Claims
- 1. A compound having the formula (I): ##STR11## or a stereoisomer thereof, wherein A is hydrogen, halo, hydroxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, C.sub.1-4 haloalkoxy, C.sub.1-4 alkylcarbonyl, C.sub.1-4 alkoxycarbonyl, phenoxy, nitro or cyano; R.sup.1 is heterocycloalkyl, heteroaryloxyalkyl, heteroaryl or heteroaryloxy wherein the heteroaryl or heterocyclyl moiety is a 5- or 6-membered ring containing one or more O, N or S heteroatoms optionally fused to a benzene ring; R.sup.2 is hydrogen, C.sub.1-6 alkyl, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkyl(C.sub.1-4)alkyl, aryl(C.sub.1-4)alkyl, aryloxy(C.sub.1-4)-alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.1-6 alkoxy, aryl, aryloxy, nitro, halo, cyano, --NR.sup.3 R.sup.4, --CO.sub.2 R.sup.3, --CONR.sup.3 R.sup.4, --COR.sup.3, --S(O).sub.n R.sup.3 or (CH.sub.2).sub.m PO(OR.sup.3).sub.2 wherein n is 0, 1 or 2, m is 0 or 1 and R.sup.3 and R.sup.4, which are the same or different, are hydrogen, C.sub.1-6 alkyl, aryl(C.sub.1-6)alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl or aryl; any of the foregoing aryl moieties, which are phenyl or naphthyl, and any of the foregoing heterocyclyl or heteroaryl moieties being optionally substituted with one or more of halo, hydroxy, mercapto, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.1-4 alkoxy, C.sub.2-4 alkenyloxy, C.sub.2-4 alkynyloxy, halo(C.sub.1-4)alkyl, halo(C.sub.1-4)alkoxy, C.sub.1-4 alkylthio, hydroxy(C.sub.1-4)alkyl, C.sub.1-4 alkoxy(C.sub.1-4)alkyl, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkyl(C.sub.1-4)alkyl, phenyl, pyridyl, pyrimidinyl, phenoxy, pyridyloxy, pyrimidinyloxy, phenyl(C.sub.1-4)alkyl in which the alkyl moiety is optionally substituted with hydroxy, pyridyl- or pyrimidinyl(C.sub.1-4)-alkyl, phenyl(C.sub.2-4)alkenyl, pyridyl- or pyrimidinyl-(C.sub.2-4)alkenyl, phenyl(C.sub.1-4)alkoxy, pyridyl- or pyrimidinyl(C.sub.1-4)alkoxy, phenoxy(C.sub.1-4)alkyl, pyridyloxy- or pyrimidinyloxy(C.sub.1-4)alkyl, C.sub.1-4 alkanoyloxy, benzoyloxy, cyano, thiocyanato, nitro, --NR'R", --NHCOR', --NHCONR'R", --CONR'R", --COOR', --OSO.sub.2 R', --SO.sub.2 R', --COR', --CR'.dbd.NR" in which R' and R" are independently hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkyl(C.sub.1-4)alkyl, phenyl or benzyl, the phenyl and benzyl groups being optionally substituted with halogen, C.sub.1-4 alkyl or C.sub.1-4 alkoxy; and any of the foregoing phenyl, pyridyl or pyrimidinyl substituents themselves being optionally substituted with one or more of halo, hydroxy, mercapto, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.1-4 alkoxy, C.sub.2-4 alkenyloxy, C.sub.2-4 alkynyloxy, halo(C.sub.1-4)alkyl, halo(C.sub.1-4)alkoxy, C.sub.1-4 alkylthio, hydroxy(C.sub.1-4)alkyl, C.sub.1-4 alkoxy(C.sub.1-4)alkyl, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkyl(C.sub.1-4)alkyl, alkanoyloxy, benzoyloxy, cyano, thiocyanato, nitro, --NR'R", --NHCOR', --NHCONR'R", --CONR'R", --COOR', --SO.sub.2 R', --OSO.sub.2 R', --COR', --CR'.dbd.NR" or --N.dbd.CR'R" in which R' and R" have the meanings given above.
