-2(4-Cl) G-3(3-CH 3 ) Cl Q-2(4-Cl) G-3(3-CF 3 ) Cl Q-2(4-Cl) G-3(3-NO 2 ) Cl Q-2(4-Cl) G-3(3-NH 2 ) Cl Q-2(4-CN) G-1(4-F) Cl Q-2(4-CN) G-1(4-NO 2 ) Cl Q-2(4-CN) G-1(4-NH 2 ) Cl Q-2(4-CN) G-1(5-F) Cl Q-2(4-CN) G-1(5-NO 2 ) Cl Q-2(4-CN) G-1(5-NH 2 ) Cl Q-2(4-CN) G-3(3-F) Cl Q-2(4-CN) G-3(3-Cl) Cl Q-2(4-CN) G-3(3-CH 3 ) Cl Q-2(4-CN) G-3(3-CF 3 ) Cl Q-2(4-CN) G-3(3-NO 2 ) Cl Q-2(4-CN) G-3(3-NH 2 ) Cl Q-3 G-1(4-F) Cl Q-3 G-1(4-NO 2 ) Cl Q-3 G-1(4-NH 2 ) Cl Q-3 G-1(5-F) Cl Q-3 G-1(5-NO 2 ) Cl Q-3 G-1(5-NH 2 ) Cl Q-3 G-3(3-F) Cl Q-3 G-3(3-Cl) Cl Q-3 G-3(3-CH 3 ) Cl Q-3 G-3(3-CF 3 ) Cl Q-3 G-3(3-NO 2 ) Cl Q-3 G-3(3-NH 2 ) Cl Q-3(3-CH 3 ) G-1(4-F) Cl Q-3(3-CH 3 ) G-1(4-NO 2 ) Cl Q-3(3-CH 3 ) G-1(4-NH 2 ) Cl Q-3(3-CH 3 ) G-1(5-F) Cl Q-3(3-CH 3 ) G-1(5-NO 2 ) Cl Q-3(3-CH 3 ) G-1(5-NH 2 ) Cl Q-3(3-CH 3 ) G-3(3-F) Cl Q-3(3-CH 3 ) G-3(3-Cl) Cl Q-3(3-CH 3 ) G-3(3-CH 3 ) Cl Q-3(3-CH 3 ) G-3(3-CF 3 ) Cl Q-3(3-CH 3 ) G-3(3-NO 2 ) Cl Q-3(3-CH 3 ) G-3(3-NH 2 ) Cl Q-3(3-Cl) G-1(4-F) Cl Q-3(3-Cl) G-1(4-NO 2 ) Cl Q-3(3-Cl) G-1(4-NH 2 ) Cl Q-3(3-Cl) G-1(5-F) Cl Q-3(3-Cl) G-1(5-NO 2 ) Cl Q-3(3-Cl) G-1(5-NH 2 ) Cl Q-3(3-Cl) G-3(3-F) Cl Q-3(3-Cl) G-3(3-Cl) Cl Q-3(3-Cl) G-3(3-CH 3 ) Cl Q-3(3-Cl) G-3(3-CF 3 ) Cl Q-3(3-Cl) G-3(3-NO 2 ) Cl Q-3(3-Cl) G-3(3-NH 2 ) Cl Q-3(3-F) G-1(4-F) Cl Q-3(3-F) G-1(4-NO 2 ) Cl Q-3(3-F) G-1(4-NH 2 ) Cl Q-3(3-F) G-1(5-F) Cl Q-3(3-F) G-1(5-NO 2 ) Cl Q-3(3-F) G-1(5-NH 2 ) Cl Q-3(3-F) G-3(3-F) Cl Q-3(3-F) G-3(3-Cl) Cl Q-3(3-F) G-3(3-CH 3 ) Cl Q-3(3-F) G-3(3-CF 3 ) Cl Q-3(3-F) G-3(3-NO 2 ) Cl Q-3(3-F) G-3(3-NH 2 ) Cl Q-3(4-Br) G-1(4-F) Cl Q-3(4-Br) G-1(4-NO 2 ) Cl Q-3(4-Br) G-1(4-NH 2 ) Cl Q-3(4-Br) G-1(5-F) Cl Q-3(4-Br) G-1(5-NO 2 ) Cl Q-3(4-Br) G-1(5-NH 2 ) Cl Q-3(4-Br) G-3(3-F) Cl Q-3(4-Br) G-3(3-Cl) Cl Q-3(4-Br) G-3(3-CH 3 ) Cl Q-3(4-Br) G-3(3-CF 3 ) Cl Q-3(4-Br) G-3(3-NO 2 ) Cl Q-3(4-Br) G-3(3-NH 2 ) Cl Q-3(4-CH 3 ) G-1(4-F) Cl Q-3(4-CH 3 ) G-1(4-NO 2 ) Cl Q-3(4-CH 3 ) G-1(4-NH 2 ) Cl Q-3(4-CH 3 ) G-1(5-F) Cl Q-3(4-CH 3 ) G-1(5-NO 2 ) Cl Q-3(4-CH 3 ) G-1(5-NH 2 ) Cl Q-3(4-CH 3 ) G-3(3-F) Cl Q-3(4-CH 3 ) G-3(3-Cl) Cl Q-3(4-CH 3 ) G-3(3-CH 3) Cl Q-3(4-CH 3 ) G-3(3-CF 3 ) Cl Q-3(4-CH 3 ) G-3(3-NO 2 ) Cl Q-3(4-CH 3 ) G-3(3-NH 2 ) Cl Q-3(4-Cl) G-1(4-F) Cl Q-3(4-Cl) G-1(4-NO 2 ) Cl Q-3(4-Cl) G-1(4-NH 2 ) Cl Q-3(4-Cl) G-1(5-F) Cl Q-3(4-Cl) G-1(5-NO 2 ) Cl Q-3(4-Cl) G-1(5-NH 2 ) Cl Q-3(4-Cl) G-3(3-F) Cl Q-3(4-Cl) G-3(3-Cl) Cl Q-3(4-Cl) G-3(3-CH 3 ) Cl Q-3(4-Cl) G-3(3-CF 3 ) Cl Q-3(4-Cl) G-3(3-NO 2 ) Cl Q-3(4-Cl) G-3(3-NH 2 ) Cl Q-3(4-CN) G-1(4-F) Cl Q-3(4-CN) G-1(4-NO 2 ) Cl Q-3(4-CN) G-1(4-NH 2 ) Cl Q-3(4-CN) G-1(5-F) Cl Q-3(4-CN) G-1(5-NO 2 ) Cl Q-3(4-CN) G-1(5-NH 2 ) Cl Q-3(4-CN) G-3(3-F) Cl Q-3(4-CN) G-3(3-Cl) Cl Q-3(4-CN) G-3(3-CH 3 ) Cl Q-3(4-CN) G-3(3-CF 3 ) Cl Q-3(4-CN) G-3(3-NO 2 ) Cl Q-3(4-CN) G-3(3-NH 2 ) Cl Q-3(4-F) G-1(4-F) Cl Q-3(4-F) G-1(4-NO 2 ) Cl Q-3(4-F) G-1(4-NH 2 ) Cl Q-3(4-F) G-1(5-F) Cl Q-3(4-F) G-1(5-NO 2 ) Cl Q-3(4-F) G-1(5-NH 2 ) Cl Q-3(4-F) G-3(3-F) Cl Q-3(4-F) G-3(3-Cl) Cl Q-3(4-F) G-3(3-CH 3 ) Cl Q-3(4-F) G-3(3-CF 3 ) Cl Q-3(4-F) G-3(3-NO 2 ) Cl Q-3(4-F) G-3(3-NH 2 ) Cl Q-3(6-F) G-1(4-F) Cl Q-3(6-F) G-1(4-NO 2 ) Cl Q-3(6-F) G-1(4-NH 2 ) Cl Q-3(6-F) G-1(5-F) Cl Q-3(6-F) G-1(5-NO 2 ) Cl Q-3(6-F) G-1(5-NH 2 ) Cl Q-3(6-F) G-3(3-F) Cl Q-3(6-F) G-3(3-Cl) Cl Q-3(6-F) G-3(3-CH 3 ) Cl Q-3(6-F) G-3(3-CF 3 ) Cl Q-3(6-F) G-3(3-NO 2 ) Cl Q-3(6-F) G-3(3-NH 2 ) Cl Q-4 G-1(4-F) Cl Q-4 G-1(4-NO 2 ) Cl Q-4 G-1(4-NH 2 ) Cl Q-4 G-1(5-F) Cl Q-4 G-1(5-NO 2 ) Cl Q-4 G-1(5-NH 2 ) Cl Q-4 G-3(3-F) Cl Q-4 G-3(3-Cl) Cl Q-4 G-3(3-CH 3 ) Cl Q-4 G-3(3-CF 3 ) Cl Q-4 G-3(3-NO 2 ) Cl Q-4 G-3(3-NH 2 ) Cl Q-4(3-CH 3 ) G-1(4-F) Cl Q-4(3-CH 3 ) G-1(4-NO 2 ) Cl Q-4(3-CH 3 ) G-1(4-NH 2 ) Cl Q-4(3-CH 3 ) G-1(5-F) Cl Q-4(3-CH 3 ) G-1(5-NO 2 ) Cl Q-4(3-CH3 ) G-1(5-NH 2 ) Cl Q-4(3-CH 3 ) G-3(3-F) Cl Q-4(3-CH 3 ) G-3(3-Cl) Cl Q-4(3-CH 3 ) G-3(3-CH 3 ) Cl Q-4(3-CH 3 ) G-3(3-CF 3 ) Cl Q-4(3-CH 3 ) G-3(3-NO 2 ) Cl Q-4(3-CH 3 ) G-3(3-NH 2 ) Cl Q-4(3-Cl) G-1(4-F) Cl Q-4(3-Cl) G-1(4-NO 2 ) Cl Q-4(3-Cl) G-1(4-NH 2 ) Cl Q-4(3-Cl) G-1(5-F) Cl Q-4(3-Cl) G-1(5-NO 2 ) Cl Q-4(3-Cl) G-1(5-NH 2 ) Cl Q-4(3-Cl) G-3(3-F) Cl Q-4(3-Cl) G-3(3-Cl) Cl Q-4(3-Cl) G-3(3-CH 3 ) Cl Q-4(3-Cl) G-3(3-CF 3 ) Cl Q-4(3-Cl) G-3(3-NO 2 ) Cl Q-4(3-Cl) G-3(3-NH 2 ) Cl Q-4(4-Br) G-1(4-F) Cl Q-4(4-Br) G-1(4-NO 2 ) Cl Q-4(4-Br) G-1(4-NH 2 ) Cl Q-4(4-Br) G-1(5-F) Cl Q-4(4-Br) G-1(5-NO 2 ) Cl Q-4(4-Br) G-1(5-NH 2 ) Cl Q-4(4-Br) G-3(3-F) Cl Q-4(4-Br) G-3(3-Cl) Cl Q-4(4-Br) G-3(3-CH 3 ) Cl Q-4(4-Br) G-3(3-CF 3 ) Cl Q-4(4-Br) G-3(3-NO 2 ) Cl Q-4(4-Br) G-3(3-NH 2 ) Cl Q-4(4-Cl) G-1(4-F) Cl Q-4(4-Cl) G-1(4-NO 2 ) Cl Q-4(4-Cl) G-1(4-NH 2 ) Cl Q-4(4-Cl) G-1(5-F) Cl Q-4(4-Cl) G-1(5-NO 2 ) Cl Q-4(4-Cl) G-1(5-NH 2 ) Cl Q-4(4-Cl) G-3(3-F) Cl Q-4(4-Cl) G-3(3-Cl) Cl Q-4(4-Cl) G-3(3-CH 3 ) Cl Q-4(4-Cl) G-3(3-CF 3 ) Cl Q-4(4-Cl) G-3(3-NO 2 ) Cl Q-4(4-Cl) G-3(3-NH 2 ) Cl Q-9 G-1(4-F) Cl Q-9 G-1(4-NO 2 ) Cl Q-9 G-1(4-NH 2 ) Cl Q-9 G-1(5-F) Cl Q-9 G-1(5-NO 2 ) Cl Q-9 G-1(5-NH 2 ) Cl Q-9 G-3(3-F) Cl Q-9 G-3(3-Cl) Cl Q-9 G-3(3-CH 3 ) Cl Q-9 G-3(3-CF 3 ) Cl Q-9 G-3(3-NO 2 ) Cl Q-9 G-3(3-NH 2 ) Cl Q-12a G-1(4-F) Cl Q-12a G-1(4-NO 2 ) Cl Q-12a G-1(4-NH 2 ) Cl Q-12a G-1(5-F) Cl Q-12a G-1(5-NO 2 ) Cl Q-12a G-1(5-NH 2 ) Cl Q-12a G-3(3-F) Cl Q-12a G-3(3-Cl) Cl Q-12a G-3(3-CH 3 ) Cl Q-12a G-3(3-CF 3 ) Cl Q-12a G-3(3-NO 2 ) Cl Q-12a G-3(3-NH 2 ) ―――――――――――――――― [Table 22]
[0171] [Chem.]
[0172] ――――――――――― Q G ――――――――――― Q-3(3-Cl) G-1(4-F) Q-3(3-Cl) G-1(2-F) Q-3(3-Cl) G-1(2-Cl) Q-3(3-Cl) G-3(3-F) Q-3(3-Cl) G-3(3-Cl) Q-3(3-Cl) G-3(3-CH 3 ) Q-3(3-Cl) G-3(3-CF 3 ) Q-3(3-CH 3 ) G-1(4-F) Q-3(3-CH 3 ) G-1(2-F) Q-3(3-CH 3 ) G-1(2-Cl) Q-3(3-CH 3 ) G-3(3-F) Q-3(3-CH 3 ) G-3(3-Cl) Q-3(3-CH 3 ) G-3(3-CH 3 ) Q-3(3-CH 3 ) G-3(3-CF 3 ) Q-4(3-Cl) G-1(4-F) Q-4(3-Cl) G-1(2-F) Q-4(3-Cl) G-1(2-Cl) Q-4(3-Cl) G-3(3-F) Q-4(3-Cl) G-3(3-Cl) Q-4(3-Cl) G-3(3-CH 3 ) Q-4(3-Cl) G-3(3-CF 3 ) Q-4(3-CH 3 ) G-1(4-F) Q-4(3-CH 3 ) G-1(2-F) Q-4(3-CH 3 ) G-1(2-Cl) Q-4(3-CH 3 ) G-3(3-F) Q-4(3-CH 3 ) G-3(3-Cl) Q-4(3-CH 3 ) G-3(3-CH 3 ) Q-4(3-CH 3 ) G-3(3-CF 3 ) Q-4(4-CH 3 ) G-1(4-F) Q-4(4-CH 3 ) G-1(2-F) Q-4(4-CH 3 ) G-1(2-Cl) Q-4(4-CH 3 ) G-3(3-F) Q-4(4-CH 3 ) G-3(3-Cl) Q-4(4-CH 3 ) G-3(3-CH 3 ) Q-4(4-CH 3 ) G-3(3-CF 3 ) Q-4(3-Br) G-1(4-F) Q-4(3-Br) G-1(2-F) Q-4(3-Br) G-1(2-Cl) Q-4(3-Br) G-3(3-F) Q-4(3-Br) G-3(3-Cl) Q-4(3-Br) G-3(3-CH 3 ) Q-4(3-Br) G-3(3-CF 3 ) Q-10(3-CH 3 ) G-1(4-F) Q-10(3-CH 3 ) G-1(2-F) Q-10(3-CH 3) G-1(2-Cl) Q-10(3-CH 3 ) G-3(3-F) Q-10(3-CH 3 ) G-3(3-Cl) Q-10(3-CH 3 ) G-3(3-CH 3 ) Q-10(3-CH 3 ) G-3(3-CF 3 ) Q-12a G-1(4-F) Q-12a G-1(2-F) Q-12a G-1(2-Cl) Q-12a G-3(3-F) Q-12a G-3(3-Cl) Q-12a G-3(3-CH 3 ) Q-12a G-3(3-CF 3 ) Q-47a G-1(4-F) Q-47a G-1(2-F) Q-47a G-1(2-Cl) Q-47a G-3(3-F) Q-47a G-3(3-Cl) Q-47a G-3(3-CH 3 ) Q-47a G-3(3-CF 3 ) Q-3(4-CN) G-1(4-F) Q-3(4-CN) G-1(2-F) Q-3(4-CN) G-1(2-Cl) Q-3(4-CN) G-3(3-F) Q-3(4-CN) G-3(3-Cl) Q-3(4-CN) G-3(3-CH 3 ) Q-3(4-CN) G-3(3-CF 3 ) Q-2(4-CN) G-1(4-F) Q-2(4-CN) G-1(2-F) Q-2(4-CN) G-1(2-Cl) Q-2(4-CN) G-3(3-F) Q-2(4-CN) G-3(3-Cl) Q-2(4-CN) G-3(3-CH 3 ) Q-2(4-CN) G-3(3-CF 3 ) Q-3(5-Cl) G-1(4-F) Q-3(5-Cl) G-1(2-F) Q-3(5-Cl) G-1(2-Cl) Q-3(5-Cl) G-3(3-F) Q-3(5-Cl) G-3(3-Cl) Q-3(5-Cl) G-3(3-CH 3 ) Q-3(5-Cl) G-3(3-CF 3 ) Q-3(5-CH 3 ) G-1(4-F) Q-3(5-CH 3 ) G-1(2-F) Q-3(5-CH 3 ) G-1(2-Cl) Q-3(5-CH 3 ) G-3(3-F) Q-3(5-CH 3 ) G-3(3-Cl) Q-3(5-CH 3 ) G-3(3-CH 3 ) Q-3(5-CH 3 ) G-3(3-CF 3 ) Q-6(3-CH 3 ) G-1(4-F) Q-6(3-CH 3 ) G-1(2-F) Q-6(3-CH 3 ) G-1(2-Cl) Q-6(3-CH 3 ) G-3(3-F) Q-6(3-CH 3 ) G-3(3-Cl) Q-6(3-CH 3) G-3(3-CH 3 ) Q-6(3-CH 3 ) G-3(3-CF 3 ) Q-6(3-Cl) G-1(4-F) Q-6(3-Cl) G-1(2-F) Q-6(3-Cl) G-1(2-Cl) Q-6(3-Cl) G-3(3-F) Q-6(3-Cl) G-3(3-Cl) Q-6(3-Cl) G-3(3-CH 3 ) Q-6(3-Cl) G-3(3-CF 3 ) Q-3(4-I) G-1(4-F) Q-3(4-I) G-1(2-F) Q-3(4-I) G-1(2-Cl) Q-3(4-I) G-3(3-F) Q-3(4-I) G-3(3-Cl) Q-3(4-I) G-3(3-CH 3 ) Q-3(4-I) G-3(3-CF 3 ) Q-10 G-1(4-F) Q-10 G-1(2-F) Q-10 G-1(2-Cl) Q-10 G-3(3-F) Q-10 G-3(3-Cl) Q-10 G-3(3-CH 3 ) Q-10 G-3(3-CF 3 ) Q-3(5-Br) G-1(4-F) Q-3(5-Br) G-1(2-F) Q-3(5-Br) G-1(2-Cl) Q-3(5-Br) G-3(3-F) Q-3(5-Br) G-3(3-Cl) Q-3(5-Br) G-3(3-CH 3 ) Q-3(5-Br) G-3(3-CF 3 ) Q-3(3-Br) G-1(4-F) Q-3(3-Br) G-1(2-F) Q-3(3-Br) G-1(2-Cl) Q-3(3-Br) G-3(3-F) Q-3(3-Br) G-3(3-Cl) Q-3(3-Br) G-3(3-CH 3 ) Q-3(3-Br) G-3(3-CF 3 ) Q-3(4-CF 3 ) G-1(4-F) Q-3(4-CF 3 ) G-1(2-F) Q-3(4-CF 3 ) G-1(2-Cl) Q-3(4-CF 3 ) G-3(3-F) Q-3(4-CF 3 ) G-3(3-Cl) Q-3(4-CF 3 ) G-3(3-CH 3 ) Q-3(4-CF 3 ) G-3(3-CF 3 ) Q-8(3-CH 3 ) G-1(4-F) Q-8(3-CH 3 ) G-1(2-F) Q-8(3-CH 3 ) G-1(2-Cl) Q-8(3-CH 3 ) G-3(3-F) Q-8(3-CH 3 ) G-3(3-Cl) Q-8(3-CH 3 ) G-3(3-CH 3 ) Q-8(3-CH 3 ) G-3(3-CF 3 ) Q-8(3-Cl) G-1(4-F) Q-8(3-Cl) G-1(2-F) Q-8(3-Cl) G-1(2-Cl) Q-8(3-Cl) G-3(3-F) Q-8(3-Cl) G-3(3-Cl) Q-8(3-Cl) G-3(3-CH 3 ) Q-8(3-Cl) G-3(3-CF 3 ) Q-1(4-F) G-1(4-F) Q-1(4-F) G-1(5-F) Q-1(4-F) G-3(3-F) Q-1(4-F) G-3(3-Cl) Q-1(4-F) G-3(3-CH 3 ) Q-1(4-F) G-3(3-CF 3 ) Q-1(4-CN) G-1(4-F) Q-1(4-CN) G-1(5-F) Q-1(4-CN) G-3(3-F) Q-1(4-CN) G-3(3-Cl) Q-1(4-CN) G-3(3-CH 3 ) Q-1(4-CN) G-3(3-CF 3 ) Q-2(4-F) G-1(4-F) Q-2(4-F) G-1(5-F) Q-2(4-F) G-3(3-F) Q-2(4-F) G-3(3-Cl) Q-2(4-F) G-3(3-CH 3 ) Q-2(4-F) G-3(3-CF 3 ) Q-2(4-Cl) G-1(4-F) Q-2(4-Cl) G-1(5-F) Q-2(4-Cl) G-3(3-F) Q-2(4-Cl) G-3(3-Cl) Q-2(4-Cl) G-3(3-CH3 ) Q-2(4-Cl) G-3(3-CF 3 ) Q-2(4-CN) G-1(5-F) Q-3 G-1(4-F) Q-3 G-1(5-F) Q-3 G-3(3-F) Q-3 G-3(3-Cl) Q-3 G-3(3-CH 3 ) Q-3 G-3(3-CF 3 ) Q-3(3-CH 3 ) G-1(5-F) Q-3(3-Cl) G-1(5-F) Q-3(3-F) G-1(4-F) Q-3(3-F) G-1(5-F) Q-3(3-F) G-3(3-F) Q-3(3-F) G-3(3-Cl) Q-3(3-F) G-3(3-CH 3 ) Q-3(3-F) G-3(3-CF 3 ) Q-3(4-Br) G-1(4-F) Q-3(4-Br) G-1(5-F) Q-3(4-Br) G-3(3-F) Q-3(4-Br) G-3(3-Cl) Q-3(4-Br) G-3(3-CH 3 ) Q-3(4-Br) G-3(3-CF 3 ) Q-3(4-CF 3 ) G-1(5-F) Q-3(4-CH 3 ) G-1(4-F) Q-3(4-CH 3 ) G-1(5-F) Q-3(4-CH 3 ) G-3(3-F) Q-3(4-CH 3 ) G-3(3-Cl) Q-3(4-CH 3 ) G-3(3-CH 3 ) Q-3(4-CH 3 ) G-3(3-CF 3 ) Q-3(4-Cl) G-1(4-F) Q-3(4-Cl) G-1(5-F) Q-3(4-Cl) G-3(3-F) Q-3(4-Cl) G-3(3-Cl) Q-3(4-Cl) G-3(3-CH 3 ) Q-3(4-Cl) G-3(3-CF 3 ) Q-3(4-CN) G-1(5-F) Q-3(4-F) G-1(4-F) Q-3(4-F) G-1(5-F) Q-3(4-F) G-3(3-F) Q-3(4-F) G-3(3-Cl) Q-3(4-F) G-3(3-CH 3 ) Q-3(4-F) G-3(3-CF 3 ) Q-3(6-F) G-1(4-F) Q-3(6-F) G-1(5-F) Q-3(6-F) G-3(3-F) Q-3(6-F) G-3(3-Cl) Q-3(6-F) G-3(3-CH 3 ) Q-3(6-F) G-3(3-CF 3 ) Q-4 G-1(4-F) Q-4 G-1(5-F) Q-4 G-3(3-F) Q-4 G-3(3-Cl) Q-4 G-3(3-CH 3 ) Q-4 G-3(3-CF 3 ) Q-4(3-CH 3 ) G-1(5-F) Q-4(3-Cl) G-1(5-F) Q-4(4-Br) G-1(4-F) Q-4(4-Br) G-1(5-F) Q-4(4-Br) G-3(3-F) Q-4(4-Br) G-3(3-Cl) Q-4(4-Br) G-3(3-CH 3 ) Q-4(4-Br) G-3(3-CF 3 ) Q-4(4-Cl) G-1(4-F) Q-4(4-Cl) G-1(5-F) Q-4(4-Cl) G-3(3-F) Q-4(4-Cl) G-3(3-Cl) Q-4(4-Cl) G-3(3-CH 3 ) Q-4(4-Cl) G-3(3-CF 3 ) Q-6(4-Cl) G-1(4-F) Q-6(4-Cl) G-1(5-F) Q-6(4-Cl) G-3(3-F) Q-6(4-Cl) G-3(3-Cl) Q-6(4-Cl) G-3(3-CH 3 ) Q-6(4-Cl) G-3(3-CF 3 ) Q-9 G-1(4-F) Q-9 G-1(5-F) Q-9 G-3(3-F) Q-9 G-3(3-Cl) Q-9 G-3(3-CH 3 ) Q-9 G-3(3-CF 3 ) Q-12a G-1(5-F) ――――――――――― [Table 23]
[0173]
Chemical formula
[0174] ―――――― Q ―――――― Q-1 Q-1(4-F) Q-1(4-Cl) Q-1(4-Br) Q-1(4-I) Q-1(4-CN) Q-1(4-CH 3 ) Q-1(4-CF 3 ) Q-2 Q-2(4-F) Q-2(4-Cl) Q-2(4-Br) Q-2(4-I) Q-2(4-CN) Q-2(4-CH 3 ) Q-2(4-CF 3 ) Q-3 Q-3(4-F) Q-3(4-Cl) Q-3(4-Br) Q-3(4-I) Q-3(4-CN) Q-3(4-CH 3 ) Q-3(4-CF 3 ) Q-4 Q-4(4-F) Q-4(4-Cl) Q-4(4-Br) Q-4(4-I) Q-4(4-CN) Q-4(4-CH 3 ) Q-4(4-CF 3 ) Q-6 Q-6(4-F) Q-6(4-Cl) Q-6(4-Br) Q-6(4-I) Q-6(4-CN) Q-6(4-CH 3 ) Q-6(4-CF 3 ) Q-9 Q-9(4-F) Q-9(4-Cl) Q-9(4-Br) Q-9(4-I) Q-9(4-CN) Q-9(4-CH 3 ) Q-9(4-CF 3 ) Q-10 Q-10(3-F) Q-10(3-Cl) Q-10(3-Br) Q-10(3-I) Q-10(3-CN) Q-10(3-CH 3 ) Q-10(3-CF 3 ) Q-12a Q-12a(4-F) Q-12a(4-Cl) Q-12a(4-Br) Q-12a(4-I) Q-12a(4-CN) Q-12a(4-CH 3 ) Q-12a(4-CF 3 ) Q-1(3-F) Q-1(3-Cl) Q-1(3-Br) Q-1(3-I) Q-1(3-CN) Q-1(3-CH 3 ) Q-1(3-CF 3 ) Q-1(2-F) Q-1(2-Cl) Q-1(2-Br) Q-1(2-I) Q-1(2-CN) Q-1(2-CH 3 ) Q-1(2-CF 3 ) Q-3(3-F) Q-3(3-Cl) Q-3(3-Br) Q-3(3-I) Q-3(3-CN) Q-3(3-CH 3 ) Q-3(3-CF 3 ) Q-3(5-F) Q-3(5-Cl) Q-3(5-Br) Q-3(5-I) Q-3(5-CN) Q-3(5-CH 3 ) Q-3(5-CF 3 ) Q-3(6-F) Q-3(6-Cl) Q-3(6-Br) Q-3(6-I) Q-3(6-CN) Q-3(6-CH 3 ) Q-3(6-CF 3 ) Q-4(3-F) Q-4(3-Cl) Q-4(3-Br) Q-4(3-I) Q-4(3-CN) Q-4(3-CH 3 ) Q-4(3-CF 3 ) Q-6(3-F) Q-6(3-Cl) Q-6(3-Br) Q-6(3-I) Q-6(3-CN) Q-6(3-CH 3 ) Q-6(3-CF 3 ) Q-9(3-F) Q-9(3-Cl) Q-9(3-Br) Q-9(3-I) Q-9(3-CN) Q-9(3-CH 3 ) Q-9(3-CF 3 ) ———————— [Table 24]
[0175] [Chemical formula]
[0176] ———————— Q ———————— Q-1 Q-1(4-F) Q-1(4-Cl) Q-1(4-Br) Q-1(4-I) Q-1(4-CN) Q-1(4-CH 3 ) Q-1(4-CF 3 ) Q-2 Q-2(4-F) Q-2(4-Cl) Q-2(4-Br) Q-2(4-I) Q-2(4-CN) Q-2(4-CH 3 ) Q-2(4-CF 3 ) Q-3 Q-3(4-F) Q-3(4-Cl) Q-3(4-Br) Q-3(4-I) Q-3(4-CN) Q-3(4-CH 3 ) Q-3(4-CF 3 ) Q-4 Q-4(4-F) Q-4(4-Cl) Q-4(4-Br) Q-4(4-I) Q-4(4-CN) Q-4(4-CH 3 ) Q-4(4-CF 3 ) Q-6 Q-6(4-F) Q-6(4-Cl) Q-6(4-Br) Q-6(4-I) Q-6(4-CN) Q-6(4-CH 3 ) Q-6(4-CF 3 ) Q-9 Q-9(4-F) Q-9(4-Cl) Q-9(4-Br) Q-9(4-I) Q-9(4-CN) Q-9(4-CH 3 ) Q-9(4-CF 3 ) Q-10 Q-10(3-F) Q-10(3-Cl) Q-10(3-Br) Q-10(3-I) Q-10(3-CN) Q-10(3-CH 3 ) Q-10(3-CF 3 ) Q-12a Q-12a(4-F) Q-12a(4-Cl) Q-12a(4-Br) Q-12a(4-I) Q-12a(4-CN) Q-12a(4-CH 3 ) Q-12a(4-CF 3 ) Q-1(3-F) Q-1(3-Cl) Q-1(3-Br) Q-1(3-I) Q-1(3-CN) Q-1(3-CH 3 ) Q-1(3-CF 3 ) Q-1(2-F) Q-1(2-Cl) Q-1(2-Br) Q-1(2-I) Q-1(2-CN) Q-1(2-CH 3 ) Q-1(2-CF 3 ) Q-3(3-F) Q-3(3-Cl) Q-3(3-Br) Q-3(3-I) Q-3(3-CN) Q-3(3-CH 3 ) Q-3(3-CF 3 ) Q-3(5-F) Q-3(5-Cl) Q-3(5-Br) Q-3(5-I) Q-3(5-CN) Q-3(5-CH 3 ) Q-3(5-CF 3 ) Q-3(6-F) Q-3(6-Cl) Q-3(6-Br) Q-3(6-I) Q-3(6-CN) Q-3(6-CH 3 ) Q-3(6-CF 3 ) Q-4(3-F) Q-4(3-Cl) Q-4(3-Br) Q-4(3-I) Q-4(3-CN) Q-4(3-CH 3 ) Q-4(3-CF 3 ) Q-6(3-F) Q-6(3-Cl) Q-6(3-Br) Q-6(3-I) Q-6(3-CN) Q-6(3-CH 3 ) Q-6(3-CF 3 ) Q-9(3-F) Q-9(3-Cl) Q-9(3-Br) Q-9(3-I) Q-9(3-CN) Q-9(3-CH 3 ) Q-9(3-CF 3 ) ———————— [Table 25]
[0177] [Chem.]
