Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
1999-06-10
2001-02-06
Shah, Mukund J. (Department: 1611)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
C544S212000, C544S238000, C544S310000, C544S182000
Reexamination Certificate
active
06184183
ABSTRACT:
TECHNICAL FIELD OF THE INVENTION
The present invention relates to novel heterocyclyluracils, to a process for their preparation and to their use as herbicides.
BACKGROUND OF THE INVENTION
Numerous heterocyclyluracils having herbicidal and/or insecticidal properties are already known (cf. JP-A 91-287 585, JP-A 93 202 031, Chem. Abstr. 116, 235 650 and Chem. Abstr. 120, 107 048). Thus, for example, 1-(3-chloro-5-trifluoromethylpyridin-2-yl)-3,6-dihydro-2,6-dioxo-4-trifluoromethyl-1(2H)-pyrimidine can be used for controlling weeds. However, at low application rates, the activity of this substance is not always satisfactory.
DETAILED DESCRIPTION OF THE INVENTION
This invention, accordingly, provides novel heterocyclyluracils of the formula
in which
R
1
represents formyl, hydroximinomethyl, cyano, carboxyl, alkoxycarbonyl, carbamoyl, thiocarbamoyl or represents optionally halogen-substituted C
1
-C
4
-alkyl,
R
2
represents hydrogen, cyano, halogen or represents opitionally halogen-substituted C
1
-C
4
-alkyl and
Het represents pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, pyrazolyl, oxazolyl, isoxazolyl or thiazolyl, where these radicals are optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of hydroxyl, mercapto, amino, cyano, nitro, carboxyl, carbamoyl, thiocarbamoyl, halogen, alkyl having 1 to 6 carbon atoms, alkoxyalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to 6 carbon atoms in the alkyl moiety, alkoxy having 1 to 6 carbon atoms, halogenoalkoxy having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkoxyalkoxy having 1 to 6 carbon atoms in each alkoxy moiety, alkylthio having 1 to 6 carbon atoms, halogenoalkylthio having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylsulphinyl having 1 to 6 carbon atoms, halogenoalkylsulphinyl having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylsulphonyl having 1 to 6 carbon atoms, halogenoalkylsulphonyl having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylcarbonyl having 1 to 6 carbon atoms in the alkyl moiety, halogenoalkylcarbonyl having 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkyl moiety, alkoxycarbonyl having 1 to 6 carbon atoms in the alkoxy moiety, halogenoalkoxycarbonyl having 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkoxy moiety, alkylamino having 1 to 6 carbon atoms, dialkylamino having 1 to 6 carbon atoms in each alkyl moiety, halogenoalkylamino having 1 to 5 halogen atoms and 1 to 6 carbon atoms, alkylaminocarbonyl having 1 to 6 carbon atoms in the alkyl moiety, dialkylaminocarbonyl having 1 to 6 carbon atoms in each alkyl moiety, alkylsulphonylamino having 1 to 6 carbon atoms in the alkyl moiety, halogenoalkylsulphonylamino having 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkyl moiety, N,N-bis-alkylsulphonylamino having 1 to 6 carbon atoms in each alkyl moiety, N,N-bis-halogenoalkylsulphonyl-amino having 1 to 5 halogen atoms and 1 to 6 carbon atoms in each halogenoalkyl moiety, N-alkyl-N-alkylsulphonyl-amino having 1 to 6 carbon atoms in the alkyl moiety and 1 to 6 carbon atoms in the alkylsulphonyl moiety, N-halogenoalkyl-N-halogenoalkylsulphonyl-amino having 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkyl moiety and 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkylsulphonyl moiety, N-alkylcarbonyl-N-alkylsulphonyl-amino having 1 to 6 carbon atoms in the alkyl moiety of the alkylcarbonyl group and 1 to 6 carbon atoms in the alkylsulphonyl moiety, N-halogenoalkylcarbonyl-N-halogenoalkylsulphonyl-amino having 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkyl moiety and 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkylsulphonyl moiety and N-alkylsulphonyl-N-phenylcarbonyl-amino having 1 to 6 carbon atoms in the alkylsulphonyl moiety and being optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen, alkyl having 1 to 4 carbon atoms dialkylamino having 1 to 4 carbon atoms in each alkyl group and alkoxy having 1 to 4 carbon atoms.