- 2. A compound according to claim 1 wherein the heteroaryl or heterocyclyl moiety of R.sup.1 is selected from the group consisting of imidazole, pyrazole, isothiazole, oxazole, isoxazole, thiadiazole, oxadiazole, isoquinoline, quinazoline, cinnoline, phthalazine, 1,2,3-benztriazine, 1,2,4-benztriazine, indole, benzothiophene, benzofuran, benzimidazole, indazole, benzthiazole, benzisothiazole, benzoxazole and benzisoxazole.
- 3. A compound according to claim 1 wherein the heteroaryl or heterocyclyl moiety of R.sup.1 is selected from the group consisting of oxazole, isoquinoline, quinazoline, benzothiophene and benzofuran.
- 4. A compound according to claim 1 wherein A is hydrogen, halo, hydroxy, methyl, methoxy, trifluoromethyl, trifluoromethoxy, C.sub.1-2 alkylcarbonyl, C.sub.1-2 alkoxycarbonyl, phenoxy, nitro or cyano; and R.sup.1 is an aromatic heterocycle selected from the group consisting of imidazole, pyrazole, isothiazole, oxazole, isoxazole, thiadiazole, oxadiazole, isoquinoline, quinazoline, cinnoline, phthalazine, 1,2,3-benztriazine, 1,2,4-benztriazine, indole, benzothiophene, benzofuran, benzimidazole, indazole, benzthiazole, benzisothiazole, benzoxazole and benzisoxazole, the heteroaromatic moieties of any of the foregoing being optionally substituted with one or more of halo, hydroxy, C.sub.1-4 alkyl, halo(C.sub.1-4)alkyl, C.sub.1-4 alkoxy, halo(C.sub.1-4)alkoxy, C.sub.1-4 alkylcarbonyl, C.sub.1-4 alkoxycarbonyl, nitro, cyano, phenyl, phenoxy, benzyl or benzyloxy; and R.sup.2 is hydrogen, halo, C.sub.1-4 alkyl, halo(C.sub.1-4)alkyl, C.sub.1-4 alkylcarbonyl, C.sub.1-4 alkoxycarbonyl, cyano or phenyl.
- 5. A compound according to claim 1 wherein A is hydrogen, halo, hydroxy, methyl, methoxy, trifluoromethyl, trifluoromethoxy, C.sub.1-2 alkylcarbonyl, C.sub.1-2 alkoxycarbonyl, phenoxy, nitro or cyano; and R.sup.1 is an aromatic heterocycle selected from the group consisting of oxazole, isoquinoline, quinazoline, benzothiophene and benzofuran, the heteroaromatic moieties of any of the foregoing being optionally substituted with one or more of halo, hydroxy, C.sub.1-4 alkyl, halo(C.sub.1-4)alkyl, C.sub.1-4 alkoxy, halo(C.sub.1-4)alkoxy, C.sub.1-4 alkylcarbonyl, C.sub.1-4 alkoxycarbonyl, nitro, cyano, phenyl, phenoxy, benzyl or benzyloxy; and R.sup.2 is hydrogen, halo, C.sub.1-4 alkyl, halo(C.sub.1-4)alkyl, C.sub.1-4 alkylcarbonyl, C.sub.1-4 alkoxycarbonyl, cyano or phenyl.
- 6. A compound of the formula: ##STR12## wherein R.sup.1 is imidazolyl, pyrazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, isoquinazolinyl, quinazolinyl, cinnolinyl, phthalazinyl, 1,2,3-benztriazinyl, 1,2,4-benztriazinyl, indolyl, benzothiophenyl, benzofuranyl, benzimidazolyl, indazolyl, benzthiazolyl, benzisothiazolyl, benzoxazolyl or benzisoxazolyl optionally substituted with one or more of halo, hydroxy, C.sub.1-4 alkyl, halo(C.sub.1-4)alkyl, C.sub.1-4 alkoxy, halo(C.sub.1-4)alkoxy, C.sub.1-4 alkylcarbonyl, C.sub.1-4 alkoxycarbonyl, nitro, cyano, phenyl, phenoxy, benzyl or benzyloxy; and R.sup.2 is hydrogen, halo, C.sub.1-4 alkyl, halo(C.sub.1-4)alkyl, C.sub.1-4 alkylcarbonyl, C.sub.1-4 alkoxycarbonyl, cyano or phenyl.