[0178] ———————— R 1 G 51 ———————— H Cl H Br H I F Cl F Br F I Cl Cl Cl Br Cl I CHF 2 Cl CHF 2 Br CHF 2 I CF 3 Cl CF 3 Br CF 3 I ———————— [Table 26]
[0179] [Chem.]
[0180] ———————— G 51 ———————— Cl Br I ———————— [Table 27]
[0181]
Chem.
[0182] ————————————— R 1 G ————————————— Cl G-7 Cl G-1 Cl G-3 Cl G-2 Cl G-7(3-F) Cl G-7(4-F) Cl G-7(5-F) Cl G-7(6-F) Cl G-1(2-F) Cl G-1(4-F) Cl G-1(5-F) Cl G-1(6-F) Cl G-3(2-F) Cl G-3(3-F) Cl G-2(2-F) Cl G-2(3-F) Cl G-2(4-F) Cl G-2(2-F,4-F) Cl G-2(2-F,5-F) Cl G-7(3-Cl) Cl G-7(4-Cl) Cl G-7(5-Cl) Cl G-7(6-Cl) Cl G-1(2-Cl) Cl G-1(4-Cl) Cl G-1(5-Cl) Cl G-1(6-Cl) Cl G-3(2-Cl) Cl G-3(3-Cl) Cl G-2(2-Cl) Cl G-2(3-Cl) Cl G-2(4-Cl) Cl G-2(2-Cl,4-Cl) Cl G-2(2-Cl,5-Cl) Cl G-7(3-CH 3 ) Cl G-7(4-CH 3 ) Cl G-7(5-CH 3 ) Cl G-7(6-CH 3 ) Cl G-1(2-CH 3 ) Cl G-1(4-CH 3 ) Cl G-1(5-CH 3 ) Cl G-1(6-CH 3 ) Cl G-3(2-CH 3 ) Cl G-3(3-CH 3 ) Cl G-2(2-CH 3 ) Cl G-2(3-CH 3 ) Cl G-2(4-CH 3 ) Cl G-2(2-CH 3 ,4-CH 3 ) Cl G-2(2-CH 3 ,5-CH 3 ) Cl G-7(3-CF 3 ) Cl G-7(4-CF 3 ) Cl G-7(5-CF 3 ) Cl G-7(6-CF 3 ) Cl G-1(2-CF 3 ) Cl G-1(4-CF 3 ) Cl G-1(5-CF 3 ) Cl G-1(6-CF 3 ) Cl G-3(2-CF 3 ) Cl G-3(3-CF 3 ) Cl G-2(2-CF 3 ) Cl G-2(3-CF 3 ) Cl G-2(4-CF 3 ) Cl G-2(2-CF 3 ,4-CF 3 ) Cl G-2(2-CF 3 ,5-CF 3 ) Cl G-1(4-NO 2 ) Cl G-1(4-NH 2 ) Cl G-1(5-NO 2 ) Cl G-1(5-NH 2 ) Cl G-3(3-NO 2 ) Cl G-3(3-NH 2 ) CF 3 G-7 CF 3 G-1 CF 3 G-3 CF 3 G-2 CF 3 G-7(3-F) CF 3 G-7(4-F) CF 3 G-7(5-F) CF 3 G-7(6-F) CF 3 G-1(2-F) CF 3 G-1(4-F) CF3 G-1(5-F) CF 3 G-1(6-F) CF 3 G-3(2-F) CF 3 G-3(3-F) CF 3 G-2(2-F) CF 3 G-2(3-F) CF 3 G-2(4-F) CF 3 G-2(2-F,4-F) CF 3 G-2(2-F,5-F) CF 3 G-7(3-Cl) CF 3 G-7(4-Cl) CF 3 G-7(5-Cl) CF 3 G-7(6-Cl) CF 3 G-1(2-Cl) CF 3 G-1(4-Cl) CF 3 G-1(5-Cl) CF 3 G-1(6-Cl) CF 3 G-3(2-Cl) CF 3 G-3(3-Cl) CF 3 G-2(2-Cl) CF 3 G-2(3-Cl) CF 3 G-2(4-Cl) CF 3 G-2(2-Cl,4-Cl) CF 3 G-2(2-Cl,5-Cl) CF 3 G-7(3-CH 3 ) CF 3 G-7(4-CH 3 ) CF3 G-7(5-CH 3 ) CF 3 G-7(6-CH 3 ) CF 3 G-1(2-CH 3 ) CF 3 G-1(4-CH 3 ) CF 3 G-1(5-CH 3 ) CF 3 G-1(6-CH 3 ) CF 3 G-3(2-CH 3 ) CF 3 G-3(3-CH 3 ) CF 3 G-2(2-CH 3 ) CF 3 G-2(3-CH 3 ) CF 3 G-2(4-CH 3 ) CF 3 G-2(2-CH 3 ,4-CH 3 ) CF 3 G-2(2-CH 3 ,5-CH 3 ) CF 3 G-7(3-CF 3 ) CF 3 G-7(4-CF 3 ) CF 3 G-7(5-CF 3 ) CF 3 G-7(6-CF 3 ) CF 3 G-1(2-CF 3 ) CF 3 G-1(4-CF 3 ) CF 3G-1(5-CF 3 ) CF 3 G-1(6-CF 3 ) CF 3 G-3(2-CF 3 ) CF 3 G-3(3-CF 3 ) CF 3 G-2(2-CF 3 ) CF 3 G-2(3-CF 3 ) CF 3 G-2(4-CF 3 ) CF 3 G-2(2-CF 3 ,4-CF 3 ) CF 3 G-2(2-CF 3 ,5-CF 3 ) CF 3 G-1(4-NO 2 ) CF 3 G-1(4-NH 2 ) CF 3 G-1(5-NO 2 ) CF 3 G-1(5-NH 2 ) CF 3 G-3(3-NO 2 ) CF 3 G-3(3-NH 2 ) CHF 2 G-7 CHF 2 G-1 CHF 2 G-3 CHF 2 G-2 CHF 2 G-7(3-F) CHF 2 G-7(4-F) CHF 2 G-7(5-F) CHF 2 G-7(6-F) CHF 2 G-1(2-F) CHF 2 G-1(4-F) CHF 2 G-1(5-F) CHF 2 G-1(6-F) CHF 2 G-3(2-F) CHF 2 G-3(3-F) CHF 2 G-2(2-F) CHF 2 G-2(3-F) CHF 2 G-2(4-F) CHF 2 G-2(2-F,4-F) CHF 2 G-2(2-F,5-F) CHF 2 G-7(3-Cl) CHF 2 G-7(4-Cl) CHF 2 G-7(5-Cl) CHF 2 G-7(6-Cl) CHF 2 G-1(2-Cl) CHF 2 G-1(4-Cl) CHF 2 G-1(5-Cl) CHF 2 G-1(6-Cl) CHF 2 G-3(2-Cl) CHF 2 G-3(3-Cl) CHF 2 G-2(2-Cl) CHF 2 G-2(3-Cl) CHF 2 G-2(4-Cl) CHF 2 G-2(2-Cl,4-Cl) CHF 2 G-2(2-Cl,5-Cl) CHF 2 G-7(3-CH 3 ) CHF 2 G-7(4-CH 3 ) CHF 2 G-7(5-CH 3 ) CHF 2 G-7(6-CH 3 ) CHF 2 G-1(2-CH 3 ) CHF 2 G-1(4-CH 3 ) CHF 2 G-1(5-CH 3 ) CHF 2 G-1(6-CH 3 ) CHF 2 G-3(2-CH 3 ) CHF 2 G-3(3-CH 3 ) CHF 2 G-2(2-CH 3 ) CHF 2 G-2(3-CH 3 ) CHF 2 G-2(4-CH 3 ) CHF 2 G-2(2-CH 3 ,4-CH 3 ) CHF 2 G-2(2-CH 3 ,5-CH 3 ) CHF 2 G-7(3-CF 3 ) CHF 2 G-7(4-CF 3 ) CHF 2 G-7(5-CF 3 ) CHF2 G-7(6-CF 3 ) CHF 2 G-1(2-CF 3 ) CHF 2 G-1(4-CF 3 ) CHF 2 G-1(5-CF 3 ) CHF 2 G-1(6-CF 3 ) CHF 2 G-3(2-CF 3 ) CHF 2 G-3(3-CF 3 ) CHF 2 G-2(2-CF 3 ) CHF 2 G-2(3-CF 3 ) CHF 2 G-2(4-CF 3 ) CHF 2 G-2(2-CF 3 ,4-CF 3 ) CHF 2 G-2(2-CF 3 ,5-CF 3 ) ――――――――――― [Table 28]
[0183]
Chem.
[0184] ―――――――― G ―――――――― G-7 G-1 G-3 G-2 G-7(3-F) G-7(4-F) G-7(5-F) G-7(6-F) G-1(2-F) G-1(4-F) G-1(5-F) G-1(6-F) G-3(2-F) G-3(3-F) G-2(2-F) G-2(3-F) G-2(4-F) G-2(2-F,4-F) G-2(2-F,5-F) G-7(3-Cl) G-7(4-Cl) G-7(5-Cl) G-7(6-Cl) G-1(2-Cl) G-1(4-Cl) G-1(5-Cl) G-1(6-Cl) G-3(2-Cl) G-3(3-Cl) G-2(2-Cl) G-2(3-Cl) G-2(4-Cl) G-2(2-Cl,4-Cl) G-2(2-Cl,5-Cl) G-7(3-CH 3 ) G-7(4-CH 3 ) G-7(5-CH 3 ) G-7(6-CH 3 ) G-1(2-CH 3 ) G-1(4-CH 3 ) G-1(5-CH 3 ) G-1(6-CH 3 ) G-3(2-CH 3 ) G-3(3-CH 3 ) G-2(2-CH 3 ) G-2(3-CH 3 ) G-2(4-CH 3 ) G-2(2-CH 3 ,4-CH 3 ) G-2(2-CH 3 ,5-CH 3 ) G-7(3-CF 3 ) G-7(4-CF 3 ) G-7(5-CF 3 ) G-7(6-CF 3 ) G-1(2-CF 3 ) G-1(4-CF 3 ) G-1(5-CF 3 ) G-1(6-CF 3 ) G-3(2-CF 3 ) G-3(3-CF 3 ) G-2(2-CF 3 ) G-2(3-CF 3 ) G-2(4-CF 3 ) G-2(2-CF 3 ,4-CF 3 ) G-2(2-CF 3 ,5-CF 3 ) G-1(4-NO 2 ) G-1(4-NH 2 ) G-1(5-NO 2 ) G-1(5-NH 2 ) G-3(3-NO 2 ) G-3(3-NH 2 ) ―――――――― [Table 29]
[0185]
Chem.
[0186] ――――――――――― Q G ――――――――――― Q-3(3-Cl) G-1(4-F) Q-3(3-Cl) G-1(2-F) Q-3(3-Cl) G-1(2-Cl) Q-3(3-Cl) G-3(3-F) Q-3(3-Cl) G-3(3-Cl) Q-3(3-Cl) G-3(3-CH 3 ) Q-3(3-Cl) G-3(3-CF 3 ) Q-3(3-CH 3 ) G-1(4-F) Q-3(3-CH 3 ) G-1(2-F) Q-3(3-CH 3 ) G-1(2-Cl) Q-3(3-CH 3 ) G-3(3-F) Q-3(3-CH 3 ) G-3(3-Cl) Q-3(3-CH 3 ) G-3(3-CH 3 ) Q-3(3-CH 3 ) G-3(3-CF 3 ) Q-4(3-Cl) G-1(4-F) Q-4(3-Cl) G-1(2-F) Q-4(3-Cl) G-1(2-Cl) Q-4(3-Cl) G-3(3-F) Q-4(3-Cl) G-3(3-Cl) Q-4(3-Cl) G-3(3-CH 3 ) Q-4(3-Cl) G-3(3-CF 3 ) Q-4(3-CH 3) G-1(4-F) Q-4(3-CH 3 ) G-1(2-F) Q-4(3-CH 3 ) G-1(2-Cl) Q-4(3-CH 3 ) G-3(3-F) Q-4(3-CH 3 ) G-3(3-Cl) Q-4(3-CH 3 ) G-3(3-CH 3 ) Q-4(3-CH 3 ) G-3(3-CF 3 ) Q-4(4-CH 3 ) G-1(4-F) Q-4(4-CH 3 ) G-1(2-F) Q-4(4-CH 3 ) G-1(2-Cl) Q-4(4-CH 3 ) G-3(3-F) Q-4(4-CH 3 ) G-3(3-Cl) Q-4(4-CH 3 ) G-3(3-CH 3 ) Q-4(4-CH 3 ) G-3(3-CF 3 ) Q-4(3-Br) G-1(4-F) Q-4(3-Br) G-1(2-F) Q-4(3-Br) G-1(2-Cl) Q-4(3-Br) G-3(3-F) Q-4(3-Br) G-3(3-Cl) Q-4(3-Br) G-3(3-CH 3 ) Q-4(3-Br) G-3(3-CF 3 ) Q-10(3-CH 3 ) G-1(4-F) Q-10(3-CH 3 ) G-1(2-F) Q-10(3-CH3 ) G-1(2-Cl) Q-10(3-CH 3 ) G-3(3-F) Q-10(3-CH 3 ) G-3(3-Cl) Q-10(3-CH 3 ) G-3(3-CH 3 ) Q-10(3-CH 3 ) G-3(3-CF 3 ) Q-12a G-1(4-F) Q-12a G-1(2-F) Q-12a G-1(2-Cl) Q-12a G-3(3-F) Q-12a G-3(3-Cl) Q-12a G-3(3-CH 3 ) Q-12a G-3(3-CF 3 ) Q-47a G-1(4-F) Q-47a G-1(2-F) Q-47a G-1(2-Cl) Q-47a G-3(3-F) Q-47a G-3(3-Cl) Q-47a G-3(3-CH 3 ) Q-47a G-3(3-CF 3 ) Q-3(4-CN) G-1(4-F) Q-3(4-CN) G-1(2-F) Q-3(4-CN) G-1(2-Cl) Q-3(4-CN) G-3(3-F) Q-3(4-CN) G-3(3-Cl) Q-3(4-CN) G-3(3-CH 3 ) Q-3(4-CN) G-3(3-CF 3 ) Q-2(4-CN) G-1(4-F) Q-2(4-CN) G-1(2-F) Q-2(4-CN) G-1(2-Cl) Q-2(4-CN) G-3(3-F) Q-2(4-CN) G-3(3-Cl) Q-2(4-CN) G-3(3-CH 3 ) Q-2(4-CN) G-3(3-CF 3 ) Q-3(5-Cl) G-1(4-F) Q-3(5-Cl) G-1(2-F) Q-3(5-Cl) G-1(2-Cl) Q-3(5-Cl) G-3(3-F) Q-3(5-Cl) G-3(3-Cl) Q-3(5-Cl) G-3(3-CH 3 ) Q-3(5-Cl) G-3(3-CF 3 ) Q-3(5-CH 3 ) G-1(4-F) Q-3(5-CH 3 ) G-1(2-F) Q-3(5-CH 3 ) G-1(2-Cl) Q-3(5-CH 3 ) G-3(3-F) Q-3(5-CH 3 ) G-3(3-Cl) Q-3(5-CH 3 ) G-3(3-CH 3 ) Q-3(5-CH 3 ) G-3(3-CF 3 ) Q-6(3-CH 3 ) G-1(4-F) Q-6(3-CH 3 ) G-1(2-F) Q-6(3-CH 3 ) G-1(2-Cl) Q-6(3-CH 3 ) G-3(3-F) Q-6(3-CH 3 ) G-3(3-Cl) Q-6(3-CH3 ) G-3(3-CH 3 ) Q-6(3-CH 3 ) G-3(3-CF 3 ) Q-6(3-Cl) G-1(4-F) Q-6(3-Cl) G-1(2-F) Q-6(3-Cl) G-1(2-Cl) Q-6(3-Cl) G-3(3-F) Q-6(3-Cl) G-3(3-Cl) Q-6(3-Cl) G-3(3-CH 3 ) Q-6(3-Cl) G-3(3-CF 3 ) Q-3(4-I) G-1(4-F) Q-3(4-I) G-1(2-F) Q-3(4-I) G-1(2-Cl) Q-3(4-I) G-3(3-F) Q-3(4-I) G-3(3-Cl) Q-3(4-I) G-3(3-CH 3 ) Q-3(4-I) G-3(3-CF 3 ) Q-10 G-1(4-F) Q-10 G-1(2-F) Q-10 G-1(2-Cl) Q-10 G-3(3-F) Q-10 G-3(3-Cl) Q-10 G-3(3-CH 3 ) Q-10 G-3(3-CF 3 ) Q-3(5-Br) G-1(4-F) Q-3(5-Br) G-1(2-F) Q-3(5-Br) G-1(2-Cl) Q-3(5-Br) G-3(3-F) Q-3(5-Br) G-3(3-Cl) Q-3(5-Br) G-3(3-CH 3 ) Q-3(5-Br) G-3(3-CF 3 ) Q-3(3-Br) G-1(4-F) Q-3(3-Br) G-1(2-F) Q-3(3-Br) G-1(2-Cl) Q-3(3-Br) G-3(3-F) Q-3(3-Br) G-3(3-Cl) Q-3(3-Br) G-3(3-CH 3 ) Q-3(3-Br) G-3(3-CF 3 ) Q-3(4-CF 3 ) G-1(4-F) Q-3(4-CF 3 ) G-1(2-F) Q-3(4-CF 3 ) G-1(2-Cl) Q-3(4-CF 3 ) G-3(3-F) Q-3(4-CF 3 ) G-3(3-Cl) Q-3(4-CF 3 ) G-3(3-CH 3 ) Q-3(4-CF 3 ) G-3(3-CF 3 ) Q-8(3-CH 3 ) G-1(4-F) Q-8(3-CH 3 ) G-1(2-F) Q-8(3-CH 3 ) G-1(2-Cl) Q-8(3-CH 3 ) G-3(3-F) Q-8(3-CH 3 ) G-3(3-Cl) Q-8(3-CH 3 ) G-3(3-CH 3 ) Q-8(3-CH 3 ) G-3(3-CF 3 ) Q-8(3-Cl) G-1(4-F) Q-8(3-Cl) G-1(2-F) Q-8(3-Cl) G-1(2-Cl) Q-8(3-Cl) G-3(3-F) Q-8(3-Cl) G-3(3-Cl) Q-8(3-Cl) G-3(3-CH 3 ) Q-8(3-Cl) G-3(3-CF 3 ) Q-1(4-F) G-1(4-F) Q-1(4-F) G-1(5-F) Q-1(4-F) G-3(3-F) Q-1(4-F) G-3(3-Cl) Q-1(4-F) G-3(3-CH 3 ) Q-1(4-F) G-3(3-CF 3 ) Q-1(4-CN) G-1(4-F) Q-1(4-CN) G-1(5-F) Q-1(4-CN) G-3(3-F) Q-1(4-CN) G-3(3-Cl) Q-1(4-CN) G-3(3-CH 3 ) Q-1(4-CN) G-3(3-CF 3 ) Q-2(4-F) G-1(4-F) Q-2(4-F) G-1(5-F) Q-2(4-F) G-3(3-F) Q-2(4-F) G-3(3-Cl) Q-2(4-F) G-3(3-CH 3 ) Q-2(4-F) G-3(3-CF 3 ) Q-2(4-Cl) G-1(4-F) Q-2(4-Cl) G-1(5-F) Q-2(4-Cl) G-3(3-F) Q-2(4-Cl) G-3(3-Cl) Q-2(4-Cl) G-3(3-CH 3 ) Q-2(4-Cl) G-3(3-CF 3 ) Q-2(4-CN) G-1(5-F) Q-3 G-1(4-F) Q-3 G-1(5-F) Q-3 G-3(3-F) Q-3 G-3(3-Cl) Q-3 G-3(3-CH 3 ) Q-3 G-3(3-CF 3 ) Q-3(3-CH 3 ) G-1(5-F) Q-3(3-Cl) G-1(5-F) Q-3(3-F) G-1(4-F) Q-3(3-F) G-1(5-F) Q-3(3-F) G-3(3-F) Q-3(3-F) G-3(3-Cl) Q-3(3-F) G-3(3-CH 