Substituted sulphonyl amino(thio)carbonyl compounds and...

Details Substituted sulphonyl amino(thio)carbonyl compounds and... Substituted sulphonyl amino(thio)carbonyl compounds and...

1999-05-13

2004-01-13

McKane, Joseph K. (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Plural active ingredients

C548S263200, C548S263400, C548S263800

Reexamination Certificate

active

06677277

ABSTRACT:

TECHNICAL FIELD OF THE INVENTION
The invention relates to novel substituted sulfonylamino(thio)carbonyl compounds, to a plurality of processes and to novel intermediates for preparing them, and to their use as herbicides.
BACKGROUND OF THE INVENTION
It is already known that certain sulfonylaminocarbonyl compounds have herbicidal properties (cf. EP 341489, EP 422469, EP 425948, EP 431291, EP 507171, EP 534266, DE 4029753). The action of these compounds, however, is not satisfactory in every respect.
DETAILED DESCRIPTION OF THE INVENTION
This invention, then, provides the novel sulfonylamino(thio)carbonyl compounds of the general formula (I)
in which
n represents the numbers 0, 1 or 2,
A represents a single bond, or oxygen or sulfur, or the grouping N—R, in which R represents hydrogen, alkyl, alkenyl, alkinyl or cycloalkyl,
Q represents oxygen or sulfur,
R
1
represents hydrogen or formyl or represents respectively optionally substituted alkyl, alkoxy, alkylamino, alkoxyamino, dialkylamino, N-alkoxy-N-alkyl-amino, alkylcarbonyl, alkoxycarbonyl, alkylsulfonyl, alkenyl, alkinyl, cycloalkyl, cycloalkylcarbonyl or cycloalkylsulfonyl,
R
2
represents cyano or halogen or represents respectively optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, dialkylaminosulfonyl, alkenyl, alkinyl, alkenyloxy or alkinyloxy, and
R
3
represents respectively optionally substituted heterocyclyl having 5 ring members of which at least one is oxygen, sulfur or nitrogen and from one to three further ring members can be nitrogen,
and salts of compounds of the formula (I).
The novel substituted sulfonylamino(thio)carbonyl compounds of the general formula (I) are obtained by reacting
(a) aminosulfonyl compounds of the general formula (II)
 in which
n, A, R
1
and R
2
are each as defined above
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,
optionally in the presence of an acid acceptor and optionally in the presence of a diluent, or
(b) sulfonyl iso(thio)cyanates of the general formula (IV)
 in which
n, A, Q, R
1
and R
2
are each as defined above
with heterocycles of the general formula (V)
H—R
3
  (V)
 in which
R
3
is as defined above,
optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent, or
(c) chlorosulfonyl compounds of the general formula (VI)
 in which
n, A, R
1
and R
2
are each as defined above
with heterocycles of the general formula (V)
H—R
3
  (V)
 in which
R
3
is as defined above
and metal (thio)cyanates of the general formula (VII)
MQCN  (VII)
 in which
Q is as defined above,
optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent, or
(d) chlorosulfonyl compounds of the general formula (VI)
 in which
n, A, R
1
and R
2
are each as defined above,
with (thio)carboxamides of the general formula (VIII)
 in which
Q and R
3
are each as defined above,
optionally in the presence of an acid acceptor and optionally in the presence of a diluent, or
(e) sulfonylamino(thio)carbonyl compounds of the general formula (IX)
 in which
n, A, Q, R
1
and R
2
are each as defined above and
Z represents halogen, alkoxy, aryloxy or arylalkoxy,
with heterocycles of the general formula (V)
H—R
3
  (V)
 in which
R
3
is as defined above,
optionally in the presence of an acid acceptor and optionally in the presence of a diluent, or
(f) heterocycles of the general formula (V)
H—R
3
  (V)
 in which
R
3
is as defined above,
with chlorosulfonyl iso(thio)cyanate, optionally in the presence of a diluent, and reacting the adducts formed in this reaction in situ with benzene derivatives of the general formula (X)
 in which
n, A, R
1
and R
2
are each as defined above,
optionally in the presence of an acid acceptor and optionally in the presence of a diluent,
and converting, if desired, the compounds of the formula (I) obtained by processes (a), (b), (c), (d), (e) or (f) by customary methods into salts.
The novel substituted sulfonylamino(thio)carbonyl compounds of the general formula (I) have strong herbicidal activity.
The invention preferably provides compounds of the formula (I) in which
n represents the numbers 0, 1 or 2,
A represents a single bond, or oxygen or sulfur, or the grouping N—R, in which R represents hydrogen, C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkinyl or C
3
-C
6
-cycloalkyl,
Q represents oxygen or sulfur,
R
1
represents hydrogen or formyl or represents respectively optionally cyano-, fluoro-, chloro-, bromo-, phenyl- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alkylamino, alkoxyamino, dialkylamino, N-alkoxy-N-alkyl-amino, alkylcarbonyl, alkoxycarbonyl, alkylsulfonyl, alkenyl or alkinyl having in each case up to 6 carbon atoms, or represents respectively optionally cyano-, fluoro-, chloro-, bromo- or C
1
-C
4
-alkyl-substituted C
3
-C
6
-cycloalkyl, C
3
-C
6
-cycloalkyl-carbonyl or C
3
-C
6
-cycloalkyl-sulfonyl,
R
2
represents cyano, fluoro, chloro or bromo or represents respectively optionally cyano-, fluoro-, chloro-, bromo- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, dialkylaminosulfonyl, alkenyl, alkinyl, alkenyloxy or alkinyloxy having in each case up to 6 carbon atoms, and
R
3
represents respectively optionally substituted heterocyclyl of the formulae below,
 in which
Q
1
, Q
2
and Q
3
each represent oxygen or sulfur, and
R
4
represents hydrogen, hydroxyl, amino or cyano, or represents C
2
-C
10
-alkylideneamino, or represents optionally fluoro-, chloro-, bromo-, 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, or represents respectively optionally fluoro-, chloro- and/or bromo-substituted C
2
-C
6
-alkenyl or C
2
-C
6
-alkinyl, or represents respectively optionally fluoro-, chloro-, bromo-, 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, or represents C
3
-C
6
-alkenyloxy, or represents di-(C
1
-C
4
-alkyl)-amino, or represents respectively optionally fluoro-, chloro-, bromo-, 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 respectively optionally fluoro-, chloro-, bromo-, 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, fluoro, chloro, bromo or iodo, or represents optionally fluoro-, chloro-, bromo-, 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, or represents respectively optionally fluoro-, chloro- and/or bromo-substituted C
2
-C
6
-alkenyl or C
2
-C
6
-alkinyl, or represents respectively optionally fluoro-, chloro-, 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
-alkylcarbonylamino, or 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, or represents di-(C
1
-C
4
-alkyl)-amino, or represents respectively optionally methyl- and/or ethyl-substituted aziridino, pyrrolidino, piperidino or morpholino, or represents respectively optionally fluoro-, chloro-, bromo-, 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 respectively optionally fluoro-, chloro-, bromo-, cyano-, nitro-, C
1
-C
4
-alkyl-, trifluoromethyl-, C
1
-C
4
-alkoxy- and/or C
1
-C
4
-alkoxy-carbonyl-s

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