Isoxazoline-substituted benzamide compounds and pest control agents

Abstract

Provided are novel pest control agents, particularly insecticides, acaricides and ectoparasiticides. 【Solution means】Formula (1): JPEG2026101111000079.jpg40159 [In the formula, W represents an oxygen atom or a sulfur atom, Q represents Q-1 or Q-2, X 1 , X 2 and X 3 each independently represents a hydrogen atom, a halogen atom, C1-C6 haloalkyl, etc., Y 1 represents a halogen atom, C1-C6 alkyl, etc., Y 2 represents a hydrogen atom, R 1 represents -C(O)R 1a , -C(O)N(R 1c )R 1b , -C(O)OR 2a , -S(O)2R 1a etc., R 2 represents a hydrogen atom, C1-C6 alkyl, etc., R 3 represents a hydrogen atom, C1-C6 alkyl, etc., R 4 represents a hydrogen atom, etc., R A represents C1-C6 alkyl, etc.]. An isoxazoline-substituted benzamide compound represented by or a salt thereof.

Description

Technical Field

[0001] The present invention relates to novel isoxazoline-substituted benzamide compounds and salts thereof, and a pest control agent, an agricultural chemical, a control agent, an insecticide or a miticide, a seed treatment agent, and a soil treatment agent, which are characterized by containing the compound as an active ingredient.

Background Art

[0002] Certain isoxazoline-substituted benzamide compounds are known to have pest control activity (see, for example, Patent Documents 1 to 5).

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Patent Document 2

Patent Document 3

Patent Document 4

Patent Document 5

Summary of the Invention

Problems to be Solved by the Invention

[0004] However, due to the long-term use of these agents, in recent years, pests have acquired drug resistance, and there have been an increasing number of situations where it has become difficult to control them with existing insecticides and fungicides that have been conventionally used. Although Patent Documents 1 and the like disclose isoxazoline-substituted benzamide compounds and the like, it is desired to develop a drug having a structure different from that of Patent Documents 1 and the like by using a synthesis method different from that of Patent Documents 1 and the like. Thus, the development of a novel drug having an excellent pest control effect has always been expected. [Means for solving the problem]

[0005] The present inventors, through diligent research aimed at solving the above-mentioned problems, have discovered that a novel isoxazoline-substituted benzamide compound represented by the following formula (1) according to the present invention is an extremely useful compound that exhibits excellent pest control activity, particularly insecticidal and acaricidal activity, and have completed the present invention.

[0006] In other words, the present invention relates to the following [1].

[0007] [1] An isoxazoline-substituted benzamide compound represented by the following formula (1), or a salt thereof.

[0008] [ka]

[0009] [In the formula, W represents an oxygen atom or a sulfur atom, Q represents Q-1 or Q-2,

[0010] [ka]

[0011] X 1 , X 2 and X 3 Each of these independently represents a hydrogen atom, a halogen atom, a cyano, a nitro, an amino, a C1-C6 alkyl, a C1-C6 alkoxy, a C1-C6 haloalkyl, or a halo(C1-C6)alkoxy. Y 1 This represents a hydrogen atom, a halogen atom, a cyano, a nitro, a C1-C6 alkyl, a C1-C6 haloalkyl, or a halo(C1-C6) alkoxy. Y 2 This represents a hydrogen atom, Or, Y 1 and Y 2 These elements combine to form a 6-membered ring -CH=CH-CH=CH-, R 1 is -C(O)R 1a 、-C(S)R 1a 、-C(O)OR 2a 、-C(O)SR 2a 、-C(O)N(R 1c )R 1b 、-C(S)N(R 1c )R 1b 、-S(O)2R 1a 、-S(O)2N(R 1c )R 1b 、-C(O)C(O)R 1a or -CHO, R 2 is a hydrogen atom, C1 - C6 alkyl, (C1 - C6) alkyl substituted by R 10 , C2 - C6 alkenyl or C2 - C6 alkynyl, R 3 is a hydrogen atom, C1 - C6 alkyl, (C1 - C6) alkyl substituted by R 6 , C1 - C6 haloalkyl, C2 - C6 alkenyl, halo(C2 - C6) alkenyl, C2 - C6 alkynyl, halo(C2 - C6) alkynyl, C3 - C 10 cycloalkyl, halo(C3 - C 10 )cycloalkyl, C1 - C6 alkoxy, halo(C1 - C6) alkoxy, -C(O)R 1d 、-C(S)R 1d 、-C(O)OR 1d 、-C(O)SR 1d 、-C(O)N(R 1f )R 1e 、-C(S)N(R 1f )R 1e 、-S(O)2R 1d 、-S(O)2N(R 1f )R 1e or -N(R 14 )R 15 represents, R 4 is a hydrogen atom, C1 - C6 alkyl, C2 - C6 alkenyl or C2 - C6 alkynyl, R A is C1 - C6 alkyl, R 16(C1-C6) alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, halo(C2-C6) alkenyl, C2-C6 alkynyl, halo(C2-C6) alkynyl, C3-C 10 Cycloalkyl, -C(O)R 1g or -C(O)OR 1h This represents, R 1a C1~C 10 Alkyl, R 7 (C1-C6) alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, halo(C2-C6) alkenyl, C2-C6 alkynyl, halo(C2-C6) alkynyl, C3-C 10 Cycloalkyl, Halo(C3~C 10 ) Cycloalkyl, R 13 C3~C substituted by 10 Cycloalkyl, phenyl, (Z 1 ) p1 Represents phenyl, D-1 to D-60, G-1 to G-60, or G-61 substituted by, D-1 to D-60 represent the following structures,

[0012] [ka]

[0013] [ka]

[0014] [ka]

[0015] G-1 to G-61 represent the following structures,

[0016] [ka]

[0017] [ka]

[0018] [ka]

[0019] R 2a C1-C6 alkyl, R 7 (C1-C6) alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, halo(C2-C6) alkenyl, C2-C6 alkynyl, halo(C2-C6) alkynyl, C3-C 10 Cycloalkyl, phenyl or (Z 1 ) p1 Represents phenyl substituted by, R 1b is a hydrogen atom, C1-C6 alkyl, R 8 (C1-C6) alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, halo(C2-C6) alkenyl, C2-C6 alkynyl, halo(C2-C6) alkynyl, C3-C 10 Cycloalkyl, C1-C6 alkoxy, halo(C1-C6)alkoxy, C1-C6 alkoxycarbonyl, phenyl or (Z 1 ) p1 Represents phenyl substituted by, R 1c This represents a hydrogen atom or a C1-C6 alkyl group. R 1d C1-C6 alkyl, R 9 (C1-C6) alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, halo(C2-C6) alkenyl, C2-C6 alkynyl, halo(C2-C6) alkynyl, C3-C 10 Cycloalkyl, Halo(C3~C 10 )Cycloalkyl, phenyl, (Z 2 ) p2 Represents phenyl, G-4 to G-10, G-50 to G-57, or G-58 substituted by, R 1eC1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C 10 Cycloalkyl, phenyl or (Z 2 ) p2 Represents phenyl substituted by, R 1f This represents a hydrogen atom or a C1-C6 alkyl group. R 1g C1-C6 alkyl, R 18 (C1-C6) alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, halo(C2-C6) alkenyl, C2-C6 alkynyl, halo(C2-C6) alkynyl, C3-C 10 Represents cycloalkyl, C1-C6 alkylamino, or di(C1-C6)alkylamino, R 1h This represents C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl. R 5 This represents a C1-C6 haloalkyl group. R 6 These are cyano, nitro, amino, hydroxy, C3-C 10 Cycloalkyl, Halo(C3~C 10 )Cycloalkyl, C1-C6 alkoxy, halo(C1-C6)alkoxy, C1-C6 alkylthio, halo(C1-C6)alkylthio, C1-C6 alkylsulfinyl, halo(C1-C6)alkylsulfinyl, C1-C6 alkylsulfonyl, halo(C1-C6)alkylsulfonyl, C1-C6 alkylamino, di(C1-C6)alkylamino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxyimino, phenyl or (Z 2 ) p2 Represents phenyl substituted by, R 7 These include cyano, C1-C6 alkoxy, halo(C1-C6) alkoxy, C1-C6 alkylthio, halo(C1-C6) alkylthio, C1-C6 alkylsulfinyl, halo(C1-C6) alkylsulfinyl, C1-C6 alkylsulfonyl, halo(C1-C6) alkylsulfonyl, and C3-C10 cycloalkyl, phenyl, (Z 1 ) p1 substituted phenyl, -N(R 14 )R 15 , represents G-1 to G-60 or G-61, R 8 is cyano, C1-C6 alkoxy, halo(C1-C6)alkoxy, phenyl or (Z 1 ) p1 substituted phenyl, R 9 is cyano, C1-C6 alkoxy, halo(C1-C6)alkoxy, C1-C6 alkylthio, halo(C1-C6)alkylthio, C1-C6 alkylsulfinyl, halo(C1-C6)alkylsulfinyl, C1-C6 alkylsulfonyl, halo(C1-C6)alkylsulfonyl or C3-C 10 cycloalkyl, R 10 is cyano, C3-C 10 cycloalkyl, C1-C6 alkoxy, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxyimino, phenyl or (Z 3 ) p3 substituted phenyl, R 11 represents a hydrogen atom or C1-C6 alkyl, R 12 represents C1-C6 alkyl, R 13 represents cyano, R 14 represents a hydrogen atom, C1-C6 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl or C1-C6 alkylsulfonyl, R 15 represents a hydrogen atom or C1-C6 alkyl, R 16These include cyano, C1-C6 alkoxy, halo(C1-C6) alkoxy, C1-C6 alkylthio, halo(C1-C6) alkylthio, C1-C6 alkylsulfinyl, halo(C1-C6) alkylsulfinyl, C1-C6 alkylsulfonyl, halo(C1-C6) alkylsulfonyl, and C3-C 10 Cycloalkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxyimino, phenyl or (Z 4 ) p4 Represents phenyl substituted by, R 17 This represents cyano, C1-C6 alkoxy, or C1-C6 alkoxy(C1-C6)alkoxy, R 18 This represents cyano, C1-C6 alkoxy, C1-C6 alkoxy(C1-C6) alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, or C1-C6 alkylsulfonyl. Z 1 These are halogen atoms, cyano, nitro, C1-C6 alkyl, R 17 (C1-C6) alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, halo(C1-C6) alkoxy, C1-C6 alkylthio, halo(C1-C6) alkylthio, C1-C6 alkylsulfinyl, halo(C1-C6) alkylsulfinyl, C1-C6 alkylsulfonyl, halo(C1-C6) alkylsulfonyl, C1-C6 alkylamino, di(C1-C6)alkylamino or C3-C 10 When representing a cycloalkyl group and p1 represents an integer of 2, 3, 4, or 5, each Z 1 They may be the same as each other or different from each other. Z 1a This represents a hydrogen atom, a halogen atom, a cyano, a nitro, a C1-C6 alkyl, a C1-C6 haloalkyl, a C1-C6 alkoxy, a halo(C1-C6) alkoxy, a C1-C6 alkylthio, a C1-C6 alkylsulfinyl, or a C1-C6 alkylsulfonyl. Z 2When p2 represents a halogen atom, cyano, C1-C6 alkyl, C1-C6 haloalkyl, or C1-C6 alkoxy, and p2 represents an integer of 2, 3, 4, or 5, each Z 2 They may be the same as each other or different from each other. Z 3 When p3 represents a halogen atom, cyano, C1-C6 alkyl, C1-C6 haloalkyl, or C1-C6 alkoxy, and p3 represents an integer of 2, 3, 4, or 5, each Z 3 They may be the same as each other or different from each other. Z 4 When p4 represents a halogen atom, cyano, C1-C6 alkyl, C1-C6 haloalkyl, or C1-C6 alkoxy, and p4 represents an integer of 2, 3, 4, or 5, each Z 4 They may be the same as each other or different from each other. p1 represents an integer of 1, 2, 3, 4, or 5. p2 represents an integer of 1, 2, 3, 4, or 5. p3 represents an integer of 1, 2, 3, 4, or 5. p4 represents an integer of 1, 2, 3, 4, or 5. q3 represents an integer of 0, 1, 2, or 3. q4 represents an integer of 0, 1, 2, 3, or 4. q5 represents an integer of 0, 1, 2, 3, 4, or 5. q6 represents an integer of 0, 1, 2, 3, 4, 5, or 6. g2 represents an integer of 0, 1, or 2. g3 represents an integer of 0, 1, 2, or 3. g4 represents an integer of 0, 1, 2, 3, or 4. r represents an integer of 0, 1, or 2. [Effects of the Invention]

[0020] The compounds of the present invention exhibit 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 useful novel isoxazoline-substituted benzamide compounds or salts thereof. [Modes for carrying out the invention]

[0021] With respect to compounds of the present invention represented by formula (1) where Q is Q-1, there exist geometric isomers having two different stereoconfigurations based on the presence of a double bond in the imino group, namely the compound represented by formula (1a) and the compound represented by formula (1b). The present invention encompasses these compounds represented by formula (1a), the compound represented by formula (1b), or mixtures containing the compounds represented by formula (1a) and the compounds represented by formula (1b) in any proportion.

[0022] [ka]

[0023] Furthermore, with respect to the amide structure of the present invention compounds represented by formula (1), R is applied to compounds where Q is Q-1. 2 , R 3 , R 4 , R 2 and R 4 , or R 2 and R 3 When the atom is a hydrogen atom, it can exist as a tautomer represented by the following equation, but the present invention encompasses all of these structures as well.

[0024] [ka]

[0025] [ka]

[0026] [ka]

[0027] [ka]

[0028] [ka]

[0029] Furthermore, regarding the amide structures of the compounds of the present invention represented by formula (1), compounds where Q is Q-2 may exist as tautomers represented by the following formula, but the present invention encompasses all of these structures as well.

[0030] [ka]

[0031] Furthermore, with respect to the amide structure of the present invention compounds represented by formula (1), R is applied to compounds where Q is Q-2. 3 or R 4 When the atom is a hydrogen atom, it can exist as a tautomer represented by the following equation, but the present invention encompasses all of these structures as well.

[0032] [ka]

[0033] [ka]

[0034] Furthermore, in the compound of formula (1) included in the present invention, the R of compound (1) 5 With respect to the optical isomers of the carbon atom to which the substituent corresponding to is attached, the compound may contain (R)-isomers and (S)-isomers in any proportion. The (R)-isomer represents the compound represented by the following formula (R-1) [hereinafter referred to as compound (R-1)], and the (S)-isomer represents the compound represented by the following formula (S-1) [hereinafter referred to as compound (S-1)].

[0035] [ka]

[0036] (In the above equations (R-1) and (S-1), X 1 , X 2 , X 3 , Y 1 , Y 2 , R 5 , W and Q, X in equation (1) above 1 , X 2 , X 3 , Y 1 , Y 2 , R 5 (Having the same meaning as W and Q) In other words, the compound of formula (1) may be a racemate in which equal amounts of compound (R-1) and compound (S-1) are present and it does not exhibit optical activity, or it may not be a racemate. The case in which the compound of formula (1) is not a racemate is when the enantiomeric excess of compound (R-1) in the compound of formula (1) is 50% or more, 60% or more, 70% or more, 80% or more, or 90% or more, or when the enantiomeric excess of compound (S-1) in the compound of formula (1) is 50% or more, 60% or more, 70% or more, 80% or more, or 90% or more. Furthermore, below, the notations (R) and (S) may be used to indicate compound (R-1) and compound (S-1), respectively.

[0037] The compounds included in this invention may have geometric isomers of E- and Z-forms depending on the type of substituent, but this invention also includes mixtures containing these E-forms, Z-forms, or E-forms and Z-forms in any proportion.

[0038] Furthermore, while compounds included in the present invention may have optically active forms due to the presence of one or more chiral carbon atoms or chiral sulfur atoms depending on the type of substituent, the present invention encompasses all optically active forms or racemic mixtures.

[0039] Furthermore, while compounds included in the present invention may have tautomers depending on the type of substituent, the present invention encompasses all tautomers or mixtures of tautomers containing them in any proportion.

[0040] Furthermore, the compounds included in the present invention may exist as one or more rotational isomers due to limited bond rotation caused by steric hindrance between substituents, but the present invention encompasses all rotational isomers or mixtures of diastereomers containing them in any proportion.

[0041] Among the compounds included in the present invention, those that can be salted according to conventional methods 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; salts of aluminum; and quaternary ammonium salts such as tetramethylammonium salt, tetrabutylammonium salt, and benzyltrimethylammonium salt.

[0042] Next, specific examples of each substituent shown in this specification are given below. Here, n- means normal, i- means iso, s- means secondary, tert- means tertiary, and Ph means phenyl.

[0043] In this specification, "halogen atoms" include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms. The term "halo" in this specification also refers to these halogen atoms.

[0044] In this specification, "Ca ~C b The designation "alkyl" refers to a linear or branched hydrocarbon group consisting of a to b carbon atoms. Specific examples include methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, tert-butyl, n-pentyl, 1,1-dimethylpropyl, and 2-ethylhexyl, each selected within a specified range of carbon atoms.

[0045] In this specification, "C a ~C bThe notation "haloalkyl" represents a linear or branched hydrocarbon group having a to b carbon atoms, in which at least some of the hydrogen atoms bonded to carbon atoms are substituted by halogen atoms. In this case, if two or more halogen atoms are substituted, these halogen atoms may be identical or different from each other. Examples include fluoromethyl, chloromethyl, bromomethyl, iodomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, trichloromethyl, bromodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2,2-difluoroethyl, 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, and 2,2-difluoroethyl. 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, etc., each selected within the specified range of carbon atoms.

[0046] In this specification, "C a ~C bThe term "alkenyl" refers to an unsaturated hydrocarbon group that has a linear or branched chain with a to b carbon atoms and contains one or more double bonds within 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, each selected within a specified range of carbon atoms.

[0047] In this specification, "halo(C) a ~C b The notation "alkenyl" represents an unsaturated hydrocarbon group having a to b carbon atoms, in a linear or branched chain configuration, and containing one or more double bonds within the molecule, where at least some of the hydrogen atoms bonded to the carbon atoms are optionally substituted by halogen atoms. In this case, if two or more halogen atoms are substituted, these halogen atoms may be identical or distinct from each other. For example, 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, 3-chloro-4,4,4-trifluoro-2-butenyl, etc. are given as specific examples, and each is selected within the specified range of carbon atoms.

[0048] In this specification, "C a ~C b The notation "alkynyl" refers to an unsaturated hydrocarbon group that has a to b carbon atoms in a linear or branched chain and contains one or more triple bonds within the molecule. Specific examples include ethynyl, propargyl, 2-butynyl, 3-butynyl, 1-pentynyl, and 1-hexynyl, each selected within a specified range of carbon atoms.

[0049] In this specification, "halo(C) a ~C b The notation "alkynyl" represents an unsaturated hydrocarbon group having a to b carbon atoms, in a linear or branched chain configuration, and possessing one or more triple bonds within the molecule, where at least some of the hydrogen atoms bonded to carbon atoms are arbitrarily substituted by halogen atoms. In this case, if two or more halogen atoms are substituted, these halogen atoms may be identical or different from each other. Specific examples include 2-chloroethynyl, 2-bromoethynyl, 2-iodoethynyl, 3-chloro-2-propynyl, 3-bromo-2-propynyl, and 3-iodo-2-propynyl, each selected within a specified range of carbon atoms.

[0050] In this specification, "C a ~C b The notation "alkoxy" represents an alkyl-O- group having a to b carbon atoms, as described above. Specific examples include methoxy, ethoxy, n-propyloxy, i-propyloxy, n-butyloxy, i-butyloxy, s-butyloxy, tert-butyloxy, and 2-ethylhexyloxy, each selected within the specified range of carbon atoms.

[0051] In this specification, "halo(C) a ~C b The notation "alkoxy" represents a haloalkyl-O- group having a to b carbon atoms, as described above. Specific examples include difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy, and 1,1,2,3,3,3-hexafluoropropyloxy, each selected within the specified range of carbon atoms.

[0052] In this specification, "C a ~C b Alkoxy(C) d ~C eThe notation ")alkoxy" means any C with the meaning described above. a ~C b This refers to an alkoxy group having d to e carbon atoms, in which hydrogen atoms bonded to carbon atoms are arbitrarily substituted by an alkoxy group, and is selected within the specified range of carbon atom numbers.

[0053] In this specification, "C a ~C b The notation "alkylthio" represents an alkyl-S-group having a to b carbon atoms, as described above. Specific examples include methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, and tert-butylthio, each selected within the specified range of carbon atoms. In this specification, "halo(C) a ~C b The notation "(alkylthio)" represents a haloalkyl-S- group having a to b carbon atoms, as described above. Specific examples 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, etc., each selected within the specified range of carbon atoms.

[0054] In this specification, "C a ~C b The notation "alkylsulfinyl" represents an alkyl-S(O)- group having a to b carbon atoms, as described above. Specific examples include methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, i-propylsulfinyl, n-butylsulfinyl, i-butylsulfinyl, s-butylsulfinyl, and tert-butylsulfinyl, each selected within the specified range of carbon atoms.

[0055] In this specification, "halo(C) a ~C b The notation "(alkylsulfinyl)" represents a haloalkyl-S(O)- group having a to b carbon atoms, as described above. Specific examples include difluoromethylsulfinyl, trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethylsulfinyl, and nonafluorobutylsulfinyl, each selected within the specified range of carbon atoms.

[0056] In this specification, "C a ~C b The notation "alkylsulfonyl" represents an alkyl-S(O)2- group having a to b carbon atoms, as described above. Specific examples include methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl, n-butylsulfonyl, i-butylsulfonyl, s-butylsulfonyl, and tert-butylsulfonyl, each selected within the specified range of carbon atoms.

[0057] In this specification, "halo(C) a ~C b The notation "alkylsulfonyl" represents a haloalkyl-S(O)2- group having a to b carbon atoms, as described above. Specific examples include difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 1,1,2,2-tetrafluoroethylsulfonyl, and 2-chloro-1,1,2-trifluoroethylsulfonyl, each selected within the specified range of carbon atoms.

[0058] In this specification, "C a ~C bThe notation "alkylamino" refers to an amino group in which one of the hydrogen atoms is replaced by an alkyl group having a to b carbon atoms. Specific examples include methylamino, ethylamino, n-propylamino, i-propylamino, n-butylamino, i-butylamino, and tert-butylamino, each selected within a specified range of carbon atoms.

[0059] In this specification, "The (C a ~C b The notation "alkylamino" represents an amino group substituted with alkyl groups, where both hydrogen atoms may be the same or different from each other, and the number of carbon atoms is a to b. Examples include dimethylamino, ethyl(methyl)amino, diethylamino, n-propyl(methyl)amino, i-propyl(methyl)amino, di(n-propyl)amino, di(n-butyl)amino, etc., and each is selected within the specified range of carbon atoms.

[0060] In this specification, "C a ~C b The notation "alkoxyimino" represents an alkoxy-N= group consisting of a to b carbon atoms, as described above. Specific examples include methoxyimino, ethoxyimino, n-propyloxyimino, i-propyloxyimino, and n-butyloxyimino, each selected within a specified range of carbon atoms.

[0061] In this specification, "C a ~C b The notation "alkylcarbonyl" represents an alkyl-C(O)- group having a to b carbon atoms, as described above. Specific examples include acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, 2-methylbutanoyl, pivaloyl, hexanoyl, and heptanol, each selected within the specified range of carbon atoms.

[0062] In this specification, "C a ~C bThe notation "alkoxycarbonyl" represents an alkyl-OC(O)- group having a to b carbon atoms, as described above. Specific examples include methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, i-propyloxycarbonyl, n-butoxycarbonyl, i-butoxycarbonyl, s-butoxycarbonyl, tert-butoxycarbonyl, and 2-ethylhexyloxycarbonyl, each selected within the specified range of carbon atoms.

[0063] In this specification, "C a ~C b The notation "alkylcarbonyloxy" represents an alkyl-C(O)-O- group consisting of a to b carbon atoms, as described above. Specific examples include acetyloxy, propionyloxy, butyryloxy, isobutyryloxy, etc., each selected within a specified range of carbon atoms.

[0064] In this specification, "C a ~C b The notation "alkoxycarbonyloxy" represents an alkoxy-C(O)-O- group having a number of carbon atoms from a to b, as described above. Specific examples include methoxycarbonyloxy, ethoxycarbonyloxy, i-butyloxycarbonyloxy, and tert-butyloxycarbonyloxy, each selected within the specified range of carbon atoms.

[0065] In this specification, "C a ~C b The notation "alkylsulfonyloxy" represents an alkylsulfonyl-O- group having a to b carbon atoms, as described above. Specific examples include methylsulfonyloxy, ethylsulfonyloxy, n-propylsulfonyloxy, i-propylsulfonyloxy, etc., each selected within the specified range of carbon atoms.

[0066] In this specification, "halo(C) a ~C bThe notation "alkylsulfonyloxy" represents an alkylsulfonyl-O- group having a to b carbon atoms, in which at least some of the hydrogen atoms bonded to carbon atoms are optionally substituted by halogen atoms. Specific examples include difluoromethylsulfonyloxy, trifluoromethylsulfonyloxy, chlorodifluoromethylsulfonyloxy, and bromodifluoromethylsulfonyloxy, each selected within the specified range of carbon atoms.

[0067] In this specification, "C a ~C b The notation "cycloalkyl" refers to a cyclic hydrocarbon group having a to b carbon atoms, which can form monocyclic or composite ring structures ranging from 3-membered to 10-membered rings. Each ring may also be arbitrarily substituted with alkyl groups within a specified range of carbon atoms. Examples include cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl, each selected within a specified range of carbon atoms.

[0068] In this specification, "halo(C) a ~C bThe notation "cycloalkyl" represents a cyclic hydrocarbon group having a to b carbon atoms, in which at least some of the hydrogen atoms bonded to carbon atoms are optionally substituted by halogen atoms, and can form monocyclic or composite ring structures ranging from 3-membered to 10-membered rings. Furthermore, each ring may be optionally substituted with alkyl within a specified range of carbon atoms, and the substitution by halogen atoms may be in the ring structure portion, the side chain portion, or both. In addition, if substituted by two or more halogen atoms, these halogen atoms may be identical or different from each other. Specific examples include 2,2-difluorocyclopropyl, 2,2-dichlorocyclopropyl, 2,2-dibromocyclopropyl, 2,2-difluoro-1-methylcyclopropyl, 2,2-dichloro-1-methylcyclopropyl, 2,2-dibromo-1-methylcyclopropyl, and 2,2,3,3-tetrafluorocyclobutyl, which are selected within the specified range of carbon atoms.

[0069] In this specification, "R 6 Replaced by (C a ~C b )alkyl", "R 7 Replaced by (C a ~C b )alkyl", "R 8 Replaced by (C a ~C b )alkyl", "R 9 Replaced by (C a ~C b )alkyl", "R 10 Replaced by (C a ~C b )alkyl", "R 16 Replaced by (C a ~C b )alkyl", "R 17 Replaced by (C a ~C b )alkyl" or "R 18 Replaced by (C a ~C bThe notation "alkyl" indicates that any hydrogen atom bonded to a carbon atom has one or more substituents R 6 , R 7 , R 8 , R 9 , R 10 , R 16 , R 17 or R 18 This represents an alkyl group having a to b carbon atoms partially or fully substituted by the substituent, selected within the specified range of carbon atoms. 6 , R 7 , R 8 , R 9 , R 10 , R 16 , R 17 or R 18 When there are two or more substituents R 6 , R 7 , R 8 , R 9 , R 10 , R 16 , R 17 or R 18 They may be the same or different from each other.

[0070] In this specification, "R 13 C replaced by a ~C b The notation "cycloalkyl" refers to the hydrogen atoms bonded to carbon atoms, with each substituent R 13 This represents a cycloalkyl group having a to b carbon atoms substituted by the substituent, and is selected within the specified range of carbon atoms. When there are two or more substituents, each substituent R 13 They may be the same or different from each other.

[0071] In this specification, "(Z 1 ) p1 Phenyl substituted by, (Z 2 ) p2 Phenyl substituted by, (Z 3 ) p3 Phenyl substituted by "(Z 4 ) p4The notation "phenyl substituted with Z" means that any hydrogen atom bonded to a carbon atom is substituted with Z. 1 , Z 2 , Z 3 or Z 4 This represents a phenyl group substituted with 1, 2, 3, or 4 p atoms. Also, p1 can be any of 1, 2, 3, 4, and 5 (Z 1 ) p1 Depending on the situation, p2 can take any value, and p2 can be chosen from 1, 2, 3, 4 and 5 (Z 2 ) p2 It can take any value depending on the situation, and p3 can be any value from 1, 2, 3, 4 and 5 (Z 3 ) p3 It can take any value depending on the situation, and p4 can be any value from 1, 2, 3, 4 and 5 (Z 4 ) p4 Depending on the substituent Z on the phenyl group, it can take any value, and each substituent Z on the phenyl group 1 , Z 2 , Z 3 or Z 4 When there are two or more of them, each Z 1 , Z 2 , Z 3 or Z 4 They may be identical to each other, or they may be different to each other.

[0072] Next, the compound of the present invention represented by formula (1) can be produced, for example, by the following method.

[0073] The compound represented by formula (1) is also referred to as "compound (1)," and the compound represented by formula (2) is also referred to as "compound (2)." Other compounds are described similarly in accordance with this convention.

[0074] Furthermore, among the compounds of the present invention, compound (R-1) or compound (S-1), in which the isoxazoline ring at position 5 is optically active, can be synthesized according to the following manufacturing method and reaction formula by using a starting material in which the isoxazoline ring at position 5 is optically active.

[0075] [Manufacturing method 1]

[0076] [ka]

[0077] (In the formula, X 1 , X 2 , X 3 , Y 1 , Y 2 , R 1 , R 2 , R 3 , R 4 and R 5 (This expresses the same meaning as above.) Compound (1-1) of the present invention can be produced by reacting compound (2) and compound (3) or a salt thereof (for example, hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, p-toluenesulfonate, etc.) with a condensing agent in a solvent or without a solvent, and if necessary, in the presence of a base.

[0078] The equivalent amount of compound (3) can be used in amounts of 1 to 100 equivalents per equivalent of compound (2).

[0079] When a solvent is used, the solvent must be inert to the reaction. Examples include water, alcohol solvents such as methanol and ethanol, ether solvents such as diethyl ether, tetrahydrofuran, 1,4-dioxane, and 1,2-dimethoxyethane, aromatic hydrocarbon solvents such as benzene, xylene, and toluene, aliphatic hydrocarbon solvents such as pentane, hexane, and cyclohexane, halogenated hydrocarbon solvents such as dichloromethane, chloroform, and 1,2-dichloroethane, nitrile solvents such as acetonitrile and propionitrile, amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and N,N'-dimethylimidazolidinone, ketone solvents such as acetone and 2-butanone, ethyl acetate, dimethyl sulfoxide, or mixtures thereof.

[0080] Examples of usable bases 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), 1,5-diazabicyclo[4.3.0]-5-nonene (DBN), HOAT (7-aza-1-hydroxybenzotriazole), and HOBT (1-hydroxybenzotriazole); inorganic bases such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium bicarbonate, potassium bicarbonate, sodium carbonate, potassium carbonate, cesium carbonate, and potassium phosphate; and metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide. The amount of base used can be 0.01 to 100 equivalents per equivalent of compound (2).

[0081] The condensing agent is not particularly limited as long as it is one that is normally used in amide synthesis, but examples include WSC (1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride), DCC (1,3-dicyclohexylcarbodiimide), CDI (carbonyldiimidazole), HATU (1-[bis(dimethylamino)methylene-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxidehexafluorophosphate), T3P (propylphosphonic anhydride), DMT-MM (4-(4,6-dimethoxy-1,3,5-triazine-2-yl)-4-methylmorpholinium chloride), etc. The equivalent amount of the condensing agent can be used in amounts of 1 to 5 equivalents per equivalent of compound (2).

[0082] The reaction temperature can be set to any temperature from -78°C to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but can usually be set to any temperature within the range of 5 minutes to 100 hours.

[0083] Some of compound (2) are known compounds, and the others can be synthesized in accordance with the methods described in, for example, International Publication No. 2005 / 085216.

[0084] Some of compound (3) are known compounds, and some are available commercially. [Manufacturing method 2]

[0085] [ka]

[0086] (In the formula, J 1 X represents a chlorine atom, a bromine atom, a C1-C4 alkylcarbonyloxy, or a C1-C4 alkoxycarbonyloxy. 1 , X 2 , X 3 , Y 1 , Y 2 , R 1 , R 2 , R 3 , R 4 and R 5 (This expresses the same meaning as above.) Compound (1-1) of the present invention can be produced by reacting compound (4) with compound (3) or its salt (for example, hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, p-toluenesulfonate, etc.) in a solvent or without a solvent, and if necessary, in the presence of a base.

[0087] The equivalent amount of compound (3) can be used in amounts of 1 to 100 equivalents per equivalent of compound (4).

[0088] When a solvent is used, the solvent used only needs to be inert to the reaction. Examples include ether solvents such as water, diethyl ether, tetrahydrofuran, 1,4-dioxane, and 1,2-dimethoxyethane; aromatic hydrocarbon solvents such as benzene, xylene, and toluene; aliphatic hydrocarbon solvents such as pentane, hexane, and cyclohexane; halogenated hydrocarbon solvents such as dichloromethane, chloroform, and 1,2-dichloroethane; nitrile solvents such as acetonitrile and propionitrile; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and N,N'-dimethylimidazolidinone; ketone solvents such as acetone and 2-butanone; ethyl acetate, dimethyl sulfoxide, or mixtures thereof.

[0089] Examples of bases that can be used in this reaction include the bases exemplified in Manufacturing Method 1. The amount of base can be used in an amount of 0.01 to 100 equivalents per equivalent of compound (4).

[0090] The reaction temperature and reaction time are within the temperature and time ranges specified in Manufacturing Method 1.

[0091] Some of compound (4) are known compounds, and the others can be synthesized in accordance with the methods described in, for example, International Publication No. 2005 / 085216. [Manufacturing method 3]

[0092] [ka]

[0093] (In the formula, J 2 X represents a leaving group such as a fluorine atom, chlorine atom, bromine atom, phenyloxy, p-nitrophenyloxy, or N-succinimidyloxy, 1 , X 2 , X 3 , Y 1 , Y 2 , R 1 , R 2 , R 3 , R 4and R 5 (This expresses the same meaning as above.) Compound (5) or its salts (e.g., hydrochloride salt, hydrobromide salt, trifluoroacetate salt, etc.) can be synthesized by reacting the compounds (1-2) of the present invention with hydrochloric acid, hydrobromic acid, trifluoroacetic acid, etc., according to the methods described in, for example, International Publication No. 2018 / 097172, International Publication No. 2014 / 013182, etc.

[0094] Next, compound (1-1) of the present invention can be produced by reacting a compound represented by compound (5) or a salt thereof (e.g., hydrochloride, hydrobromide, trifluoroacetate, etc.) with compound (6) or compound (7) in a solvent or without a solvent, and if necessary, in the presence of a base.

[0095] The equivalent amount of compound (6) or compound (7) can be used in amounts of 1 to 50 equivalents per equivalent of compound (5).

[0096] When a solvent is used, it is sufficient that the solvent is inert to the reaction; for example, the solvents exemplified in Manufacturing Method 2 are examples.

[0097] Examples of bases that can be used in this reaction include the bases exemplified in Manufacturing Method 1. The amount of base can be used in an amount of 0.01 to 100 equivalents per equivalent of compound (5).

[0098] The reaction temperature and reaction time are within the temperature and time ranges specified in Manufacturing Method 1.

[0099] The compounds (1-2) of the present invention can be synthesized according to the method of Production Method 1.

[0100] Some of compounds (6) and (7) are known compounds, and some are commercially available. Others can be synthesized according to general synthetic methods for known compounds, for example, according to the methods described in Tetrahedron Lett., 2006, Vol. 47, p. 3405, etc. [Manufacturing method 4]

[0101] [ka]

[0102] (In the formula, W 1 represents an oxygen atom or a sulfur atom, X 1 , X 2 , X 3 , Y 1 , Y 2 , R 2 , R 3 , R 4 , R 5 and R 1b (This expresses the same meaning as above.) Compounds (1-3) of the present invention can be produced by reacting a compound represented by compound (5) or a salt thereof (e.g., hydrochloride, hydrobromide, trifluoroacetate, etc.) with compound (8) in a solvent or without a solvent, and if necessary, in the presence of a base.

[0103] The equivalent amount of compound (8) can be used in amounts of 1 to 50 equivalents per equivalent of compound (5).

[0104] When a solvent is used, it is sufficient that the solvent is inert to the reaction; for example, the solvents exemplified in Manufacturing Method 2 are examples.

[0105] Examples of bases that can be used in this reaction include the bases exemplified in Manufacturing Method 1. The amount of base can be used in an amount of 0.01 to 100 equivalents per equivalent of compound (5).

[0106] The reaction temperature and reaction time are within the temperature and time ranges specified in Manufacturing Method 1.

[0107] Compound (5) can be synthesized according to manufacturing method 3 or the method of reaction formula 1. Some of compound (8) are known compounds, and some are available commercially. [Manufacturing method 5]

[0108] [ka]

[0109] (In the formula, R a represents C1-C6 alkyl, X 1 , X 2 , X 3 , Y 1 , Y 2 , R 1 , R 2 , R 3 , R 4 , R 5 and J 1 (This expresses the same meaning as above.) Compound (10) can be synthesized by reacting compound (4) and compound (9) in a solvent or without a solvent, and if necessary, in the presence of a base.

[0110] The equivalent amount of compound (9) can be used in amounts of 1 to 50 equivalents per equivalent of compound (4).

[0111] When a solvent is used, it is sufficient that the solvent is inert to the reaction; for example, the solvents exemplified in Manufacturing Method 2 are examples.

[0112] Examples of bases that can be used in this reaction include the bases exemplified in Manufacturing Method 1. The amount of base can be used in an amount of 0.01 to 100 equivalents per equivalent of compound (4).

[0113] The reaction temperature and reaction time are within the temperature and time ranges specified in Manufacturing Method 1.

[0114] Furthermore, compound (1-1) of the present invention can be synthesized by reacting compound (10) with compound (11) or its salt (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, p-toluenesulfonate, etc.) in a solvent or without a solvent, and if necessary, in the presence of a base.

[0115] The equivalent amount of compound (11) can be used in amounts of 1 to 50 equivalents per equivalent of compound (10).

[0116] When a solvent is used, it is sufficient that the solvent is inert to the reaction; for example, the solvents exemplified in Manufacturing Method 1 can be used.

[0117] Examples of bases that can be used in this reaction include the bases exemplified in Manufacturing Method 1. The amount of base can be used in an amount of 0.01 to 100 equivalents per equivalent of compound (10).

[0118] The reaction temperature and reaction time are within the temperature and time ranges specified in Manufacturing Method 1.

[0119] Some of compound (9) are known compounds, and some are available commercially. Others can be synthesized in accordance with general synthesis methods for known compounds, such as the method using acid anhydrides described in International Publication No. 2016 / 110822, etc., the method using acid halides described in International Publication No. 2011 / 160020, etc.

[0120] Some of compound (11) are known compounds, and some are available commercially.

[0121] [Manufacturing method 6]

[0122] [ka]

[0123] (In the formula, J 3 X represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom, a C1-C4 alkyl sulfonyloxy, a halo(C1-C4) alkyl sulfonyloxy, or a p-toluenesulfonyloxy. 1 , X 2 , X 3 , Y 1 , Y 2 , R 1 , R 2 , R 3 , R4 and R 5 (This expresses the same meaning as above.) In the compound (1) of the present invention, W represents an oxygen atom, and R 2 Compound (1-1) of the present invention can be synthesized by reacting a compound represented by formula (1-4), in which the atom is a hydrogen atom [hereinafter referred to as Compound (1-4) of the present invention] with compound (12) in a solvent or without a solvent, and if necessary, in the presence of a base.

[0124] The equivalent amount of compound (12) of the present invention can be used in an amount of 1 to 50 equivalents per equivalent of compound (1-4).

[0125] When a solvent is used, it is sufficient that the solvent is inert to the reaction; for example, the solvents exemplified in Manufacturing Method 2 are examples.

[0126] Examples of bases that can be used in this reaction include the bases exemplified in Manufacturing Method 1. The amount of base can be used in an amount of 0.01 to 100 equivalents per equivalent of Compound (1-4) of the present invention.

[0127] The reaction temperature and reaction time are within the temperature and time ranges specified in Manufacturing Method 1.

[0128] The compounds (1-4) of the present invention can be synthesized according to the method of production method 3.

[0129] Some of compound (12) are known compounds, and some are available commercially. [Manufacturing method 7]

[0130] [ka]

[0131] (In the formula, X 1 , X 2 , X 3 , Y 1 , Y 2 , R 1 , R 3 , R 4 , R5 , J 3 and R A (This expresses the same meaning as above.) Compound (1-5) of the present invention can be synthesized by reacting compound (1-4) and compound (12a) in a solvent or without a solvent, and if necessary, in the presence of a base.

[0132] The equivalent amount of compound (12a) can be used in an amount of 1 to 50 equivalents per equivalent of compound (1-4) of the present invention.

[0133] When a solvent is used, it is sufficient that the solvent is inert to the reaction; for example, the solvents exemplified in Manufacturing Method 2 are examples.

[0134] Examples of bases that can be used in this reaction include the bases exemplified in Manufacturing Method 1. The amount of base can be used in an amount of 0.01 to 100 equivalents per equivalent of Compound (1-4) of the present invention.

[0135] The reaction temperature and reaction time are within the temperature and time ranges specified in Manufacturing Method 1.

[0136] The compounds (1-4) of the present invention can be synthesized according to the method of production method 3.

[0137] Some of the compounds (12a) are known compounds, and some are available commercially. [Manufacturing method 8]

[0138] [ka]

[0139] (In the formula, X 1 , X 2 , X 3 , Y 1 , Y 2 , R 1 , R 3 , R 4 , R 5 , R a , J1 and R A (This expresses the same meaning as above.) Compound (14) can be synthesized by reacting compound (4) and compound (13) in a solvent or without a solvent, and if necessary, in the presence of a base.

[0140] The equivalent amount of compound (13) can be used in amounts of 1 to 50 equivalents per equivalent of compound (4).

[0141] When a solvent is used, it is sufficient that the solvent is inert to the reaction; for example, the solvents exemplified in Manufacturing Method 2 are examples.

[0142] Examples of bases that can be used in this reaction include the bases exemplified in Manufacturing Method 1. The amount of base can be used in an amount of 0.01 to 100 equivalents per equivalent of compound (4).

[0143] The reaction temperature and reaction time are within the temperature and time ranges specified in Manufacturing Method 1.

[0144] Furthermore, compounds (1-5) of the present invention can be synthesized by reacting compound (14) with compound (11) or its salt (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, p-toluenesulfonate, etc.) in a solvent or without a solvent, and if necessary, in the presence of a base.

[0145] The equivalent amount of compound (11) can be used in amounts of 1 to 50 equivalents per equivalent of compound (14).

[0146] When a solvent is used, it is sufficient that the solvent is inert to the reaction; for example, the solvents exemplified in Manufacturing Method 1 can be used.

[0147] Examples of bases that can be used in this reaction include the bases exemplified in Manufacturing Method 1. The amount of base can be used in an amount of 0.01 to 100 equivalents per equivalent of compound (14).

[0148] The reaction temperature and reaction time are within the temperature and time ranges specified in Manufacturing Method 1.

[0149] Some of compound (13) are known compounds, and some are available commercially. Others can be synthesized in accordance with general synthesis methods for known compounds, such as those described in International Publication No. 2006 / 138350, etc. [Manufacturing method 9]

[0150] [ka]

[0151] (In the formula, X 1 , X 2 , X 3 , Y 1 , Y 2 , R 5 (And Q have the same meaning as above.) Compound (1) of the present invention can be synthesized by reacting one of the compounds (1-6) of the present invention, in which W is an oxygen atom, with 1 to 10 equivalents of phosphorus pentasulfide or Lawesson's reagent [2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosfetan-2,4-disulfide] relative to compound (1) of the present invention, in or without a solvent.

[0152] When a solvent is used, it is sufficient that the solvent is inert to the reaction; for example, the solvents exemplified in Manufacturing Method 2 are examples.

[0153] The reaction temperature and reaction time are within the temperature and time ranges specified in Manufacturing Method 1. [Manufacturing method 10]

[0154] [ka]

[0155] (In the formula, X 1 , X 2 , X 3 , Y1 , Y 2 , R 5 (And Q have the same meaning as above.) Compounds (1-6) of the present invention can be synthesized by reacting compound (15) with 1 to 10 equivalents of hydroxylamine or its salt (e.g., hydrochloride, sulfate, etc.) in a solvent or without a solvent, and if necessary, in the presence of a base.

[0156] When a solvent is used, it is sufficient that the solvent is inert to the reaction; for example, the solvents exemplified in Manufacturing Method 2 are examples.

[0157] Examples of bases that can be used in this reaction include the bases exemplified in Production Example 1. The amount of base can be used in an amount of 0.01 to 100 equivalents per equivalent of compound (15).

[0158] The reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.

