Nitrogen-containing condensed heterocyclic compounds having an oxime group, herbicides for agricultural and horticultural use containing the compounds, and methods for using the same

Abstract

In order to eliminate the food crisis brought about by the increase in the world's population expected to occur in the near future, the present invention seeks to develop a new herbicide having both high safety for crops and excellent herbicidal activity against weeds, and solves this technical problem by using an agricultural and horticultural herbicide containing a compound represented by the following general formula (1) or a salt thereof as an active ingredient and a method for using the same.

Description

Technical Field

[0001] The present invention relates to a nitrogen-containing condensed heterocyclic compound having an oxime group and a salt thereof, an agricultural and horticultural herbicide containing the compound or its salt as an active ingredient, and a method for using the agricultural and horticultural herbicide. Background Art

[0002] Patent Document 1 describes that a certain nitrogen-containing condensed heterocyclic compound having an oxime group has insecticidal activity. However, the specific structure of the compound of the present invention is not described in this document, nor is there any disclosure or suggestion of a compound that can be used as a herbicide.

[0003] Prior Art Documents

[0004] Patent Documents

[0005] Patent Document 1: Pamphlet of International Publication No. 2017 / 065183 Summary of the Invention

[0006] Technical Problem to be Solved by the Invention

[0007] For eliminating the food crisis caused by the increase in the world population expected in the near future, a stable supply of food is essential. For a stable food supply, it is necessary to economically and effectively dry and kill or control weeds that will become obstacles during cultivation and harvesting, and the development of new herbicides and plant growth regulators as solutions has become increasingly important. In response to such social needs, the technical problem of the present invention is to provide a new herbicide having both high safety for crops and excellent herbicidal activity against weeds. In addition, due to the aging of agricultural workers, various labor-saving application methods are required, and there is also a demand for the development of an agricultural and horticultural herbicide having characteristics suitable for these application methods.

[0008] Technical Means for Solving the Technical Problem

[0009] The inventors of the present application conducted intensive research to develop a new agricultural and horticultural herbicide, and as a result, found that a nitrogen-containing condensed heterocyclic compound having an oxime group represented by the general formula (1) of the present invention or a salt thereof can be used as an agricultural and horticultural herbicide, thereby completing the present invention.

[0010] That is, the present invention is as follows:

[0011] (1) A compound represented by the general formula (1) or a salt thereof, wherein,

[0012] [Chemical Formula 1]

[0013]

[0014] In the formula,

[0015] R 1 represents:

[0016] (a1) a halogen atom;

[0017] (a2) a cyano group;

[0018] (a3) a nitro group;

[0019] (a4) a formyl group;

[0020] (a5) a carboxyl group;

[0021] (a6) a (C1-C6) alkyl group;

[0022] (a7) a (C2-C6) alkenyl group;

[0023] (a8) a (C2-C6) alkynyl group;

[0024] (a9) a (C3-C6) cycloalkyl group;

[0025] (a10) a halo(C1-C6)alkyl group;

[0026] (a11) a halo(C2-C6)alkenyl group;

[0027] (a12) a halo(C2-C6)alkynyl group;

[0028] (a13) a halo(C3-C6)cycloalkyl group;

[0029] (a14) a hydroxy(C1-C6)alkyl group;

[0030] (a15) a hydroxyhalo(C1-C6)alkyl group;

[0031] (a16) a (C1-C6)alkoxy(C1-C6)alkyl group;

[0032] (a17) a di(C1-C6)alkoxy(C1-C6)alkyl group;

[0033] (a18) a halo(C1-C6)alkoxy(C1-C6)alkyl group;

[0034] (a19) a (C1-C6)alkoxyhalo(C1-C6)alkyl group;

[0035] (a20) a halo(C1-C6)alkoxyhalo(C1-C6)alkyl group;

[0036] (a21) a (C3-C6)cycloalkyl(C1-C6)alkyl group;

[0037] (a22) a (C1-C6)alkoxy group;

[0038] (a23) Halo (C1-C6) alkoxy;

[0039] (a24) (C1-C6) alkylthio;

[0040] (a25) (C1-C6) alkylsulfinyl;

[0041] (a26) (C1-C6) alkylsulfonyl;

[0042] (a27) Halo (C1-C6) alkylthio;

[0043] (a28) Halo (C1-C6) alkylsulfinyl;

[0044] (a29) Halo (C1-C6) alkylsulfonyl;

[0045] (a30) R 8 (R 9 ) N group, where R 8 and R 9represents a hydrogen atom, a hydroxyl group, an amino group, di(C1-C6)alkylamino, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C2-C6)alkenyloxy, halo(C1-C6)alkyl, halo(C2-C6)alkenyl, halo(C2-C6)alkynyl, halo(C1-C6)alkoxy, halo(C3-C6)cycloalkyl, (C3-C6)cycloalkyl(C1-C6)alkyl, cyano(C1-C6)alkyl, (C1-C6)alkylcarbonyl, halo(C1-C6)alkylcarbonyl, (C1-C6)alkoxycarbonyl, halo(C1-C6)alkoxycarbonyl, (C1-C6)alkylmercapto-carbonyl, (C1-C6)alkylsulfonyl, halo(C1-C6)alkylsulfonyl, N-(C1-C6)alkylcarbamoyl, N,N-di(C1-C6)alkylcarbamoyl, N-(C1-C6)alkylsulfamoyl, N,N-di(C1-C6)alkylsulfamoyl, N-halo(C1-C6)alkylcarbamoyl, (C1-C6)alkoxycarbonyl(C1-C6)alkyl, (C1-C6)alkoxy(C1-C6)alkyl, di(C1-C6)alkoxy(C1-C6)alkyl, (C1-C6)alkoxy(C1-C6)alkylcarbonyl, thietanyl, 1,1-dioxothietanyl, tetrahydrofuranyl, thiazolyl, 2-oxotetrahydrofuranyl, phenyl, phenyl having 1 to 5 substituents which are the same or different and are each independently selected from a halogen atom, a cyano group, (C1-C6)alkyl, halo(C1-C6)alkyl, (C1-C6)alkoxy, halo(C1-C6)alkoxy, (C3-C6)cycloalkyl, (C1-C6)alkylthio, halo(C1-C6)alkylthio, (C1-C6)alkylsulfinyl, halo(C1-C6)alkylsulfinyl, (C1-C6)alkylsulfonyl and halo(C1-C6)alkylsulfonyl on the ring, or phenyl(C1-C6)alkyl, and, R 8 and R 9 are optionally the same or different and are optionally bonded to each other to form a 4- to 6-membered ring;

[0046] (a31)R 10 (R 11 )N(C1-C6)alkyl, wherein R 10 and R 11 represent a hydrogen atom, (C1-C6)alkyl, halo(C1-C6)alkyl, (C3-C6)cycloalkyl, (C3-C6)cycloalkyl(C1-C6)alkyl, (C1-C6)alkylcarbonyl, halo(C1-C6)alkylcarbonyl, (C1-C6)alkoxycarbonyl, halo(C1-C6)alkoxycarbonyl, (C1-C6)alkylsulfonyl or halo(C1-C6)alkylsulfonyl, and, R 10 and R11 Optionally the same or different, and optionally bonded to each other to form a 4- to 6-membered ring;

[0047] (a32) (C1-C6) alkylthio (C1-C6) alkyl;

[0048] (a33) (C1-C6) alkylsulfinyl (C1-C6) alkyl;

[0049] (a34) (C1-C6) alkylsulfonyl (C1-C6) alkyl;

[0050] (a35) halo (C1-C6) alkylthio (C1-C6) alkyl;

[0051] (a36) halo (C1-C6) alkylsulfinyl (C1-C6) alkyl;

[0052] (a37) halo (C1-C6) alkylsulfonyl (C1-C6) alkyl;

[0053] (a38) (C1-C6) alkylthio halo (C1-C6) alkyl;

[0054] (a39) (C1-C6) alkylsulfinyl halo (C1-C6) alkyl;

[0055] (a40) (C1-C6) alkylsulfonyl halo (C1-C6) alkyl;

[0056] (a41) halo (C1-C6) alkylthio halo (C1-C6) alkyl;

[0057] (a42) halo (C1-C6) alkylsulfinyl halo (C1-C6) alkyl;

[0058] (a43) halo (C1-C6) alkylsulfonyl halo (C1-C6) alkyl;

[0059] (a44) (C1-C6) alkylcarbonyl;

[0060] (a45) (C1-C6) alkoxycarbonyl;

[0061] (a46) halo (C1-C6) alkylcarbonyl;

[0062] (a47) halo (C1-C6) alkoxycarbonyl;

[0063] (a48) (C1-C6) alkylcarbonyloxy;

[0064] (a49) halo (C1-C6) alkylcarbonyloxy;

[0065] (a50) R10 (R 11 )N-carbonyl, where R 10 and R 11 are the same as the said R 10 and R 11 ;

[0066] (a51)R 10 (R 11 )N-carbonyloxy, where R 10 and R 11 are the same as the said R 10 and R 11 ;

[0067] (a52)R 10 (R 11 )N-sulfonyl, where R 10 and R 11 are the same as the said R 10 and R 11 ;

[0068] (a53)(C1-C6)alkylsulfonyloxy;

[0069] (a54)halo(C1-C6)alkylsulfonyloxy;

[0070] (a55)(C1-C6)alkoxyimino(C1-C3)alkyl;

[0071] (a56)halo(C1-C6)alkoxyimino(C1-C3)alkyl;

[0072] (a57)phenyl;

[0073] (a58)phenyl having 1 to 5 substituents, which are optionally the same or different and are selected from a halogen atom, a cyano group, a nitro group, a formyl group, (C1-C6)alkyl, halo(C1-C6)alkyl, (C1-C6)alkoxy, halo(C1-C6)alkoxy, (C3-C6)cycloalkyl(C1-C6)alkyl, R 10 (R 11 )N(C1-C6)alkyl, R 10 (R 11 )N group, (C1-C6)alkylthio, halo(C1-C6)alkylthio, (C1-C6)alkylsulfinyl, halo(C1-C6)alkylsulfinyl, (C1-C6)alkylsulfonyl and halo(C1-C6)alkylsulfonyl, where R 10 (R 11 )N(C1-C6)alkyl in which R 10 and R 11 are the same as the said R 10 and R 11Same, R 10 (R 11 ) The R in the N group 10 and R 11 is the same as the said R 10 and R 11 ;

[0074] (a59) Pyridyl;

[0075] (a60) Having 1 to 4 optionally identical or different substituents selected from halogen atoms, cyano group, nitro group, formyl group, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C3-C6) cycloalkyl (C1-C6) alkyl group, R 10 (R 11 ) N(C1-C6) alkyl group, R 10 (R 11 ) N group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group, (C1-C6) alkylsulfinyl group, halo (C1-C6) alkylsulfinyl group, (C1-C6) alkylsulfonyl group and halo (C1-C6) alkylsulfonyl group of the pyridyl group, wherein, R 10 (R 11 ) The R in the N(C1-C6) alkyl group 10 and R 11 is the same as the said R 10 and R 11 ; 10 (R 11 ) The R in the N group 10 and R 11 is the same as the said R 10 and R 11 ;

[0076] (a61) Pyrazolyl;

[0077] (a62) Having 1 to 3 optionally identical or different substituents selected from halogen atoms, cyano group, nitro group, formyl group, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C3-C6) cycloalkyl (C1-C6) alkyl group, R 10 (R 11 ) N(C1-C6) alkyl group, R 10 (R 11 ) N group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group, (C1-C6) alkylsulfinyl group, halo (C1-C6) alkylsulfinyl group, (C1-C6) alkylsulfonyl group and halo (C1-C6) alkylsulfonyl group of the pyrazolyl group, wherein, R 10 (R 11) R in (C1-C6)alkyl 10 and R 11 with said R 10 and R 11 being the same, R 10 (R 11 ) R in the N group 10 and R 11 with said R 10 and R 11 being the same;

[0078] (a63) Phenoxy;

[0079] (a64) Having 1 to 5 optionally identical or different substituents selected from halogen atoms, cyano groups, nitro groups, formyl groups, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C3-C6)cycloalkyl(C1-C6)alkyl groups, R 10 (R 11 )N(C1-C6)alkyl, R 10 (R 11 )N group, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups on the phenoxy, wherein, R 10 (R 11 ) R in the N(C1-C6)alkyl 10 and R 11 with said R 10 and R 11 being the same, R 10 (R 11 ) R in the N group 10 and R 11 with said R 10 and R 11 being the same;

[0080] (a65) Dioxolanyl;

[0081] (a66) Having 1 to 4 optionally identical or different substituents selected from halogen atoms, cyano groups, nitro groups, formyl groups, carbonyl groups, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C3-C6)cycloalkyl(C1-C6)alkyl groups, R 10 (R 11)Dioxolanyl with substituents among (C1-C6)alkyl, (C1-C6)alkylthio, halo(C1-C6)alkylthio, (C1-C6)alkylsulfinyl, halo(C1-C6)alkylsulfinyl, (C1-C6)alkylsulfonyl and halo(C1-C6)alkylsulfonyl, wherein R 10 (R 11 )N(C1-C6)alkyl, the R 10 and R 11 are the same as the said R 10 and R 11 ;

[0082] (a67)Dioxanyl;

[0083] (a68)Having 1 to 6 optionally identical or different substituents selected from halogen atom, cyano group, nitro group, formyl group, carbonyl group, (C1-C6)alkyl, halo(C1-C6)alkyl, (C1-C6)alkoxy, halo(C1-C6)alkoxy, (C3-C6)cycloalkyl(C1-C6)alkyl, R 10 (R 11 )N(C1-C6)alkyl, dioxanyl with substituents among (C1-C6)alkylthio, halo(C1-C6)alkylthio, (C1-C6)alkylsulfinyl, halo(C1-C6)alkylsulfinyl, (C1-C6)alkylsulfonyl and halo(C1-C6)alkylsulfonyl, wherein R 10 (R 11 )N(C1-C6)alkyl, the R 10 and R 11 are the same as the said R 10 and R 11 ;

[0084] (a69)(C1-C6)alkylene formed by bonding of adjacent 2 substituents (R 1 ), optionally substituted by 1 to 4 optionally identical or different substituents selected from halogen atom, phenyl group and (C1-C6)alkyl; or

[0085] (a70)Methylenedioxy optionally substituted by 1 or 2 optionally identical or different substituents selected from halogen atom, phenyl group and (C1-C6)alkyl, formed by bonding of adjacent 2 substituents (R 1 ),

[0086] When m represents an integer of 2 or more, R 1 are optionally identical or different,

[0087] m represents 0, 1, 2, 3 or 4,

[0088] R 2 represents:

[0089] (b1) hydrogen atom;

[0090] (b2) (C1-C6) alkyl;

[0091] (b3) (C3-C6) cycloalkyl;

[0092] (b4) (C2-C6) alkenyl;

[0093] (b5) (C2-C6) alkynyl;

[0094] (b6) halo(C1-C6)alkyl;

[0095] (b7) halo(C2-C6)alkenyl;

[0096] (b8) halo(C2-C6)alkynyl;

[0097] (b9) (C1-C6) alkoxy(C1-C6)alkyl;

[0098] (b10) (C1-C6) alkylthio(C1-C6)alkyl;

[0099] (b11) (C1-C6) alkylsulfinyl(C1-C6)alkyl;

[0100] (b12) (C1-C6) alkylsulfonyl(C1-C6)alkyl;

[0101] (b13) (C3-C6) cycloalkyl(C1-C6)alkyl;

[0102] (b14) (C1-C6) alkoxy

[0103] (b15) (C1-C6) alkylcarbonyl;

[0104] (b16) (C1-C6) alkoxycarbonyl;

[0105] (b17) halo(C1-C6)alkoxy

[0106] (b18) halo(C1-C6)alkylcarbonyl;

[0107] (b19) halo(C1-C6)alkoxycarbonyl;

[0108] (b20) R 10 (R 11 )N carbonyl, wherein, R 10 and R 11 are the same as the said R 10 and R 11 ; or

[0109] (b21)R 10 (R 11 )N-sulfonyl, wherein R 10 and R 11 are the same as the said R 10 and R 11 ;

[0110] R 3 represents:

[0111] (c1) a hydrogen atom;

[0112] (c2) a halogen group;

[0113] (c3) a cyano group;

[0114] (c4) a carboxyl group;

[0115] (c5) a formamido group;

[0116] (c6) a (C1-C6) alkyl group;

[0117] (c7) a (C2-C6) alkenyl group;

[0118] (c8) a (C2-C6) alkynyl group;

[0119] (c9) a halo (C1-C6) alkyl group;

[0120] (c10) a halo (C2-C6) alkenyl group;

[0121] (c11) a halo (C2-C6) alkynyl group;

[0122] (c12) R 8 (R 9 )N group, wherein R 8 and R 9 are the same as the said R 8 and R 9 ;

[0123] (c13) a (C1-C6) alkoxy group;

[0124] (c14) a halo (C1-C6) alkoxy group;

[0125] (c15) a (C1-C6) alkoxy (C1-C6) alkyl group; or

[0126] (c16) a (C1-C6) alkoxycarbonyl (C1-C6) alkyl group,

[0127] R 4 represents:

[0128] (d1) a hydrogen atom;

[0129] (d2) (C1-C6) alkyl;

[0130] (d3) (C2-C6) alkenyl;

[0131] (d4) (C2-C6) alkynyl;

[0132] (d5) (C3-C6) cycloalkyl;

[0133] (d6) halo(C1-C6)alkyl;

[0134] (d7) halo(C2-C6)alkenyl;

[0135] (d8) halo(C2-C6)alkynyl;

[0136] (d9) (C1-C6) alkoxy(C1-C6)alkyl;

[0137] (d10) halo(C1-C6)alkoxy(C1-C6)alkyl;

[0138] (d11) (C1-C6) alkoxyhalo(C1-C6)alkyl;

[0139] (d12) halo(C1-C6)alkoxyhalo(C1-C6)alkyl;

[0140] (d13) (C3-C6) cycloalkyl(C1-C6)alkyl;

[0141] (d14) cyano(C1-C6)alkyl;

[0142] (d15) (C1-C6) alkylthio(C1-C6)alkyl;

[0143] (d16) (C1-C6) alkylsulfinyl(C1-C6)alkyl;

[0144] (d17) (C1-C6) alkylsulfonyl(C1-C6)alkyl;

[0145] (d18) carboxy(C1-C6)alkyl;

[0146] (d19) phenyl(C1-C6)alkyl;

[0147] (d20)phenyl(C1-C6)alkyl having 1 to 5 substituents, which may be the same or different and are each independently selected from a halogen atom, a cyano group, a nitro group, a formyl group, a (C1-C6)alkyl group, a halo(C1-C6)alkyl group, a (C1-C6)alkoxy group, a halo(C1-C6)alkoxy group, a (C3-C6)cycloalkyl(C1-C6)alkyl group, a (C1-C6)alkylthio group, a halo(C1-C6)alkylthio group, a (C1-C6)alkylsulfinyl group, a halo(C1-C6)alkylsulfinyl group, a (C1-C6)alkylsulfonyl group, and a halo(C1-C6)alkylsulfonyl group, on the ring;

[0148] (d21)R 10 (R 11 )N-alkyl, wherein R 10 and R 11 are the same as the said R 10 and R 11 ;

[0149] (d22)(C1-C6)alkylcarbonyl;

[0150] (d23)(C1-C6)alkoxycarbonyl;

[0151] (d24)(C1-C6)alkylsulfonyl;

[0152] (d25)halo(C1-C6)alkylcarbonyl;

[0153] (d26)halo(C1-C6)alkoxycarbonyl;

[0154] (d27)halo(C1-C6)alkylsulfonyl;

[0155] (d28)R 10 (R 11 )N-carbonyl, wherein R 10 and R 11 are the same as the said R 10 and R 11 ;

[0156] (d29)R 10 (R 11 )N-sulfonyl, wherein R 10 and R 11 are the same as the said R 10 and R 11 ;

[0157] (d30)phenyl;

[0158] (d31) having 1 to 5 optionally identical or different substituents selected from halogen atoms, cyano groups, nitro groups, formyl groups, (C1-C6) alkyl groups, halo (C1-C6) alkyl groups, (C1-C6) alkoxy groups, halo (C1-C6) alkoxy groups, (C3-C6) cycloalkyl (C1-C6) alkyl groups, R 10 (R 11 )N group, (C1-C6) alkylthio groups, halo (C1-C6) alkylthio groups, (C1-C6) alkylsulfinyl groups, halo (C1-C6) alkylsulfinyl groups, (C1-C6) alkylsulfonyl groups and halo (C1-C6) alkylsulfonyl groups, wherein R 10 (R 11 )N group, R 10 and R 11 are the same as the said R 10 and R 11 ; or

[0159] (d32) (C1-C6) alkoxycarbonyl (C1-C6) alkyl,

[0160] A 1 、A 2 and A 3 represent CR 5 or a nitrogen atom, A 1 、A 2 and A 3 are optionally identical or different, wherein R 5 in CR 5 represents a hydrogen atom, a halogen atom, a cyano group, a (C1-C6) alkyl group, a halo (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo (C1-C6) alkoxy group, R 10 (R 11 )N group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group or a (C1-C6) alkylsulfonyl group, R 10 (R 11 )N group, R 10 and R 11 are the same as the said R 10 and R 11 ;

[0161] Q represents:

[0162] (e1) a halogen atom;

[0163] (e2) a cyano group;

[0164] (e3) a nitro group;

[0165] (e4) a formyl group;

[0166] (e5) a (C1-C6) alkyl group;

[0167] (e6) (C2-C6) alkenyl;

[0168] (e7) (C2-C6) alkynyl;

[0169] (e8) halo (C1-C6) alkyl;

[0170] (e9) halo (C2-C6) alkenyl;

[0171] (e10) halo (C2-C6) alkynyl;

[0172] (e11) (C1-C6) alkoxy;

[0173] (e12) halo (C1-C6) alkoxy;

[0174] (e13) hydroxy (C1-C6) alkyl;

[0175] (e14) dihydroxy (C1-C6) alkyl;

[0176] (e15) (C1-C6) alkoxy (C1-C6) alkyl;

[0177] (e16) (C1-C6) alkoxy (C2-C6) alkenyl;

[0178] (e17) R 8 (R 9 ) N group, where R 8 and R 9 are the same as the said R 8 and R 9 ;

[0179] (e18) dioxolanyl;

[0180] (e19) having on the ring 1 or 2 optionally identical or different substituents selected from halogen atom, cyano group, nitro group, formyl group, carbonyl group, (C1-C6) alkyl, halo (C1-C6) alkyl, (C1-C6) alkoxy, halo (C1-C6) alkoxy, (C3-C6) cycloalkyl (C1-C6) alkyl, R 10 (R 11 ) N (C1-C6) alkyl, (C1-C6) alkylthio, halo (C1-C6) alkylthio, (C1-C6) alkylsulfinyl, halo (C1-C6) alkylsulfinyl, (C1-C6) alkylsulfonyl and halo (C1-C6) alkylsulfonyl of the dioxolanyl, where R 10 (R 11 ) N (C1-C6) alkyl of R 10 and R 11 are the same as the said R10 and R 11 are the same;

[0181] (e20) dioxacyclohexyl;

[0182] (e21) dioxacyclohexyl having on the ring 1 to 3 optionally identical or different substituents selected from halogen atoms, cyano, nitro, formyl, carbonyl, (C1-C6)alkyl, halo(C1-C6)alkyl, (C1-C6)alkoxy, halo(C1-C6)alkoxy, (C3-C6)cycloalkyl(C1-C6)alkyl, R 10 (R 11 )N(C1-C6)alkyl, (C1-C6)alkylthio, halo(C1-C6)alkylthio, (C1-C6)alkylsulfinyl, halo(C1-C6)alkylsulfinyl, (C1-C6)alkylsulfonyl and halo(C1-C6)alkylsulfonyl, wherein R 10 (R 11 )N(C1-C6)alkyl, the R 10 and R 11 is the same as the said R 10 and R 11 ;

[0183] (e22) phenyl;

[0184] (e23) phenyl having on the ring 1 to 5 optionally identical or different substituents selected from halogen atoms, cyano, nitro, formyl, (C1-C6)alkyl, halo(C1-C6)alkyl, (C1-C6)alkoxy, halo(C1-C6)alkoxy, (C3-C6)cycloalkyl(C1-C6)alkyl, R 10 (R 11 )N group, (C1-C6)alkylthio, halo(C1-C6)alkylthio, (C1-C6)alkylsulfinyl, halo(C1-C6)alkylsulfinyl, (C1-C6)alkylsulfonyl and halo(C1-C6)alkylsulfonyl, wherein R 10 (R 11 )N group, the R 10 and R 11 is the same as the said R 10 and R 11 ;

[0185] (e24) imidazolyl;

[0186] (e25) imidazolyl having on the ring 1 to 3 optionally identical or different substituents selected from halogen atoms, cyano, nitro, formyl, (C1-C6)alkyl, halo(C1-C6)alkyl, (C1-C6)alkoxy, halo(C1-C6)alkoxy, (C3-C6)cycloalkyl(C1-C6)alkyl, R10 (R 11 )N group, (C1-C6) alkylthio group, halogenated (C1-C6) alkylthio group, (C1-C6) alkylsulfinyl group, halogenated (C1-C6) alkylsulfinyl group, (C1-C6) alkylsulfonyl group and halogenated (C1-C6) alkylsulfonyl group, where the substituent of the imidazolyl group, where R 10 (R 11 )N group, the R in 10 and R 11 is the same as the R 10 and R 11 ;

[0187] (e26) Oxadiazolyl group;

[0188] (e27) having a substituent selected from a halogen atom, a cyano group, a nitro group, a formyl group, a (C1-C6) alkyl group, a halogenated (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halogenated (C1-C6) alkoxy group, a (C3-C6) cycloalkyl(C1-C6) alkyl group, R 10 (R 11 )N group, (C1-C6) alkylthio group, halogenated (C1-C6) alkylthio group, (C1-C6) alkylsulfinyl group, halogenated (C1-C6) alkylsulfinyl group, (C1-C6) alkylsulfonyl group and halogenated (C1-C6) alkylsulfonyl group, where the substituent of the oxadiazolyl group, where R 10 (R 11 )N group, the R in 10 and R 11 is the same as the R 10 and R 11 ;

[0189] (e28) S(O) p R 6 group, in the formula, R 6 represents a hydrogen atom, a (C1-C6) alkyl group, a (C2-C6) alkenyl group, a (C2-C6) alkynyl group, a halogenated (C1-C6) alkyl group, a halogenated (C2-C6) alkenyl group, a halogenated (C2-C6) alkynyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a halogenated (C3-C6) cycloalkyl group, a phenyl(C1-C6) alkyl group, a (C1-C6) alkoxyphenyl(C1-C6) alkyl group, a (C1-C6) alkylphenyl(C1-C6) alkyl group, a tris(C1-C6) alkylsilylphenyl(C1-C6) alkyl group or an N(R 8 )R 9 group, p represents 0, 1 or 2, where the R in the N(R 8 )R 9 group 8 and R 9 is the same as the R 8 and R9 Same;

[0190] (e29)C(O)R 7 group, wherein R 7 represents hydroxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, halo(C1-C6)alkyl, halo(C2-C6)alkenyl, halo(C2-C6)alkynyl, (C1-C6)alkoxycarbonyl(C1-C6)alkyl, phenyl(C1-C6)alkyl, phenyl(C1-C6)alkoxy, (C1-C6)alkoxy, (C2-C6)alkenyloxy, (C2-C6)alkynyloxy, (C3-C6)cycloalkoxy, halo(C1-C6)alkoxy, halo(C2-C6)alkynyloxy, phenoxy, (C1-C6)alkoxycarbonyl(C1-C6)alkoxy, (C1-C6)alkylthio, phenyl, thiazolidinyl or N(R 8 )R 9 group, wherein, N(R 8 )R 9 in the group N(R 8 and R 9 is the same as the said R 8 and R 9 Same;

[0191] (e30)Thiocarboxamido;

[0192] (e31)N-(C1-C6)alkylaminothiocarbonyl;

[0193] (e32)N,N-di(C1-C6)alkylaminothiocarbonyl;

[0194] (e33)[Chemical formula 2]

[0195]

[0196] wherein, R 6 and R 8 is the same as the said R 6 and R 8 Same;

[0197] (e34)Hydroxyimino(C1-C3)alkyl;

[0198] (e35)(C1-C6)alkoxyimino(C1-C3)alkyl;

[0199] (e36)Halo(C1-C6)alkoxyimino(C1-C3)alkyl;

[0200] (e37)Hydrazono(C1-C3)alkyl;

[0201] (e38) (C1-C6) alkylhydrazono (C1-C3) alkyl;

[0202] (e39) bis((C1-C6) alkylhydrazono) (C1-C3) alkyl;

[0203] (e40) phenyl (C1-C6) alkoxyimino (C1-C3) alkyl;

[0204] (e41) (C2-C6) alkenyloxyimino (C1-C3) alkyl;

[0205] (e42) bis((C1-C6) alkoxyphosphonyl);

[0206] (e43) bis((C1-C6) alkoxyphosphonyl)amino;

[0207] (e44) hydroxy;

[0208] (e45) (C1-C6) alkoxy (C1-C6) alkoxy;

[0209] (e46) (C1-C6) alkoxyiminoamino (C1-C3) alkyl;

[0210] (e47) cyano (C1-C6) alkyl;

[0211] (e48) cyano (C2-C6) alkenyl;

[0212] (e49) dicyano (C1-C6) alkyl; or

[0213] (e50) dicyano (C2-C6) alkenyl.

[0214] (2) The compound or a salt thereof according to (1), wherein,

[0215] A 1 、A 2 and A 3 are the same as A 1 、A 2 and A 3 in (1),

[0216] R 1 represents:

[0217] (a1) a halogen atom;

[0218] (a2) cyano;

[0219] (a3) nitro;

[0220] (a4) formyl;

[0221] (a5) carboxyl;

[0222] (a6) (C1-C6) alkyl;

[0223] (a7) (C2-C6) alkenyl;

[0224] (a8) (C2-C6) alkynyl;

[0225] (a9) (C3-C6) cycloalkyl;

[0226] (a10) halo(C1-C6)alkyl;

[0227] (a11) halo(C2-C6)alkenyl;

[0228] (a12) halo(C2-C6)alkynyl;

[0229] (a14) hydroxy(C1-C6)alkyl;

[0230] (a15) hydroxyhalo(C1-C6)alkyl;

[0231] (a16) (C1-C6) alkoxy(C1-C6)alkyl;

[0232] (a17) di(C1-C6) alkoxy(C1-C6)alkyl;

[0233] (a18) halo(C1-C6) alkoxy(C1-C6)alkyl;

[0234] (a19) (C1-C6) alkoxyhalo(C1-C6)alkyl;

[0235] (a20) halo(C1-C6) alkoxyhalo(C1-C6)alkyl;

[0236] (a21) (C3-C6) cycloalkyl(C1-C6)alkyl;

[0237] (a22) (C1-C6) alkoxy;

[0238] (a23) halo(C1-C6) alkoxy;

[0239] (a24) (C1-C6) alkylthio;

[0240] (a25) (C1-C6) alkylsulfinyl;

[0241] (a26) (C1-C6) alkylsulfonyl;

[0242] (a27) halo(C1-C6) alkylthio;

[0243] (a28) halo(C1-C6) alkylsulfinyl;

[0244] (a29) halo(C1-C6)alkylsulfonyl;

[0245] (a30) R 8 (R 9 )N group, wherein, R 8 and R 9 represent a hydrogen atom, a hydroxyl group, an amino group, a di(C1-C6)alkylamino group, a (C1-C6)alkyl group, a (C3-C6)cycloalkyl group, a (C2-C6)alkenyl group, a (C2-C6)alkynyl group, a (C1-C6)alkoxy group, a (C2-C6)alkenyloxy group, a halo(C1-C6)alkyl group, a halo(C2-C6)alkenyl group, a halo(C2-C6)alkynyl group, a halo(C3-C6)cycloalkyl group, a (C3-C6)cycloalkyl(C1-C6)alkyl group, a cyano(C1-C6)alkyl group, a (C1-C6)alkylcarbonyl group, a halo(C1-C6)alkylcarbonyl group, a (C1-C6)alkoxycarbonyl group, a halo(C1-C6)alkoxycarbonyl group, a (C1-C6)alkylmercapto carbonyl group, a (C1-C6)alkylsulfonyl group, a halo(C1-C6)alkylsulfonyl group, an N-(C1-C6)alkylformamido group, an N,N-di(C1-C6)alkylformamido group, an N-(C1-C6)alkylsulfamoyl group, an N,N-di(C1-C6)alkylsulfamoyl group, an N-halo(C1-C6)alkylformamido group, a (C1-C6)alkoxycarbonyl(C1-C6)alkyl group, a (C1-C6)alkoxy(C1-C6)alkyl group, a di(C1-C6)alkoxy(C1-C6)alkyl group, a (C1-C6)alkoxy(C1-C6)alkylcarbonyl group, a thiolanyl group, a 1,1-dioxothiolanyl group, a tetrahydrofuranyl group, a thiazolyl group, a 2-oxotetrahydrofuranyl group, a phenyl group, a phenyl group having 1 to 5 substituents which are the same or different and are each independently selected from a halogen atom, a cyano group, a (C1-C6)alkyl group, a halo(C1-C6)alkyl group, a (C1-C6)alkoxy group and a halo(C1-C6)alkoxy group on the ring, or a phenyl(C1-C6)alkyl group, and, R 8 and R 9 are optionally the same or different and are optionally bonded to each other to form a 4- to 6-membered ring;

[0246] (a31) R 10 (R 11 )N(C1-C6)alkyl, wherein, R 10 and R 11represents a hydrogen atom, (C1-C6)alkyl, halo(C1-C6)alkyl, (C3-C6)cycloalkyl, (C3-C6)cycloalkyl(C1-C6)alkyl, (C1-C6)alkylcarbonyl, halo(C1-C6)alkylcarbonyl, (C1-C6)alkoxycarbonyl, halo(C1-C6)alkoxycarbonyl, (C1-C6)alkylsulfonyl or halo(C1-C6)alkylsulfonyl, and, R 10 and R 11 are optionally the same or different and are optionally bonded to each other to form a 4- to 6-membered ring;

[0247] (a32)(C1-C6)alkylthio(C1-C6)alkyl;

[0248] (a33)(C1-C6)alkylsulfinyl(C1-C6)alkyl;

[0249] (a34)(C1-C6)alkylsulfonyl(C1-C6)alkyl;

[0250] (a35)halo(C1-C6)alkylthio(C1-C6)alkyl;

[0251] (a36)halo(C1-C6)alkylsulfinyl(C1-C6)alkyl;

[0252] (a37)halo(C1-C6)alkylsulfonyl(C1-C6)alkyl;

[0253] (a44)(C1-C6)alkylcarbonyl;

[0254] (a45)(C1-C6)alkoxycarbonyl;

[0255] (a46)halo(C1-C6)alkylcarbonyl;

[0256] (a47)halo(C1-C6)alkoxycarbonyl;

[0257] (a50)R 10 (R 11 )N-carbonyl, wherein, R 10 and R 11 are the same as the said R 10 and R 11 ;

[0258] (a52)R 10 (R 11 )N-sulfonyl, wherein, R 10 and R 11 are the same as the said R 10 and R 11 ;

[0259] (a55) (C1-C6) alkoxyimino (C1-C3) alkyl;

[0260] (a56) halo (C1-C6) alkoxyimino (C1-C3) alkyl;

[0261] (a57) phenyl;

[0262] (a58) having on the ring 1 to 5 optionally identical or different substituents selected from halogen atom, cyano group, nitro group, formyl group, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C3-C6) cycloalkyl (C1-C6) alkyl group, R 10 (R 11 ) N (C1-C6) alkyl group, R 10 (R 11 ) N group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group, (C1-C6) alkylsulfinyl group, halo (C1-C6) alkylsulfinyl group, (C1-C6) alkylsulfonyl group and halo (C1-C6) alkylsulfonyl group, wherein, R 10 (R 11 ) N (C1-C6) alkyl group in R 10 and R 11 is the same as the said R 10 and R 11 ; R 10 (R 11 ) N group in R 10 and R 11 is the same as the said R 10 and R 11 ;

[0263] (a59) pyridyl;

[0264] (a60) having on the ring 1 to 4 optionally identical or different substituents selected from halogen atom, cyano group, nitro group, formyl group, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C3-C6) cycloalkyl (C1-C6) alkyl group, R 10 (R 11 ) N (C1-C6) alkyl group, R 10 (R 11 ) N group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group, (C1-C6) alkylsulfinyl group, halo (C1-C6) alkylsulfinyl group, (C1-C6) alkylsulfonyl group and halo (C1-C6) alkylsulfonyl group, wherein, R 10 (R 11 ) N (C1-C6) alkyl group in R10 and R 11 with the said R 10 and R 11 is the same, R 10 (R 11 ) R in the N group 10 and R 11 with the said R 10 and R 11 is the same;

[0265] (a61) pyrazolyl;

[0266] (a62) having 1 to 3 optionally identical or different substituents selected from halogen atoms, cyano group, nitro group, formyl group, (C1-C6) alkyl group, halogenated (C1-C6) alkyl group, (C1-C6) alkoxy group, halogenated (C1-C6) alkoxy group, (C3-C6) cycloalkyl (C1-C6) alkyl group, R 10 (R 11 ) N(C1-C6) alkyl group, R 10 (R 11 ) N group, (C1-C6) alkylthio group, halogenated (C1-C6) alkylthio group, (C1-C6) alkylsulfinyl group, halogenated (C1-C6) alkylsulfinyl group, (C1-C6) alkylsulfonyl group and halogenated (C1-C6) alkylsulfonyl group of the pyrazolyl group, wherein, R 10 (R 11 ) R in the N(C1-C6) alkyl group 10 and R 11 with the said R 10 and R 11 is the same, R 10 (R 11 ) R in the N group 10 and R 11 with the said R 10 and R 11 is the same;

[0267] (a63) phenoxy;

[0268] (a64) having 1 to 5 optionally identical or different substituents selected from halogen atoms, cyano group, nitro group, formyl group, (C1-C6) alkyl group, halogenated (C1-C6) alkyl group, (C1-C6) alkoxy group, halogenated (C1-C6) alkoxy group, (C3-C6) cycloalkyl (C1-C6) alkyl group, R 10 (R 11 ) N(C1-C6) alkyl group, R 10 (R 11)Phenoxy groups substituted with substituents selected from N groups, (C1-C6) alkylthio groups, halogenated (C1-C6) alkylthio groups, (C1-C6) alkylsulfinyl groups, halogenated (C1-C6) alkylsulfinyl groups, (C1-C6) alkylsulfonyl groups, and halogenated (C1-C6) alkylsulfonyl groups, where R 10 (R 11 )N(C1-C6) alkyl groups, where R 10 and R 11 are the same as the said R 10 and R 11 ; R 10 (R 11 )N groups, where R 10 and R 11 are the same as the said R 10 and R 11 ;

[0269] (a65) Dioxolanyl;

[0270] (a66) Dioxolanyl having 1 to 4 optionally identical or different substituents selected from halogen atoms, cyano groups, nitro groups, formyl groups, carbonyl groups, (C1-C6) alkyl groups, halogenated (C1-C6) alkyl groups, (C1-C6) alkoxy groups, halogenated (C1-C6) alkoxy groups, (C3-C6) cycloalkyl(C1-C6) alkyl groups, R 10 (R 11 )N(C1-C6) alkyl groups, (C1-C6) alkylthio groups, halogenated (C1-C6) alkylthio groups, (C1-C6) alkylsulfinyl groups, halogenated (C1-C6) alkylsulfinyl groups, (C1-C6) alkylsulfonyl groups, and halogenated (C1-C6) alkylsulfonyl groups, where R 10 (R 11 )N(C1-C6) alkyl groups, where R 10 and R 11 are the same as the said R 10 and R 11 ;

[0271] (a67) Dioxanyl;

[0272] (a68) Dioxanyl having 1 to 6 optionally identical or different substituents selected from halogen atoms, cyano groups, nitro groups, formyl groups, carbonyl groups, (C1-C6) alkyl groups, halogenated (C1-C6) alkyl groups, (C1-C6) alkoxy groups, halogenated (C1-C6) alkoxy groups, (C3-C6) cycloalkyl(C1-C6) alkyl groups, R 10 (R 11)A dioxolanyl group as a substituent in N(C1-C6)alkyl, (C1-C6)alkylthio, halo(C1-C6)alkylthio, (C1-C6)alkylsulfinyl, halo(C1-C6)alkylsulfinyl, (C1-C6)alkylsulfonyl and halo(C1-C6)alkylsulfonyl, wherein R 10 (R 11 ) in N(C1-C6)alkyl 10 and R 11 are the same as the said R 10 and R 11 ;

[0273] (a69) A (C1-C6)alkylene group formed by bonding of two adjacent substituents (R 1 ), optionally substituted by 1 or 2 substituents which are the same or different and are selected from a halogen atom, a phenyl group and a (C1-C6)alkyl group; or

[0274] (a70) A methylenedioxy group formed by bonding of two adjacent substituents (R 1 ), optionally substituted by 1 or 2 substituents which are the same or different and are selected from a halogen atom, a phenyl group and a (C1-C6)alkyl group,

[0275] When m represents an integer of 2 or more, R 1 are optionally the same or different,

[0276] m represents 0, 1, 2, 3 or 4,

[0277] R 2 represents:

[0278] (b1) A hydrogen atom;

[0279] (b2) A (C1-C6)alkyl group;

[0280] (b3) A (C3-C6)cycloalkyl group;

[0281] (b4) A (C2-C6)alkenyl group;

[0282] (b5) A (C2-C6)alkynyl group;

[0283] (b6) A halo(C1-C6)alkyl group;

[0284] (b7) A halo(C2-C6)alkenyl group;

[0285] (b8) A halo(C2-C6)alkynyl group;

[0286] (b9) A (C1-C6)alkoxy(C1-C6)alkyl group;

[0287] (b10) (C1-C6) alkylthio (C1-C6) alkyl;

[0288] (b11) (C1-C6) alkylsulfinyl (C1-C6) alkyl;

[0289] (b12) (C1-C6) alkylsulfonyl (C1-C6) alkyl;

[0290] (b13) (C3-C6) cycloalkyl (C1-C6) alkyl;

[0291] (b15) (C1-C6) alkylcarbonyl;

[0292] (b16) (C1-C6) alkoxycarbonyl;

[0293] (b18) halo (C1-C6) alkylcarbonyl; or

[0294] (b21) R 10 (R 11 ) N-sulfonyl, wherein, R 10 and R 11 are the same as the said R 10 and R 11 ;

[0295] R 3 represents:

[0296] (c1) hydrogen atom;

[0297] (c2) halo group;

[0298] (c3) cyano group;

[0299] (c4) carboxyl group;

[0300] (c5) formamido group;

[0301] (c6) (C1-C6) alkyl;

[0302] (c9) halo (C1-C6) alkyl;

[0303] (c12) R 8 (R 9 ) N group, wherein, R 8 and R 9 are the same as the said R 8 and R 9 ;

[0304] (c13) (C1-C6) alkoxy;

[0305] (c14) halo (C1-C6) alkoxy;

