Substituted phenyl uracils

Details Substituted phenyl uracils Substituted phenyl uracils

2002-01-10

2003-05-13

Ford, John M. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C544S309000, C544S311000, C544S312000, C544S313000, C544S314000

Reexamination Certificate

active

06562759

ABSTRACT:

FIELD OF THE INVENTION
The invention relates to novel substituted phenyluracils, to processes for their preparation and to their use as herbicides.
BACKGROUND OF THE INVENTION
Certain substituted aryluracils are already known from the (patent) literature (cf. EP-A-255 047, EP-A-260 621, EP-A-408 382, EP-A-438 209, EP-A-473 551, EP-A-517 181, EP-A-542 685, EP-A-563 384, WO-A-91/00278, WO-A-91/07393, WO-A-93/06090, WO-A-93/14073, WO-A-95/06641, WO-A-97/45418, U.S. Pat. Nos. 4,979,982, 5,084,084, 5,127,935, 5,154,755, 5,169,430, 5,486,610, 5,356,863). However, these compounds have hitherto not attained any particular significance.
SUMMARY OF THE INVENTION
A substituted phenyluracil of the general formula (I)
which has herbicidal activity.
DETAILED DESCRIPTION OF THE INVENTION
A represents alkanediyl or alkenediyl, each of which has 2 to 5 carbon atoms and each of which is optionally substituted by cyano, halogen or by in each case optionally halogen- or C
1
-C
4
-alkoxy-substituted C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy-carbonyl or C
2
-C
4
-alkenyl or interrupted by O (oxygen), or represents cyclohexane-1,2-diyl or 1,2-phenylene,
Q
1
represents O (oxygen) or S (sulphur),
Q
2
represents O (oxygen) or S (sulphur),
R
1
represents hydrogen, amino or optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl having 1 to 4 carbon atoms,
R
2
represents optionally halogen-substituted alkyl having 1 to 4 carbon atoms,
R
3
represents hydrogen, halogen or optionally halogen-substituted alkyl having 1 to 4 carbon atoms,
R
4
represents hydrogen, cyano, carbamoyl, thiocarbamoyl or halogen,
R
5
represents cyano, carbamoyl, thiocarbamoyl or in each case optionally halogen-substituted alkyl or alkoxy having in each case 1 to 4 carbon atoms, and
R
6
represents hydrogen or alkyl having 1 to 4 carbon atoms.
Preferred substituents or ranges of the radicals present in the formulae listed above and below are defined below.
A preferably represents ethane-1,2-diyl (dimethylene), propane-1,3-diyl (tri-methylene), ethene-1,2-diyl or propene-1,3-diyl, each of which is optionally substituted by cyano, fluorine, chlorine, bromine or by in each case optionally fluorine- and/or chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, ethenyl or propenyl or interrupted by O (oxygen), or represents cyclohexane-1,2-diyl or 1,2-phenylene.
Q
1
preferably represents O (oxygen).
Q
2
preferably represents O (oxygen).
R
1
preferably represents hydrogen, amino or in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl.
R
2
preferably represents in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl.
R
3
preferably represents hydrogen, fluorine, chlorine or in each case optionally fluorine- and/or chlorine-substituted methyl or ethyl.
R
4
preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine or bromine.
R
5
preferably represents cyano, carbamoyl, thiocarbamoyl or in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, methoxy or ethoxy.
R
6
preferably represents hydrogen, methyl or ethyl.
A particularly preferably represents in each case optionally fluorine-, chlorine-, methyl-, ethyl-, methoxycarbonyl- or ethoxycarbonyl-substituted ethane-1,2-diyl (dimethylene), propane-1,3-diyl (trimethylene) or ethene-1,2-diyl, or represents cyclohexane-1,2-diyl or 1,2-phenylene.
R
1
particularly preferably represents hydrogen, amino or methyl.
R
2
particularly preferably represents in each case fluorine- and/or chlorine-substituted methyl or ethyl.
R
3
particularly preferably represents hydrogen, fluorine, chlorine or optionally fluorine- and/or chlorine-substituted methyl.
R
4
particularly preferably represents hydrogen, fluorine or chlorine.
R
5
particularly preferably represents cyano, carbamoyl, thiocarbamoyl or in each case optionally fluorine- and/or chlorine-substituted methyl or methoxy.
R
6
particularly preferably represents hydrogen or methyl.
A very particularly preferably represents in each case optionally fluorine-, chlorine-, methyl-, ethyl-, methoxycarbonyl- or ethoxycarbonyl-substituted ethane-1,2-diyl (dimethylene) or propane-1,3-diyl (trimethylene).
R
1
very particularly preferably represents methyl.
R
2
very particularly preferably represents trifluoromethyl.
R
3
very particularly preferably represents hydrogen, chlorine or methyl.
R
4
very particularly preferably represents fluorine or chlorine.
R
5
very particularly preferably represents cyano or thiocarbamoyl.
R
6
very particularly preferably represents hydrogen.
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 one another as desired, i.e. including combinations between the given preferred ranges.
Preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings listed above as being preferred.
Particular preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings listed above as being particularly preferred.
Very particular preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings listed above as being very particularly preferred.
Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl, are—including in combination with heteroatoms, such as in alkoxy—in each case straight-chain or branched as far as this is possible.
Optionally substituted radicals can be mono- or polysubstituted, where in the case of polysubstitution the substituents can be identical or different.
The novel substituted phenyluracils of the general formula (I) have interesting biological properties. In particular, they have strong herbicidal activity.
The novel substituted phenyluracils of the general formula (I) are obtained when phenyluracils of the general formula (II)
in which
R
1
, R
2
, R
3
, R
4
, R
5
and R
6
are each as defined above,
are reacted with dinucleophilic compounds of the general formula (III)
in which
A, Q
1
and Q
2
are each as defined above,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
and subsequent reactions within the scope of the above definition of substituents are carried out, if appropriate, by customary methods on the resulting compounds of the general formula (I).
The compounds of the general formula (I) can be converted by customary methods into other compounds of the general formula (I) according to the above definition of substituents, for example by amination or alkylation (for example R
1
: H→NH
2
, H→CH
3
), or else, for example, by reaction with hydrogen sulphide (R
5
: CN→CSNH
2
).
The compounds of the general formula (I) according to the invention in which R
5
represents cyano can in principle also be prepared according to the following formula scheme:
(X: halogen, in particular chlorine or bromine)
Using, for example, 1-(4-cyano-2-chloro-5-formyl-phenyl)-3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidine and propane-1,3-diol as starting materials, the course of the reaction in the process according to the invention can be illustrated by the following formula scheme:
The formula (II) provides a general definition of the phenyluracils to be used as starting materials in the process according to the invention for preparing compounds of the general formula (I). In the general formula (II), R
1
, R
2
, R
3
, R
4
, R
5
and R
6
each preferably have those meanings which have already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred, particularly preferred or very particularly preferred for R
1
,

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