[0159] Furthermore, optically active compounds (1-6) of the present invention can also be synthesized by reacting compound (15) with hydroxylamine or a salt thereof (e.g., hydrochloride, sulfate, etc.) in the presence of an asymmetric catalyst and, if necessary, a base, in accordance with methods known in the literature (for example, the methods described in International Publication No. 2013 / 069731, International Publication No. 2016 / 023787, International Publication No. 2017 / 176948, International Publication No. 2020 / 094434, etc.).

[0160] The compound (5) used in manufacturing method 3 can also be synthesized, for example, as shown in reaction formula 1. [Reaction Equation 1]

[0161] [ka]

[0162] (In the formula, X 1 , X 2 , X 3 , Y 1 , Y 2, R 2 , R 3 , R 4 , R 5 and J 1 (This expresses the same meaning as above.) Compound (5) can be synthesized by reacting compound (4) with compound (16) or its salt (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, p-toluenesulfonate, etc.) in a solvent or without a solvent, and if necessary, in the presence of a base.

[0163] The equivalent amount of compound (16) can be used in amounts of 1 to 50 equivalents per equivalent of compound (4).

[0164] When a solvent is used, it is sufficient that the solvent is inert to the reaction; for example, the solvents exemplified in Manufacturing Method 2 are examples.

[0165] Examples of bases that can be used in this reaction include the bases exemplified in Manufacturing Method 1. The amount of base can be used in an amount of 0.01 to 100 equivalents per equivalent of compound (4).

[0166] The reaction temperature and reaction time are within the temperature and time ranges specified in Manufacturing Method 1.

[0167] Some of the compounds (16) are known compounds, and some are available commercially.

[0168] The compound (4) used in manufacturing method 2 can also be synthesized, for example, by the reaction shown in reaction equation 2. [Reaction Equation 2]

[0169] [ka]

[0170] (In the formula, X 1 , X 2 , X 3 , Y 1 , Y 2 , R 5and J 1 (This expresses the same meaning as above.) Compound (4) can be synthesized by reacting compound (2) with a halogenating agent such as thionyl chloride, phosphorus pentachloride, or oxalyl chloride, according to known methods described in the literature, for example, the method described in Journal of Medicinal Chemistry [J.Med.Chem.] 1991, Vol. 34, p. 1630, etc., or by reacting compound (4) with an organic acid halide such as pivaloyl chloride or isobutyl chloroformate, in the presence of a base if necessary, according to the method described in Tetrahedron Lett. 2003, Vol. 44, p. 4819, Journal of Medicinal Chemistry [J.Med.Chem.] 1991, Vol. 34, p. 222, etc.

[0171] Of the compounds (15) used in manufacturing method 10, the compound represented by formula (15-1a) where Q is Q-1 [hereinafter referred to as compound (15-1a)] can be synthesized, for example, by reaction formula 3, reaction formula 4, reaction formula 5, or reaction formula 6 below. In addition, of the compounds (15), the compound represented by formula (15-1b) where Q is Q-2 [hereinafter referred to as compound (15-1b)] can be synthesized, for example, by reaction formula 7 below. [Reaction Equation 3]

[0172] [ka]

[0173] (In the formula, X 1 , X 2 , X 3 , Y 1 , Y 2 , R 1 , R 2 , R 3 , R 4 and R 5 (This expresses the same meaning as above.) Compound (15-1a) can be produced by reacting compound (17) with compound (3) or its salt (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, p-toluenesulfonate, etc.) with a condensing agent in a solvent or without a solvent, and if necessary, in the presence of a base.

[0174] The equivalent amount of compound (3) can be used in amounts of 1 to 100 equivalents per equivalent of compound (17).

[0175] When a solvent is used, it is sufficient that the solvent is inert to the reaction; for example, the solvents exemplified in Manufacturing Method 2 are examples.

[0176] Examples of bases that can be used in this reaction include the bases exemplified in Production Example 1. The amount of base can be used in an amount of 0.01 to 100 equivalents per equivalent of compound (17).

[0177] Examples of condensing agents used in this reaction include the condensing agents exemplified in Production Example 1. The amount of condensing agent can be used in an amount of 1 to 5 equivalents per equivalent of compound (17).

[0178] The reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.

[0179] Some of compound (17) are known compounds, while others can be synthesized in accordance with general methods for synthesizing known compounds, such as those described in International Publication No. 2007 / 074789, etc. [Reaction Equation 4]

[0180] [ka]

[0181] (In the formula, X 1 , X 2 , X 3 , Y 1 , Y 2 , R 1 , R2 , R 3 , R 4 , R 5 and J 1 (This expresses the same meaning as above.) Compound (15-1a) can be synthesized by reacting compound (18) with compound (3) or its salt (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, p-toluenesulfonate, etc.) in a solvent or without a solvent, and if necessary, in the presence of a base.

[0182] The equivalent amount of compound (3) can be used in amounts of 1 to 50 equivalents per equivalent of compound (18).

[0183] When a solvent is used, it is sufficient that the solvent is inert to the reaction; for example, the solvents exemplified in Manufacturing Method 2 are examples.

[0184] Examples of bases that can be used in this reaction include the bases exemplified in Production Example 1. The amount of base can be used in an amount of 0.01 to 100 equivalents per equivalent of compound (18).

[0185] The reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.

[0186] Some of compound (18) are known compounds, while others can be synthesized in accordance with general methods for synthesizing known compounds, such as those described in International Publication No. 2007 / 074789, etc. [Reaction Equation 5]

[0187] [ka]

[0188] (In the formula, X 1 , X 2 , X 3 , Y 1 , Y 2 , R 1 , R 2 , R 3, R 4 , R 5 and J 2 (This expresses the same meaning as above.) Compound (19) can be reacted with hydrochloric acid, hydrobromic acid, trifluoroacetic acid, etc., in accordance with the methods described in, for example, International Publication No. 2018 / 097172, International Publication No. 2014 / 013182, etc., to synthesize compound (20) or its salts (e.g., hydrochloride salt, hydrobromide salt, trifluoroacetate salt, etc.).

[0189] Next, compound (15-1a) can be produced by reacting a compound represented by compound (20) or a salt thereof (e.g., hydrochloride, hydrobromide, trifluoroacetate, etc.) with compound (6) or compound (7) in a solvent or without a solvent, and if necessary, in the presence of a base.

[0190] The equivalent amount of compound (6) or compound (7) can be used in amounts of 1 to 50 equivalents per equivalent of compound (20).

[0191] When a solvent is used, it is sufficient that the solvent is inert to the reaction; for example, the solvents exemplified in Manufacturing Method 2 are examples.

[0192] Examples of bases that can be used in this reaction include the bases exemplified in Production Example 1. The amount of base can be used in an amount of 0.01 to 100 equivalents per equivalent of compound (20).

[0193] The reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.

[0194] Compound (19) can be synthesized according to the method of reaction formula 3.

[0195] [Reaction Equation 6]

[0196] [ka]

[0197] (In the formula, X 1 , X 2 , X 3 , Y 1 , Y 2 , R 1 , R 2 , R 3 , R 4 , R 5 and J 3 (This expresses the same meaning as above.) Of the compounds (15), R 2 Compound (15-1a) can be synthesized by reacting a compound represented by formula (21), where is a hydrogen atom and Q is Q-1 [hereinafter referred to as compound (21)], with compound (12) in a solvent or without a solvent, and if necessary, in the presence of a base.

[0198] The equivalent amount of compound (12) can be used in amounts of 1 to 50 equivalents per equivalent of compound (21).

[0199] When a solvent is used, it is sufficient that the solvent is inert to the reaction; for example, the solvents exemplified in Manufacturing Method 2 are examples.

[0200] Examples of bases that can be used in this reaction include the bases exemplified in Production Example 1. The amount of base can be used in an amount of 0.01 to 100 equivalents per equivalent of compound (21).

[0201] The reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.

[0202] [Reaction Equation 7]

[0203] [ka]

[0204] (In the formula, X 1 , X 2 , X 3 , Y 1 , Y 2 , R 1 , R 3 , R 4, R 5 , J 3 and R A (This expresses the same meaning as above.) Compound (15-1b) can be synthesized by reacting compound (21) and compound (12a) in a solvent or without a solvent, and if necessary, in the presence of a base.

[0205] The equivalent amount of compound (12a) can be used in amounts of 1 to 50 equivalents per equivalent of compound (21).

[0206] When a solvent is used, it is sufficient that the solvent is inert to the reaction; for example, the solvents exemplified in Manufacturing Method 2 are examples.

[0207] Examples of bases that can be used in this reaction include the bases exemplified in Production Example 1. The amount of base can be used in an amount of 0.01 to 100 equivalents per equivalent of compound (21).

[0208] The reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.

[0209] The compound (10) used in manufacturing method 5 can also be synthesized, for example, by the reaction shown in reaction formula 8.

[0210] [Reaction Equation 8]

[0211] [ka]

[0212] (In the formula, X 1 , X 2 , X 3 , Y 1 , Y 2 , R 1 , R 2 , R 5 and R a (This expresses the same meaning as above.) Compound (10) can be produced by reacting compound (2) and compound (9) with a condensing agent in a solvent or without a solvent, and if necessary, in the presence of a base.

[0213] The equivalent amount of compound (9) can be used in amounts of 1 to 100 equivalents per equivalent of compound (2).

[0214] When a solvent is used, it is sufficient that the solvent is inert to the reaction; for example, the solvents exemplified in Manufacturing Method 2 are examples.

[0215] Examples of bases that can be used in this reaction include the bases exemplified in Production Example 1. The amount of base can be used in an amount of 0.01 to 100 equivalents per equivalent of compound (2).

[0216] Examples of condensing agents used in this reaction include the condensing agents exemplified in Production Example 1. The amount of condensing agent can be used in an amount of 1 to 5 equivalents per equivalent of compound (2).

[0217] The reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.

[0218] Compound (2) used in manufacturing method 1, reaction formula 2, and reaction formula 8 can also be synthesized, for example, by reaction formula 9 or reaction formula 10.

[0219] [Reaction Equation 9]

[0220] [ka]

[0221] (In the formula, R b represents C1-C4 alkyl, X 1 , X 2 , X 3 , Y 1 , Y 2 and R 5 (This expresses the same meaning as above.) Compound (23) can be produced by reacting compound (22) in a solvent in the presence of an acid.

[0222] Examples of solvents that can be used include alcoholic solvents such as methanol, ethanol, 1-propanol, 2-propanol, and 1-butanol.

[0223] Examples of acids that can be used in this reaction include hydrochloric acid and sulfuric acid. The amount of acid used can be 1 to 100 equivalents per equivalent of compound (22).

[0224] The reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.

[0225] Next, compound (2) can be synthesized by reacting compound (23) with a base in a solvent or without a solvent.

[0226] When using a solvent, examples include water, ether solvents such as tetrahydrofuran, 1,4-dioxane, and 1,2-dimethoxyethane, aromatic hydrocarbon solvents such as benzene, xylene, and toluene, alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, and 1-butanol, or mixtures thereof.

[0227] Examples of bases that can be used in this reaction include sodium hydroxide, potassium hydroxide, and lithium hydroxide. The amount of base used can be 1 to 20 equivalents per equivalent of compound (23).

[0228] The reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.

[0229] Some of compound (22) are known compounds, while others can be synthesized in accordance with general methods for synthesizing known compounds, such as those described in International Publication No. 2007 / 026965, etc.

[0230] [Reaction Equation 10]

[0231] [ka]

[0232] (In the formula, X 1 , X 2 , X 3 , Y 1 , Y 2 and R 5 (This expresses the same meaning as above.) Compound (2) can be produced by reacting compound (22) in a solvent in the presence of an acid.

[0233] Examples of solvents that can be used include water, ether solvents such as tetrahydrofuran, 1,4-dioxane, and 1,2-dimethoxyethane, aromatic hydrocarbon solvents such as benzene, xylene, and toluene, alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, and 1-butanol, acetic acid, propionic acid, trifluoroacetic acid, or mixtures thereof.

[0234] Examples of acids that can be used in this reaction include hydrochloric acid and sulfuric acid. The amount of acid used can be 1 to 100 equivalents per equivalent of compound (22).

[0235] The reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.

[0236] In the reactions of Production Methods 1 to 10 and Reaction Schemes 1 to 10, the reaction mixture after the reaction is completed can be concentrated by direct concentration, or by dissolving it in an organic solvent and then washing it with water and concentrating it, or by immersing it in ice water, extracting the organic solvent, and then concentrating it, thereby obtaining the target compound of the present invention. Furthermore, if purification becomes necessary, it can be separated and purified by any purification method such as recrystallization, column chromatography, thin-layer chromatography, or liquid chromatography preparative separation.

[0237] In this invention, the term "pest control agent" refers to a pest control agent targeting harmful arthropods in fields such as agriculture and horticulture or livestock and hygiene (internal and external parasites in mammals or birds as livestock or pets, as well as household and commercial hygiene pests and nuisance pests).

[0238] Furthermore, in this invention, "agricultural chemicals" refers to insecticides, acaricides, nematicides, herbicides, and fungicides used in the fields of agriculture and horticulture.

[0239] In this specification, "sanitary pests" refers to harmful invertebrates that cause severe pain, swelling, itching, and other allergic symptoms in target animals by biting or stinging them, sometimes leading to fatal anaphylactic shock, or that transmit serious diseases through blood-sucking, sometimes resulting in death; invertebrates that sometimes contaminate food with pathogens such as viruses, bacteria, and parasites through contact; invertebrates whose living bodies, carcasses, molted exoskeletons, and feces act as allergens, causing allergic diseases such as bronchial asthma, rhinitis, conjunctivitis, and atopic dermatitis; invertebrates that cause economic damage by damaging food, clothing, and housing; and invertebrates that do not directly cause harm but cause discomfort by appearing in or invading human living environments. More specifically, this refers to ants that bite with their mandibles, wasps that sting with their venomous stingers, mosquitoes and assassin bugs that suck blood from the skin, and termites that are omnivorous and damage buildings such as houses.

[0240] In this specification, "nuisance insects" refer to insects that do not directly harm humans in the human living environment, but cause discomfort and psychological harm due to their appearance or form.

[0241] Insects, mites, crustaceans, mollusks, nematodes, ectoparasites, and endoparasites that can be controlled using the compounds of the present invention include, for example, the following organisms, but the present invention is not limited to these.

[0242] Pests include: 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 leaf roller (Caloptilia theivora), Peach fruit moth (Carposina sasakii), Rice stem borer (Chilo suppressalis), Rice leaf roller (Cnaphalocrocis medinalis), Yellow peach moth(Conogethespunctiferalis), Carpenter moth (Cossus insularis), Threespotted plusia (Ctenoplusia agnata), Codling moth (Cydia pomonella), Pine moth (Dendrolimus spectabilis), Janane hemlock caterpillar (Dendrolimus superans), Cucumber moth (Diaphania indica), sugarcane borer (Diatraea saccharalis), Eilema fuscodorsalis (Eilema fuscodorsalis), Eilema laevis (Eilema laevis), Lesser corn stalk Borer (Elasmopalpus lignosellus), Grape berry moth (Endopiza viteana), Limabean pod borer (Etiella zinckenella), Euproctis piperita (Euproctis piperita), Tea tussock moth (Euproctis pseudoconspersa), Japanese bamboo lappet moth (Euthrix albomaculata), Drinker moth (Euthrix potatoria), Oriental lappet (Gastropacha orientalis), Mulberry pyralid (Glyphodes pyloalis), Plum fruit moth (Grapholita dimorpha), Oriental fruit moth (Grapholita dimorpha) molesta), Sweetpotato leaffolder(Helcystogramma triannullella), CottonBollworm (Helicoverpa armigera), Oriental tobacco budworm (Helicoverpa assulta), American tobacco worm (Helicoverpa zea), Tobacco budworm (Heliothis virescens), Cabbage webworm (Hellula undalis), Oriental tea tortrix (Homona magnanima), Fall webworm moth (Hyphantria cunea), Pearleaf worm (Illiberis pruni), Prunus bud moth (Illiberis rotundata), Quercus lasiocampid (Kunugia undans), Yamada moth (Kunugia yamadai), Soybean pod borer (Leguminivora glycinivorella), Mulberry tiger moth (Lemyra imparilis), Gypsy moth (Lymantria dispar), Peach leafminer (Lyonetia clerkella), Silver-spotted leafminer (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 butterfly (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, white-skinned armyworm (Spodoptera)(exigua), 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), Sweetpotato 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 beetle (Epilachna varivestis), Large twenty-eight-spotted ladybird (Epilachna vigintioctomaculata), Twenty-eight-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), Sweetpotato 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 (Phyllotretastriolata), 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 ant (Solenopsis spp.), Asian giant hornet (Vespa mandarinia), Japanese yellow hornet (Vespa simillima), etc. Order Diptera; Yellow fever mosquito (Aedes aegypti), Asian tiger mosquito (Aedes albopictus), Aedes species (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), Korean mosquito (Anopheles koreicus), Anopheles lesteri (Anopheles Anopheles spp., 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 Calliphora lata (Calliphoralata), Calliphora species (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., Sprayed 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 (Gasterophilus 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 (Hydrotaeairritans), Hydrotaea spp., Warble fly (Hypoderma bovis), Common cattle grub (Hypoderma lineatum), Hypoderma spp., Black gnat (Leptoconops) Lipoptena nipponensis), Lipoptena capreoli, Lipoptena cervi, Lipoptena spp., Cabbage leafminer (Liriomyza brassicae), Tomato leafminer (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 Common green bottle fly (Lucilia sericata), Lucilia species (Lucilia spp.), Lutzomyia species (Lutzomyia spp.)), Hessian fly (Mayetiola destructor), Sheep ked (Melophagus ovinus), Melophagus spp., Sweet 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 blowfly (Phormia regina), Prosimulium yezoensis, Northern blowfly (Protophormia terraenovae), Przhevalskiana silenus, Apple maggot (Rhagoletis pomonella), Rhinoestrus spp., Fresh fly (Sarcophaga carnaria), Flesh fly (Sarcophaga peregrina), sarcophaga species (Sarcophaga spp.), black fly (Simulium ochraceum), Simulium reptans, black fly species (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.), Wilhelmia equine, Wilhelmia spp., Wohlfahrtia spp., etc. Order Hemiptera; Green stink bug (Acrosternumhilare), 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 aphid (Brachycaudus helichrysi), radish aphid (Cabbage)aphid (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), stink bug (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), two-spotted leafhopper (Grape)Leafhopper (Epiacanthus stramineus), Wooly apple aphid (Eriosoma lanigerum), Cabbage bug (Eurydema rugosa), Brown stink bug (Euschistus servus), Whitespotted spined bug (Eysarcoris aeneus), Large spined whitespotted 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 leafhopper leafhopper (Macrosteles fascifrons), Grape Leafhopper (MacrostelesStriifrons), Sugarcane spittlebug (Mahanarva fimbriolata), Blackmargined 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), Southern spiny stink 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 peach scale insectScale (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 bug 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), False Snow Scale (Unaspis citri), Euonymus Scale (Unaspis euonymi), Arrowhead Scale (Unaspis yanonensis), Grape Aphid (Viteus vitifolii), etc. Order Thysanoptera; includes species such as Flower thrips (Frankliniellaintonsa), 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. Order 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 Blattodea (cockroaches): 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. Order Isoptera; including the Formosanus termite (Coptotermes formosanus), the Japanese termite (Reticulitermes speratus), the Taiwanese termite (Odontotermes formosanus), etc. Order Acari; Cyclamen mite (Phytonemus pallidus), broad mite (Polyphagotarsonemus latus), striped broad mite (Tarsonemus bilobatus), Chinese cabbage mite (Penthaleus erythrocephalus), winter grain mite (Penthaleus major), rice spider mite (Oligonychus shinkajii), citrus red mite (Panonychus citri), mulberry spider mite (Panonychus mori), European red mite (Panonychus ulmi), Kanzawa spider mite (Tetranychus kanzawai), Two-spotted spider mite (Tetranychus urticae), Tea rust mite (Acaphylla theavagrans), Tulip rust mite (Aceria tulipae), Tomato rust mite (Aculops lycopersici), Pink citrus rust mite (Aculops pelekassi), Apple rust mite (Aculus schlechtendali), False pear rust mite (Eriophyes chibaensis), Citrus rust mite (Phyllocoptruta oleivora), Bulb mite (Rhizoglyphus robini), Mold mite (Tyrophagus putrescentiae), spinach mite 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 * 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), stag beetle tick (Dermacentor spp.), American dog tick (Dermacentor variabilis), poultry red mite (Dermanyssus gallinae), Dermanyssus spp., American house dust mite (Dermatophagoides farina), house dust mite (Dermatophagoides pteronyssinus), Eutrombicula wichmanni, storage mite (Glycyphagus destructor), house itch mite (GlycyphagusHaemaphysalis domesticus), Haemaphysalis cinnabarina, Common rodent tick (Haemaphysalis concinna), Yellow dog tick (Haemaphysalis leachi), Bush tick (Haemaphysalis longicornis), Haemaphysalis isotophila, Red sheep tick (Haemaphysalis punctate), Haemophysalis spp., Haplochthonius simplex, Trombiculid mite (Helenicula miyagawai), Tortoise tick (Hyalomma aegyptium), Hyalomma anatrichum Ixodes 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 species (Ixodesspp.), 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., Railietia spp., Brown ear tick (Rhipicephalus appendiculatus), Brown ear tick (Rhipicephalus bursa), Rhipicephalus capensis (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 species (Sarcoptes spp.), Sarcoptes Swiss (Sarcoptes suis), Itch mite (Sarcoptis canis), Sternostoma species (Sternostoma spp.), red mites (Trombicula akamushi), Trombicula species (Trombicula(spp.), Cheese mite (Tyrophagus putrescentiae), Tyrophagus spp., Varroa mite (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), Animal louse (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. Mallophaga (order of lice); 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), Flufflouse (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), Animal louse (Trichodectes Werneckiella equi, Werneckiella spp., etc. Flea order (Siphonaptera); includes chicken flea (Ceratophyllus gallinae), dog flea (Ctenocephalides canis), cat flea (Ctenocephalides felis), sticktight flea (Echidnophaga gallinacean), human flea (Pulex irritans), sand flea (Tunga penetrans), oriental rat flea (Xenopsylla cheopis), etc. Other parasites include monogeneans (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., and Gyrodactylus. spp.), Heteraxine heterocerca, Heterobothrium okamotoi, Lamellodiscus spp., copepod (Lepeophtheirus cuneifer), Lepeophtheirus hippoglossi, Lepeophtheirus pectoralis, salmon louse (Lepeophtheirus salmonis), Microcotyle sebastis, Microcotyle sebastisci, Neobenedenia, Neobenedenia congeri, Neobenedenia gillere 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., Miniature tapeworm (Hymenolepis diminuta), Membranous tapeworm (Hymenolepis spp.), Joyeuxiella spp., Ligura spp., Mesocestoides spp., Beneden's tapeworm (Moniezia) Moniezia spp., Paranoplocephala spp., Railietina spp., Schistocephalus spp., Spirometra spp., Stilesia spp.), including the beef tapeworm (Taenia saginata), the pork tapeworm (Taenia solium), the cat tapeworm (Taenia taeniaeformis), the thysaniezia spp., and the 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., Echinostoma (spp.), small pancreatic fluke Eurytrema coelomaticum, pancreatic fluke Eurytrema pancreaticum, Eurytrema spp., giant liver fluke Fasciola gigantica, sheep liver fluke Fasciola hepatica, Fasciola spp., Fasciolides spp., large intestinal fluke Fasciolopsis bruski, large intestinal fluke Fasciolopsis spp., Fischoederius spp., Gastrothylacus 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), Diprotostoma. Species such as Paramphistomum spp., Plagiorchis spp., Posthodiplostomum spp., Prosthogonimus spp., Schistosoma haematobium, Schistosoma japonicum, Schistosoma mansoni, Schistosoma spp., Trichobilharzia spp., Troglotrema spp., Typhlocoelum spp., etc. Nematodes; feline lungworm species (Aelurostrongylus spp.), Amidostomum species, hookworm species (Ancylostoma spp.), bloodworm species (Angiostrongylus spp.), Anisakis species, chicken roundworm (Ascaridia galli), Ascaridia species (Ascaridia spp.), roundworm species (Ascaris spp.), pig roundworm (Ascaris suum), Aspiculus species (Aspiculus spp.), Brugia species (Brugia spp.), Bunostomum species (Bunostomum spp.), whipworm species (Capillaria spp.), Chabertia species (Chabertia spp.), intestinal worm (Cooperia oncophora) (oncophora), Cooperia spp., Crenosoma spp., Cyathostoma spp., Cyclococercus spp., Cylicostephanus spp., Cylindropharynx spp., Cystocaulus spp., Dictyocaulus spp., Dirofilaria immitis, Dirofilaria spp., Dracunculus spp., Draschia spp., Elaphostrongylus spp.) Enoplida, Enterobius spp., Filaroides spp., Filicollis 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., 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., 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., Syngamus spp., Syphacia spp., Thelazia spp., Toxascaris spp., Toxocara This includes species such as Trichomosoides, Trichinella, Triconema, Trichostrongylus colubriformis, Trichostrongylus, Trichouris, Triodontphorus, Uncinaria, Wuchereria, etc. Protozoa; Babesis 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 Examples include Toxoplasma spp., Trichomonadidae spp., and Trypanosomsa cruzi.

[0243] Furthermore, the compounds of the present invention are effective against pests that have developed resistance to existing insecticides such as organophosphorus compounds, carbamate compounds, and pyrethroid compounds.

[0244] In other words, the compounds of the present invention can effectively control harmful organisms belonging to the following orders at low concentrations: insects such as Mycoptera (collimobiota), Blattodea (cockroaches), Orthoptera (grasshoppers), Termites, Thysanoptera (thrips), Hemiptera (true bugs and leafhoppers), Lepidoptera (butterflies and moths), Coleoptera (beetles and lice), Hymenoptera (bees and wasps), Diptera (flies), Isoptera (fleas and lice), Crustaceans such as Lepidoptera, Fish lice, and Cyclops, Mites, Gastropoda, Tapeworms, Trematodes, Nematodes, Protozoa, etc.

[0245] On the other hand, the compounds of the present invention have extremely useful characteristics, having almost no adverse effects on mammals, fish, crustaceans, and beneficial insects (useful insects such as honeybees and bumblebees, as well as natural enemies such as parasitic wasps, aphid wasps, tachinid flies, stink bugs, and predatory mites).

[0246] When using the compound of the present invention, it is usually mixed with a suitable solid or liquid carrier, and optionally a surfactant, penetrating agent, spreading agent, thickener, antifreeze, binder, anticaking agent, disintegrant, defoaming agent, preservative, decomposition inhibitor, etc., can be added to produce a formulation of any dosage form, such as a soluble concentrate, emulsifiable concentrate, wettable powder, water-soluble powder, water-dispersible granule, water-soluble granule, suspension concentrate, concentrated emulsion, suspoemulsion, microemulsion, dustable powder, granule, tablet, or emulsifiable gel. Furthermore, from the viewpoint of saving labor and improving safety, the above-mentioned formulations of any dosage form can also be supplied in water-soluble packaging such as water-soluble capsules or bags made of water-soluble film.

[0247] As solid carriers, for example, natural minerals such as quartz, calcite, meerschmiform, dolomite, chalk, kaolinite, pyrophyllite, sericite, halosite, metahalosite, kibushi clay, kaolinite, pottery stone, ziecklite, allophane, shirasu, kira, talc, bentonite, activated clay, acid clay, pumice, attapulgite, zeolite, diatomaceous earth, etc.; fired products of natural minerals such as fired clay, perlite, shirasu balloons, vermiculite, attapulgite clay, fired diatomaceous earth, etc.; magnesium carbonate, calcium carbonate, sodium carbonate, Inorganic salts such as 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 benzoic acid salts; plant materials 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; etc.

[0248] Examples of liquid carriers include xylene, alkyl (C9 or C9). 10Aromatic hydrocarbons such as benzene, phenylxylethane, alkyl (C1 or C3, etc.) naphthalene; aliphatic hydrocarbons such as machine oil, normal paraffin, isoparaffin, naphthene; mixtures of aromatic and aliphatic hydrocarbons such as kerosene; alcohols such as ethanol, 2-propanol, cyclohexanol, phenoxyethanol, benzyl alcohol; polyhydric alcohols such as ethylene glycol, propylene glycol, diethylene glycol, hexylene glycol, polyethylene glycol, 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, propylene glycol monophenyl ether; ketones such as acetophenone, cyclohexanone, γ-butyrolactone; esters such as fatty acid methyl esters, dialkyl succinate esters, dialkyl glutamate esters, dialkyl adipate esters, dialkyl phthalate esters; N-alkyl (C1, C8, or C 12 Examples include acid amides such as pyrrolidone; oils and fats such as soybean oil, linseed oil, rapeseed oil, coconut oil, cottonseed oil, and castor oil; dimethyl sulfoxide, water; and others.

[0249] These solid and liquid carriers may be used individually or in combination of two or more types.

[0250] Examples of surfactants include nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl (mono or di)phenyl ethers, polyoxyethylene (mono, di or tri)styrylphenyl 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, alkyl glycosides; alkyl sulfate salts, alkylbenzene sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene Examples of surfactants include anionic surfactants such as naphthalene sulfonates, alkylnaphthalene sulfonates, salts of formalin condensates of naphthalene sulfonic acid, salts of formalin condensates of alkylnaphthalene sulfonic acid, polyoxyethylene alkyl ether sulfate or phosphate ester salts, polyoxyethylene (mono or di)alkylphenyl ether sulfate or phosphate ester salts, polyoxyethylene (mono, di or tri)styrylphenyl ether sulfate or phosphate ester salts, polycarboxylate salts (e.g., polyacrylates, polymaleates, copolymers of maleic acid and olefins, etc.), and polystyrene sulfonates; cationic surfactants such as alkylamine salts and alkyl quaternary ammonium salts; amphoteric surfactants such as amino acid type and betaine type; silicone-based surfactants, fluorine-based surfactants, etc.

[0251] The content of these surfactants is not particularly limited, but is generally in the range of 0.05 to 20 parts by mass per 100 parts by mass of the formulation of the present invention. Furthermore, these surfactants may be used individually or in combination of two or more types.

[0252] The appropriate application amount of the compound of the present invention varies depending on the application situation, timing of application, method of application, and cultivated crop, but generally, an amount of approximately 0.005 to 50 kg of the active ingredient per hectare (ha) is suitable.

[0253] On the other hand, when using the compound of the present invention as a control agent for internal or external parasites in mammals and birds as livestock and companion animals, an effective amount of the compound of the present invention can be administered orally with pharmaceutical additives; parenterally by injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.); transdermally by immersion, spray, bath, washing, pouring-on, spotting-on, dusting, etc.; nasal administration; etc. The compound of the present invention can also be administered in the form of molded products using fragments, plates, bands, collars, ear marks, rim bands, labeling devices, etc.

[0254] For administration, the compound of the present invention can be in any dosage form suitable for the route of administration.

[0255] When using the compound of the present invention to eliminate external or internal parasites, the preferred dosage of the active ingredient, compound (1), depends on the type of parasite to be controlled, the species of the animal to be administered to, or the method of administration. However, it is usually 0.01 to 100 mg / kg, preferably 0.01 to 50 mg / kg, per kilogram of body weight of the animal to be administered to. In particular, the dosage for dogs may vary depending on the breed or age of the dog, or the external parasite to be controlled, but it is usually 1 to 5000 mg / kg, preferably 1 to 100 mg / kg, per kilogram of live body weight of the dog.

[0256] When administering the compound of the present invention to eliminate external or internal parasites, the administration interval depends on the type of parasite to be controlled, the species of the animal to be administered to, or the method of administration, but can usually be set arbitrarily within the range of daily to once a year. Preferably, it is once a week to once every six months, and more preferably daily (24 hours), monthly, once a month, once every two months, once every three months, or once every six months.

[0257] Furthermore, when using the compound of the present invention to control external parasites in dogs, possible timings for administering the compound to dogs include, for example, oral administration to the dog 30 minutes immediately before the start of feeding or 120 minutes after the end of feeding. The times 30 minutes before the start of feeding and 120 minutes after the end of feeding are based on the act of the dog consuming the food given to it for the purpose of nutritional intake. For example, if the dog's feeding time is 20 minutes, the prescribed time is a total of 170 minutes, from 30 minutes before the start of feeding to 120 minutes after the end of feeding, based on the act of eating. This also includes cases where feeding is interrupted, the compound of the present invention is administered orally, and then feeding is resumed. In this specification, "feeding" means the act of an animal consuming food.

[0258] Generally, the number of times a dog eats per day varies depending on the breed, age, and habits, but typically it is 3-4 times a day for dogs under 6 months old, 2-3 times a day for dogs between 6 months and 1 year old, 2 times a day for adult dogs between 1 and 5 years old, and 2-3 times a day for senior dogs over 6 years old. In this invention, "eating" refers to the act of eating for the purpose of obtaining nutrients, and does not include the act of giving food or other items for the purpose of training or discipline dogs.

[0259] Examples of dosage forms that can be prepared include solid preparations such as powders, granules, wettable powders, pellets, tablets, pills, capsules, and molded products containing active compounds; liquid preparations such as injectable solutions, oral solutions, and solutions for use on the skin or in body cavities; liquid preparations such as pour-on preparations, spot-on preparations, flowables, and emulsions; and semi-solid preparations such as ointments and gels.

[0260] Examples of dosage forms for orally administering the compound of the present invention include solid preparations such as tablets, chewables, capsules, pills, boluses, granules, and powders; semi-solid preparations such as pastes and gels; and liquid preparations such as drinks.

[0261] Furthermore, examples of dosage forms for transdermal administration include solid preparations such as powders; semi-solid preparations such as creams, salves and ointments, pastes, and gels; and liquid preparations such as sprays, aerosols, solutions and emulsions, suspensions, and lotions.

[0262] Furthermore, when administered by injection, the dosage form may include liquid preparations such as solutions and emulsions and suspensions, while when administered intranasally, the dosage form may include liquid preparations such as aerosols.

[0263] Furthermore, when applied as a spray treatment to animal housing environments such as livestock barns, suitable formulations include solid preparations such as wettable powders, dusts, and granules; and liquid preparations such as emulsions and flowable supplements.

[0264] Furthermore, the formulations used in the parasite control agents of the present invention are not limited to these dosage forms.

[0265] The solid preparation can be administered orally as is, or diluted with water and used for transdermal administration, or sprayed onto the animal housing environment such as livestock barns.

[0266] Solid preparations used for oral administration can be prepared by mixing compound (1) of the present invention or a salt thereof with one or more excipients and binders suitable for oral administration, and, if necessary, physiologically acceptable additives such as lubricants, disintegrants, dyes, and pigments, and molding them into a desired shape.

[0267] Examples of excipients and binders include sugars or sugar derivatives such as lactose, sucrose, mannitol, and sorbitol; starches such as corn starch, wheat starch, rice starch, and potato starch; cellulose or cellulose derivatives such as methylcellulose, carboxymethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, and hydroxypropylmethylcellulose; proteins or protein derivatives such as zein and gelatin; and synthetic polymer compounds such as honey, gum arabic glue, polyvinyl alcohol, and polyvinylpyrrolidone.

[0268] Examples of lubricants include magnesium stearate, and examples of disintegrants include cellulose, agar, alginic acid, cross-linked polyvinylpyrrolidinone, and carbonates.

[0269] Furthermore, in the case of solid preparations used for oral administration, particularly solid preparations such as chewable tablets, additives are used to impart a taste, texture, and flavor preferred by the animal being administered the drug. However, the carriers and additives used in the solid preparations of the parasite control agent composition of the present invention are not limited to these.

[0270] The liquid preparation can be administered directly transdermally or by injection, mixed with feed for oral administration, diluted with water for oral or transdermal administration, or sprayed onto the animal housing environment such as livestock barns.

[0271] Injectable solutions can be administered intravenously, intramuscularly, and subcutaneously. Injectable solutions can be prepared by dissolving the active compound in a suitable solvent and, if necessary, adding additives such as solubilizers, acids, bases, buffer salts, antioxidants, and protective agents.

[0272] Suitable solvents include water, ethanol, butanol, benzyl alcohol, glycerin, propylene glycol, polyethylene glycol, N-methylpyrrolidone and mixtures thereof, physiologically acceptable vegetable oils, and synthetic oils suitable for injection.

[0273] Examples of solubilizing agents include polyvinylpyrrolidone, polyoxyethylated castor oil, and polyoxyethylated sorbitan esters.

[0274] Examples of protective agents include benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid esters, and n-butanol.

[0275] Oral solutions can be administered directly or diluted. They can be prepared in the same way as injectable solutions.

[0276] Flowable formulations, emulsions, etc., can be administered directly or diluted percutaneously, or by environmental treatment.

[0277] Liquid preparations for use on the skin can be administered by dropping, spreading, rubbing, spraying, dispensing, or by immersion (soaking, bathing, or washing). These liquid preparations can be prepared in the same way as injectable preparations.

[0278] Pour-on and spot-on agents are applied by dropping or spraying onto a limited area of ​​the skin, thereby allowing the active compound to penetrate the skin and act systemically.

[0279] Droplets and laxatives can be prepared by dissolving, suspending, or emulsifying the active ingredient in a suitable skin-compatible solvent or solvent mixture. If necessary, auxiliary agents such as surfactants, colorants, absorption enhancers, antioxidants, light stabilizers, and adhesives may be added.

[0280] 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-oxymethylene-1,3-dioxolane.

[0281] Absorption-enhancing substances include DMSO (dimethyl sulfoxide), isopropyl myristate, dipropylene glycol pelargonic acid, silicone oil, aliphatic esters, triglycerides, or fatty alcohols.

[0282] Antioxidants include sulfites, metabisulfites, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole, or tocopherol.

[0283] Emulsions can be administered orally, transdermally, or by injection. Emulsions can be prepared by dissolving the active ingredient in a hydrophobic or hydrophilic phase and homogenizing this with a solvent in another phase using a suitable emulsifier, and if necessary, further with auxiliary agents such as colorants, absorption enhancers, protective agents, antioxidants, light-shielding agents, and thickeners.

[0284] Examples of hydrophobic phases (oils) include paraffin oil, silicone oil, sesame oil, almond oil, castor oil, synthetic triglycerides, ethyl stearate, di-n-butyl adipate, hexyl lauryl acid, dipropylene glycol pelargonate, esters of branched short-chain fatty acids and saturated fatty acids with chain lengths of C16-C18, isopropyl myristate, isopropyl palmitate, caprylic / capric acid esters of saturated fatty alcohols with chain lengths of C12-C18, isopropyl stearate, oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, waxy fatty acid esters, dibutyl phthalate, diisopropyl adipate, isotridecyl alcohol, 2-octyldodecanol, cetyl stearyl alcohol, and oleyl alcohol.

[0285] Examples of hydrophilic phases include water, propylene glycol, glycerin, and sorbitol.

[0286] Examples of emulsifiers include nonionic surfactants such as polyoxyethylated castor oil, polyoxyethylated sorbitan monoolefinate, sorbitan monostearate, glyceryl monostearate, polyoxyethyl stearate, and alkylphenol polyglycol ethers; amphoteric surfactants such as disodium N-lauryl-β-iminodipropionate and lecithin; anionic surfactants such as sodium lauryl sulfate, fatty alcohol sulfate ethers, and monoethanolamine salts of mono / dialkyl polyglycol orthophosphate esters; and cationic surfactants such as cetyltrimethylammonium chloride.

[0287] Other auxiliary agents include carboxymethylcellulose, methylcellulose, polyacrylate, alginate, gelatin, gum arabic, polyvinylpyrrolidone, polyvinyl alcohol, methyl vinyl ether, copolymer of maleic anhydride, polyethylene glycol, wax, and colloidal silica.

[0288] The semi-solid preparation can be administered by applying or spreading it on the skin, or by introducing it into a body cavity. The gel can be prepared by adding a thickener sufficient to produce a transparent substance with ointment-like viscosity to the solution prepared as described above for the injectable liquid preparation.

[0289] Seed treatment in this invention refers to a treatment method that exerts control efficacy against harmful arthropods by directly or near the seeds, seed potatoes, or bulbs of crops that are to be protected from damage such as ingestion by harmful arthropods, by applying an active ingredient. Specifically, examples include spraying, coating, immersion, impregnation, coating, film coating, and pellet coating. The seed treatment agent is the substance of this invention that is applied to seed treatment.

[0290] Soil treatment in this invention refers to methods of controlling harmful organisms by directly applying an active ingredient to the rhizosphere of plants that are to be protected from damage such as feeding by harmful organisms, or by allowing the active ingredient to permeate and move into the plant body from the roots, etc. Specifically, these include, for example, planting hole treatment (spraying in planting holes, mixing in planting hole treatment soil), base treatment (spraying at the base of the plant, mixing at the base of the plant, drenching at the base of the plant, base treatment in the latter half of the seedling stage), furrow treatment (spraying in planting furrows, mixing in planting furrow soil), furrowing treatment (spraying in furrows, mixing in furrow soil, spraying in furrows during the growing season), furrowing treatment at sowing (spraying in furrows at sowing, mixing in furrow soil at sowing), overall treatment (spraying in soil over the entire area, mixing in soil over the entire area), side-dressing treatment, and water surface treatment (application to the entire water surface, fringe water treatment). (Surface application), other soil application treatments (granular foliar application during the growing season, application under the tree canopy or around the main trunk, soil surface application, soil surface mixing, application in seed holes, soil surface application on ridges, application between plants), other drenching treatments (soil drenching, drenching during the seedling stage, chemical injection treatment, drenching at the base of the plant, chemical drip irrigation, chemigation), seedling tray treatments (seedling tray application, seedling tray drenching, Examples of treatments include flooding seedling trays with chemical solution, seedling bed treatment (seedling bed spraying, seedling bed drenching, watered seedling bed spraying), seedling soaking, seedling growing medium mixing treatment (soil mixing, covering soil mixing), pre-covering application at sowing, post-covering application at sowing, stem injection treatment, trunk injection treatment, trunk spray treatment, and other treatments (plowing in, topsoil mixing, rainwater drainage area mixing, planting location treatment, granular flower cluster application, paste fertilizer mixing). Soil treatment agents are substances of the present invention that are applied to soil treatment.

[0291] Next, examples of formulations using the compound of the present invention are shown. However, the formulation examples of the present invention are not limited to these. In the following formulation examples, "parts" means parts by mass.

[0292] [Wettable powder] 0.1 to 80 parts of the compound of the present invention Solid carrier 5-98.9 parts Surfactant 1-10 parts Other 0-5 parts Other examples include anti-caking agents and anti-decomposition agents.

[0293] 〔emulsion〕 0.1 to 30 parts of the compound of the present invention Liquid carrier 45-95 parts Surfactant 4.9-15 parts Other 0-10 copies Other examples include spreading agents and decomposition inhibitors.

[0294] [Suspension] 0.1 to 70 parts of the compound of the present invention Liquid carrier: 15-98.89 parts Surfactant 1-12 parts Other 0.01-30 copies Other examples include antifreezes and thickeners.

[0295] [Granular wettable powder] 0.1 to 90 parts of the compound of the present invention Solid carrier 0-98.9 parts Surfactant 1-20 parts Other 0-10 copies Other examples include binders and decomposition inhibitors.

[0296] [Liquid formulation] 0.01 to 70 parts of the compound of the present invention Liquid carrier 20-99.99 parts Other 0-10 copies Other examples include antifreezes and spreading agents.

[0297] [Granules] 0.01 to 80 parts of the compound of the present invention Solid carrier 10-99.99 parts Other 0-10 copies Other examples include binders and decomposition inhibitors.

[0298] [Powder] 0.01 to 30 parts of the compound of the present invention Solid carrier 65-99.99 parts Other 0-5 parts Other examples include drift inhibitors and decomposition inhibitors.

[0299] Next, we will show more specifically some examples of formulations containing the compound of the present invention as an active ingredient, but the present invention is not limited to these.

[0300] [Example of formulation 1] Wettable powder Compound No. 1-001 of the present invention: 20 parts Pyrophyllite 74 units Solpol 5039, 4 parts (Toho Chemical Industry Co., Ltd. product name, mixture of nonionic and anionic surfactants) Carplex #80D 2 parts (Shionogi & Co., Ltd. product name, synthetic hydrated silica) The above ingredients are uniformly mixed and ground to make a wettable powder.

[0301] [Example of formulation 2] Emulsion Compound No. 1-001 of the present invention: 5 parts Xylene 75 units N-methylpyrrolidone 15 parts Solpol 2680, 5 copies (A product name of Toho Chemical Industry Co., Ltd., a mixture of nonionic and anionic surfactants) Mix the above ingredients uniformly to form an emulsion.

[0302] [Example of formulation 3] Suspension Compound No. 1-001 of the present invention: 25 parts Agrizol S-710, 10 units (Product name, nonionic surfactant, manufactured by Kao Corporation) Lunox 1000C 0.5 bu (A product name of Toho Chemical Industry Co., Ltd., anionic surfactant) Xanthan gum 0.2 parts Water 64.3 parts After uniformly mixing the above ingredients, wet grinding is performed to obtain a suspension.

[0303] [Example of formulation 4] Granular wettable powder Compound No. 1-001 of the present invention: 75 parts Hightenol NE-15 5 parts (A product name of Daiichi Kogyo Seiyaku Co., Ltd., anionic surfactant) Vanillex N 10 copies (Nippon Paper Industries Co., Ltd. product name, anionic surfactant) Carplex #80D 10 pieces (Shionogi & Co., Ltd. product name, synthetic hydrated silica) After uniformly mixing and grinding the above ingredients, a small amount of water is added and stirred, then granulated using an extruder, dried, and used to obtain a wettable powder granule.