3 ) Q-3(3-F) G-3(3-CF 3 ) Q-3(4-Br) G-1(4-F) Q-3(4-Br) G-1(5-F) Q-3(4-Br) G-3(3-F) Q-3(4-Br) G-3(3-Cl) Q-3(4-Br) G-3(3-CH 3 ) Q-3(4-Br) G-3(3-CF 3 ) Q-3(4-CF 3 ) G-1(5-F) Q-3(4-CH 3 ) G-1(4-F) Q-3(4-CH 3 ) G-1(5-F) Q-3(4-CH 3 ) G-3(3-F) Q-3(4-CH 3) G-3(3-Cl) Q-3(4-CH 3 ) G-3(3-CH 3 ) Q-3(4-CH 3 ) G-3(3-CF 3 ) Q-3(4-Cl) G-1(4-F) Q-3(4-Cl) G-1(5-F) Q-3(4-Cl) G-3(3-F) Q-3(4-Cl) G-3(3-Cl) Q-3(4-Cl) G-3(3-CH 3 ) Q-3(4-Cl) G-3(3-CF 3 ) Q-3(4-CN) G-1(5-F) Q-3(4-F) G-1(4-F) Q-3(4-F) G-1(5-F) Q-3(4-F) G-3(3-F) Q-3(4-F) G-3(3-Cl) Q-3(4-F) G-3(3-CH 3 ) Q-3(4-F) G-3(3-CF 3 ) Q-3(6-F) G-1(4-F) Q-3(6-F) G-1(5-F) Q-3(6-F) G-3(3-F) Q-3(6-F) G-3(3-Cl) Q-3(6-F) G-3(3-CH 3 ) Q-3(6-F) G-3(3-CF 3 ) Q-4 G-1(4-F) Q-4 G-1(5-F) Q-4 G-3(3-F) Q-4 G-3(3-Cl) Q-4 G-3(3-CH 3 ) Q-4 G-3(3-CF 3 ) Q-4(3-CH3 ) G-1(5-F) Q-4(3-Cl) G-1(5-F) Q-4(4-Br) G-1(4-F) Q-4(4-Br) G-1(5-F) Q-4(4-Br) G-3(3-F) Q-4(4-Br) G-3(3-Cl) Q-4(4-Br) G-3(3-CH 3 ) Q-4(4-Br) G-3(3-CF 3 ) Q-4(4-Cl) G-1(4-F) Q-4(4-Cl) G-1(5-F) Q-4(4-Cl) G-3(3-F) Q-4(4-Cl) G-3(3-Cl) Q-4(4-Cl) G-3(3-CH 3 ) Q-4(4-Cl) G-3(3-CF 3 ) Q-6(4-Cl) G-1(4-F) Q-6(4-Cl) G-1(5-F) Q-6(4-Cl) G-3(3-F) Q-6(4-Cl) G-3(3-Cl) Q-6(4-Cl) G-3(3-CH 3 ) Q-6(4-Cl) G-3(3-CF 3 ) Q-9 G-1(4-F) Q-9 G-1(5-F) Q-9 G-3(3-F) Q-9 G-3(3-Cl) Q-9 G-3(3-CH 3 ) Q-9 G-3(3-CF 3 ) Q-12a G-1(5-F) ――――――――――― [Table 30]
[0187] [Chemical Formula]
[0188] ――――――――――― Q G ――――――――――― Q-3(3-Cl) G-1(4-F) Q-3(3-Cl) G-1(2-F) Q-3(3-Cl) G-1(2-Cl) Q-3(3-Cl) G-3(3-F) Q-3(3-Cl) G-3(3-Cl) Q-3(3-Cl) G-3(3-CH 3 ) Q-3(3-Cl) G-3(3-CF 3 ) Q-3(3-CH 3 ) G-1(4-F) Q-3(3-CH 3 ) G-1(2-F) Q-3(3-CH 3 ) G-1(2-Cl) Q-3(3-CH 3 ) G-3(3-F) Q-3(3-CH 3 ) G-3(3-Cl) Q-3(3-CH 3 ) G-3(3-CH 3 ) Q-3(3-CH 3 ) G-3(3-CF 3 ) Q-4(3-Cl) G-1(4-F) Q-4(3-Cl) G-1(2-F) Q-4(3-Cl) G-1(2-Cl) Q-4(3-Cl) G-3(3-F) Q-4(3-Cl) G-3(3-Cl) Q-4(3-Cl) G-3(3-CH 3 ) Q-4(3-Cl) G-3(3-CF 3 ) Q-4(3-CH 3) G-1(4-F) Q-4(3-CH 3 ) G-1(2-F) Q-4(3-CH 3 ) G-1(2-Cl) Q-4(3-CH 3 ) G-3(3-F) Q-4(3-CH 3 ) G-3(3-Cl) Q-4(3-CH 3 ) G-3(3-CH 3 ) Q-4(3-CH 3 ) G-3(3-CF 3 ) Q-4(4-CH 3 ) G-1(4-F) Q-4(4-CH 3 ) G-1(2-F) Q-4(4-CH 3 ) G-1(2-Cl) Q-4(4-CH 3 ) G-3(3-F) Q-4(4-CH 3 ) G-3(3-Cl) Q-4(4-CH 3 ) G-3(3-CH 3 ) Q-4(4-CH 3 ) G-3(3-CF 3 ) Q-4(3-Br) G-1(4-F) Q-4(3-Br) G-1(2-F) Q-4(3-Br) G-1(2-Cl) Q-4(3-Br) G-3(3-F) Q-4(3-Br) G-3(3-Cl) Q-4(3-Br) G-3(3-CH 3 ) Q-4(3-Br) G-3(3-CF 3 ) Q-10(3-CH 3 ) G-1(4-F) Q-10(3-CH 3 ) G-1(2-F) Q-10(3-CH3 ) G-1(2-Cl) Q-10(3-CH 3 ) G-3(3-F) Q-10(3-CH 3 ) G-3(3-Cl) Q-10(3-CH 3 ) G-3(3-CH 3 ) Q-10(3-CH 3 ) G-3(3-CF 3 ) Q-12a G-1(4-F) Q-12a G-1(2-F) Q-12a G-1(2-Cl) Q-12a G-3(3-F) Q-12a G-3(3-Cl) Q-12a G-3(3-CH 3 ) Q-12a G-3(3-CF 3 ) Q-47a G-1(4-F) Q-47a G-1(2-F) Q-47a G-1(2-Cl) Q-47a G-3(3-F) Q-47a G-3(3-Cl) Q-47a G-3(3-CH 3 ) Q-47a G-3(3-CF 3 ) Q-3(4-CN) G-1(4-F) Q-3(4-CN) G-1(2-F) Q-3(4-CN) G-1(2-Cl) Q-3(4-CN) G-3(3-F) Q-3(4-CN) G-3(3-Cl) Q-3(4-CN) G-3(3-CH 3 ) Q-3(4-CN) G-3(3-CF 3 ) Q-2(4-CN) G-1(4-F) Q-2(4-CN) G-1(2-F) Q-2(4-CN) G-1(2-Cl) Q-2(4-CN) G-3(3-F) Q-2(4-CN) G-3(3-Cl) Q-2(4-CN) G-3(3-CH 3 ) Q-2(4-CN) G-3(3-CF 3 ) Q-3(5-Cl) G-1(4-F) Q-3(5-Cl) G-1(2-F) Q-3(5-Cl) G-1(2-Cl) Q-3(5-Cl) G-3(3-F) Q-3(5-Cl) G-3(3-Cl) Q-3(5-Cl) G-3(3-CH 3 ) Q-3(5-Cl) G-3(3-CF 3 ) Q-3(5-CH 3 ) G-1(4-F) Q-3(5-CH 3 ) G-1(2-F) Q-3(5-CH 3 ) G-1(2-Cl) Q-3(5-CH 3 ) G-3(3-F) Q-3(5-CH 3 ) G-3(3-Cl) Q-3(5-CH 3 ) G-3(3-CH 3 ) Q-3(5-CH 3 ) G-3(3-CF 3 ) Q-6(3-CH 3 ) G-1(4-F) Q-6(3-CH 3 ) G-1(2-F) Q-6(3-CH 3 ) G-1(2-Cl) Q-6(3-CH 3 ) G-3(3-F) Q-6(3-CH 3 ) G-3(3-Cl) Q-6(3-CH3 ) G-3(3-CH 3 ) Q-6(3-CH 3 ) G-3(3-CF 3 ) Q-6(3-Cl) G-1(4-F) Q-6(3-Cl) G-1(2-F) Q-6(3-Cl) G-1(2-Cl) Q-6(3-Cl) G-3(3-F) Q-6(3-Cl) G-3(3-Cl) Q-6(3-Cl) G-3(3-CH 3 ) Q-6(3-Cl) G-3(3-CF 3 ) Q-3(4-I) G-1(4-F) Q-3(4-I) G-1(2-F) Q-3(4-I) G-1(2-Cl) Q-3(4-I) G-3(3-F) Q-3(4-I) G-3(3-Cl) Q-3(4-I) G-3(3-CH 3 ) Q-3(4-I) G-3(3-CF 3 ) Q-10 G-1(4-F) Q-10 G-1(2-F) Q-10 G-1(2-Cl) Q-10 G-3(3-F) Q-10 G-3(3-Cl) Q-10 G-3(3-CH 3 ) Q-10 G-3(3-CF 3 ) Q-3(5-Br) G-1(4-F) Q-3(5-Br) G-1(2-F) Q-3(5-Br) G-1(2-Cl) Q-3(5-Br) G-3(3-F) Q-3(5-Br) G-3(3-Cl) Q-3(5-Br) G-3(3-CH 3 ) Q-3(5-Br) G-3(3-CF 3 ) Q-3(3-Br) G-1(4-F) Q-3(3-Br) G-1(2-F) Q-3(3-Br) G-1(2-Cl) Q-3(3-Br) G-3(3-F) Q-3(3-Br) G-3(3-Cl) Q-3(3-Br) G-3(3-CH 3 ) Q-3(3-Br) G-3(3-CF 3 ) Q-3(4-CF 3 ) G-1(4-F) Q-3(4-CF 3 ) G-1(2-F) Q-3(4-CF 3 ) G-1(2-Cl) Q-3(4-CF 3 ) G-3(3-F) Q-3(4-CF 3 ) G-3(3-Cl) Q-3(4-CF 3 ) G-3(3-CH 3 ) Q-3(4-CF 3 ) G-3(3-CF 3 ) Q-8(3-CH 3 ) G-1(4-F) Q-8(3-CH 3 ) G-1(2-F) Q-8(3-CH 3 ) G-1(2-Cl) Q-8(3-CH 3 ) G-3(3-F) Q-8(3-CH 3 ) G-3(3-Cl) Q-8(3-CH 3 ) G-3(3-CH 3 ) Q-8(3-CH 3 ) G-3(3-CF 3 ) Q-8(3-Cl) G-1(4-F) Q-8(3-Cl) G-1(2-F) Q-8(3-Cl) G-1(2-Cl) Q-8(3-Cl) G-3(3-F) Q-8(3-Cl) G-3(3-Cl) Q-8(3-Cl) G-3(3-CH 3 ) Q-8(3-Cl) G-3(3-CF 3 ) Q-1(4-F) G-1(4-F) Q-1(4-F) G-1(5-F) Q-1(4-F) G-3(3-F) Q-1(4-F) G-3(3-Cl) Q-1(4-F) G-3(3-CH 3 ) Q-1(4-F) G-3(3-CF 3 ) Q-1(4-CN) G-1(4-F) Q-1(4-CN) G-1(5-F) Q-1(4-CN) G-3(3-F) Q-1(4-CN) G-3(3-Cl) Q-1(4-CN) G-3(3-CH 3 ) Q-1(4-CN) G-3(3-CF 3 ) Q-2(4-F) G-1(4-F) Q-2(4-F) G-1(5-F) Q-2(4-F) G-3(3-F) Q-2(4-F) G-3(3-Cl) Q-2(4-F) G-3(3-CH 3 ) Q-2(4-F) G-3(3-CF 3 ) Q-2(4-Cl) G-1(4-F) Q-2(4-Cl) G-1(5-F) Q-2(4-Cl) G-3(3-F) Q-2(4-Cl) G-3(3-Cl) Q-2(4-Cl) G-3(3-CH 3 ) Q-2(4-Cl) G-3(3-CF 3 ) Q-2(4-CN) G-1(5-F) Q-3 G-1(4-F) Q-3 G-1(5-F) Q-3 G-3(3-F) Q-3 G-3(3-Cl) Q-3 G-3(3-CH 3 ) Q-3 G-3(3-CF 3 ) Q-3(3-CH 3 ) G-1(5-F) Q-3(3-Cl) G-1(5-F) Q-3(3-F) G-1(4-F) Q-3(3-F) G-1(5-F) Q-3(3-F) G-3(3-F) Q-3(3-F) G-3(3-Cl) Q-3(3-F) G-3(3-CH 3 ) Q-3(3-F) G-3(3-CF 3 ) Q-3(4-Br) G-1(4-F) Q-3(4-Br) G-1(5-F) Q-3(4-Br) G-3(3-F) Q-3(4-Br) G-3(3-Cl) Q-3(4-Br) G-3(3-CH 3 ) Q-3(4-Br) G-3(3-CF 3 ) Q-3(4-CF 3 ) G-1(5-F) Q-3(4-CH 3 ) G-1(4-F) Q-3(4-CH 3 ) G-1(5-F) Q-3(4-CH 3 ) G-3(3-F) Q-3(4-CH 3) G-3(3-Cl) Q-3(4-CH 3 ) G-3(3-CH 3 ) Q-3(4-CH 3 ) G-3(3-CF 3 ) Q-3(4-Cl) G-1(4-F) Q-3(4-Cl) G-1(5-F) Q-3(4-Cl) G-3(3-F) Q-3(4-Cl) G-3(3-Cl) Q-3(4-Cl) G-3(3-CH 3 ) Q-3(4-Cl) G-3(3-CF 3 ) Q-3(4-CN) G-1(5-F) Q-3(4-F) G-1(4-F) Q-3(4-F) G-1(5-F) Q-3(4-F) G-3(3-F) Q-3(4-F) G-3(3-Cl) Q-3(4-F) G-3(3-CH 3 ) Q-3(4-F) G-3(3-CF 3 ) Q-3(6-F) G-1(4-F) Q-3(6-F) G-1(5-F) Q-3(6-F) G-3(3-F) Q-3(6-F) G-3(3-Cl) Q-3(6-F) G-3(3-CH 3 ) Q-3(6-F) G-3(3-CF 3 ) Q-4 G-1(4-F) Q-4 G-1(5-F) Q-4 G-3(3-F) Q-4 G-3(3-Cl) Q-4 G-3(3-CH 3 ) Q-4 G-3(3-CF 3 ) Q-4(3-CH3 ) G-1(5-F) Q-4(3-Cl) G-1(5-F) Q-4(4-Br) G-1(4-F) Q-4(4-Br) G-1(5-F) Q-4(4-Br) G-3(3-F) Q-4(4-Br) G-3(3-Cl) Q-4(4-Br) G-3(3-CH 3 ) Q-4(4-Br) G-3(3-CF 3 ) Q-4(4-Cl) G-1(4-F) Q-4(4-Cl) G-1(5-F) Q-4(4-Cl) G-3(3-F) Q-4(4-Cl) G-3(3-Cl) Q-4(4-Cl) G-3(3-CH 3 ) Q-4(4-Cl) G-3(3-CF 3 ) Q-6(4-Cl) G-1(4-F) Q-6(4-Cl) G-1(5-F) Q-6(4-Cl) G-3(3-F) Q-6(4-Cl) G-3(3-Cl) Q-6(4-Cl) G-3(3-CH 3 ) Q-6(4-Cl) G-3(3-CF 3 ) Q-9 G-1(4-F) Q-9 G-1(5-F) Q-9 G-3(3-F) Q-9 G-3(3-Cl) Q-9 G-3(3-CH 3 ) Q-9 G-3(3-CF 3 ) Q-12a G-1(5-F) ――――――――――― The pest control agent in the present invention means a pest control agent targeting harmful arthropods in the agricultural and horticultural fields or the livestock and sanitation fields (internal and external parasites of mammals or birds as livestock or pets, and household and commercial sanitary pests and nuisance pests), etc.
[0189] In addition, the agricultural chemicals in the present invention refer to insecticides, acaricides, nematicides, herbicides, fungicides, and the like in the agricultural and horticultural fields.
[0190] In this specification, sanitary pests refer to harmful invertebrates that bite target animals, causing allergic symptoms such as severe pain, swelling, and itching, and in some cases causing fatal anaphylactic shock, or that sometimes transmit serious diseases and even cause death by sucking blood, invertebrates that sometimes contaminate food with pathogens such as viruses, bacteria, and parasites by contacting food, invertebrates whose live bodies, carcasses, molted shells, feces, etc. become allergens and cause allergic diseases such as bronchial asthma, rhinitis, conjunctivitis, and atopic dermatitis, invertebrates that cause economic damage by eating food, clothing, housing, etc., and invertebrates that do not directly harm people but cause discomfort by occurring and invading their living environments, etc. More specifically, it refers to ants that bite with their mandibles, hornets that sting with their poisonous stingers, mosquitoes and assassin bugs that suck blood through the skin, and termites that are omnivorous and damage buildings such as houses.
[0191] In this specification, the term "nuisance pests" refers to pests that do not directly harm humans in their living environment, but that cause discomfort and psychological harm due to their appearance or shape.
