Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-01-12
2002-02-19
Raymond, Richard L. (Department: 1611)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C544S309000
Reexamination Certificate
active
06348471
ABSTRACT:
The invention relates to novel pyrimidyloxyphenylacetic acid derivatives, 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 pyrimidyloxyphenylacetic acid derivatives, such as, for example, methyl 2-(methoxyimino)-2-[[4-(2,2,2-trifluoroethoxy)-2-pyrimidyl]oxy]-phenylacetate, 2-(methoxyimino)-N-methyl-2-[[4-(2,2,2-trifluoro-ethoxy)-2-pyrimidyl]oxy]-phenylacetamide, methyl 2-(methoxyimino)-2-[[4-(2,2,2-trifluoro-1-methylethoxy)-2-pyrimidyl]oxy]-phenylacetate and 2-(methoxyimino)-N-methyl-2-[[4-(2,2,2-trifluoro-1-methylethoxy)-2-pyrimidyl]oxy]-phenylacefamide, which have a constitution similar to those described below, have fungicidal properties (compare, for example, WO 95-24396 or EP 398692). However, the fungicidal activity of these compounds is unsatisfactory, in particular at low application rates.
This invention, accordingly, provides the novel pyrimidyloxyphenylacetic acid derivatives of the general formula (I)
in which
R represents in each case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl or cycloalkenyl, except for 2,2,2-trifluoroethyl and 1-methyl-2,2,2-trifluoroethyl,
Q represents oxygen or —NH—, 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 definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkinyl, are in each case straight-chain or branched, including 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.
Cycloalkyl represents saturated, carbocyclic, cyclic compounds which optionally form a polycyclic ring system with other carbocyclic, fused-on or bridged rings.
Cycloalkenyl represents carbocyclic, cyclic compounds which contain at least one double bond and which optionally form a polycyclic ring system with other carbocyclic, fused-on or bridged rings.
Furthermore, it has been found that the novel pyrimidyloxyphenylacetic acid derivatives of the general formula (I) are obtained when (process a) 4-halogeno-2-phenoxypyrimidines of the general formula (II)
in which
Q, L
1
, L
2
, L
3
and L
4
are as defined above and
X represents halogen
are reacted with an alcohol of the general formula
R—O—H (III),
in which
R is 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 is as defined above and
R
1
represents alkyl or arylalkyl,
are reacted with a 2-(1-hydroxyphenyl-1-methoximino)acetic acid derivative of the general formula
in which
Q, 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 pyrimidyloxyphenylacetic acid derivatives of the general formula (I) have very strong fungicidal activity.
Surprisingly, the compounds according to the invention have better fungicidal activity than methyl 2-(methoxyimino)-2-[[4-(2,2,2-trifluoroethoxy)-2-pyrimidyl]oxy]-phenylacetate, 2-(methoxyimino)-N-methyl-2-[[4-(2,2,2-trifluoroethoxy)-2-pyrimidyl]oxy]-phenylacetamide, methyl 2-(methoxyimino)-2-[[4-(2,2,2-trifluoro-1-methylethoxy)-2-pyrimidyl]oxy]-phenylacetate and 2-(methoxyimino)-N-methyl-2-[[4-(2,2,2-trifluoro-1-methylethoxy)-2-pyrimidyl]oxy]-phenylacetamide, which are constitutionally similar prior-art compounds of 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 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.
Preference is given to pyrimidyloxyphenylacetic acid derivatives of the formula (I) in which
R represents alkyl having 4 to 12 carbon atoms which is optionally mono- to n-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,
Q represents oxygen or —NH— 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, and preferably represents hydrogen or methyl and in particular hydrogen.
Preference is also given to pyrimidyloxyphenylacetic acid derivatives of the formula (I) in which
R represents methyl which is optionally mono-, di- or trisubstituted by halogen or represents ethyl which is optionally mono-, di-, tetra- or penta-substituted by halogen and/or 1 to 2 alkoxy groups having 1 to 8 carbon atoms, or represents n-propyl which is optionally mono-, di-, tri-, tetra- penta-, hexa- or hepta-substituted by halogen and/or 1 to 2 alkoxy groups having 1 to 8 carbon atoms or represents i-propyl which is optionally mono-, di-, tetra-, penta-, hexa- or hepta-substituted by halogen and/or 1 to 2 alkoxy groups having 1 to 8 carbon atoms,
Q represents oxygen or —NH— 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, preferably represents hydrogen or methyl and in particular hydrogen.
Preference is furthermore given to pyrimidyloxyphenylacetic acid derivatives of the formula (I) in which
R represents alkenyl or alkinyl having 2 to 12 carbon atoms which is optionally mono- to n-substituted (where n is 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 (which for their part may optionally be substituted by halogen, alkyl having 1 to 4 carbon atoms, alkenyl having 2 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms or halogenoalkenyl having 2 to 4 carbon atoms and 1 to 3 halogen atoms),
Q represents oxygen or —NH— 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, preferably represents hydrogen or methyl and in particular hydrogen.
Preference is furthermore given to pyrimidyloxyphenylacetic acid derivatives of the formula (I) in which
R represents cycloalkyl, cycloalkenyl, cycloalkylalkyl or cycloalkenylalkyl having 3 to 8 carbon atoms in the cycloalkyl or cycloalkenyl moiety and 1 to 4 carbon atoms in the alkyl moiety, which is optionally mono- to pentasubstituted by halogen, alkyl having 1 to 4 carbon atoms, alkenyl having 2 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms or halogenoalkenyl having 2 to 4 carbon atoms and 1 to 3 halogen atoms,
Q represents oxygen or —NH— 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 alkylsulpho
Dutzmann Stefan
Gayer Herbert
Gerdes Peter
Heinemann Ulrich
Mauler-Machnik Astrid
Bayer Aktiengesellschaft
Gil Joseph C.
Liu Hong
Raymond Richard L.
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