[0304] [Formulation example 5] Granules Compound No. 1-001 of the present invention: 5 parts Bentonite 50 copies Talc 45 pieces After uniformly mixing and grinding the above ingredients, a small amount of water is added and stirred, then granulated using an extrusion granulator, and dried to obtain granules.

[0305] [Formulation Example 6] Powder Compound No. 1-001 of the present invention, 3 parts Carplex #80D 0.5 bu (Shionogi & Co., Ltd. product name, synthetic hydrated silica) Kaolinite 95 copies Diisopropyl phosphate 1.5 parts The above ingredients are uniformly mixed and ground to obtain a powder.

[0306] When using the above-mentioned formulation, dilute it with water 1 to 10,000 times, or spray it directly without dilution.

[0307] [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 3 parts sodium salt of naphthalene sulfonic acid formalin condensate Emulsion-type silicone (1 part) Silicon dioxide (3 parts) Kaolin 45 copies [Formulation Example 8] Water-soluble concentrate 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] Spray liquid Compound No. 1-001 of the present invention, 2 parts Dimethyl sulfoxide 10 parts 2-Propanol 35 parts Acetone 53 units [Example 10] Transdermal solution Compound No. 1-001 of the present invention: 5 parts Hexylene glycol 50 parts 2-Propanol 45 parts [Example 11] Transdermal solution Compound No. 1-001 of the present invention: 5 parts Propylene glycol monomethyl ether 50 parts Dipropylene glycol 45 parts [Example 12] Solution for transdermal administration (dropping) Compound No. 1-001 of the present invention, 2 parts Light liquid paraffin 98 parts [Example 13] Solution for transdermal administration (dropping) Compound No. 1-001 of the present invention, 2 parts Light liquid paraffin 58 parts Olive oil 30 units ODO 9 (Product name of Nisshin Oillio Group Co., Ltd., Medium-Chain Triglyceride Oil) Shin-Etsu Silicone, Part 1 Furthermore, when using the compound of the present invention as an agricultural chemical or animal drug, it may be mixed with other chemicals as needed during formulation or application.

[0308] By applying a mixture of pesticides, it is possible to reduce costs by decreasing the amount of pesticide applied, and to broaden the control spectrum and achieve higher pest control efficacy through the synergistic effects of the mixed pesticides. In this case, it is also possible to combine multiple known pesticides simultaneously.

[0309] For example, examples of pesticides that can be used in combination with the compounds of the present invention include compounds described in The Pesticide Manual, 18th edition, 2018. Antiparasitic drugs and antibiotics that can be used in combination as veterinary drugs are also listed below, but are not necessarily limited to these.

[0310] Insecticides: abamectin, acephate, acequinocyl, acetamiprid, acrinathrin, acynonapyr, afidopyropen, afoxolaner, alanicarb, aldicarb, allethrin, 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, biorethmetrin smethrin), bistrifluron, bisulflufen, broflanilide, bromopropylate, buprofezin, butocarboxim, carbaryl, carbofuran, carbosulfan, cartap, chinomethionate, chlorantraniliprole,Chlorethoxyfos, chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, chlorobezilate, chloroprallethrin, chlorpyrifos, chlorpyrifos-methyl, chromafenozide Nozide), clofentezine, clothianidin, cyanophos, cyantraniliprole, cyclaniliprole, cycloprothrin, cyenopyrafen, cyetpyrafen, cyflumetofen, cyfluthrin, cyhalodianide (cyha lodiamide), cyhalothrin, cyhexatine, cypermethrin, cyphenothrin, cyproflanilide, cyromazine, deltamethrin, diacloden, diafenthiuron, diazinon, dichlorvos, dichloromesothiaz (dicloromezotiaz), 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, ethiofencarb, ethiprole, etofenprox, etoxazole, etrimfos, Febantel, fenazaquin, fenbutatin oxide oxide), fenitrothion, fenmezoditiaz, fenobucarb, fenothiocarb, fenoxycarb, fenpropathrin, fenpyroximate, fenthion, fenvalerate, fipronil, flometoquin, flonicamid, fluacrypyrim, fluazuron azuron), flubendiamide, fluchlorodiniliprole, flucycloxuron, flucythrinate, flufenerim, flufenoxuron, flufenprox, flufiprole, fluhexafon, flumethrin, flupentiofenox, flupyradifurone,Flupyrimin, flupyroxystrobin, fluralaner, fluvalinate, fluxametamide, fonophos, formetanate, formothion, furathiocarb, gamma-cyhalothrin, halfenprox ), halofenozide, heptafluthrin, hexaflumuron, hexythiazox, hydramethylnon, imidacloprid, imiprothrin, indazapyroxamet, indoxacarb, indoxacarb-MP, isocycloserum ( isocycloseram, isofenphos, isoflualanam, isoprocarb, isoxathion, kappa-bifenthrin, kappa-tefluthrin, lambda-cyhalothrin, ledprona, lepimectin, lufenuron Malathion, meperfluthrin, metaflumizone, metalcarb, metaldehyde, methacrifos, methamidophos, methidathion, methomyl, mesoprene, methoxychlor, methoxyfenozide,Methyl bromide, metofluthrin, milbemectin, momfluorothrin, monocrotophos, muscalure, nicofluprole, nitenpyram, novaluron, nobiflumulon, omethoate, oxazosulfyl, oxydemeth oxydemeton-methyl, oxydeprofos, parathion, parathion-methyl, pentachlorophenol, permethrin, phenothrin, phenthoate, phorate, phosalone, phosmet, phosphamidone ), phoxim, pioxaniliprole, piperflanilide, pirimicarb, pirimiphos-methyl, praziquantel, profenofos, profluthrin, propaphos, propargite, prothiofos, pu Lotrifenbute, pyflubumide, pymetrozine, pyraclofos, pyrafluprole, pyrethrins, pyridaben, pyridalyl, pyrifluquinazon, pyrimidifen, pyriprole, pyriproxyfen,Resmethrin, rotenone, silafluofen, spidoxamat, spinetoram, spinosad, spirobudifen, spirodiclofen, spiromesifen, spiropidion, spirotetramat, spiromesifen esifen), sulfiflumin, sulfotep, sulfoxaflor, sulprofos, tau-fluvalinate, tebfenozide, tebufenpyrad, teflubenzuron, tefluthorin, terbufos, tetrachlorantraniliprole chlorantraniliprole), tetrachlorvinphos, tetramethrin, tetramethylfluthrin, tetraniliprole, thiacloprid, thiamethoxam, thiocyclam, thiodicarb, thiofanox, thiometon meton), thiolantraniliprole, tolfenpyrad, tralomethrin, transfluthrin, trizamate, triazuron, trichlorfon, triflumezopyrim, triflumuron, tyclopyrazoflor,Vamidothion and zeta-cypermethrin, etc.

[0311] 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, Benzamorf, Benzovindiflupyr, Binapacryl, Biphenyl, Bitertanol, Bixafen, Blastoicidin-S, Bordeaux mixture Cheshunt mixture), boscalid, bromoconazole, bupirimate, butthiobate, butylamine, calcium polysulfide, captafol, captan, carbamorph, carbendazim, carboxin, carpropamid, carvone, cheshunt mixture(mixture), chinomethionate, 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 Chromate, coumoxystrobin, cresol, cufraneb, cuprobam, cyazofamid, cyclafuramid, cycloheximide, cyflufenamid, cymoxanil, cypendazole, cyproconazole, cyprodinil, cyprofuram, dazomet, debacarb, decafentin, dehydroacetate acid), diclobentiazox, dichlofluanid, dichlorone, dichlorophen, dichlozoline, diclobutrazol, diclocymet, diclomezine, dichloran, diethofencarb, difenoconazole,Diflumetorim, Dimethirimol, Dimethomorph, Dimoxystrobin, Diniconazole, Diniconazole-M, Dinobuton, Dinocap, Dinocap-4, Dinocap-6, Dinocton, Dinosulfon, Dinotel Dinoterbon, diphenylamine, dipymetitrone, dipyrithione, disulfiram, ditalimfos, dithianon, DNOC, dodemorph, dodine, drazoxolon, edifenphos, enestrobin, enoxa Enoxastrobin, Epoxiconazole, Etaboxam, Etaconazole, Etem, Ethirimol, Ethoxyquin, Etridiazole, Famoxadone, Fenamidone, Fenaminosulf, Fenaminstrobin, Phenapanil (fenapanil), fenarimol, fenbuconazole, fenfuram, fenhexamid, fenitropan, fenoxanil, fenpiclonil, fenpicoxamid, fenpropidin, fenpropimorph, fenpyrazamine,Fentin, Ferbam, Ferimzone, Florylpicoxamide, Fluazinam, Flubeneteram, Fludioxonil, Flufenoxadiazam, Flufenoxystrobin, Fluindapyr, Flumetylsulforim etylsulforim, flumetover, flumorph, fluopicolide, fluopimomide, fluopyram, fluoroimide, fluotrimazole, fluoxapiprolin, fluoxastrobin, fluoxytioconazole, Fluquinconazole, flusilazole, flusulfamide, flutolanil, flutianil, flutriafol, fluxapyroxad, folpet, fosetyl-aluminium, fthalide, fuberidazole, flaxyl ralaxyl), furametpyr, furcarbanil, furconazole, furconazole-cis, furmecyclox, furophanate, glyodin, griseofulvin, guazatine, halacrinate, hexachlorobenzene,Hexaconazole, hexylthiofos, 8-hydroxyquinoline sulfate, hymexazol, imazalil, imibenconazole, iminoctadine-albesilate, iminoctadine-triacetate, inpyrfluxam, iodocarb, ipconazole, ipfentrifluconazole fluconazole, ipflufenoquin, iprobenfos, iprodione, iprovalicarb, isofetamide, isoflucypram, isotianil, isoprothiolane, isopyrazam, isovaledione, kasugama Kasugamycin, Kresoxim-methyl, Laminarin, Mancopper, Mancozeb, Mandestrobin, Mandipropamid, Maneb, Mebenil, Mecarbinzid, Mefentrifluconazole, Mepanip Mepanipyrim, mepronil, meptyldinocap, metalaxyl, metalaxyl-M, metam, metarylpicoxamid, metazoxolon, metconazole, methasulfocarb, metofloxam,Methyltetraprole, metiram, metominostrobin, metrafenone, metsulfovax, milneb, myclobutanil, myclozolin, nabam, naftifine, natamycin, organonicickel (nickel bis (dimethyldithiocarbamate)), nitrostyrene, nitrothal-isopropyl, nuarimol, octhilinone, ofurace, orysastrobin, oxadixyl, oxathiapiprolin, oxine copper), oxpoconazole fumarate, oxycarboxin, pefurazoate, penconazole, pencycuron, penflufen, pentachlorophenol, penthiopyrad, 2-phenylphenol, phosdiphen, phthalide, picarbutrazox, picoxystrobin, piperalin, polycarbamate, polyoxins, polyoxorim, potassium azide, potassium bicarbonate carbonate, probenazole, prochloraz, procymidone,Propamocarb hydrochloride, propiconazole, propineb, proquinazid, prothiocarb, pyrazophos, pyribencarb, pyrifenox, pyrimethanil, pyriminostrobin, pyroquilon, prothiocarb, prothioconazole, pydiflumetofen, pyracarbolid, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyrapropoyne, pyradiflumid Pyridaclomethyl, pyridaclomethyl, pyridinitril, pyriophenone, pyrisoxazole, pyroxychlor, pyroxyfur, quinacetol-sulfate, quinazamid, quinconazole, quinoxyfen, quinofumelin, quintozene, rabenzazole, salicylanilide, seboctylamine, sedaxane, silthiofam, simeconazole, sodium bicarbonate Hydrogen carbonate, sodium hypochlorite, spiroxamine, sulfur, tebuconazole,Tebufloquin, tecloftalam, tecnazene, tecoram, tetraconazole, thiabendazole, thiadifluor, thicyofen, tifluzamide, thiochlorfenphim, thiophanate, thiophanate-methyl thiram, tiadinil, tioxymid, tolclofos-methyl, tolprocarb, tolylfluanid, triadimefon, triadimenol, triamiphos, triarimol, triazbutil, triazoxide, tributyltin oxide Examples include oxide, trichlamide, triclopyricarb, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, validamycin, valifenalate, vinclozolin, zarilamid, zinc naphthenate, zinc sulfate, zineb, ziram, zoxamide, shiitake mycelium extract, and shiitake fruiting body extract.

[0312] Nematicides: Aldoxycarb, benclothiaz, caduafos, cyclobutrifluram, DBCP, diclofenthion, DSP, etoprophos, fenamiphos, fensulfothion, fluazaindol Examples include lizine, fluensulfone, fosthiazate, fosthietan, imicyafos, isamidofos, isazofos, oxamyl, thiaxazafen, thionazin, tioxazafen, and trifluenfuronate.

[0313] Antiparasitic drugs: esfenvalerate, fenpropathrin, fenvalerate, alpha-cypermethrin, 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, chlorthulon, closantel, coumaphos, dichlorophen, diethylcarbamazine, diminazene, dinitolmide, dithiazanine iodide iodide), emodepside, epsiplantel, febantel, fenbendazole, flubendazole, glycopyramide, imidocarb, levamisole, mebendazole, mebendazole, mefloquine hydrochloride, melarsamine hydrochloride, 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.

[0314] Antibiotics: Amoxicillin, ampicillin, cefapirin, cefazolin sodium, cefquinome, ceftiofur, penicillin, chlortetracycline, oxytetracycline, danofloxacin, difloxacin, oxolinicacid, enrofloxacin, florfenicol These include lincomycin, lomefloxacin, marbofloxacin, miloxacin, mirosamycin, norfloxacin, ofloxacin, orbifloxacin, valnemulin, thiamphenicol, tiamulin fumarate, tilmicosin phosphate, acetylisovaleryltylosin acetate, tylosin phosphate, tulathromycin, ketoconazole, miconazole nitrate, and clavulanic acid.

[0315] The development of pest control agents aimed at controlling various pests and diseases, such as those affecting agriculture and horticulture, forestry, and public health, has progressed, and a wide variety of these agents have been put into practical use to this day.

[0316] However, due to the long-term use of these chemicals, pests and diseases have recently acquired resistance to these agents, making control with conventional insecticides and fungicides increasingly difficult. Furthermore, some existing pest control agents are highly toxic, or remain in the environment for extended periods, leading to problems that disrupt ecosystems. Under these circumstances, there is a constant need for the development of novel pest control agents that not only possess high pest control activity but also have low toxicity and low persistence.

[0317] The compound of this invention exhibits excellent insecticidal and acaricidal activity against many agricultural pests, spider mites, sanitary disease pests, and internal or external parasites of mammals or birds, and also has a long residual effect. Furthermore, it provides sufficient control even against pests that have acquired resistance to existing insecticides. In addition, it has almost no adverse effects on mammals, fish, and beneficial insects, has low persistence, and places a light burden on the environment.

[0318] 〔summary〕 As described above, the present invention relates to the following [1] to

[11] . [1] An isoxazoline-substituted benzamide compound represented by the following formula (1), or a salt thereof.

[0319] [ka]

[0320] [In the formula, W represents an oxygen atom or a sulfur atom, Q represents Q-1 or Q-2,

[0321] [ka]

[0322] X 1 , X 2 and X 3Each of these independently represents a hydrogen atom, a halogen atom, a cyano, a nitro, an amino, a C1-C6 alkyl, a C1-C6 alkoxy, a C1-C6 haloalkyl, or a halo(C1-C6)alkoxy. Y 1 This represents a hydrogen atom, a halogen atom, a cyano, a nitro, a C1-C6 alkyl, a C1-C6 haloalkyl, or a halo(C1-C6) alkoxy. Y 2 This represents a hydrogen atom, Or, Y 1 and Y 2 These elements combine to form a 6-membered ring -CH=CH-CH=CH-, R 1 is -C(O)R 1a ,-C(S)R 1a , -C(O)OR 2a -C(O)SR 2a ,-C(O)N(R 1c )R 1b ,-C(S)N(R 1c )R 1b -S(O)2R 1a -S(O)2N(R 1c )R 1b ,-C(O)C(O)R 1a Or it represents -CHO, R 2 is a hydrogen atom, C1-C6 alkyl, R 10 Represents (C1-C6) alkyl, C2-C6 alkenyl, or C2-C6 alkynyl substituted by R 3 is a hydrogen atom, C1-C6 alkyl, R 6 (C1-C6) alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, halo(C2-C6) alkenyl, C2-C6 alkynyl, halo(C2-C6) alkynyl, C3-C 10 Cycloalkyl, Halo(C3~C 10 )Cycloalkyl, C1-C6 alkoxy, Halo(C1-C6)alkoxy, -C(O)R 1d ,-C(S)R 1d , -C(O)OR 1d -C(O)SR 1d ,-C(O)N(R 1f)R 1e ,-C(S)N(R 1f )R 1e -S(O)2R 1d -S(O)2N(R 1f )R 1e or -N(R 14 )R 15 This represents, R 4 This represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, or a C2-C6 alkynyl group. R A C1-C6 alkyl, R 16 (C1-C6) alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, halo(C2-C6) alkenyl, C2-C6 alkynyl, halo(C2-C6) alkynyl, C3-C 10 Cycloalkyl, -C(O)R 1g or -C(O)OR 1h This represents, R 1a C1~C 10 Alkyl, R 7 (C1-C6) alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, halo(C2-C6) alkenyl, C2-C6 alkynyl, halo(C2-C6) alkynyl, C3-C 10 Cycloalkyl, Halo(C3~C 10 ) Cycloalkyl, R 13 C3~C substituted by 10 Cycloalkyl, phenyl, (Z 1 ) p1 Represents phenyl, D-1 to D-60, G-1 to G-60, or G-61 substituted by, D-1 to D-60 represent the following structures,

[0323] [ka]

[0324] [ka]

[0325] [ka]

[0326] G-1 to G-61 represent the following structures,

[0327] [ka]

[0328] [ka]

[0329] [ka]

[0330] R 2a C1-C6 alkyl, R 7 (C1-C6) alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, halo(C2-C6) alkenyl, C2-C6 alkynyl, halo(C2-C6) alkynyl, C3-C 10 Cycloalkyl, phenyl or (Z 1 ) p1 Represents phenyl substituted by, R 1b is a hydrogen atom, C1-C6 alkyl, R 8 (C1-C6) alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, halo(C2-C6) alkenyl, C2-C6 alkynyl, halo(C2-C6) alkynyl, C3-C 10 Cycloalkyl, C1-C6 alkoxy, halo(C1-C6)alkoxy, C1-C6 alkoxycarbonyl, phenyl or (Z 1 ) p1 Represents phenyl substituted by, R 1c This represents a hydrogen atom or a C1-C6 alkyl group. R 1dC1-C6 alkyl, R 9 (C1-C6) alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, halo(C2-C6) alkenyl, C2-C6 alkynyl, halo(C2-C6) alkynyl, C3-C 10 Cycloalkyl, Halo(C3~C 10 )Cycloalkyl, phenyl, (Z 2 ) p2 Represents phenyl, G-4 to G-10, G-50 to G-57, or G-58 substituted by, R 1e C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C 10 Cycloalkyl, phenyl or (Z 2 ) p2 Represents phenyl substituted by, R 1f This represents a hydrogen atom or a C1-C6 alkyl group. R 1g C1-C6 alkyl, R 18 (C1-C6) alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, halo(C2-C6) alkenyl, C2-C6 alkynyl, halo(C2-C6) alkynyl, C3-C 10 Represents cycloalkyl, C1-C6 alkylamino, or di(C1-C6)alkylamino, R 1h This represents C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl. R 5 This represents a C1-C6 haloalkyl group. R 6 These are cyano, nitro, amino, hydroxy, C3-C 10 Cycloalkyl, Halo(C3~C 10)Cycloalkyl, C1-C6 alkoxy, halo(C1-C6)alkoxy, C1-C6 alkylthio, halo(C1-C6)alkylthio, C1-C6 alkylsulfinyl, halo(C1-C6)alkylsulfinyl, C1-C6 alkylsulfonyl, halo(C1-C6)alkylsulfonyl, C1-C6 alkylamino, di(C1-C6)alkylamino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxyimino, phenyl or (Z 2 ) p2 Represents phenyl substituted by, R 7 These include cyano, C1-C6 alkoxy, halo(C1-C6) alkoxy, C1-C6 alkylthio, halo(C1-C6) alkylthio, C1-C6 alkylsulfinyl, halo(C1-C6) alkylsulfinyl, C1-C6 alkylsulfonyl, halo(C1-C6) alkylsulfonyl, and C3-C 10 Cycloalkyl, phenyl, (Z 1 ) p1 Phenyl substituted by -N(R 14 )R 15 , represents G-1 to G-60 or G-61, R 8 This includes cyano, C1-C6 alkoxy, halo(C1-C6) alkoxy, phenyl or (Z 1 ) p1 Represents phenyl substituted by, R 9 This includes cyano, C1-C6 alkoxy, halo(C1-C6) alkoxy, C1-C6 alkylthio, halo(C1-C6) alkylthio, C1-C6 alkylsulfinyl, halo(C1-C6) alkylsulfinyl, C1-C6 alkylsulfonyl, halo(C1-C6) alkylsulfonyl, or C3-C 10 Represents cycloalkyl, R 10 This is cyanoacrylate, C3~C 10 Cycloalkyl, C1-C6 alkoxy, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxyimino, phenyl or (Z 3 ) p3Represents phenyl substituted by, R 11 This represents a hydrogen atom or a C1-C6 alkyl group. R 12 This represents C1-C6 alkyl, R 13 This represents cyano, R 14 This represents a hydrogen atom, a C1-C6 alkyl group, a C1-C6 alkylcarbonyl group, a C1-C6 alkoxycarbonyl group, or a C1-C6 alkylsulfonyl group. R 15 This represents a hydrogen atom or a C1-C6 alkyl group. R 16 These include cyano, C1-C6 alkoxy, halo(C1-C6) alkoxy, C1-C6 alkylthio, halo(C1-C6) alkylthio, C1-C6 alkylsulfinyl, halo(C1-C6) alkylsulfinyl, C1-C6 alkylsulfonyl, halo(C1-C6) alkylsulfonyl, and C3-C 10 Cycloalkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxyimino, phenyl or (Z 4 ) p4 Represents phenyl substituted by, R 17 This represents cyano, C1-C6 alkoxy, or C1-C6 alkoxy(C1-C6)alkoxy, R 18 This represents cyano, C1-C6 alkoxy, C1-C6 alkoxy(C1-C6) alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, or C1-C6 alkylsulfonyl. Z 1 These are halogen atoms, cyano, nitro, C1-C6 alkyl, R 17(C1-C6) alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, halo(C1-C6) alkoxy, C1-C6 alkylthio, halo(C1-C6) alkylthio, C1-C6 alkylsulfinyl, halo(C1-C6) alkylsulfinyl, C1-C6 alkylsulfonyl, halo(C1-C6) alkylsulfonyl, C1-C6 alkylamino, di(C1-C6)alkylamino or C3-C 10 When representing a cycloalkyl group and p1 represents an integer of 2, 3, 4, or 5, each Z 1 They may be the same as each other or different from each other. Z 1a This represents a hydrogen atom, a halogen atom, a cyano, a nitro, a C1-C6 alkyl, a C1-C6 haloalkyl, a C1-C6 alkoxy, a halo(C1-C6) alkoxy, a C1-C6 alkylthio, a C1-C6 alkylsulfinyl, or a C1-C6 alkylsulfonyl. Z 2 When p2 represents a halogen atom, cyano, C1-C6 alkyl, C1-C6 haloalkyl, or C1-C6 alkoxy, and p2 represents an integer of 2, 3, 4, or 5, each Z 2 They may be the same as each other or different from each other. Z 3 When p3 represents a halogen atom, cyano, C1-C6 alkyl, C1-C6 haloalkyl, or C1-C6 alkoxy, and p3 represents an integer of 2, 3, 4, or 5, each Z 3 They may be the same as each other or different from each other. Z 4 When p4 represents a halogen atom, cyano, C1-C6 alkyl, C1-C6 haloalkyl, or C1-C6 alkoxy, and p4 represents an integer of 2, 3, 4, or 5, each Z 4 They may be the same as each other or different from each other. p1 represents an integer of 1, 2, 3, 4, or 5. p2 represents an integer of 1, 2, 3, 4, or 5. p3 represents an integer of 1, 2, 3, 4, or 5. p4 represents an integer of 1, 2, 3, 4, or 5. q3 represents an integer of 0, 1, 2, or 3. q4 represents an integer of 0, 1, 2, 3, or 4. q5 represents an integer of 0, 1, 2, 3, 4, or 5. q6 represents an integer of 0, 1, 2, 3, 4, 5, or 6. g2 represents an integer of 0, 1, or 2. g3 represents an integer of 0, 1, 2, or 3. g4 represents an integer of 0, 1, 2, 3, or 4. r represents an integer of 0, 1, or 2. [2] W represents an oxygen atom. X 1 , X 2 and X 3 Each of these independently represents a hydrogen atom, a halogen atom, or a C1-C6 haloalkyl group. Y 1 This represents a hydrogen atom, a halogen atom, a nitro, a C1-C6 alkyl, or a C1-C6 haloalkyl. Or, Y 1 and Y 2 These elements combine to form a 6-membered ring -CH=CH-CH=CH-, R 1 is -C(O)R 1a , -C(O)OR 2a -C(O)SR 2a ,-C(O)N(R 1c )R 1b ,-C(S)N(R 1c )R 1b -S(O)2R 1a -S(O)2N(R 1c )R 1b ,-C(O)C(O)R 1a Or it represents -CHO, R 3 is a hydrogen atom, C1-C6 alkyl, R 6 (C1-C6) alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C 10 Cycloalkyl, C1-C6 alkoxy, -C(O)R 1d , -C(O)OR 1d ,-C(O)N(R1f )R 1e Or -S(O)2R 1d This represents, R 4 This represents a hydrogen atom, a C1-C6 alkyl group, or a C2-C6 alkynyl group. R A C1-C6 alkyl, R 16 Represents (C1-C6) alkyl, C2-C6 alkenyl, or C2-C6 alkynyl substituted by R 1a C1~C 10 Alkyl, R 7 (C1-C6) alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, halo(C2-C6) alkenyl, C2-C6 alkynyl, C3-C 10 Cycloalkyl, Halo(C3~C 10 ) Cycloalkyl, R 13 C3~C substituted by 10 Cycloalkyl, phenyl, (Z 1 ) p1 Represents phenyl, D-2, D-3, D-14, D-23, D-30, D-37, D-58, G-1, G-2, G-4~G-10, G-12~G-20, G-22~G-27, G-39, G-50~G-57 or G-58 substituted by R 2a C1-C6 alkyl, R 7 Represents (C1-C6) alkyl, C1-C6 haloalkyl, or C2-C6 alkenyl substituted by R 1b is a hydrogen atom, C1-C6 alkyl, R 8 (C1-C6) alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C 10 Cycloalkyl, C1-C6 alkoxy, C1-C6 alkoxycarbonyl, phenyl or (Z 1 ) p1 Represents phenyl substituted by, R 1d C1-C6 alkyl, R 9 (C1-C6) alkyl, C2-C6 alkenyl, C3-C 10Cycloalkyl, Halo(C3~C 10 )Cycloalkyl, phenyl, (Z 2 ) p2 Represents phenyl, G-5, or G-51 substituted by, R 1e C1-C6 alkyl, C2-C6 alkenyl, C3-C 10 Cycloalkyl or (Z 2 ) p2 Represents phenyl substituted by, R 6 This is cyanoacrylate, C3~C 10 Represents cycloalkyl, C1-C6 alkoxy, or phenyl, R 7 These are C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfonyl, and C3-C 10 Cycloalkyl, phenyl, -N(R 14 )R 15 , represents G-11, G-21 or G-30, R 8 This represents a C1-C6 alkoxy or phenyl molecule. R 9 This represents C1-C6 alkoxy, R 10 C3~C 10 Cycloalkyl, C1-C6 alkoxy, C1-C6 alkoxyimino, phenyl or (Z 3 ) p3 Represents phenyl substituted by, R 14 This represents C1-C6 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, or C1-C6 alkylsulfonyl. R 16 C3~C 10 Cycloalkyl, C1-C6 alkoxyimino, phenyl or (Z 4 ) p4 Represents phenyl substituted by, R 17 This represents a C1-C6 alkoxy (C1-C6) alkoxy, Z 1 These are halogen atoms, cyano, nitro, C1-C6 alkyl, R 17When p1 represents an integer of 2, each Z 1 They may be the same as each other or different from each other. Z 1a This represents a hydrogen atom, Z 2 When a halogen atom or C1-C6 alkyl group is represented and p2 is an integer of 2, each Z 2 They may be the same as each other or different from each other. Z 3 This represents a halogen atom, Z 4 This represents a halogen atom, p1 represents an integer of 1 or 2, p2 represents an integer of 1 or 2. p3 represents an integer of 1, p4 represents the integer 1, q3 represents an integer of 0, q4 represents an integer of 0. q5 represents an integer of 0, g3 represents an integer of 0 or 1. g4 represents an integer of 0, 1, or 2. r represents 0, and is an isoxazoline-substituted benzamide compound or a salt thereof as described in [1] above. [3] A pest control agent containing one or more isoxazoline-substituted benzamide compounds and salts thereof selected from any one of the above items [1] to [2] as an active ingredient. [4] A pesticide containing one or more isoxazoline-substituted benzamide compounds and their salts selected from any one of the above items [1] to [2] as an active ingredient. [5] A control agent for internal or external parasites of mammals or birds, containing one or more isoxazoline-substituted benzamide compounds and salts thereof selected from any one of the above items [1] to [2] as an active ingredient. [6] The control agent according to [5] above, wherein the external parasite is a flea or a tick. [7] An insecticide or acaricide containing one or more isoxazoline-substituted benzamide compounds and salts thereof selected from any one of the above items [1] to [2] as an active ingredient. [8] A seed treatment agent containing one or more isoxazoline-substituted benzamide compounds and salts thereof selected from any one of the above items [1] to [2] as an active ingredient. [9] The seed treatment agent described in [8] above, wherein the seed treatment is performed by immersion treatment.

[10] A soil treatment agent containing one or more isoxazoline-substituted benzamide compounds and salts thereof selected from any one of the above items [1] to [2] as an active ingredient.

[11] The soil treatment agent described in

[10] above, wherein the soil treatment is carried out by soil drenching. [Examples]

[0331] The present invention will be further described below by illustrating examples of the synthesis and testing of the compounds of the present invention, but the present invention is not limited thereto.

[0332] The intermediate-pressure preparative liquid chromatography described in the synthesis example was performed using a YAMAZEN Corporation intermediate-pressure preparative apparatus; YFLC-Wprep (flow rate 18 ml / min, silica gel column 40 μm).

[0333] Furthermore, a Waters Prep15 SFC system was used for supercritical fluid chromatography preparative chromatography.

[0334] Furthermore, the proton nuclear magnetic resonance spectra described below (hereinafter, 1The chemical shift values ​​of ¹H-NMR (referred to as ¹H-NMR) were measured using Me₄Si (tetramethylsilane) as the reference material, in deuterated chloroform or deuterated dimethyl sulfoxide solvent, at 300 MHz (model: JNM-ECX300 or JNM-ECP300, JEOL) or 400 MHz (model: JNM-ECZ400S, JEOL). 1 The symbols used in the chemical shift values ​​of H-NMR represent the following: s: singlet, d: doublet, dd: double doublet, t: triplet, q: quartet, m: multiplet, brs: broad singlet The following high-performance liquid chromatography (HPLC) or supercritical fluid chromatography (SFC) measurement conditions were used to determine the optical purity. Condition A HPLC system: Shimadzu Corporation; 20A system Flow rate: 0.8 ml / min Oven temperature: 40℃ Mobile phase: n-hexane:2-propanol = 4:1 (volume ratio) Column: Daicel Chiralpak AD-H (inner diameter 4.6 mm, length 250 mm, particle size 5 μm) Measurement wavelength: 254nm Condition B HPLC system: Shimadzu Corporation; 20A system Flow rate: 0.8 ml / min Oven temperature: 40℃ Mobile phase: n-hexane:2-propanol:diethylamine = 80:20:0.1 (volume ratio) Column: Daicel Chiralpak AD-H (inner diameter 4.6 mm, length 250 mm, particle size 5 μm) Measurement wavelength: 254nm Condition C HPLC system: Shimadzu Corporation; 20A system Flow rate: 0.8 ml / min Oven temperature: 40℃ Mobile phase: n-hexane:2-propanol = 3:2 (volume ratio) Column: Daicel Chiralpak AD-H (inner diameter 4.6 mm, length 250 mm, particle size 5 μm) Measurement wavelength: 254nm Condition D HPLC system: Shimadzu Corporation; 20A system Flow rate: 2.0 ml / min Oven temperature: 40℃ Mobile phase: n-hexane:2-propanol = 4:1 (volume ratio) Column: Daicel Chiralpak AD-H (inner diameter 4.6 mm, length 250 mm, particle size 5 μm) Measurement wavelength: 254nm Condition E HPLC system: Shimadzu Corporation; 20A system Flow rate: 2.0 ml / min Oven temperature: 40℃ Mobile phase: n-hexane:2-propanol = 2:1 (volume ratio) Column: Daicel Chiralpak IB (inner diameter 4.6 mm, length 150 mm, particle size 5 μm) Measurement wavelength: 254nm Condition F SFC equipment: Waters; ACQUITY UPC2 (UPC Square) system Flow rate: 2.0 ml / min Oven temperature: 40℃ Mobile phase: Carbon dioxide: Methanol = 3:2 (volume ratio) Column: Daicel Chiralpak IA-3 (inner diameter 4.6 mm, length 150 mm, particle size 3 μm) Measurement wavelength: PDA (210-400nm) Condition G SFC equipment: Waters; ACQUITY UPC2 (UPC Square) system Flow rate: 2.0 ml / min Oven temperature: 40℃ Mobile phase: Carbon dioxide: Methanol = 3:1 (volume ratio) Column: Daicel Chiralpak IA-3 (inner diameter 4.6 mm, length 150 mm, particle size 3 μm) Measurement wavelength: PDA (210-400nm) Condition H SFC equipment: Waters; ACQUITY UPC2 (UPC Square) system Flow rate: 2.0 ml / min Oven temperature: 40℃ Mobile phase: Carbon dioxide: Methanol = 3:1 (volume ratio) Column: Daicel Chiralpak IB-3 (inner diameter 4.6 mm, length 150 mm, particle size 3 μm) Measurement wavelength: PDA (210-400nm) Condition I SFC equipment: Waters; ACQUITY UPC2 (UPC Square) system Flow rate: 2.0 ml / min Oven temperature: 40℃ Mobile phase: Carbon dioxide: Methanol = 55:45 (volume ratio) Column: Daicel Chiralpak IJ (inner diameter 4.6 mm, length 150 mm, particle size 5 μm) Measurement wavelength: PDA (210-400nm) Condition J SFC equipment: Waters; ACQUITY UPC2 (UPC Square) system Flow rate: 2.0 ml / min Oven temperature: 40℃ Mobile phase: Carbon dioxide: Methanol = 65:35 (volume ratio) Column: Daicel Chiralpak IJ (inner diameter 4.6 mm, length 150 mm, particle size 5 μm) Measurement wavelength: PDA (210-400nm) Condition K SFC equipment: Waters; ACQUITY UPC2 (UPC Square) system Flow rate: 2.0 ml / min Oven temperature: 40℃ Mobile phase: Carbon dioxide: Methanol = 65:35 (volume ratio) Column: Daicel Chiralpak IG (inner diameter 4.6 mm, length 150 mm, particle size 5 μm) Measurement wavelength: PDA (210-400nm) Condition L SFC equipment: Waters; ACQUITY UPC2 (UPC Square) system Flow rate: 2.0 ml / min Oven temperature: 40℃ Mobile phase: Carbon dioxide: Methanol = 1:1 (volume ratio) Column: Daicel Chiralpak IJ (inner diameter 4.6 mm, length 150 mm, particle size 5 μm) Measurement wavelength: PDA (210-400nm) Condition M SFC equipment: Waters; ACQUITY UPC2 (UPC Square) system Flow rate: 2.0 ml / min Oven temperature: 40℃ Mobile phase: Carbon dioxide: Methanol = 4:1 (volume ratio) Column: Daicel Chiralpak IJ (inner diameter 4.6 mm, length 150 mm, particle size 5 μm) Measurement wavelength: PDA (210-400nm) Condition N SFC equipment: Waters; ACQUITY UPC2 (UPC Square) system Flow rate: 2.0 ml / min Oven temperature: 40℃ Mobile phase: Carbon dioxide: Methanol = 7:3 (volume ratio) Column: Daicel Chiralpak IA-3 (inner diameter 4.6 mm, length 150 mm, particle size 3 μm) Measurement wavelength: PDA (210-400nm) Condition O HPLC system: Shimadzu Corporation; 20A system Flow rate: 2.0 ml / min Oven temperature: 40℃ Mobile phase: n-hexane:2-propanol:trifluoroacetic acid = 80:20:0.1 (volume ratio) Column: Daicel Chiralpak AD-H (inner diameter 4.6 mm, length 250 mm, particle size 5 μm) Measurement wavelength: 254nm Condition P HPLC system: Shimadzu Corporation; 20A system Flow rate: 2.0 ml / min Oven temperature: 40℃ Mobile phase: n-hexane:2-propanol = 9:1 (volume ratio) Column: Daicel Chiralpak AD-H (inner diameter 4.6 mm, length 250 mm, particle size 5 μm) Measurement wavelength: 254nm Condition Q SFC equipment: Waters; ACQUITY UPC2 (UPC Square) system Flow rate: 2.0 ml / min Oven temperature: 40℃ Mobile phase: Carbon dioxide: Methanol = 3:2 (volume ratio) Column: Daicel Chiralpak IJ (inner diameter 4.6 mm, length 150 mm, particle size 5 μm) Measurement wavelength: PDA (210-400nm) Condition R SFC equipment: Waters; ACQUITY UPC2 (UPC Square) system Flow rate: 2.0 ml / min Oven temperature: 40℃ Mobile phase: Carbon dioxide: Methanol = 3:1 (volume ratio) Column: Daicel Chiralpak IJ (inner diameter 4.6 mm, length 150 mm, particle size 5 μm) Measurement wavelength: PDA (210-400nm) Condition S SFC equipment: Waters; ACQUITY UPC2 (UPC Square) system Flow rate: 2.0 ml / min Oven temperature: 40℃ Mobile phase: Carbon dioxide: Methanol = 85:15 (volume ratio) Column: Daicel Chiralpak IJ (inner diameter 4.6 mm, length 150 mm, particle size 5 μm) Measurement wavelength: PDA (210-400nm) Condition T HPLC system: Shimadzu Corporation; 20A system Flow rate: 0.8 ml / min Oven temperature: 40℃ Mobile phase: n-hexane:2-propanol = 9:1 (volume ratio) Column: Daicel Chiralpak AD-H (inner diameter 4.6 mm, length 250 mm, particle size 5 μm) Measurement wavelength: 254nm Condition U HPLC system: Shimadzu Corporation; 20A system Flow rate: 2.0 ml / min Oven temperature: 40℃ Mobile phase: n-hexane:2-propanol = 20:1 (volume ratio) Column: Daicel Chiralpak AD-H (inner diameter 4.6 mm, length 250 mm, particle size 5 μm) Measurement wavelength: 254nm Condition V HPLC system: Shimadzu Corporation; 20A system Flow rate: 2.0 ml / min Oven temperature: 40℃ Mobile phase: n-hexane:2-propanol = 4:1 (volume ratio) Column: Daicel Chiralpak IJ-3 (inner diameter 4.6 mm, length 150 mm, particle size 3 μm) Measurement wavelength: 254nm Condition W HPLC system: Shimadzu Corporation; 20A system Flow rate: 2.0 ml / min Oven temperature: 40℃ Mobile phase: n-hexane:2-propanol:diethylamine = 90:10:0.1 (volume ratio) Column: Daicel Chiralpak AD-H (inner diameter 4.6 mm, length 250 mm, particle size 5 μm) Measurement wavelength: 254nm Of the peaks indicating optical isomers detected under conditions A to W, the one with the larger percentage area ratio was designated as the "main peak," and the one with the smaller percentage area ratio was designated as the "minor peak." A JASCO P-2200 optical spectrometer was used to measure optical rotation.