[0306] (c15) (C1-C6) alkoxy (C1-C6) alkyl; or

[0307] (c16) (C1-C6) alkoxycarbonyl (C1-C6) alkyl,

[0308] R 4 represents:

[0309] (d1) a hydrogen atom;

[0310] (d2) (C1-C6) alkyl;

[0311] (d3) (C2-C6) alkenyl;

[0312] (d4) (C2-C6) alkynyl;

[0313] (d5) (C3-C6) cycloalkyl;

[0314] (d6) halo (C1-C6) alkyl;

[0315] (d7) halo (C2-C6) alkenyl;

[0316] (d8) halo (C2-C6) alkynyl;

[0317] (d9) (C1-C6) alkoxy (C1-C6) alkyl;

[0318] (d10) halo (C1-C6) alkoxy (C1-C6) alkyl;

[0319] (d13) (C3-C6) cycloalkyl (C1-C6) alkyl;

[0320] (d14) cyano (C1-C6) alkyl;

[0321] (d15) (C1-C6) alkylthio (C1-C6) alkyl;

[0322] (d16) (C1-C6) alkylsulfinyl (C1-C6) alkyl;

[0323] (d17) (C1-C6) alkylsulfonyl (C1-C6) alkyl;

[0324] (d18) carboxy (C1-C6) alkyl;

[0325] (d19) phenyl (C1-C6) alkyl;

[0326] (d20)phenyl(C1-C6)alkyl having 1 to 5 substituents, which may be the same or different, selected from a halogen atom, a cyano group, a nitro group, a formyl group, a (C1-C6)alkyl group, a halo(C1-C6)alkyl group, a (C1-C6)alkoxy group, a halo(C1-C6)alkoxy group, a (C3-C6)cycloalkyl(C1-C6)alkyl group, a (C1-C6)alkylthio group, a halo(C1-C6)alkylthio group, a (C1-C6)alkylsulfinyl group, a halo(C1-C6)alkylsulfinyl group, a (C1-C6)alkylsulfonyl group and a halo(C1-C6)alkylsulfonyl group on the ring;

[0327] (d22)(C1-C6)alkylcarbonyl;

[0328] (d23)(C1-C6)alkoxycarbonyl;

[0329] (d24)(C1-C6)alkylsulfonyl;

[0330] (d25)halo(C1-C6)alkylcarbonyl;

[0331] (d26)halo(C1-C6)alkoxycarbonyl;

[0332] (d27)halo(C1-C6)alkylsulfonyl;

[0333] (d30)phenyl;

[0334] (d31)phenyl having 1 to 5 substituents, which may be the same or different, selected from a halogen atom, a cyano group, a nitro group, a formyl group, a (C1-C6)alkyl group, a halo(C1-C6)alkyl group, a (C1-C6)alkoxy group, a halo(C1-C6)alkoxy group, a (C3-C6)cycloalkyl(C1-C6)alkyl group, R 10 (R 11 )N group, a (C1-C6)alkylthio group, a halo(C1-C6)alkylthio group, a (C1-C6)alkylsulfinyl group, a halo(C1-C6)alkylsulfinyl group, a (C1-C6)alkylsulfonyl group and a halo(C1-C6)alkylsulfonyl group on the ring, wherein R 10 (R 11 )N group's R 10 and R 11 are the same as the said R 10 and R 11 ; or

[0335] (d32)(C1-C6)alkoxycarbonyl(C1-C6)alkyl,

[0336] Q represents:

[0337] (e1)a halogen atom;

[0338] (e2) cyano group;

[0339] (e4) formyl group;

[0340] (e5) (C1-C6) alkyl group;

[0341] (e6) (C2-C6) alkenyl group;

[0342] (e7) (C2-C6) alkynyl group;

[0343] (e8) halo (C1-C6) alkyl group;

[0344] (e11) (C1-C6) alkoxy group;

[0345] (e12) halo (C1-C6) alkoxy group;

[0346] (e13) hydroxy (C1-C6) alkyl group;

[0347] (e14) dihydroxy (C1-C6) alkyl group;

[0348] (e15) (C1-C6) alkoxy (C1-C6) alkyl group;

[0349] (e16) (C1-C6) alkoxy (C2-C6) alkenyl group;

[0350] (e17) R 8 (R 9 )N group, wherein, R 8 and R 9 are the same as the said R 8 and R 9 ;

[0351] (e18) dioxolanyl group;

[0352] (e19) dioxolanyl group having 1 or 2 substituents which are optionally the same or different and are selected from carbonyl group and (C1-C6) alkyl group on the ring;

[0353] (e20) dioxanyl group;

[0354] (e21) dioxanyl group having 1 to 3 substituents which are optionally the same or different and are selected from halogen atom, cyano group, nitro group, formyl group, carbonyl group, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C3-C6) cycloalkyl (C1-C6) alkyl group, R 10 (R 11)Dioxacyclohexyl groups with substituents among (C1-C6)alkyl, (C1-C6)alkylthio, halo(C1-C6)alkylthio, (C1-C6)alkylsulfinyl, halo(C1-C6)alkylsulfinyl, (C1-C6)alkylsulfonyl and halo(C1-C6)alkylsulfonyl, where R 10 (R 11 )N(C1-C6)alkyl, where R 10 and R 11 are the same as the R 10 and R 11 ;

[0355] (e22)phenyl;

[0356] (e23)phenyl groups having on the ring 1 to 5 optionally identical or different substituents selected from halogen atoms, cyano, nitro, formyl, (C1-C6)alkyl, halo(C1-C6)alkyl, (C1-C6)alkoxy, halo(C1-C6)alkoxy, (C3-C6)cycloalkyl(C1-C6)alkyl, R 10 (R 11 )N groups, (C1-C6)alkylthio, halo(C1-C6)alkylthio, (C1-C6)alkylsulfinyl, halo(C1-C6)alkylsulfinyl, (C1-C6)alkylsulfonyl and halo(C1-C6)alkylsulfonyl, where R 10 (R 11 )N group, where R 10 and R 11 are the same as the R 10 and R 11 ;

[0357] (e24)imidazolyl;

[0358] (e25)imidazolyl groups having on the ring 1 to 3 optionally identical or different substituents selected from halogen atoms, cyano, nitro, formyl, (C1-C6)alkyl, halo(C1-C6)alkyl, (C1-C6)alkoxy, halo(C1-C6)alkoxy, (C3-C6)cycloalkyl(C1-C6)alkyl, R 10 (R 11 )N groups, (C1-C6)alkylthio, halo(C1-C6)alkylthio, (C1-C6)alkylsulfinyl, halo(C1-C6)alkylsulfinyl, (C1-C6)alkylsulfonyl and halo(C1-C6)alkylsulfonyl, where R 10 (R 11 )N group, where R 10 and R 11 are the same as the R 10 and R 11 ;

[0359] (e26) Oxadiazolyl;

[0360] (e27) Oxadiazolyl having, on the ring, a substituent selected from a halogen atom, a cyano group, a nitro group, a formyl group, a (C1-C6)alkyl group, a halo(C1-C6)alkyl group, a (C1-C6)alkoxy group, a halo(C1-C6)alkoxy group, a (C3-C6)cycloalkyl(C1-C6)alkyl group, R 10 (R 11 )N group, a (C1-C6)alkylthio group, a halo(C1-C6)alkylthio group, a (C1-C6)alkylsulfinyl group, a halo(C1-C6)alkylsulfinyl group, a (C1-C6)alkylsulfonyl group and a halo(C1-C6)alkylsulfonyl group, wherein R 10 (R 11 )N group, R 10 and R 11 are the same as the said R 10 and R 11 ;

[0361] (e28) S(O) p R 6 group, in the formula, R 6 represents a hydrogen atom, a (C1-C6)alkyl group, a (C2-C6)alkenyl group, a (C2-C6)alkynyl group, a halo(C1-C6)alkyl group, a halo(C2-C6)alkenyl group, a halo(C2-C6)alkynyl group, a (C1-C6)alkoxy group, a (C3-C6)cycloalkyl group, a halo(C3-C6)cycloalkyl group, a phenyl(C1-C6)alkyl group, a (C1-C6)alkoxyphenyl(C1-C6)alkyl group, a (C1-C6)alkylphenyl(C1-C6)alkyl group, a tris(C1-C6)alkylsilylphenyl(C1-C6)alkyl group or an N(R 8 )R 9 group, p represents 0, 1 or 2, wherein R 8 )R 9 group, R 8 and R 9 are the same as the said R 8 and R 9 ;

[0362] (e29) C(O)R 7 group, in the formula, R 7represents hydroxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, halo(C1-C6)alkyl, halo(C2-C6)alkenyl, halo(C2-C6)alkynyl, (C1-C6)alkoxycarbonyl(C1-C6)alkyl, phenyl(C1-C6)alkyl, phenyl(C1-C6)alkoxy, (C1-C6)alkoxy, (C2-C6)alkenyloxy, (C2-C6)alkynyloxy, (C3-C6)cycloalkoxy, halo(C1-C6)alkoxy, halo(C2-C6)alkynyloxy, phenoxy, (C1-C6)alkoxycarbonyl(C1-C6)alkoxy, (C1-C6)alkylthio, phenyl, thiazolidinyl or N(R 8 )R 9 group, wherein, in the N(R 8 )R 9 group, R 8 and R 9 are the same as the said R 8 and R 9 ;

[0363] (e30)thiocarboxamido;

[0364] (e31)N-(C1-C6)alkylaminothiocarbonyl;

[0365] (e32)N,N-di(C1-C6)alkylaminothiocarbonyl;

[0366] (e33)[Chemical Formula 3]

[0367]

[0368] wherein, R 6 and R 8 are the same as the said R 6 and R 8 ;

[0369] (e34)hydroxyimino(C1-C3)alkyl;

[0370] (e35)(C1-C6)alkoxyimino(C1-C3)alkyl;

[0371] (e36)halo(C1-C6)alkoxyimino(C1-C3)alkyl;

[0372] (e37)hydrazono(C1-C3)alkyl;

[0373] (e38)(C1-C6)alkylhydrazono(C1-C3)alkyl;

[0374] (e39)di(C1-C6)alkylhydrazono(C1-C3)alkyl;

[0375] (e40)Phenyl(C1-C6)alkoxyimino(C1-C3)alkyl;

[0376] (e41)(C2-C6)alkenyloxyimino(C1-C3)alkyl;

[0377] (e42)Bis(C1-C6)alkoxyphosphonyl;

[0378] (e43)Bis(C1-C6)alkoxyphosphonylamino;

[0379] (e44)Hydroxy;

[0380] (e45)(C1-C6)alkoxy(C1-C6)alkoxy; or

[0381] (e46)(C1-C6)alkoxyiminoamino(C1-C3)alkyl.

[0382] (3)The compound according to (1) or (2), or a salt thereof, wherein,

[0383] R 1 represents:

[0384] (a1)Halogen atom;

[0385] (a2)Cyano;

[0386] (a3)Nitro;

[0387] (a4)Formyl;

[0388] (a5)Carboxyl;

[0389] (a6)(C1-C6)alkyl;

[0390] (a7)(C2-C6)alkenyl;

[0391] (a9)(C3-C6)cycloalkyl;

[0392] (a10)Halogenated(C1-C6)alkyl;

[0393] (a14)Hydroxy(C1-C6)alkyl;

[0394] (a16)(C1-C6)alkoxy(C1-C6)alkyl;

[0395] (a17)Bis(C1-C6)alkoxy(C1-C6)alkyl;

[0396] (a22)(C1-C6)alkoxy;

[0397] (a23)Halogenated(C1-C6)alkoxy;

[0398] (a24) (C1-C6) alkylthio;

[0399] (a26) (C1-C6) alkylsulfonyl;

[0400] (a27) halo(C1-C6) alkylthio;

[0401] (a28) halo(C1-C6) alkylsulfinyl;

[0402] (a29) halo(C1-C6) alkylsulfonyl;

[0403] (a30) R 8 (R 9 )N group, wherein, R 8 and R 9 represent a hydrogen atom, a hydroxyl group, an amino group, di(C1-C6) alkylamino, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C2-C6) alkenyloxy, halo(C1-C6) alkyl, halo(C3-C6) cycloalkyl, (C3-C6) cycloalkyl(C1-C6) alkyl, (C1-C6) alkylcarbonyl, halo(C1-C6) alkylcarbonyl, (C1-C6) alkoxycarbonyl, (C1-C6) alkylsulfonyl, N,N-di(C1-C6) alkylsulfamoyl, (C1-C6) alkoxy(C1-C6) alkyl, di(C1-C6) alkoxy(C1-C6) alkyl, thietanyl, thiazolyl or 2-oxotetrahydrofuranyl, and, R 8 and R 9 are optionally the same or different and are optionally bonded to each other to form a 4- to 6-membered ring;

[0404] (a31) R 10 (R 11 )N(C1-C6) alkyl, wherein, R 10 and R 11 represent a hydrogen atom or (C1-C6) alkyl, and, R 10 and R 11 are optionally the same or different and are optionally bonded to each other to form a 4- to 6-membered ring;

[0405] (a32) (C1-C6) alkylthio(C1-C6) alkyl;

[0406] (a33) (C1-C6) alkylsulfinyl(C1-C6) alkyl;

[0407] (a34) (C1-C6) alkylsulfonyl(C1-C6) alkyl;

[0408] (a45) (C1-C6) alkoxycarbonyl;

[0409] (a52) R 10 (R 11 ) N-sulfonyl, wherein R 10 and R 11 are the same as the said R 10 and R 11 ;

[0410] (a55) (C1-C6) alkoxyimino (C1-C3) alkyl;

[0411] (a57) phenyl;

[0412] (a58) phenyl having 1 to 5 optionally identical or different substituents selected from halogen atoms and (C1-C6) alkoxy groups on the ring;

[0413] (a59) pyridyl;

[0414] (a62) pyrazolyl having 1 to 3 optionally identical or different (C1-C6) alkyl groups on the ring;

[0415] (a65) dioxolanyl;

[0416] (a67) dioxanyl;

[0417] (a69) (C1-C6) alkylene formed by bonding of two adjacent substituents (R 1 ); or

[0418] (a70) methylenedioxy optionally substituted by 1 or 2 halogen atoms and formed by bonding of two adjacent substituents (R 1 );

[0419] When m represents an integer of 2 or more, R 1 are optionally identical or different,

[0420] m represents 0, 1, 2, 3 or 4,

[0421] R 2 represents:

[0422] (b1) hydrogen atom;

[0423] (b2) (C1-C6) alkyl;

[0424] (b3) (C3-C6) cycloalkyl;

[0425] (b5) (C2-C6) alkynyl;

[0426] (b6) halo (C1-C6) alkyl; or

[0427] (b9) (C1-C6) alkoxy (C1-C6) alkyl,

[0428] R 3 represents:

[0429] (c1) a hydrogen atom;

[0430] (c3) a cyano group;

[0431] (c5) a formamido group;

[0432] (c6) (C1-C6) alkyl;

[0433] (c12) R 8 (R 9 ) N group, where R 8 and R 9 is the same as the said R 8 and R 9 ;

[0434] (c13) (C1-C6) alkoxy; or

[0435] (c16) (C1-C6) alkoxycarbonyl (C1-C6) alkyl,

[0436] R 4 represents:

[0437] (d1) a hydrogen atom;

[0438] (d2) (C1-C6) alkyl;

[0439] (d3) (C2-C6) alkenyl;

[0440] (d4) (C2-C6) alkynyl;

[0441] (d6) halo (C1-C6) alkyl;

[0442] (d9) (C1-C6) alkoxy (C1-C6) alkyl;

[0443] (d13) (C3-C6) cycloalkyl (C1-C6) alkyl;

[0444] (d14) cyano (C1-C6) alkyl;

[0445] (d15) (C1-C6) alkylthio (C1-C6) alkyl;

[0446] (d16) (C1-C6) alkylsulfinyl (C1-C6) alkyl;

[0447] (d17) (C1-C6) alkylsulfonyl (C1-C6) alkyl;

[0448] (d18) carboxy(C1-C6)alkyl;

[0449] (d19) phenyl(C1-C6)alkyl;

[0450] (d20) phenyl(C1-C6)alkyl having 1 to 5 halogen atoms which may be the same or different on the ring;

[0451] (d22)(C1-C6)alkylcarbonyl;

[0452] (d23) (C1-C6) alkoxycarbonyl;

[0453] (d24) (C1-C6) alkylsulfonyl;

[0454] (d30) phenyl; or

[0455] (d32) (C1-C6) alkoxycarbonyl (C1-C6) alkyl,

[0456] A 1 , A 2 and A 3 Represents CR 5 or nitrogen atom, A 1 , A 2 and A 3 Optional same or different, wherein CR 5 R 5 represents a hydrogen atom, a halogen atom, a (C1-C6) alkyl group or R 10 (R 11 )N group, where R 10 and R 11 With the R 10 and R 11 same,

[0457] Q means:

[0458] (e1) a halogen atom;

[0459] (e2) cyano;

[0460] (e4) formyl;

[0461] (e5) (C1-C6) alkyl;

[0462] (e6)(C2-C6)alkenyl;

[0463] (e8) halo(C1-C6)alkyl;

[0464] (e11) (C1-C6) alkoxy;

[0465] (e13) hydroxy(C1-C6)alkyl;

[0466] (e14) dihydroxy (C1-C6) alkyl;

[0467] (e16) (C1-C6) alkoxy (C2-C6) alkenyl;

[0468] (e17) R 8 (R 9 )N group, wherein R 8 and R 9 are the same as the said R 8 and R 9 ;

[0469] (e18) dioxolanyl;

[0470] (e19) dioxolanyl having 1 or 2 substituents which are the same or different and selected from carbonyl group and (C1-C6) alkyl group on the ring;

[0471] (e20) dioxanyl;

[0472] (e22) phenyl;

[0473] (e24) imidazolyl;

[0474] (e27) oxadiazolyl having (C1-C6) alkyl group on the ring;

[0475] (e28) S(O) p R 6 group, wherein R 6 represents a hydrogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, phenyl (C1-C6) alkyl group, (C1-C6) alkoxyphenyl (C1-C6) alkyl group, (C1-C6) alkylphenyl (C1-C6) alkyl group, tris (C1-C6) alkylsilylphenyl (C1-C6) alkyl group or N(R 8 )R 9 group, p represents 0, 1 or 2, wherein R 8 )R 9 in the N(R 8 and R 9 are the same as the said R 8 and R 9 ;

[0476] (e29) C(O)R 7 group, wherein R 7Represents a hydroxyl group, (C1-C6) alkyl, (C1-C6) alkoxycarbonyl (C1-C6) alkyl, phenyl (C1-C6) alkoxy, (C1-C6) alkoxy, (C2-C6) alkynyloxy, (C3-C6) cycloalkoxy, phenoxy, (C1-C6) alkoxycarbonyl (C1-C6) alkoxy, (C1-C6) alkylthio, thiazolidinyl or N(R 8 )R 9 group, where N(R 8 )R 9 in the group, R 8 and R 9 are the same as the said R 8 and R 9 ;

[0477] (e31) N-(C1-C6) alkylaminothiocarbonyl;

[0478] (e33) [Chemical formula 4]

[0479]

[0480] In the formula, R 6 and R 8 are the same as the said R 6 and R 8 ;

[0481] (e35) (C1-C6) alkoxyimino (C1-C3) alkyl;

[0482] (e36) Halo (C1-C6) alkoxyimino (C1-C3) alkyl;

[0483] (e37) Hydrazono (C1-C3) alkyl;

[0484] (e40) Phenyl (C1-C6) alkoxyimino (C1-C3) alkyl;

[0485] (e41) (C2-C6) alkenyloxyimino (C1-C3) alkyl;

[0486] (e42) Di (C1-C6) alkoxyphosphonyl;

[0487] (e43) Di (C1-C6) alkoxyphosphonylamino;

[0488] (e44) Hydroxyl; or

[0489] (e45) (C1-C6) alkoxy (C1-C6) alkoxy.

[0490] (4) The compound or its salt according to the said (1), where

[0491] A1 represents a nitrogen atom,

[0492] A 2 and A 3 optionally the same or different, represents CR 5 .

[0493] (5) The compound or its salt according to (2) above, wherein,

[0494] A 1 represents a nitrogen atom,

[0495] A 2 and A 3 optionally the same or different, represents CR 5 .

[0496] (6) The compound or its salt according to (3) above, wherein,

[0497] A 1 represents a nitrogen atom,

[0498] A 2 and A 3 optionally the same or different, represents CR 5 .

[0499] (7) The compound or its salt according to (2) above, wherein,

[0500] A 1 、A 2 and A 3 optionally the same or different, represents CR 5 .

[0501] (8) The compound or its salt according to (3) above, wherein,

[0502] A 1 、A 2 and A 3 optionally the same or different, represents CR 5 .

[0503] (9) The compound or its salt according to (3) above, wherein,

[0504] A 1 and A 3 optionally the same or different, represents CR 5 ,

[0505] A 2 represents a nitrogen atom.

[0506] (10) The compound or its salt according to (3) above, wherein,

[0507] A1 With A 2 Optionally the same or different, representing CR 5 ,

[0508] A 3 Represents a nitrogen atom.

[0509] (11) The compound or its salt according to (3) above, wherein,

[0510] A 1 and A 3 Represents a nitrogen atom,

[0511] A 2 Represents CR 5 .

[0512] (12) The compound or its salt according to (2) above, wherein,

[0513] A 1 and A 2 Represents a nitrogen atom, A 3 Represents CR 5 .

[0514] (13) The compound or its salt according to (3) above, wherein,

[0515] A 1 and A 2 Represents a nitrogen atom, A 3 Represents CR 5 .

[0516] (14) The compound or its salt according to (3) above, wherein,

[0517] A 1 Represents CR 5 , A 2 and A 3 Represents a nitrogen atom.

[0518] (15) A herbicide for agricultural and horticultural use, characterized in that it contains the compound or its salt according to any one of (1) to (14) above as an active ingredient.

[0519] (16) A method for using a herbicide for agricultural and horticultural use, characterized in that an effective amount of the herbicide for agricultural and horticultural use according to (15) above is used to treat weeds, soil, paddy fields or cultivation carriers.

[0520] (17) A method for controlling weeds, characterized in that an effective amount of the herbicide for agricultural and horticultural use according to (15) above is used to treat weeds, soil, paddy fields or cultivation carriers.

[0521] Advantages of the Invention

[0522] The nitrogen-containing condensed heterocyclic compound having an oxime group or a salt thereof according to the present invention has excellent effects as a herbicide for agriculture and horticulture. Detailed embodiments

[0523] In the definition of the general formula (1) of the inventive compound of the present application, "halogenated" means "halogen atom", and represents a chlorine atom, a bromine atom, an iodine atom or a fluorine atom.

[0524] "(C1-C6) alkyl" represents, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, tert-pentyl, neopentyl, 2,3-dimethylpropyl, 1-ethylpropyl, 1-methylbutyl, 2-methylbutyl, n-hexyl, isohexyl, 2-hexyl, 3-hexyl, 2-methylpentyl, 3-methylpentyl, 1,1,2-trimethylpropyl, 3,3-dimethylbutyl, etc., which are straight-chain or branched-chain alkyl groups having 1 to 6 carbon atoms.

[0525] "(C2-C6) alkenyl" represents, for example, vinyl, allyl, isopropenyl, 1-butenyl, 2-butenyl, 2-methyl-2-propenyl, 1-methyl-2-propenyl, 2-methyl-1-propenyl, pentenyl, 1-hexenyl, 3,3-dimethyl-1-butenyl, etc., which are straight-chain or branched-chain alkenyl groups having 2 to 6 carbon atoms, and "(C2-C6) alkynyl" represents, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 3-methyl-1-propynyl, 2-methyl-3-propynyl, pentynyl, 1-hexynyl, 3-methyl-1-butynyl, 3,3-dimethyl-1-butynyl, etc., which are straight-chain or branched-chain alkynyl groups having 2 to 6 carbon atoms.

[0526] "(C3-C6) cycloalkyl" represents, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc., which are cyclic alkyl groups having 3 to 6 carbon atoms. As "(C1-C6) alkoxy", for example, it represents methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, n-pentyloxy, isopentyloxy, tert-pentyloxy, neopentyloxy, 2,3-dimethylpropoxy, 1-ethylpropoxy, 1-methylbutoxy, n-hexyloxy, isohexyloxy, 1,1,2-trimethylpropoxy, etc., which are straight-chain or branched-chain alkoxy groups having 1 to 6 carbon atoms. As "(C2-C6) alkenoxy", for example, it represents propenyloxy, butenyloxy, pentyloxy, hexyloxy, etc., which are straight-chain or branched-chain alkenoxy groups having 2 to 6 carbon atoms. As "(C2-C6) alkynyloxy", for example, it represents propynyloxy, butynyloxy, pentyloxy, hexyloxy, etc., which are straight-chain or branched-chain alkynyloxy groups having 2 to 6 carbon atoms.

[0527] As the “(C1-C6) alkylthio group”, for example, it represents a straight-chain or branched-chain alkylthio group with 1 to 6 carbon atoms such as methylthio group, ethylthio group, n-propylthio group, isopropylthio group, n-butylthio group, sec-butylthio group, tert-butylthio group, n-pentylthio group, isopentylthio group, tert-pentylthio group, neopentylthio group, 2,3-dimethylpropylthio group, 1-ethylpropylthio group, 1-methylbutylthio group, n-hexylthio group, isohexylthio group, 1,1,2-trimethylpropylthio group, etc.

[0528] As the “(C1-C6) alkylsulfinyl group”, for example, it represents a straight-chain or branched-chain alkylsulfinyl group with 1 to 6 carbon atoms such as methylsulfinyl group, ethylsulfinyl group, n-propylsulfinyl group, isopropylsulfinyl group, n-butylsulfinyl group, sec-butylsulfinyl group, tert-butylsulfinyl group, n-pentylsulfinyl group, isopentylsulfinyl group, tert-pentylsulfinyl group, neopentylsulfinyl group, 2,3-dimethylpropylsulfinyl group, 1-ethylpropylsulfinyl group, 1-methylbutylsulfinyl group, n-hexylsulfinyl group, isohexylsulfinyl group, 1,1,2-trimethylpropylsulfinyl group, etc.

[0529] As the “(C1-C6) alkylsulfonyl group”, for example, it represents a straight-chain or branched-chain alkylsulfonyl group with 1 to 6 carbon atoms such as methylsulfonyl group, ethylsulfonyl group, n-propylsulfonyl group, isopropylsulfonyl group, n-butylsulfonyl group, sec-butylsulfonyl group, tert-butylsulfonyl group, n-pentylsulfonyl group, isopentylsulfonyl group, tert-pentylsulfonyl group, neopentylsulfonyl group, 2,3-dimethylpropylsulfonyl group, 1-ethylpropylsulfonyl group, 1-methylbutylsulfonyl group, n-hexylsulfonyl group, isohexylsulfonyl group, 1,1,2-trimethylpropylsulfonyl group, etc.

[0530] “(C1-C6) alkylcarbonyl” represents, for example, an alkylcarbonyl group having the (C1-C6) alkyl group such as acetyl group, propionyl group, butyryl group, 2-methylpropionyl group, valeryl group, 2-methylbutyryl group, 3-methylbutyryl group, pivaloyl group, hexanoyl group, etc., and an alkylcarbonyl group with 2 to 7 carbon atoms.

[0531] “(C1-C6) alkylcarbonyloxy” represents, for example, an alkylcarbonyloxy group having the (C1-C6) alkyl group such as acetyloxy group, propionyloxy group, butyryloxy group, 2-methylpropionyloxy group, valeryloxy group, 2-methylbutyryloxy group, 3-methylbutyryloxy group, pivaloyloxy group, hexanoyloxy group, etc., and an alkylcarbonyloxy group with 2 to 7 carbon atoms.

[0532] As "(C1-C6) alkylsulfonyloxy", for example, it represents linear or branched alkylsulfonyloxy with 1 to 6 carbon atoms such as methylsulfonyloxy, ethylsulfonyloxy, n-propylsulfonyloxy, isopropylsulfonyloxy, n-butylsulfonyloxy, sec-butylsulfonyloxy, tert-butylsulfonyloxy, n-pentylsulfonyloxy, isopentylsulfonyloxy, tert-pentylsulfonyloxy, neopentylsulfonyloxy, 2,3-dimethylpropylsulfonyloxy, 1-ethylpropylsulfonyloxy, 1-methylbutylsulfonyloxy, n-hexylsulfonyloxy, isohexylsulfonyloxy, 1,1,2-trimethylpropylsulfonyloxy, etc.

[0533] "N-(C1-C6) alkylformamido" represents, for example, alkylformamido with 2 to 7 carbon atoms having linear or branched alkyl with 1 to 6 carbon atoms such as N-methylformamido, N-ethylformamido, N-n-propylformamido, N-isopropylformamido, N-n-butylformamido, N-isobutylformamido, N-sec-butylformamido, N-tert-butylformamido, N-n-pentylformamido, N-isopentylformamido, N-tert-pentylformamido, N-neopentylformamido, N-n-hexylformamido, N-isohexylformamido, etc.

[0534] "(C1-C6) alkoxycarbonyl" represents, for example, alkoxycarbonyl with 2 to 7 carbon atoms such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, pentyloxycarbonyl, etc. having the (C1-C6) alkoxy.

[0535] "N-(C1-C6) alkylsulfamoyl" represents, for example, N-alkylsulfamoyl with 1 to 6 carbon atoms such as N-methylsulfamoyl, N-ethylsulfamoyl, N-n-propylsulfamoyl, N-isopropylsulfamoyl, N-n-butylsulfamoyl, N-isobutylsulfamoyl, N-sec-butylsulfamoyl, N-tert-butylsulfamoyl, N-n-pentylsulfamoyl, N-isopentylsulfamoyl, N-tert-pentylsulfamoyl, N-neopentylsulfamoyl, N-(2,3-dimethylpropyl)sulfamoyl, N-(1-ethylpropyl)sulfamoyl, N-(1-methylbutyl)sulfamoyl, N-(2-methylbutyl)sulfamoyl, N-n-hexylsulfamoyl, N-isohexylsulfamoyl, N-(2-hexyl)sulfamoyl, N-(3-hexyl)sulfamoyl, N-(2-methylpentyl)sulfamoyl, N-(3-methylpentyl)sulfamoyl, N-(1,1,2-trimethylpropyl)sulfamoyl, N-(3,3-dimethylbutyl)sulfamoyl, etc.

[0536] “(C1-C6) alkylthiolcarbonyl” means, for example, alkylthiolcarbonyls having 1 to 6 carbon atoms such as methylthiolcarbonyl, ethylthiolcarbonyl, n-propylthiolcarbonyl, isopropylthiolcarbonyl, n-butylthiolcarbonyl, isobutylthiolcarbonyl, sec-butylthiolcarbonyl, tert-butylthiolcarbonyl, 2,3-dimethylpropylthiolcarbonyl, etc.

[0537] In the above-mentioned “(C1-C6) alkyl”, “(C2-C6) alkenyl”, “(C2-C6) alkynyl”, “(C1-C6) alkoxy”, “(C1-C6) alkylthio”, “(C1-C6) alkylsulfinyl”, “(C1-C6) alkylsulfonyl”, “(C3-C6) cycloalkyl”, “(C1-C6) alkylcarbonyl”, “(C1-C6) alkoxycarbonyl”, “(C1-C6) alkylcarbonyloxy”, “(C1-C6) alkylsulfonyloxy”, etc., the substitutable positions are optionally substituted by one or more halogen atoms. When there are two or more substituted halogen atoms, the halogen atoms are optionally the same or different.

[0538] In this case, they are respectively denoted as “halo(C1-C6) alkyl”, “halo(C2-C6) alkenyl”, “halo(C2-C6) alkynyl”, “halo(C1-C6) alkoxy”, “halo(C1-C6) alkylthio”, “halo(C1-C6) alkylsulfinyl”, “halo(C1-C6) alkylsulfonyl”, “halo(C3-C6) cycloalkyl”, “halo(C1-C6) alkylcarbonyl”, “halo(C1-C6) alkoxycarbonyl”, “halo(C1-C6) alkylcarbonyloxy”, “halo(C1-C6) alkylsulfonyloxy”, etc.

[0539] Expressions such as “(C1-C6)”, “(C2-C6)”, “(C3-C6)” represent the range of the number of carbon atoms of various substituents. Further, for the groups to which the above substituents are bonded, the above definitions can also be represented. For example, in the case of “(C1-C6) alkoxy(C1-C6) alkyl”, it means that a straight-chain or branched alkoxy having 1 to 6 carbon atoms is bonded to a straight-chain or branched alkyl having 1 to 6 carbon atoms.

[0540] Examples of the salts of the compound represented by the general formula (1) of the present invention include inorganic acid salts such as hydrochloride, sulfate, nitrate, phosphate, etc., organic acid salts such as acetate, fumarate, maleate, oxalate, methanesulfonate, benzenesulfonate, p-toluenesulfonate, etc., and salts with inorganic or organic bases such as sodium ion, potassium ion, calcium ion, trimethylammonium, etc.

[0541] Regarding the nitrogen-containing condensed heterocyclic compound represented by the general formula (1) of the present invention and its salts, there may be one or more chiral centers in its structural formula, and there may also be two or more optical isomers and diastereoisomers. The present invention includes all various optical isomers and mixtures containing these optical isomers in any proportion. In addition, regarding the nitrogen-containing condensed heterocyclic compound represented by the general formula (1) of the present invention and its salts, there may be two geometric isomers derived from carbon-carbon double bonds and carbon-nitrogen double bonds in its structural formula. The present invention includes all various geometric isomers and mixtures containing these geometric isomers in any proportion. That is, regarding the oxime group in the compound represented by the general formula (1) of the present invention, it can be an E (entgegen) isomer, a Z (zusammen) isomer, or a mixture of the two isomers.

[0542] Regarding the compound represented by the general formula (1) of the present invention, the following preferred embodiments are shown.

[0543] As R 1 , it is preferably a group of the above (a1), (a2), (a3), (a4), (a5), (a6), (a7), (a8), (a9), (a10), (a11), (a12), (a14), (a15), (a16), (a17), (a18), (a19), (a20), (a21), (a22), (a23), (a24), (a25), (a26), (a27), (a28), (a29), (a30), (a31), (a32), (a33), (a34), (a35), (a36), (a37), (a44), (a45), (a46), (a47), (a50), (a52), (a55), (a56), (a57), (a58), (a59), (a60), (a61), (a62), (a63), (a64), (a65), (a66), (a67), (a68), (a69) or (a70),

[0544] More preferably, a group of the above (a1), (a2), (a3), (a4), (a5), (a6), (a7), (a9), (a10), (a14), (a16), (a17), (a22), (a23), (a24), (a26), (a27), (a28), (a29), (a30), (a31), (a32), (a33), (a34), (a45), (a52), (a55), (a57), (a58), (a59), (a62), (a65), (a67), (a69) or (a70) can be enumerated.

[0545] As m, 0, 1, 2, 3 or 4 can be preferably cited.

[0546] As R 2 , it is preferably a group of the above (b1), (b2), (b3), (b4), (b5), (b6), (b7), (b8), (b9), (b10), (b11), (b12), (b13), (b15), (b16), (b18) or (b21),

[0547] and more preferably, a group of the above (b1), (b2), (b3), (b5), (b6) or (b9) can be cited.

[0548] As R 3 , it is preferably a group of the above (c1), (c2), (c3), (c4), (c5), (c6), (c9), (c12), (c13), (c14), (c15) or (c16),

[0549] and more preferably, a group of the above (c1), (c3), (c5), (c6), (c12), (c13) or (c16) can be cited.

[0550] As R 4 , it is preferably a group of the above (d1), (d2), (d3), (d4), (d5), (d6), (d7), (d8), (d9), (d10), (d13), (d14), (d15), (d16), (d17), (d18), (d19), (d20), (d22), (d23), (d24), (d25), (d26), (d27), (d30), (d31) or (d32),

[0551] and more preferably, a group of the above (d1), (d2), (d3), (d4), (d6), (d9), (d13), (d14), (d15), (d16), (d17), (d18), (d19), (d20), (d22), (d23), (d24), (d30) or (d32) can be cited.

[0552] As A 1 、A 2 and A 3 , it is preferably CR 5 (wherein, R 5 represents a hydrogen atom, a halogen atom, a cyano group, a (C1-C6) alkyl group, a halogenated (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halogenated (C1-C6) alkoxy group, R 10 (R 11 )N group (wherein, R 10 and R11 with the said R 10 and R 11 being the same), (C1-C6) alkylthio, (C1-C6) alkylsulfinyl or (C1-C6) alkylsulfonyl) or a nitrogen atom,

[0553] More preferably, CR 5 (wherein, R 5 is a hydrogen atom, a halogen atom, (C1-C6) alkyl or R 10 (R 11 )N group (wherein, R 10 and R 11 are the same as the said R 10 and R 11 )) or a nitrogen atom.

[0554] A 1 、A 2 and A 3 are optionally the same or different.

[0555] As Q, it is preferably a group of the above (e1), (e2), (e4), (e5), (e6), (e7), (e8), (e11), (e12), (e13), (e14), (e15), (e16), (e17), (e18), (e19), (e20), (e21), (e22), (e23), (e24), (e25), (e26), (e27), (e28), (e29), (e30), (e31), (e32), (e33), (e34), (e35), (e36), (e37), (e38), (e39), (e40), (e41), (e42), (e43), (e44), (e45) or (e46),

[0556] More preferably, groups of (e1), (e2), (e4), (e5), (e6), (e8), (e11), (e13), (e14), (e16), (e17), (e18), (e19), (e20), (e22), (e24), (e27), (e28), (e29), (e31), (e33), (e35), (e36), (e37), (e40), (e41), (e42), (e43), (e44) or (e45) can be enumerated.

[0557] Various compounds of the present invention can be prepared, for example, by the following preparation methods, but the present invention is not limited thereto.

[0558] Preparation Method 1

[0559] [Chemical Formula 5]

[0560]

[0561] In the formula, A 1 、A 2 、A 3 、R 1 、R 2 、R 4 、R 6 and m are the same as the aforementioned A 1 、A 2 、A 3 、R 1 、R 2 、R 4 、R 6 and m, p' represents 1 or 2, and R' represents, for example, a (C1-C4) alkyl group such as a methyl group or an ethyl group.

[0562] The compound represented by the general formula (1-1) and the compound represented by the general formula (1-2) of the present invention can be prepared from the compound represented by the general formula (2-1) through the following steps [a], [b], [c], [d] and [e]. In addition, the preparation method of the compound represented by the general formula (2-1) as the starting material will be described later.

[0563] Preparation method of step [a]

[0564] By subjecting the compound represented by the general formula (2-1) and the compound represented by the general formula (3) to a condensation reaction in the presence of a base, a condensing agent and an inert solvent to form an amide compound, and then subjecting it to a dehydration reaction in the presence of an acid and an inert solvent, the compound represented by the general formula (4) can be prepared.

[0565] Examples of the condensing agent that can be used in this condensation reaction include acid activators such as carbonyl chloride, phosphorus trichloride, phosphorus oxychloride, oxalyl chloride, and thionyl chloride, carbodiimides such as N,N'-dicyclohexylcarbodiimide (DCC) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDCI). In addition, phosphorus pentoxide, polyphosphoric acid, N,N'-carbonyldiimidazole, 2-chloro-1-methylpyridinium iodide (Mukaiyama reagent), 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), triphenylphosphine / carbon tetrachloride, tripyrrolidinophosphonium bromide hexafluorophosphate (BROP), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP), N,N,N',N'-bis(tetramethylene)chlorouronium tetrafluoroborate, O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HBTU), O-(1H-benzotriazol-1-yl)-N,N,N',N'-bis(tetramethylene)uronium hexafluorophosphate, O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate (TBTU), O-(1H-benzotriazol-1-yl)-N,N,N',N'-bis(tetramethylene)uronium tetrafluoroborate, O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU), 1-hydroxybenzotriazole (HOBt), propylphosphonic anhydride (T3P), and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholine hydrochloride (DMT-MM). These reagents can be used alone or in combination of two or more. Regarding the amount of the condensing agent, it can be appropriately selected within the range of 0.5 to 5 times the molar amount relative to the compound represented by the general formula (2-1).

[0566] Examples of the base that can be used in this condensation reaction include carbonates such as lithium carbonate, lithium hydrogencarbonate, sodium carbonate, sodium hydrogencarbonate, potassium carbonate, potassium hydrogencarbonate, calcium carbonate, and magnesium carbonate, acetates such as lithium acetate, sodium acetate, and potassium acetate, and organic bases such as pyridine, methylpyridine, dimethylpyridine, triethylamine, tributylamine, and N,N-diisopropylethylamine. Regarding the amount of the base, it can be appropriately selected within the range of 0.5 to 5 times the molar amount relative to the compound represented by the general formula (2-1), and this base can also be used as a solvent.

[0567] As an inert solvent that can be used in this condensation reaction, a solvent that does not significantly hinder this reaction is sufficient. For example, linear or cyclic saturated hydrocarbons such as pentane, hexane, and cyclohexane, linear or cyclic ethers such as diethyl ether, tetrahydrofuran (THF), and dioxane, aromatic hydrocarbons such as benzene, toluene, and xylene, halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride, nitriles such as acetonitrile and isopropyl cyanide, polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, and 1,3-dimethyl-2-imidazolidinone can be cited. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it is an amount that can dissolve the reaction reagents, and it can be appropriately selected within the range of 0.5 L to 100 L relative to 1 mole of the compound represented by the general formula (2-1). In addition, when the base is used as a solvent, a solvent may not be used.

[0568] Since this condensation reaction is an equimolar reaction, each compound can be used in equimolar amounts, but any one of the compounds can also be used in excess. Regarding the reaction temperature, it can generally be carried out within the range of about 0 °C to the boiling point of the solvent used. Regarding the reaction time, although it varies depending on the reaction scale, reaction temperature, etc. and is not fixed, it can be appropriately selected within the range of several minutes to 48 hours.

[0569] After the reaction is completed, the target product can be separated from the reaction system containing the target product by a conventional method, and it can also be purified by recrystallization, column chromatography, etc. as needed to prepare the target product. In addition, it can also be used in the subsequent dehydration reaction without separation.

[0570] As the acid that can be used in this dehydration reaction, inorganic acids such as hydrochloric acid, sulfuric acid, and nitric acid, organic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, and benzoic acid, sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, and p-toluenesulfonic acid, and phosphoric acid can be cited. Regarding its amount, it can be appropriately selected within the range of 0.01-fold molar to 10-fold molar relative to the amide compound, and this acid can also be used as a solvent.

[0571] As an inert solvent that can be used in this dehydration reaction, a solvent that does not significantly hinder the progress of this reaction is sufficient. For example, aromatic hydrocarbons such as benzene, toluene, and xylene, halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, linear or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran, esters such as ethyl acetate, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, ketones such as acetone and methyl ethyl ketone, polar solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone, etc. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it is an amount that can dissolve the reaction reagents, and it can be appropriately selected within the range of 0.5 L to 100 L relative to 1 mole of the amide compound obtained in the condensation reaction. In addition, when the acid is used as the solvent, the solvent can be not used.

[0572] Regarding the reaction temperature, it can be carried out in the range from room temperature to the boiling point of the inert solvent used. Regarding the reaction time, although it is not fixed due to the reaction scale and reaction temperature, it can be appropriately selected within the range of several minutes to 48 hours.

