Unsaturated oxime ethers and their use as fungicides

Details Unsaturated oxime ethers and their use as fungicides Unsaturated oxime ethers and their use as fungicides

2000-08-08

2001-10-16

Richter, Johann (Department: 1621)

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

Organic compounds

Amino nitrogen containing

C558S256000, C560S035000, C562S440000, C504S147000, C544S335000, C544S336000, C546S329000, C548S214000

Reexamination Certificate

active

06303818

ABSTRACT:

The present invention relates to certain oxime ether compounds, compositions containing these compounds, and methods for controlling fungi by the use of a fungitoxic amount of the compounds or compositions.
Compounds having certain oxime ether structures are disclosed in U.S. Pat. No.5,055,471 are useful as fungicides. We have discovered new oxime ether structures which possess a substituted alkenyl moiety which possess broad spectrum fungicidal properties.
The oxime ethers of the present invention have the Formula (I)
wherein X is N or CH; Y is O, S, or NR
6;
A is hydrogen, halo, cyano, (C
1
-C
12
)alkyl, or (C
1
-C
12
)alkoxy;
R
1
and R
6
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, (C
2
-C
8
)alkenyl, halo(C
2
-C
8
)alkenyl, (C
2
-C
8
)alkynyl, halo(C
2
-C
8
)alkynyl, cyano, aryl, aralkyl, heterocyclic, or heterocyclic(C
1
-C
4
)alkyl;
R
3
is hydrogen or (C
1
-C
4
)alkyl;
R
4
and R
5
are independently hydrogen, (C
1
-C
4
)alkyl, aryl, aralkyl, aryl(C
2
-C
8
)alkenyl, aryl(C
2
-C
8
)alkynyl, heterocyclic, or heterocyclic(C
1
-C
4
)alkyl, wherein in each aryl, aralkyl, aryl(C
2
-C
8
)alkenyl, aryl(C
2
-C
8
)alkynyl, heterocyclic or heterocyclic(C
1
-C
4
)alkyl 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 ethylenic bond, in Formula I, are both substituted and wherein if one of R
4
and R
5
is hydrogen or (C
1
-C
4
)alkyl then the other of R
4
and R
5
is other than hydrogen or (C
1
-C
4
)alkyl.
The aforementioned (C
1
-C
4
)alkyl, (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 substituted with up to three substituents selected from the group consisting of nitro, halomethyl, (C
1
-C
4
)alkoxycarbonyl, and cyano.
The term alkyl includes both branched and straight chain alkyl groups containing from 1 to 12 carbon atoms. Typical alkyl groups include for example, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, isobutyl, t-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, isooctyl, nonyl, decyl, undecyl, and dodecyl. The term haloalkyl refers to an alkyl group substituted with 1 to 3 halogens.
The term alkenyl refers to an ethylenically unsaturated hydrocarbon group, straight or branched, having a chain length of 2 to 8 carbon atoms and 1 or 2 ethylenic bonds. The term haloalkenyl refers to an alkenyl group substituted with 1 to 3 halogen atoms. The term alkynyl refers to an unsaturated hydrocarbon group, straight or branched, having a chain length of 2 to 12 carbon atoms and I or 2 acetylenic bonds.
The term aryl includes phenyl and naphthyl which maybe substituted with up to five substituents independently selected from halogen, cyano, nitro, trihalomethyl, phenyl, phenoxy, (C
1
-C
4
)alkyl, (C
1
-C
4
)alkoxy, (C
1
-C
4
)alkylthio, (C
1
-C
4
)alkylsulfoxide, halo(C
1
-C)alkyl, halo(C
1
-C
4
)alkoxy, halo(C
2
-C
8
)alkenyl, halo(C
2
-C
8
)alkynyl, heterocyclic, phenoxy, (C
1
-C
4
)alkylamino, (C
1
-C
4
)dialkylamino, and phenyl. Each aryl may be substituted with one or more substituents independently selected from halogen, cyano, trihalomethyl, phenyl, phenoxy(C
1
-C
4
)alkyl, (C
1
-C
4
)alkoxy and (C
1
-C
4