[0192] Specific examples of insects, mites, crustaceans, mollusks, nematodes, ectoparasites and endoparasites that can be controlled using the compound of the present invention include, but are not limited to, the following organisms:
[0193] Pests include the following: Lepidoptera; Allium leafminer (Acrolepiopsis sapporensis), Yam leafminer (Acrolepiopsis suzukiella), Smaller tea tortrix (Adoxophyes honmai), Summer fruit tortrix (Adoxophyes orana fasciata), Fruit-piercing moth (Adris tyrannus), Sweet potato leaf worm (Aedia leucomelas), Black cutworm (Agrotis ipsilon), Turnip moth (Agrotis segetum), Cotton leafworm (Alabama argillacea), Asiatic leafroller (Archips breviplicanus), Apple tortrix (Archips fuscocupreanus), Oriental tussock moth (Artaxa subflava), Bamboo zygaenid (Artona martini), Japanese giant looper (Ascotis selenaria), Asiatic common looper (Autographa nigrisigna), Pear leaf miner (Bucculatrix pyrivorella), Tea leafroller (Caloptilia theivora), Peach fruit moth (Carposina sasakii), Rice stem borer (Chilo suppressalis), Rice leafroller (Cnaphalocrocis medinalis), Yellow peach moth (Conogethespunctiferalis), Carpenter moth (Cossus insularis), Threespotted plusia (Ctenoplusia agnata), Codling moth (Cydia pomonella), Pine moth (Dendrolimus spectabilis), Jananese hemlock caterpillar (Dendrolimus superans), Cucumber moth (Diaphania indica), Sugarcane borer (Diatraea saccharalis), Mountain stalk moth (Eilema fuscodorsalis), Corn moth (Eilema laevis), Lesser corn stalk moth borer (Elasmopalpus lignosellus), Grape berry moth (Endopiza viteana), Limabean pod borer (Etiella zinckenella), Japanese tussock moth (Euproctis piperita), Tea tussock moth (Euproctis pseudoconspersa), Japanese bamboo lappet moth (Euthrix albomaculata), Drinker moth (Euthrix potatoria), Oriental lappet moth (Gastropacha orientalis), Mulberry pyralid (Glyphodes pyloalis), Plum fruit moth (Grapholita dimorpha), Oriental fruit moth (Grapholita molesta), Sweetpotato leaffolder(Helcystogramma triannullella), Cottonbollworm (Helicoverpa armigera), Oriental tobacco budworm (Helicoverpa assulta), Corn earworm (Helicoverpa zea), Tobacco budworm (Heliothis virescens), Cabbage webworm (Hellula undalis), Oriental tea tortrix (Homona magnanima), Fall webworm moth (Hyphantria cunea), Pearlleaf worm (Illiberis pruni), Prunus bud moth (Illiberis rotundata), Quercus lasiocampid (Kunugia undans), Quercus lasiocampid (Kunugia yamadai), Soybean pod borer (Leguminivora glycinivorella), Mulberry tiger moth (Lemyra imparilis), Gypsy moth (Lymantria dispar), Peach leafminer (Lyonetia clerkella), Silver leafminer moth (Lyonetia prunifoliella malinella), Cabbage armyworm (Mamestra brassicae), Tomato hornworm (Manduca quinquemaculata), Tobacco hornworm (Manduca sexta), Soybean podworm (Matsumuraeses phaseoli), Oriental moth (Monema flavescens), Rice green caterpillar (Narangaaenescens), White-spotted tussock moth (Orgyia thyellina), Asian corn borer (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), Adzuki bean borer (Ostrinia scapulalis), Dark fruit-tree tortrix (Pandemis heparana), Bluegrass webworm (Parapediasia teterrella), Green cochlid (Parasa consocia), Parasa lepida (Parasa lepida), Chinese cochlid (Parasa sinica), Straight swift (Parnara guttata), Pink bollworm (Pectinophora gossypiella), Citrus leafminer (Phyllocnistis citrella), Apple leafminer (Phyllonorycter ringoniella), Large white (Pieris brassicae), Cabbage white butterfly (Pieris rapae crucivora), Diamondback moth (Plutella xylostella), Oriental armyworm (Pseudaletia separata), Soybean looper (Pseudoplusia includens), Swan moth (Sphrageidus similis), Lawn grass cutworm (Spodoptera depravata), Southern armyworm (Spodoptera eridania), Beet armyworm (Spodopteraexigua), Fall armyworm (Spodoptera frugiperda), Cotton leafworm (Spodoptera littoralis), Common cutworm (Spodoptera litura), Persimmon fruit moth (Stathmopoda masinissa), Peach tree borer (Synanthedon exitiosa), Cherry tree borer (Synanthedon hector), Toleria romanovi (Toleria romanovi), Cabbage looper (Trichoplusia ni), etc. Coleoptera: Common bean weevil (Acanthoscelides obtectus), Cupreous chafer (Anomala cuprea), Soybean beetle (Anomala rufocuprea), Asian long-horn beetle (Anoplophora glabripennis), White-spotted longicorn beetle (Anoplophora malasiaca), Boll weevil (Anthonomus grandis), Cucurbit leaf beetle (Aulacophora femoralis), Adzuki bean beetle (Callosobruchus chinensis), Beet flea beetle (Chaetocnema concinna), Sweet potato weevil (Cylas formicarius), Reaf beetle (Demotina fasciculata), Northern corn rootworm (Diabrotica barberi), Southern corn rootworm (Diabrotica undecimpunctata), Western corn rootworm (Diabrotica virgifera), Rice plant weevil (Echinocnemus squameus), Mexican been beetle (Epilachna varivestis), Large twenty-eight-spotted ladybird (Epilachna vigintioctomaculata), Twentyeight-spotted ladybird (Epilachna vigintioctopunctata), Epuraeadomina (Epuraea domina), West Indian sweet potato weevil (Euscepes postfasciatus), Citrus flower chafer (Gametis jucunda), White-fringed beetle (Graphognatus leucoloma), Yellowish elongate chafer (Heptophylla picea), Alfalfa weevil (Hypera postica), Tobacco beetle (Lasioderma serricorne), Colorado potato beetle (Leptinotarsa decemlineata), Rice water weevil (Lissohoptrus oryzophilus), Sweet potato wireworm (Melanotus fortnumi), Sugarcane wireworm (Melanotus tamsuyensis), Pollen beetle (Meligethes aeneus), Japanese pine sawyer (Monochamus alternatus), Black vine weevil (Otiorhynchus sulcatus), Rice leaf beetle (Oulema oryzae), Rove beetle (Paederus fuscipes), Mustard leaf beetle (Phaedon cochleariae), Striped flea beetle (Phyllotreta striolata), Japanese beetle (Popillia japonica), Yellow-spotted longicorn beetle(Psacothea hilaris), Solanum flea beetlebeetle (Psylliodes angusticollis), peach curculio (Rhynchites heros), granary weevil (Sitophilus granarius), maize weevil (Sitophilus zeamais), hunting billbug (Sphenophorus venatus vestitus), yellow mealworm (Tenebrio molitor), red flour beetle (Tribolium castaneum), grape borer (Xylotrechus pyrrhoderus), etc. Hymenoptera: Chestnut sawfly (Apethymus kuri), Large rose sawfly (Arge pagana), Cabbage sawfly (Athalia infumata), Turnip sawfly (Athalia rosae), Japanese carpenter ant (Camponotus japonicus), Chestnut gall wasp (Dryocosmus kuriphilus), Army ant (Eciton burchellii, E. schmitti), Argentine ant (Linepithema humile), Pharaoh ant (Monomorium pharaonis), Bulldog ant (Myrmecia spp.), European pine sawfly Sawfly (Neodiprion sertifer), Fire ants (Solenopsis spp.), Asian giant hornet (Vespa mandarinia), Japanese yellow hornet (Vespa simillima), etc. Diptera: Yellow fever mosquito (Aedes aegypti), Asian tiger mosquito (Aedes albopictus), Aedes spp., Aedes taeniorhynchus, Rice leaf miner (Agromyza oryzae), Mexican fruit fly (Anastrepha ludens), African malaria mosquito (Anopheles gambiae), African malaria mosquito (Anopheles hyrcanus sinensis), Anopheles koreicus (Anopheles koreicus), Anopheles lesteri (Anopheles lesteri, Anopheles maculipennis, Anopheles spp., Soybean pod gall midge (Asphondylia yushimai), Atylotus spp., Melon fly (Bactrocera cucurbitae), Oriental fruit fly (Bactrocera dorsalis), Queensland fruit fly (Bactrocera tryoni), Japanese orange fly (Bactrocera tsuneonis), Boophthora erythrocephala, Braula coeca, Braula spp., Calliphora erythrocephala erythrocephala), the blowfly Calliphora lata, Calliphora spp.), Bottle fly (Calliphora vicina), Mediterranean fruit fly (Ceratitis capitata), Pea leaf miner (Chromatomyia horticola), Old World screw-worm fly (Chrysomya bezziana), Blow fly (Chrysomya chloropyga), Oriental latrine fly (Chrysomya megacephala), Chrysomya spp., Splayed deerfly (Chrysops caecutiens), Chrysops relictus, Chrysops spp., Deer fly (Chrysops suavis, Chrysozona pluvialis, New World screw-worm fly (Cochliomyia hominivorax), House mosquito (Culex pipiens molestus), House mosquito (Culex pipiens pallens), Culex quinquefasciatus, Culex tarsalis, Culex tritaeniorhynchus, Culex spp., Biting midge (Culicoides arakawae), Culicoides spp., Bot flies (Cuterebra spp.), Onion fly (Delia antiqua), Seed corn maggot (Delia platura), Human botfly (Dermatobia hominis), Japanese fruit fly (Drosophila suzukii), Eusimulium spp., Lesser house fly (Fannia canicularis), Fannia spp., Horse nose bot fly (Gasterophilus haemorrhoidalis), Gasterophilus inermis, Horse bot fly (Gasterophilus intestinalis), Throat bot fly (Gasterophilus nasalis), Gasterophilus nigricornis nigricornis, Gasterophilus pecorum, Gasterophilus spp., Tsetse fly (Glossina morsitans, G. palpalis), Glossina spp., Horn fly (Haematobia irritans), Haematobia irritans exigua, Haematobia spp., Haematobia stimulans, Haematopota italic, Common horse fly (Haematopota pluvialis), Haematopota spp., Forest fly (Hippobosca equina), Hippobosca spp.), Hippobosca variegate, Hybomitra ciurea, Hybomitra spp., Smaller rice leaf miner (Hydrellia griseola), Hydrotaea albipuncta, Sheep headfly (Hydrotaea irritans), Hydrotaea spp., Warble fly (Hypoderma bovis), Common cattle grub (Hypoderma lineatum), Hypoderma spp., Black gnat (Leptoconops nipponensis), Lipoptena capreoli, Lipoptena cervi, Lipoptena spp., Cabbage leafminer (Liriomyza brassicae), Tomato leaf miner (Liriomyza bryoniae), Stone leek leafminer (Liriomyza chinensis), Pea leafminer (Liriomyza huidobrensis), Tomato leafminer (Liriomyza sativae), Serpentine leafminer (Liriomyza trifolii), Australian sheep blowfly (Lucilia cuprina), Green bottle fly (Lucilia illustris), Common green bottle fly (Lucilia sericata), Lucilia spp., Lutzomyia spp.), Hessian fly (Mayetiola destructor), Sheep ked (Melophagus ovinus), Melophagus spp., Sweat fly (Morellia simplex), Morellia spp., Face fly (Musca autumnalis), Housefly (Musca domestica), Musca spp., Australian bush fly (Musca vetustissima), Odagmia ornate, Odagmia spp., Sheep nasal bot fly (Oestrus ovis), Oestrus spp., Beet leaf miner (Pegomya cunicularia), Philipomyia spp., Phlebotomus longipalpis, Phlebotomus papatasi, Sandfly (Phlebotomus spp.), Black blow fly (Phormia regina), Prosimulium yezoensis, Northern blowfly (Protophormia terraenovae), Przhevalskiana silenus, Apple maggot (Rhagoletis pomonella), Rhinoestrus spp., Flesh fly (Sarcophaga carnaria), Flesh fly (Sarcophaga peregrina, Sarcophaga spp., Black fly (Simulium ochraceum), Simulium reptans, Simulium spp.), Orange wheat blossom midge (Sitodiplosis mosellana), Stable fly (Stomoxys calcitrans), Stomoxys spp., Tabanus atratus, Tabanus bromius, Greenhead horse fly (Tabanus nigrovittatus), Tabanus spodopterus, Tabanus spp., Tabanus sudeticus, Horse fly (Tabanus trigonus), Moth fly (Telmatoscopus albipunctatus), Tipula paludosa, Tipula spp. spp.), Wilhelmia equine, Wilhelmia spp., Wohlfahrtia spp., etc. Hemiptera: green stink bug (Acrosternum hilare), Pea aphid (Acyrthosiphon pisum), Camellia spiny whitefly (Aleurocanthus camelliae), Orange spiny whitefly (Aleurocanthus spiniferus), Indian cotton leafhopper (Amrasca devastans), California red scale (Aonidiella aurantii), Cowpea aphid (Aphis craccivora), Black bean aphid (Aphis fabae), Soybean aphid (Aphis glycines), Cotton aphid (Aphis gossypii), Green apple aphid (Aphis pomi), Spiraea aphid (Aphis spiraecola), Pale greenplant bug (Apolygus spinolae), Grape leafhopper (Arboridia apicalis), Foxglove aphid (Aulacorthum solani), Beardsley leafhopper (Balclutha saltuella), Silverleaf whitefly (Bemisia argentifolii), Sweetpotato whitefly (Bemisia tabaci), True chinch bug (Blissus leucopterus), Leafcurl plum Aphid (Brachycaudus helichrysi), Cabbageaphid (Brevicoryne brassicae), Oriental chinch bug (Cavelerius saccharivorus), Indian wax scale (Ceroplastes ceriferus), Red wax scale (Ceroplastes rubens), Walnut aphid (Chromaphis juglandicola), Bed bug (Cimex lectularius), Rice stink bug (Cletus punctiger), Citricola scale (Coccus pseudomagnoliarum), San jose scale (Comstockaspis perniciosa), Citrus whitefly (Dialeurodes citri), Asian citrus psyllid (Diaphorina citri), stinkbag (Dichelops furcatus), Russian wheat aphid (Diuraphis noxia), Sloe bug (Dolycoris baccarum), Giant margarodid scale (Drosicha corpulenta), Rosy apple aphid (Dysaphis plantaginea), Red cotton bug (Dysdercus cingulatus), Potato leafhopper (Empoasca fabae), persimmon leafhopper (Empoasca nipponica), Tea green leafhopper (Empoasca onukii), Bean's smaller green leafhopper Leafhopper (Empoasca sakaii), GrapeLeafhopper (Epiacanthus stramineus), Wooly apple aphid (Eriosoma lanigerum), Cabbage bug (Eurydema rugosa), brown stink bug (Euschistus servus), White spotted spined bug (Eysarcoris aeneus), Large spiny stink bug (Eysarcoris lewisi), White-spotted stink bug (Eysarcoris ventralis), Tea scale (Fiorinia theae), Shield bug (Glaucias subpunctatus), Island fleahopper (Halticus insularis), Brown marmorated stink bug (Halyomorpha halys), Mealy plum aphid (Hyalopterus pruni), Cottony cushion scale (Icerya purchasi), Small brown planthopper (Laodelphax striatellus), Rice bug (Leptocorisa chinensis), Turnip aphid (Lipaphis erysimi), Western tarnished plant bug (Lygus hesperus), Tarnished plant bug (Lygus lineolaris), Potato aphid (Macrosiphum euphorbiae), Aster Grape Leafhopper (Macrosteles fascifrons)striifrons), Sugarcane spittlebug (Mahanarva fimbriolata), Black margined aphid (Monellia caryella), Green peach aphid (Myzus persicae), Lettuce aphid (Nasonovia ribisnigri), Onion aphid (Neotoxoptera formosana), Green rice leafhopper (Nephotettix cincticeps), Eastern green stink bug (Nezara antennata), Southern green stink bug (Nezara viridula), Brown rice planthopper (Nilaparvata lugens), Squash bug (Paradasynus spinosus), Cotton mealy bug (Phenacoccus solani), Redbanded stink bug (Piezodorus guildinii), Redbanded shield bug (Piezodorus hybneri), Citrus mealybug (Planococcus citri), Japanese mealybug (Planococcus kraunhiae), Brown-winged green bug (Plautia crossota), Peony scale (Pseudaonidia paeoniae), Cotton fleahopper (Pseudatomoscelis seriatus), Mulberry scale (Pseudaulacaspis pentagona), White peachscale (Pseudaulacaspis prunicola), Comstock mealybug (Pseudococcus comstocki), Grape mealybug (Pseudococcus maritimus), Pear sucker (Psylla pyrisuga), Blood-sucking bug (Rhodnius prolixus), Bird cherry-oat aphid (Rhopalosiphum padi), Rice root aphid (Rhopalosiphum rufiabdominalis), Rhopalid bug (Rhopalus maculatus), Bean bug (Riptortus clavatus), Greenbug (Schizaphis graminum), Japanese black rice bug (Scotinophora lurida), Corn leaf aphid (Sitobion akebiae), English grain aphid (Sitobion avenae), White-backed rice planthopper (Sogatella furcifera), Rice stink bug (Stenodema sibiricum), Sorghum plant bug (Stenotus rubrovittatus), Azalea lace bug (Stephanitis pyrioides), Seed bug (Togo hemipterus), Black citrus aphid (Toxoptera aurantii), Brown citrus aphid (Toxoptera citricida), Greenhouse whitefly whitefly (Trialeurodesvaporariorum), Mexican kissing bug (Triatoma dimidiata), Brazilian kissing bug (Triatoma infestans), Rice leaf bug (Trigonotylus caelestialium), Citrus snow scale (Unaspis citri), Euonymus scale (Unaspis euonymi), Arrowhead scale (Unaspis yanonensis), Grape phylloxera (Viteus vitifolii), etc. Thysanoptera: Flower thrips (Frankliniella intonsa), Western flower thrips (Frankliniella occidentalis), Greenhouse thrips (Heliothrips haemorrhoidalis), Japanese gall-forming thrips (Ponticulothrips diospyrosi), Yellow tea thrips (Scirtothrips dorsalis), Melon thrips (Thrips palmi), Onion thrips (Thrips tabaci), etc. Orthoptera: Australian plague locust (Chortoicetes terminifera), Oriental mole cricket (Gryllotalpa orientalis), Migratory locust (Locusta migratoria), Lesser paddy grasshopper (Oxya japonica), Rice grasshopper (Oxya yezoensis), Desert locust (Schistocerca gregaria), Emma field cricket (Teleogryllus emma), etc. Order Cockroaches (Dictyoptera): German cockroach (Blattella germanica), Formosan subterranean termite (Coptotermes formosanus), Daikoku dry-wood termite (Cryptotermes domesticus), Western dry-wood termite (Incisitermes minor), Black-winged subterranean termite (Odontotermes formosanus), American cockroach (Periplaneta americana), Smoky-brown cockroach (Periplaneta fuliginosa), Japanese cockroach (Periplaneta japonica), Japanese subterranean termite (Reticulitermes speratus), etc. Isoptera: Formosan termites Coptotermes formosanus (Coptotermes formosanus), Japanese termites Reticulitermes speratus (Reticulitermes speratus), Taiwan termites Odontotermes formosanus (Odontotermes formosanus), etc. Acari: Cyclamen mite (Phytonemus pallidus), Broad mite (Polyphagotarsonemus latus), Tarsonemus bilobatus (Tarsonemus bilobatus), Chinese cabbage mite (Penthaleus erythrocephalus), Winter grain mite (Penthaleus major), Rice spider mite (Oligonychus shinkajii), Citrus red mite (Panonychus citri), Mulberry red mite (Panonychus mori), European red mite (Panonychus ulmi), Kanzawa spider mite (Tetranychus kanzawai), Two-spotted spider mite (Tetranychus urticae), Tea long-spotted rust mite (Acaphylla theavagrans), Dry bulb mite (Aceria tulipae), Tomato erineum mite (Aculops lycopersici), Pink citrus rust mite (Aculops pelekassi), Apple rust mite (Aculus schlechtendali), Pear rust mite (Eriophyes chibaensis), Citrus rust mite (Phyllocoptruta oleivora), Bulb mite (Rhizoglyphus robini), Mold mite (Tyrophagus putrescentiae), Tyrophagus similis (Tyrophagussimilis), Acarapis spp., Honey bee tracheal mite (Acarapis woodi), Acarus spp., Lone star tick (Amblyomma americanum), Cayenne tick (Amblyomma cajennense), South African bont tick (Amblyomma hebraeum), Gulf coast tick (Amblyomma maculatum), Amblyomma spp., Tropical bont tick (Amblyomma variegatum), Fowl tick (Argas persicus), Pigeon tick (Argas reflexus), Argas spp., Blue cattle tick (Boophilus annulatus, Boophilus calceratus, African blue tick (Boophilus decoloratus), Tropical cattle tick (Boophilus microplus), Boophilus spp., Caloglyphus spp., Chelacaropsis moorei, Cheyletiella blakei, Rabbit fur mite (Cheyletiella parasitovorax), Cheyletiella spp., Cheyletiella yasguri, Cheyletus eruditus, Cheyletus malaccensis, Chorioptic mange mite (Chorioptes bovis), Chorioptes species (Chorioptesspp.), Cytodites spp., Cattle follicle mite (Demodex bovis), Demodex caballi, Dog follicle mite (Demodex canis), Demodex caprae, Cat follicle mite (Demodex cati), Demodex equi, Face mite (Demodex folliculorum), Demodex ovis, Demodex spp., Sarcoptes suis mite (Demodex suis), Winter tick (Dermacentor albipictus), Rocky Mountain wood tick (Dermacentor andersoni), Ornate sheep tick tick (Dermacentor marginatus), meadow tick (Dermacentor pictus), ornate dog tick (Dermacentor reticulatus), Dermacentor spp., American dog tick (Dermacentor variabilis), Poultry red mite (Dermanyssus gallinae), Dermacentor spp., American house dust mite (Dermatophagoides farina), House dust mite (Dermatophagoides pteronyssinus), Japanese chigger (Eutrombicula wichmanni), Storage mite (Glycyphagus destructor), House itch mite (Glycyphagusdomesticus, Haemaphysalis cinnabarina, Common rodent tick (Haemaphysalis concinna), Yellow dog tick (Haemaphysalis leachi), Bush tick (Haemaphysalis longicornis), Haemaphysalis otophila, Red sheep tick (Haemaphysalis punctate), Haemophysalis spp., Haplochthonius simplex, Trombiculid mite (Helenicula miyagawai), Tortoise tick (Hyalomma aegyptium), Hyalomma anatolicum anatolicum), Bont-legged tick (Hyalomma marginatum), Hyalomma mauritanicus, Hyalomma spp., Small smooth bont-legged tick (Hyalomma transiens), Hypodectes spp., Dog tick (Ixodes canisuga), Hedgehog tick (Ixodes hexagonus), Australian paralysis tick (Ixodes holocyclus), Western black-legged tick (Ixodes pilosus), castor bean tick (Ixodes ricinus), Karoo paralysis tick (Ixodes rubicundus, Deer tick (Ixodes scapularis), Ixodes speciesspp.), Knemidocoptes spp., Laminosioptes spp., Leptotrombidium akamushi, Leptotrombidium pallida, Tsutsugamushi mite (Leptotrombidium scutellare), Listrophorus spp., Feather mite (Megninia cubitalis), Myobia spp., Neoschoengastia xerothermobia, Harvest mite (Neotrombicula autumnalis), Neotrombicula desaleri, Cat mange mite (Notoedres cati), Notoedres spp., Ornithocheyletia spp., Soft tick (Ornithodorus moubata), Ornithodorus spp., Tropical fowl mite (Ornithonyssus bursa), Ornithonyssus spp., Northern fowl mite (Ornithonyssus sylviarum), Spinose ear tick (Otobius megnini), Otobius spp., Dog ear mite (Otodectes cynotis), Otodectes spp., Canine nasal mite mite (Pneumonyssoides caninum), Pneumonyssoides mange, Pneumonyssus spp., Pneumonyssus spp., Psorergatesspp.), Psoroptic mite (Psoroptes communis), Rabbit ear mite (Psoroptes cuniculi), Psoroptes equi, Sheep scab mite (Psoroptes ovis), Psoroptes ovis, Psoroptes spp., Feather mite (Pterolichus obtusus), Pterolichus spp., Raillietia spp., Brown ear tick (Rhipicephalus appendiculatus), Brown ear tick (Rhipicephalus bursa), Rhipicephalus capensis, Asian blue tick(Rhipicephalus evertsi), Kennel tick(Rhipicephalus sanguineus), Rhipicephalus spp., Rhipicephalus turanicus, Rhipicephalus zambeziensis, Sarcoptes bovis, Sarcoptes equi, Sarcoptes ovis, Sarcoptes rupicaprae(=S. caprae), Itch mite(Sarcoptes scabiei, Sarcoptes spp., Sarcoptes suis, Itch mite (Sarcoptis canis), Sternostoma spp., Trombicula akamushi, Trombicula spp.spp.), Cheese mites (Tyrophagus putrescentiae), Tyrophagus spp., Varroa mites (Varroa jacobsoni), Varroa spp., etc. Order Anoplurida: Short-nosed cattle louse (Haematopinus eurysternus), Tail switch louse (Haematopinus quadripertusus), Pig louse (Haematopinus spp.), Large pig louse (Haematopinus suis), Buffalo louse (Haematopinus tuberculatus), Rabbit louse (Haemodipsus ventricosus), Dog sucking louse (Linognathus setosus), Linognathus spp., Long-nosed cattle louse (Linognathus vituri), Head louse (Pediculus humanus), Pediculus spp., Mouse louse (Polyplax serratus), Crab louse (Pthirus pubis), Pthirus spp., Little blue cattle louse (Solenopotes capillatus), Solenopotes spp., etc. Order Mallophaga: Goat biting louse (Bovicola caprae), Bovicola limbata, Sheep body louse (Bovicola ovis), Bovicola spp., Chicken head louse (Cuclotogaster heterographa), Cattle chewing louse (Damalinia bovis), Felicola spp., Cat louse (Felicola subrostrata), Brown chicken louse (Goniodes dissmilis), Fluff louse (Goniodes gallinae), Large hen louse (Goniodes gigas), Lepikentron ovis, Lepikentron spp., Wing louse (Lipeurus caponis), Body louse (Menacanthus cornutus), Small body louse (Menacanthus pallidulus), Menacanthus spp., Chicken body louse (Menacanthus stramineus), Chicken shaft louse (Menopon gallinae), Menopon spp., Dog biting louse (Trichodectes canis), Trichodectes spp. spp.), Werneckiella equi, Werneckiella spp., etc. Order Siphonaptera: Hen flea (Ceratophyllus gallinae), Dog flea (Ctenocephalides canis), Cat flea (Ctenocephalides felis), Sticktight flea (Echidnophaga gallinacean), Human flea (Pulex irritans), Chigoe flea (Tunga penetrans), Oriental rat flea (Xenopsylla cheopis), etc. Other parasites include Monogenea; Benedenia epinepheli, Benedenia hoshinai, Benedenia sekii, Benedenia seriolae, Bivagina tai, Sea louse (Caligus curtus), Caligus elongates, Caligus labaracis, Caligus longipedis, Caligus orientalis, Caligus teres, Dactylogyrus spp., Gyrodactylus spp. spp., Heteraxine heterocerca, Heterobothrium okamotoi, Lamellodiscus spp., Copepods (Lepeophtheirus cuneifer), Lepeophtheirus hippoglossi, Lepeophtheirus pectoralis, Salmon louse (Lepeophtheirus salmonis), Microcotyle sebastis, Microcotyle sebastisci, Neobenedenia, Neobenedenia congeri, Neobenedenia girellae, Neoheterobothrium hirame, Polystoma spp., Pseudocaligus fugu, Zeuxapta japonica, etc. Tapeworms (Cestoda); Andyra spp., Anoplocephala spp., Avitellina spp., Bertiella spp., Bothridium spp., Cittotaenia spp., Davainea spp., Diorchis spp., Manson's tapeworm (Diphyllobothrium erinacei), fish tapeworm (Diphyllobothrium latum), Diphyllobothrium spp., Diphyllogonoporus spp., Diplopylidium spp., Dog tapeworm Tapeworm (Dipylidium caninum), Dipylidium spp., dog tapeworm (Echinococcus granulosus), fox tapeworm (Echinococcus multilocularis), Echinococcus spp., Echinocotyle spp., Echinolepsis spp., Hydatigera spp., Hymenolepis diminuta, Hymenolepis spp., Joyeuxiella spp., Ligura spp., Mesocestoides spp., Moniezia benedeni, Moniezia spp., Paranoplocephala spp., Raillietina spp., Schistocephalus spp., Spirometra spp., Stilesia spp.), beef tapeworm (Taenia saginata), pork tapeworm (Taenia solium), Taenia spp., cat tapeworm (Taenia taeniaeformis), Thysaniezia spp., Thysanosomsa spp., etc. Trematoda: Austrobilharzia spp., Brachylaema spp., Calicophoron spp., Catatropis spp., Chinese river fluke (Clonorchis sinensis), Clonorchis spp., Collyriclum spp., Cotylophoron spp., Cyclocoelum spp., Dicrocoelium spp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp. spp.), Echinostoma spp., Eurytrema coelomaticum, pancreas fluke (Eurytrema pancreaticum), Eurytrema spp., liver fluke (Fasciola gigantica), sheep liver fluke (Fasciola hepatica), Fasciola spp., Fasciolides spp., large intestinal fluke (Fasciolopsis bruski), Fasciolopsis spp., Fischoederius spp., Gastrothylacus spp. spp., Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeum spp., Leucochloridium spp., Metagonimus spp., Metorchis spp.), Nanophyetus spp., Notocotylus spp., Opisthorchis spp., Ornithobilharzia spp., Paragonimus spp., Oriental lung fluke (Paragonimus westermani), Paramphistomum spp., Plagiorchis spp., Posthodiplostomum spp., Prosthogonimus spp., Schistosoma haematobium, Schistosoma japonicum, Schistosoma mansoni mansoni, Schistosoma spp., Trichobilharzia spp., Troglotrema spp., Typhlocoelum spp., etc., Nematoda; Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Anisakis spp., Ascaridia galli, Ascaridia spp., Ascaris spp., Ascaris suum, Aspiculuris spp. spp.), Brugia spp., Bunostomum spp., Capillaria spp., Chabertia spp., intestinal worm (Cooperia oncophora), Cooperia spp., Crenosoma spp., Cyathostoma spp.), Cyclococcus spp., Cylicostephanus spp., Cylindropharynx spp., Cystocaulus spp., Dictyocaulus spp., Dirofilaria immitis, Dirofilaria spp., Dracunculus spp., Draschia spp., Elaphostrongylus spp., Enoplida spp., Enterobius spp., Filaroides spp., Filicollis spp. spp.), Globocephalus spp., Gnathostoma spp., Gongylonema spp., Gyalocephalus spp., Habronema spp., Barber's pole worm (Haemonchus contortus), Haemonchus spp., Heterakis spp., Hyostrongylus spp., Litomosoides spp., Loa spp., Macracanthorhynchus spp., Marshallagia spp., Metastrongylus spp. spp.), Micronema spp., Moniliformis spp., Muellerius spp., Nematodirus spp., Neostrongylus spp., Obeliscoides spp.), Oeophagostomum dentatum, Oesophagodontus spp., Oesophagostomum radiatum, Oesophagostomum spp., Ollulanus spp., Onchocerca gibsoni, Onchocerca spp., Brown stomach worm (Ostertagia ostertagi), Ostertagia spp., Oxyuris spp., Parabronema spp., Paraacrenosoma spp., Parafilaria spp., Parafilaroides spp. spp., Parascaris spp., Parelaphostrongylus spp., Passalurus spp., Physaloptera spp., Pneumostrongylus spp., Poteriostomum spp., Prostenorchis spp., Protostrongylus spp., Setaria spp., Spicocaulus spp., Stephanofilaria spp., Stephanurus spp., Strongyloides spp., Strongylus spp. spp., Syngamus spp., Syphacia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Trichinella spp., Trichomosoides spp.), Trichonema spp., ruminant nematode (Trichostrongylus colubriformis), Trichostrongylus spp., Trichuris spp., Triodontophorus spp., Uncinaria spp., Wuchereria spp., etc. Protozoa; Babesia spp., Eimeria acervulina, Eimeria bovis, Eimeria brunette, Eimeria maxima, Eimeria necatrix, Eimeria ovinoidalis, Eimeria spp., Eimeria tenella, Entamoeba histolytica, Giardia spp., Histomanas spp., Plasmodium spp., Theileria spp. spp.), Toxoplasma spp., Trichomonadidae spp., Trypanosomsa cruzi, and the like.