[0335] Synthesis Example 1: Synthesis of (S)-N-(amino(tert-butoxycarbonylamino)methylene)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide [Inventive Compound No. 1-002(S)] To a 6 ml solution of N,N-dimethylformamide containing 500 mg of (S)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzoic acid [optical purity: 98%ee [condition: O, retention time: 1.94 min (main peak), 6.23 min (minor peak)]] synthesized according to Example 4-3-14 of International Publication No. 2009 / 001942, and then according to Examples 1, 3, and 4 of Japanese Patent Publication No. 2011-051977, 298 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 228 mg of 1-(tert-butoxycarbonyl)guanidine, and 30 mg of 1-hydroxy-7-azabenzotriazole, the mixture was sequentially stirred overnight at room temperature. After the reaction was complete, 5 ml of water was added and the mixture was extracted with 5 ml of ethyl acetate. The resulting organic layer was dried over saturated brine and anhydrous sodium sulfate, and the solvent was removed under reduced pressure. 10 ml of hexane was added to the residue, and the solvent was removed under reduced pressure to obtain 688 mg of the target product as a white solid. Melting point: 86-88°C Optical purity: 98%ee Condition A; Retention time 6.27 minutes (main peak), 9.78 minutes (minor peak) 1 H-NMR (CDCl3, Me4Si, 300MHz) δ: 8.63 (brs, 2H), 7.85-7.80 (m, 1H), 7.55-7.50 (m, 4H), 7.45-7.20 (m, 1H), 4.09 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 2.57 (s, 3H), 1.50 (s, 9H). Synthesis Example 2: Synthesis of (S)-N-(amino(methylsulfonamide)methylene)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide [Inventive Compound No. 1-004(S)] Step 1: Synthesis of (S)-N-(diaminomethylene)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide hydrochloride 1.68 g of (S)-N-(amino(tert-butoxycarbonylamino)methylene)4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide, synthesized by the same method as in Synthesis Example 1, was added to 30 ml of a 4 mol / l hydrogen chloride solution of 1,4-dioxane, and the mixture was stirred at 60°C for 1.5 hours. After the reaction was complete, the solvent was removed under reduced pressure to obtain 1.68 g of the target product as a crude white solid. 1 Based on 1H-NMR, the target substance was estimated to be a monohydrochloride salt. Melting point: 107-109°C Optical purity: 98%ee Condition B; Retention time 5.31 minutes (main peak), 8.32 minutes (minor peak) 1 H-NMR (CDCl3, Me4Si, 300MHz) δ: 11.48 (s, 1H), 8.72 (s, 2H), 8.56 (s, 2H), 7.84 (d, J=8.1 Hz, 1H), 7.60-7.40 (m, 5H), 4.08 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4Hz, 1H), 2.55 (s, 3H). Step 2: Synthesis of (S)-N-(amino(methylsulfonamide)methylene)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide [Inventive Compound No. 1-004(S)] To a 5 ml solution of dichloromethane containing 504 mg of (S)-N-(diaminomethylene)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide hydrochloride, 0.511 ml of triethylamine, 319 mg of methanesulfonic anhydride, and 20 mg of 4-dimethylaminopyridine were sequentially added, and the mixture was stirred overnight at room temperature. After the reaction was complete, 5 ml of water was added, and the mixture was extracted with 5 ml of dichloromethane. The resulting organic layer was dried with saturated brine, then with anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel chromatography [eluent: ethyl acetate:hexane = 10:90 to 50:50 gradient (volume ratio, the same applies hereafter)], and 82 mg of the target product was obtained as a white solid. Melting point: 164~166℃ Optical purity: 97%ee Condition A; Retention time 11.29 minutes (main peak), 14.94 minutes (minor peak) 1 H-NMR (CDCl3, Me4Si, 300MHz) δ: 9.12 (brs, 1H), 8.98 (s, 1H), 7.65-7.55 (m, 3H), 7.55-7.45 (m, 2H), 7.45-7.30 (m, 2H), 4.09 (d, J=17.4 Hz, 1H), 3.72 (d, J=17.4 Hz, 1H), 2.99 (s, 3H), 2.53 (s, 3H). Synthesis Example 3: Synthesis of (S)-N-(amino(N-methylmethylsulfonamide)methylene)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide [Invention Compound No. 1-088(S)] and (S)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-N,2-dimethyl-N-(N'-(methylsulfonyl)carbamimidoyl)benzamide [Invention Compound No. 8-002(S)] To 3 ml of N,N-dimethylformamide solution containing 285 mg of (S)-N-(amino(methylsulfonamide)methylene)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide, synthesized by the same method as in Synthesis Example 2, 80 mg of potassium bicarbonate and 0.05 ml of iodomethane were sequentially added, and the mixture was stirred at room temperature for 20 hours. To the reaction mixture, 27 mg of potassium bicarbonate and 0.017 ml of iodomethane were added, and the mixture was stirred for a further 24 hours. After the reaction was complete, 5 ml of water was added, and the mixture was extracted with 5 ml of ethyl acetate. The resulting organic layer was dried with saturated brine, then with anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel chromatography (using a gradient of ethyl acetate:hexane = 10:90 to 50:50 as the eluent) to obtain 70 mg of compound No. 1-088(S) and 160 mg of compound No. 8-002(S) as white amorphous materials, respectively. Compound No. 1-088(S) of the present invention Optical purity: 98%ee Condition A; Retention time 11.11 minutes (main peak), 24.29 minutes (minor peak) 1 H-NMR (CDCl3, Me4Si, 300MHz) δ: 8.06 (d, J=8.1 Hz, 1H), 7.60-7.40 (m, 6H), 4.09 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 3.47 (s, 3H), 3.18 (s, 3H), 2.64 (s, 3H). Compound No. 8-002(S) of the present invention Optical purity: 98%ee Condition A; Retention time 12.96 minutes (main peak), 15.35 minutes (minor peak) 1H-NMR (CDCl3, Me4Si, 300MHz) δ: 9.65 (brs, 1H), 7.93 (brs, 1H), 7.60-7.45 (m, 4H), 7.44 (dd, J=1.8, 1.8 Hz, 1H), 7.28 (d, J=8.4 Hz, 1H), 4.08 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 3.10 (s, 3H), 3.05 (s, 3H), 2.37 (s, 3H). Synthesis Example 4: Synthesis of N-(amino(3-methylthioureido)methylene)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide [Inventive Compound No. 1-009] Synthesis Example 2: 120 mg of N-(diaminomethylene)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide hydrochloride, synthesized by the same method as in Step 1, was dissolved in 3 ml of 1,2-dichloroethane. 0.135 ml of triethylamine and 32 mg of methyl isothiocyanate were added sequentially, and the mixture was stirred under reflux temperature for 5 hours. After the reaction was complete, 5 ml of water was added, and the mixture was extracted with 5 ml of dichloromethane. The resulting organic layer was dried with saturated brine, then with anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel chromatography (eluent: ethyl acetate:hexane = 10:90 to 50:50 gradient) to obtain 53 mg of the target product as a white solid. Melting point: 93-95°C 1 H-NMR (CDCl3, Me4Si, 300MHz) δ: 7.80-7.40 (m, 6H), 4.09 (d, J=17.4 Hz, 1H), 3.71 (d, J=17.4 Hz, 1H), 3.09 and 2.95 (d, J=5.1 Hz, 3H), 2.57 and 2.55 (s, 3H). Synthesis Example 5: Synthesis of N-((methoxycarbonylamino)(methylamino)methylene)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide [Inventive Compound No. 1-010] Step 1: Synthesis of N-((methoxycarbonylamino)(methylthio)methylene)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide To a 20 ml solution of 872 mg of methyl(amino(methylthio)methylene)carbamate in dichloromethane, 1.3 ml of pyridine was added. Under ice cooling, 10 ml of a dichloromethane solution of 2.3 g of 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzoyl chloride was added, and the mixture was stirred overnight at room temperature. After the reaction was complete, 15 ml of water was added, and the mixture was extracted with 10 ml of dichloromethane. The resulting organic layer was dried with saturated brine, then with anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel chromatography (eluent: ethyl acetate:hexane = 5:95 to 30:70 gradient) to obtain 2.63 g of the target product as a white amorphous material. 1 H-NMR (CDCl3, Me4Si, 300MHz) δ: 8.60-7.40 (m, 6H), 4.15-4.05 (m, 1H), 3.84 and 3.80 (s, 3H), 3.70 (d, J=17.4 Hz, 1H), 2.66 and 2.59 (s, 3H), 2.53 and 2.48 (s, 3H). Step 2: Synthesis of N-((methoxycarbonylamino)(methylamino)methylene)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide [Inventive Compound No. 1-010] To a 2 ml solution of acetonitrile containing 120 mg of N-((methoxycarbonylamino)(methylthio)methylene)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide, 0.164 ml of tetrahydrofuran solution of 2 mol / l methylamine was added and the mixture was stirred at room temperature for 1.5 hours. After the reaction was complete, the solvent was removed under reduced pressure. The resulting residue was purified by silica gel chromatography (eluent: ethyl acetate:hexane = 10:90 to 30:70 gradient) to obtain 131 mg of the target product as a white amorphous material. 1 H-NMR (CDCl3, Me4Si, 300MHz) δ: 9.10-8.40 (m, 1H), 8.10-7.40 (m, 6H), 4.15-4.05 (m, 1H), 3.82 and 3.72 (s, 3H), 3.70 (d, J=17.4 Hz, 1H), 3.10-3.05 (m, 3H), 2.64 and 2.56 (s, 3H). Synthesis Example 6: Synthesis of (S)-N-(amino(3,3-dimethylureido)methylene)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide [Inventive Compound No. 1-007(S)] Synthesis Example 2: 150 mg of (S)-N-(diaminomethylene)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide hydrochloride, synthesized by the same method as in Step 1, was dissolved in 2 ml of pyridine. 0.111 ml of dimethylcarbamoyl chloride was added, and the mixture was stirred at 100°C for 2.5 hours. After the reaction was complete, 3 ml of 1 mol / l hydrochloric acid was added, and the mixture was extracted with 5 ml of ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel chromatography (eluent: ethyl acetate:hexane = 10:90 to 50:50 gradient) to obtain 75 mg of the target product as a colorless oily substance. Optical purity: 98%ee Condition A; Retention time 8.53 minutes (main peak), 9.79 minutes (minor peak) 1 H-NMR (CDCl3, Me4Si, 300MHz) δ: 8.11 (d, J=8.1 Hz, 1H), 7.70-7.50 (m, 4H), 7.43 (dd, J=1.8, 1.8 Hz, 1H), 4.09 (d, J=17.4 Hz, 1H), 3.71 (d, J=17.4 Hz 1H), 3.32 (s, 3H), 3.04 (s, 3H), 2.57 (s, 3H). Synthesis Example 7: Synthesis of (S)-4-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-N-(N'-(dimethylcarbamoyl)carbamimidoyl)-N,2-dimethylbenzamide [Inventive Compound No. 8-003(S)] To 4 ml of N,N-dimethylformamide solution of 290 mg of (S)-N-(amino(3,3-dimethylureido)methylene)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide, synthesized by the same method as in Synthesis Example 6, 227 mg of potassium carbonate and 0.102 ml of iodomethane were sequentially added, and the mixture was stirred at 50°C for 2 hours. After the reaction was complete, 5 ml of water was added, and the mixture was extracted with 5 ml of ethyl acetate. The resulting organic layer was dried with saturated brine, then with anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel chromatography (eluent: ethyl acetate:hexane = 10:90 to 50:50 gradient) to obtain 105 mg of the present invention compound No. 8-003(S) as a colorless oily substance. Optical purity: 99%ee Condition A; Retention time 10.98 minutes (main peak), 13.28 minutes (minor peak) 1H-NMR (CDCl3, Me4Si, 300MHz) δ: 9.82 (brs, 1H), 9.13 (brs, 1H), 7.60-7.50 (m, 4H), 7.43 (dd, J=1.8, 1.8 Hz, 1H), 7.28 (d, J=7.8 Hz, 1H), 4.09 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 3.12 (s, 3H), 3.07 (s, 3H), 2.97 (s, 3H), 2.37 (s, 3H). Synthesis Example 8: Synthesis of (S)-4-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-N-(N-ethyl-N'-(methylsulfonyl)carbamimidoyl)-N,2-dimethylbenzamide [Inventive Compound No. 8-013(S)] Step 1: Synthesis of methyl(S)-4-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzoyl)-N-methyl-N'-(methylsulfonyl)carbamimidothioate 6 ml of tetrahydrofuran solution of methyl-N'-methyl-N-(methylsulfonyl)carbamimidothioate was mixed with 201 mg of tert-butoxypotassium under ice cooling and stirred at the same temperature for 1 hour. Then, 3 ml of tetrahydrofuran solution of 522 mg of (S)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzoyl chloride was added to the reaction mixture and stirred at 70°C for another 1 hour. After the reaction was complete, 5 ml of saturated ammonium chloride aqueous solution was added at room temperature and extracted with 10 ml of ethyl acetate. The resulting organic layer was dried with saturated brine and then with anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel chromatography (eluent: ethyl acetate:hexane = 10:90 to 50:50 gradient) to obtain 409 mg of the target product as a colorless oily substance. Optical purity: 98%ee Condition A; Retention time 23.28 minutes (main peak), 49.42 minutes (minor peak) 1 H-NMR (CDCl3, Me4Si, 300MHz) δ: 7.55-7.40 (m, 6H), 4.08 (d, J=17.4 Hz, 1H), 3.69 (d, J=17.4 Hz, 1H), 3.31 (s, 3H), 3.07 (s, 3H), 2.45 (s, 3H), 2.39 (s, 3H). Step 2: Synthesis of (S)-4-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-N-(N-ethyl-N'-(methylsulfonyl)carbamimidoyl)-N,2-dimethylbenzamide [Inventive Compound No. 8-013(S)] 2 ml of N,N-dimethylformamide solution of methyl(S)-4-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzoyl)-N-methyl-N'-(methylsulfonyl)carbamimidothioate was added to 0.25 ml of tetrahydrofuran solution of 2 mol / l ethylamine and stirred at room temperature for 1 hour. After the reaction was complete, 3 ml of water was added and the mixture was extracted with 5 ml of ethyl acetate. The resulting organic layer was dried with saturated brine, then with anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel chromatography (eluent: ethyl acetate:hexane = 10:90 to 60:40 gradient) to obtain 87 mg of the target product as a colorless oily substance. Optical purity: 99%ee Condition A; Retention time 10.60 minutes (main peak), 17.68 minutes (minor peak) 1 H-NMR (CDCl3, Me4Si, 300MHz) δ: 7.60-7.35 (m, 6H), 7.24 (brs, 1H), 4.08 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 3.45-3.35 (m, 2H), 3.22 (s, 3H), 2.70-2.40 (m, 6H), 1.35-1.15 (m, 3H). Synthesis Example 9: Synthesis of N-(amino(methoxycarbonylamino)methylene)-4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide [Inventive Compound No. 4-002] Synthesis Example 2: To 2 ml of a 1,2-dichloroethane solution containing 135 mg of N-(diaminomethylene)-4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide hydrochloride, synthesized in the same manner as in Step 1, 0.183 ml of triethylamine and 0.031 ml of methyl chloroformate were sequentially added, and the mixture was stirred at room temperature for 1.5 hours. After the reaction was complete, 3 ml of water was added, and the mixture was extracted with 2 ml of dichloromethane. The resulting organic layer was dried with saturated brine, then with anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel chromatography (eluent: ethyl acetate:hexane = 10:90 to 60:40 gradient) to obtain 69 mg of the target product as a white solid. Melting point: 100~102℃ 1 H-NMR (CDCl3, Me4Si, 300MHz) δ: 8.99 (brs, 1H), 7.65-7.55 (m, 3H), 7.50-7.45 (m, 2H), 4.09 (d, J=17.4 Hz 1H), 3.69 (d, J=17.4 Hz, 1H), 3.65-3.55 (m, 3H), 2.46 (s, 3H). Synthesis Example 10: Synthesis of (S)-N-(amino(methoxycarbonylamino)methylene)-4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide [Invention Compound No. 4-002(S)] and (R)-N-(amino(methoxycarbonylamino)methylene)-4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide [Invention Compound No. 4-002(R)] 266 mg of N-(amino(methoxycarbonylamino)methylene)-4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide, synthesized in Synthesis Example 9, was subjected to optical isomer separation using supercritical fluid chromatography. The separation conditions are shown below. Flow rate: 15 ml / min Oven temperature: 40°C Mobile phase: Carbon dioxide: Methanol = 3:2 (volume ratio) Column: Daicel Chiralpak IA (20mm inner diameter, 250mm length, 5μm particle size) By concentrating the fraction with a retention time of 12.71 minutes under reduced pressure, 90 mg of compound No. 4-002(S) of the present invention was obtained as a colorless oily substance, and by concentrating the fraction with a retention time of 17.53 minutes under reduced pressure, 88 mg of compound No. 4-002(R) of the present invention was obtained as a colorless oily substance. Compound No. 4-002(S) of the present invention Optical purity:>99%ee Condition F; Retention time 2.56 minutes (main peak), 3.59 minutes (minor peak) Compound No. 4-002(R) of the present invention Optical purity:>99%ee Condition F; Retention time 2.56 minutes (minor peak), 3.59 minutes (main peak) Synthesis Example 11: Synthesis of (S)-N-(amino(3,3-dimethylureido)methylene)-2-chloro-4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)benzamide [Inventive Compound No. 4-033(S)] Step 1: Synthesis of 2-chloro-4-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluoro-3-hydroxybutanoyl)benzoic acid To a solution of 6.81 g of 1-(3,5-dichloro-4-fluorophenyl)-2,2,2-trifluoroethane-1-one in 52 ml of toluene, 5.18 g of 4-acetyl-2-chlorobenzoic acid and 4 ml of diethylamine were sequentially added, and the mixture was stirred at 60°C for 1 hour. After the reaction was complete, 50 ml of hexane was added at room temperature, and the resulting solid was washed with 20 ml of hexane. The solid was dissolved in 20 ml of ethyl acetate, 5 ml of 12 mol / l hydrochloric acid was added, and the mixture was extracted with 5 ml of ethyl acetate. The resulting organic layer was dried with saturated brine, then with anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain 10.1 g of the target product as a brown dendritic substance. 1 H-NMR (CDCl3, Me4Si, 300MHz) δ: 8.11 (d, J=8.1 Hz, 1H), 8.01 (d, J=1.5 Hz, 1H), 7.88 (dd, J=1.5, 8.1 Hz, 1H), 7.55 (d, J=6.3 Hz, 2H), 5.40 (brs, 1H), 3.82 (d, J=17.7 Hz, 1H), 3.72 (d, J=17.7 Hz, 1H). Step 2: Synthesis of 2-chloro-4-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluoro-2-butenoyl)benzoic acid To a solution of 10.1 g of 2-chloro-4-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluoro-3-hydroxybutanoyl)benzoic acid in 44 ml of toluene, 12 ml of triethylamine, 3.3 ml of acetic anhydride, and 268 mg of 4-dimethylaminopyridine were sequentially added, and the mixture was stirred at 80°C for 3 hours. After the reaction was complete, 10 ml of 12 mol / l hydrochloric acid was added at room temperature, and the mixture was extracted with 20 ml of ethyl acetate. The resulting organic layer was dried with saturated brine, then with anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain 9.73 g of the target product as a brown solid. Melting point: 131-133°C 1H-NMR (CDCl3, Me4Si, 300MHz) δ: 8.05 (d, J=7.8 Hz, 1H), 7.90 (d, J=1.5 Hz, 1H), 7.77 (dd, J=1.8, 7.8 Hz, 1H), 7.40-7.35 (m, 1H), 7.25 (d, J=6.6 Hz, 2H). Step 3: Synthesis of N-(amino(tert-butoxycarbonylamino)methylene)-2-chloro-4-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluoro-2-butenoyl)benzamide To a solution of 876 mg of 2-chloro-4-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluoro-2-butenoyl)benzoic acid in 6 ml of N,N-dimethylformamide, 570 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 379 mg of 1-(tert-butoxycarbonyl)guanidine, and 14 mg of 1-hydroxy-7-azabenzotriazole were sequentially added, and the mixture was stirred overnight at room temperature. After the reaction was complete, 5 ml of water was added, and the mixture was extracted with 5 ml of ethyl acetate. The resulting organic layer was dried over saturated brine and anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel chromatography (eluent: ethyl acetate:hexane = 10:90 to 60:40 gradient) to obtain 951 mg of the target product as a brown solid. Melting point: 78-80°C 1 H-NMR (CDCl3, Me4Si, 300MHz) δ: 9.17 (brs, 2H), 8.67 (brs, 1H), 7.85-7.70 (m, 3H), 7.45-7.35 (m, 1H), 7.25 (d, J=6.3 Hz, 2H), 1.48 (s, 9H). Step 4: Synthesis of 2-chloro-N-(diaminomethylene)-4-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluoro-2-butenoyl)benzamide hydrochloride 951 mg of N-(amino(tert-butoxycarbonylamino)methylene)-2-chloro-4-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluoro-2-butenoyl)benzamide was added to 5 ml of 1,4-dioxane solution in 4 mol / l hydrogen chloride and stirred at 70°C for 4 hours. After the reaction was complete, the solvent was removed under reduced pressure to obtain 827 mg of the target product as a white solid. 1 Based on 1H-NMR, the target substance was estimated to be a monohydrochloride salt. Melting point: 86-88°C 1 H-NMR (CDCl3, Me4Si, 300MHz) δ: 11.76 (s, 1H), 8.70-8.55 (m, 4H), 7.95-7.75 (m, 3H), 7.45-7.40 (m, 1H), 7.25 (d, J=6.6 Hz, 2H). Step 5: Synthesis of N-(amino(3,3-dimethylureido)methylene)-2-chloro-4-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluoro-2-butenoyl)benzamide To a solution of 393 mg of 2-chloro-N-(diaminomethylene)-4-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluoro-2-butenoyl)benzamide hydrochloride in 3 ml of 1,4-dioxane, 0.667 ml of diisopropylethylamine and 0.144 ml of dimethylcarbamoyl chloride were added and the mixture was stirred at 100°C for 8 hours. Subsequently, 0.072 ml of dimethylcarbamoyl chloride was added and the mixture was stirred at the same temperature for a further 7 hours. After the reaction mixture was allowed to cool to room temperature, 1 ml of water was added and the mixture was extracted with 5 ml of ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel chromatography (eluent: ethyl acetate:hexane = 10:90 to 60:40 gradient) to obtain 85 mg of the target product as a colorless oily substance. 1H-NMR (CDCl3, Me4Si, 300MHz) δ: 9.30 (brs, 1H),7.90-7.65 (m, 3H), 7.45-7.35 (m, 1H), 7.26 (d, J=4.8 Hz, 2H). 3.05 (brs, 6H). Step 6: Synthesis of (S)-N-(amino(3,3-dimethylureido)methylene)-2-chloro-4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)benzamide [Inventive Compound No. 4-033(S)] To a solution of 70 mg of N-(amino(3,3-dimethylureido)methylene)-2-chloro-4-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluoro-2-butenoyl)benzamide in 2.5 ml of dichloromethane, 0.028 ml of 30% by mass sodium hydroxide aqueous solution and 8 mg of N-(acridine-9-ylmethyl)-quinine-1-ium bromide were added, and the mixture was cooled to -20°C. Then, 0.015 ml of 50% by mass hydroxylamine aqueous solution was added dropwise, and the mixture was stirred overnight. After the reaction was complete, 1 ml of water was added at room temperature, and the mixture was extracted with 2 ml of chloroform. The resulting organic layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel chromatography (eluent: ethyl acetate:hexane = 10:90 to 70:30 gradient) to obtain 45 mg of the target product as a colorless oily substance. Optical purity: 62%ee Condition A; Retention time 9.25 minutes (main peak), 11.57 minutes (minor peak) 1 H-NMR (CDCl3, Me4Si, 400MHz) δ:9.32 (brs, 1H), 7.70-7.65 (m, 2H), 7.60-7.55 (m, 3H), 4.07 (d, J=17.2 Hz, 1H), 3.69 (d, J=17.2 Hz, 1H), 3.04 (brs, 6H). Synthesis Example 12: Synthesis of (S)-N-(amino(tert-butoxycarbonylamino)methylene)-4-(5-(3-bromo-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide [Invention Compound No. 11-001(S)] Step 1: Synthesis of 4-(3-(3-bromo-5-(trifluoromethyl)phenyl)-4,4,4-trifluoro-2-butenoyl)-2-methylbenzamide To a 60 ml solution of 7.07 g of 1-(3-bromo-5-(trifluoromethyl)phenyl)-2,2,2-trifluoroethane-1-one, 3 g of 4-acetyl-2-methylbenzamide and 0.176 ml of 40% by mass tetrabutylammonium hydroxide aqueous solution were sequentially added, and the mixture was heated under reflux for 4 hours while dehydrating in a Dean-Stark apparatus. 1.1 g of 1-(3-bromo-5-(trifluoromethyl)phenyl)-2,2,2-trifluoroethane-1-one and 0.088 ml of 40% by mass tetrabutylammonium hydroxide aqueous solution were added, and the mixture was stirred at the same temperature for a further 6 hours. After the reaction was complete, the mixture was allowed to cool to room temperature, 50 ml of ethyl acetate and 50 ml of water were added, and the mixture was extracted with 30 ml of ethyl acetate. The resulting organic layer was dried with saturated brine, then with anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel chromatography (using a gradient of ethyl acetate:hexane = 20:80 to 60:40 as the eluent), and 7.1 g of the target product was obtained as a pale yellow solid. Melting point: 146~148℃ 1 H-NMR (CDCl3, Me4Si, 300MHz) δ: 7.75-7.40 (m, 6H), 5.69 (brs, 2H), 2.52 (s, 3H). Step 2: Synthesis of (S)-4-(5-(3-bromo-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide To a solution of 7 g of 4-(3-(3-bromo-5-(trifluoromethyl)phenyl)-4,4,4-trifluoro-2-butenoyl)-2-methylbenzamide in 146 ml of dichloromethane, 3.21 ml of 50% by mass sodium hydroxide aqueous solution and 868 mg of N-(acridine-9-ylmethyl)-quinine-1-ium bromide were added and the mixture was cooled to -20°C. 6.1 ml of aqueous solution of 2.03 g of hydroxylamine hydrochloride was added dropwise, and the mixture was stirred overnight at the same temperature. After the reaction was complete, 15 ml of 6 mol / l hydrochloric acid was added at room temperature, and the mixture was extracted with 50 ml of chloroform. The resulting organic layer was washed with 15 ml of 6 mol / l hydrochloric acid, dried with saturated brine, and then with anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain 7.88 g of the target product as a pale yellow amorphous material. Optical purity: 86%ee Condition T; Retention time 7.58 minutes (main peak), 11.10 minutes (minor peak) 1 H-NMR (CDCl3, Me4Si, 300MHz) δ:7.96 (s, 1H), 7.84 (s, 1H), 7.80 (s, 1H), 7.55-7.45 (m, 3H), 5.70 (brs, 2H), 4.13 (d, J=17.4 Hz, 1H), 3.71 (d, =17.4 Hz, 1H), 2.53 (s, 3H). Step 3: Synthesis of (S)-4-(5-(3-bromo-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzoic acid 7.65 g of (S)-4-(5-(3-bromo-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide was dissolved in 62 ml of n-butanol. 4.1 ml of sulfuric acid was added, and the mixture was stirred at 120°C for 4 hours. After stirring overnight at room temperature, the temperature was raised again to 120°C and stirred for 1.5 hours. After the reaction was complete, 60 ml of 6 mol / l sodium hydroxide aqueous solution was added under ice cooling, and the mixture was stirred overnight at room temperature. After the reaction was complete, 12 mol / l hydrochloric acid was added under ice cooling until the pH reached 4, and the mixture was extracted with 30 ml of ethyl acetate. The resulting organic layer was dried with saturated brine, then with anhydrous sodium sulfate, and the solvent was removed under reduced pressure. 50 ml of toluene was added to the resulting residue, and the solvent was removed again under reduced pressure to obtain 7.55 g of the target product as a pale yellow oily substance. Optical purity: 85%ee Condition O; Retention time 1.79 minutes (main peak), 4.73 minutes (minor peak) 1 H-NMR (CDCl3, Me4Si, 400MHz) δ:8.15-8.05 (m, 1H), 7.98 (s, 1H), 7.85 (s, 1H), 7.81 (s, 1H), 7.60-7.50 (m, 2H), 4.16 (d, J=17.2 Hz, 1H), 3.74 (d, J=17.2 Hz, 1H), 2.69 (s, 3H). Step 4: Synthesis of (S)-N-(amino(tert-butoxycarbonylamino)methylene)-4-(5-(3-bromo-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide [Invention Compound No. 11-001(S)] To a solution of 3.5 g of (S)-4-(5-(3-bromo-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzoic acid in 20 ml of N,N-dimethylformamide, 2.03 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 1.35 g of 1-(tert-butoxycarbonyl)guanidine, and 96 mg of 1-hydroxy-7-azabenzotriazole were sequentially added, and the mixture was stirred overnight at room temperature. After the reaction was complete, 10 ml of water was added, and the mixture was extracted with 10 ml of ethyl acetate. The resulting organic layer was dried over saturated brine and anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel chromatography (eluent: ethyl acetate:hexane = 10:90 to 60:40 gradient) to obtain 3.57 g of the target product as a white solid. Melting point: 95-97°C Optical purity: 85%ee Condition A; Retention time 4.80 minutes (main peak), 6.91 minutes (minor peak) 1 H-NMR (CDCl3, Me4Si, 400MHz) δ:8.63 (brs, 1H), 7.97 (s, 1H), 7.85-7.80 (m, 3H), 7.55-7.50 (m, 2H), 4.14 (d, J=17.2 Hz, 1H), 3.72 (d, J=17.2 Hz, 1H), 2.58 (s, 3H), 1.51 (s, 9H). Synthesis Example 13: Synthesis of (S)-N-(amino(methoxycarbonylamino)methylene)-4-(5-(3-bromo-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide [Inventive Compound No. 11-005(S)] Step 1: Synthesis of (S)-N-(diaminomethylene)-4-(5-(3-bromo-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide hydrochloride 921 mg of (S)-N-(amino(tert-butoxycarbonylamino)methylene)4-(5-(3-bromo-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide was added to 10 ml of 1,4-dioxane solution in 4 mol / l hydrogen chloride, and the mixture was stirred at 70°C for 3 hours. After the reaction was complete, the solvent was removed under reduced pressure to obtain 890 g of the target product as a yellow amorphous material. 1 Based on 1H-NMR, the target substance was estimated to be a monohydrochloride salt. Optical purity: 84%ee Condition W; Retention time 3.27 minutes (main peak), 7.17 minutes (minor peak) 1 H-NMR (CDCl3, Me4Si, 300MHz) δ: 11.49 (s, 1H), 8.74 (brs, 2H), 8.56 (brs, 2H), 7.95-7.75 (m, 4H), 7.65-7.50 (m, 2H), 4.14 (d, J=17.4 Hz, 1H), 3.74 (d, J=17.4 Hz, 1H), 2.55 (s, 3H). Step 2: Synthesis of (S)-N-(amino(methoxycarbonylamino)methylene)-4-(5-(3-bromo-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide [Inventive Compound No. 11-005(S)] 830 mg of (S)-N-(diaminomethylene)-4-(5-(3-bromo-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide hydrochloride was dissolved in 7.2 ml of dichloromethane. Under ice cooling, 0.807 ml of triethylamine and 0.111 ml of methyl chloroformate were sequentially added, and the mixture was stirred at the same temperature for 1 hour. After the reaction was complete, 5 ml of water was added, and the mixture was extracted with 5 ml of chloroform. The resulting organic layer was dried with saturated brine, then with anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel chromatography (eluent: ethyl acetate:hexane = 10:90 to 60:40 gradient) to obtain 590 mg of the target product as a white solid. Melting point: 151-154°C Optical purity: 88%ee Condition R; retention time 1.97 minutes (main peak), 2.85 minutes (minor peak) 1 H-NMR (CDCl3, Me4Si, 400MHz) δ: 8.93 (brs, 1H), 7.98 (s, 1H), 7.85 (s, 1H), 7.81 (s, 1H), 7.70-7.60 (m, 2H), 7.55-7.45 (m, 2H), 4.14 (d, J=17.4 Hz, 1H), 3.73 (d, J=17.4 Hz, 1H), 3.62 (s, 3H), 2.47 (s, 3H). Synthesis Example 14: Synthesis of (S)-N-(amino(ethylsulfonamide)methylene)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide [Inventive Compound No. 1-025(S)] Step 1: Synthesis of (S)-N-(diaminomethylene)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide 275 mg of guanidine hydrochloride was added to 2 ml of 3 mol / l sodium hydroxide aqueous solution, cooled to 0°C, and then 5 ml of tetrahydrofuran solution of 629 mg of (S)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzoyl chloride was added dropwise, and the mixture was stirred at the same temperature for 1.5 hours. After the reaction was complete, 5 ml of saturated saline solution was added, and the mixture was extracted with 5 ml of ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain 779 mg of the target product as a colorless oily substance. Optical purity: 98%ee Condition B; Retention time 5.35 minutes (main peak), 8.38 minutes (minor peak) 1 H-NMR (CDCl3, Me4Si, 400MHz) δ:7.76 (d, J=8.0 Hz, 1H), 7.55-7.45 (m, 2H), 7.43 (dd, J=2.0, 2.0 Hz, 1H), 6.45 (brs, 2H), 4.09 (d, J=17.2 Hz, 141H), 3.70 (d, J=17.2 Hz, 1H), 2.55 (s, 3H). Step 2: Synthesis of (S)-N-(amino(ethylsulfonamide)methylene)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide [Inventive Compound No. 1-025(S)] To a 5 ml solution of (S)-N-(diaminomethylene)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide, 0.602 ml of triethylamine and 0.204 ml of ethanesulfonyl chloride were sequentially added at room temperature, and the mixture was stirred at the same temperature for 40 minutes. After the reaction was complete, 5 ml of water was added, and the mixture was extracted with 5 ml of dichloromethane. The resulting organic layer was dried with saturated brine, then with anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel chromatography (eluent: ethyl acetate:hexane = 10:90 to 50:50 gradient) to obtain 471 mg of the target product as a white solid. Melting point: 183-185℃ Optical purity: 99%ee Condition A; Holding time 11.49 minutes (main peak), 15.60 minutes (minor peak) 1 H-NMR (CDCl3, Me4Si, 400MHz) δ: 8.91 (s, 1H), 7.65-7.55 (m, 3H), 7.55-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.09 (d, J=17.2 Hz, 1H), 3.71 (d, J=17.2 Hz, 1H), 3.10 (q, J=7.2 Hz, 2H), 2.56 (s, 3H), 1.40 (t, J=7.2 Hz, 3H). [Reference example] The following is a reference example of a method for producing the manufacturing intermediate of the compound of the present invention.

[0336] Reference Example 1: Synthesis of (S)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzoic acid 5.0 g (91% ee) of (S)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide, 25 g of acetic acid, and 12.5 g of 50% by mass sulfuric acid were mixed and stirred at 120°C for 24 hours. After the reaction was complete, 25 mL of water was added at room temperature and the mixture was extracted with 58 mL of toluene. The resulting organic layer was washed three times with 25 mL of water and then dried over anhydrous sodium sulfate. By removing the solvent under reduced pressure, 5.0 g of the target product was obtained as a pale yellow oily substance. Optical purity: 92%ee Condition O; Retention time 1.94 minutes (main peak), 6.23 minutes (minor peak) 1 H-NMR (CDCl3, Me4Si, 300MHz) δ:8.15-8.05 (m, 1H), 7.60-7.50 (m, 4H), 7.45-7.40 (m, 1H), 4.10 (d, J=18.0 Hz, 1H), 3.71 (d, J=18.0 Hz, 1H), 2.67 (s, 3H). Reference Example 2: Synthesis of (S)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzoyl chloride To a solution of 18.2 g (80% ee) of (S)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzoic acid in 104 ml of toluene, 132 mg of triethylamine was added and the mixture was heated to 75°C. 6.21 g of thionyl chloride was added dropwise, and the mixture was stirred at the same temperature for 1.5 hours. After the reaction was complete, the solvent was removed under reduced pressure to obtain 18 g of the target product as a white solid. Melting point: 103-105℃ 1 H-NMR (CDCl3, Me4Si, 400MHz) δ:8.26 (d, J=8.4 Hz, 1H), 7.65-7.40 (m, 5H), 4.10 (d, J=17.2 Hz, 1H), 3.72 (d, J=17.2 Hz, 1H), 2.61 (s, 3H). Reference Example 3: Synthesis of (S)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide To a solution of 18.3 g of 4-(3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-butenoyl)-2-methylbenzamide in 228 ml of dichloromethane, 1.09 g of N-(acridine-9-ylmethyl)-kinin-1-ium bromide was added and the mixture was cooled to -15°C. Then, 11.4 ml of 30% by mass aqueous sodium hydroxide solution and 6.02 g of 50% by mass aqueous hydroxylamine solution were added, and the mixture was stirred at the same temperature for 2.5 hours. After the reaction was complete, the temperature was raised to 0°C, 114 ml of 2 mol / l hydrochloric acid was added dropwise, and the mixture was stirred at the same temperature for 1 hour, followed by liquid-liquid separation. The organic layer was washed with 100 ml of water, and the solvent was removed under reduced pressure to obtain 17.6 g of the target product as a white solid. Melting point: 146-148℃ Optical purity: 91%ee Condition A; Retention time 6.16 minutes (main peak), 8.43 minutes (minor peak) 1 H-NMR (CDCl3, Me4Si, 400MHz) δ: 7.55-7.50 (m, 5H), 7.45-7.40 (m, 1H), 5.80-5.70 (m, 2H), 4.09 (d, J=17.6 Hz, 1H), 3.70 (d, J=17.6 Hz, 1H), 2.53 (s, 3H). Reference Example 4: Synthesis of (S)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzoic acid Following the methods of Examples 1, 3, and 4 of Japanese Patent Publication No. 2011-051977, 202.4 g of (S)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzoic acid was obtained as a white solid from 464.2 g of 0.5 toluene-hydrate of 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzoic acid. Melting point: 134-136℃ Optical purity: 98%ee Reference Example 5: Synthesis of (S)-4-(5-(3-bromo-5-chlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide Following the method of Reference Example 3, 120.6 g of (S)-4-(5-(3-bromo-5-chlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzamide was obtained as a brown amorphous material from 111.5 g of 4-(3-(3-bromo-5-chlorophenyl)-4,4,4-trifluoro-2-butenoyl)-2-methylbenzamide. Optical purity: 91%ee Condition P; retention time 4.16 minutes (main peak), 6.82 minutes (minor peak) 1 H-NMR (CDCl3, Me4Si, 400MHz)δ: 7.65-7.50 (m, 6H), 5.77 (brs, 2H), 4.09 (d, J=17.2 Hz, 1H), 3.70 (d, J=17.2 Hz, 1H), 2.53 (s, 3H). Reference Example 6: Synthesis of (S)-4-(5-(3-bromo-5-chlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzoic acid Following the method of Reference Example 4, 106.4 g of (S)-4-(5-(3-bromo-5-chlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzoic acid was obtained as a brown amorphous material from 120.6 g of 4-(5-(3-bromo-5-chlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methylbenzoic acid. Optical purity: 91%ee Condition O; Retention time 1.93 minutes (main peak), 6.77 minutes (minor peak) 1H-NMR (CDCl3, Me4Si, 400MHz) δ:8.15-8.05 (m, 1H), 7.70-7.60 (m, 1H), 7.60-7.50 (m, 4H), 4.11 (d, J=17.6 Hz, 1H), 3.72 (d, J=17.6 Hz, 1H), 2.69 (s, 3H). The compounds of the present invention can be synthesized in accordance with the above synthesis examples. Examples prepared in the same manner as synthesis examples 1 to 14 are shown in Tables 1 to 16, but the isoxazoline-substituted benzamide compounds included in the present invention are not limited to these.

[0337] In the table, Me represents methyl, and similarly, Et represents ethyl, n-Pr or Pr-n represents n-propyl, i-Pr or Pr-i represents isopropyl, c-Pr or Pr-c represents cyclopropyl, n-Bu or Bu-n represents n-butyl, i-Bu or Bu-i represents isobutyl, t-Bu or Bu-t represents tert-butyl, c-Bu or Bu-c represents cyclobutyl, c-Pen or Pen-c represents cyclopentyl, c-Hex or Hex-c represents cyclohexyl, n-Oct or Oct-n represents n-octyl, and Ph represents phenyl.

[0338] Furthermore, in the table, for example, the "4-" in "4-F-Ph" indicates the substitution position on the phenyl group, as described below. For example, "4-F-Ph" represents 4-fluorophenyl.

[0339] [ka]

[0340] "2,4-F2-Ph" represents 2,4-difluorophenyl.

[0341] [ka]

[0342] Furthermore, in the table, the structures represented by D-2a, D-3a, D-14a, D-23a, D-30a, D-37a, D-58a, G-1a, G-2a, G-4a~G-9a, G-9b, G-10a~G-27a, G-30a, G-39a, G-50a~G-58a, T-1~T-8 and T-9 represent the following structures, respectively.

[0343] [ka]

[0344] [ka]

[0345] [ka]

[0346] [ka]

[0347] [ka]

[0348] In the structural formulas shown in the diagram above, the numbers indicate the substitution positions. For example, the notation "(G-10a)(3-Me)" in the table represents the following structure. The absence of a substituent designation indicates an unsubstituted molecule.

[0349] [ka]

[0350] Furthermore, the notation "*1" indicates that the compound is a solid, "*2" indicates that the compound is an oily, resinous, or amorphous compound with no melting point, and "mp" indicates the melting point (unit: °C).

[0351] [Table 1]

[0352] [Chem.]

