Sulfamoyl compounds and agricultural and horticultural fungicides

Abstract

A sulfamoyl compound of the general formulae (1): 1

Description

TECHNICAL FIELD

[0001] The present invention relates to novel sulfamoyl compounds, and agricultural chemicals (insecticides, fungicides, herbicides, plant growth controlling agents and the like.), particularly agricultural and horticultural fungicides.

BACKGROUND ART

[0002] JP-A-3-170464, JP-A-6-32785, JP-A-7-2803 and JP-A-7-215971 describe that certain sulfamoyl compounds have bactericidal activities.

[0003] Even the compounds described in the above-described early publications are unsatisfactory in potency and residual effectiveness, thus developments of more useful agricultural and horticultural fungicide have been desired.

DISCLOSURE OF THE INVENTION

[0004] Under the circumstances, the present inventors have made extensive research with a view to developing excellent fungicide and, as a result, have found that novel sulfamoyl compounds have remarkable controlling activity as agricultural and horticultural fungicide, thus accomplishing the present invention.

[0005] That is, the present invention relates to [1] to [38].

[0006] [1] A sulfamoyl compound of the general formulae (1): 2

[0007] wherein

[0008] R1 and R2 are each independently C1-4 alkyl, or R1 and R2 together are C4-6 alkylene or C4-6 alkyleneoxy,

[0009] Y is H, halogen, C1-8 alkyl, C1-8 alkoxy, C1-8 alkylthio, C1-8 haloalkyl, C1-8 haloalkoxy or C1-8 haloalkylthio,

[0010] A is 3

[0011] W is a chemical bond or O,

[0012] V is O or S,

[0013] D, E, F and G are each independently N, CR7, CR8, CR9 or CR10, and

[0014] R3, R4, R5, R6, R7, R8, R9, R10 and R11 are each independently H, C1-8 alkyl, C3-8 cycloalkyl, C2-8 alkenyl, C5-8 cycloalkenyl, C2-8 alkynyl, C1-8 alkoxy, C3-8 cycloalkyloxy, C5-8 cycloalkenyloxy, C2-8 alkenyloxy, C2-8 alkynyloxy, C1-8 alkylthio, C3-8 cycloalkylthio, C5-8 cycloalkenylthio, C2-8 alkenylthio. C2-8 alkynylthio, C1-8 haloalkyl, C1-8 haloalkoxy, C1-8 haloalkylthio, C2-8 haloalkenyl, C2-8 haloalkenyloxy, C2-8 haloalkenylthio, C2-8 haloalkynyl, C2-8 haloalkynyloxy, C2-8 haloalkynylthio, phenyl which may be substituted (the kinds of substituent include halogen, C1-8 alkyl, C1-8 haloalkyl, C1-8 alkoxy, C1-8 haloalkoxy, C1-8 alkylthio, C1-8 haloalkylthio, C1-6 alkylsulfoxy, C1-6 alkylsulfonyl, CN, NO2 and C1-6 alkoxycarbonyl, the number of the substituents is 1 to 5, and the substituents may be identical or different.), phenyl C1-4 alkyl which may be substituted, benzylthio which may be substituted, benzyloxy which may be substituted, phenoxy C1-4 alkyl which may be substituted, phenoxy which may be substituted, phenylthio C1-4 alkyl which may be substituted, phenylthio which may be substituted, benzoyl which may be substituted, benzoyl C1-4 alkyl which may be substituted, benzoyloxy which may be substituted, benzoyloxy C1-4 alkyl which may be substituted, naphthyl which may be substituted, 5- or 6-membered heterocyclic ring which may be substituted, C1-8 hydroxyalkyl, C1-8 hydroxyhaloalkyl, C1-6 alkoxy C1-4 alkyl, C1-6 haloalkoxy C1-4 alkyl, C1-6 haloalkylthio C1-4 alkyl, C1-10 dialkoxy C1-4 alkyl, C1-3 alkylenedioxy C1-4 alkyl, C1-6 alkylthio C1-4 alkyl, C1-10 dialkylthio C1-4 alkyl, C1-3 alkylenedithio C1-4 alkyl, C1-6 alkoxycarbonyl, C1-6 haloalkoxycarbonyl, C1-6 alkoxyoxalyl, CHO, CO2H, C1-6 alkoxycarbonyl C1-4 alkyl, C1-6 haloalkoxycarbonyl C1-4 alkyl, NH2, C1-6 alkylamino, C1-6 alkylcarbonylamino, C1-6 alkylcarbonylamino C1-4 alkyl, C1-6 haloalkylcarbonylamino, C1-6 haloalkylcarbonylamino C1-4 alkyl, C1-6 alkoxycarbonylamino, C1-6 alkoxycarbonylamino C1-4 alkyl, C1-6 alkylsulfonylamino, C1-6 alkylsulfonylamino C1-4 alkyl, C1-6 haloalkylsulfonylamino, C1-6 haloalkylsulfonylamino C1-4 alkyl, C1-6 dialkylamino, C1-6 dialkylamino C1-4 alkyl, C1-6 dialkylaminocarbonyl, C1-6 dialkylaminocarbonyl C1-4 alkyl, C2-6 alkyleneimino, C2-6 alkyleneimino C1-4 alkyl, C2-6 alkyleneiminocarbonyl, C2-6 alkyleneiminocarbonyl C1-4 alkyl, C1-6 alkylcarbonyl, C1-6 alkylcarbonyloxy, C1-6 haloalkylcarbonyl, C1-6 haloalkylcarbonyloxy, C1-6 alkylcarbonyl C1-4 alkyl, C1-6 alkylcarbonyloxy C1-4 alkyl, C1-6 haloalkylcarbonyl C1-4 alkyl, C1-6 haloalkylcarbonyloxy C1-4 alkyl, hydroxyimino C1-4 alkyl, C1-6 alkoxyimino C1-4 alkyl, C1-6 alkylcarbonyloxyimino C1-4 alkyl, C1-6 alkylsulfonyloxyimino C1-4 alkyl, C1-6 alkylsulfoxy, C1-6 haloalkylsulfoxy, C1-6 alkylsulfoxy C1-4 alkyl, C1-6 haloalkylsulfoxy C1-4 alkyl, C1-6 alkylsulfonyl, C1-6 haloalkylsulfonyl, C1-6 alkylsulfonyl C1-4 alkyl, C1-6 haloalkylsulfonyl C1-4 alkyl, C1-6 alkylsulfonyloxy, C1-6 haloalkylsulfonyloxy, C1-6 alkylsulfonyloxy C1-4 alkyl, C1-6 haloalkylsulfonyloxy C1-4 alkyl, C1-6 haloalkoxysulfonyl, C1-6 haloalkoxysulfonyl C1-4 alkyl, C1-6 dialkylsulfamoyl, C1-6 dialkylsulfamoyl C1-4 alkyl, C1-6 alkoxysulfonyl, C1-6 alkoxysulfonyl C1-4 alkyl, C2-6 cyanoalkyl, CN, C1-6 thiocarbamoyl, C1-6 nitroalkyl, NO2 or halogen, or two of R3, R4, R5, R6, R7, R8, R9, R10 and R11 together are C1-3 alkylenedioxy which may be substituted, or C3-6 alkylene.

[0015] [2] A sulfamoyl compound described in [1] above, in which A is A-1.

[0016] [3] A sulfamoyl compound described in [1] above, in which A is A-2.

[0017] [4] A sulfamoyl compound described in [1] above, in which A is A-3.

[0018] [5] A sulfamoyl compound described in [1] above, in which A is A-4.

[0019] [6] A sulfamoyl compound described in [1] above, in which A is A-5 or A-6.

[0020] [7] A sulfamoyl compound described in [1] above, in which A is A-7 or A-8.

[0021] [8] A sulfamoyl compound described in [1] above, in which A is A-9 or A-10.

[0022] [9] A sulfamoyl compound described in [1] above, in which B is B-1.

[0023] [10] A sulfamoyl compound described in [1] above, in which B is B-2.

[0024] [11] A sulfamoyl compound described in [1] above, in which B is B-3 or B-4.

[0025] [12] A sulfamoyl compound described in [1] above, in which B is B-5.

[0026] [13] A sulfamoyl compound described in [1] above, in which B is B-6 or B-7.

[0027] [14] A sulfamoyl compound described in [1] above, in which B is B-8 or B-9.

[0028] [15] A sulfamoyl compound described in [1] above, in which B is B-10.

[0029] [16] A sulfamoyl compound described in [1] above, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR7, CR8, CR9 or CR10, and R3 is C1-8 alkylthio.

[0030] [17] A sulfamoyl compound described in [1] above, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR7, CR8, CR9 or CR10, and R3 is C1-8 alkyl.

[0031] [18] A sulfamoyl compound described in [1] above, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR7, CR8, CR9 or CR10, and R3 is C1-8 haloalkyl.

[0032] [19] A sulfamoyl compound described in [1] above, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR7, CR8, CR9 or CR10, and R3 is halogen.

[0033] [20] A sulfamoyl compound described in [1] above, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR7, CR8, CR9 or CR10, and R3 is H.

[0034] [21] A sulfamoyl compound described in [1] above, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR7, CR8, CR9 or CR10, and R3 is CN.

[0035] [22] A sulfamoyl compound described in [1] above, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-2, D, E, F and G are CR7, CR8, CR9 or CR10, and any of R3, R4, R5 and R6 is H.

[0036] [23] A sulfamoyl compound described in [1] above, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-4, and at least one of R3, R4, R5 and R6 is phenyl which may be substituted.

[0037] [24] A sulfamoyl compound described in [1] above, in which R1 and R2 are Me, Y is H, W is a chemical bond, and B is B-1.

[0038] [25] A sulfamoyl compound described in [1] above, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR7, CR8, CR9 or CR10, R3 is C1-8 alkyl, and R4 is halogen.

[0039] [26] A sulfamoyl compound described in [1] above, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR7, CR8, CR9 or CR10, and any of R3 and R4 is halogen.

[0040] [27] A sulfamoyl compound described in [1] above, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR7, CR8, CR9 or CR10, R3 is C1-8 alkyl, and R4 is H or C1-8 alkyl.

[0041] [28] A sulfamoyl compound described in [1] above, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR7, CR8, CR9 or CR10, R3 is C1-8 haloalkyl, and R4 is H, halogen or C1-8 alkyl.

[0042] [29] A sulfamoyl compound described in [1] above, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR7, CR8, CR9 or CR10, R3 is H or C1-8 alkyl, and R4 is C1-6 alkoxycarbonyl.

[0043] [30] A sulfamoyl compound described in [1] above, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR7, CR8, CR9 or CR10, R3 is H, and R4 is halogen.

[0044] [31] A sulfamoyl compound described in [1] above, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR7, CR8, CR9 or CR10, R3 is CN, and R4 is H or C1-8 alkyl.

[0045] [32] A sulfamoyl compound described in [1] above, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, any of D, E, F and G is CH, R3 is C1-8 alkyl, and R4 is halogen.

[0046] [33] A sulfamoyl compound described in [1] above, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, any of D, E, F and G is CH, and any of R3 and R4 is halogen.

[0047] [34] A sulfamoyl compound described in [1] above, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, any of D, E, F and G is CH, R3 is C1-8 haloalkyl, and R4 is H or C1-3 alkyl.

[0048] [35] A sulfamoyl compound described in [1] above, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, any of D, E, F and G is CH, R3 is Me or Et, and R4 is Cl or Br.

[0049] [36] A sulfamoyl compound described in [1] above, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, any of D, E, F and G is CH, R3 is Cl or Br, and R4 is Cl or Br.

[0050] [37] An agricultural chemical containing as the active ingredient at least one sulfamoyl compound described in [1] to [36] above.

[0051] [38] An agricultural chemical as described in [37] above, in which the agricultural chemical is an agricultural and horticultural fungicide.

[0052] In the compounds of the general formula (1), examples of C1-4 alkyl for R1 and R2 are methyl, ethyl, n- or i-propyl, n-, i- or s-butyl and the like.

[0053] Examples of C4-6 alkylene formed by R1 and R2 together are piperidine including the N to which R1 and R2 are bonded and the like.

[0054] Examples of C4-6 alkyleneoxy formed by R1 and R2 together are morpholine including the N to which R1 and R2 are bonded and the like.

[0055] The definitions of substituents Y, R3, R4, R5, R6, R7, R8, R9, R10 and R11 have following meanings.

[0056] Examples of C1-8 alkyl are methyl, ethyl, n- or i-propyl, n- or i-butyl, n-pentyl and the like.

[0057] Examples of C3-8 cycloalkyl are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like.

[0058] Examples of C2-8 alkenyl are allyl, vinyl and the like.

[0059] Examples of C5-8 cycloalkenyl are cyclopentenyl and the like.

[0060] Examples of C2-8 alkynyl are propargyl and the like.

[0061] Examples of C1-8 alkoxy are methoxy, ethoxy and the like.

[0062] Examples of C3-8 cycloalkyloxy are cyclopropyloxy and the like.

[0063] Examples of C3-8 cycloalkenyloxy are cyclopentenyl-3-oxy and the like.

[0064] Examples of C2-8 alkenyloxy are allyloxy and the like.

[0065] Examples of C2-8 alkynyloxy are propargyloxy and the like.

[0066] Examples of C1-8 alkylthio are methylthio, ethylthio, n- or i-propylthio and the like.

[0067] Examples of C3-8 cycloalkylthio are cyclopentylthio and the like.

[0068] Examples of C3-8 cycloalkenylthio are cyclopentenyl-3-thio and the like.

[0069] Examples of C2-8 alkenylthio are allylthio and the like.

[0070] Examples of C2-8 alkynylthio are propargylthio and the like.

[0071] Examples of C1-8 haloalkoxy are trifluoromethoxy and the like.

[0072] Examples of C1-8 haloalkylthio are trifluoromethylthio and the like.

[0073] Examples of C1-8 haloalkyl are chloromethyl, dichloromethyl, dichlorofluoromethyl, trifluoromethyl and the like.

[0074] Examples of C2-8 haloalkenyl are 3-chloroallyl and the like.

[0075] Examples of C2-8 haloalkenyloxy are 3-chloroallyloxy and the like.

[0076] Examples of C2-8 haloalkenylthio are 3-chloroallylthio and the like.

[0077] Examples of C2-8 haloalkynyl are iodopropargyl and the like.

[0078] Examples of C2-8 haloalkynyloxy are iodopropargyloxy and the like.

[0079] Examples of C2-8 haloalkynylthio are iodopropargylthio and the like.

[0080] Examples of C1-8 hydroxyalkyl are hydroxymethyl, 1-hydroxyethyl and the like.

[0081] Examples of C1-8 hydroxyhaloalkyl are 2,2,2-trifluoro-1-hydroxyethyl and the like.

[0082] Examples of C1-6 alkoxy C1-4 alkyl are methoxymethyl, methoxyethyl and the like.

[0083] Examples of C1-6 haloalkoxy C1-4 alkyl are trifluoroethoxymethyl and the like.

[0084] Examples of C1-6 alkylthio C1-4 alkyl are methylthiomethyl, ethylthiomethyl, methylthioethyl and the like.

[0085] Examples of C1-6 haloalkylthio C1-4 alkyl are trifluoroethylthiomethyl and the like.

[0086] Examples of C1-10 dialkoxy C1-4 alkyl are dimethoxymethyl, diethoxymethyl and the like.

[0087] Examples of C1-10 dialkylthio C1-4 alkyl are dimethylthiomethyl, diethylthiomethyl and the like.

[0088] Examples of C1-3 alkylenedioxy C1-4 alkyl are ethylenedioxymethyl and the like.

[0089] Examples of C1-3 alkylenedithio C1-4 alkyl are ethylenedithiomethyl and the like.

[0090] Examples of phenoxy C1-4 alkyl which may be substituted are phenoxymethyl and the like.

[0091] Examples of phenoxy which may be substituted are phenoxy and the like.

[0092] Examples of phenylthio C1-4 alkyl which may be substituted are phenylthiomethyl and the like.

[0093] Examples of phenylthio which may be substituted are phenylthio and the like.

[0094] Examples of phenyl C1-4 alkyl which may be substituted are benzyl, phenethyl and the like.

[0095] Examples of benzylthio which may be substituted are benzylthio and the like.

[0096] Examples of benzyloxy which may be substituted are benzyloxy and the like.

[0097] Examples of phenyl which may be substituted are phenyl and the like.

[0098] Examples of benzoyl which may be substituted are benzoyl and the like.

[0099] Examples of benzoyl C1-4 alkyl which may be substituted are benzoylmethyl and the like.

[0100] Examples of benzoyloxy which may be substituted are benzoyloxy and the like.

[0101] Examples of benzoyloxy C1-4 alkyl which may be substituted are benzoyloxymethyl and the like.

[0102] Examples of naphthyl which may be substituted are naphthyl and the like.

[0103] Examples of 5- or 6-membered heterocyclic ring are pyridine, thiophene, furan, thiazole and the like.