)alkylthio, Typical phenyl substituents, where both positions on the phenyl ring adjacent to the ethylenic bond, in Formula I, are substituted include, for example 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-triethoxy, 2,3,6-triethoxy, 2,4,6-triethoxy, 2, 3,4,6-tetramethyl, 2,3,5,6-tetramethyl, 2,3,4,5,6-pentaxiiethyl, 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-diphenyl, 2,6-diphenoxy, 2,6-dibenzyl, 2,6-bis(trifluoromethyl), 2,3,6-tris-(trifluoromethyl), 2,4,6-tris-(trifiuoromethyl), 2,3,4,5-tetra-(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-tri-(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-(trifluoromethoxy), 2-bromo-6-cyano, 2-chloro-6-fluoro, 2-chloro-6-(trifluoromethyl), 2-chloro-6-methyl, 2-chloro-6-(trifluoromethoxy), 2-chloro-6-cyano, 2-fluoro-6-(trifluoromethyl), 2-fluoro-6-methyl 2-fluoro-6-(trifluoromethoxy).
The term heterocyclic refers to a substituted 6 membered unsaturated ring selected from 3-pridinyl, 4-pyridinyl, 5-pyrimidinyl, 3-pyridazinyl or a 5 membered unsaturated ring selected from 3-thienyl, 3-furyl, 3-pyrrolyl, 4-isoxazolyl, 4-isothiazolyl and 4-pyrazolyl wherein both the positions on the heterocyclic ring adjacent to the ethylenic bond in Formula I are substituted and the ring is substituted with from 2 to 4 substituents independently selected from (C
1
-C
4
) alkyl, (C
3
-C
7
)cycloalkyl, trihalomethyl, trihalomethoxy, halogen, cyano, (C
1
-C
4
)alkoxycarbonyl, nitro, phenyl, and phenoxy.
The term arylalkyl is used to describe a group wherein the alkyl chain is from 1 to 10 carbon atoms and can be a branched or straight chain, preferably a straight chain, with the aryl portion as defined above, forming a terminal portion of the arylalkyl moiety. Typical arylalkyl moieties are optionally substituted benzyl, phenethyl, phenpropyl, and phenbutyl moieties. Typical benzyl moieties wherein both positions on the phenyl ring, adjacent to the methylene which is bonded to the ethylenic bond in formula I, are substituted include, for example 2,6-dichlorobenzyl, 2,3,6-trichlorobenzyl, 2,4,6-trichlorobenzyl, 2,6-difluorobenzyl, 2,3,6-fluorobenzyl, 2,4,6-trifluorobenzyl, 2,6-bis(trifluoromethyl)benzyl, 2,3,6-tris(trifluoromethyl)benzyl, 2,4,6-tris(trifluoromethyl)benzyl, 2,3,4,6-tetrachlorobenzyl, 2,3,5,6-tetrachlorobenzyl, 2,3,4,5,6-pentachlorobenzyl, 2,3,4,6-tetrabromobenzyl, 2,3,5,6-tetrabromobenzyl, 2,3,4,5,6-pentabromobenzyl, 2,3,4,6-tetrafluorobenzyl, 2,3,5,6-tetrafluorobenzyl, and 2,3,4,5,6-pentafluorobenzyl. Typical phenethyl moieties wherein both positions on the phenyl ring, adjacent to the ethyl moiety which is bonded to the ethylenic bond in Formula I, are substituted include, for example 2-(2,6-dichlorophenyl)ethyl, 2-(2,3,6-trichlorophenyl)ethyl, 2-(2,4,6-trichlorophenyl)-ethyl, 2-(2,6-difluorophenyl)ethyl, 2-(2,3,6-trifluorophenyl)ethyl, 2-(2,4,6-trifluorophenyl)ethyl, 2-(2,6-dimethylphenyl)ethyl, 2-(2,3,6-trimethylphenyl)-ethyl, 2-(2,4,6-trimethylphenyl)ethyl, 2-(2,6-bis-(trifiluoromethyl)-phenyl)ethyl, 2-(2,3,6-tris(trifluoromethyl)-phenyl)ethyl 2-(2,4,6-tris(trifluoromethyl)-phenyl)ethyl, 2-(2,6-dimethoxyphenyl)ethyl, 2-(2,3,6-trimethoxy-phenyl)ethyl, and 2-(2,4,6-trimethoxyphenyl)ethyl. Typical phenpropyl moieties wherein both positions on the phenyl ring, adjacent to the propyl moiety which is bonded to ethylenic bond in Formula I, are substituted include, for example 3(2,6-dichlorophenyl)propyl, 3-(2,3,6-trichlorophenyl)propyl, 3-(2,4,6-trichlorophenyl)propyl, 3-(2,6-difluorophenyl)propyl, 3-(2, 3,6-trifluorophenyl)-propyl, 3-(2,4,6-trifluorophenyl)propyl, 3-(2,6-dimethylphenyl)propyl, 3-(2,3,6-trimethyl-phenyl)propyl, 3-(2,4,6-trimethylphenyl)propyl and 3-(2,6-bis(trifluoromethyl)-phenyl)propyl. Typical phenbutyl moieties wherein both positions on the phenyl ring, adjacent to the butyl moiety which is bonded to ethylenic bond in Formula I, are substituted include, for example 4-(2,6-di-chlorophenyl)butyl, 4-(2,3,6-trichlorophenyl)butyl, 4-

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