Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
2001-09-25
2002-09-17
Raymond, Richard L. (Department: 1624)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
C504S216000, C504S254000, C504S275000, C504S277000, C504S280000, C504S282000, C504S283000, C546S296000, C546S300000, C548S325100, C548S325500, C548S368400, C548S545000, C548S563000
Reexamination Certificate
active
06451736
ABSTRACT:
The invention relates to novel substituted aromatic thiocarboxamides, to processes for their preparation and to their use as herbicides.
It is already known that certain aromatic carbothioamides, for example 2,6-dichloro-benzothioamide (“chlorthiamid”), possess herbicidal properties (cf. GB-B 987253). However, the activity of this previously known compound, especially at low application rates and concentrations, is not entirely satisfactory in all areas of application.
The novel substituted aromatic thiocarboxamides have now been found of the general formula (I)
in which
R
1
represents hydrogen or halogen,
R
2
represents the following group
—A
1
—A
2
—A
3
in which
A
1
represents a single bond, or represents oxygen, sulphur, —SO—, —SO
2
—, —CO— or the group —N—A
4
—, in which A
4
represents hydrogen, hydroxyl, alkyl, alkenyl, alkinyl, alkoxy, aryl, alkylsulphonyl or arylsulphonyl,
A
1
additionally represents in each case optionally substituted alkanediyl, alkenediyl, alkinediyl, cycloalkanediyl, cycloalkenediyl or arenediyl,
A
2
represents a single bond, or represents oxygen, sulphur, —SO—, —SO
2
—, —CO— or the group —N—A
4
—, in which A
4
represents hydrogen, hydroxyl, alkyl, alkenyl, alkinyl, aryl, alkoxy, alkylsulphonyl or arylsulphonyl,
A
2
additionally represents in each case optionally substituted alkanediyl, alkenediyl, alkinediyl, cycloalkanediyl, cycloalkenediyl or arenediyl,
A
3
represents hydrogen, hydroxyl, amino, cyano, isocyano, thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulpho, chlorosulphonyl, halogen or represents in each case 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
3
represents hydrogen or halogen or together with R
2
represents an alkanediyl or an alkenediyl group which optionally contains at the beginning (or end) or within the hydrocarbon chain an oxygen atom, a sulphur atom, an SO
2
group, an NH group, an N-alkyl group, a carbonyl group and/or a thiocarbonyl group, and
Z represents in each case optionally substituted monocyclic or bicyclic, saturated or unsaturated heterocyclyl, heterocyclylamino or heterocyclylimino.
The novel substituted aromatic thiocarboxamides of the general formula (I) are obtained if substituted aromatic nitriles of the general formula (II)
in which
R
1
, R
2
, R
3
and Z have the meanings given above are reacted with hydrogen sulphide (H
2
S) or with thioacetamide, optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent.
The novel substituted aromatic thiocarboxamides of the general formula (I) are notable for strong and selective herbicidal activity.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkinyl—alone or in conjunction with heteroatoms, such as in alkoxy, alkylthio or alkylamino—are each straight-chain or branched.
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, especially fluorine or chlorine.