[0104] Examples of C1-6 alkoxycarbonyl are methoxycarbonyl and the like.

[0105] Examples of C1-6 alkoxycarbonyl C1-4 alkyl are methoxycarbonylmethyl and the like.

[0106] Examples of C1-6 haloalkoxycarbonyl are fluoroethoxycarbonyl and the like.

[0107] Examples of C1-6 haloalkoxycarbonyl C1-4 alkyl are fluoroethoxycarbonylmethyl and the like.

[0108] Examples of C1-6 alkoxyoxalyl are methoxyoxalyl, ethoxyoxalyl and the like.

[0109] Examples of C1-6 dialkylamino are dimethylamino and the like.

[0110] Examples of C1-6 alkylamino are methylamino and the like.

[0111] Examples of C1-6 dialkylamino C1-4 alkyl are dimethylaminomethyl and the like.

[0112] Examples of C2-6 alkyleneimino are pyrrolidino, piperidino and the like.

[0113] Examples of C2-6 alkyleneiminocarbonyl are pyrrolidinocarbonyl, piperidinocarbonyl and the like.

[0114] Examples of C2-6 alkyleneimino C1-4 alkyl are pyrrolidinomethyl, piperidinomethyl and the like.

[0115] Examples of C2-6 alkyleneiminocarbonyl C1-4 alkyl are pyrrolidinocarbonylmethyl, piperidinocarbonylmethyl and the like.

[0116] Examples of C1-6 alkylcarbonylamino are acethylamino and the like.

[0117] Examples of C1-6 alkoxycarbonylamino are methoxycarbonylamino and the like.

[0118] Examples of C1-6 haloalkylcarbonylamino are trifluoroacethylamino and the like.

[0119] Examples of C1-6 alkylsulfonylamino are methanesulfonylamino and the like.

[0120] Examples of C1-6 haloalkylsulfonylamino are chloromethylsulfonylamino and the like.

[0121] Examples of C1-6 alkylcarbonylamino C1-4 alkyl are acetylaminomethyl and the like.

[0122] Examples of C1-6 alkoxycarbonylamino C1-4 alkyl are methoxycarbonylaminomethyl and the like.

[0123] Examples of C1-6 haloalkylcarbonylamino C1-4 alkyl are trifluoroacetylaminomethyl and the like.

[0124] Examples of C1-6 alkylsulfonylamino C1-4 alkyl are methanesulfonylaminomethyl and the like.

[0125] Examples of C1-6 haloalkylsulfonylamino C1-4 alkyl are chloromethylsulfonylaminomethyl and the like.

[0126] Examples of C1-6 dialkylaminocarbonyl are dimethylaminocarbonyl and the like.

[0127] Examples of C1-6 dialkylaminocarbonyl C1-4 alkyl are dimethylaminocarbonylmethyl and the like.

[0128] Examples of C1-6 alkylcarbonyl are acetyl and the like.

[0129] Examples of C1-6 haloalkylcarbonyl are trifluoroacetyl and the like.

[0130] Examples of C1-6 alkylcarbonyloxy are acetyloxy and the like.

[0131] Examples of C1-6 haloalkylcarbonyloxy are trifluoroacetyloxy and the like.

[0132] Examples of C1-6 alkylcarbonyl C1-4 alkyl are acetylmethyl and the like.

[0133] Examples of C1-6 haloalkylcarbonyl C1-4 alkyl are trifluoroacetylmethyl and the like.

[0134] Examples of C1-6 alkylcarbonyloxy C1-4 alkyl are acetyloxymethyl and the like.

[0135] Examples of C1-6 haloalkylcarbonyloxy C1-4 alkyl are trifluoroacetyloxymethyl and the like.

[0136] Examples of hydroxyimino C1-4 alkyl are hydroxyiminomethyl and the like.

[0137] Examples of alkoxyimino C1-4 alkyl are methoxyiminomethyl and the like.

[0138] Examples of C1-6 alkylcarbonyloxyimino C1-4 alkyl are acetyloxyiminomethyl and the like.

[0139] Examples of C1-6 alkylsulfonyloxyimino C1-4 alkyl are methanesulfonyloxyiminomethyl and the like.

[0140] Examples of C1-6 alkylsulfoxy are methylsulfoxy and the like.

[0141] Examples of C1-6 alkylsulfoxy C1-4 alkyl are methylsulfoxymethyl, ethylsulfoxymethyl, methylsulfoxyethyl and the like.

[0142] Examples of C1-6 alkylsulfonyl are methanesulfonyl and the like.

[0143] Examples of C1-6 alkylsulfonyloxy are methanesulfonyloxy and the like.

[0144] Examples of C1-6 alkylsulfonyl C1-4 alkyl are methylsulfonylmethyl, ethylsulfonylmethyl, methylsulfonylethyl and the like.

[0145] Examples of C1-6 alkylsulfonyloxy C1-4 alkyl are methylsulfonyloxymethyl and the like.

[0146] Examples of C1-6 haloalkylsulfoxy are chloromethylsulfoxy and the like.

[0147] Examples of C1-6 haloalkylsulfoxy C1-4 alkyl are chloromethylsulfoxymethyl and the like.

[0148] Examples of C1-6 haloalkylsulfonyl are trifluoromethylsulfonyl and the like.

[0149] Examples of C1-6 haloalkylsulfonyloxy are trifluoromethylsulfonyloxy and the like.

[0150] Examples of C1-6 haloalkylsulfonyl C1-4 alkyl are trifluoromethylsulfonylmethyl and the like.

[0151] Examples of C1-6 haloalkylsulfonyloxy C1-4 alkyl are trifluoromethylsulfonyloxymethyl and the like.

[0152] Examples of C1-6 dialkylsulfamoyl are dimethylsulfamoyl and the like.

[0153] Examples of C1-6 dialkylsulfamoyl C1-4 alkyl are dimethylsulfamoylmethyl and the like.

[0154] Examples of C1-6 alkoxysulfonyl are methoxysulfonyl and the like.

[0155] Examples of C1-6 alkoxysulfonyl C1-4 alkyl are methoxysulfonylmethyl and the like.

[0156] Examples of C1-6 haloalkoxysulfonyl are fluoroethoxysulfonyl and the like.

[0157] Examples of C1-6 haloalkoxysulfonyl C1-4 alkyl are fluoroethoxysulfonylmethyl and the like.

[0158] Examples of C1-6 nitroalkyl are nitromethyl and the like.

[0159] Examples of C2-6 cyanoalkyl are cyanomethyl and the like.

[0160] Examples of C1-6 thiocarbamoyl are CSNH2 and the like.

[0161] Examples of halogen are F, Cl, Br and I.

[0162] Examples of C1-3 alkylenedioxy which may be substituted with halogen are difluoromethylenedioxy, tetrafluoroethylenedioxy and the like.

[0163] Next, the compounds of the invention of the formula (1) are shown in Tables 1 to 11. However, the present invention should not be construed as being limited thereto.

[0164] In the Tables, Me denotes methyl, Et denotes ethyl, Pr denotes propyl, Bu denotes butyl, n- denotes normal, i- denotes iso, s- denotes secondary, t- denotes tertiary, Ph denotes phenyl, Bn denotes benzyl, and Ac denotes acetyl.

TABLE 1
4
5
6
7
8
9
10
11
12
13
14
15
	Compound No.	R3	R4
	1-1	H	H
	1-2	Me	H
	1-3	Et	H
	1-4	n-Pr	H
	1-5	i-Pr	H
	1-6	n-Bu	H
	1-7	Ph	H
	1-8	Bn	H
	1-9	F	H
	1-10	Cl	H
	1-11	Br	H
	1-12	I	H
	1-13	SMe	H
	1-14	SEt	H
	1-15	CH2OMe	H
	1-16	CClF2	H
	1-17	CHF2	H
	1-18	CHFCl	H
	1-19	CH2Cl	H
	1-20	CF3	H
	1-21	CN	H
	1-22	CHO	H
	1-23	C2F5	H
	1-24	CH═NOMe	H
	1-25	CO2Me	H
	1-26	CO2Et	H
	1-27	CONMe2	H
	1-28	COMe	H
	1-29	COPh	H
	1-30	CH2CO2Me	H
	1-31	NO2	H
	1-32	H	Cl
	1-33	Me	Cl
	1-34	Et	Cl
	1-35	n-Pr	Cl
	1-36	i-Pr	Cl
	1-37	n-Bu	Cl
	1-38	Ph	Cl
	1-39	Bn	Cl
	1-40	F	Cl
	1-41	Cl	Cl
	1-42	Br	Cl
	1-43	I	Cl
	1-44	SMe	Cl
	1-45	SEt	Cl
	1-46	CH2OMe	Cl
	1-47	CHF2	Cl
	1-48	CHFCl	Cl
	1-49	CH2Cl	Cl
	1-50	CF3	Cl
	1-51	CN	Cl
	1-52	CHO	Cl
	1-53	C2F5	Cl
	1-54	CH═NOMe	Cl
	1-55	CO2Me	Cl
	1-56	CO2Et	Cl
	1-57	CONMe2	Cl
	1-58	COMe	Cl
	1-59	CClF2	Cl
	1-60	CH2CO2Me	Cl
	1-61	NO2	Cl
	1-62	H	Br
	1-63	Me	Br
	1-64	Et	Br
	1-65	n-Pr	Br
	1-66	i-Pr	Br
	1-67	n-Bu	Br
	1-68	Ph	Br
	1-69	Bn	Br
	1-70	F	Br
	1-71	Cl	Br
	1-72	Br	Br
	1-73	I	Br
	1-74	SMe	Br
	1-75	SEt	Br
	1-76	CH2OMe	Br
	1-77	CHF2	Br
	1-78	CHFCl	Br
	1-79	CH2Cl	Br
	1-80	CF3	Br
	1-81	CN	Br
	1-82	CHO	Br
	1-83	C2F5	Br
	1-84	CH═NOMe	Br
	1-85	CO2Me	Br
	1-86	CO2Et	Br
	1-87	CONMe2	Br
	1-88	COMe	Br
	1-89	CClF2	Br
	1-90	CH2CO2Me	Br
	1-91	NO2	Br
	1-92	H	I
	1-93	Me	I
	1-94	Et	I
	1-95	n-Pr	I
	1-96	n-Bu	I
	1-97	Ph	I
	1-98	F	I
	1-99	Cl	I
	1-100	Br	I
	1-101	I	I
	1-102	SMe	I
	1-103	CF3	I
	1-104	CN	I
	1-105	H	F
	1-106	Me	F
	1-107	Et	F
	1-108	n-Pr	F
	1-109	n-Bu	F
	1-110	Ph	F
	1-111	F	F
	1-112	Cl	F
	1-113	Br	F
	1-114	CO2Et	F
	1-115	SMe	F
	1-116	CF3	F
	1-117	CN	F
	1-118	H	Me
	1-119	Me	Me
	1-120	Et	Me
	1-121	n-Pr	Me
	1-122	CF2Cl	Me
	1-123	CHF2	Me
	1-124	F	Me
	1-125	Cl	Me
	1-126	Br	Me
	1-127	I	Me
	1-128	SMe	Me
	1-129	CF3	Me
	1-130	CN	Me
	1-131	CHO	Me
	1-132	CH═NOH	Me
	1-133	CH═NOMe	Me
	1-134	CH═NOAc	Me
	1-135	H	Et
	1-136	Me	Et
	1-137	Et	Et
	1-138	n-Pr	Et
	1-139	F	Et
	1-140	Cl	Et
	1-141	Br	Et
	1-142	CHF2	Et
	1-143	CClF2	Et
	1-144	CF3	Et
	1-145	CN	Et
	1-146	CHO	Et
	1-147	—(CH2)3—
	1-148	—(CH2)4—
	1-149	—(CH2)5—
	1-150	—(CH2)6—
	1-151	H	Ph
	1-152	Me	Ph
	1-153	Et	Ph
	1-154	n-Pr	Ph
	1-155	F	Ph
	1-156	Cl	Ph
	1-157	Br	Ph
	1-158	I	Ph
	1-159	SMe	Ph
	1-160	CF3	Ph
	1-161	CN	Ph
	1-162	CHO	Ph
	1-163	H	Bn
	1-164	Me	Bn
	1-165	Et	Bn
	1-166	n-Pr	Bn
	1-167	F	Bn
	1-168	Cl	Bn
	1-169	Br	Bn
	1-170	I	Bn
	1-171	SMe	Bn
	1-172	CF3	Bn
	1-173	CN	Bn
	1-174	H	CF3
	1-175	Me	CF3
	1-176	Et	CF3
	1-177	n-Pr	CF3
	1-178	n-Bu	CF3
	1-179	Ph	CF3
	1-180	F	CF3
	1-181	Cl	CF3
	1-182	Br	CF3
	1-183	I	CF3
	1-184	SMe	CF3
	1-185	CF3	CF3
	1-186	CN	CF3
	1-187	H	CHO
	1-188	Me	CHO
	1-189	Et	CHO
	1-190	n-Pr	CHO
	1-191	n-Bu	CHO
	1-192	F	CHO
	1-193	Cl	CHO
	1-194	Br	CHO
	1-195	I	CHO
	1-196	SMe	CHO
	1-197	CF3	CHO
	1-198	CN	CHO
	1-199	H	CH═NOH
	1-200	Me	CH═NOH
	1-201	Et	CH═NOH
	1-202	n-Pr	CH═NOH
	1-203	F	CH═NOH
	1-204	Cl	CH═NOH
	1-205	Br	CH═NOH
	1-206	I	CH═NOH
	1-207	SMe	CH═NOH
	1-208	CF3	CH═NOH
	1-209	CN	CH═NOH
	1-210	H	CH═NOMe
	1-211	Me	CH═NOMe
	1-212	Et	CH═NOMe
	1-213	n-Pr	CH═NOMe
	1-214	F	CH═NOMe
	1-215	Cl	CH═NOMe
	1-216	Br	CH═NOMe
	1-217	I	CH═NOMe
	1-218	SMe	CH═NOMe
	1-219	CF3	CH═NOMe
	1-220	CN	CH═NOMe
	1-221	H	CH═NOAc
	1-222	Me	CH═NOAc
	1-223	Et	CH═NOAc
	1-224	n-Pr	CH═NOAc
	1-225	F	CH═NOAc
	1-226	Cl	CH═NOAc
	1-227	Br	CH═NOAc
	1-228	I	CH═NOAc
	1-229	SMe	CH═NOAc
	1-230	CF3	CH═NOAc
	1-231	CN	CH═NOAc
	1-232	H	COMe
	1-233	Me	COMe
	1-234	Et	COMe
	1-235	n-Pr	COMe
	1-236	n-Bu	COMe
	1-237	F	COMe
	1-238	Cl	COMe
	1-239	Br	COMe
	1-240	I	COMe
	1-241	SMe	COMe
	1-242	CF3	COMe
	1-243	CN	COMe
	1-244	H	COEt
	1-245	Me	COEt
	1-246	Et	COEt
	1-247	n-Pr	COEt
	1-248	n-Bu	COEt
	1-249	Ph	COEt
	1-250	F	COEt
	1-251	Cl	COEt
	1-252	Br	COEt
	1-253	I	COEt
	1-254	SMe	COEt
	1-255	CF3	COEt
	1-256	CN	COEt
	1-257	H	COPh
	1-258	Me	COPh
	1-259	Et	COPh
	1-260	n-Pr	COPh
	1-261	F	COPh
	1-262	Cl	COPh
	1-263	Br	COPh
	1-264	I	COPh
	1-265	H	COCF3
	1-266	Me	COCF3
	1-267	Et	COCF3
	1-268	n-Pr	COCF3
	1-269	F	COCF3
	1-270	Cl	COCF3
	1-271	Br	COCF3
	1-272	I	COCF3
	1-273	SMe	COCF3
	1-274	CF3	COCF3
	1-275	CN	COCF3
	1-276	H	CO2Me
	1-277	Me	CO2Me
	1-278	Et	CO2Me
	1-279	n-Pr	CO2Me
	1-280	n-Bu	CO2Me
	1-281	Ph	CO2Me
	1-282	F	CO2Me
	1-283	Cl	CO2Me
	1-284	Br	CO2Me
	1-285	I	CO2Me
	1-286	SMe	CO2Me
	1-287	CF3	CO2Me
	1-288	CN	CO2Me
	1-289	H	CO2Et
	1-290	Me	CO2Et
	1-291	Et	CO2Et
	1-292	F	CO2Et
	1-293	Cl	CO2Et
	1-294	Br	CO2Et
	1-295	SMe	CO2Et
	1-296	CF3	CO2Et
	1-297	CN	CO2Et
	1-298	H	CO2n-Pr
	1-299	Me	CO2n-Pr
	1-300	Et	CO2n-Pr
	1-301	F	CO2n-Pr
	1-302	Cl	CO2n-Pr
	1-303	Br	CO2n-Pr
	1-304	SMe	CO2n-Pr
	1-305	CF3	CO2n-Pr
	1-306	CN	CO2n-Pr
	1-307	H	CO2I—Pr
	1-309	Et	CO2I—Pr
	1-310	F	CO2I—Pr
	1-311	Cl	CO2I—Pr
	1-312	Br	CO2I—Pr
	1-313	SMe	CO2I—Pr
	1-314	CF3	CO2I—Pr
	1-315	CN	CO2I—Pr
	1-316	H	CO2n-Bu
	1-317	Me	CO2n-Bu
	1-318	Et	CO2n-Bu
	1-319	F	CO2n-Bu
	1-320	Cl	CO2n-Bu
	1-321	Br	CO2n-Bu
	1-322	SMe	CO2n-Bu
	1-323	CF3	CO2n-Bu
	1-324	CN	CO2n-Bu
	1-325	H	CO2I—Bu
	1-326	Me	CO2I—Bu
	1-327	Et	CO2I—Bu
	1-328	F	CO2I—Bu
	1-329	Cl	CO2I—Bu
	1-330	Br	CO2I—Bu
	1-331	SMe	CO2I—Bu
	1-332	CF3	CO2I—Bu
	1-333	CN	CO2I—Bu
	1-334	H	CO2s-Bu
	1-335	Me	CO2s-Bu
	1-336	Et	CO2s-Bu
	1-337	F	CO2s-Bu
	1-338	Cl	CO2s-Bu
	1-339	Br	CO2s-Bu
	1-340	SMe	CO2s-Bu
	1-341	CF3	CO2s-Bu
	1-342	CN	CO2s-Bu
	1-343	H	CO2t-Bu
	1-344	Me	CO2t-Bu
	1-345	Et	CO2t-Bu
	1-346	F	CO2t-Bu
	1-347	Cl	CO2t-Bu
	1-348	Br	CO2t-Bu
	1-349	SMe	CO2t-Bu
	1-350	CF3	CO2t-Bu
	1-351	CN	CO2t-Bu
	1-352	H	CO2Ph
	1-353	Me	CO2Ph
	1-354	Et	CO2Ph
	1-355	F	CO2Ph
	1-356	Cl	CO2Ph
	1-357	Br	CO2Ph
	1-358	SMe	CO2Ph
	1-359	CF3	CO2Ph
	1-360	CN	CO2Ph
	1-361	H	COCO2Me
	1-362	Me	COCO2Me
	1-363	F	COCO2Me
	1-364	Cl	COCO2Me
	1-365	Br	COCO2Me
	1-366	SMe	COCO2Me
	1-367	CF3	COCO2Me
	1-368	CN	COCO2Me
	1-369	H	COCO2Et
	1-370	Me	COCO2Et
	1-371	F	COCO2Et
	1-372	Cl	COCO2Et
	1-373	Br	COCO2Et
	1-374	SMe	COCO2Et
	1-375	CF3	COCO2Et
	1-376	CN	COCO2Et
	1-377	H	SMe
	1-378	Me	SMe
	1-379	Et	SMe
	1-380	n-Pr	SMe
	1-381	F	SMe
	1-382	Cl	SMe
	1-383	Br	SMe
	1-384	I	SMe
	1-385	SMe	SMe
	1-386	CF3	SMe
	1-387	CN	SMe
	1-388	H	SOMe
	1-389	Me	SOMe
	1-390	Et	SOMe
	1-391	Cl	SOMe
	1-392	Br	SOMe
	1-393	CF3	SOMe
	1-394	CN	SOMe
	1-395	H	SO2Me
	1-396	Me	SO2Me
	1-397	Et	SO2Me
	1-398	Cl	SO2Me
	1-399	Br	SO2Me
	1-400	CF3	SO2Me
	1-401	CN	SO2Me
	1-402	H	SPh
	1-403	Me	SPh
	1-404	Et	SPh
	1-405	n-Pr	SPh
	1-406	F	SPh
	1-407	Cl	SPh
	1-408	Br	SPh
	1-409	I	SPh
	1-410	SMe	SPh
	1-411	CF3	SPh
	1-412	CN	SPh
	1-413	H	SOPh
	1-414	Me	SOPh
	1-415	Et	SOPh
	1-416	Cl	SOPh
	1-417	Br	SOPh
	1-418	CF3	SOPh
	1-419	CN	SOPh
	1-420	H	SO2Ph
	1-421	Me	SO2Ph
	1-422	Et	SO2Ph
	1-423	Cl	SO2Ph
	1-424	Br	SO2Ph
	1-425	CF3	SO2Ph
	1-426	CN	SO2Ph
	1-427	H	NO2
	1-428	Me	NO2
	1-429	Et	NO2
	1-430	Cl	NO2
	1-431	Br	NO2
	1-432	SMe	NO2
	1-433	CF3	NO2
	1-434	CN	NO2
	1-435	H	CN
	1-436	Me	CN
	1-437	Et	CN
	1-438	n-Pr	CN
	1-439	F	CN
	1-440	Cl	CN
	1-441	Br	CN
	1-442	SMe	CN
	1-443	CF3	CN
	1-444	CN	CN
	1-445	H	CH2CN
	1-446	Me	CH2CN
	1-447	Et	CH2CN
	1-448	n-Pr	CH2CN
	1-449	Cl	CH2CN
	1-450	Br	CH2CN
	1-451	SMe	CH2CN
	1-452	CF3	CH2CN
	1-453	CN	CH2CN
	1-454	H	OMe
	1-455	Me	OMe
	1-456	Et	OMe
	1-457	Cl	OMe
	1-458	Br	OMe
	1-459	SMe	OMe
	1-460	CF3	OMe
	1-461	CN	OMe
	1-462	H	CH2NMe2
	1-463	Me	CH2NMe2
	1-464	Et	CH2NMe2
	1-465	Cl	CH2NMe2
	1-466	Br	CH2NMe2
	1-467	SMe	CH2NMe2
	1-468	CF3	CH2NMe2
	1-469	CN	CH2NMe2
	1-470	H	OCOMe
	1-471	Me	OCOMe
	1-472	Et	OCOMe
	1-473	Cl	OCOMe
	1-474	Br	OCOMe
	1-475	SMe	OCOMe
	1-476	CF3	OCOMe
	1-477	CN	OCOMe
	1-478	H	CH(OMe)2
	1-479	Me	CH(OMe)2
	1-480	Et	CH(OMe)2
	1-481	n-Pr	CH(OMe)2
	1-482	Cl	CH(OMe)2
	1-483	Br	CH(OMe)2
	1-484	SMe	CH(OMe)2
	1-485	CF3	CH(OMe)2
	1-486	CN	CH(OMe)2
	1-487	H	CH(SMe)2
	1-488	Me	CH(SMe)2
	1-489	Et	CH(SMe)2
	1-490	n-Pr	CH(SMe)2
	1-491	Cl	CH(SMe)2
	1-492	Br	CH(SMe)2
	1-493	SMe	CH(SMe)2
	1-494	CF3	CH(SMe)2
	1-495	CN	CH(SMe)2
	1-496	H	CH2Cl
	1-497	Me	CH2Cl
	1-498	Et	CH2Cl
	1-499	n-Pr	CH2Cl
	1-500	F	CH2Cl
	1-501	Cl	CH2Cl
	1-502	Br	CH2Cl
	1-503	I	CH2Cl
	1-504	SMe	CH2Cl
	1-505	CF3	CH2Cl
	1-506	CN	CH2Cl
	1-507	H	CH2OH
	1-508	Me	CH2OH
	1-509	Et	CH2OH
	1-510	n-Pr	CH2OH
	1-511	F	CH2OH
	1-512	Cl	CH2OH
	1-513	Br	CH2OH
	1-514	SMe	CH2OH
	1-515	CF3	CH2OH
	1-516	CN	CH2OH
	1-517	H	CH(OH)Me
	1-518	Me	CH(OH)Me
	1-519	Et	CH(OH)Me
	1-520	n-Pr	CH(OH)Me
	1-521	F	CH(OH)Me
	1-522	Cl	CH(OH)Me
	1-523	Br	CH(OH)Me
	1-524	SMe	CH(OH)Me
	1-525	CF3	CH(OH)Me
	1-526	CN	CH(OH)Me
	1-527	H	CH(OH)Et
	1-528	Me	CH(OH)Et
	1-529	Et	CH(OH)Et
	1-530	n-Pr	CH(OH)Et
	1-531	F	CH(OH)Et
	1-532	Cl	CH(OH)Et
	1-533	Br	CH(OH)Et
	1-534	SMe	CH(OH)Et
	1-535	CF3	CH(OH)Et
	1-536	CN	CH(OH)Et
	1-537	H	CH(OH)CF3
	1-538	Me	CH(OH)CF3
	1-539	Et	CH(OH)CF3
	1-540	n-Pr	CH(OH)CF3
	1-541	F	CH(OH)CF3
	1-542	Cl	CH(OH)CF3
	1-543	Br	CH(OH)CF3
	1-544	SMe	CH(OH)CF3
	1-545	CF3	CH(OH)CF3
	1-546	CN	CH(OH)CF3
	1-547	H	CH2OMe
	1-548	Me	CH2OMe
	1-549	Et	CH2OMe
	1-550	n-Pr	CH2OMe
	1-551	F	CH2OMe
	1-552	Cl	CH2OMe
	1-553	Br	CH2OMe
	1-554	SMe	CH2OMe
	1-555	CF3	CH2OMe
	1-556	CN	CH2OMe
	1-557	H	CONMe2
	1-558	Me	CONMe2
	1-559	Et	CONMe2
	1-560	n-Pr	CONMe2
	1-561	F	CONMe2
	1-562	Cl	CONMe2
	1-563	Br	CONMe2
	1-564	SMe	CONMe2
	1-565	CF3	CONMe2
	1-566	CN	CONMe2
	1-567	H	CO(4-CF3Ph)
	1-568	Me	CO(4-CF3Ph)
	1-569	Et	CO(4-CF3Ph)
	1-570	Cl	CO(4-CF3Ph)
	1-571	Br	CO(4-CF3Ph)

