(en)A sulfamoyl compound of the general formulae (1):
wherein
R 1 and R 2 are each independently C 1-4 alkyl, or R 1 and R 2 together are C 4-6 alkylene or C 4-6 alkyleneoxy,
Y is H, halogen, C 1-8 alkyl, C 1-8 alkoxy, C 1-8 alkylthio, C 1-8 haloalkyl, C 1-8 haloalkoxy or C 1-8 haloalkylthio,
A is a predetermined heterocyclic group,
B is a predetermined heterocyclic group which is identical with or different from A,
W is a chemical bond or O,
V is O or S,
D, E, F and G are each independently N, CR 7 , CR 8 , CR 9 or CR 10 , and
R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are each independently predetermined group such as H, or an unsubstituted or substituted aliphatic, aromatic or heterocyclic group. The sulfamoyl compound is useful as an agricultural and horticultural fungicide.

1.ApplicationNumber: US-96435701-A
1.PublishNumber: US-6620812-B2
2.Date Publish: 20030916
3.Inventor: TAKEYAMA TOSHIAKI
HAMADA TOSHIMASA
TAKAHASHI HIROAKI
WATANABE JUNICHI
YAMAGISHI KAZUHIRO
NISHIOKA MASANORI
SUZUKI HIROYUKI

4.Inventor Harmonized: TAKEYAMA TOSHIAKI(JP)
HAMADA TOSHIMASA(JP)
TAKAHASHI HIROAKI(JP)
WATANABE JUNICHI(JP)
YAMAGISHI KAZUHIRO(JP)
NISHIOKA MASANORI(JP)
SUZUKI HIROYUKI(JP)

5.Country: US
6.Claims:
(en)A sulfamoyl compound of the general formulae (1):
wherein
R 1 and R 2 are each independently C 1-4 alkyl, or R 1 and R 2 together are C 4-6 alkylene or C 4-6 alkyleneoxy,
Y is H, halogen, C 1-8 alkyl, C 1-8 alkoxy, C 1-8 alkylthio, C 1-8 haloalkyl, C 1-8 haloalkoxy or C 1-8 haloalkylthio,
A is a predetermined heterocyclic group,
B is a predetermined heterocyclic group which is identical with or different from A,
W is a chemical bond or O,
V is O or S,
D, E, F and G are each independently N, CR 7 , CR 8 , CR 9 or CR 10 , and
R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are each independently predetermined group such as H, or an unsubstituted or substituted aliphatic, aromatic or heterocyclic group. The sulfamoyl compound is useful as an agricultural and horticultural fungicide.

7.Description:
(en)This is a division of application Ser. No. 09/529,817, filed on Jun. 2, 2000, now U.S. Pat. No. 6,350,748, which is a 371 of PCT/JP98/04808, filed Oct. 23, 1998.


TECHNICAL FIELD
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
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.
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
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.
That is, the present invention relates to [1] to [38].
[1] A sulfamoyl compound of the general formulae (1):
wherein
R 1 and R 2 are each independently C 1-4 alkyl, or R 1 and R 2 together are C 4-6 alkylene or C 4-6 alkyleneoxy,
Y is H, halogen, C 1-8 alkyl, C 1-8 alkoxy, C 1-8 alkylthio, C 1-8 haloalkyl, C 1-8 haloalkoxy or C 1-8 haloalkylthio,
A is

