Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1996-10-28
2000-06-20
Dees, Jose' G.
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
504273, 5482622, 5482632, 5482634, 5482636, 5482638, 5482642, 5482648, 5482652, 5482656, 5482646, 5482672, 5482694, C07D24908, C07D24912
Patent
active
06077813&
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP95/01507 filed Apr. 21, 1995.
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-dichlorobenzothioamide ("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) ##STR2## in which
R.sup.1 represents hydrogen or halogen,
R.sup.2 represents the following group
A.sup.1 represents a single bond, or represents oxygen, sulphur, --SO--, --SO.sub.2 --, --CO-- or the group --N--A.sup.4 --, in which A.sup.4 represents hydrogen, hydroxyl, alkyl, alkenyl, alkinyl, alkoxy, aryl, alkylsulphonyl or arylsulphonyl,
A.sup.1 additionally represents in each case optionally substituted alkanediyl, alkenediyl, alkinediyl, cycloalkanediyl, cycloalkenediyl or arenediyl,
A.sup.2 represents a single bond, or represents oxygen, sulphur, --SO--, --SO.sub.2 --, --CO-- or the group --N--A.sup.4 --, in which A.sup.4 represents hydrogen, hydroxyl, alkyl, alkenyl, alkinyl, aryl, alkoxy, alkylsulphonyl or arylsulphonyl,
A.sup.2 additionally represents in each case optionally substituted alkanediyl, alkenediyl, alkinediyl, cycloalkanediyl, cycloalkenediyl or arenediyl,
A.sup.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.sup.3 represents hydrogen or halogen or together with R.sup.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.sub.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 nitrites of the general formula (II) ##STR3## in which
R.sup.1, R.sup.2, R.sup.3 and Z have the meanings given above are reacted with hydrogen sulphide (H.sub.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 (1) 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.sup.1 represents hydrogen, fluorine, chlorine or bromine,
R.sup.2 represents the following group
A.sup.1 represents a single bond, or represents oxygen, sulphur, --SO--, --SO.sub.2 --, --CO-- or the group --N--A.sup.4 --, in which A.sup.4 represents hydrogen, hydroxyl, C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.4 -alkenyl, C.sub.3 -C.sub.4 -alkinyl,
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Andree Roland
Dollinger Markus
Drewes Mark-Wilhelm
Findeisen Kurt
Haas Wilhelm
Badio Barbara
Bayer Aktiengesellschaft
Dees Jos,e G.
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