[0165]

TABLE 2
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
Compound No.	R7	R8	R9	R10
2-1	F	H	H	H
2-2	H	F	H	H
2-3	H	H	F	H
2-4	H	H	H	F
2-5	Cl	H	H	H
2-6	H	Cl	H	H
2-7	H	H	Cl	H
2-8	H	H	H	Cl
2-9	Br	H	H	H
2-10	H	Br	H	H
2-11	H	H	Br	H
2-12	H	H	H	Br
2-13	I	H	H	H
2-14	H	I	H	H
2-15	H	H	I	H
2-16	H	H	H	I
2-17	Me	H	H	H
2-18	H	Me	H	H
2-19	H	H	Me	H
2-20	H	H	H	Me
2-21	Et	H	H	H
2-22	H	Et	H	H
2-23	H	H	Et	H
2-24	H	H	H	Et
2-25	MeO	H	H	H
2-26	H	MeO	H	H
2-27	H	H	MeO	H
2-28	H	H	H	MeO
2-29	NO2	H	H	H
2-30	H	NO2	H	H
2-31	H	H	NO2	H
2-32	H	H	H	NO2
2-33	CN	H	H	H
2-34	H	CN	H	H
2-35	H	H	CN	H
2-36	H	H	H	CN
2-37	CF3	H	H	H
2-38	H	CF3	H	H
2-39	H	H	CF3	H
2-40	H	H	H	CF3
2-41	CO2Me	H	H	H
2-42	H	CO2Me	H	H
2-43	H	H	CO2Me	H
2-44	H	H	H	CO2Me

[0166]

TABLE 3
40
41
Compound No.	R7	R8	R9	R10
3-1	H	H	H	H
3-2	F	H	H	H
3-3	H	F	H	H
3-4	H	H	F	H
3-5	H	H	H	F
3-6	Cl	H	H	H
3-7	H	Cl	H	H
3-8	H	H	Cl	H
3-9	H	H	H	Cl
3-10	Br	H	H	H
3-11	H	Br	H	H
3-12	H	H	Br	H
3-13	H	H	H	Br
3-14	Me	H	H	H
3-15	H	Me	H	H
3-16	H	H	Me	H
3-17	H	H	H	Me
3-18	CF3	H	H	H
3-19	H	CF3	H	H
3-20	H	H	CF3	H
3-21	H	H	H	CF3

[0167]

TABLE 4
42
43
44
45
or
46
Compound No.	R3	R4
4-1	H	H
4-2	H	Me
4-3	H	Et
4-4	H	Cl
4-5	H	Br
4-6	H	CF3
4-7	Me	H
4-8	Me	Me
4-9	Me	Et
4-10	Me	Cl
4-11	Me	Br
4-12	Me	CF3
4-13	Et	H
4-14	Et	Me
4-15	Et	Et
4-16	Et	Cl
4-17	Et	Br
4-18	Et	CF3
4-19	Cl	H
4-20	Cl	Me
4-21	Cl	Et
4-22	Cl	Cl
4-23	Cl	Br
4-24	Cl	CF3
4-25	Br	H
4-26	Br	Me
4-27	Br	Et
4-28	Br	Br
4-29	Br	CF3

[0168]