[0194] Furthermore, the compound of the present invention is also effective against pests which have developed resistance to existing insecticides such as organophosphorus compounds, carbamate compounds and pyrethroid compounds.
[0195] That is, the compound of the present invention can effectively control pests belonging to the orders of Collembola, Dictyoptera (Cockroaches), Orthoptera (Orthoptera), Termitidae, Thysanoptera (Thysanoptera), Hemiptera (Hemiptera and Cicadellidae), Lepidoptera (Lepidoptera), Coleoptera (Coleoptera), Hymenoptera (Hymenoptera), Diptera (Fleas), Isoptera (Fleas), and Phthiraptera, etc., crustaceans such as Lepidoptera, Cyprinodontida, and Cyclopida, mites, gastropods, cestodes, trematodes, nematodes, protozoa, etc., at a low concentration.
[0196] On the other hand, the compound of the present invention has an extremely useful feature of having almost no adverse effect on mammals, fish, crustaceans, and beneficial insects (useful insects such as honeybees and bumblebees, and natural enemies such as glossy wasps, oil wasps, parasite flies, swarm bugs, and phytoseiid mites).
[0197] When the compound of the present invention is used, it is usually mixed with a suitable solid or liquid carrier, and if desired, a surfactant, a penetrant, a spreading agent, a thickener, an antifreeze agent, a binder, an anticaking agent, a disintegrant, an antifoaming agent, a preservative, a decomposition inhibitor, or the like may be added to the compound, and the compound may be used in practice as a formulation of 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 tablet, or an emulsifiable gel. From the viewpoint of labor saving and safety improvement, the preparation of any of the above dosage forms can be provided by being enclosed in a water-soluble package such as a water-soluble capsule or a bag made of a water-soluble film.
[0198] Examples of solid carriers include natural minerals such as quartz, calcite, sepiolite, dolomite, chalk, kaolinite, pyrophyllite, sericite, halloysite, metahaloysite, wood-bush clay, frog-eye clay, pottery stone, ziglite, allophane, shirasu, kira, talc, bentonite, activated clay, acid clay, pumice, attapulgite, zeolite, and diatomaceous earth; calcined products of natural minerals such as calcined clay, perlite, shirasu balloon, vermiculite, attapulgus clay, and calcined diatomaceous earth; magnesium carbonate, calcium carbonate, sodium carbonate, Examples of suitable inorganic salts include sodium bicarbonate, ammonium sulfate, sodium sulfate, magnesium sulfate, diammonium hydrogen phosphate, ammonium dihydrogen phosphate, and potassium chloride; sugars such as glucose, fructose, sucrose, and lactose; polysaccharides such as starch, powdered cellulose, and dextrin; organic substances such as urea, urea derivatives, benzoic acid, and salts of benzoic acid; plants such as wood flour, cork flour, corn cobs, walnut shells, and tobacco stalks; fly ash, white carbon (e.g., hydrated synthetic silica, anhydrous synthetic silica, hydrated synthetic silicate, etc.), and fertilizers.
[0199] The liquid carrier may be, for example, xylene, alkyl (C 9 Or C 10 etc.) Benzene, phenyl xylyl ethane, alkyl (C 1 Or C 3Aromatic hydrocarbons such as naphthalene; aliphatic hydrocarbons such as machine oil, normal paraffin, isoparaffin, naphthene; mixtures of aromatic and aliphatic hydrocarbons such as kerosene; alcohols such as ethanol, isopropyl alcohol, cyclohexanol, phenoxyethanol, benzyl alcohol; polyhydric alcohols such as ethylene glycol, propylene glycol, diethylene glycol, hexylene glycol, polyethylene glycol, and polypropylene glycol; ethers such as propyl cellosolve, butyl cellosolve, phenyl cellosolve, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, and propylene glycol monophenyl ether; ketones such as acetophenone, cyclohexanone, and γ-butyrolactone; esters such as fatty acid methyl esters, dialkyl succinate esters, dialkyl glutamate esters, dialkyl adipic esters, and dialkyl phthalate esters; N-alkyl(C 1 , C 8 Or C 12 etc.) acid amides such as pyrrolidone; oils and fats such as soybean oil, linseed oil, rapeseed oil, coconut oil, cottonseed oil, castor oil; dimethyl sulfoxide, water; etc.
[0200] These solid carriers and liquid carriers may be used alone or in combination of two or more kinds.
[0201] Examples of the surfactant include nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl (mono- or di-)phenyl ethers, polyoxyethylene (mono-, di- or tri-)styryl phenyl ethers, polyoxyethylene polyoxypropylene block copolymers, polyoxyethylene fatty acid (mono- or di-)esters, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, castor oil ethylene oxide adducts, acetylene glycol, acetylene alcohol, ethylene oxide adducts of acetylene glycol, ethylene oxide adducts of acetylene alcohol, and alkyl glycosides; alkyl sulfates, alkyl benzene sulfonates, lignin sulfonates, alkyl sulfosuccinates, and naphthalene sulfonates. anionic surfactants such as alkyl phenyl ether sulfonates, alkyl naphthalene sulfonates, salts of formalin condensates of naphthalene sulfonic acid, salts of formalin condensates of alkyl naphthalene sulfonic acid, polyoxyethylene alkyl ether sulfates or phosphate ester salts, polyoxyethylene (mono- or di-) alkyl phenyl ether sulfates or phosphate ester salts, polyoxyethylene (mono-, di-, or tri-) styryl phenyl ether sulfates or phosphate ester salts, polycarboxylates (e.g., polyacrylates, polymaleates, copolymers of maleic acid and olefins, etc.), and polystyrene sulfonates; cationic surfactants such as alkyl amine salts and alkyl quaternary ammonium salts; amphoteric surfactants such as amino acid types and betaine types; silicone-based surfactants, and fluorine-based surfactants.
[0202] The content of these surfactants is not particularly limited, but is usually preferably in the range of 0.05 to 20 parts by mass per 100 parts by mass of the preparation of the present invention. These surfactants may be used alone or in combination of two or more kinds.
[0203] The dosage of the compound of the present invention varies depending on the application site, application time, application method, cultivated crop, etc., but usually, an amount of about 0.005 to 50 kg of active ingredient per hectare (ha) is appropriate.
[0204] On the other hand, when the compound of the present invention is used for controlling internal or external parasites in mammals and birds as livestock and pets, an effective amount of the compound of the present invention can be administered together with a formulation additive by oral administration, parenteral administration such as injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), percutaneous administration such as immersion, spraying, bathing, washing, pouring-on, spotting-on, dusting, etc., intranasal administration, etc. The compound of the present invention can also be administered by a molded product using a strip, plate, band, collar, ear mark, limb band, marking device, etc.
[0205] For administration, the compound of the present invention may be formulated into any dosage form suitable for the administration route.
[0206] When the compound of the present invention is used to eliminate external or internal parasites, the preferred dosage of the compound (1) of the present invention as an active ingredient depends on the type of target parasite to be controlled, the species of the target animal to be administered, the administration method, etc., but is usually 0.01 to 100 mg / kg, preferably 0.01 to 50 mg / kg per kg of live weight of the target animal to be administered. In particular, the dosage for dogs may vary depending on the type or age of the target dog, or the external parasite to be controlled, but is usually 1 to 5000 mg / kg, preferably 1 to 100 mg / kg per kg of live weight of the target dog.
[0207] When external or internal parasites are eliminated by administering the compound of the present invention, the administration interval depends on the type of target parasite to be controlled, the species of the target animal to be administered, the administration method, etc., but can usually be set arbitrarily within the range of once every day to once every year. It is preferably once every week to once every six months, and more preferably once every day (24 hours), every month, once every month, once every two months, once every three months, or once every six months.
[0208] In addition, when the compound of the present invention is used to control external parasites in dogs, the timing of administration of the compound of the present invention to dogs can be, for example, 30 minutes before the start of feeding or 120 minutes after the end of feeding. Here, 30 minutes before the start of feeding and 120 minutes after the end of feeding are based on the act of eating food given to the dog for the purpose of nutritional intake. For example, if the dog's feeding time is 20 minutes, the specified time is based on the eating act and is a total of 170 minutes from 30 minutes before the start of feeding to 120 minutes after the end of feeding. This also includes a case where the feeding is interrupted once during the feeding, and the feeding is resumed after the compound of the present invention is orally administered. In this specification, feeding means the act of an animal eating food.
[0209] In general, the number of times a dog is fed per day varies depending on the breed, age, and habits, but is usually 3 to 4 times a day for dogs under six months old, 2 to 3 times a day for dogs between six months and one year old, 2 to 3 times a day for adult dogs about 1 to 5 years old, and 2 to 3 times a day for dogs 6 years old or older. In the present invention, feeding refers to the act of eating for the purpose of taking in nutrients, and does not include the act of feeding food or the like for the purpose of disciplining or training a dog.
[0210] Any dosage form that may be prepared includes solid preparations such as powders, granules, wettable powders, pellets, tablets, boli, capsules, molded products containing the active compound, etc.; liquid preparations such as injectable solutions, oral solutions, solutions for use on the skin or in body cavities, etc.; solution preparations such as pour-on solutions, spot-on solutions, flowable solutions, emulsions, etc.; semi-solid preparations such as ointments, gels, etc.;
[0211] Examples of the dosage form when the compound of the present invention is orally administered include solid preparations such as tablets, chewables, capsules, pills, boluses, granules, powders, etc.; semi-solid preparations such as pastes and gels; and liquid preparations such as drinks.
[0212] Furthermore, examples of dosage forms for transdermal administration include solid preparations such as powders; semi-solid preparations such as creams, ointments, pastes, gels, etc.; and liquid preparations such as sprays, aerosols, solutions and emulsions, suspensions, lotions, etc.
[0213] Furthermore, dosage forms for administration by injection include liquid preparations such as solutions and emulsions and suspensions, and dosage forms for administration via the nose include liquid preparations such as aerosols.
[0214] In addition, examples of the formulation for spraying in animal rearing environments such as livestock barns include solid preparations such as wettable powders, dusts, and granules; and liquid preparations such as emulsions and suspension concentrates.
[0215] However, the formulations used in the parasite control agent of the present invention are not limited to these dosage forms.
[0216] The solid preparation can be administered orally as it is, or diluted with water and used for transdermal administration or for spraying in the animal rearing environment such as livestock pens.
[0217] A solid preparation for oral administration can be prepared by mixing the compound (1) of the present invention or a salt thereof with one or more excipients and binders suitable for oral administration, and further, if necessary, with physiologically acceptable additives such as lubricants, disintegrants, dyes, pigments, etc., and molding the mixture into a desired shape.
[0218] Examples of excipients and binders include sugars or sugar derivatives such as lactose, sucrose, mannitol, sorbitol, etc.; starches such as corn starch, wheat starch, rice starch, potato starch, etc.; celluloses or cellulose derivatives such as methylcellulose, carboxymethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, etc.; proteins or protein derivatives such as zein and gelatin; and synthetic polymer compounds such as honey, gum arabic paste, polyvinyl alcohol, polyvinylpyrrolidone, etc.
[0219] Examples of the lubricant include magnesium stearate, and examples of the disintegrant include cellulose, agar, alginic acid, cross-linked polyvinylpyrrolidinone, carbonates, and the like.
[0220] Furthermore, among solid preparations used for oral administration, particularly in the case of solid preparations such as chewable preparations, additives are used to impart a taste, texture, and flavor preferred by the animal to which the preparation is administered; however, the carriers and additives used in solid preparations of the parasite control composition are not limited to these.
[0221] The liquid preparation can be administered as it is, transdermally or by injection, or it can be mixed with feed and administered orally, diluted with water and administered orally or transdermally, or it can be sprayed in the animal rearing environment such as a livestock house.
[0222] Injectable solutions can be administered intravenously, intramuscularly, or subcutaneously. Injectable solutions can be prepared by dissolving an active compound in a suitable solvent and adding, if necessary, additives such as a solubilizer, an acid, a base, a buffer salt, an antioxidant, a protective agent, etc.
[0223] Suitable solvents include water, ethanol, butanol, benzyl alcohol, glycerin, propylene glycol, polyethylene glycol, N-methylpyrrolidone and mixtures thereof, physiologically acceptable vegetable oils, synthetic oils suitable for injection, and the like.
[0224] The solubilizing agent includes polyvinylpyrrolidone, polyoxyethylated castor oil, polyoxyethylated sorbitan ester, and the like.
[0225] Examples of the protecting agent include benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid esters, and n-butanol.
[0226] Oral liquid preparations can be administered directly or after dilution, and can be prepared in the same manner as injectable liquid preparations.
[0227] Flowables, emulsions, etc. can be administered directly or diluted, transdermally, or via environmental treatment.
[0228] Solutions for use on the skin can be administered by dropping, spreading, rubbing, spraying, sprinkling, or by application by immersion (immersion, bathing, or washing). These solutions can be prepared in the same way as solutions for injection.
[0229] Pour-on and spot-on agents are applied or sprayed onto a limited area of the skin, allowing the active compound to penetrate the skin and act systemically.
[0230] Drops and drops can be prepared by dissolving, suspending or emulsifying the active ingredient in a suitable skin-compatible solvent or solvent mixture, and, if necessary, adding auxiliary agents such as surfactants, colorants, absorption promoters, antioxidants, light stabilizers, adhesives, etc.
[0231] Suitable solvents include water, alkanols, glycols, polyethylene glycol, polypropylene glycol, glycerin, benzyl alcohol, phenylethanol, phenoxyethanol, ethyl acetate, butyl acetate, benzyl benzoate, dipropylene glycol monomethyl ether, diethylene glycol monobutyl ether, acetone, methyl ethyl ketone, aromatic and / or aliphatic hydrocarbons, vegetable or synthetic oils, DMF (N,N-dimethylformamide), liquid paraffin, light liquid paraffin, silicone, dimethylacetamide, N-methylpyrrolidone, or 2,2-dimethyl-4-oxy-methylene-1,3-dioxolane.
[0232] Absorption enhancers include DMSO (dimethyl sulfoxide), isopropyl myristate, dipropylene glycol pelargonate, silicone oil, aliphatic esters, triglycerides, fatty alcohols, and the like.
[0233] Antioxidants include sulfites, metabisulfites, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole, tocopherol, and the like.
[0234] Emulsifiable concentrates can be administered orally, transdermally or by injection. Emulsifiable concentrates can be prepared by dissolving an active ingredient in a hydrophobic or hydrophilic phase, and homogenizing the solution with a suitable emulsifier and, if necessary, with a colorant, an absorption promoter, a protective agent, an antioxidant, a light-shielding agent, a thickening agent and other auxiliary agents, by the solvent of the other phase.
[0235] Examples of the hydrophobic phase (oil) include paraffin oil, silicone oil, sesame oil, almond oil, castor oil, synthetic triglyceride, ethyl stearate, di-n-butyl adipate, hexyl laurate, dipropylene glycol pelargonate, esters of branched short-chain fatty acids and saturated fatty acids having chain lengths of C16 to C18, isopropyl myristate, isopropyl palmitate, caprylic / capric acid esters of saturated fatty alcohols having chain lengths of C12 to C18, isopropyl stearate, oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, waxy fatty acid esters, dibutyl phthalate, diisopropyl adipate, isotridecyl alcohol, 2-octyldodecanol, cetylstearyl alcohol, and oleyl alcohol.
[0236] Hydrophilic phases include water, propylene glycol, glycerin, sorbitol, and the like.
[0237] Examples of the emulsifier include nonionic surfactants such as polyoxyethylated castor oil, polyoxyethylated sorbitan monoolefinate, sorbitan monostearate, glycerin monostearate, polyoxyethyl stearate, and alkylphenol polyglycol ether; amphoteric surfactants such as disodium N-lauryl-β-iminodipropionate and lecithin; anionic surfactants such as sodium lauryl sulfate, fatty alcohol sulfate ether, and monoethanolamine salts of mono / dialkyl polyglycol orthophosphate esters; and cationic surfactants such as cetyltrimethylammonium chloride.
[0238] Other adjuvants include carboxymethylcellulose, methylcellulose, polyacrylates, alginates, gelatin, gum arabic, polyvinylpyrrolidone, polyvinyl alcohol, methyl vinyl ether, copolymers of maleic anhydride, polyethylene glycol, waxes, colloidal silica, and the like.
[0239] Semisolid preparations can be administered by painting or spreading on the skin or by introduction into a body cavity. Gels can be prepared by adding to the solutions prepared as described above for the injectable solutions sufficient thickener to produce a clear material with an ointment-like consistency.
[0240] Next, formulation examples using the compound of the present invention are shown. However, the formulation examples containing the compound of the present invention are not limited to these. In the following formulation examples, "parts" means parts by mass.
[0241] [Wettable powder] 0.1 to 80 parts of the compound of the present invention Solid carrier 5 to 98.9 parts Surfactant 1-10 parts Others 0~5 Other examples include anti-caking agents, anti-decomposition agents, etc.
[0242] 〔emulsion〕 Compound of the present invention 0.1 to 30 parts Liquid carrier 45-95 parts Surfactant 4.9 to 15 parts Others 0-10 Other examples of the additives include a spreading agent and a decomposition inhibitor.
[0243] [Suspension Agent] 0.1 to 70 parts of the compound of the present invention Liquid carrier 15 to 98.89 parts Surfactant 1-12 parts Others 0.01 to 30 parts Other examples include antifreeze agents and thickeners.
[0244] [Water dispersible granule] 0.1 to 90 parts of the compound of the present invention Solid carrier 0 to 98.9 parts Surfactant 1-20 parts Others 0-10 Other examples include binders, anti-decomposition agents, etc.
[0245] [Liquid] Compound of the present invention 0.01 to 70 parts Liquid carrier 20 to 99.99 parts Others 0-10 Other examples include antifreeze agents, spreading agents, etc.
[0246] [Granules] Compound of the present invention 0.01 to 80 parts Solid carrier 10 to 99.99 parts Others 0-10 Other examples include binders, anti-decomposition agents, etc.
[0247] [Powder] Compound of the present invention 0.01 to 30 parts Solid carrier 65 to 99.99 parts Others 0~5 Other examples include drift inhibitors and decomposition inhibitors.
[0248] Next, the formulation examples using the compound of the present invention as an active ingredient are shown in more detail, but the present invention is not limited to these. Note that the compound No. 1-001 of the present invention shown below means N-(4-fluorophenyl)-6-[3-(6-fluoropyridin-3-yl)-4-(trifluoromethyl)phenyl]-4-hydroxy-2-oxo-1,2,5,6-tetrahydropyridine-3-carboxamide described in Synthesis Example 1 described later.
[0249] [Mixing Example 1] Hydrating agent Compound No. 1-001 of the present invention 20 parts Pyrophyllite 74 parts Solpol 5039 4th part (Product name of Toho Chemical Industry Co., Ltd., a mixture of nonionic and anionic surfactants) Carplex #80D Part 2 (Shionogi & Co., Ltd. product name, synthetic hydrous silicic acid) The above ingredients are mixed uniformly and pulverized to prepare a wettable powder.
[0250] [Formulation Example 2] Emulsion Compound No. 1-001 of the present invention Part 5 Xylene 75 parts N-Methylpyrrolidone 15 parts Solpol 2680 5 parts (Product name of Toho Chemical Industry Co., Ltd., a mixture of nonionic and anionic surfactants) The above ingredients are mixed uniformly to prepare an emulsion.
[0251] [Formulation Example 3] Suspension agent Compound No. 1-001 of the present invention 25 parts Agrisol S-710 10 parts (Kao Corporation product name, non-ionic surfactant) Lunox 1000C 0.5 parts (Product name of Toho Chemical Industry Co., Ltd., anionic surfactant) Xanthan gum 0.2 parts Water 64.3 parts After the above ingredients are mixed uniformly, they are wet-pulverized to form a suspension.
[0252] [Mixing Example 4] Granular water dispersible agent Compound No. 1-001 of the present invention 75 parts High Tenor NE-15 5 parts (Dai-ichi Kogyo Seiyaku Co., Ltd. product name, anionic surfactant) Vanillex N 10 parts (Product name of Nippon Paper Industries, anionic surfactant) Carplex #80D 10 copies (Shionogi & Co., Ltd. product name, synthetic hydrous silicic acid) After the above ingredients are uniformly mixed and pulverized, a small amount of water is added, the mixture is stirred and mixed, granulated in an extrusion granulator, and dried to give a water dispersible granule.
[0253] [Formulation example 5] Granules Compound No. 1-001 of the present invention Part 5 Bentonite 50 parts Talc 45 parts After the above ingredients are uniformly mixed and pulverized, a small amount of water is added and the mixture is stirred and mixed, granulated in an extrusion granulator, and dried to give granules.
[0254] [Mixing Example 6] Powder Compound No. 1-001 of the present invention Part 3 Carplex #80D 0.5 parts (Shionogi & Co., Ltd. product name, synthetic hydrous silicic acid) Kaolinite 95 parts Diisopropyl phosphate 1.5 parts The above ingredients are mixed and ground uniformly to obtain a powder.
[0255] When used, the above formulation is diluted 1 to 10,000 times with water, or directly sprayed without dilution.
[0256] [Formulation Example 7] Wettable powder preparation Compound No. 1-001 of the present invention 25 parts Sodium diisobutylnaphthalene sulfonate 1 part Calcium n-dodecylbenzenesulfonate 10 parts Alkylaryl polyglycol ether 12 parts Sodium salt of naphthalenesulfonic acid formalin condensate 3 parts Emulsion type silicone 1 part Silicon dioxide 3 parts Kaolin 45 parts [Formulation Example 8] Water-soluble thickener preparation Compound No. 1-001 of the present invention 20 parts Polyoxyethylene lauryl ether 3 parts Sodium dioctyl sulfosuccinate 3.5 parts Dimethyl sulfoxide 37 parts 2-Propanol 36.5 parts [Formulation Example 9] Liquid agent for spraying Compound No. 1-001 of the present invention Part 2 Dimethyl sulfoxide 10 parts 2-Propanol 35 parts 53 parts acetone [Formulation Example 10] Liquid for transdermal administration Compound No. 1-001 of the present invention Part 5 Hexylene glycol 50 parts 2-Propanol 45 parts [Formulation Example 11] Liquid for transdermal administration Compound No. 1-001 of the present invention Part 5 Propylene glycol monomethyl ether 50 parts Dipropylene glycol 45 parts [Formulation Example 12] Liquid for transdermal administration (dropping) Compound No. 1-001 of the present invention Part 2 Light liquid paraffin 98 parts [Formulation Example 13] Liquid for transdermal administration (dropping) Compound No. 1-001 of the present invention Part 2 Light liquid paraffin 58 parts 30 parts olive oil ODO 9th Division (Product name of Nisshin Oillio Group, medium chain fatty acid oil) Shin-Etsu Silicone Division 1 In addition, when the compound of the present invention is used as an agricultural chemical or an animal drug, it may be mixed with other types of drugs when formulated or applied as necessary. By mixing and applying, it is possible to reduce the amount of drug applied, thereby reducing costs, and to expand the control spectrum and achieve a higher pest control effect due to the synergistic effect of the mixed drug. In this case, it is also possible to combine the compound with multiple known drugs at the same time.
[0257] For example, types of pesticides to be mixed with the compound of the present invention include, for example, compounds listed in The Pesticide Manual, 18th Edition, 2018 and The Pesticide Manual, 19th Edition, 2021. Specific examples of the generic names of antiparasitic drugs and antibiotics to be mixed and used as veterinary drugs are as follows, but are not necessarily limited to these.
