Aryl and heteroarylcyclopropyl oxime ethers and their use as...

Details Aryl and heteroarylcyclopropyl oxime ethers and their use as... Aryl and heteroarylcyclopropyl oxime ethers and their use as...

2000-05-15

2002-02-19

Kumar, Shailendra (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

C514S503000, C514S531000, C514S618000, C514S619000, C558S256000, C560S035000, C562S440000

Reexamination Certificate

active

06348627

ABSTRACT:

The present invention relates to certain aryl cyclopropyl oxime ether compounds, compositions containing these compounds, and methods for controlling fungi by the use of a fungitoxic amount of these compounds.
Compounds having certain oxime ether structures are disclosed in U.S. Pat. Nos. 5,194,662 and 5,292,759. We have discovered a group of cyclopropyl oxime ethers which possess a substituted aryl and heterocyclic moieties which possess broad spectrum fungicidal properties.
The cyclopropyloxime ethers of the present invention have the Formula (I)
wherein X is N or CH; Z is O, S, or NR
8
;
A is hydrogen, halo, cyano, (C
1
-C
12
)alkyl, or (C
1
-C
12
)alkoxy;
R
1
and R
8
are independently hydrogen or (C
1
-C
4
)alkyl;
R
2
is hydrogen, (C
1
-C
12
)alkyl, halo(C
1
-C
12
)alkyl, (C
3
-C
7
)cycloalkyl, halo(C
3
-C
7
)cycloalkyl, (C
2
-C
8
)alkenyl, halo(C
2
-C
8
)alkenyl, (C
2
-C
8
)alkynyl, halo(C
2
-C
8
)alkynyl, or cyano;
R
3
is hydrogen, (C
1
-C
12
)alkyl, halo(C
1
-C
12
)alkyl, (C
3
-C
7
)cycloalkyl, halo(C
3
-C
7
)cycloalkyl, (C
2
-C
8
)alkenyl, halo(C
2
-C
8
)alkenyl, (C
2
-C
8
)alkynyl, or halo(C
2
-C
8
)alkynyl;
R
4
and R
5
are independently hydrogen, (C
1
-C
12
)alkyl, halo(C
1
-C
12
)alkyl, (C
3
-C
7
)cycloalkyl, halo(C
3
-C
7
)cycloalkyl, (C
2
-C
8
)alkenyl, halo(C
2
-C
8
)alkenyl, (C
2
-C
8
)alkynyl, halo(C
2
-C
8
)alkynyl, halo, cyano, or (C
1
-C
4
)alkoxycarbonyl; and wherein
A) R
7
is aryl, arylalkyl, heterocyclic or heterocyclic(C
1
-C
4
)alkyl wherein the aryl or heterocyclic ring is substituted with from 2 to 5 substituents and wherein the positions on the aryl or heterocyclic ring adjacent to the bond to the cyclopropyl ring are both substituted and R
6
is hydrogen, (C
1
-C
12
)alkyl, halo(C
1
-C
12
)alkyl, (C
3
-C
7
)cycloalkyl, halo(C
3
-C
7
)cycloalkyl, (C
2
-C
8
)alkenyl, halo(C
2
-C
8
)alkenyl, (C
2
-C
8
)alkynyl, or halo(C
2
-C
8
)alkynyl; or
B) R
7
is aryl, arylalkyl, heterocyclic or heterocyclic(C
1
-C
4
)alkyl wherein the aryl or heterocyclic ring is unsubstituted or substituted from 1 to 4 substituents wherein at least one of the positions on the aryl or heterocyclic ring adjacent to the bond to the cyclopropyl ring is a hydrogen and R
6
is (C
1
-C
12
)alkyl, halo(C
1
-C
12
)alkyl, (C
3
-C
7
)cycloalkyl, halo(C
3
-C
7
)cycloalkyl, (C
2
-C
8
)alkenyl, halo(C
2
-
8
)alkenyl, (C
2
-C
8
)alkynyl, or halo(C
2
-C
8
)alkynyl; and their salts, complexes, enantiomorphs, and stereoisomers; and mixtures thereof.
