Substituted 2-aryl-1,2,4-triazine-3,5-di(thi)ones

Details Substituted 2-aryl-1,2,4-triazine-3,5-di(thi)ones Substituted 2-aryl-1,2,4-triazine-3,5-di(thi)ones

2001-11-29

2003-08-19

Ford, John M. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S225000, C544S112000, C544S182000

Reexamination Certificate

active

06608004

ABSTRACT:

The invention relates to novel substituted 2-aryl-1,2,4-triazine-3,5-di(thi)ones, to processes for their preparation and to their use as herbicides.
It is known that certain substituted 2-aryl-1,2,4-triazin-(ethi)ones have herbicidal properties (cf. EP-A-11693, EP-A-271170, WO-A-86/00072, WO-A-97/30980, U.S. Pat. Nos. 4,755,217, 4,878,941, 4,956,004, 5,262,390, 5,344,812). However, the compounds known from the patent applications or patents stated have not attained any importance worth mentioning.
This invention, accordingly, provides novel substituted 2-aryl-1,2,4-triazine-3,5-di(thi)ones of the general formula (I)
in which
Q
1
represents oxygen or sulphur,
Q
2
represents oxygen or sulphur,
R
1
represents hydrogen, cyano, amino, represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylcarbonyl or alkoxycarbonyl having in each case 1 to 6 carbon atoms in the alkyl groups, represents in each case optionally halogen-substituted alkenyl, alkenylcarbonyl, alkenyloxycarbonyl, alkinyl, alkinylcarbonyl or alkenyloxycarbonyl having in each case 2 to 6 carbon atoms in the alkenyl or alkinyl groups, 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 1 to 4 carbon atoms in the alkyl moiety,
R
2
represents hydrogen, halogen, nitro, carboxyl, cyano, thiocarbamoyl, amino, represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino having in each case 1 to 6 carbon atoms in the alkyl groups, represents in each case optionally halogen-substituted alkenyl, alkenyloxy, alkenylthio, alkinyl, alkinyloxy or alkinylthio having in each case 2 to 6 carbon atoms in the alkenyl or alkinyl groups, 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 1 to 6 carbon atoms in the alkyl moiety,
R
3
represents hydrogen, cyano or halogen,
R
4
represents cyano or thiocarbamoyl,
R
5
represents hydrogen, represents alkoxycarbonyl having 1 to 6 carbon atoms in the alkoxy group, or represents one of the radicals —R
7
, —O—R
7
, —SR
7
, —NH—R
7
or —NR
7
R
8
,
R
6
represents amino, hydroxyl or represents one of the radicals —R
7
or —NR
7
R
8
,
R
7
represents straight-chain or branched alkyl having 1 to 10 carbon atoms which is optionally mono- or polysubstituted by identical or different substituents, possible substituents being:
cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, in each case straight-chain or branched alkoxy, alkoxyalkoxy, alkylcarbonyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkoxycarbonyl, N-alkyl-aminocarbonyl, N,N-dialkyl-aminocarbonyl, trialkylsilyl or alkylsulphonylaminocarbonyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, or heterocyclyl, where the heterocyclyl radical is a five- to seven-membered, optionally benzo-fused, saturated or unsaturated heterocycle having 1 to 3 identical or different heteroatoms, in particular nitrogen, oxygen and/or sulphur, or
R
7
represents alkenyl or alkinyl having in each case 2 to 8 carbon atoms and being in each case optionally mono- or polysubstituted by identical or different halogens, or
R
7
represents cycloalkyl or cycloalkylalkyl having in each case 3 to 7 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl moiety and being in each case optionally mono- or polysubstituted by identical or different substituents from the group consisting of cyano, halogen and C
1
-C
4
-alkyl, or
R
7
represents aryl, arylalkyl, bis-aryl-alkyl, arylalkenyl, aryloxyalkyl or arylalkoxyalkyl having in each case 6 to 10 carbon atoms in the aryl moiety and optionally up to 4 carbon atoms in the straight-chain or branched alkyl moiety or alkenyl moiety and being in each case optionally mono- or polysubstituted in the aryl moiety by identical or different substituents, or represents a saturated or unsaturated five- to seven-membered heterocyclyl radical having 1 to 3 identical or different heteroatoms—in particular nitrogen, oxygen and/or sulphur—and being optionally mono- or polysubstituted by identical or different substituents and/or benzo-fused, possible aryl or heterocyclyl substituents being:
halogen, cyano, nitro, amino, methylenedioxy, N-(C
1
-C
4
-alkyl-carbonyl)-amino, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl having in each case 1 to 6 carbon atoms and 1 to 3 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties and phenyl which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen and straight-chain or branched alkyl or alkoxy having in each case 1 to 6 carbon atoms and straight-chain or branched halogenoalkyl or halogenoalkoxy having in each case 1 to 6 carbon atoms and 1 to 3 identical or different halogen atoms, and
R
8
represents hydrogen or represents straight-chain or branched alkyl having 1 to 8 carbon atoms which is optionally mono- or polysubstituted by identical or different substituents, possible substituents being:
cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, in each case straight-chain or branched alkoxy, alkoxyalkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, trialkylsilyl or alkylsulphonylaminocarbonyl having in each case 1 to 8 carbon atoms in the individual alkyl moieties or heterocyclyl, where the heterocyclyl radical is a five- to seven-membered, optionally benzo-fused, saturated or unsaturated heterocycle having 1 to 3 identical or different heteroatoms, in particular nitrogen, oxygen and/or sulphur, or
R
8
represents alkenyl or alkinyl having in each case 2 to 8 carbon atoms and being in each case optionally mono- or polysubstituted by identical or different halogens, or
R
8
represents cycloalkyl having 3 to 7 carbon atoms which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of cyano, halogen and straight-chain or branched alkyl having 1 to 4 carbon atoms, or
R
8
together with R
7
represents alkanediyl (alkylene) having 2 to 6 carbon atoms which is optionally interrupted by O (oxygen), S (sulphur), NH or N—(C
1
-C
4
-alkyl).
Preferred substituents or ranges of the radicals present in the formulae shown above and below are defined below.
R
1
preferably represents hydrogen, cyano, amino, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-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, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, represents in each case optionally fluorine-, chlorine- or bromine-substituted propenyl, butenyl, propenylcarbonyl, butenylcarbonyl, propenyloxycarbonyl, butenyloxycarbonyl, represents propinyl, butinyl, propinylcarbonyl, butinylcarbonyl, propinyloxycarbonyl or butinyloxycarbonyl, or represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl.
R
2
preferably represents hydrogen, nitro, carboxyl, cyano, thiocarbamoyl, amino, fluorine, chlorine, bromine, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-subst

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