Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Nitrogen containing other than solely as a nitrogen in an...
Reexamination Certificate
1999-12-08
2002-08-27
Shah, Mukund J. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Nitrogen containing other than solely as a nitrogen in an...
C514S619000, C564S074000, C564S138000, C564S168000
Reexamination Certificate
active
06441043
ABSTRACT:
FIELD OF THE INVENTION
The invention relates to novel glyoxylic acid amides, to a plurality of processes for their preparation and to their use for controlling pests.
BACKGROUND OF THE INVESTIGATION
It is already known that certain glyoxylic acid amides of a constitution similar to that of the compounds described below have fungicidal properties (compare, for example, WO 9623763, WO 9631464 or WO 9714673). However, the fungicidal activity of these compounds is in many cases unsatisfactory.
DETAILED DESCRIPTION OF THE INVENTION
Novel compounds of the general formula (I) have been found
in which
A represents optionally substituted, unbranched alkanediyl,
Q represents oxygen or sulphur,
R
1
represents in each case optionally substituted cycloalkyl, cycloalkenyl, aryl or heterocyclyl, or
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
, Y5, Y
6
, Y
7
and Y
8
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.
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.
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 unbranched alkanediyl having 2 to 6 carbon atoms which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen, hydroxyl, straight-chain or branched, alkoxy, having 1 to 6 carbon atoms and cycloalkyl having 3 to 6 carbon atoms,
Q represents oxygen o r sulphur,
R
1
represents cycloalkyl, cycloalkenyl, aryl or heterocyclyl, each of which is optionally mono- to pentasubstituted, where the possible substituents are preferably selected from the list below:
halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl;
in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 8 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 halogenoalkyl, 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, aryloxy, arylthio, arylalkyl, arylalkyloxy, arylalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylalkyl, heterocyclylalkyloxy or heterocyclylalkylthio, 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
R
1
represents phenyl or naphthyl having a fused-on cycloalkyl ring having 3 to 10 ring members, where the cycloalkyl moiety is optionally substituted by 1 to 4 alkyl chains having in each case 1-4 carbon atoms and where the phenyl or naphthyl moiety optionally carries the substituents mentioned for Y
1
to Y
8
,or
R
1
represents benzoheterocyclyl having 3 to 12 ring members in the heterocyclyl moiety and one, two or three hetero atoms and being optionally mono- or polysubstituted by identical or different substituents, where pr
Seitz Thomas
Stenzel Klaus
Bayer Aktiengesellschaft
Gil Joseph C.
Harmuth Raymond J.
McKenzie Thomas
Shah Mukund J.
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