Substituted thiazol(in) ylideneamino sulfonylamino...

Details Substituted thiazol(in) ylideneamino sulfonylamino... Substituted thiazol(in) ylideneamino sulfonylamino...

2001-04-27

2002-06-11

Gerstl, Robert (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C548S194000

Reexamination Certificate

active

06403535

ABSTRACT:

The invention relates to novel substituted thiazol(in)ylideneaminosulphonylamino-(thio)carbonyl-triazolinones, to a plurality of processes for their preparation and to their use as herbicides.
It is already known that certain substituted thiazol(in)ylideneaminosulphonyl-amino(thio)carbonyl-triazolinones have herbicidal properties (cf. EP 341 489, EP 422 469, EP 425 948, EP 431 291, EP 507 171, WO 93/24482, WO 94/08979, WO 95/27703, WO 96/22982). However, the activity of these compounds is not entirely satisfactory.
This invention, accordingly provides novel substituted thiazoli(di)nylimino-sulphonylamino(thio)carbonyl-triazolinones of the general formula (I),
in which
Q represents oxygen or sulphur,
R
1
represents hydrogen, amino, alkylideneamino or represents an in each case optionally substituted radical from the group consisting of alkyl, alkoxy, alkylamino, dialkylamino, alkanoylamino, alkenyl, alkinyl, alkenyloxy, cycloalkyl, cycloalkylalkyl, cycloalkylamino, aryl and arylalkyl,
R
2
represents hydrogen, cyano, halogen or represents an in each case optionally substituted radical from the group consisting of alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkenyl, alkinyl, alkenyloxy, alkenylthio, alkenylamino, cycloalkyl, cycloalkylalkyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, aryl, aryloxy, arylthio, arylamino, arylalkyl, arylalkoxy, arylalkylthio and arylalkylamino,
R
3
represents an in each case optionally substituted radical from the group consisting of alkyl, alkoxy, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl and arylalkyl,
R
4
represents hydrogen, cyano, halogen or optionally substituted alkyl,
R
5
represents hydrogen, cyano, halogen or optionally substituted alkyl,
and salts of compounds of the formula (I).
The general formula (I) is the sum of the compounds defined by the general formulae (IA) and (IB) below.
In the general formulae (IA) and (IB), Q, R
1
, R
2
, R
3
, R
4
and R
5
each have the meanings given above in the definition of the compounds of the general formula (I). If in the compounds of the formula (IB) R
4
and R
5
are both different from hydrogen, cis/trans isomerism may occur; the invention embraces in each case both isomers and cis/trans mixtures of any isomer ratio.
The novel compounds of the general formula (I) are obtained when
(a) chlorosulphonylamino(thio)carbonyltriazolinones of the general formula (III)
 in which
Q, R
1
and R
2
are each as defined above,
are reacted with iminothiazoli(di)nes of the general formula (III)
 in which
R
3
, R
4
and R
5
are each as defined above,
-or with acid adducts of compounds of the general formula (III)-,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
and, if appropriate, the resulting compounds of the formula (I) are converted by customary methods into salts,
 or when
(b) triazolinones of the general formula (IV)
 in which
R
1
and R
2
are each as defined above,
are reacted with chlorosulphonyl iso(thio)cyanate of the general formula (V)
Cl—SO
2
—N═C═Q  (V)
 in which
Q is as defined above,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
and the resulting chlorosulphonylamino(thio)carbonyltriazolinones of the general formula (II)
 in which
Q, R
1
and R
2
are each as defined above,
are reacted with iminothiazoli(di)nes of the general formula (III)
 in which
R
3
, R
4
and R
5
are each as defined above,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
and, if appropriate, the resulting compounds of the formula (I) are converted by customary methods into salts.
Further possible preparation methods for the compounds of the general formula (I) according to the invention are listed below, Q, R
1
, R
2
, R
3
, R
4
and R
5
being in each case as defined above.