B is A-1 to A-10, or
W is a chemical bond or O,
V is O or S,
D, E, F and G are each independently N, CR 7 , CR 8 , CR 9 or CR 10 , and
R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are each independently H, C 1-8 alkyl, C 3-8 cycloalkyl, C 2-8 alkenyl, C 5-8 cycloalkenyl, C 2-8 alkynyl, C 1-8 alkoxy, C 3-8 cycloalkyloxy, C 5-8 cycloalkenyloxy, C 2-8 alkenyloxy, C 2-8 alkynyloxy, C 1-8 alkylthio, C 3-8 cycloalkylthio, C 5-8 cycloalkenylthio, C 2-8 alkenylthio. C 2-8 alkynylthio, C 1-8 haloalkyl, C 1-8 haloalkoxy, C 1-8 haloalkylthio, C 2-8 haloalkenyl, C 2-8 haloalkenyloxy, C 2-8 haloalkenylthio, C 2-8 haloalkynyl, C 2-8 haloalkynyloxy, C 2-8 haloalkynylthio, phenyl which may be substituted (the kinds of substituent include halogen, C 1-8 alkyl, C 1-8 haloalkyl, C 1-8 alkoxy, C 1-8 haloalkoxy, C 1-8 alkylthio, C 1-8 haloalkylthio, C 1-6 alkylsulfoxy, C 1-6 alkylsulfonyl, CN, NO 2 and C 1-6 alkoxycarbonyl, the number of the substituents is 1 to 5, and the substituents may be identical or different.), phenyl C 1-4 alkyl which may be substituted, benzylthio which may be substituted, benzyloxy which may be substituted, phenoxy C 1-4 alkyl which may be substituted, phenoxy which may be substituted, phenylthio C 1-4 alkyl which may be substituted, phenylthio which may be substituted, benzoyl which may be substituted, benzoyl C 1-4 alkyl which may be substituted, benzoyloxy which may be substituted, benzoyloxy C 1-4 alkyl which may be substituted, naphthyl which may be substituted, 5- or 6-membered heterocyclic ring which may be substituted, C 1-8 hydroxyalkyl, C 1-8 hydroxyhaloalkyl, C 1-6 alkoxy C 1-4 alkyl, C 1-6 haloalkoxy C 1-4 alkyl, C 1-6 haloalkylthio C 1-4 alkyl, C 1-10 dialkoxy C 1-4 alkyl, C 1-3 alkylenedioxy C 1-4 alkyl, C 1-6 alkylthio C 1-4 alkyl, C 1-10 dialkylthio C 1-4 alkyl, C 1-3 alkylenedithio C 1-4 alkyl, C 1-6 alkoxycarbonyl, C 1-6 haloalkoxycarbonyl, C 1-6 alkoxyoxalyl, CHO, CO 2 H, C 1-6 alkoxycarbonyl C 1-4 alkyl, C 1-6 haloalkoxycarbonyl C 1-4 alkyl, NH 2 , C 1-6 alkylamino, C 1-6 alkylcarbonylamino, C 1-6 alkylcarbonylamino C 1-4 alkyl, C 1-6 haloalkylcarbonylamino, C 1-6 haloalkylcarbonylamino C 1-4 alkyl, C 1-6 alkoxycarbonylamino, C 1-6 alkoxycarbonylamino C 1-4 alkyl, C 1-6 alkylsulfonylamino, C 1-6 alkylsulfonylamino C 1-4 alkyl, C 1-6 haloalkylsulfonylamino, C 1-6 haloalkylsulfonylamino C 1-4 alkyl, C 1-6 dialkylamino, C 1-6 dialkylamino C 1-4 alkyl, C 1-6 dialkylaminocarbonyl, C 1-6 dialkylaminocarbonyl C 1-4 alkyl, C 2-6 alkyleneimino, C 2-6 alkyleneimino C 1-4 alkyl, C 2-6 alkyleneiminocarbonyl, C 2-6 alkyleneiminocarbonyl C 1-4 alkyl, C 1-6 alkylcarbonyl, C 1-6 alkylcarbonyloxy, C 1-6 haloalkylcarbonyl, C 1-6 haloalkylcarbonyloxy, C 1-6 alkylcarbonyl C 1-4 alkyl, C 1-6 alkylcarbonyloxy C 1-4 alkyl, C 1-6 haloalkylcarbonyl C 1-4 alkyl, C 1-6 haloalkylcarbonyloxy C 1-4 alkyl, hydroxyimino C 1-4 alkyl, C 1-6 alkoxyimino C 1-4 alkyl, C 1-6 alkylcarbonyloxyimino C 1-4 alkyl, C 1-6 alkylsulfonyloxyimino C 1-4 alkyl, C 1-6 alkylsulfoxy, C 1-6 haloalkylsulfoxy, C 1-6 alkylsulfoxy C 1-4 alkyl, C 1-6 haloalkylsulfoxy C 1-4 alkyl, C 1-6 alkylsulfonyl, C 1-6 haloalkylsulfonyl, C 1-6 alkylsulfonyl C 1-4 alkyl, C 1-6 haloalkylsulfonyl C 1-4 alkyl, C 1-6 alkylsulfonyloxy, C 1-6 haloalkylsulfonyloxy, C 1-6 alkylsulfonyloxy C 1-4 alkyl, C 1-6 haloalkylsulfonyloxy C 1-4 alkyl, C 1-6 haloalkoxysulfonyl, C 1-6 haloalkoxysulfonyl C 1-4 alkyl, C 1-6 dialkylsulfamoyl, C 1-6 dialkylsulfamoyl C 1-4 alkyl, C 1-6 alkoxysulfonyl, C 1-6 alkoxysulfonyl C 1-4 alkyl, C 2-6 cyanoalkyl, CN, C 1-6 thiocarbamoyl, C 1-6 nitroalkyl, NO 2 or halogen, or
two of R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 together are C 1-3 alkylenedioxy which may be substituted, or C 3-6 alkylene.
[2] A sulfamoyl compound described in [1] above, in which A is A-1.
[3] A sulfamoyl compound described in [1] above, in which A is A-2.
[4] A sulfamoyl compound described in [1] above, in which A is A-3.
[5] A sulfamoyl compound described in [1] above, in which A is A-4.
[6] A sulfamoyl compound described in [1] above, in which A is A-5 or A-6.
[7] A sulfamoyl compound described in [1] above, in which A is A-7 or A-8.
[8] A sulfamoyl compound described in [1] above, in which A is A-9 or A-10.
[9] A sulfamoyl compound described in [1] above, in which B is B-1.
[10] A sulfamoyl compound described in [1] above, in which B is B-2.
[11] A sulfamoyl compound described in [1] above, in which B is B-3 or B-4.
[12] A sulfamoyl compound described in [1] above, in which B is B-5.
[13] A sulfamoyl compound described in [1] above, in which B is B-6 or B-7.
[14] A sulfamoyl compound described in [1] above, in which B is B-8 or B-9.
[15] A sulfamoyl compound described in [1] above, in which B is B-10.
[16] A sulfamoyl compound described in [1] above, in which R 1 and R 2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR 7 , CR 8 , CR 9 or CR 10 , and R 3 is C 1-8 alkylthio.
[17] A sulfamoyl compound described in [1] above, in which R 1 and R 2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR 7 , CR 8 , CR 9 or CR 10 , and R 3 is C 1-8 alkyl.
[18] A sulfamoyl compound described in [1] above, in which R 1 and R 2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR 7 , CR 8 , CR 9 or CR 10 , and R 3 is C 1-8 haloalkyl.
[19] A sulfamoyl compound described in [1] above, in which R 1 and R 2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR 7 , CR 8 , CR 9 or CR 10 , and R 3 is halogen.
[20] A sulfamoyl compound described in [1] above, in which R 1 and R 2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR 7 , CR 8 , CR 9 or CR 10 , and R 3 is H.
[21] A sulfamoyl compound described in [1] above, in which R 1 and R 2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR 7 , CR 8 , CR 9 or CR 10 , and R 3 is CN.
[22] A sulfamoyl compound described in [1] above, in which R 1 and R 2 are Me, Y is H, W is a chemical bond, A is A-2, D, E, F and G are CR 7 , CR 8 , CR 9 or CR 10 , and any of R 3 , R 4 , R 5 and R 6 is H.
[23] A sulfamoyl compound described in [1] above, in which R 1 and R 2 are Me, Y is H, W is a chemical bond, A is A-4, and at least one of R 3 , R 4 , R 5 and R 6 is phenyl which may be substituted.
[24] A sulfamoyl compound described in [1] above, in which R 1 and R 2 are Me, Y is H, W is a chemical bond, and B is B-1.
[25] A sulfamoyl compound described in [1] above, in which R 1 and R 2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR 7 , CR 8 , CR 9 or CR 10 , R 3 is C 1-8 alkyl, and R 4 is halogen.
[26] A sulfamoyl compound described in [1] above, in which R 1 and R 2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR 7 , CR 8 , CR 9 or CR 10 , and any of R 3 and R 4 is halogen.
[27] A sulfamoyl compound described in [1] above, in which R 1 and R 2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR 7 , CR 8 , CR 9 or CR 10 , R 3 is C 1-8 alkyl, and R 4 is H or C 1-8 alkyl.
[28] A sulfamoyl compound described in [1] above, in which R 1 and R 2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR 7 , CR 8 , CR 9 or CR 10 , R 3 is C 1-8 haloalkyl, and R 4 is H, halogen or C 1-8 alkyl.
[29] A sulfamoyl compound described in [1] above, in which R 1 and R 2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR 7 , CR 8 , CR 9 or CR 10 , R 3 is H or C 1-8 alkyl, and R 4 is C 1-6 alkoxycarbonyl.
[30] A sulfamoyl compound described in [1] above, in which R 1 and R 2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR 7 , CR 8 , CR 9 or CR 10 , R 3 is H, and R 4 is halogen.
[31] A sulfamoyl compound described in [1] above, in which R 1 and R 2 are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are CR 7 , CR 8 , CR 9 or CR 10 , R 3 is CN, and R 4 is H or C 1-8 alkyl.
[32] A sulfamoyl compound described in [1] above, in which R 1 and R 2 are Me, Y is H, W is a chemical bond, A is A-1, any of D, E, F and G is CH, R 3 is C 1-8 alkyl, and R 4 is halogen.
[33] A sulfamoyl compound described in [1] above, in which R 1 and R 2 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 R 3 and R 4 is halogen.
[34] A sulfamoyl compound described in [1] above, in which R 1 and R 2 are Me, Y is H, W is a chemical bond, A is A-1, any of D, E, F and G is CH, R 3 is C 1-8 haloalkyl, and R 4 is H or C 1-3 alkyl.
[35] A sulfamoyl compound described in [1] above, in which R 1 and R 2 are Me, Y is H, W is a chemical bond, A is A-1, any of D, E, F and G is CH, R 3 is Me or Et, and R 4 is Cl or Br.
[36] A sulfamoyl compound described in [1] above, in which R 1 and R 2 are Me, Y is H, W is a chemical bond, A is A-1, any of D, E, F and G is CH, R 3 is Cl or Br, and R 4 is Cl or Br.
[37] An agricultural chemical containing as the active ingredient at least one sulfamoyl compound described in [1] to [36] above.
[38] An agricultural chemical as described in [37] above, in which the agricultural chemical is an agricultural and horticultural fungicide.
In the compounds of the general formula (1), examples of C 1-4 alkyl for R 1 and R 2 are methyl, ethyl, n- or i-propyl, n-, i- or s-butyl and the like.
Examples of C 4-6 alkylene formed by R 1 and R 2 together are piperidine including the N to which R 1 and R 2 are bonded and the like.
