Substituted heterocyclyl-2H-chromenes

Details Substituted heterocyclyl-2H-chromenes Substituted heterocyclyl-2H-chromenes

2002-02-05

2003-06-03

Stockton, Laura L. (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S230000, C504S238000, C504S243000, C504S273000, C504S280000, C504S282000, C504S285000, C504S286000, C544S310000, C544S238000, C544S215000, C548S263200, C548S263400, C548S360100, C548S364400, C548S454000

Reexamination Certificate

active

06573219

ABSTRACT:

This application is a 371 of PCT/EP00/07263 filed Jul. 28, 2000.
The invention relates to novel substituted heterocyclyl-2H-chromenes, to a process for their preparation and to their use as herbicides.
It is already known that certain substituted heterocyclyl-2H-chromenes have herbicidal properties (cf. JP-A-09301973—cited in Chem. Abstracts 128:34781). However, these compounds have hitherto not attained any particular importance.
This invention, accordingly, provides the novel substituted heterocyclyl-2H-chromenes of the general formula (I)
in which
R
1
represents hydrogen, cyano or halogen,
R
2
represents cyano, thiocarbamoyl, halogen or represents in each case substituted alkyl or alkoxy,
R
3
represents hydrogen, amino, nitro, formyl, carboxyl, cyano, carbamoyl, thiocarbamoyl, halogen, represents hydroxyiminoalkyl or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonylamino, alkoxyiminoalkyl, alkenyl, alkenyloxy, alkenylthio, alkinyl, alkinyloxy, alkinylthio, cycloalkyl, cycloalkylalkyl, cycloalkyloxycarbonyl, phenyl or benzyl,
R
4
represents hydrogen, halogen or optionally substituted alkyl,
R
5
represents hydrogen, halogen or optionally substituted alkyl, and
Z represents one of the heterocyclic groupings below
 where
Q represents O (oxygen) or S (sulphur),
R
6
represents hydrogen, amino, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino, alkoxycarbonyl, dialkylamino, alkenyl, alkenyloxy, alkenylthio, alkinyl, alkinyloxy, alkinylthio, cycloalkyl or cycloalkylalkyl, and
R
7
represents hydrogen, hydroxyl, amino, cyano, or represents in each case optionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylamino, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, phenyl or phenylalkyl,
where, if appropriate, two adjacent radicals—R
6
and R
6
, R
7
and R
7
or R
6
and R
7
—together represent alkanediyl or alkenediyl, each of which is optionally substituted and/or optionally interrupted at the beginning (and/or at the end) or within the hydrocarbon chain by O (oxygen), S (sulphur) or a grouping selected from the group consisting of —SO—, SO
2
—, —NH— and —N(alkyl)—.
In the definitions, the hydrocarbon chains, such as alkyl or alkanediyl, are in each case straight-chain or branched—including in combination with heteroatoms, such as in alkoxy.
R
1
preferably represents hydrogen, cyano, fluorine, chlorine or bromine.
R
2
preferably represents cyano, thiocarbamoyl, fluorine, chlorine, bromine, or represents in each case optionally fluorine- and/or chlorine-substituted alkyl or alkoxy having in each case 1 to 4 carbon atoms.
R
3
preferably represents hydrogen, amino, nitro, formyl, carboxyl, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, represents hydroxyiminoalkyl having up to 6 carbon atoms, represents in each case optionally cyano-, hydroxyl-, fluorine-, chlorine-, bromine-, C
1
-C
4
-alkoxy-, C
1
-C
4
-alkyl-thio-, C
1
-C
4
-alkylsulphinyl-, C
1
-C
4
-alkylsulphonyl-, C
1
-C
4
-alkylsulphonyloxy- or C
1
-C
4
-alkylcarbonyloxy-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case up to 6 carbon atoms, represents in each case optionally cyano-, fluorine-, chlorine-, bromine- or C
1
-C
4
