Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
1999-12-02
2001-10-23
Shah, Mukund J. (Department: 1611)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C514S256000, C514S269000, C514S361000, C544S215000, C544S216000, C544S315000, C548S129000, C548S132000, C560S008000
Reexamination Certificate
active
06306855
ABSTRACT:
The invention relates to novel fluoromethoximino compounds, to processes for their preparation and to their use as pesticides, and also to novel intermediates and to a plurality of processes for their preparation.
It is already known that certain fluoromethoximino compounds which are constitutionally similar to the compounds described below have fungicidal properties (compare, for example, WO 95/17 376 and DE-9 611 653). However, in many cases, the fungicidal activity of these compounds is unsatisfactory.
This invention, accordingly, provides the novel fluoromethoximino compounds of the general formula (I)
in which
Q
1
represents oxygen or —NH—,
R represents a grouping
in which
Ar represents optionally substituted aryl,
Q
2
represents oxygen or sulphur,
X represents hydrogen or halogen 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.
Aryl preferably represents aromatic, mono- or polycyclic hydrocarbon rings, such as, in particular, phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or naphthyl, especially phenyl.
Halogen preferably represents fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine.
Furthermore, it has been found that the novel fluoromethoximino compounds of the general formula (I) are obtained when (process a) hydroxyaryl compounds of the general formula (II)
in which
Q
1
, L
1
, L
2
, L
3
and L
4
are as defined above,
are reacted with a heterocyclyl derivative of the general formulae (III), (IV), (V), (VI), (VII) or (VIII)
in which
Ar, Q
2
and X are as defined above and
X
1
, X
2
, X
3
, X
4
, X
5
and X
6
represent halogen, alkylsulphonyl or arylsulphonyl,
if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent.
It is also possible to obtain fluoromethoximino compounds of the formula (I) where the meaning of Q
1
is NH (process a1) by reacting fluoromethoximino compounds of the formula (I) according to the invention where the meaning of Q
1
is oxygen with methylamine, if appropriate in the presence of a diluent, such as, for example, methanol, ethanol or tetrahydrofuran.
Finally, it has been found that the fluoromethoximino compounds of the formula (I) have very good microbicidal properties and can be used for protecting plants against harmful organisms.
Surprisingly, the substances according to the invention have better activity than constitutionally similar active compounds of the prior art with the same direction of action.
If appropriate, the compounds according to the invention can be present as mixtures of different possible isomeric forms, in particular stereoisomers, such as, for example, E and Z. What is claimed are both the E and the Z isomers, and also any mixtures of these isomers.
The invention preferably provides compounds of the formula (I) in which
Q
1
represents oxygen or —NH—,
R represents a grouping
in which
Ar represents optionally mono- to trisubstituted phenyl or optionally mono- to tetrasubstituted naphthyl, where the possible substituents are preferably selected from the list below:
halogen, cyano, nitro, amino, hydroxyl, mercapto, 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, 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 11 identical or different halogen atoms, in each case straight-chain or branched alkylamino, cycloalkylamino, 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 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, cycloalkenyl, cycloalkoxy or cycloalkenyloxy having in each case 3 to 7 carbon atoms and being in each case optionally substituted by 1 to 4 halogen atoms, and saturated heterocyclyl which is attached via nitrogen,
Q
2
represents oxygen or sulphur,
X represents hydrogen, fluorine, chlorine or bromine 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, represents 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.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkenyl or alkinyl, are in each case straight-chain or branched, including in combination with heteroatoms, such as in alkoxy, alkylthio or alkylamino.
Cycloalkyl represents saturated, carbocyclic cyclic compounds which, if appropriate, form a polycyclic ring system with other carbocyclic, fused-on or bridged rings.
The invention relates in particular to compounds of the formula (I) in which
Q
1
represents oxygen or —NH—,
R represents a grouping
in which
Ar represents phenyl which is optionally mono- or disubstituted by identical or different substitutents, where the possible substituents are preferably selected from the list below:
fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, but-3-en-2-yl, 2-methylpropenyl, cyclopropyl, methoxy, ethoxy, n- or i-propoxy, allyloxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl, ethoximinoethyl, in each case doubly attached propylene, butylene or pentylene or in each case doubly attached methylenedioxy or ethylenedioxy, each of which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, chlorine, methyl, trifluoromethyl and ethyl,
Q
2
represents oxygen or sulphur,
X represents hydrogen, fluorine or chlorine and
L
1
, L
2
, L
3
and L
4
are identical or different and independently of one another each represents hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl.
Very particular preference is given to compounds of the general formula (I) in which
Q
1
represents oxygen or —NH—,
R represents a grouping Ar
in which
Ar represents phenyl which is optionally mono- or disubstituted by identical or different substituents, where the possible substituents are preferably selected from the list below:
fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, but-3-en-2-yl, 2-methylpropenyl, cyclopropyl, methoxy, ethoxy, n- or i-propoxy, allyloxy, methylthio, et
Buschhaus Hans-Ulrich
Dutzmann Stefan
Gayer Herbert
Gerdes Peter
Heinemann Ulrich
Balasubramanian Venkataraman
Bayer Aktiengesellschaft
Gil Joseph C.
Shah Mukund J.
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