[0353] ―――――――――――――――――――――――――――――――――――― No. Y 1 R 4 R 3 R 2 R 1 m.p.(℃) ―――――――――――――――――――――――――――――――――――― 1-001 Me H H H C(O)Me 81-83 1-001(S) Me H H H C(O)Me 156-158 1-002 Me H H H C(O)OBu-t 88-89 1-002(S) Me H H H C(O)OBu-t 86-88 1-003 Me H H H C(O)OMe 167-169 1-003(S) Me H H H C(O)OMe 185-187 1-004 Me H H H S(O)2Me 136-138 1-004(S) Me H H H S(O)2Me 164-166 1-005 Me H H H S(O)2CF3 194-196 1-005(S) Me H H H S(O)2CF3 192-194 1-006 Me H H H C(O)OEt 161-163 1-007 Me H H H C(O)NMe2 88-90 1-007(S) Me H H H C(O)NMe2 *2 1-008 Me H H H S(O)2NMe2 86-88 1-008(S) Me H H H S(O)2NMe2 171-173 1-009 Me H H H C(S)NHMe 93-95 1-010 Me H Me H C(O)OMe *2 1-011 Me H Et H C(O)OMe *2 1-012 Me Me Me H C(O)OMe *2 1-013 Me H Pr-i H C(O)OMe *2 1-014 Me Me Et H C(O)OMe *2 1-015 Me H CH2Pr-c H C(O)OMe *2 1-016 Me H CH2C≡CH H C(O)OMe *2 1-017 Me H C(O)OPr-i H C(O)OPr-i *2 1-018 Me H H H C(O)OPr-i *2 1-019 Me H H H C(O)NHEt 182-184 1-020 Me H H H C(O)NHMe 182-184 1-020(S) Me H H H C(O)NHMe 179-181 1-021 Me H CH2CF3H C(O)OMe *2 1-022 Me H H H C(O)SBu-t *2 1-023 Me H H H C(O)OCH2CH=CH2155-157 1-024 Me H H H C(O)OCH2CH2OMe *2 1-025 Me H H H S(O)2Et *2 1-025(S) Me H H H S(O)2Et 183-185 1-026 Me H H H C(S)NHPr-c *2 1-027 Me H H H C(O)NHPr-i *2 1-028 Me H H H S(O)2CH2Cl *2 1-029 Me H H H C(O)NH2*2 1-030 Me H H H S(O)2Pr-i *2 1-030(S) Me H H H S(O)2Pr-i *2 1-031 Me H H H S(O)2Pr-c 138-140 1-031(S) Me H H H S(O)2Pr-c 122-124 1-032 Me H H H S(O)2(4-Me-Ph) 216-217 1-033 Me H Me H S(O)2Me 217-219 1-034 Me H Et H S(O)2Me 199-201 1-035 Me Me Me H S(O)2Me 215-217 1-036 Me H Pr-i H S(O)2Me *2 1-037 Me H CH2C≡CH H S(O)2Me *2 1-038 Me H H H S(O)2NH291-93 1-039 Me H H H S(O)2NHC(O)OMe 117-119 1-040 Me H H H S(O)2NHC(O)OEt 117-119 1-041 Me H H H S(O)2NHC(O)OBu-t *2 1-042 Me H H H S(O)2Pr-n *2 1-042(S) Me H H H S(O)2Pr-n 171-173 1-043 Me H H H S(O)2(4-F-Ph) 175-177 1-044 Me H H H S(O)2(4-CF3-Ph) 243-245 1-045 Me H Pr-c H C(O)OMe *2 1-046 Me H CH2CH2OMe H C(O)OMe *2 1-047 Me H CH2CN H C(O)OMe *2 1-048 Me H CH2CH=CH2H C(O)OCH2CH=CH2*2 1-049 Me H CH2CH=CH2H C(O)OMe *2 1-050 Me H OMe H C(O)OMe *2 1-051 Cl H H H C(O)OBu-t *2 1-051(S) Cl H H H C(O)OBu-t *2 1-052 Br H H H C(O)OBu-t 155-157 1-052(S) Br H H H C(O)OBu-t *2 1-053 Me H H H C(O)Ph 170-172 1-054 Me H H H C(O)(4-CN-Ph) 168-170 1-055 Me H H H C(O)(4-OCF3-Ph) 156-158 1-056 Me H H H C(O)(4-CF3-Ph) 172-175 1-057 Me H H H C(O)(3-CF3-Ph) 177-179 1-058 Me H H H C(O)(2-CF3-Ph) *2 1-059 Me H H H C(O)CH2CF3250-251 1-060 Cl H H H S(O)2Me *2 1-060(S) Cl H H H S(O)2Me 140-143 1-060(R) Cl H H H S(O)2Me 147-150 1-061 Br H H H S(O)2Me *2 1-061(S) Br H H H S(O)2Me 150-152 1-061(R) Br H H H S(O)2Me 148-151 1-062 H H H H C(O)OBu-t 107-109 1-063 Me H C(O)N(Me)Et H C(O)N(Me)Et *2 1-064 Me H H H S(O)2N(Me)Pr-i *2 1-065 Me H H H C(O)N(Me)Pr-i *2 1-066 Me H H Me C(O)OBu-t 91-94 1-067 Cl H H H C(O)OMe 164-166 1-068 Cl H H H C(O)NMe2*2 1-069 Me H Me H C(O)NMe2*2 1-070 Me H Et H C(O)NMe2*2 1-071 Me H H H C(O)N(Me)Et *2 1-072 Me H H H S(O)2N(Me)Et *2 1-073 Me H H Me C(O)OMe 175-177 1-074 Me H H H C(O)Et 89-91 1-075 Me H C(O)Et H C(O)Et *2 1-076 Me H H H C(O)Pr-n 89-91 1-077 Me H C(O)Pr-n H C(O)Pr-n *2 1-078 Me H H H C(O)Pr-c 111-113 1-078(S) Me H H H C(O)Pr-c 206-208 1-079 Me H C(O)Pr-c H C(O)Pr-c 96-98 1-080 Me H H H C(O)CH2OMe *2 1-081 Me H H H C(O)Pr-i 194-196 1-082 Me H C(O)Pr-i H C(O)Pr-i *2 1-083 Me H H H C(O)C(Me)=CH2*2 1-084 Me H C(O)C(Me)=CH2H C(O)C(Me)=CH291-93 1-085 Me H H H C(O)(2,4-F2-Ph) 105-107 1-086 Me H C(O)(2,4-F2-Ph) H C(O)(2,4-F2-Ph) *2 1-087 Me H H H C(O)N(Me)Ph 108-109 1-088 Me H H Me S(O)2Me *2 1-088(S) Me H H Me S(O)2Me *2 1-089 Me H H H C(S)NHCH2CH=CH293-95 1-090 Me H H H C(S)NMe298-100 1-091 Me H H H C(O)NHPr-c 110-112 1-092 Me H C(O)NHPr-c H C(O)NHPr-c 122-124 1-093 Me H H H C(O)NHPr-n 101-103 1-094 Me H C(O)NHPr-n H C(O)NHPr-n 103-105 1-095 Me H H H C(O)NHPen-c 122-124 1-096 Me H C(O)NHPen-c H C(O)NHPen-c 123-125 1-097 Me H H H C(O)NHHex-c 182-184 1-098 Me H C(O)NHHex-c H C(O)NHHex-c *2 1-099 Me H H H C(O)NHCH2CH=CH2112-114 1-100 Me H C(O)NHCH2CH=CH2H C(O)NHCH2CH=CH2107-109 1-101 Me H H H C(O)NH(4-CF3-Ph) 99-101 1-102 Me H C(O)NH(4-CF3-Ph) H C(O)NH(4-CF3-Ph) 117-119 1-103 H H H H C(O)NMe291-93 1-104 Br H H H C(O)NMe2211-213 1-105 Br H H H C(O)OMe 98-100 1-106 Br H H H C(O)OEt 190-191 1-107 Br H H H C(O)NHMe 178-180 1-108 H H H H C(O)OMe 225-227 1-109 H H H H C(O)OEt 98-100 1-110 H H H H C(O)NHMe 182-184 1-111 Cl H H H C(O)Me 184-186 1-112 Br H H H C(O)Me 202-204 1-113 H H H H C(O)Me 154-156 1-114 Me H H H C(S)NHHex-c *2 1-115 Me H H H C(O)NHCH2Ph *2 1-116 Me H H H C(O)NHCH2CH2Cl *2 1-117 Me H H H C(O)NHPh 127-129 1-118 Me H H H C(O)NH(4-Cl-Ph) 139-141 1-119 Me H H H C(O)NH(3,5-F2-Ph) *2 1-120 Me H H H C(O)NHCH2CH2OMe *2 1-121 Me H H H C(O)NHCH2CF3140-142 1-122 Me H H H C(O)NHBu-n 153-154 1-123 Me H H H C(O)NEt2*2 1-124 Me H H H C(O)N(Me)OMe *2 1-125 Me H H Et S(O)2Me 89-91 1-126 Me H H H C(O)CF3*2 1-127 Me H H H C(O)CHF2*2 1-128 Me H H Et C(O)OMe 192-194 1-129 Me H H CH2CH=CH2C(O)OMe 155-157 1-130 Me H H CH2C≡CH C(O)OMe 94-96 1-131 Me H H H S(O)2NHMe 98-100 1-131(S) Me H H H S(O)2NHMe *2 1-132 Me H H CH2CH=CH2S(O)2Me 79-81 1-133 Me H H H C(O)NHBu-t 131-133 1-134 Me H H H C(O)OCH2Ph 101-103 1-135 Me H H H C(O)OCH2CCl3123-125 1-136 Me H H H C(S)NHPh 98-100 1-137 Me H H H C(O)CH2S(O)2Pr-i *2 1-138 H H H H S(O)2Me 212-214 1-139 H H H Me S(O)2Me 171-173 1-140 Cl H H Me S(O)2Me *2 1-141 Me H H H C(O)CH2NMe282-84 1-142 Me H H H CHO 200-201 1-142(S) Me H H H CHO *2 1-143 Br H H Me S(O)2Me *2 1-143(S) Br H H Me S(O)2Me *2 1-143(R) Br H H Me S(O)2Me *2 1-144 Me H H H C(O)CH=C(Me)CF3*2 1-145 Me H C(O)OMe H S(O)2Me 207-209 1-145(S) Me H C(O)OMe H S(O)2Me *2 1-146 Me H H H C(O)C(O)Me *2 1-147 NO2H H H S(O)2Me 216-218 1-148 Cl H H H C(O)Pr-c 223-225 1-148(S) Cl H H H C(O)Pr-c 102-104 1-149 Me H H Me S(O)2Pr-c *2 1-149(S) Me H H Me S(O)2Pr-c *2 1-150 Me H H H C(O)CH2NHC(O)OMe 117-119 1-151 Me H H H C(O)CH2NHS(O)2Me 180-182 1-152 Me H H H C(O)Bu-i 186-187 1-153 Me H H H C(O)CH2Pr-c 161-163 1-154 Me H H H C(O)(T-3) 140-142 1-155 Me H H H C(O)CH2NHC(O)OBu-t 109-111 1-156 Me H H H C(O)CH2NHC(O)Me 96-98 1-157 Cl H H H S(O)2Et *2 1-157(S) Cl H H H S(O)2Et 229-231 1-158 Cl H H H S(O)2Pr-c *2 1-159 Br H H H S(O)2Pr-c *2 1-160 Me H H H C(O)(T-4) *2 1-161 Me H H H C(O)C≡CMe *2 1-162 Me H H H C(O)(T-1) 178-179 1-163 Me H H H C(O)(T-5) *2 1-163(S) Me H H H C(O)(T-5) 87-89 1-164 Me H H H C(O)(T-2) 168-169 1-165 Me H H H C(O)(4-Me-Ph) 181-183 1-166 Me H H H C(O)(4-Cl-Ph) 186-188 1-167 Me H H H C(O)(4-NO2-Ph) 121-123 1-168 Me H H H C(O)(4-OMe-Ph) *2 1-169 Me H H H C(O)(4-F-Ph) 161-163 1-170 Me H H H C(O)(4-SMe-Ph) *2 1-171 Me H H H C(O)(3-F-4-CN-Ph) *2 1-172 Me H H H C(O)(3-CN-Ph) *2 1-173 Me H H H C(O)(2-Cl-4-S(O)2Me-Ph) *2 1-174 Me H Me H S(O)2NMe279-81 1-174(S) Me H Me H S(O)2NMe2*2 1-175 Me H H H C(O)Bu-c 194-196 1-176 Me H H H C(O)(T-6) 184-186 1-177 Me H H H C(O)(T-7) 194-196 1-178 Me H H H C(O)(2-Cl-Ph) *2 1-179 Me H H H C(O)(3-Cl-Ph) 149-151 1-180 Me H H H C(O)(2-F-4-CF3-Ph) 173-175 1-181 Me H H H C(O)(2-S(O)2Me-4-CF3-Ph) *2 1-182 Me H H H C(O)(2-NO2-4-S(O)2Me-Ph) *2 1-183 Me H H H C(O)(2-Cl-4-F-Ph) *2 1-184 Cl H H H C(O)NHMe 125-127 1-185 Cl H H H C(O)OEt 169-171 1-186 Cl H H H C(O)(T-5) 184-186 1-186(S) Cl H H H C(O)(T-5) 212-214 1-187 Cl H H H C(O)(T-4) *2 1-188 Br H H H C(O)(T-5) 208-209 1-189 Br H H H C(O)(T-4) *2 1-190 Br H H H S(O)2Et *2 1-190(S) Br H H H S(O)2Et 151-153 1-190(R) Br H H H S(O)2Et *2 1-191 Br H H H S(O)2Pr-n *2 1-192 Br H H H C(O)Pr-c 212-213 1-192(S) Br H H H C(O)Pr-c 206-208 1-192(R) Br H H H C(O)Pr-c 208-210 1-193 Me H Me H S(O)2Et 85-87 1-193(S) Me H Me H S(O)2Et *2 1-194 Me H Et H S(O)2Et 85-88 1-194(S) Me H Et H S(O)2Et *2 1-195 Me Me Me H S(O)2Et 85-89 1-196 Me H OMe H S(O)2Et *2 1-197 Me H H H C(O)(T-8) 2 1-198 Me H H H C(O)(T-9) 107-109 1-199 Me H H Me S(O)2Et *2 1-199(S) Me H H Me S(O)2Et *2 1-200 Cl H H H S(O)2NMe2*2 1-201 Br H H H S(O)2NMe2*2 1-202 CF3H H H C(O)OBu-t *2 1-203 Me CH2C≡CH CH2C≡CH H S(O)2Me *2 1-204 Et H H H C(O)OBu-t 96-98 1-205 CF3H H H S(O)2NMe2*2 1-206 Et H H H S(O)2NMe284-86 1-207 Et H H H C(O)Me 186-188 1-208 Me H C(O)OBu-t H S(O)2Et *2 1-209 Et H H H C(O)(T-5) *2 1-210 Et H C(O)(T-5) H C(O)(T-5) *2 1-211 Et H H H S(O)2Et *2 1-212 Et H H H C(O)Pr-c 174-176 1-213 Et H H H C(O)OMe *2 1-214 Et H H H C(O)NHMe 117-119 1-215 Et H H H S(O)2Me 181-183 1-216 CF3H H H C(O)(T-5) 217-219 1-217 CF3H H H C(O)Me 217-219 1-218 Et H C(O)Me H C(O)Me *2 1-219 Me H H CH2Pr-c S(O)2Me *2 1-220 Me H H CH2OMe S(O)2Me *2 1-221 Me H CH2OMe H S(O)2Me *2 1-222 CF3H H H S(O)2Et 196-198 1-223 CF3H H H C(O)Pr-c 189-191 1-224 CF3H H H C(O)OMe *2 1-225 CF3H H H C(O)NHMe 169-171 1-226 CF3H H H S(O)2Me *2 1-227 Me H C(O)Me H S(O)2Me *2 1-227(S) Me H C(O)Me H S(O)2Me *2 1-228 Me H H CH2Ph S(O)2Me *2 1-229 Me H H CH2(2-F-Ph) S(O)2Me *2 1-230 Me H H CH2C(Me)=NOMe S(O)2Me 117-119 1-231 Me H H Pr-n S(O)2Me *2 1-232 Me H C(O)Pr-c H S(O)2Me *2 1-232(S) Me H C(O)Pr-c H S(O)2Me *2 1-233 Me H C(O)NMe2H S(O)2Me 209-211 1-234 Me H C(O)Ph H S(O)2Me *2 1-234(S) Me H C(O)Ph H S(O)2Me *2 1-235 Me H C(O)Pr-i H S(O)2Me *2 1-235(S) Me H C(O)Pr-i H S(O)2Me *2 1-236 Me H C(O)Et H S(O)2Me *2 1-236(S) Me H C(O)Et H S(O)2Me *2 1-237 Me H C(O)NHMe H S(O)2Me *2 1-237(S) Me H C(O)NHMe H S(O)2Me 139-141 1-238(S) Me HC(O)CH2OMe HS(O)2Et *2 1-239(S) Me HC(O)(G-5a) HS(O)2Et *2 1-240(S) Me HC(O)Me HS(O)2Et *2 1-241(S) Me HC(O)Et HS(O)2Et *2 1-242(S) Me HC(O)OEt HS(O)2Et *2 1-243(S) Me HC(O)Me HS(O)2NMe2*2 1-244(S) Me HC(O)Et HS(O)2NMe2*2 1-245(S) Me HC(O)OEt HS(O)2NMe2*2 1-246(S) Me H Pr-c HS(O)2NMe2*2 1-247(S) Me H CH2Ph ​​HS(O)2NMe2*2 1-248(S) Me HHHS(O)2(4-NO2-Ph) 212-214 1-249(S) Me H Et HS(O)2NMe2*2 1-250(S) Me H CH2CH2OMe HS(O)2NMe2*2 1-251(S) Me HC(O)OMe HS(O)2Et *2 1-252(S) Me HC(O)NHMe HS(O)2NMe2*2 1-253(S) Me HC(O)NHEt HS(O)2NMe2*2 1-254(S) Me HC(O)OMe HS(O)2NMe2*2 1-255 Me HC(O)NHET HS(O)2Me *2 1-255(S) Me HC(O)NHEt HS(O)2Me *2 1-256 Me HC(O)OEt HS(O)2Me *2 1-256(S) Me HC(O)OEt HS(O)2Me *2 1-257(S) Me H H H S(O)2(2-CF3-Ph) *2 1-258(S) Me H OEt H S(O)2Et *2 1-259(S) Me H C(O)NHMe H C(O)NHMe 119-121 1-260(S) Me H C(O)Et H C(O)OMe *2 1-261(S) Me H C(O)NHMe H C(O)OMe *2 1-262(S) Me H C(O)Pr-c H C(O)OMe *2 1-263(S) Me H C(O)OMe H C(O)OMe *2 1-264(S) Me H C(O)Me H C(O)NHMe 80-82 1-265(S) Me H C(O)Me H C(O)Pr-c *2 1-266(S) Me H C(O)Et H C(O)Pr-c *2 1-267(S) Me H C(O)Ph H C(O)Pr-c *2 1-268(S) Me H C(O)Pr-c H C(O)Pr-c *2 1-269(S) Me H C(O)Pr-i H C(O)Pr-c *2 1-270(S) Me H C(O)OEt H C(O)Pr-c *2 1-271(S) Me H C(O)Bu-i H C(O)Pr-c *2 1-272(S) Me H C(O)(G-5a) H C(O)Pr-c *2 1-273(S) Me H C(O)(G-51a) H C(O)Pr-c *2 1-274(S) Me H H Me S(O)2NMe2*2 1-275(S) Cl H H H S(O)2CF3184-186 1-276(S) Me H C(O)Me H S(O)2CF3*2 1-277(S) Me H C(O)(G-5a) H S(O)2CF3*2 1-278(S) Me H C(O)OMe H S(O)2CF3*2 1-279(S) Me H C(O)OEt H S(O)2CF3*2 1-280(S) Me H S(O)2Me H S(O)2Me 240-242 1-281(S) Me H OEt H S(O)2NMe2*2 1-282(S) Me H C(O)Pr-c H S(O)2Et *2 1-283(S) Me H C(O)Ph H S(O)2NMe2*2 1-284(S) Me H C(O)Pr-c H S(O)2NMe2*2 1-285(S) Me H CH2CH2OMe H S(O)2Et *2 1-286(S) Me H C(O)Et H C(O)NHMe *2 1-287(S) Me H C(O)Ph H C(O)NHMe 175-177 1-288(S) Me H C(O)NHMe H C(O)Pr-c *2 1-289(S) Me H C(O)Me H C(O)(T-5) *2 1-290(S) Me H C(O)Et H C(O)(T-5) *2 1-291(S) Me H C(O)NHMe H C(O)(T-5) *2 1-292(S) Me H C(O)Ph H C(O)(T-5) *2 1-293(S) Me H C(O)Pr-c H C(O)(T-5) *2 1-294(S) Me H C(O)OMe H C(O)(T-5) *2 1-295(S) Me H C(O)Pr-c H S(O)2CF3*2 1-296(S) Me H H H S(O)2(4-CN-Ph) 215-216 1-297(S) Me H H H S(O)2Hex-c *2 1-298(S) Me H H H S(O)2CH2CH=CH2*2 1-299(S) Me H H H S(O)2CH2CF3*2 1-300(S) Me H H H S(O)2CH2CH2OMe 153-154 1-301(S) Me H H H S(O)2(3-CF3-Ph) 177-179 1-302(S) Me H H H S(O)2Oct-n 136-138 1-303(S) Me H Pr-i H S(O)2Et *2 1-304(S) Me H H H S(O)2(2-F-Ph) 152-154 1-305(S) Me H H H S(O)2(4-Cl-Ph) 213-215 1-306(S) Me H H H S(O)2(4-Br-Ph) 222-224 1-307(S) Cl H C(O)OMe H S(O)2Et 192-194 1-308(S) Cl H C(O)OEt H S(O)2Et *2 1-309(S) Me H C(O)OMe H S(O)2Pr-c 99-101 1-310(S) Me H C(O)OEt H S(O)2Pr-c 126-128 1-311(S) Me H H H S(O)2CF2CF2CF2CF3157-159 1-312(S) Me H OMe H S(O)2NMe2*2 1-313(S) Me H C(O)Bu-i H S(O)2Et *2 1-314(S) Me H C(O)Ph H S(O)2Et *2 1-315(S) Me H C(O)Pr-i H S(O)2Et *2 1-316(S) Me H C(O)Pr-i H S(O)2NMe2*2 1-317(S) Me H C(O)Ph H S(O)2CF3*2 1-318(S) Me HC(O)Pr-i HS(O)2CF3*2 1-319(S) Me HC(O)NHEt HS(O)2CF3131-133 1-320(S) Me HC(O)Et HS(O)2CF3*2 1-321(S) Me HC(O)(G-51a) HS(O)2Et 222-224 1-322(S) Me HC(O)NHMe HS(O)2Et *2 1-323(S) Me HC(O)NHEt HS(O)2Et *2 1-324(S) Me H Pr-c HS(O)2Et *2 1-325(S) Me H CH2Ph ​​HS(O)2Et *2 1-326(S) Me H Pr-n HS(O)2Et *2 1-327 Me HH Et S(O)2Et 152-154 1-327(S) Me HH Et S(O)2Et 142-144 1-328(S) Me HH CH2CH=CH2S(O)2Et *2 1-329(S) Me HH CH2&C≡CH S(O)2Et *2 1-330(S) Me HH CH2Pr-c S(O)2Et *2 1-331(S) Me HH CH2Ph ​​S(O)2Et *2 1-332(S) Me HH Et S(O)2NMe2*2 1-333(S) Me HH CH2OMe S(O)2Et 127-129 ―――――――――――――――――――――――――――――――――――― [Table 2]

[0354]

Chem.

[0355] ―――――――――――――――――――――――――――――――――――― No. Y 1 R 4 R 3 R 2 R 1 m.p.(°C) ―――――――――――――――――――――――――――――――――――― 2-001 Me H H H C(O)OBu-t 86-88 2-001(S) Me H H H C(O)OBu-t 99-101 2-002 Me H H H C(O)OMe 91-93 2-003 Me H H H C(O)NMe2 79-81 2-004 Me H H H S(O)2Me 105-107 2-004(S) Me H H H S(O)2Me 151-153 2-005 Me H H H C(O)Me 192-194 2-006 Me H H H C(O)(T-5) *2 2-006(S) Me H H H C(O)(T-5) *2 2-007 Me H H H C(O)Pr-c *2 2-007(S) Me H H H C(O)Pr-c 190-192 2-008 Me H H H C(O)NHMe 174-176 2-008(S) Me H H H C(O)NHMe 191-193 2-008(R) Me H H H C(O)NHMe 191-193 2-009 Me H H H S(O)2Et *2 2-009(S) Me H H H S(O)2Et 97-99 2-009(R) Me H H H S(O)2Et 189-191 2-010 Me H H H C(O)OEt *2 2-011 Me H H H C(O)NHEt *2 2-012 Cl H H H C(O)OBu-t 144-146 2-013 Cl H H H C(O)(T-5) 194-196 2-013(S) Cl H H H C(O)(T-5) 198-200 2-014 Cl H H H C(O)(T-4) 91-94 2-015 Cl H H H C(O)Me 209-211 2-016 Cl H H H C(O)NHMe 120-122 2-017 Cl H H H C(O)OMe 169-170 2-018 Cl H H H C(O)Pr-c 239-240 2-018(S) Cl H H H C(O)Pr-c 227-228 2-019 Cl H H H S(O)2Me *2 2-019(S) Cl H H H S(O)2Me *2 2-020 Cl H H H S(O)2Et 111-113 2-020(S) Cl H H H S(O)2Et *2 2-021 Me H H H S(O)2Pr-c *2 2-022 Cl H H H S(O)2Pr-c *2 2-023 Cl H H H C(O)NMe2159-161 2-024 Cl H H H C(O)N(Me)OMe *2 2-025 Me H H H S(O)2NMe2*2 2-025(S) Me H H H S(O)2NMe2187-189 2-026 Br H H H S(O)2Et *2 2-026(S) Br H H H S(O)2Et *2 2-027 Br H H H S(O)2Me *2 2-027(S) Br H H H S(O)2Me *2 2-028 Br H H H C(O)OMe *2 2-028(S) Br H H H C(O)OMe *2 2-029 Br H H H C(O)NHMe 132-134 2-029(S) Br H H H C(O)NHMe 154-156 2-030 Me H H H S(O)2NH2*2 2-031 Cl H H H S(O)2NMe2*2 2-031(S) Cl H H H S(O)2NMe2*2 2-032 Br H H H S(O)2NMe2*2 2-032(S) Br H H H S(O)2NMe2195-197 2-033 Br H H H C(O)(T-5) 217-218 2-033(S) Br H H H C(O)(T-5) 194-196 2-034 Br H H H CHO *2 2-035 Br H H H C(O)Pr-c 209-211 2-035(S) Br H H H C(O)Pr-c 204-206 2-036(S) Me H H H S(O)2CF3196-198 2-037(S) Me H H Me S(O)2NMe2*2 2-038(S) Me H H Et S(O)2NMe2129-131 2-039 Me H H H S(O)2NHMe *2 2-039(S) Me H H H S(O)2NHMe *2 2-040(S) Me H H Me S(O)2Et *2 2-041 Me H H Et S(O)2Et *2 2-041(S) Me H H Et S(O)2Et 142 - 144 2-042(S) Me H H Me S(O)2Me *2 2-043(S) Me H H Et S(O)2Me *2 ―――――――――――――――――――――――――――――――――――― [Table 3]

[0356] [Chem.]

[0357] ―――――――――――――――――――――――――――――――――――― No. Y 1 R 4 R 3 R 2 R 1 m.p.(℃) ―――――――――――――――――――――――――――――――――――― 3-001 Me H H H C(O)OBu-t *2 3-002 Me H H H S(O)2Me *2 3-003 Me H H H C(O)NMe2 171 - 173 3-004 Me H H H C(O)OMe *2 3-005 Me H H H S(O)2NMe2 *2 3-005(S) Me H H H S(O)2NMe2 181 - 183 3-005(R) Me H H H S(O)2NMe2 181 - 183 3-006 Me H H H C(O)Me 204 - 206 3-007 Me H H H C(O)Pr-c 218 - 220 3-007(S) Me H H H C(O)Pr-c 240 - 242 3-007(R) Me H H H C(O)Pr-c 243-245 3-008 Me H H H C(O)Et 195-196 3-009 Me H H H C(O)Pr-i 210-212 3-010 Me H H H S(O)2Et *2 3-011 Me H H H C(O)NHMe 200-202 3-011(S) Me H H H C(O)NHMe 196-198 3-011(R) Me H H H C(O)NHMe 196-198 3-012 Me H H H C(O)(T-5) 221-222 3-013 Me H H H S(O)2Pr-c *2 3-014 Cl H H H C(O)OBu-t 97-99 3-015 Cl H H H C(O)OMe *2 3-016 Cl H H H C(O)Pr-c 242-244 3-017 Cl H H H S(O)2Et *2 3-018 Cl H H H C(O)NHMe 189-191 3-019 Cl H H H C(O)NMe2182-184 3-020 Cl H H H C(O)(T-5) 234-236 3-021 Cl H H H C(O)Me 234-236 3-022 Cl H H H S(O)2Me *2 3-023 Cl H H H S(O)2NMe2*2 3-023(S) Cl H H H S(O)2NMe2140-143 3-023(R) Cl H H H S(O)2NMe2140-143 3-024 Br H H H C(O)Me 209-211 3-025 Br H H H C(O)OBu-t *2 3-026 Br H H H C(O)(T-5) 213-215 3-027 Br H H H S(O)2Et 134-136 3-028 Br H H H C(O)Pr-c 234-236 3-029 Br H H H C(O)OMe 118-120 3-030 Br H H H C(O)NHMe 173-175 3-031 Br H H H S(O)2Me *2 3-032 Br H H H S(O)2NMe2*2 ―――――――――――――――――――――――――――――――――――― [Table 4]

[0358] [Chemistry]

[0359] ―――――――――――――――――――――――――――――――――――― No. Y 1 R 4 R 3 R 2 R 1 m.p.(℃) ―――――――――――――――――――――――――――――――――――― 4-001 Me H H H C(O)OBu-t 159-161 4-002 Me H H H C(O)OMe 100-102 4-002(S) Me H H H C(O)OMe *2 4-002(R) Me H H H C(O)OMe *2 4-003 Me H H H S(O)2Me 110-112 4-003(S) Me H H H S(O)2Me 208-210 4-003(R) Me H H H S(O)2Me 208-210 4-004 Me H H H C(O)NMe298-100 4-004(S) Me H H H C(O)NMe298-100 4-004(R) Me H H H C(O)NMe2105-107 4-005 Me H H H C(O)Me 176-178 4-005(S) Me H H H C(O)Me 164-166 4-005(R) Me H H H C(O)Me 196-198 4-006 Me H H H S(O)2Pr-c 125-127 4-007 Me H H H C(O)Pr-c *2 4-008 Me H H Me S(O)2Pr-c *2 4-009 Me H H H C(O)Et 184-186 4-010 Me H H H C(O)OEt *2 4-011 Me H H H C(O)NHMe 192-194 4-012 Me H H H C(O)CH2CH2SMe 163-164 4-013 Me H H H C(O)(4-CN-Ph) 210-212 4-014 Me H H H S(O)2CH2Cl 188-190 4-015 Me H H H C(O)N(Me)OMe *2 4-016 Me H H H C(S)NHMe *2 4-017 Me H H H C(O)N(Me)Et *2 4-018 Cl H H H C(O)Me 196-198 4-018(S) Cl H H H C(O)Me 192-194 4-018(R) Cl H H H C(O)Me 195-197 4-019 Cl H H H C(O)OBu-t 106-108 4-020 Me H H H S(O)2Et *2 4-020(S) Me H H H S(O)2Et 202-204 4-021 Me H H Me S(O)2Me *2 4-021(S) Me H H Me S(O)2Me *2 4-021(R) Me H H Me S(O)2Me *2 4-022 Me H H Me S(O)2Et *2 4-023 Me H H H C(O)(2,4-F2-Ph) 178-180 4-024 Me H H H C(O)Pr-n 208-210 4-025 Me H H H C(O)Pr-i 199-200 4-026 Cl H H H C(O)(4-CN-Ph) *2 4-027 Cl H H H S(O)2Me 199-201 4-028 Cl H H H C(O)Pr-c 96-98 4-029 Cl H H H C(O)Et 226-228 4-030 Cl H H H C(O)OMe *2 4-030(S) Cl H H H C(O)OMe *2 4-030(R) Cl H H H C(O)OMe *2 4-031 Cl H H H C(O)OEt *2 4-032 Cl H H H C(O)NHMe 179-181 4-033 Cl H H H C(O)NMe2*2 4-033(S) Cl H H H C(O)NMe2*2 4-034 Me H H H S(O)2(4-Me-Ph) 145-147 4-035 Me H H H S(O)2(4-CF3-Ph) 225-227 4-036 Me H H H S(O)2Pr-n *2 4-037 Me H H H C(O)(T-5) 206-209 4-038 Cl H H H C(O)(T-5) 192-196 4-039 Br H H H C(O)OBu-t 186-188 4-039(S) Br H H H C(O)OBu-t 109-111 4-040 Br H H H C(O)NHMe 172-174 4-041 Br H H H C(O)OMe *2 4-041(S) Br H H H C(O)OMe *2 4-042 Cl H H H S(O)2Et 186-188 4-042(S) Cl H H H S(O)2Et 194-196 4-042(R) Cl H H H S(O)2Et 194-196 4-043 Cl H H H S(O)2Pr-n 173-175 4-044 Me H H Me C(O)OMe 172-174 4-045 Me H H Et C(O)OMe 177-179 4-046 Me H Me H C(O)OMe *2 4-047 Me H Et H C(O)OMe *2 4-048 Me H H H S(O)2Pr-i *2 4-049 Cl H H H S(O)2Pr-c 189-191 4-050 Me H H H S(O)2NMe2123-125 4-050(S) Me H H H S(O)2NMe2192-194 4-051 Br H H H C(O)(T-5) 213-215 4-051(S) Br H H H C(O)(T-5) 202-204 4-052 Br H H H S(O)2Et *2 4-052(S) Br H H H S(O)2Et *2 4-053 Br H H H C(O)Pr-c 233-235 4-053(S) Br H H H C(O)Pr-c 204-206 4-054 Br H H H S(O)2NMe2*2 4-054(S) Br H H H S(O)2NMe2195-197 4-055 Br H H H S(O)2Me *2 4-055(S) Br H H H S(O)2Me *2 4-056 Br H H H C(O)Me 187-189 4-056(S) Br H H H C(O)Me 202-204 4-057 Cl H H H S(O)2NMe2*2 4-057(S) Cl H H H S(O)2NMe2202-204 4-058 H H H H C(O)OBu-t 104-106 4-059 H H H H C(O)(T-5) *2 4-060 H H H H S(O)2Me 237-239 4-061 H H H H S(O)2Pr-c 247-249 4-062 H H H H S(O)2Et 228-230 4-063 H H H H C(O)Pr-c *2 4-064 H H H H C(O)OMe 176-178 4-065 H H H H C(O)NHMe 196-198 ―――――――――――――――――――――――――――――――――――― [Table 5]

[0360] [Chem.]

[0361] ―――――――――――――――――――――――――――――――――――― No. Y 1 R 4 R 3R 2 R 1 m.p.(℃) ―――――――――――――――――――――――――――――――――――― 5-001 Me H H H C(O)OBu-t 159-161 5-002 Me H H H C(O)OMe 103-105 5-002(S) Me H H H C(O)OMe 186-188 5-002(R) Me H H H C(O)OMe 186-188 5-003 Me H H H S(O)2Me 107-109 5-004 Me H H H C(O)NMe2 107-109 5-005 Me H H H C(O)Me 171-173 5-006 Me H H H C(O)(T-5) 187-189 5-007 Me H H H C(O)NHMe 143-145 5-008 Me H H H C(O)Pr-c 207-208 5-009 Me H H H S(O)2Et *2 5-010 Me H H H S(O)2NMe2 *2 5-011 Cl H H H C(O)(T-5) 201-203 5-012 Cl H H H S(O)2Et 133-135 5-013 Cl H H H C(O)Pr-c 229-231 5-014 Cl H H H C(O)OMe *2 5-015 Cl H H H C(O)NHMe 187-189 5-016 Cl H H H S(O)2Me 143-145 ―――――――――――――――――――――――――――――――――――― [Table 6]

[0362]

Chem.

[0363] ―――――――――――――――――――――――――――――――――――― No. Y 1 R 4 R 3 R 2 R 1 m.p.(℃) ―――――――――――――――――――――――――――――――――――― 6-001 Me H H H C(O)OBu-t 166-168 6-002 Me H H H C(O)Me 197-199 6-003 Me H H H C(O)NMe284-86 6-004 Me H H H C(O)OMe 96-98 6-004(S) Me H H H C(O)OMe *2 6-004(R) Me H H H C(O)OMe *2 6-005 Me H H H S(O)2Me 112-114 6-006 Me H H H C(O)Pr-c 208-209 6-006(S) Me H H H C(O)Pr-c 227-229 6-006(R) Me H H H C(O)Pr-c 227-229 6-007 Me H H H C(O)(T-5) 186-188 6-008 Me H H H C(O)NHMe 184-186 6-008(S) Me H H H C(O)NHMe 194-196 6-008(R) Me H H H C(O)NHMe 189-191 6-009 Me H H H S(O)2Et 139-141 6-009(S) Me H H H S(O)2Et 93-96 6-009(R) Me H H H S(O)2Et 154-156 6-010 Me H H H S(O)2Pr-c 142-144 6-011 Cl H H H C(O)OBu-t 154-155 6-011(S) Cl H H H C(O)OBu-t *2 6-012 Cl H H H C(O)Me 193-196 6-012(S) Cl H H H C(O)Me 211-213 6-013 Cl H H H C(O)(T-5) 172-174 6-013(S) Cl H H H C(O)(T-5) 174-176 6-014 Cl H H H C(O)Pr-c 230-232 6-014(S) Cl H H H C(O)Pr-c 219-221 6-015 Cl H H H S(O)2Me *2 6-015(S) Cl H H H S(O)2Me *2 6-016 Cl H H H S(O)2Et *2 6-016(S) Cl H H H S(O)2Et *2 6-017 Cl H H H C(O)NHMe 170-172 6-017(S) Cl H H H C(O)NHMe 181-183 6-018 Cl H H H C(O)OMe 118-120 6-018(S) Cl H H H C(O)OMe *2 6-019 Cl H H H C(O)NMe2*2 6-020 Cl H H H S(O)2NMe2*2 6-020(S) Cl H H H S(O)2NMe2103-105 6-021 Me H H H S(O)2NMe2*2 6-021(S) Me H H H S(O)2NMe2172-174 6-022 Br H H H C(O)OBu-t 152-154 6-022(S) Br H H H C(O)OBu-t 97-99 6-023 Br H H H S(O)2NMe2*2 6-023(S) Br H H H S(O)2NMe2*2 6-024 Br H H H C(O)Me 222-224 6-025 Br H H H C(O)(T-5) 201-202 6-025(S) Br H H H C(O)(T-5) 206-208 6-026 Br H H H S(O)2Me *2 6-026(S) Br H H H S(O)2Me 128-130 6-027 Br H H H S(O)2Et *2 6-027(S) Br H H H S(O)2Et *2 6-028 Br H H H C(O)Pr-c 208-210 6-028(S) Br H H H C(O)Pr-c 229-230 6-029 Br H H H C(O)OMe *2 6-029(S) Br H H H C(O)OMe *2 6-030 Br H H H C(O)NHMe 173-175 6-030(S) Br H H H C(O)NHMe 182-183 ―――――――――――――――――――――――――――――――――――― [Table 7]

[0364] [Chemical formula]

[0365] ――――――――――――――――――――――――――――――――――――<​​​​​​​​​​m.p. (°C) ―――――――――――――――――――――――――――――――――――― 7-001 Me H H H C(O)OBu-t 91-93 7-002 Me H H H C(O)Me 151-153 7-003 Me H H H C(O)NMe2 101-103 7-004 Me H H H C(O)OMe 113-115 7-005 Me H H H S(O)2Me 119-121 7-006 Me H H H C(O)Pr-c 209-211 7-007 Me H H H C(O)(T-5) 194-196 7-008 Me H H H S(O)2Et *2 ―――――――――――――――――――――――――――――――――――― [Table 8]

[0366]

Chem.

[0367] ―――――――――――――――――――――――――――――――――――― No. Y 1 R 4 R 3 R A R 1 m.p. (°C) ―――――――――――――――――――――――――――――――――――― 8-001 Me H H Me C(O)OMe *2 8-002 Me H H Me S(O)2Me *2 8-002(S) Me H H Me S(O)2Me *2 8-003 Me H H Me C(O)NMe2 *2 8-003(S) Me H H Me C(O)NMe2 *2 8-004 Me H H Et C(O)NMe285-87 8-005 Me H H CH2CH=CH2C(O)NMe2*2 8-006 Me Me Me Me S(O)2Me *2 8-006(S) Me Me Me Me S(O)2Me *2 8-007 Me H H Et S(O)2Me 109-111 8-008 H H H Me S(O)2Me 88-90 8-009 Cl H H Me S(O)2Me *2 8-009(S) Cl H H Me S(O)2Me *2 8-009(R) Cl H H Me S(O)2Me *2 8-010 Br H H Me S(O)2Me *2 8-010(S) Br H H Me S(O)2Me *2 8-010(R) Br H H Me S(O)2Me *2 8-011 Me H H Me S(O)2Et *2 8-011(S) Me H H Me S(O)2Et *2 8-012 Me H Me Me S(O)2Me 105-107 8-012(S) Me H Me Me S(O)2Me *2 8-013 Me H Et Me S(O)2Me 102-104 8-013(S) Me H Et Me S(O)2Me *2 8-014 Me H H Me S(O)2Pr-c 214-216 8-014(S) Me H H Me S(O)2Pr-c *2 8-015 Me H H CH2CH=CH2S(O)2Me 95-97 8-016 Me H H CH2C≡CH S(O)2Me *2 8-017 Me H H CH2Pr-c S(O)2Me *2 8-018 Me H H CH2C(Me)=NOMe S(O)2Me *2 8-019 Me H H CH2Ph S(O)2Me *2 8-020 Me H H CH2(2-F-Ph) S(O)2Me *2 8-021 Me H H Pr-n S(O)2Me *2 8-022(S) Me H H Me S(O)2NMe2*2 8-023(S) Me H H Me C(O)Pr-c *2 8-024(S) Me H H Me C(O)(T-5) *2 8-025(S) Me H H Me C(O)Me 105-107 8-026 Me H H Et S(O)2Et 199-201 8-026(S) Me H H Et S(O)2Et *2 8-027(S) Me H H CH2CH=CH2S(O)2Et *2 8-028(S) Me H H CH2C≡CH S(O)2Et *2 8-029(S) Me H H CH2Pr-c S(O)2Et *2 8-030(S) Me H H CH2Ph S(O)2Et *2 8-031(S) Me H H Et S(O)2NMe2191-193 8-032(S) Me H H CH2OMe S(O)2Et *2 ―――――――――――――――――――――――――――――――――――― [Table 9]

[0368] [Chemical formula]

[0369] ―――――――――――――――――――――――――――――――――――― No. Y 1 R 4 R3 R A R 1 Melting point (°C) ―――――――――――――――――――――――――――――――――――― 9-001 Me H H Me C(O)NMe2 108-110 9-002 Me H H Me S(O)2Pr-c *2 9-003 Me H H Me S(O)2Me 175-177 9-003(S) Me H H Me S(O)2Me *2 9-003(R) Me H H Me S(O)2Me *2 9-004 Me H H Me S(O)2Et *2 ―――――――――――――――――――――――――――――――――――― [Table 10]

[0370]

Chem.

[0371] ―――――――――――――――――――――――――――――――――――― No. X 1 X 2 X 3 Y 1 R 1 Melting point (°C) ―――――――――――――――――――――――――――――――――――― 10-001 Cl H Cl Me S(O)2(D-14a) *2 10-002 Cl H Cl Me S(O)2(D-37a) 117-119 10-003 Cl H Cl Me C(O)(D-58a) *2 10-004 Cl H Cl Me C(O)(D-14a) *2 10-005 Cl H Cl Me C(O)(D-37a) 95-97 10-006 Cl H Cl Me C(O)(G-52a) 126-128 10-007 Cl H Cl Me C(O)(G-51a) 155-157 10-008 Cl H Cl Me C(O)(G-10a)(3-Me) 149-150 10-009 Cl H Cl Me C(O)(G-9a) 108-110 10-010 Cl H Cl Me C(O)(G-57a) 208-210 10-011 Cl H Cl Me C(O)(G-50a) 170-171 10-012 Cl H Cl Me C(O)(G-8a) 189-190 10-013 Cl H Cl Me C(O)(G-7a) 175-177 10-014 Cl H Cl Me C(O)(G-6a) 87-89 10-015 Cl H Cl Me C(O)(G-4a) 117-119 10-016 Cl H Cl Me C(O)(G-5a)(3-Br) 165-167 10-017 Cl H Cl Me C(O)(G-2a) 183-185 10-018 Cl H Cl Me C(O)(G-1a)(4-CF3) 203-205 10-019 Cl H Cl Me C(O)(G-25a) 211-213 10-020 Cl H Cl Me C(O)(G-26a) 131-133 10-021 Cl H Cl Me C(O)(G-27a) 240-241 10-022 Cl H Cl Me C(O)(G-22a) 188-190 10-023 Cl H Cl Me C(O)(G-23a) 140-142 10-024 Cl H Cl Me C(O)(G-24a) 163-165 10-025 Cl H Cl Me C(O)(G-9b) 232-234 10-026 Cl H Cl Me C(O)(G-12a)(5-Me) 122-124 10-027 Cl H Cl Me C(O)(G-15a)(4,5-Cl2) 106-108 10-028 Cl H Cl Me C(O)(D-30a) *2 10-029 Cl H Cl Me C(O)(G-17a) 148-150 10-030 Cl H Cl Me C(O)(G-13a)(3,5-Me2) *2 10-031 Cl H Cl Me C(O)(G-16a) 223-224 10-032 Cl H Cl Me C(O)(G-18a) *2 10-033 Cl H Cl Me C(O)CH2(G-21a) >300 10-034 Cl H Cl Me C(O)CH2(G-30a) 122-124 10-035 Cl H Cl Me C(O)CH2(G-11a) 131-133 10-036 Cl H Cl Me C(O)(D-3a) 94-96 10-037 Cl H Cl Me C(O)(G-14a) 127-129 10-038 Cl H Cl Me C(O)(G-20a) 202-204 10-039 Cl H Cl Me C(O)(G-19a) 234-236 10-040 Cl H Cl Me C(O)(G-55a) 102-104 10-041 Cl H Cl Me C(O)(G-56a) 219-221 10-042 Cl H Cl Me C(O)(G-58a) *2 10-043 Cl H Cl Me S(O)2(G-7a) 122-124 10-044 Cl H Cl Me S(O)2(G-9b)(3,5-Me2) *2 10-045 Cl H Cl Me C(O)(G-39a) *2 10-046 Cl H Cl Me C(O)(G-54a)(2-Cl) 117 - 119 10-047 Cl H Cl Me C(O)(G-53a) 112 - 114 10-048 Cl H Cl Me C(O)(D-2a) *2 10-049 Cl H Cl Me C(O)(D-23a) *2 10-050 Cl H Cl Me C(O)(G-51a)(2-Cl-6-CF3) *2 10-051 Cl H Cl Me C(O)(G-51a)(2-Br-6-CF3) *2 10-052 Cl H Cl Me C(O)(G-51a)(2-CH2OCH2CH2OMe-6-CF3) *2 10-053 Cl H Cl Me C(O)(G-51a)(2-Me-6-CF3) *2 10-054 Cl H Cl Me C(O)(G-51a)(2,6-Cl2) *2 10-055 Cl H Cl Me C(O)(G-51a)(2-Cl-6-Me) *2 10-056(S) Cl H Cl Me S(O)2(G-51a) 206 - 208 10-057(S) Cl H Cl Me S(O)2(G-8a) *2 ―――――――――――――――――――――――――――――――――――― [Table 11]

[0372] [Chemical formula]

[0373] ―――――――――――――――――――――――――――――――――――― No. Y 1 R 4 R 3 R 2 R 1m.p.(℃) ―――――――――――――――――――――――――――――――――――― 11-001 Me H H H C(O)OBu-t 155-157 11-001(S) Me H H H C(O)OBu-t 95-97 11-002 Me H H H C(O)Pr-c 187-189 11-002(S) Me H H H C(O)Pr-c 224-226 11-002(R) Me H H H C(O)Pr-c 227-229 11-003 Me H H H C(O)Et 176-178 11-004 Me H H H C(O)NHMe 190-192 11-004(S) Me H H H C(O)NHMe 194-196 11-004(R) Me H H H C(O)NHMe 201-203 11-005 Me H H H C(O)OMe *2 11-005(S) Me H H H C(O)OMe 151-154 11-005(R) Me H H H C(O)OMe 159-161 11-006 Me H H H S(O)2Me 153-155 11-007 Me H H H S(O)2Et 137-139 11-007(S) Me H H H S(O)2Et 154-156 11-008 Me H H H C(O)Me 179-181 11-009 Me H H H C(O)(T-5) 201-203 11-009(S) Me H H H C(O)(T-5) 206-208 11-010 Me H H H C(O)NMe2*2 11-011 Me H H H C(O)N(Me)Et *2 11-012 Me H H H C(O)N(Me)OMe *2 11-013 Me H H H S(O)2Pr-c *2 11-014 Me H H H S(O)2CF3186-188 11-015 Me H Me H C(O)OMe *2 11-016 Cl H H H C(O)OBu-t 94-96 11-016(S) Cl H H H C(O)OBu-t *2 11-017 Me H H Me C(O)OMe *2 11-018 Me H H Et C(O)OMe *2 11-019 Me H H CH2C≡CH C(O)OMe *2 11-020 Cl H H H C(O)Pr-c 217-219 11-020(S) Cl H H H C(O)Pr-c 229-232 11-021 Cl H H H C(O)OMe *2 11-021(S) Cl H H H C(O)OMe *2 11-022 Cl H H H S(O)2Et *2 11-022(S) Cl H H H S(O)2Et *2 11-023 Cl H H H C(O)NHMe 198-200 11-023(S) Cl H H H C(O)NHMe 187-189 11-024 Cl H H H C(O)NMe2*2 11-025 Cl H H H S(O)2Me *2 11-025(S) Cl H H H S(O)2Me 94-96 11-026 Me H H H S(O)2NMe2*2 11-026(S) Me H H H S(O)2NMe2*2 11-027 Cl H H H C(O)Me 201-203 11 - 027(S) Cl H H H C(O)Me 214 - 216 11 - 028 Cl H H H C(O)(T - 5) 181 - 183 11 - 028(S) Cl H H H C(O)(T - 5) 184 - 186 11 - 029 Cl H H H S(O)2NMe2*2 11 - 029(S) Cl H H H S(O)2NMe2 109 - 111 11 - 030(S) Br H H H C(O)OBu - t 99 - 101 11 - 031(S) Br H H H S(O)2Et *2 11 - 032(S) Br H H H C(O)(T - 5) 203 - 205 11 - 033(S) Br H H H C(O)Pr - c 234 - 235 11 - 034(S) Br H H H C(O)OMe *2 11 - 035(S) Br H H H C(O)NHMe 176 - 178 11 - 036(S) Br H H H S(O)2Me 126 - 128 11 - 037(S) Br H H H S(O)2NMe2*2 ―――――――――――――――――――――――――――――――――――― [Table 12]

[0374] [Chemical Structure]

[0375] ―――――――――――――――――――――――――――――――――――― No. Y 1 R 4 R 3 R 2 R 1 m.p.(℃) ―――――――――――――――――――――――――――――――――――― 12 - 001 Me H H H C(O)Me 214 - 216 12 - 002 Cl H H H C(O)Me 207 - 209 12 - 003 Me H H H C(O)OBu - t 157 - 159 12 - 004 Me H H H S(O)2NMe2*2 12 - 005 Me H H H C(O)(T - 5)*2 12 - 006 Me H H H S(O)2Et*2 12 - 007 Me H H H C(O)Pr - c*2 12 - 008 Me H H H C(O)OMe*2 12 - 008(S) Me H H H C(O)OMe 191 - 193 12 - 008(R) Me H H H C(O)OMe 187 - 189 12 - 009 Me H H H C(O)NHMe 127 - 128 12 - 010 Me H H H S(O)2Me*2 12 - 011 Cl H H H C(O)OBu - t 85 - 87 12 - 012 Cl H H H C(O)(T - 5) 206 - 208 12 - 013 Cl H H H S(O)2Et*2 12 - 014 Cl H H H C(O)Pr - c 226 - 228 12 - 015 Cl H H H C(O)OMe 119 - 121 12 - 016 Cl H H H C(O)NHMe 161 - 163 12 - 017 Cl H H H S(O)2Me*2 ―――――――――――――――――――――――――――――――――――― [Table 13]

[0376] [Chemistry]

[0377] ————————————————————————————————————————————————————————————————————— No. Y 1 R 4 R 3 R 2 R 1 m.p.(℃) ————————————————————————————————————————————————————————————————————— 13 - 001 Me H H H C(O)OBu - t 162 - 164 13 - 002 Me H H H C(O)(T - 5) *2 13 - 003 Me H H H C(O)Pr - c *2 13 - 004 Me H H H C(O)OMe *2 13 - 005 Me H H H S(O)2Et 109 - 111 13 - 006 Me H H H C(O)NMe2*2 13 - 007 Me H H H C(O)NHMe 144 - 146 13 - 008 Me H H H S(O)2Me *2 13 - 009 Me H H H C(O)Me 172 - 174 13 - 010 Cl H H H C(O)Me 184 - 186 13 - 011 Cl H H H C(O)(T - 5) 185 - 186 13 - 012 Cl H H H S(O)2Et *2 13 - 013 Cl H H H C(O)Pr - c 202 - 204 13 - 014 Cl H H H C(O)OMe *2 13 - 015 Cl H H H C(O)OBu - t 180 - 182 13 - 016 Cl H H H C(O)NHMe 154 - 156 13 - 017 Cl H H H S(O)2Me *2 ————————————————————————————————————————————————————————————————————— [Table 14] (这里推测是将“第14表”翻译为“Table 14”,因为文档中前面的“表”都是用“Table”表示,不确定是否符合原文准确意思,你可根据实际情况调整)

[0378] [Chemical formula]

[0379] ―――――――――――――――――――――――――――――――――――― No. Y 1 R 4 R 3 R 2 R 1 m.p.(°C) ―――――――――――――――――――――――――――――――――――― 14-001 Me H H H C(O)OBu-t 102-104 14-002 Me H H H C(O)(T-5) *2 14-003 Me H H H S(O)2Me *2 14-004 Me H H H S(O)2Et *2 ―――――――――――――――――――――――――――――――――――― [Table 15]

[0380] [Chemical formula]

[0381] ―――――――――――――――――――――――――――――――――――― No. X 1 X 2 X 3 R 1 m.p.(°C) ―――――――――――――――――――――――――――――――――――― 15-001 Cl H Cl C(O)OBu-t 116-118 15-002 Cl H Cl C(O)(T-5) *2 15-003 Cl H Cl C(O)Pr-c *2 15-004 Cl H Cl C(O)NHMe 223-225 15-005 Cl H Cl C(O)OMe *2 15-006 Cl H Cl S(O)2Me *2 15-007 Cl H Cl C(O)Me *2 [Table 16]

[0382] [ka]

[0383] ------------------------------------------------------------------ No. Y 1 R 4 R 3 R A R 1 mp(℃) ------------------------------------------------------------------ 16-001(S) Me HH Me S(O)2NMe2*2 16-002(S) Me HH Et S(O)2NMe2191-193 16-003(S) Me HH Me S(O)2Et *2 16-004 Me HH Et S(O)2Et 207-209 16-004(S) Me HH Et S(O)2Et *2 16-005(S) Me HH Me S(O)2Me *2 16-006(S) Me HH Et S(O)2Me *2 ------------------------------------------------------------------ Among the compounds of the present invention shown in Tables 1 to 16, compounds for which the melting point is not specified. 1 The 1H-NMR data is shown in Table 17.

