Herbicidal arylimino-substituted triazoles, thiadiazoles or oxad

Details Herbicidal arylimino-substituted triazoles, thiadiazoles or oxad Herbicidal arylimino-substituted triazoles, thiadiazoles or oxad

1997-01-07

1998-06-16

Gerstl, Robert

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

504263, 504265, 544134, 548141, 548144, C07D285135, A01N 4382

Patent

active

057670412

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/EP95/02547 filed Jun. 30, 1995.
The invention relates to novel substituted aryliminoheterocycles, to processes for their preparation and to their use as herbicides.
Substituted aryliminoheterocycles have not been disclosed as yet as biologically active substances.
There have now been found novel substituted aryliminoheterocycles of the general formula (I) ##STR3## in which A represents oxygen, sulphur or the group N--R.sup.1 where alkenyl or alkinyl, ##STR4## where Q represents oxygen, sulphur or the group N--R.sup.1 (where R.sup.1 has the abovementioned meaning) and alkyl, alkenyl, alkinyl, cycloalkyl or cycloalkenyl, or alkinyl, and aryl or heteroaryl.
Thus, the general formula (I) represents the isomeric compounds of the general formulae (IA) and (IB) below. ##STR5##
The novel substituted aryliminoheterocycles of the general formula (I) are obtained when arylimino compounds of the general formula (II) ##STR6## in which A, R, R.sup.2 and Ar have the abovementioned meanings--and/or compounds which are tautomeric to these--are cyclized with reactive carbonic acid derivatives of the general formula (III) ##STR7## in which Q has the abovementioned meaning and in the presence of a diluent (IB), in the event that R.sup.2 in these formulae represents hydrogen, are reacted with alkylating agents of the general formula (IV) in the presence of a diluent.
The novel substituted aryliminoheterocycles of the general formula (I) are distinguished by a powerful 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, chlorine or bromine, in particular fluorine or chlorine.
The invention preferably relates to compounds of the formula (I) in which which is optionally substituted by cyano, halogen, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkyl-carbonyl or C.sub.1 -C.sub.4 -alkoxy-carbonyl, or represents alkenyl or alkinyl each of which has 2 to 6 carbon atoms and each of which is optionally substituted by halogen, ##STR8## where Q represents oxygen, sulphur or the group N--R.sup.1 (where R.sup.1 has the meaning given above as being preferred) and carbon atoms which is optionally substituted by cyano, halogen, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkyl-carbonyl or C.sub.1 -C.sub.4 -alkoxy-carbonyl, or represents alkenyl or alkinyl each of which has 2 to 6 carbon atoms and each of which is optionally substituted by halogen, or represents cycloalkyl having 3 to 6 carbon atoms or cycloalkenyl having 5 or 6 carbon atoms each of which is optionally substituted by halogen or C.sub.1 -C.sub.4 -alkyl, is optionally substituted by cyano, halogen, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkyl-carbonyl or C.sub.1 -C.sub.4 -alkoxy-carbonyl, or represents alkenyl or alkinyl each of which has 2 to 6 carbon atoms and each of which is optionally substituted by halogen, and below, ##STR9## each of which is optionally substituted, and in which R.sup.3 represents hydrogen or halogen, each case optionally halogen-substituted C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy, --SO.sub.2 --, --CO-- or the group --N--A.sup.4 -- where A.sup.4 represents hydrogen, hydroxyl, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, phenyl, C.sub.1 -C.sub.4 -alkylsulphonyl or phenylsulphonyl or -C.sub.6 -alkenediyl, C.sub.2 -C.sub.6 -azaalkenediyl, C.sub.2 -C.sub.6 -alkinediyl, C.sub.3 -C.sub.6 -cycloalkanediyl, C.sub.3 -C.sub.6 -cycloalkenediyl or phenylene, each of which is optionally substituted by fluorine, chlorine or bromine, --SO.sub.2 --, --CO-- or the group --N--A.sup.4 -- where A.sup.4 represents hydrogen, hydroxyl, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, phenyl, C.sub.1 -C.sub.4 -alkylsulphonyl or phenylsulphonyl or -C.sub.6 -alkenediyl, C.sub.2 -C.sub.6 -azaalkenediyl, C.sub.2 -C.sub.6 -alkinediyl, C.sub.3 -C.sub.6 -cycloalkanediyl, C.sub.3 -C.sub.6 -cycloalkenediyl or phenylene, each of

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