Examples of C 4-6 alkyleneoxy formed by R 1 and R 2 together are morpholine including the N to which R 1 and R 2 are bonded and the like.
The definitions of substituents Y, R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 have following meanings.
Examples of C 1-8 alkyl are methyl, ethyl, n- or i-propyl, n- or i-butyl, n-pentyl and the like.
Examples of C 3-8 cycloalkyl are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like.
Examples of C 2-8 alkenyl are allyl, vinyl and the like.
Examples of C 5-8 cycloalkenyl are cyclopentenyl and the like.
Examples of C 2-8 alkynyl are propargyl and the like.
Examples of C 1-8 alkoxy are methoxy, ethoxy and the like.
Examples of C 3-8 cycloalkyloxy are cyclopropyloxy and the like.
Examples of C 3-8 cycloalkenyloxy are cyclopentenyl-3-oxy and the like.
Examples of C 2-8 alkenyloxy are allyloxy and the like.
Examples of C 2-8 alkynyloxy are propargyloxy and the like.
Examples of C 1-8 alkylthio are methylthio, ethylthio, n- or i-propylthio and the like.
Examples of C 3-8 cycloalkylthio are cyclopentylthio and the like.
Examples of C 3-8 cycloalkenylthio are cyclopentenyl-3-thio and the like.
Examples of C 2-8 alkenylthio are allylthio and the like.
Examples of C 2-8 alkynylthio are propargylthio and the like.
Examples of C 1-8 haloalkoxy are trifluoromethoxy and the like.
Examples of C 1-8 haloalkylthio are trifluoromethylthio and the like.
Examples of C 1-8 haloalkyl are chloromethyl, dichloromethyl, dichlorofluoromethyl, trifluoromethyl and the like.
Examples of C 2-8 haloalkenyl are 3-chloroallyl and the like.
Examples of C 2-8 haloalkenyloxy are 3-chloroallyloxy and the like.
Examples of C 2-8 haloalkenylthio are 3-chloroallylthio and the like.
Examples of C 2-8 haloalkynyl are iodopropargyl and the like.
Examples of C 2-8 haloalkynyloxy are iodopropargyloxy and the like.
Examples of C 2-8 haloalkynylthio are iodopropargylthio and the like.
Examples of C 1-8 hydroxyalkyl are hydroxymethyl, 1-hydroxyethyl and the like.
Examples of C 1-8 hydroxyhaloalkyl are 2,2,2-trifluoro-1-hydroxyethyl and the like.
Examples of C 1-6 alkoxy C 1-4 alkyl are methoxymethyl, methoxyethyl and the like.
Examples of C 1-6 haloalkoxy C 1-4 alkyl are trifluoroethoxymethyl and the like.
Examples of C 1-6 alkylthio C 1-4 alkyl are methylthiomethyl, ethylthiomethyl, methylthioethyl and the like.
Examples of C 1-6 haloalkylthio C 1-4 alkyl are trifluoroethylthiomethyl and the like.
Examples of C 1-10 dialkoxy C 1-4 alkyl are dimethoxymethyl, diethoxymethyl and the like.
Examples of C 1-10 dialkylthio C 1-4 alkyl are dimethylthiomethyl, diethylthiomethyl and the like.
Examples of C 1-3 alkylenedioxy C 1-4 alkyl are ethylenedioxymethyl and the like.
Examples of C 1-3 alkylenedithio C 1-4 alkyl are ethylenedithiomethyl and the like.
Examples of phenoxy C 1-4 alkyl which may be substituted are phenoxymethyl and the like.
Examples of phenoxy which may be substituted are phenoxy and the like.
Examples of phenylthio C 1-4 alkyl which may be substituted are phenylthiomethyl and the like.
Examples of phenylthio which may be substituted are phenylthio and the like.
Examples of phenyl C 1-4 alkyl which may be substituted are benzyl, phenethyl and the like.
Examples of benzylthio which may be substituted are benzylthio and the like.
Examples of benzyloxy which may be substituted are benzyloxy and the like.
Examples of phenyl which may be substituted are phenyl and the like.
Examples of benzoyl which may be substituted are benzoyl and the like.
Examples of benzoyl C 1-4 alkyl which may be substituted are benzoylmethyl and the like.
Examples of benzoyloxy which may be substituted are benzoyloxy and the like.
Examples of benzoyloxy C 1-4 alkyl which may be substituted are benzoyloxymethyl and the like.
Examples of naphthyl which may be substituted are naphthyl and the like.
Examples of 5- or 6-membered heterocyclic ring are pyridine, thiophene, furan, thiazole and the like.
Examples of C 1-6 alkoxycarbonyl are methoxycarbonyl and the like.
Examples of C 1-6 alkoxycarbonyl C 1-4 alkyl are methoxycarbonylmethyl and the like.
Examples of C 1-6 haloalkoxycarbonyl are fluoroethoxycarbonyl and the like.
Examples of C 1-6 haloalkoxycarbonyl C 1-4 alkyl are fluoroethoxycarbonylmethyl and the like.
Examples of C 1-6 alkoxyoxalyl are methoxyoxalyl, ethoxyoxalyl and the like.
Examples of C 1-6 dialkylamino are dimethylamino and the like.
Examples of C 1-6 alkylamino are methylamino and the like.
Examples of C 1-6 dialkylamino C 1-4 alkyl are dimethylaminomethyl and the like.
Examples of C 2-6 alkyleneimino are pyrrolidino, piperidino and the like.
Examples of C 2-6 alkyleneiminocarbonyl are pyrrolidinocarbonyl, piperidinocarbonyl and the like.
Examples of C 2-6 alkyleneimino C 1-4 alkyl are pyrrolidinomethyl, piperidinomethyl and the like.
Examples of C 2-6 alkyleneiminocarbonyl C 1-4 alkyl are pyrrolidinocarbonylmethyl, piperidinocarbonylmethyl and the like.
Examples of C 1-6 alkylcarbonylamino are acethylamino and the like.
Examples of C 1-6 alkoxycarbonylamino are methoxycarbonylamino and the like.
Examples of C 1-6 haloalkylcarbonylamino are trifluoroacethylamino and the like.
Examples of C 1-6 alkylsulfonylamino are methanesulfonylamino and the like.
Examples of C 1-6 haloalkylsulfonylamino are chloromethylsulfonylamino and the like.
Examples of C 1-6 alkylcarbonylamino C 1-4 alkyl are acetylaminomethyl and the like.
Examples of C 1-6 alkoxycarbonylamino C 1-4 alkyl are methoxycarbonylaminomethyl and the like.
Examples of C 1-6 haloalkylcarbonylamino C 1-4 alkyl are trifluoroacetylaminomethyl and the like.
Examples of C 1-6 alkylsulfonylamino C 1-4 alkyl are methanesulfonylaminomethyl and the like.
Examples of C 1-6 haloalkylsulfonylamino C 1-4 alkyl are chloromethylsulfonylaminomethyl and the like.
Examples of C 1-6 dialkylaminocarbonyl are dimethylaminocarbonyl and the like.
Examples of C 1-6 dialkylaminocarbonyl C 1-4 alkyl are dimethylaminocarbonylmethyl and the like.
Examples of C 1-6 alkylcarbonyl are acetyl and the like.
Examples of C 1-6 haloalkylcarbonyl are trifluoroacetyl and the like.
Examples of C 1-6 alkylcarbonyloxy are acetyloxy and the like.
Examples of C 1-6 haloalkylcarbonyloxy are trifluoroacetyloxy and the like.
Examples of C 1-6 alkylcarbonyl C 1-4 alkyl are acetylmethyl and the like.
Examples of C 1-6 haloalkylcarbonyl C 1-4 alkyl are trifluoroacetylmethyl and the like.
Examples of C 1-6 alkylcarbonyloxy C 1-4 alkyl are acetyloxymethyl and the like.
Examples of C 1-6 haloalkylcarbonyloxy C 1-4 alkyl are trifluoroacetyloxymethyl and the like.
Examples of hydroxyimino C 1-4 alkyl are hydroxyiminomethyl and the like.
Examples of alkoxyimino C 1-4 alkyl are methoxyiminomethyl and the like.
Examples of C 1-6 alkylcarbonyloxyimino C 1-4 alkyl are acetyloxyiminomethyl and the like.
Examples of C 1-6 alkylsulfonyloxyimino C 1-4 alkyl are methanesulfonyloxyiminomethyl and the like.
Examples of C 1-6 alkylsulfoxy are methylsulfoxy and the like.
Examples of C 1-6 alkylsulfoxy C 1-4 alkyl are methylsulfoxymethyl, ethylsulfoxymethyl, methylsulfoxyethyl and the like.
Examples of C 1-6 alkylsulfonyl are methanesulfonyl and the like.
Examples of C 1-6 alkylsulfonyloxy are methanesulfonyloxy and the like.
Examples of C 1-6 alkylsulfonyl C 1-4 alkyl are methylsulfonylmethyl, ethylsulfonylmethyl, methylsulfonylethyl and the like.
Examples of C 1-6 alkylsulfonyloxy C 1-4 alkyl are methylsulfonyloxymethyl and the like.
Examples of C 1-6 haloalkylsulfoxy are chloromethylsulfoxy and the like.
Examples of C 1-6 haloalkylsulfoxy C 1-4 alkyl are chloromethylsulfoxymethyl and the like.
Examples of C 1-6 haloalkylsulfonyl are trifluoromethylsulfonyl and the like.
Examples of C 1-6 haloalkylsulfonyloxy are trifluoromethylsulfonyloxy and the like.
Examples of C 1-6 haloalkylsulfonyl C 1-4 alkyl are trifluoromethylsulfonylmethyl and the like.
Examples of C 1-6 haloalkylsulfonyloxy C 1-4 alkyl are trifluoromethylsulfonyloxymethyl and the like.
Examples of C 1-6 dialkylsulfamoyl are dimethylsulfamoyl and the like.
Examples of C 1-6 dialkylsulfamoyl C 1-4 alkyl are dimethylsulfamoylmethyl and the like.
Examples of C 1-6 alkoxysulfonyl are methoxysulfonyl and the like.
Examples of C 1-6 alkoxysulfonyl C 1-4 alkyl are methoxysulfonylmethyl and the like.
Examples of C 1-6 haloalkoxysulfonyl are fluoroethoxysulfonyl and the like.
Examples of C 1-6 haloalkoxysulfonyl C 1-4 alkyl are fluoroethoxysulfonylmethyl and the like.
Examples of C 1-6 nitroalkyl are nitromethyl and the like.
Examples of C 2-6 cyanoalkyl are cyanomethyl and the like.
Examples of C 1-6 thiocarbamoyl are CSNH 2 and the like.
Examples of halogen are F, Cl, Br and I.
Examples of C 1-3 alkylenedioxy which may be substituted with halogen are difluoromethylenedioxy, tetrafluoroethylenedioxy and the like.
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.
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

























































































































