[0573] After the reaction is completed, the target product can be separated from the reaction system containing the target product by a conventional method, and the target product can be prepared by purification through recrystallization, column chromatography, etc. as needed. In addition, it can also be supplied to the next process without separation.

[0574] Preparation method of step [b]

[0575] By reacting the compound represented by the general formula (4) with the thiol compound represented by the general formula HSR 6 (5) in the presence of a base and an inert solvent, the compound represented by the general formula (6) can be prepared.

[0576] Examples of the base used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, and potassium bicarbonate, acetates such as sodium acetate and potassium acetate, alkali metal alcoholates such as potassium tert-butoxide, sodium methoxide, and sodium ethoxide, tertiary amines such as triethylamine, N,N-diisopropylethylamine, and 1,8-diazabicyclo[5.4.0]undec-7-ene, nitrogen-containing aromatic compounds such as pyridine and N,N-dimethyl-4-aminopyridine, etc. The amount used is usually in the range of 1-fold mole to 10-fold moles relative to the compound represented by the general formula (4). In addition, when the base salt of the compound represented by the general formula (5) is used, the base can be not used.

[0577] As an inert solvent used in this reaction, a solvent that does not significantly hinder the progress of this reaction is sufficient. Examples thereof include aromatic hydrocarbons such as benzene, toluene, and xylene, halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, chain or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran, esters such as ethyl acetate, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, ketones such as acetone and methyl ethyl ketone, and polar solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it is an amount that dissolves the reaction reagents, and it can be appropriately selected within the range of 0.5 L to 100 L relative to 1 mole of the compound represented by the general formula (4).

[0578] Since this reaction is an equimolar reaction, the compound represented by the general formula (4) and the compound represented by the general formula (5) can be used in equimolar amounts, but either reactant can also be used in excess. Regarding the reaction temperature, it can be carried out in the range from -20 °C to the boiling point of the inert solvent used. Regarding the reaction time, although it is not fixed depending on the reaction scale and reaction temperature, it can be carried out within the range of several minutes to 48 hours. After the reaction is completed, the target product can be separated from the reaction system containing the target product by a conventional method, and the target product can be prepared by purification through recrystallization, column chromatography, etc. as needed. In addition, it can also be supplied to the next process without separation.

[0579] Preparation method of step [c]

[0580] The compound represented by the general formula (7) can be prepared by deprotecting the compound represented by the general formula (6) in the presence of an acid and an inert solvent.

[0581] Examples of the acid used in this reaction include inorganic acids such as hydrochloric acid, sulfuric acid, and nitric acid, organic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, and benzoic acid, sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, and p-toluenesulfonic acid, and phosphoric acid. Regarding the amount thereof, it can be appropriately selected within the range of 0.01-fold mole to 10-fold moles relative to the compound represented by the general formula (6), and this acid can also be used as a solvent.

[0582] As an inert solvent used in this reaction, a solvent that does not significantly hinder the progress of this reaction is sufficient. Examples thereof include aromatic hydrocarbons such as benzene, toluene, and xylene, halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, linear or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran, esters such as ethyl acetate, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, ketones such as acetone and methyl ethyl ketone, polar solvents such as dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone, and water. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it is an amount sufficient to dissolve the reaction reagents, and it can be appropriately selected within the range of 0.5 L to 100 L relative to 1 mol of the compound represented by the general formula (6). In addition, when the acid is used as the solvent, the solvent may not be used.

[0583] Regarding the reaction temperature, it can be carried out in the range from room temperature to the boiling point of the inert solvent used. Regarding the reaction time, although it is not fixed due to the reaction scale and reaction temperature, it can be carried out within the range of several minutes to 48 hours.

[0584] After the reaction is completed, the target product can be separated from the reaction system containing the target product by a conventional method, and the target product can be prepared by purification through recrystallization, column chromatography, etc. as needed. In addition, it can also be supplied to the next process without separation.

[0585] Preparation method of step [d]

[0586] By reacting the compound represented by the general formula (7) with the compound represented by the general formula (8) according to the method described in ORGANIC FUNCTIONAL GROUP PREPARATIONS III 2nd edition (ACADEMIC PRESS, INC.), the compound represented by the general formula (1-1) of the present invention can be prepared. After the reaction is completed, the target product can be separated from the reaction system containing the target product by a conventional method, and the target product can also be prepared by purification through recrystallization, column chromatography, etc. as needed. In addition, it can also be supplied to the next process without separation.

[0587] Preparation method of step [e]

[0588] By reacting the compound represented by the general formula (1-1) with an oxidizing agent in an inert solvent, the compound represented by the general formula (1-2) of the present invention can be prepared.

[0589] As the oxidizing agent used in this reaction, peroxides such as hydrogen peroxide, peroxybenzoic acid, and m-chloroperoxybenzoic acid can be exemplified. These oxidizing agents can be appropriately selected within the range of 1 to 5 times the molar amount of the compound represented by the general formula (1-1).

[0590] As the inert solvent that can be used in this reaction, any solvent that does not significantly hinder this reaction can be used. Examples include chain or cyclic ethers such as diethyl ether, tetrahydrofuran, and dioxane; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; nitriles such as acetonitrile; esters such as ethyl acetate; organic acids such as formic acid and acetic acid; polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, 1,3-dimethyl-2-imidazolidinone, and water. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it can dissolve the reaction reagents, and it can be appropriately selected within the range of 0.5 L to 100 L relative to 1 mole of the compound represented by the general formula (1-1).

[0591] In this reaction, regarding the reaction temperature, it can be appropriately selected within the range of -10°C to the reflux temperature of the inert solvent used. Regarding the reaction time, although it varies depending on the reaction scale, reaction temperature, etc. and is not fixed, it can be appropriately selected within the range of several minutes to 48 hours.

[0592] After the reaction is completed, the target product can be separated from the reaction system containing the target product by a conventional method, and the target product can be prepared by purification through recrystallization, column chromatography, etc. as needed.

[0593] Preparation Method 2

[0594] [Chemical Formula 6]

[0595]

[0596] In the formula, A 1 , A 2 , A 3 , R 1 , R 2 , R 4 , R 6 and m are the same as those of the aforementioned A 1 , A 2 , A 3 , R 1 , R 2 , R 4 , R 6 and m. p' represents 1 or 2, and R' represents a (C1-C4) alkyl group such as methyl or ethyl, for example.

[0597] The compound represented by the general formula (1-3) of the present invention can be prepared from the compound represented by the general formula (2-2) through the steps [a], [b] and [e] of the above Preparation Method 1. In addition, the preparation method of the compound represented by the general formula (2-2) as the starting material will be described later.

[0598] Preparation Method 3

[0599] [Chemical Formula 7]

[0600]

[0601] In the formula, A 1 、A 2 、A 3 、R 1 、R 2 、R 4 、R 6 、R 8 、R 9 and m are the same as those of the above A 1 、A 2 、A 3 、R 1 、R 2 、R 4 、R 6 、R 8 、R 9 and m, p' represents 1 or 2, R' represents a (C1-C4) alkyl group such as a methyl group or an ethyl group, and L represents a leaving group such as bromine or chlorine.

[0602] The compound represented by the general formula (1-4), the compound represented by the general formula (1-5) and the compound represented by the general formula (1-6) of the present invention can be prepared from the compound represented by the general formula (2-3) through the following step [f] and the steps [a], [b] and [e] of the above Preparation Method 1. In addition, the preparation method of the compound represented by the general formula (2-3) as the starting material will be described later.

[0603] Preparation Method of Step [f]

[0604] By reacting the compound represented by the general formula (1-5) with the compound represented by the general formula (12) or the compound represented by the general formula (13) in the presence of a base and an inert solvent, the compound represented by the general formula (1-6) of the present invention can be prepared.

[0605] Examples of bases that can be used in this reaction include alkyllithiums such as methyllithium, n-butyllithium, sec-butyllithium, tert-butyllithium, etc., organometallic compounds such as lithium hexamethyldisilazide, sodium hexamethyldisilazide, etc., hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, etc., carbonates such as lithium carbonate, lithium hydrogencarbonate, sodium carbonate, sodium hydrogencarbonate, potassium carbonate, potassium hydrogencarbonate, calcium carbonate, magnesium carbonate, etc., acetates such as lithium acetate, sodium acetate, potassium acetate, etc., alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, potassium tert-butoxide, etc., metal hydrides such as sodium hydride, potassium hydride, etc., organic bases such as pyridine, methylpyridine, dimethylpyridine, triethylamine, tributylamine, N,N-diisopropylethylamine, etc. The amount used is generally in the range of 1 to 10 times the molar amount relative to the compound represented by the general formula (1-5).

[0606] Examples of inert solvents that can be used in this reaction include linear or cyclic saturated hydrocarbons such as pentane, hexane, cyclohexane, etc., linear or cyclic ethers such as diethyl ether, tetrahydrofuran (THF), dioxane, etc., aromatic hydrocarbons such as benzene, toluene, xylene, etc. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it can dissolve the reaction reagents, and it can be appropriately selected in the range of 0.5 L to 100 L relative to 1 mol of the compound represented by the general formula (1-5).

[0607] Since this reaction is an equimolar reaction, each compound can be used in an equimolar amount, or any one compound can be used in excess. Regarding the reaction temperature, it is generally carried out in the range of about -78 °C to the boiling point of the solvent used. Regarding the reaction time, although it varies depending on the reaction scale, reaction temperature, etc. and is not fixed, it can be appropriately selected in the range of several minutes to 48 hours.

[0608] After the reaction is completed, the target product can be separated from the reaction system containing the target product by a conventional method, and the target product can be prepared by purification through recrystallization, column chromatography, etc. as needed.

[0609] Preparation method 4

[0610] [Chemical formula 8]

[0611]

[0612] In the formula, A 1 , A 2 , A 3 , R 1 , R 2 , R 4 , R 8 , R 9 and m and the said A 1 , A2 、A 3 、R 1 、R 2 、R 4 、R 8 、R 9 and m are the same. R' represents, for example, a (C1-C4) alkyl group such as a methyl group or an ethyl group, R" represents, for example, a tertiary (C4-C6) alkyl group such as a tert-butyl group or a tri(C1-C3) alkylsilyl group such as a trimethylsilyl group, and L represents, for example, a leaving group such as bromine or chlorine.

[0613] The compounds represented by the general formula (1-7) and the compounds represented by the general formula (1-8) of the present invention can be prepared from the compounds represented by the general formula (11) through the following steps [g] and [h] and the step [f] of the above preparation method 3.

[0614] Preparation method of step [g]

[0615] By reacting the compound represented by the general formula (11) with the benzyl mercaptan compound represented by the general formula (14) in the presence of a base and an inert solvent, the compound represented by the general formula (15) can be prepared.

[0616] Examples of the base used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, and potassium bicarbonate, acetates such as sodium acetate and potassium acetate, alkali metal alcoholates such as potassium tert-butoxide, sodium methoxide, and sodium ethoxide, tertiary amines such as triethylamine, N,N-diisopropylethylamine, and 1,8-diazabicyclo[5.4.0]undec-7-ene, and nitrogen-containing aromatic compounds such as pyridine and N,N-dimethyl-4-aminopyridine. Regarding the amount thereof, it is usually used in the range of 1 to 10 times the molar amount relative to the compound represented by the general formula (11). In addition, when using the base salt of the compound represented by the general formula (14), the base may not be used.

[0617] As the inert solvent used in this reaction, any solvent that does not significantly hinder the progress of this reaction can be used. Examples include aromatic hydrocarbons such as benzene, toluene, and xylene, halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, chain or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran, esters such as ethyl acetate, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, ketones such as acetone and methyl ethyl ketone, and polar solvents such as dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone, and water. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent is not particularly limited as long as it is an amount that can dissolve the reaction reagents, and it can be appropriately selected in the range of 0.5 L to 100 L relative to 1 mole of the compound represented by the general formula (11).

[0618] Since this reaction is an equimolar reaction, it is sufficient to use the compound represented by the general formula (11) and the compound represented by the general formula (14) in equimolar amounts, and either compound can also be used in excess. Regarding the reaction temperature, it can be carried out in the range from -20°C to the boiling point of the inert solvent used. Regarding the reaction time, although it is not fixed due to the reaction scale and reaction temperature, it can be carried out within the range of several minutes to 48 hours.

[0619] After the reaction is completed, the target product can be separated from the reaction system containing the target product by a conventional method, and it can also be purified by recrystallization, column chromatography, etc. as needed to prepare the target product. In addition, it can also be used in the next process without separation.

[0620] Preparation method of step [h]

[0621] By reacting the compound represented by the general formula (15) with a halogenating agent in the presence of an inert solvent to carry out chlorosulfonylation, and then carrying out an amination reaction with the compound represented by the general formula (16) in the presence or absence of an inert solvent and a base, the compound represented by the general formula (1-7) of the present invention can be prepared.

[0622] Examples of the halogenating agent used in this chlorosulfonylation reaction include thionyl chloride, chlorine, sulfonyl chloride, 1,3-dichloro-5,5-dimethylhydantoin, N-chlorosuccinimide, etc. These halogenating agents can be appropriately selected within the range of 0.5 to 5 times the molar amount relative to the compound represented by the general formula (15).

[0623] The inert solvent used in this chlorosulfonylation reaction is a solvent that does not significantly hinder the progress of this reaction. Examples include halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, nitriles such as acetonitrile and propionitrile, organic acids such as acetic acid and propionic acid, and water. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it is an amount that can dissolve the reaction reagents, and it can be appropriately selected within the range of 0.5 L to 100 L relative to 1 mole of the compound represented by the general formula (15).

[0624] Since this chlorosulfonylation reaction is an equimolar reaction, it is sufficient to use each reactant in equimolar amounts, and either reactant can also be used in excess. Regarding the reaction temperature, it can be carried out in the range from room temperature to the boiling point of the inert solvent used. Regarding the reaction time, although it is not fixed due to the reaction scale and reaction temperature, it can be carried out within the range of several minutes to 48 hours.

[0625] After the reaction is completed, when the chlorosulfonylated product is stable, the target product can be separated from the reaction system containing the target product by conventional methods, and can also be purified by recrystallization, column chromatography, etc. as needed. In addition, when the chlorosulfonylated product is unstable, the reaction system can be directly used in subsequent reactions without purification.

[0626] Examples of the base used in this amination reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, acetate salts such as sodium acetate, potassium acetate, alkali metal alkoxides such as potassium tert-butoxide, sodium methoxide, sodium ethoxide, tertiary amines such as triethylamine, N,N-diisopropylethylamine, 1,8-diazabicyclo[5.4.0]undec-7-ene, and nitrogen-containing aromatic compounds such as pyridine, N,N-dimethyl-4-aminopyridine. Regarding the amount used, it is usually used in the range of 1 to 10 times the molar amount relative to the compound represented by the general formula (15).

[0627] Examples of the inert solvent that can be used in this amination reaction include aromatic hydrocarbons such as benzene, toluene, and xylene, halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, chain or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran, alcohols such as methanol, ethanol, propanol, and isopropanol, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, and inert solvents of polar solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it is an amount that can dissolve the reaction reagents, and can be appropriately selected in the range of 0.5 L to 100 L relative to 1 mole of the compound represented by the general formula (15).

[0628] Since this amination reaction is an equimolar reaction, each compound can be used in an equimolar amount, or any one compound can be used in excess. Regarding the reaction temperature, it can be carried out in the range from room temperature to the boiling point of the inert solvent used. Regarding the reaction time, although it is not fixed due to the reaction scale and reaction temperature, it can be carried out in the range of several minutes to 48 hours.

[0629] After the reaction is completed, the target product can be separated from the reaction system containing the target product by conventional methods, and the target product can be prepared by purification by recrystallization, column chromatography, etc. as needed.

[0630] Preparation Method 5

[0631] [Chemical Formula 9]

[0632]

[0633] In the formula, A 1 , A 2 , A 3 , R 1 , R 2 , R 4 , R 6 and m are the same as those of the aforementioned A 1 , A 2 , A 3 , R 1 , R 2 , R 4 , R 6 and m, p' represents 1 or 2, R 3’ represents (C1-C6) alkoxy or R 8 (R 9 )N group (R 8 and R 9 are the same as those of the aforementioned R 8 and R 9 ), X represents a halogen atom such as fluorine, chlorine, bromine, iodine, etc., and L represents a leaving group such as bromine or chlorine, etc.

[0634] The compounds represented by the general formula (1-9), the compounds represented by the general formula (1-10), the compounds represented by the general formula (1-11), and the compounds represented by the general formula (1-12) of the present invention can be prepared from the compounds represented by the general formula (7) through the following steps [d'], [i], [j] and [k] and the step [e] of the aforementioned preparation method 1.

[0635] Preparation method of step [d']

[0636] By reacting the compound represented by the general formula (7) with the compound represented by the general formula (8') according to the method described in "Preparation of Organic Functional Groups", 2nd Edition (ACADEMIC PRESS, INC.), the compound represented by the general formula (17) can be prepared. After the reaction is completed, the target product can be separated from the reaction system containing the target product by a conventional method, or the target product can be prepared by purification through recrystallization, column chromatography, etc. as needed. In addition, it can also be used in the next step without separation.

[0637] Preparation method of step [i]

[0638] By reacting the compound represented by the general formula (17) with a halogenating agent in the presence or absence of an inert solvent and a base, the compound represented by the general formula (1-9) of the present invention can be prepared.

[0639] As an inert solvent that can be used in this reaction, any solvent that does not significantly hinder the reaction can be used. For example, alcohols such as methanol and ethanol, aromatic hydrocarbons such as benzene, toluene, and xylene, ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone, halogenated hydrocarbons such as chloroform and dichloromethane, esters such as ethyl acetate and methyl acetate, linear or cyclic ethers such as tetrahydrofuran, diethyl ether, methyl tert-butyl ether, 1,2-dimethoxyethane, and dioxane, nitriles such as acetonitrile, polar solvents such as N,N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, and water can be cited. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it is an amount that can dissolve the reaction reagents, and it can be appropriately selected within the range of 0.5 L to 100 L relative to 1 mole of the compound represented by the general formula (17).

[0640] As the base that can be used in this reaction, alkali metal hydrides such as sodium hydride, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal carbonates such as sodium carbonate and potassium carbonate, inorganic salts, organic bases such as pyridine, DBU (1,8-diazabicyclo[5.4.0]undec-7-ene), and triethylamine can be cited. Regarding its amount, it can be appropriately selected within the range of equimolar to excess molar relative to the compound represented by the general formula (17) for the reaction.

[0641] As the halogenating agent that can be used in this reaction, N-halosuccinimides such as N-chlorosuccinimide and N-bromosuccinimide, hypohalite alkali metal salts such as sodium hypochlorite, hypohalite esters such as tert-butyl hypochlorite, elemental halogens such as chlorine, and sulfonyl chloride can be cited. Regarding its amount, it is usually appropriately selected within the range of equimolar to excess molar relative to the compound represented by the general formula (17) for the reaction.

[0642] Regarding the reaction temperature, it can be appropriately selected within the range of -50°C to the boiling point range of the inert solvent used, and preferably from room temperature to 80°C. Regarding the reaction time, although it is not fixed due to the reaction scale and reaction temperature, it is in the range of several minutes to 48 hours. After the reaction is completed, when the compound represented by the general formula (1-9) is stable, the target product can be separated from the reaction system containing the target product according to a conventional method, and can also be purified by recrystallization, column chromatography, etc. as needed to prepare the target product, or can be directly used in the subsequent reaction without separation. When the compound represented by the general formula (1-9) is unstable, it can be directly used in the subsequent reaction without purifying the reaction solution.

[0643] Preparation method of step [j]

[0644] The compound represented by the general formula (1-10) of the present invention can be prepared by reacting the compound represented by the general formula (1-9) with the compound represented by the general formula (18) in the presence or absence of an inert solvent and a base.

[0645] Examples of the base used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, and potassium bicarbonate; acetates such as sodium acetate and potassium acetate; alkali metal alcoholates such as potassium tert-butoxide, sodium methoxide, and sodium ethoxide; tertiary amines such as triethylamine, N,N-diisopropylethylamine, and 1,8-diazabicyclo[5.4.0]undec-7-ene; and nitrogen-containing aromatic compounds such as pyridine and N,N-dimethyl-4-aminopyridine. Regarding the amount used, it is usually used in the range of 1 to 10 times the molar amount relative to the compound represented by the general formula (1-9). In addition, when using the base salt of the compound represented by the general formula (18), the base may not be used.

[0646] Examples of the inert solvent used in this reaction include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; chain or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran; esters such as ethyl acetate; amides such as N,N-dimethylformamide and N,N-dimethylacetamide; ketones such as acetone and methyl ethyl ketone; and polar solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it is an amount that dissolves the reaction reagents, and it can be appropriately selected in the range of 0.5 L to 100 L relative to 1 mole of the compound represented by the general formula (1-9).

[0647] Since this reaction is an equimolar reaction, the compound represented by the general formula (1-9) and the compound represented by the general formula (18) can be used in equimolar amounts, and either compound can also be used in excess. Regarding the reaction temperature, it can be carried out in the range from -20 °C to the boiling point of the inert solvent used. Regarding the reaction time, although it is not fixed depending on the reaction scale and reaction temperature, it can be carried out in the range of several minutes to 48 hours.

[0648] After the reaction is completed, the target product can be separated from the reaction system containing the target product by a conventional method, and it can also be purified by recrystallization, column chromatography, etc. as needed to prepare the target product. In addition, it can also be used in the next process without separation.

[0649] Preparation method of step [k]

[0650] The compound represented by the general formula (1-11) of the present invention can be prepared by reacting the compound represented by the general formula (1-10) with the compound represented by the general formula (19) in the presence of an inert solvent and a base.

[0651] Examples of the base used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, and potassium bicarbonate; acetates such as sodium acetate and potassium acetate; alkali metal alkoxides such as potassium tert-butoxide, sodium methoxide, and sodium ethoxide; tertiary amines such as triethylamine, N,N-diisopropylethylamine, and 1,8-diazabicyclo[5.4.0]undec-7-ene; and nitrogen-containing aromatic compounds such as pyridine and N,N-dimethyl-4-aminopyridine. Regarding the amount used, it is usually used in the range of 1 to 10 times the molar amount relative to the compound represented by the general formula (1-10).

[0652] As the inert solvent used in this reaction, any solvent that does not significantly hinder the progress of this reaction can be used, such as aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; chain or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran; esters such as ethyl acetate; amides such as N,N-dimethylformamide and N,N-dimethylacetamide; ketones such as acetone and methyl ethyl ketone; and polar solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it can dissolve the reaction reagents, and it can be appropriately selected in the range of 0.5 L to 100 L relative to 1 mol of the compound represented by the general formula (1-10).

[0653] Since this reaction is an equimolar reaction, the compound represented by the general formula (1-10) and the compound represented by the general formula (19) can be used in equimolar amounts, and either compound can also be used in excess. Regarding the reaction temperature, it can be carried out in the range from -20 °C to the boiling point of the inert solvent used. Regarding the reaction time, although it is not fixed due to the reaction scale and reaction temperature, it can be carried out in the range of several minutes to 48 hours.

[0654] After the reaction is completed, the target product can be separated from the reaction system containing the target product by a conventional method, and it can also be purified by recrystallization, column chromatography, etc. as needed to prepare the target product.

[0655] Preparation method 6

[0656] [Chemical formula 10]

[0657]

[0658] In the formula, A1 、A 2 、A 3 、R 1 、R 2 、R 4 and m are the same as the said A 1 、A 2 、A 3 、R 1 、R 2 、R 4 and m, R represents (C1-C6) alkoxy, (C2-C6) alkynyloxy or R 7’ (R 8 (R 9 )N group (R 8 and R 9 are the same as the said R 8 and R 9 ), R represents (C1-C4) alkyl such as methyl, ethyl, etc.

[0659] The compounds represented by the general formula (1-13) and the compounds represented by the general formula (1-14) of the present invention can be prepared from the compounds represented by the general formula (20) through the following steps [l], [m], [n], [o] and [p] and the step [d] of the above preparation method 1. In addition, the compounds represented by the general formula (20) as starting materials can be prepared by the method described in the International Publication No. 2013 / 018928 handbook.

[0660] Preparation method of step [l]

[0661] By following the method described in Japanese Patent Laid-Open No. 2005-272338 (Heck reaction), the compounds represented by the general formula (21) in which ester groups are introduced at the 3- and 6-positions can be synthesized from the compounds represented by the general formula (20). After the reaction is completed, the target product can be separated from the reaction system containing the target product by a conventional method, or the target product can be purified by recrystallization, column chromatography, etc. as needed to prepare the target product. In addition, it can also be used in the next step without separation.

[0662] Preparation method of step [m]

[0663] By reducing the compounds represented by the general formula (21) in the presence of an inert solvent using a reducing agent, the compounds represented by the general formula (22) can be prepared.

[0664] Examples of the reducing agent that can be used in this reaction include sodium borohydride, sodium cyanoborohydride, sodium bis(2-methoxyethoxy)aluminum hydride, hydrogen / palladium-carbon, hydrogen / Raney nickel, etc. Regarding the amount of use, it is usually used in the range of 0.5 to 10 times the molar amount relative to the compounds represented by the general formula (21).

[0665] As an inert solvent that can be used in this reaction, any solvent that does not significantly hinder this reaction can be used. Examples include alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol; linear or cyclic ethers such as diethyl ether, tetrahydrofuran (THF), and dioxane; and acids such as acetic acid and propionic acid. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it can dissolve the reaction reagents, and it can be appropriately selected within the range of 0.5 L to 100 L relative to 1 mole of the compound represented by the general formula (21).

[0666] In this reaction, regarding the reaction temperature, it is usually carried out within the range of about 0 °C to the boiling point of the solvent used. Regarding the reaction time, although it varies depending on the reaction scale, reaction temperature, etc. and is not fixed, it is usually appropriately selected within the range of several minutes to 48 hours.

[0667] After the reaction is completed, the target product can be separated from the reaction system containing the target product by a conventional method, and it can also be purified by recrystallization, column chromatography, etc. as needed to prepare the target product. In addition, it can also be used in the next process without separation.

[0668] Preparation method of step [n]

[0669] By oxidizing the compound represented by the general formula (22) in the presence of an inert solvent using an oxidizing agent, the compound represented by the general formula (23) can be prepared.

[0670] Examples of the oxidizing agent that can be used in this reaction include manganese dioxide, chromic acid, ammonium cerium nitrate (CAN), silver carbonate, pyridine sulfate anhydride, activated DMSO (dimethyl sulfoxide), etc. It can be carried out according to the methods described in known literatures for converting ordinary alcohols into aldehydes or ketones (for example, refer to "New Experimental Chemistry Course", Volume 15 (I), p. 71 - 84, 120 - 123, 804 - 843, 923, 1004 - 1006, 1977, edited by the Chemical Society of Japan, MARUZEN GROUP and Chem. Pharm. Bull., 30(5), p1921 - 1924 (1982)).

[0671] As the inert solvent used in this reaction, any solvent that does not significantly hinder the progress of this reaction is acceptable. Examples include aromatic hydrocarbons such as benzene, toluene, and xylene, halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, chain or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran, esters such as ethyl acetate, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, ketones such as acetone and methyl ethyl ketone, polar solvents such as dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone, and water. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it is an amount sufficient to dissolve the reaction reagents, and it can be appropriately selected within the range of 0.5 L to 100 L relative to 1 mole of the compound represented by the general formula (22).

[0672] Preparation method of step [o]

[0673] The compound represented by the general formula (1-13) of the present invention can be prepared by subjecting the compound represented by the general formula (24) to hydrolysis in the presence of a base, water, and an inert solvent.

[0674] Examples of the base that can be used in this reaction include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide, and organic bases.

[0675] As the inert solvent that can be used in this reaction, any solvent that does not significantly hinder this reaction is acceptable. Examples include chain or cyclic saturated hydrocarbons such as pentane, hexane, and cyclohexane, chain or cyclic ethers such as diethyl ether, tetrahydrofuran (THF), and dioxane, and non-polar solvents such as aromatic hydrocarbons such as benzene, toluene, and xylene. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it is an amount sufficient to dissolve the reaction reagents, and it can be appropriately selected within the range of 0.5 L to 100 L relative to 1 mole of the compound represented by the general formula (24).

[0676] Regarding the reaction temperature, it is generally carried out within the range of about 0 °C to the boiling point of the solvent used. Regarding the reaction time, although it varies depending on the reaction scale, reaction temperature, etc. and is not fixed, it can be appropriately selected within the range of several minutes to 48 hours. After the reaction is completed, the target product can be separated from the reaction system containing the target product by a conventional method, and it can also be purified by recrystallization, column chromatography, etc. as needed to prepare the target product. In addition, it can also be used in the next step without separation.

[0677] Preparation method of step [p]

[0678] The compound represented by the general formula (1-13), the compound represented by the general formula (25) and a condensing agent are reacted in the presence of a base and an inert solvent to prepare the compound represented by the general formula (1-14) of the present invention.

[0679] Examples of the condensing agent that can be used in this condensation reaction include acid activators such as carbonyl chloride, phosphorus trichloride, phosphorus oxychloride, oxalyl chloride and thionyl chloride, carbodiimides such as N,N'-dicyclohexylcarbodiimide (DCC) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDCI). In addition, phosphorus pentoxide, polyphosphoric acid, N,N'-carbonyldiimidazole, 2-chloro-1-methylpyridinium iodide (Mukaiyama reagent), 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), triphenylphosphine / carbon tetrachloride, tripyrrolidinophosphonium bromide hexafluorophosphate (BROP), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP), N,N,N',N'-bis(tetramethylene)chlorourea tetrafluoroborate, O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethylurea hexafluorophosphate (HBTU), O-(1H-benzotriazol-1-yl)-N,N,N',N'-bis(tetramethylene)urea hexafluorophosphate, O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethylurea tetrafluoroborate (TBTU), O-(1H-benzotriazol-1-yl)-N,N,N',N'-bis(tetramethylene)urea tetrafluoroborate, O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethylurea hexafluorophosphate (HATU), 1-hydroxybenzotriazole (HOBt), propylphosphonic anhydride (T3P) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholine hydrochloride (DMT-MM). These reagents can be used alone or in combination of two or more. Regarding the amount of the condensing agent, it can be appropriately selected within the range of 0.5 to 5 times the molar amount relative to the compound represented by the general formula (1-13).

[0680] Examples of the base that can be used in this condensation reaction include carbonates such as lithium carbonate, lithium hydrogencarbonate, sodium carbonate, sodium hydrogencarbonate, potassium carbonate, potassium hydrogencarbonate, calcium carbonate and magnesium carbonate, acetates such as lithium acetate, sodium acetate and potassium acetate, and organic bases such as pyridine, methylpyridine, dimethylpyridine, triethylamine, tributylamine and N,N-diisopropylethylamine. Regarding the amount of the base, it can be appropriately selected within the range of 0.5 to 5 times the molar amount relative to the compound represented by the general formula (1-13), and this base can also be used as a solvent.

[0681] As an inert solvent that can be used in this condensation reaction, any solvent that does not significantly hinder this reaction is acceptable. Examples include linear or cyclic saturated hydrocarbons such as pentane, hexane, and cyclohexane; linear or cyclic ethers such as diethyl ether, tetrahydrofuran (THF), and dioxane; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; nitriles such as acetonitrile and isopropyl cyanide; and polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, and 1,3-dimethyl-2-imidazolidinone. These inert solvents can be used alone or in combination of two or more. In addition, when the base is used as a solvent, a solvent may not be used. The amount of the inert solvent is not particularly limited as long as it is an amount that dissolves the reaction reagents, and it can be appropriately selected within the range of 0.5 L to 100 L relative to 1 mole of the compound represented by the general formula (1-13).

[0682] Since this condensation reaction is an equimolar reaction, each compound can be used in an equimolar amount, and any one of the compounds can also be used in excess. Regarding the reaction temperature, it is generally sufficient to carry out the reaction within the range of about 0 °C to the boiling point of the solvent used. Regarding the reaction time, although it varies depending on the reaction scale, reaction temperature, etc. and is not fixed, it can be appropriately selected within the range of several minutes to 48 hours.

[0683] After the reaction is completed, the target product can be separated from the reaction system containing the target product by a conventional method, and the target product can also be prepared by purification through recrystallization, column chromatography, etc. as needed.

[0684] Preparation Method 7

[0685] [Chemical Formula 11]

[0686]

[0687] In the formula, A 1 , A 2 , A 3 , R 1 , R 2 , R 4 and m are the same as those of the aforementioned A 1 , A 2 , A 3 , R 1 , R 2 , R 4 and m. R 7’ represents (C1-C6) alkoxy, (C2-C6) alkynyloxy, or R 8 (R 9 )N group (R 8 and R 9 are the same as those of the aforementioned R 8 and R 9The same), R represents, for example, a (C1-C4) alkyl group such as a methyl group or an ethyl group.

[0688] The compound represented by the general formula (1-15) of the present invention can be prepared from the compound represented by the general formula (21) through the following processes [q] and [r], the process [d] of the above preparation method 1, and the processes [o] and [p] of the above preparation method 6.

[0689] Preparation method of process [q]

[0690] By subjecting the aromatic ring carboxylic acid ester represented by the general formula (21) and the acetate represented by the general formula (26) to a Claisen condensation reaction (Org. React. 1942, 1, 266), the compound represented by the general formula (27) can be prepared.

[0691] Preparation method of process [r]

[0692] By subjecting the compound represented by the general formula (27) to decarboxylation in the presence of an acid and an inert solvent, the compound represented by the general formula (28) can be prepared.

[0693] Examples of the acid used in this reaction include inorganic acids such as hydrochloric acid, sulfuric acid, and nitric acid, organic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, and benzoic acid, sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, and p-toluenesulfonic acid, and phosphoric acid. Regarding the amount thereof, it can be appropriately selected within the range of 0.01 to 10 times the molar amount relative to the compound represented by the general formula (27), and this acid can also be used as a solvent.

[0694] The inert solvent used in this reaction is a solvent that does not significantly hinder the progress of this reaction. Examples thereof include chain or cyclic saturated hydrocarbons such as pentane, hexane, and cyclohexane, aromatic hydrocarbons such as benzene, toluene, and xylene, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, chain or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, and 1,3-dimethyl-2-imidazolidinone, alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol, and water. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it is an amount that dissolves the reaction reagents, and it can be appropriately selected within the range of 0.5 L to 100 L relative to 1 mole of the compound represented by the general formula (27).

[0695] In this reaction, regarding the reaction temperature, it is usually carried out within the range of about 0 °C to the boiling point of the solvent used. Regarding the reaction time, although it varies depending on the reaction scale, reaction temperature, etc. and is not fixed, it is usually appropriately selected within the range of several minutes to 48 hours.

[0696] After the reaction is completed, the target product can be separated from the reaction system containing the target product by conventional methods, or the target product can be prepared by purification through recrystallization, column chromatography, etc. as needed.

[0697] Preparation method 8

[0698] [Chemical formula 12]

[0699]

[0700] In the formula, A 1 , A 2 , A 3 , R 1 , R 2 , R 4 , R 8 , R 9 and m are the same as the aforementioned A 1 , A 2 , A 3 , R 1 , R 2 , R 4 , R 8 , R 9 and m, R 7’ represents (C1-C6) alkoxy, (C2-C6) alkynyloxy or R 8 (R 9 )N group (R 8 and R 9 are the same as the aforementioned R 8 and R 9 ), R represents (C1-C4) alkyl such as methyl, ethyl, etc., and L represents a leaving group such as bromine or chlorine.

[0701] The compound represented by the general formula (1-16) of the present invention can be prepared from the compound represented by the general formula (21) through the following processes [s] and [t], the process [f] of the above preparation method 3, the processes [d'] and [k] of the above preparation method 5, and the processes [o] and [p] of the above preparation method 6.

[0702] Preparation method of process [s]

[0703] By reacting the compound represented by the general formula (21) with ammonia in the presence or absence of an inert solvent and a base, the compound represented by the general formula (30) can be prepared.

[0704] As the base used in this reaction, inorganic bases or organic bases can be cited. As inorganic bases, for example, hydroxides of alkali metal atoms such as sodium hydroxide and potassium hydroxide, hydrides of alkali metals such as sodium hydride and potassium hydride, alkali metal salts of alcohols such as sodium ethoxide and potassium tert-butoxide, carbonates such as sodium carbonate, potassium carbonate, and sodium bicarbonate can be cited. As organic bases, for example, triethylamine, pyridine, DBU, etc. can be cited. Regarding the amount used, it can be appropriately selected within the range of 0.01 to 10 times the molar amount relative to the compound represented by the general formula (21).

[0705] As the inert solvent used in this reaction, a solvent that does not significantly hinder the progress of this reaction is sufficient. Aromatic hydrocarbons such as benzene, toluene, and xylene, halogenated aliphatic hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, chain or cyclic ethers such as diethyl ether, dioxane, and tetrahydrofuran, esters such as ethyl acetate, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone, and inert solvents such as acetone, methyl ethyl ketone, or water can be cited. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it is an amount that dissolves the reaction reagents, and it can be appropriately selected within the range of 0.5 L to 100 L relative to 1 mole of the compound represented by the general formula (21).

[0706] In this reaction, regarding the reaction temperature, it is usually carried out within the range of about 0 °C to the boiling point of the solvent used. Regarding the reaction time, although it varies depending on the reaction scale, reaction temperature, etc. and is not fixed, it is usually appropriately selected within the range of several minutes to 48 hours.

[0707] After the reaction is completed, the target product can be separated from the reaction system containing the target product by a conventional method, and it can also be purified by recrystallization, column chromatography, etc. as needed to prepare the target product. In addition, it can also be used in the next step without purification.

[0708] Preparation method of step [t]

[0709] By reacting the compound represented by the general formula (30) with a dehydrating agent in the presence or absence of an inert solvent and a base, the compound represented by the general formula (31) can be prepared.

[0710] As the dehydrating agent used in this reaction, trifluoroacetic anhydride, phosphorus oxychloride, phosphorus pentoxide, etc. can be cited. Regarding the amount used, it can be appropriately selected within the range of 1 to 10 times the molar amount relative to the compound represented by the general formula (30).

[0711] As the base used in this reaction, inorganic bases or organic bases can be cited. As inorganic bases, for example, hydroxides of alkali metal atoms such as sodium hydroxide and potassium hydroxide, hydrides of alkali metals such as sodium hydride and potassium hydride, alkali metal salts of alcohols such as sodium ethoxide and potassium tert-butoxide, and carbonates such as sodium carbonate, potassium carbonate, and sodium bicarbonate can be cited. As organic bases, for example, triethylamine, pyridine, DBU, etc. can be cited. Regarding the amount thereof, it can be appropriately selected within the range of 0.01-fold mole to 10-fold moles relative to the compound represented by the general formula (30).

[0712] As the inert solvent used in this reaction, a solvent that does not significantly hinder the progress of this reaction is sufficient. Aromatic hydrocarbons such as benzene, toluene, and xylene, halogenated aliphatic hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, chain or cyclic ethers such as diethyl ether, dioxane, and tetrahydrofuran, esters such as ethyl acetate, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, and inert solvents such as dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone, and acetone and methyl ethyl ketone can be cited. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent is not particularly limited as long as it is an amount that dissolves the reaction reagents, and it can be appropriately selected within the range of 0.5 L to 100 L relative to 1 mole of the compound represented by the general formula (30).

[0713] In this reaction, regarding the reaction temperature, it can generally be carried out within the range of about 0 °C to the boiling point of the solvent used. Regarding the reaction time, although it varies depending on the reaction scale, reaction temperature, etc. and is not fixed, it can generally be appropriately selected within the range of several minutes to 48 hours.

[0714] After the reaction is completed, the target product can be separated from the reaction system containing the target product by a conventional method, and the target product can also be prepared by purification through recrystallization, column chromatography, etc. as needed.

[0715] Preparation method 9

[0716] [Chemical formula 13]

[0717]

[0718] In the formula, A 1 , A 2 , A 3 , R 1 , R 2 , R 4 and m are the same as the above A 1 , A 2 , A 3 , R 1 , R 2 , R 4 and m, and R3’ represents a (C1-C6) alkoxy group or R 8 (R 9 )N group (R 8 and R 9 being the same as the aforementioned R 8 and R 9 being the same), R 7’ represents a (C1-C6) alkoxy group, a (C2-C6) alkynyloxy group or R 8 (R 9 )N group (R 8 and R 9 being the same as the aforementioned R 8 and R 9 being the same), R represents a (C1-C4) alkyl group such as a methyl group or an ethyl group, X represents a halogen atom such as fluorine, chlorine, bromine, iodine, etc., and L represents a leaving group such as bromine or chlorine.

[0719] The compound represented by the general formula (1-17) of the present invention can be prepared from the compound represented by the general formula (23) through the steps [d'], [i], [j] and [k] of the above preparation method 5 and the steps [o] and [p] of the above preparation method 6.

[0720] Preparation method 10

[0721] [Chemical formula 14]

[0722]

[0723] In the formula, A 1 , A 2 , R 1 , R 2 , R 4 , R 6 and m are the same as the aforementioned A 1 , A 2 , R 1 , R 2 , R 4 , R 6 and m, p' represents 1 or 2, R represents a (C1-C4) alkyl group such as a methyl group or an ethyl group, Ak represents a (C1-C6) alkyl group, and X represents a halogen atom such as fluorine, chlorine, bromine, iodine, etc.

[0724] The compound represented by the general formula (1-18) of the present invention, the compound represented by the general formula (1-19) and the compound represented by the general formula (1-20) can be prepared from the compound represented by the general formula (20) through the following steps [u], [v], [w] and [x], the steps [b], [d] and [e] of the above preparation method 1, the step [l] of the above preparation method 6 and the steps [s] and [t] of the above preparation method 8.

[0725] Preparation method of process [u]

[0726] By reacting the compound represented by the general formula (40) with sodium azide in an inert solvent and reducing it using a reducing agent, the compound represented by the general formula (41) can be prepared.

[0727] As the inert solvent used in this reaction, a solvent that does not significantly hinder the progress of this reaction is sufficient. Examples include aromatic hydrocarbons such as benzene, toluene, and xylene, halogenated aliphatic hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride, alcohols such as methanol and ethanol, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, chain or cyclic ethers such as diethyl ether, dioxane, and tetrahydrofuran, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone, N-methyl-2-pyrrolidone, water, and other inert solvents. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it is an amount that dissolves the reaction reagents, and it can be appropriately selected within the range of 0.5 L to 100 L relative to 1 mole of the compound represented by the general formula (40).

[0728] As the reducing agent used in this reaction, examples include triphenylphosphine, sodium borohydride, hydrogen / palladium-carbon, hydrogen / Raney nickel, etc. Regarding its amount, it is usually used within the range of 0.5-fold molar to 10-fold molar relative to the compound represented by the general formula (40).

[0729] In this reaction, regarding the reaction temperature, it is usually carried out within the range of about 0 °C to the boiling point of the solvent used. Regarding the reaction time, although it varies depending on the reaction scale, reaction temperature, etc. and is not fixed, it can usually be appropriately selected within the range of several minutes to 48 hours.

[0730] After the reaction is completed, the target product can be separated from the reaction system containing the target product by a conventional method, and the target product can be prepared by purification through recrystallization, column chromatography, etc. as needed.