Furthermore, it has been found that heterocyclyluracils of the formula (I) are obtained when
a) in a first step aminoalkenoic esters of the formula
in which
R
1
and R
2
are each as defined above and
R represents alkyl, aryl or arylalkyl are either reacted
&agr;) with heterocyclyl isocyanates of the formula
O═C═N—Het (III),
in which
Het is as defined above,
or
&bgr;) with heterocyclyl carbamates of the formula
in which
Het is as defined above and
R
3
represents alkyl, aryl or arylalkyl,
in each case if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent,
and
b) in a second step the resulting heterocyclyluracils of the formula
in which
R
1
, R
2
and Het are each as defined above are reacted with 1-aminooxy-2,4-dinitrobenzene of the formula
if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent.
Finally, it has been found that the novel heterocyclyluracils of the formula (I) have very good herbicidal properties.
Surprisingly, the heterocyclyluracils of the formula (I) according to the invention have considerably better herbicidal activity than the constitutionally most similar active compounds of the prior art which have the same direction of action.
In the present case, alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, halogenoalkyl, halogenoalkoxy and halogenoalkylthio are in each case to be understood as straight-chain or branched radicals.
Unless stated otherwise, halogen in the present case represents fluorine, chlorine, bromine or iodine.
The formula (I) provides a general definition of the heterocyclyluracils according to the invention. Preference is given to compounds of the formula (I) in which
R
1
represents formyl, hydroximinomethyl, cyano, carboxyl, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy moiety, carbamoyl, thiocarbamoyl or represents alkyl having 1 to 3 carbon atoms which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of fluorine and chlorine,
R
2
represents hydrogen, cyano, fluorine, chlorine, bromine or represents alkyl having 1 to 3 carbon atoms which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of fluorine and chlorine and
Het represents pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, pyrazolyl, oxazolyl, isoxazolyl or thiazolyl, where these radicals are optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of hydroxyl, mercapto, amino, cyano, nitro, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, alkyl having 1 to 4 carbon atoms, alkoxyalkyl having 1 to 4 carbon atoms in the alkyl moiety and 1 or 2 carbon atoms in the alkoxy moiety, alkoxy having 1 to 4 carbon atoms, halogenoalkoxy having 1 to 3 fluorine and/or chlorine atoms and 1 to 4 carbon atoms, alkoxyalkoxy having 1 to 4 carbon atoms in each alkoxy moiety, alkylthio having 1 to 4 carbon atoms, halogenoalkylthio having 1 to 3 fluorine and/or chlorine atoms and 1 to 4 carbon atoms, alkylsulphinyl having 1 to 4 carbon atoms, halogenoalkylsulphinyl having 1 to 3 fluorine and/or chlorine atoms and 1 to 4 carbon atoms, alkylsulphonyl having 1 to 4 carbon atoms, halogenoalkylsulphonyl having 1 to 3 fluorine and/or chlorine atoms and 1 to 4 carbon atoms, alkylcarbonyl having 1 to 4 carbon atoms in the alkyl moiety, halogenoalkylcarbonyl having 1 to 3 fluorine and/or chlorine atoms and 1 to 4 carbon atoms in the halogenoalkyl moiety, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy moiety, halogenoalkoxycarbonyl having 1 to 3 fluorine and/or chlorine atoms and 1 to 4 carbon atoms in the halogenoalkoxy moiety, alkylamino having 1 to 4 carbon atoms, dialkylamino having 1 to 4 carbon atoms in each alkyl moiety, halogenoalkylamino having 1 to 3 halogen atoms and 1 to 4 carbon atoms, alkylaminocar
Andree Roland
Dollinger Markus
Drewes Mark Wilhelm
Bayer Aktiengesellschaft
Gil Joseph C.
Liu Hong
Shah Mukund J.
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