Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2000-02-08
2001-06-26
Raymond, Richard L. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C544S066000, C549S467000
Reexamination Certificate
active
06251899
ABSTRACT:
This application is the National Stage Application of PCT/EP98/04821, which claims priority from German Application 197 35 196.4, filed Aug. 14, 1997 and from German Application 197 37 723.8, filed Aug. 29, 1997.
TECHNICAL FIELD OF THE INVENTION
The invention relates to novel methoximinomethyloxadiazines, to two processes for their preparation and to their use as pesticides, and also to novel intermediates and to processes for their preparation.
BACKGROUND OF THE INVENTION
It is already known that certain methoximinomethyloxadiazines have fungicidal activity (WO 96-25406). 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 methoximinomethyloxadiazines of the general formula (I)
in which
Z represents cycloalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, each of which is optionally substituted,
Q represents oxygen or sulphur,
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, or represents alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl, each of which is optionally substituted by halogen.
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 combination with heteroatoms, 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 also aromatic, annular compounds in which at least one ring member is a heteroatom, i.e. an atom which is different from carbon. If the ring contains a plurality of heteroatoms, these can be identical or different. Preferred heteroatoms are oxygen, nitrogen or sulphur. If the ring contains a plurality of oxygen atoms, these are not adjacent. If appropriate, the annular compounds form, together with other carbocylic or heterocyclic, fused or bridged rings, a polycyclic ring system. Preference is given to mono- or bicyclic ring systems, in particular to mono- or bicyclic aromatic ring systems.
Cycloalkyl represents saturated carbocyclic annular compounds which may form, together with other carbocyclic, fused or bridged rings, a polycyclic ring system.
Furthermore, it has been found that the novel methoximinomethyloxadiazines of the general formula (I) are obtained when
a) 3-(2-hydroxy-phenyl)-3-methoxyiminomethyl-oxadiazines of the formula (II),
in which
L
1
, L
2
, L
3
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
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 methoximinomethyloxadiazines of general formula (I) have very potent fungicidal activity.
The compounds according to the invention may be present as mixtures of different possible isomeric forms, in particular of stereoisomers, such as, for example, E and Z. 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 or cycloalkylalkyl having in each case 3 to 7 carbon atoms in the cycloalkyl moiety and 1 to 4 carbon atoms in the alkyl moiety and being in each case optionally mono- to pentasubstituted by halogen or alkyl;
represents heterocyclyl or heterocyclylalkyl having in each case 3 to 7 ring members and 1 to 4 carbon atoms in the alkyl moiety and being in each case optionally substituted by halogen or alkyl having 1 to 4 carbon atoms;
or represents aryl or arylalkyl having in each case 6 to 10 carbon atoms in the aryl moiety and 1 to 4 carbon atoms in the alkyl moiety and being in each case optionally mono- to tetrasubstituted in the aryl moiety by identical or different substituents, the possible substituents preferably being selected from the list below:
halogen, cyano, nitro, amino, formyl, carbamoyl, thiocarbamoyl;
alkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 8 carbon atoms and being in each case straight-chain or branched;
alkenyl or alkenyloxy having in each case 2 to 6 carbon atoms and being in each case 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 and being in each case 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 and being in each case straight-chain or branched;
alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylamino-carbonyl, dialkylaminocarbonyl, dialkylaminocarbonyl, arylalkylamino-carbonyl, alkenylcarbonyl or alkinylcarbonyl having 1 to 6 carbon atoms in the hydrocarbon chains in question and being in each case straight-chain or branched;
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 each of which is optionally mono- to tetrasubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, oxo, methyl, trifluoromethyl and ethyl;
or a grouping
in which
A
1
represents hydrogen or alkyl having 1 to 4 carbon atoms or cycloalkyl having 3 to 6 carbon atoms and
A
2
represents hydroxyl, amino, methylamino, methyl, phenyl, benzyl, alkoxy, alkylamino, dialkylamino having 1 to 4 carbon atoms in the alkyl chains in question,
Q represeents oxygen or sulphur,
X represents fluorine, chlorine or bromine, preferably represents fluorine or chlorine and in particular represents fluorine and
L
1
, L
2
, L
3
and L
4
are identical or different and, independently of one another 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, preferably represents hydrogen or methyl and in particular represents hydrogen.
The invention in particular relates to compounds of the formula (I), in which
Z represents cyclobutyl, cyclopentyl or cyclohexyl, each of which is optionally mono- to pentasubstituted by fluorine, chlorine, methyl or ethyl;
represents thienyl, pyridyl, furyl, thienylmethyl, pyridylmethyl or furylmethyl, each of which is optionally substituted by methyl, ethyl, fluorine, chlorine or bromine;
or represents phenyl or benzyl, each of which is optionally mono- to tetrasubstituted by identical or different substituents, the possible substituents being selected from the list below:
fluorine, chlorine, bromine, cyano, nitro, amino, formyl, carbamoyl, thio-carbamoyl,
methyl, ethyl, n- or i-propyl n-, i-, s- or t-butyl, methoxymethyl,
methoxy, ethoxy, n- or i-propoxy,
methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl,
methylaminomethyl, dimethylaminomethyl,
vinyl, allyl,
Gayer Herbert
Gerdes Peter
Hanssler Gerd
Heinemann Ulrich
Kruger Bernd-Wieland
Bayer Aktiengesellschaft
Gil Joseph C.
McKenzie Thomas
Raymond Richard L.
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