TABLE 5
47
48
49
50
51
52
53
54
55
Compound No.	R3	R4	R5	R6
5-1	H	Ph	H	H
5-2	Cl	Ph	H	H
5-3	H	Ph	Cl	H
5-4	H	Ph	H	Cl
5-5	Cl	Ph	Cl	H
5-6	Cl	Ph	H	Cl
5-7	H	Ph	Cl	Cl
5-8	Cl	Ph	Cl	Cl
5-9	Br	Ph	Cl	H
5-10	Cl	Ph	Br	H
5-11	Br	Ph	H	Cl
5-12	Cl	Ph	H	Br
5-13	H	Ph	Br	Cl
5-14	H	Ph	Cl	Br
5-15	Br	Ph	Cl	Cl
5-16	Cl	Ph	Br	Cl
5-17	Cl	Ph	Cl	Br
5-18	Br	Ph	Br	Cl
5-19	Br	Ph	Cl	Br
5-20	Cl	Ph	Br	Br
5-21	Me	Ph	H	H
5-22	H	Ph	Me	H
5-23	H	Ph	H	Me
5-24	Me	Ph	Cl	H
5-25	Me	Ph	H	Cl
5-26	Me	Ph	Cl	Cl
5-27	Me	Ph	Br	Cl
5-28	Me	Ph	Cl	Br
5-29	Cl	Ph	Me	H
5-30	H	Ph	Me	Cl
5-31	Cl	Ph	Me	Cl
5-32	Br	Ph	Me	Cl
5-33	Cl	Ph	Me	Br
5-34	Cl	Ph	H	Me
5-35	H	Ph	Cl	Me
5-36	Cl	Ph	Cl	Me
5-37	Br	Ph	Cl	Me
5-38	Cl	Ph	Br	Me
5-39	Br	Ph	H	H
5-40	H	Ph	Br	H
5-41	H	Ph	H	Br
5-42	Br	Ph	Br	H
5-43	Br	Ph	H	Br
5-44	H	Ph	Br	Br
5-45	Br	Ph	Br	Br
5-46	Me	Ph	Br	H
5-47	Me	Ph	H	Br
5-48	Me	Ph	Br	Br
5-49	Br	Ph	Me	H
5-50	H	Ph	Me	Br
5-51	Br	Ph	Me	Br
5-52	Br	Ph	H	Me
5-53	H	Ph	Br	Me
5-54	Br	Ph	Br	Me
5-55	Me	Ph	Me	H
5-56	Me	Ph	Me	Cl
5-57	Me	Ph	Me	Br
5-58	H	Ph	Me	Me
5-59	Cl	Ph	Me	Me
5-60	Br	Ph	Me	Me
5-61	Me	Ph	H	Me
5-62	Me	Ph	Cl	Me
5-63	Me	Ph	Br	Me
5-64	CO2Me	Ph	Me	H
5-65	Me	Ph	CO2Me	H
5-66	CO2Me	Ph	Me	Cl
5-67	Me	Ph	CO2Me	Cl
5-68	CO2Me	Ph	Me	Br
5-69	Me	Ph	CO2Me	Br
5-70	Ac	Ph	Me	H
5-71	Me	Ph	Ac	H
5-72	Ac	Ph	Me	Cl
5-73	Me	Ph	Ac	Cl
5-74	Ac	Ph	Me	Br
5-75	Me	Ph	Ac	Br
5-76	CN	Ph	Me	H
5-77	Me	Ph	CN	H
5-78	CN	Ph	Me	Cl
5-79	Me	Ph	CN	Cl
5-80	CN	Ph	Me	Br
5-81	Me	Ph	CN	Br
5-82	H	Ph	CO2Me	Me
5-83	H	Ph	Me	CO2Me
5-84	Cl	Ph	CO2Me	Me
5-85	Cl	Ph	Me	CO2Me
5-86	Br	Ph	CO2Me	Me
5-87	Br	Ph	Me	CO2Me
5-88	H	Ph	Ac	Me
5-89	H	Ph	Me	Ac
5-90	Cl	Ph	Ac	Me
5-91	Cl	Ph	Me	Ac
5-92	Br	Ph	Ac	Me
5-93	Br	Ph	Me	Ac
5-94	H	Ph	CN	Me
5-95	H	Ph	Me	CN
5-96	Cl	Ph	CN	Me
5-97	Cl	Ph	Me	CN
5-98	Br	Ph	CN	Me
5-99	Br	Ph	Me	CN
5-100	CO2Me	Ph	H	Me
5-101	Me	Ph	H	CO2Me
5-102	CO2Me	Ph	Cl	Me
5-103	Me	Ph	Cl	CO2Me
5-104	CO2Me	Ph	Br	Me
5-105	Me	Ph	Br	CO2Me
5-106	Ac	Ph	H	Me
5-107	Me	Ph	H	Ac
5-108	Ac	Ph	Cl	Me
5-109	Me	Ph	Cl	Ac
5-110	Ac	Ph	Br	Me
5-111	Me	Ph	Br	Ac
5-112	CN	Ph	H	Me
5-113	Me	Ph	H	CN
5-114	CN	Ph	Cl	Me
5-115	Me	Ph	Cl	CN
5-116	CN	Ph	Br	Me
5-117	Me	Ph	Br	CN
5-118	Et	Ph	H	H
5-119	H	Ph	Et	H
5-120	H	Ph	H	Et
5-121	Et	Ph	Cl	H
5-122	Et	Ph	H	Cl
5-123	Et	Ph	Cl	Cl
5-124	Et	Ph	Br	Cl
5-125	Et	Ph	Cl	Br
5-126	Cl	Ph	Et	H
5-127	H	Ph	Et	Cl
5-128	Cl	Ph	Et	Cl
5-129	Br	Ph	Et	Cl
5-130	Cl	Ph	Et	Br
5-131	Cl	Ph	H	Et
5-132	H	Ph	Cl	Et
5-133	Cl	Ph	Cl	Et
5-134	Br	Ph	Cl	Et
5-135	Cl	Ph	Br	Et
5-136	Et	Ph	Br	H
5-137	Et	Ph	H	Br
5-138	Et	Ph	Br	Br
5-139	Br	Ph	Et	H
5-140	H	Ph	Et	Br
5-141	Br	Ph	Et	Br
5-142	Br	Ph	H	Et
5-143	H	Ph	Br	Et
5-144	Br	Ph	Br	Et
5-145	CN	Ph	H	H
5-146	H	Ph	CN	H
5-147	H	Ph	H	CN
5-148	CN	Ph	Cl	H
5-149	CN	Ph	H	Cl
5-150	CN	Ph	Cl	Cl
5-151	CN	Ph	Br	Cl
5-152	CN	Ph	Cl	Br
5-153	Cl	Ph	CN	H
5-154	H	Ph	CN	Cl
5-155	Cl	Ph	CN	Cl
5-156	Br	Ph	CN	Cl
5-157	Cl	Ph	CN	Br
5-158	Cl	Ph	H	CN
5-159	H	Ph	Cl	CN
5-160	Br	Ph	H	CN
5-161	H	Ph	Br	CN
5-162	CN	Ph	Br	H
5-163	CN	Ph	H	Br
5-164	CN	Ph	Br	Br
5-165	Br	Ph	CN	H
5-166	H	Ph	CN	Br
5-167	Br	Ph	CN	Br
5-168	Cl	Ph	Cl	CN
5-169	Cl	Ph	Br	CN
5-170	Br	Ph	Cl	CN
5-171	Br	Ph	Br	CN
5-172	CF3	Ph	H	H
5-173	H	Ph	CF3	H
5-174	H	Ph	H	CF3
5-175	CF3	Ph	Cl	H
5-176	CF3	Ph	H	Cl
5-177	CF3	Ph	Cl	Cl
5-178	CF3	Ph	Br	Cl
5-179	CF3	Ph	Cl	Br
5-180	Cl	Ph	CF3	H
5-181	H	Ph	CF3	Cl
5-182	Cl	Ph	CF3	Cl
5-183	Br	Ph	CF3	Cl
5-184	Cl	Ph	CF3	Br
5-185	Cl	Ph	H	CF3
5-186	H	Ph	Cl	CF3
5-187	Cl	Ph	Cl	CF3
5-188	Br	Ph	Cl	CF3
5-189	Cl	Ph	Br	CF3
5-190	CF3	Ph	Br	H
5-191	CF3	Ph	H	Br
5-192	CF3	Ph	Br	Br
5-193	Br	Ph	CF3	H
5-194	H	Ph	CF3	Br
5-195	Br	Ph	CF3	Br
5-196	Br	Ph	H	CF3
5-197	H	Ph	Br	CF3
5-198	Br	Ph	Br	CF3
5-199	NO2	Ph	H	H
5-200	H	Ph	NO2	H
5-201	H	Ph	H	NO2
5-202	NO2	Ph	Cl	H
5-203	NO2	Ph	H	Cl
5-204	NO2	Ph	Cl	Cl
5-205	NO2	Ph	Br	Cl
5-206	NO2	Ph	Cl	Br
5-207	Cl	Ph	NO2	H
5-208	H	Ph	NO2	Cl
5-209	Cl	Ph	NO2	Cl
5-210	Br	Ph	NO2	Cl
5-211	Cl	Ph	NO2	Br
5-212	Cl	Ph	H	NO2
5-213	H	Ph	Cl	NO2
5-214	Cl	Ph	Cl	NO2
5-215	Br	Ph	Cl	NO2
5-216	Cl	Ph	Br	NO2
5-217	NO2	Ph	Br	H
5-218	NO2	Ph	H	Br
5-219	NO2	Ph	Br	Br
5-220	Br	Ph	NO2	H
5-221	H	Ph	NO2	Br
5-222	Br	Ph	NO2	Br
5-223	Br	Ph	H	NO2
5-224	H	Ph	Br	NO2
5-225	Br	Ph	Br	NO2
5-226	CO2Me	Ph	H	H
5-227	H	Ph	CO2Me	H
5-228	H	Ph	H	CO2Me
5-229	CO2Me	Ph	Cl	H
5-230	CO2Me	Ph	H	Cl
5-231	CO2Me	Ph	Cl	Cl
5-232	CO2Me	Ph	Br	Cl
5-233	CO2Me	Ph	Cl	Br
5-234	Cl	Ph	CO2Me	H
5-235	H	Ph	CO2Me	Cl
5-236	Cl	Ph	CO2Me	Cl
5-237	Br	Ph	CO2Me	Cl
5-238	Cl	Ph	CO2Me	Br
5-239	Cl	Ph	H	CO2Me
5-240	H	Ph	Cl	CO2Me
5-241	Cl	Ph	Cl	CO2Me
5-242	Br	Ph	Cl	CO2Me
5-243	Cl	Ph	Br	CO2Me
5-244	CO2Me	Ph	Br	H
5-245	CO2Me	Ph	H	Br
5-246	CO2Me	Ph	Br	Br
5-247	Br	Ph	CO2Me	H
5-248	H	Ph	CO2Me	Br
5-249	Br	Ph	CO2Me	Br
5-250	Br	Ph	H	CO2Me
5-251	H	Ph	Br	CO2Me
5-252	Br	Ph	Br	CO2Me
5-253	Ac	Ph	H	H
5-254	H	Ph	Ac	H
5-255	H	Ph	H	Ac
5-256	Ac	Ph	Cl	H
5-257	Ac	Ph	H	Cl
5-258	Ac	Ph	Cl	Cl
5-259	Ac	Ph	Br	Cl
5-260	Ac	Ph	Cl	Br
5-261	Cl	Ph	Ac	H
5-262	H	Ph	Ac	Cl
5-263	Cl	Ph	Ac	Cl
5-264	Br	Ph	Ac	Cl
5-265	Cl	Ph	Ac	Br
5-266	Cl	Ph	H	Ac
5-267	H	Ph	Cl	Ac
5-268	Cl	Ph	Cl	Ac
5-269	Br	Ph	Cl	Ac
5-270	Cl	Ph	Br	Ac
5-271	Ac	Ph	Br	H
5-272	Ac	Ph	H	Br
5-273	Ac	Ph	Br	Br
5-274	Br	Ph	Ac	H
5-275	H	Ph	Ac	Br
5-276	Br	Ph	Ac	Br
5-277	Br	Ph	H	Ac
5-278	H	Ph	Br	Ac
5-279	Br	Ph	Br	Ac
5-280	Ph	H	H	H
5-281	Ph	Cl	H	H
5-282	Ph	H	Cl	H
5-283	Ph	H	H	Cl
5-284	Ph	Cl	Cl	H
5-285	Ph	Br	Cl	H
5-286	Ph	Cl	Br	H
5-287	Ph	Cl	H	Cl
5-288	Ph	Br	H	Cl
5-289	Ph	Cl	H	Br
5-290	Ph	H	Cl	Cl
5-291	Ph	H	Br	Cl
5-292	Ph	H	Cl	Br
5-293	Ph	Cl	Cl	Cl
5-294	Ph	Br	Cl	Cl
5-295	Ph	Cl	Br	Cl
5-296	Ph	Cl	Cl	Br
5-297	Ph	Br	Br	Cl
5-298	Ph	Br	Cl	Br
5-299	Ph	Cl	Br	Br
5-300	Ph	Me	H	H
5-301	Ph	H	Me	H
5-302	Ph	H	H	Me
5-303	Ph	Me	Cl	H
5-304	Ph	Me	H	Cl
5-305	Ph	Me	Cl	Cl
5-306	Ph	Me	Br	Cl
5-307	Ph	Me	Cl	Br
5-308	Ph	Cl	Me	H
5-309	Ph	H	Me	Cl
5-310	Ph	Cl	Me	Cl
5-311	Ph	Cl	Me	Br
5-312	Ph	Cl	H	Me
5-313	Ph	H	Cl	Me
5-314	Ph	Cl	Cl	Me
5-315	Ph	Br	H	H
5-316	Ph	H	Br	H
5-317	Ph	H	H	Br
5-318	Ph	Br	Br	H
5-319	Ph	Br	H	Br
5-320	Ph	H	Br	Br
5-321	Ph	Br	Br	Br
5-322	Ph	Me	Br	H
5-323	Ph	Me	H	Br
5-324	Ph	Me	Br	Br
5-325	Ph	Br	Me	H
5-326	Ph	H	Me	Br
5-327	Ph	Br	Me	Br
5-328	Ph	Br	Me	Cl
5-329	Ph	Br	H	Me
5-330	Ph	H	Br	Me
5-331	Ph	Br	Br	Me
5-332	Ph	CN	H	H
5-333	Ph	H	CN	H
5-334	Ph	H	H	CN
5-335	Ph	CN	Cl	H
5-336	Ph	CN	H	Cl
5-337	Ph	CN	Cl	Cl
5-338	Ph	CN	Br	Cl
5-339	Ph	CN	Cl	Br
5-340	Ph	Cl	CN	H
5-341	Ph	H	CN	Cl
5-342	Ph	Cl	CN	Cl
5-343	Ph	Br	CN	Cl
5-344	Ph	Cl	CN	Br
5-345	Ph	Cl	H	CN
5-346	Ph	H	Cl	CN
5-347	Ph	Cl	Cl	CN
5-348	Ph	Br	Cl	CN
5-349	Ph	Cl	Br	CN
5-350	Ph	CN	Br	H
5-351	Ph	CN	H	Br
5-352	Ph	CN	Br	Br
5-353	Ph	Br	CN	H
5-354	Ph	H	CN	Br
5-355	Ph	Br	CN	Br
5-356	Ph	Br	H	CN
5-357	Ph	H	Br	CN
5-358	Ph	Br	Br	CN
5-359	Ph	CF3	H	H
5-360	Ph	H	CF3	H
5-361	Ph	H	H	CF3
5-362	Ph	CF3	Cl	H
5-363	Ph	CF3	H	Cl
5-364	Ph	CF3	Cl	Cl
5-365	Ph	CF3	Br	Cl
5-366	Ph	CF3	Cl	Br
5-367	Ph	Cl	CF3	H
5-368	Ph	H	CF3	Cl
5-369	Ph	Cl	CF3	Cl
5-370	Ph	Br	CF3	Cl
5-371	Ph	Cl	CF3	Br
5-372	Ph	Cl	H	CF3
5-373	Ph	H	Cl	CF3
5-374	Ph	Cl	Cl	CF3
5-375	Ph	Br	Cl	CF3
5-376	Ph	Cl	Br	CF3
5-377	Ph	CF3	Br	H
5-378	Ph	CF3	H	Br
5-379	Ph	CF3	Br	Br
5-380	Ph	Br	CF3	H
5-381	Ph	H	CF3	Br
5-382	Ph	Br	CF3	Br
5-383	Ph	Br	H	CF3
5-384	Ph	H	Br	CF3
5-385	Ph	Br	Br	CF3
5-386	Ph	NO2	H	H
5-387	Ph	H	NO2	H
5-388	Ph	H	H	NO2
5-389	Ph	NO2	Cl	H
5-390	Ph	NO2	H	Cl
5-391	Ph	NO2	Cl	Cl
5-392	Ph	NO2	Br	Cl
5-393	Ph	NO2	Cl	Br
5-394	Ph	Cl	NO2	H
5-395	Ph	H	NO2	Cl
5-396	Ph	Cl	NO2	Cl
5-397	Ph	Br	NO2	Cl
5-398	Ph	Cl	NO2	Br
5-399	Ph	NO2	Br	H
5-400	Ph	NO2	H	Br
5-401	Ph	NO2	Br	Br
5-402	Ph	Br	NO2	H
5-403	Ph	H	NO2	Br
5-404	Ph	Br	NO2	Br
5-405	Ph	CO2Me	H	H
5-406	Ph	H	CO2Me	H
5-407	Ph	H	H	CO2Me
5-408	Ph	CO2Me	Cl	H
5-409	Ph	CO2Me	H	Cl
5-410	Ph	CO2Me	Cl	Cl
5-411	Ph	CO2Me	Br	Cl
5-412	Ph	CO2Me	Cl	Br
5-413	Ph	Cl	CO2Me	H
5-414	Ph	H	CO2Me	Cl
5-415	Ph	Cl	CO2Me	Cl
5-416	Ph	Br	CO2Me	Cl
5-417	Ph	Cl	CO2Me	Br
5-418	Ph	Cl	H	CO2Me
5-419	Ph	H	Cl	CO2Me
5-420	Ph	Cl	Cl	CO2Me
5-421	Ph	Br	Cl	CO2Me
5-422	Ph	Cl	Br	CO2Me
5-423	Ph	Cl	Br	Me
5-424	Ph	Br	Cl	Me
5-425	Ph	CO2Me	Br	H
5-426	Ph	CO2Me	H	Br
5-427	Ph	CO2Me	Br	Br
5-428	Ph	Br	CO2Me	H
5-429	Ph	H	CO2Me	Br
5-430	Ph	Br	CO2Me	Br
5-431	Ph	Br	H	CO2Me
5-432	Ph	H	Br	CO2Me
5-433	Ph	Br	Br	CO2Me
5-434	Ph	CO2Et	Cl	H
5-435	Ph	CO2Et	H	Cl
5-436	Ph	CO2Et	Cl	Cl
5-437	Ph	CO2Et	Br	Cl
5-438	Ph	CO2Et	Cl	Br
5-439	Ph	CO2Et	Br	Br
5-440	Ph	Cl	CO2Et	H
5-441	Ph	H	CO2Et	Cl
5-442	Ph	Cl	CO2Et	Cl
5-443	Ph	Br	CO2Et	Cl
5-444	Ph	Cl	CO2Et	Br
5-445	Ph	Br	CO2Et	Br
5-446	Ph	H	H	CO2Et
5-447	Ph	Cl	H	CO2Et
5-448	Ph	H	Cl	CO2Et
5-449	Ph	Cl	Cl	CO2Et
5-450	Ph	Cl	Br	CO2Et
5-451	Ph	Br	Cl	CO2Et
5-452	Ph	Br	Br	CO2Et
5-453	Ph	H	H	Ac
5-454	Ph	Cl	H	Ac
5-455	Ph	H	Cl	Ac
5-456	Ph	Cl	Cl	Ac
5-457	Ph	H	H	Et
5-458	Ph	Cl	H	Et
5-459	Ph	H	Cl	Et
5-460	Ph	Cl	Cl	Et
5-461	Ph	H	H	Ph
5-462	Ph	Cl	H	Ph
5-463	Ph	H	Cl	Ph
5-464	Ph	Cl	Cl	Ph
5-465	Ph	Ph	H	H
5-466	H	Ph	Ph	H
5-467	H	Ph	H	Ph
5-468	Ph	Ph	Cl	H
5-469	Ph	Ph	H	Cl
5-470	Ph	Ph	Cl	Cl
5-471	Ph	Ph	Br	Cl
5-472	Ph	Ph	Cl	Br
5-473	Ph	Ph	Br	H
5-474	Ph	Ph	H	Br
5-475	Ph	Ph	Br	Br
5-476	Cl	Ph	Ph	H
5-477	Cl	Ph	Ph	Cl
5-478	Br	Ph	Ph	H
5-479	Br	Ph	Ph	Cl
5-480	Br	Ph	Ph	Br
5-481	Cl	Ph	H	Ph
5-482	H	Ph	Cl	Ph
5-483	Br	Ph	H	Ph
5-484	H	Ph	Br	Ph
5-485	Cl	Ph	Cl	Ph
5-486	Br	Ph	Cl	Ph
5-487	Cl	Ph	Br	Ph
5-488	Br	Ph	Br	Ph
5-489	CO2Et	Ph	H	H
5-490	H	Ph	CO2Et	H
5-491	H	Ph	H	CO2Et
5-492	CO2Et	Ph	Cl	H
5-493	CO2Et	Ph	H	Cl
5-494	CO2Et	Ph	Cl	Cl
5-495	Cl	Ph	CO2Et	H
5-496	H	Ph	CO2Et	Cl
5-497	Cl	Ph	CO2Et	Cl
5-498	Cl	Ph	H	CO2Et
5-499	H	Ph	Cl	CO2Et
5-500	Cl	Ph	Cl	CO2Et
5-501	CO2Et	Ph	Br	H
5-502	CO2Et	Ph	H	Br
5-503	CO2Et	Ph	Cl	Br
5-504	CO2Et	Ph	Br	Cl
5-505	CO2Et	Ph	Br	Br
5-506	Br	Ph	CO2Et	H
5-507	H	Ph	CO2Et	Br
5-508	Br	Ph	CO2Et	Br
5-509	Cl	Ph	CO2Et	Br
5-510	Br	Ph	CO2Et	Cl
5-511	Br	Ph	H	CO2Et
5-512	H	Ph	Br	CO2Et
5-513	Br	Ph	Br	CO2Et
5-514	Cl	Ph	Br	CO2Et
5-515	Br	Ph	Cl	CO2Et
5-516	H	Ph	CO2Et	Me
5-517	Cl	Ph	CO2Et	Me
5-518	Br	Ph	CO2Et	Me
5-519	Me	Ph	CO2Et	H
5-520	Me	Ph	CO2Et	Cl
5-521	Me	Ph	CO2Et	Br
5-522	Ph	H	H	NO2
5-523	Ph	Cl	H	NO2
5-524	Ph	H	Cl	NO2
5-525	Ph	Cl	Cl	NO2