[0731] Process [v]

[0732] By halogenating the compound represented by the general formula (41) in the presence of an inert solvent using a halogenating agent, the compound represented by the general formula (42) can be prepared.

[0733] As an inert solvent that can be used in this reaction, any solvent that does not significantly hinder this reaction is acceptable. Examples include alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol; chain or cyclic ethers such as diethyl ether, tetrahydrofuran, and dioxane; aromatic hydrocarbons such as benzene, toluene, and xylene; esters such as ethyl acetate; polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, 1,3-dimethyl-2-imidazolidinone, water, and acetic acid. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent is not particularly limited as long as it can dissolve the reaction reagents, and it can be appropriately selected within the range of 0.5 L to 100 L relative to 1 mole of the compound represented by the general formula (41).

[0734] As the halogenating agent, examples include halogen molecules of chlorine, bromine, and iodine; halogenated succinimides such as NCS and NBS; halogenated hydantoins such as DIH; and sulfonyl chloride. Regarding the amount of the halogenating agent, it can be appropriately selected within the range of 0.5-fold mole to 10-fold mole relative to the compound represented by the general formula (41).

[0735] In this reaction, regarding the reaction temperature, it can be appropriately selected within the range from -30°C to the reflux temperature of the inert solvent used. Regarding the reaction time, although it varies depending on the reaction scale, reaction temperature, etc. and is not fixed, it can be appropriately selected within the range of several minutes to 48 hours.

[0736] After the reaction is completed, the target product can be separated from the reaction system containing the target product by conventional methods, and it can also be purified by recrystallization, column chromatography, etc. as needed to prepare the target product. In addition, it can also be supplied to the next process without separation.

[0737] Preparation method of step [w]

[0738] By reacting the compound represented by the general formula (42) with the compound represented by the general formula (43) in the presence of a metal catalyst, a base, and an inert solvent, the compound represented by the general formula (44) can be prepared.

[0739] As the metal catalyst that can be used in this reaction, examples include palladium catalysts, nickel catalysts, iron catalysts, ruthenium catalysts, platinum catalysts, rhodium catalysts, iridium catalysts, etc. These metal catalysts can be used in the form of "metal", "supported metal", "metal salts such as metal chlorides, bromides, iodides, nitrates, sulfates, carbonates, oxalates, acetates, or oxides", "complexes such as olefin complexes, phosphine complexes, amine complexes, ammonia complexes, or acetylacetonate complexes". Preferably, it is a palladium catalyst.

[0740] As the palladium catalyst, palladium metals such as palladium black and spongy palladium can be cited. In addition, supported palladium metals such as palladium / aluminum oxide, palladium / carbon, palladium / silicon dioxide, and palladium / Y-type zeolite can be cited. Further, metal salts such as palladium chloride, palladium bromide, palladium iodide, and palladium acetate can be cited. Furthermore, complexes such as π-allylpalladium chloride dimer, palladium acetylacetonate, bis(acetonitrile)dichloropalladium, bis(benzonitrile)dichloropalladium, bis(dibenzylideneacetone)palladium, tris(dibenzylideneacetone)dipalladium, tris(dibenzylideneacetone)dipalladium (chloroform adduct), dichlorodiaminepalladium, bis(triphenylphosphine)dichloropalladium, bis(tricyclohexylphosphine)dichloropalladium, tetrakis(triphenylphosphine)palladium, dichloro[1,2-bis(diphenylphosphino)ethane]palladium, dichloro[1,3-bis(diphenylphosphino)propane]palladium, dichloro[1,4-bis(diphenylphosphino)butane]palladium, dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium, and diphenylphosphinoferrocene dichloropalladium-dichloromethane complex can be cited. Regarding the amount of these metal catalysts used, it can be appropriately selected within the range of 0.001 to 0.5 times the molar amount relative to the compound represented by the general formula (42).

[0741] These palladium catalysts can be used alone or further in combination with a tertiary phosphine. As the tertiary phosphine that can be used, triphenylphosphine, trimethylphosphine, triethylphosphine, tributylphosphine, tris(tert-butyl)phosphine, tricyclohexylphosphine, tri-o-tolylphosphine, trioctylphosphine, 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene, 2-(di-tert-butylphosphino)biphenyl, 2-(dicyclohexylphosphino)biphenyl, 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino)propane, 1,4-bis(diphenylphosphino)butane, 1,1'-bis(diphenylphosphino)ferrocene, (R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthalene, (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthalene, and (±)-2,2'-bis(diphenylphosphino)-1,1'-binaphthalene can be cited. Regarding the amount of these tertiary phosphines used, it can be appropriately selected within the range of 0.5 to 10 times the molar amount relative to the metal catalyst.

[0742] As the base that can be used in this reaction, inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium bicarbonate, and potassium bicarbonate, alkali metal hydrides such as sodium hydride and potassium hydride, and alcoholates such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide can be cited. Regarding the amount of the base used, it can usually be used within the range of about 1 to 5 times the molar amount relative to the compound represented by the general formula (42).

[0743] As an inert solvent that can be used in this reaction, any solvent that does not significantly hinder this reaction is acceptable. Examples include alcohols such as methanol, ethanol, propanol, butanol, 2-propanol, etc., linear or cyclic ethers such as diethyl ether, tetrahydrofuran, dioxane, 1,2-dimethoxyethane (DME), etc., aromatic hydrocarbons such as benzene, toluene, xylene, etc., halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, etc., halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, etc., nitriles such as acetonitrile, esters such as ethyl acetate, polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone, and water. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent is not particularly limited as long as it is an amount that can dissolve the reaction reagents, and it can be appropriately selected within the range of 0.5 L to 100 L relative to 1 mole of the compound represented by the general formula (42).

[0744] Since this reaction is an equimolar reaction, each compound can be used in equimolar amounts, and any one of the compounds can also be used in excess.

[0745] In this reaction, regarding the reaction temperature, it is usually carried out within the range of about 0 °C to the boiling point of the solvent used. Regarding the reaction time, although it is not fixed due to the reaction scale, reaction temperature, etc., it can be appropriately selected within the range of several minutes to 48 hours. In addition, this reaction can also be carried out, for example, in an atmosphere of an inert gas such as nitrogen or argon.

[0746] After the reaction is completed, the target product can be separated from the reaction system containing the target product by conventional methods, and it can also be purified by recrystallization, column chromatography, etc. as needed to prepare the target product. In addition, it can also be supplied to the next process without separation.

[0747] Preparation method of step [x]

[0748] By converting the amino group of the compound represented by the general formula (44) into a halogen atom according to the Sandmeyer reaction, i.e., the method described in Chem. Rev. 1988, 88, 765, the compound represented by the general formula (45) can be prepared.

[0749] After the reaction is completed, the target product can be separated from the reaction system containing the target product by conventional methods, and it can also be purified by recrystallization, column chromatography, etc. as needed to prepare the target product.

[0750] Preparation method 11

[0751] [Chemical formula 15]

[0752]

[0753] In the formula, A 1, A 3 , R 1 , R 2 , R 4 and m are the same as the said A 1 , A 3 , R 1 , R 2 , R 4 and m, where R 7’ represents (C1-C6) alkoxy, (C2-C6) alkynyloxy or R 8 (R 9 )N group (R 8 and R 9 are the same as the said R 8 and R 9 ), R represents (C1-C4) alkyl such as methyl, ethyl, etc., Ak represents (C1-C6) alkyl, and X represents halogen atoms such as fluorine, chlorine, bromine, iodine, etc.

[0754] The compounds represented by the general formula (1-21) of the present invention and the compounds represented by the general formula (1-22) are prepared from the compounds represented by the general formula (21) through the following processes [y] and [z], the process [d] of the above preparation method 1, the processes [o] and [p] of the above preparation method 6, and the processes [v], [w] and [x] of the above preparation method 10.

[0755] Preparation method of process [y]

[0756] By reacting the compound represented by the general formula (47) in the presence of diphenylphosphoric acid amide and tert-butanol according to the method described in J.A.Chem.Soc.1972, 94, 6203-6205, and then reacting in the presence of an acid and an inert solvent, the compound represented by the general formula (48) can be prepared.

[0757] Examples of the acid that can be used in this reaction include inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, organic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, benzoic acid, sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, etc. Regarding its dosage, it is usually appropriately selected within the range of 1 to 10 times the molar amount relative to the compound represented by the general formula (47), and it can also be used as a solvent.

[0758] As an inert solvent that can be used in this reaction, any solvent that does not significantly hinder the progress of this reaction is acceptable. Examples include aromatic hydrocarbons such as benzene, toluene, and xylene, halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, linear or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran, esters such as ethyl acetate, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, ketones such as acetone and methyl ethyl ketone, and polar solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it is an amount that can dissolve the reaction reagents, and it can be appropriately selected within the range of 0.5 L to 100 L relative to 1 mole of the compound represented by the general formula (47).

[0759] In this reaction, regarding the reaction temperature, it can generally be carried out in the range from -10 °C to the boiling point of the inert solvent used. Regarding the reaction time, although it is not fixed due to the reaction scale and reaction temperature, it can generally be carried out within the range of several minutes to 48 hours.

[0760] After the reaction is completed, the target product can be separated from the reaction system containing the target product by conventional methods, and it can also be purified by recrystallization, column chromatography, etc. as needed to prepare the target product. In addition, it can also be supplied to the next process without separation.

[0761] Preparation method of step [z]

[0762] By reacting the compound represented by the general formula (51) with tributyl(1-ethoxyvinyl)tin in the presence of a palladium catalyst and an inert solvent, and then performing an acid treatment, the compound represented by the general formula (52) can be prepared.

[0763] Examples of the palladium catalyst that can be used in this reaction include bis(triphenylphosphine)palladium(II) chloride, palladium(II) acetate, palladium(II) chloride, tetrakis(triphenylphosphine)palladium(0), and bis(tri-tert-butylphosphine)palladium(0). Regarding the amount of the palladium catalyst used, it can be appropriately selected within the range of 0.001-fold mole to 0.5-fold mole relative to the compound represented by the general formula (51).

[0764] As the inert solvent used in this reaction, any solvent that does not significantly hinder the progress of this reaction is acceptable. Examples include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; linear or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran; esters such as ethyl acetate; amides such as N,N-dimethylformamide and N,N-dimethylacetamide; ketones such as acetone and methyl ethyl ketone; alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol; and polar solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it can dissolve the reaction reagents, and it can be appropriately selected within the range of 0.5 L to 100 L relative to 1 mole of the compound represented by the general formula (51).

[0765] Examples of the acid that can be used in this reaction include inorganic acids such as hydrochloric acid, sulfuric acid, and nitric acid; organic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, and benzoic acid; and sulfonic acids such as methanesulfonic acid and trifluoromethanesulfonic acid. Regarding the amount thereof, it can generally be appropriately selected within the range of 1-fold mole to 10-fold moles relative to the compound represented by the general formula (51).

[0766] In this reaction, regarding the reaction temperature, it can generally be carried out within the range of 0 °C to the boiling point of the inert solvent used. Regarding the reaction time, although it is not fixed due to the reaction scale and reaction temperature, it can generally be carried out within the range of several minutes to 48 hours.

[0767] After the reaction is completed, the target product can be separated from the reaction system containing the target product by a conventional method, and it can also be purified by recrystallization, column chromatography, etc. as needed to prepare the target product. In addition, it can also be supplied to the next process without separation.

[0768] Preparation Method 12

[0769] [Chemical Formula 16]

[0770]

[0771] In the formula, A 1 、A 2 、A 3 、R 1 、R 2 、R 3 、R 4 、R 6 、R 8 and m are the same as those of the A 1 、A 2 、A 3 、R 1 、R 2, R 3 , R 4 , R 6 , R 8 and m are the same, and L represents a leaving group such as bromine or chlorine, for example.

[0772] The compounds represented by the general formula (1-23) and the compounds represented by the general formula (1-24) of the present invention can be prepared from the compounds represented by the general formula (1-11) through the following step [aa] and step [f] of the above preparation method 3.

[0773] Preparation method of step [aa]

[0774] By reacting the compound represented by the general formula (1-11) with a nitrogen source in the presence of an inert solvent and a hypervalent iodine reagent, the compound represented by the general formula (1-23) of the present invention can be prepared.

[0775] Examples of the nitrogen source that can be used in this reaction include ammonia, ammonium carbamate, ammonium carbonate, etc. Regarding the amount thereof, it is usually appropriately selected within the range of 1 to 10 times the molar amount of the compound represented by the general formula (1-11).

[0776] Examples of the hypervalent iodine reagent that can be used in this reaction include iodobenzenediacetic acid, etc. Regarding the amount thereof, it is usually appropriately selected within the range of 1 to 10 times the molar amount of the compound represented by the general formula (1-11).

[0777] Examples of the inert solvent that can be used in this reaction include aromatic hydrocarbons such as benzene, toluene, and xylene, halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, linear or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran, esters such as ethyl acetate, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, ketones such as acetone and methyl ethyl ketone, alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol, acetonitrile, dimethyl sulfoxide,

[0778] polar solvents such as 1,3-dimethyl-2-imidazolidinone, etc. These polar solvents can be used alone or in combination of two or more. The amount of the inert solvent is not particularly limited as long as it is an amount that can dissolve the reaction reagents, and it can be appropriately selected within the range of 0.5 L to 100 L relative to 1 mole of the compound represented by the general formula (1-11).

[0779] In this reaction, regarding the reaction temperature, it can generally be carried out in the range from 0 °C to the boiling point of the inert solvent used. Regarding the reaction time, although it is not fixed due to the reaction scale and reaction temperature, it can generally be carried out within the range of several minutes to 48 hours.

[0780] After the reaction is completed, the target product can be separated from the reaction system containing the target product by conventional methods, or the target product can be prepared by purification through recrystallization, column chromatography, etc. as needed.

[0781] Preparation Method 13

[0782] [Chemical Formula 17]

[0783]

[0784] In the formula, A 1 , A 2 , A 3 , R 1 , R 2 , R 4 , R 8 , R 9 and m are the same as those of the said A 1 , A 2 , A 3 , R 1 , R 2 , R 4 , R 8 , R 9 and m. R” represents, for example, a tertiary (C4-C6) alkyl group such as a tert-butyl group or a tris(C1-C3)alkylsilyl group such as a trimethylsilyl group, X represents, for example, a halogen atom such as fluorine, chlorine, bromine, iodine, etc., and L represents, for example, a leaving group such as bromine or chlorine.

[0785] The compound represented by the general formula (1-7) of the present invention can be prepared from the compound represented by the general formula (62) through the following process [ae], the process [a] of the above Preparation Method 1, the processes [g] and [h] of the above Preparation Method 4, and the processes [d’] and [k] of the above Preparation Method 5.

[0786] Preparation method of process [ae]

[0787] This process is: a process of preparing the compound represented by the general formula (65) by reacting the compound represented by the general formula (64) with a cyaniding agent in the presence or absence of a metal catalyst and in the presence of a base and an inert solvent.

[0788] Examples of the cyaniding agent that can be used in this reaction include sodium cyanide, potassium cyanide, trimethylsilyl cyanide, zinc cyanide, etc. Regarding the amount thereof, it can usually be used in the range of about 1 to 10 times the molar amount relative to the compound represented by the general formula (64).

[0789] Examples of the base that can be used in this reaction include carbonates such as lithium carbonate, lithium hydrogencarbonate, sodium carbonate, sodium hydrogencarbonate, potassium carbonate, potassium hydrogencarbonate, calcium carbonate, and magnesium carbonate; acetates such as lithium acetate, sodium acetate, and potassium acetate; and organic bases such as pyridine, methylpyridine, dimethylpyridine, triethylamine, tributylamine, N,N - diisopropylethylamine, and 1,4 - diazabicyclo[2.2.2]octane. Regarding the amount used, it can generally be used in the range of about 1 to 5 times the molar amount relative to the compound represented by the general formula (64).

[0790] Examples of the metal catalyst that can be used in this reaction include palladium catalysts, nickel catalysts, iron catalysts, ruthenium catalysts, platinum catalysts, rhodium catalysts, iridium catalysts, etc. These metal catalysts can be "metal", "supported metal", "metal salts such as metal chlorides, bromides, iodides, nitrates, sulfates, carbonates, oxalates, acetates, or oxides", "complexes such as olefin complexes, phosphine complexes, amine complexes, ammonia complexes, or acetylacetonate complexes". A palladium catalyst is preferred.

[0791] Examples of the palladium catalyst include palladium metals such as palladium black and spongy palladium. In addition, supported palladium metals such as palladium / aluminum oxide, palladium / carbon, palladium / silica, and palladium / Y - type zeolite can also be cited. In addition, metal salts such as palladium chloride, palladium bromide, palladium iodide, and palladium acetate can be cited. Further, complexes such as π - allyl palladium chloride dimer, palladium acetylacetonate, bis(acetonitrile)dichloropalladium, bis(benzonitrile)dichloropalladium, bis(dibenzylideneacetone)palladium, tris(dibenzylideneacetone)dipalladium, tris(dibenzylideneacetone)dipalladium (chloroform adduct), dichlorodiamine palladium, bis(triphenylphosphine)dichloropalladium, bis(tricyclohexylphosphine)dichloropalladium, tetrakis(triphenylphosphine)palladium, dichloro[1,2 - bis(diphenylphosphino)ethane]palladium, dichloro[1,3 - bis(diphenylphosphino)propane]palladium, dichloro[1,4 - bis(diphenylphosphino)butane]palladium, dichloro[1,1’ - bis(diphenylphosphino)ferrocene]palladium, and diphenylphosphinoferrocene dichloropalladium - dichloromethane complex can be cited. Regarding the amount of these metal catalysts used, it can be appropriately selected within the range of 0.001 to 0.5 times the molar amount relative to the compound represented by the general formula (64).

[0792] These palladium catalysts can be used alone or further in combination with a tertiary phosphine. Examples of the tertiary phosphine that can be used include triphenylphosphine, trimethylphosphine, triethylphosphine, tributylphosphine, tris(tert-butyl)phosphine, tricyclohexylphosphine, tri-o-tolylphosphine, trioctylphosphine, 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene, 2-(di-tert-butylphosphino)biphenyl, 2-(dicyclohexylphosphino)biphenyl, 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino)propane, 1,4-bis(diphenylphosphino)butane, 1,1'-bis(diphenylphosphino)ferrocene, (R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthalene, (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthalene, (±)-2,2'-bis(diphenylphosphino)-1,1'-binaphthalene, etc. Regarding the amount of these tertiary phosphines, it can be appropriately selected within the range of 0.5 to 10 times the molar amount relative to the metal catalyst.

[0793] As the inert solvent that can be used in this reaction, any solvent that does not significantly hinder this reaction can be used. Examples include alcohols such as methanol, ethanol, propanol, butanol, 2-propanol, etc., linear or cyclic saturated hydrocarbons such as pentane, hexane, cyclohexane, etc., aromatic hydrocarbons such as benzene, toluene, xylene, etc., halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, etc., halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, etc., linear or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, tetrahydrofuran, cyclopentyl methyl ether, etc., esters such as ethyl acetate, etc., nitriles such as acetonitrile, propionitrile, etc., amides such as N,N-dimethylformamide, N,N-dimethylacetamide, etc., ketones such as acetone, methyl ethyl ketone, etc., polar solvents such as dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone, etc., water, etc. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent is not particularly limited as long as it can dissolve the reaction reagents, and it can be appropriately selected within the range of 0.5 L to 100 L relative to 1 mol of the compound represented by the general formula (64).

[0794] In this reaction, regarding the reaction temperature, it is usually carried out within the range of about 0 °C to the boiling point of the solvent used. Regarding the reaction time, although it varies depending on the reaction scale, reaction temperature, etc. and is not fixed, it can be appropriately selected within the range of several minutes to 48 hours.

[0795] After the reaction is completed, the target product can be separated from the reaction system containing the target product by a conventional method, and it can also be purified by recrystallization, column chromatography, etc. as needed to prepare the target product. In addition, it can also be used in the next reaction without separation.

[0796] Preparation Method 14

[0797] [Chemical Formula 18]

[0798]

[0799] Wherein, A 1 、A 2 、A 3 、R 1 、R 2 、R 4 and m are the same as the aforementioned A 1 、A 2 、A 3 、R 1 、R 2 、R 4 and m, Y represents a carbon atom, an oxygen atom, a sulfur atom or a nitrogen atom optionally substituted by an alkyl group such as a methyl group, an ethyl group (C1-C4), and q represents 1 or 2.

[0800] The compound represented by the general formula (1-25) of the present invention can be prepared from the compound represented by the general formula (2-4) through the following process [af] and the process [a] of the aforementioned preparation method 1. In addition, the preparation method of the compound represented by the general formula (2-4) as the starting material is described later.

[0801] Preparation method of process [af]

[0802] By hydrolyzing the compound represented by the general formula (2-4) in the presence of an acid and an inert solvent, the compound represented by the general formula (67) can be prepared.

[0803] Examples of the acid used in this reaction include inorganic acids such as hydrochloric acid, sulfuric acid, and nitric acid, organic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, and benzoic acid, sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, and p-toluenesulfonic acid, and phosphoric acid. Regarding its dosage, it can be appropriately selected within the range of 0.01 times to 10 times the molar amount relative to the compound represented by the general formula (2-4), and this acid can also be used as a solvent.

[0804] As an inert solvent that can be used in this reaction, a solvent that does not significantly hinder the progress of this reaction is sufficient. For example, aromatic hydrocarbons such as benzene, toluene, and xylene, halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, linear or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran, esters such as ethyl acetate, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, ketones such as acetone and methyl ethyl ketone, polar solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone, etc. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent is not particularly limited as long as it is an amount that can dissolve the reaction reagents, and it can be appropriately selected within the range of 0.5 L to 100 L relative to 1 mole of the compound represented by the general formula (2-4). In addition, when the acid is used as the solvent, the solvent may not be used.

[0805] Regarding the reaction temperature, it can be carried out in the range from room temperature to the boiling point of the inert solvent used. Regarding the reaction time, although it is not fixed due to the reaction scale and reaction temperature, it can be appropriately selected within the range of several minutes to 48 hours.

[0806] After the reaction is completed, the target product can be separated from the reaction system containing the target product by a conventional method, and it can also be purified by recrystallization, column chromatography, etc. as needed to prepare the target product. In addition, it can also be supplied to the next process without separation.

[0807] Preparation Method 15

[0808] [Chemical Formula 19]

[0809]

[0810] In the formula, A 1 、A 2 、A 3 、R 1 、R 2 、R 4 、R 8 、R 9 and m are the same as those of the aforementioned A 1 、A 2 、A 3 、R 1 、R 2 、R 4 、R 8 、R 9 and m, and R” represents, for example, a tertiary (C4-C6) alkyl such as a tert-butyl group or a tris(C1-C3)alkylsilyl such as a trimethylsilyl group.

[0811] The compound represented by the general formula (1-7) of the present invention can be prepared from the compound represented by the general formula (2-5) through step [a] of the above Preparation Method 1 and step [h] of the above Preparation Method 4. In addition, the preparation method of the compound represented by the general formula (2-5) as the starting material is described later.

[0812] Preparation Method 16

[0813] [Chemical formula 20]

[0814]

[0815] In the formula, A 1 、A 2 、A 3 、R 1 、R 2 、R 4 、R 8 、R 9 and m are the same as those of the aforementioned A 1 、A 2 、A 3 、R 1 、R 2 、R 4 、R 8 、R 9 and m. R” represents a tertiary (C4-C6) alkyl such as tert-butyl or a tris(C1-C3)alkylsilyl such as trimethylsilyl, X represents a halogen atom such as fluorine, chlorine, bromine, iodine, etc., and L represents a leaving group such as bromine or chlorine.

[0816] The compound represented by the general formula (1-7) of the present invention can be prepared from the compound represented by the general formula (2-6) through step [a] of the above Preparation Method 1, step [h] of the above Preparation Method 4, step [d'] and [k] of the above Preparation Method 5, and step [ae] of the above Preparation Method 4. In addition, the preparation method of the compound represented by the general formula (2-6) as the starting material is described later.

[0817] Preparation method of the compound represented by the general formula (2-1)

[0818] [Chemical formula 21]

[0819]

[0820] In the formula, A 1 、A 2 and A 3 are the same as those of the aforementioned A 1 、A 2 and A 3are the same; R and R’ represent, for example, (C1-C4) alkyl groups such as methyl and ethyl groups, and X represents, for example, halogen atoms such as fluorine, chlorine, bromine, and iodine atoms.

[0821] The compound represented by the general formula (2-1), which is the starting material for Preparation Method 1, can be prepared from the compound represented by the general formula (53) through the following steps [ab], [ac], and [ad], Step [e] of Preparation Method 1, and Step [o] of Preparation Method 6.

[0822] Preparation method of Step [ab]

[0823] By reacting the compound represented by the general formula (54) with a vinyl metal compound in the presence of an inert solvent, a metal catalyst, and a base, the compound represented by the general formula (55) can be prepared.

[0824] Examples of the metal catalyst that can be used in this reaction include palladium catalysts, nickel catalysts, iron catalysts, ruthenium catalysts, platinum catalysts, rhodium catalysts, iridium catalysts, etc. These metal catalysts can be used as "metal", "supported metal", "metal salts such as metal chlorides, bromides, iodides, nitrates, sulfates, carbonates, oxalates, acetates, or oxides", "complexes such as olefin complexes, phosphine complexes, amine complexes, ammonia complexes, or acetylacetonate complexes". A palladium catalyst is preferred.

[0825] Examples of the palladium catalyst include palladium metals such as palladium black and spongy palladium. In addition, supported palladium metals such as palladium / aluminum oxide, palladium / carbon, palladium / silica, and palladium / Y-type zeolite can also be cited. In addition, metal salts such as palladium chloride, palladium bromide, palladium iodide, and palladium acetate can also be cited. Further, examples include π-allyl palladium chloride dimer, palladium acetylacetonate, bis(acetonitrile) dichloropalladium, bis(benzonitrile) dichloropalladium, bis(dibenzylideneacetone) palladium, tris(dibenzylideneacetone) dipalladium, tris(dibenzylideneacetone) dipalladium (chloroform adduct), dichloro diamine palladium, bis(triphenylphosphine) dichloropalladium, bis(tricyclohexylphosphine) dichloropalladium, tetrakis(triphenylphosphine) palladium, dichloro[1,2-bis(diphenylphosphino)ethane] palladium, dichloro[1,3-bis(diphenylphosphino)propane] palladium, dichloro[1,4-bis(diphenylphosphino)butane] palladium, dichloro[1,1'-bis(diphenylphosphino)ferrocene] palladium, diphenylphosphino ferrocene dichloropalladium-dichloromethane complex, etc. Regarding the amount of the palladium catalyst used, it can be appropriately selected within the range of 0.001 to 0.5 times the molar amount relative to the compound represented by the general formula (54).

[0826] These palladium catalysts can be used alone or further in combination with a tertiary phosphine. Examples of the tertiary phosphine that can be used include triphenylphosphine, trimethylphosphine, triethylphosphine, tributylphosphine, tris(tert-butyl)phosphine, tricyclohexylphosphine, tri-o-tolylphosphine, trioctylphosphine, 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene, 2-(di-tert-butylphosphino)biphenyl, 2-(dicyclohexylphosphino)biphenyl, 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino)propane, 1,4-bis(diphenylphosphino)butane, 1,1'-bis(diphenylphosphino)ferrocene, (R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthalene, (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthalene, (±)-2,2'-bis(diphenylphosphino)-1,1'-binaphthalene, etc. The amount of these tertiary phosphines can be appropriately selected within the range of 0.5 to 10 times the molar amount relative to the palladium catalyst.

[0827] Examples of the vinyl metal compound that can be used in this reaction include vinylmagnesium bromide, vinylmagnesium chloride, vinylzinc chloride, tributylvinyltin, potassium vinyltrifluoroborate, vinylboronic acid, vinylboronic anhydride, 2-methyl-2,4-pentanediol vinylborate, pinacol vinylborate, vinyltriethoxysilane, etc., and a vinylboronic acid compound is preferred. The amount of the vinyl metal compound can be appropriately selected within the range of 0.8 to 3 times the molar amount relative to the compound represented by the general formula (54).

[0828] Examples of the base that can be used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium bicarbonate, potassium bicarbonate, etc., alkali metal hydrides such as sodium hydride, potassium hydride, and alcoholates such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, etc. The amount of the base can generally be used within the range of about 1 to 5 times the molar amount relative to the compound represented by the general formula (54).

[0829] As an inert solvent that can be used in this reaction, any solvent that does not significantly hinder this reaction is acceptable. Examples include alcohols such as methanol, ethanol, propanol, butanol, 2-propanol, etc., linear or cyclic ethers such as diethyl ether, tetrahydrofuran, dioxane, 1,2-dimethoxyethane (DME), etc., aromatic hydrocarbons such as benzene, toluene, xylene, etc., halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, etc., halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, etc., nitriles such as acetonitrile, esters such as ethyl acetate, polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone, and water. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent is not particularly limited as long as it can dissolve the reaction reagents, and it can be appropriately selected within the range of 0.5 L to 100 L relative to 1 mole of the compound represented by the general formula (54).

[0830] In this reaction, regarding the reaction temperature, it is usually carried out within the range of about 0 °C to the boiling point of the solvent used. Regarding the reaction time, although it is not fixed due to the reaction scale, reaction temperature, etc., it can be appropriately selected within the range of several minutes to 48 hours. In addition, this reaction can be carried out, for example, in an atmosphere of an inert gas such as nitrogen or argon. After the reaction is completed, the target product can be separated from the reaction system containing the target product by a conventional method, and it can also be purified by recrystallization, column chromatography, etc. as needed to prepare the target product. In addition, it can also be supplied to the next process without separation.

[0831] Preparation method of step [ac]

[0832] By following the method described in the 4th Edition of the Experimental Chemistry Lecture 23, Organic Chemistry V, Oxidation Reactions (MARUZEN GROUP), after converting the compound represented by the general formula (55) into a diol in the presence of osmium tetroxide and an oxidizing agent, and then following the method described in the New Experimental Chemistry Lecture 15, Oxidation and Reduction I-1 (MARUZEN GROUP), reacting the periodate compound in the presence of an inert solvent, the compound represented by the general formula (56) of the present invention can be prepared. After the reaction is completed, the target product can be separated from the reaction system containing the target product by a conventional method, and it can also be purified by recrystallization, column chromatography, etc. as needed to prepare the target product. In addition, it can also be supplied to the next process without separation.

[0833] Preparation method of step [ad]

[0834] The compound represented by the general formula (57) of the present invention can be prepared by converting the formyl group of the compound represented by the general formula (56) into a cyclic acetal group according to the method described in "Protective Groups in Organic Synthesis" (4th Edition, Greene’s Protective GROUP SinOrganic SYNTHESIS(4thEditon)). After the reaction is completed, the target product can be separated from the reaction system containing the target product by a conventional method, or the target product can be prepared by purification through recrystallization, column chromatography, etc. as needed. In addition, it can also be used in the next step without separation.

[0835] Method for preparing the compound represented by the general formula (2-2)

[0836] [Chemical formula 22]

[0837]

[0838] In the formula, A 1 , A 2 , A 3 and R 4 are the same as the aforementioned A 1 , A 2 , A 3 and R 4 . R and R' represent, for example, (C1-C4) alkyl groups such as methyl and ethyl, and X represents, for example, halogen atoms such as fluorine, chlorine, bromine, and iodine.

[0839] The compound represented by the general formula (2-2) as the starting material for Preparation Method 2 can be prepared from the compound represented by the general formula (54) through Step [d] of the aforementioned Preparation Method 1, Step [o] of the aforementioned Preparation Method 6, and Step [z] of the aforementioned Preparation Method 11.

[0840] Method for preparing the compound represented by the general formula (2-3)

[0841] [Chemical formula 23]

[0842]

[0843] In the formula, A 1 , A 2 , A 3 and R 4 are the same as the aforementioned A 1 , A 2 , A 3 and R 4 . R and R' represent, for example, (C1-C4) alkyl groups such as methyl and ethyl, and X represents, for example, halogen atoms such as fluorine, chlorine, bromine, and iodine.

[0844] The compound represented by the general formula (2-3), which is the starting material for Preparation Method 3, can be prepared from the compound represented by the general formula (54) through Step [d] of the above Preparation Method 1, Step [o] of the above Preparation Method 6, and Step [ae] of the above Preparation Method 13.

[0845] Preparation method of the compound represented by the general formula (2-4)

[0846] [Chemical formula 24]

[0847]

[0848] In the formula, A 1 , A 2 , A 3 and R 4 are the same as the said A 1 , A 2 , A 3 and R 4 . R represents an alkyl group of (C1-C4) such as methyl, ethyl, etc. Y represents a carbon atom, an oxygen atom, a sulfur atom or a nitrogen atom optionally substituted by an alkyl group of (C1-C4) such as methyl, ethyl, etc. q represents 1 or 2.

[0849] The compound represented by the general formula (2-4), which is the starting material for Preparation Method 14, can be prepared from the compound represented by the general formula (68) through the following Step [ag], Step [d] of the above Preparation Method 1, Step [l] of the above Preparation Method 6, and Steps [s] and [t] of the above Preparation Method 8.

[0850] Preparation method of Step [ag]

[0851] By reacting the compound represented by the general formula (72) with the compound represented by the general formula (77) in the presence of a metal catalyst, a base and an inert solvent, the compound represented by the general formula (2-4) can be prepared.

[0852] Examples of the metal catalyst that can be used in this reaction include palladium catalysts, nickel catalysts, iron catalysts, ruthenium catalysts, platinum catalysts, rhodium catalysts, iridium catalysts, etc. These metal catalysts can be used as "metal", "supported metal", "metal salts such as metal chlorides, bromides, iodides, nitrates, sulfates, carbonates, oxalates, acetates or oxides", "complexes such as olefin complexes, phosphine complexes, amine complexes, ammonia complexes or acetylacetonate complexes". A palladium catalyst is preferred.

[0853] As a palladium catalyst, palladium metals such as palladium black and spongy palladium can be cited. In addition, supported palladium metals such as palladium / aluminum oxide, palladium / carbon, palladium / silica, and palladium / Y-type zeolite can also be cited. Further, metal salts such as palladium chloride, palladium bromide, palladium iodide, and palladium acetate can be cited. Furthermore, complexes such as π-allylpalladium chloride dimer, palladium acetylacetonate, bis(acetonitrile)dichloropalladium, bis(benzonitrile)dichloropalladium, bis(dibenzylideneacetone)palladium, tris(dibenzylideneacetone)dipalladium, tris(dibenzylideneacetone)dipalladium (chloroform adduct), dichlorodiaminepalladium, bis(triphenylphosphine)dichloropalladium, bis(tricyclohexylphosphine)dichloropalladium, tetrakis(triphenylphosphine)palladium, dichloro[1,2-bis(diphenylphosphino)ethane]palladium, dichloro[1,3-bis(diphenylphosphino)propane]palladium, dichloro[1,4-bis(diphenylphosphino)butane]palladium, dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium, diphenylphosphinoferrocene dichloropalladium-dichloromethane complex can be cited. Regarding the amount of these metal catalysts used, it can be appropriately selected within the range of 0.001 to 0.5 times the molar amount relative to the compound represented by the general formula (72).

[0854] These palladium catalysts can be used alone or further in combination with a tertiary phosphine. As the tertiary phosphine that can be used, triphenylphosphine, trimethylphosphine, triethylphosphine, tributylphosphine, tris(tert-butyl)phosphine, tricyclohexylphosphine, tri-o-tolylphosphine, trioctylphosphine, 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene, 2-(di-tert-butylphosphino)biphenyl, 2-(dicyclohexylphosphino)biphenyl, 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino)propane, 1,4-bis(diphenylphosphino)butane, 1,1'-bis(diphenylphosphino)ferrocene, (R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthalene, (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthalene, (±)-2,2'-bis(diphenylphosphino)-1,1'-binaphthalene, etc. can be cited. Regarding the amount of these tertiary phosphines used, it can be appropriately selected within the range of 0.5 to 10 times the molar amount relative to the metal catalyst.

[0855] As the base that can be used in this reaction, inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium bicarbonate, and potassium bicarbonate, alkali metal hydrides such as sodium hydride and potassium hydride, and alcoholates such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide can be cited. Regarding the amount of the base used, it can usually be used within the range of about 1 to 5 times the molar amount relative to the compound represented by the general formula (72).

[0856] As an inert solvent that can be used in this reaction, any solvent that does not significantly hinder this reaction is acceptable. Examples include alcohols such as methanol, ethanol, propanol, butanol, 2-propanol, etc.; linear or cyclic ethers such as diethyl ether, tetrahydrofuran, dioxane, 1,2-dimethoxyethane (DME), etc.; aromatic hydrocarbons such as benzene, toluene, xylene, etc.; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, etc.; halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, etc.; nitriles such as acetonitrile, etc.; esters such as ethyl acetate, etc.; polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone, etc., and water. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it is an amount that can dissolve the reaction reagents, and it can be appropriately selected within the range of 0.5 L to 100 L relative to 1 mole of the compound represented by the general formula (72).

[0857] Since this reaction is an equimolar reaction, each compound can be used in equimolar amounts, and any one of the compounds can also be used in excess.

[0858] In this reaction, regarding the reaction temperature, it is usually carried out within the range of about 0 °C to the boiling point of the solvent used. Regarding the reaction time, although it is not fixed due to the reaction scale, reaction temperature, etc., it can be appropriately selected within the range of several minutes to 48 hours. In addition, this reaction can be carried out, for example, in an atmosphere of an inert gas such as nitrogen or argon.

[0859] After the reaction is completed, the target product can be separated from the reaction system containing the target product by conventional methods, and it can also be purified by recrystallization, column chromatography, etc. as needed to prepare the target product. In addition, it can also be used in the next process without separation.

[0860] Preparation method of the compound represented by the general formula (2-5)

[0861] [Chemical formula 25]

[0862]

[0863] In the formula, A 1 , A 2 , A 3 and R 4 are the same as the aforementioned A 1 , A 2 , A 3 and R 4 . R represents, for example, an alkyl group of (C1-C4) such as a methyl group or an ethyl group, R” represents, for example, a tertiary (C4-C6) alkyl group such as a tert-butyl group or a tri(C1-C3)alkylsilyl group such as a trimethylsilyl group, and X represents, for example, a halogen atom such as fluorine, chlorine, bromine, or iodine.

[0864] The compound represented by the general formula (2-5) as the starting material of Preparation Method 15 can be prepared from the compound represented by the general formula (73) through Step [g] of the above Preparation Method 4, Step [d] of the above Preparation Method 5, Step [o] of the above Preparation Method 6, and Step [ae] of the above Preparation Method 13.

[0865] Preparation method of the compound represented by the general formula (2-6)

[0866] [Chemical formula 26]

[0867]

[0868] In the formula, A 1 , A 2 and A 3 are the same as the said A 1 , A 2 and A 3 ; R represents, for example, an alkyl group of (C1-C4) such as methyl or ethyl; R” represents, for example, a tertiary (C4-C6) alkyl group such as tert-butyl or a tri (C1-C3) alkylsilyl group such as trimethylsilyl; X represents, for example, a halogen atom such as fluorine, chlorine, bromine or iodine.

[0869] The compound represented by the general formula (2-6) as the starting material of Preparation Method 16 can be prepared from the compound represented by the general formula (74) through Step [o] of the above Preparation Method 6.

[0870] The representative examples of the compound represented by the general formula (1) of the present invention are exemplified in Tables 1 to 8 below, but the present invention is not limited to these examples.

[0871] Next, specific examples of the compounds of the present invention are shown below. In the following tables, Me represents methyl, Et represents ethyl, i-Pr represents isopropyl, n-Pr represents n-propyl, c-Pr represents cyclopropyl, n-Bu represents n-butyl, i-Bu represents isobutyl, c-Bu represents cyclobutyl, t-Bu represents tert-butyl, Ac represents acetyl, Ph represents phenyl, Bn represents benzyl, and TMS represents trimethylsilyl. The physical property values represent melting point (°C), refractive index (n D ) or H 1 -NMR. The parentheses of the refractive index represent the measurement temperature (°C). The H 1 -NMR data are shown in Table 10.

[0872] [Chemical formula 27]

[0873]

[0874] The position numbers in the table are the numbers defined in the general formula (1a).

