Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
1999-09-10
2001-08-28
Shah, Mukund J. (Department: 1611)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C544S065000
Reexamination Certificate
active
06281209
ABSTRACT:
The invention relates to novel alkoximinomethyldioxazine derivatives, to a process for their preparation and to their use as fungicides, and also to novel intermediates and to a plurality of processes for their preparation.
It is already known that certain alkoximinomethyldioxazine derivatives of a constitution similar to those described below have fungicidal properties (compare, for example, WO-A 9504728). However, the fungicidal activity of these compounds, in particular at low application rates, leaves something to be desired. The novel alkoximinomethyldioxazine derivatives of the general formula (I) have now been found
in which
G represents a single bond, alkanediyl which is optionally interrupted by heteroatoms (but where the carbon atom to which R
1
is attached is always linked to a carbon atom of the alkanediyl chain) or a grouping
in which
R
3
represents in each case optionally substituted alkyl or cycloalkyl,
R
1
represents hydrogen, cyano or in each case optionally substituted alkyl or cycloalkyl,
R
2
represents hydrogen or in each case optionally substituted alkyl or cycloalkyl,
Z represents in each case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl and
E
1
, E
2
, E
3
and E
4
are identical or different and, independently of one another, each represents hydrogen, alkyl, halogenoalkyl or hydroxyalkyl, or
E
1
and E
2
or E
1
and E
3
or E
3
and E
4
together with the respective carbon atoms to which they are attached form a cycloaliphatic ring and
L
1
, L
2
, L
3
and L
4
, are identical or different and, independently of one another, each represents hydrogen, halogen, cyano, nitro, in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl.
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 heteroatoms, such as in alkoxy, alkylthio or alkylamino. If an alkyl or alkanediyl chain is interrupted by more than one heteroatom, these can be identical or different. If an alkyl or alkanediyl chain is interrupted by more than one oxygen atom, two oxygen atoms are not directly adjacent.
Halogen generally represents fluorine, chlorine, bromine or iodine, and also pseudohalogens, such as, for example, cyano, preferably fluorine, chlorine, bromine or cyano, in particular fluorine or chlorine.
Aryl represents aromatic, mono or polycyclic hydrocarbon rings, such as, for example, phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl of naphthyl, in particular phenyl.
Heterocyclyl represents saturated or unsaturated, and also aromatic, cyclic 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 can be identical or different. Preferred heteroatoms are oxygen, nitrogen or sulphur. If appropriate, the cyclic compounds form a polycyclic ring system together with other carbocyclic or heterocyclic, fused-on or bridged rings. 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, if appropriate, form a polycyclic ring system with other carbocyclic, fused-on or bridged rings.
Furthermore, it has been found that the novel alkoximinomethyldioxazine derivatives of the general formula (I) are obtained when (process a) 3-(1-hydroxyphenyl-1-alkoximinomethyl)dioxazines of the general formula
in which
E
1
, E
2
, E
3
, E
4
, L
1
, L
2
, L
3
and L
4
each as defined above, are reacted with an acrylic acid halide of the general formula (III)
in which
G, R
1
, R
2
and Z are each as defined above, and
X represents halogen,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor.
Finally, it has been found that the novel alkoximinomethyldioxazine derivatives of the general formula (I) have very strong fungicidal activity.
The compounds according to the invention may, if appropriate, be present as mixtures of different possible isomeric forms, in particular of stereoisomers, such as, for example, 20
E- and Z- or optical isomers. What is claimed are both the E and the Z isomers, the individual enantiomers, the racemates, and also any mixtures of these isomers.
The present application preferably provides alkoximinomethyldioxazin derivatives of the formula (I) in which
R
1
represents hydrogen, cyano or represents alkyl having 1 to 6 carbon atoms which is optionally substituted by halogen or alkoxy having 1 to 4 carbon atoms or represents cycloalkyl having 3 to 8 carbon atoms which is optionally substituted by halogen, alkyl or alkoxy having in each case 1 to 4 carbon atoms,
R
2
represents hydrogen or represents alkyl having 1 to 6 carbon atoms which is optionally substituted by halogen or alkoxy having 1 to 4 carbon atoms or represents cycloalkyl having 3 to 8 carbon atoms which is optionally substituted by halogen, alkyl or alkoxy having in each case 1 to 4 carbon atoms,
G represents a single bond, alkanediyl having 1 to 5 chain members which is optionally interrupted by one or two heteroatoms (but where the carbon atom to which R
1
is attached is always linked to a carbon atom of the alkanediyl chain) or a grouping
in which
R
3
represents hydrogen or represents alkyl having 1 to 6 carbon atoms, alkenyl having 2 to 6 carbon atoms or alkinyl having 2 to 6 carbon atoms, each of which is optionally substituted by halogen or alkoxy having 1 to 4 carbon atoms, or represents cycloalkyl having 3 to 8 carbon atoms which is optionally substituted by halogen, alkyl or alkoxy having in each case 1 to 4 carbon atoms or represents arylalkyl having 1 to 4 carbon atoms in the alkyl moiety, which is optionally substituted in the aryl moiety, where the substituents are selected from the list below:
halogen, cyano, nitro, formyl, carbamoyl, thiocarbamoyl, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms, in each case straight-chain or branched alkenyl, alkenyloxy or alkinyloxy having in each case 2 to 6 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkyl-sulphinyl 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 11 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, in each case doubly attached alkylene or dioxyalkylene having in each case 1 to 6 carbon atoms and being in each case optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen and straight or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,
Z represents alkyl having 1 to 8 carbon atoms, which is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen, cyano, hydroxyl, amino, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-alkylsulphinyl and C
1
-C
4
-alkylsulphonyl (each of which may optionally be substituted by halogen);
represents in each case optionally halogen-substituted alkenyl or alkinyl having in each case up to 8 carbon atoms; or represents phenyl, naphthyl, cycloalkyl or cycloalkenyl having in each case 3 to 8 carbon atoms and being in each case optionally mono- or polysubstituted by identical or different substituents, or represents heterocyclyl having 3 to 7 ring members, at least one of which represents oxygen, sulphur or nitrogen and another one or two of which optiona
Dutzmann Stefan
Gallenkamp Bernd
Gayer Herbert
Gerdes Peter
Heinemann Ulrich
Bayer Aktiengesellschaft
Gil Joseph C.
Liu Hong
Shah Mukund J.
Zurcher Jackie Ann
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