[0384] [Table 17] --------------------------------------------------------------------------- No. 1H-NMR ――――――――――――――――――――――――――――――――――――― 1-007(S) (CDCl3, Me4Si, 300MHz) δ: 8.11 (d, J=8.1 Hz, 1H), 7.70-7.50 (m, 4H), 7.43 (dd, J=1.8, 1.8 Hz, 1H), 4.09 (d, J=17.4 Hz, 1H), 3.71 (d, J=17.4 Hz 1H), 3.32 (s, 3H), 3.04 (s, 3H), 2.57 (s, 3H). 1-010 (CDCl3, Me4Si, 300MHz) δ: 9.10-8.40 (m, 1H), 8.10-7.40 (m, 6H), 4.15-4.05 (m, 1H), 3.82 and 3.72 (s, 3H), 3.70 (d, J=17.4 Hz, 1H), 3.10-3.05 (m, 3H), 2.64 and 2.56 (s, 3H). 1-011 (CDCl3, Me4Si, 300MHz) δ: 9.10-8.45 (m, 1H), 8.05-7.40 (m, 6H), 4.15-4.05 (m, 1H), 3.82 and 3.72 (s, 3H), 3.70 (d, J=17.4 Hz, 1H), 3.60-3.45 (m, 2H), 2.63 and 2.57 (s, 3H), 1.30-1.20 (m, 3H). 1-012 (CDCl3, Me4Si, 300MHz) δ: 11.4 (s, 1H), 8.00-7.75 (m, 1H), 7.60-7.40 (m, 5H), 4.08 (d, J=17.7 Hz, 1H), 3.80-3.65 (m, 4H), 3.19 (s, 6H), 2.60-2.55 (m, 3H). 1-013 (CDCl3, Me4Si, 300MHz) δ: 9.03 and 8.35 (d, J=7.8 Hz, 1H), 8.05-7.20 (m, 6H), 4.45-4.30 (m, 1H), 4.15-4.05 (m, 1H), 3.81 and 3.72 (s, 3H), 3.70 (d, J=17.4 Hz, 1H), 2.63 and 2.57 (s, 3H), 1.29 and 1.28 (d, J=6.6 Hz, 6H). 1-014 (CDCl3, Me4Si, 300MHz) δ: 11.4 (s, 1H), 8.00-7.75 (m, 1H), 7.55-7.40 (m, 5H), 4.08 (d, J=17.4 Hz, 1H), 3.80-3.60 (m, 6H), 3.12 (s, 3H), 2.60-2.55 (m, 3H), 1.29 (t, J=7.2 Hz, 3H). 1-015 (CDCl3, Me4Si, 300MHz) δ: 9.20-8.55 (m, 1H), 8.05-7.40 (m, 6H), 4.15-4.05 (m, 1H), 3.83 and 3.71 (s, 3H), 3.7 (d, J=17.4 Hz, 1H), 3.40-3.35 (m, 2H), 2.62 and 2.58 (s, 3H), 1.20-1.05 (m, 1H), 0.65-0.55 (m, 2H), 0.35-0.25 (m, 2H). 1-016 (CDCl3, Me4Si, 300MHz) δ: 9.30-8.60 (m, 1H), 8.10-7.40 (m, 6H), 4.35-4.30 (m, 2H), 4.10-4.05 (m, 1H), 3.83 and 3.73 (s, 3H), 3.70 (d, J=17.4 Hz, 1H), 2.63 and 2.57 (s, 3H), 2.32 and 2.30 (t, J=2.7 Hz, 1H). 1-017 (CDCl3, Me4Si, 300MHz) δ: 11.36 (brs, 1H), 7.60-7.35 (m, 6H), 5.05-5.00 (m, 2H), 4.08 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4Hz, 1H), 2.65 (s, 3H), 1.33 (d, J=6.3 Hz, 12H). 1-018 (CDCl3, Me4Si, 300MHz) δ: 9.33 (brs, 1H), 8.80 (brs, 1H), 7.70 (d, J=8.1 Hz, 1H), 7.55-7.40 (m, 5H), 5.00-4.90 (m, 1H), 4.09 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 2.49 (s, 3H), 1.25 (d, J=6.6 Hz, 6H). 1-021 (CDCl3, Me4Si, 300MHz) δ: 9.55-8.80 (m, 1H), 8.05-7.40 (m, 6H), 4.30-4.05 (m, 3H), 3.86 and 3.74 (s, 3H), 3.70 (d, J=17.4 Hz, 1H), 2.61 and 2.59 (s, 3H). 1-022 (CDCl3, Me4Si, 300MHz) δ: 7.60-7.45 (m, 5H), 7.43 (dd, J=1.8, 1.8 Hz, 1H), 4.08 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 2.52 (s, 3H), 1.41 (s, 9H). 1-024 (CDCl3, Me4Si, 300MHz) δ: 7.69 (d, J=8.21 Hz, 1H), 7.55-7.50 (m, 4H), 7.43 (dd, J=2.1, 2.1 Hz, 1H), 4.30-4.25 (m, 2H), 4.08 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 3.65-3.60 (m, 2H), 3.39 (s, 3H), 2.53 (s, 3H). 1-025 (CDCl3, Me4Si, 300MHz) δ: 8.90 (s, 1H), 7.60-7.50 (m, 5H), 7.45-7.40 (m, 1H), 4.08 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 3.08 (q, J=7.2 Hz, 2H), 2.55 (s, 3H), 1.39 (t, J=7.2 Hz, 3H). 1-026 (CDCl3, Me4Si, 300MHz) δ: 8.84 (brs, 1H), 7.80-7.70 (m, 1H), 7.60-7.50 (m, 4H), 7.43 (dd, J=1.8, 1.8 Hz, 1H), 6.70-6.50 (m, 1H), 4.09 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 3.05-2.95 (m, 1H), 2.57 and 2.56 (s, 3H), 0.95-0.85 (m, 2H), 0.65-0.60 (m, 2H). 1-027 (CDCl3, Me4Si, 300MHz) δ: 7.67 (d, J=8.4 Hz, 1H), 7.60-7.50 (m, 4H), 7.43 (dd, J=1.8, 1.8 Hz, 1H), 4.08 (d, J=17.4 Hz, 1H), 3.89 (brs, 1H), 3.70 (d, J=17.4 Hz, 1H), 2.54 (s, 3H), 1.16 (d, J=6.3 Hz, 6H). 1-028 (CDCl3, Me4Si, 300MHz) δ: 9.29 (brs, 1H), 9.13 (brs, 1H), 7.65-7.40 (m, 6H), 4.53 (s, 2H), 4.08 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 2.56 (s, 3H). 1-029 (CDCl3, Me4Si, 300MHz) δ: 7.63 (d, J=8.1 Hz, 1H), 7.55-7.50 (m, 4H), 7.23 (dd, J=1.8, 1.8 Hz, 1H), 5.06 (brs, 1H), 4.08 (d, J=17.4 Hz, 1H), 3.69 (d, J=17.4 Hz, 1H), 2.53 (s, 3H). 1-030 (CDCl3, Me4Si, 300MHz) δ: 8.86 (s, 1H), 7.60-7.50 (m, 5H), 7.43 (dd, J=1.8, 1.8 Hz, 1H), 4.08 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 3.25-3.15 (m, 1H), 2.55 (s, 3H), 1.39 (d, J=6.6 Hz, 6H). 1-030(S) (CDCl3, Me4Si, 300MHz) δ: 8.88 (s, 1H), 7.65-7.40 (m, 6H), 4.15-4.05 (m, 1H), 3.70 (d, J=17.5 Hz, 1H), 3.25-3.10 (m, 1H), 2.55 (s, 3H), 1.39 (d, J=6.9Hz, 6H). 1-036 (CDCl3, Me4Si, 300MHz) δ: 11.13 (s, 1H), 9.02 (d, J=7.5 Hz, 1H), 7.65-7.50 (m, 5H), 7.42 (dd, J=1.8, 1.8 Hz, 1H), 4.20-4.05 (m, 2H), 3.70 (d, J=17.4 Hz, 1H), 3.04 (s, 3H), 2.56 (s, 3H), 1.29 (d, J=6.3 Hz, 6H). 1-037 (CDCl3, Me4Si, 300MHz) δ: 11.15 (s, 1H), 9.32 (t, J=5.1 Hz, 1H), 7.65-7.40 (m, 6H), 4.20 (dd, J=2.4, 5.1 Hz, 2H), 4.09 (d, J=17.4 Hz, 1H), 3.72 (d, J=17.4 Hz, 1H), 3.07 (s, 3H), 2.56 (s, 3H), 2.34 (t, J=2.4 Hz, 1H). 1-041 (CDCl3, Me4Si, 300MHz) δ: 9.66 (s, 1H), 9.23 (d, J=2.7 Hz, 1H), 7.83 (brs, 1H), 7.70-7.40 (m, 6H), 4.09 (d, J=17.4 Hz, 1H), 3.71 (d, J=17.4 Hz, 1H), 2.53 (s, 3H), 1.80 (brs, 1H), 1.46 (s, 9H). 1-042 (CDCl3, Me4Si, 300MHz) δ: 8.88 (s, 1H), 7.60-7.55 (m, 3H), 7.50-7.45 (m, 2H), 7.43 (dd, J=2.1, 2.1 Hz, 1H), 4.08 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 3.05-3.00 (m, 2H), 2.55 (s, 3H), 1.90-1.85 (m, 2H), 1.06 (t, J=7.2 Hz, 3H). 1-045 (CDCl3, Me4Si, 300MHz) δ: 9.10-8.45 (m, 1H), 8.15-7.20 (m, 6H), 4.15-4.05 (m, 1H), 3.80-3.65 (m, 4H), 3.10-3.00 (m, 1H), 2.67 and 2.55 (s, 3H), 1.66 (s, 1H), 0.95-0.85 (m, 2H), 0.70-0.65 (m, 2H). 1-046 (CDCl3, Me4Si, 300MHz) δ: 9.35-8.75 (m, 1H), 8.05-7.40 (m, 6H), 4.15-4.05 (m, 1H), 3.80-3.55 (m, 8H), 3.41 and 3.40 (s, 3H), 2.62 and 2.57 (s, 3H), 1.70 (s, 1H). 1-047 (CDCl3, Me4Si, 300MHz) δ: 9.45-8.75 (m, 1H), 8.15-7.40 (m, 6H), 4.40 (dd, J=6.0, 6.0 Hz, 2H), 4.15-4.05 (m, 1H), 3.86 ans 3.76 (s, 3H), 3.71 (d, J=17.4 Hz, 1H), 2.64 and 2.57 (s, 3H), 1.67 (brs, 1H). 1-048 (CDCl3, Me4Si, 300MHz) δ: 8.90-8.85 (m, 1H), 7.70-7.45 (m, 6H), 6.00-5.80 (m, 2H), 5.35-5.10 (m, 4H), 4.20-4.00 (m, 3H), 3.90-3.80 (m, 2H), 3.69 (d, J=17.4 Hz, 1H), 2.63 and 2.56 (s, 3H). 1-049 (CDCl3, Me4Si, 300MHz) δ: 9.20-8.55 (m, 1H), 7.70-7.40 (m, 6H), 6.00-5.80 (m, 1H), 5.35-5.10 (m, 2H), 4.20-4.00 (m, 3H), 3.84 and 3.72 (s, 3H), 3.70-3.65 (m, 1H), 2.62 and 2.55 (s, 3H). 1-050 (CDCl3, Me4Si, 300MHz) δ: 10.04 (s, 1H), 9.57 and 8.72 (s, 1H), 7.65-7.35 (m, 6H), 4.08 (d, J=17.4 Hz, 1H), 3.92 and 3.89 (s, 3H), 3.79 (s, 3H), 3.70 (d, J=17.4 H, 1H), 2.56 and 2.53 (s, 3H). 1-051 (CDCl3, Me4Si, 300MHz) δ: 7.90-7.60 (m, 3H), 7.50-7.40 (m, 3H), 4.07 (d, J=17.4 Hz, 1H), 3.69 (d, J=17.4 Hz, 1H), 1.50-1.45 (m, 9H). 1-051(S) (CDCl3, Me4Si, 400MHz) δ: 8.83 (brs, 1H), 8.67 (brs, 1H), 7.80 (d, J=8.0 Hz, 1H), 7.67 (d, J=1.6 Hz, 1H),7.60 (dd, J=1.6, 8.0 Hz, 1H), 7.50 (d, J=2.0 Hz, 2H), 7.44 (dd, J=2.0, 2.0 Hz, 1H), 4.07 (d, J=17.2 Hz, 1H), 3.69 (d, J=17.2 Hz, 1H), 1.51 (s, 9H). 1-052(S) (CDCl3, Me4Si, 400MHz) δ: 8.85 (brs, 1H), 8.66 (s, 1H), 7.85 (d, J=1.6 Hz, 1H), 7.77 (d, J=8.0 Hz, 1H), 7.65 (dd, J=1.6, 8.0 Hz, 1H), 7.50 (d, J=1.6 Hz, 2H), 7.44 (dd, J=1.6, 1.6 Hz, 1H), 4.07 (d, J=17.2 Hz, 1H), 3.69 (d, J=17.2 Hz, 1H), 1.51 (s, 9H). 1-058 (CDCl3, Me4Si, 300MHz) δ: 7.75-7.40 (m, 11H), 4.08 (d, J=17.4 Hz, 1H), 3.69 (d, J=17.4 Hz, 1H), 2.60-2.50 (m, 3H). 1-060 (CDCl3, Me4Si, 300MHz) δ: 9.15-8.90 (m, 2H), 7.80-7.65 (m, 3H), 7.60-7.50 (m, 1H), 7.50-7.45 (m, 2H), 7.45-7.30 (m, 1H), 4.08 (d, J=17.4 Hz, 1H), 3.71 (d, J=17.4 Hz, 1H), 3.00 (s, 3H). 1-061 (CDCl3, Me4Si, 300MHz) δ: 9.15-8.85 (m, 2H), 7.94 (d, J=1.5 Hz, 1H), 7.75 (dd, J=1.5, 8.1 Hz, 1H), 7.64 (d, J=8.1 Hz, 1H), 7.55-7.40 (m, 4H), 4.07 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 3.00 (s, 3H). 1-063 (CDCl3, Me4Si, 300MHz) δ: 7.70-7.65 (m, 1H), 7.55-7.50 (m, 4H), 7.45-7.40 (m, 1H), 4.08 (d, J=17.4 Hz, 1H), 3.69 (d, J=17.4 Hz, 1H), 3.18 (q, J=7.5 Hz, 4H), 2.76 (s, 6H), 2.54 (s, 3H), 1.13 (t, J=7.5 Hz, 6H). 1-064 (CDCl3, Me4Si, 300MHz) δ: 8.77 (brs, 1H), 7.60-7.50 (m, 5H), 7.45-7.40 (m, 1H), 4.20-4.05 (m, 2H), 3.75-3.65 (m, 1H), 2.71 (s, 3H), 2.54 (s, 3H), 1.16 (d, J=6.9 Hz, 6H). 1-065 (CDCl3, Me4Si, 300MHz) δ: 9.40 (brs, 1H), 8.37 (brs, 1H), 7.70-7.65 (m, 1H), 7.60-7.50 (m, 4H), 7.45-7.35 (m, 1H), 4.70-4.55 (m, 1H), 4.08 (d, J=17.4 Hz, 1H), 3.69 (d, J=17.4 Hz, 1H), 2.95-2.70 (m, 3H), 2.54 (s, 3H), 1.13 (d, J=6.9 Hz, 6H). 1-068 (CDCl3, Me4Si, 300MHz) δ: 9.36 (brs, 1H), 7.70-7.15 (m, 7H), 4.06 (d, J=17.4 Hz, 1H), 3.68 (d, J=17.4 Hz, 1H), 3.05 (s, 6H). 1-069 (CDCl3, Me4Si, 300MHz) δ: 9.40-8.70 (m, 1H), 8.00-7.40 (m, 6H), 4.06 (d, J=17.4 Hz, 1H), 3.69 (d, J=17.4 Hz, 1H), 3.15-2.95 (m, 9H), 2.64 and 2.53 (s, 3H). 1-070 (CDCl3, Me4Si, 300MHz) δ: 9.45-8.70 (m, 1H), 8.00-7.45 (m, 5H), 7.45-7.40 (m, 1H), 4.06 (d, J=17.4 Hz, 1H), 3.69 (d, J=17.4 Hz, 1H), 3.60-3.40 (m, 2H), 3.15-2.95 (m, 6H), 2.63 and 2.54 (s, 3H), 1.30-1.20 (m, 3H). 1-071 (CDCl3, Me4Si, 300MHz) δ: 9.39 (brs, 1H), 8.36 (brs, 1H), 7.70-7.65 (m, 1H), 7.60-7.50 (m, 4H), 7.45-7.40 (m, 1H), 4.08 (d, J=17.4 Hz, 1H), 3.69 (d, J=17.4 Hz, 1H), 3.08 (q, J=.7.2 Hz, 2H), 2.76 (s, 3H), 2.54 (s, 3H), 1.13 (t, J=7.2 Hz, 3H). 1-072 (CDCl3, Me4Si, 300MHz) δ: 8.81 (s, 1H), 7.60-7.45 (m, 5H), 7.45-7.40 (m, 1H), 4.08 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 3.17 (q, J=7.2 Hz, 2H), 2.78 (s, 3H), 2.54 (s, 3H), 1.19 (t, J=7.2 Hz, 3H). 1-075 (CDCl3, Me4Si, 300MHz) δ: 12.18 (brs, 1H), 8.20 (brs, 1H), 7.90-7.50 (m, 5H), 7.42 (dd, J=1.8, 1.8 Hz, 1H), 4.09 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 2.70-2.60 (m, 7H), 1.24 (t, J=7.5 Hz, 6H). 1-077 (CDCl3, Me4Si, 300MHz) δ: 12.15 (brs, 1H), 8.29 (brs, 1H), 7.55-7.45 (m, 5H), 7.42 (dd, J=1.5, 1.5 Hz, 1H), 4.09 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 2.65-2.55 (m, 7H), 1.80-1.70 (m, 4H), 1.01 (t, J=7.5 Hz, 6H). 1-080 (CDCl3, Me4Si, 300MHz) δ: 9.39 (brs, 2H), 7.93 (d, J=7.8 Hz, 1H), 7.55-7.45 (m, 4H), 7.43 (dd, J=1.8, 1.8 Hz, 1H), 4.09 (d, J=17.4 Hz, 1H), 4.04 (s, 2H), 3.70 (d, J=17.4 Hz, 1H), 3.50 (s, 3H), 2.60 (s, 3H). 1-082 (CDCl3, Me4Si, 300MHz) δ: 12.30 (brs, 1H), 8.38 (brs, 1H), 7.55-7.45 (m, 5H), 7.42 (dd, J=1.8, 1.8 Hz, 1H), 4.09 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 2.85-2.75 (m, 2H), 2.67 (s, 3H), 1.30-1.25 (m, 12H). 1-083 (CDCl3, Me4Si, 300MHz) δ: 7.85-7.80 (m, 1H), 7.55-7.45 (m, 4H), 7.45-7.50 (m, 1H), 6.07 (s, 1H), 5.68 (d, J=1.5 Hz, 1H), 4.09 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 2.57 (s, 3H), 2.05-2.00 (m, 3H). 1-086 (CDCl3, Me4Si, 300MHz) δ: 8.15-8.05 (m, 2H), 7.85-7.40 (m, 6H), 7.00-6.90 (m, 4H), 4.09 (d, J=17.4 Hz, 1H), 3.71 (d, J=17.4 Hz, 1H), 2.65-2.55 (m, 3H). 1-088 (CDCl3, Me4Si, 300MHz) δ: 8.06 (d, J=8.1 Hz, 1H), 7.60-7.40 (m, 6H), 4.09 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 3.47 (s, 3H), 3.18 (s, 3H), 2.64 (s, 3H). 1-088(S) (CDCl3, Me4Si, 300MHz) δ: 8.06 (d, J=8.1 Hz, 1H), 7.60-7.40 (m, 6H), 4.09 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 3.47 (s, 3H), 3.18 (s, 3H), 2.64 (s, 3H). 1-098 (CDCl3, Me4Si, 300MHz) δ: 10.62 (s, 1H), 9.00 (d, J=9.0 Hz, 1H), 7.65-7.40 (m, 6H), 5.04 (d, J=8.4 Hz, 1H), 4.06 (d, J=17.4 Hz, 1H), 3.80-3.60 (m, 3H), 2.55 (s, 3H), 2.00-1.90 (m, 4H), 1.75-1.55 (m, 6H), 1.50-1.15 (m, 10H). 1-114 (CDCl3, Me4Si, 300MHz) δ: 7.80-7.70 (m, 1H), 7.60-7.50 (m, 4H), 7.43 (dd, J=1.8, 1.8 Hz, 1H), 4.09 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 2.57 and 2.55 (s, 3H), 2.10-2.00 (m, 1H), 1.75-1.15 (m, 10H). 1-115 (CDCl3, Me4Si, 300MHz) δ: 8.50 (brs, 1H), 7.60-7.20 (m, 11H), 5.61 (brs, 1H), 4.37 (d, J=6.0 Hz, 2H), 4.06 (d, J=17.4 Hz, 1H), 3.67 (d, J=17.4 Hz, 1H), 2.51 (s, 3H). 1-116 (CDCl3, Me4Si, 300MHz) δ: 8.96 (brs, 1H), 8.00-7.40 (m, 6H), 5.20 (brs, 1H), 4.15-4.05 (m, 1H), 3.75-3.50 (m, 5H), 2.63 and 2.57 (s, 3H). 1-119 (CDCl3, Me4Si, 300MHz) δ: 8.77 (brs, 1H), 7.65-7.55 (m, 3H), 7.55-7.50 (m, 2H), 7.43 (dd, J=1.8, 2.1 Hz, 1H), 7.05-7.00 (m, 3H), 6.50-6.45 (m, 1H), 4.09 (d, J=17.4 Hz, 1H), 3.71 (d, J=17.4 Hz, 1H), 2.57 (s, 3H). 1-120 (CDCl3, Me4Si, 300MHz) δ: 8.45 (brs, 1H), 7.65-7.50 (m, 5H), 7.43 (dd, J=1.8, 1.8 Hz, 1H), 6.65 (brs, 1H), 4.08 (d, J=17.4 Hz, 1H), 3.69 (d, J=17.4 Hz, 1H), 3.45-3.25 (m, 7H), 2.52 (s, 3H). 1-123 (CDCl3, Me4Si, 300MHz) δ: 9.36 (brs, 1H), 8.32 (brs, 1H), 7.70-7.65 (m, 1H), 7.55-7.50 (m, 4H), 7.42 (dd, J=1.8, 1.8 Hz, 1H), 4.08 (d, J=17.4 Hz, 1H), 3.69 (d, J=17.4 Hz, 1H), 3.55-3.25 (m, 4H), 2.54 (s, 3H), 1.30-1.05 (m, 6H). 1-124 (CDCl3, Me4Si, 300MHz) δ: 9.00 (brs, 1H), 7.80 (d, J=8.7 Hz, 1H), 7.55-7.50 (m, 4H), 7.42 (dd, J=1.8, 1.8 Hz, 1H), 4.08 (d, J=17.4 Hz, 1H), 3.79 (s, 3H), 3.70 (d, J=17.4 Hz, 1H), 3.23 (s, 3H), 2.57 (s, 3H). 1-126 (CDCl3, Me4Si, 300MHz) δ: 9.57 (brs, 1H), 8.85 (brs, 1H), 7.65-7.50 (m, 3H), 7.50-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.09 (d, =17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 2.56 (s, 3H). 1-127 (CDCl3, Me4Si, 300MHz) δ: 9.43 (brs, 1H), 8.83 (brs, 1H), 7.65-7.50 (m, 5H), 7.43 (dd, J=1.8, 1.8 Hz, 1H), 5.80 (t, J=55.2 Hz, 1H), 4.09 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 2.57 (s, 3H). 1-131(S) (CDCl3, Me4Si, 400MHz) δ: 9.25-9.00 (m, 2H), 7.60-7.40 (m, 6H), 4.85-4.75 (m, 1H), 4.08 (d, J=17.2 Hz, 1H), 3.72 (d, J=17.2 Hz, 1H), 2.72 (d, J=5.2 Hz, 3H), 2.49 (s, 3H). 1-137 ((CD3)2SO, Me4Si, 300MHz) δ: 7.85-7.75 (m, 2H), 7.65-7.60 (m, 4H), 4.45-4.25 (m, 4H), 3.70-3.55 (m, 1H), 2.50-2.45 (m, 3H), 1.29 (d, J=6.9 Hz, 6H). 1-140 (CDCl3, Me4Si, 400MHz) δ: 10.28 (brs, 1H), 7.94 (d, J=8.0 Hz, 1H), 7.68 (d, J=1.2 Hz, 1H), 7.62 (dd, J=1.2, 8.0 Hz, 1H), 7.51 (d, J=1.6 Hz, 2H), 7.44 (dd, J=1.6, 1.6 Hz, 1H), 4.08 (d, J=17.2 Hz, 1H), 3.70 (d, J=17.2 Hz, 1H), 3.46 (s, 3H), 3.19 (s, 3H). 1-142(S) (CDCl3, Me4Si, 400MHz) δ: 7.75-7.40 (m, 6H), 4.15-4.05 (m, 1H), 3.72 (d, J=17.3 Hz, 1H), 2.51 (s, 3H). 1-143 (CDCl3, Me4Si, 300MHz) δ: 10.24 (brs, 1H), 7.95-7.85 (m, 2H), 7.67 (dd, J=1.8, 8.1 Hz, 1H), 7.50-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.07 (d, J=17.4 Hz, 1H), 3.69 (d, J=17.4 Hz, 1H), 3.46 (s, 3H), 3.19 (s, 3H). 1-143(S) (CDCl3, Me4Si, 400MHz) δ: 10.23 (brs, 1H), 7.95-7.65 (m, 3H), 7.55-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.07 (d, J=17.2 Hz, 1H), 3.70 (d, J=17.2 Hz, 1H), 3.45 (s, 3H), 3.18 (s, 3H). 1-143(R) (CDCl3, Me4Si, 400MHz) δ: 10.23 (brs, 1H), 7.95-7.65 (m, 3H), 7.55-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.07 (d, J=17.2 Hz, 1H), 3.70 (d, J=17.2 Hz, 1H), 3.45 (s, 3H), 3.18 (s, 3H). 1-144 (CDCl3, Me4Si, 300MHz) δ: 7.75-7.70 (m, 1H), 7.55-7.50 (m, 4H), 7.45-7.40 (m, 1H), 6.40-6.35 (m, 1H), 4.09 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 2.57 (s, 3H), 2.25 (s, 3H). 1-145(S) (CDCl3, Me4Si, 300MHz) δ: 7.65-7.55 (m, 3H), 7.55-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.15-4.00 (m, 1H), 3.85 (s, 3H), 3.75-3.65 (m, 1H), 3.15 (s, 3H), 2.60 (s, 3H). 1-146 ((CD3)2SO, Me4Si, 300MHz) δ: 11.32 (brs, 1H), 9.84 (s, 1H), 7.96 (d, J=8.4 Hz, 1H), 7.82 (dd, J=2.1, 2.1 Hz, 1H), 7.65-7.55 (m, 5H), 6.78 (s, 1H), 4.45-4.25 (m, 2H), 2.57 (s, 3H), 1.47 (s, 3H). 1-149 (CDCl3, Me4Si, 300MHz) δ: 10.34 (brs, 2H), 8.07 (d, J=8.1 Hz, 1H), 7.81 (brs, 1H), 7.55-7.40 (m, 4H), 4.10 (d, J=17.4 Hz, 1H), 3.71 (d, J=17.4 Hz, 1H), 3.48 (s, 3H), 2.80-2.70 (m, 1H), 2.65 (s, 3H), 1.40-1.35 (m, 2H), 1.20-1.15 (m, 2H). 1-149(S) (CDCl3, Me4Si, 400MHz) δ: 10.34 (brs, 1H), 8.07 (d, J=8.0 Hz, 1H), 7.79 (brs, 1H), 7.55-7.40 (m, 5H), 4.10 (d, J=17.2 Hz, 1H), 3.71 (d, J=17.2 Hz, 1H), 3.48 (s, 3H), 2.80-2.70 (m, 1H), 2.64 (s, 3H), 1.40-1.35 (m, 2H), 1.20-1.10 (m, 2H). 1-157 (CDCl3, Me4Si, 400MHz) δ: 9.07 (brs, 1H), 8.85 (s, 1H), 7.80-7.75 (m, 2H), 7.70-7.65 (m, 1H), 7.50 (d, J=1.6 Hz, 2H), 7.45-7.40 (m, 1H), 4.08 (d, J=17.2 Hz, 1H), 3.71 (d, J=17.2 Hz, 1H), 3.07 (q, J=7.2 Hz, 2H), 1.38 (t, J=7.2 Hz, 3H). 1-158 (CDCl3, Me4Si, 300MHz) δ: 8.83 (s, 1H), 7.80-7.70 (m, 2H), 7.69 (dd, J=1.2, 7.8 Hz, 1H), 7.49 (d, J=1.2 Hz, 2H), 7.45-7.40 (m, 1H), 4.07 (d, J=17.4 Hz, 1H), 3.69 (d, J=17.4 Hz, 1H), 2.60-2.50 (m, 1H), 1.30-1.15 (m, 2H), 1.00-0.95 (m, 2H). 1-159 (CDCl3, Me4Si, 300MHz) δ: 8.77 (s, 1H), 7.95 (d, J=1.5 Hz, 1H), 7.74 (dd, J=1.5, 8.1 Hz, 1H), 7.64 (d, J=8.1 Hz, 1H), 7.49 (d, J=1.2 Hz, 2H), 7.45-7.40 (m, 1H), 4.07 (d, J=17.4 Hz, 1H), 3.69 (d, J=17.4 Hz, 1H), 2.60-2.50 (m, 1H), 1.25-1.20 (m, 2H), 1.05-0.95 (m, 2H). 1-160 (CDCl3, Me4Si, 300MHz) δ: 10.32 (brs, 1H), 9.19 (brs, 1H), 8.41 (brs, 1H), 7.65-7.60 (m, 3H), 7.55-7.50 (m, 2H), 7.45-7.40 (m, 1H), 4.09 (d, J=17.4 Hz, 1H), 3.71 (d, J=17.4 Hz, 1H), 2.55 (s, 3H), 1.65-1.60 (m, 2H), 1.55-1.50 (m, 2H). 1-161 (CDCl3, Me4Si, 300MHz) δ: 7.65-7.60 (m, 3H), 7.55-7.50 (m, 2H), 7.45-7.40 (m, 1H), 4.10 (d, J=17.4 Hz, 1H), 3.72 (d, J=17.4 Hz, 1H), 2.53 (s, 3H), 2.22 (s, 3H). 1-163 (CDCl3, Me4Si, 300MHz) δ: 9.66 (brs, 2H), 7.65-7.60 (m, 1H), 7.55-7.50 (m, 4H), 7.43 (dd, J=1.8, 1.8 Hz, 1H), 4.08 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 2.45-2.35 (m, 4H), 2.20-2.10 (m, 1H), 1.75-1.65 (m, 1H). 1-168 (CDCl3, Me4Si, 300MHz) δ: 8.05-7.95 (m, 2H), 7.85-7.75 (m, 1H), 7.65-7.50 (m, 4H), 7.45-7.40 (m, 1H), 7.00-6.90 (m, 2H), 4.15-4.05 (m, 1H), 3.88 (s, 3H), 3.75-3.70 (m, 1H), 2.65-2.55 (m, 3H). 1-170 (CDCl3, Me4Si, 300MHz) δ: 8.00-7.95 (m, 3H), 7.65-7.50 (m, 4H), 7.45-7.40 (m, 1H), 7.35-7.25 (m, 2H), 4.15-4.05 (m, 1H), 3.75-3.65 (m, 1H), 2.65-2.50 (m, 6H). 1-171 (CDCl3, Me4Si, 300MHz) δ: 9.24 (brs, 1H), 8.10-7.95 (m, 2H), 7.70-7.60 (m, 4H), 7.55-7.50 (m, 2H), 7.50-7.40 (m, 1H), 4.10 (d, J=17.4 Hz, 1H), 3.72 (d, J=17.4 Hz, 1H), 2.59 (s, 3H). 1-172 (CDCl3, Me4Si, 300MHz) δ: 9.16 (brs, 1H), 8.50-8.45 (m, 1H), 8.40-8.30 (m, 1H), 7.80-7.50 (m, 7H), 7.44 (dd, J=1.5, 1.5Hz, 1H), 4.10 (d, J=17.4 Hz, 1H), 3.72 (d, J=17.4 Hz, 1H), 2.59 (s, 3H). 1-173 (CDCl3, Me4Si, 300MHz) δ: 8.00-7.95 (m, 1H), 7.90-7.80 (m, 2H), 7.70-7.50 (m, 5H), 7.45-7.40 (m, 1H), 4.09 (d, J=17.4 Hz, 1H), 3.71 (d, J=17.4 Hz, 1H), 3.06 (s, 3H), 2.56 (s, 3H). 1-174(S) (CDCl3, Me4Si, 300MHz) δ: 11.00 (s, 1H), 9.10-9.00 (m, 1H), 7.65-7.50 (m, 3H), 7.55-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.15-4.00 (m, 1H), 3.75-3.65 (m, 1H), 3.05-2.95 (m, 3H), 2.75 (s, 6H), 2.55 (s, 3H). 1-178 (CDCl3, Me4Si, 300MHz) δ: 7.80-7.75 (m, 1H), 7.70-7.60 (m, 1H), 7.55-7.45 (m, 4H), 7.45-7.40 (m, 3H), 7.40-7.30 (m, 1H), 4.09 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 2.54 (s, 3H). 1-181 (CDCl3, Me4Si, 300MHz) δ: 9.35 (brs, 1H), 8.50 (brs, 1H), 8.35 (s, 1H), 7.91 (dd, J=0.9, 7.8 Hz, 1H), 7.81 (d, J=7.8 Hz 1H), 7.70-7.55 (m, 3H), 7.55-7.50 (m, 2H), 7.44 (dd, J=1.8, 1.8 Hz, 1H), 4.10 (d, J=17.4 Hz, 1H), 3.71 (d, J=17.4 Hz, 1H), 3.43 (s, 3H), 2.58 (s, 3H). 1-182 (CDCl3, Me4Si, 300MHz) δ: 9.34 (brs, 1H), 8.45 (brs, 1H), 8.34 (d, J=1.8 Hz, 1H), 8.17 (dd, J=1.8, 8.1 Hz, 1H), 7.99 (d, J=7.8 Hz, 1H), 7.65-7.55 (m, 3H), 7.55-7.50 (m, 2H), 7.43 (dd, J=1.8, 1.8 Hz, 1H), 4.09 (d, J=17.4 Hz, 1H), 3.71 (d, J=17.4 Hz, 1H), 3.11 (s, 3H), 2.58 (s, 3H). 1-183 (CDCl3, Me4Si, 300MHz) δ: 7.80-7.70 (m, 2H), 7.55-7.50 (m, 4H), 7.43 (dd, J=1.8, 1.8 Hz, 1H), 7.17 (dd, J=2.1, 10.8 Hz, 1H), 7.10-7.00 (m, 1H), 4.09 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 2.54 (s, 3H). 1-187 (CDCl3, Me4Si, 400MHz) δ: 9.12 (brs, 1H), 7.80-7.65 (m, 3H), 7.55-7.50 (m, 2H), 7.45-7.40 (m, 1H), 4.08 (d, J=17.2 Hz, 1H), 3.71 (d, J=17.2 Hz, 1H), 1.65-1.50 (m, 4H). 1-189 (CDCl3, Me4Si, 400MHz) δ: 9.15-8.90 (m, 2H), 7.95 (d, J=1.2 Hz, 1H), 7.75 (dd, J=1.2, 8.4 Hz, 1H), 7.66 (d, J=8.0 Hz, 1H), 7.55-7.50 (m, 2H), 7.45-7.40 (m, 1H), 4.08 (d, J=17.2 Hz, 1H), 3.70 (d, J=17.2 Hz, 1H), 1.65-1.50 (m, 4H). 1-190 (CDCl3, Me4Si, 300MHz) δ: 9.26 (brs, 1H), 8.81 (s, 1H), 7.94 (s, 1H), 7.75-7.70 (m, 1H), 7.65-7.40 (m, 5H), 4.07 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 3.06 (q, J=7.5 Hz, 2H), 1.37 (t, J=7.5 Hz, 3H). 1-190(R) (CDCl3, Me4Si, 400MHz) δ: 8.78 (s, 1H), 8.00-7.90 (m, 1H), 7.80-7.60 (m, 2H), 7.55-7.40 (m, 3H), 4.07 (d, J=17.2 Hz, 1H), 3.70 (d, J=17.2 Hz, 1H), 3.09 (q, J=7.2 Hz, 2H), 1.39 (t, J=7.2 Hz, 3H). 1-191 (CDCl3, Me4Si, 300MHz) δ: 9.11 (brs, 1H), 8.79 (s, 1H), 7.95-7.90 (m, 1H), 7.75-7.70 (m, 1H), 7.65-7.40 (m, 5H), 4.07 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 3.10-2.95 (m, 2H), 1.95-1.75 (m, 2H), 1.03 (t, J=7.5 Hz, 3H). 1-193(S) (CDCl3, Me4Si, 400MHz) δ: 11.23 (s, 1H), 9.12 (d, J=4.8 Hz, 1H), 7.65-7.60 (m, 2H), 7.57 (dd, J=2.0, 8.4 Hz, 1H), 7.51 (d, J=2.0 Hz, 1H), 7.44 (dd, J=2.0, 2.0 Hz, 1H), 4.07 (d, J=17.2 Hz, 1H), 3.70 (d, J=17.2 Hz, 1H), 3.12 (q, J=7.2 Hz, 2H), 3.00 (d, J=4.8 Hz, 3H), 2.56 (s, 3H), 1.40 (t, J=7.2 Hz, 3H). 1-194(S) (CDCl3, Me4Si, 300MHz) δ: 11.25 (s, 1H), 9.20-9.02 (m, 1H), 7.65-7.50 (m, 3H), 7.55-7.45 (m, 2H), 7.45-7.35 (m, 1H), 4.20-4.00 (m, 1H), 3.75-3.60 (m, 1H), 3.55-3.35 (m, 2H), 3.20-3.00 (m, 2H), 2.60 (s, 3H), 1.45-1.35 (m, 3H), 1.35-1.20 (m, 3H). 1-196 (CDCl3, Me4Si, 400MHz) δ: 11.20-11.10 (m, 1H), 7.65-7.55 (m, 3H), 7.55-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.10-4.05 (m, 1H), 3.90 and 3.85 (s, 3H), 3.70 (d, J=17.2 Hz, 1H), 3.52 and 3.15 (q, J=7.2 Hz, 2H), 2.56 and 2.54 (s, 3H), 1.46 and 1.43 (t, J=7.2 Hz, 3H). 1-197 (CDCl3, Me4Si, 400MHz) δ: 9.22 (brs, 1H), 7.75-7.70 (m, 1H), 7.60-7.50 (m, 4H), 7.45-7.40 (m, 1H), 4.09 (d, J=17.2 Hz, 1H), 3.71 (d, J=17.2 Hz, 1H), 2.65-2.55 (m, 1H), 2.54 (s, 3H), 2.15 (dd, J=7.2, 7.2 Hz, 1H), 1.87 (dd, J=7.2, 10.0 Hz, 1H). 1-199 (CDCl3, Me4Si, 400MHz) δ: 10.31 (brs, 1H), 8.06 (d, J=8.0 Hz, 1H), 7.90-7.40 (m, 5H), 4.10 (d, J=17.2 Hz, 1H), 3.71 (d, J=17.2 Hz, 1H), 3.47 (s, 3H), 3.37 (q, J=7.2 Hz, 2H), 2.64 (s, 3H), 1.45 (t, J=7.2 Hz, 3H). 1-199(S) (CDCl3, Me4Si, 300MHz) δ: 8.06 (d, J=8.4 Hz, 1H), 7.55-7.45 (m, 4H), 7.45-7.40 (m, 1H), 4.09 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 3.47 (s, 3H), 3.18 (q, J=7.5 Hz, 2H), 2.64 (s, 3H), 1.45 (t, J=7.5 Hz, 3H). 1-200 (CDCl3, Me4Si, 400MHz) δ: 8.80 (s, 1H), 7.79 (d, J=1.6 Hz, 1H), 7.77 (d, J=8.0 Hz, 1H), 7.70 (dd, J=1.6, 8.0 Hz, 1H), 7.50 (d, J=1.2 Hz, 2H), 7.50-7.40 (m, 1H), 4.09 (d, J=17.2 Hz, 1H), 3.72 (d, J=17.2 Hz, 1H), 2.77 (s, 6H). 1-201 (CDCl3, Me4Si, 400MHz) δ: 8.77 (s, 1H), 7.96 (s, 1H), 7.80-7.60 (m, 2H), 7.55-7.40 (m, 3H), 4.08 (d, J=17.2 Hz, 1H), 3.72 (d, J=17.2 Hz, 1H), 2.76 (s, 6H). 1-202 (CDCl3, Me4Si, 400MHz) δ: 8.86 (s, 1H), 8.67 (s, 1H), 7.92 (s, 1H), 7.88 (d, J=8.1Hz, 1H), 7.77 (d, J=8.1Hz, 1H), 7.55-7.40 (m, 3H), 4.11 (d, J=17.2Hz, 1H), 3.73 (d, J=17.2Hz, 1H), 1.52 (s, 9H). 1-203 (CDCl3, Me4Si, 400MHz) δ: 9.48 (s, 1H), 7.76 (d, J=8.0 Hz, 1H), 7.65-7.40 (m, 5H), 4.50-4.35 (m, 4H), 4.08 (d, J=17.2 Hz, 1H), 3.70 (d, J=17.2 Hz, 1H), 3.05 (s, 3H), 2.56 (s, 3H), 2.45-2.35 (m, 2H). 1-205 (CDCl3, Me4Si, 400MHz) δ: 8.69 (s, 1H), 8.05 (s, 1H), 8.00-7.65 (m, 2H), 7.55-7.45 (m, 3H), 4.13 (d, J=17.6Hz, 1H), 3.76 (d, J=17.6Hz, 1H), 2.74 (s, 6H). 1-208 (CDCl3, Me4Si, 300MHz) δ: 11.22 (s, 1H), 7.60-7.40 (m, 6H), 4.08 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 3.15 (q, J=7.2 Hz, 2H), 2.56 (s, 3H), 1.52 (s, 9H), 1.42 (t, J=7.2 Hz, 3H). 1-209 (CDCl3, Me4Si, 400MHz) δ: 7.65 (d, J = 8.1 Hz, 1H), 7.65-7.60 (m, 1H), 7.60-7.50 (m, 3H), 7.45-7.40 (m, 1H), 4.10 (d, J=17.2 Hz, 1H), 3.71 (d, J=17.2 Hz, 1H), 2.95-2.85 (m, 2H), 2.55-2.40 (m, 1H), 2.20-2.05 (m, 1H), 1.80-1.65 (m, 1H), 1.30-1.20 (m, 3H). 1-210 (CDCl3, Me4Si, 400MHz) δ: 7.70-7.50 (m, 5H), 7.45-7.40 (m, 1H), 4.10 (d, J=17.2 Hz, 1H), 3.71 (d, J=17.2 Hz, 1H), 3.00-2.80 (m, 2H), 2.40-2.15 (m, 2H), 1.90-1.70 (m, 2H), 1.60-1.50 (m, 2H), 1.35-1.20 (m, 3H). 1-211 (CDCl3, Me4Si, 400MHz) δ: 8.89 (s, 1H), 7.65 (s, 1H), 7.60-7.40 (m, 5H), 4.20-4.00 (m, 1H), 3.80-3.65 (m, 1H), 3.15-3.00 (m, 2H), 2.95-2.80 (m, 2H), 1.45-1.35 (m, 3H), 1.35-1.20 (m, 3H). 1-213 (CDCl3, Me4Si, 400MHz) δ: 8.92 (brs, 1H), 7.65-7.55 (m, 2H), 7.55-7.45 (m, 3H), 7.45-7.40 (m, 1H), 4.20-4.00 (m, 1H), 3.80-3.60 (m, 4H), 2.95-2.80 (m, 2H), 1.30-1.20 (m, 3H). 1-218 (CDCl3, Me4Si, 400MHz) δ: 12.14 (brs, 1H), 8.12 (brs, 1H), 7.60-7.50 (m, 5H), 7.45-7.40 (m, 1H), 4.20-4.05 (m, 1H), 3.72 (d, J=17.2 Hz, 1H), 3.10-2.95 (m, 2H), 2.44 (s, 6H), 1.30-1.20 (m, 3H). 1-219 (CDCl3, Me4Si, 400MHz) δ: 10.46 (brs, 1H), 8.05 (d, J=8.1 Hz, 1H), 7.70-7.50 (m, 4H), 7.45-7.40 (m, 1H), 4.20-4.05 (m, 1H),4.00-3.90 (m, 2H), 3.72 (d, J=17.2 Hz, 1H), 3.29 (s, 3H), 2.65 (s, 3H), 1.45-1.30 (m, 1H), 0.60-0.50 (m, 2H), 0.50-0.40 (m, 2H). 1-220 (CDCl3, Me4Si, 400MHz) δ: 10.22 (brs, 1H), 8.08 (d, J=7.7 Hz, 1H), 7.60-7.50 (m, 4H), 7.45-7.40 (m, 1H), 5.34 (s, 2H), 4.15-4.05 (m, 1H), 3.71 (d, J=17.2 Hz, 1H), 3.50 (s, 3H), 3.43 (s, 3H), 2.64 (s, 3H). 1-221 (CDCl3, Me4Si, 400MHz) δ: 8.89 (s, 1H), 7.65 (s, 1H), 7.60-7.40 (m, 5H), 4.20-4.00 (m, 1H), 3.80-3.65 (m, 1H), 3.15-3.00 (m, 2H), 2.95-2.80 (m, 2H), 1.45-1.35 (m, 3H), 1.35-1.20 (m, 3H). 1-224 (CDCl3, Me4Si, 400MHz) δ: 9.31 (s, 1H), 8.70 (s, 1H), 7.94 (s, 1H), 7.89 (d, J=8.1Hz, 1H), 7.77 (d, J=8.1Hz, 1H), 7.55-7.40 (m, 3H), 4.15-3.70 (m, 5H). 1-226 (CDCl3, Me4Si, 400MHz) δ: 8.76 (s, 1H), 8.10-7.65 (m, 3H), 7.55-7.45 (m, 3H), 4.12 (d, J=17.2Hz, 1H), 3.75 (d, J=17.2Hz, 1H), 3.01 (s, 3H). 1-227 (CDCl3, Me4Si, 400MHz) δ: 7.65-7.60 (m, 3H), 7.55-7.50 (m, 2H), 7.45-7.40 (m, 1H), 4.15-4.05 (m, 1H), 3.72 (d, J=17.2 Hz, 1H), 3.13 (s, 3H), 2.56 (s, 3H), 2.42 (s, 3H). 1-227(S) (CDCl3, Me4Si, 300MHz) δ: 7.65-7.55 (m, 3H), 7.55-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.15-4.00 (m, 1H), 3.75-3.65 (m, 1H), 3.15 (s, 3H), 2.60 (s, 3H), 2.45 (s, 3H). 1-228 (CDCl3, Me4Si, 400MHz) δ: 10.45 (brs, 1H), 8.00-7.90 (m, 1H), 7.55-7.40 (m, 7H), 7.40-7.25 (m, 3H), 5.30 (s, 2H), 4.15-4.05 (m, 1H), 3.70 (d, J=17.2 Hz, 1H), 2.98 (s, 3H), 2.62 (s, 3H). 1-229 (CDCl3, Me4Si, 400MHz) δ: 7.83 (d, J=8.1 Hz, 1H), 7.55-7.50 (m, 2H), 7.50-7.40 (m, 4H), 7.30-7.25 (m, 1H), 7.20-7.00 (m, 2H), 5.34 (s, 2H), 4.15-4.00 (m, 1H), 3.69 (d, J=17.2 Hz, 1H), 3.20 (s, 3H), 2.57 (s, 3H). 1-231 (CDCl3, Me4Si, 400MHz) δ: 8.04 (d, J=8.1 Hz, 1H), 7.65-7.50 (m, 4H), 7.45-7.40 (m, 1H), 4.15-4.05 (m, 1H), 4.00-3.90 (m, 2H), 3.72 (d, J=17.2 Hz, 1H), 3.20 (s, 3H), 2.65 (s, 3H), 1.90-1.75 (m, 2H), 1.05-0.90 (m, 3H). 1-232 (CDCl3, Me4Si, 400MHz) δ: 11.50-10.90 (m, 2H), 7.70-7.55 (m, 3H), 7.55-7.50 (m, 2H), 7.50-7.40 (m, 1H), 4.20-4.00 (m, 1H), 3.75-3.65 (m, 1H), 3.15 (s, 3H), 2.55 (s, 3H), 1.90-1.75 (m, 1H), 1.25-0.95 (m, 4H). 1-232(S) (CDCl3, Me4Si, 300MHz) δ: 7.60-7.55 (m, 3H), 7.55-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.15-4.00 (m, 1H), 3.75-3.60 (m, 1H), 3.15 (s, 3H), 2.60 (s, 3H), 1.85 (brs, 1H), 1.25-1.15 (m, 2H), 1.15-1.00 (m, 2H). 1-234 (CDCl3, Me4Si, 400MHz) δ: 8.00-7.90 (m, 2H), 7.75-7.60 (m, 4H), 7.60-7.50 (m, 4H), 7.45-7.40 (m, 1H), 4.20-4.05 (m, 1H), 3.80-3.65 (m, 1H), 3.15 (s, 3H), 2.60 (s, 3H). 1-234(S) (CDCl3, Me4Si, 300MHz) δ: 8.00-7.90 (m, 2H), 7.75-7.50 (m, 8H), 7.45-7.40 (m, 1H), 4.20-4.05 (m, 1H), 3.80-3.65 (m, 1H), 3.20 (s, 3H), 2.60 (s, 3H). 1-235 (CDCl3, Me4Si, 400MHz) δ: 7.65-7.60 (m, 3H), 7.55-7.50 (m, 2H), 7.45-7.40 (m, 1H), 4.15-4.05 (m, 1H), 3.75-3.65 (m, 1H), 3.15 (s, 3H), 2.75-2.60 (m, 1H), 2.55 (s, 3H), 1.30-1.25 (m, 6H). 1-235(S) (CDCl3, Me4Si, 300MHz) δ: 7.65-7.55 (m, 3H), 7.55-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.15-4.00 (m, 1H), 3.75-3.65 (m, 1H), 3.15 (s, 3H), 2.80-2.60 (m, 1H), 2.60 (s, 3H), 1.30-1.20 (m, 6H). 1-236 (CDCl3, Me4Si, 400MHz) δ: 7.65-7.60 (m, 3H), 7.55-7.50 (m, 2H), 7.45-7.40 (m, 1H), 4.15-4.05 (m, 1H), 3.75-3.65 (m, 1H), 3.15 (s, 3H), 2.75-2.55 (m, 2H), 2.55 (s, 3H), 1.25-1.15 (m, 3H). 1-236(S) (CDCl3, Me4Si, 300MHz) δ: 7.65-7.60 (m, 3H), 7.55-7.50 (m, 2H), 7.45-7.40 (m, 1H), 4.15-4.05 (m, 1H), 3.75-3.65 (m, 1H), 3.15 (s, 3H), 2.75-2.55 (m, 2H), 2.55 (s, 3H), 1.25-1.15 (m, 3H). 1-237 (CDCl3, Me4Si, 400MHz) δ: 11.25 (brs, 1H), 11.00 (brs, 1H), 8.05 (brs, 1H), 7.65-7.60 (m, 3H), 7.55-7.50 (m, 2H), 7.45-7.40 (m, 1H), 4.15-4.00 (m, 1H), 3.75-3.70 (m, 1H), 3.15 (s, 3H), 3.00-2.90 (m, 3H), 2.60 (s, 3H). 1-238(S) (CDCl3, Me4Si, 400MHz) δ: 7.65-7.55 (m, 3H), 7.55-7.50 (m, 2H), 7.50-7.40 (m, 1H), 4.15-4.05 (m, 3H), 3.75-3.65 (m, 1H), 3.55 (s, 3H), 3.25-3.10 (m, 2H), 2.60 (s, 3H), 1.50-1.35 (m, 3H). 1-239(S) (CDCl3, Me4Si, 400MHz) δ: 7.75-7.55 (m, 4H), 7.55-7.50 (m, 2H), 7.45-7.40 (m, 1H), 7.40-7.35 (m, 1H), 6.70-6.60 (m, 1H), 4.15-4.05 (m, 1H), 3.75-3.65 (m, 1H), 3.30-3.15 (m, 2H), 2.60 (s, 3H), 1.50-1.40 (m, 3H). 1-240(S) (CDCl3, Me4Si, 300MHz) δ: 7.65-7.55 (m, 3H), 7.55-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.15-4.00 (m, 1H), 3.75-3.65 (m, 1H), 3.25-3.10 (m, 2H), 2.60 (s, 3H), 2.50-2.35 (m, 3H), 1.50-1.35 (m, 3H). 1-241(S) (CDCl3, Me4Si, 300MHz) δ: 7.65-7.55 (m, 3H), 7.55-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.15-4.00 (m, 1H), 3.75-3.70 (m, 1H), 3.25-3.10 (m, 2H), 2.75-2.50 (m, 2H), 2.55 (s, 3H), 1.50-1.35 (m, 3H), 1.30-1.15 (m, 3H). 1-242(S) (CDCl3, Me4Si, 300MHz) δ: 11.15 (brs, 1H), 7.65-7.55 (m, 3H), 7.55-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.35-4.20 (m, 2H), 4.15-4.00 (m, 1H), 3.75-3.65 (m, 1H), 3.25-3.10 (m, 2H), 2.60 (s, 3H), 1.50-1.40 (m, 3H), 1.40-1.30 (m, 3H). 1-243(S) (CDCl3, Me4Si, 300MHz) δ: 11.80-10.25 (m, 2H), 7.70-7.55 (m, 3H), 7.55-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.15-4.00 (m, 1H), 3.75-3.65 (m, 1H), 2.95-2.65 (m, 6H), 2.55 (s, 3H), 2.55-2.15 (m, 3H). 1-244(S) (CDCl3, Me4Si, 300MHz) δ: 11.85-10.25 (m, 2H), 7.70-7.55 (m, 3H), 7.55-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.20-4.00 (m, 1H), 3.75-3.60 (m, 1H), 2.95-2.40 (m, 8H), 2.55 (s, 3H), 1.30-1.20 (m, 3H). 1-245(S) (CDCl3, Me4Si, 300MHz) δ: 11.20-10.75 (m, 1H), 7.70-7.55 (m, 3H), 7.55-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.35-4.20 (m, 2H), 4.20-4.00 (m, 1H), 3.80-3.60 (m, 1H), 2.95-2.65 (m, 6H), 2.55 (s, 3H), 1.40-1.30 (m, 3H). 1-246(S) (CDCl3, Me4Si, 300MHz) δ: 10.95 (s, 1H), 9.10-9.00 (m, 1H), 7.65-7.50 (m, 3H), 7.50-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.15-4.00 (m, 1H), 3.75-3.60 (m, 1H), 2.95-2.80 (m, 1H), 2.80 (s, 6H), 2.55 (s, 3H), 0.95-0.80 (m, 2H), 0.75-0.65 (m, 2H). 1-247(S) (CDCl3, Me4Si, 300MHz) δ: 11.05 (s, 1H), 9.50-9.35 (m, 1H), 7.65-7.50 (m, 3H), 7.50-7.45 (m, 2H), 7.45-7.40 (m, 1H), 7.40-7.30 (m, 5H), 4.65-4.55 (m, 2H), 4.15-4.00 (m, 1H), 3.75-3.65 (m, 1H), 2.60 (s, 6H), 2.55 (s, 3H). 1-249(S) (CDCl3, Me4Si, 300MHz) δ: 11.00 (s, 1H), 9.10-9.00 (m, 1H), 7.65-7.50 (m, 3H), 7.50-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.15-4.00 (m, 1H), 3.75-3.65 (m, 1H), 3.55-3.40 (m, 2H), 2.80 (s, 6H), 2.60 (s, 3H), 1.35-1.20 (m, 3H). 1-250(S) (CDCl3, Me4Si, 300MHz) δ: 11.00 (s, 1H), 9.30-9.20 (m, 1H), 7.65-7.55 (m, 3H), 7.55-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.10-4.00 (m, 1H), 3.75-3.65 (m, 1H), 3.65-3.55 (m, 4H), 3.45 (s, 3H), 2.75 (s, 6H), 2.60 (s, 3H). 1-251(S) (CDCl3, Me4Si, 400MHz) δ: 11.15 (s, 1H), 7.70-7.55 (m, 3H), 7.55-7.50 (m, 2H), 7.45-7.40 (m, 1H), 4.15-4.00 (m, 1H), 3.85 (s, 3H), 3.75-3.65 (m, 1H), 3.25-3.10 (m, 2H), 2.60 (s, 3H), 1.50-1.40 (m, 3H). 