Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2001-04-06
2002-08-27
Owens, Amelia (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S336000, C514S444000, C549S060000, C549S292000, C546S282100, C504S292000
Reexamination Certificate
active
06441030
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to novel 3-phenyl-pyrones, to a process for their preparation and to their use as pesticides, fungicides and herbicides.
BACKGROUND OF THE INVENTION
Numerous oxymethoxy-3-phenyl-pyrone derivatives having pesticidal, fungicidal and herbicidal properties have already been disclosed (c.f. WO 97-19 941). The activity of these substances is good; however, at low application rates and at certain indications, it sometimes leaves something to be desired.
Furthermore 3-(2-methyl-4-fluorophenyl)-4-hydroxy-5-methyl-6-(pyrid-2-yl)-pyrone and 3-(2-methyl4-chlorophenyl)-4-hydroxy-5-methyl-6-(4-fluorophenyl)-pyrone have already been described as intermediates (cf. WO 97-19 941). However, biological properties of these substances have hitherto not been mentioned.
SUMMARY OF THE INVENTION
Novel 3-phenyl-pyrones of the formula
have pesticidal, and herbicidal activity.
DETAILED DESCRIPTION
This invention, accordingly, provides novel 3-phenyl-pyrones of the formula
in which
X represents alkyl and
Y represents halogen
X represents halogen and
Y represents alkyl,
A represents hydrogen, alkyl or optionally substituted aryl and
D represents hydrogen, alkyl, optionally substituted cycloalkyl, optionally substituted aryl or optionally substituted heterocyclyl, or
D represents a radical of the formula
in which
R represents optionally substituted phenyl, or
A and D together with the carbon atoms to which they are attached represent an optionally substituted carbocycle or represent an optionally substituted heterocycle,
except for the compounds of the formulae
Depending on the nature of the substituents, the compounds of the formula (I) can be present as geometrical and/or optical isomers or isomer mixtures of varying composition, which can, if desired, be separated in a customary manner. The present invention relates both to the pure isomers and to isomer mixtures. For the sake of simplicity, hereinbelow 3-phenyl-pyrones of the formula (I) are always referred to, although this may mean both the pure isomers and, if appropriate, also mixtures having various proportions of isomers.
The 3-phenyl-pyrones of the formula (I) can be depicted by the formula
The broken line is meant to indicate that these substances can be present in the two tautomeric forms
The 3-phenyl-pyrones according to the invention can be present as mixtures of compounds of the formulae (I) and (Ia), or else in the form of pure isomers. Mixtures of compounds of the formulae (1) and (Ia) can be separated by physical means, for example by chromatographic methods.
For reasons of clarity, hereinbelow only one of the possible isomers is shown in each case. This does not exclude that the compounds, if appropriate, may be present in the form of the isomer mixtures or in the other isomeric form in question.
Furthermore, it has been found that the 3-phenyl-pyrones of the formula (I) can be prepared by reacting
&agr;) either carbonyl compounds of the formula
in which
A and D are each as defined above or
&bgr;) silyl ethers of the formula
in which
A and D are each as defined above and
Alk represents alkyl having 1 to 4 carbon atoms,
in each case with ketene derivatives of the formula
in which
X and Y are each as defined above and
Hal represents chlorine or bromine,
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 3-phenyl-pyrones of the formula (I) according to the invention have very good pesticidal, fungicidal and herbicidal activity.
Surprisingly, the 3-phenyl-pyrones of the formula (I) according to the invention are more suitable for use as pesticides, fungicides and herbicides than the constitutionally most similar prior-art active compounds of the same direction of action.
The formula (I) provides a general definition of the 3-phenyl-pyrones according to the invention. Preference is given to compounds of the formula (I), in which
X represents alkyl having 1 to 6 carbon atoms and
Y represents fluorine, chlorine or bromine or
X represents fluorine, chlorine or bromine and
Y represents alkyl having 1 to 6 carbon atoms.
