Heterocyclyluracil

Details Heterocyclyluracil Heterocyclyluracil

1999-06-11

2001-02-13

Ford, John M. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C544S310000

Reexamination Certificate

active

06187716

ABSTRACT:

TECHNICAL FIELD OF THE INVENTION
The present invention relates to novel heterocyclyluracils, to a plurality of processes 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-trifluoromethyl-pyridin-2-yl)-3,6-dihydro-2,6-dioxo-4-trifluoromethyl-1(2H)-pyrimidine can be employed 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 hydrogen or represents optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted C
1
-C
4
-alkyl,
R
2
represents formyl, hydroximinomethyl, cyano, carboxyl, alkoxycarbonyl, carbamoyl, thiocarbamoyl or represents optionally halogen-substituted C
1
-C
4
-alkyl,
R
3
represents hydrogen, cyano, halogen or represents optionally halogen-substituted C
1
-C
4
-alkyl and
Het represents the radical of the formula
 in which
R
4
represents hydroxyl, mercapto, amino, nitro, cyano, carbamoyl, thiocarbamoyl, 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, halogeno-alkylthio 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-halogeno-alkylcarbonyl-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 or represents N-alkylsulphonyl-N-phenylcarbonyl-amino having 1 to 6 carbon atoms in the alkylsulphonyl moiety which is optionally mono- to trisubstituted by identical or different substituents 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,
R
5
represents hydroxyl, mercapto, amino, nitro, cyano, carboxyl, carbamoyl, halogen, alkyl having 1 to 6 carbon atoms, thiocarbamoyl, 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 or represents 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 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, and
m represents integers from 0 to 3,
or
Het represents the radical of the formula
 in which
R
6
represents hydroxyl, mercapto, amino, carboxyl, carbamoyl, thiocarbamoyl, 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

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