1-252(S) (CDCl3, Me4Si, 300MHz) δ: 11.05 (brs, 1H), 10.90 (brs, 1H), 8.20-8.05 (m, 1H), 7.70-7.60 (m, 3H), 7.55-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.15-4.00 (m, 1H), 3.80-3.65 (m, 1H), 3.00-2.90 (m, 3H), 2.80 (s, 6H), 2.60 (s, 3H). 1-253(S) (CDCl3, Me4Si, 300MHz) δ: 11.00 (brs, 1H), 10.85 (brs, 1H), 8.20-8.10 (m, 1H), 7.65-7.55 (m, 3H), 7.55-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.15-4.00 (m, 1H), 3.75-3.65 (m, 1H), 3.45-3.30 (m, 2H), 2.80 (s, 6H), 2.60 (s, 3H), 1.30-1.20 (m, 3H). 1-254(S) (CDCl3, Me4Si, 300MHz) δ: 11.10 (brs, 1H), 10.90 (brs, 1H), 7.70-7.55 (m, 3H), 7.55-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.15-4.00 (m, 1H), 3.85 (s, 3H), 3.75-3.65 (m, 1H), 2.90-2.65 (m, 6H), 2.60 (s, 3H). 1-255 (CDCl3, Me4Si, 400MHz) δ: 11.20 (brs, 1H), 10.91 (brs, 1H), 8.09 (brs, 1H), 7.65-7.60 (m, 2H), 7.55-7.50 (m, 3H), 7.45-7.40 (m, 1H), 4.10-4.05 (m, 1H), 3.70 (d, J=17.2 Hz, 1H), 3.45-3.30 (m, 2H), 3.15 (s, 3H), 2.57 (s, 3H), 1.25-1.20 (m, 3H). 1-255(S) (CDCl3, Me4Si, 300MHz) δ: 11.20 (brs, 1H), 10.90 (brs, 1H), 8.10 (brs, 1H), 7.65-7.60 (m, 3H), 7.55-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.15-4.00 (m, 1H), 3.75-3.65 (m, 1H), 3.45-3.30 (m, 2H), 3.15 (s, 3H), 2.60 (s, 3H), 1.30-1.15 (m, 3H). 1-256 (CDCl3, Me4Si, 300MHz) δ: 11.17 (brs, 1H), 7.65-7.60 (m, 3H), 7.55-7.50 (m, 2H), 7.45-7.40 (m, 1H), 4.35-4.25 (m, 2H), 4.15-4.05 (m, 1H), 3.71 (d, J=17.2 Hz, 1H), 3.13 (s, 3H), 2.57 (s, 3H), 1.35 (t, J=7.2 Hz, 3H). 1-256(S) (CDCl3, Me4Si, 300MHz) δ: 11.20 (brs, 1H), 7.65-7.55 (m, 3H), 7.55-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.35-4.20 (m, 2H), 4.15-4.00 (m, 1H), 3.75-3.65 (m, 1H), 3.15 (s, 3H), 2.60 (s, 3H), 1.40-1.30 (m, 3H). 1-257(S) (CDCl3, Me4Si, 300MHz) δ: 9.06 (s, 1H), 8.35-8.30 (m, 1H), 7.90-7.80 (m, 1H), 7.75-7.40 (m, 8H), 4.15-4.00 (m, 1H), 3.70 (d, J=17.5 Hz, 1H), 2.53 (s, 3H). 1-258(S) (CDCl3, Me4Si, 300MHz) δ: 11.20-11.05 (m, 1H), 7.65-7.45 (m, 5H), 7.45-7.40 (m, 1H), 4.20-4.00 (m, 3H), 3.75-3.65 (m, 1H), 3.25-3.05 (m, 2H), 2.55 (s, 3H), 1.50-1.20 (m, 6H). 1-260(S) (CDCl3, Me4Si, 400MHz) δ: 12.25-11.55 (m, 1H), 7.60-7.40 (m, 6H), 4.15-4.05 (m, 1H), 3.85-3.70 (m, 4H), 2.70-2.55 (m, 5H), 1.30-1.20 (m, 3H). 1-261(S) (CDCl3, Me4Si, 400MHz) δ: 10.85-10.20 (m, 1H), 9.30-9.10 (m, 1H), 7.80-7.40 (m, 6H), 4.15-4.10 (m, 1H), 3.90-3.65 (m, 4H), 2.95-2.85 (m, 3H), 2.58 (s, 3H), 2.51 (s, 1H). 1-262(S) (CDCl3, Me4Si, 400MHz) δ: 11.55-8.40 (m, 1H), 7.60-7.40 (m, 6H), 4.15-4.05 (m, 1H), 3.85-3.70 (m, 4H), 2.64 (s, 3H), 1.90-1.75 (m, 1H), 1.25-1.05 (m, 4H). 1-263(S) (CDCl3, Me4Si, 400MHz) δ: 11.35 (s, 1H), 7.65-7.40 (m, 6H), 4.15-4.05 (m, 1H), 3.83 (s, 6H), 3.75-3.70 (m, 1H), 2.62 (s, 3H). 1-265(S) (CDCl3, Me4Si, 300MHz) δ: 11.90-8.10 (m, 1H), 7.60-7.40 (m, 6H), 4.20-4.05 (m, 1H), 3.71 (d, J=17.6 Hz, 1H), 2.65-2.55 (m, 3H), 2.48 (s, 3H), 1.95-1.80 (m, 1H), 1.25-0.95 (m, 4H). 1-266(S) (CDCl3, Me4Si, 300MHz) δ: 12.10-8.10 (m, 1H), 7.60-7.40 (m, 6H), 4.20-4.05 (m, 1H), 3.72 (d, J=17.6 Hz, 1H), 2.75-2.60 (m, 5H), 2.00-1.85 (m, 1H), 1.30-0.90 (m, 7H). 1-267(S) (CDCl3, Me4Si, 300MHz) δ: 8.02 (d, J=7.6 Hz, 2H), 7.60-7.40 (m, 9H), 4.20-4.05 (m, 1H), 3.72 (d, J=17.6 Hz, 1H), 2.65-2.50 (m, 3H), 2.10-2.00 (m, 1H), 1.30-1.00 (m, 4H). 1-268(S) (CDCl3, Me4Si, 300MHz) δ: 12.45-8.10 (m, 1H), 7.55-7.40 (m, 6H), 4.20-4.05 (m, 1H), 3.71 (d, J=17.6 Hz, 1H), 2.65-2.55 (m, 3H), 2.00-1.95 (m, 2H), 1.30-0.95 (m, 8H). 1-269(S) (CDCl3, Me4Si, 300MHz) δ: 12.36 (s, 1H), 8.28 (s, 1H), 7.55-7.40 (m, 6H), 4.20-4.05 (m, 1H), 3.71 (d, J=17.6 Hz, 1H), 2.85-2.55 (m, 4H), 2.05-2.00 (m, 1H), 1.35-0.95 (m, 10H). 1-270(S) (CDCl3, Me4Si, 300MHz) δ: 7.60-7.40 (m, 6H), 4.35-4.05 (m, 3H), 3.70 (d. J=17.6 Hz, 1H), 2.65-2.55 (m, 3H), 1.95-1.80 (m, 1H), 1.40-0.95 (m, 7H). 1-271(S) (CDCl3, Me4Si, 300MHz) δ: 8.20 (s, 1H), 7.55-7.40 (m, 6H), 4.20-4.05 (m, 1H), 3.71 (d, J=17.6 Hz, 1H), 2.66 (s, 3H), 2.51 (d, J=7.2 Hz, 2H), 2.30-2.10 (m, 1H), 2.00-1.90 (m, 1H), 1.25-0.90 (m, 10H). 1-272(S) (CDCl3, Me4Si, 300MHz) δ: 7.65-7.25 (m, 8H), 6.55 (s, 1H), 4.20-4.05 (m, 1H), 3.72 (d, J=17.6 Hz, 1H), 2.64 (s, 3H), 2.10-1.95 (m, 1H), 1.30-1.00 (m, 4H). 1-273(S) (CDCl3, Me4Si, 300MHz) δ: 9.14 (s, 1H), 8.67 (s, 1H), 8.30 (d, J=7.8 Hz, 1H), 7.65-7.30 (m, 7H), 4.20-4.05 (m, 1H), 3.77 (d, J=17.6 Hz, 1H), 2.58 (s, 3H), 2.05-1.95 (m, 1H), 1.30-1.10 (m, 4H). 1-274(S) (CDCl3, Me4Si, 300MHz) δ: 8.03 (d, J=8.2 Hz, 1H), 7.54-7.40 (m, 5H), 4.10 (d, J=17.6 Hz, 1H), 3.71 (d, J=17.6 Hz, 1H), 3.42 (s, 3H), 2.97 (s, 6H), 2.64 (s, 3H). 1-276(S) (CDCl3, Me4Si, 300MHz) δ: 7.70-7.45 (m, 5H), 7.45-7.40 (m, 1H), 4.15-4.00 (m, 1H), 3.75-3.60 (m, 1H), 2.60 (s, 3H), 2.55 (s, 3H). 1-277(S) (CDCl3, Me4Si, 300MHz) δ: 11.80 (brs, 1H), 7.75-7.70 (m, 1H), 7.65-7.60 (m, 3H), 7.55-7.45 (m, 3H), 7.45-7.40 (m, 1H), 6.75-6.65 (m, 1H), 4.15-4.05 (m, 1H), 3.80-3.65 (m, 1H), 2.60 (s, 3H). 1-278(S) (CDCl3, Me4Si, 300MHz) δ: 7.70-7.55 (m, 3H), 7.55-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.15-4.00 (m, 1H), 3.95 (s, 3H), 3.75-3.65 (m, 1H), 2.60 (s, 3H). 1-279(S) (CDCl3, Me4Si, 300MHz) δ: 7.65-7.55 (m, 3H), 7.55-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.40-4.20 (m, 2H), 4.15-4.00 (m, 1H), 3.75-3.65 (m, 1H), 2.55 (s, 3H), 1.40-1.30 (m, 3H). 1-281(S) (CDCl3, Me4Si, 400MHz) δ: 11.08 (brs, 1H), 10.91 (brs, 1H), 7.70-7.50 (m, 5H), 7.45-7.40 (m, 1H), 4.15-4.05 (m, 3H), 3.71 (d, J=17.2 Hz, 1H), 3.00 (s, 3H), 2.81 (s, 3H), 2.56 (s, 3H), 1.34 (t, J=7.2 Hz, 3H). 1-282(S) (CDCl3, Me4Si, 300MHz) δ: 7.60-7.55 (m, 3H), 7.50-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.07 (d, J=17.0 Hz, 1H), 3.69 (d, J=17.0 Hz, 1H), 3.25-3.10 (m, 2H), 2.55 (s, 3H), 1.43 (t, J=7.3 Hz, 3H), 1.25-1.15 (m, 2H), 1.15-1.05 (m, 2H). 1-283(S) (CDCl3, Me4Si, 300MHz) δ: 12.09 (brs, 1H), 11.41 (brs, 1H), 8.05-7.90 (m, 2H), 7.70-7.50 (m, 8H), 7.45-7.40 (m, 1H), 4.20-4.05 (m, 1H), 3.72 (d, J=17.4 Hz, 1H), 2.90 (s, 3H), 2.80 (s, 3H), 2.59 (s, 3H). 1-284(S) (CDCl3, Me4Si, 300MHz) δ: 11.88 (brs, 1H), 10.58 (brs, 1H), 7.65-7.55 (m, 3H), 7.55-7.50 (m, 2H), 7.45-7.40 (m, 1H), 4.15-4.05 (m, 1H), 3.70 (d, J=17.4 Hz, 1H), 2.85-2.70 (m, 6H), 2.55 (s, 3H), 1.65-1.50 (m, 1H), 1.20-1.15 (m, 2H), 1.15-1.00 (m, 2H). 1-285(S) (CDCl3, Me4Si, 300MHz) δ: 11.22 (s, 1H), 9.37 (brs, 1H), 7.65-7.55 (m, 3H), 7.55-7.50 (m, 2H), 7.45-7.40 (m, 1H), 4.08 (d, J=17.2 Hz, 1H), 3.70 (d, J=17.2 Hz, 1H), 3.65-3.50 (m, 4H), 3.42 (s, 3H), 3.15-3.05 (m, 2H), 2.57 (s, 3H), 1.39 (t, J=7.3 Hz, 3H). 1-286(S) (CDCl3, Me4Si, 300MHz) δ: 10.90-10.80 (m, 1H), 9.50-9.20 (m, 1H), 7.85-7.40 (m, 6H), 4.20-4.05 (m, 1H), 3.73 (d, J=17.5 Hz, 1H), 3.00-2.85 (m, 3H), 2.60-2.50 (m, 5H), 1.30-1.20 (m, 3H). 1-288(S) (CDCl3, Me4Si, 300MHz) δ: 10.95-10.80 (m, 1H), 9.45-9.20 (m, 1H), 7.85-7.40 (m, 6H), 4.20-4.05 (m, 1H), 3.80-3.65 (m, 1H), 3.00-2.80 (m, 3H), 2.65-2.55 (m, 3H), 2.00-1.65 (m, 1H), 1.35-0.95 (m, 4H). 1-289(S) (CDCl3, Me4Si, 300MHz) δ: 7.60-7.40 (m, 6H), 4.09 (d, J=17.5 Hz, 1H), 3.70 (d, J=17.5 Hz, 1H), 2.61 (s, 3H), 2.45 (s, 3H), 2.25-2.15 (m, 1H), 2.05-1.75 (m, 2H). 1-290(S) (CDCl3, Me4Si, 300MHz) δ: 8.05-7.40 (m, 6H), 4.20-4.05 (m, 1H), 3.71 (d, J=17.5 Hz, 1H), 2.75-2.40 (m, 6H), 2.30-2.10 (m, 1H), 1.85-1.70 (m, 1H), 1.35-1.15 (m, 3H). 1-291(S) (CDCl3, Me4Si, 300MHz) δ: 10.95-10.65 (m, 1H), 9.20-9.05 (m, 1H), 7.85-7.40 (m, 6H), 4.20-4.05 (m, 1H), 3.80-3.65 (m, 1H), 3.00-2.85 (m, 3H), 2.65-2.50 (m, 4H), 2.35-1.75 (m, 2H). 1-292(S) (CDCl3, Me4Si, 300MHz) δ: 8.10-7.40 (m, 11H), 4.20-4.05 (m, 1H), 3.80-3.45 (m, 2H), 2.65-2.55 (m, 3H), 2.35-2.25 (m, 1H), 1.85-1.80 (m, 1H). 1-293(S) (CDCl3, Me4Si, 300MHz) δ: 7.65-7.40 (m, 6H), 4.20-4.05 (m, 1H), 3.70 (d, J=17.2 Hz, 1H), 2.65-2.55 (m, 3H), 2.30-2.20 (m, 1H), 2.00-1.55 (m, 3H), 1.25-1.00 (m, 4H). 1-294(S) (CDCl3, Me4Si, 300MHz) δ: 7.60-7.40 (m, 6H), 4.09 (d, J=17.5 Hz, 1H), 3.85 (s, 3H), 3.70 (d, J=17.5 Hz, 1H), 2.61 (s, 3H), 2.35-2.15 (m, 1H), 1.85-1.60 (m, 2H). 1-295(S) (CDCl3, Me4Si, 300MHz) δ: 7.65-7.55 (m, 3H), 7.50-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.08 (d, J=17.2 Hz, 1H), 3.70 (d, J=17.2 Hz, 1H), 2.56 (s, 3H), 2.05-1.95 (m, 1H), 1.30-1.25 (m, 2H), 1.20-1.10 (m, 2H). 1-297(S) (CDCl3, Me4Si, 300MHz) δ: 8.90-8.85 (m, 1H), 7.65-7.40 (m, 6H), 4.15-4.05 (m, 1H), 3.70 (d, J=17.5 Hz, 1H), 2.95-2.80 (m, 1H), 2.55 (s, 3H), 2.25-2.20 (m, 2H), 1.95-1.85 (m, 2H), 1.75-1.15 (m, 6H). 1-298(S) (CDCl3, Me4Si, 300MHz) δ: 8.92 (s, 1H), 7.65-7.40 (m, 6H), 6.05-5.85 (m, 1H), 5.50-5.35 (m, 2H), 4.20-4.05 (m, 1H), 3.85-3.65 (m, 3H), 2.55 (s, 3H). 1-299(S) (CDCl3, Me4Si, 300MHz) δ: 9.20-9.15 (m, 1H), 7.65-7.40 (m, 6H), 4.09 (d, J=17.5 Hz, 1H), 3.85 (q, J=9.0 Hz, 2H), 3.74 (d, J=17.5 Hz, 1H), 2.56 (s, 3H). 1-303(S) (CDCl3, Me4Si, 300MHz) δ: 11.20 (s, 1H), 9.15-8.95 (m, 1H), 7.65-7.45 (m, 5H), 7.45-7.40 (m, 1H), 4.25-4.05 (m, 3H), 3.70 (d, J=17.4 Hz, 1H), 3.15 (q, J=7.4 Hz, 2H), 2.60 (s, 3H), 1.40 (t, J=7.5 Hz, 3H), 1.30 (d, J=6.1 Hz, 6H). 1-308(S) (CDCl3, Me4Si, 400MHz) δ: 11.20 (brs, 1H), 7.80-7.75 (m, 1H), 7.70-7.55 (m, 2H), 7.50-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.30 (q, J=7.2 Hz, 2H), 4.15-4.00 (m, 1H), 3.70 (d, J=17.4 Hz, 1H), 3.15-3.00 (m, 2H), 1.45-1.30 (m, 6H). 1-312(S) (CDCl3, Me4Si, 400MHz) δ: 11.10 (brs, 1H), 10.90 (brs, 1H), 7.65-7.50 (m, 5H), 7.50-7.40 (m, 1H), 4.15-4.05 (m, 1H), 3.90 and 3.80 (s, 3H), 3.75-3.65 (m, 1H), 3.05-2.75 (m, 6H), 2.60-2.50 (m, 3H). 1-313(S) (CDCl3, Me4Si, 400MHz) δ: 7.65-7.55 (m, 3H), 7.55-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.10 (d, J=17.2 Hz, 1H), 3.70 (d, J=17.2 Hz, 1H), 3.25-3.10 (m, 2H), 2.60 (s, 3H), 2.55-2.10 (m, 3H), 1.45 (t, J=7.3 Hz, 3H), 1.00 (d, J=6.6 Hz, 6H). 1-314(S) (CDCl3, Me4Si, 300MHz) δ: 8.00-7.90 (m, 2H), 7.75-7.45 (m, 8H), 7.45-7.40 (m, 1H), 4.15-4.05 (m, 1H), 3.75 (d, J=17.4 Hz, 1H), 3.25 (q, J=7.4 Hz, 2H), 2.60 (s, 3H), 1.50 (t, J=7.3 Hz, 3H). 1-315(S) (CDCl3, Me4Si, 300MHz) δ: 7.65-7.55 (m, 3H), 7.55-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.010 (d, J=16.7 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 3.15 (q, J=7.3 Hz, 2H), 2.80-2.60 (m, 1H), 2.60 (s, 3H), 1.45 (t, J=7.3 Hz, 3H), 1.30 (d, J=6.8 Hz, 6H). 1-316(S) (CDCl3, Me4Si, 300MHz) δ: 11.80 and 11.45 (brs, 1H), 10.90 and 10.50 (brs, 1H), 7.65-7.55 (m, 3H), 7.55-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.15-4.00 (m, 1H), 3.70 (d, J=17.4 Hz, 1H), 2.95-2.45 (m, 9H), 1.30-1.20 (m, 6H). 1-317(S) (CDCl3, Me4Si, 300MHz) δ: 8.00-7.90 (m, 2H), 7.75-7.45 (m, 8H), 7.45-7.40 (m, 1H), 4.10 (d, J=17.7 Hz, 1H), 3.72 (d, J=17.1 Hz, 1H), 2.60 (s, 3H). 1-318(S) (CDCl3, Me4Si, 300MHz) δ: 7.65-7.55 (m, 3H), 7.55-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.10 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 2.95-2.75 (m, 1H), 2.60 (s, 3H), 1.30 (d, J=7.2 Hz, 6H). 1-320(S) (CDCl3, Me4Si, 300MHz) δ: 7.70-7.55 (m, 3H), 7.55-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.10 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 2.80 (q, J=7.3 Hz, 2H), 2.60 (s, 3H), 1.25 (t, J=6.8 Hz, 3H). 1-322(S) (CDCl3, Me4Si, 300MHz) δ: 11.30 (brs, 1H), 10.95 (brs, 1H), 8.00 (brs, 1H), 7.65-7.60 (m, 3H), 7.55-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.20-4.00 (m, 1H), 3.70 (d, J=17.4 Hz, 1H), 3.25-3.15 (m, 2H), 3.00-2.90 (m, 3H), 2.60 (s, 3H), 1.45 (t, J=7.5 Hz, 3H). 1-323(S) (CDCl3, Me4Si, 400MHz) δ: 11.30 (brs, 1H), 10.95 (brs, 1H), 8.15 (brs, 1H), 7.65-7.60 (m, 3H), 7.55-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.10 (d, J=17.2 Hz, 1H), 3.70 (d, J=17.2 Hz, 1H), 3.45-3.35 (m, 2H), 3.20 (q, J=7.5 Hz, 2H), 2.60 (s, 3H), 1.45 (t, J=7.3 Hz, 3H), 1.25 (t, J=7.2 Hz, 3H). 1-324(S) (CDCl3, Me4Si, 300MHz) δ: 11.20 (s, 1H), 9.15 (brs, 1H), 7.65-7.50 (m, 3H), 7.55-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.15-4.00 (m, 1H), 3.70 (d, J=17.4 Hz, 1H), 3.15 (q, J=7.4 Hz, 2H), 2.95-2.80 (m, 1H), 2.55 (s, 3H), 1.45 (t, J=7.3 Hz, 3H), 0.95-0.80 (m, 2H), 0.75-0.60 (m, 2H). 1-325(S) (CDCl3, Me4Si, 300MHz) δ: 11.25 (s, 1H), 9.55-9.40 (m, 1H), 7.65-7.45 (m, 5H), 7.45-7.25 (m, 6H), 4.65-4.55 (m, 2H), 4.15-4.00 (m, 1H), 3.70 (d, J=17.0 Hz, 1H), 3.10 (q, J=7.4 Hz, 2H), 2.55 (s, 3H), 1.35-1.25 (m, 3H). 1-326(S) (CDCl3, Me4Si, 300MHz) δ: 11.25 (s, 1H), 9.25-9.10 (m, 1H), 7.65-7.50 (m, 3H), 7.55-7.45 (m, 2H), 7.45-7.40 (m, 1H), 4.15-4.00 (m, 1H), 3.70 (d, J=17.4 Hz, 1H), 3.45-3.30 (m, 2H), 3.20-3.05 (m, 2H), 2.60 (s, 3H), 1.75-1.60 (m, 2H), 1.40 (t, J=7.3 Hz, 3H), 1.00 (t, J=7.3 Hz, 3H). 1-328(S) (CDCl3, Me4Si, 300MHz) δ: 8.10-8.00 (m, 1H), 7.70-7.40 (m, 5H), 6.10-5.95 (m, 1H), 5.45-5.20 (m, 2H), 4.65-4.60 (m, 2H), 4.10-4.00 (m, 1H), 3.75-3.65 (m, 1H), 3.45-3.05 (m, 2H), 2.65-2.55 (m, 3H), 1.50-1.35 (m ,3H). 1-329(S) (CDCl3, Me4Si, 300MHz) δ: 11.22 (s, 1H), 9.33 (s, 1H), 7.65-7.40 (m, 6H), 4.25-4.00 (m, 3H), 3.75-3.65 (m, 1H), 3.60-3.40 (m ,1H), 3.13 (q, J=7.4 Hz, 2H), 2.57 (s, 3H), 1.41 (t, J=7.4 Hz, 3H). 1-330(S) (CDCl3, Me4Si, 300MHz) δ: 8.10-7.40 (m, 6H), 4.15-4.05 (m, 1H), 3.94 (d, J=7.2 Hz, 2H), 3.71 (d, J=17.2 Hz, 1H), 3.41 (q, J=7.4 Hz, 2H), 2.65 (s, 3H), 1.50-1.35 (m, 4H), 0.60-0.40 (m, 4H). 1-331(S) (CDCl3, Me4Si, 300MHz) δ: 7.95-7.85 (m, 1H), 7.55-7.25 (m, 10H), 5.27 (s, 2H), 4.20-4.05 (m, 1H), 3.69 (d, J=17.5 Hz, 1H), 3.20 (q, J=7.4 Hz, 2H), 2.59 (s, 3H), 1.38 (t, J=7.4 Hz, 3H). 1-332(S) (CDCl3, Me4Si, 300MHz) δ: 8.00 (d, J=8.1 Hz, 1H), 7.55-7.40 (m, 5H), 4.15-4.00 (m, 3H), 3.70 (d, J=17.4 Hz, 1H), 2.95 (s, 6H), 2.64 (s, 3H), 1.35 (t, J=6.9 Hz, 3H). 2-006 (CDCl3, Me4Si, 300MHz) δ: 7.73 (d, J=8.4 Hz, 1H), 7.70-7.65 (m, 1H), 7.60-7.50 (m, 4H), 4.09 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 2.56 (s, 3H), 2.55-2.45 (m, 1H), 2.20-2.10 (m, 1H), 1.80-1.65 (m, 1H). 2-006(S) (CDCl3, Me4Si, 400MHz) δ: 9.93 (brs, 2H), 7.67 (s, 1H), 7.65-7.55 (m, 3H), 7.50-7.40 (m, 2H), 4.10 (d, J=17.2 Hz, 1H), 3.74 (d, J=17.2 Hz, 1H), 2.50-2.35 (m, 4H), 2.20-2.05 (m, 1H), 1.75-1.65 (m, 1H). 2-007 (CDCl3, Me4Si, 300MHz) δ: 7.87 (d, J=9.0 Hz, 1H), 7.66 (s, 1H), 7.60-7.50 (m, 4H), 4.09 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 2.58 (s, 3H), 1.60-1.50 (m, 1H), 1.15-0.95 (m, 4H). 2-009 (CDCl3, Me4Si, 400MHz) δ: 8.92 (brs, 1H), 7.65-7.50 (m, 6H), 4.09 (d, J=17.6 Hz, 1H), 3.71 (d, J=17.6 Hz, 1H), 3.09 (q, J=7.2 Hz, 2H), 2.55 (s, 3H), 1.40 (t, J=7.2 Hz, 3H). 2-010 (CDCl3, Me4Si, 400MHz) δ: 8.79 (brs, 1H), 7.71 (d, J=8.0 Hz, 1H), 7.65-7.60 (m, 1H), 7.60-7.50 (m, 4H), 4.19 (q, J=7.2 Hz, 2H), 4.09 (d, J=17.6 Hz, 1H), 3.70 (d, J=17.6 Hz, 1H), 2.53 (s, 3H), 1.31 (t, J=7.2 Hz, 3H). 2-011 (CDCl3, Me4Si, 400MHz) δ: 7.70-7.50 (m, 6H), 4.08 (d, J=17.6 Hz, 1H), 3.70 (d, J=17.6 Hz, 1H), 3.45-3.25 (m, 2H), 2.54 (s, 3H), 1.20-1.10 (m, 3H). 2-019 (CDCl3, Me4Si, 400MHz) δ: 9.20-8.90 (m, 2H), 7.80-7.50 (m, 7H), 4.08 (d, J=17.2 Hz, 1H), 3.71 (d, J=17.2 Hz, 1H), 3.01 (s, 3H). 2-019(S) (CDCl3, Me4Si, 400MHz) δ: 9.00 (brs, 1H), 8.88 (s, 1H), 7.80-7.75 (m, 2H), 7.75-7.65 (m, 1H), 7.64 (s, 1H), 7.60-7.55 (m, 1H), 7.54 (s, 1H), 4.08 (d, J=17.2 Hz, 1H), 3.70 (d, J=17.2 Hz, 1H), 3.02 (s, 3H). 2-020(S) (CDCl3, Me4Si, 400MHz) δ: 9.32 (brs, 1H), 8.88 (s, 1H), 7.77 (s, 1H), 7.75-7.55 (m, 4H), 7.54 (s, 1H), 4.09 (d, J=17.2 Hz, 1H), 3.74 (d, J=17.2 Hz, 1H), 3.05 (q, J=7.2 Hz, 2H), 1.36 (t, J=7.2 Hz, 3H). 2-021 (CDCl3, Me4Si, 300MHz) δ: 8.90 (s, 1H), 7.65-7.55 (m, 6H), 4.08 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 2.60-2.45 (m, 4H), 1.25-1.15 (m, 2H), 1.05-0.95 (m, 2H). 2-022 (CDCl3, Me4Si, 300MHz) δ: 8.81 (s, 1H), 7.80-7.75 (m, 2H), 7.69 (dd, J=1.5, 8.1 Hz, 1H), 7.65-7.55 (m, 3H), 4.07 (d, J=17.2 Hz, 1H), 3.69 (d, J=17.2 Hz, 1H), 2.60-2.50 (m, 1H), 1.25-1.15 (m, 2H), 1.05-0.95 (m, 2H). 2-024 (CDCl3, Me4Si, 400MHz) δ: 9.03 (s, 1H), 7.80-7.70 (m, 1H), 7.70-7.55 (m, 5H), 4.07 (d, J=17.2 Hz, 1H), 3.80 (s, 3H), 3.69 (d, J=17.2 Hz, 1H), 3.23 (s, 3H). 2-025 (CDCl3, Me4Si, 400MHz) δ: 8.91 (s, 1H), 7.70-7.50 (m, 6H), 4.09 (d, J=17.2 Hz, 1H), 3.72 (d, J=17.2 Hz, 1H), 2.77 (s, 6H), 2.42 (s, 3H). 2-026 (CDCl3, Me4Si, 400MHz) δ: 9.23 (brs, 1H), 8.29 (s, 1H), 7.93 (s, 1H), 7.80-7.55 (m, 6H), 4.07 (d, J=17.2 Hz, 1H), 3.71 (d, J=17.2 Hz, 1H), 3.03 (q, J=7.2 Hz, 2H), 1.40 (t, J=7.2 Hz, 3H). 2-026(S) (CDCl3, Me4Si, 400MHz) δ: 8.79 (brs, 1H), 7.96 (s, 1H), 7.70-7.50 (m, 5H), 4.07 (d, J=17.2 Hz, 1H), 3.70 (d, J=17.2 Hz, 1H), 3.15-3.05 (m, 2H), 1.45-1.35 (m, 3H). 2-027 (CDCl3, Me4Si, 400MHz) δ: 8.84 (s, 1H), 7.97 (d, J=1.2 Hz, 1H), 7.76 (dd, J=1.2, 8.0 Hz, 1H), 7.70-7.50 (m, 5H), 4.08 (d, J=17.2 Hz, 1H), 3.71 (d, J=17.2 Hz, 1H), 3.03 (s, 3H). 2-027(S) (CDCl3, Me4Si, 300MHz) δ: 8.29 (brs, 1H), 7.95 (d, J=1.5 Hz, 1H), 7.75 (dd, J=1.8, 7.8 Hz, 1H), 7.70-7.50 (m, 4H), 4.07 (d, J=17.4 Hz, 1H), 3.69 (d, J=17.4 Hz, 1H), 3.02 (s, 3H). 2-028 (CDCl3, Me4Si, 400MHz) δ: 9.68 (brs, 1H), 8.84 (s, 1H), 7.85-7.80 (m, 1H), 7.75-7.50 (m, 5H), 4.07 (d, J=17.2 Hz, 1H), 3.70 (d, J=17.2 Hz, 1H), 3.64 (s, 3H). 2-028(S) (CDCl3, Me4Si, 400MHz) δ: 9.47 (brs, 1H), 8.80 (brs, 1H), 7.86 (s, 1H), 7.70-7.50 (m, 5H), 4.07 (d, J=17.2 Hz, 1H), 3.75-3.65 (m, 4H). 2-030 (CDCl3, Me4Si, 300MHz) δ: 9.10-9.00 (m, 2H), 7.65-750 (m, 6H), 7.35-7.25 (m, 1H), 5.08 (s, 2H), 4.08 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 2.48 (s, 3H). 2-031 (CDCl3, Me4Si, 300MHz) δ: 8.79 (s, 1H), 7.78 (d, J=1.5 Hz, 1H), 7.75 (d, J=8.1 Hz, 1H), 7.69 (dd, J=1.5, 8.1 Hz, 1H), 7.65-7.50 (m, 3H), 4.08 (d, J=17.4 Hz, 1H), 3.71 (d, J=17.4 Hz, 1H), 2.76 (s, 6H). 2-031(S) (CDCl3, Me4Si, 300MHz) δ: 9.01 (brs, 1H), 8.79 (S, 1H), 7.78 (d, J=1.5 Hz, 1H), 7.74 (d, J=8.1 Hz, 1H), 7.69 (dd, J=1.5, 8.1 Hz, 1H), 7.65-7.50 (m, 3H), 4.08 (d, J=17.4 Hz, 1H), 3.71 (d, J=17.4 Hz, 1H), 2.76 (s, 6H). 2-032 (CDCl3, Me4Si, 300MHz) δ: 8.76 (s, 1H), 8.00-7.95 (m, 1H), 7.80-7.50 (m, 4H), 4.08 (d, J=17.4 Hz, 1H), 3.71 (d, J=17.4 Hz, 1H), 2.75 (s, 6H). 2-034 (CDCl3, Me4Si, 400MHz) δ: 7.92 (brs, 1H), 7.88 (s, 1H), 7.70-7.50 (5H), 4.08 (d, J=17.2 Hz, 1H), 3.70 (d, J=17.2 Hz, 1H). 2-037(S) (CDCl3, Me4Si, 300MHz) δ: 10.43 (brs, 1H), 8.03 (d, J=8.1Hz, 1H), 7.65-7.45 (m, 5H), 4.09 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 3.42 (s, 3H), 2.97 (s, 6H), 2.64 (s, 3H). 2-039 (CDCl3, Me4Si, 300MHz) δ: 8.93 (s, 1H), 7.65-7.55 (m, 6H), 4.35-4.25 (m, 1H), 4.08 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 2.78 (d, J=5.4 Hz, 3H), 2.54 (s, 3H). 2-039(S) (CDCl3, Me4Si, 300MHz) δ: 9.00-8.95 (m, 2H), 7.65-7.50 (m, 6H), 4.45-4.35 (m, 1H), 4.08 (d, J=17.2 Hz, 1H), 3.70 (d, J=17.2 Hz, 1H), 2.77 (d, J=5.7 Hz, 3H), 2.54 (s, 3H). 2-040(S) (CDCl3, Me4Si, 300MHz) δ: 8.06 (d, J=8.1 Hz, 1H), 7.65-7.45 (m, 5H), 4.09 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 3.47 (s, 3H), 3.36 (q, J=7.5 Hz, 2H), 2.64 (s, 3H), 1.45 (t, J=7.5 Hz, 3H). 2-041 (CDCl3, Me4Si, 300MHz) δ: 8.02 (d, J=8.4 Hz, 1H), 7.70-7.45 (m, 6H), 4.15-4.05 (m, 3H), 3.70 (d, J=18.0 Hz, 1H), 3.35 (q, J=7.2 Hz, 2H), 2.64 (s, 3H), 1.45 (t, J=7.2 Hz, 3H), 1.37 (t, J=6.9 Hz, 3H). 2-042(S) (CDCl3, Me4Si, 300MHz) δ: 8.06 (d, J=8.1 Hz, 1H), 7.70-7.45 (m, 5H), 4.09 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 3.47 (s, 3H), 3.18 (s, 3H), 2.64 (s, 3H). 2-043(S) (CDCl3, Me4Si, 300MHz) δ: 8.03 (d, J=8.1 Hz, 1H), 7.70-7.50 (m, 5H), 4.20-4.05 (m, 3H), 3.71 (d, J=17.4 Hz, 1H), 3.21 (s, 3H), 2.64 (s, 3H), 1.38 (t, J=6.9 Hz, 3H). 3-001 (CDCl3, Me4Si, 300MHz) δ: 8.08 (s, 2H), 7.96 (s, 1H), 7.83 (d, J=7.8 Hz, 1H), 7.60-7.50 (m, 2H), 4.20 (d, J=17.1 Hz, 1H), 3.74 (d, J=17.1 Hz, 1H), 2.58 (s, 3H), 1.52 (s, 9H) 3-002 (CDCl3, Me4Si, 300MHz) δ: 8.93 (s, 1H), 8.08 (s, 2H), 7.98 (s, 1H), 7.65-7.55 (m, 3H), 4.21 (d, J=17.4 Hz, 1H), 3.76 (d, J=17.4 Hz, 1H), 3.02 (s, 3H), 2.56 (s, 3H). 3-004 (CDCl3, Me4Si, 300MHz) δ: 8.09 (s, 2H), 7.97 (s, 1H), 7.60-7.55 (m, 1H), 7.50-7.45 (m, 2H), 4.20 (d, J=17.4 Hz, 1H), 3.76 (d, J=17.4 Hz, 1H), 3.60-3.55 (m, 3H), 2.45 (s, 3H). 3-005 (CDCl3, Me4Si, 300MHz) δ: 8.84 (brs, 1H), 8.08 (s, 2H), 7.97 (s, 1H), 7.65-7.50 (m, 3H), 4.20 (d, J=17.4 Hz, 1H), 3.75 (d, J=17.4 Hz, 1H), 2.78 (s, 6H), 2.56 (s, 3H). 3-010 (CDCl3, Me4Si, 300MHz) δ: 8.90 (s, 1H), 8.08 (s, 2H), 7.98 (s, 1H), 7.65-7.55 (m, 3H), 4.21 (d, J=17.4 Hz, 1H), 3.76 (d, J=17.4 Hz, 1H), 3.09 (q, J=7.2 Hz, 2H), 2.56 (s, 3H), 1.39 (t, J=7.2 Hz, 3H). 3-013 (CDCl3, Me4Si, 300MHz) δ: 8.90 (s, 1H), 8.08 (s, 2H), 7.98 (s, 1H), 7.65-7.55 (m, 3H), 4.21 (d, J=17.4 Hz, 1H), 3.76 (d, J=17.4 Hz, 1H), 2.60-2.50 (m, 4H), 1.25-1.15 (m, 2H), 1.05-0.95 (m, 2H). 3-015 (CDCl3, Me4Si, 400MHz) δ: 10.11 (brs, 1H), 8.89 (brs, 1H), 8.09 (s, 2H), 7.99 (s, 1H), 7.70-7.60 (m, 2H), 7.60-7.50 (m, 1H), 4.21 (d, J=17.2 Hz, 1H), 3.78 (d, J=17.2 Hz, 1H), 3.59 (s, 3H). 3-017 (CDCl3, Me4Si, 400MHz) δ: 9.42 (brs, 1H), 9.04 (s, 1H), 8.08 (s, 2H), 7.99 (s, 1H), 7.79 (s, 1H), 7.75-7.55 (m, 3H), 4.22 (d, J=17.2 Hz, 1H), 3.82 (d, J=17.2 Hz, 1H), 3.10-3.00 (m, 2H), 1.40-1.30 (m, 3H). 3-022 (CDCl3, Me4Si, 400MHz) δ: 8.86 (s, 1H), 8.07 (s, 2H), 7.99 (s, 1H), 7.85-7.75 (m, 2H), 7.73 (dd, J=2.0, 8.4 Hz, 1H), 4.20 (d, J=17.2 Hz, 1H), 3.76 (d, J=17.2 Hz, 1H), 3.03 (s, 3H). 3-023 (CDCl3, Me4Si, 300MHz) δ: 8.75 (s, 1H), 8.07 (s, 2H), 7.98 (s, 1H), 7.80-7.65 (m, 3H), 4.19 (d, J=17.4 Hz, 1H), 3.76 (d, J=17.4 Hz, 1H), 2.78 (s, 6H). 3-025 (CDCl3, Me4Si, 400MHz) δ: 8.80 (brs, 1H), 8.67 (s, 1H), 8.08 (s, 2H), 7.96 (s, 1H), 7.87 (d, J=1.6 Hz, 1H), 7.76 (d, J=8.0 Hz, 1H), 7.67 (d, J=1.6, 8.0 Hz, 1H), 4.08 (d, J=17.2 Hz, 1H), 3.74 (d, J=17.2 Hz, 1H), 1.51 (s, 9H). 3-031 (CDCl3, Me4Si, 400MHz) δ: 9.28 (brs, 1H), 8.92 (s, 1H), 8.08 (s, 2H), 7.99 (s, 1H), 7.94 (s, 1H), 7.80-7.55 (m, 3H), 4.22 (d, J=17.2 Hz, 1H), 3.81 (d, J=17.2 Hz, 1H), 2.96 (s, 3H). 3-032 (CDCl3, Me4Si, 400MHz) δ: 8.72 (brs, 1H), 8.08 (s, 1H), 7.99 (d, J=1.6 Hz, 2H), 7.78 (dd, J=1.6, 8.0 Hz, 1H), 7.70 (d, J=8.0 Hz, 1H), 4.20 (d, J=17.2 Hz, 1H), 3.76 (d, J=17.2 Hz, 1H), 2.78 (s, 6H). 4-002 (S)(CDCl3, Me4Si, 300MHz) δ: 9.87 (brs, 1H), 9.01 (brs, 1H), 7.60-7.40 (m, 5H), 4.09 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 3.58 (s, 3H), 2.43 (s, 3H). 4-002 (R)(CDCl3, Me4Si, 300MHz) δ: 9.87 (brs, 1H), 9.01 (brs, 1H), 7.60-7.40 (m, 5H), 4.09 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 3.58 (s, 3H), 2.43 (s, 3H). 4-007 (CDCl3, Me4Si, 300MHz) δ: 9.38 (brs, 3H), 7.85 (d, J=8.1 Hz, 1H), 7.60-7.50 (m, 4H), 4.10 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 2.55 (s, 3H), 1.50-1.40 (m, 1H), 1.10-0.85 (m, 4H). 4-008 (CDCl3, Me4Si, 300MHz) δ: 10.32 (brs, 1H), 8.07 (d, J=7.8 Hz, 1H), 7.78 (brs, 1H), 7.59 (d, J=6.3 Hz, 2H), 7.55-7.45 (m, 2H), 4.10 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 3.48 (s, 3H), 2.80-2.70 (m, 1H), 2.65 (s, 3H), 1.40-1.35 (m, 2H), 1.20-1.15 (m, 2H). 4-010 (CDCl3, Me4Si, 300MHz) δ: 9.85-8.45 (m, 3H), 7.70-7.65 (m, 1H), 7.59 (d, J=6.0 Hz, 2H), 7.50-7.45 (m, 2H), 4.20-4.05 (m, 3H), 3.69 (d, J=17.7 Hz, 1H), 2.47 (s, 3H), 1.30-1.25 (m, 3H). 4-015 (CDCl3, Me4Si, 300MHz) δ: 8.95 (brs, 1H), 7.81 (d, J=9.0 Hz, 1H), 7.59 (d, J=6.0 Hz, 2H), 7.55-7.45 (m, 2H), 4.08 (d, J=17.4 Hz, 1H), 3.79 (s, 3H), 3.68 (d, J=17.4 Hz, 1H), 3.23 (s, 3H), 2.57 (s, 3H). 4-016 (CDCl3, Me4Si, 300MHz) δ: 9.05-8.85 (m, 1H), 7.75-7.70 (m, 1H), 7.60-7.55 (m, 4H), 6.75-6.55 (m, 1H), 4.10 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 3.10-2.95 (m, 3H), 2.60-2.55 (m, 3H). 4-017 (CDCl3, Me4Si, 300MHz) δ: 9.35 (brs, 1H), 8.37 (brs, 1H), 7.70-7.45 (m, 5H), 4.08 (d, J=17.4 Hz, 1H), 3.68 (d, J=17.4 Hz, 1H), 3.55-3.30 (m, 2H), 3.10-2.85 (m, 3H), 2.55-2.50 (m, 3H), 1.20-1.05 (m, 3H). 4-020 (CDCl3, Me4Si, 300MHz) δ: 8.89 (s, 1H), 7.65-7.55 (m, 5H), 4.09 (d, J=17.4 Hz, 1H), 3.69 (d, J=17.4 Hz, 1H), 3.09 (q, J=7.5 Hz, 2H), 2.55 (s, 3H), 1.40 (t, J=7.5 Hz, 3H). 4-021 (CDCl3, Me4Si, 300MHz) δ: 10.35 (brs, 1H), 8.06 (d, J=7.8 Hz, 1H), 7.60-7.45 (m, 4H), 4.10 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 3.46 (s, 3H), 3.18 (s, 3H), 2.64 (s, 3H). 4-021(S) (CDCl3, Me4Si, 400MHz) δ: 10.35 (brs, 1H), 8.06 (d, J=8.0 Hz, 1H), 7.90-7.45 (m, 5H), 4.11 (d, J=17.2 Hz, 1H), 3.71 (d, J=17.2 Hz, 1H), 3.46 (s, 3H), 3.19 (s, 3H), 2.64 (s, 3H). 4-021(R) (CDCl3, Me4Si, 400MHz) δ: 10.35 (brs, 1H), 8.06 (d, J=8.0 Hz, 1H), 7.90-7.45 (m, 5H), 4.11 (d, J=17.2 Hz, 1H), 3.71 (d, J=17.2 Hz, 1H), 3.46 (s, 3H), 3.19 (s, 3H), 2.64 (s, 3H). 4-022 (CDCl3, Me4Si, 300MHz) δ: 10.31 (brs, 2H), 8.06 (d, J=8.4 Hz, 1H), 7.59 (d, J=6.3 Hz, 2H), 7.55-7.45 (m, 2H), 4.10 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 3.48 (s, 3H), 3.37 (q, J=7.5 Hz, 2H), 2.64 (s, 3H), 1.45 (t, J=7.5 Hz, 3H). 4-026 (CDCl3, Me4Si, 300MHz) δ: 8.25-8.15 (m, 2H), 7.85-7.65 (m, 5H), 7.59 (d, J=6.3 Hz, 2H), 4.09 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H). 4-030 (CDCl3, Me4Si, 300MHz) δ: 9.33 (brs, 1H), 8.84 (brs, 1H), 7.80-7.55 (m, 5H), 4.07 (d, J=17.4 Hz, 1H), 3.75-3.70 (m, 3H), 3.68 (d, J=17.4 Hz, 1H). 4-030(S) (CDCl3, Me4Si, 400MHz) δ: 8.88 (brs, 1H), 7.75-7.50 (m, 5H), 4.08 (d, J=17.2 Hz, 1H), 3.71 (d, J=17.2 Hz, 1H), 3.62 (s, 3H). 4-030(R) (CDCl3, Me4Si, 400MHz) δ: 8.88 (brs, 1H), 7.75-7.50 (m, 5H), 4.08 (d, J=17.2 Hz, 1H), 3.71 (d, J=17.2 Hz, 1H), 3.62 (s, 3H). 4-031 (CDCl3, Me4Si, 300MHz) δ: 9.03 (brs, 1H), 8.73 (brs, 1H), 7.77 (d, J=8.1 Hz, 1H), 7.70-7.55 (m, 4H), 4.22 (q, J=7.2 Hz, 2H), 4.07 (d, J=17.4 Hz, 1H), 3.67 (d, J=17.4 Hz, 1H), 1.31 (t, J=7.2 Hz, 3H). 4-033 (CDCl3, Me4Si, 300MHz) δ: 9.33 (brs, 1H), 7.70-7.55 (m, 5H), 4.08 (d, J=17.4 Hz, 1H), 3.69 (d, J=17.4 Hz, 1H), 3.15-2.90 (m, 6H). 4-033(S) (CDCl3, Me4Si, 400MHz) δ:9.32 (brs, 1H), 7.70-7.65 (m, 2H), 7.60-7.55 (m, 3H), 4.07 (d, J=17.2 Hz, 1H), 3.69 (d, J=17.2 Hz, 1H), 3.04 (brs, 6H). 4-036 (CDCl3, Me4Si, 400MHz) δ: 8.90 (s, 1H), 7.65-7.55 (m, 5H), 4.09 (d, J=17.6 Hz, 1H), 3.70 (d, J=17.6 Hz, 1H), 3.10-3.00 (m, 2H), 2.55 (s, 3H), 1.95-1.80 (m, 2H), 1.06 (t, J=7.6 Hz, 3H). 4-041 (CDCl3, Me4Si, 300MHz) δ: 9.50 (brs, 1H), 8.80 (brs, 1H), 7.85 (s, 1H), 7.70-7.60 (m, 2H), 7.58 (d, J=5.7 Hz, 2H), 4.07 (d, J=17.4 Hz, 1H), 3.75-3.65 (m, 4H). 4-041(S) (CDCl3, Me4Si, 400MHz) δ: 9.83 (brs, 1H), 8.85 (s, 1H), 7.90-7.80 (m, 1H), 7.70-7.50 (m, 4H), 4.07 (d, J=17.2 Hz, 1H), 3.70 (d, J=17.2 Hz, 1H), 3.61 (s, 3H). 4-046 (CDCl3, Me4Si, 400MHz) δ: 9.10-8.40 (m, 1H), 8.10-7.45 (m, 5H), 4.15-4.05 (m, 1H), 3.83 and 3.73 (s, 3H), 3.69 (d, J=17.2 Hz, 1H), 3.10-3.05 (m, 3H), 2.64 and 2.56 (s, 3H). 4-047 (CDCl3, Me4Si, 400MHz) δ: 9.10-8.45 (m, 1H), 8.05-7.50 (m, 5H), 4.15-4.05 (m, 1H), 3.85-3.65 (m, 4H), 3.60-3.50 (m, 2H), 2.63 and 2.57 (s, 3H), 1.30-1.25 (m, 3H). 4-048 (CDCl3, Me4Si, 400MHz) δ: 8.90 (s, 1H), 7.65-7.55 (m, 6H), 4.09 (d, J=17.2 Hz, 1H), 3.70 (d, J=17.2 Hz, 1H), 3.25-3.15 (m, 1H), 2.54 (s, 3H), 1.39 (d, J=6.8 Hz, 6H). 4-052 (CDCl3, Me4Si, 400MHz) δ: 9.29 (brs, 1H), 8.85 (s, 1H), 7.93 (d, J=1.6 Hz, 1H), 7.72 (dd, J=1.6, 8.4 Hz, 1H), 7.62 (d, J=8.4 Hz, 1H), 7.58 (d, J=6.0 Hz, 2H), 4.10 (d, J=17.2 Hz, 1H), 3.73 (d, J=17.2 Hz, 1H), 3.03 (q, J=7.2 Hz, 2H), 1.34 (t, J=7.2 Hz, 3H). 4-052(S) (CDCl3, Me4Si, 400MHz) δ: 9.37 (brs, 1H), 8.83 (s, 1H), 8.00-7.90 (m, 1H), 7.85-7.50 (m, 5H), 4.07 (d, J=17.2 Hz, 1H), 3.75-3.65 (m, 1H), 3.10-2.95 (m, 2H), 1.40-1.30 (m, 3H). 4-054 (CDCl3, Me4Si, 300MHz) δ: 9.15 (brs, 1H), 8.80 (s, 1H), 7.96 (d, J=1.5 Hz, 1H), 7.74 (dd, J=1.5, 8.1 Hz, 1H), 7.70-7.50 (m, 4H), 4.09 (d, J=17.4 Hz, 1H), 3.73 (d, J=17.4 Hz, 1H), 2.74 (s, 6H). 4-055 (CDCl3, Me4Si, 400MHz) δ: 8.29 (brs, 1H), 7.96 (d, J=1.6 Hz, 1H), 7.70 (dd, J=1.6, 8.0 Hz, 1H), 7.67 (d, J=8.0 Hz, 1H), 7.58 (d, J=6.0 Hz, 2H), 4.08 (d, J=17.2 Hz, 1H), 3.69 (d, J=17.2 Hz, 1H), 3.03 (s, 3H). 4-055(S) (CDCl3, Me4Si, 300MHz) δ: 8.81 (brs, 1H), 7.95 (d, J=1.2 Hz, 1H), 7.74 (dd, J=1.2, 8.4 Hz, 1H), 7.66 (d, J=8.4 Hz, 1H), 7.57 (d, J=6.3 Hz, 2H), 4.07 (d, J=17.4 Hz, 1H), 3.68 (d, J=17.4 H, 1H), 3.02 (s, 3H). 4-057 (CDCl3, Me4Si, 400MHz) δ: 8.77 (brs, 1H), 7.80-7.75 (m, 2H), 7.70 (dd, J=1.6, 8.0 Hz, 1H), 7.58 (d, J=6.0 Hz, 2H), 4.08 (d, J=17.2 Hz, 1H), 3.70 (d, J=17.2 Hz, 1H), 2.78 (s, 6H). 4-059 (CDCl3, Me4Si, 300MHz) δ: 9.54 (brs, 1H), 8.12 (d, J=8.4 Hz, 2H), 7.72 (d, J=8.4 Hz, 2H), 7.59 (d, J=6.0 Hz, 2H), 4.11 (d, J=17.4 Hz, 1H), 3.72 (d, J=17.4 Hz, 1H), 2.50-2.35 (m, 1H), 2.30-2.15 (m, 1H), 1.95-1.70 (m, 1H). 4-063 (CDCl3, Me4Si, 300MHz) δ: 9.25 (brs, 1H), 8.20 (d, J=8.4 Hz, 2H), 7.70 (d, J=8.4 Hz, 2H), 7.58 (d, J=6.0 Hz, 2H), 4.12 (d, J=17.4 Hz, 1H), 3.72 (d, J=17.4 Hz, 1H), 1.50-1.35 (m, 1H), 1.10-0.95 (m, 2H), 0.90-0.80 (m, 2H). 5-009 (CDCl3, Me4Si, 300MHz) δ: 9.19 (brs, 1H), 8.93 (s, 1H), 7.63 (s, 2H), 7.60 (s, 1H), 7.60-7.50 (m, 2H), 4.10 (d, J=17.4 Hz, 1H), 3.71 (d, J=17.4 Hz, 1H), 3.06 (q, J=7.2 Hz, 2H), 2.59 (s, 3H), 1.37 (t, J=7.2 Hz, 3H). 5-010 (CDCl3, Me4Si, 400MHz) δ: 9.25-8.80 (m, 2H), 7.70-7.50 (m, 5H), 4.11 (d, J=17.2 Hz, 1H), 3.74 (d, J=17.2 Hz, 1H), 2.75 (s, 6H), 2.53 (s, 3H). 5-014 (CDCl3, Me4Si, 400MHz) δ: 8.78 (brs, 1H), 7.75-7.50 (m, 5H), 4.08 (d, J=17.2 Hz, 1H), 3.74 (s, 3H), 3.69 (d, J=17.2 Hz, 1H). 6-004(S) (CDCl3, Me4Si, 400MHz) δ: 8.87 (brs, 1H), 7.82 (s, 1H), 7.76 (s, 1H), 7.70 (s, 1H), 7.65 (d, J=7.6 Hz, 1H), 7.55-7.45 (m, 2H), 4.14 (d, J=17.2 Hz, 1H), 3.73 (d, J=17.2 Hz, 1H), 3.67 (s, 3H). 6-004(R) (CDCl3, Me4Si, 400MHz) δ: 8.87 (brs, 1H), 7.82 (s, 1H), 7.76 (s, 1H), 7.70 (s, 1H), 7.65 (d, J=7.6 Hz, 1H), 7.55-7.45 (m, 2H), 4.14 (d, J=17.2 Hz, 1H), 3.73 (d, J=17.2 Hz, 1H), 3.67 (s, 3H). 6-011(S) (CDCl3, Me4Si, 400MHz) δ: 9.10-8.70 (m, 3H), 7.95-7.55 (m, 6H), 4.15-4.10 (m, 1H), 3.71 (d, J=17.2 Hz, 1H), 1.51 (s, 9H). 6-015 (CDCl3, Me4Si, 400MHz) δ: 9.10 (brs, 1H), 8.89 (s, 1H), 7.80-7.70 (m, 5H), 7.55 (brs, 1H), 4.14 (d, J=17.2 Hz, 1H), 3.74 (d, J=17.2 Hz, 1H), 3.00 (s, 3H). 6-015(S) (CDCl3, Me4Si, 400MHz) δ: 8.88 (brs, 1H), 7.85-7.70 (m, 6H), 4.20-4.10 (m, 1H), 3.80-3.65 (m, 1H), 3.02 (s, 3H). 6-016 (CDCl3, Me4Si, 400MHz) δ: 8.99 (brs, 1H), 8.84 (s, 1H), 7.85-7.70 (m, 6H), 4.14 (d, J=17.2 Hz, 1H), 3.74 (d, J=17.2 Hz, 1H), 3.08 (q, J=7.2 Hz, 2H), 1.38 (t, J=7.2 Hz, 3H). 6-016(S) (CDCl3, Me4Si, 400MHz) δ: 8.84 (brs, 1H), 7.85-7.70 (m, 6H), 4.20-4.10 (m, 1H), 3.73 (d, J=17.2 Hz, 1H), 3.15-3.05 (m, 2H), 1.40-1.30 (m, 3H). 6-018(S) (CDCl3, Me4Si, 400MHz) δ: 8.80 (brs, 1H), 7.85-7.80 (m, 1H), 7.80-7.65 (m, 4H), 7.65-7.55 (m, 1H), 4.15-4.05 (m, 1H), 3.75-3.65 (m, 4H). 6-019 (CDCl3, Me4Si, 400MHz) δ: 9.32 (brs, 1H), 7.85 (s, 1H), 7.76 (s, 1H), 7.70-7.50 (m, 4H), 4.13 (d, J=17.2 Hz, 1H), 3.73 (d, J=17.2 Hz, 1H), 3.15-2.90 (m, 6H). 6-020 (CDCl3, Me4Si, 400MHz) δ: 9.10 (brs, 1H), 8.82 (s, 1H), 7.85-7.75 (m, 2H), 7.75-7.70 (m, 4H), 4.15 (d, J=17.2 Hz, 1H), 3.76 (d, J=17.2 Hz, 1H), 2.76 (s, 6H). 6-021 (CDCl3, Me4Si, 300MHz) δ: 8.85 (brs, 1H), 7.81 (s, 1H), 7.75 (s, 1H), 7.70 (s, 1H), 7.65-7.55 (m, 3H), 4.14 (d, J=17.4 Hz, 1H), 3.73 (d, J=17.4 Hz, 1H), 2.78 (s, 6H), 2.43 (s, 3H). 6-023 (CDCl3, Me4Si, 400MHz) δ: 8.75 (brs, 1H), 8.00-7.50 (m, 7H), 4.14 (d, J=17.2 Hz, 1H)...