[0258] Insecticides: abamectin, acephate, acequinocyl, acetamiprid, acrinathrin, acinonapyr, afidopyropen, afoxolaner, alanycarb, aldicarb, allethrin, a alpha-cypermethrin, alpha-endosulfan, amidoflumet, amitraz, azamethiphos, azinphos-ethyl, azinphos-methyl, azocyclotin, bacillus thuringiensis thuringiensis, bendiocarb, benfluthrin, benfuracarb, bensultap, benzoximate, benzpyrimoxan, beta-cyfluthrin, beta-cypermethrin, bifenazate, bifenthrin, bioallethrin, bioresmethrin smethrin, bistrifluron, broflanilide, bromopropylate, buprofezin, butocarboxim, carbaryl, carbofuran, carbosulfan, cartap, chinomethionat, chlorantraniliprole, chlorethxyfos,Chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, chlorobezilate, chloroprallethrin, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clofentezine tezine, clothianidin, cyanophos, cyantraniliprole, cyclaniliprole, cycloprothrin, cyenopyrafen, cyetpyrafen, cyflumetofen, cyfluthrin, cyhalodiamide, cyhalothrin halothrin, cyhexatine, cypermethrin, cyphenothrin, cyproflanilide, cyromazine, deltamethrin, diacloden, diafenthiuron, diazinon, dichlorvos, dichloromezotiaz, Dicofol, dienochlor, diflovidazin, diflubenzuron, dimefluthrin, dimethoate, dimethylvinphos, dimpropyridaz, dinotefuran, diofenolan, disulfoton, DNOC,dT-80-phthalthrin, emamectin-benzoate, empenthrin, endosulfan, EPN, epsilon-metofluthrin, epsilon-momfluorothrin, esfenvalerate, ethifencarb, ethiprole, etofenprox, etoxazole, etrimfos, Febantel, fenazaquin, fenbutatin oxide oxide), fenitrothion, fenmezoditiaz, fenobucarb, fenothiocarb, fenoxycarb, fenpropathrin, fenpyroximate, fenthion, fenvalerate, fipronil, flometoquin, flonicamid, fluacrypyrim, fluazuron, Rubendiamide, fluchlorodiniliprole, flucycloxuron, flucythrinate, flufenerim, flufenoxuron, flufenprox, flufiprole, fluhexafon, flumethrin, flupentiofenox, flupyradifurone, flupyrimin,Flupyroxystrobin (flupyroxystrobin), fluralaner, fluvalinate, fluxametamide, fonophos, formetanate, formothion, furathiocarb, gamma-cyhalothrin, halfenprox, halofenozide ( halofenozide, heptafluthrin, hexaflumuron, hexythiazox, hydramethylnon, imidacloprid, imiprothrin, indazapyroxamet, indoxacarb, indoxacarb-MP, isocycloceram ocycloseram, isofenphos, isoprocarb, isoxathion, kappa-bifenthrin, kappa-tefluthrin, lambda-cyhalothrin, ledprona, lepimectin, lufenuron, malathion, meperidine Fluthrin, 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, oxydepro 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 afluprole, pyrethrins, pyridaben, pyridalyl, pyrifluquinazon, pyrimidifen, pyriprole, pyriproxyfen, resmethrin, rotenone, silafluofen, spidoxamat, spinetoram,Spinosad, spirobudifen, spirodiclofen, spiromesifen, spiropidione, spirotetramat, spiromesifen, sulfiflumin, sulfotep, sulfoxaflor, sulprofos ofos, tau-fluvalinate, tebufenozide, tebufenpyrad, teflubenzuron, tefluthorin, terbufos, tetrachlorantraniliprole, tetrachlorvinphos, tetramethrin, tetramethylfluthrin, tetraniliprole, thiacloprid, thiamethoxam, thiocyclam, thiodicarb, thiofanox, thiometon, thioantraniliprole, tolfenpyrad, Tralomethrin, transfluthrin, triazamate, triazuron, trichlorfon, triflumezopyrim, triflumuron, tyclopyrazoflor, vamidothion, and zeta-cypermethrin, etc.
[0259] Fungicides: acibenzolar-S-methyl, acypetacs, aldimorph, allyl alcohol, ametoctradin, aminopyrifen, amisulbrom, amobam, ampropylfos, anilazine, azaconazole, azithiram, azoxystrobin, barium polysulfide. polysulfide, benalaxyl, benalaxyl-M, benodanil, benomyl, benquinox, bentaluron, benthiavalicarb-isopropyl, benthiazole, benzamacril, benzamorph, benzovindiflupyr, binapacryl, biphenyl, bitertanol, bixafen, blasticidin-S, Bordeaux mixture mixture), boscalid, bromoconazole, bupirimate, buthiobate, butylamine, calcium polysulfide, captafol, captan, carbamorph, carbendazim, carboxin, carpropamid, carvone, cheshunt mixturemixture), chinomethionat, chlobenthiazone, chloraniformethane, chloranil, chlorfenazole, chloroneb, chloroinconazide, 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, decaphentin, dehydroacetic acid acid), dichlobentiazox, dichlofluanid, dichlon, dichlorophen, dichlozoline, diclobutrazol, diclocymet, diclomezine, dicloran, diethofencarb, difenoconazole, diflumetorim, dimethirimol, dimethomorph, dimoxystrobin, diniconazole, diniconazole-M -M), dinobuton, dinocap, dinocap-4, dinocap-6, dinocton, dinosulfon, dinoterbone, diphenylamine, dipymetitrone, dipyrithione, disulfiram, ditalimfos, dithianon, DNOC, dodemorph, dodine, drazoxolon, edifenphos, enestrobin, enoxastrobin,Epoxiconazole, ethaboxam, etaconazole, etem, ethirimol, ethoxyquin, etridiazole, famoxadone, fenamidone, fenaminosulf, phenaminestrobin, fenapanil, fenarimol narimol, fenbuconazole, fenfuram, fenhexamid, fenitropan, fenoxanil, fenpiclonil, fenpicoxamid, fenpropidin, fenpropimorph, fenpyrazamine, fentin, ferbam erbam, ferimzone, florylpicoxamid, fluazinam, flubeneteram, fludioxonil, flufenoxadiazam, flufenoxystrobin, fluindapyr, flumetylsulforim, flumetylsulforim, flumetylsulforim metover, flumorph, fluopicolide, fluopimomide, fluopyram, fluoroimide, fluotrimazole, fluoxapiprolin, fluoxastrobin, fluoxytioconazole, fluquinconazole,Flusilazole, flusulfamide, flutolanil, flutianil, flutriafol, fluxapyroxad, folpet, fosetyl-aluminium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbanil, fur Conazole, fluconazole-cis, furmecyclox, furophanate, glyodin, griseofulvin, guazatine, halacrinate, hexachlorobenzene, hexaconazole, hexylthiofos, oxyquinoline sulfate (8-hydroxyquinoline sulfate), sulfate, hymexazol, imazalil, imibenconazole, iminoctadine-albesilate, iminoctadine-triacetate, inpyrfluxam, iodocarb, ipconazole, ipfentrifluconazole rifluconazole, ipflufenoquin, iprobenfos, iprodione, iprovalicarb, isofetamide, isoflecithin, isotianil, isoprothiolane, isopyrazam, isovaledione,Kasugamycin, kresoxim-methyl, laminarin, mancopper, mancozeb, mandestrobin, mandipropamid, maneb, mebenil, mecarbinzid, mefentrifluconazole, mepanipyrim, mepronil, meptyldinocap, metalaxyl, metalaxyl-M, metam, meta ylpicoxamid (metarylpicoxamid), metazoxolone, metconazole, methasulfocarb, metofuroxam, metyltetraprole, metiram, metominostrobin, metrafenone, metsulfovax, milneb, myclobutanil, myclozolin, nabam, naftifine, natamycin, organic nickel bis (dimethyldithiocarbamate), nitrostyrene, nitrothal-isopropyl, nuarimol, octhinoline, ofurace, orysastrobin, oxadixyl, oxathiapiprolin, oxyquinoline copper, oxpoconazole fumarate, oxycarboxin,Pefurazoate, penconazole, pencycuron, penflufen, pentachlorophenol, penthiopyrad, orthophenylphenol, phosdiphen, phthalide, picarbutrazox, picoxystrobin, piperalin, polycarbamate, polyoxins, polyoxin-D, potassium azide, potassium hydrogen carbonate, probenazole, prochloraz, procymidone, propamocarb hydrochloride hydrochloride), propiconazole, propineb, proquinazid, prothiocarb, pyrazophos, pyribencarb, pyrifenox, pyrimethanil, pyriminostrobin, pyroquilon, prothiocarb, prothioconazole thioconazole), pydiflumetofen, pyracarbolid, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyrapropoyne, pyraziflumid, pyridaclomethyl, pyridinitril, pyriophenone,pyrisoxazole, pyroxychlor, pyroxyfur, quinacetol-sulfate, quinazamid, quinconazole, quinoxyfen, quinofumelin, quintozene, rabenzazole, salicylanilide, seboctylamine, sedaxane, silthiofam, simeconazole, sodium hydrogen carbonate, sodium hypochlorite hypochlorite, spiroxamine, sulfur, tebuconazole, tebufloquin, tecloftalam, tecnazene, tecoram, tetraconazole, thiabendazole, thiadifluor, thicyofen, thifluzamide, thiochlorfenphim, thiophanate e), thiophanate-methyl, thiuram, tiadinil, tioximid, 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.
[0260] Nematicides: aldoxycarb, benclothiaz, cadusafos, cyclobutrifluram, DBCP, dichlofenthion, DSP, ethoprophos, fenamiphos, fensulfothion, fluazaindolizine (fluazaindolizine), fluensulfone, fosthiazate, fosthietan, imicyafos, isamidofos, isazofos, oxamyl, thionazin, tioxazafen and trifluenfuronate and the like.
[0261] Parasiticides: esfenvalerate, fenpropathrin, fenvalerate, alphacypermethrin, bifenthrin, cypermethrin, deltamethrin, etofenprox, lambda-cyhalothrin, permethrin, tefluthrin fluthrin, 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, fenocarb, carbofuran, afoxolaner, fluralaner, fluxametamide, sarolaner, lotilaner,Tigolaner, esafoxolaner, modoflaner, umifoxolaner, mivorilaner, avermectin, ivermectin, doramectin, eprinomectin, madeuramycin, milbemycin, milbemycin oxime oxime, moxidectin, selamectin, indoxacarb, amitraz, bistrifluron, spinosad, albendazole, atovaquone, bithionol, cambendazole, carnidazole, chloroquine, clazuril, clorsulon, closantel, coumaphos, dichlorophen, diethylcarbamazine, diminazene, dinitolmide, dithiazanine iodide iodide, emodepside, epsiprantel, febantel, fenbendazole, flubendazole, glycalpyramide, imidocarb, levamisole, mebendazole, mebendazole, mefloquine hydrochloride, melarsomine dihydrochloride,metronidazole, methylidine, monepantel, morantel tartrate, niclosamide, oxantel pamoate, oxantel tartrate, oxibendazole, oxyclozanide, piperazine adipate, piperazine citrate, piperazine phosphate, praziquantel, pyrantel pamoate, rafoxanide, tetramisole hydrochloride, thiabendazole, and triclabendazole, etc.
[0262] Antibiotics: amoxicillin, ampicillin, cefapirin, cefazolin sodium, cefquinome, ceftiofur, penicillin, chlortetracycline, oxytetracycline, danofloxacin, difloxacin, oxolinic acid acid, enrofloxacin, florfenicol, lincomycin, lomefloxacin, marbofloxacin, miloxacin, mirosamycin, norfloxacin, ofloxacin, orbifloxacin, valnemulin, thiamphenicol, tiamulin fumarate, tilmicosin phosphate, tylosin acetate isovalerate, tylosin phosphate phosphate, tulathromycin, ketoconazole, miconazole nitrate, and clavulanic acid, etc.
[0263] The compound of the present invention has excellent insecticidal and acaricidal activity against many agricultural pests, spider mites, and internal or external parasites of mammals or birds, and also exerts a sufficient control effect against pests that have acquired resistance to existing insecticides. Furthermore, it has almost no adverse effect on mammals, fish, and beneficial insects, has low residual properties, and is a light burden on the environment. Therefore, the present invention can provide a useful novel pest control agent.
[0264] In light of the above, the embodiments of the present invention relate to the following [1] to
[26] .
[0265] [1] Formula (1):
[0266] [ka]
[0267] [In the formula, Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-15, Q-16, Q-17, Q-18, Q-19, Q-20, Q-21, Q-22, Q-23, Q-24, Q-25, Q-26, Q-27, Q-28, Q-2 9, Q-30, Q-31, Q-32, Q-33, Q-34, Q-35, Q-36, Q-37, Q-38, Q-39, Q-40, Q-41, Q-42, Q-43, Q-44, Q-45, Q-46, Q-47, Q-48, Q-49, Q-50, Q-51, Q-52, Q-53, Q-54, Q-55 or Q-56;
[0268] [ka]
[0269] [ka]
[0270] Z 1 is a halogen atom, C 1 ~C 6 Alkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Alkynyl, halo(C 1 ~C 6 ) alkyl, halo(C 2 ~C 6 ) alkenyl, halo(C 2 ~C 6 ) alkynyl, C1 ~C 6 Alkoxy, halo(C 1 ~C 6 ) Alkoxy, C 2 ~C 6 Alkoxy(C 1 ~C 6 ) Alkoxy, C 2 ~C 6 Alkenyloxy, halo(C 2 ~C 6 ) alkenyloxy, C 2 ~C 6 Alkynyloxy, halo(C 2 ~C 6 ) alkynyloxy, C 1 ~C 6 Alkylthio, C 1 ~C 6 Alkylsulfinyl, C 1 ~C 6 Alkyl sulfonyl, halo(C 1 ~C 6 ) Alkylthio, Halo(C 1 ~C 6 ) alkylsulfinyl, halo(C 1 ~C 6 ) Alkyl sulfonyl, C 2 ~C 6 Alkenylthio, C 2 ~C 6 Alkenylsulfinyl, C 2 ~C 6 Alkenylsulfonyl, halo(C 2 ~C 6 ) alkenylthio, halo(C 2 ~C 6 ) alkenylsulfinyl, halo(C 2 ~C 6 ) alkenylsulfonyl, C 2 ~C 6 Alkynylthio, C 2 ~C 6 Alkynylsulfinyl, C 2 ~C 6 Alkynylsulfonyl, halo(C 2 ~C 6 ) Alkynylthio, halo(C 2 ~C 6 ) Alkynylsulfinyl, halo(C2 ~C 6 ) Alkynylsulfonyl, -NH 2 , C 1 ~C 6 Alkylamino, di(C 1 ~C 6 ) alkylamino, halo(C 1 ~C 6 ) Alkylamino, dihalo(C 1 ~C 6 ) Alkylamino, formyl, carboxy, C 1 ~C 6 Alkylcarbonyl, halo(C 1 ~C 6 ) Alkylcarbonyl, C 1 ~C 6 Alkoxycarbonyl, halo(C 1 ~C 6 ) alkoxycarbonyl, C 1 ~C 6 Alkylaminocarbonyl, halo(C 1 ~C 6 ) alkylaminocarbonyl, di(C 1 ~C 6 ) Alkylaminocarbonyl, Hydroxy, C 1 ~C 6 Alkylcarbonyloxy, C 1 ~C 6 Alkoxycarbonyloxy, C 1 ~C 6 Alkyl sulfonyloxy, halo(C 1 ~C 6 ) Alkylsulfonyloxy, -SO 3 H, C 1 ~C 6 Alkylaminosulfonyl, di(C 1 ~C 6 ) alkylaminosulfonyl, -C(=NOR 12 )R 13 , cyano or nitro; R 12 is a hydrogen atom or C 1 ~C 6 represents an alkyl group, R 13 is a hydrogen atom or C 1 ~C 6 represents an alkyl group, Z 3 is a hydrogen atom or C 1 ~C 6 represents an alkyl group, J represents J-1 or J-2;
[0271] [ka]
[0272] A 1 represents a nitrogen atom or CH; G stands for G-1, G-2, G-3, G-4, G-5, G-6, G-7, G-8, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G -17, G-18, G-19, G-20, G-21, G-22, G-23, G-24, G-25, G-26, G-27, G-28, G-29, G-30, G-31, G- 32, G-33, G-34, G-35, G-36, G-37, G-38, G-39, G-40, G-41, G-42, G-43, G-44, G-45, G-46, G-4 7, represents G-48, G-49, G-50, G-51, G-52, G-53, G-54, G-55, G-56, G-57, G-58, G-59, G-60 or G-61;
[0273] [ka]
[0274] [ka]
[0275] Z 2 is a halogen atom, C 1 ~C 6 Alkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Alkynyl, halo(C 1 ~C 6 ) alkyl, halo(C 2 ~C 6) alkenyl, halo(C 2 ~C 6 ) alkynyl, C 1 ~C 6 Alkoxy, halo(C 1 ~C 6 ) Alkoxy, C 1 ~C 6 Alkoxy(C 1 ~C 6 ) Alkoxy, C 2 ~C 6 Alkenyloxy, halo(C 2 ~C 6 ) alkenyloxy, C 2 ~C 6 Alkynyloxy, halo(C 2 ~C 6 ) alkynyloxy, C 1 ~C 6 Alkylthio, C 1 ~C 6 Alkylsulfinyl, C 1 ~C 6 Alkyl sulfonyl, halo(C 1 ~C 6 ) Alkylthio, Halo(C 1 ~C 6 ) alkylsulfinyl, halo(C 1 ~C 6 ) Alkyl sulfonyl, C 2 ~C 6 Alkenylthio, C 2 ~C 6 Alkenylsulfinyl, C 2 ~C 6 Alkenylsulfonyl, halo(C 2 ~C 6 ) alkenylthio, halo(C 2 ~C 6 ) alkenylsulfinyl, halo(C 2 ~C 6 ) alkenylsulfonyl, C 2 ~C 6 Alkynylthio, C 2 ~C 6 Alkynylsulfinyl, C 2 ~C 6 Alkynylsulfonyl, halo(C 2 ~C 6) Alkynylthio, halo(C 2 ~C 6 ) Alkynylsulfinyl, halo(C 2 ~C 6 ) Alkynylsulfonyl, -NH 2 , C 1 ~C 6 Alkylamino, di(C 1 ~C 6 ) alkylamino, halo(C 1 ~C 6 ) Alkylamino, dihalo(C 1 ~C 6 ) Alkylamino, formyl, carboxy, C 1 ~C 6 Alkylcarbonyl, halo(C 1 ~C 6 ) Alkylcarbonyl, C 1 ~C 6 Alkoxycarbonyl, halo(C 1 ~C 6 ) alkoxycarbonyl, C 1 ~C 6 Alkylaminocarbonyl, halo(C 1 ~C 6 ) alkylaminocarbonyl, di(C 1 ~C 6 ) Alkylaminocarbonyl, Hydroxy, C 1 ~C 6 Alkylcarbonyloxy, C 1 ~C 6 Alkoxycarbonyloxy, C 1 ~C 6 Alkyl sulfonyloxy, halo(C 1 ~C 6 ) Alkylsulfonyloxy, -SO 3 H, C 1 ~C 6 Alkylaminosulfonyl, di(C 1 ~C 6 ) alkylaminosulfonyl, -C(=NOR 14 )R 15 , nitro or cyano; R 14 is a hydrogen atom or C 1 ~C 6 represents an alkyl group, R 15 is a hydrogen atom or C 1 ~C 6 represents an alkyl group, Z 4 is C 1 ~C 6 represents an alkyl group, R 1 is a hydrogen atom, a halogen atom, or a halo(C 1 ~C 6 ) Alkyl, C 1 ~C 6 represents alkyl or cyano; R 2 is a hydrogen atom, C 1 ~C 6 Alkyl, halo(C 1 ~C 6 ) Alkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Alkynyl, C 3 ~C 6 Cycloalkyl, -C(O)R 4 , -C(O)OR 5 , D-1, D-2 or D-3;
[0276] [ka]
[0277] R 4 is C 1 ~C 6 Alkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Alkynyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 6 Alkylcarbonyl, di(C 1 ~C 6 ) alkylamino or R 6 Replaced by (C 1 ~C 6 ) alkyl, R 6 is a halogen atom, C 1 ~C6 Alkoxy, cyano, nitro, phenyl or R 8 represents a phenyl substituted with Z 5 is a halogen atom, C 1 ~C 6 Alkyl, C 1 ~C 6 represents alkoxy, cyano or nitro, R 8 is a halogen atom, C 1 ~C 6 Alkyl, C 1 ~C 6 represents alkoxy, cyano or nitro, R 5 is C 1 ~C 6 Alkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Alkynyl, C 3 ~C 6 Cycloalkyl, R 9 Replaced by (C 1 ~C 6 ) alkyl, phenyl or R 10 represents a phenyl substituted with R 9 is a halogen atom, C 1 ~C 6 Alkoxy, cyano, nitro, phenyl or R 11 represents a phenyl substituted with R 10 is a halogen atom, C 1 ~C 6 Alkyl, C 1 ~C 6 represents alkoxy, cyano or nitro, R 11 is a halogen atom, C 1 ~C 6 Alkyl, C 1 ~C 6 represents alkoxy, cyano or nitro, R 3 is a hydrogen atom, C 1 ~C 6 Alkyl, halo(C 1 ~C 6) Alkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Alkynyl, C 3 ~C 6 Cycloalkyl or C 1 ~C 6 represents an alkylcarbonyl; X represents an oxygen atom or a sulfur atom; Y represents an oxygen atom or a sulfur atom; t1 represents an integer of 0 or 1; t2 represents an integer of 0, 1 or 2; t3 represents an integer of 0, 1, 2 or 3; t4 represents an integer of 0, 1, 2, 3 or 4; t5 represents an integer of 0, 1, 2, 3, 4, or 5. and t8 represents an integer of 0, 1, 2, 3 or 4.] or a salt thereof.
[0278] [2] A 1 represents a nitrogen atom, or a salt thereof.
[0279] [3] Z 1 is a halogen atom, C 1 ~C 6 Alkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Alkynyl, halo(C 1 ~C 6 ) Alkyl, C 1 ~C 6 Alkoxy, halo(C 1 ~C 6 ) Alkoxy, C 1 ~C 6 Alkylthio, C 1 ~C 6 Alkylsulfinyl, C 1 ~C 6 Alkyl sulfonyl, halo(C 1 ~C 6 ) Alkylthio, Halo(C1 ~C 6 ) alkylsulfinyl, halo(C 1 ~C 6 ) Alkylsulfonyl, -NH 2 , C 1 ~C 6 Alkylamino, di(C 1 ~C 6 ) Alkylamino, Carboxy, C 1 ~C 6 Alkyl carbonyl, C 1 ~C 6 Alkoxycarbonyl, C 1 ~C 6 Alkylaminocarbonyl, di(C 1 ~C 6 ) Alkylaminocarbonyl, Hydroxy, C 1 ~C 6 Alkylcarbonyloxy, C 1 ~C 6 represents alkylsulfonyloxy, cyano or nitro; Z 2 is a halogen atom, C 1 ~C 6 Alkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Alkynyl, halo(C 1 ~C 6 ) alkyl, halo(C 2 ~C 6 ) alkenyl, halo(C 2 ~C 6 ) alkynyl, C 1 ~C 6 Alkoxy, halo(C 1 ~C 6 ) Alkoxy, C 1 ~C 6 Alkylthio, C 1 ~C 6 Alkylsulfinyl, C 1 ~C 6 Alkyl sulfonyl, halo(C 1 ~C 6 ) Alkylthio, Halo(C 1 ~C 6 ) alkylsulfinyl, halo(C 1 ~C6 ) Alkylsulfonyl, -NH 2 , C 1 ~C 6 Alkylamino, di(C 1 ~C 6 ) Alkylamino, Carboxy, C 1 ~C 6 Alkyl carbonyl, C 1 ~C 6 Alkoxycarbonyl, C 1 ~C 6 Alkylaminocarbonyl, di(C 1 ~C 6 ) Alkylaminocarbonyl, Hydroxy, C 1 ~C 6 Alkylcarbonyloxy, C 1 ~C 6 Alkylsulfonyloxy, -C(=NOR 14 )R 15 , nitro or cyano; Z 5 is a halogen atom, C 1 ~C 6 Alkyl or C 1 ~C 6 represents alkoxy, R 1 is a hydrogen atom, a halogen atom or a halo(C 1 ~C 6 ) alkyl, R 2 is a hydrogen atom, -C(O)R 4 , -C(O)OR 5 , D-1, D-2 or D-3; R 3 represents a hydrogen atom, Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-15, Q-16, Q-17, Q-18, Q-19, Q-20, Q-21, Q-22, Q-23, Q-25, Q-26, Q-27, Q-29, Q-30, Q-31, Q-32, Q-33, Q-38, Q-39, Q-40, Q-41, Q-42, Q-43, Q-44, Q-45, Q-46, Q-47, Q-50, Q-51, Q-52 or Q-54; G stands for G-1, G-2, G-3, G-4, G-5, G-6, G-7, G-8, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G- 16, G-17, G-18, G-19, G-20, G-21, G-22, G-23, G-24, G-25, G-26, G-27, G-28, G-29, G-30 , G-31, G-32, G-33, G-34, G-35, G-37, G-38, G-40, G-41, G-42, G-43, G-45, G-47, G-48, G-50, G-53, G-54, G-55 or G-57, or a salt thereof.
[0280] [4] J represents J-1, A 1 represents a nitrogen atom, or a salt thereof.
[0281] [5] The aryltetrahydropyridine compound or a salt thereof according to any one of the above [1] to [3], wherein J represents J-2.
[0282] [6] The aryltetrahydropyridine compound or a salt thereof according to any one of the above [1] to [5], wherein G represents G-1, G-3, G-4, G-5, G-7, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-21, G-22, G-23, G-24, G-25, G-26, G-27, G-28, G-29, G-30, G-31, G-32, G-34, G-35, G-37, G-38, G-40, G-41, G-42, G-43, G-45, G-47, G-48, G-50, G-53, G-55 or G-57.