Compound No.
R 3
R 4





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
CH 2 OMe
H


1-16
CClF 2
H


1-17
CHF 2
H


1-18
CHFCl
H


1-19
CH 2 Cl
H


1-20
CF 3
H


1-21
CN
H


1-22
CHO
H


1-23
C 2 F 5
H


1-24
CH═NOMe
H


1-25
CO 2 Me
H


1-26
CO 2 Et
H


1-27
CONMe 2
H


1-28
COMe
H


1-29
COPh
H


1-30
CH 2 CO 2 Me
H


1-31
NO 2
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
CH 2 OMe
Cl


1-47
CHF 2
Cl


1-48
CHFCl
Cl


1-49
CH 2 Cl
Cl


1-50
CF 3
Cl


1-51
CN
Cl


1-52
CHO
Cl


1-53
C 2 F 5
Cl


1-54
CH═NOMe
Cl


1-55
CO 2 Me
Cl


1-56
CO 2 Et
Cl


1-57
CONMe 2
Cl


1-58
COMe
Cl


1-59
CClF 2
Cl


1-60
CH 2 CO 2 Me
Cl


1-61
NO 2
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
CH 2 OMe
Br


1-77
CHF 2
Br


1-78
CHFCl
Br


1-79
CH 2 Cl
Br


1-80
CF 3
Br


1-81
CN
Br


1-82
CHO
Br


1-83
C 2 F 5
Br


1-84
CH═NOMe
Br


1-85
CO 2 Me
Br


1-86
CO 2 Et
Br


1-87
CONMe 2
Br


1-88
COMe
Br


1-89
CClF 2
Br


1-90
CH 2 CO 2 Me
Br


1-91
NO 2
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
CF 3
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
CO 2 Et
F


1-115
SMe
F


1-116
CF 3
F


1-117
CN
F


1-118
H
Me


1-119
Me
Me


1-120
Et
Me


1-121
n-Pr
Me


1-122
CF 2 Cl
Me


1-123
CHF 2
Me


1-124
F
Me


1-125
Cl
Me


1-126
Br
Me


1-127
I
Me


1-128
SMe
Me


1-129
CF 3
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
CHF 2
Et


1-143
CClF 2
Et


1-144
CF 3
Et


1-145
CN
Et


1-146
CHO
Et






1-147
—(CH 2 ) 3 —


1-148
—(CH 2 ) 4 —


1-149
—(CH 2 ) 5 —


1-150
—(CH 2 ) 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
CF 3
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
CF 3
Bn


1-173
CN
Bn


1-174
H
CF 3


1-175
Me
CF 3


1-176
Et
CF 3


1-177
n-Pr
CF 3


1-178
n-Bu
CF 3


1-179
Ph
CF 3


1-180
F
CF 3


1-181
Cl
CF 3


1-182
Br
CF 3


1-183
I
CF 3


1-184
SMe
CF 3


1-185
CF 3
CF 3


1-186
CN
CF 3


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
CF 3
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
CF 3
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
CF 3
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
CF 3
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
CF 3
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
CF 3
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
COCF 3