[0875] [Table 1-1]

[0876] Table 1

[0877] 化合物编号 <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 6 > 物性值 1-1 H H H And And 1-2 H H H i-Pr And 1-3 H H H <![CDATA[CH2CF3]]> And 167-168 1-4 H Me H And And 1-5 H Me H i-Pr And 1-6 H Me H <![CDATA[CH2CF3]]> And NMR 1-7 H Me Me And Me NMR 1-8 H Me Me i-Pr Me 1-9 H Me Me <![CDATA[CH2CF3]]> Me 1-10 H Me <![CDATA[NH2]]> H Me NMR 1-11 H Me <![CDATA[NH2]]> And Me 78-80 1-12 H Me <![CDATA[NH2]]> n-Pr Me 131-132 1-13 H Me <![CDATA[NH2]]> i-Pr Me 178-180 1-14 H Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> Me 1-15 H Me <![CDATA[NH2]]> And NHMe 97-98 1-16 H Me <![CDATA[NH2]]> n-Pr NHMe NMR 1-17 H Me <![CDATA[NH2]]> i-Pr NHMe 98-99 1-18 H Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> NHMe 170-171 1-19 H Me <![CDATA[NHCOCF3]]> And Me 78-80 1-20 H Me <![CDATA[NHCOCF3]]> i-Pr Me 1-21 H Me <![CDATA[NHCOCF3]]> <![CDATA[CH2CF3]]> Me 1-22 H Me NHMe And Me NMR 1-23 H Me NHMe i-Pr Me 1-24 H Me NHMe <![CDATA[CH2CF3]]> Me 1-25 H And H i-Pr And 1-26 H And H <![CDATA[CH2CF3]]> And NMR 1-27 H i-Pr H And And 1-28 H i-Pr H i-Pr And 1-29 H i-Pr H <![CDATA[CH2CF3]]> And NMR 1-30 H <![CDATA[CH2C≡CH]]> H And And

[0878] [Table 1-2]

[0879] Continued Table 1

[0880] 化合物编号 <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 6 > 物性值 1-31 H <![CDATA[CH2C≡CH]]> H i-Pr And 1-32 H <![CDATA[CH2C≡CH]]> H <![CDATA[CH2CF3]]> And NMR 1-33 H <![CDATA[CH2CF3]]> H And And 1-34 H <![CDATA[CH2CF3]]> H i-Pr And 1-35 H <![CDATA[CH2CF3]]> H <![CDATA[CH2CF3]]> And NMR 1-36 H <![CDATA[CH2OCH3]]> H And And 1-37 H <![CDATA[CH2OCH3]]> H i-Pr And 1-38 H <![CDATA[CH2OCH3]]> H <![CDATA[CH2CF3]]> And NMR 1-39 4-Br Me H And And NMR 1-40 4-Br Me H i-Pr And 1-41 4-Br Me H <![CDATA[CH2CF3]]> And NMR 1-42 4-Br Me Me And And 1-43 4-Br Me Me i-Pr And 1-44 4-Br Me Me <![CDATA[CH2CF3]]> And 1-45 4-Br Me <![CDATA[NH2]]> And And 1-46 4-Br Me <![CDATA[NH2]]> i-Pr And 1-47 4-Br Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> And 1-48 4-Me Me H And And 1-49 4-Me Me H i-Pr And 1-50 4-Me Me H <![CDATA[CH2CF3]]> And 1-51 4-Me Me Me And Me NMR 1-52 4-Me Me Me i-Pr Me 1-53 4-Me Me Me <![CDATA[CH2CF3]]> Me 1-54 4-Me Me <![CDATA[NH2]]> And Me 170-171 1-55 4-Me Me <![CDATA[NH2]]> i-Pr Me 1-56 4-Me Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> Me 1-57 4-Me Me <![CDATA[NH2]]> And NHMe 187-188 1-58 4-And Me <![CDATA[NH2]]> And Me 214-215 1-59 4-And Me <![CDATA[NH2]]> i-Pr Me 1-60 4-And Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> Me

[0881] [Table 1-3]

[0882] Continued Table 1

[0883] 化合物编号 <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 6 > 物性值 1-61 4-And Me <![CDATA[NH2]]> And NHMe NMR 1-62 5-F Me H And Me 1-63 5-F Me Me And Me NMR 1-64 5-F Me <![CDATA[NH2]]> And Me 155-156 1-65 5-F Me <![CDATA[NH2]]> n-Pr Me 110-111 1-66 5-F Me <![CDATA[NH2]]> And NHMe NMR 1-67 5-F Me <![CDATA[NH2]]> n-Pr NHMe NMR 1-68 5-Cl Me H And Me 1-69 5-Cl Me Me And Me 143-144 1-70 5-Cl Me <![CDATA[NH2]]> Me Me 218-221 1-71 5-Cl Me <![CDATA[NH2]]> And Me 176-177 1-72 5-Cl Me H i-Pr Me 1-73 5-Cl Me Me i-Pr Me 1-74 5-Cl Me <![CDATA[NH2]]> i-Pr Me 172-173 1-75 5-Cl Me <![CDATA[NH2]]> Me NHMe 190-191 1-76 5-Cl Me <![CDATA[NH2]]> And NHMe 203-204 1-77 5-Cl Me <![CDATA[NH2]]> i-Pr NHMe 190-191 1-78 5-Cl Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> NHMe 1-79 5-Cl Me <![CDATA[NH2]]> And <![CDATA[NMe2]]> 1-80 5-Cl Me <![CDATA[NH2]]> i-Pr <![CDATA[NMe2]]> 154-156 1-81 5-Br H H And And 1-82 5-Br H H i-Pr And 1-83 5-Br H H <![CDATA[CH2CF3]]> And 187-188 1-84 5-Br Me H And And 152-153 1-85 5-Br Me H i-Pr And 1-86 5-Br Me H <![CDATA[CH2CF3]]> And NMR 1-87 5-Br Me Me And Me 171-172 1-88 5-Br Me Me i-Pr Me 1-89 5-Br Me Me <![CDATA[CH2CF3]]> Me 1-90 5-Br Me <![CDATA[NH2]]> And Me 151-152

[0884] [Table 1-4]

[0885] Continued Table 1

[0886] 化合物编号 <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 6 > 物性值 1-91 5-Br Me <![CDATA[NH2]]> i-Pr Me 1-92 5-Br Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> Me 1-93 5-Br Me <![CDATA[NH2]]> And NHMe 1-94 5-Br Me <![CDATA[NH2]]> i-Pr NHMe 1-95 5-Br Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> NHMe 1-96 5-Me H H And Me 1-97 5-Me H Me And Me 1-98 5-Me H <![CDATA[NH2]]> And Me 226-227 1-99 5-Me Me H Me Me 1-100 5-Me Me Me Me Me 1-101 5-Me Me <![CDATA[NH2]]> H Me NMR 1-102 5-Me Me <![CDATA[NH2]]> Me Me 170-171 1-103 5-Me Me <![CDATA[NH2]]> i-Pr Me 171-172 1-104 5-Me Me <![CDATA[NH2]]> n-Pr Me 188-189 1-105 5-Me Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> Me 1-106 5-Me Me H And Me 1-107 5-Me Me Me And Me 144-145 1-108 5-Me Me <![CDATA[NH2]]> And Me 80-83 1-109 5-Me Me <![CDATA[NHCOCF3]]> And Me 95-97 1-110 5-Me Me <![CDATA[NH2]]> <![CDATA[CH2C H2OCH3]]> Me 143-144 1-111 5-Me Me <![CDATA[NH2]]> And And NMR 1-112 5-Me Me <![CDATA[NH2]]> i-Pr And 1-113 5-Me Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> And 1-114 5-Me Me <![CDATA[NH2]]> Me NHMe 165-167 1-115 5-Me Me <![CDATA[NH2]]> And NHMe 196-197 1-116 5-Me Me <![CDATA[NH2]]> And <![CDATA[NMe2]]> NMR 1-117 5-Me Me <![CDATA[NH2]]> n-Pr NHMe 161-162 1-118 5-Me Me <![CDATA[NH2]]> i-Pr NHMe 172-173 1-119 5-Me Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> NHMe 1-120 5-Me Me CN H Me 267-268

[0887] [Table 1-5]

[0888] Continued Table 1

[0889] 化合物编号 <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 6 > 物性值 1-121 5-Me Me CN And Me 202-203 1-122 5-Me Me CN i-Pr Me 1-123 5-Me Me CN <![CDATA[CH2CF3]]> Me 1-124 5-Me And <![CDATA[NH2]]> And Me 79-80 1-125 5-Me And <![CDATA[NH2]]> And NHMe 153-154 1-126 5-Me n-Pr <![CDATA[NH2]]> And Me 157-158 1-127 5-Me i-Pr <![CDATA[NH2]]> And Me 216-217 1-128 5-Me c-Pr <![CDATA[NH2]]> And Me NMR 1-129 5-And Me H Me Me 1-130 5-And Me Me Me Me 1-131 5-And Me <![CDATA[NH2]]> Me Me 76 1-132 5-And Me <![CDATA[NH2]]> Me NHMe 98 1-133 5-And Me H And Me 1-134 5-And Me Me And Me NMR 1-135 5-And Me <![CDATA[NH2]]> And Me 137-138 1-136 5-And Me <![CDATA[NH2]]> And NHMe 166-167 1-137 5-And Me H And Me 1-138 5-And Me Me And Me 1-139 5-And Me <![CDATA[NH2]]> i-Pr Me 80-81 1-140 5-And Me <![CDATA[NH2]]> i-Pr NHMe 73-74 1-141 <![CDATA[5-CH=CH2]]> Me H And And NMR 1-142 <![CDATA[5-CH=CH2]]> Me Me And Me 1-143 <![CDATA[5-CH=CH2]]> Me <![CDATA[NH2]]> And Me NMR 1-144 5-C≡CH Me H And Me 1-145 5-C≡CH Me Me And Me 1-146 5-C≡CH Me <![CDATA[NH2]]> And Me 1-147 5-c-Pr Me H And Me 1-148 5-c-Pr Me Me And Me NMR 1-149 5-C-Pr Me <![CDATA[NH2]]> And Me 1-150 5-n-Pr Me H And Me

[0890] [Table 1-6]

[0891] Continued Table 1

[0892] 化合物编号 <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 6 > 物性值 1-151 5-n-Pr Me Me And Me NMR 1-152 5-n-Pr Me <![CDATA[NH2]]> And Me 1-153 5-i-Pr Me H And Me 1-154 5-i-Pr Me Me And Me NMR 1-155 5-i-Pr Me <![CDATA[NH2]]> And Me 65-66 1-156 5-i-Pr Me <![CDATA[NH2]]> And NHMe 65-66 1-157 5-正戊基 Me Me And Me NMR 1-158 5-t-Bu Me Me And Me NMR 1-159 <![CDATA[5-CH2OH]]> Me H And Me 1-160 <![CDATA[5-CH2OH]]> Me Me And Me 112-113 1-161 <![CDATA[5-CH2OH]]> Me <![CDATA[NH2]]> And Me 178-179 1-162 <![CDATA[5-CH2OCH3]]> Me H And Me 1-163 <![CDATA[5-CH2OCH3]]> Me Me And Me 123-124 1-164 <![CDATA[5-CH2OCH3]]> Me <![CDATA[NH2]]> And Me NMR 1-165 <![CDATA[5-CH2SCH3]]> Me Me And Me NMR 1-166 <![CDATA[5-CH2SOCH3]]> Me Me And Me NMR 1-167 <![CDATA[5-CH2SO2CH3]]> Me Me And Me NMR 1-168 <![CDATA[5-CH2SCH3]]> Me <![CDATA[NH2]]> And Me 1-169 <![CDATA[5-CH2SOCH3]]> Me <![CDATA[NH2]]> And Me 1-170 <![CDATA[5-CH2SO2CH3]]> Me <![CDATA[NH2]]> And Me 1-171 <![CDATA[5-CH2NHCH3]]> Me Me And Me NMR 1-172 <![CDATA[5-CH2N(CH3)2]]> Me Me And Me NMR 1-173 <![CDATA[5-CH2N(CH2CH3)2]]> Me Me And Me NMR 1-174 <![CDATA[5-CH2F]]> Me Me And Me 109-110 1-175 <![CDATA[5-CH2Cl]]> Me Me And Me NMR 1-176 <![CDATA[5-CHF2]]> Me H And Me 1-177 <![CDATA[5-CHF2]]> Me Me And Me 178-179 1-178 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> H Me 259-260 1-179 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Me Me 81-82 1-180 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> And Me 172-173

[0893] [Table 1-7]

[0894] Continued Table 1

[0895] 化合物编号 <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 6 > 物性值 1-181 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> i-Pr Me 205-206 1-182 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> Me 1-183 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> And And 87-88 1-184 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> And n-Pr NMR 1-185 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> And i-Pr 185-186 1-186 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> And NHMe 175-176 1-187 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Ac Me 195-196 1-188 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> <![CDATA[CH2C≡CH]]> Me 142-143 1-189 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> Me 184-185 1-190 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> <![CDATA[CH2CH=CH2]]> Me 164-165 1-191 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> <![CDATA[CH2CHF2]]> Me 161-162 1-192 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> <![CDATA[CH2CN]]> Me 227-228 1-193 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> <![CDATA[CH2-c-Pr]]> Me 206-207 1-194 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> <![CDATA[CH2SCH3]]> Me 161-162 1-195 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> <![CDATA[CH2SOCH3]]> Me 47-48 1-196 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> <![CDATA[CH2SO2CH3]]> Me 79-80 1-197 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> <![CDATA[CO2Me]]> Me 224-225 1-198 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Ph Me 187-188 1-199 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> <![CDATA[SO2Me]]> Me 225-226 1-200 <![CDATA[5-CF3]]> Me Me And Me 132-133 1-201 <![CDATA[5-CF3]]> Me Me i-Pr Me 1-202 <![CDATA[5-CF3]]> Me Me <![CDATA[CH2CF3]]> Me 1-203 <![CDATA[5-CF3]]> Me Me And NHMe 217-218 1-204 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Me Me 108 1-205 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> And Me 149-150 1-206 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr Me NMR 1-207 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> Me 1-208 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> <![CDATA[CH2C(CH3)=CH2]]> Me 168-169 1-209 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Me NHMe 212-213 1-210 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> And NHMe 173-174

[0896] [Table 1-8]

[0897] Continued Table 1

[0898] 化合物编号 <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 6 > 物性值 1-211 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr NHMe 103-104 1-212 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> NHMe 1-213 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> And <![CDATA[NMe2]]> 1-214 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr <![CDATA[NMe2]]> 171-173 1-215 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr NHOMe 103-105 1-216 <![CDATA[5-CF3]]> Me NHMe And Me 154-155 1-217 <![CDATA[5-CF3]]> Me NHMe And NHMe 204-205 1-218 <![CDATA[5-CF3]]> Me NHMe i-Pr Me 1-219 <![CDATA[5-CF3]]> Me NHMe i-Pr NHMe 1-220 <![CDATA[5-CF3]]> Me <![CDATA[NMe2]]> And Me 150-151 1-221 <![CDATA[5-CF3]]> Me <![CDATA[NMe2]]> And NHMe 183-184 1-222 <![CDATA[5-CF3]]> Me <![CDATA[NMe2]]> i-Pr Me 1-223 <![CDATA[5-CF3]]> Me <![CDATA[NMe2]]> i-Pr NHMe 1-224 5-OMe Me H And Me 1-225 5-OMe Me Me And Me NMR 1-226 5-OMe Me <![CDATA[NH2]]> And Me 115-118 1-227 5-OMe Me <![CDATA[NH2]]> And NHMe 186-188 1-228 5-OMe Me <![CDATA[NH2]]> i-Pr Me 168-170 1-229 5-OMe Me <![CDATA[NH2]]> i-Pr NHMe 159 1-230 5-OEt Me H And Me 1-231 5-OEt Me Me And Me 1-232 5-OEt Me <![CDATA[NH2]]> And Me 1-233 5-OEt Me <![CDATA[NH2]]> And NHMe 232 1-234 5-Oi-Pr Me <![CDATA[NH2]]> And Me 104-106 1-235 <![CDATA[5-OCHF2]]> Me H And Me 1-236 <![CDATA[5-OCHF2]]> Me Me And Me 1-237 <![CDATA[5-OCHF2]]> Me <![CDATA[NH2]]> And Me 140 1-238 <![CDATA[5-OCHF2]]> Me <![CDATA[NH2]]> i-Pr Me 121-122 1-239 <![CDATA[5-OCHF2]]> Me <![CDATA[NH2]]> And NHMe 151-153 1-240 <![CDATA[5-OCHF2]]> Me <![CDATA[NH2]]> i-Pr NHMe 96

[0899] [Table 1-9]

[0900] Continued Table 1

[0901] 化合物编号 <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 6 > 物性值 1-241 <![CDATA[5-OCF3]]> Me H And And 51-52 1-242 <![CDATA[5-OCF3]]> Me H <![CDATA[CH2CF3]]> And 39-40 1-243 <![CDATA[5-OCF3]]> Me H <![CDATA[CH2CHF2]]> And 50-51 1-244 <![CDATA[5-OCF3]]> Me Me And And 1-245 <![CDATA[5-OCF3]]> Me <![CDATA[NH2]]> And Me 87-88 1-246 5-NO2 Me Me And Me 174-175 1-247 <![CDATA[5-NH2]]> Me Me And Me NMR 1-248 5-NHAc Me Me And Me NMR 1-249 5-SMe Me <![CDATA[NH2]]> And Me NMR 1-250 5-SOMe Me <![CDATA[NH2]]> And Me 1-251 <![CDATA[5-SO2Me]]> Me <![CDATA[NH2]]> And Me 1-252 5-SEt Me Me And Me NMR 1-253 5-SOEt Me Me And Me 1-254 <![CDATA[5-SO2Et]]> Me Me And Me 1-255 <![CDATA[5-SCF3]]> Me H Me And NMR 1-256 <![CDATA[5-SCF3]]> Me H And Me 73-74 1-257 <![CDATA[5-SCF3]]> Me H And And NMR 1-258 <![CDATA[5-SCF3]]> Me H And i-Pr 157-158 1-259 <![CDATA[5-SCF3]]> Me H And n-Pr 102-103 1-260 <![CDATA[5-SCF3]]> Me H <![CDATA[CH2CF2CF3]]> And 45-46 1-261 <![CDATA[5-SCF3]]> Me H <![CDATA[CH2CF2CHF2]]> And NMR 1-262 <![CDATA[5-SCF3]]> Me H <![CDATA[CH2CF3]]> And NMR 1-263 <![CDATA[5-SCF3]]> Me H <![CDATA[CH2CHF2]]> And NMR 1-264 <![CDATA[5-SCF3]]> Me H i-Pr And 139-140 1-265 <![CDATA[5-SCF3]]> Me Me And Me 101-102 1-266 <![CDATA[5-SCF3]]> Me Me i-Pr Me 1-267 <![CDATA[5-SCF3]]> Me <![CDATA[NH2]]> And Me 1-268 <![CDATA[5-SCF3]]> Me <![CDATA[NH2]]> i-Pr Me 1-269 <![CDATA[5-SOCF3]]> Me H And Me 80-81 1-270 <![CDATA[5-SOCF3]]> Me H And And NMR

[0902] [Table 1-10]

[0903] Continued Table 1

[0904]

[0905] The "*" in the compound number indicates the Z isomer.

[0906] [Table 1-11]

[0907] Continuation of Table 1

[0908] 化合物编号 <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 6 > 物性值 1-301 <![CDATA[5-SO2CF3]]> Me <![CDATA[NH2]]> And Me 1.4292(21.6℃) 1-302 <![CDATA[5-SO2CF3]]> Me <![CDATA[NH2]]> i-Pr Me 1-303 <![CDATA[5-SO2NMe2]]> Me Me And Me 1-304 5-CHO Me Me And Me 190-191 1-305 5-CHO Me <![CDATA[NH2]]> And Me 242-243 1-306 5-CN Me Me And Me 119-120 1-307 5-COMe Me Me And Me 1-308 <![CDATA[5-CO2H]]> Me Me And Me 265-266 1-309 <![CDATA[5-CO2Me]]> Me Me And Me 162-163 1-310 <![CDATA[5-CO2Me]]> Me <![CDATA[NH2]]> And Me 198-199 1-311 <![CDATA[5-CO2Et]]> Me <![CDATA[NH2]]> And Me 190-191 1-312 5-CONHMe Me Me And Me 1-313 5-CH=N-OMe Me Me And Me 176-177 1-314 <![CDATA[5-CH(OCH3)2]]> Me Me And Me NMR 1-315 5-二噁烷-2-基 Me Me And Me 92-93 1-316 5-二氧戊环-2-基 Me Me And Me NMR 1-317 5-Ph Me Me And Me NMR 1-318 5-(4-F-Ph) Me Me And Me 168-169 1-319 5-(4-OMe-Ph) Me Me And Me 88-89 1-320 5-(吡啶-3-基) Me Me And Me NMR 1-321 5-(1-甲基-1H-吡唑-5-基) Me Me And Me NMR 1-322 6-F Me H And And 1.4237(24.4℃) 1-323 6-F Me H i-Pr And 1.4289(24.2℃) 1-324 6-F Me H <![CDATA[CH2CF3]]> And 1.4664(24-0℃) 1-325 6-Cl Me H And And 1.4198(24.8℃) 1-326 6-Cl Me H i-Pr And 1.4025(24.8℃) 1-327 6-Cl Me H <![CDATA[CH2CF3]]> And 1.4707(24.7℃) 1-328 6-Br Me H And And 90-91 1-329 6-Me Me H And And 1.4235(24.5℃) 1-330 <![CDATA[6-CH=CH2]]> Me H And And 1.3319(24.5℃)

[0909] [Table 1-12]

[0910] Continuation of Table 1

[0911]

[0912] "●" indicates the bonding to the benzimidazole ring, and the number indicates the bonding position.

[0913] [Table 1-13]

[0914] Continuation of Table 1

[0915] 化合物编号 <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 6 > 物性值 1-353 H Me <![CDATA[NH2]]> n-Bu NHMe 1-354 H Me <![CDATA[NH2]]> i-Bu NHMe 1-355 4-Cl Me <![CDATA[NH2]]> And Me 198-199 1-356 4-Cl Me <![CDATA[NH2]]> And NHMe 186-187 1-357 <![CDATA[4-CF3]]> Me <![CDATA[NH2]]> And Me 1-358 <![CDATA[4-CF3]]> Me <![CDATA[NH2]]> And NHMe 1-359 4-OMe Me <![CDATA[NH2]]> Me Me 168-169 1-360 4-OMe Me <![CDATA[NH2]]> And Me 160-161 1-361 4-OMe Me <![CDATA[NH2]]> i-Pr Me 188-190 1-362 4-OMe Me <![CDATA[NH2]]> Me NHMe 173-174 1-363 4-OMe Me <![CDATA[NH2]]> And NHMe 176-177 1-364 4-OMe Me <![CDATA[NH2]]> i-Pr NHMe 185-186 1-365 5-Cl Me <![CDATA[NH2]]> Me <![CDATA[NMe2]]> 106-108 1-366 5-l Me <![CDATA[NH2]]> And Me 1-367 5-l Me <![CDATA[NH2]]> And NHMe 1-368 5-Me Me <![CDATA[NH2]]> <![CDATA[CH2CH2OCH3]]> NHMe 154-155 1-369 5-Me Me <![CDATA[NH2]]> n-Bu Me 167-168 1-370 5-Me Me <![CDATA[NH2]]> i-Bu Me 170-171 1-371 5-Me Me <![CDATA[NH2]]> n-Bu NHMe 1-372 5-Me Me <![CDATA[NH2]]> i-Bu NHMe 1-373 5-Me Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> Me 66-67 1-374 5-Me Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> NHMe 1-375 5-Me Me <![CDATA[NH2]]> c-Pr Me 1-376 5-Me Me <![CDATA[NH2]]> c-Pr NHMe 1-377 5-c-Pr Me <![CDATA[NH2]]> Et Me 1-378 5-C-Pr Me <![CDATA[NH2]]> Et NHMe 1-379 5-OMe Me <![CDATA[NH2]]> Me NHMe 182-185 1-380 5-OMe Me <![CDATA[NH2]]> Me Me 181-182 1-381 <![CDATA[5-OCHF2]]> Me <![CDATA[NH2]]> Me Me 1-382 <![CDATA[5-OCHF2]]> Me <![CDATA[NH2]]> Me NHMe 181-182

[0916] [Table 1-14]

[0917] Continuation of Table 1

[0918] compound number <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 6 > 物性值 1-383 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> c-Pr Me 1-384 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> c-Pr NHMe 1-385 4,5-di-Me Me <![CDATA[NH2]]> Et Me 1-386 4,5-di-Me Me <![CDATA[NH2]]> Et NHMe 1-387 <![CDATA[5-NO2]]> Me <![CDATA[NH2]]> Et Me 238-239 1-388 H Me <![CDATA[NH2]]> Et Me 1-389 H Me <![CDATA[NH2]]> Et NHMe 1-390 4,5-diMe Me <![CDATA[NH2]]> Et Me NMR 1-391 H Me <![CDATA[NH2]]> Me Me 84-85 1-392 H Me <![CDATA[NH2]]> Me NHMe 94-96 1-393 <![CDATA[4-CF3]]> Me <![CDATA[NH2]]> Me Me 245-246 1-394 <![CDATA[4-CF3]]> Me <![CDATA[NH2]]> Et Me 224-225 1-395 <![CDATA[4-CF3]]> Me <![CDATA[NH2]]> Me NHMe NMR 1-396 <![CDATA[4-CF3]]> Me <![CDATA[NH2]]> Et NHMe NMR 1-397 5-Me Me <![CDATA[NH2]]> <![CDATA[CH2CH=C H2]]> NHMe 170-171 1-398 5-F Me <![CDATA[NH2]]> Me NHMe NMR 1-399 5-F Me <![CDATA[NH2]]> Me Me NMR 1-400 H Me <![CDATA[NH2]]> Et N(Me)Ac 219-220 1-401 H Me <![CDATA[NH2]]> Et <![CDATA[NMe2]]> NMR 1-402 5-OMe Me <![CDATA[NH2]]> Me <![CDATA[NMe2]]> 154-156 1-403 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> <![CDATA[CH2CO2Me]]> Me NMR 1-404 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> n-Pr Me 1-405 H Me <![CDATA[NH2]]> n-Bu Me 1-406 5-OMe Me <![CDATA[NH2]]> n-Pr Me 1-407 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> n-Pr Me 1-408 5-F Me <![CDATA[NH2]]> i-Pr Me 1-409 5-Cl Me <![CDATA[NH2]]> n-Pr Me 1-410 5-Et Me <![CDATA[NH2]]> n-Pr Me 1-411 5-Br Me <![CDATA[NH2]]> Me Me 1-412 5-F Me <![CDATA[NH2]]> i-Pr NHMe 1-413 5-OMe Me <![CDATA[NH2]]> n-Pr NHMe

[0919] [Table 1-15]

[0920] Continuation of Table 1

[0921] compound number <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 6 > 物性值 1-414 5-Et Me <![CDATA[NH2]]> n-Pr NHMe 1-415 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> n-Pr NHMe 1-416 5-Cl Me <![CDATA[NH2]]> n-Pr NHMe 1-417 5-i-Pr Me <![CDATA[NH2]]> n-Pr NHMe 1-418 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> n-Pr NHMe 1-419 5-i-Pr Me <![CDATA[NH2]]> i-Pr NHMe 1-420 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> i-Pr NHMe 1-421 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Me NHMe 1-422 5-i-Pr Me <![CDATA[NH2]]> Me NHMe 1-423 5-Br Me <![CDATA[NH2]]> i-Pr Me 1-424 5-Br Me <![CDATA[NH2]]> n-Pr Me

[0922] [Chemical Formula 28]

[0923]

[0924] The position numbers in the table are the numbers defined in the general formula (1b).

[0925] [Table 2-1]

[0926] Table 2

[0927] compound number <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 7 > 物性值 2-1 H Me H Et OMe 109-110 2-2 H Me Me Et OH 239-241 2-3 H Me Me Et OMe 111-113 2-4 H Me Me Et OET 80-83 2-5 H Me Me Et <![CDATA[NMe2]]> 136-138 2-6 H Me <![CDATA[NH2]]> H OMe 232-233 2-7 H Me <![CDATA[NH2]]> Me OMe 172-173 2-8 H Me <![CDATA[NH2]]> Et OMe 2-9 <![CDATA[4-CO2Me]]> Me Me Et OMe 2-10 <![CDATA[4-CO2Me]]> Me <![CDATA[NH2]]> Et OMe 177-178 2-11 <![CDATA[4-CO2Me]]> Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> OMe 77-78 2-12 5-Cl Me <![CDATA[NH2]]> H OMe 256-258 2-13 5-Cl Me <![CDATA[NH2]]> Et OH 277 2-14 5-Cl Me H Et OMe 2-15 5-Cl Me Me Et OMe 2-16 5-Cl Me <![CDATA[NH2]]> Et OMe 175-176 2-17 5-Cl Me <![CDATA[NH2]]> Et OET 2-18 5-Cl Me <![CDATA[NH2]]> Et NH-t-Bu 81 2-19 5-Cl Me <![CDATA[NH2]]> Et <![CDATA[NMe2]]> 2-20 5-Cl Me <![CDATA[NH2]]> i-Pr OH 223-225 2-21 5-Cl Me <![CDATA[NH2]]> i-Pr OMe 156 2-22 5-Cl Me <![CDATA[NH2]]> i-Pr OET 2-23 5-Cl Me <![CDATA[NH2]]> i-Pr NH-t-Bu 85-87 2-24 5-Cl Me <![CDATA[NH2]]> i-Pr <![CDATA[NMe2]]> 2-25 5-Br Me H Et OMe 119-120 2-26 5-Br Me Me Et OMe 2-27 5-Br Me <![CDATA[NH2]]> Et OMe 2-28 5-Me Me Me Et Me 135-138 2-29 5-Me Me Me Et <![CDATA[CH2CO2Me]]> 169-171 2-30 5-Me Me Me Et OH 252-253

[0928] [Table 2-2]

[0929] Continuation of Table 2

[0930] compound number <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 7 > 物性值 2-31 5-Me Me Me Et OMe 142-144 2-32 5-Me Me Me Et OET 121-122 2-33 5-Me Me Me Et <![CDATA[NMe2]]> 199-201 2-34 5-Me Me <![CDATA[NH2]]> Et H 206-207 2-35 5-Me Me <![CDATA[NH2]]> Et Me NMR 2-36 5-Me Me <![CDATA[NH2]]> Et OMe 137-138 2-37 5-Me Me <![CDATA[NH2]]> Et OET 108-109 2-38 5-Me Me <![CDATA[NH2]]> Et Oi-Pr 2-39 <![CDATA[5-CF3]]> Me H Et OET 2-40 <![CDATA[5-CF3]]> Me Me Et OET 2-41 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> H OMe 241-242 2-42 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Me OMe 170-171 2-43 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Et OH 121-122 2-44 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Et OMe 153-154 2-45 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Et OET 119-12O 2-46 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Et Oi-Pr NMR 2-47 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Et <![CDATA[OCH2CO2Me]]> 99-100 2-48 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Et NHMe 153-154 2-49 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Et NHEt 178-179 2-50 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Et NH-i-Pr 182-183 2-51 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Et NH-t-Bu 107-108 2-52 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Et <![CDATA[NMe2]]> NMR 2-53 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> n-Pr OH 202-203 2-54 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> n-Pr OMe 145-146 2-55 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> n-Pr NHMe 178-179 2-56 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> n-Pr NHEt 136-137 2-57 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> n-Pr NH-i-Pr 180-181 2-58 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> n-Pr NH-t-Bu NMR 2-59 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> n-Pr OET 110-111 2-60 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr OH 256-257

[0931] [Table 2-3]

[0932] Continuation of Table 2

[0933] compound number <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 7 > 物性值 2-61 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr OMe 108-109 2-62 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr OET NMR 2-63 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr Oi-Pr NMR 2-64 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr <![CDATA[OCH2CO2Me]]> 108-109 2-65 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr NHMe NMR 2-66 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr NHEt 91-92 2-67 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr NH-i-Pr 87-88 2-68 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr NH-t-Bu 72-73 2-69 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr <![CDATA[NMe2]]> NMR 2-70 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr N(Me)OMe 138-139 2-71 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr SET NMR 2-72 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> OMe 150-151 2-73 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> OET NMR 2-74 <![CDATA[5-CF3]]> Me NHAc Et OET 131-132 2-75 5-SMe Me <![CDATA[NH2]]> Et OMe 2-76 5-SOMe Me <![CDATA[NH2]]> Et OMe 2-77 <![CDATA[5-SO2Me]]> Me <![CDATA[NH2]]> Et OMe 180-181 2-78 5-SMe Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> OMe 2-79 5-SOMe Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> OMe 2-80 <![CDATA[5-SO2Me]]> Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> OMe 230-231 2-81 <![CDATA[5-SCF3]]> Me H Et OH 195-196 2-82 <![CDATA[5-SCF3]]> Me H Et OMe NMR 2-83 <![CDATA[5-SCF3]]> Me H Et OET NMR 2-84 <![CDATA[5-SCF3]]> Me H Et On-Pr NMR 2-85 <![CDATA[5-SCF3]]> Me H Et Oi-Pr NMR 2-86 <![CDATA[5-SCF3]]> Me H Et Ot-Bu 85-86 2-87 <![CDATA[5-SCF3]]> Me H Et <![CDATA[OCH2C≡CH]]> 151-152 2-88 <![CDATA[5-SCF3]]> Me H Et <![CDATA[NH2]]> 233-234 2-89 <![CDATA[5-SCF3]]> Me H Et NHMe 169-170 2-90 <![CDATA[5-SCF3]]> Me H Et NHEt 140-141

[0934] [Table 2-4]

[0935] Continuation of Table 2

[0936] compound number <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 7 > 物性值 2-91 <![CDATA[5-SCF3]]> Me H Et NH-i-Pr 142-143 2-92 <![CDATA[5-SCF3]]> Me H Et NH-c-Pr 175-176 2-93 <![CDATA[5-SCF3]]> Me H Et <![CDATA[NHCH2CF3]]> 160-161 2-94 <![CDATA[5-SCF3]]> Me H Et <![CDATA[NHCH2CHF2]]> 162-163 2-95 <![CDATA[5-SCF3]]> Me H Et <![CDATA[NMe2]]> 118-119 2-96 <![CDATA[5-SCF3]]> Me H Et <![CDATA[NEt2]]> 109-110 2-97 <![CDATA[5-SCF3]]> Me H Et N(Me)Et 114-115 2-98 <![CDATA[5-SCF3]]> Me H Et N(Me)-i-Pr 153-154 2-99 <![CDATA[5-SCF3]]> Me H Et <![CDATA[NHSO2NMe2]]> 173-175 2-100 <![CDATA[5-SCF3]]> Me H Et pyrrolidine-1-基 72-73 2-101 <![CDATA[5-SCF3]]> Me H <![CDATA[CH2CF3]]> OMe 92-93 2-102 <![CDATA[5-SCF3]]> Me Me H OMe NMR 2-103 <![CDATA[5-SCF3]]> Me Me Me OMe NMR 2-104 <![CDATA[5-SCF3]]> Me Me Et OH 164-165 2-105 <![CDATA[5-SCF3]]> Me Me Et OMe 121-122 2-106＊ <![CDATA[5-SCF3]]> Me Me Et OMe NMR 2-107 <![CDATA[5-SCF3]]> Me Me Et OET 106-107 2-108 <![CDATA[5-SCF3]]> Me Me Et NHMe 161-162 2-109 <![CDATA[5-SCF3]]> Me Me Et <![CDATA[NMe2]]> 159-160 2-110 <![CDATA[5-SCF3]]> Me Me i-Pr OMe NMR 2-111 <![CDATA[5-SCF3]]> Me Me t-Bu OMe NMR 2-112 <![CDATA[5-SCF3]]> Me Me <![CDATA[CH2CF3]]> OMe 159-160 2-113 <![CDATA[5-SCF3]]> Me Me <![CDATA[CH2CH=CH2]]> OMe NMR 2-114 <![CDATA[5-SCF3]]> Me Me <![CDATA[CH2CHF2]]> OMe NMR 2-115 <![CDATA[5-SCF3]]> Me Me <![CDATA[CH2CO2H]]> OMe 2-116 <![CDATA[5-SCF3]]> Me Me Bn OMe NMR 2-117 <![CDATA[5-SCF3]]> Me Me <![CDATA[CH2(4-Cl-Ph)]]> OMe NMR 2-118 <![CDATA[5-SCF3]]> Me Me <![CDATA[CH(CH3)Ph]]> OMe 2-119 <![CDATA[5-SCF3]]> Me Me <![CDATA[CH2CH2(4-Cl-Ph)]]> OMe NMR 2-120 <![CDATA[5-SCF3]]> Me <![CDATA[CH2CO2CH3]]> Et OMe 1.4963(20.1℃)

[0937] The "*" in the compound number indicates the Z isomer.

[0938] [Table 2-5]

[0939] Continuation of Table 2

[0940] compound number <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 7 > 物性值 2-121 <![CDATA[5-SCF3]]> Me <![CDATA[NH2]]> H OMe 199-200 2-122 <![CDATA[5-SCF3]]> Me <![CDATA[NH2]]> Me OMe 59-60 2-123 <![CDATA[5-SCF3]]> Me <![CDATA[NH2]]> Et OMe 46-47 2-124 <![CDATA[5-SCF3]]> Me <![CDATA[NH2]]> Et OET 2-125 <![CDATA[5-SCF3]]> Me <![CDATA[NH2]]> i-Pr OMe 2-126 <![CDATA[5-SCF3]]> Me <![CDATA[NH2]]> n-Pr OMe NMR 2-127 <![CDATA[5-SCF3]]> Me <![CDATA[NH2]]> n-Bu OMe NMR 2-128 <![CDATA[5-SCF3]]> Me <![CDATA[NH2]]> n-Bu On-Bu 92-93 2-129 <![CDATA[5-SCF3]]> Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> OMe 145-146 2-130 <![CDATA[5-SCF3]]> Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> OET 2-131 <![CDATA[5-SCF3]]> Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> <![CDATA[NMe2]]> 2-132 <![CDATA[5-SCF3]]> Me <![CDATA[NH2]]> Bn OBn NMR 2-133 <![CDATA[5-SCF3]]> Me <![CDATA[NH2]]> Bn OMe NMR 2-134 <![CDATA[5-SCF3]]> Me NHMe H OMe NMR 2-135 <![CDATA[5-SCF3]]> Me NHMe Et OMe NMR 2-136 <![CDATA[5-SCF3]]> Me <![CDATA[NMe2]]> Et OMe NMR 2-137 <![CDATA[5-SCF3]]> Me OMe H OMe 224-226 2-138 <![CDATA[5-SCF3]]> Me OMe Et OMe 108-109 2-139 <![CDATA[5-SOCF3]]> Me H Et OH 2-140 <![CDATA[5-SOCF3]]> Me H Et OMe 2-141 <![CDATA[5-SOCF3]]> Me H Et OET 2-142 <![CDATA[5-SOCF3]]> Me H Et On-Pr 2-143 <![CDATA[5-SOCF3]]> Me H Et Oi-Pr 2-144 <![CDATA[5-SOCF3]]> Me H Et Ot-Bu 2-145 <![CDATA[5-SOCF3]]> Me H Et <![CDATA[OCH2C≡CH]]> 2-146 <![CDATA[5-SOCF3]]> Me H Et <![CDATA[NH2]]> 2-147 <![CDATA[5-SOCF3]]> Me H Et NHMe NMR 2-148 <![CDATA[5-SOCF3]]> Me H Et NHEt 2-149 <![CDATA[5-SOCF3]]> Me H Et NH-i-Pr 2-150 <![CDATA[5-SOCF3]]> Me H Et NH-c-Pr

[0941] [Table 2-6]

[0942] Continuation of Table 2

[0943] compound number <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 7 > 物性值 2-151 <![CDATA[5-SOCF3]]> Me H Et <![CDATA[NHCH2CF3]]> 2-152 <![CDATA[5-SOCF3]]> Me H Et <![CDATA[NHCH2CHF2]]> 2-153 <![CDATA[5-SOCF3]]> Me H Et <![CDATA[NMe2]]> 2-154 <![CDATA[5-SOCF3]]> Me H Et <![CDATA[NEt2]]> 2-155 <![CDATA[5-SOCF3]]> Me H Et N(Me)Et 2-156 <![CDATA[5-SOCF3]]> Me H Et N(Me)-i-Pr 2-157 <![CDATA[5-SOCF3]]> Me H Et <![CDATA[N HSO2NMe2]]> 2-158 <![CDATA[5-SOCF3]]> Me H Et 吡咯烷-1-基 2-159 <![CDATA[5-SOCF3]]> Me H <![CDATA[CH2CF3]]> OMe NMR 2-160 <![CDATA[5-SOCF3]]> Me Me H OMe 2-161 <![CDATA[5-SOCF3]]> Me Me Me OMe 2-162 <![CDATA[5-SOCF3]]> Me Me Et OH 2-163 <![CDATA[5-SOCF3]]> Me Me Et OMe 166-167 2-164 <![CDATA[5-SOCF3]]> Me Me Et OEt 2-165 <![CDATA[5-SOCF3]]> Me Me Et NHMe NMR 2-166 <![CDATA[5-SOCF3]]> Me Me Et <![CDATA[NMe2]]> 2-167 <![CDATA[5-SOCF3]]> Me Me i-Pr OMe 2-168 <![CDATA[5-SOCF3]]> Me Me t-Bu OMe 2-169 <![CDATA[5-SOCF3]]> Me Me <![CDATA[CH2CF3]]> OMe 2-170 <![CDATA[5-SOCF3]]> Me Me <![CDATA[CH2CH=CH2]]> OMe 2-171 <![CDATA[5-SOCF3]]> Me Me <![CDATA[CH2CHF2]]> OMe 2-172 <![CDATA[5-SOCF3]]> Me Me <![CDATA[CH2CO2H]]> OMe 2-173 <![CDATA[5-SOCF3]]> Me Me Bn OMe 2-174 <![CDATA[5-SOCF3]]> Me Me <![CDATA[CH2(4-Cl-Ph)]]> OMe 2-175 <![CDATA[5-SOCF3]]> Me Me <![CDATA[CH(CH3)Ph]]> OMe 2-176 <![CDATA[5-SOCF3]]> Me Me <![CDATA[CH2CH2(4-CI-Ph)]]> OMe 2-177 <![CDATA[5-SOCF3]]> Me <![CDATA[CH2CO2CH3]]> Et OMe 2-178 <![CDATA[5-SOCF3]]> Me <![CDATA[NH2]]> H OMe 2-179 <![CDATA[5-SOCF3]]> Me <![CDATA[NH2]]> Me OMe 2-180 <![CDATA[5-SOCF3]]> Me <![CDATA[NH2]]> Et OMe

[0944] [Table 2-7]

[0945] Continuation of Table 2

[0946] 化合物编号 <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 7 > 物性值 2-181 <![CDATA[5-SOCF3]]> Me <![CDATA[NH2]]> Et OEt NMR 2-182 <![CDATA[5-SOCF3]]> Me <![CDATA[NH2]]> i-Pr OMe 2-183 <![CDATA[5-SOCF3]]> Me <![CDATA[NH2]]> n-Pr OMe 2-184 <![CDATA[5-SOCF3]]> Me <![CDATA[NH2]]> n-Bu OMe 2-185 <![CDATA[5-SOCF3]]> Me <![CDATA[NH2]]> n-Bu O-n-Bu 2-186 <![CDATA[5-SOCF3]]> Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> OMe 2-187 <![CDATA[5-SOCF3]]> Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> OEt 2-188 <![CDATA[5-SOCF3]]> Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> <![CDATA[NMe2]]> 2-189 <![CDATA[5-SOCF3]]> Me <![CDATA[NH2]]> Bn OBn 2-190 <![CDATA[5-SOCF3]]> Me <![CDATA[NH2]]> Bn OMe 2-191 <![CDATA[5-SOCF3]]> Me NHMe H OMe 2-192 <![CDATA[5-SOCF3]]> Me NHMe Et OMe 2-193 <![CDATA[5-SOCF3]]> Me <![CDATA[NMe2]]> Et OMe 2-194 <![CDATA[5-SOCF3]]> Me OMe H OMe 2-195 <![CDATA[5-SOCF3]]> Me OMe Et OMe 2-196 <![CDATA[5-SO2CF3]]> Me H Et OH 2-197 <![CDATA[5-SO2CF3]]> Me H Et OMe 2-198 <![CDATA[5-SO2CF3]]> Me H Et OEt 2-199 <![CDATA[5-SO2CF3]]> Me H Et O-n-Pr 2-200 <![CDATA[5-SO2CF3]]> Me H Et O-i-Pr 2-201 <![CDATA[5-SO2CF3]]> Me H Et O-t-Bu 2-202 <![CDATA[5-SO2CF3]]> Me H Et <![CDATA[OCH2C≡CH]]> 2-203 <![CDATA[5-SO2CF3]]> Me H Et <![CDATA[NH2]]> 2-204 <![CDATA[5-SO2CF3]]> Me H Et NHMe 203-204 2-205 <![CDATA[5-SO2CF3]]> Me H Et NHEt 2-206 <![CDATA[5-SO2CF3]]> Me H Et NH-i-Pr 2-207 <![CDATA[5-SO2CF3]]> Me H Et NH-c-Pr 2-208 <![CDATA[5-SO2CF3]]> Me H Et <![CDATA[NHCH2CF3]]> 2-209 <![CDATA[5-SO2CF3]]> Me H Et <![CDATA[NHCH2CHF2]]> 2-210 <![CDATA[5-SO2CF3]]> Me H Et <![CDATA[NMe2]]>

[0947] [Table 2-8]