[0283] [7] Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-20, Q-22, Q-29, Q-31, Q-45, Q-47, or Q-52; Z 1 is a halogen atom, C 1 ~C 6 Alkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Alkynyl, halo(C 1 ~C 6 ) Alkyl, C 1 ~C 6 Alkoxy, halo(C 1 ~C 6 ) Alkoxy, C 1 ~C 6 Alkylthio, C 1 ~C 6 Alkylsulfinyl, C 1 ~C 6 Alkyl sulfonyl, halo(C 1 ~C 6 ) Alkylthio, Carboxy, C 1 ~C 6 Alkyl carbonyl, C 1 ~C 6 Alkoxycarbonyl, C 1 ~C 6 represents alkylaminocarbonyl, hydroxy, cyano or nitro; G represents G-1, G-2, G-3, G-4, G-5, G-6, G-7, G-8, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-27, G-28, or G-40; Z 2 is a halogen atom, C 1 ~C 6 Alkyl, C 2 ~C 6 Alkenyl, halo(C 1 ~C 6 ) Alkyl, C 1 ~C 6 Alkoxy, halo(C 1 ~C 6 ) Alkoxy, C1 ~C 6 Alkylthio, C 1 ~C 6 Alkylsulfinyl, C 1 ~C 6 Alkylsulfonyl, -NH 2 , Ji (C 1 ~C 6 ) Alkylamino, C 1 ~C 6 Alkyl carbonyl, C 1 ~C 6 Alkoxycarbonyl, hydroxy, -C(=NOR 14 )R 15 , nitro or cyano; R 14 is C 1 ~C 6 represents an alkyl group, R 1 is a hydrogen atom, a halogen atom or a halo(C 1 ~C 6 ) alkyl, R 2 is a hydrogen atom, -C(O)R 4 , -C(O)OR 5 , D-1, D-2 or D-3; R 4 is C 1 ~C 6 Alkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 6 Alkylcarbonyl or R 6 Replaced by (C 1 ~C 6 ) alkyl, R 6 is a halogen atom or C 1 ~C 6 represents alkoxy, Z 5 is C 1 ~C 6 represents an alkyl group, R 5 is C 1 ~C 6 Alkyl or C 2 ~C 6 represents alkenyl, R3 represents a hydrogen atom, The aryltetrahydropyridine compound or a salt thereof according to the above [1], wherein X represents an oxygen atom.
[0284] [8] The aryltetrahydropyridine compound or a salt thereof according to the above [7], wherein G represents G-1, G-3, G-4, G-5, G-7, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-27, G-28 or G-40.
[0285] [9] Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-12, Q-13, Q-14, Q-20, Q-22, Q-29, Q-45 or Q-47; Z 1 is a halogen atom, C 1 ~C 6 Alkyl, halo(C 1 ~C 6 ) Alkyl, C 1 ~C 6 Alkoxy, halo(C 1 ~C 6 ) Alkoxy, C 1 ~C 6 Alkylthio, C 1 ~C 6 Alkylsulfinyl, C 1 ~C 6 Alkyl sulfonyl, halo(C 1 ~C 6 ) Alkylthio, C 1 ~C 6 represents alkoxycarbonyl, cyano or nitro; Z 3 is C 1 ~C 6 represents an alkyl group, Z 2 is a halogen atom, C 1 ~C 6 Alkyl, halo(C 1 ~C 6 ) Alkyl, C 1 ~C 6Alkoxy, halo(C 1 ~C 6 ) Alkoxy, C 1 ~C 6 Alkylthio, C 1 ~C 6 Alkylsulfinyl, C 1 ~C 6 Alkylsulfonyl, -NH 2 , hydroxy, nitro or cyano, or a salt thereof according to the above [8].
[0286]
[10] J represents J-1, A 1 represents a nitrogen atom, Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-12, Q-13, Q-14 or Q-22; G represents G-1, G-3, G-4 or G-5; Z 2 is a halogen atom, C 1 ~C 6 Alkyl, halo(C 1 ~C 6 ) Alkyl, C 1 ~C 6 Alkoxy, halo(C 1 ~C 6 ) alkoxy or nitro; R 2 is a hydrogen atom or -C(O)OR 5 represents R 5 is C 1 ~C 6 represents an alkyl group, The aryltetrahydropyridine compound or a salt thereof according to the above [9], wherein Y represents an oxygen atom.
[0287]
[11] Q represents Q-1, Q-2, Q-3, Q-4, Q-6, Q-9 or Q-12; Z 1 is a halogen atom, C 1 ~C 6 Alkyl, halo(C 1 ~C6 ) alkyl, cyano or nitro; G represents G-1 or G-3; Z 2 is a halogen atom, C 1 ~C 6 Alkyl or halo(C 1 ~C 6 ) alkyl, R 1 is a halogen atom or halo(C 1 ~C 6 ) alkyl, R 2 represents a hydrogen atom, or a salt thereof.
[0288]
[12] J represents J-2, Q represents Q-1, Q-2, Q-3, Q-4, Q-6, Q-9, Q-10, Q-12, Q-20, Q-29, Q-45 or Q-47; Z 1 is a halogen atom, C 1 ~C 6 Alkyl, halo(C 1 ~C 6 ) Alkyl, C 1 ~C 6 Alkoxy, C 1 ~C 6 represents alkoxycarbonyl, cyano or nitro; G represents G-1, G-3, G-7, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-27, G-28, or G-40; Z 2 is a halogen atom, C 1 ~C 6 Alkyl, halo(C 1 ~C 6 ) Alkyl, C 1 ~C 6 Alkoxy, C 1 ~C 6 Alkylthio, C 1 ~C 6 Alkylsulfinyl, C 1 ~C6 Alkylsulfonyl, -NH 2 or a salt thereof according to the above [9], wherein R is an aryltetrahydropyridine compound or a salt thereof.
[0289]
[13] Q represents Q-1, Q-2, Q-3, Q-4, Q-6, Q-9 or Q-12; Z 1 is a halogen atom, C 1 ~C 6 Alkyl, halo(C 1 ~C 6 ) alkyl, cyano or nitro; G represents G-1, G-3 or G-7; Z 2 is a halogen atom, C 1 ~C 6 Alkyl or halo(C 1 ~C 6 ) alkyl, R 2 represents a hydrogen atom, or a salt thereof.
[0290]
[14] Formula (1-1):
[0291] [ka]
[0292] [In the formula, J represents J-1 or J-2,
[0293] [ka]
[0294] A 1 represents a nitrogen atom, G represents G-1, G-2, G-3, G-4, G-5, G-6, G-7, G-8, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-27, G-28, or G-40;
[0295] [ka]
[0296] Z 2 is a halogen atom, C 1 ~C 6 Alkyl, C 2 ~C 6 Alkenyl, halo(C 1 ~C 6 ) Alkyl, C 1 ~C 6 Alkoxy, halo(C 1 ~C 6 ) Alkoxy, C 1 ~C 6 Alkylthio, C 1 ~C 6 Alkylsulfinyl, C 1 ~C 6 Alkylsulfonyl, di(C 1 ~C 6 ) Alkylamino, C 1 ~C 6 Alkyl carbonyl, C 1 ~C 6 Alkoxycarbonyl, hydroxy, -C(=NOR 14 )R 15 , nitro or cyano; R 14 is C 1 ~C 6 represents an alkyl group, R 15 is a hydrogen atom or C 1 ~C 6 represents an alkyl group, Z 4 is C 1 ~C 6 represents an alkyl group, R 1 is a hydrogen atom, a halogen atom or a halo(C 1~C 6 ) alkyl, R 51 is C 1 ~C 6 represents an alkyl group, t2 represents an integer of 0, 1 or 2; t3 represents an integer of 0, 1, 2 or 3; t4 represents an integer of 0, 1, 2, 3 or 4; and t5 represents an integer of 0, 1, 2, 3, 4 or 5.], which is an intermediate for producing the aryltetrahydropyridine compound or a salt thereof according to any one of the above items [1] to
[13] .
[0297]
[15] J represents J-1, G represents G-1, G-2 or G-3; Z 2 is a halogen atom or C 1 ~C 6 represents an alkyl group, R 1 is a halogen atom or halo(C 1 ~C 6 15. An intermediate for producing the aryltetrahydropyridine compound or a salt thereof according to the above item 14, wherein R represents an alkyl group.
[0298]
[16] Formula (1-2):
[0299] [ka]
[0300] [In the formula, R 52 is a hydrogen atom or C 1 ~C 6 represents an alkyl group, R 2 is a hydrogen atom, -C(O)R 4 Or -C(O)OR 5 represents R 4 is C 1 ~C 6 represents an alkyl group, R 5 is C1 ~C 6 represents an alkyl group, Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-20, Q-22, Q-29, Q-31, Q-45 or Q-52;
[0301] [ka]
[0302] Z 1 is a halogen atom, C 1 ~C 6 Alkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Alkynyl, halo(C 1 ~C 6 ) Alkyl, C 1 ~C 6 Alkoxy, halo(C 1 ~C 6 ) Alkoxy, C 1 ~C 6 Alkylthio, C 1 ~C 6 Alkylsulfinyl, C 1 ~C 6 Alkyl sulfonyl, halo(C 1 ~C 6 ) Alkylthio, Carboxy, C 1 ~C 6 Alkyl carbonyl, C 1 ~C 6 Alkoxycarbonyl, C 1 ~C 6 represents alkylaminocarbonyl, hydroxy, cyano or nitro; Z 3 is a hydrogen atom or C 1 ~C 6 represents an alkyl group, t1 represents an integer of 0 or 1; t2 represents an integer of 0, 1 or 2; t3 represents an integer of 0, 1, 2 or 3; t4 represents an integer of 0, 1, 2, 3 or 4; and t5 represents an integer of 0, 1, 2, 3, 4 or 5.], which is an intermediate for producing the aryltetrahydropyridine compound or a salt thereof according to any one of the above items [1] to
[13] .
[0303]
[17] Q represents Q-1, Q-2, Q-3, Q-4, Q-6 or Q-9; Z 1 is a halogen atom, C 1 ~C 6 represents alkyl or cyano; R 2 is a hydrogen atom or -C(O)OR 5 An intermediate for producing the aryltetrahydropyridine compound or a salt thereof according to the above
[16] ,
[0304]
[18] A pest control agent comprising one or more aryltetrahydropyridine compounds and salts thereof as described in any one of [1] to
[13] above as an active ingredient.
[0305]
[19] An agricultural chemical comprising, as an active ingredient, one or more selected from the aryltetrahydropyridine compounds and salts thereof according to any one of [1] to
[13] above.
[0306]
[20] An agent for controlling internal or external parasites of mammals or birds, comprising one or more of the aryltetrahydropyridine compounds and salts thereof according to any one of [1] to
[13] above as an active ingredient.
[0307] 〔twenty one〕 The control agent according to the above
[20] , wherein the ectoparasite is of the order Fleas or Acarina.
[0308] 〔twenty two〕 An insecticide or acaricide comprising, as an active ingredient, one or more selected from the aryltetrahydropyridine compounds and salts thereof according to any one of [1] to
[13] above.
[0309] 〔twenty three〕 A seed treatment agent comprising, as an active ingredient, one or more selected from the aryltetrahydropyridine compounds and salts thereof according to any one of [1] to
[13] above.
[0310] 〔twenty four〕 The seed treatment agent according to the above
[23] , wherein the seed treatment is carried out by immersion treatment.
[0311] 〔twenty five〕 A soil treatment agent comprising one or more aryltetrahydropyridine compounds selected from the aryltetrahydropyridine compounds according to any one of [1] to
[13] above as active ingredients.
[0312]
[26] The soil treatment agent according to the above
[25] , wherein the soil treatment is carried out by soil drench treatment. EXAMPLES
[0313] The present invention will be explained in more detail below by describing synthesis examples and test examples of the compounds of the present invention as examples, but the present invention is not limited to these.
[0314] The medium pressure preparative liquid chromatography described in the synthesis examples was carried out using a medium pressure preparative apparatus manufactured by Yamazen Corporation; YFLC-Wprep (flow rate 18 ml / min, silica gel 40 μm column).
[0315] In addition, the proton nuclear magnetic resonance spectrum described below (hereinafter, 1 The chemical shift values of H-NMR are expressed as Me 4Using Si (tetramethylsilane), measurements were performed in a deuterated chloroform solvent at 300 MHz (model: JNM-ECX300 or JNM-ECP300, manufactured by JEOL) or 400 MHz (model: JNM-ECZ400S, manufactured by JEOL). 1 The symbols in the H-NMR chemical shift values have the following meanings. s: singlet, d: doublet, dd: double doublet, t: triplet, q: quartet, m: multiplet, brs: broad singlet Synthesis Example 1: Synthesis of N-(4-fluorophenyl)-6-[3-(6-fluoropyridin-3-yl)-4-(trifluoromethyl)phenyl]-4-hydroxy-2-oxo-1,2,5,6-tetrahydropyridine-3-carboxamide (Compound No. 1-001 of the present invention) 6-[3-bromo-4(trifluoromethyl)phenyl]-N-(4-fluorophenyl)-4-hydroxy-2-oxo-1,2,5,6-tetrahydropyridine-3-carboxamide 94mg, 1,4-dioxane 1.6ml and water 0.4ml mixed solution was added with 2-fluoropyridine-5-boronic acid 42mg, potassium carbonate 83mg and [1,1'-bis(diphenylphosphino)ferrocene]palladium (divalent) dichloride dichloromethane adduct 16mg, and stirred at 90℃ for 5 hours under nitrogen atmosphere. After the reaction was completed, 1mol / l hydrochloric acid 5ml was added and extracted with ethyl acetate (5ml x 3 times). The obtained organic layer was dehydrated and dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography [n-hexane:ethyl acetate = gradient from 100:0 to 0:100 (volume ratio, the same applies below)] to obtain 31 mg of the target product as a white solid.
[0316] Melting point: 200-202℃ 1H-NMR (300MHz):δ11.5-12.0(m, 1H), 8.18(brs, 1H), 7.85(d, J=8.7Hz, 1H), 7.65-7.8(m, 1H), 7.4-7.65(m, 4H), 7.33(brs, 1H), 6.95-7.1(m, 3H), 5.45-5.7(m, 1H), 4.8-5.0(m, 1H), 2.75-3.0(m, 2H). Synthesis Example 2: Synthesis of 6'-chloro-N-(4-chlorophenyl)-6''-fluoro-4-hydroxy-6-oxo-1,2,3,6-tetrahydro-[2,3':5',3''-terpyridine]-5-carboxamide (Compound No. 2-035 of the present invention) To a mixed solution of 100 mg of ethyl 6'-chloro-6''-fluoro-4-hydroxy-6-oxo-1,2,3,6-tetrahydro-[2,3':5',3''-terpyridine]-5-carboxylate and 0.7 ml of 1,4-dioxane, 32 mg of 4-chloroaniline was added and stirred at 80°C for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure. The resulting residue was washed with a mixed solution of ethyl acetate:n-hexane = 1:2 to obtain 41 mg of the target product as a light brown solid.
[0317] Melting point: 199~201℃ 1 H-NMR (300MHz):δ11.6(brs, 1H), 8.48(brs, 1H), 8.29(brs, 1H), 7.85-8.0(m, 1H), 7.65-7.8(m, 1H), 7.4-7.6(m, 2H), 7.25-7.35(m, 2H), 7.05-7.15(m, 2H), 5.3-5.8(m, 1H), 4.85-4.95(m, 1H), 2.7-3.05(m, 2H). Synthesis Example 3: Synthesis of N-(5-fluoropyridin-2-yl)-6-(3-(2-fluoropyridin-4-yl)-1,2,4-oxadiazol-5-yl)-4-hydroxy-2-oxo-1,2,5,6-tetrahydropyridine-3-carboxamide (Compound No. 3-036 of the present invention) To a mixed solution of 50 mg of 6-(((2-fluoroisonicotinimidamide)oxy)carbonyl)-N-(5-fluoropyridin-2-yl)-4-hydroxy-2-oxo-1,2,5,6-tetrahydropyridine-3-carboxamide and 1.7 ml of toluene, 17 mg of triethylamine was added and stirred at 110°C for 3 hours. After the reaction was completed, the solvent was distilled off under reduced pressure. 5 ml of 1 mol / l hydrochloric acid was added to the obtained residue, and the mixture was extracted with ethyl acetate (5 ml x 3 times). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. 1 ml of N,N-dimethylformamide, 3 ml of water, and 1 ml of 1 mol / l hydrochloric acid were added to the obtained residue. The precipitated solid was collected by filtration to obtain 39 mg of the target product as a white solid.
[0318] Melting point: 159-161℃ The synthesis examples of the intermediates for producing the compounds of the present invention used in Synthesis Example 2 are described below.
[0319] Intermediate synthesis example 1: Synthesis of ethyl 6'-chloro-6''-fluoro-4-hydroxy-6-oxo-1,2,3,6-tetrahydro-[2,3':5',3''-terpyridine]-5-carboxylate Step 1: Synthesis of ethyl 3-(5-bromo-6-chloropyridin-3-yl)-3-(3-ethoxy-3-oxopropanamido)propanoate To a mixed solution of 13 g of ethyl 3-amino-3-(5-bromo-6-chloropyridin-3-yl)propanoate, 142 ml of ethyl acetate, 7.2 g of sodium hydrogen carbonate, and 142 ml of water, 6.7 g of ethyl malonyl chloride was added at 0° C. After completion of the reaction, the obtained organic layer was dehydrated and dried over saturated saline and anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 18 g of the target product as a brown oil.
[0320] 1H-NMR (300MHz);δ8.3-8.4(m, 2H), 7.9-7.95(m, 1H), 5.35-5.5(m, 1H), 4.24(q, J=7.2Hz, 2H), 4.13(q, J=7.2Hz, 2H), 3.36(brs, 2H), 2.89(d, J=5.7Hz, 2H), 1.31(t, J=7.2Hz, 3H), 1.20(t, J=7.2Hz, 3H). Step 2: Synthesis of ethyl 5'-bromo-6'-chloro-4-hydroxy-6-oxo-1,2,3,6-tetrahydro-[2,3'-bipyridine]-5-carboxylate To a mixed solution of 22 g of ethyl 3-(5-bromo-6-chloropyridin-3-yl)-3-(3-ethoxy-3-oxopropanamido)propanoate and 94 ml of dehydrated ethanol, 2.0 g of sodium hydride [manufactured by Yoneyama Pharmaceutical Co., Ltd., product name: sodium hydride. oily (about 63% by mass), purity: 57.5-67.5%, product code 03414] was added, and the mixture was stirred at 55°C for 5 hours under a nitrogen atmosphere. After the reaction was completed, the solvent was distilled off under reduced pressure. 150 ml of dipropyl ether was added to the obtained residue, and the mixture was extracted with 150 ml of water. 35% by mass hydrochloric acid was added to the obtained aqueous layer until the pH became 2, and the mixture was extracted with a mixed solution of ethyl acetate:tetrahydrofuran = 9:1 (150 ml x 3 times). The obtained organic layer was dehydrated and dried with saturated saline and anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 16 g of the target product as a brown solid.
[0321] Melting point: 124~126℃ 1 H-NMR (400MHz);δ8.36(d, J=2.0Hz, 1H), 7.98(d, J=2.4Hz, 1H), 6.00(brs, 1H), 4.7-4.8(m, 1H), 4.35-4.5(m, 2H), 2.7-3.05(m, 2H), 1.40(t, J=7.2Hz, 3H). Step 3: Preparation of ethyl 6'-chloro-6''-fluoro-4-hydroxy-6-oxo-1,2,3,6-tetrahydro-[2,3':5',3''-terpyridine]-5-carboxylate To a mixture of 5.6 g of ethyl 5'-bromo-6'-chloro-4-hydroxy-6-oxo-1,2,3,6-tetrahydro-[2,3'-bipyridine]-5-carboxylate, 40 ml of 1,4-dioxane, and 10 ml of water, 1.9 g of 2-fluoropyridine-5-boronic acid, 9.5 g of tripotassium phosphate, and 606 mg of [1,1'-bis(diphenylphosphino)ferrocene]palladium (divalent) dichloride dichloromethane adduct were added, and the mixture was stirred at 55°C for 2 hours under a nitrogen atmosphere. After the reaction was completed, 200 ml of diisopropyl ether was added, and the mixture was extracted with a mixture of 10 g of potassium carbonate and 74 ml of water. 35% by mass hydrochloric acid was added to the obtained aqueous layer until the pH became 2, and the mixture was extracted with ethyl acetate (150 ml x 3 times). The obtained organic layer was dehydrated and dried with saturated saline and anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was washed with a mixed solution of ethanol:diisopropyl ether=1:2 to obtain 2.0 g of the desired product as a light brown solid.
[0322] Melting point: 178~180℃ 1 H-NMR (400MHz);δ8.47(d, J=2.4Hz, 1H), 8.30(brs, 1H), 7.9-8.0(m, 1H), 7.71(d, J=2.0Hz, 1H), 7.05-7.1(m, 1H), 5.70(brs, 1H), 4.8-4.9(m, 2H), 4.35-4.5(m, 2H), 2.7-3.05(m, 2H), 1.40(t, J=7.2Hz, 3H). The synthesis examples of the intermediates for producing the compounds of the present invention used in Synthesis Example 3 are described below.
[0323] Intermediate synthesis example 2: Synthesis of 6-(((2-fluoroisonicotinimidamide)oxy)carbonyl)-N-(5-fluoropyridin-2-yl)-4-hydroxy-2-oxo-1,2,5,6-tetrahydropyridine-3-carboxamide Step 1: Synthesis of di-tert-butyl 5-((5-fluoropyridin-2-yl)carbamoyl)-4-hydroxy-6-oxo-3,6-dihydropyridine-1,2(2H)-dicarboxylate To a mixed solution of 18.3 g of di-tert-butyl 4-hydroxy-6-oxo-3,6-dihydropyridine-1,2(2H)-dicarboxylate and 60 ml of acetonitrile, 4.0 g of imidazole and 6.6 g of 1,1'-carbonyldiimidazole were added and stirred at 85°C for 30 minutes. After cooling to room temperature, 6.6 g of 5-fluoropyridin-2-amine was added and stirred for 18 hours. 350 ml of diisopropyl ether was added and stirred at 0°C for 1.5 hours, and the precipitated solid was collected by filtration. The obtained solid was washed with a mixed solution of acetonitrile:diisopropyl ether = 1:5, and 26.3 g of the target product was obtained as a pale red solid.
[0324] Melting point: 152-154℃ Step 2: Synthesis of 5-((5-fluoropyridin-2-yl)carbamoyl)-4-hydroxy-6-oxo-1,2,3,6-tetrahydropyridine-2-carboxylic acid To a mixed solution of 15.4 g of di-tert-butyl 5-((5-fluoropyridin-2-yl)carbamoyl)-4-hydroxy-6-oxo-3,6-dihydropyridine-1,2(2H)-dicarboxylate and 70 ml of dichloromethane, 50 ml of trifluoroacetic acid was added and stirred at room temperature for 25 hours. 140 ml of toluene was added and the solvent was distilled off under reduced pressure. 100 ml of toluene was added and the solvent was distilled off under reduced pressure. 100 ml of toluene was added and the solvent was distilled off under reduced pressure. 100 ml of chloroform was added and the solid was filtered. The obtained solid was washed with chloroform to obtain 14.6 g of the target product as a white solid.
[0325] Melting point: 223~225℃ Step 3: Synthesis of 6-(((2-fluoroisonicotinimidamide)oxy)carbonyl)-N-(5-fluoropyridin-2-yl)-4-hydroxy-2-oxo-1,2,5,6-tetrahydropyridine-3-carboxamide 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride 72 mg and 1-hydroxy-7-azabenzotriazole 5 mg were added to a mixed solution of 5-((5-fluoropyridin-2-yl)carbamoyl)-4-hydroxy-6-oxo-1,2,3,6-tetrahydropyridine-2-carboxylic acid 100 mg, 2-fluoro-N-hydroxyisonicotinimidamide 55 mg and N,N-dimethylformamide 4 ml, and the mixture was stirred at room temperature for 1 hour. After the reaction was completed, water 12 ml and 1 mol / l hydrochloric acid 1 ml were added, and the precipitated solid was filtered. The obtained solid was washed with water to obtain 80 mg of the target product as a white solid.
[0326] Melting point: 146-148℃ The compound of the present invention and the intermediates can be synthesized according to the above-mentioned production method and synthesis examples. Tables 31 to 36 show examples of aryltetrahydropyridine compounds produced in the same manner as Synthesis Examples 1 to 3, but the aryltetrahydropyridine compounds of the present invention are not limited to these. Tables 37 to 39 show examples of intermediates produced in the same manner as Synthesis Examples 1 and 2, but the intermediates of the present invention are not limited to these.
[0327] In addition, in the table, Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12a, Q-12b, Q-13, Q-14, Q-20, Q-22, Q-29, Q-31a, Q-45a, Q-47a and Q-52a respectively represent the following structures.
[0328] [ka]
[0329] In addition, in the table, G-1, G-2, G-3, G-4, G-5, G-6a, G-7, G-8a, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-27, G-28 and G-40 each represent the following structures.
[0330] [ka]
[0331] In addition, the descriptions D-1, D-2 and D-3 in the table respectively represent the following structures.