1-266
Me
COCF 3


1-267
Et
COCF 3


1-268
n-Pr
COCF 3


1-269
F
COCF 3


1-270
Cl
COCF 3


1-271
Br
COCF 3


1-272
I
COCF 3


1-273
SMe
COCF 3


1-274
CF 3
COCF 3


1-275
CN
COCF 3


1-276
H
CO 2 Me


1-277
Me
CO 2 Me


1-278
Et
CO 2 Me


1-279
n-Pr
CO 2 Me


1-280
n-Bu
CO 2 Me


1-281
Ph
CO 2 Me


1-282
F
CO 2 Me


1-283
Cl
CO 2 Me


1-284
Br
CO 2 Me


1-285
I
CO 2 Me


1-286
SMe
CO 2 Me


1-287
CF 3
CO 2 Me


1-288
CN
CO 2 Me


1-289
H
CO 2 Et


1-290
Me
CO 2 Et


1-291
Et
CO 2 Et


1-292
F
CO 2 Et


1-293
Cl
CO 2 Et


1-294
Br
CO 2 Et


1-295
SMe
CO 2 Et


1-296
CF 3
CO 2 Et


1-297
CN
CO 2 Et


1-298
H
CO 2 n-Pr


1-299
Me
CO 2 n-Pr


1-300
Et
CO 2 n-Pr


1-301
F
CO 2 n-Pr


1-302
Cl
CO 2 n-Pr


1-303
Br
CO 2 n-Pr


1-304
SMe
CO 2 n-Pr


1-305
CF 3
CO 2 n-Pr


1-306
CN
CO 2 n-Pr


1-307
H
CO 2 I—Pr


1-309
Et
CO 2 I—Pr


1-310
F
CO 2 I—Pr


1-311
Cl
CO 2 I—Pr


1-312
Br
CO 2 I—Pr


1-313
SMe
CO 2 I—Pr


1-314
CF 3
CO 2 I—Pr


1-315
CN
CO 2 I—Pr


1-316
H
CO 2 n-Bu


1-317
Me
CO 2 n-Bu


1-318
Et
CO 2 n-Bu


1-319
F
CO 2 n-Bu


1-320
Cl
CO 2 n-Bu


1-321
Br
CO 2 n-Bu


1-322
SMe
CO 2 n-Bu


1-323
CF 3
CO 2 n-Bu


1-324
CN
CO 2 n-Bu


1-325
H
CO 2 I—Bu


1-326
Me
CO 2 I—Bu


1-327
Et
CO 2 I—Bu


1-328
F
CO 2 I—Bu


1-329
Cl
CO 2 I—Bu


1-330
Br
CO 2 I—Bu


1-331
SMe
CO 2 I—Bu


1-332
CF 3
CO 2 I—Bu


1-333
CN
CO 2 I—Bu


1-334
H
CO 2 s-Bu


1-335
Me
CO 2 s-Bu


1-336
Et
CO 2 s-Bu


1-337
F
CO 2 s-Bu


1-338
Cl
CO 2 s-Bu


1-339
Br
CO 2 s-Bu


1-340
SMe
CO 2 s-Bu


1-341
CF 3
CO 2 s-Bu


1-342
CN
CO 2 s-Bu


1-343
H
CO 2 t-Bu


1-344
Me
CO 2 t-Bu


1-345
Et
CO 2 t-Bu


1-346
F
CO 2 t-Bu


1-347
Cl
CO 2 t-Bu


1-348
Br
CO 2 t-Bu


1-349
SMe
CO 2 t-Bu


1-350
CF 3
CO 2 t-Bu


1-351
CN
CO 2 t-Bu


1-352
H
CO 2 Ph


1-353
Me
CO 2 Ph


1-354
Et
CO 2 Ph


1-355
F
CO 2 Ph


1-356
Cl
CO 2 Ph


1-357
Br
CO 2 Ph


1-358
SMe
CO 2 Ph


1-359
CF 3
CO 2 Ph


1-360
CN
CO 2 Ph


1-361
H
COCO 2 Me


1-362
Me
COCO 2 Me


1-363
F
COCO 2 Me


1-364
Cl
COCO 2 Me


1-365
Br
COCO 2 Me


1-366
SMe
COCO 2 Me


1-367
CF 3
COCO 2 Me


1-368
CN
COCO 2 Me


1-369
H
COCO 2 Et


1-370
Me
COCO 2 Et


1-371
F
COCO 2 Et


1-372
Cl
COCO 2 Et


1-373
Br
COCO 2 Et


1-374
SMe
COCO 2 Et


1-375
CF 3
COCO 2 Et


1-376
CN
COCO 2 Et


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
CF 3
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
CF 3
SOMe


1-394
CN
SOMe


1-395
H
SO 2 Me


1-396
Me
SO 2 Me


1-397
Et
SO 2 Me


1-398
Cl
SO 2 Me


1-399
Br
SO 2 Me


1-400
CF 3
SO 2 Me


1-401
CN
SO 2 Me


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
CF 3
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
CF 3
SOPh


1-419
CN
SOPh


1-420
H
SO 2 Ph


1-421
Me
SO 2 Ph


1-422
Et
SO 2 Ph


1-423
Cl
SO 2 Ph


1-424
Br
SO 2 Ph


1-425
CF 3
SO 2 Ph


1-426
CN
SO 2 Ph


1-427
H
NO 2


1-428
Me
NO 2


1-429
Et
NO 2


1-430
Cl
NO 2


1-431
Br
NO 2


1-432
SMe
NO 2


1-433
CF 3
NO 2


1-434
CN
NO 2


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
CF 3
CN


1-444
CN
CN


1-445
H
CH 2 CN


1-446
Me
CH 2 CN


1-447
Et
CH 2 CN


1-448
n-Pr
CH 2 CN


1-449
Cl
CH 2 CN


1-450
Br
CH 2 CN


1-451
SMe
CH 2 CN


1-452
CF 3
CH 2 CN


1-453
CN
CH 2 CN


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
CF 3
OMe


1-461
CN
OMe


1-462
H
CH 2 NMe 2


1-463
Me
CH 2 NMe 2


1-464
Et
CH 2 NMe 2


1-465
Cl
CH 2 NMe 2


1-466
Br
CH 2 NMe 2


1-467
SMe
CH 2 NMe 2


1-468
CF 3
CH 2 NMe 2


1-469
CN
CH 2 NMe 2


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
CF 3
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
CF 3
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
CF 3
CH(SMe) 2


1-495
CN
CH(SMe) 2


1-496
H
CH 2 Cl


1-497
Me
CH 2 Cl


1-498
Et
CH 2 Cl


1-499
n-Pr
CH 2 Cl


1-500
F
CH 2 Cl


1-501
Cl
CH 2 Cl


1-502
Br
CH 2 Cl


1-503
I
CH 2 Cl


1-504
SMe
CH 2 Cl


1-505
CF 3
CH 2 Cl


1-506
CN
CH 2 Cl


1-507
H
CH 2 OH


1-508
Me
CH 2 OH


1-509
Et
CH 2 OH


1-510
n-Pr
CH 2 OH


1-511
F
CH 2 OH


1-512
Cl
CH 2 OH


1-513
Br
CH 2 OH


1-514
SMe
CH 2 OH


1-515
CF 3
CH 2 OH


1-516
CN
CH 2 OH


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
CF 3
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
CF 3
CH(OH)Et


1-536
CN
CH(OH)Et


1-537
H
CH(OH)CF 3


1-538
Me
CH(OH)CF 3


1-539
Et
CH(OH)CF 3


1-540
n-Pr
CH(OH)CF 3


1-541
F
CH(OH)CF 3


1-542
Cl
CH(OH)CF 3


1-543
Br
CH(OH)CF 3


1-544
SMe
CH(OH)CF 3


1-545
CF 3
CH(OH)CF 3


1-546
CN
CH(OH)CF 3


1-547
H
CH 2 OMe


1-548
Me
CH 2 OMe


1-549
Et
CH 2 OMe


1-550
n-Pr
CH 2 OMe


1-551
F
CH 2 OMe


1-552
Cl
CH 2 OMe


1-553
Br
CH 2 OMe


1-554
SMe
CH 2 OMe


1-555
CF 3
CH 2 OMe


1-556
CN
CH 2 OMe


1-557
H
CONMe 2


1-558
Me
CONMe 2


1-559
Et
CONMe 2


1-560
n-Pr
CONMe 2


1-561
F
CONMe 2


1-562
Cl
CONMe 2


1-563
Br
CONMe 2


1-564
SMe
CONMe 2


1-565
CF 3
CONMe 2


1-566
CN
CONMe 2


1-567
H
CO(4-CF 3 Ph)


1-568
Me
CO(4-CF 3 Ph)


1-569
Et
CO(4-CF 3 Ph)


1-570
Cl
CO(4-CF 3 Ph)


1-571
Br
CO(4-CF 3 Ph)

















































































































































































































































































































































































































































































































































































































































