Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
1999-09-28
2001-07-17
Raymond, Richard L. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C544S065000, C544S314000, C544S315000, C544S317000
Reexamination Certificate
active
06262051
ABSTRACT:
The invention relates to novel methoximinomethyldioxazines, to a plurality of processes for their preparation and to their use as fungicides, and also to novel intermediates and to a process for their preparation.
It is already known that certain methoximinomethyldioxazines, of a similar constitution to those described below, have fungicidal properties (compare, for example, WO-A 9504728). However, the fungicidal activity of these compounds is unsatisfactory, in particular at low application rates.
This invention, accordingly, provides the novel compounds of the general formula (I)
in which
R represents in each case optionally substituted alkyl, arylalkyl, arylalkenyl, alkenyl, alkinyl or cycloalkyl,
Q represents oxygen, sulphur, —NH— or ,
where R
1
represents alkyl,
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 definition, 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.
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 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 methoximinomethyldioxazines of the general formula (I) are obtained when (process a) 4-halogeno-2-phenoxypyrimidines of the general formula (II)
in which
E
1
, E
2
, E
3
, E
4
, L
1
, L
2
, L
3
and L
4
are as defined above and
X represents halogen, in particular chlorine,
are reacted with a nucleophilic compound of the general formula
R—Q—H (III),
in which
R and Q are as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor,
or when (process b) alkylsulphonylpyrimidines of the general formula (IV)
in which
R and Q are as defined above and
R
1
represents alkyl or arylalkyl,
are reacted with a 3-(1-hydroxyphenyl-1-methoximinomethyl)dioxazine of the general formula
in which
E
1
, E
2
, E
3
, E
4
, L
1
, L
2
, L
3
and L
4
are as defined above,
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 methoximinomethyldioxazines of the general formula (I) have very strong fungicidal action.
If appropriate, the compounds according to the invention can be present as mixtures of different possible isomeric forms, in particular of stereoisomers, such as, for example, E and Z, or optical isomers. What is claimed are both the E and the Z isomers, the individual enantiomers, the racemates, and any mixtures of these isomers.
The present application preferably provides compounds of the formula (I) in which
R
represents methyl which is optionally mono- to trisubstituted by halogen and/or monosubstituted by cycloalkyl having 3 to 6 carbon atoms, where the cycloalkyl groups for their part are optionally substituted by 1 to 4 halogen atoms and/or 1 to 3 alkyl groups having 1 to 3 carbon atoms, or
represents alkyl, alkenyl or alkinyl having 2 to 12 carbon atoms, which is optionally monosubstituted to n-times substituted (where n represents the number of the hydrogen atoms of the unsubstituted hydrocarbon radical in question) by halogen and/or 1 to 2 alkoxy groups having 1 to 8 carbon atoms and/or 1 to 2 cycloalkyl groups having 3 to 6 carbon atoms (where the cycloalkyl groups for their part are optionally substituted by 1 to 4 halogen atoms and/or 1 to 3 alkyl groups having 1 to 3 carbon atoms), or
represents cycloalkyl having 3 to 8 carbon atoms which is optionally mono- to pentasubstituted by alkyl having 1 to 4 carbon atoms, halogen and/or alkoxy having 1 to 4 carbon atoms or
represents arylalkyl or arylalkenyl having 1 to 5 carbon atoms in the alkyl moiety and 2 to 5 carbon atoms in the alkenyl moiety, respectively, and 6 to 10 carbon atoms in the aryl moiety, which is optionally mono- to pentasubstituted in the aryl moiety, where the substituents of the aryl moiety are preferably selected from the list below:
halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl;
alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms;
alkenyl or alkenyloxy having in each case 2 to 6 carbon atoms;
halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
halogenoalkenyl or halogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms;
alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxy-carbonyl or alkylsulphonyloxy, 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 from the group consisting of halogen, 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;
cycloalkyl having 3 to 8 carbon atoms;
heterocyclyl or heterocyclyl-methyl having in each case 3 to 7 ring members, 1 to 3 of which are in each case identical or different heteroatoms—in particular nitrogen, oxygen and/or sulphur—or a grouping
in which
A
1
represents alkyl having 1 to 4 carbon atoms or cycloalkyl having 1 to 6 carbon atoms and
A
2
represents optionally cyano-, alkoxy-, alkylthio-, alkylamino-, dialkylamino- or phenyl-substituted alkyl having 1 to 4 carbon atoms, alkenyl or alkinyl having in each case 2 to 4 carbon atoms,
Q represents oxygen, sulphur, —NH—or
where R
1
represents alkyl having 1 to 4 carbon atoms,
E
1
, E
2
, E
3
and E
4
are identical or different and independently of one another represent hydrogen, alkyl or hydroxyalkyl having in each case 1 to 4 carbon atoms or halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, 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 having 5, 6 or 7 carbon atoms 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, or alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms and being in each case optionally substituted by 1 to 5 halogen atoms.
The present application relates in particular to compounds of the formula (I) in which
R
Dutzmann Stefan
Gallenkamp Bernd
Gayer Herbert
Gerdes Peter
Hanssler Gerd
Balasubramanian Venkataraman
Bayer Aktiengesellschaft
Gil Joseph C.
Raymond Richard L.
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