[0948] Continuation of Table 2

[0949] 化合物编号 <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 7 > 物性值 2-211 <![CDATA[5-SO2CF3]]> Me H Et <![CDATA[NEt2]]> 2-212 <![CDATA[5-SO2CF3]]> Me H Et N(Me)Et 2-213 <![CDATA[5-SO2CF3]]> Me H Et N(Me)-i-Pr 2-214 <![CDATA[5-SO2CF3]]> Me H Et <![CDATA[NHSO2NMe2]]> 2-215 <![CDATA[5-SO2CF3]]> Me H Et 吡咯烷-1-基 2-216 <![CDATA[5-SO2CF3]]> Me H <![CDATA[CH2CF3]]> OMe NMR 2-217 <![CDATA[5-SO2CF3]]> Me Me H OMe 2-218 <![CDATA[5-SO2CF3]]> Me Me Me OMe 2-219 <![CDATA[5-SO2CF3]]> Me Me Et OH 249-250 2-220 <![CDATA[5-SO2CF3]]> Me Me Et OMe 88-89 2-221 <![CDATA[5-SO2CF3]]> Me Me Et OEt NMR 2-222 <![CDATA[5-SO2CF3]]> Me Me Et Me 179-180 2-223 <![CDATA[5-SO2CF3]]> Me Me Et <![CDATA[NH2]]> 239-240 2-224 <![CDATA[5-SO2CF3]]> Me Me Et NHAc 181-184 2-225 <![CDATA[5-SO2CF3]]> Me Me Et NHMe 199-200 2-226 <![CDATA[5-SO2CF3]]> Me Me Et <![CDATA[NMe2]]> 191-193 2-227 <![CDATA[5-SO2CF3]]> Me Me Et N(Me)OMe 141-143 2-228 <![CDATA[5-SO2CF3]]> Me Me i-Pr OMe 2-229 <![CDATA[5-SO2CF3]]> Me Me i-Pr OEt 2-230 <![CDATA[5-SO2CF3]]> Me Me t-Bu OMe 2-231 <![CDATA[5-SO2CF3]]> Me Me <![CDATA[CH2CF3]]> OMe 186-187 2-232 <![CDATA[5-SO2CF3]]> Me Me <![CDATA[CH2CH=CH2]]> OMe 2-233 <![CDATA[5-SO2CF3]]> Me Me <![CDATA[CH2CHF2]]> OMe 2-234 <![CDATA[5-SO2CF3]]> Me Me <![CDATA[CH2CO2H]]> OMe 2-235 <![CDATA[5-SO2CF3]]> Me Me Bn OMe 2-236 <![CDATA[5-SO2CF3]]> Me Me <![CDATA[CH2(4-Cl-Ph)]]> OMe 2-237 <![CDATA[5-SO2CF3]]> Me Me <![CDATA[CH(CH3)Ph]]> OMe 2-238 <![CDATA[5-SO2CF3]]> Me Me <![CDATA[CH2CH2(4-CI-Ph)]]> OMe 2-239 <![CDATA[5-SO2CF3]]> Me <![CDATA[CH2CO2CH3]]> Et OMe 2-240 <![CDATA[5-SO2CF3]]> Me <![CDATA[NH2]]> H OMe

[0950] [Table 2-9]

[0951] Continuation of Table 2

[0952] 化合物编号 <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 7 > 物性值 2-241 <![CDATA[5-SO2CF3]]> Me <![CDATA[NH2]]> Me OMe 2-242 <![CDATA[5-SO2CF3]]> Me <![CDATA[NH2]]> Et OMe 2-243 <![CDATA[5-SO2CF3]]> Me <![CDATA[NH2]]> Et OEt NMR 2-244 <![CDATA[5-SO2CF3]]> Me <![CDATA[NH2]]> i-Pr OMe 2-245 <![CDATA[5-SO2CF3]]> Me <![CDATA[NH2]]> n-Pr OMe 2-246 <![CDATA[5-SO2CF3]]> Me <![CDATA[NH2]]> n-Bu OMe 2-247 <![CDATA[5-SO2CF3]]> Me <![CDATA[NH2]]> n-Bu O-n-Bu 2-248 <![CDATA[5-SO2CF3]]> Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> OMe 2-249 <![CDATA[5-SO2CF3]]> Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> OEt 137-138 2-250 <![CDATA[5-SO2CF3]]> Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> <![CDATA[NMe2]]> 207-208 2-251 <![CDATA[5-SO2CF3]]> Me <![CDATA[NH2]]> Bn OBn 2-252 <![CDATA[5-SO2CF3]]> Me <![CDATA[NH2]]> Bn OMe 2-253 <![CDATA[5-SO2CF3]]> Me NHMe H OMe 2-254 <![CDATA[5-SO2CF3]]> Me NHMe Et OMe 2-255 <![CDATA[5-SO2CF3]]> Me <![CDATA[NMe2]]> Et OMe 2-256 <![CDATA[5-SO2CF3]]> Me OMe H OMe 2-257 <![CDATA[5-SO2CF3]]> Me OMe Et OMe 2-258 5-Me-6-Br Me Me Et Me 192-193 2-259 5,7-di-Br Me H Et OMe 127-128 2-260 5,7-di-Cl Me H Et OMe NMR 2-261 5-Me-6,7-di-Br Me Me Et Me 221-224 2-262 H Me <![CDATA[NH2]]> i-Pr OMe NMR 2-263 H Me <![CDATA[NH2]]> i-Pr OH 183-184 2-264 H Me <![CDATA[NH2]]> i-Pr NHEt 2-265 H Me <![CDATA[NH2]]> i-Pr <![CDATA[NEt2]]> 2-266 H Me <![CDATA[NH2]]> i-Pr <![CDATA[NHCH2CF3]]> 188-189 2-267 H Me <![CDATA[NH2]]> i-Pr 吡咯烷-1-基 2-268 H Me <![CDATA[NH2]]> i-Pr N(Me)OMe 2-269 H Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> OH NMR 2-270 H Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> OMe NMR

[0953] [Table 2-10]

[0954] Continuation of Table 2

[0955] Compound No. <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 7 > Physical properties 2-271 H Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> NHE 2-272 H Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> <![CDATA[NEt2]]> 2-273 H Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> <![CDATA[NHCH2CF3]]> 2-274 H Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> Pyrrolidin-1-yl 2-275 H Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> N(Me)OMe NMR 2-276 5-Me Me <![CDATA[NH2]]> E <![CDATA[NMe2]]> 175-176 2-277 5-Me Me <![CDATA[NH2]]> E <![CDATA[NEt2]]> 161-162 2-278 5-Me Me <![CDATA[NH2]]> E NH(thietan-3-yl) 199-200 2-279 5-Me Me <![CDATA[NH2]]> E NHE 2-280 5-Me Me <![CDATA[NH2]]> E NH(1,1-dioxothietane-3-yl) 2-281 5-Me Me <![CDATA[NH2]]> E <![CDATA[NHCH2CF3]]> 194-195 2-282 5-Me Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> oH NMR 2-283 5-Me Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> OMe NMR 2-284 5-Me Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> <![CDATA[NHCH2CF3]]> 2-285 5-Me Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> <![CDATA[NEt2]]> NMR 2-286 5-Me Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> NHE NMR 2-287 5-Me Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> Pyrrolidin-1-yl 2-288 5-Me Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> N(Me)OMe NMR 2-289 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr <![CDATA[NHNH2]]> NMR 2-290 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Me NHE 193-194 2-291 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Me <![CDATA[NH2]]> 233-234 2-292 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Me OH 161-162 2-293 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Me OPh 69-70 2-294 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Me Oc-Bu NMR 2-295 <![CDATA[5.CF3]]> Me <![CDATA[NH2]]> E NH-c-Pr 2-296 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> E NHP 2-297 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> E NH(4-OMePh) 2-298 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> E <![CDATA[NH(4-CF3Ph)]]> 2-299 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> E <![CDATA[NHCH2CH2Cl]]> 2-300 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> E NHOMe

[0956] [Table 2-11]

[0957] Continuation of Table 2

[0958] Compound No. <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 7 > Physical properties 2-301 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> E NH(thietan-3-yl) 2-302 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> E <![CDATA[NHCH2CF3]]> NMR 2-303 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> E <![CDATA[NHCH2CN]]> 2-304 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> E NHOE NMR 2-305 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> E NHO-i-Pr NMR 2-306 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> E NHO-n-Pr NMR 2-307 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> E <![CDATA[NHCH2CHF2]]> 2-308 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> E NH(3,3-difluorocyclobutane) NMR 2-309 5-CF3 Me <![CDATA[NH2]]> E <![CDATA[NMe2]]> 2-310 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> E <![CDATA[NEt2]]> NMR 2-311 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> E <![CDATA[N(Me)CH2C≡CH]]> NMR 2-312 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> E <![CDATA[NH(CH2C≡CH)]]> NMR 2-313 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> E <![CDATA[NHOCH2CH=CH2]]> NMR 2-314 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> E N(Me)Et NMR 2-315 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> E N(Me)-i-Pr NMR 2-316 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> E N(Et)-i-Pr NMR 2-317 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> E N(Me)OMe NMR 2-318 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> E NH(tetrahydrofuran-3-yl) 2-319 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> E Pyrrolidin-1-yl NMR 2-320 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> E 3-Pyrrolidine-1-yl 2-321 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> E Morpholin-4-yl NMR 2-322 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> E 3,3,4,4-Tetrafluoropyrrolidin-1-yl NMR 2-323 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> E Thiazolidin-3-yl NMR 2-324 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> E NH(thiazol-2-yl) NMR 2-325 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> E <![CDATA[NHCH2CHF2]]> NMR 2-326 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> E <![CDATA[NHNMe2]]> NMR 2-327 5-Me Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> <![CDATA[NHCH2CH2F]]> NMR 2-328 5-Me Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> <![CDATA[NHCH2CHF2]]> NMR 2-329 5-Me Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> NH-c-Pr NMR 2-330 5-Me Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> NHCH(Me)-c-Pr NMR

[0959] [Table 2-12]

[0960] Continuation of Table 2

[0961] Compound No. <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > R7 Physical property value 2-331 5-Me Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> <![CDATA[NHCH2CH=CH0]]> NMR 2-332 5-Me Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> <![CDATA[NHCH2CH2OMe]]> NMR 2-333 5-Me Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> NH-oxacyclopentane-2-one-3-yl NMR 2-334 5-Me Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> NH[(1R)-2-methoxy-1-methylethyl] NMR 2-335 5-Me Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> <![CDATA[NHCH2CH(OMe)2]]> NMR 2-336 5-Me Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> NHOMe NMR 2-337 5-Me Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> NHOE NMR 2-338 5-Me Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> <![CDATA[NHOCH2CH=CH2]]> NMR 2-339 5-Me Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> N(Me)Et NMR 2-340 5-Me Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> N(Me)-i-Pr NMR 2-341 5-Me Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> N(Et)-i-Pr NMR 2-342 5-Me Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> 3,3,4,4-Tetrafluoropyrrolidin-1-yl NMR 2-343 5-Me Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> <![CDATA[N(Me)CH2C≡CH]]> NMR 2-344 5-Me Me <![CDATA[NH2]]> <![CDATA[CH2CF3]]> N(Me)OH NMR 2-345 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Me N(Me)OMe NMR 2-346 5-Me Me <![CDATA[NH2]]> E N(Me)OMe NMR

[0962] [Chemical Formula 29]

[0963]

[0964] The position numbers in the table are the numbers defined in the general formula (1c).

[0965] [Table 3-1]

[0966] Table 3

[0967] Compound No. <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 5 > Q Physical properties 3-1 H Me Me E H H 3-2 H Me Me E H Cl 116-118 3-3 H Me Me E H C(Me)=N-OEt 142-143 3-4 H Me Me <![CDATA[CH2CF3]]> H H 145-146 3-5 H Me Me <![CDATA[CH2CF3]]> H Cl 3-6 5-Me Me Me H H Cl 212-213 3-7 5-Me Me Me And H F 3-8 5-Me Me Me And H Cl 133-135 3-9 5-Me Me Me And H OMe 130-131 3-10 5-Me Me Me And H OEt 153-155 3-11 5-Me Me Me And H SMe 87-89 3-12 5-Me Me Me And H SOMe 202-203 3-13 5-Me Me Me And H <![CDATA[C(OEt)=CH2]]> 90-93 3-14 5-Me Me <![CDATA[CONH2]]> And H OEt 224-225 3-15 5-Me Me <![CDATA[NH2]]> Me H <![CDATA[SCH2(4-t-BuPh)]]> NMR 3-16 5-Me Me <![CDATA[NH2]]> And H F 87-88 3-17 5-Me Me <![CDATA[NH2]]> And H Cl 131-132 3-18 5-Me Me <![CDATA[NH2]]> And H CN 235-237 3-19 5-Me Me <![CDATA[NH2]]> And H <![CDATA[CF3]]> NMR 3-20 5-Me Me <![CDATA[NH2]]> And H <![CDATA[CH2OH]]> 134-136 3-21 5-Me Me <![CDATA[NH2]]> And H <![CDATA[CH(OH)CH3]]> NMR 3-22 5-Me Me <![CDATA[NH2]]> And H <![CDATA[CH(OH)CH2OH]]> NMR 3-23 5-Me Me <![CDATA[NH2]]> And H <![CDATA[CH=CH2]]> NMR 3-24 5-Me Me <![CDATA[NH2]]> And H <![CDATA[C(Me)=CH2]]> NMR 3-25 5-Me Me <![CDATA[NH2]]> And H CH=N-NHMe 84-85 3-26 5-Me Me <![CDATA[NH2]]> And H CH=N-OME 212-213 3-27 5-Me Me <![CDATA[NH2]]> And H <![CDATA[SCF3]]> 116-117 3-28 5-Me Me <![CDATA[NH2]]> And H <![CDATA[SCH2(4-t-BuPh)]]> 116-117 3-29 5-Me Me <![CDATA[NH2]]> And H SMe 165-166 3-30 5-Me Me <![CDATA[NH2]]> And H SOMe

[0968] [Table 3-2]

[0969] Continued Table 3

[0970]

[0971] [Table 3-3]

[0972] Continued Table 3

[0973]

[0974] The "*" in the compound number indicates the Z isomer.

[0975] [Table 3-4]

[0976] Continued Table 3

[0977]

[0978] The "*" in the compound number indicates the Z isomer.

[0979] [Table 3-5]

[0980] Continued Table 3

[0981]

[0982] The "●" in the structural formula indicates the bonding position.

[0983] [Table 3-6]

[0984] Continued Table 3

[0985]

[0986] The "●" in the structural formula indicates the bonding position.

[0987] [Table 3-7]

[0988] Continued Table 3

[0989]

[0990] The "●" in the structural formula indicates the bonding position.

[0991] [Table 3-8]

[0992] Continued from Table 3

[0993] 化合物编号 <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 5 > Q 物性值 3-165 H Me <![CDATA[NH2]]> And H <![CDATA[N(Me)CO2Me]]> 3-166 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> And H <![CDATA[N(Et)CO2Me]]> 3-167 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> iPr H <![CDATA[N(Et)CO2Me]]> 3-168 5-Me Me <![CDATA[NH2]]> And H <![CDATA[N(Et)CO2Me]]> 3-169 H Me <![CDATA[NH2]]> And H <![CDATA[N(Et)CO2Me]]> 3-170 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> And H <![CDATA[NHCO2Me]]> 3-171 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> iPr H <![CDATA[NHCO2Me]]> 3-172 5-Me Me <![CDATA[NH2]]> And H <![CDATA[NHCO2Me]]> 3-173 H Me <![CDATA[NH2]]> And H <![CDATA[NHCO2Me]]> 3-174 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> And H <![CDATA[NHCO2Et]]> 3-175 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> iPr H <![CDATA[NHCO2Et]]> 3-176 5-Me Me <![CDATA[NH2]]> And H <![CDATA[NHCO2Et]]> 3-177 H Me <![CDATA[NH2]]> And H <![CDATA[NHCO2Et]]> 3-178 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> And H N(Me)Ac 3-179 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> iPr H N(Me)Ac 3-180 5-Me Me <![CDATA[NH2]]> And H N(Me)Ac 3-181 H Me <![CDATA[NH2]]> And H N(Me)Ac 3-182 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> And H N(Et)Ac 3-183 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> iPr H N(Et)Ac 3-184 5-Me Me <![CDATA[NH2]]> And H N(Et)Ac 3-185 H Me <![CDATA[NH2]]> And H N(Et)Ac 3-186 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> And H <![CDATA[N(NH2)CO2Me]]> 3-187 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> iPr H <![CDATA[N(NH2)CO2Me]]> 3-188 5-Me Me <![CDATA[NH2]]> And H <![CDATA[N(NH2)CO2Me]]> 3-189 H Me <![CDATA[NH2]]> And H <![CDATA[N(NH2)CO2Me]]>

[0994] [Table 3-9]

[0995] Continued from Table 3

[0996]

[0997] [Table 3-10]

[0998] Continued from Table 3

[0999] 化合物编号 <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 5 > Q 物性值 3-210 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> And H <![CDATA[N(Me)C(=O)NMe2]]> 3-211 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> iPr H <![CDATA[N(Me)C(=O)NMe2]]> 3-212 5-Me Me <![CDATA[NH2]]> And H <![CDATA[N(Me)C(=O)NMe2]]> 3-213 H Me <![CDATA[NH2]]> And H <![CDATA[N(Me)C(=O)NMe2]]> 3-214 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> And H <![CDATA[NHC(=O)CH2OMe]]> 3-215 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> iPr H <![CDATA[NHC(=O)CH2OMe]]> 3-216 5-Me Me <![CDATA[NH2]]> And H <![CDATA[NHC(=O)CH2OMe]]> 3-217 H Me <![CDATA[NH2]]> And H <![CDATA[NHC(=O)CH2OMe]]> 3-218 H Me <![CDATA[NH2]]> Me 4′-Me <![CDATA[CO2Me]]> 3-219 H Me <![CDATA[NH2]]> Me 4′-Me <![CDATA[SO2Me]]> 3-220 H Me <![CDATA[NH2]]> Me 4′-Me <![CDATA[SO2NHMe]]> 3-221 H Me <![CDATA[NH2]]> And 4′-Me <![CDATA[CO2Me]]> 3-222 H Me <![CDATA[NH2]]> And 4′-Me <![CDATA[SO2Me]]> 3-223 H Me <![CDATA[NH2]]> And 4′-Me <![CDATA[SO2NHMe]]> 3-224 H Me <![CDATA[NH2]]> i-Pr 4′-Me <![CDATA[CO2Me]]> 3-225 H Me <![CDATA[NH2]]> i-Pr 4′-Me <![CDATA[SO2Me]]> 3-226 H Me <![CDATA[NH2]]> i-Pr 4′-Me <![CDATA[SO2NHMe]]> 3-227 5-Me Me <![CDATA[NH2]]> Me 4′-Me <![CDATA[CO2Me]]> 3-228 5-Me Me <![CDATA[NH2]]> Me 4′-Me <![CDATA[SO2Me]]> 3-229 5-Me Me <![CDATA[NH2]]> Me 4′-Me <![CDATA[SO2NHMe]]> 3-230 5-Me Me <![CDATA[NH2]]> i-Pr 4′-Me CO2Me 3-231 5-Me Me <![CDATA[NH2]]> i-Pr 4′-Me <![CDATA[SO2Me]]> 3-232 5-Me Me <![CDATA[NH2]]> i-Pr 4′-Me <![CDATA[SO2NHMe]]> 3-233 5-OMe Me <![CDATA[NH2]]> Me 4′-Me <![CDATA[CO2Me]]> 3-234 5-OMe Me <![CDATA[NH2]]> Me 4′-Me <![CDATA[SO2Me]]> 3-235 5-OMe Me <![CDATA[NH2]]> Me 4′-Me <![CDATA[SO2NHMe]]> 3-236 5-OMe Me <![CDATA[NH2]]> And 4′-Me <![CDATA[CO2Me]]> 3-237 5-OMe Me <![CDATA[NH2]]> And 4′-Me <![CDATA[SO2Me]]> 3-238 5-OMe Me <![CDATA[NH2]]> And 4′-Me <![CDATA[SO2NHMe]]> 3-239 5-OMe Me <![CDATA[NH2]]> i-Pr 4′-Me <![CDATA[CO2Me]]> 3-240 5-OMe Me <![CDATA[NH2]]> i-Pr 4′-Me <![CDATA[SO2Me]]> 3-241 5-OMe Me <![CDATA[NH2]]> i-Pr 4′-Me <![CDATA[SO2NHMe]]>

[1000] [Table 3-11]

[1001] Continued from Table 3

[1002] 化合物编号 <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 5 > Q 物性值 3-242 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Me 4′-Me <![CDATA[CO2Me]]> 3-243 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Me 4′-Me <![CDATA[SO2Me]]> 3-244 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Me 4′-Me <![CDATA[SO2NHMe]]> 3-245 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> And 4′-Me <![CDATA[CO2Me]]> 3-246 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> And 4′-Me <![CDATA[SO2Me]]> 3-247 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> And 4′-Me <![CDATA[SO2NHMe]]> 3-248 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> i-Pr 4′-Me <![CDATA[CO2Me]]> 3-249 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> i-Pr 4′-Me <![CDATA[SO2Me]]> 3-250 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> i-Pr 4′-Me <![CDATA[SO2NHMe]]> 3-251 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Me 4′-Me <![CDATA[CO2Me]]> 3-252 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Me 4′-Me <![CDATA[SO2Me]]> 3-253 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Me 4′-Me <![CDATA[SO2NHMe]]> 3-254 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> And 4′-Me <![CDATA[CO2Me]]> 3-255 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr 4′-Me <![CDATA[CO2Me]]> 3-256 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr 4′-Me <![CDATA[SO2Me]]> 3-257 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr 4′-Me <![CDATA[SO2NHMe]]> 3-258 H Me Me Me 4′-Me <![CDATA[CO2Me]]> 3-259 H Me Me Me 4′-Me <![CDATA[SO2Me]]> 3-260 H Me Me Me 4′-Me <![CDATA[SO2NHMe]]> 3-261 H Me Me Et 4′-Me <![CDATA[CO2Me]]> 3-262 H Me Me Et 4′-Me <![CDATA[SO2Me]]> 3-263 H Me Me Et 4′-Me <![CDATA[SO2NHMe]]> 3-264 H Me Me i-Pr 4′-Me <![CDATA[CO2Me]]> 3-265 H Me Me i-Pr 4′-Me <![CDATA[SO2Me]]> 3-266 H Me Me i-Pr 4′-Me <![CDATA[SO2NHMe]]> 3-267 5-Me Me Me Me 4′-Me <![CDATA[CO2Me]]> 3-268 5-Me Me Me Me 4′-Me <![CDATA[SO2Me]]> 3-269 5-Me Me Me Me 4′-Me <![CDATA[SO2NHMe]]> 3-270 5-Me Me Me Et 4′-Me <![CDATA[CO2Me]]> 3-271 5-Me Me Me Et 4′-Me <![CDATA[SO2Me]]> 3-272 5-Me Me Me Et 4′-Me <![CDATA[SO2NHMe]]>

[1003] [Table 3-12]

[1004] Continued from Table 3

[1005] 化合物编号 <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 5 > Q 物性值 3-273 5-Me Me Me i-Pr 4′-Me <![CDATA[CO2Me]]> 3-274 5-Me Me Me i-Pr 4′-Me <![CDATA[SO2Me]]> 3-275 5-Me Me Me i-Pr 4′-Me <![CDATA[SO2NHMe]]> 3-276 5-OMe Me Me Me 4′-Me <![CDATA[CO2Me]]> 3-277 5-OMe Me Me Me 4′-Me <![CDATA[SO2Me]]> 3-278 5-OMe Me Me Me 4′-Me <![CDATA[SO2NHMe]]> 3-279 5-OMe Me Me Et 4′-Me <![CDATA[CO2Me]]> 3-280 5-OMe Me Me Et 4′-Me <![CDATA[SO2Me]]> 3-281 5-OMe Me Me Et 4′-Me <![CDATA[SO2NHMe]]> 3-282 5-OMe Me Me i-Pr 4′-Me <![CDATA[CO2Me]]> 3-283 5-OMe Me Me i-Pr 4′-Me <![CDATA[SO2Me]]> 3-284 5-OMe Me Me i-Pr 4′-Me <![CDATA[SO2NHMe]]> 3-285 <![CDATA[5-CHF2]]> Me Me Me 4′-Me <![CDATA[CO2Me]]> 3-286 <![CDATA[5-CHF2]]> Me Me Me 4′-Me <![CDATA[SO2Me]]> 3-287 <![CDATA[5-CHF2]]> Me Me Me 4′-Me <![CDATA[SO2NHMe]]> 3-288 <![CDATA[5-CHF2]]> Me Me Et 4′-Me <![CDATA[CO2Me]]> 3-289 <![CDATA[5-CHF2]]> Me Me Et 4′-Me <![CDATA[SO2Me]]> 3-290 <![CDATA[5-CHF2]]> Me Me Et 4′-Me <![CDATA[SO2NHMe]]> 3-291 <![CDATA[5-CHF2]]> Me Me i-Pr 4′-Me <![CDATA[CO2Me]]> 3-292 <![CDATA[5-CHF2]]> Me Me i-Pr 4′-Me <![CDATA[SO2Me]]> 3-293 <![CDATA[5-CHF2]]> Me Me i-Pr 4′-Me <![CDATA[SO2NHMe]]> 3-294 <![CDATA[5-CF3]]> Me Me Me 4′-Me <![CDATA[CO2Me]]> 3-295 <![CDATA[5-CF3]]> Me Me Me 4′-Me <![CDATA[SO2Me]]> 3-296 <![CDATA[5-CF3]]> Me Me Me 4′-Me <![CDATA[SO2NHMe]]> 3-297 <![CDATA[5-CF3]]> Me Me Et 4′-Me <![CDATA[CO2Me]]> 3-298 <![CDATA[5-CF3]]> Me Me Et 4′-Me <![CDATA[SO2Me]]> 3-299 5-CF3 Me Me Et 4′-Me <![CDATA[SO2NHMe]]> 3-300 <![CDATA[5-CF3]]> Me Me i-Pr 4′-Me <![CDATA[CO2Me]]> 3-301 <![CDATA[5-CF3]]> Me Me i-Pr 4′-Me <![CDATA[SO2Me]]> 3-302 <![CDATA[5-CF3]]> Me Me i-Pr 4′-Me <![CDATA[SO2NHMe]]>

[1006] [Chemical Formula 30]

[1007]

[1008] The position numbers in the table are the numbers defined in the general formula (1d).

[1009] [Table 4-1]

[1010] Table 4

[1011] 化合物编号 <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 5 > Q 物性值 4-1 H Me <![CDATA[NH2]]> Me H <![CDATA[CO2Me]]> 4-2 H Me <![CDATA[NH2]]> Me H <![CDATA[SO2Me]]> 4-3 H Me <![CDATA[NH2]]> Me H <![CDATA[SO2NHMe]]> 4-4 H Me <![CDATA[NH2]]> Et H <![CDATA[CO2Me]]> 4-5 H Me <![CDATA[NH2]]> Et H <![CDATA[SO2Me]]> 4-6 H Me <![CDATA[NH2]]> Et H <![CDATA[SO2NHMe]]> 4-7 H Me <![CDATA[NH2]]> i-Pr H <![CDATA[CO2Me]]> 4-8 H Me <![CDATA[NH2]]> i-Pr H <![CDATA[SO2Me]]> 4-9 H Me <![CDATA[NH2]]> i-Pr H <![CDATA[SO2NHMe]]> 4-10 5-Me Me <![CDATA[NH2]]> Me H <![CDATA[CO2Me]]> 4-11 5-Me Me <![CDATA[NH2]]> Me H <![CDATA[SO2Me]]> 4-12 5-Me Me <![CDATA[NH2]]> Me H <![CDATA[SO2NHMe]]> 4-13 5-Me Me <![CDATA[NH2]]> Et H <![CDATA[CO2Me]]> 4-14 5-Me Me <![CDATA[NH2]]> Et H <![CDATA[CONMe2]]> 212-213 4-15 5-Me Me <![CDATA[NH2]]> Et H <![CDATA[SO2Me]]> 72-73 4-16 5-Me Me <![CDATA[NH2]]> Et H <![CDATA[SO2NHMe]]> NMR 4-17 5-Me Me <![CDATA[NH2]]> i-Pr H <![CDATA[CO2Me]]> 4-18 5-Me Me <![CDATA[NH2]]> i-Pr H <![CDATA[SO2Me]]> 4-19 5-Me Me <![CDATA[NH2]]> i-Pr H <![CDATA[SO2NHMe]]> 4-20 5-Me Me <![CDATA[NH2]]> Et 4′-Me Br 224-226 4-21 5-Me Me <![CDATA[NH2]]> Et 4′-Me <![CDATA[CO2H]]> 4-22 5-Me Me <![CDATA[NH2]]> Et 4′-Me <![CDATA[CO2Me]]> 1.3869(21.0℃) 4-23 5-OMe Me <![CDATA[NH2]]> Me H <![CDATA[CO2Me]]> 4-24 5-OMe Me <![CDATA[NH2]]> Me H <![CDATA[SO2Me]]> 4-25 5-OMe Me <![CDATA[NH2]]> Me H <![CDATA[SO2NHMe]]> 4-26 5-OMe Me <![CDATA[NH2]]> Et H <![CDATA[CO2Me]]> 4-27 5-OMe Me <![CDATA[NH2]]> Et H <![CDATA[SO2Me]]> 4-28 5-OMe Me <![CDATA[NH2]]> Et H <![CDATA[SO2NHMe]]> 4-29 5-OMe Me <![CDATA[NH2]]> i-Pr H <![CDATA[CO2Me]]> 4-30 5-OMe Me <![CDATA[NH2]]> i-Pr H <![CDATA[SO2Me]]>

[1012] [Table 4-2]

[1013] Continued from Table 4

[1014] 化合物编号 <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 5 > Q 物性值 4-31 5-OMe Me <![CDATA[NH2]]> i-Pr H <![CDATA[SO2NHMe]]> 4-32 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Me H <![CDATA[CO2Me]]> 4-33 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Me H <![CDATA[SO2Me]]> 4-34 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Me H <![CDATA[SO2NHMe]]> 4-35 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Et H <![CDATA[CO2Me]]> 4-36 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Et H <![CDATA[SO2Me]]> 4-37 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Et H <![CDATA[SO2NHMe]]> 4-38 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> i-Pr H <![CDATA[CO2Me]]> 4-39 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> i-Pr H <![CDATA[SO2Me]]> 4-40 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> i-Pr H <![CDATA[SO2NHMe]]> 4-41 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Me H <![CDATA[CO2Me]]> 4-42 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Me H <![CDATA[SO2Me]]> 4-43 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Me H <![CDATA[SO2NHMe]]> 4-44 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Et H <![CDATA[CO2Me]]> 4-45 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Et H <![CDATA[SO2Me]]> 4-46 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Et H <![CDATA[SO2NHMe]]> NMR 4-47 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr H <![CDATA[CO2Me]]> 4-48 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr H <![CDATA[SO2Me]]> 4-49 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr H <![CDATA[SO2NHMe]]> 118-119 4-50 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr H <![CDATA[SO2NMe2]]> NMR 4-51 H Me Me Me H <![CDATA[CO2Me]]> 4-52 H Me Me Me H <![CDATA[SO2Me]]> 4-53 H Me Me Me H <![CDATA[SO2NHMe]]> 4-54 H Me Me Et H <![CDATA[CO2Me]]> 120-121 4-55 H Me Me Et H <![CDATA[SO2Me]]> 4-56 H Me Me Et H <![CDATA[SO2NHMe]]> 4-57 H Me Me i-Pr H <![CDATA[CO2Me]]> 4-58 H Me Me i-Pr H <![CDATA[SO2Me]]> 4-59 H Me Me i-Pr H <![CDATA[SO2NHMe]]> 4-60 H Me Me <![CDATA[CH2CF3]]> H <![CDATA[C(Me)=N-OCH2CF3]]> NMR

[1015] [Table 4-3]

[1016] Continued from Table 4

[1017] 化合物编号 <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 5 > Q 物性值 4-61 H Me Me <![CDATA[CH2CF3]]> H <![CDATA[CO2Me]]> 133-134 4-62＊ H Me Me <![CDATA[CH2CF3]]> H <![CDATA[CO2Me]]> NMR 4-63 5-Me Me Me Me H <![CDATA[CO2Me]]> 4-64 5-Me Me Me Me H <![CDATA[SO2Me]]> 4-65 5-Me Me Me Me H <![CDATA[SO2NHMe]]> 4-66 5-Me Me Me Et H <![CDATA[CO2Me]]> 4-67 5-Me Me Me Et H SMe NMR 4-68 5-Me Me Me Et H <![CDATA[SO2Me]]> NMR 4-69 5-Me Me Me Et H <![CDATA[SO2NHMe]]> 4-70 5-Me Me Me i-Pr H <![CDATA[CO2Me]]> 4-71 5-Me Me Me i-Pr H <![CDATA[SO2Me]]> 4-72 5-Me Me Me i-Pr H <![CDATA[SO2NHMe]]> 4-73 5-OMe Me Me Me H <![CDATA[CO2Me]]> 4-74 5-OMe Me Me Me H <![CDATA[SO2Me]]> 4-75 5-OMe Me Me Me H <![CDATA[SO2NHMe]]> 4-76 5-OMe Me Me Et H <![CDATA[CO2Me]]> 4-77 5-OMe Me Me Et H <![CDATA[SO2Me]]> 4-78 5-OMe Me Me Et H <![CDATA[SO2NHMe]]> 4-79 5-OMe Me Me i-Pr H <![CDATA[CO2Me]]> 4-80 5-OMe Me Me i-Pr H <![CDATA[SO2Me]]> 4-81 5-OMe Me Me i-Pr H <![CDATA[SO2NHMe]]> 4-82 <![CDATA[5-CHF2]]> Me Me Me H <![CDATA[CO2Me]]> 4-83 <![CDATA[5-CHF2]]> Me Me Me H <![CDATA[SO2Me]]> 4-84 <![CDATA[5-CHF2]]> Me Me Me H <![CDATA[SO2NHMe]]> 4-85 <![CDATA[5-CHF2]]> Me Me Et H <![CDATA[CO2Me]]> 4-86 <![CDATA[5-CHF2]]> Me Me Et H <![CDATA[SO2Me]]> 4-87 <![CDATA[5-CHF2]]> Me Me Et H <![CDATA[SO2NHMe]]> 4-88 <![CDATA[5-CHF2]]> Me Me i-Pr H <![CDATA[CO2Me]]> 4-89 <![CDATA[5-CHF2]]> Me Me i-Pr H <![CDATA[SO2Me]]> 4-90 <![CDATA[5-CHF2]]> Me Me i-Pr H <![CDATA[SO2NHMe]]>

[1018] The "*" in the compound number indicates the Z isomer.

[1019] [Table 4-4]

[1020] Continued from Table 4

[1021] 化合物编号 <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 5 > Q 物性值 4-91 <![CDATA[5-CF3]]> Me Me Me H <![CDATA[CO2Me]]> 4-92 <![CDATA[5-CF3]]> Me Me Me H <![CDATA[SO2Me]]> 4-93 <![CDATA[5-CF3]]> Me Me Me H <![CDATA[SO2NHMe]]> 4-94 <![CDATA[5-CF3]]> Me Me Et H <![CDATA[CO2Me]]> 4-95 <![CDATA[5-CF3]]> Me Me Et H <![CDATA[SO2Me]]> 4-96 <![CDATA[5-CF3]]> Me Me Et H <![CDATA[SO2NHMe]]> 4-97 <![CDATA[5-CF3]]> Me Me i-Pr H <![CDATA[CO2Me]]> 4-98 <![CDATA[5-CF3]]> Me Me i-Pr H <![CDATA[SO2Me]]> 4-99 <![CDATA[5-CF3]]> Me Me i-Pr H <![CDATA[SO2NHMe]]> 4-100 <![CDATA[5-SCF3]]> Me Me Et H Me NMR 4-101＊ <![CDATA[5-SCF3]]> Me Me Et H Me NMR 4-102 <![CDATA[5-SCF3]]> Me Me Et H OH 134-135 4-103 <![CDATA[5-SCF3]]> Me Me Et H <![CDATA[OCH2OMe]]> 72-73 4-104＊ <![CDATA[5-SCF3]]> Me Me Et H <![CDATA[OCH2OMe]]> NMR 4-105 <![CDATA[5-SCF3]]> Me Me Et 4′-Me Br 166 4-106＊ <![CDATA[5-SCF3]]> Me Me Et 4′-Me Br 1.6285(24.2℃) 4-107 <![CDATA[5-SCF3]]> Me Me Et 1′-Me <![CDATA[CO2Me]]> 112-115 4-108 <![CDATA[5-SCF3]]> Me Me Et 4′-Me <![CDATA[CO2Me]]> 1.3494(26.7℃) 4-109＊ <![CDATA[5-SCF3]]> Me Me Et 4′-Me <![CDATA[CO2Me]]> NMR 4-110 5-Br Me Me <![CDATA[CH2CF3]]> H <![CDATA[CO2Me]]> 129-130 4-111 5-I Me Me Et H <![CDATA[CO2Me]]> NMR 4-112 <![CDATA[5-SO2NH2]]> Me Me Et H <![CDATA[CO2Me]]> 177-178 4-113 <![CDATA[5-SO2NMe2]]> Me Me Et H <![CDATA[CO2Me]]> NMR 4-114 6-Br Me Me <![CDATA[CH2CF3]]> H <![CDATA[CO2Me]]> 147-148 4-115 <![CDATA[6-SO2NH2]]> Me Me Et H <![CDATA[CO2Me]]> 89-90 4-116 5,6-di-Br Me Me <![CDATA[CH2CF3]]> H <![CDATA[CO2Me]]> 173-174 4-117 <![CDATA[5-SCF3]]> Me H Et H <![CDATA[SO2Et]]> 1.4796(20.0℃) 4-118 <![CDATA[5-SCF3]]> Me H <![CDATA[CH2CHF2]]> H <![CDATA[SO2Et]]> 1.4029(20.1℃) 4-119 <![CDATA[5-SCF3]]> Me H <![CDATA[CH2CF3]]> H <![CDATA[SO2Et]]> 1.4292(20.1℃) 4-120 <![CDATA[5-SO2CF3]]> Me H <![CDATA[CH2CHF2]]> H <![CDATA[SO2Et]]> 47-48

[1022] The "*" in the compound number indicates the Z isomer.

[1023] [Table 4-5]

[1024] Continued from Table 4

[1025] 化合物编号 <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 5 > Q 物性值 4-121 <![CDATA[5-SO2CF3]]> Me H <![CDATA[CH2CF3]]> H <![CDATA[SO2Et]]> 58-59 4-122 H Me <![CDATA[NH2]]> Me 4′-Me <![CDATA[CO2Me]]> 4-123 H Me <![CDATA[NH2]]> Me 4′-Me <![CDATA[SO2Me]]> 4-124 H Me <![CDATA[NH2]]> Me 4′-Me <![CDATA[SO2NHMe]]> 4-125 H Me <![CDATA[NH2]]> Et 4′-Me <![CDATA[CO2Me]]> 4-126 H Me <![CDATA[NH2]]> Et 4′-Me <![CDATA[SO2Me]]> 4-127 H Me <![CDATA[NH2]]> Et 4′-Me <![CDATA[SO2NHMe]]> 4-128 H Me <![CDATA[NH2]]> i-Pr 4′-Me <![CDATA[CO2Me]]> 4-129 H Me <![CDATA[NH2]]> i-Pr 4′-Me <![CDATA[SO2Me]]> 4-130 H Me <![CDATA[NH2]]> i-Pr 4′-Me <![CDATA[SO2NHMe]]> 4-131 5-Me Me <![CDATA[NH2]]> Me 4′-Me CO2Me 4-132 5-Me Me <![CDATA[NH2]]> Me 4′-Me <![CDATA[SO2Me]]> 4-133 5-Me Me <![CDATA[NH2]]> Me 4′-Me <![CDATA[SO2NHMe]]> 4-134 5-Me Me <![CDATA[NH2]]> Et 4′-Me <![CDATA[SO2Me]]> 4-135 5-Me Me <![CDATA[NH2]]> Et 4′-Me <![CDATA[SO2NHMe]]> 4-136 5-Me Me <![CDATA[NH2]]> i-Pr 4′-Me <![CDATA[CO2Me]]> 4-137 5-Me Me <![CDATA[NH2]]> i-Pr 4′-Me <![CDATA[SO2Me]]> 4-138 5-Me Me <![CDATA[NH2]]> i-Pr 4′-Me <![CDATA[SO2NHMe]]> 4-139 5-OMe Me <![CDATA[NH2]]> Me 4′-Me <![CDATA[CO2Me]]> 4-140 5-OMe Me <![CDATA[NH2]]> Me 4′-Me <![CDATA[SO2Me]]> 4-141 5-OMe Me <![CDATA[NH2]]> Me 4′-Me <![CDATA[SO2NHMe]]> 4-142 5-OMe Me <![CDATA[NH2]]> Et 4′-Me <![CDATA[CO2Me]]> 4-143 5-OMe Me <![CDATA[NH2]]> Et 4′-Me <![CDATA[SO2Me]]> 4-144 5-OMe Me <![CDATA[NH2]]> Et 4′-Me SO2NHMe 4-145 5-OMe Me <![CDATA[NH2]]> i-Pr 4′-Me <![CDATA[CO2Me]]> 4-146 5-OMe Me <![CDATA[NH2]]> i-Pr 4′-Me <![CDATA[SO2Me]]> 4-147 5-OMe Me <![CDATA[NH2]]> i-Pr 4′-Me <![CDATA[SO2NHMe]]> 4-148 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Me 4′-Me <![CDATA[CO2Me]]> 4-149 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Me 4′-Me <![CDATA[SO2Me]]> 4-150 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Me 4′-Me <![CDATA[SO2NHMe]]>

[1026] [Table 4-6]

[1027] Continued from Table 4

[1028] 化合物编号 <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 5 > Q 物性值 4-151 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Et 4′-Me <![CDATA[CO2Me]]> 4-152 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Et 4′-Me <![CDATA[SO2Me]]> 4-153 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Et 4′-Me <![CDATA[SO2NHMe]]> 4-154 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> i-Pr 4′-Me <![CDATA[CO2Me]]> 4-155 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> i-Pr 4′-Me <![CDATA[SO2Me]]> 4-156 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> i-Pr 4′-Me <![CDATA[SO2NHMe]]> 4-157 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Me 4′-Me <![CDATA[CO2Me]]> 4-158 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Me 4′-Me <![CDATA[SO2Me]]> 4-159 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Me 4′-Me <![CDATA[SO2NHMe]]> 4-160 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Et 4′-Me <![CDATA[CO2Me]]> 4-161 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Et 4′-Me <![CDATA[SO2Me]]> 4-162 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Et 4′-Me <![CDATA[SO2NHMe]]> 4-163 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr 4′-Me <![CDATA[CO2Me]]> 4-164 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr 4′-Me <![CDATA[SO2Me]]> 4-165 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr 4′-Me <![CDATA[SO2NHMe]]> 4-166 H Me Me Me 4′-Me <![CDATA[CO2Me]]> 4-167 H Me Me Me 4′-Me <![CDATA[SO2Me]]> 4-168 H Me Me Me 4′-Me <![CDATA[SO2NHMe]]> 4-169 H Me Me Et 4′-Me <![CDATA[CO2Me]]> 4-170 H Me Me Et 4′-Me <![CDATA[SO2Me]]> 4-171 H Me Me Et 4′-Me <![CDATA[SO2NHMe]]> 4-172 H Me Me i-Pr 4′-Me <![CDATA[CO2Me]]> 4-173 H Me Me i-Pr 4′-Me <![CDATA[SO2Me]]> 4-174 H Me Me i-Pr 4′-Me <![CDATA[SO2NHMe]]> 4-175 5-Me Me Me Me 4′-Me <![CDATA[CO2Me]]> 4-176 5-Me Me Me Me 4′-Me <![CDATA[SO2Me]]> 4-177 5-Me Me Me Me 4′-Me <![CDATA[SO2NHMe]]> 4-178 5-Me Me Me Et 4′-Me <![CDATA[CO2Me]]> 4-179 5-Me Me Me Et 4′-Me <![CDATA[SO2Me]]> 4-180 5-Me Me Me Et 4′-Me <![CDATA[SO2NHMe]]>

[1029] [Table 4-7]

[1030] Continued from Table 4

[1031] 化合物编号 <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 5 > Q 物性值 4-181 5-Me Me Me i-Pr 4′-Me <![CDATA[CO2Me]]> 4-182 5-Me Me Me i-Pr 4′-Me <![CDATA[SO2Me]]> 4-183 5-Me Me Me i-Pr 4′-Me <![CDATA[SO2NHMe]]> 4-184 5-OMe Me Me Me 4′-Me <![CDATA[CO2Me]]> 4-185 5-OMe Me Me Me 4′-Me <![CDATA[SO2Me]]> 4-186 5-OMe Me Me Me 4′-Me <![CDATA[SO2NHMe]]> 4-187 5-OMe Me Me Et 4′-Me <![CDATA[CO2Me]]> 4-188 5-OMe Me Me Et 4′-Me <![CDATA[SO2Me]]> 4-189 5-OMe Me Me Et 4′-Me <![CDATA[SO2NHMe]]> 4-190 5-OMe Me Me i-Pr 4′-Me <![CDATA[CO2Me]]> 4-191 5-OMe Me Me i-Pr 4′-Me <![CDATA[SO2Me]]> 4-192 5-OMe Me Me i-Pr 4′-Me <![CDATA[SO2NHMe]]> 4-193 <![CDATA[5-CHF2]]> Me Me Me 4′-Me <![CDATA[CO2Me]]> 4-194 <![CDATA[5-CHF2]]> Me Me Me 4′-Me <![CDATA[SO2Me]]> 4-195 <![CDATA[5-CHF2]]> Me Me Me 4′-Me <![CDATA[SO2NHMe]]> 4-196 <![CDATA[5-CHF2]]> Me Me Et 4′-Me <![CDATA[Co2Me]]> 4-197 <![CDATA[5-CHF2]]> Me Me Et 4′-Me <![CDATA[SO2Me]]> 4-198 <![CDATA[5-CHF2]]> Me Me Et 4′-Me <![CDATA[So2NHMe]]> 4-199 <![CDATA[5-CHF2]]> Me Me i-Pr 4′-Me <![CDATA[CO2Me]]> 4-200 <![CDATA[5-CHF2]]> Me Me i-Pr 4′-Me <![CDATA[SO2Me]]> 4-201 <![CDATA[5-CHF2]]> Me Me i-Pr 4′-Me <![CDATA[SO2NHMe]]> 4-202 <![CDATA[5-CF3]]> Me Me Me 4′-Me <![CDATA[CO2Me]]> 4-203 <![CDATA[5-CF3]]> Me Me Me 4′-Me <![CDATA[SO2Me]]> 4-204 <![CDATA[5-CF3]]> Me Me Me 4′-Me <![CDATA[SO2NHMe]]> 4-205 <![CDATA[5-CF3]]> Me Me Et 4′-Me <![CDATA[CO2Me]]> 4-206 <![CDATA[5-CF3]]> Me Me Et 4′-Me <![CDATA[SO2Me]]> 4-207 <![CDATA[5-CF3]]> Me Me Et 4′-Me <![CDATA[SO2NHMe]]> 4-208 <![CDATA[5-CF3]]> Me Me i-Pr 4′-Me <![CDATA[CO2Me]]> 4-209 <![CDATA[5-CF3]]> Me Me i-Pr 4′-Me <![CDATA[SO2Me]]> 4-210 <![CDATA[5-CF3]]> Me Me i-Pr 4′-Me <![CDATA[SO2NHMe]]>

[1032] [Table 4-8]

[1033] Continued from Table 4

[1034]

[1035] The "●" in the structural formula indicates the bonding position.