The invention preferably relates to compounds of the formula (I) in which
R
1
represents hydrogen, fluorine, chlorine or bromine,
R
2
represents the following group
—A
1
—A
2
—A
3
in which
A
1
represents a single bond, or represents oxygen, sulphur, —SO—, —SO
2
—, —CO— or the group —N—A
4
—, in which A
4
represents hydrogen, hydroxyl, C
1
-C
4
-alkyl, C
3
-C
4
-alkenyl, C
3
-C
4
-alkinyl, C
1
-C
4
-alkoxy, phenyl, C
1
-C
4
-alkylsulphonyl or phenylsulphonyl,
A
1
additionally represents in each case optionally fluorine- or chlorine-substituted C
1
-C
6
-alkanediyl, C
2
-C
6
-alkenediyl, C
2
-C
6
-alkinediyl, C
3
-C
6
-cycloalkanediyl, C
3
-C
6
-cycloalkenediyl or phenylene,
A
2
represents a single bond, or represents oxygen, sulphur, —SO—, —SO
2
—, —CO—or the group —N—A
4
—, in which A
4
represents hydrogen, hydroxyl, C
1
-C
4
-alkyl, C
3
-C
4
-alkenyl, C
3
-C
4
-alkinyl, C
1
-C
4
-alkoxy, phenyl, C
1
-C
4
-alkylsulphonyl or phenylsulphonyl,
A
2
additionally represents in each case optionally fluorine- or chlorine-substituted C
1
-C
6
-alkanediyl, C
2
-C
6
-alkenediyl, C
2
-C
6
-alkinediyl, C
3
-C
6
-cycloalkanediyl, C
3
-C
6
-cycloalkenediyl or phenylene,
A
3
represents hydrogen, hydroxyl, amino, cyano, isocyano, thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulpho, chlorosulphonyl, halogen, or represents in each case optionally halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy(thio)phosphoryl having in each case 1 to 6 carbon atoms in the alkyl groups, or represents in each case optionally halogen-substituted alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkinyl, alkinyloxy, alkinylamino or alkinyloxycarbonyl having in each case 2 to 6 carbon atoms in the alkenyl, alkylidene or alkinyl groups, or represents in each case optionally halogen-, cyano-, carboxyl-, C
1
-C
4
-alkyl- and/or C
1
-C
4
-alkoxy-carbonyl-substituted cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl groups, or represents in each case optionally nitro-, cyano-, carboxyl-, halogen-, C
1
-C
4
-alkyl-, C
1
-C
4
-halogenoalkyl-, C
1
-C
4
-alkyloxy-, C
1
-C
4
-halogenoalkyloxy- and/or C
1
-C
4
-alkoxy-carbonyl-substituted phenyl, phenyloxy, phenyl-C
1
-C
4
-alkyl, phenyl-C
1
-C
4
-alkoxy, phenyloxycarbonyl or phenyl-C
1
-C
4
-alkoxycarbonyl, (in each case optionally totally or partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolyl-C
1
-C
4
-alkyl, furyl-C
1
-C
4
-alkyl, thienyl-C
1
-C
4
-alkyl, oxazolyl-C
1
-C
4
-alkyl, isoxazole-C
1
-C
4
-alkyl, thiazole-C
1
-C
4
-alkyl, pyridinyl-C
1
-C
4
-alkyl, pyrimidinyl-C
1
-C
4
-alkyl, pyrazolylmethoxy or furylmethoxy, or represents perhydropyranylmethoxy or pyridylmethoxy,
R
3
represents hydrogen, fluorine, chlorine or bromine or together with R
2
represents an alkanediyl or alkenediyl group having in each case up to 4 carbon atoms which optionally contains at the beginning (or end) or within the hydrocarbon chain an oxygen atom, a sulphur atom, an SO
2
group, an NH group, an N—C
1
-C
4
-alkyl group, a carbonyl group and/or a thiocarbonyl group, and
Z represents in each case monocyclic or bicyclic, saturated or unsaturated heterocyclyl, heterocyclylamino or heterocyclylimino having in each case 2 to 6 carbon atoms and 1 to 4 nitrogen atoms in the heterocyclic ring system, which optionally additionally contains an oxygen atom or sulphur atom and/or optionally up to three groups from the series —CO—, —CS—, —SO— and/or SO
2
—, and which is optionally substituted by one or more groups from the series nitro, hydroxyl, amino, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, C
1
-C
6
-alkyl (which is optionally substituted by halogen or C
1
-C
4
-alkoxy), C
2
-C
6
-alkenyl or C
2
-C
6
-alkinyl (which are in each case optionally substituted by halogen), C
1
-C
6
-alkoxy or C
1
-C
6
-alkoxy-carbonyl (which are in each case optionally substituted by halogen or C
1
-C
4
-alkoxy), C
2
-C
6
-alkenyloxy or C
2
-C
6
-alkinyloxy (which are in each case optionally substituted by halogen), C
1
-C
6
-alkylthio, C
2
-C
6
-alkenylthio or C
2
-C
6
-alkinylthio (which are in each case optionally substituted by halogen), C
1
-C
6
-alkylamino or
Andree Roland
Dollinger Markus
Drewes Mark-Wilhelm
Findeisen Kurt
Haas Wilhelm
Bayer Aktiengesellschaft
Norris & McLaughlin & Marcus
Raymond Richard L.
LandOfFree
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