Substituted triazoloazine sulphonamides

Details Substituted triazoloazine sulphonamides Substituted triazoloazine sulphonamides

1999-05-10

2001-10-02

Morris, Patricia L. (Department: 1625)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S241000, C544S065000, C544S263000, C514S229200, C514S258100

Reexamination Certificate

active

06297195

ABSTRACT:

TECHNICAL FIELD OF THE INVENTION
The invention relates to novel substituted triazoloazinesulphonamides, to processes for their preparation and to their use as plant treatment agents.
BACKGROUND OF THE INVENTION
A large number of triazoloazinesulphonamides is already known from the (patent) literature (cf. EP 142152, EP 244847, EP 375076, U.S. Pat. No. 4,605,433, U.S. Pat. No. 5,163,995, WO 89/10368, Pestic. Sci. 29 (1990), 341-355).
DETAILED DESCRIPTION OF THE INVENTION
Novel substituted triazoloazinesulphonamides of the general formula (I)
in which
Q
1
represents nitrogen or a CH grouping,
Q
2
represents nitrogen or a CH grouping,
R
1
represents hydrogen, halogen or represents C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-alkylamino or di-(C
1
-C
4
-alkyl)-amino, each of which is optionally substituted by hydroxyl, halogen or C
1
-C
4
-alkoxy,
R
2
represents hydrogen, halogen or represents C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-alkylamino or di-(C
1
-C
4
-alkyl)-amino, each of which is optionally substituted by halogen, and
Ar represents 4-cyano-2,5-difluoro-phenyl, 2,6-dimethoxy-phenyl, 2-bromo-3-trifluoromethyl-phenyl, 2-bromo-5-trifluoromethyl-phenyl, 4-bromo-2,6-dimethyl-phenyl, 6-chloro-pyridin-3-yl-methyl or one of the 5- or 6-membered (hetero)cyclic groupings below:
in which
m in each case represents the numbers 1 or 2,
n in each case represents the numbers 0, 1 or 2,
A
1
represents optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted C
1
-C
4
-alkyl or represents optionally cyano-, halogen- or C
1
-C
4
-alkyl-substituted C
3
-C
6
-cycloalkyl,
A
2
represents C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-alkylsulphinyl or C
1
-C
4
-alkylsulphonyl, each of which is optionally substituted by halogen,
R
3
represents optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted C
1
-C
4
-alkyl,
A
4
represents optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted C
1
-C
4
-alkyl,
A
5
represents optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted C
2
-C
4
-alkyl, represents optionally halogen-substituted C
2
-C
4
-alkenyl or represents optionally cyano-, halogen- or C
1
-C
4
-alkyl-substituted C
3
-C
6
-cycloalkyl-C
1
-C
4
-alkyl,
A
6
represents halogen or represents C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
2
-C
4
-alkenyl or C
2
-C
4
-alkenyloxy, each of which is optionally substituted by halogen,
A
7
represents cyano-, halogen- or C
1
-C
4
-alkoxy-substituted C
1
-C
4
-alkyl,
A
8
represents cyano, nitro or optionally halogen-substituted C
1
-C
4
-alkyl,
A
9
represents cyano, halogen or optionally halogen-substituted C
1
-C
4
-alkyl,
A
10
represents optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted C
1
-C
4
-alkyl or represents optionally cyano-, halogen- or C
1
-C
4
-alkyl-substituted C
3
-C
6
-cycloalkyl,
A
11
represents hydrogen or represents C
1
-C
4
-alkyl, C
1
-C
4
-alkyl-carbonyl, C
1
-C
4
-alkoxycarbonyl or C
1
-C
4
-alkylsulphonyl, each of which is optionally substituted by cyano, halogen or C
1
-C
4
-alkoxy,
A
12
represents hydrogen, cyano, halogen or optionally halogen-substituted C
1
-C
4
-alkyl,
A
13
represents cyano, carbamoyl, 5,6-dihydro-1,4,2-dioxazin-3-yl, halogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkyl-carbonyl or C
1
-C
4
-alkoxy-carbonyl,
A
14
represents hydrogen, represents cyano, carbamoyl, halogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkylcarbonyl or C
1
-C
4
-alkoxy-carbonyl,
A
15
represents hydrogen, represents cyano, carbamoyl, halogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkylcarbonyl or C
1
-C
4
-alkoxy-carbonyl, or together with A
14
represents a fused benzo grouping,
A
16
represents hydrogen, cyano, halogen or represents C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-alkylsulphinyl or C
