Aromatic compounds

Details Aromatic compounds Aromatic compounds

1995-06-07

2002-03-12

Raymond, Richard L. (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

C514S349000, C514S357000, C514S438000, C514S448000, C514S450000, C514S452000, C514S465000, C514S466000, C514S470000, C544S058100, C546S300000, C546S335000, C549S072000, C549S077000, C549S355000, C549S362000, C549S365000, C549S442000, C549S466000, C549S467000

Reexamination Certificate

active

06355634

ABSTRACT:

The present invention relates to oxime ethers of the general formula
in which R
1
is C
1-4
alkyl, (Y—X) is CH
2
═, C
1-2
alkylthio-CH═ or C
1-2
alkyl-ON═ and Z is an aldimino or ketimino group, namely in particular a group
in which R
2
is hydrogen, C
1-4
alkyl, C
1-4
haloalkyl, C
3-6
cycloalkyl, C
2-4
alkenyl, C
2-4
alkynyl, C
1-2
alkoxymethyl, C
1-2
alkylthiomethyl, C
1-4
alkylsulfonyl, C
1-3
alkoxy, C
1-3
alkylthio or cyano, and R
3
is C
1-6
alkyl, aryl-C
1-4
alkyl, heteroaryl-C
1-4
alkyl, C
2-12
alkenyl, aryl-C
2-4
alkenyl, aryloxy-C
1-4
alkyl, heteroaryloxy-C
1-4
alkyl, heteroaryl-C
2-4
alkenyl, C
3-6
cycloalkyl, aryl, heteroaryl, C
2-5
alkanoyl, aroyl or heteroaroyl, or R
2
and R
3
together with the carbon atom to which they are bonded form a substituted or unsubstituted four- to seven-membered saturated or unsaturated ring which may contain an oxygen atom, sulfur atom and/or nitrogen atom and which can additionally have a substituted or unsubstituted fused benzene ring.
The compounds according to the invention have fungicidal properties and are suitable as fungicidal active compounds, in particular for use in agriculture and horticulture.
The invention furthermore relates to a process for the preparation of the compounds according to the invention, to fungicidal compositions comprising such compounds as active substances, and to the use of such compounds and compositions for controlling fungi in agriculture and in horticulture.
In a narrower sense, the present invention relates to oxime ethers of the formula I in which R
1
is C
1-4
alkyl, (Y—X) is CH
2
═, C
1-2
alkylthio-CH═ or C
1-2
alkyl-ON═ and Z is an aldimino or ketimino group, namely in particular a group
in which R
2
is hydrogen, C
1-4
alkyl, C
1-4
haloalkyl or C
3-6
cycloalkyl and R
3
is C
1-6
alkyl, aryl-C
1-4
alkyl, heteroaryl-C
1-4
alkyl, C
2-6
alkenyl, aryl-C
2-4
alkenyl, heteroaryl-C
2-4
alkenyl, C
3-6
cycloalkyl, aryl, heteroaryl, C
2-5
alkanoyl, aroyl or heteroaroyl, or R
2
and R
3
together with the carbon atom to which they are bonded form a substituted or unsubstituted four- to seven-membered saturated ring which may contain an oxygen or sulfur atom and which can additionally have a substituted or unsubstituted fused benzene ring.
In the above formula I and in the following text, all groups “alkyl” and “alkenyl”, as such or as part of larger groups, for example heteroarylalkyl, can be straight-chain or branched, depending on the number of carbon atoms. Moreover, the alkenyl groups can have one or more double bonds. Halogen as a substituent is fluorine, chlorine, bromine or iodine, fluorine, chlorine and bromine being preferred. A haloalkyl group can have one or more identical or different halogen substituents. Aryl is understood as meaning, in particular, phenyl, naphthyl, phenanthryl or fluorenyl. Heteroaryl is a heterocyclic group having aromatic character and 1-3 hetero atoms N, O and/or S. Preferred rings are triazole or other five-membered and six-membered rings having 1-2 hetero atoms which, in turn, can additionally have one or two fused benzene rings. Examples which may mentioned and which do not represent any limitation but which, for the sake of simplicity, are referred to as “Het*group” in the following text, are pyrrolyl, pyridyl, furyl, thienyl, isoxazolyl, thiazolyl, pyrazinyl, pyridazinyl, imidazolyl, pyrimidinyl or triazolyl, or such a group with fused benzene, for example quinolinyl, quinoxalinyl, benzofuryl, benzothienyl or dibenzofuryl. This also applies analogously to “aryl” or “heteroaryl” as part of a larger group, for example aralkyl or heteroarylalkyl. Each of the aryl and heteroaryl groups can have one or more of the following substituents: halogen, C
1-4
alkyl, C
1-4
haloalkyl, aryl-C
1-4
alkyl, aryloxy-C
1-4
alkyl, C
2-4
alkenyl, aryl-C
