Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1997-02-24
1999-03-02
Ford, John M.
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
504242, 544353, 544319, C07D23936, C07D23940, A01N 4354
Patent
active
058771212
DESCRIPTION:
BRIEF SUMMARY
The invention relates to novel substituted pyrimidin(ethi)ones, a process for their preparation and their use as herbicides.
Substituted pyrimidinones as potential herbicides already form the subject matter of one patent application, but they have hitherto not attained any major importance (cf. EP-A European Published Specification) 568041).
Novel substituted pyrimidin(ethi)ones of the general formula (I) have now been found ##STR2## in which
Q represents oxygen or sulphur,
R.sup.1 represents hydrogen, cyano, nitro, halogen, alkyl or halogenoalkyl,
R.sup.2 represents cyano or thiocarbamoyl,
R.sup.3 represents the following grouping
A.sup.1 represents a single bond, or oxygen, sulphur, --SO--, --SO.sub.2 --, --CO-- or the grouping --N--A.sup.4 -- where A.sup.4 represents hydrogen, hydroxyl, amino, alkyl, alkoxy, aryl, alkylcarbonyl, alkoxycarbonyl, alkylsulphonyl, arylcarbonyl or arylsulphonyl, or
A.sup.1 also represents respectively optionally substituted alkanediyl, alkenediyl, azaalkenediyl, alkinediyl, cycloalkanediyl, cycloalkenediyl or arenediyl,
A.sup.2 represents a single bond, or oxygen, sulphur, --SO--, --SO.sub.2 --, --CO-- or the grouping --N--A.sup.4 -- where A.sup.4 represents hydrogen, alkyl, aryl, alkylcarbonyl, alkylsulphonyl or arylsulphonyl,
A.sup.2 also represents respectively optionally substituted alkanediyl, alkenediyl, azaalkenediyl, alkinediyl, cycloalkanediyl, cycloalkenediyl or arenediyl, and
A.sup.3 represents hydrogen, hydroxyl, mercapto, amino, cyano, isocyano, thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulpho, chlorosulphonyl, halogen or respectively optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkoxycarbonyl, dialkoxy(thio)phosphoryl, alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkinyl, alkinyloxy, alkinylamino, alkinyloxycarbonyl, cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl, cycloalkylalkoxycarbonyl, aryl, aryloxy, arylalkyl, arylalkoxy, aryloxycarbonyl, arylalkoxycarbonyl, heterocyclyl, heterocyclylalkyl, heterocyclylalkoxy or heterocyclylalkoxycarbonyl,
R.sup.4 represents hydrogen, halogen, alkyl or halogenoalkyl, and
R.sup.5 represents alkyl or halogenoalkyl or together with R.sup.4 represents alkanediyl.
The novel substituted pyrimidin(ethi)ones of the general formula (I) are obtained by reacting
halogenoarenes of the general formula (II) ##STR3## in which
R.sup.1, R.sup.2 and R.sup.3 have the abovementioned meanings, and
X represents halogen,
with pyrimidin(ethi)ones of the general formula (III) ##STR4## in which
Q, R.sup.4 and R.sup.5 have the abovementioned meanings,
if necessary in the presence of an acid acceptor and if necessary in the presence of a diluent, and optionally subjecting, in the resulting compounds of the formula (I), the groups designated Q, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 in a conventional manner to further chemical modifications within the purview of the radical definitions given above.
The novel substituted pyrimidin(ethi)ones of the general formula (I) are distinguished by strong and selective herbicidal activity.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkinyl--also when attached to heteroatoms, as in alkoxy, alkylthio or alkylamino--are in each case straight-chain or branched.
Halogen represents in general fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
The invention preferably relates to compounds of the formula (I) in which
Q represents oxygen or sulphur,
R.sup.1 represents hydrogen, cyano, nitro, fluorine, chlorine, bromine or optionally fluorine- and/or chlorine-substituted alkyl having 1 to 4 carbon atoms,
R.sup.2 represents cyano or thiocarbamoyl,
R.sup.3 represents the following grouping
A.sup.1 represents a single bond, or oxygen, sulphur, --SO--, --SO.sub.2 --, --CO-- or the grouping --N--A.sup.4 -- where A.sup.4 represents hy
Andree Roland
Dollinger Markus
Drewes Mark Wilhelm
Santel Hans-Joachim
Bayer Aktiengesellschaft
Ford John M.
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