(c) Reaction of triazolinone derivatives of the general formula (VI)
 in which
Q, R
1
and R
2
are each as defined above and
Z represents halogen, alkoxy, aralkoxy or aryloxy,
with aminosulphonyliminothiazoli(di)nes of the general formula (VII)
 in which
R
3
, R
4
and R
5
are each as defined above,
if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent,
(d) reaction of triazolinones of the general formula (IV)
 in which
R
1
and R
2
are each as defined above,
with sulphonamide derivatives of the general formula (IX)
 in which
Q, R
3
, R
4
and R
5
are each as defined above and
Z represents halogen, alkoxy, aralkoxy or aryloxy,
if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent.
The novel compounds of the general formula (I) have strong herbicidal activity.
Furthermore, the following applies to the definitions in formula (I):
Q preferably represents oxygen or sulphur.
R
1
preferably represents hydrogen, amino, C
1
-C
6
-alkylideneamino, represents optionally fluorine-, chlorine-, bromine-, cyano-, C
1
-C
4
-alkoxy-, C
1
-C
4
-alkyl-carbonyl- or C
1
-C
4
-alkoxy-carbonyl-substituted C
1
-C
6
-alkyl, represents in each case optionally fluorine-, chlorine- and/or bromine-substituted C
2
-C
6
-alkenyl or C
2
-C
6
-alkinyl, represents C
1
-C
6
-alkyloxy or C
2
-C
6
-alkenyloxy, represents in each case optionally fluorine- and/or chlorine-substituted C
1
-C
6
-alkylamino, di-(C
1
-C
4
-alkyl)-amino or C
1
-C
4
-alkanoylamino, represents in each case optionally fluorine-, chlorine-, bromine- and/or C
1
-C
4
-alkyl-substituted C
3
-C
6
-cycloalkyl or C
3
-C
6
-cycloalkyl-C
1
-C
4
-alkyl, or represents in each case optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C
1
-C
4
-alkyl-, trifluoromethyl-, C
1
-C
4
-alkoxy- and/or C
1
-C
4
-alkoxy-carbonyl-substituted phenyl or phenyl-C
1
-C
4
-alkyl.
R
2
preferably represents hydrogen, cyano, fluorine, chlorine, bromine, iodine, represents in each case optionally fluorine-, chlorine-, bromine-, cyano-, C
1-C
4
-alkoxy-, C
1
-C
4
-alkylthio-, C
1
-C
4
-alkylsulphinyl-, C
1
-C
4
-alkylsulphonyl-, C
1
-C
4
-alkyl-carbonyl-, C
1
-C
4
-alkoxy-carbonyl- or C
3
-C
6
-cycloalkyl-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino or dialkylamino having in each case 1 to 6 carbon atoms in the alkyl groups, represents in each case optionally fluorine-, chlorine- and/or bromine-substituted alkenyl, alkenyloxy, alkenylthio or alkenylamino having in each case 2 to 6 carbon atoms in the alkenyl groups, represents alkinyl having 2 to 6 carbon atoms, represents in each case optionally fluorine-, chlorine-, bromine-, cyano- and/or C
1
-C
4
-alkyl-substituted cycloalkyl, cycloalkylalkyl, cycloalkyloxy, cycloalkylthio or cycloalkylamino having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 3 carbon atoms in the alkyl moiety, represents in each case optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C
1
-C
4
-alkyl-, trifluoromethyl-, C
1
-C
4
-alkoxy, difluoromethoxy- or trifluoromethoxy-substituted phenyl, phenoxy, phenylthio, phenylamino, benzyl, benzyloxy, benzylthio or benzylamino.
R
3
preferably represents optionally cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-, C
1
-C
4
-alkoxy-, C
1
-C
4
-alkylthio-, C
1
-C
4
-alkylsulphinyl-, C
1
-C
4
-alkylsulphonyl-, C
1
-C
4
-alkyl-carbonyl-, C
1
-C
4
-alkoxy-carbonyl-, C
1
-C
4
-alkylamino-carbonyl- or di-C
1
-C
4
-alkyl-amino-carbonyl-substituted alkyl having 1 to 6 carbon atoms, represents optionally cyano-, fluorine-, chlorine- or C
1
-C
4
-alkoxy-substituted alkoxy having 1 to 6 carbon atoms, represents in each case optionally cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-, bromine-, C
1
-C
4
-alkyl-carbonyl-, C
1
-C
4
-alkoxy-carbonyl-, C
1
-C
4
-alkylamino-carbonyl- or di-C
1
-C
4
-alkyl-amino-carbonyl-substituted alkenyl or alkinyl having in each case 2 to 6 carbon atoms, represents in each case optionally cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-, bromine-, C
1
-C
4
-alkyl-,

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