[0169]

TABLE 6
56
57
58
59
60
61
62
63
64
65
66
67
Compound
No.	R3	R4	R7	R8	R9	R10	R11
6-1	H	H	Me	H	H	H	H
6-2	H	H	H	Me	H	H	H
6-3	H	H	H	H	Me	H	H
6-4	H	H	Cl	H	H	H	H
6-5	H	H	H	Cl	H	H	H
6-6	H	H	H	H	Cl	H	H
6-7	H	H	Br	H	H	H	H
6-8	H	H	H	Br	H	H	H
6-9	H	H	H	H	Br	H	H
6-10	H	H	CF3	H	H	H	H
6-11	H	H	H	CF3	H	H	H
6-12	H	H	H	H	CF3	H	H
6-13	H	Cl	Me	H	H	H	H
6-14	H	Cl	H	Me	H	H	H
6-15	H	Cl	H	H	Me	H	H
6-16	H	Cl	Cl	H	H	H	H
6-17	H	Cl	H	Cl	H	H	H
6-18	H	Cl	H	H	Cl	H	H
6-19	H	Cl	Br	H	H	H	H
6-20	H	Cl	H	Br	H	H	H
6-21	H	Cl	H	H	Br	H	H
6-22	H	Cl	CF3	H	H	H	H
6-23	H	Cl	H	CF3	H	H	H
6-24	H	Cl	H	H	CF3	H	H
6-25	H	Br	Me	H	H	H	H
6-26	H	Br	H	Me	H	H	H
6-27	H	Br	H	H	Me	H	H
6-28	H	Br	Cl	H	H	H	H
6-29	H	Br	H	Cl	H	H	H
6-30	H	Br	H	H	Cl	H	H
6-31	H	Br	Br	H	H	H	H
6-32	H	Br	H	Br	H	H	H
6-33	H	Br	H	H	Br	H	H
6-34	H	Br	CF3	H	H	H	H
6-35	H	Br	H	CF3	H	H	H
6-36	H	Br	H	H	CF3	H	H
6-37	H	Me	Me	H	H	H	H
6-38	H	Me	H	Me	H	H	H
6-39	H	Me	H	H	Me	H	H
6-40	H	Me	Cl	H	H	H	H
6-41	H	Me	H	Cl	H	H	H
6-42	H	Me	H	H	Cl	H	H
6-43	H	Me	Br	H	H	H	H
6-44	H	Me	H	Br	H	H	H
6-45	H	Me	H	H	Br	H	H
6-46	H	Me	CF3	H	H	H	H
6-47	H	Me	H	CF3	H	H	H
6-48	H	Me	H	H	CF3	H	H
6-49	Me	Cl	Me	H	H	H	H
6-50	Me	Cl	H	Me	H	H	H
6-51	Me	Cl	H	H	Me	H	H
6-52	Me	Cl	Cl	H	H	H	H
6-53	Me	Cl	H	Cl	H	H	H
6-54	Me	Cl	H	H	Cl	H	H
6-55	Me	Cl	Br	H	H	H	H
6-56	Me	Cl	H	Br	H	H	H
6-57	Me	Cl	H	H	Br	H	H
6-58	Me	Cl	CF3	H	H	H	H
6-59	Me	Cl	H	CF3	H	H	H
6-60	Me	Cl	H	H	CF3	H	H
6-61	Me	Br	Me	H	H	H	H
6-62	Me	Br	H	Me	H	H	H
6-63	Me	Br	H	H	Me	H	H
6-64	Me	Br	Cl	H	H	H	H
6-65	Me	Br	H	Cl	H	H	H
6-66	Me	Br	H	H	Cl	H	H
6-67	Me	Br	Br	H	H	H	H
6-68	Me	Br	H	Br	H	H	H
6-69	Me	Br	H	H	Br	H	H
6-70	Me	Br	CF3	H	H	H	H
6-71	Me	Br	H	CF3	H	H	H
6-72	Me	Br	H	H	CF3	H	H
6-73	Cl	Cl	Me	H	H	H	H
6-74	Cl	Cl	H	Me	H	H	H
6-75	Cl	Cl	H	H	Me	H	H
6-76	Cl	Cl	Cl	H	H	H	H
6-77	Cl	Cl	H	Cl	H	H	H
6-78	Cl	Cl	H	H	Cl	H	H
6-79	Cl	Cl	Br	H	H	H	H
6-80	Cl	Cl	H	Br	H	H	H
6-81	Cl	Cl	H	H	Br	H	H
6-82	Cl	Cl	CF3	H	H	H	H
6-83	Cl	Cl	H	CF3	H	H	H
6-84	Cl	Cl	H	H	CF3	H	H
6-85	Cl	Br	Me	H	H	H	H
6-86	Cl	Br	H	Me	H	H	H
6-87	Cl	Br	H	H	Me	H	H
6-88	Cl	Br	Cl	H	H	H	H
6-89	Cl	Br	H	Cl	H	H	H
6-90	Cl	Br	H	H	Cl	H	H
6-91	Cl	Br	Br	H	H	H	H
6-92	Cl	Br	H	Br	H	H	H
6-93	Cl	Br	H	H	Br	H	H
6-94	Cl	Br	CF3	H	H	H	H
6-95	Cl	Br	H	CF3	H	H	H
6-96	Cl	Br	H	H	CF3	H	H
6-97	Br	Br	Me	H	H	H	H
6-98	Br	Br	H	Me	H	H	H
6-99	Br	Br	H	H	Me	H	H
6-100	Br	Br	Cl	H	H	H	H
6-101	Br	Br	H	Cl	H	H	H
6-102	Br	Br	H	H	Cl	H	H
6-103	Br	Br	Br	H	H	H	H
6-104	Br	Br	H	Br	H	H	H
6-105	Br	Br	H	H	Br	H	H
6-106	Br	Br	CF3	H	H	H	H
6-107	Br	Br	H	CF3	H	H	H
6-108	Br	Br	H	H	CF3	H	H
6-109	Me	Me	Me	H	H	H	H
6-110	Me	Me	H	Me	H	H	H
6-111	Me	Me	H	H	Me	H	H
6-112	Me	Me	Cl	H	H	H	H
6-113	Me	Me	H	Cl	H	H	H
6-114	Me	Me	H	H	Cl	H	H
6-115	Me	Me	Br	H	H	H	H
6-116	Me	Me	H	Br	H	H	H
6-117	Me	Me	H	H	Br	H	H
6-118	Me	Me	CF3	H	H	H	H
6-119	Me	Me	H	CF3	H	H	H
6-120	Me	Me	H	H	CF3	H	H
6-121	H	H	Me	Cl	H	H	H
6-122	H	H	Me	H	Cl	H	H
6-123	H	H	Me	H	H	Cl	H
6-124	H	H	Me	H	H	H	Cl
6-125	H	H	Cl	Me	H	H	H
6-126	H	H	H	Me	Cl	H	H
6-127	H	H	H	Me	H	Cl	H
6-128	H	H	H	Me	H	H	Cl
6-129	H	H	Cl	H	Me	H	H
6-130	H	H	H	Cl	Me	H	H
6-131	H	H	Cl	Cl	H	H	H
6-132	H	H	Cl	H	Cl	H	H
6-133	H	H	Cl	H	H	Cl	H
6-134	H	H	Cl	H	H	H	Cl
6-135	H	H	H	Cl	Cl	H	H
6-136	H	H	H	Cl	H	Cl	H
6-137	H	H	CF3	Cl	H	H	H
6-138	H	H	CF3	H	Cl	H	H
6-139	H	H	CF3	H	H	Cl	H
6-140	H	H	CF3	H	H	H	Cl
6-141	H	H	Cl	CF3	H	H	H
6-142	H	H	H	CF3	Cl	H	H
6-143	H	H	H	CF3	H	Cl	H
6-144	H	H	H	CF3	H	H	Cl
6-145	H	H	Cl	H	CF3	H	H
6-146	H	H	H	Cl	CF3	H	H
6-147	H	Cl	Me	Cl	H	H	H
6-148	H	Cl	Me	H	Cl	H	H
6-149	H	Cl	Me	H	H	Cl	H
6-150	H	Cl	Me	H	H	H	Cl
6-151	H	Cl	Cl	Me	H	H	H
6-152	H	Cl	H	Me	Cl	H	H
6-153	H	Cl	H	Me	H	Cl	H
6-154	H	Cl	H	Me	H	H	Cl
6-155	H	Cl	Cl	H	Me	H	H
6-156	H	Cl	H	Cl	Me	H	H
6-157	H	Cl	Cl	Cl	H	H	H
6-158	H	Cl	Cl	H	Cl	H	H
6-159	H	Cl	Cl	H	H	Cl	H
6-160	H	Cl	Cl	H	H	H	Cl
6-161	H	Cl	H	Cl	Cl	H	H
6-162	H	Cl	H	Cl	H	Cl	H
6-163	H	Br	Me	Cl	H	H	H
6-164	H	Br	Me	H	Cl	H	H
6-165	H	Br	Me	H	H	Cl	H
6-166	H	Br	Me	H	H	H	Cl
6-167	H	Br	Cl	Me	H	H	H
6-168	H	Br	H	Me	Cl	H	H
6-169	H	Br	H	Me	H	Cl	H
6-170	H	Br	H	Me	H	H	Cl
6-171	H	Br	Cl	H	Me	H	H
6-172	H	Br	H	Cl	Me	H	H
6-173	H	Br	Cl	Cl	H	H	H
6-174	H	Br	Cl	H	Cl	H	H
6-175	H	Br	Cl	H	H	Cl	H
6-176	H	Br	Cl	H	H	H	Cl
6-177	H	Br	H	Cl	Cl	H	H
6-178	H	Br	H	Cl	H	Cl	H
6-179	H	Me	Me	Cl	H	H	H
6-180	H	Me	Me	H	Cl	H	H
6-181	H	Me	Me	H	H	Cl	H
6-182	H	Me	Me	H	H	H	Cl
6-183	H	Me	Cl	Me	H	H	H
6-184	H	Me	H	Me	Cl	H	H
6-185	H	Me	H	Me	H	Cl	H
6-186	H	Me	H	Me	H	H	Cl
6-187	H	Me	Cl	H	Me	H	H
6-188	H	Me	H	Cl	Me	H	H
6-189	H	Me	Cl	Cl	H	H	H
6-190	H	Me	Cl	H	Cl	H	H
6-191	H	Me	Cl	H	H	Cl	H
6-192	H	Me	Cl	H	H	H	Cl
6-193	H	Me	H	Cl	Cl	H	H
6-194	H	Me	H	Cl	H	Cl	H
6-195	Cl	Me	Me	Cl	H	H	H
6-196	Cl	Me	Me	H	Cl	H	H
6-197	Cl	Me	Me	H	H	Cl	H
6-198	Cl	Me	Me	H	H	H	Cl
6-199	Cl	Me	Cl	Me	H	H	H
6-200	Cl	Me	H	Me	Cl	H	H
6-201	Cl	Me	H	Me	H	Cl	H
6-202	Cl	Me	H	Me	H	H	Cl
6-203	Cl	Me	Cl	H	Me	H	H
6-204	Cl	Me	H	Cl	Me	H	H
6-205	Cl	Me	Cl	Cl	H	H	H
6-206	Cl	Me	Cl	H	Cl	H	H
6-207	Cl	Me	Cl	H	H	Cl	H
6-208	Cl	Me	Cl	H	H	H	Cl
6-209	Cl	Me	H	Cl	Cl	H	H
6-210	Cl	Me	H	Cl	H	Cl	H
6-211	Br	Me	Me	Cl	H	H	H
6-212	Br	Me	Me	H	Cl	H	H
6-213	Br	Me	Me	H	H	Cl	H
6-214	Br	Me	Me	H	H	H	Cl
6-215	Br	Me	Cl	Me	H	H	H
6-216	Br	Me	H	Me	Cl	H	H
6-217	Br	Me	H	Me	H	Cl	H
6-218	Br	Me	H	Me	H	H	Cl
6-219	Br	Me	Cl	H	Me	H	H
6-220	Br	Me	H	Cl	Me	H	H
6-221	Br	Me	Cl	Cl	H	H	H
6-222	Br	Me	Cl	H	Cl	H	H
6-223	Br	Me	Cl	H	H	Cl	H
6-224	Br	Me	Cl	H	H	H	Cl
6-225	Br	Me	H	Cl	Cl	H	H
6-226	Br	Me	H	Cl	H	Cl	H

[0170]

TABLE 7
68
69
70
71
72
73
74
75
76
77
	Compound
	No.	R3	R7	R8	R9	R10
	7-1	H	H	H	H	H
	7-2	Me	H	H	H	H
	7-3	Et	H	H	H	H
	7-4	Ph	H	H	H	H
	7-5	Cl	H	H	H	H
	7-6	Br	H	H	H	H
	7-7	CF3	H	H	H	H
	7-8	H	Cl	H	H	H
	7-9	H	H	Cl	H	H
	7-10	H	H	H	Cl	H
	7-11	H	H	H	H	Cl
	7-12	H	Br	H	H	H
	7-13	H	H	Br	H	H
	7-14	H	H	H	Br	H
	7-15	H	H	H	H	Br

[0171]

