Substituted 1,3,5- triazines

Details Substituted 1,3,5- triazines Substituted 1,3,5- triazines

2001-07-13

2003-11-11

Raymond, Richard L. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C544S206000, C544S207000, C544S208000, C544S209000

Reexamination Certificate

active

06645915

ABSTRACT:

FIELD OF THE INVENTION
The invention relates to novel substituted 1,3,5-triazines, to processes and novel intermediates for their preparation and to their use as herbicides.
BACKGROUND OF THE INVENTION
Some substituted 1,3,5-triazines having herbicidal action have already been disclosed (see JP-A 19400/1961, U.S. Pat. Nos. 3,816,419, 3,932,167, JP-A 192873/1983, WO-A 90/09378). Likewise, the compounds (R)-6-chloro-N-(1-cyclohexyl-ethyl)-N′-ethyl-1,3,5-triazine-2,4-diamine, (S)-6-chloro-N-(1-cyclohexylethyl)-N′-ethyl-1,3,5-triazine-2,4-diamine and (R,S)-6-chloro-N-(1-cyclohexyl-ethyl)-N′-ethyl-1,3,5-triazine-2,4-diamine have already been disclosed in the literature as herbicidally active compounds (cf. Z. Naturforsch., C: Biosc. (1987), 42, 663-669—cited in Chem. Abstracts 107:91770). However, these compounds have hitherto not attained any particular importance.
SUMMARY OF THE INVENTION
Substituted cyclohexylalkylamino-1,3,5-triazines may be used as herbcides.
DETAILED DESCRIPTION
This invention, accordingly, provides novel substituted cyclohexylalkylamino-1,3,5-triazines of the general formula (I)
in which
A represents CHR
3
R
4
or represents C
1
-halogenoalkyl-substituted C
3
-C
6
-cycloalkyl, C
3
-C
6
-alkinyl or C
1
-C
4
-cyanoalkyl, where
R
3
and R
4
simultaneously or independently of one another represent optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted C
1
-C
6
-alkyl, represent C
1
-C
4
-halogenoalkyl or represent C
3
-C
7
-cycloalkyl which is optionally substituted by nitro, cyano, hydroxyl, halogen, by for its part in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms or by for its part optionally cyano-, halogen- or C
1
-C
4
-alkyl-substituted cycloalkyl having 3 to 6 carbon atoms and where the total number of carbon atoms of R
3
and R
4
is greater than 3,
R
1
represents amino, formylamino, represents dialkylaminoalkylideneamino having up to 6 carbon atoms, or represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkylcarbonylamino, alkoxycarbonyl-amino or alkylaminocarbonylamino having in each case 1 to 6 carbon atoms in the alkyl groups, and
R
2
represents in each case optionally hydroxyl-, cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms or represents optionally cyano-, halogen- or C
1
-C
4
-alkyl-substituted cycloalkyl having 3 to 6 carbon atoms.
Preferred substituents or ranges of the radicals present in the formulae listed above and below are described below.
A preferably represents CHR
3
R
4
, preferably represents C
1
-halogenoalkyl-substituted C
5
-C
6
-cycloalkyl, preferably represents 1,1-dimethyl-2-propinyl or preferably represents 1-cyano-1-methylethyl, where
R
3
and R
4
preferably simultaneously or independently represent optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted C
1
-C
5
-alkyl, represent C
1
-C
3
-halogenoalkyl or represent C
3
-C
6
-cycloalkyl which is optionally substituted by nitro, cyano, hydroxyl, fluorine, chlorine, bromine, by for its part in each case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-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, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, or by for its part in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, and where the total number of carbon atoms of R
3
and R
4
is greater than 3,
R
1
preferably represents amino, formylamino, dimethylaminomethyleneamino or diethylaminomethyleneamino, or represents in each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted acetyl-amino, propionylamino, n- or i-butyroylamino, methoxycarbonylamino, ethoxycarbonylamino, n- or i-propoxycarbonylamino, methylaminocarbonylamino, ethylaminocarbonylamino, n- or i-propylaminocarbonylamino.
R
2
preferably represents in each case optionally hydroxyl-, cyano-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-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, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, or represents in each case optionally cyano-, fluorine-, chlorine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
A particularly preferably represents CHR
3
R
4
, represents trifluoromethyl-substituted cyclohexyl, represents 1,1-dimethyl-2-propinyl or represents 1-cyano-1-methylethyl, where
R
3
and R
4
particularly preferably simultaneously or independently represent in each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, s-, i- or t-butyl, represent 2-fluoroethyl, 2-chloroethyl, 1-fluoroethyl, 3-fluoropropyl or 3-chloropropyl or represent cyclopentyl or cyclohexyl, where the cycloalkyl radicals are optionally substituted by hydroxyl, fluorine, chlorine, by for its part in each case optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, or by for its part in each case optionally fluorine-, chlorine-, methyl-, ethyl-, n- or i-propyl-substituted cyclohexyl, and where the total number of carbon atoms of R
3
and R
4
is greater than 3,
R
1
particularly preferably represents amino, formylamino, dimethylaminomethyleneamino, acetylamino or propionylamino.
R
2
particularly preferably represents in each case optionally fluorine-, chlorine-, methoxy-, ethoxy-substituted methyl, ethyl, n- or i-propyl.
A very particularly preferably represents CHR
3
R
4
, represents trifluoromethyl-substituted cyclohexyl, represents 1,1-dimethyl-2-propinyl or represents 1-cyano-1-methylethyl, where
R
3
and R
4
very particularly preferably simultaneously or independently represent methyl, ethyl, n- or i-propyl, represent 2-fluoroethyl, 2-chloroethyl, 1-fluoroethyl, 3-fluoropropyl or 3-chloropropyl or represent cyclopentyl or cyclohexyl and where the total number of carbon atoms of R
3
and R
4
is greater than 3.
R
1
very particularly preferably represents amino, formylamino, ethylcarbonylamino or methylcarbonylamino.
R
2
very particularly preferably represents 1-fluoroethyl, difluorochloromethyl, dichloromethyl or 1-fluoro-1-methylethyl.
The abovementioned general or preferred radical definitions apply both to the end products of the formula (I) and, correspondingly, to the starting materials or intermediates required in each case for the preparation. These radical definitions can be combined with each other as desired, i.e. including combinations between the given preferred ranges.
Preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings listed above as being preferred.
Particular preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings mentioned above as being particularly preferred.
Very particular preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings listed above

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