[0332] [ka]
[0333] The numbers in the above structural formula indicate the substituents (Z 1 ) t1 , (Z 1 ) t2 , (Z 1 ) t3 , (Z 1 ) t4 , (Z 1 ) t5 , (Z 2 ) t2 , (Z ...
Claims
1. Formula (1): 【Chemistry 1】 [In the formula, Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-15, Q-16, Q-17, Q-18, Q-19, Q-20, Q-21, Q-22, Q-23, Q-24, Q-25, Q-26, Q-27, Q-28, Q-2 9, Q-30, Q-31, Q-32, Q-33, Q-34, Q-35, Q-36, Q-37, Q-38, Q-39, Q-40, Q-41, Q-42, Q-43, Q-44, Q-45, Q-46, Q-47, Q-48, Q-49, Q-50, Q-51, Q-52, Q-53, Q-54, Q-55 or Q-56; 【Chemistry 2】 【Chemistry 3】 Z 1 is a halogen atom, C 1 ~C 6 Alkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Alkynyl, halo(C 1 ~C 6 ) alkyl, halo (C 2 ~C 6 ) alkenyl, halo(C 2 ~C 6 ) alkynyl, C 1 ~C 6 Alkoxy, halo(C 1 ~C 6 ) Alkoxy, C 2 ~C 6 Alkoxy (C 1 ~C 6 ) Alkoxy, C 2 ~C 6 Alkenyloxy, halo(C 2 ~C 6 ) alkenyloxy, C 2 ~C 6 Alkynyloxy, halo(C 2 ~C 6 ) alkynyloxy, C 1 ~C 6 Alkylthio, C 1 ~C 6 Alkylsulfinyl, C 1 ~C 6 Alkyl sulfonyl, halo(C 1 ~C 6 ) alkylthio, halo(C 1 ~C 6 ) alkylsulfinyl, halo(C 1 ~C 6 ) alkylsulfonyl, C 2 ~C 6 Alkenylthio, C 2 ~C 6 Alkenylsulfinyl, C 2 ~C 6 Alkenylsulfonyl, halo(C 2 ~C 6 ) alkenylthio, halo(C 2 ~C 6 ) alkenylsulfinyl, halo(C 2 ~C 6 ) alkenylsulfonyl, C 2 ~C 6 Alkynylthio, C 2 ~C 6 Alkynylsulfinyl, C 2 ~C 6 Alkynylsulfonyl, halo(C 2 ~C 6 ) alkynylthio, halo(C 2 ~C 6 ) alkynylsulfinyl, halo(C 2 ~C 6 ) alkynylsulfonyl, -NH 2 , C 1 ~C 6 Alkylamino, di(C 1 ~C 6 ) alkylamino, halo(C 1 ~C 6 ) alkylamino, dihalo (C 1 ~C 6 ) alkylamino, formyl, carboxy, C 1 ~C 6 Alkylcarbonyl, halo(C 1 ~C 6 ) alkylcarbonyl, C 1 ~C 6 Alkoxycarbonyl, halo(C 1 ~C 6 ) alkoxycarbonyl, C 1 ~C 6 Alkylaminocarbonyl, halo(C 1 ~C 6 ) alkylaminocarbonyl, di(C 1 ~C 6 ) alkylaminocarbonyl, hydroxy, C 1 ~C 6 Alkylcarbonyloxy, C 1 ~C 6 Alkoxycarbonyloxy, C 1 ~C 6 Alkyl sulfonyloxy, halo(C 1 ~C 6 ) Alkylsulfonyloxy, -SO 3 H.C. 1 ~C 6 Alkylaminosulfonyl, di(C 1 ~C 6 ) alkylaminosulfonyl, -C(=NOR 12 ) R 13 , cyano or nitro; R 12 is a hydrogen atom or C 1 ~C 6 represents an alkyl group, R 13 is a hydrogen atom or C 1 ~C 6 represents an alkyl group, Z 3 is a hydrogen atom or C 1 ~C 6 represents an alkyl group, J represents J-1 or J-2; 【Chemistry 4】 A 1 represents a nitrogen atom or CH; G is G-1, G-2, G-3, G-4, G-5, G-6, G-7, G-8, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G -17, G-18, G-19, G-20, G-21, G-22, G-23, G-24, G-25, G-26, G-27, G-28, G-29, G-30, G-31, G- 32, G-33, G-34, G-35, G-36, G-37, G-38, G-39, G-40, G-41, G-42, G-43, G-44, G-45, G-46, G-4 7, G-48, G-49, G-50, G-51, G-52, G-53, G-54, G-55, G-56, G-57, G-58, G-59, G-60 or G-61; 【Chemistry 5】 【Chemistry 6】 Z 2 is a halogen atom, C 1 ~C 6 Alkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Alkynyl, halo(C 1 ~C 6 ) alkyl, halo (C 2 ~C 6 ) alkenyl, halo(C 2 ~C 6 ) alkynyl, C 1 ~C 6 Alkoxy, halo(C 1 ~C 6 ) Alkoxy, C 1 ~C 6 Alkoxy (C 1 ~C 6 ) Alkoxy, C 2 ~C 6 Alkenyloxy, halo(C 2 ~C 6 ) alkenyloxy, C 2 ~C 6 Alkynyloxy, halo(C 2 ~C 6 ) alkynyloxy, C 1 ~C 6 Alkylthio, C 1 ~C 6 Alkylsulfinyl, C 1 ~C 6 Alkyl sulfonyl, halo(C 1 ~C 6 ) alkylthio, halo(C 1 ~C 6 ) alkylsulfinyl, halo(C 1 ~C 6 ) alkylsulfonyl, C 2 ~C 6 Alkenylthio, C 2 ~C 6 Alkenylsulfinyl, C 2 ~C 6 Alkenylsulfonyl, halo(C 2 ~C 6 ) alkenylthio, halo(C 2 ~C 6 ) alkenylsulfinyl, halo(C 2 ~C 6 ) alkenylsulfonyl, C 2 ~C 6 Alkynylthio, C 2 ~C 6 Alkynylsulfinyl, C 2 ~C 6 Alkynylsulfonyl, halo(C 2 ~C 6 ) alkynylthio, halo(C 2 ~C 6 ) alkynylsulfinyl, halo(C 2 ~C 6 ) alkynylsulfonyl, -NH 2 , C 1 ~C 6 Alkylamino, di(C 1 ~C 6 ) alkylamino, halo(C 1 ~C 6 ) alkylamino, dihalo (C 1 ~C 6 ) alkylamino, formyl, carboxy, C 1 ~C 6 Alkylcarbonyl, halo(C 1 ~C 6 ) alkylcarbonyl, C 1 ~C 6 Alkoxycarbonyl, halo(C 1 ~C 6 ) alkoxycarbonyl, C 1 ~C 6 Alkylaminocarbonyl, halo(C 1 ~C 6 ) alkylaminocarbonyl, di(C 1 ~C 6 ) alkylaminocarbonyl, hydroxy, C 1 ~C 6 Alkylcarbonyloxy, C 1 ~C 6 Alkoxycarbonyloxy, C 1 ~C 6 Alkyl sulfonyloxy, halo(C 1 ~C 6 ) Alkylsulfonyloxy, -SO 3 H.C. 1 ~C 6 Alkylaminosulfonyl, di(C 1 ~C 6 ) alkylaminosulfonyl, -C(=NOR 14 ) R 15 , nitro or cyano; R 14 is a hydrogen atom or C 1 ~C 6 represents an alkyl group, R 15 is a hydrogen atom or C 1 ~C 6 represents an alkyl group, Z 4 is C 1 ~C 6 represents an alkyl group, R 1 represents a hydrogen atom, a halogen atom, or a halo(C 1 ~C 6 ) alkyl, C 1 ~C 6 represents alkyl or cyano; R 2 is a hydrogen atom, C 1 ~C 6 Alkyl, halo (C 1 ~C 6 ) alkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Alkynyl, C 3 ~C 6 Cycloalkyl, —C(O)R 4 , -C(O)OR 5 , D-1, D-2 or D-3; 【Chemistry 7】 R 4 is C 1 ~C 6 Alkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Alkynyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 6 Alkylcarbonyl, di(C 1 ~C 6 ) alkylamino or R 6 (C 1 ~C 6 ) alkyl; R 6 is a halogen atom, C 1 ~C 6 Alkoxy, cyano, nitro, phenyl or R 8 represents a phenyl substituted with Z 5 is a halogen atom, C 1 ~C 6 Alkyl, C 1 ~C 6 represents alkoxy, cyano or nitro, R 8 is a halogen atom, C 1 ~C 6 Alkyl, C 1 ~C 6 represents alkoxy, cyano or nitro, R 5 is C 1 ~C 6 Alkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Alkynyl, C 3 ~C 6 Cycloalkyl, R 9 (C 1 ~C 6 ) alkyl, phenyl or R 10 represents a phenyl substituted with R 9 is a halogen atom, C 1 ~C 6 Alkoxy, cyano, nitro, phenyl or R 11 represents a phenyl substituted with R 10 is a halogen atom, C 1 ~C 6 Alkyl, C 1 ~C 6 represents alkoxy, cyano or nitro, R 11 is a halogen atom, C 1 ~C 6 Alkyl, C 1 ~C 6 represents alkoxy, cyano or nitro, R 3 is a hydrogen atom, C 1 ~C 6 Alkyl, halo (C 1 ~C 6 ) alkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Alkynyl, C 3 ~C 6 Cycloalkyl or C 1 ~C 6 represents alkylcarbonyl, X represents an oxygen atom or a sulfur atom; Y represents an oxygen atom or a sulfur atom; t1 represents an integer of 0 or 1; t2 represents an integer of 0, 1 or 2; t3 represents an integer of 0, 1, 2 or 3; t4 represents an integer of 0, 1, 2, 3 or 4; t5 represents an integer of 0, 1, 2, 3, 4 or 5; and t8 represents an integer of 0, 1, 2, 3 or 4.] or a salt thereof.
2. A 1 The aryltetrahydropyridine compound or a salt thereof according to claim 1 , wherein represents a nitrogen atom.
3. Z 1 is a halogen atom, C 1 ~C 6 Alkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Alkynyl, halo(C 1 ~C 6 ) alkyl, C 1 ~C 6 Alkoxy, halo(C 1 ~C 6 ) Alkoxy, C 1 ~C 6 Alkylthio, C 1 ~C 6 Alkylsulfinyl, C 1 ~C 6 Alkyl sulfonyl, halo(C 1 ~C 6 ) alkylthio, halo(C 1 ~C 6 ) alkylsulfinyl, halo(C 1 ~C 6 ) alkylsulfonyl, -NH 2 , C 1 ~C 6 Alkylamino, di(C 1 ~C 6 ) alkylamino, carboxy, C 1 ~C 6 Alkylcarbonyl, C 1 ~C 6 Alkoxycarbonyl, C 1 ~C 6 Alkylaminocarbonyl, di(C 1 ~C 6 ) alkylaminocarbonyl, hydroxy, C 1 ~C 6 Alkylcarbonyloxy, C 1 ~C 6 represents alkylsulfonyloxy, cyano or nitro; Z 2 is a halogen atom, C 1 ~C 6 Alkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Alkynyl, halo(C 1 ~C 6 ) alkyl, halo (C 2 ~C 6 ) alkenyl, halo(C 2 ~C 6 ) alkynyl, C 1 ~C 6 Alkoxy, halo(C 1 ~C 6 ) Alkoxy, C 1 ~C 6 Alkylthio, C 1 ~C 6 Alkylsulfinyl, C 1 ~C 6 Alkyl sulfonyl, halo(C 1 ~C 6 ) alkylthio, halo(C 1 ~C 6 ) alkylsulfinyl, halo(C 1 ~C 6 ) alkylsulfonyl, -NH 2 , C 1 ~C 6 Alkylamino, di(C 1 ~C 6 ) alkylamino, carboxy, C 1 ~C 6 Alkylcarbonyl, C 1 ~C 6 Alkoxycarbonyl, C 1 ~C 6 Alkylaminocarbonyl, di(C 1 ~C 6 ) alkylaminocarbonyl, hydroxy, C 1 ~C 6 Alkylcarbonyloxy, C 1 ~C 6 Alkylsulfonyloxy, -C(=NOR 14 ) R 15 , nitro or cyano; Z 5 is a halogen atom, C 1 ~C 6 Alkyl or C 1 ~C 6 represents alkoxy, R 1 is a hydrogen atom, a halogen atom or a halo(C 1 ~C 6 ) alkyl; R 2 is a hydrogen atom, -C(O)R 4 , -C(O)OR 5 , D-1, D-2 or D-3; R 3 represents a hydrogen atom, Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-15, Q-16, Q-17, Q-18, Q-19, Q-20, Q-21, Q-22, Q-23, Q-25, Q-26, Q-27, Q-29, Q-30, Q-31, Q-32, Q-33, Q-38, Q-39, Q-40, Q-41, Q-42, Q-43, Q-44, Q-45, Q-46, Q-47, Q-50, Q-51, Q-52 or Q-54; G is G-1, G-2, G-3, G-4, G-5, G-6, G-7, G-8, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G -16, G-17, G-18, G-19, G-20, G-21, G-22, G-23, G-24, G-25, G-26, G-27, G-28, G-29, G- The aryltetrahydropyridine compound or a salt thereof according to any one of claims 1 to 2, wherein G-30, G-31, G-32, G-33, G-34, G-35, G-37, G-38, G-40, G-41, G-42, G-43, G-45, G-47, G-48, G-50, G-53, G-54, G-55 or G-57.
4. J represents J-1; A 1 The aryltetrahydropyridine compound or a salt thereof according to any one of claims 1 to 3, wherein represents a nitrogen atom.
5. The aryltetrahydropyridine compound or a salt thereof according to any one of claims 1 to 3, wherein J represents J-2.
6. The aryltetrahydropyridine compound or a salt thereof according to any one of claims 1 to 5, wherein G represents G-1, G-3, G-4, G-5, G-7, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-21, G-22, G-23, G-24, G-25, G-26, G-27, G-28, G-29, G-30, G-31, G-32, G-34, G-35, G-37, G-38, G-40, G-41, G-42, G-43, G-45, G-47, G-48, G-50, G-53, G-55, or G-57.
7. Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-20, Q-22, Q-29, Q-31, Q-45, Q-47 or Q-52; Z 1 is a halogen atom, C 1 ~C 6 Alkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Alkynyl, halo(C 1 ~C 6 ) alkyl, C 1 ~C 6 Alkoxy, halo(C 1 ~C 6 ) Alkoxy, C 1 ~C 6 Alkylthio, C 1 ~C 6 Alkylsulfinyl, C 1 ~C 6 Alkyl sulfonyl, halo(C 1 ~C 6 ) alkylthio, carboxy, C 1 ~C 6 Alkylcarbonyl, C 1 ~C 6 Alkoxycarbonyl, C 1 ~C 6 represents alkylaminocarbonyl, hydroxy, cyano or nitro; G represents G-1, G-2, G-3, G-4, G-5, G-6, G-7, G-8, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-27, G-28, or G-40; Z 2 is a halogen atom, C 1 ~C 6 Alkyl, C 2 ~C 6 Alkenyl, halo(C 1 ~C 6 ) alkyl, C 1 ~C 6 Alkoxy, halo(C 1 ~C 6 ) Alkoxy, C 1 ~C 6 Alkylthio, C 1 ~C 6 Alkylsulfinyl, C 1 ~C 6 Alkylsulfonyl, -NH 2 , Ji (C 1 ~C 6 ) alkylamino, C 1 ~C 6 Alkylcarbonyl, C 1 ~C 6 Alkoxycarbonyl, hydroxy, -C(=NOR 14 ) R 15 , nitro or cyano; R 14 is C 1 ~C 6 represents an alkyl group, R 1 is a hydrogen atom, a halogen atom or a halo(C 1 ~C 6 ) alkyl; R 2 is a hydrogen atom, -C(O)R 4 , -C(O)OR 5 , D-1, D-2 or D-3; R 4 is C 1 ~C 6 Alkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 6 Alkylcarbonyl or R 6 (C 1 ~C 6 ) alkyl; R 6 is a halogen atom or C 1 ~C 6 represents alkoxy, Z 5 is C 1 ~C 6 represents an alkyl group, R 5 is C 1 ~C 6 Alkyl or C 2 ~C 6 represents alkenyl, R 3 represents a hydrogen atom, The aryltetrahydropyridine compound or a salt thereof according to claim 1, wherein X represents an oxygen atom.
8. The aryltetrahydropyridine compound or a salt thereof according to claim 7, wherein G represents G-1, G-3, G-4, G-5, G-7, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-27, G-28, or G-40.
9. Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-12, Q-13, Q-14, Q-20, Q-22, Q-29, Q-45 or Q-47; Z 1 is a halogen atom, C 1 ~C 6 Alkyl, halo (C 1 ~C 6 ) alkyl, C 1 ~C 6 Alkoxy, halo(C 1 ~C 6 ) Alkoxy, C 1 ~C 6 Alkylthio, C 1 ~C 6 Alkylsulfinyl, C 1 ~C 6 Alkyl sulfonyl, halo(C 1 ~C 6 ) alkylthio, C 1 ~C 6 represents alkoxycarbonyl, cyano or nitro; Z 3 is C 1 ~C 6 represents an alkyl group, Z 2 is a halogen atom, C 1 ~C 6 Alkyl, halo (C 1 ~C 6 ) alkyl, C 1 ~C 6 Alkoxy, halo(C 1 ~C 6 ) Alkoxy, C 1 ~C 6 Alkylthio, C 1 ~C 6 Alkylsulfinyl, C 1 ~C 6 Alkylsulfonyl, -NH 2 9. The aryltetrahydropyridine compound or a salt thereof according to claim 8, wherein R represents hydroxy, nitro or cyano.
10. J represents J-1; A 1 represents a nitrogen atom, Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-12, Q-13, Q-14, Q-22 or Q-29; G represents G-1, G-3, G-4 or G-5; Z 2 is a halogen atom, C 1 ~C 6 Alkyl, halo (C 1 ~C 6 ) alkyl, C 1 ~C 6 Alkoxy, halo(C 1 ~C 6 ) represents alkoxy or nitro, R 2 is a hydrogen atom or -C(O)OR 5 represents R 5 is C 1 ~C 6 represents an alkyl group, The aryltetrahydropyridine compound or a salt thereof according to claim 9, wherein Y represents an oxygen atom.
11. Q represents Q-1, Q-2, Q-3, Q-4, Q-6, Q-9 or Q-12; Z 1 is a halogen atom, C 1 ~C 6 Alkyl, halo (C 1 ~C 6 ) alkyl, cyano or nitro; G represents G-1 or G-3; Z 2 is a halogen atom, C 1 ~C 6 Alkyl or halo(C 1 ~C 6 ) alkyl; R 1 is a halogen atom or halo(C 1 ~C 6 ) alkyl; R 2 The aryltetrahydropyridine compound or a salt thereof according to claim 10, wherein represents a hydrogen atom.
12. J represents J-2; Q represents Q-1, Q-2, Q-3, Q-4, Q-6, Q-9, Q-10, Q-12, Q-20, Q-29, Q-45 or Q-47; Z 1 is a halogen atom, C 1 ~C 6 Alkyl, halo (C 1 ~C 6 ) alkyl, C 1 ~C 6 Alkoxy, C 1 ~C 6 represents alkoxycarbonyl, cyano or nitro; G represents G-1, G-3, G-7, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-27, G-28 or G-40; Z 2 is a halogen atom, C 1 ~C 6 Alkyl, halo (C 1 ~C 6 ) alkyl, C 1 ~C 6 Alkoxy, C 1 ~C 6 Alkylthio, C 1 ~C 6 Alkylsulfinyl, C 1 ~C 6 Alkylsulfonyl, -NH 2 10. The aryltetrahydropyridine compound or a salt thereof according to claim 9, wherein R is 0 or 1.
13. Q represents Q-1, Q-2, Q-3, Q-4, Q-6, Q-9 or Q-12; Z 1 is a halogen atom, C 1 ~C 6 Alkyl, halo (C 1 ~C 6 ) alkyl, cyano or nitro; G represents G-1, G-3 or G-7; Z 2 is a halogen atom, C 1 ~C 6 Alkyl or halo(C 1 ~C 6 ) alkyl; R 2 The aryltetrahydropyridine compound or a salt thereof according to claim 12, wherein represents a hydrogen atom.
14. Formula (1-1): 【Chemistry 8】 [In the formula, J represents J-1 or J-2, 【Chemistry 9】 A 1 represents a nitrogen atom, G represents G-1, G-2, G-3, G-4, G-5, G-6, G-7, G-8, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-27, G-28, or G-40; 【Chemistry 10】 Z 2 is a halogen atom, C 1 ~C 6 Alkyl, C 2 ~C 6 Alkenyl, halo(C 1 ~C 6 ) alkyl, C 1 ~C 6 Alkoxy, halo(C 1 ~C 6 ) Alkoxy, C 1 ~C 6 Alkylthio, C 1 ~C 6 Alkylsulfinyl, C 1 ~C 6 Alkylsulfonyl, di(C 1 ~C 6 ) alkylamino, C 1 ~C 6 Alkylcarbonyl, C 1 ~C 6 Alkoxycarbonyl, hydroxy, -C(=NOR 14 ) R 15 , nitro or cyano; R 14 is C 1 ~C 6 represents an alkyl group, R 15 is a hydrogen atom or C 1 ~C 6 represents an alkyl group, Z 4 is C 1 ~C 6 represents an alkyl group, R 1 is a hydrogen atom, a halogen atom or a halo(C 1 ~C 6 ) alkyl; R 51 is C 1 ~C 6 represents an alkyl group, t2 represents an integer of 0, 1 or 2; t3 represents an integer of 0, 1, 2 or 3; t4 represents an integer of 0, 1, 2, 3 or 4; and t5 represents an integer of 0, 1, 2, 3, 4 or 5.]. The intermediate for producing the aryltetrahydropyridine compound or a salt thereof according to any one of claims 1 to 13,
15. J represents J-1; G represents G-1, G-2 or G-3; Z 2 is a halogen atom or C 1 ~C 6 represents an alkyl group, R 1 is a halogen atom or halo(C 1 ~C 6 15. An intermediate for producing the aryltetrahydropyridine compound or a salt thereof according to claim 14, wherein R is an alkyl group.
16. Formula (1-2): 【Chemistry 11】 [In the formula, R 52 is a hydrogen atom or C 1 ~C 6 represents an alkyl group, R 2 is a hydrogen atom, -C(O)R 4 Or -C(O)OR 5 represents R 4 is C 1 ~C 6 represents an alkyl group, R 5 is C 1 ~C 6 represents an alkyl group, Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-20, Q-22, Q-29, Q-31, Q-45 or Q-52; 【Chemistry 12】 Z 1 is a halogen atom, C 1 ~C 6 Alkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Alkynyl, halo(C 1 ~C 6 ) alkyl, C 1 ~C 6 Alkoxy, halo(C 1 ~C 6 ) Alkoxy, C 1 ~C 6 Alkylthio, C 1 ~C 6 Alkylsulfinyl, C 1 ~C 6 Alkyl sulfonyl, halo(C 1 ~C 6 ) alkylthio, carboxy, C 1 ~C 6 Alkylcarbonyl, C 1 ~C 6 Alkoxycarbonyl, C 1 ~C 6 represents alkylaminocarbonyl, hydroxy, cyano or nitro; Z 3 is a hydrogen atom or C 1 ~C 6 represents an alkyl group, t1 represents an integer of 0 or 1; t2 represents an integer of 0, 1 or 2; t3 represents an integer of 0, 1, 2 or 3; t4 represents an integer of 0, 1, 2, 3 or 4; and t5 represents an integer of 0, 1, 2, 3, 4 or 5. The intermediate for producing the aryltetrahydropyridine compound or a salt thereof according to any one of claims 1 to 13, represented by the formula:
17. Q represents Q-1, Q-2, Q-3, Q-4, Q-6 or Q-9; Z 1 is a halogen atom, C 1 ~C 6 represents alkyl or cyano; R 2 is a hydrogen atom or -C(O)OR 5 17. An intermediate for producing the aryltetrahydropyridine compound or a salt thereof according to claim 16, which represents:
18. A pest control agent comprising, as an active ingredient, one or more selected from the aryltetrahydropyridine compounds and salts thereof according to any one of claims 1 to 13.
19. 14. An agricultural chemical comprising, as an active ingredient, one or more selected from the aryltetrahydropyridine compounds and salts thereof according to any one of claims 1 to 13.
20. 14. An agent for controlling internal or external parasites of mammals or birds, comprising one or more selected from the aryltetrahydropyridine compounds and salts thereof according to any one of claims 1 to 13 as an active ingredient.
21. The control agent according to claim 20, wherein the ectoparasite is of the order Fleas or Acarina.
22. 14. An insecticide or acaricide comprising, as an active ingredient, one or more selected from the aryltetrahydropyridine compounds and salts thereof according to any one of claims 1 to 13.
23. A seed treatment agent comprising, as an active ingredient, one or more selected from the aryltetrahydropyridine compounds and salts thereof according to any one of claims 1 to 13.
24. The seed treatment agent according to claim 23, wherein the seed treatment is carried out by immersion treatment.
25. A soil treatment agent comprising, as an active ingredient, one or more aryltetrahydropyridine compounds selected from the aryltetrahydropyridine compounds according to any one of claims 1 to 13.
26. The soil treatment agent according to claim 25, wherein the soil treatment is carried out by soil drench treatment.
Citation Information
Patent Citations
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