TABLE 8
78
79
80
81
82
83
84
85
86
87
88
89
Compound
No.	R3	R4	R7	R8	R9	R10	R11
8-1	H	H	H	H	H	H	H
8-2	H	Cl	H	H	H	H	H
8-3	H	Br	H	H	H	H	H
8-4	H	NO2	H	H	H	H	H
8-5	H	CO2Me	H	H	H	H	H
8-6	H	CN	H	H	H	H	H
8-7	H	Me	H	H	H	H	H
8-8	H	Et	H	H	H	H	H
8-9	H	Ph	H	H	H	H	H
8-10	Me	H	H	H	H	H	H
8-11	Me	Cl	H	H	H	H	H
8-12	Me	Br	H	H	H	H	H
8-13	Me	NO2	H	H	H	H	H
8-14	Me	CO2Me	H	H	H	H	H
8-15	Me	CN	H	H	H	H	H
8-16	Me	Me	H	H	H	H	H
8-17	Me	Et	H	H	H	H	H
8-18	Me	Ph	H	H	H	H	H
8-19	Et	H	H	H	H	H	H
8-20	Et	Cl	H	H	H	H	H
8-21	Et	Br	H	H	H	H	H
8-22	Et	NO2	H	H	H	H	H
8-23	Et	CO2Me	H	H	H	H	H
8-24	Et	CN	H	H	H	H	H
8-25	Et	Me	H	H	H	H	H
8-26	Et	Et	H	H	H	H	H
8-27	Et	Ph	H	H	H	H	H
8-28	n-Pr	H	H	H	H	H	H
8-29	n-Pr	Cl	H	H	H	H	H
8-30	n-Pr	Br	H	H	H	H	H
8-31	n-Pr	NO2	H	H	H	H	H
8-32	n-Pr	CO2Me	H	H	H	H	H
8-33	n-Pr	CN	H	H	H	H	H
8-34	n-Pr	Me	H	H	H	H	H
8-35	n-Pr	Et	H	H	H	H	H
8-36	n-Pr	Ph	H	H	H	H	H
8-37	Cl	H	H	H	H	H	H
8-38	Cl	Cl	H	H	H	H	H
8-39	Cl	Br	H	H	H	H	H
8-40	Cl	NO2	H	H	H	H	H
8-41	Cl	CO2Me	H	H	H	H	H
8-42	Cl	CN	H	H	H	H	H
8-43	Cl	Me	H	H	H	H	H
8-44	Cl	Et	H	H	H	H	H
8-45	Cl	Ph	H	H	H	H	H
8-46	Br	H	H	H	H	H	H
8-47	Br	Cl	H	H	H	H	H
8-48	Br	Br	H	H	H	H	H
8-49	Br	NO2	H	H	H	H	H
8-50	Br	CO2Me	H	H	H	H	H
8-51	Br	CN	H	H	H	H	H
8-52	Br	Me	H	H	H	H	H
8-53	Br	Et	H	H	H	H	H
8-54	Br	Ph	H	H	H	H	H
8-55	CF3	H	H	H	H	H	H
8-56	CF3	Cl	H	H	H	H	H
8-57	CF3	Br	H	H	H	H	H
8-58	CF3	NO2	H	H	H	H	H
8-59	CF3	CO2Me	H	H	H	H	H
8-60	CF3	CN	H	H	H	H	H
8-61	CF3	Me	H	H	H	H	H
8-62	CF3	Et	H	H	H	H	H
8-63	CF3	Ph	H	H	H	H	H
8-64	Ph	H	H	H	H	H	H
8-65	Ph	Cl	H	H	H	H	H
8-66	Ph	Br	H	H	H	H	H
8-67	Ph	NO2	H	H	H	H	H
8-68	Ph	CO2Me	H	H	H	H	H
8-69	Ph	CN	H	H	H	H	H
8-70	Ph	Me	H	H	H	H	H
8-71	Ph	Et	H	H	H	H	H
8-72	Ph	Ph	H	H	H	H	H
8-73	Me	Cl	Me	H	H	H	H
8-74	Me	Cl	H	Me	H	H	H
8-75	Me	Cl	H	H	Me	H	H
8-76	Me	Cl	Cl	H	H	H	H
8-77	Me	Cl	H	Cl	H	H	H
8-78	Me	Cl	H	H	Cl	H	H
8-79	Me	Cl	Br	H	H	H	H
8-80	Me	Cl	H	Br	H	H	H
8-81	Me	Cl	H	H	Br	H	H
8-82	Me	Cl	CF3	H	H	H	H
8-83	Me	Cl	H	CF3	H	H	H
8-84	Me	Cl	H	H	CF3	H	H
8-85	Me	Br	Me	H	H	H	H
8-86	Me	Br	H	Me	H	H	H
8-87	Me	Br	H	H	Me	H	H
8-88	Me	Br	Cl	H	H	H	H
8-89	Me	Br	H	Cl	H	H	H
8-90	Me	Br	H	H	Cl	H	H
8-91	Me	Br	Br	H	H	H	H
8-92	Me	Br	H	Br	H	H	H
8-93	Me	Br	H	H	Br	H	H
8-94	Me	Br	CF3	H	H	H	H
8-95	Me	Br	H	CF3	H	H	H
8-96	Me	Br	H	H	CF3	H	H

[0172]

TABLE 9
90
91
92
93
94
95
96
97
or
98
Compound
No.	R3	R4	R7	R8	R9	R10
9-1	H	H	H	H	H	H
9-2	H	Cl	H	H	H	H
9-3	H	Br	H	H	H	H
9-4	H	NO2	H	H	H	H
9-5	H	CN	H	H	H	H
9-6	H	CF3	H	H	H	H
9-7	H	Me	H	H	H	H
9-8	H	Et	H	H	H	H
9-9	H	SMe	H	H	H	H
9-10	H	CO2Me	H	H	H	H
9-11	Me	H	H	H	H	H
9-12	Me	Cl	H	H	H	H
9-13	Me	Br	H	H	H	H
9-14	Me	NO2	H	H	H	H
9-15	Me	CN	H	H	H	H
9-16	Me	CF3	H	H	H	H
9-17	Me	Me	H	H	H	H
9-18	Me	Et	H	H	H	H
9-19	Me	SMe	H	H	H	H
9-20	Me	CO2Me	H	H	H	H
9-21	Et	H	H	H	H	H
9-22	Et	Cl	H	H	H	H
9-23	Et	Br	H	H	H	H
9-24	Et	NO2	H	H	H	H
9-25	Et	CN	H	H	H	H
9-26	Et	CF3	ii	H	H	H
9-27	Et	Me	H	H	H	H
9-28	Et	Et	H	H	H	H
9-29	Et	SMe	H	H	H	H
9-30	Et	CO2Me	H	H	H	H
9-31	Cl	H	H	H	H	H
9-32	Cl	Me	H	H	H	H
9-33	Cl	Et	H	H	H	H
9-34	Cl	CN	H	H	H	H
9-35	Cl	CF3	H	H	H	H
9-36	Cl	Cl	H	H	H	H
9-37	Cl	Br	H	H	H	H
9-38	Cl	NO2	H	H	H	H
9-39	Cl	SMe	H	H	H	H
9-40	Cl	CO2Me	H	H	H	H
9-41	Br	H	H	H	H	H
9-42	Br	Me	H	H	H	H
9-43	Br	Et	H	H	H	H
9-44	Br	CN	H	H	H	H
9-45	Br	CF3	H	H	H	H
9-46	Br	Cl	H	H	H	H
9-47	Br	Br	H	H	H	H
9-48	Br	NO2	H	H	H	H
9-49	Br	SMe	H	H	H	H
9-50	Br	CO2Me	H	H	H	H
9-51	CF3	H	H	H	H	H
9-52	CF3	Me	H	H	H	H
9-53	CF3	Et	H	H	H	H
9-54	CF3	CN	H	H	H	H
9-55	CF3	CF3	H	H	H	H
9-56	CF3	Cl	H	H	H	H
9-57	CF3	Br	H	H	H	H
9-58	CF3	NO2	H	H	H	H
9-59	CF3	SMe	H	H	H	H
9-60	CF3	CO2Me	H	H	H	H
9-61	SMe	H	H	H	H	H
9-62	SMe	Cl	H	H	H	H
9-63	SMe	Br	H	H	H	H
9-64	SMe	NO2	H	H	H	H
9-65	SMe	CN	H	H	H	H
9-66	SMe	CF3	H	H	H	H
9-67	SMe	Me	H	H	H	H
9-68	SMe	Et	H	H	H	H
9-69	SMe	SMe	H	H	H	H
9-70	SMe	CO2Me	H	H	H	H
9-71	CN	H	H	H	H	H
9-72	CN	Me	H	H	H	H
9-73	CN	Et	H	H	H	H
9-74	CN	CN	H	H	H	H
9-75	CN	CF3	H	H	H	H
9-76	CN	Cl	H	H	H	H
9-77	CN	Br	H	H	H	H
9-78	CN	NO2	H	H	H	H
9-79	CN	SMe	H	H	H	H
9-80	CN	CO2Me	H	H	H	H
9-81	Me	H	Me	H	H	H
9-82	Me	H	H	Me	H	H
9-83	Me	H	H	H	Me	H
9-84	Me	H	H	H	H	Me
9-85	Me	H	F	H	H	H
9-86	Me	H	H	F	H	H
9-87	Me	H	H	H	F	H
9-88	Me	H	H	H	H	F
9-89	Me	H	Cl	H	H	H
9-90	Me	H	H	Cl	H	H
9-91	Me	H	H	H	Cl	H
9-92	Me	H	H	H	H	Cl
9-93	Me	H	Br	H	H	H
9-94	Me	H	H	Br	H	H
9-95	Me	H	H	H	Br	H
9-96	Me	H	H	H	H	Br
9-97	Me	Cl	Me	H	H	H
9-98	Me	Cl	H	Me	H	H
9-99	Me	Cl	H	H	Me	H
9-100	Me	Cl	H	H	H	Me
9-101	Me	Cl	F	H	H	H
9-102	Me	Cl	H	F	H	H
9-103	Me	Cl	H	H	F	H
9-104	Me	Cl	H	H	H	F
9-105	Me	Cl	Cl	H	H	H
9-106	Me	Cl	H	Cl	H	H
9-107	Me	Cl	H	H	Cl	H
9-108	Me	Cl	H	H	H	Cl
9-109	Me	Cl	Br	H	H	H
9-110	Me	Cl	H	Br	H	H
9-111	Me	Cl	H	H	Br	H
9-112	Me	Cl	H	H	H	Br
9-113	Me	Br	Me	H	H	H
9-114	Me	Br	H	Me	H	H
9-115	Me	Br	H	H	Me	H
9-116	Me	Br	H	H	H	Me
9-117	Me	Br	F	H	H	H
9-118	Me	Br	H	F	H	H
9-119	Me	Br	H	H	F	H
9-120	Me	Br	H	H	H	F
9-121	Me	Br	Cl	H	H	H
9-122	Me	Br	H	Cl	H	H
9-123	Me	Br	H	H	Cl	H
9-124	Me	Br	H	H	H	Cl
9-125	Me	Br	Br	H	H	H
9-126	Me	Br	H	Br	H	H
9-127	Me	Br	H	H	Br	H
9-128	Me	Br	H	H	H	Br

[0173]

TABLE 10
99
100
101
102
103
104
	Compound
	No.	R3	R7	R8	R9	R10
	10-1	H	H	H	H	H
	10-2	Me	H	H	H	H
	10-3	Et	H	H	H	H
	10-4	n-Pr	H	H	H	H
	10-5	Cl	H	H	H	H
	10-6	Br	H	H	H	H
	10-7	Sme	H	H	H	H
	10-8	CF3	H	H	H	H
	10-9	CN	H	H	H	H
	10-10	H	Me	H	H	H
	10-11	H	H	Me	H	H
	10-12	H	H	H	Me	H
	10-13	H	H	H	H	Me
	10-14	H	F	H	H	H
	10-15	H	H	F	H	H
	10-16	H	H	H	F	H
	10-17	H	H	H	H	F
	10-18	H	Cl	H	H	H
	10-19	H	H	Cl	H	H
	10-20	H	H	H	Cl	H
	10-21	H	H	H	H	Cl
	10-22	H	Br	H	H	H
	10-23	H	H	Br	H	H
	10-24	H	H	H	Br	H
	10-25	H	H	H	H	Br
	10-26	Me	Me	H	H	H
	10-27	Me	H	Me	H	H
	10-28	Me	H	H	Me	H
	10-29	Me	H	H	H	Me
	10-30	Me	F	H	H	H
	10-31	Me	H	F	H	H
	10-32	Me	H	H	F	H
	10-33	Me	H	H	H	F
	10-34	Me	Cl	H	H	H
	10-35	Me	H	Cl	H	H
	10-36	Me	H	H	Cl	H
	10-37	Me	H	H	H	Cl
	10-38	Me	Br	H	H	H
	10-39	Me	H	Br	H	H
	10-40	Me	H	H	Br	H
	10-41	Me	H	H	H	Br
	10-42	Et	Me	H	H	H
	10-43	Et	H	Me	H	H
	10-44	Et	H	H	Me	H
	10-45	Et	H	H	H	Me
	10-46	Et	F	H	H	H
	10-47	Et	H	F	H	H
	10-48	Et	H	H	F	H
	10-49	Et	H	H	H	F
	10-50	Et	Cl	H	H	H
	10-51	Et	H	Cl	H	H
	10-52	Et	H	H	Cl	H
	10-53	Et	H	H	H	Cl
	10-54	Et	Br	H	H	H
	10-55	Et	H	Br	H	H
	10-56	Et	H	H	Br	H
	10-57	Et	H	H	H	Br
	10-58	Cl	Me	H	H	H
	10-59	Cl	H	Me	H	H
	10-60	Cl	H	H	Me	H
	10-61	Cl	H	H	H	Me
	10-62	Cl	F	H	H	H
	10-63	Cl	H	F	H	H
	10-64	Cl	H	H	F	H
	10-65	Cl	H	H	H	F
	10-66	Cl	Cl	H	H	H
	10-67	Cl	H	Cl	H	H
	10-68	Cl	H	H	Cl	H
	10-69	Cl	H	H	H	Cl
	10-70	Cl	Br	H	H	H
	10-71	Cl	H	Br	H	H
	10-72	Cl	H	H	Br	H
	10-73	Cl	H	H	H	Br
	10-74	Br	Me	H	H	H
	10-75	Br	H	Me	H	H
	10-76	Br	H	H	Me	H
	10-77	Br	H	H	H	Me
	10-78	Br	F	H	H	H
	10-79	Br	H	F	H	H
	10-80	Br	H	H	F	H
	10-81	Br	H	H	H	F
	10-82	Br	Cl	H	H	H
	10-83	Br	H	Cl	H	H
	10-84	Br	H	H	Cl	H
	10-85	Br	H	H	H	Cl
	10-86	Br	Br	H	H	H
	10-87	Br	H	Br	H	H
	10-88	Br	H	H	Br	H
	10-89	Br	H	H	H	Br

[0174]

TABLE 11
105
or
106
Compound
No.	R7	R8	R9	R10	R11
11-1	H	H	H	H	H
11-2	Me	H	H	H	H
11-3	H	Me	H	H	H
11-4	H	H	Me	H	H
11-5	Et	H	H	H	H
11-6	H	Et	H	H	H
11-7	H	H	Et	H	H
11-8	F	H	H	H	H
11-9	H	F	H	H	H
11-10	H	H	F	H	H
11-11	Cl	H	H	H	H
11-12	H	Cl	H	H	H
11-13	H	H	Cl	H	H
11-14	Br	H	H	H	H
11-15	H	Br	H	H	H
11-16	H	H	Br	H	H
11-17	CF3	H	H	H	H
11-18	H	CF3	H	H	H
11-19	H	H	CF3	H	H
11-20	OCF3	H	H	H	H
11-21	H	OCF3	H	H	H
11-22	H	H	OCF3	H	H
11-23	Ph	H	H	H	H
11-24	H	Ph	H	H	H
11-25	H	H	Ph	H	H
11-26	Oph	H	H	H	H
11-27	H	OPh	H	H	H
11-28	H	H	OPh	H	H
11-29	Bn	H	H	H	H
11-30	H	En	H	H	H
11-31	H	H	En	H	H
11-32	CO2Me	H	H	H	H
11-33	H	CO2Me	H	H	H
11-34	H	H	CO2Me	H	H
11-35	CN	H	H	H	H
11-36	H	CN	H	H	H
11-37	H	H	CN	H	H
11-38	NO2	H	H	H	H
11-39	H	NO2	H	H	H
11-40	H	H	NO2	H	H
11-41	Ome	H	H	H	H
11-42	H	OMe	H	H	H
11-43	H	H	OMe	H	H
11-44	Me	Cl	H	H	H
11-45	Me	H	Cl	H	H
11-46	Me	H	H	Cl	H
11-47	Me	H	H	H	Cl
11-48	Cl	Me	H	H	H
11-49	H	Me	Cl	H	H
11-50	H	Me	H	Cl	H
11-51	H	Me	H	H	Cl
11-52	Cl	H	Me	H	H
11-53	H	Cl	Me	H	H
11-54	Me	Me	H	H	H
11-55	Me	H	Me	H	H
11-56	Me	H	H	Me	H
11-57	Me	H	H	H	Me
11-58	H	Me	Me	H	H
11-59	H	Me	H	Me	H
11-60	Cl	Cl	H	H	H
11-61	Cl	H	Cl	H	H
11-62	Cl	H	H	Cl	H
11-63	Cl	H	H	H	Cl
11-64	H	Cl	Cl	H	H
11-65	H	Cl	H	Cl	H

[0175] Next, methods for preparing the compound of the invention will be explained below. However, the present invention should not be construed as being limited thereto.

Preparation Method 1

[0176] The compound of the invention can be prepared by reacting a compound of the formula (2)

A—H  (2)

[0177] wherein A has the same meaning as defined above, with a compound of the formula (3) 107

[0178] wherein R1, R2 and Y have the same meanings as defined above, and X is halogen.

Preparation Method 2

[0179] The compound of the invention can be prepared by reacting a compound of the formula (4) 108

[0180] wherein B and Y have the same meanings as defined above, with a compound of the formula (5)

R1R2NSO2X

[0181] wherein R1 and R2 have the same meanings as defined above and X is halogen.