1
-C
4
-alkylsulphonyl, each of which is optionally substituted by halogen,
A
17
represents hydrogen, cyano, halogen or optionally halogen-substituted C
1
-C
4
-alkyl,
A
18
represents hydrogen, cyano, halogen or optionally halogen-substituted C
1
-C
4
-alkyl,
A
19
represents hydrogen or C
1
-C
4
-alkyl,
A
20
represents C
1
-C
4
-alkyl or C
2
-C
4
-alkenyl,
A
21
represents cyano, halogen, C
1
-C
4
-alkyl or C
1
-C
4
-halogenoalkyl,
A
22
represents C
1
-C
4
-alkyl or C
1
-C
4
-halogenoalkyl,
A
23
represents C
1
-C
4
-alkyl,
A
24
on its own represents C
1
-C
4
-alkyl or together with A
23
represents C
2
-C
4
-alkanediyl,
A
25
represents cyano, halogen, C
1
-C
4
-alkyl or C
1
-C
4
-halogenoalkyl,
A
26
represents C
1
-C
4
-alkyl,
A
27
represents cyano, halogen, C
1
-C
4
-alkyl, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-alkoxy or C
1
-C
4
-halogenoalkoxy,
A
28
represents hydrogen, difluoromethyl, C
1
-C
4
-alkyl-carbonyl, C
1
-C
4
-alkoxy-carbonyl or C
1
-C
4
-alkylsulphonyl,
A
29
represents cyano, halogen, C
1
-C
4
-alkyl or C
1
-C
4
-halogenoalkyl,
A
30
represents hydrogen, C
1
-C
4
-alkyl or C
1
-C
4
-alkoxy,
A
31
represents hydrogen or C
1
-C
4
-alkyl,
A
32
represents cyano, halogen, C
1
-C
4
-alkyl or C
1
-C
4
-halogenoalkyl,
A
33
represents hydrogen, C
1
-C
4
-alkyl or C
1
-C
4
-alkoxy,
A
34
represents hydrogen or C
1
-C
4
-alkyl,
A
35
represents cyano, halogen, C
1
-C
4
-alkyl or C
1
-C
4
-halogenoalkyl,
A
36
represents hydrogen, C
1
-C
4
-alkyl, C
3
-C
6
-cycloalkyl or phenyl,
A
37
represents hydrogen, C
1
-C
4
-alkyl, C
3
-C
6
-cycloalkyl or phenyl,
A
38
represents hydrogen, halogen, represents C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy or C
1
-C
4
-alkylthio, each of which is optionally substituted by cyano, halogen or C
1
-C
4
-alkoxy, or represents C
3
-C
6
-cycloalkyl, C
3
-C
6
-cycloalkyloxy or C
3
-C
6
-cycloalkyl-C
1
-C
4
-alkyl, each of which is optionally substituted by cyano, halogen or C
1
-C
4
-alkyl, and
A
39
represents hydrogen, represents C
1
-C
4
-alkyl or C
1
-C
4
-alkoxy, each of which is optionally substituted by cyano, halogen or C
1
-C
4
-alkoxy, or represents C
3
-C
6
-cycloalkyl, C
3
-C
6
-cycloalkyloxy or C
3
-C
6
-cycloalkyl-C
1
-C
4
-alkyl, each of which is optionally substituted by cyano, halogen or C
1
-C
4
-alkyl,
and also salts of the compounds of the formula (I) have now been found.
The novel substituted triazoloazinesulphonamides of the general formula (I) are obtained when substituted triazoloazinesulphonyl chlorides of the general formula (II)
in which
Q
1
, Q
2
, R
1
and R
2
are each as defined above
are reacted with amino(hetero)arenes of the general formula (III)
 H
2
N—Ar  (III)
in which
Ar is as defined above,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent and, if appropriate, further transformation reactions within the framework of the above definition of substituents are carried out by customary methods on the resulting compounds of the formula (I).
The novel substituted triazoloazinesulphonamides of the general formula (I) have interesting biological properties, allowing their use as plant treatment agents. They have strong herbicidal, fungicidal and insecticidal activity and in particular have excellent and selective herbicidal action.
The invention preferably provides compounds of the formula (I) in which
Q
1
represents nitrogen or a CH grouping,
Q
2
represents nitrogen or a CH grouping,
R
1
represents hydrogen, fluorine, chlorine, bromine or represents methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino, each of which is optionally substituted by fluorine, chlorine, methoxy or ethoxy,
R
2
represents hydrogen, fluorine, chlorine, bromine or represents methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino, each of which is optionally substituted by fluorine, chlorine, methoxy or ethoxy,
Ar represents 4-cyano-2,5-difluoro-phenyl, 2,6-dimethoxy-phenyl, 2-bromo-3-trifluoromethyl-phenyl, 2-bromo-5-trifluoromethyl-phenyl, 4-bromo-2,6-dimethyl-phenyl, 6-chloro-pyridin-3-y

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