Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
1999-11-16
2001-06-12
Ford, John M. (Department: 1624)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
C544S311000, C544S312000
Reexamination Certificate
active
06245715
ABSTRACT:
TECHNICAL FIELD OF THE INVENTION
The invention relates to novel substituted iminoalkoxy-phenyluracils, to processes for their preparation and to their use as herbicides.
BACKGROUND OF THE INVENTION
Certain substituted aryluracils, such as, for example, the compound 3-[4-chloro-2-fluoro-5-(2-oxo-propoxy)-phenyl]-1-methyl-6-trifluoromethyl-(1H,3H)-pyrimidine-2,4-dione, are already known from the (patent) literature (cf. EP 255047). However, these compounds have hitherto not obtained any particular importance.
DETAILED DESCRIPTION OF THE INVENTION
This invention, accordingly, provides novel substituted iminoalkoxy-phenyluracils of the general formula (I)
in which
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, thiocarbamoyl or halogen,
R
5
represents cyano, thiocarbamoyl or halogen,
R
6
represents hydrogen or optionally substituted alkyl,
R
7
represents optionally substituted alkyl, and
R
8
represents hydroxyl, amino or represents in each case an optionally substituted radical from the group consisting of alkyl, alkoxy, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino, alkylsulphonylamino, alkenyl, alkinyl, alkenyloxy, alkinyloxy, aryl, aryloxy, arylamino, arylcarbonylamino, arylsulphonylamino, arylalkyl, arylalkylamino, arylalkylcarbonylarnino or arylalkylsulphonylamino.
The novel substituted iminoalkoxy-phenyluracils of the general formula (I) are obtained when substitued oxoalkoxy-phenyluracils of the general formula (II)
in which
R
1
, R
2
, R
3
, R
4
, R
5
, R
6
and R
7
are as defined above,
are reacted with amino compounds of the general formula (III)
H
2
N—R
8
(III)
in which
R
8
is as defined above
or with acid adducts of compounds of the general formula (III)
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, and electrophilic or nucleophilic substitution reactions or addition reactions within the scope of the definition of the substituents are subsequently carried out, if appropriate.
The compounds of the general formula (I) can be converted by customary methods into other compounds of the general formula (I) in accordance with the above definition, for example by amination or alkylation (for example R
1
: H→NH
2
, H→CH
3
), reaction with dicyanogen or hydrogen sulphide (for example R
5
: Br→CN, CN→CSNH
2
, cf. the Preparation Examples).
The novel substituted iminoalkoxy-phenyluracils of the general formula (I) have strong and selective herbicidal activity.
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 fluorine, chlorien or bromine, in particular fluorine or chlorine.
The invention preferably provides compounds of the formula (I) in which
R
1
represents hydrogen, amino or optionally cyano-, fluorine-, chlorine- or C
1
-C
4
-alkoxy-substituted C
1
-C
6
-alkyl,
R
2
represents carboxyl, cyano, carbamoyl, thiocarbamoyl or represents in each case optionally cyano-, fluorine-, chlorine- or C
1
-C
4
-alkoxy-substituted C
1
-C
4
-alkyl or C
1
-C
4
-alkoxycarbonyl,
R
3
represents hydrogen, fluorine, chlorine, bromine or optionally fluorine- or chlorine-substituted C
1
-C
4
-alkyl,
R
4
represents hydrogen, cyano, thiocarbamoyl, fluorine, chlorine or bromine,
R
5
represents cyano, thiocarbamoyl, fluorine, chlorine or bromine,
R
6
represents hydrogen or optionally cyano-, fluorine-, chlorine- or C
1
-C
4
-alkoxy-substituted C
1
-C
6
-alkyl,
R
7
represents optionally cyano-, fluorine-, chlorine- or C
1
-C
4
-alkoxy-substituted C
1
-C
6
-alkyl, and
R
8
represents hydroxyl, represents amino or represents in each case optionally carboxyl-, cyano-, halogen-, C
1
-C
4
-alkoxy- or C
1
-C
4
-alkoxy-carbonyl-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino or alkylsulphonylamino having in each case 1 to 6 carbon atoms,
R
8
furthermore represents in each case optionally halogen-substituted alkenyl, alkinyl, alkenyloxy or alkinyloxy having in each case 3 to 6 carbon atoms, or
R
8
furthermore represents in each case optionally nitro-, cyano-, carboxyl-, halogen-, C
1
-C
4
-alkyl-, C
1
-C
4
-halogenoalkyl-, C
1
-C
4
-alkoxy- or C
1
-C
4
-halogenoalkoxy-substituted aryl, aryloxy, arylamino, arylcarbonylamino, arylsulphonylamino, arylalkyl, arylalkylamino, arylalkylcarbonylamino or arylalkylsulphonylamino having in each case 6 or 10 carbon atoms in the aryl moiety and optionally 1 to 4 carbon atoms in the alkyl moiety.
The invention in particular relates to compounds of the formula (I) in which
R
1
represents hydrogen, represents amino or represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
R
2
represents carboxyl, cyano, carbamoyl, thiocarbamoyl or represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, methoxycarbonyl or ethoxycarbonyl,
R
3
represents hydrogen, fluorine, chlorine, bromine or represents in each case optionally fluorine- or chlorine-substituted methyl or ethyl,
R
4
represents hydrogen, fluorine or chlorine,
R
5
represents cyano, thiocarbamoyl, chlorine or bromine,
R
6
represents hydrogen or represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
R
7
represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, and
R
8
represents hydroxyl, represents amino, or represents in each case optionally carboxyl-, cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, acetylamino, propionylamino, methoxycarbonylamino, ethoxycarbonylamino, methylsulphonylamino or ethylsulphonylamino, or
R
8
furthermore represents in each case optionally fluorine-, chlorine- or bromine-substituted propenyl, butenyl, propinyl, butinyl, propenyloxy, butenyloxy, propinyloxy or butinyloxy, or
R
8
furthermore represents in each case optionally nitro-, cyano-, carboxyl-, fluorine-, chlorine-, bromine- methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butoxy-, difluoromethoxy-, trifluoromethoxy-substituted phenyl, phenoxy, phenylamino, benzoylamino, phenylsulphonylamino, benzyl, benzylamino, benzylcarbonylamino or benzylsulphonylamino.
The abovementioned general or preferred radical definitions apply both to the end products of the formula (I) and, correspondingly, to the starting materials or intermediates required in each case for the preparation. These radical definitions can be combined with each other as desired, i.e. including combinations between the given preferred ranges.
Using, for example, 3-[4-chloro-2-fluoro-5-(2-oxo-propoxy)-phenyl]-1-methyl-6-trifluoromethyl-(1H,3H)-pyrimidine-2,4-dione and O-methylhydroxylamine as starting materials, the course of the reaction in the preparation process according to the invention can be illustrated by the following scheme:
The formula (II) provides a general definition of the oxoalkoxy-phenyluracils to be used as starting materials in the process according to the invention for preparing compounds of the formula (I). In the formula (II), R
1
, R
2
, R
3
, R
4
, R
5
, R
6
and R
7
preferably or in particular have those meanings which have already been me
Andree Roland
Dollinger Markus
Drewes Mark Wilhelm
Bayer Aktiengesellschaft
Ford John M.
Gil Joseph C.
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