-alkoxy-substituted alkylcarbonyl, alkoxycarbonyl, alkylcarbonylamino or alkoxyiminoalkyl having in each case up to 6 carbon atoms, represents in each case optionally cyano-, fluorine-, chlorine- or bromine-substituted alkenyl, alkenyloxy, alkenylthio, alkinyl, alkinyloxy or alkinylthio having in each case up to 6 carbon atoms, represents in each case optionally cyano-, fluorine-, chlorine-, bromine- or C
1
-C
4
-alkyl-substituted cycloalkyl, cycloalkylalkyl or cycloalkyloxycarbonyl having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally up to 4 carbon atoms in the alkyl moiety, or represents in each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, C
1
-C
4
-alkyl- or C
1
-C
4
-alkoxy-substituted phenyl or benzyl.
R
4
preferably represents hydrogen, fluorine, chlorine, bromine, or represents optionally cyano-, fluorine-, chlorine- or C
1
-C
4
-alkoxy-substituted alkyl having 1 to 6 carbon atoms.
R
5
preferably represents hydrogen, fluorine, chlorine, bromine, or represents optionally cyano-, fluorine-, chlorine- or C
1
-C
4
-alkoxy-substituted alkyl having 1 to 6 carbon atoms.
Z preferably represents one of the heterocyclic groupings below
 where
Q preferably represents O (oxygen) or S (sulphur).
R
6
preferably represents hydrogen, amino, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino or alkoxycarbonyl having in each case up to 6 carbon atoms, represents dialkylamino having in each case up to 4 carbon atoms in the alkyl groups, represents in each case optionally cyano- or halogen-substituted alkenyl, alkinyl, alkenyloxy, alkinyloxy, alkenylthio, alkinylthio having in each case up to 6 carbon atoms, or represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkyl-substituted cycloalkyl or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally up to 4 carbon atoms in the alkyl moiety.
R
7
preferably represents hydrogen, hydroxyl, amino, cyano, represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alkoxycarbonyl or alkylamino having in each case up to 6 carbon atoms, represents in each case optionally cyano- or halogen-substituted alkenyl or alkinyl having in each case up to 6 carbon atoms, represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkyl-substituted cycloalkyl or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally up to 4 carbon atoms in the alkyl moiety, or represents in each case optionally nitro-, cyano-, halogen-, C
1
-C
4
-alkyl- or C
1
-C
4
-alkoxy-substituted phenyl, benzyl or phenylethyl.
Two adjacent radicals—R
6
and R
6
, R
7
and R
7
or R
6
and R
7
—preferably together represent alkanediyl or alkenediyl having in each case up to 5 carbon atoms and being in each case optionally substituted by halogen and/or interrupted at the beginning (and/or at the end) or within the hydrocarbon chain by O (oxygen), S (sulphur) or a grouping selected from the group consisting of —SO—, —SO
2
—, —NH— and —N(C
1
-C
4
-alkyl)—.
R
1
particularly preferably represents hydrogen, fluorine or chlorine.
R
2
particularly preferably represents cyano, thiocarbamoyl, fluorine, chlorine, bromine, trifluoromethyl, difluoromethoxy or trifluoromethoxy.
R
3
particularly preferably represents hydrogen, amino, nitro, formyl, carboxyl, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, represents hydroxyiminomethyl, hydroxyiminoethyl or hydroxyiminopropyl, represents in each case optionally cyano-, hydroxyl-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl- or ethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted acetyl, propionyl, n-or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, acetylamino, propionylamino, n- or i-butyroylamino, methoxyiminomethyl, ethoxyiminomethyl, methoxyiminoethyl or ethoxyiminoethyl, represents in each case optionally cyano-, fluorine- or chlorine-substituted propenyl, butenyl, propenyloxy, butenyloxy, propenylthio, butenylthio, propinyl, butinyl, propinyloxy, butinyloxy, propinylthio or butinylthio, represents in each case optionally cyano-, fluori

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