A preferably represents hydrogen, alkyl having 1 to 12 carbon atoms or represents phenyl which may be mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen, C
1
-C
6
-alkyl, C
1
-C
6
-halogenoalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-halogenoalkoxy, cyano and nitro,
D preferably represents hydrogen, alkyl having 1 to 12 carbon atoms, represents cycloalkyl having 3 to 8 carbon atoms which is optionally substituted by halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms and/or halogenoalkyl having 1 to 4 carbon atoms,
or represents phenyl which may be mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen, C
1
-C
6
-alkyl, C
1
-C
6
-halogenoalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-halogenoalkoxy, cyano, nitro, phenyl and/or phenoxy, where the two lastmentioned radicals for their part may be mono- or disubstituted by halogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-halogenoalkyl and/or C
1
-C
4
-halogenoalkoxy,
or represents 5- or 6-membered heteroaryl having 1 or 2 heteroatoms selected from the group consisting of oxygen, sulphur and nitrogen, where these radicals may be mono- or disubstituted by halogen, C
1
-C
6
-alkyl, C
1
-C
6
-halogenoalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-halogenoalkoxy, cyano and/or nitro,
or represents a radical of the formula
in which
R preferably represents phenyl which may be mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen, C
1
-C
6
-alkyl, C
1
-C
6
-halogenoalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-halogenoalkoxy, cyano and/or nitro,
A and D together furthermore also preferably represent a C
3
-C
6
-alkanediyl, C
3
-C
6
-alkenediyl or C
4
-C
6
-alkanedienediyl group in which in each case optionally one methylene group is replaced by oxygen or sulphur, and which are in each case optionally substituted by halogen, C
1
-C
6
-alkyl, C
1
-C
6
-halogenoalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-halogenoalkoxy, or by a further C
3
-C
6
-alkanediyl-, C
3
-C
6
-alkenediyl- or C
4
-C
6
-alkanedienediyl group which forms a fused-on ring and in which in each case optionally one methylene group is replaced by oxygen or sulphur and which are optionally substituted by C
1
-C
6
-alkyl.
In the compounds of the formula (I), particularly preferably,
X represents alkyl having 1 to 4 carbon atoms and
Y represents fluorine, chlorine or bromine or
X represents chlorine or bromine and
Y represents alkyl having 1 to 4 carbon atoms,
A particularly preferably represents hydrogen, alkyl having 1 to 8 carbon atoms or represents phenyl which may be mono- to trisubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, C
1
-C
4
-alkyl, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-halogenoalkoxy, cyano and nitro,
D particularly preferably represents hydrogen, alkyl having 1 to 10 carbon atoms, represents cycloalkyl having 3 to 7 carbon atoms which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, C
1
-C
3
-alkyl, C
1
-C
2
-alkoxy, C
1
-C
2
-halogenoalkyl,
or represents phenyl which may be mono- to trisubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, C
1
-C
4
-alkyl, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-halogenoalkoxy, cyano, nitro, phenyl and/or phenoxy, where the two last mentioned radicals for their part may be mono- or disubstituted by fluorine, chlorine, bromine, methyl, ethyl, methoxy, trifluoromethyl, trifluoromethoxy and/or difluoromethoxy,
or represents furanyl, pyridyl, imidazolyl, triazolyl, pyrazolyl, pyrimidinyl, thiazolyl or thienyl, where these radicals may be mono- or disubstituted by fluorine, chlorine, bromine, C
1
-C
4
-alkyl, C
1
-C
4
-halogenoal
Andersch Wolfram
Erdelen Christoph
Fischer Reiner
Graff Alan
Hänssler Gerd
Bayer Aktiengesellschaft
Gil Joseph C.
Mrozinski, Jr. John E.
Owens Amelia
LandOfFree
3-phenyl-pyrones does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with 3-phenyl-pyrones, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and 3-phenyl-pyrones will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2955362