Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2003-05-12
2004-03-23
Ramsuer, Robert W. (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C544S239000, C544S315000, C544S318000, C546S294000, C546S303000, C548S127000, C548S165000, C548S166000, C548S173000, C548S182000, C548S186000, C548S221000
Reexamination Certificate
active
06710045
ABSTRACT:
The present invention relates to novel heterocyclic fluoroalkenyl thioethers, to processes for their preparation and to their use as pesticides.
It is known that certain heterocyclic fluoroalkenyl thioethers have insecticidal, acaricidal and/or nematicidal properties (cf., for example, U.S. Pat. No. 3,914,251, U.S. Pat. No. 5,952,359, WO 99/52874, WO 99/52882, JP 10287659 or JP 11140063). However, in particular at low application rates and concentrations of active compound, the efficacy and/or activity spectrum of these compounds is not always entirely satisfactory.
This invention now provides novel heterocyclic fluoroalkenyl thioethers of the formula (I)
in which
m represents integers from 3 to 10,
n represents 0, 1 or 2 and
Het represents the following, in each case optionally substituted, groupings:
except for compounds where R
1
=alkyl, Y=oxygen and X=hydrogen.
Furthermore, it has been found that the heterocyclic fluoroalkenyl thioethers of the formula (I) are obtained when
a) mercapto derivatives of the formula (II)
Het—SH (II)
in which
Het is as defined above
are reacted with fluoroalkenyl halides of the formula (III)
in which
m is as defined above and
Hal represents halogen, preferably bromine or chlorine,
in the presence of a diluent and if appropriate in the presence of a basic reaction auxiliary, where it is also possible to use the compounds of the formula (II) in the form of their salts, preferably the alkali metal salts, such as, in particular, the sodium or potassium salts; and, if appropriate,
b) the resulting heterocyclic fluoroalkenyl thioethers of the formula (Ia) according to the invention
in which
Het and m are each as defined above
are oxidized with an oxidizing agent, if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst.
Finally, it has been found that the novel heterocyclic fluoroalkenyl thioethers of the formula (I) have highly pronounced biological properties and are suitable especially for controlling animal pests, in particular insects, arachnids and nematodes, encountered in agriculture, in forests, in the protection of stored products and materials and in the hygiene sector.
The formula (I) provides a general definition of the heterocyclic fluoroalkenyl thioethers according to the invention.
Preferred substituents or ranges of the radicals listed in the formulae mentioned above and below are illustrated below:
m preferably represents integers from 3 to 8.
n preferably represents 0 or 2.
Het preferably represents the following groupings, each of which is optionally mono- or polysubstituted by C
1
-C
8
-alkyl, C
1
-C
8
-alkoxy, C
1
-C
8
-alkylthio, C
1
-C
8
-alkylsulphinyl, C
1
-C
8
-alkylsulphonyl or C
2
-C
8
-alkenyl, each of which is optionally mono- or polysubstituted by identical or different halogens, phenyl which is optionally mono- to pentasubstituted by identical or different substituents from the group consisting of halogen, nitro, cyano, thiocyanato, and C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy or C
1
-C
4
-alkylthio, each of which is optionally mono- or polysubstituted by identical or different halogens, or by 5- or 6-membered heterocyclyl having 1 to 3 N, O or S heteroatoms, which is optionally mono- to pentasubstituted by identical or different substituents from the group consisting of halogen, nitro, cyano, thiocyanato, and C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy or C
1
-C
4
-alkylthio, each of which is optionally mono- or polysubstituted by identical or different halogens:
m particularly preferably represents integers from 3 to 6.
n particularly preferably represents 0.
Het particularly preferably represents the following groupings, each of which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, of C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-alkylthio, C
1
-C
6
-alkylsulphinyl, C
1
-C
6
-alkylsulphonyl or C
2
-C
6
-alkenyl, each of which is optionally mono- to pentasubstituted by identical or different substituents from the group consisting of fluorine and chlorine, of phenyl which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, nitro, cyano, thiocyanato, and C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy or C
1
-C
4
-alkylthio, each of which is optionally mono- to pentasubstituted by identical or different substitutents from the group consisting of fluorine and chlorine and of furyl, thienyl, pyrazolyl, pyridinyl or pyrimidinyl, each of which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, nitro, cyano, thiocyanato, and C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy or C
1
-C
4
-alkylthio, each of which is optionally mono- to pentasubstituted by identical or different substituents from the group consisting of fluorine and chlorine:
m very particularly preferably represents 4.
Het very particularly preferably represents the following groupings, each of which is optionally mono- to disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine and of methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i- or neo-pentyl, each of which is optionally mono- to pentasubstituted by identical or different substituents from the group consisting of fluorine and chlorine, of methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, of methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl; ethenyl, propenyl, butenyl, pentenyl or hexenyl, of phenyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, nitro, cyano, thiocyanato, and methyl, ethyl, methoxy, ethoxy, methylthio and ethylthio, each of which is optionally mono- to pentasubstituted by identical or different substituents from the group consisting of fluorine and chlorine, and of thienyl or pyridyl, each of which is optionally mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, nitro, cyano, thiocyanato, and methyl, ethyl, methoxy, ethoxy, methylthio and ethylthio, each of which is optionally mono- to pentasubstituted by identical or different substituents from the group consisting of fluorine and chlorine:
Het most preferably represents the following groupings, each of which is optionally mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, fluorine-substituted methylthio and optionally chlorine-substituted phenyl:
The abovementioned general or preferred radical definitions or illustrations apply both to the end products and, correspondingly, to the starting materials and intermediates. These radical definitions can be combined with one another as desired, i.e. including combinations between the respective preferred ranges.
Preference according to the invention is given to the compounds of the formula (I) which contain a combination of the meanings listed above as being preferred (preferable).
Particular preference according to the invention is given to compounds of the formula (I) which contain a combination of the meanings listed above as being particularly preferred.
Very particular preference according to the invention is given to the compounds of the formula (I) which contain a combination of the meanings listed above as being very particularly preferred.
Most preference according to the invention is given to the compounds of the formula (I) which contain a combination of the meanings listed above as being most preferred.
In the radical definitions listed above and below, hydrocarbon radicals, such as alkyl, are in each case straight-chain or branched as far as this is possible—including in combinations with heteroatoms, such as in alkoxy.
Using, for example, 2-mercaptobenzothiazole and 6,6,5-trifluorohex-5-enyl bromide as starting ma
Andersch Wolfram
Erdelen Christoph
Gallenkamp Bernd
Hansen Olaf
Harder Achim
Bayer CropScience AG
Henderson Richard E. L.
Ramsuer Robert W.
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