Preparation Method 3

[0182] The compound of the invention can be prepared by oxidizing a compound of the formula (6) 109

[0183] wherein R1, R2, A and Y have the same meanings as defined above, with an oxidizing agent.

[0184] In (Preparation Method 1), a sulfamoyl derivative (1) can be synthesized by reacting (2) with a halosulfonyltriazole (3) in the presence of a base.

[0185] The solvent may be any solvent so far as It is inert to the reaction. There may be employed, for example, ethers such as dioxane, dimethoxyethane and tetrahydrofuran, aromatic hydrocarbons such as toluene, xylene and chlorobenzene, halogenated hydrocarbons such as dichloroethane and chloroform, ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone, nitriles such as acetonitrile, tertiary amines such as pyridine, triethylamine and tributylamine, amides such as N,N-dimethylformamide, sulfur compounds such as dimethyl sulfoxide and sulfolane, nitro compounds such as nitrorethane and nitrobenzene, esters such as methyl acetate, or mixtures thereof. The reaction can be performed at a reaction temperature from −78° C. to the boiling point of the solvent.

[0186] As for the base, there may be employed, for example, organic bases such as pyridine, 4-dimethylaminopyridine, triethylamine, diethylisopropylamine and N,N-diethylaniline, inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate and potassium hydrogen carbonate, metal hydrides such as sodium hydride, metal alkoxides such as sodium methoxide and potassium t-butoxide, organic metal amides such as lithium diisopropylamide, organic metal compounds such as n-butyl lithium, and the like.

[0187] In the (Preparation Method 2), the sulfamoyl derivative (1) can be synthesized by reacting (4) with a dialkylsulfamoyl halide (5) in the presence of a base.

[0188] The solvent may be any solvent so far as it is inert to the reaction. There may be employed, for example, ethers such as dioxane, dimethoxyethane and tetrahydrofuran, aromatic hydrocarbons such as toluene, xylene and chlorobenzene, halogenated hydrocarbons such as dichloroethane and chloroform, ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone, nitriles such as acetonitrile, tertiary amines such as pyridine, triethylamine and tributylamine, amides such as N,N-dimethylformamide, sulfur compounds such as dimethyl sulfoxide and sulfolane, nitro compounds such as nitroethane and nitrobenzene, esters such as methyl acetate, or mixtures thereof. The reaction can be performed at a reaction temperature from −78° C. to the boiling point of the solvent.

[0189] As for the base, there may be employed, for example, organic bases such as pyridine, 4-dimethylaminopyridine, triethylamine, diethylisopropylamine and N,N-diethylaniline, inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate and potassium hydrogen carbonate, metal hydrides such as sodium hydride, metal alkoxides such as sodium methoxide and potassium t-butoxide, organic metal amides such as lithium diisopropylamide, organic metal compounds such as n-butyl lithium, and the like.

[0190] In the (Preparation Method 3), the sulfamoyl derivative (1) can be synthesized by oxidizing (6) with an oxidizing agent.

[0191] The solvent may be any solvent so far as it is inert to the reaction. There may be employed, for example, ethers such as dioxane, dimethoxyethane and tetrahydrofuran, aromatic hydrocarbons such as toluene, xylene and chlorobenzene, halogenated hydrocarbons such as dichloroethane and chloroform, ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone, nitriles such as acetonitrile, amides such as N,N-dimethylformamide, esters such as ethyl acetate, carboxylic acids such as acetic acid, water, or mixtures thereof. The reaction can be performed at a reaction temperature from −78° C. to the boiling point of the solvent.

[0192] As for the oxidizing agent, there may be employed, for example, peroxides such as hydrogen peroxide, peracetic acid, 3-chloro perbenzoic acid, sodium percarbonate, and the like.

[0193] The starting compounds of the method, compounds (2), (3), (4) and (6) can be readily synthesized by known methods (see Dai Yuki Kagaku vol. 14, 299-514 for the compound (2), JP-A-5-43557 and/or JP-A-7-215971 for the compound (3), Chem. Pharm. Bull. 41(7) 1226-1231 (1993) for the compound (4), and JP-A-9-143181 for the compound (6).) or methods analogous thereto.

[0194] As for the plant diseases which are target for control by the compound of the invention, there may be mentioned: rice blast (Pyricularia oryzae), helminthosporium leaf spot (Cochliobolus miyabeanus), sheath blight (Rhizoctonia solani), barley and wheat: powdery mildew (Erysiphe graminis f. sp. hordei, f. sp. tritici), stripe (Pyrenophora graminea), net blotch (Pyrenophora teres), scab (Gibberella zeae), rust (Puccinia striiformis, P. graminis, P. recondita, P. hordei), snow blight (Tipula sp., Micronectriella nivais), loose smut (Ustilago tritici, U. nuda), eye spot (Pseudocercosporella herpotrichoides), scald (Rhynchosporium secalis), spekled leaf blotch (Septoria tritici), glume blotch (Leptosphaeria nodorum), citrus: melanose (Diaporthe citri), scab (Elsinoe fawcetti), green mold and blue mold (Penicillium digitalum, P. italicum), apple: blossom blight (Sclerotinia mali), canker (Valsa mali), powdery mildew (Podosphaera lcucotricha), alternaria leaf spot (Alternaria mali), scab (Venturia inaequalis), pear: scab (Venturia nashicola), black spot (Alternaria kikuchiana), rust (Gymnosporangium haracanum), peach: brown rot (Sclerolinia cinerea), scab (Clcadosporium carpophilum), phomopsis rot (Phomopsis sp.), grape: downy mildew (Plasmopara viticola), anthracnose (Elsinoe ampelina), ripe rot (Glomerella cingulata), powdery mildew (Uncinula necator), rust (Phakopsora ampelopsidis), kaki: anthracnose (Gloeosporium kakj), angular leaf spot and circular leaf spot (Cercospora kakj, Mycosphaerella nawae), melons: downy mildew (Pseudoperenospora cubensis), anthracnose (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea), gummy stem blight (Mycosphaerella melonis), tomato: late blight (Phytophthora infestans), early blight (Alternaria solani), leaf mold (Cladosporium fulvum), egg plant: brown spot (Phomopsis vexans), powdery mildew (Erysiphe cichoracoarum), rape: black rot (Alternaria japonica), white rot (Cercosporella brassicae), oion: rust (Puccinia allii), soybean: purple stain of seed (Cercospora kikuchii), sphaceloma scab (Elisinoe glycines), black spot (Diaporthe phaseololum), kidney bean: anthracnose (Colletotrichum lindemuthianum), peanut: leaf spot (Mycosphaerella personatum), brown leaf spot (Cercospora arachidicola), pea: powdery mildew (Erysiphe pisi), potato: late blight (Alternaria solani), strawberry: powdery mildew (Sphaerotheca humuli), tea plant: net blister blast (Exobasidium reticulatum), white scab (Elsinoe leucospila), tobacco: brown spot (Alternaria lingipes), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), beet: cercospora leaf (Cercospora beticola), rose: black spot (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa), chrysanthemum: leaf spot (Septoria chrysanthemiindici), rust (Puccinia horiana), various crops: gray mold (Botrytis cinerea), various crops: sclerotinia rot (Sclerotinia sclerotiorum), and the like.

[0195] Upon use of the compound of the invention as agricultural and horticultural fungicides, they are generally mixed with a suitable carrier, for example, solid carriers such as clay, talc, bentonite and diatomaceous earth, or liquid carriers such as water, alcohols (methanol, ethanol, etc.), aromatic hydrocarbons (benzene, toluene, methylnaphthalene, etc.), chlorinated hydrocarbons, ethers, ketones, esters (ethyl acetate, etc.), acid amides (dimethylformamide, etc.), or the like to be applied. If desired, emulsifying agents, dispersants, suspension agents, penetrating agents, spreading agents, stabilizers and the like may be added so that the compounds can be subjected to practical application in any of formulation forms such as liquid formulation, emulsifiable concentrate, wettable powder, dust formulation, granule, or flowable powder.

[0196] The compound of the invention can be mixed or used in combination with various active compounds such as fungicides, bactericides, acaricides, nematicides and insecticides or other biologically active compounds. Common names of these active compounds will be listed below concretely. However, the invention should not be construed as being limited thereto.

[0197] Fungicidally active compounds: acibenzolar, ampropyfos, anilazine, azaconazole, azoxystrobin, benalaxyl, benodail, benomyl, benzamacril, binapacryl, biphenyl, bitertanol, bethoxazine, bordeaux mixture, blasticidin-S, bromoconazole, bupirimate, buthiobate, calcium polysulfide, captafol, captan, copper oxychloride, carpropamid, carbendazim, carboxin, chinomethionat, chlobenthiazone, chlorfenazol, chloroneb, chlorothalonil, chlozolinate, cufraneb, cymoxanil, cyproconazol, cyprodinil, cyprofuram, debacarb, dichlorophen, dichlobutrazol, dichlofluanid, dichlormedine, dichloran, diethofencarb, dichlocymet, difenoconazole, diflumetorim, dimethirimol, dimethomorph, diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodemorph, dodine, drazoxolon, edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole, famoxadone, fenarimol, febuconazole, fenfuram, fenpiclonil, fenpropidin, fenpropimorph, fentin, ferbam, ferimzone, fluazinam, fludioxonil, fluoroimide, fluquinconazole, flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetyl-aluminium, fuberidazole, furalaxyl, fenamidone, fenhexamid, guazatine, hexachlorobenzene, hexaconazole, hymexazol, imazalil, imibenconazol, iminoctadine, ipconazole, iprobenfos, iprodione, isoprothiolane, iprovalicarb, kasugamycin, kresoxim-methyl, mancopper, mancozeb, maneb, umepanipyrim, mepronil, metalaxyl, metconazole, metiram, metominostrobin, myclobutanil, nabam, nickel bis(dimethyldithiocarbamate), nitrothal-isopropyl, nuarimol, octhilinone, ofurace, oxadixyl, oxycarboxin, oxpoconazole fumarate, pefurzoate, penconazole, pencycuron, phthalide, piperalin, polyoxins, probenazole, prochloraz, procymidone, propamocarb hydrochloride, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, quinoxyfen, quintozene, sulfur, spiroxamine, tebuconazole, tecnazene, tetraconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram, tolclofos-methyl, tolylfluanid, triadimefon, toriadimenol, triazoxide, tricyclazole, tridemorph, triflumizole, triforine, triticonazole, validamycin, vinclozolin, zineb, ziram.

[0198] Bactericidally active compounds: streptomycin, oxyterracycline, oxolinic acid.

[0199] Nematicidally active compounds: aldoxycarb, fosthiazate, fosthietan, oxamyl, fenamiphos.

[0200] Acaricidally active compounds: amitraz, bromopropylate, chinomethionat, chlorobenzilate, clofentezine, cyhexatine, dicofol, dienochlor, ethoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenproximate, halfenprox, hexythiazox, milbemectin, propargite, pyridaben, pyrimidifen, tebufenpyrad,

[0201] Insecticidally active compounds: abamectin, acephate, acetamipirid, azinphos-methyl, bendiocarb, benfuracarb, bensultap, bifenthrin, buprofezin, butocarboxim, carbaryl, carbofuran, carbosulfan, cartap, chlorfenapyr, chlorpyrifos, chlorfenvinphos, chlorfluazuron, clothianidin, chlromafenozide, chlorpyrifos-methyl, cyfluthrin, beta-cyfluthrin, cypermethrin, cyromazine, cyhalothrin, lambda-cyhalothrin, deltamethrin, diafenthiuron, diazinon, diacloden, diflubenzuron, dimethylvinphos, diofenolan, disulfoton, dimethoate, EPN, esfenvalerate, ethiofencarb, ethiprole, etofenprox, etrimfos, fenitrothion, fenobucarb, fenoxycarb, fenpropathrin, fenvalerate, fipronil, flucythrinate, flufenoxuron, flufenprox, tau-fluvalinate, fonophos, formetanate, formothion, furathiocarb, halofenozide, hexaflumuron, hydramethylnon, imidacloprid, isofenphos, indoxacarb, isoprocarb, isoxathion, lufenuron, malathion, metaldehyde, metahamidophos, methidathion, methacrifos, metalcarb, methomyl, methoprene, methoxychlor, methoxyfenozide, monocrotophos, muscalure, nitenpyram, omethoate, oxydemeton-methyl, oxamyl, parathion, parathion-methyl, permethrin, phenthoate, phoxim, phorate, phosalone, phosmet, phosphamidon, pirimicarb, pirimiphos-methyl, profenofos, pymetrozine, pyraclofos, pyriproxyfen, rotenone, sulprofos, silafluofen, spinosad, sulfotep, tebfenozide, teflubenzuron, tefluthorin, terbufos, tetrachlorovinphos, thiodicarb, thiamethoxam, thiofanox, thiometon, tolfenpyrad, tralomethrin, trichlorfon, triazuron, triflumuron, vamidothion.

[0202] When used as agricultural and horticultural fungicides, the compounds of the invention can be applied by foliage application, soil treatment, seed disinfection and the like. They are also effective in general methods usually utilized by those skilled in the art.

[0203] Further, if necessary, other herbicides, and various insecticides, fungicides, plant growth regulators, synergists and the like may be mixed at formulation or spraying and used together. An application rate of the compound of the invention varies due to an application field, an application period, an application method, a target disease, a cultured crop and the like, but generally it is suitable to apply about 0.005-50 kg of the active ingredient per hectare.

[0204] Next, formulation examples of fungicides containing the compound of the invention as active ingredients are shown as follows. However, the present invention should not be construed as being limited thereto. In the following formulation examples, all “parts” means are “parts by weight”.

[0205] Formulation Example 1 Emulsifiable Concentrate

Compound of the invention	20	parts
Methylnaphthalene	55	parts
Cyclohexanone	20	parts
Sorpol 2680 (mixture of nonionic surfactant and	5	parts
anionic surfactant: Toho Kagaku Kogyo K.K., trade name)

[0206] The above components are mixed uniformly to make an emulsion. Upon use, the emulsion is diluted by 50-20,000 times to apply 0.005-50 kg of the active ingredient per hectare.

[0207] Formulation Example 2 Wettable Powder

Compound of the invention	25	parts
Zeeklite PEP (mixture of kaolinite and celisite:	66	parts
Zeeklite Industry K.K., Ltd.)
Solpol 5039 (anionic surfactant: Toho Kagaku Kogyo	4	parts
K.K., trade name)
Carplex #80 (white carbon: Shionogi Seiyaku K.K.,	3	parts
trade name)
Calcium ligninsulfonate	2	parts

[0208] The above components are mixed and grounded uniformly to make a wettable powder. Upon use, the wettable powder is diluted to 50 to 20,000 times to spray 0.005 to 50 kg of active ingredient per hectare.

[0209] Formulation Example 3 Dust Formulation

	Compound of the invention	3	parts
	Carplex #80 (white carbon: Shionogi Seiyaku K.K.,	0.5	part
	trade name)
	Clay	95	parts
	Diisopropyl phosphate	1.5	parts

[0210] The above components are mixed and grounded uniformly to make a dust formulation. Upon use, the dust formulation is applied with 0.005 to 50 kg of active ingredient per hectare.

[0211] Formulation Example 4 Granule

	Compound of the invention	5	parts
	Bentonite	30	parts
	Talc	64	parts
	Calcium ligninsulfonate	1	part

[0212] The above components are mixed and grounded uniformly, stirred to mix with addition of a small amount of water, granulated by an extrusion granulator and dried to make a granule. Upon use, the granule is applied with 0.005 to 50 kg of active ingredient per hectare.

[0213] Formulation Example 5 Flowable Powder

Compound of the invention	25	parts
Solpol 3353 (nonionic surfactant: Toho Kagaku Kogyo	5	parts
K.K., trade name)
Lunox 1000C (anionic surfactant: Toho Kagaku Kogyo	0.5	part
K.K., trade name)
Xanthan gum (natural polymer)	0.2	part
Sodium benzoate	0.4	part
Propylene glycol	10	parts
Water	58.9	parts

[0214] The above components except for the active ingredient (the compound of the invention) are dissolved uniformly, to which the compound of the invention is added, stirred well, and thereafter water-grounded in a sand mill to obtain a flowable powder. Upon use, the flowable powder is diluted by 50-20,000 times to apply 0.005-50 kg of the active ingredient per hectare.

BEST MODE FOR CARRYING OUT THE INVENTION

[0215] Next, the present invention will be explained concretely by examples. However, the present invention should not be construed as being limited thereto.

EXAMPLE 1

[0216] Preparation of 1-(N,N-dimethylsulfamoyl)-3-(2-methyl-3-chloroindol-1-yl)sulfonyl-1,2,4-triazole (1-33(a))

[0217] 0.6 g of 2-methyl-3-chloroindole was dissolved in 20 ml of tetrahydrofuran, and 0.17 g of sodium hydride (55% or more) was added thereto with stirring under ice-cooling. After stirring at room temperature for 1 hour, the solution was ice-cooled again and 1.0 g of 1-N,N-dimethylsulfamoyl-3-chlorosulfonyl-1,2,4-triazole was added, and then the mixture was stirred at room temperature for 3 hours. After completion of the reaction, diluted hydrochloric acid was added and the reaction mixture was extracted with ethyl acetate. After distilling off the solvent, the residue was purified by column chromatography to obtain 0.73 g of the titled compound.