2-4
alkenyl, C
2-4
alkynyl, C
3-6
cycloalkyl, aryl, C
1-4
alkoxy, C
1-4
haloalkoxy, aryl-C
1-4
alkoxy, C
1-4
alkylthio, aryloxy, cyano, nitro, C
2-4
haloalkenyl, C
2-4
haloalkynyl, C
2-4
alkenyloxy, C
2-4
haloalkenyloxy, C
3-4
alkynyloxy, C
3-4
haloalkynyloxy, cyclopropylmethoxy, cyclopropyl (unsubstituted or mono- to trisubstituted by halogen and/or methyl), cyanomethoxy (—OCH
2
CN), C
1-4
alkoxymethyl, C
1-4
alkylthiomethyl, C
1-4
alkylsulfinylmethyl, C
1-4
alkylsulfonylmethyl, arylthio, thiocyanato, C
1-4
alkoxyiminomethyl, C
1-4
alkanoyloxy and C
1-4
alkoxycarbonyl; and also a heteroaryl radical, a heteroaryl-C
1-4
alkyl radical, a heteroaryloxy-C
1-4
alkyl radical, a heteroaryl-C
2-4
alkenyl radical, a heteroaryl-C
1-4
alkoxy radical or a heteroaryloxy radical; the term heteroaryl being understood as meaning a representative of the abovementioned “Het*group”.
Almost all of the abovementioned substituents for aryl and heteroaryl groups can occur once to twice, preferably once, with the exception of C
1-4
alkyl, which is suitable as a substituent up to four times and halogen, which can occur up to three times, and, in the case of fluorine, also up to five times.
The preferred aryl radical is phenyl, whether on its own or as part of another substituent. Accordingly, benzoyl is preferred as aroyl.
C
2
Alkanoyl is acetyl. Haloalkyl is understood as meaning alkyl groups which are up to hexasubstituted by identical or different substituents from the series comprising F, Cl, Br and/or I. Examples of haloalkyl groups, on their own or as part of another substituent (such as haloalkoxy) are CH
2
Cl, CHCl
2
, CCl
3
, CHBr
2
, CH
2
CH
2
Cl, CHCl—CHCl
2
, CF
2
Cl, CH
2
I, CF
3
, C
2
F
5
, CF
2
—CF
2
Cl, CHF
2
, CH
2
F, CF
2
CHFCF
3
.
Trifluoromethyl, difluoromethoxy and trifluoromethoxy are preferred.
Moreover, the aryl groups (in particular phenyl) can carry a five-, six- or seven-membered saturated or unsaturated ring which has one or two oxygen atoms and which can be unsubstituted or mono- or polysubstituted by methyl, methoxy, phenyl, halogen, cyano or oxo (C═O). Examples of such groups are 5-benzofuryl, 6-benzodioxanyl and 5-( 1,3-benzodioxolyl).
In the event that R
2
and R
3
together with the carbon atom to which they are bonded form a substituted or unsubstituted ring as has been described in greater detail above, suitable substituents of the ring
are, in particular, C
1-6
alkyl or substituted or unsubstituted phenyl. It is also possible for the fused benzene ring which may be present to be substituted. Possible substituents of the phenyl group, or of the benzene ring itself, are those mentioned above in connection with the aryl group.
If asymmetric carbon atoms are present in the compounds of the formula I, the compounds exist in optically active form. Merely because of the presence of the aliphatic or imino double bond X═C and the imino double bond of the aldimino or ketimino group Z, the compounds exist in any case in the [E] or [Z] form. Atropisomerism can also occur. The formula I is intended to embrace all these isomeric forms which are possible as well as their mixtures, for example racemic mixtures and any desired [E/Z] mixtures.
In the case of the compounds of the formula I, R
1
is preferably methyl; and, independently thereof, (Y—X) is preferably methylene, methylthiomethylene (CH—SCH
3
) or methoxyimino (N-OCH
3
); compounds in which R
1
is methoxyimino are particularly preferred.
In the group (R
2
)(R
3
)C═N—, R
2
is preferably hydrogen, C
1-4
alkyl (in particular methyl or ethyl), C
1-4
haloalkyl (in particular trifluoromethyl) or C
3-6
cycloalkyl (in particular cyclopropyl), and R
3
is preferably substituted or unsubstituted phenyl, naphthyl (in particular &bgr;-naphthyl) or benzyl, possible substituents preferably being up to three identical or different halogen atoms (in particular fluorine, chlorine and/or bromine), C
1-4
alkyl groups (in particular methyl), C
1-4
haloalkyl groups (in particular trifluoromethyl), C
1-4
haloalkoxy groups (in particular trifluoromethoxy) and alkylenedioxy (in particular 3,4-methylenedioxy), or heteroaryl, in particular furyl which is unsubstituted or substituted by up to two methyl groups, or thienyl, pyr

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