Substituted azolylsulphonylphenyluracils

Details Substituted azolylsulphonylphenyluracils Substituted azolylsulphonylphenyluracils

1997-04-25

2000-06-13

Ford, John M.

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

544310, C07D23954, A01N 4354

Patent

active

06074989&

DESCRIPTION:

BRIEF SUMMARY
The invention relates to novel substituted azolylsulphonylphenyluracils, a process for their preparation and their use as herbicides.
Certain heterocyclylsulphonylphenyluracils, such as, for example, the compounds 1-[2-chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1(2H)-pyri diminyl)-4-fluoro-phenylsulphonyl]-pyrrolidine and 4-[2-chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1(2H)-pyri midinyl)-4-fluoro-phenylsulphonyl]-morpholine, are known to have herbicidal properties (cf. U.S. Pat. No. 5,169,430). However, the activity of these compounds is not always entirely satisfactory, in particular at low application rates and active compound concentrations.
This invention, then, provides novel substituted azolylsulphonylphenyluracils of the general formula (I) ##STR2## in which Az represents optionally substituted azolyl, substituted radical of the group consisting of alkyl and alkoxy, substituted radical from the group consisting of alkyl, alkenyl or alkinyl.
The novel substituted azolylsulphonylphenyluracils of the general formula (I) are obtained when chlorosulphonylphenyluracils of the general formula (II) ##STR3## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are each as defined above, in the presence of a diluent.
The novel substituted azolylsulphonylphenyluracils of the general formula (I) have a pronounced and selective herbicidal action.
Preference is given to compounds of the formula (I) in which optionally mono- to trisubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, amino, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, halogeno-C.sub.1 -C.sub.4 -alkyl, halogeno-C.sub.1 -C.sub.4 -alkoxy or halogeno-C.sub.1 -C.sub.4 -alkylthio, respectively optionally fluorine- and/or chlorine-substituted radical from the group consisting of C.sub.1 -C.sub.4 -alkyl and C.sub.1 -C.sub.4 -alkoxy, fluorine- and/or chlorine-substituted C.sub.1 -C.sub.4 -alkyl, chlorine-substituted C.sub.1 -C.sub.4 -alkyl, and cyano-, fluorine- and/or chlorine-, methoxy- or ethoxy-substituted radical from the group consisting of C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkenyl and C.sub.1 -C.sub.4 -alkinyl
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkenyl or alkinyl are in each case--even in combination with heteroatoms, such as in alkoxy--straight-chain or branched.
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
The invention provides in particular compounds of the formula (I) in which di- or trisubstituted by identical or different substituents from the group consisting of chlorine, bromine, methyl, ethyl or trifluoromethyl, optionally fluorine- and/or chlorine-substituted methyl or ethyl, chlorine-substituted methyl or ethyl, and and/or chlorine-substituted methyl, ethyl, n- or i-propyl, propenyl or propinyl
The abovementioned general or preferred radical definitions apply both to the end products and to the corresponding precursors or intermediates. These radical definitions can be combined with each other as desired, that is to say combinations between the respective ranges of preferred compounds are also possible.
Examples of compounds of the formula (I) are listed in groups below. ##STR4##
Az has, for example, the meanings listed below: pyrazol-1-yl, imidazol-1-yl, 1,2,4-triazol-1-yl, 1,3,4-triazol-1-yl, 3-methyl-pyrazol-1-yl, 4-methyl-pyrazol-1-yl, 5-methyl-pyrazol-1-yl, 3,5-dimethyl-pyrazol-1-yl, 3,4,5-trimethyl-pyrazol-1-yl, 4-chloro-pyrazol-1-yl, 4-bromo-pyrazol-1-yl, 4-chloro-3-methyl-pyrazol-1-yl, 4-bromo-3-methyl-pyrazol-1-yl, 4-chloro-3,5-dimethyl-pyrazol-1-yl, 4-bromo-3,5-dimethyl-pyrazol-1-yl, 2-methyl-imidazol-1-yl, 4-methyl-imidazol-1-yl, 2,4-dimethyl-imidazol-1-yl and 3,5-dimethyl-1,2,4-triazol-1-yl. ##STR5##
Az has, for example, the meanings listed above for group 1. ##STR6##
Az has, for example, the meanings listed above for group 1. ##STR7##
Az has, for exam

REFERENCES:
patent: 5169430 (1992-12-01), Strunk

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