Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
2002-03-04
2004-06-29
Balasubramanian, Venkataraman (Department: 1624)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
C544S207000, C544S212000, C549S049000, C549S050000
Reexamination Certificate
active
06756342
ABSTRACT:
The invention relates to novel substituted thienocycloalk(en)ylamino-1,3,5-triazines, to processes for their preparation including the novel intermediates, and to their use as herbicides.
A number of substituted thienylalkylamino-1,3,5-triazines are already known from the (patent) literature (cf. WO-A-98/15537, WO-A-98/15539, DE-A-19744232). However, these compounds have hitherto not attained any particular importance. Substituted thienocycloalk(en)ylamino-1,3,5-triazines have hitherto not been disclosed at all.
This invention, accordingly, provides the novel thienocycloalk(en)ylamino-1,3,5-triazines of the general formula (I)
in which
R
1
represents hydrogen or represents optionally substituted alkyl,
R
2
represents hydrogen, represents formyl or represents in each case optionally substituted alkyl, alkylcarbonyl, alkoxycarbonyl or alkylaminocarbonyl,
or the grouping N(R
1
R
2
) also represents dialkylaminoalkylideneamino,
R
3
represents hydrogen, represents halogen, represents optionally substituted alkyl, represents in each case optionally substituted alkylcarbonyl, alkoxycarbonyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl, represents in each case optionally substituted alkenyl or alkinyl, or represents optionally substituted cycloalkyl, and
Z represents one of the thienocycloalk(en)yl groupings below
in which
m represents the numbers 0, 1, 2, 3 or 4,
n represents the numbers 0, 1 or 2,
A
1
represents O (oxygen), S (sulphur), —CO—, —CS— or alkanediyl (alkylene),
A
2
represents O (oxygen), S (sulphur), —CO—, —CS— or alkanediyl (alkylene),
A
3
represents O (oxygen), S (sulphur), —CO—, —CS— or alkanediyl (alkylene),
with the proviso that at least one of the groupings A
1
, A
2
, A
3
represents alkanediyl and that two adjacent groups do not simultaneously represent S or O—
R
4
represents amino, cyano, carbamoyl, thiocarbamoyl, formyl, halogen, or represents in each case optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino, alkylsulphonylamino, alkenyl, alkinyl, alkenylcarbonyl, alkinylcarbonyl, carbonyl, aryl arylcarbonyl or arylalkyl, and
R
5
represents nitro, amino, cyano, carbamoyl, thiocarbamoyl, formyl, halogen, or represents in each case optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino, alkylsulphonylamino, alkenyl, alkinyl, alkenylcarbonyl, alkinylcarbonyl, aryl, arylcarbonyl or arylalkyl.
Saturated or unsaturated hydrocarbon groupings, such as alkyl, alkanediyl, alkenyl or alkinyl, are—including in combinations with heteroatoms, such as in alkoxy—in each case straight-chain or branched, as far as this is possible.
Optionally substituted radicals can be mono- or polysubstituted, where in the case of polysubstitution the substituents can be identical or different.
Preferred substituents or ranges of the radicals present in the formulae shown above and below are defined below.
m preferably represents the numbers 0, 1 or 2.
A
1
preferably represents O (oxygen), S (sulphur), —CO—, —CS— or alkanediyl (alkylene) having 1 to 3 carbon atoms.
A
2
preferably represents O (oxygen), S (sulphur), —CO—, —CS— or alkanediyl (alkylene) having 1 to 3 carbon atoms.
A
3
preferably represents O (oxygen), S (sulphur), —CO—, —CS— or alkanediyl (alkylene) having 1 to 3 carbon atoms.
In the preferred compounds, at least one of the groupings A
1
, A
2
, A
3
represents alkanediyl having 1 to 3 carbon atoms, and two adjacent groups do not simultaneously represent S or O.
R
1
preferably represents hydrogen or represents optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl having 1 to 6 carbon atoms.
R
2
preferably represents hydrogen, represents formyl or represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkylcarbonyl, alkoxycarbonyl or alkylaminocarbonyl having in each case 1 to 6 carbon atoms in the alkyl groups.
The grouping N(R
1
R
2
) preferably also represents dialkylaminoalkylideneamino having in each case up to 4 carbon atoms in the alkyl groups or alkylidene groups.
R
3
preferably represents hydrogen, represents halogen, represents optionally cyano-, halogen-, hydroxyl-, C
1
-C
4
-alkoxy- or C
1
-C
4
-alkylthio-substituted alkyl having 1 to 6 carbon atoms, represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkylcarbonyl, alkoxycarbonyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups, represents in each case optionally halogen-substituted alkenyl or alkinyl having in each case 2 to 6 carbon atoms, or represents optionally cyano-, halogen- or C
1
-C
4
-alkyl-substituted cycloalkyl having 3 to 6 carbon atoms.
R
4
preferably represents amino, cyano, carbamoyl, thiocarbamoyl, formyl, halogen, represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino or alkylsulphonylamino having in each case 1 to 6 carbon atoms in the alkyl groups, represents in each case optionally cyano- or halogen-substituted alkenyl, alkinyl, alkenylcarbonyl or alkinylcarbonyl having in each case 2 to 6 carbon atoms in the alkenyl or alkinyl groups, or represents in each case optionally nitro-, cyano-, halogen-, C
1
-C
4
-alkyl-, C
1
-C
4
-halogenoalkyl-, C
1
-C
4
-alkoxy-, C
1
-C
4
-halogenoalkoxy- or C
1
-C
4
-alkoxy-carbonyl-substituted aryl, arylcarbonyl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety.
R
5
preferably represents nitro, amino, cyano, carbamoyl, thiocarbamoyl, formyl, halogen, represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino or alkylsulphonylamino having in each case 1 to 6 carbon atoms in the alkyl groups, represents in each case optionally cyano- or halogen-substituted alkenyl, alkinyl, alkenylcarbonyl or alkinylcarbonyl having in each case 2 to 6 carbon atoms in the alkenyl or alkinyl groups, or represents in each case optionally nitro-, cyano:-, halogen-, C
1
-C
4
-alkyl-, C
1
-C
4
-halogenoalkyl-, C
1
-C
4
-alkoxy-, C
1
-C
4
-halogenoalkoxy- or C
1
-C
4
-alkoxy-carbonyl substituted aryl, arylcarbonyl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety.
A
1
particularly preferably represents O (oxygen), S (sulphur), —CO—, —CS—, methylene, dimethylene or trimethylene.
A
2
particularly preferably represents O (oxygen), S (sulphur), —CO—, —CS—, methylene, dimethylene or trimethylene.
A
3
particularly preferably represents O (oxygen), S (sulphur), —CO—, —CS—, methylene, dimethylene or trimethylene.
In the preferred compounds, at least one of the groupings A
1
, A
2
, A
3
represents methylene, dimethylene or trimethylene, and two adjacent groups do not simultaneously represent S or O.
R
1
particularly preferably represents hydrogen or represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl.
R
2
particularly preferably represents hydrogen, represents formyl or represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylamino-carbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl.
The grouping N(R
1
R
2
) particularly preferably also represents dimethylaminomethyleneamino or diethylaminomethyleneamino.
R
3
particularly preferably represents hydrogen, represents fluorine, chlorine, bromine, represents in each case opti
Drewes Mark Wilhelm
Feucht Dieter
Kather Kristian
Lehr Stefan
Pontzen Rolf
Balasubramanian Venkataraman
Bayer Aktiengesellschaft
Harmuth Raymond J.
Henderson Richard E. L.
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