Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1999-01-11
2001-05-01
McKane, Joseph K. (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C549S074000, C549S491000, C560S129000, C560S251000, C560S252000, C560S256000, C548S491000, CD22S122000
Reexamination Certificate
active
06225334
ABSTRACT:
The invention relates to novel glyoxylic acid derivatives, to a process for their preparation and to their use as pesticides.
This invention provides novel compounds of the general formula (I)
in which
A represents a single bond or optionally substituted alkylene,
Q represents oxygen or sulphur,
n represents a number 0 or 1,
R
1
represents cycloalkyl, cycloalkenyl, aryl or heterocyclyl, each of which is optionally substituted,
R
2
, in the case that n represents the number 1, represents one of the groupings below:
or, in the case that n represents the number 0,
R
2
represents hydroxyl, amino, or represents alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylamino, dialkylamino, arylamino, cycloalkyl, cycloalkenyl, cycloalkoxy, cycloalkenyloxy, cycloalkylamino, aryl, arylalkyl, arylalkoxy or heterocyclyl, each of which is optionally substituted,
or, in the case that n represents the number 0 and
R
1
represents optionally substituted benzoheterocyclyl which is attached on the benzene ring and has one, two or three heteroatoms (but at most one heteroatom representing oxygen), or
R
1
represents a tricycle
in which
G
1
and G
2
independently of one another 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
, Y
7
and Y
8
independently of one another each represent hydrogen, halogen, cyano, nitro, or represent alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkylsulphinyl, alkylsulphonyl or cycloalkyl, each of which is optionally substituted, or
R
2
then represents hydroxyl, amino or represents alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylamino, dialkylamino, arylamino, cycloalkyl, cycloalkenyl, cycloalkoxy, cycloalkenyloxy, cycloalkylamino, aryl, arylalkyl, arylalkoxy or heterocyclyl, each of which is optionally substituted, or represents one of the groupings below:
Q
1
and Q
2
independently of one another each represent oxygen or sulphur,
R
5
represents hydrogen or represents 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 aryl,
R
3
represents hydrogen or represents alkyl, alkenyl, alkinyl or cycloalkyl, each of which is optionally substituted,
R
4
represents cycloalkyl, cycloalkenyl, aryl or heterocyclyl, each of which is optionally substituted.
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 a in combination with heteroatoms, such as an 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, annular compounds in which at least one ring member is a heteroatom, i.e. an atom different from carbon. If the ring contains a plurality of heteroatoms, these may be identical or different. Preferred heteroatoms are oxygen, nitrogen or sulphur.
If appropriate, annular 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 annular compounds which may, if appropriate, form a polycyclic ring system together with other carbocyclic fused-on or bridged rings.
Cycloalkenyl represents carbocyclic annular compounds which contain at least one double bond and which may, if appropriated, form a polycyclic ring system together with other carbocyclic fused-on or bridged rings.
Preference is given to compounds of the general formula (I-I)
in which
A represents a single bond or optionally substituted alkylene,
Q represents oxygen or sulphur,
R
1
represents cycloalkyl, cycloalkenyl, aryl or heterocyclyl, each of which is optionally substituted,
R
2
represents one of the groupings below:
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 aryl,
R
3
represents hydrogen or represents alkyl, alkenyl, alkinyl or cycloalkyl, each of which is optionally substituted,
R
4
represents cycloalkyl, cycloalkenyl, aryl or heterocyclyl, each of which is optionally substituted.
The invention preferably provides compounds of the formula (I-I) in which
A represents a single bond or represents alkylene having 1 to 6 carbon atoms which is optionally mono- or polysubstituted by identical or different substituents, the possible substituents preferably being selected from the list below:
halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl;
alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms and being in each case straight-chain or branched;
alkenyl or alkenyloxy having in each case 2 to 6 carbon atoms and being 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 and being 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 and being 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 and being in each case straight-chain or branched;
cycloalkyl having 3 to 6 carbon atoms;
and also 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 i 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 alkylene or dioxyalkylene having in each case 1 to 6 carbon atoms and being in each case doubly attached and 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,
Q represents oxygen or sulphur,
R
1
represents aryl, cycloalkyl or cycloalkenyl having 3 to 7 carbon atoms, or heterocyclyl having 3 to 12 ring members, each of which is optionally mono- or polysubstituted by identical or different substituents, the possible substituents preferably being selected from the list below:
halogen, cyano, nitro, amino,
Seitz Thomas
Stenzel Klaus
Wachendorff-Neumann Ulrike
Bayer Aktiengesellschaft
McKane Joseph K.
Norris & McLaughlin & Marcus
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