TABLE 2









































































































































































































































































































Compound No.
R 7
R 8
R 9
R 10



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
NO 2
H
H
H

2-30
H
NO 2
H
H

2-31
H
H
NO 2
H

2-32
H
H
H
NO 2

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
CF 3
H
H
H

2-38
H
CF 3
H
H

2-39
H
H
CF 3
H

2-40
H
H
H
CF 3

2-41
CO 2 Me
H
H
H

2-42
H
CO 2 Me
H
H

2-43
H
H
CO 2 Me
H

2-44
H
H
H
CO 2 Me




















































































































TABLE 3

































Compound No.
R 7
R 8
R 9
R 10



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
CF 3
H
H
H

3-19
H
CF 3
H
H

3-20
H
H
CF 3
H

3-21
H
H
H
CF 3

















































TABLE 4



















































or



















Compound No.
R 3
R 4



4-1
H
H

4-2
H
Me

4-3
H
Et

4-4
H
Cl

4-5
H
Br

4-6
H
CF 3

4-7
Me
H

4-8
Me
Me

4-9
Me
Et

4-10
Me
Cl

4-11
Me
Br

4-12
Me
CF 3

4-13
Et
H

4-14
Et
Me

4-15
Et
Et

4-16
Et
Cl

4-17
Et
Br

4-18
Et
CF 3

4-19
Cl
H

4-20
Cl
Me

4-21
Cl
Et

4-22
Cl
Cl

4-23
Cl
Br

4-24
Cl
CF 3

4-25
Br
H

4-26
Br
Me

4-27
Br
Et

4-28
Br
Br

4-29
Br
CF 3

































































TABLE 5





















































































































Compound No.
R 3
R 4
R 5
R 6



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
CO 2 Me
Ph
Me
H

5-65
Me
Ph
CO 2 Me
H

5-66
CO 2 Me
Ph
Me
Cl

5-67
Me
Ph
CO 2 Me
Cl

5-68
CO 2 Me
Ph
Me
Br

5-69
Me
Ph
CO 2 Me
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
CO 2 Me
Me

