Thienylsulphonylamino(thio)carbonyl compounds

Details Thienylsulphonylamino(thio)carbonyl compounds Thienylsulphonylamino(thio)carbonyl compounds

2002-10-31

2004-02-03

Morris, Patricia L. (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C549S062000, C549S065000, C549S066000

Reexamination Certificate

active

06686478

ABSTRACT:

The invention relates to novel thienylsulphonylamino(thio)carbonyl compounds, to a plurality of processes and novel intermediates for their preparation and to their use as herbicides.
It is already known that certain sulphonylaminocarbonyl compounds have herbicidal properties (cf. EP 341489, EP 422469, EP 425948, EP 431291, EP 507171, EP 534266, DE 4029753). However, the activity of these compounds is not in all respects satisfactory.
This invention, accordingly, provides the novel thienylsulphonylamino(thio)carbonyl compounds of the general formula (I),
in which
Q represents oxygen or sulphur,
R
1
represents cyano, halogen or in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy or alkinyloxy having in each case up to 6 carbon atoms,
R
2
represents cyano, halogen or in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy or alkinyloxy having in each case up to 6 carbon atoms, and
R
3
represents in each case optionally substituted heterocyclyl having 5 ring members, at least one of which represents oxygen, sulphur or nitrogen and one to three others may represent nitrogen,
and salts of compounds of the formula (I).
The novel thienylsulphonylamino(thio)carbonyl compounds of the general formula (I) are obtained when
(a) sulphonamides of the general formula (II)
 in which
R
1
and R
2
are each as defined above,
are reacted with (thio)carboxylic acid derivatives of the general formula (III)
 in which
Q and R
3
are each as defined above and
Z represents halogen, alkoxy, aryloxy or arylalkoxy,
if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent,
or when
(b) sulphonyl iso(thio)cyanates of the general formula (IV)
 in which
Q, R
1
and R
2
are each as defined above,
are reacted with heterocycles of the general formula (V)
H—R
3-1
  (V)
in which
R
3-1
represents optionally substituted heterocyclyl having 5 ring members, at least one of which represents >N—H,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or when
(c) sulphonyl chlorides of the general formula (VI)
 in which
R
1
and R
2
are each as defined above,
are reacted with heterocycles of the general formula (V)
H—R
3-1
  (V)
in which
R
3-1
is as defined above under (b),
and metal (thio)cyanates of the general formula (VII)
MQCN  (VII)
in which
Q is as defined above and
M represents a metal equivalent,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or when
(d) sulphonyl chlorides of the general formula (VI)
 in which
R
1
and R
2
are each as defined above,
are reacted with (thio)carboxamides of the general formula (VIII)
 in which
Q and R
3
are each as defined above under formula (I),
if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent,
or when
(e) sulphonylamino(thio)carbonyl compounds of the general formula (IX)
 in which
Q, R
1
and R
2
are each as defined above and
Z represents halogen, alkoxy, aryloxy or arylalkoxy,
are reacted with heterocycles of the general formula (V)
H—R
3-1
  (V)
in which
R
3-1
is as defined above under (b),
if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent,
and the compounds of the formula (I) obtained by the processes (a), (b), (c), (d) or (e) are, if appropriate, converted into salts by customary methods.
According to their nature, the processes (b), (c) and (e) are only suitable for preparing those compounds of the formula (I) in which R
3
represents R
3-1
.
The novel thienylsulphonylamino(thio)carbonyl compounds of the general formula (I) have strong herbicidal activity.
The invention preferably provides compounds of the formula (I) in which
Q represents oxygen or sulphur,
R
1
represents cyano, halogen, represents optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted C
1
-C
4
-alkyl, represents in each case optionally cyano- or halogen-substituted C
2
-C
4
-alkenyl or C
2
-C
4
-alkinyl, represents optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted C
1
-C
4
-alkoxy, or represents in each case optionally cyano- or halogen-substituted C
2
-C
4
-alkenyloxy or C
2
-C
4
-alkinyloxy,
R
2
represents cyano, halogen, represents optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted C
1
-C
4
-alkyl, represents in each case optionally cyano- or halogen-substituted C
2
-C
4
-alkenyl or C
2
-C
4
-alkinyl, represents optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted C
1
-C
4
-alkoxy, or represents in each case optionally cyano- or halogen-substituted C
2
-C
4
-alkenyloxy or C
2
-C
4
-alkinyloxy, and
R
3
represents in each case optionally substituted heterocyclyl of the formulae below
 in which
Q
1
, Q
2
and Q
3
each represent oxygen or sulphur and
R
4
represents hydrogen, hydroxyl, amino, cyano, represents C
2
-C
10
-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 in each case optionally fluorine-, chlorine-, bromine-, cyano-, C
1
-C
4
-alkoxy- or C
1
-C
4
-alkoxy-carbonyl-substituted C
1
-C
6
-alkoxy, C
1
-C
6
-alkylamino or C
1
-C
6
-alkyl-carbonylamino, represents C
3
-C
6
-alkenyloxy, represents di-(C
1
-C
4
-alkyl)-amino, represents in each case optionally fluorine-, chlorine-, bromine-, cyano- and/or C
1
-C
4
-alkyl-substituted C
3
-C
6
-cycloalkyl, C
3
-C
6
-cycloalkylamino 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 and/or C
1
-C
4
-alkoxy-substituted phenyl or phenyl-C
1
-C
4
-alkyl,
R
5
represents hydrogen, hydroxyl, mercapto, amino, cyano, fluorine, chlorine, bromine, iodine, 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 in each case optionally fluorine-, chlorine-, cyano-, C
1
-C
4
-alkoxy- or C
1
-C
4
-alkoxy-carbonyl-substituted C
1
-C
6
-alkoxy, C
1
-C
6
-alkylthio, C
1
-C
6
-alkylamino or C
1
-C
6
-alkyl-carbonylamino, represents C
3
-C
6
-alkenyloxy, C
3
-C
6
-alkinyloxy, C
3
-C
6
-alkenylthio, C
3
-C
6
-alkinylthio, C
3
-C
6
-alkenylamino or C
3
-C
6
-alkinylamino, represents di-(C
1
-C
4
-alkyl)-amino, represents in each case optionally methyl- and/or ethyl-substituted aziridino, pyrrolidino, piperidino or morpholino, represents in each case optionally fluorine-, chlorine-, bromine-, cyano- and/or C
1
-C
4
-alkyl-substituted C
3
-C
6
-cycloalkyl, C
5
-C
6
-cycloalkenyl, C
3
-C
6
-cycloalkyloxy, C
3
-C
6
-cycloalkylthio, C
3
-C
6
-cycloalkylamino, C
3
-C
6
-cycloalkyl-C
1
-C
4
-alkyl, C
3
-C
6
-cycloalkyl-C
1
-C
4
-alkoxy, C
3
-C
6
-cycloalkyl-C
1
-C
4
-alkylthio or C
3
-C
6
-cycloalkyl-C
1
-C
4
-alkylamino, 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, phenyl-C
1
-C
4
-alkyl, phenoxy, phenyl-C
1
-C
4
-alkoxy, phenylthio, phenyl-C
1
-C
4
-alkylthio, phenylamino or phenyl-C
1
-C
4
-alkylamino, or
R
4
and R
5
together represent optionally branched alkanediyl having 3 to 11 carbon atoms, furthermore
R
6
, R
7
and R
8
are identical or different and each represent hydrogen, cyano, fluorine, chlorine, bromine, or represent in each case optionally fluorine-, chlorine-, bromine- or C
1
-C
4
-alkoxy-substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkenylthio, alkinylthio, alkylsulphi

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