[1036] [Table 4-9]

[1037] Continued from Table 4

[1038]

[1039] The "●" in the structural formula indicates the bonding position.

[1040] [Table 4-10]

[1041] Continued from Table 4

[1042]

[1043] The "●" in the structural formula indicates the bonding position.

[1044] [Table 4-11]

[1045] Continued from Table 4

[1046]

[1047] "●" in the structural formula indicates the bonding position.

[1048] [Table 4-12]

[1049] Continued from Table 4

[1050]

[1051] "●" in the structural formula indicates the bonding position.

[1052] [Table 4-13]

[1053] Continued from Table 4

[1054]

[1055] "●" in the structural formula indicates the bonding position.

[1056] [Table 4-14]

[1057] Continued from Table 4

[1058]

[1059] "●" in the structural formula indicates the bonding position.

[1060] [Table 4-15]

[1061] Continued from Table 4

[1062]

[1063] "●" in the structural formula indicates the bonding position.

[1064] [Chemical Formula 31]

[1065]

[1066] The position numbers in the table are the numbers defined in the general formula (1e).

[1067] [Table 5-1]

[1068] Table 5

[1069] 化合物编号 <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 5 > Q 物性值 5-1 H Me <![CDATA[NH2]]> Me H <![CDATA[CO2Me]]> 5-2 H Me <![CDATA[NH2]]> Me H <![CDATA[SO2Me]]> 5-3 H Me <![CDATA[NH2]]> Me H <![CDATA[SO2NHMe]]> 5-4 H Me <![CDATA[NH2]]> Et H <![CDATA[CO2Me]]> 5-5 H Me <![CDATA[NH2]]> Et H <![CDATA[SO2Me]]> 5-6 H Me <![CDATA[NH2]]> Et H <![CDATA[SO2NHMe]]> 5-7 H Me <![CDATA[NH2]]> i-Pr H <![CDATA[CO2Me]]> 5-8 H Me <![CDATA[NH2]]> i-Pr H <![CDATA[SO2Me]]> 5-9 H Me <![CDATA[NH2]]> i-Pr H <![CDATA[SO2NHMe]]> 5-10 5-Me Me <![CDATA[NH2]]> Me H <![CDATA[CO2Me]]> 5-11 5-Me Me <![CDATA[NH2]]> Me H <![CDATA[SO2Me]]> 5-12 5-Me Me <![CDATA[NH2]]> Me H <![CDATA[SO2NHMe]]> 5-13 5-Me Me <![CDATA[NH2]]> Et H Cl 130-131 5-14 5-Me Me <![CDATA[NH2]]> Et H <![CDATA[CO2Me]]> 5-15 5-Me Me <![CDATA[NH2]]> Et H SMe 133-134 5-16 5-Me Me <![CDATA[NH2]]> Et H <![CDATA[SO2Me]]> 181-182 5-17 5-Me Me <![CDATA[NH2]]> Et H <![CDATA[SO2NHMe]]> 5-18 5-Me Me <![CDATA[NH2]]> i-Pr H <![CDATA[CO2Me]]> 5-19 5-Me Me <![CDATA[NH2]]> i-Pr H <![CDATA[SO2Me]]> 5-20 5-Me Me <![CDATA[NH2]]> i-Pr H <![CDATA[SO2NHMe]]> 5-21 5-OMe Me <![CDATA[NH2]]> Me H <![CDATA[CO2Me]]> 5-22 5-OMe Me <![CDATA[NH2]]> Me H <![CDATA[SO2Me]]> 5-23 5-OMe Me <![CDATA[NH2]]> Me H <![CDATA[SO2NHMe]]> 5-24 5-OMe Me <![CDATA[NH2]]> Et H <![CDATA[CO2Me]]> 5-25 5-OMe Me <![CDATA[NH2]]> Et H <![CDATA[SO2Me]]> 5-26 5-OMe Me <![CDATA[NH2]]> Et H <![CDATA[SO2NHMe]]> 5-27 5-OMe Me <![CDATA[NH2]]> i-Pr H <![CDATA[CO2Me]]> 5-28 5-OMe Me <![CDATA[NH2]]> i-Pr H <![CDATA[SO2Me]]> 5-29 5-OMe Me <![CDATA[NH2]]> i-Pr H <![CDATA[SO2NHMe]]> 5-30 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Me H <![CDATA[CO2Me]]>

[1070] [Table 5-2]

[1071] Continued from Table 5

[1072] 化合物编号 <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 5 > Q 物性值 5-31 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Me H <![CDATA[SO2Me]]> 5-32 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Me H <![CDATA[SO2NHMe]]> 5-33 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Et H <![CDATA[CO2Me]]> 5-34 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Et H <![CDATA[SO2Me]]> 5-35 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Et H <![CDATA[SO2NHMe]]> 5-36 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> i-Pr H <![CDATA[CO2Me]]> 5-37 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> i-Pr H <![CDATA[SO2Me]]> 5-38 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> i-Pr H <![CDATA[SO2NHMe]]> 5-39 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Me H <![CDATA[CO2Me]]> 5-40 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Me H <![CDATA[SO2Me]]> 5-41 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Me H <![CDATA[SO2NHMe]]> 5-42 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Et H <![CDATA[CO2Me]]> 5-43 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Et H <![CDATA[SO2Me]]> 5-44 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Et H <![CDATA[SO2NHMe]]> 5-45 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr H <![CDATA[CO2Me]]> 5-46 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr H <![CDATA[SO2Me]]> 5-47 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr H <![CDATA[SO2NHMe]]> 5-48 H Me Me Me H <![CDATA[CO2Me]]> 5-49 H Me Me Me H <![CDATA[SO2Me]]> 5-50 H Me Me Me H <![CDATA[SO2NHMe]]> 5-51 H Me Me Et H <![CDATA[CO2Me]]> 5-52 H Me Me Et H <![CDATA[SO2Me]]> 5-53 H Me Me Et H <![CDATA[SO2NHMe]]> 5-54 H Me Me i-Pr H <![CDATA[CO2Me]]> 5-55 H Me Me i-Pr H <![CDATA[SO2Me]]> 5-56 H Me Me i-Pr H <![CDATA[SO2NHMe]]> 5-57 5-Me Me Me Me H <![CDATA[CO2Me]]> 5-58 5-Me Me Me Me H <![CDATA[SO2Me]]> 5-59 5-Me Me Me Me H <![CDATA[SO2NHMe]]> 5-60 5-Me Me Me Et H <![CDATA[CO2Me]]>

[1073] [Table 5-3]

[1074] Continued from Table 5

[1075] 化合物编号 <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 5 > Q 物性值 5-61 5-Me Me Me Et H <![CDATA[SO2Me]]> 183-184 5-62 5-Me Me Me Et H <![CDATA[SO2NHMe]]> 5-63 5-Me Me Me i-Pr H <![CDATA[CO2Me]]> 5-64 5-Me Me Me i-Pr H <![CDATA[SO2Me]]> 5-65 5-Me Me Me i-Pr H <![CDATA[SO2NHMe]]> 5-66 5-OMe Me Me Me H <![CDATA[CO2Me]]> 5-67 5-OMe Me Me Me H <![CDATA[SO2Me]]> 5-68 5-OMe Me Me Me H <![CDATA[SO2NHMe]]> 5-69 5-OMe Me Me Et H <![CDATA[CO2Me]]> 5-70 5-OMe Me Me Et H <![CDATA[SO2Me]]> 5-71 5-OMe Me Me Et H <![CDATA[SO2NHMe]]> 5-72 5-OMe Me Me i-Pr H <![CDATA[CO2Me]]> 5-73 5-OMe Me Me i-Pr H <![CDATA[SO2Me]]> 5-74 5-OMe Me Me i-Pr H <![CDATA[SO2NHMe]]> 5-75 <![CDATA[5-CHF2]]> Me Me Me H <![CDATA[CO2Me]]> 5-76 <![CDATA[5-CHF2]]> Me Me Me H <![CDATA[SO2Me]]> 5-77 <![CDATA[5-CHF2]]> Me Me Me H <![CDATA[SO2NHMe]]> 5-78 <![CDATA[5-CHF2]]> Me Me Et H <![CDATA[CO2Me]]> 5-79 <![CDATA[5-CHF2]]> Me Me Et H <![CDATA[SO2Me]]> 5-80 <![CDATA[5-CHF2]]> Me Me Et H <![CDATA[SO2NHMe]]> 5-81 <![CDATA[5-CHF2]]> Me Me i-Pr H <![CDATA[CO2Me]]> 5-82 <![CDATA[5-CHF2]]> Me Me i-Pr H <![CDATA[SO2Me]]> 5-83 <![CDATA[5-CHF2]]> Me Me i-Pr H <![CDATA[SO2NHMe]]> 5-84 <![CDATA[5-CF3]]> Me Me Me H <![CDATA[CO2Me]]> 5-85 <![CDATA[5-CF3]]> Me Me Me H <![CDATA[SO2Me]]> 5-86 <![CDATA[5-CF3]]> Me Me Me H <![CDATA[SO2NHMe]]> 5-87 <![CDATA[5-CF3]]> Me Me Et H <![CDATA[CO2Me]]> 5-88 <![CDATA[5-CF3]]> Me Me Et H <![CDATA[SO2Me]]> 5-89 <![CDATA[5-CF3]]> Me Me Et H <![CDATA[SO2NHMe]]> 5-90 <![CDATA[5-CF3]]> Me Me i-Pr H <![CDATA[CO2Me]]>

[1076] [Table 5-4]

[1077] Continued from Table 5

[1078] 化合物编号 <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 5 > Q 物性值 5-91 <![CDATA[5-CF3]]> Me Me i-Pr H <![CDATA[SO2Me]]> 5-92 <![CDATA[5-CF3]]> Me Me i-Pr H <![CDATA[SO2NHMe]]> 5-93 <![CDATA[5-SCF3]]> Me Me Me H C(Me)=N-OMe 141-143 5-94 <![CDATA[5-SCF3]]> Me Me Et H SEt 113-115 5-95 <![CDATA[5-SCF3]]> Me H Et H <![CDATA[CO2H]]> 240-246 5-96 <![CDATA[5-SCF3]]> Me H Et H <![CDATA[CO2Me]]> 178-180 5-97 <![CDATA[5-SCF3]]> Me H Et H CONHMe 187-190 5-98 <![CDATA[5-SCF3]]> Me H Et H <![CDATA[CONMe2]]> 172-175 5-99 <![CDATA[5-SCF3]]> Me H <![CDATA[CH2CF3]]> H <![CDATA[CO2Me]]> 149-152 5-100 <![CDATA[5-SO2CF3]]> Me H <![CDATA[CH2CF3]]> H <![CDATA[CO2Me]]> 155-160 5-101 H Me <![CDATA[NH2]]> Me 6′-Me <![CDATA[CO2Me]]> 5-102 H Me <![CDATA[NH2]]> Me 6′-Me <![CDATA[SO2Me]]> 5-103 H Me <![CDATA[NH2]]> Me 6′-Me <![CDATA[SO2NHMe]]> 5-104 H Me <![CDATA[NH2]]> Et 6′-Me <![CDATA[CO2Me]]> 5-105 H Me <![CDATA[NH2]]> Et 6′-Me <![CDATA[SO2Me]]> 5-106 H Me <![CDATA[NH2]]> Et 6′-Me <![CDATA[SO2NHMe]]> 5-107 H Me <![CDATA[NH2]]> i-Pr 6′-Me <![CDATA[CO2Me]]> 5-108 H Me <![CDATA[NH2]]> i-Pr 6′-Me <![CDATA[SO2Me]]> 5-109 H Me <![CDATA[NH2]]> i-Pr 6′-Me <![CDATA[SO2NHMe]]> 5-110 5-Me Me <![CDATA[NH2]]> Me 6′-Me <![CDATA[CO2Me]]> 5-111 5-Me Me <![CDATA[NH2]]> Me 6′-Me <![CDATA[SO2Me]]> 5-112 5-Me Me <![CDATA[NH2]]> Me 6′-Me <![CDATA[SO2NHMe]]> 5-113 5-Me Me <![CDATA[NH2]]> Et 6′-Me <![CDATA[CO2Me]]> 5-114 5-Me Me <![CDATA[NH2]]> Et 6′-Me <![CDATA[SO2Me]]> 5-115 5-Me Me <![CDATA[NH2]]> Et 6′-Me <![CDATA[SO2NHMe]]> 5-116 5-Me Me <![CDATA[NH2]]> i-Pr 6′-Me <![CDATA[CO2Me]]> 5-117 5-Me Me <![CDATA[NH2]]> i-Pr 6′-Me <![CDATA[SO2Me]]> 5-118 5-Me Me <![CDATA[NH2]]> i-Pr 6′-Me <![CDATA[SO2NHMe]]> 5-119 5-OMe Me <![CDATA[NH2]]> Me 6′-Me <![CDATA[CO2Me]]> 5-120 5-OMe Me <![CDATA[NH2]]> Me 6′-Me <![CDATA[SO2Me]]>

[1079] [Table 5-5]

[1080] Continued from Table 5

[1081] 化合物编号 <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 5 > Q 物性值 5-121 5-OMe Me <![CDATA[NH2]]> Me 6′-Me <![CDATA[SO2NHMe]]> 5-122 5-OMe Me <![CDATA[NH2]]> Et 6′-Me <![CDATA[CO2Me]]> 5-123 5-OMe Me <![CDATA[NH2]]> Et 6′-Me <![CDATA[SO2Me]]> 5-124 5-OMe Me <![CDATA[NH2]]> Et 6′-Me <![CDATA[SO2NHMe]]> 5-125 5-OMe Me <![CDATA[NH2]]> i-Pr 6′-Me <![CDATA[CO2Me]]> 5-126 5-OMe Me <![CDATA[NH2]]> i-Pr 6′-Me <![CDATA[SO2Me]]> 5-127 5-OMe Me <![CDATA[NH2]]> i-Pr 6′-Me <![CDATA[SO2NHMe]]> 5-128 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Me 6′-Me <![CDATA[CO2Me]]> 5-129 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Me 6′-Me <![CDATA[SO2Me]]> 5-130 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Me 6′-Me <![CDATA[SO2NHMe]]> 5-131 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Et 6′-Me <![CDATA[CO2Me]]> 5-132 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Et 6′-Me <![CDATA[SO2Me]]> 5-133 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Et 6′-Me <![CDATA[SO2NHMe]]> 5-134 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> i-Pr 6′-Me <![CDATA[CO2Me]]> 5-135 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> i-Pr 6′-Me <![CDATA[SO2Me]]> 5-136 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> i-Pr 6′-Me <![CDATA[SO2NHMe]]> 5-137 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Me 6′-Me <![CDATA[CO2Me]]> 5-138 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Me 6′-Me <![CDATA[SO2Me]]> 5-139 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Me 6′-Me <![CDATA[SO2NHMe]]> 5-140 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Et 6′-Me <![CDATA[CO2Me]]> 5-141 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Et 6′-Me <![CDATA[SO2Me]]> 5-142 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Et 6′-Me <![CDATA[SO2NHMe]]> 5-143 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr 6′-Me <![CDATA[CO2Me]]> 5-144 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr 6′-Me <![CDATA[SO2Me]]> 5-145 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr 6′-Me <![CDATA[SO2NHMe]]> 5-146 H Me Me Me 6′-Me <![CDATA[CO2Me]]> 5-147 H Me Me Me 6′-Me <![CDATA[SO2Me]]> 5-148 H Me Me Me 6′-Me <![CDATA[SO2NHMe]]> 5-149 H Me Me Et 6′-Me <![CDATA[CO2Me]]> 5-150 H Me Me Et 6′-Me <![CDATA[SO2Me]]>

[1082] [Table 5-6]

[1083] Continued from Table 5

[1084] 化合物编号 <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 5 > Q 物性值 5-151 H Me Me Et 6′-Me <![CDATA[SO2NHMe]]> 5-152 H Me Me i-Pr 6′-Me <![CDATA[CO2Me]]> 5-153 H Me Me i-Pr 6′-Me <![CDATA[SO2Me]]> 5-154 H Me Me i-Pr 6′-Me <![CDATA[SO2NHMe]]> 5-155 5-Me Me Me Me 6′-Me <![CDATA[CO2Me]]> 5-156 5-Me Me Me Me 6′-Me <![CDATA[SO2Me]]> 5-157 5-Me Me Me Me 6′-Me <![CDATA[SO2NHMe]]> 5-158 5-Me Me Me Et 6′-Me <![CDATA[CO2Me]]> 5-159 5-Me Me Me Et 6′-Me <![CDATA[SO2Me]]> 5-160 5-Me Me Me Et 6′-Me <![CDATA[SO2NHMe]]> 5-161 5-Me Me Me i-Pr 6′-Me <![CDATA[CO2Me]]> 5-162 5-Me Me Me i-Pr 6′-Me <![CDATA[SO2Me]]> 5-163 5-Me Me Me i-Pr 6′-Me <![CDATA[SO2NHMe]]> 5-164 5-OMe Me Me Me 6′-Me <![CDATA[CO2Me]]> 5-165 5-OMe Me Me Me 6′-Me <![CDATA[SO2Me]]> 5-166 5-OMe Me Me Me 6′-Me <![CDATA[SO2NHMe]]> 5-167 5-OMe Me Me Et 6′-Me <![CDATA[CO2Me]]> 5-168 5-OMe Me Me Et 6′-Me <![CDATA[SO2Me]]> 5-169 5-OMe Me Me Et 6′-Me <![CDATA[SO2NHMe]]> 5-170 5-OMe Me Me i-Pr 6′-Me <![CDATA[CO2Me]]> 5-171 5-OMe Me Me i-Pr 6′-Me <![CDATA[SO2Me]]> 5-172 5-OMe Me Me i-Pr 6′-Me <![CDATA[SO2NHMe]]> 5-173 5-CHF2 Me Me Me 6′-Me <![CDATA[CO2Me]]> 5-174 <![CDATA[5-CHF2]]> Me Me Me 6′-Me <![CDATA[SO2Me]]> 5-175 <![CDATA[5-CHF2]]> Me Me Me 6′-Me <![CDATA[SO2NHMe]]> 5-176 <![CDATA[5-CHF2]]> Me Me Et 6′-Me <![CDATA[CO2Me]]> 5-177 <![CDATA[5-CHF2]]> Me Me Et 6′-Me <![CDATA[SO2Me]]> 5-178 <![CDATA[5-CHF2]]> Me Me Et 6′-Me <![CDATA[SO2NHMe]]> 5-179 <![CDATA[5-CHF2]]> Me Me i-Pr 6′-Me <![CDATA[CO2Me]]> 5-180 <![CDATA[5-CHF2]]> Me Me i-Pr 6′-Me <![CDATA[SO2Me]]>

[1085] [Table 5-7]

[1086] Continued from Table 5

[1087]

[1088] "●" in the structural formula indicates the bonding position.

[1089] [Table 5-8]

[1090] Continued from Table 5

[1091]

[1092] "●" in the structural formula indicates the bonding position.

[1093] [Table 5-9]

[1094] Continued from Table 5

[1095]

[1096] "●" in the structural formula indicates the bonding position.

[1097] [Table 5-10]

[1098] Continued from Table 5

[1099]

[1100] "●" in the structural formula indicates the bonding position.

[1101] [Table 5-11]

[1102] Continued from Table 5

[1103]

[1104] "●" in the structural formula indicates the bonding position.

[1105] [Table 5-12]

[1106] Continuation of Table 5

[1107]

[1108] "●" in the structural formula indicates the bonding position.

[1109] [Table 5-13]

[1110] Continuation of Table 5

[1111]

[1112] "●" in the structural formula indicates the bonding position.

[1113] [Table 5-14]

[1114] Continuation of Table 5

[1115]

[1116] "●" in the structural formula indicates the bonding position.

[1117] [Table 5-15]

[1118] Continuation of Table 5

[1119]

[1120] "●" in the structural formula indicates the bonding position.

[1121] [Chemical Formula 32]

[1122]

[1123] The position numbers in the table are the numbers defined in the general formula (1f).

[1124] [Table 6-1]

[1125] Table 6

[1126] 化合物编号 <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 5 > Q 物性值 6-1 H Me <![CDATA[NH2]]> Me H <![CDATA[CO2Me]]> 6-2 H Me <![CDATA[NH2]]> Me H <![CDATA[SO2Me]]> 6-3 H Me <![CDATA[NH2]]> Me H <![CDATA[SO2NHMe]]> 6-4 H Me <![CDATA[NH2]]> Et H <![CDATA[CO2Me]]> 6-5 H Me <![CDATA[NH2]]> Et H <![CDATA[SO2Me]]> 6-6 H Me <![CDATA[NH2]]> Et H <![CDATA[SO2NHMe]]> 6-7 H Me <![CDATA[NH2]]> i-Pr H <![CDATA[CO2Me]]> 6-8 H Me <![CDATA[NH2]]> i-Pr H <![CDATA[SO2Me]]> 6-9 H Me <![CDATA[NH2]]> i-Pr H <![CDATA[SO2NHMe]]> 6-10 5-Me Me <![CDATA[NH2]]> Me H <![CDATA[CO2Me]]> 6-11 5-Me Me <![CDATA[NH2]]> Me H <![CDATA[SO2Me]]> 6-12 5-Me Me <![CDATA[NH2]]> Me H <![CDATA[SO2NHMe]]> 6-13 5-Me Me <![CDATA[NH2]]> Et H <![CDATA[CO2Me]]> 6-14 5-Me Me <![CDATA[NH2]]> Et H <![CDATA[CO2Et]]> 197-198 6-15 5-Me Me <![CDATA[NH2]]> Et H <![CDATA[SO2Me]]> 238-239 6-16 5-Me Me <![CDATA[NH2]]> Et H <![CDATA[SO2NHMe]]> 6-17 5-Me Me <![CDATA[NH2]]> Et H <![CDATA[C(NH2)=N-OEt]]> 94-95 6-18 5-Me Me <![CDATA[NH2]]> i-Pr H <![CDATA[CO2Me]]> 6-19 5-Me Me <![CDATA[NH2]]> i-Pr H <![CDATA[SO2Me]]> 6-20 5-Me Me <![CDATA[NH2]]> i-Pr H <![CDATA[SO2NHMe]]> 6-21 5-OMe Me <![CDATA[NH2]]> Me H <![CDATA[CO2Me]]> 6-22 5-OMe Me <![CDATA[NH2]]> Me H <![CDATA[SO2Me]]> 6-23 5-OMe Me <![CDATA[NH2]]> Me H <![CDATA[SO2NHMe]]> 6-24 5-OMe Me <![CDATA[NH2]]> Et H <![CDATA[CO2Me]]> 6-25 5-OMe Me <![CDATA[NH2]]> Et H <![CDATA[SO2Me]]> 6-26 5-OMe Me <![CDATA[NH2]]> Et H <![CDATA[SO2NHMe]]> 6-27 5-OMe Me <![CDATA[NH2]]> i-Pr H <![CDATA[CO2Me]]> 6-28 5-OMe Me <![CDATA[NH2]]> i-Pr H <![CDATA[SO2Me]]> 6-29 5-OMe Me <![CDATA[NH2]]> i-Pr H <![CDATA[SO2NHMe]]> 6-30 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Me H <![CDATA[CO2Me]]>

[1127] [Table 6-2]

[1128] Continuation of Table 6

[1129] 化合物编号 <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 5 > Q 物性值 6-31 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Me H <![CDATA[SO2Me]]> 6-32 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Me H <![CDATA[SO2NHMe]]> 6-33 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Et H <![CDATA[CO2Me]]> 6-34 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Et H <![CDATA[SO2Me]]> 6-35 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> Et H <![CDATA[SO2NHMe]]> 6-36 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> i-Pr H <![CDATA[CO2Me]]> 6-37 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> i-Pr H <![CDATA[SO2Me]]> 6-38 <![CDATA[5-CHF2]]> Me <![CDATA[NH2]]> i-Pr H <![CDATA[SO2NHMe]]> 6-39 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Me H <![CDATA[CO2Me]]> 6-40 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Me H <![CDATA[SO2Me]]> 6-41 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Me H <![CDATA[SO2NHMe]]> 6-42 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Et H <![CDATA[CO2Me]]> 6-43 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Et H <![CDATA[SO2Me]]> 6-44 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> Et H <![CDATA[SO2NHMe]]> 6-45 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr H <![CDATA[CO2Me]]> 6-46 <![CDATA[5-CF3]]> Me <![CDATA[NH2]]> i-Pr H <![CDATA[SO2Me]]> 6-47 <![CDATA[5-CF3]]> Me &...

Claims

1. A compound represented by the general formula (1) or a salt thereof, wherein, [Chemical formula 1] In formula (1), R 1 means: (a1) A halogen atom; (a2) A cyano group; (a3) A nitro group; (a4) A formyl group; (a5) A carboxyl group; (a6) A (C1-C6) alkyl group; (a7) A (C2-C6) alkenyl group; (a8) A (C2-C6) alkynyl group; (a9) A (C3-C6) cycloalkyl group; (a10) A halo(C1-C6)alkyl group; (a11) A halo(C2-C6)alkenyl group; (a12) A halo(C2-C6)alkynyl group; (a14) A hydroxy(C1-C6)alkyl group; (a15) A hydroxyhalo(C1-C6)alkyl group; (a16) A (C1-C6)alkoxy(C1-C6)alkyl group; (a17) A bis(C1-C6)alkoxy(C1-C6)alkyl group; (a18) A halo(C1-C6)alkoxy(C1-C6)alkyl group; (a19) A (C1-C6)alkoxyhalo(C1-C6)alkyl group; (a20) A halo(C1-C6)alkoxyhalo(C1-C6)alkyl group; (a21) A (C3-C6)cycloalkyl(C1-C6)alkyl group; (a22) A (C1-C6)alkoxy group; (a23) A halo(C1-C6)alkoxy group; (a24) A (C1-C6)alkylthio group; (a25) A (C1-C6)alkylsulfinyl group; (a26) A (C1-C6)alkylsulfonyl group; (a27) A halo(C1-C6)alkylthio group; (a28) A halo(C1-C6)alkylsulfinyl group; (a29) A halo(C1-C6)alkylsulfonyl group; (a30)R 8 (R 9 )N group, where R 8 and R 9 represent a hydrogen atom, a hydroxyl group, an amino group, a di(C1-C6)alkylamino group, a (C1-C6)alkyl group, a (C3-C6)cycloalkyl group, a (C2-C6)alkenyl group, a (C2-C6)alkynyl group, a (C1-C6)alkoxy group, a (C2-C6)alkenyloxy group, a halo(C1-C6)alkyl group, a halo(C2-C6)alkenyl group, a halo(C2-C6)alkynyl group, a halo(C1-C6)alkoxy group, a halo(C3-C6)cycloalkyl group, a (C3-C6)cycloalkyl(C1-C6)alkyl group, a cyano(C1-C6)alkyl group, a (C1-C6)alkylcarbonyl group, a halo(C1-C6)alkylcarbonyl group, a (C1-C6)alkoxycarbonyl group, a halo(C1-C6)alkoxycarbonyl group, a (C1-C6)alkylmercapto-carbonyl group, a (C1-C6)alkylsulfonyl group, a halo(C1-C6)alkylsulfonyl group, an N-(C1-C6)alkylformamido group, an N,N-di(C1-C6)alkylformamido group, an N-(C1-C6)alkylsulfamoyl group, an N,N-di(C1-C6)alkylsulfamoyl group, an N-halo(C1-C6)alkylformamido group, a (C1-C6)alkoxycarbonyl(C1-C6)alkyl group, a (C1-C6)alkoxy(C1-C6)alkyl group, a di(C1-C6)alkoxy(C1-C6)alkyl group, a (C1-C6)alkoxy(C1-C6)alkylcarbonyl group, a thietanyl group, a 1,1-dioxothietanyl group, a tetrahydrofuranyl group, a thiazolyl group, a 2-oxotetrahydrofuranyl group, a phenyl group, a phenyl group having 1 to 5 substituents which are the same or different and are each independently selected from a halogen atom, a cyano group, a (C1-C6)alkyl group, a halo(C1-C6)alkyl group, a (C1-C6)alkoxy group, a halo(C1-C6)alkoxy group, a (C3-C6)cycloalkyl group, a (C1-C6)alkylthio group, a halo(C1-C6)alkylthio group, a (C1-C6)alkylsulfinyl group, a halo(C1-C6)alkylsulfinyl group, a (C1-C6)alkylsulfonyl group and a halo(C1-C6)alkylsulfonyl group on the ring, or a phenyl(C1-C6)alkyl group, and R 8 and R 9 are optionally the same or different and are optionally bonded to each other to form a 4- to 6-membered ring; (a31)R 10 (R 11 )N(C1-C6)alkyl, wherein R 10 and R 11 represent a hydrogen atom, (C1-C6)alkyl, halo(C1-C6)alkyl, (C3-C6)cycloalkyl, (C3-C6)cycloalkyl(C1-C6)alkyl, (C1-C6)alkylcarbonyl, halo(C1-C6)alkylcarbonyl, (C1-C6)alkoxycarbonyl, halo(C1-C6)alkoxycarbonyl, (C1-C6)alkylsulfonyl or halo(C1-C6)alkylsulfonyl, and R 10 and R 11 are optionally the same or different and are optionally bonded to each other to form a 4- to 6-membered ring; (a32) A (C1-C6)alkylthio(C1-C6)alkyl group; (a33) A (C1-C6)alkylsulfinyl(C1-C6)alkyl group; (a34) A (C1-C6)alkylsulfonyl(C1-C6)alkyl group; (a35) A halo(C1-C6)alkylthio(C1-C6)alkyl group; (a36) A halo(C1-C6)alkylsulfinyl(C1-C6)alkyl group; (a37) A halo(C1-C6)alkylsulfonyl(C1-C6)alkyl group; (a44) A (C1-C6)alkylcarbonyl group; (a45) A (C1-C6)alkoxycarbonyl group; (a46) A halo(C1-C6)alkylcarbonyl group; (a47) A halo(C1-C6)alkoxycarbonyl group; (a50)R 10 (R 11 )N-carbonyl, where R 10 and R 11 are the same as the R in the (a31)R 10 (R 11 )N(C1-C6)alkyl; 10 and R 11 are identical; (a52)R 10 (R 11 )N-sulfonyl, wherein R 10 and R 11 are the same as the R in the said (a31)R 10 (R 11 )N(C1-C6)alkyl; 10 and R 11 are identical; (a55) A (C1-C6)alkoxyimino(C1-C3)alkyl group; (a56) A halo(C1-C6)alkoxyimino(C1-C3)alkyl group; (a57) A phenyl group; (a58) having 1 to 5 optionally identical or different substituents selected from halogen atoms, cyano groups, nitro groups, formyl groups, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C3-C6)cycloalkyl(C1-C6)alkyl groups, R 10 (R 11 )N(C1-C6)alkyl groups, R 10 (R 11 )N groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups, where the R 10 (R 11 )N(C1-C6)alkyl group's R 10 and R 11 is the same as the (a31)R 10 (R 11 )N(C1-C6)alkyl group's said R 10 and R 11 , R 10 (R 11 )N group's R 10 and R 11 is the same as the (a31)R 10 (R 11 )N(C1-C6)alkyl group's said R 10 and R 11 ; (a59) A pyridyl group; (a60) A pyridyl group having, on the ring, 1 to 4 optionally identical or different substituents selected from a halogen atom, a cyano group, a nitro group, a formyl group, a (C1-C6) alkyl group, a halo (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo (C1-C6) alkoxy group, a (C3-C6) cycloalkyl (C1-C6) alkyl group, R 10 (R 11 )N(C1-C6) alkyl, R 10 (R 11 )N group, a (C1-C6) alkylthio group, a halo (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a halo (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group and a halo (C1-C6) alkylsulfonyl group, wherein R 10 (R 11 )N(C1-C6) alkyl has the same R 10 and R 11 as the (a31) R 10 (R 11 )N(C1-C6) alkyl, and R 10 and R 11 in the R 10 (R 11 )N group has the same R 10 and R 11 as the (a31) R 10 (R 11 )N(C1-C6) alkyl, and R 10 and R 11 are the same; (a61) A pyrazolyl group; (a62) having 1 to 3 optionally identical or different substituents selected from halogen atoms, cyano groups, nitro groups, formyl groups, (C1-C6) alkyl groups, halo (C1-C6) alkyl groups, (C1-C6) alkoxy groups, halo (C1-C6) alkoxy groups, (C3-C6) cycloalkyl (C1-C6) alkyl groups, R 10 (R 11 )N(C1-C6) alkyl groups, R 10 (R 11 )N groups, (C1-C6) alkylthio groups, halo (C1-C6) alkylthio groups, (C1-C6) alkylsulfinyl groups, halo (C1-C6) alkylsulfinyl groups, (C1-C6) alkylsulfonyl groups and halo (C1-C6) alkylsulfonyl groups, wherein R 10 (R 11 )N(C1-C6) alkyl group, the R 10 and R 11 are the same as the R 10 (R 11 )N(C1-C6) alkyl group in the (a31)R 10 and R 11 , and R 10 (R 11 )N group, the R 10 and R 11 are the same as the R 10 (R 11 )N(C1-C6) alkyl group in the (a31)R 10 and R 11 ; (a63) A phenoxy group; (a64) having 1 to 5 optionally identical or different substituents selected from halogen atoms, cyano groups, nitro groups, formyl groups, (C1-C6) alkyl groups, halo (C1-C6) alkyl groups, (C1-C6) alkoxy groups, halo (C1-C6) alkoxy groups, (C3-C6) cycloalkyl (C1-C6) alkyl groups, R 10 (R 11 )N(C1-C6) alkyl groups, R 10 (R 11 )N groups, (C1-C6) alkylthio groups, halo (C1-C6) alkylthio groups, (C1-C6) alkylsulfinyl groups, halo (C1-C6) alkylsulfinyl groups, (C1-C6) alkylsulfonyl groups and halo (C1-C6) alkylsulfonyl groups, wherein R 10 (R 11 )N(C1-C6) alkyl groups, the R 10 and R 11 are the same as the (a31) R 10 (R 11 )N(C1-C6) alkyl groups, the R 10 and R 11 ; R 10 (R 11 )N groups, the R 10 and R 11 are the same as the (a31) R 10 (R 11 )N(C1-C6) alkyl groups, the R 10 and R 11 ; (a65) A dioxolanyl group; (a66) having 1 to 4 optionally identical or different substituents selected from halogen atoms, cyano group, nitro group, formyl group, carbonyl group, (C1-C6)alkyl group, halo(C1-C6)alkyl group, (C1-C6)alkoxy group, halo(C1-C6)alkoxy group, (C3-C6)cycloalkyl(C1-C6)alkyl group, R 10 (R 11 )N(C1-C6)alkyl group, (C1-C6)alkylthio group, halo(C1-C6)alkylthio group, (C1-C6)alkylsulfinyl group, halo(C1-C6)alkylsulfinyl group, (C1-C6)alkylsulfonyl group and halo(C1-C6)alkylsulfonyl group, wherein R 10 (R 11 )N(C1-C6)alkyl group of R 10 and R 11 is the same as the R 10 (R 11 )N(C1-C6)alkyl group of the (a31)R 10 and R 11 ; (a67) A dioxanyl group; (a68) having 1 to 6 optionally identical or different substituents selected from halogen atoms, cyano groups, nitro groups, formyl groups, carbonyl groups, (C1-C6) alkyl groups, halo (C1-C6) alkyl groups, (C1-C6) alkoxy groups, halo (C1-C6) alkoxy groups, (C3-C6) cycloalkyl (C1-C6) alkyl groups, R 10 (R 11 )N(C1-C6) alkyl groups, (C1-C6) alkylthio groups, halo (C1-C6) alkylthio groups, (C1-C6) alkylsulfinyl groups, halo (C1-C6) alkylsulfinyl groups, (C1-C6) alkylsulfonyl groups and halo (C1-C6) alkylsulfonyl groups on a dioxolane ring, wherein R 10 (R 11 )N(C1-C6) alkyl group, the R 10 and R 11 are the same as the R 10 (R 11 )N(C1-C6) alkyl group in the (a31)R 10 and R 11 ; (a69) A (C1-C6)alkylene formed by bonding of two adjacent substituents and optionally substituted with 1 to 4 substituents independently selected from a halogen atom, a phenyl group, and a (C1-C6)alkyl group; or (a70) A methylenedioxy group formed by bonding of two adjacent substituents, optionally substituted by one or two substituents independently selected from a halogen atom, a phenyl group, and a (C1-C6) alkyl group, which may be the same or different; when m represents an integer of 2 or more, R 1 which may be the same or different, m represents 0, 1, 2, 3, or 4, R 2 means: (b1) A hydrogen atom; (b2) A (C1-C6)alkyl group; (b3) A (C3-C6)cycloalkyl group; (b4) (C2-C6) alkenyl; (b5) (C2-C6) alkynyl; (b6) halo (C1-C6) alkyl; (b7) halo (C2-C6) alkenyl; (b8) halo (C2-C6) alkynyl; (b9) (C1-C6) alkoxy (C1-C6) alkyl; (b10) (C1-C6) alkylthio (C1-C6) alkyl; (b11) (C1-C6) alkylsulfinyl (C1-C6) alkyl; (b12) (C1-C6) alkylsulfonyl (C1-C6) alkyl; (b13) (C3-C6) cycloalkyl (C1-C6) alkyl; (b15) (C1-C6) alkylcarbonyl; (b16) (C1-C6) alkoxycarbonyl; (b18) halo (C1-C6) alkylcarbonyl; or (b21)R 10 (R 11 )N-sulfonyl, wherein R 10 and R 11 are the same as the R in the said (a31)R 10 (R 11 )N(C1-C6)alkyl, 10 and R 11 are identical. R 3 means: (c1) hydrogen atom; (c2) halogen group; (c3) cyano group; (c4) carboxyl group; (c5) formamido group; (c6) (C1-C6) alkyl; (c9) halo (C1-C6) alkyl; (c12)R 8 (R 9 )N group, where R 8 and R 9 are the same as the R 8 (R 9 ) in the N group; 8 and R 9 are the same; (c13) (C1-C6) alkoxy; (c14) halo (C1-C6) alkoxy; (c15) (C1-C6) alkoxy (C1-C6) alkyl; or (c16) (C1-C6) alkoxycarbonyl (C1-C6) alkyl, R 4 means: (d1) hydrogen atom; (d2) (C1-C6) alkyl; (d3) (C2-C6) alkenyl; (d4) (C2-C6) alkynyl; (d5) (C3-C6) cycloalkyl; (d6) halo (C1-C6) alkyl; (d7) halo (C2-C6) alkenyl; (d8) halo (C2-C6) alkynyl; (d9) (C1-C6) alkoxy (C1-C6) alkyl; (d10) halo (C1-C6) alkoxy (C1-C6) alkyl; (d13) (C3-C6) cycloalkyl (C1-C6) alkyl; (d14) cyano (C1-C6) alkyl; (d15) (C1-C6) alkylthio (C1-C6) alkyl; (d16) (C1-C6) alkylsulfinyl (C1-C6) alkyl; (d17) (C1-C6) alkylsulfonyl (C1-C6) alkyl; (d18) carboxyl (C1-C6) alkyl; (d19) phenyl (C1-C6) alkyl; (d20) phenyl (C1-C6) alkyl having 1 to 5 substituents, which are the same or different and are selected from a halogen atom, cyano group, nitro group, formyl group, (C1-C6) alkyl, halo (C1-C6) alkyl, (C1-C6) alkoxy, halo (C1-C6) alkoxy, (C3-C6) cycloalkyl (C1-C6) alkyl, (C1-C6) alkylthio, halo (C1-C6) alkylthio, (C1-C6) alkylsulfinyl, halo (C1-C6) alkylsulfinyl, (C1-C6) alkylsulfonyl, and halo (C1-C6) alkylsulfonyl, on the ring; (d22) (C1-C6) alkylcarbonyl; (d23) (C1-C6) alkoxycarbonyl; (d24) (C1-C6) alkylsulfonyl; (d25)Halogenated (C1-C6) alkylcarbonyl; (d26)Halogenated (C1-C6) alkoxycarbonyl; (d27)Halogenated (C1-C6) alkylsulfonyl; (d30)phenyl; (d31) having 1 to 5 optionally identical or different substituents selected from halogen atoms, cyano groups, nitro groups, formyl groups, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C3-C6)cycloalkyl(C1-C6)alkyl groups, R 10 (R 11 )N groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups, where R 10 (R 11 )N groups in which R 10 and R 11 are the same as the R 10 (R 11 )N(C1-C6)alkyl groups in the (a31)R 10 and R 11 ; or (d32)(C1-C6) alkoxycarbonyl (C1-C6) alkyl, A 1 、A 2 and A 3 represent CR 5 or a nitrogen atom, A 1 、A 2 and A 3 are optionally the same or different, wherein, R 5 in CR 5 represents a hydrogen atom, a halogen atom, a cyano group, a (C1-C6) alkyl group, a halo(C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkoxy group, R 10 (R 11 )N group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group or a (C1-C6) alkylsulfonyl group, R 10 (R 11 )N group in which R 10 and R 11 are the same as R 10 (R 11 )N(C1-C6) alkyl group in the (a31)R 10 and R 11 and are the same, Q represents: (e1)halogen atom; (e2)cyano; (e4)formyl; (e5)(C1-C6) alkyl; (e6)(C2-C6) alkenyl; (e7)(C2-C6) alkynyl; (e8)halogenated (C1-C6) alkyl; (e11)(C1-C6) alkoxy; (e12)halogenated (C1-C6) alkoxy; (e13)hydroxy (C1-C6) alkyl; (e14)dihydroxy (C1-C6) alkyl; (e15)(C1-C6) alkoxy (C1-C6) alkyl; (e16)(C1-C6) alkoxy (C2-C6) alkenyl; (e17)R 8 (R 9 )N group, wherein R 8 and R 9 are the same as the R 8 (R 9 ) in the N group, and the R 8 and R 9 are the same; (e18)dioxolanyl; (e19) having 1 or 2 optionally identical or different substituents selected from halogen atoms, cyano group, nitro group, formyl group, carbonyl group, (C1-C6)alkyl, halo(C1-C6)alkyl, (C1-C6)alkoxy, halo(C1-C6)alkoxy, (C3-C6)cycloalkyl(C1-C6)alkyl, R 10 (R 11 )N(C1-C6)alkyl, (C1-C6)alkylthio, halo(C1-C6)alkylthio, (C1-C6)alkylsulfinyl, halo(C1-C6)alkylsulfinyl, (C1-C6)alkylsulfonyl and halo(C1-C6)alkylsulfonyl on the dioxolanyl ring, wherein R 10 (R 11 )N(C1-C6)alkyl of R 10 and R 11 is the same as the R 10 (R 11 )N(C1-C6)alkyl of the (a31)R 10 and R 11 ; (e20)dioxanyl; (e21) having 1 to 3 optionally identical or different substituents selected from halogen atoms, cyano groups, nitro groups, formyl groups, carbonyl groups, (C1-C6) alkyl groups, halo (C1-C6) alkyl groups, (C1-C6) alkoxy groups, halo (C1-C6) alkoxy groups, (C3-C6) cycloalkyl (C1-C6) alkyl groups, R 10 (R 11 )N(C1-C6) alkyl groups, (C1-C6) alkylthio groups, halo (C1-C6) alkylthio groups, (C1-C6) alkylsulfinyl groups, halo (C1-C6) alkylsulfinyl groups, (C1-C6) alkylsulfonyl groups and halo (C1-C6) alkylsulfonyl groups of the dioxanyl group, wherein R 10 (R 11 )N(C1-C6) alkyl group of R 10 and R 11 is the same as the (a31) R 10 (R 11 )N(C1-C6) alkyl group of the R 10 and R 11 ; (e22)phenyl; (e23) having 1 to 5 optionally identical or different substituents selected from halogen atoms, cyano group, nitro group, formyl group, (C1-C6)alkyl group, halo(C1-C6)alkyl group, (C1-C6)alkoxy group, halo(C1-C6)alkoxy group, (C3-C6)cycloalkyl(C1-C6)alkyl group, R 10 (R 11 )N group, (C1-C6)alkylthio group, halo(C1-C6)alkylthio group, (C1-C6)alkylsulfinyl group, halo(C1-C6)alkylsulfinyl group, (C1-C6)alkylsulfonyl group and halo(C1-C6)alkylsulfonyl group, wherein R 10 (R 11 )N group, R 10 and R 11 are the same as R 10 (R 11 )N(C1-C6)alkyl group in (a31)R 10 and R 11 ; (e24) imidazolyl group; (e25) having 1 to 3 optionally identical or different substituents selected from halogen atoms, cyano groups, nitro groups, formyl groups, (C1-C6) alkyl groups, halo (C1-C6) alkyl groups, (C1-C6) alkoxy groups, halo (C1-C6) alkoxy groups, (C3-C6) cycloalkyl (C1-C6) alkyl groups, R 10 (R 11 )N groups, (C1-C6) alkylthio groups, halo (C1-C6) alkylthio groups, (C1-C6) alkylsulfinyl groups, halo (C1-C6) alkylsulfinyl groups, (C1-C6) alkylsulfonyl groups and halo (C1-C6) alkylsulfonyl groups, wherein R 10 (R 11 )N groups in which R 10 and R 11 are the same as the R 10 (R 11 )N(C1-C6) alkyl groups in the (a31)R 10 and R 11 ; (e26)oxadiazolyl; (e27) having a substituent selected from a halogen atom, a cyano group, a nitro group, a formyl group, a (C1-C6) alkyl group, a halogenated (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halogenated (C1-C6) alkoxy group, a (C3-C6) cycloalkyl (C1-C6) alkyl group, R 10 (R 11 )N group, a (C1-C6) alkylthio group, a halogenated (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a halogenated (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, and a halogenated (C1-C6) alkylsulfonyl group, wherein R 10 (R 11 )N group, R 10 and R 11 is the same as the R 10 (R 11 )N(C1-C6) alkyl group in the (a31)R 10 and R 11 ; (e28)S(O) p R 6 group, wherein R 6 represents a hydrogen atom, (C1-C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, halo(C1-C6) alkyl, halo(C2-C6) alkenyl, halo(C2-C6) alkynyl, (C1-C6) alkoxy, (C3-C6) cycloalkyl, halo(C3-C6) cycloalkyl, phenyl(C1-C6) alkyl, (C1-C6) alkoxyphenyl(C1-C6) alkyl, (C1-C6) alkylphenyl(C1-C6) alkyl, tris(C1-C6) alkylsilylphenyl(C1-C6) alkyl or N(R 8 )R 9 group, p represents 0, 1 or 2, wherein the R 8 )R 9 groups in the N(R 8 )R 9 group and the R 8 (R 9 )N group in the (a30)R 8 and R 9 are the same; (e29)C(O)R 7 a radical, wherein R 7 represents hydroxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, halo(C1-C6)alkyl, halo(C2-C6)alkenyl, halo(C2-C6)alkynyl, (C1-C6)alkoxycarbonyl(C1-C6)alkyl, phenyl(C1-C6)alkyl, phenyl(C1-C6)alkoxy, (C1-C6)alkoxy, (C2-C6)alkenyloxy, (C2-C6)alkynyloxy, (C3-C6)cycloalkoxy, halo(C1-C6)alkoxy, halo(C2-C6)alkynyloxy, phenoxy, (C1-C6)alkoxycarbonyl(C1-C6)alkoxy, (C1-C6)alkylthio, phenyl, thiazolidinyl or N(R 8 )R 9 a radical, wherein the R 8 )R 9 in the N(R 8 )R 9 radical and the R 8 (R 9 )N radical in the (a30)R 8 and R 9 are the same; (e30)thiocarboxamido; (e31)N-(C1-C6) alkylaminothiocarbonyl; (e32)N,N-bis(C1-C6) alkylaminothiocarbonyl; (e33)[Chemical Formula 2] Wherein, R 6 is the same as the R in the (e28) S (O) p R 6 in the group; the R 6 is the same as the R 8 in the (a30) R 8 (R 9 ) N group; 8 identical. (e34)hydroxyimino (C1-C3) alkyl; (e35)(C1-C6) alkoxyimino (C1-C3) alkyl; (e36)halogenated (C1-C6) alkoxyimino (C1-C3) alkyl; (e37)hydrazono (C1-C3) alkyl; (e38)(C1-C6) alkylhydrazono (C1-C3) alkyl; (e39)bis(C1-C6) alkylhydrazono (C1-C3) alkyl; (e40)phenyl (C1-C6) alkoxyimino (C1-C3) alkyl; (e41)(C2-C6) alkenyloxyimino (C1-C3) alkyl; (e42)bis(C1-C6) alkoxyphosphinyl; (e43)bis(C1-C6) alkoxyphosphinylamino; (e44)hydroxy; (e45)(C1-C6) alkoxy (C1-C6) alkoxy; (e46)(C1-C6) alkoxyiminoamino (C1-C3) alkyl.