The aforementioned (C
1
-C
12
)alkyl, (C
2
-C
8
)alkenyl, (C
2
-C
8
)alkynyl and (C
3
-C
7
)cycloalkyl groups may be optionally and independently substituted with up to three substituents selected from nitro, halomethyl, (C
1
-C
4
)alkoxycarbonyl, and cyano.
The term alkyl includes both branched and straight chain alkyl groups from 1 to 12 carbon atoms. Typical alkyl groups are methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, isobutyl, t-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, isooctyl, nonyl, decyl, undecyl, dodecyl and the like. The term haloalkyl refers to an alkyl group substituted with from 1 to 3 halogens.
The term alkenyl refers to an ethylenically unsaturated hydrocarbon group, straight or branched, having a chain length of from 2 to 8 carbon atoms and 1 or 2 ethylenic bonds. The term haloalkenyl refers to an alkenyl group substituted with from 1 to 3 halogen atoms. The term alkynyl refers to an unsaturated hydrocarbon group, straight or branched, having a chain length of from 2 to 8 carbon atoms and 1 or 2 acetylenic bonds.
The term aryl includes phenyl and naphthyl which maybe substituted with up to four substituents independently selected from halogen, cyano, nitro, trihalomethyl, trihalomethoxy, phenyl, phenoxy, (C
1
-C
4
)alkyl, (C
3
-C
7
)cycloalkyl, (C
2
-C
8
)alkenyl, (C
1
-C
4
)alkoxy, (C
1
-C
4
)alkylthio, (C
1
-C
4
)alkylsulfoxide, halo(C
1
-C
4
)alkyl, halo(C
1
-C
4
)alkoxy, halo(C
3
-C
7
)cycloalkyl, halo(C
2
-C
8
)alkenyl, or (C
1
-C
4
)alkoxycarbonyl. Typical phenyl substituents, wherein at least one of the positions on the phenyl ring adjacent to the bond to the cyclopropyl ring is substituted with hydrogen include but are not limited to 2-chloro, 3-chloro, 4-chloro, 2-fluoro, 3-fluoro, 4-fluoro, 2-bromo, 3-bromo, 4-bromo, 2-methyl, 3-methyl, 4-methyl, 2-trifluoromethyl, 3-trifluoromethyl, 4-trifluoromethyl, 2-methoxy, 3-methoxy, 4-methoxy, 2-trifluoromethoxy, 3-trifluoromethoxy, 4-trifluoromethoxy, 2-cyano, 3-cyano, 4-cyano, 2,3-dichloro, 2,3-difluoro, 2,3-dibromo, 2,3-dimethyl, 2,3-dimethoxy, 2,3-bis(trifluoromethyl), 2,3bis-(trifluoromethoxy), 2,4-difluoro, 2,4-dichloro, 2,4-dibromo, 2,4-dimethyl, 2,4-dimethoxy, 2,4-bis(trifluoromethyl), 2,4-bis(trifluoromethoxy), 2,5-difluoro, 2,5-dichloro, 2,5-dibromo, 2,5-dimethyl, 2,5-dimethoxy, 2,5-bis(trifluoromethyl), 2,5-bis-(trifluoromethoxy), 3,4-difluoro, 3,4-dichloro, 3,4-dibromo, 3,4-dimethyl, 3,4-dimethoxy, 3,4-bis(trifluoromethyl), 3,4-bis(trifluoromethoxy), 3,5-difluoro, 3,5-dichloro, 3,5-dibromo, 3,5-dimethyl, 3,5-bis(trifluoromethyl), 3,5-bis(trifluoromethoxy), 2,3,4-trifluoro, 2,3,4-trichloro, 2,3,4-tribromo, 2,3,4-trimethyl, 2,3,4-trimethoxy, 2,3,4-tris(trifluoromethyl), 2,3,4-tris(trifluoromethoxy), 2,3,5-trifluoro, 2,3,5-trichloro, 2,3,5-tribromo, 2,3,5-trimethyl, 2,3,5-tris(trifluoromethyl), 