Organic compounds -- part of the class 532-570 series – Organic compounds – Nitrogen attached directly or indirectly to the purine ring...
Reexamination Certificate
1999-06-02
2001-01-16
Shah, Mukund J. (Department: 1611)
Organic compounds -- part of the class 532-570 series
Organic compounds
Nitrogen attached directly or indirectly to the purine ring...
C544S310000, C544S311000
Reexamination Certificate
active
06175010
ABSTRACT:
TECHNICAL FIELD OF THE INVENTION
The present invention relates to novel 3-amino-1-cyanophenyl-uracils, to a process for their preparation and to their use as herbicides.
BACKGROUND OF THE INVENTION
It is already known that certain 3-alkyl-1-cyanophenyl-uracils have herbicidal properties (cf. EP-A 0 473 551). Thus, for example, isopropyl 2-cyano-5-[3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluoro-benzoate can be used for controlling weeds. However, at low application rates, the efficacy of this substance is not always satisfactory.
DETAILED DESCRIPTION OF THE INVENTION
This invention, accordingly, provides novel 3-amino-1-cyano-phenyl-uracils of the formula
in which
R
1
represents hydrogen or represents in each case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl,
R
2
represents hydrogen, cyano or halogen,
R
3
represents hydrogen, halogen or optionally substituted alkyl,
R
4
represents optionally substituted alkyl.
Furthermore, it has been found that 3-amino-1-cyanophenyl-uracils of the formula (I) are obtained when 1-cyanophenyl-uracils of the formula
in which
R
1
, R
2
, R
3
and R
4
are each as defined above,
are reacted with an electrophilic aminating agent,
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 3-amino-1-cyanophenyl-uracils of the formula (I) have very good herbicidal properties.
Surprisingly, the 3-amino-1-cyanophenyl-uracils of the formula (I) according to the invention have considerably better herbicidal activity than isopropyl 2-cyano-5-[3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluoro-benzoate, which is a prior-art active compound of similar constitution and the same direction of action.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkenyl or alkinyl, are in each case straight-chain or branched.
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably represents fluorine, chlorine or bromine, in particular represents fluorine or chlorine.
The formula (I) provides a general definition of the 3-amino-1-cyanophenyl-uracils according to the invention. Preference is given to compounds of the formula (I) in which
R
1
represents hydrogen or represents optionally cyano-, carboxyl-, halogen-, C
1
-C
4
-alkoxy- or C
1
-C
4
-alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms or
represents in each case optionally cyano-, carboxyl- or C
1
-C
4
-alkoxy-carbonyl-substituted alkenyl or alkinyl having in each case 2 to 6 carbon atoms, or
represents cycloalkyl or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety and being in each case optionally mono- to tetrasubstituted by identical or different substituents selected from the group consisting of cyano, carboxyl, halogen, C
1
-C
4
-alkyl and C
1
-C
4
-alkoxy-carbonyl, or represents aryl or arylalkyl having 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety and being in each case optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of nitro, cyano, carboxyl, halogen, C
1
-C
4
-alkyl, halogeno-C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, halogeno-C
1
-C
4
-alkoxy and/or C
1
-C
4
-alkoxy-carbonyl, or
represents heterocyclyl or heterocyclylalkyl from the series oxetanyl, furyl, furylmethyl, tetrahydrofuryl, tetrahydrofurylmethyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, oxadiazolyl, pyridinyl, pyridinylmethyl, each of which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of cyano, carboxyl, halogen, C
1
-C
4
-alkyl, halogeno-C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy and/or halogeno-C
1
-C
4
-alkoxy,
R
2
represents hydrogen, cyano, fluorine, chlorine or bromine,
R
3
represents hydrogen, fluorine, chlorine, bromine or represents alkyl having 1 to 4 carbon atoms which is optionally mono- to pentasubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine and bromine, and
R
4
represents alkyl having 1 to 4 carbon atoms or represents halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms.
Particular preference is given to compounds of the formula (I) in which
R
1
represents hydrogen or represents optionally cyano-, carboxyl-, fluorine-, chlorine-, methoxy-, ethoxy-, propoxy-, methoxycarbonyl-, ethoxycarbonyl- or propoxycarbonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or
represents in each case optionally cyano-, carboxyl-, methoxycarbonyl- or ethoxycarbonyl-substituted propenyl, butenyl, propinyl or butinyl, or
represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each of which is optionally mono- to tetrasubstituted by identical or different substituents selected from the group consisting of cyano, carboxyl, fluorine, chlorine, methyl, ethyl, methoxycarbonyl and ethoxycarbonyl, or represents phenyl or benzyl, each of which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of nitro, cyano, carboxyl, fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl and ethoxycarbonyl, or
represents heterocyclyl or heterocyclylalkyl from the series oxetanyl, furyl, furylmethyl, tetrahydrofuryl, tetrahydrofurylmethyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, oxadiazolyl, pyridinyl, pyridinylmethyl, each of which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of cyano, carboxyl, fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy and trifluoromethoxy,
R
2
represents hydrogen, fluorine or chlorine,
R
3
represents hydrogen, fluorine, chlorine, methyl, ethyl or represents halogenoalkyl having 1 or 2 carbon atoms and 1 to 3 fluorine and/or chlorine atoms and
R
4
represents methyl, ethyl or represents halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 fluorine and/or chlorine atoms.
The abovementioned general or preferred radical definitions apply both to the end products of the formula (I) and also, correspondingly, to the starting materials or intermediates required in each case for the preparation. These radical definitions can be combined with each other at will, i.e. including combinations between the given preferred ranges.
Examples of the compounds of the formula (I) according to the invention are listed in the groups below.
R
1
here has the following meanings:
hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, fluoroethyl, chloroethyl, chlorofluoroethyl, difluoroethyl, dichloroethyl, trifluoroethyl, trichloroethyl, chlorodifluoroethyl, fluoropropyl, chloropropyl, difluoropropyl, dichloropropyl, trifluoropropyl, trichloropropyl, cyanoethyl, cyanopropyl, cyanobutyl, carboxymethyl, carboxyethyl, carboxypropyl, carboxybutyl, methoxymethyl, ethoxymethyl, propoxymethyl, methoxyethyl, ethoxyethyl, propoxyethyl, methoxypropyl, ethoxypropyl, propoxypropyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylethyl, propoxycarbonylethyl, methoxycarbonylpropyl, ethoxycarbonylpropyl, propoxycarbonylpropyl, 1-propen-3-yl (allyl), 3-methyl-1-propen-3-yl, 2-buten-4-yl (crotonyl), 1-propin-3-yl (propargyl), 3-methyl-1-propin-3-yl, 2-butin-4-yl, cyclopropyl, cyanocyclopropyl, carboxycyclopropyl, difluorocyclopropyl, dichlorocyclopropyl, methylcyclopropyl, methoxycarbonylcyclopropyl, ethoxycarbonylcyclopropyl, cyclobutyl, cyanocyclobutyl, carboxycyclobutyl, difluorocyclopropyl, trifluorocyclobutyl, tetrafluorocyclobutyl, chlorotrifluorocyclobutyl, methylcyclobutyl, cyclopentyl, cyanocyc
Andree Roland
Dollinger Markus
Drewes Mark Wilhelm
Bayer Aktiengesellschaft
Gil Joseph C.
Liu Hong
Shah Mukund J.
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