5-83
H
Ph
Me
CO 2 Me

5-84
Cl
Ph
CO 2 Me
Me

5-85
Cl
Ph
Me
CO 2 Me

5-86
Br
Ph
CO 2 Me
Me

5-87
Br
Ph
Me
CO 2 Me

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
CO 2 Me
Ph
H
Me

5-101
Me
Ph
H
CO 2 Me

5-102
CO 2 Me
Ph
Cl
Me

5-103
Me
Ph
Cl
CO 2 Me

5-104
CO 2 Me
Ph
Br
Me

5-105
Me
Ph
Br
CO 2 Me

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
CF 3
Ph
H
H

5-173
H
Ph
CF 3
H

5-174
H
Ph
H
CF 3

5-175
CF 3
Ph
Cl
H

5-176
CF 3
Ph
H
Cl

5-177
CF 3
Ph
Cl
Cl

5-178
CF 3
Ph
Br
Cl

5-179
CF 3
Ph
Cl
Br

5-180
Cl
Ph
CF 3
H

5-181
H
Ph
CF 3
Cl

5-182
Cl
Ph
CF 3
Cl

5-183
Br
Ph
CF 3
Cl

5-184
Cl
Ph
CF 3
Br

5-185
Cl
Ph
H
CF 3

5-186
H
Ph
Cl
CF 3

5-187
Cl
Ph
Cl
CF 3

5-188
Br
Ph
Cl
CF 3

5-189
Cl
Ph
Br
CF 3

5-190
CF 3
Ph
Br
H

5-191
CF 3
Ph
H
Br

5-192
CF 3
Ph
Br
Br

5-193
Br
Ph
CF 3
H

5-194
H
Ph
CF 3
Br

5-195
Br
Ph
CF 3
Br

5-196
Br
Ph
H
CF 3

5-197
H
Ph
Br
CF 3

5-198
Br
Ph
Br
CF 3

5-199
NO 2
Ph
H
H

5-200
H
Ph
NO 2
H

5-201
H
Ph
H
NO 2

5-202
NO 2
Ph
Cl
H

5-203
NO 2
Ph
H
Cl

5-204
NO 2
Ph
Cl
Cl

5-205
NO 2
Ph
Br
Cl

5-206
NO 2
Ph
Cl
Br

5-207
Cl
Ph
NO 2
H

5-208
H
Ph
NO 2
Cl

5-209
Cl
Ph
NO 2
Cl

5-210
Br
Ph
NO 2
Cl

5-211
Cl
Ph
NO 2
Br

5-212
Cl
Ph
H
NO 2

5-213
H
Ph
Cl
NO 2

5-214
Cl
Ph
Cl
NO 2

5-215
Br
Ph
Cl
NO 2

5-216
Cl
Ph
Br
NO 2

5-217
NO 2
Ph
Br
H

5-218
NO 2
Ph
H
Br

5-219
NO 2
Ph
Br
Br

5-220
Br
Ph
NO 2
H

5-221
H
Ph
NO 2
Br

5-222
Br
Ph
NO 2
Br

5-223
Br
Ph
H
NO 2

5-224
H
Ph
Br
NO 2

5-225
Br
Ph
Br
NO 2

5-226
CO 2 Me
Ph
H
H

5-227
H
Ph
CO 2 Me
H

5-228
H
Ph
H
CO 2 Me

5-229
CO 2 Me
Ph
Cl
H

5-230
CO 2 Me
Ph
H
Cl

5-231
CO 2 Me
Ph
Cl
Cl

5-232
CO 2 Me
Ph
Br
Cl

5-233
CO 2 Me
Ph
Cl
Br

5-234
Cl
Ph
CO 2 Me
H

5-235
H
Ph
CO 2 Me
Cl

5-236
Cl
Ph
CO 2 Me
Cl

5-237
Br
Ph
CO 2 Me
Cl

5-238
Cl
Ph
CO 2 Me
Br

5-239
Cl
Ph
H
CO 2 Me

5-240
H
Ph
Cl
CO 2 Me

5-241
Cl
Ph
Cl
CO 2 Me

5-242
Br
Ph
Cl
CO 2 Me

5-243
Cl
Ph
Br
CO 2 Me

5-244
CO 2 Me
Ph
Br
H

5-245
CO 2 Me
Ph
H
Br

5-246
CO 2 Me
Ph
Br
Br

5-247
Br
Ph
CO 2 Me
H

5-248
H
Ph
CO 2 Me
Br

5-249
Br
Ph
CO 2 Me
Br

5-250
Br
Ph
H
CO 2 Me

5-251
H
Ph
Br
CO 2 Me

5-252
Br
Ph
Br
CO 2 Me

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
CF 3
H
H

5-360
Ph
H
CF 3
H

5-361
Ph
H
H
CF 3

5-362
Ph
CF 3
Cl
H

5-363
Ph
CF 3
H
Cl

5-364
Ph
CF 3
Cl
Cl

5-365
Ph
CF 3
Br
Cl

5-366
Ph
CF 3
Cl
Br

5-367
Ph
Cl
CF 3
H

5-368
Ph
H
CF 3
Cl

5-369
Ph
Cl
CF 3
Cl

5-370
Ph
Br
CF 3
Cl

5-371
Ph
Cl
CF 3
Br

5-372
Ph
Cl
H
CF 3

5-373
Ph
H
Cl
CF 3

5-374
Ph
Cl
Cl
CF 3

5-375
Ph
Br
Cl
CF 3

5-376
Ph
Cl
Br
CF 3

5-377
Ph
CF 3
Br
H

5-378
Ph
CF 3
H
Br

5-379
Ph
CF 3
Br
Br

5-380
Ph
Br
CF 3
H

5-381
Ph
H
CF 3
Br

5-382
Ph
Br
CF 3
Br

5-383
Ph
Br
H
CF 3

5-384
Ph
H
Br
CF 3

5-385
Ph
Br
Br
CF 3

5-386
Ph
NO 2
H
H

5-387
Ph
H
NO 2
H

5-388
Ph
H
H
NO 2

5-389
Ph
NO 2
Cl
H

5-390
Ph
NO 2
H
Cl

5-391
Ph
NO 2
Cl
Cl

5-392
Ph
NO 2
Br
Cl

5-393
Ph
NO 2
Cl
Br

5-394
Ph
Cl
NO 2
H

5-395
Ph
H
NO 2
Cl

5-396
Ph
Cl
NO 2
Cl

5-397
Ph
Br
NO 2
Cl

5-398
Ph
Cl
NO 2
Br

5-399
Ph
NO 2
Br
H

5-400
Ph
NO 2
H
Br

5-401
Ph
NO 2
Br
Br

5-402
Ph
Br
NO 2
H

5-403
Ph
H
NO 2
Br

5-404
Ph
Br
NO 2
Br

5-405
Ph
CO 2 Me
H
H

5-406
Ph
H
CO 2 Me
H

5-407
Ph
H
H
CO 2 Me

5-408
Ph
CO 2 Me
Cl
H

5-409
Ph
CO 2 Me
H
Cl

5-410
Ph
CO 2 Me
Cl
Cl

5-411
Ph
CO 2 Me
Br
Cl

5-412
Ph
CO 2 Me
Cl
Br

5-413
Ph
Cl
CO 2 Me
H

5-414
Ph
H
CO 2 Me
Cl

5-415
Ph
Cl
CO 2 Me
Cl

5-416
Ph
Br
CO 2 Me
Cl

5-417
Ph
Cl
CO 2 Me
Br

5-418
Ph
Cl
H
CO 2 Me

5-419
Ph
H
Cl
CO 2 Me

5-420
Ph
Cl
Cl
CO 2 Me

5-421
Ph
Br
Cl
CO 2 Me

5-422
Ph
Cl
Br
CO 2 Me

5-423
Ph
Cl
Br
Me

5-424
Ph
Br
Cl
Me

5-425
Ph
CO 2 Me
Br
H

5-426
Ph
CO 2 Me
H
Br

5-427
Ph
CO 2 Me
Br
Br

5-428
Ph
Br
CO 2 Me
H

5-429
Ph
H
CO 2 Me
Br

5-430
Ph
Br
CO 2 Me
Br

5-431
Ph
Br
H
CO 2 Me

5-432
Ph
H
Br
CO 2 Me

5-433
Ph
Br
Br
CO 2 Me

5-434
Ph
CO 2 Et
Cl
H

5-435
Ph
CO 2 Et
H
Cl

5-436
Ph
CO 2 Et
Cl
Cl

5-437
Ph
CO 2 Et
Br
Cl

5-438
Ph
CO 2 Et
Cl
Br

5-439
Ph
CO 2 Et
Br
Br

5-440
Ph
Cl
CO 2 Et
H

5-441
Ph
H
CO 2 Et
Cl

5-442
Ph
Cl
CO 2 Et
Cl

5-443
Ph
Br
CO 2 Et
Cl

5-444
Ph
Cl
CO 2 Et
Br

5-445
Ph
Br
CO 2 Et
Br

5-446
Ph
H
H
CO 2 Et

5-447
Ph
Cl
H
CO 2 Et

5-448
Ph
H
Cl
CO 2 Et

5-449
Ph
Cl
Cl
CO 2 Et

5-450
Ph
Cl
Br
CO 2 Et

5-451
Ph
Br
Cl
CO 2 Et

5-452
Ph
Br
Br
CO 2 Et

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
CO 2 Et
Ph
H
H

5-490
H
Ph
CO 2 Et
H

5-491
H
Ph
H
CO 2 Et

5-492
CO 2 Et
Ph
Cl
H

5-493
CO 2 Et
Ph
H
Cl

5-494
CO 2 Et
Ph
Cl
Cl

5-495
Cl
Ph
CO 2 Et
H

5-496
H
Ph
CO 2 Et
Cl

5-497
Cl
Ph
CO 2 Et
Cl

5-498
Cl
Ph
H
CO 2 Et

5-499
H
Ph
Cl
CO 2 Et

5-500
Cl
Ph
Cl
CO 2 Et

5-501
CO 2 Et
Ph
Br
H

5-502
CO 2 Et
Ph
H
Br

5-503
CO 2 Et
Ph
Cl
Br

5-504
CO 2 Et
Ph
Br
Cl

5-505
CO 2 Et
Ph
Br
Br

5-506
Br
Ph
CO 2 Et
H

5-507
H
Ph
CO 2 Et
Br

5-508
Br
Ph
CO 2 Et
Br

5-509
Cl
Ph
CO 2 Et
Br

5-510
Br
Ph
CO 2 Et
Cl

5-511
Br
Ph
H
CO 2 Et

5-512
H
Ph
Br
CO 2 Et

5-513
Br
Ph
Br
CO 2 Et

5-514
Cl
Ph
Br
CO 2 Et

5-515
Br
Ph
Cl
CO 2 Et

5-516
H
Ph
CO 2 Et
Me

5-517
Cl
Ph
CO 2 Et
Me

5-518
Br
Ph
CO 2 Et
Me

5-519
Me
Ph
CO 2 Et
H

5-520
Me
Ph
CO 2 Et
Cl

5-521
Me
Ph
CO 2 Et
Br

5-522
Ph
H
H
NO 2

5-523
Ph
Cl
H
NO 2

5-524
Ph
H
Cl
NO 2

5-525
Ph
Cl
Cl
NO 2























































































































































































































































































































































































































































































































































































TABLE 6




























































































































































Compound








No.
R 3
R 4
R 7
R 8
R 9
R 10
R 11



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
CF 3
H
H
H
H

6-11
H
H
H
CF 3
H
H
H

6-12
H
H
H
H
CF 3
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
CF 3
H
H
H
H

6-23
H
Cl
H
CF 3
H
H
H

6-24
H
Cl
H
H
CF 3
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
CF 3
H
H
H
H

6-35
H
Br
H
CF 3
H
H
H

6-36
H
Br
H
H
CF 3
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
CF 3
H
H
H
H

6-47
H
Me
H
CF 3
H
H
H

6-48
H
Me
H
H
CF 3
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
CF 3
H
H
H
H

6-59
Me
Cl
H
CF 3
H
H
H

6-60
Me
Cl
H
H
CF 3
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
CF 3
H
H
H
H

6-71
Me
Br
H
CF 3
H
H
H

6-72
Me
Br
H
H
CF 3
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
CF 3
H
H
H
H

6-83
Cl
Cl
H
CF 3
H
H
H

6-84
Cl
Cl
H
H
CF 3
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
CF 3
H
H
H
H

6-95
Cl
Br
H
CF 3
H
H
H

6-96
Cl
Br
H
H
CF 3
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
CF 3
H
H
H
H

6-107
Br
Br
H
CF 3
H
H
H

6-108
Br
Br
H
H
CF 3
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
CF 3
H
H
H
H

6-119
Me
Me
H
CF 3
H
H
H

6-120
Me
Me
H
H
CF 3
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
CF 3
Cl
H
H
H

