Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Nitrogen containing other than solely as a nitrogen in an...
Reexamination Certificate
2000-06-30
2004-05-04
Padmanabhan, Sreeni (Department: 1621)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Nitrogen containing other than solely as a nitrogen in an...
C514S456000, C514S464000, C514S519000, C514S520000, C514S619000, C549S049000, C549S058000, C549S505000, C549S506000, C549S366000, C549S441000, C558S389000, C564S074000, C564S133000, C564S134000, C564S164000, C564S165000
Reexamination Certificate
active
06730705
ABSTRACT:
The invention relates to new alkoximinoacetic acid amides, a process for their preparation and their use as agents for combating pests.
New compounds of the general formula (I)
in which
A represents a single bond or optionally substituted alkylene,
Q represents oxygen or sulphur,
R
1
represents in each case optionally substituted cycloalkyl, cycloalkenyl, aryl or heterocyclyl,
R
2
and R
3
are identical or different and in each case represent hydrogen or in each case optionally substituted alkyl, alkenyl, alkinyl or cycloalkyl, and
R
4
represents in each case optionally substituted cycloalkyl, cycloalkenyl, aryl or heterocyclyl,
have been found.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkinyl, including when linked with heteroatoms, such as in alkoxy, alkylthio or alkylamino, are in each case straight-chain or branched.
Halogen in general 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 or phenanthryl, preferably phenyl or naphthyl, in particular phenyl.
Heterocyclyl represents saturated or unsaturated and aromatic, cyclic compounds in which at least one ring member is a heteroatom, i.e. an atom which differs from carbon. If the ring contains several heteroatoms, these can be identical or different. Heteroatoms are preferably oxygen, nitrogen or sulphur.
Cyclic compounds optionally form a polycyclic ring system together with further carbocyclic or heterocyclic fused-on or bridged rings. Mono- or bicyclic ring systems, in particular mono- or bicyclic aromatic ring systems, are preferred.
Cycloalkyl represents saturated carbocyclic, cyclic compounds which optionally form a polycyclic ring system with further carbocyclic, fused-on or bridged rings.
Cycloalkenyl represents carbocyclic, cyclic compounds which contain at least one double bond and optionally form a polycyclic ring system with further carbocyclic, fused-on or bridged rings.
Finally, it has been found that the new alkoximinoacetic acid amides of the general formula (I) have a very potent fungicidal action.
Where appropriate, the compounds according to the invention are in the form of mixtures of various possible isomeric forms, in particular stereoisomers, such as, for example, E and Z, threo and erythro and optical isomers. Both the E and the Z isomers and also the threo and erythro isomers as well as the optical isomers and any desired mixtures of these isomers are described and claimed.
The invention preferably relates to compounds of the formula (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 chosen from the following list:
halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl or 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 parts;
cycloalkyl having 3 to 6 carbon atoms;
and substituted aryl or heterocyclyl, in each case optionally mono- or poly-substituted in an identical or different manner by
halogen, cyano and/or straight-chain or branched alkyl having 1 to 4 carbon atoms
and/or straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms
and/or straight-chain or branched alkoxy or alkylthio having 1 to 4 carbon atoms
and/or straight-chain or branched halogenoalkoxy or halogenoalkylthio having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms
and/or in each case divalent alkylene or dioxyalkylene having in each case 1 to 6 carbon atoms and optionally mono- or polysubstituted in an identical or different manner by halogen and/or straight-chain or branched alkyl having 1 to 4 carbon atoms and/or 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, in each case optionally mono- or polysubstituted by identical or different substituents, the possible substituents preferably being chosen from the following list:
halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl or 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, alkyicarbonyloxy, alkoxycarbonyt, alkylsulphonyloxy, hydroximinoalkyl or alkoximinoalkyl having in each case 1 to 8 carbon atoms in the individual alkyl parts;
in each case divalent alkylene or dioxyalkylene having in each case 1 to 6 carbon atoms and in each case optionally mono- or polysubstituted in an identical or different manner by halogen and/or straight-chain or branched alkyl having 1 to 4 carbon atoms and/or straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms;
cycloalkyl having 3 to 6 carbon atoms;
and substituted aryl, aryloxy, arylthio, arylalkyl, arylalkyloxy, arylalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylalkyl, heterocyclylalkyloxy or heterocyclylalkylthio, in each case optionally mono- or polysubstituted in an identical or different manner by
halogen, cyano and/or straight-chain or branched alkyl having 1 to 4 carbon atoms
and/or straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms
and/or straight-chain or branched alkoxy or alkylthio having 1 to 4 carbon atoms
and/or straight-chain or branched halogenoalkoxy or halogenoalkylthio having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms
and/or in each case divalent alkylene or dioxyalkylene having in each case 1 to 6 carbon atoms and optionally mono- or polysubstituted in an identical or different manner by halogen and/or straight-chain or branched alkyl having 1 to 4 carbon atoms and/or straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,
R
2
represents hydrogen, or represents alkyl having 1 to 4 carbon atoms, alkenyl or alkinyl having in each case 2 to 4 carbon atoms or cycloalkyl having 3 to 6 carbon atoms, in each case optionally mono- or polysubstituted in an identical or different manner by halogen, cyano, hydroxyl, amino, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-alkylsulphinyl or C
1
-C
4
-alkylsulphonyl (which can in each case be optionally substituted by halogen) or by op
Hänssler Gerd
Seitz Thomas
Stenzel Klaus
Bayer Aktiengesellschaft
Norris McLaughlin & Marcus P.A.
Padmanabhan Sreeni
LandOfFree
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