EXAMPLE 2

[0218] Preparation of 1-(N,N-dimethylsulfamoyl)-3-(3-chloroindazol-1-yl)sulfonyl-1,2,4-triazole (7-5(a))

[0219] 0.5 g of 3-chloroindazole was dissolved in 20 ml of tetrahydrofuran, and 0.4 g of triethylamine was added thereto with stirring under ice-cooling. Thereafter, 0.94 g of 1-N,N-dimethylsulfamoyl-3-chlorosulfonyl-1,2,4-triazole was added, and then the mixture was stirred at room temperature for 16 hours. After completion of the reaction, the reaction mixture was neutralized with diluted hydrochloric acid, and extracted with ethyl acetate. After distilling off the solvent, the residue was purified by column chromatography to obtain 0.94 g of the titled compound.

EXAMPLE 3

[0220] Preparation of 1-(N,N-dimethylsulfamoyl)-3-(3-phenyl-4-chloro-5-methylpyrazol-1-yl)sulfonyl-1,2,4-triazole (8-11(a))

[0221] 0.56 g of 3-phenyl-4-chloro-5-methylpyrazole was dissolved in 20 ml of tetrahydrofuran, and 0.47 g of triethylamine was added thereto with stirring under ice-cooling. Thereafter, 0.8 g of 1-N,N-dimethylsulfamoyl-3-chlorosulfonyl-1,2,4-triazole was added, and then the mixture was stirred at room temperature for 16 hours. After completion of the reaction, the reaction mixture was neutralized with diluted hydrochloric acid, and extracted with ethyl acetate. After distilling off the solvent, the residue was purified by column chromatography to obtain 1.04 g of the titled compound.

EXAMPLE 4

[0222] Preparation of 1-dimethylsulfamoyl-3-(4-trifluoromethylbenzoyl)-1,2,4-triazole (11-19(a))

[0223] 0.31 g of 3-(4-trifluoromethylbenzoyl) -1,2,4-triazole was dissolved in 3 ml of DMF, 0.21 g of potassium carbonate was added thereto, and then 0.22 g of dimethylsulfamoyl chloride was added at room temperature with stirring. After stirring the reaction mixture for 1.5 hours at room temperature, water was added to precipitate crystals, and the crystals were collected by filtration and washed with diethyl ether. Drying of the mixture under reducing pressure afforded 0.31 g of the titled compound.

EXAMPLE 5

[0224] Preparation of 1-dimethylsulfamoyl-3-(2-methylimidazo[1.2-a]pyridin-3-ylsulfonyl)-1,2,4-triazole (10-2(a))

[0225] 1.2 g of 1-dimethylsulfamoyl-3-(2-methylimidazo[1.2-a]pyridin-3-ylsulfenyl)-1,2,4-triazole was dissolved in a mixture of 20 ml of acetonitrile and 20 ml of water, and 3.0 g of sodium percarbonate was added thereto at room temperature. After stirring the mixture for 1 hour at room temperature, additional 3.0 g of sodium percarbonate was added. After completion of the reaction, the reaction mixture was neutralized with diluted hydrochloric acid and extracted with ethyl acetate. After distilling off the solvent, the residue was purified by column chromatography to obtain 0.3 g of the titled compound.

[0226] Next, the physical properties of the compounds of the formula (1) prepared according to these methods are shown in Table 12.

TABLE 12
Compound No. Property (m.p. ° C.)
1-1(a)       98-100
1-2(a)       74-76
1-3(a)       70-72
1-4(a)       70-72
1-9(a)       136-139
1-10(a)      118-121
1-11(a)      138-139
1-12(a)      138-139
1-13(a)      96-98
1-14(a)      Oil
1-20(a)      125-126
1-21(a)      120-122
1-22(a)      118-121
1-23(a)      78-79
1-26(a)      141-142.5
1-27(a)      60-61
1-31(a)      158-161
1-32(a)      145.5-146.5
1-33(a)      120-122
1-34(a)      81-82
1-35(a)      71-72
1-38(a)      128-129
1-41(a)      151-154
1-42(a)      140-141
1-42(i)      Oil
1-42(k)      142-145
1-42(l)      167.5-171
1-43(a)      118.5-120
1-44(a)      149-150
1-45(a)      Oil
1-50(a)      124-126
1-51(a)      181-182
1-56(a)      94-95
1-57(a)      61-63
1-62(a)      147.5-149
1-63(a)      134.5-136
1-71(a)      159-159.5
1-72(a)      104-107
1-81(a)      163-165
1-105(a)     135-137
1-118(a)     137-140
1-119(a)     139-140
1-125(a)     129-131
1-126(a)     119-121
1-130(a)     142-145
1-131(a)     128-129
1-133(a)     113-115
1-135(a)     80-81
1-136(c)     134.5-135.5
1-148(a)     112-113
1-152(a)     120-122
1-161(a)     Oil
1-163(a)     134.5-136
1-168(a)     138-139.5
1-187(a)     172-174
1-188(a)     166-168
1-211(a)     94-95
1-222(a)     126-127
1-232(a)     172-174
1-233(a)     164-165
1-243(a)     Oil
1-258(a)     125-128
1-265(a)     142-143.5
1-266(a)     114-117
1-276(a)     177.5-179
1-276(j)     87-89
1-277(a)     132-133
1-283(a)     112-113
1-289(a)     138.5-139.5
1-290(a)     142-143
1-298(a)     90-92
1-311(a)     142-143
1-316(a)     65-66.5
1-316(j)     91-92
1-326(a)     82-84
1-343(a)     Oil
1-353(a)     160-163
1-370(a)     Oil
1-378(a)     93-94
1-396(a)     149-151
1-403(a)     129-131
1-414(a)     151.5-153
1-421(a)     107-108.5
1-435(a)     184-186
1-440(a)     194.5-195.5
1-445(a)     50-53
1-470(a)     120-122
1-497(a)     119-121
1-508(a)     148-150
1-518(a)     Oil
1-537(a)     153-155
1-548(a)     204-206
             (decomposition)
1-557(a)     Oil
1-568(a)     51-53
2-2(a)       134-135
2-2(b)       160-161
2-2(n)       184-186
2-2(o)       180-181.5
2-3(b)       140.5-142
2-3(n)       151.5-152.5
2-3(o)       162.5-163
2-4(b)       176-180
2-5(a)       143-144
2-5(b)       174-176
2-6(a)       104-105
2-6(d)       141-143
2-6(e)       168-169
2-6(n)       173-175
2-7(a)       117-118
2-7(b)       142-145
2-7(n)       143-144
2-8(b)       177-179
2-8(x)       123-124
2-10(a)      112.5-114
2-10(b)      143-145
2-10(n)      163-164.5
2-10(v)      138-141
2-11(e)      149-150.5
2-14(a)      85.5-87
2-14(b)      150.5-153
2-17(a)      145-147
2-17(b)      181-183
2-18(a)      86-87
2-18(b)      134-136
2-19(a)      82-83
2-19(b)      136-138
2-20(a)      109-110
2-20(b)      148-149
2-24(a)      61-63
2-24(b)      81-83
2-26(a)      126.5-127.5
2-30(a)      177-179
2-30(b)      174-176
2-34(a)      156-157
2-34(b)      181-183
2-39(e)      126-128
2-44(b)      162-163
3-1(a)       160-162
5-1(a)       115-118
5-22(a)      Oil
5-23(a)      39-42
5-34(a)      55-58
             (decomposition)
5-58(a)      44-47
5-82(a)      121-123
5-146(a)     182-184
5-146(h)     145.5-147.5
5-153(a)     139-140
5-165(a)     128-129.5
5-227(a)     42-45
5-234(a)     Oil
5-247(a)     Oil
5-254(a)     68-70
5-254(h)     Oil
5-261(a)     151-154
5-274(a)     173-176
5-490(a)     126-129
5-495(a)     149-150.5
5-506(a)     145-147
6-6(a)       163.5-164.5
6-30(a)      54-56
7-1(a),(b)   135-137
             (mixture)
7-2(e)       135-136
7-5(a)       164-165
8-1(a)       154.5-155.5
8-10(a)      110.5-111
8-11(a)      125-128
10-2(a)      179.5-181
11-1(a)      81-82
11-17(a)     89-91
11-18(a)     62-63
11-19(a)     121-122
11-24(a)     133-135

[0227] Usefulness of the compound of the invention will be explained concretely by the following test examples. However, the present invention should not be construed as being limited thereto.

Test Example 1

[0228] Test on Cucumber Downy Mildew Controlling Effect

[0229] Cucumber (species: Sagami Hanjiro) grown in a pot having a diameter of 7 cm was applied at 1.5 leaf stage by means of a spray-gun with 20 ml per a pot of agent solution which was prepared by diluting the emulsifiable concentrate of the compound of the invention with water to 500 ppm.

[0230] A day after application, spore suspension of cucumber downy midlew pathogen (Pseudoperonospora cubensis) (2×105 /ml) was sprayed for inoculation. Inoculated cucumber was placed in an inoculation box at a temperature of 25° C. and a humidity of 95% or more for one day and night. Thereafter, the cucumber was placed in a greenhouse and determined a ratio of disease spot area formed after 7 days from inoculation to inoculated leaves to calculate a control value according to the following equation:

control value=[ 1−(disease spot area proportion in treated part/disease spot area proportion in non-treated part)]×100

[0231] As a result, the following compounds showed a controlling value of 100.

[0232] The compound of the invention No.: 1-1(a), 1-2(a), 1-3(a), 1-4(a), 1-9(a), 1-10(a), 1-11(a), 1-12(a), 1-13(a), 1-14(a), 1-20(a), 1-21(a), 1-22(a), 1-23(a), 1-32(a), 1-33(a), 1-34(a), 1-35(a), 1-38(a), 1-41(a), 1-42(a), 1-43(a), 1-44(a), 1-45(a), 1-50(a), 1-51(a), 1-56(a), 1-62(a), 1-63(a), 1-71(a), 1-72(a), 1-81(a), 1-105(a), 1-118(a), 1-119(a), 1-125(a), 1-126(a), 1-130(a), 1-131(a), 1-133(a), 1-135(a), 1-136(c), 1-148(a), 1-152(a), 1-161(a), 1-163(a), 1-168(a), 1-187(a), 1-188(a), 1-211(a), 1-222(a), 1-232(a), 1-233(a), 1-243(a), 1-258(a), 1-265(a), 1-266(a), 1-276(a), 1-277(a), 1-283(a), 1-289(a), 1-290(a), 1-298(a), 1-311(a), 1-316(a), 1-326(a), 1-343(a), 1-353(a), 1-370(a), 1-378(a), 1-396(a), 1-403(a), 1-414(a), 1-421(a), 1-435(a), 1-440(a), 1-445(a), 1-470(a), 1-497(a), 1-508(a), 1-518(a), 1-537(a), 1-548(a), 1-568(a), 2-2(a), 2-2(b), 2-2(n), 2-2(o), 2-3(b), 2-3(n), 2-3(o), 2-4(b), 2-5(a), 2-5(b), 2-6(a), 2-6(d), 2-6(e), 2-6(n), 2-7(a), 2-7(b), 2-7(n), 2-8(b), 2-8(x), 2-10(a), 2-10(b), 2-10(n), 2-10(v), 2-11(e), 2-14(a), 2-14(b), 2-17(a), 2-17(b), 2-18(a), 2-18(b), 2-19(a), 2-19(b), 2-20(a), 2-20(b), 2-24(a), 2-24(b), 2-26(a), 2-34(a), 2-34(b), 2-39(e), 2-44(b), 3-1(a), 5-1(a), 5-22(a), 5-23(a), 5-34(a), 5-58(a), 5-82(a), 5-146(a), 5-153(a), 5-165(a), 5-227(a), 5-234(a), 5-247(a), 5-254(a), 5-261(a), 5-274(a), 5-490(a), 5-495(a), 5-506(a), 6-6(a), 6-30(a), 7-1(a), (b), 7-2(e), 7-5(a), 8-1(a), 8-10 (a), 8-11(a), 10-2(a), 11-l(a), 11-17(a), 11-18 (a), 11-19(a), 11-24(a).

INDUSTRIAL APPLICABILITY

[0233] These compounds are novel, exhibit excellent agricultural and horticultural fungicidal effect and have no phytotoxicity on useful crops so that they are useful as agricultural and horticultural fungicides.

Claims

1. A sulfamoyl compound of the general formulae (1):

2. A sulfamoyl compound according to claim 1, in which A is A-1.

3. A sulfamoyl compound according to claim 1, in which A is A-2.

4. A sulfamoyl compound according to claim 1, in which A is A-3.

5. A sulfamoyl compound according to claim 1, in which A is A-4.

6. A sulfamoyl compound according to claim 1, in which A is A-5 or A-6.

7. A sulfamoyl compound according to claim 1, in which A is A-7 or A-8.

8. A sulfamoyl compound according to claim 1, in which A is A-9 or A-10.

9. A sulfamoyl compound according to claim 1, in which B is B-1.

10. A sulfamoyl compound according to claim 1, in which B is B-2.

11. A sulfamoyl compound according to claim 1, in which B is B-3 or B-4.

12. A sulfamoyl compound according to claim 1, in which B is B-5.

13. A sulfamoyl compound according to claim 1, in which B is B-6 or B-7.

14. A sulfamoyl compound according to claim 1, in which B is B-8 or B-9.

15. A sulfamoyl compound according to claim 1, in which B is B-10.

16. A sulfamoyl compound according to claim 1, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR7, CR8, CR9 or CR10, and R3 is C1-8 alkylthio.

17. A sulfamoyl compound according to claim 1, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR7, CR8, CR9 or CR10, and R3 is C1-8 alkyl.

18. A sulfamoyl compound according to claim 1, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR7, CR8, CR9 or CR10, and R3 is C1-8 haloalkyl.

19. A sulfamoyl compound according to claim 1, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR7, CR8, CR9 or CR10, and R3 is halogen.

20. A sulfamoyl compound according to claim 1, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR7, CR8, CR9 or CR10, and R3 is H.

21. A sulfamoyl compound according to claim 1, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR7, CR8, CR9 or CR10, and R3 is CN.

22. A sulfamoyl compound according to claim 1, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-2, D, E, F and G are CR7, CR8, CR9 or CR10, and any of R3, R4, R5 and R6 is H.

23. A sulfamoyl compound according to claim 1, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-4, and at least one of R3, R4, R5 and R6 is phenyl which may be substituted.

24. A sulfamoyl compound according to claim 1, in which R1 and R2 are Me, Y is H, W is a chemical bond, and B is B-1.

25. A sulfamoyl compound according to claim 1, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR7, CR8, CR9 or CR10, R3 is C1-8 alkyl, and R4 is halogen.

26. A sulfamoyl compound according to claim 1, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR7, CR8, CR9 or CR10, and any of R3 and R4 is halogen.

27. A sulfamoyl compound according to claim 1, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR7, CR8, CR9 or CR10, R3 is C1-8 alkyl, and R4 is H or C1-8 alkyl.

28. A sulfamoyl compound according to claim 1, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR7, CR8, CR9 or CR10, R3 is C1-8 haloalkyl, and R4 is H, halogen or C1-8 alkyl.

29. A sulfamoyl compound according to claim 1, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR7, CR8, CR9 or CR10, R3 is H or C1-8 alkyl, and R4 is C1-6 alkoxycarbonyl.

30. A sulfamoyl compound according to claim 1, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR7, CR8, CR9 or CR10, R3 is H, and R4 is halogen.

31. A sulfamoyl compound according to claim 1, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR7, CR8, CR9 or CR10, R3 is CN, and R4 is H or C1-8 alkyl.

32. A sulfamoyl compound according to claim 1, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, any of D, E, F and G is CH, R3 is C1-8 alkyl, and R4 is halogen.

33. A sulfamoyl compound according to claim 1, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, any of D, E, F and G is CH, and any of R3 and R4 is halogen.

34. A sulfamoyl compound according to claim 1, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, any of D, E, F and G is CH, R3 is C1-8 haloalkyl, and R4 is H or C1-3 alkyl.

35. A sulfamoyl compound according to claim 1, in which R1 and R2 are Me, Y is H. W is a chemical bond, A is A-1, any of D, E, F and G is CH, R3 is Me or Et, and R4 is Cl or Br.

36. A sulfamoyl compound according to claim 1, in which R1 and R2 are Me, Y is H, W is a chemical bond, A is A-1, any of D, E, F and G is CH, R3 is Cl or Br, and R4 is Cl or Br.

37. An agricultural chemical containing as the active ingredient at least one sulfamoyl compound according to any one of claims 1 to 36 .

38. An agricultural chemical according to claim 37, in which the agricultural chemical is an agricultural and horticultural fungicide.