Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Nitrogen containing other than solely as a nitrogen in an...
Reexamination Certificate
1999-05-12
2001-11-06
Raymond, Richard L. (Department: 1611)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Nitrogen containing other than solely as a nitrogen in an...
C514S620000, C564S074000, C564S164000
Reexamination Certificate
active
06313173
ABSTRACT:
TECHNICAL FIELD OF THE INVENTION
The invention relates to novel glyoxylic acid amides, to a plurality of processes for their preparation and to their use as pesticides.
DETAILED DESCRIPTION OF THE INVENTION
Novel compounds of the general formula (I) have been found
in which
A represents optionally substituted branched alkanediyl, represents optionally substituted straight-chain or branched alkanediyl which is interrupted by one or more hetero atoms, represents optionally substituted cycloalkanediyl or represents optionally substituted phenylene,
Q represents oxygen or sulphur,
R
1
represents in each case optionally substituted cycloalkyl, cycloalkenyl, aryl or heterocyclyl,
R
1
represents aryl having a fused-on cycloalkyl ring where both the aryl moiety and the cycloalkyl moiety optionally carry further substituents, or
R
1
represents optionally substituted benzoheterocyclyl having one, two or three hetero atoms, or
R
1
represents a tricycle
in which
G
1
and G
2
independently of one another each represent a single bond, alkanediyl, alkenediyl, oxygen, sulphur, —NH—, —N(alkyl)- or carbonyl,
G
3
and G
4
independently of one another each represent nitrogen or a grouping
and
Y
1
, Y
2
, Y
3
, Y
4
, Y
5
, Y
6
, Y7 and Y8 independently of one another each represent hydrogen, halogen, cyano, nitro, in each case optionally substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkylsulphinyl, alkylsulphonyl or cycloalkyl,
R
2
represents hydroxyl, amino or in each case optionally substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylamino, dialkylamino, arylamino, cycloalkyl, cycloalkenyl, cycloalkoxy, cycloalkenyloxy, cycloalkylamino, aryl, arylalkyl, arylalkoxy or heterocyclyl or one of the following groupings:
in which
Q
1
and Q
2
independently of one another each represent oxygen or sulphur,
R
5
represents hydrogen or optionally substituted alkyl or aryl,
R
6
represents optionally substituted alkyl or aryl,
R
7
represents hydrogen or optionally substituted alkyl or aryl,
R
8
represents optionally substituted alkyl or aryl, or
R
7
and R
8
together with the linking nitrogen atom represent an optionally alkyl-substituted heterocyclic ring,
R
9
represents optionally substituted alkyl, dialkylamino, saturated heterocyclyl which is attached via nitrogen, or represents aryl,
R
3
represents hydrogen or in each case optionally substituted alkyl, alkenyl, alkinyl or cycloalkyl,
R
4
represents in each case optionally substituted cycloalkyl, cycloalkenyl, aryl or heterocyclyl.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkinyl, are in each case straight-chain or branched, including in combination with hetero atoms, such as in alkoxy, alkylthio or alkylamino. If an alkyl or alkanediyl chain is interrupted by more than one hetero atom, these are identical or different. If a hetero atom represents nitrogen, it is optionally substituted by alkyl, preferably alkyl having 1 to 4 carbon atoms. If an alkyl or alkanediyl chain is interrupted by more than one oxygen atom, these oxygen atoms are not directly adjacent. Hetero atoms may be positioned both at the beginning, in the middle or at the end of the chain.
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
Aryl represents aromatic, mono- or polycyclic hydrocarbon rings, such as, for example, phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or naphthyl, in particular phenyl.
Heterocyclyl represents saturated or unsaturated, and also aromatic, cyclic compounds in which at least one ring member is a hetero atom, i.e. an atom which is different from carbon. If the ring contains a plurality of hetero atoms, these may be identical or different. Preferred hetero atoms are oxygen, nitrogen or sulphur. If the ring contains a plurality of oxygen atoms, these oxygen atoms are not directly adjacent.
If appropriate, cyclic compounds form, together with other carbocyclic or heterocyclic fused-on or bridged rings, a polycyclic ring system. Preference is given to mono- or bicyclic ring systems, in particular to mono- or bicyclic aromatic ring systems.
Cycloalkyl represents saturated carbocyclic cyclic compounds which may, if appropriate, form a polycyclic ring system together with other carbocyclic fused-on or bridged rings.
Cycloalkenyl represents carbocyclic cyclic compounds which contain at least one double bond and which may, if appropriate, form a polycyclic ring system together with other carbocyclic fused-on or bridged rings.
Benzoheterocyclyl represents a heterocyclic ring having a fused-on benzene ring.
Finally, it has been found that the novel glyoxylic acid amides of the general formula (I) have very strong fungicidal activity.
If appropriate, the compounds according to the invention are present as mixtures of various possible isomeric forms, in particular of stereoisomers, such as, for example, E and Z, cis or trans, threo and erythro, and also optical isomers. Both the E and the Z isomers, and also the threo and erythro, and also the optical isomers, and any mixtures of these isomers are described and claimed.
The invention preferably provides compounds of the formula (I) in which
A represents branched alkanediyl having 3 to 6 carbon atoms and being optionally mono- to trisubstituted by identical or different substituents, represents straight-chain or branched alkanediyl having 2 to 6 chain members and being mono- to trisubstituted by identical or different substituents and interrupted by one or two hetero atoms, where the possible substituents are in each case preferably selected from the list below:
halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl;
in each case straight-chain or branched alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms;
in each case straight-chain or branched alkenyl or alkenyloxy having in each case 2 to 6 carbon atoms;
in each case straight-chain or branched halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
in each case straight-chain or branched halogenoalkenyl or halogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy, hydroximinoalkyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties;
cycloalkyl having 3 to 6 carbon atoms;
and aryl or heterocyclyl, each of which is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of
halogen, cyano and straight-chain or branched alkyl having 1 to 4 carbon atoms
and straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms
and straight-chain or branched alkoxy or alkylthio having 1 to 4 carbon atoms
and straight-chain or branched halogenoalkoxy or halogenoalkylthio having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms
and in each case doubly attached alkylene or dioxyalkylene having in each case 1 to 6 carbon atoms and being optionally mono- or polysubstituted by
identical or different substituents selected from the group consisting of halogen and straight-chain or branched alkyl having 1 to 4 carbon atoms
and straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, or
A represents cycloalkane-1,2-diyl having 3 to 8 carbon atoms or o-phenylene, each of which is optionally mono- to trisubstituted by identical or different substituents, possible substituents being the substituents mentioned above for A, and also alkyl having 1 to 6 carbon atoms and halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 halogen atoms,
Q represents oxygen or sulphu
Seitz Thomas
Stenzel Klaus
Bayer Aktiengesellschaft
Norris & McLaughlin & Marcus
Raymond Richard L.
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