2,3,5-tris(trifluoromethoxy), 2,4,5-trifluoro, 2,4,5-trichloro, 2,4,5-tribromo, 2,4,5-trimethyl, 2,4,5-trimethoxy, 2,4,5-tris(trifluoromethyl), 2,4,5-tris(trifluoromethoxy), 3,4,5-trifluoro, 3,4,5-trichloro, 3,4,5-tribromo, 3,4,5-trimethyl, 3,4,5-trimethoxy, 3,4,5-tris(trifluoromethyl), 3,4,5-tris(trifluoromethoxy), 2,3,4,5-tetrafluoro, 2,3,4,5-tetrachloro, 2,3,4,5-tetrabromo, 2,3,4,5-tetramethyl, 2,3,4,5-tetramethoxy, 2,3,4,5-tetra(trifluoromethyl), and 2,3,4,5-tetra(tetrafluoromethoxy.
Typical phenyl substituents, where both positions on the phenyl ring adjacent to the bond to the cyclopropyl rings are substituted include but are not limited to 2,6-dichloro, 2,3,6-trichloro, 2,4,6-trichloro, 2,6-difluoro, 2,3,6-trifluoro, 2,4,6-trifluoro, 2,6-dibromo, 2,3,6-tribromo, 2,4,6-tribromo 2,3,4,6-tetrachloro, 2,3,5,6-tetrachloro, 2,3,4,5,6-pentachloro, 2,3,4,6-tetrabromo, 2,3,5,6-tetrabromo, 2,3,4,5,6-pentabromo, 2,3,4,6-tetrafluoro, 2,3,5,6-tetrafluoro, 2,3,4,5,6-pentafluoro, 2,6-dimethyl, 2,3,6-trimethyl, 2,4,6-trimethyl, 2,6-dimethoxy, 2,3,6-trimethoxy, 2,4,6-trimethoxy, 2,6-diethoxy, 2,3,6-triethoxy, 2,4,6-triethoxy, 2,3,4,6-tetramethyl, 2,3,5,6-tetramethyl, 2,3,4,5,6-pentamethyl, 2,3,4,6-tetramethoxy, 2,3,5,6-tetramethoxy, 2,3,4,5,6-pentamethoxy, 2,3,4,6-tetraethoxy, 2,3,5,6-tetraethoxy, 2,3,4,5,6-pentaethoxy, 2,6-dicyano, 2,3,6-tricyano, 2,4,6-tricyano, 2,6-dinitro, 2,6-diphenyl, 2,6-diphenoxy, 2,6-dibenzyl, 2,6-bis(trifluoromethyl), 2,3,6-tris(trifluoromethyl), 2,4,6-tris-(trifluoromethyl), 2,3,4,6-tetra(trifluoromethyl), 2,3,5,6-tetra(trifluoromethyl), 2,3,4,5,6-penta(trifluoromethyl), 2,6-bis-(trifluoromethoxy), 2,3,6-tris(trifluoromethoxy), 2,4,6-tris(trifluoromethoxy), 2,3,4,5-tetra(trifluoromethoxy), 2,3,4,6-tetra-(trifluoromethoxy), 2,3,5,6-tetra(trifluoromethoxy), 2,3,4,5,6-penta(trifluoromethoxy), 2-bromo-6-chloro, 2-bromo-6-fluoro, 2-bromo-6-(trifluoromethyl), 2-bromo-6-methyl, 2-bromo-6-methoxy, 2-bromo-6-(trifluoromethoxy), 2-bromo-6-cyano, 2-chloro-6-fluoro, 2-chloro-6-(trifluoromethyl), 2-chloro-6-methyl, 2-chloro-6-methoxy, 2-chloro-6-trifluoromethoxy), 2-chloro-6-cyano, 2-fluoro-6-(trifluoromethyl), 2-fluoro-6-methyl, 2-fluoro-6-methoxy, 2-fluoro-6-(trifluoromethoxy), 6-cyano-2-fluoro, 2-methyl-6-(trifluoromethyl), 6-methoxy-2-methyl, 2-methyl-6-(trifluoromethoxy), 6-cyano-2-methyl, 3,6-dichoro-2-fluoro, 3-chloro-2,6-difluoro, 4-chloro-2,6-difluoro, 2-bromo-3,6-dichoro, 2,3-dibromo-6-chloro, 3-chloro-2,6-dibromo, 2,6-dichloro-3-fluoro, 2,3-dichloro-6-fluoro, 2-chloro-3,6-difluoro, 3-bromo-2,6-dichloro, 3-bromo-2,6-fluoro, 3-bromo-6-chloro-2-fluoro, 2-bromo-5-chloro-6-fluoro, 2,6-dibromo-3-fluoro, 2,5-dibromo-6-fluoro, 2,4-dichloro-6-fluoro, 2,6-chloro-4-fluoro, 2,4,-dichloro-6-bromo, 2,6-dichloro-4-bromo, 2,4-difluoro-6-chloro, 2,4-difluoro-

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