6-138
H
H
CF 3
H
Cl
H
H

6-139
H
H
CF 3
H
H
Cl
H

6-140
H
H
CF 3
H
H
H
Cl

6-141
H
H
Cl
CF 3
H
H
H

6-142
H
H
H
CF 3
Cl
H
H

6-143
H
H
H
CF 3
H
Cl
H

6-144
H
H
H
CF 3
H
H
Cl

6-145
H
H
Cl
H
CF 3
H
H

6-146
H
H
H
Cl
CF 3
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



















































































































































































































































































TABLE 7




































































































































Compound







No.
R 3
R 7
R 8
R 9
R 10













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
CF 3
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
































































TABLE 8




























































































































































Compound








No.
R 3
R 4
R 7
R 8
R 9
R 10
R 11



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
NO 2
H
H
H
H
H

8-5
H
CO 2 Me
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
NO 2
H
H
H
H
H

8-14
Me
CO 2 Me
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
NO 2
H
H
H
H
H

8-23
Et
CO 2 Me
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
NO 2
H
H
H
H
H

8-32
n-Pr
CO 2 Me
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
NO 2
H
H
H
H
H

8-41
Cl
CO 2 Me
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
NO 2
H
H
H
H
H

8-50
Br
CO 2 Me
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
CF 3
H
H
H
H
H
H

8-56
CF 3
Cl
H
H
H
H
H

8-57
CF 3
Br
H
H
H
H
H

8-58
CF 3
NO 2
H
H
H
H
H

8-59
CF 3
CO 2 Me
H
H
H
H
H

8-60
CF 3
CN
H
H
H
H
H

8-61
CF 3
Me
H
H
H
H
H

8-62
CF 3
Et
H
H
H
H
H

8-63
CF 3
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
NO 2
H
H
H
H
H

8-68
Ph
CO 2 Me
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
CF 3
H
H
H
H

8-83
Me
Cl
H
CF 3
H
H
H

8-84
Me
Cl
H
H
CF 3
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
CF 3
H
H
H
H

8-95
Me
Br
H
CF 3
H
H
H

8-96
Me
Br
H
H
CF 3
H
H

















































































































































TABLE 9



































































































or























Compound







No.
R 3
R 4
R 7
R 8
R 9
R 10



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
NO 2
H
H
H
H

9-5
H
CN
H
H
H
H

9-6
H
CF 3
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
CO 2 Me
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
NO 2
H
H
H
H

9-15
Me
CN
H
H
H
H

9-16
Me
CF 3
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
CO 2 Me
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
NO 2
H
H
H
H

9-25
Et
CN
H
H
H
H

9-26
Et
CF 3
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
CO 2 Me
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
CF 3
H
H
H
H

9-36
Cl
Cl
H
H
H
H

9-37
Cl
Br
H
H
H
H

9-38
Cl
NO 2
H
H
H
H

9-39
Cl
SMe
H
H
H
H

9-40
Cl
CO 2 Me
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
CF 3
H
H
H
H

9-46
Br
Cl
H
H
H
H

9-47
Br
Br
H
H
H
H

9-48
Br
NO 2
H
H
H
H

9-49
Br
SMe
H
H
H
H

9-50
Br
CO 2 Me
H
H
H
H

9-51
CF 3
H
H
H
H
H

9-52
CF 3
Me
H
H
H
H

9-53
CF 3
Et
H
H
H
H

9-54
CF 3
CN
H
H
H
H

9-55
CF 3
CF 3
H
H
H
H

9-56
CF 3
Cl
H
H
H
H

9-57
CF 3
Br
H
H
H
H

9-58
CF 3
NO 2
H
H
H
H

9-59
CF 3
SMe
H
H
H
H

9-60
CF 3
CO 2 Me
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
NO 2
H
H
H
H

9-65
SMe
CN
H
H
H
H

9-66
SMe
CF 3
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
CO 2 Me
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
CF 3
H
H
H
H

9-76
CN
Cl
H
H
H
H

9-77
CN
Br
H
H
H
H

9-78
CN
NO 2
H
H
H
H

9-79
CN
SMe
H
H
H
H

9-80
CN
CO 2 Me
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













































































































































































TABLE 10




















































































Compound







No.
R 3
R 7
R 8
R 9
R 10





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
CF 3
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































































































































TABLE 11















or






















Compound






No.
R 7
R 8
R 9
R 10
R 11



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
CF 3
H
H
H
H

11-18
H
CF 3
H
H
H

11-19
H
H
CF 3
H
H

11-20
OCF 3
H
H
H
H

11-21
H
OCF 3
H
H
H

11-22
H
H
OCF 3
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
CO 2 Me
H
H
H
H

11-33
H
CO 2 Me
H
H
H

11-34
H
H
CO 2 Me
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
NO 2
H
H
H
H

11-39
H
NO 2
H
H
H

11-40
H
H
NO 2
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



























































































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


A—H (2)


wherein A has the same meaning as defined above, with a compound of the formula (3)
wherein R 1 , R 2 and Y have the same meanings as defined above, and X is halogen.
Preparation Method 2
The compound of the invention can be prepared by reacting a compound of the formula (4)
wherein B and Y have the same meanings as defined above, with a compound of the formula (5)


R 1 R 2 NSO 2 X


wherein R 1 and R 2 have the same meanings as defined above and X is halogen.
Preparation Method 3
The compound of the invention can be prepared by oxidizing a compound of the formula (6)
wherein R 1 , R 2 , A and Y have the same meanings as defined above, with an oxidizing agent.
In (Preparation Method 1), a sulfamoyl derivative (1) can be synthesized by reacting (2) with a halosulfonyltriazole (3) in the presence of a base.
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.
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.
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.
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.
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.
In the (Preparation Method 3), the sulfamoyl derivative (1) can be synthesized by oxidizing (6) with an oxidizing agent.
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.
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.
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.
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.
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.
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.
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.
Bactericidally active compounds: streptomycin, oxyterracycline, oxolinic acid.
Nematicidally active compounds: aldoxycarb, fosthiazate, fosthietan, oxamyl, fenamiphos.
Acaricidally active compounds: amitraz, bromopropylate, chinomethionat, chlorobenzilate, clofentezine, cyhexatine, dicofol, dienochlor, ethoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenproximate, halfenprox, hexythiazox, milbemectin, propargite, pyridaben, pyrimidifen, tebufenpyrad,
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.
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.
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.
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”.
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)


















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.
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





















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.
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



















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.
Formulation Example 4 Granule












Compound of the invention
5
parts


Bentonite
30
parts


Talc
64
parts


Calcium ligninsulfonate
1
part


















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.
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






















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


EXAMPLE 1
Preparation of 1-(N,N-dimethylsulfamoyl)-3-(2-methyl-3-chloroindol-1-yl)sulfonyl-1,2,4-triazole (1-33(a))
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
Preparation of 1-(N,N-dimethylsulfamoyl)-3-(3-chloroindazol-1-yl)sulfonyl-1,2,4-triazole (7-5(a))
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
Preparation of 1-(N,N-dimethylsulfamoyl)-3-(3-phenyl-4-chloro-5-methylpyrazol-1-yl)sulfonyl-1,2,4-triazole (8-11(a))
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
Preparation of 1-dimethylsulfamoyl-3-(4-trifluoromethylbenzoyl)-1,2,4-triazole (11-19(a))
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
Preparation of 1-dimethylsulfamoyl-3-(2-methylimidazo[1.2-a]pyridin-3-ylsulfonyl)-1,2,4-triazole (10-2(a))
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.
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
































































































































































































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
Test on Cucumber Downy Mildew Controlling Effect
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.
A day after application, spore suspension of cucumber downy midlew pathogen ( Pseudoperonospora cubensis ) (2×10 5 /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


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