Claims

1. An isoxazoline-substituted benzamide compound represented by the following formula (1), or a salt thereof. 【Chemistry 1】 [In the formula, W represents an oxygen atom or a sulfur atom, Q represents Q-1 or Q-2, 【Chemistry 2】 X １ , X ２ and X ３ each independently represents a hydrogen atom, a halogen atom, cyano, nitro, amino, C １ to C ６ alkyl, C １ to C ６ alkoxy, C １ to C ６ haloalkyl or halo(C １ to C ６ )alkoxy, Y １ These are hydrogen atoms, halogen atoms, cyano, nitro, and C. １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl or Halo(C) １ ~C ６ ) Represents alkoxy, Y ２ This represents a hydrogen atom, Or, Y １ and Y ２ These elements combine to form a 6-membered ring -CH=CH-CH=CH-, R １ represents -C(O)R １ａ -C(S)R １ａ -C(O)OR ２ａ -C(O)SR ２ａ -C(O)N(R １ｃ )R １ｂ -C(S)N(R １ｃ )R １ｂ -S(O) ２ R １ａ -S(O) ２ N(R １ｃ )R １ｂ -C(O)C(O)R １ａ or -CHO, R ２ C is a hydrogen atom. １ ~C ６ Alkyl, R １０ Replaced by (C １ ~C ６ ) alkyl, C ２ ~C ６ Alkenyl or C ２ ~C ６ Representing Alkinil, R ３ C is a hydrogen atom. １ ~C ６ Alkyl, R ６ Replaced by (C １ ~C ６ ) alkyl, C １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenil, Halo (C) ２ ~C ６ ) Alkenil, C ２ ~C ６ Alkinil, Halo (C) ２ ~C ６ ) Alkinyl, C ３ ~C １０ Cycloalkyl, Halo(C) ３ ~C １０ ) Cycloalkyl, C １ ~C ６ Alkoxy, Halo(C) １ ~C ６ ) Alkoxy, -C(O)R １d , -C(S)R １d , -C(O)OR １d , -C(O)SR １d , -C(O)N(R １f )R １e , -C(S)N(R １f )R １e , -S(O) ２ R １d , -S(O) ２ N(R) １f )R １e or -N(R １４ ) R １５ This represents, R ４ represents a hydrogen atom, C １ to C ６ alkyl, C ２ to C ６ alkenyl or C ２ to C ６ alkynyl, and R Ａ is C １ to C ６ alkyl, R １６ substituted by (C １ to C ６ ) alkyl, C １ to C ６ haloalkyl, C ２ to C ６ alkenyl, halo(C ２ to C ６ ) alkenyl, C ２ to C ６ alkynyl, halo(C ２ to C ６ ) alkynyl, C ３ to C １０ cycloalkyl, -C(O)R １ｇ or -C(O)OR １ｈ represents, R １ａ C １ ~C １０ Alkyl, R ７ Replaced by (C １ ~C ６ ) alkyl, C １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenil, Halo (C) ２ ~C ６ ) Alkenil, C ２ ~C ６ Alkinil, Halo (C) ２ ~C ６ ) Alkinyl, C ３ ~C １０ Cycloalkyl, Halo(C) ３ ~C １０ ) Cycloalkyl, R １３ C replaced by ３ ~C １０ Cycloalkyl, phenyl, (Z １ ) ｐ１ Represents phenyl, D-1 to D-60, G-1 to G-60, or G-61 substituted by, D-1 to D-60 represent the following structures, 【Transformation 3】 【Chemistry 4】 【Transformation 5】 G-1 to G-61 represent the following structures, 【Transformation 6】 【Transformation 7】 【Transformation 8】 R ２ａ C １ ~C ６ Alkyl, R ７ Replaced by (C １ ~C ６ ) alkyl, C １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenil, Halo (C) ２ ~C ６ ) Alkenil, C ２ ~C ６ Alkinil, Halo (C) ２ ~C ６ ) Alkinyl, C ３ ~C １０ Cycloalkyl, phenyl or (Z １ ) ｐ１ Represents phenyl substituted by, R １ｂ C is a hydrogen atom. １ ~C ６ Alkyl, R ８ Replaced by (C １ ~C ６ ) alkyl, C １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenil, Halo (C) ２ ~C ６ ) Alkenil, C ２ ~C ６ Alkinil, Halo (C) ２ ~C ６ ) Alkinyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxy, Halo(C) １ ~C ６ ) Alkoxy, C １ ~C ６ Alkoxycarbonyl, phenyl or (Z １ ) ｐ１ Represents phenyl substituted by, R １ｃ is a hydrogen atom or C １ ~C ６ Represents alkyl, R １ｄ C １ ~C ６ Alkyl, R ９ Replaced by (C １ ~C ６ ) alkyl, C １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenil, Halo (C) ２ ~C ６ ) Alkenil, C ２ ~C ６ Alkinil, Halo (C) ２ ~C ６ ) Alkinyl, C ３ ~C １０ Cycloalkyl, Halo(C) ３ ~C １０ )Cycloalkyl, phenyl, (Z ２ ) ｐ２ Represents phenyl, G-4 to G-10, G-50 to G-57, or G-58 substituted by, R １ｅ C is a hydrogen atom. １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinyl, C ３ ~C １０ Cycloalkyl, phenyl or (Z ２ ) ｐ２ Represents phenyl substituted by, R １ｆ is a hydrogen atom or C １ ~C ６ Represents alkyl, R １ｇ C １ ~C ６ Alkyl, R １８ Replaced by (C １ ~C ６ ) alkyl, C １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenil, Halo (C) ２ ~C ６ ) Alkenil, C ２ ~C ６ Alkinil, Halo (C) ２ ~C ６ ) Alkinyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkylamino or di(C) １ ~C ６ ) Represents alkylamino, R １ｈ C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl or C ２ ~C ６ Representing Alkinnil, R ５ C １ ~C ６ Represents a haloalkyl group, R ６ C is cyano, nitro, amino, hydroxy, C ３ ~C １０ Cycloalkyl, Halo(C) ３ ~C １０ ) Cycloalkyl, C １ ~C ６ Alkoxy, Halo(C) １ ~C ６ ) Alkoxy, C １ ~C ６ Alkylthio, Halo(C) １ ~C ６ ) Alkylthio, C １ ~C ６ Alkyl sulfinyl, halo(C) １ ~C ６ ) Alkyl sulfinyl, C １ ~C ６ Alkyl sulfonyl, halo(C) １ ~C ６ ) Alkyl sulfonyl, C １ ~C ６ Alkylamino, di(C) １ ~C ６ ) Alkylamino, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkoxyimino, phenyl or (Z ２ ) ｐ２ Represents phenyl substituted by, R ７ is cyano, C １ ~C ６ Alkoxy, Halo(C) １ ~C ６ ) Alkoxy, C １ ~C ６ Alkylthio, Halo(C) １ ~C ６ ) Alkylthio, C １ ~C ６ Alkyl sulfinyl, halo(C) １ ~C ６ ) Alkyl sulfinyl, C １ ~C ６ Alkyl sulfonyl, halo(C) １ ~C ６ ) Alkyl sulfonyl, C ３ ~C １０ Cycloalkyl, phenyl, (Z １ ) ｐ１ Phenyl substituted by -N(R １４ ) R １５ , represents G-1 to G-60 or G-61, R ８ is cyano, C １ ~C ６ Alkoxy, Halo(C) １ ~C ６ ) Alkoxy, phenyl or (Z １ ) ｐ１ Represents phenyl substituted by, R ９ is cyano, C １ ~C ６ Alkoxy, Halo(C) １ ~C ６ ) Alkoxy, C １ ~C ６ Alkylthio, Halo(C) １ ~C ６ ) Alkylthio, C １ ~C ６ Alkyl sulfinyl, halo(C) １ ~C ６ ) Alkyl sulfinyl, C １ ~C ６ Alkyl sulfonyl, halo(C) １ ~C ６ ) Alkyl sulfonyl or C ３ ~C １０ Represents cycloalkyl, R １０ is cyano, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkoxyimino, phenyl or (Z ３ ) ｐ３ Represents phenyl substituted by, R １１ is a hydrogen atom or C １ ~C ６ Represents alkyl, R １２ C １ ~C ６ Represents alkyl, R １３ This represents Cyano, R １４ C is a hydrogen atom. １ ~C ６ Alkyl, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl or C １ ~C ６ Represents alkylsulfonyl, R １５ is a hydrogen atom or C １ ~C ６ Represents alkyl, R １６ is cyano, C １ ~C ６ Alkoxy, Halo(C) １ ~C ６ ) Alkoxy, C １ ~C ６ Alkylthio, Halo(C) １ ~C ６ ) Alkylthio, C １ ~C ６ Alkyl sulfinyl, halo(C) １ ~C ６ ) Alkyl sulfinyl, C １ ~C ６ Alkyl sulfonyl, halo(C) １ ~C ６ ) Alkyl sulfonyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkoxyimino, phenyl or (Z ４ ) ｐ４ Represents phenyl substituted by, R １７ is cyano, C １ ~C ６ Alkoxy or C １ ~C ６ Alkoxy (C １ ~C ６ ) Represents alkoxy, R １８ is cyano, C １ ~C ６ Alkoxy, C １ ~C ６ Alkoxy (C １ ~C ６ ) Alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkyl sulfinyl or C １ ~C ６ Represents alkylsulfonyl, Z １ These are halogen atoms, cyano, nitro, and C. １ ~C ６ Alkyl, R １７ Replaced by (C １ ~C ６ ) alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, Halo(C) １ ~C ６ ) Alkoxy, C １ ~C ６ Alkylthio, Halo(C) １ ~C ６ ) Alkylthio, C １ ~C ６ Alkyl sulfinyl, halo(C) １ ~C ６ ) Alkyl sulfinyl, C １ ~C ６ Alkyl sulfonyl, halo(C) １ ~C ６ ) Alkyl sulfonyl, C １ ~C ６ Alkylamino, di(C) １ ~C ６ ) Alkylamino or C ３ ~C １０ When representing a cycloalkyl group and p1 represents an integer of 2, 3, 4, or 5, each Z １ They may be the same as each other or different from each other. Z １ａ These are hydrogen atoms, halogen atoms, cyano, nitro, and C. １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, Halo(C) １ ~C ６ ) Alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkyl sulfinyl or C １ ~C ６ Represents alkylsulfonyl, Z ２ is a halogen atom, cyano, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl or C １ ~C ６ When an alkoxy is represented and p2 represents an integer of 2, 3, 4, or 5, each Z ２ They may be the same as each other or different from each other. Z ３ is a halogen atom, cyano, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl or C １ ~C ６ When an alkoxy is represented and p3 represents an integer of 2, 3, 4, or 5, each Z ３ They may be the same as each other or different from each other. Z ４ is a halogen atom, cyano, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl or C １ ~C ６ When an alkoxy is represented and p4 represents an integer of 2, 3, 4, or 5, each Z ４ They may be the same as each other or different from each other. p1 represents an integer of 1, 2, 3, 4, or 5. p2 represents an integer of 1, 2, 3, 4, or 5. p3 represents an integer of 1, 2, 3, 4, or 5. p4 represents an integer of 1, 2, 3, 4, or 5. q3 represents an integer of 0, 1, 2, or 3. q4 represents an integer of 0, 1, 2, 3, or 4. q5 represents an integer of 0, 1, 2, 3, 4, or 5. q6 represents an integer of 0, 1, 2, 3, 4, 5, or 6. g2 represents an integer of 0, 1, or 2. g3 represents an integer of 0, 1, 2, or 3. g4 represents an integer of 0, 1, 2, 3, or 4. r represents an integer of 0, 1, or 2.

2. W represents an oxygen atom, X １ , X ２ and X ３ Each of these is independently a hydrogen atom, a halogen atom, or C １ ~C ６ Represents a haloalkyl group, Y １ is a hydrogen atom, a halogen atom, nitro, C １ ~C ６ Alkyl or C １ ~C ６ Represents a haloalkyl group, Or, Y １ and Y ２ These elements combine to form a 6-membered ring -CH=CH-CH=CH-, R １ is -C(O)R １ａ ,-C(O)OR ２ａ ,-C(O)SR ２ａ ,-C(O)N(R １ｃ )R １ｂ ,-C(S)N(R １ｃ )R １ｂ ,-S(O) ２ R １ａ ,-S(O) ２ N(R １ｃ )R １ｂ ,-C(O)C(O)R １ａ or -CHO, R ３ C is a hydrogen atom. １ ~C ６ Alkyl, R ６ Replaced by (C １ ~C ６ ) alkyl, C １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxy, -C(O)R １ｄ , -C(O)OR １ｄ , -C(O)N(R １ｆ )R １ｅ or -S(O) ２ R １d This represents, R ４ C is a hydrogen atom. １ ~C ６ Alkyl or C ２ ~C ６ Representing Alkinnil, R Ａ C １ ~C ６ Alkyl, R １６ Replaced by (C １ ~C ６ ) alkyl, C ２ ~C ６ Alkenyl or C ２ ~C ６ Representing Alkinnil, R １ａ C １ ~C １０ Alkyl, R ７ Replaced by (C １ ~C ６ ) alkyl, C １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenil, Halo (C) ２ ~C ６ ) Alkenil, C ２ ~C ６ Alkinyl, C ３ ~C １０ Cycloalkyl, Halo(C) ３ ~C １０ ) Cycloalkyl, R １３ C replaced by ３ ~C １０ Cycloalkyl, phenyl, (Z １ ) ｐ１ Represents phenyl, D-2, D-3, D-14, D-23, D-30, D-37, D-58, G-1, G-2, G-4 to G-10, G-12 to G-20, G-22 to G-27, G-39, G-50 to G-57 or G-58 substituted by, R ２ａ C １ ~C ６ Alkyl, R ７ Replaced by (C １ ~C ６ ) alkyl, C １ ~C ６ Haloalkyl or C ２ ~C ６ Representing Alkenil, R １ｂ C is a hydrogen atom. １ ~C ６ Alkyl, R ８ Replaced by (C １ ~C ６ ) alkyl, C １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenil, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Alkoxycarbonyl, phenyl or (Z １ ) ｐ１ Represents phenyl substituted by, R １ｄ C １ ~C ６ Alkyl, R ９ Replaced by (C １ ~C ６ ) alkyl, C ２ ~C ６ Alkenil, C ３ ~C １０ Cycloalkyl, Halo(C) ３ ~C １０ )Cycloalkyl, phenyl, (Z ２ ) ｐ２ Represents phenyl, G-5, or G-51 substituted by, R １ｅ C １ ~C ６ Alkyl, C ２ ~C ６ Alkenil, C ３ ~C １０ Cycloalkyl or (Z ２ ) ｐ２ Represents phenyl substituted by, R ６ is cyano, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Represents alkoxy or phenyl, R ７ C １ ~C ６ Alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkyl sulfonyl, C ３ ~C １０ Cycloalkyl, phenyl, -N(R １４ ) R １５ , represents G-11, G-21 or G-30, R ８ C １ ~C ６ Represents alkoxy or phenyl, R ９ C １ ~C ６ Represents alkoxy, R １０ C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Alkoxyimino, phenyl or (Z ３ ) ｐ３ Represents phenyl substituted by, R １４ C １ ~C ６ Alkyl, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl or C １ ~C ６ Represents alkylsulfonyl, R １６ C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxyimino, phenyl or (Z ４ ) ｐ４ Represents phenyl substituted by, R １７ C １ ~C ６ Alkoxy (C １ ~C ６ ) Represents alkoxy, Z １ These are halogen atoms, cyano, nitro, and C. １ ~C ６ Alkyl, R １７ Replaced by (C １ ~C ６ ) alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, Halo(C) １ ~C ６ ) Alkoxy, C １ ~C ６ Alkylthio or C １ ~C ６ When representing alkylsulfonyl and p1 represents an integer of 2, each Z １ They may be the same as each other or different from each other. Z １ａ This represents a hydrogen atom, Z ２ is a halogen atom or C １ ~C ６ When representing an alkyl group and p2 represents an integer of 2, each Z ２ They may be the same as each other or different from each other. Z ３ This represents a halogen atom, Z ４ This represents a halogen atom, p1 represents an integer of 1 or 2, p2 represents an integer of 1 or 2, p3 represents an integer of 1, p4 represents an integer of 1, q3 represents an integer of 0, q4 represents an integer of 0. q5 represents an integer of 0, g3 represents an integer of 0 or 1. g4 represents an integer of 0, 1, or 2. The isoxazoline-substituted benzamide compound or salt thereof according to claim 1, wherein r represents 0.

3. A pest control agent containing one or more selected from the isoxazoline-substituted benzamide compounds and salts thereof described in any one of claims 1 to 2 as an active ingredient.

4. A pesticide containing one or more isoxazoline-substituted benzamide compounds and salts thereof selected from any one of claims 1 to 2 as an active ingredient.

5. A control agent for internal or external parasites of mammals or birds, comprising one or more selected from isoxazoline-substituted benzamide compounds and salts thereof as described in any one of claims 1 to 2, as an active ingredient.

6. The control agent according to claim 5, wherein the external parasite is a flea or a tick.

7. An insecticide or acaricide containing one or more isoxazoline-substituted benzamide compounds and salts thereof selected from any one of claims 1 to 2 as an active ingredient.

8. A seed treatment agent containing one or more selected from the isoxazoline-substituted benzamide compounds and salts thereof described in any one of claims 1 to 2 as an active ingredient.

9. The seed treatment agent according to claim 8, wherein the seed treatment is performed by immersion treatment.

10. A soil treatment agent containing one or more selected from the isoxazoline-substituted benzamide compounds and salts thereof described in any one of claims 1 to 2 as an active ingredient.

11. The soil treatment agent according to claim 10, wherein the soil treatment is performed by soil drenching.

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