Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
1999-11-18
2002-01-08
Gerstl, Robert (Department: 1613)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C560S060000
Reexamination Certificate
active
06337401
ABSTRACT:
The invention relates to new fluoromethoxyacrylic acid derivatives, a process for their preparation and their use as pesticides, as well as to new intermediates and a plurality of processes for their preparation.
It has already been disclosed that certain fluoromethoxyacrylic acid derivatives which are similar in constitution to the compounds described below have fungicidal properties (compare, for example, WO 9517376). The fungicidal action of these compounds, however, is unsatisfactory in many cases.
The new fluoromethoxyacrylic acid derivatives have now been found, of the general formula (I)
in which
Ar represents substituted aryl and
Q represents optionally substituted alkoxy.
Aryl represents aromatic, mono- or polycyclic hydrocarbon rings, such as, for example, phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or naphthyl, in particular phenyl.
The compounds according to the invention, if appropriate, can exist as mixtures of various possible isomeric forms, in particular of stereoisomers, such as, for example, E- and Z-. Both the E- and the Z-isomers, and also any desired mixtures of these isomers, are claimed.
The invention preferably relates to compounds of the formula (I), in which
Ar represents mono- to trisubstituted phenyl or optionally mono- to tetrasubstituted naphthyl, the possible substituents preferably being selected from the list below: halogen, cyano, nitro; alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl, each of which is straight-chain or branched and has 1 to 6 carbon atoms; alkenyl, alkenyloxy or alkinyloxy, each of which is straight-chain or branched and has 2 to 6 carbon atoms; halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl, each of which is straight-chain or branched and has 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; halogenoalkenyl or halogenoalkenyloxy, each of which is straight-chain or branched and has 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms; alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy, hydroximinoalkyl or alkoximinoalkyl, each of which is straight-chain or branched and has 1 to 6 carbon atoms in the individual alkyl moieties; alkylene or dioxyalkylene, each having 1 to 6 carbon atoms, and each of which is divalent and is optionally mono- or polysubstituted, identically or differently, 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; or cycloalkyl having 3 to 6 carbon atoms, and
Q represents C
1
-C
6
-alkoxy which is optionally substituted by halogen or C
1
-C
4
-alkoxy.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkenyl or alkinyl, even linked to heteroatoms, such as in alkoxy, alkylthio or alkylamino, are each straight-chain or branched.
Halogen in general represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine.
Cycloalkyl represents saturated, carbocyclic ring compounds, which optionally form a polycyclic ring system with other carbocyclic, fused or bridged rings.
The invention relates in particular to compounds of the formula (I), in which
Ar represents phenyl which is mono- or disubstituted, identically or differently, the possible substituents preferably being selected from the list below: fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, methoxy, ethoxy, n- or i-propoxy, 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, or methylenedioxy, ethylenedioxy, each of which is divalent and is optionally mono- to tetrasubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl or ethyl, and
Q represents methoxy or ethoxy.
The abovementioned radical definitions, given in general or in preferred ranges, apply both to the final products of the formula (I) and correspondingly to the starting substances or intermediates needed in each case for preparation.
These radical definitions can be combined with one another, i.e. also between the given ranges of preferred compounds, in any desired manner.
It has furthermore been found that the fluoromethoxyacrylic acid derivatives of the formula (I) have very good microbicidal properties and can be employed for the protection of plants against harmful organisms.
Surprisingly, the substances according to the invention show a better action than constitutionally similar, previously known active compounds of the same direction of action.
Finally, it has been found that both the new and the known fluoromethoxyacrylic acid derivatives of the general formula (Ia)
in which
Ar
1
represents optionally substituted aryl and
Q
1
represents optionally substituted alkoxy,
are obtained when (process a) hydroxyaryl compounds of the general formula (II)
in which
Q
1
has the meaning indicated above,
are reacted with a thiadiazole derivative of the general formula (III)
in which
Ar
1
has the meaning indicated above and
X represents halogen, alkylsulphonyl or arylsulphonyl,
if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent.
It is to be regarded as particularly surprising here that the process according to the invention proceeds with considerably higher yields than the process known according to the prior art.
In process a) according to the invention, preferably compounds of the formula (Ia) are prepared in which
Ar
1
represents phenyl which is optionally mono- to trisubstituted or naphthyl which is optionally mono- to tetrasubstituted, the possible substituents preferably being selected from the list below: halogen, cyano, nitro; alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl, each of which is straight-chain or branched and has 1 to 6 carbon atoms; alkenyl, alkenyloxy or alkinyloxy, each of which is straight-chain or branched and has 2 to 6 carbon atoms; halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl, each of which is straight-chain or branched and has 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; balogenoalkenyl or halogenoalkenyloxy, each of which is straight-chain or branched and has 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms; alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy, hydroximinoalkyl or alkoximinoalkyl, each of which is straight-chain or branched and has 1 to 6 carbon atoms in the individual alkyl moieties; alkylene or dioxyalkylene, each having 1 to 6 carbon atoms, and each of which is divalent and is optionally mono- or polysubstituted, identically or differently, 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 or cycloalkyl having 3 to 6 carbon atoms; and
Q
1
represents C
1
-C
6
-alkoxy which is optionally substituted by halogen or C
1
-C
4
-alkoxy.
In particular, in process a) according to the invention, compounds of the formula (Ia) can be prepared in which
Ar
1
represents phenyl which is optionally mono- or disubstituted, identically or differently, the possible substituents preferably being selected from the list below: fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl, tri
Dutzmann Stefan
Gayer Herbert
Gerdes Peter
Heinemann Ulrich
Marhold Albrecht
Bayer Aktiengesellschaft
Gerstl Robert
Norris & McLaughlin & Marcus
LandOfFree
Fluoromethoxyacrylic acid derivatives and their use as pest... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Fluoromethoxyacrylic acid derivatives and their use as pest..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Fluoromethoxyacrylic acid derivatives and their use as pest... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2852060