Substituted acylamino phenyl uracils

Details Substituted acylamino phenyl uracils Substituted acylamino phenyl uracils

2001-02-20

2003-09-09

Ford, John M. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C544S310000, C544S311000, C544S312000, C544S296000

Reexamination Certificate

active

06617281

ABSTRACT:

This application is a 371 National Application of PCT/EP99/04743, filed Jul. 7, 1999.
FIELD OF THE INVENTION
The invention relates to new substituted acylaminophenyl-uracils, to processes for their preparation, and to their use as herbicides.
BACKGROUND OF THE INVENTION
Certain substituted aryluracils have already been disclosed in the (patent) literature (cf. EP-A-408382, U.S. Pat. No. 5,084,084, U.S. Pat. No. 5,127,935, U.S. Pat. No. 5,154,755, EP-A-563384, U.S. Pat. No. 5,356,863, WO-A-95/29168, WO-A-96/35679, WO-A-97/01542, WO-A-97/09319, WO-A-98/06706). However, these compounds have not gained any particular importance to date.
SUMMARY OF THE INVENTION
Novel substituted acylaminophenyl-uracils have the general formula (I)
in which:
n represents the numbers 0 or 1,
A represents in each case optionally substituted alkanediyl(alkylene) or acycloalkanediyl, or—with the proviso that n then represents 1—also represents a single bond or is attached to Ar via an alkanediyl grouping,
Ar represents in each case optionally substituted aryl, arylalkyl, heterocyclyl or heterocyclylalkyl,
Q represents O, S, SO, SO
2
, NH or N(alkyl),
R
1
represents hydrogen, amino or optionally substituted alkyl,
R
2
represents carboxyl, cyano, carbamoyl, thiocarbamoyl or represents in each case optionally substituted alkyl or alkoxycarbonyl,
R
3
represents hydrogen, halogen or optionally substituted alkyl,
R
4
represents hydrogen, cyano, carbamoyl, thiocarbamoyl or halogen,
R
5
represents cyano, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted alkyl or alkoxy, and
R
6
represents hydrogen or represents in each case optionally substituted alkyl, alkylcarbonyl, alkoxycarbonyl, alkylsulphonyl, alkenyl, alkenylcarbonyl, alkenylsulphonyl, alkinyl, cycloalkylcarbonyl, cycloalkylsulphonyl, arylcarbonyl, arylsulphonyl, arylalkylcarbonyl, arylalkylsulphonyl, heterocyclylcarbonyl or heterocyclylsulphonyl.
DETAILED DESCRIPTION
In the definitions, the hydrocarbon chains, such as alkyl or alkanediyl—also in connection with heteroatoms such as in alkoxy—are in each case straight-chain or branched.
In as far as the compounds of the general formula (I) according to the invention contain asymmetrically substituted carbon atoms, the invention relates in each case to the R enantiomers and the S enantiomers and to any mixtures of these enantiomers, in particular the racemates.
A preferably represents in each case optionally halogen-substituted alkanediyl (alkylene) having 1 to 6 carbon atoms or cycloalkanediyl having 3 to 6 carbon atoms or—in the case that n then represents 1—also represents a single bond or is attached to Ar via an alkanediyl grouping having 1 to 3 carbon atoms;
Ar preferably represents in each case optionally substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety, or represents in each case optionally substituted heterocyclyl or heterocyclylalkyl having in each case 1 to 5 carbon atoms and at least one heteroatom (up to 4 nitrogen atoms and/or optionally 1 or 2 oxygen or sulphur atoms),
where the substituents that are possible in each case are preferably selected from the following list:
nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, C
1
-C
4
-alkyl, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-halogenoalkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-halogenoalkylthio, C
1
-C
4
-alkylsulphinyl, C
1
-C
4
-halogenoalkylsulphinyl, C
1
-C
4
-alkylsulphonyl, C
1
-C
4
-lalogenoalkylsulphonyl, C
1
-C
4
-alkylamino, di-(C
1
-C
4
-alkyl)-amino, C
1
-C
4
-alkyl-carbonyl, C
1
-C
4
-alkoxycarbonyl, C
1
-C
4
-alkylamino-carbonyl, di-(C
1
-C
4
-alkyl)-amino-carbonyl, di-(C
1
-C
4
-alkyl)-amino-sulphonyl,
Q preferably represents O (oxygen), S (sulphur), SO, SO
2
, NH or N(C
1
-C
4
-alkyl),
R
1
