Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1999-05-05
2001-05-22
Ford, John M. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C544S319000
Reexamination Certificate
active
06235743
ABSTRACT:
TECHNICAL FIELD OF THE INVENTION
The invention relates to novel halogenopyrimidines, to two processes for their preparation and to their use as microbicides.
BACKGROUND OF THE INVENTION
Certain pyrimidines with a similar substitution pattern and their fungicidal action are already known (GB-A 2253624). However, the activity of these prior art compounds, in particular at low application rates and concentrations, is not entirely satisfactory in all areas of use.
DETAILED DESCRIPTION OF THE INVENTION
This invention, accordingly, provides the novel halogenopyrimidines of the general formula (I)
in which
Z represents respectively optionally substituted cycloalkyl, aryl or heterocyclyl,
R represents hydrogen or alkyl,
Q represents oxygen or sulphur and
X represents halogen,
L
1
, L
2
, L
3
and L
4
are identical or different and, independently of one another, each represents hydrogen, halogen, cyano, nitro, respectively 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 in combinations with hetero atoms, such as, for example, in alkoxy, alkylthio or alkylamino.
Aryl represents aromatic mono- or polycyclic hydrocarbon rings, such as, for example, phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or naphthyl, in particular phenyl.
Heterocyclyl represents saturated or unsaturated, and aromatic, ring-shaped compounds in which at least one ring member is a hetero atom, i.e. an atom other than carbon. If the ring contains more than one hetero atom, these may be identical or different. Preferred hetero atoms are oxygen, nitrogen or sulphur. Optionally, the ring-shaped compounds may form a polycyclic ring system together with other carbocyclic or heterocyclic fused or bridged rings. Preference is given to mono- or bicyclic ring systems, in particular to mono- or bicyclic aromatic ring systems.
Cycloalkyl represents saturated carbocyclic compounds in the form of a ring which may form a polycyclic ring system together with other carbocyclic fused or bridged rings.
Furthermore, it has been found that the novel halogenopyrimidines of the general formula (I) are obtained when
a) 2-(2-hydroxy-phenyl)-2-methoxyimino-acetamides of the formula (II)
in which
R, L
1
, L
2
, L
4
and L
4
are each as defined above are reacted with a substituted halogenopyrimidine of the general formula (III)
in which
Z, Q and X are each as defined above and
Y
1
represents halogen,
if appropriate in the presence of a diluent, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a catalyst, or
b) phenoxypyrimidines of the general formula (IV)
in which
R, X, L
1
, L
2
, L
3
and L
4
are each as defined above and
Y
2
represents halogen
are reacted with a ring compound of the general formula (V)
Z—Q—H (V)
in which
Z and Q are each as defined above,
if appropriate in the presence of a diluent, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a catalyst.
Finally, it has been found that the novel halogenopyrimidines of the general formula (I) have very strong fungicidal activity.
The compounds according to the invention may be present as mixtures of various possible isomeric forms, in particular of stereoisomers such as, for example, E- and Z-isomers. Both the E- and the Z-isomers and any mixtures of these isomers are claimed.
The invention preferably provides compounds of the formula (I) in which
Z
represents cycloalkyl having 3 to 7 carbon atoms which is in each case optionally mono- to disubstituted by halogen, alkyl or hydroxyl;
represents heterocyclyl having 3 to 7 ring members which is optionally substituted by alkyl having 1 to 4 carbon atoms;
or represents phenyl or naphthyl, each of which is optionally mono- to tetrasubstituted by identical or different substituents, the possible substituents preferably being selected from the list below:
halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl;
respectively straight-chain or branched alkyl, hydroxyalkyl, oxoalkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, dialkoxyalkyl, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 8 carbon atoms;
respectively straight-chain or branched alkenyl or alkenyloxy having in each case 2 to 6 carbon atoms;
respectively 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;
respectively 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;
respectively straight-chain or branched alkylamino, dialkylamino,
alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, arylalkylaminocarbonyl,dialkylaminocarbonyloxy, alkenylcarbonyl or alkinylcarbonyl having 1 to 6 carbon atoms in the respective hydrocarbon chains;
cycloalkyl or cycloalkyloxy having in each case 3 to 6 carbon atoms;
alkylene having 3 or 4 carbon atoms, oxyalkylene having 2 or 3 carbon atoms or dioxyalkylene having 1 or 2 carbon atoms, each of which is doubly attached and in each case optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, chlorine, oxo, methyl, trifluoromethyl and ethyl;
A
1
represents hydrogen, hydroxyl or alkyl having 1 to 4 carbon atoms or cycloalkyl having 1 to 6 carbon atoms and
A
2
represents hydroxyl, amino, methylamino, phenyl, benzyl or represents respectively optionally cyano-, hydroxyl-, alkoxy-, alkylthio-, alkylamino-, dialkylamino- or phenyl-substituted alkyl or alkoxy having 1 to 4 carbon atoms, or represents alkenyloxy or alkinyloxy having in each case 2 to 4 carbon atoms,
and phenyl, phenoxy, phenylthio, benzoyl, benzoylethenyl, cinnamoyl, heterocyclyl or phenylalkyl, phenylalkyloxy, phenylalkylthio or heterocyclyl-alkyl having in each case 1 to 3 carbon atoms in the respective alkyl moieties, each of which is optionally mono- to trisubstituted in the ring moiety by halogen and/or straight-chain or branched alkyl or alkoxy having 1 to 4 carbon atoms,
R represents hydrogen or methyl,
Q represents oxygen or sulphur and
X represents fluorine, chlorine, bromine or iodine,
L
1
, L
2
, L
3
and L
4
are identical or different and, independently of one another, each represents hydrogen, halogen, cyano, nitro, or represent 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.
The invention in particular provides compounds of the formula (I) in which
Z
represents cyclopentyl or cyclohexyl, each of which is optinally mono- to disubstituted by fluorine, chlorine, methyl, ethyl or hydroxyl;
represents optionally methyl- or ethyl-substituted thienyl, pyridyl or furyl;
or represents phenyl or naphthyl, each of which is optionally mono- to tetrasubstituted by identical or different substituents, the possible substituents preferably being selected from the list below:
fluorine, chlorine, bromine, iodine, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl,
methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, 1-, 2-, 3-, neo-pentyl, 1-, 2-, 3-, 4-(2-methylbutyl), 1-, 2-, 3-hexyl, 1-, 2-, 3-, 4-, 5-(2-methylpentyl), 1-, 2-, 3-(3-methylpentyl), 2-ethylbutyl, 1-, 3-, 4-(2,2-dimethylbutyl), 1-, 2-(2,3-dimethylbutyl), hydroxymethyl, hydroxyethyl, 3-oxobutyl, methoxymethyl, dimethoxymethyl,
methoxy, ethoxy, n- or i-propoxy,
methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl,
vinyl, allyl, 2-methylallyl, propen-1-yl, crotonyl, propargyl, vinyloxy, allyloxy, 2-methylallyloxy, propen-1-yloxy, crotonyloxy, propargyloxy,
trifluoromethyl, trifluoroethyl,
dif
Dutzmann Stefan
Gayer Herbert
Gerdes Peter
Hanssler Gerd
Heinemann Ulrich
Bayer Aktiengesellschaft
Ford John M.
Gil Joseph C.
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