- 7. A compound according to claim 1 wherein R.sup.1 is oxazolyl, isoquinolinyl, quinazolinyl, benzothiophenyl or benzofuranyl optionally substituted with one or more of halo, hydroxy, C.sub.1-4 alkyl, halo(C.sub.1-4)alkyl, C.sub.1-4 alkoxy, halo(C.sub.1-4)alkoxy, C.sub.1-4 alkylcarbonyl, C.sub.1-4 alkoxycarbonyl, nitro, cyano, phenyl, phenoxy, benzyl or benzyloxy.
- 8. A fungicidal composition comprising, as an active ingredient, a compound as defined in claim 1 and a fungicidally acceptable carrier or diluent therefor.
- 9. A process for combating fungi which comprises applying to a plant, to a seed of a plant or to the locus thereof, a fungicidally effective amount of a compound as claimed in claim 1.
Priority Claims (2)
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8827149 |
Nov 1988 |
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8905383 |
Mar 1989 |
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Parent Case Info
This is a continuation of application Ser. No. 08/295,424, filed Aug. 25, 1994, now U.S. Pat. No. 5,432,197, which is a continuation of Ser. No. 08/142,109, filed Oct. 28, 1993, now U.S. Pat. No. 5,371,084, which is a continuation of Ser. No. 07/744,518, filed Aug. 13, 1991, now abandoned, which is a division of Ser. No. 07/436,752, filed Nov. 15, 1989, now U.S. Pat. No. 5,055,471.
US Referenced Citations (9)
Number |
Name |
Date |
Kind |
4773034 |
Schirmer et al. |
Sep 1988 |
|
4829085 |
Wendult et al. |
May 1989 |
|
5055471 |
De Fraine et al. |
Oct 1991 |
|
5104872 |
Tsubata et al. |
Apr 1992 |
|
5194662 |
Brand et al. |
Mar 1993 |
|
5298527 |
Grammenos et al. |
Mar 1994 |
|
5334607 |
Sauter et al. |
Aug 1994 |
|
5371084 |
De Fraine et al. |
Dec 1994 |
|
5432197 |
De Fraine et al. |
Jul 1995 |
|
Foreign Referenced Citations (14)
Number |
Date |
Country |
0024888 |
Oct 1981 |
EPX |
0178826 |
Apr 1986 |
EPX |
0203606 |
Dec 1986 |
EPX |
0226917 |
Jul 1987 |
EPX |
0230773 |
Aug 1987 |
EPX |
0241901 |
Oct 1987 |
EPX |
0251082 |
Jan 1988 |
EPX |
0253313 |
Jan 1988 |
EPX |
0273572 |
Jul 1988 |
EPX |
2430416 |
Jan 1980 |
FRX |
3208330 |
Sep 1983 |
DEX |
2308330 |
Sep 1983 |
DEX |
1318681 |
May 1973 |
GBX |
WO9007493 |
Jul 1990 |
WOX |
Non-Patent Literature Citations (9)
Entry |
Watanabe et al., Chemical Abstracts, vol. 115, abstract 91848q. 1991. |
Chemical Abstracts, 92 (1980) 198103b. |
Chemical Abstracts, 111 (1989) 92323u. |
Chemical Abstracts, 105 (1986) 78670z. |
Chemical Abstracts, 107 (1987) 193307s. |
Chemical Abstracts, 81 (1974) 22306d. |
Chemical Abstracts 107 (1987) 194794h. |
Chemical Abstracts, vol. 114 (1990) 6032f. |
Chemical Abstracts, vol. 115 (1990) 91847. |
Divisions (1)
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436752 |
Nov 1989 |
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Continuations (3)
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295424 |
Aug 1994 |
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142109 |
Oct 1993 |
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744518 |
Aug 1991 |
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