preferably represents hydrogen, amino or optionally cyano-, carboxyl-, halogen-, C
1
-C
4
-alkoxy-or C
1
-C
4
-alkoxycarbonyl-substituted alkyl having 1 to 6 carbon atoms,
R
2
preferably represents carboxyl, cyano, carbamoyl, thiocarbamoyl or represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl or alkoxycarbonyl having in each case 1 to 6 carbon atoms in the alkyl groups,
R
3
preferably represents hydrogen, halogen or optionally halogen-substituted alkyl having 1 to 6 carbon atoms,
R
4
preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine or chlorine,
R
5
preferably represents cyano, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally halogen-substituted alkyl or alkoxy having in each case 1 to 4 carbon atoms, and
R
6
preferably represents hydrogen, represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkylcarbonyl or alkoxycarbonyl having in each case 1 to 6 carbon atoms in the alkyl groups, represents optionally halogen-substituted alkylsulphonyl having 1 to 6 carbon atoms, represents in each case optionally halogen-substituted alkenyl, alkenylcarbonyl, alkenylsulphonyl or alkinyl having in each case up to 6 carbon atoms, represents in each case optionally halogen-substituted cycloalkylcarbonyl or cycloalkylsulphonyl having in each case 3 to 6 carbon atoms in the cycloalkyl groups, represents in each case optionally nitro-, cyano-, halogen-, C
1
-C
4
-alkyl-, C
1
-C
4
-halogenoalkyl-, C
1
-C
4
-alkoxy-, C
1
-C
4
-halogenoalkoxy-, C
1
-C
4
-alkylthio-, C
1
-C
4
-halogenoalkylthio-, C
1
-C
4
-alkylsulphinyl-, C
1
-C
4
-halogenoalkylsulphinyl-, C
1
-C
4
-alkylsulphonyl-, C
1
-C
4
-halogenoalkylsulphonyl, C
1
-C
4
-alkyl-carbonyl-, C
1
-C
4
-alkoxy-carbonyl- or di-(C
1
-C
4
-alkyl-amino)-sulphonyl-substituted arylcarbonyl, arylsulphonyl, arylalkylcarbonyl or arylalkylsulphonyl having in each case 6 or 10 carbon atoms in the aryl groups and optionally 1 to 4 carbon atoms in the alkyl moiety, or represents in each case optionally nitro-, cyano-, halogen-, C
1
-C
4
-alkyl-, C
1
-C
4
-halogenoalkyl-, C
1
-C
4
-alkoxy-, C
1
-C
4
-halogenoalkoxy-, C
1
-C
4
-alkylthio-, C
1
-C
4
-halogenoalkylthio-, C
1
-C
4
-alkylsulphinyl-, C
1
-C
4
-halogenoalkylsulphinyl-, C
1
-C
4
-alkylsulphonyl-, C
1
-C
4
-halogenoalkylsulphonyl-, C
1
-C
4
-alkyl-carbonyl-, C
1
-C
4
-alkoxy-carbonyl- or di-(C
1
-C
4
-alkyl-amino)-sulphonyl-substituted heterocyclyl-carbonyl or heterocyclylsulphonyl having 1 to 5 carbon atoms and 1 to 4 nitrogen atoms and/or 1 or 2 oxygen or sulphur atoms;
A particularly preferably represents in each case optionally fluorine- and/or chlorine-substituted methylene, ethane-1,1-diyl(ethylidene), ethane-1,2-diyl (dimethylene), propane-1,1-diyl(propylidene), propane-1,2-diyl or propane-1,3-diyl(trimethylene), cyclopropane-1,1-diyl, cyclopropane-1,2-diyl, cyclobutane-1,1-diyl, cyclopentane-1,1-diyl or cyclohexane-1,1-diyl, or—in the case that n then represents 1—also represents a single bond, or is attached to Ar via a 1,2-ethanediyl(dimethylene) grouping;
Ar particularly preferably represents in each case optionally substituted phenyl, naphthyl, benzyl, 1-phenyl-ethyl, 2-phenyl-ethyl, 1-phenyl-propyl, 2-phenyl-propyl or 3-phenyl-propyl, or represents in each case optionally substituted heterocyclyl or heterocyclylalkyl selected from the group consisting of oxiranyl, oxiranylmethyl, oxetanyl, oxetanylmethyl, furyl, furylmethyl, tetrahydrofuryl, tetrahydrofurylmethyl, thienyl, thienylmethyl, tetrahydrothienyl, tetrahydrothienylmethyl, benzofuryl, benzofurylmethyl, dihydrobenzofuryl, dihydrobenzofurylmethyl, benzothienyl, benzothienylmethyl, pyrrolyl, pyrrolylmethyl, pyrazolyl, pyrazolylmethyl, pyranyl, pyranylmethyl, benzopyranyl, benzopyranylmethyl, dihydrobenzopyranyl, dihydrobenzopyranylmethyl, tetrahydrobenzopyranyl, tetrahydrobenzopyranylmethyl, pyridinyl, pyridinylmethyl, pyrimidinyl, pyrimidinylmethyl,
where the substituents that arc possible in each case are preferably selected from the following list:
nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or

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