2. The compound or its salt according to claim 1, wherein, A 1 、A 2 and A 3 and A in claim 1 1 、A 2 and A 3 are the same R 1 means: (a1)halogen atom; (a2)cyano; (a3)nitro; (a4)formyl; (a5)carboxyl; (a6)(C1-C6) alkyl; (a7)(C2-C6) alkenyl; (a8)(C2-C6) alkynyl; (a9)(C3-C6) cycloalkyl; (a10)halogenated (C1-C6) alkyl; (a11)halogenated (C2-C6) alkenyl; (a12)halogenated (C2-C6) alkynyl; (a14)hydroxy (C1-C6) alkyl; (a15)hydroxyhalogenated (C1-C6) alkyl; (a16)(C1-C6) alkoxy (C1-C6) alkyl; (a17)bis(C1-C6) alkoxy (C1-C6) alkyl; (a18)halo(C1-C6)alkoxy(C1-C6)alkyl; (a19)(C1-C6)alkoxyhalo(C1-C6)alkyl; (a20)halo(C1-C6)alkoxyhalo(C1-C6)alkyl; (a21)(C3-C6)cycloalkyl(C1-C6)alkyl; (a22)(C1-C6)alkoxy; (a23)halo(C1-C6)alkoxy; (a24)(C1-C6)alkylthio; (a25)(C1-C6)alkylsulfinyl; (a26)(C1-C6)alkylsulfonyl; (a27)halo(C1-C6)alkylthio; (a28)halo(C1-C6)alkylsulfinyl; (a29)halo(C1-C6)alkylsulfonyl; (a30)R 8 (R 9 )N group, where R 8 and R 9 represent a hydrogen atom, a hydroxyl group, an amino group, a di(C1-C6)alkylamino group, a (C1-C6)alkyl group, a (C3-C6)cycloalkyl group, a (C2-C6)alkenyl group, a (C2-C6)alkynyl group, a (C1-C6)alkoxy group, a (C2-C6)alkenyloxy group, a halo(C1-C6)alkyl group, a halo(C2-C6)alkenyl group, a halo(C2-C6)alkynyl group, a halo(C3-C6)cycloalkyl group, a (C3-C6)cycloalkyl(C1-C6)alkyl group, a cyano(C1-C6)alkyl group, a (C1-C6)alkylcarbonyl group, a halo(C1-C6)alkylcarbonyl group, a (C1-C6)alkoxycarbonyl group, a halo(C1-C6)alkoxycarbonyl group, a (C1-C6)alkylmercapto-carbonyl group, a (C1-C6)alkylsulfonyl group, a halo(C1-C6)alkylsulfonyl group, an N-(C1-C6)alkylformamido group, an N,N-di(C1-C6)alkylformamido group, an N-(C1-C6)alkylsulfamoyl group, an N,N-di(C1-C6)alkylsulfamoyl group, an N-halo(C1-C6)alkylformamido group, a (C1-C6)alkoxycarbonyl(C1-C6)alkyl group, a (C1-C6)alkoxy(C1-C6)alkyl group, a di(C1-C6)alkoxy(C1-C6)alkyl group, a (C1-C6)alkoxy(C1-C6)alkylcarbonyl group, a thietanyl group, a 1,1-dioxothietanyl group, a tetrahydrofuranyl group, a thiazolyl group, a 2-oxotetrahydrofuranyl group, a phenyl group, a phenyl group having 1 to 5 substituents which are the same or different and are each independently selected from a halogen atom, a cyano group, a (C1-C6)alkyl group, a halo(C1-C6)alkyl group, a (C1-C6)alkoxy group and a halo(C1-C6)alkoxy group on the ring, or a phenyl(C1-C6)alkyl group, and, R 8 and R 9 are optionally the same or different and are optionally bonded to each other to form a 4- to 6-membered ring; (a31)R 10 (R 11 )N(C1-C6)alkyl, wherein R 10 and R 11 represent a hydrogen atom, (C1-C6)alkyl, halo(C1-C6)alkyl, (C3-C6)cycloalkyl, (C3-C6)cycloalkyl(C1-C6)alkyl, (C1-C6)alkylcarbonyl, halo(C1-C6)alkylcarbonyl, (C1-C6)alkoxycarbonyl, halo(C1-C6)alkoxycarbonyl, (C1-C6)alkylsulfonyl or halo(C1-C6)alkylsulfonyl, and R 10 and R 11 are optionally the same or different and are optionally bonded to each other to form a 4- to 6-membered ring; (a32)(C1-C6)alkylthio(C1-C6)alkyl; (a33)(C1-C6)alkylsulfinyl(C1-C6)alkyl; (a34)(C1-C6)alkylsulfonyl(C1-C6)alkyl; (a35)halo(C1-C6)alkylthio(C1-C6)alkyl; (a36)halo(C1-C6)alkylsulfinyl(C1-C6)alkyl; (a37)halo(C1-C6)alkylsulfonyl(C1-C6)alkyl; (a44)(C1-C6)alkylcarbonyl; (a45)(C1-C6)alkoxycarbonyl; (a46)halo(C1-C6)alkylcarbonyl; (a47)halo(C1-C6)alkoxycarbonyl; (a50)R 10 (R 11 )N-carbonyl, wherein R 10 and R 11 are the same as the R in the said (a31)R 10 (R 11 )N(C1-C6)alkyl; 10 and R 11 are identical; (a52)R 10 (R 11 )N-sulfonyl, wherein R 10 and R 11 are the same as the R in the said (a31)R 10 (R 11 )N(C1-C6)alkyl; 10 and R 11 are identical; (a55)(C1-C6)alkoxyimino(C1-C3)alkyl; (a56)halo(C1-C6)alkoxyimino(C1-C3)alkyl; (a57)phenyl; (a58) having 1 to 5 optionally identical or different substituents selected from halogen atoms, cyano groups, nitro groups, formyl groups, (C1-C6) alkyl groups, halo(C1-C6) alkyl groups, (C1-C6) alkoxy groups, halo(C1-C6) alkoxy groups, (C3-C6) cycloalkyl(C1-C6) alkyl groups, R 10 (R 11 )N(C1-C6) alkyl groups, R 10 (R 11 )N groups, (C1-C6) alkylthio groups, halo(C1-C6) alkylthio groups, (C1-C6) alkylsulfinyl groups, halo(C1-C6) alkylsulfinyl groups, (C1-C6) alkylsulfonyl groups and halo(C1-C6) alkylsulfonyl groups, and phenyl groups substituted with the substituents, R 10 (R 11 )N(C1-C6) alkyl groups, the R 10 and R 11 in (a31) R 10 (R 11 )N(C1-C6) alkyl groups are the same as the R 10 and R 11 in (a31) R 10 (R 11 )N groups, the R 10 and R 11 in (a31) R 10 (R 11 )N(C1-C6) alkyl groups are the same as the R 10 and R 11 in (a31) R ; (a59)pyridyl; (a60) A pyridyl group having 1 to 4 optionally identical or different substituents selected from a halogen atom, a cyano group, a nitro group, a formyl group, a (C1-C6) alkyl group, a halo (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo (C1-C6) alkoxy group, a (C3-C6) cycloalkyl (C1-C6) alkyl group, R 10 (R 11 )N(C1-C6) alkyl, R 10 (R 11 )N group, a (C1-C6) alkylthio group, a halo (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a halo (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, and a halo (C1-C6) alkylsulfonyl group, wherein R 10 (R 11 )N(C1-C6) alkyl has the same R 10 and R 11 as the (a31) R 10 (R 11 )N(C1-C6) alkyl, and R 10 and R 11 are the same; R 10 (R 11 )N group has the same R 10 and R 11 as the (a31) R 10 (R 11 )N(C1-C6) alkyl, and R 10 and R 11 are the same; (a61)pyrazolyl; (a62) having 1 to 3 optionally identical or different substituents selected from halogen atoms, cyano groups, nitro groups, formyl groups, (C1-C6) alkyl groups, halo (C1-C6) alkyl groups, (C1-C6) alkoxy groups, halo (C1-C6) alkoxy groups, (C3-C6) cycloalkyl (C1-C6) alkyl groups, R 10 (R 11 )N(C1-C6) alkyl groups, R 10 (R 11 )N groups, (C1-C6) alkylthio groups, halo (C1-C6) alkylthio groups, (C1-C6) alkylsulfinyl groups, halo (C1-C6) alkylsulfinyl groups, (C1-C6) alkylsulfonyl groups and halo (C1-C6) alkylsulfonyl groups, wherein R 10 (R 11 )N(C1-C6) alkyl groups, the R 10 and R 11 is the same as the (a31) R 10 (R 11 )N(C1-C6) alkyl groups, the R 10 and R 11 ; R 10 (R 11 )N groups, the R 10 and R 11 is the same as the (a31) R 10 (R 11 )N(C1-C6) alkyl groups, the R 10 and R 11 ; (a63)phenoxy; (a64) having 1 to 5 optionally identical or different substituents selected from halogen atoms, cyano groups, nitro groups, formyl groups, (C1-C6) alkyl groups, halo (C1-C6) alkyl groups, (C1-C6) alkoxy groups, halo (C1-C6) alkoxy groups, (C3-C6) cycloalkyl (C1-C6) alkyl groups, R 10 (R 11 )N(C1-C6) alkyl groups, R 10 (R 11 )N groups, (C1-C6) alkylthio groups, halo (C1-C6) alkylthio groups, (C1-C6) alkylsulfinyl groups, halo (C1-C6) alkylsulfinyl groups, (C1-C6) alkylsulfonyl groups and halo (C1-C6) alkylsulfonyl groups, where the R 10 (R 11 )N(C1-C6) alkyl group's R 10 and R 11 is the same as the (a31) R 10 (R 11 )N(C1-C6) alkyl group's said R 10 and R 11 , and the R 10 (R 11 )N group's R 10 and R 11 is the same as the (a31) R 10 (R 11 )N(C1-C6) alkyl group's said R 10 and R 11 ; (a65)dioxolanyl; (a66) having 1 to 4 optionally identical or different substituents selected from halogen atoms, cyano group, nitro group, formyl group, carbonyl group, (C1-C6)alkyl group, halo(C1-C6)alkyl group, (C1-C6)alkoxy group, halo(C1-C6)alkoxy group, (C3-C6)cycloalkyl(C1-C6)alkyl group, R 10 (R 11 )N(C1-C6)alkyl group, (C1-C6)alkylthio group, halo(C1-C6)alkylthio group, (C1-C6)alkylsulfinyl group, halo(C1-C6)alkylsulfinyl group, (C1-C6)alkylsulfonyl group and halo(C1-C6)alkylsulfonyl group on the dioxolanyl ring, wherein R 10 (R 11 )N(C1-C6)alkyl group of R 10 and R 11 is the same as the (a31)R 10 (R 11 )N(C1-C6)alkyl group of the R 10 and R 11 ; (a67)dioxanyl; (a68) having 1 to 6 optionally identical or different substituents selected from halogen atoms, cyano group, nitro group, formyl group, carbonyl group, (C1-C6)alkyl group, halo(C1-C6)alkyl group, (C1-C6)alkoxy group, halo(C1-C6)alkoxy group, (C3-C6)cycloalkyl(C1-C6)alkyl group, R 10 (R 11 )N(C1-C6)alkyl group, (C1-C6)alkylthio group, halo(C1-C6)alkylthio group, (C1-C6)alkylsulfinyl group, halo(C1-C6)alkylsulfinyl group, (C1-C6)alkylsulfonyl group and halo(C1-C6)alkylsulfonyl group on the dioxacyclohexyl group, wherein R 10 (R 11 )N(C1-C6)alkyl group of R 10 and R 11 is the same as the (a31)R 10 (R 11 )N(C1-C6)alkyl group of the R 10 and R 11 ; (a69)(C1-C6)alkylene formed by bonding of two adjacent substituents, optionally substituted by 1 or 2 substituents independently selected from a halogen atom, phenyl, and (C1-C6)alkyl; or (a70)methylenedioxy formed by bonding of two adjacent substituents, optionally substituted by 1 or 2 substituents independently selected from a halogen atom, phenyl, and (C1-C6)alkyl, When m represents an integer of 2 or more, R 1 are each independently selected to be the same or different, m represents 0, 1, 2, 3, or 4, R 2 means: (b1)hydrogen atom; (b2)(C1-C6)alkyl; (b3)(C3-C6)cycloalkyl; (b4)(C2-C6)alkenyl; (b5)(C2-C6)alkynyl; (b6)halo(C1-C6)alkyl; (b7)halo(C2-C6)alkenyl; (b8)halo(C2-C6)alkynyl; (b9)(C1-C6)alkoxy(C1-C6)alkyl; (b10)(C1-C6)alkylthio(C1-C6)alkyl; (b11)(C1-C6)alkylsulfinyl(C1-C6)alkyl; (b12)(C1-C6)alkylsulfonyl(C1-C6)alkyl; (b13) (C3-C6) cycloalkyl (C1-C6) alkyl; (b15) (C1-C6) alkylcarbonyl; (b16) (C1-C6) alkoxycarbonyl; (b18) halo (C1-C6) alkylcarbonyl; or (b21)R 10 (R 11 )N-sulfonyl, wherein R 10 and R 11 are the same as the R in the said (a31)R 10 (R 11 )N(C1-C6)alkyl, 10 and R 11 are identical, R 3 means: (c1) hydrogen atom; (c2) halogen group; (c3) cyano group; (c4) carboxyl group; (c5) formamido group; (c6) (C1-C6) alkyl; (c9) halo (C1-C6) alkyl; (c12)R 8 (R 9 )N group, wherein R 8 and R 9 are the same as the R 8 (R 9 ) in the N group of (a30)R 8 and R 9 respectively; (c13) (C1-C6) alkoxy; (c14) halo (C1-C6) alkoxy; (c15) (C1-C6) alkoxy (C1-C6) alkyl; or (c16) (C1-C6) alkoxycarbonyl (C1-C6) alkyl, R 4 means: (d1) hydrogen atom; (d2) (C1-C6) alkyl; (d3) (C2-C6) alkenyl; (d4) (C2-C6) alkynyl; (d5) (C3-C6) cycloalkyl; (d6) halo (C1-C6) alkyl; (d7) halo (C2-C6) alkenyl; (d8) halo (C2-C6) alkynyl; (d9) (C1-C6) alkoxy (C1-C6) alkyl; (d10) halo (C1-C6) alkoxy (C1-C6) alkyl; (d13) (C3-C6) cycloalkyl (C1-C6) alkyl; (d14) cyano (C1-C6) alkyl; (d15) (C1-C6) alkylthio (C1-C6) alkyl; (d16) (C1-C6) alkylsulfinyl (C1-C6) alkyl; (d17) (C1-C6) alkylsulfonyl (C1-C6) alkyl; (d18) carboxy (C1-C6) alkyl; (d19) phenyl (C1-C6) alkyl; (d20) phenyl (C1-C6) alkyl having 1 to 5 substituents, which may be the same or different, selected from a halogen atom, a cyano group, a nitro group, a formyl group, a (C1-C6) alkyl group, a halo (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo (C1-C6) alkoxy group, a (C3-C6) cycloalkyl (C1-C6) alkyl group, a (C1-C6) alkylthio group, a halo (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a halo (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, and a halo (C1-C6) alkylsulfonyl group, on the ring; (d22) (C1-C6) alkylcarbonyl; (d23) (C1-C6) alkoxycarbonyl; (d24) (C1-C6) alkylsulfonyl; (d25) halo (C1-C6) alkylcarbonyl; (d26) halo (C1-C6) alkoxycarbonyl; (d27) halo (C1-C6) alkylsulfonyl; (d30) phenyl; (d31) having 1 to 5 optionally identical or different substituents selected from halogen atoms, cyano group, nitro group, formyl group, (C1-C6)alkyl, halo(C1-C6)alkyl, (C1-C6)alkoxy, halo(C1-C6)alkoxy, (C3-C6)cycloalkyl(C1-C6)alkyl, R 10 (R 11 )N group, (C1-C6)alkylthio, halo(C1-C6)alkylthio, (C1-C6)alkylsulfinyl, halo(C1-C6)alkylsulfinyl, (C1-C6)alkylsulfonyl and halo(C1-C6)alkylsulfonyl, wherein R 10 (R 11 )N group, R 10 and R 11 is the same as the (a31)R 10 (R 11 )N(C1-C6)alkyl, R 10 and R 11 ; or (d32) (C1-C6) alkoxycarbonyl (C1-C6) alkyl, Q represents: (e1) halogen atom; (e2) cyano group; (e4) formyl group; (e5) (C1-C6) alkyl; (e6) (C2-C6) alkenyl; (e7) (C2-C6) alkynyl; (e8) halo (C1-C6) alkyl; (e11) (C1-C6) alkoxy; (e12) halo (C1-C6) alkoxy; (e13) hydroxy (C1-C6) alkyl; (e14) dihydroxy (C1-C6) alkyl; (e15) (C1-C6) alkoxy (C1-C6) alkyl; (e16) (C1-C6) alkoxy (C2-C6) alkenyl; (e17)R 8 (R 9 )N group, wherein, R 8 and R 9 are the same as the R 8 (R 9 ) in the N group; 8 and R 9 are identical; (e18) dioxolanyl; (e19) dioxolanyl having 1 or 2 substituents on the ring, which are the same or different and are selected from carbonyl and (C1-C6) alkyl; (e20) dioxanyl; (e21) having 1 to 3 optionally identical or different substituents selected from halogen atoms, cyano groups, nitro groups, formyl groups, carbonyl groups, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C3-C6)cycloalkyl(C1-C6)alkyl groups, R 10 (R 11 )N(C1-C6)alkyl groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups, wherein R 10 (R 11 )N(C1-C6)alkyl group of R 10 and R 11 is the same as the (a31)R 10 (R 11 )N(C1-C6)alkyl group of the R 10 and R 11 ; (e22) phenyl; (e23) having 1 to 5, optionally identical or different, substituents selected from halogen atoms, cyano groups, nitro groups, formyl groups, (C1-C6) alkyl groups, halogenated (C1-C6) alkyl groups, (C1-C6) alkoxy groups, halogenated (C1-C6) alkoxy groups, (C3-C6) cycloalkyl(C1-C6) alkyl groups, R 10 (R 11 )N group, (C1-C6) alkylthio groups, halogenated (C1-C6) alkylthio groups, (C1-C6) alkylsulfinyl groups, halogenated (C1-C6) alkylsulfinyl groups, (C1-C6) alkylsulfonyl groups and halogenated (C1-C6) alkylsulfonyl groups, wherein R 10 (R 11 )N group in which R 10 and R 11 are the same as the R 10 (R 11 )N(C1-C6) alkyl group in the (a31)R 10 and R 11 ; (e24) imidazolyl; (e25) having 1 to 3 optionally identical or different substituents selected from halogen atoms, cyano groups, nitro groups, formyl groups, (C1-C6) alkyl groups, halo (C1-C6) alkyl groups, (C1-C6) alkoxy groups, halo (C1-C6) alkoxy groups, (C3-C6) cycloalkyl (C1-C6) alkyl groups, R 10 (R 11 )N group, (C1-C6) alkylthio groups, halo (C1-C6) alkylthio groups, (C1-C6) alkylsulfinyl groups, halo (C1-C6) alkylsulfinyl groups, (C1-C6) alkylsulfonyl groups and halo (C1-C6) alkylsulfonyl groups, and an imidazolyl group having a substituent selected from the group consisting of: wherein, R 10 (R 11 )N group, R 10 and R 11 and the (a31) R 10 (R 11 )N(C1-C6) alkyl group, the R 10 and R 11 are the same; (e26) oxadiazolyl; (e27) having a substituent selected from a halogen atom, a cyano group, a nitro group, a formyl group, a (C1-C6) alkyl group, a halogenated (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halogenated (C1-C6) alkoxy group, a (C3-C6) cycloalkyl(C1-C6) alkyl group, R 10 (R 11 )N group, a (C1-C6) alkylthio group, a halogenated (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a halogenated (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, and a halogenated (C1-C6) alkylsulfonyl group, wherein R 10 (R 11 )N group, R 10 and R 11 are the same as the R 10 (R 11 )N(C1-C6) alkyl group in the (a31)R 10 and R 11 ; (e28)S(O) p R 6 group, wherein R 6 represents a hydrogen atom, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, halo(C1-C6)alkyl, halo(C2-C6)alkenyl, halo(C2-C6)alkynyl, (C1-C6)alkoxy, (C3-C6)cycloalkyl, halo(C3-C6)cycloalkyl, phenyl(C1-C6)alkyl, (C1-C6)alkoxyphenyl(C1-C6)alkyl, (C1-C6)alkylphenyl(C1-C6)alkyl, tris(C1-C6)alkylsilylphenyl(C1-C6)alkyl or N(R 8 )R 9 group, p represents 0, 1 or 2, wherein the R 8 )R 9 in the N(R 8 )R 9 group and the R 8 (R 9 )N group in the (a30)R 8 and R 9 are the same; (e29)C(O)R 7 group, wherein R 7 represents hydroxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, halo(C1-C6)alkyl, halo(C2-C6)alkenyl, halo(C2-C6)alkynyl, (C1-C6)alkoxycarbonyl(C1-C6)alkyl, phenyl(C1-C6)alkyl, phenyl(C1-C6)alkoxy, (C1-C6)alkoxy, (C2-C6)alkenyloxy, (C2-C6)alkynyloxy, (C3-C6)cycloalkoxy, halo(C1-C6)alkoxy, halo(C2-C6)alkynyloxy, phenoxy, (C1-C6)alkoxycarbonyl(C1-C6)alkoxy, (C1-C6)alkylthio, phenyl, thiazolidinyl or N(R 8 )R 9 group, wherein the R 8 )R 9 in the N(R 8 )R 9 group and the R 8 (R 9 )N group in the (a30)R 8 and R 9 are the same; (e30) thiocarboxamido; (e31) N-(C1-C6) alkylaminothiocarbonyl; (e32) N,N-di(C1-C6) alkylaminothiocarbonyl; (e33) [Chemical Formula 3] In the formula, R 6 is the same as the R in the (e28) S (O) p R 6 in the group, and R 6 is the same as the R 8 in the (a30) R 8 (R 9 ) N group; 8 Same; (e34) hydroxyimino (C1-C3) alkyl; (e35) (C1-C6) alkoxyimino (C1-C3) alkyl; (e36) halo (C1-C6) alkoxyimino (C1-C3) alkyl; (e37) hydrazono (C1-C3) alkyl; (e38) (C1-C6) alkylhydrazono (C1-C3) alkyl; (e39) di(C1-C6) alkylhydrazono (C1-C3) alkyl; (e40) phenyl (C1-C6) alkoxyimino (C1-C3) alkyl; (e41) (C2-C6) alkenyloxyimino (C1-C3) alkyl; (e42) di(C1-C6) alkoxyphosphonyl; (e43) di(C1-C6) alkoxyphosphonylamino; (e44) hydroxy; (e45) (C1-C6) alkoxy (C1-C6) alkoxy; or (e46) (C1-C6) alkoxyiminoamino (C1-C3) alkyl.

3. The compound or its salt according to claim 1 or 2, wherein, R 1 means: (a1) halogen atom; (a2) cyano; (a3) nitro; (a4) formyl; (a5) carboxyl; (a6) (C1-C6) alkyl; (a7) (C2-C6) alkenyl; (a9) (C3-C6) cycloalkyl; (a10) halo (C1-C6) alkyl; (a14) hydroxy (C1-C6) alkyl; (a16) (C1-C6) alkoxy (C1-C6) alkyl; (a17) di(C1-C6) alkoxy (C1-C6) alkyl; (a22) (C1-C6) alkoxy; (a23) halo (C1-C6) alkoxy; (a24) (C1-C6) alkylthio; (a26) (C1-C6) alkylsulfonyl; (a27) halo (C1-C6) alkylthio; (a28) halo (C1-C6) alkylsulfinyl; (a29) halo (C1-C6) alkylsulfonyl; (a30)R 8 (R 9 )N group, wherein R 8 and R 9 represent a hydrogen atom, a hydroxyl group, an amino group, a di(C1-C6)alkylamino group, a (C1-C6)alkyl group, a (C3-C6)cycloalkyl group, a (C2-C6)alkenyl group, a (C2-C6)alkynyl group, a (C1-C6)alkoxy group, a (C2-C6)alkenyloxy group, a halo(C1-C6)alkyl group, a halo(C3-C6)cycloalkyl group, a (C3-C6)cycloalkyl(C1-C6)alkyl group, a (C1-C6)alkylcarbonyl group, a halo(C1-C6)alkylcarbonyl group, a (C1-C6)alkoxycarbonyl group, a (C1-C6)alkylsulfonyl group, an N,N-di(C1-C6)alkylaminosulfonyl group, a (C1-C6)alkoxy(C1-C6)alkyl group, a di(C1-C6)alkoxy(C1-C6)alkyl group, a thietanyl group, a thiazolyl group or a 2-oxotetrahydrofuranyl group, and R 8 and R 9 are optionally the same or different and are optionally bonded to each other to form a 4- to 6-membered ring; (a31)R 10 (R 11 )N(C1-C6)alkyl, wherein R 10 and R 11 represent a hydrogen atom or (C1-C6)alkyl, and R 10 and R 11 are optionally the same or different and are optionally bonded to each other to form a 4- to 6-membered ring; (a32) (C1-C6) alkylthio (C1-C6) alkyl; (a33) (C1-C6) alkylsulfinyl (C1-C6) alkyl; (a34) (C1-C6) alkylsulfonyl(C1-C6) alkyl; (a45) (C1-C6) alkoxycarbonyl; (a52)R 10 (R 11 )N-sulfonyl, wherein R 10 and R 11 are the same as the R in the said (a31)R 10 (R 11 )N(C1-C6)alkyl; 10 and R 11 are identical; (a55) (C1-C6) alkoxyimino(C1-C3) alkyl; (a57) phenyl; (a58) phenyl having 1 to 5 substituents, which may be the same or different, selected from halogen atoms and (C1-C6) alkoxy groups on the ring; (a59) pyridyl; (a62) pyrazolyl having 1 to 3 (C1-C6) alkyl groups, which may be the same or different, on the ring; (a65) dioxolanyl; (a67) dioxanyl; (a69) (C1-C6) alkylene formed by bonding of two adjacent substituents; or (a70) methylenedioxy optionally substituted with 1 or 2 halogen atoms, formed by bonding of two adjacent substituents, When m represents an integer of 2 or more, R 1 optionally the same or different, m represents 0, 1, 2, 3 or 4, R 2 means: (b1) hydrogen atom; (b2) (C1-C6) alkyl; (b3) (C3-C6) cycloalkyl; (b5) (C2-C6) alkynyl; (b6) halo(C1-C6) alkyl; or (b9) (C1-C6) alkoxy(C1-C6) alkyl, R 3 means: (c1) hydrogen atom; (c3) cyano; (c5) formamido; (c6) (C1-C6) alkyl; (c12)R 8 (R 9 )N group, wherein R 8 and R 9 are the same as the R 8 (R 9 ) in the N group of (a30)R 8 and R 9 ; (c13) (C1-C6) alkoxy; or (c16) (C1-C6) alkoxycarbonyl(C1-C6) alkyl, R 4 means: (d1) hydrogen atom; (d2) (C1-C6) alkyl; (d3) (C2-C6) alkenyl; (d4) (C2-C6) alkynyl; (d6) halo(C1-C6) alkyl; (d9) (C1-C6) alkoxy(C1-C6) alkyl; (d13) (C3-C6) cycloalkyl(C1-C6) alkyl; (d14) cyano(C1-C6) alkyl; (d15) (C1-C6) alkylthio(C1-C6) alkyl; (d16) (C1-C6) alkylsulfinyl(C1-C6) alkyl; (d17) (C1-C6) alkylsulfonyl(C1-C6) alkyl; (d18) carboxy(C1-C6) alkyl; (d19) phenyl(C1-C6) alkyl; (d20) phenyl(C1-C6) alkyl having 1 to 5 halogen atoms, which may be the same or different, on the ring; (d22) (C1-C6) alkylcarbonyl; (d23) (C1-C6) alkoxycarbonyl; (d24) (C1-C6) alkylsulfonyl; (d30) phenyl; or (d32) (C1-C6) alkoxycarbonyl(C1-C6) alkyl, A 1 , A 2 and A 3 Represents CR 5 or nitrogen atom, A 1 , A 2 and A 3 Optional same or different, wherein CR 5 R 5 represents a hydrogen atom, a halogen atom, a (C1-C6) alkyl group or R 10 (R 11 )N-based, R 10 (R 11 )R in N-base 10 and R 11 With the (a31)R 10 (R 11 )N(C1-C6)alkyl 10 and R 11 same, Q represents: (e1) halogen atom; (e2) cyano; (e4) formyl; (e5) (C1-C6) alkyl; (e6) (C2-C6) alkenyl; (e8) halo(C1-C6) alkyl; (e11) (C1-C6) alkoxy; (e13) hydroxy(C1-C6) alkyl; (e14) dihydroxy(C1-C6) alkyl; (e16) (C1-C6) alkoxy(C2-C6) alkenyl; (e17)R 8 (R 9 )N group, where R 8 and R 9 are the same as the R 8 (R 9 ) in the N group; 8 and R 9 are identical; (e18) dioxolanyl; (e19)A dioxolanyl group having 1 or 2 optional substituents which are the same or different and selected from a carbonyl group and (C1-C6) alkyl groups on the ring; (e20)A dioxanyl group; (e22)A phenyl group; (e24)An imidazolyl group; (e27)An oxadiazolyl group having (C1-C6) alkyl groups on the ring; (e28)S(O) p R 6 group, wherein R 6 represents a hydrogen atom, (C1-C6)alkyl, halo(C1-C6)alkyl, phenyl(C1-C6)alkyl, (C1-C6)alkoxyphenyl(C1-C6)alkyl, (C1-C6)alkylphenyl(C1-C6)alkyl, tris(C1-C6)alkylsilylphenyl(C1-C6)alkyl or N(R 8 )R 9 group, p represents 0, 1 or 2, wherein the R 8 )R 9 in the N(R 8 )R 9 group and the R 8 (R 9 )N group in the (a30)R 8 and R 9 are the same; (e29)C(O)R 7 group, wherein R 7 represents hydroxy, (C1-C6)alkyl, (C1-C6)alkoxycarbonyl(C1-C6)alkyl, phenyl(C1-C6)alkoxy, (C1-C6)alkoxy, (C2-C6)alkynyloxy, (C3-C6)cycloalkoxy, phenoxy, (C1-C6)alkoxycarbonyl(C1-C6)alkoxy, (C1-C6)alkylthio, thiazolidinyl or N(R 8 )R 9 group, wherein the R 8 )R 9 in the N(R 8 )R 9 group and the R 8 (R 9 )N group in the (a30)R 8 and R 9 are the same; (e31)N-(C1-C6) alkylaminothiocarbonyl; (e33)[Chemical formula 4] In the formula, R 6 is the same as the R in the (e28) S(O) p R 6 group, and R 6 is the same as the R 8 in the (a30) R 8 (R 9 )N group; 8 Same; (e35)(C1-C6) alkoxyimino (C1-C3) alkyl; (e36)Halogenated (C1-C6) alkoxyimino (C1-C3) alkyl; (e37)Hydrazono (C1-C3) alkyl; (e40)Phenyl (C1-C6) alkoxyimino (C1-C3) alkyl; (e41)(C2-C6) alkenyloxyimino (C1-C3) alkyl; (e42)Bis(C1-C6) alkoxyphosphonyl; (e43)Bis(C1-C6) alkoxyphosphonylamino; (e44)Hydroxy; or (e45)(C1-C6) alkoxy (C1-C6) alkoxy.

4. The compound or its salt according to claim 1, wherein, A 1 represents a nitrogen atom, A 2 With A 3 Optionally the same or different, representing CR 5 。 5. The compound or its salt according to claim 2, wherein, A 1 represents a nitrogen atom, A 2 with A 3 optionally the same or different, represents CR 5 .

6. The compound or its salt according to claim 3, wherein, A 1 represents a nitrogen atom, A 2 With A 3 Optionally the same or different, representing CR 5 .

7. The compound or its salt according to claim 2, wherein, A 1 , A 2 and A 3 Optional same or different, means CR 5 .

8. The compound or its salt according to claim 3, wherein, A 1 , A 2 and A 3 Optional same or different, means CR 5 .

9. The compound or its salt according to claim 3, wherein, A 1 and A 3 optionally the same or different, representing CR 5 , A 2 represents a nitrogen atom.

10. The compound or its salt according to claim 3, wherein, A 1 With A 2 Optionally the same or different, representing CR 5 , A 3 represents a nitrogen atom.

11. The compound or its salt according to claim 3, wherein, A 1 and A 3 represent a nitrogen atom, A 2 represents CR 5 .

12. The compound or its salt according to claim 2, wherein, A 1 and A 2 represents a nitrogen atom, A 3 represents CR 5 .

13. The compound or its salt according to claim 3, wherein, A 1 and A 2 represents a nitrogen atom, A 3 represents CR 5 .

14. The compound or its salt according to claim 3, wherein, A 1 represents CR 5 , A 2 and A 3 represent nitrogen atoms.

15. A herbicide for agricultural horticulture, characterized in that, Containing the compound or its salt according to any one of claims 1 to 14 as an active ingredient.

16. A method for using a herbicide for agricultural horticulture, characterized in that, Treating weeds, soil, paddy fields or cultivation carriers with an effective amount of the agricultural and horticultural herbicide according to claim 15.

17. A method for controlling weeds, characterized in that, Treating weeds, soil, paddy fields or cultivation carriers with an effective amount of the agricultural and horticultural herbicide according to claim 15.

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