Herbicidal sulphonylamino(thio)carbonyl compounds

Details Herbicidal sulphonylamino(thio)carbonyl compounds Herbicidal sulphonylamino(thio)carbonyl compounds

2001-04-20

2003-02-25

Raymond, Richard L. (Department: 1624)

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

Organic compounds

Nitriles

C562S833000, C562S870000, C564S089000

Reexamination Certificate

active

06525211

ABSTRACT:

The invention relates to novel sulphonylamino(thio)carbonyl compounds, to a number of processes and to novel intermediates for their preparation, and to their use as herbicides.
It is already known that certain sulphonylaminocarbonyl compounds, such as, for example, the compounds 4,5-dimethoxy-2-(2-methoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, 4,5-dimethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, 4,5-diethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one and N-(2,5-dimethoxy-phenylsulphonyl)-1,5-dimethyl-1H-pyrazole-3-carbox-amide possess 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 in every respect satisfactory.
The novel sulphonylamino(thio)carbonyl compounds have now been found of the general formula (I),
in which
A represents a single bond, oxygen, sulphur or the group N—R, in which R represents hydrogen, alkyl, alkenyl, alkinyl or cycloalkyl,
Q represents oxygen or sulphur,
R
1
represents hydrogen or formyl or represents in each case optionally substituted alkyl, alkenyl, alkinyl, alkylcarbonyl, alkoxycarbonyl, alkylsulphonyl, cycloalkyl, cycloalkylcarbonyl or cycloalkylsulphonyl,
R
2
represents cyano or halogen or represents in each case optionally substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy or alkinyloxy, and
R
3
represents in each case optionally substituted heterocyclyl having 5 ring members of which at least one is oxygen, sulphur or nitrogen and from one to three further ring members can be nitrogen,
and salts of compounds of the formula (I),
the previously known compounds 4,5-dimethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, 4,5-diethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one and N-(2,5-dimethoxy-phenylsulphonyl)-1,5-dimethyl-1H-pyrazole-3-carboxamiide being excluded by disclaimer.
The novel sulphonylamino(thio)carbonyl compounds of the general formula (I) are obtained if
(a) aminosulphonyl compounds of the general formula (II)
 in which
A, R
1
and R
2
have the meanings given above
are reacted with (thio)carboxylic acid derivatives of the general formula (III)
 in which
Q and R
3
have the meanings given 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 if
(b) sulphonyl iso(thio)cyanates of the general formula (I)
 in which
A, Q, R
1
and R
2
have the meanings given above
are reacted with heterocycles of the general formula (V)
H—R
3
  (V)
 in which
R
3
has the meaning given above,
optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent,
or if
(c) chlorosulphonyl compounds of the general formula (VI)
 in which
A, R
1
and R
2
have the meanings given above
are reacted with heterocycles of the general formula (V)
H—R
3
  (V)
 in which
R
3
has the meaning given above
and metal (thio)cyanates of the general formula (VII)
MQCN  (VII)
 in which
Q has the meaning given above, and
M represents an alkali metal or alkaline earth metal equivalent,
optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent,
or if
(d) chlorosulphonyl compounds of the general formula (VI)
 in which
A, R
1
and R
2
have the meanings given above
are reacted with (thio)carboxamides of the general formula (VIII)
 in which
Q and R
3
have the meanings given above,
optionally in the presence of an acid acceptor and optionally in the presence of a diluent,
or if
(e) sulphonylamino(thio)carbonyl compounds of the general formula (IX)
 in which
A, Q, R
1
and R
2
have the meanings given above, and
Z represents halogen, alkoxy, aryloxy or arylalkoxy,
are reacted with heterocycles of the general formula (V)
H—R
3
  (V)
 in which
R
3
has the meaning given above,
optionally in the presence of an acid acceptor and optionally in the presence of a diluent,
or if
(f) heterocycles of the general formula (V)
H—R
3
  (V)
 in which
R
3
has the meaning given above,
are reacted with chlorosulphonyl iso(thio)cyanate, optionally in the presence of a diluent, and the adducts formed in this reaction are reacted in situ with benzene derivatives of the general formula (X)
 in which
A, R
1
and R
2
have the meanings given above,
optionally in the presence of an acid acceptor and optionally in the presence of a diluent,
and, if desired, the compounds of the formula (I) obtained by processes (a), (b), (c), (d), (e) or (f) are converted into salts by customary methods.
The novel sulphonylamino(thio)carbonyl compounds of the general formula (I) are distinguished by a strong herbicidal activity.
The invention relates preferably to compounds of the formula (I) in which
A represents a single bond, oxygen, sulphur or the group 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 sulphur,
R
1
represents hydrogen or formyl or represents in each case optionally cyano-, fluoro-, chloro-, bromo-, phenyl- or C
1
-C
4
-alkoxy-substituted alkyl, alkenyl, alkinyl, alkylcarbonyl, alkoxycarbonyl or alkylsulphonyl having in each case up to 6 carbon atoms, or represents in each case 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-sulphonyl,
R
2
represents cyano, fluoro, chloro or bromo or represents in each case optionally cyano-, fluoro-, chloro-, bromo- 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 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 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 in each case optionally fluoro-, chloro- and/or bromo-substituted C
2
-C
6
-alkenyl or C
2
-C
6
-alkinyl, or represents in each case 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 in each case 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 in each case optionally fluoro-, chloro-, bromo-, cyano-, nitro-, C
1
-C
4
-alkyl-, trifluoromethyl- and/or C
1
-C
4
-alkoxy-substituted phenyl, phenylamino 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 in each case optionally fluoro-, chloro- and/or bromo-substituted C
2
-C
6
-alkenyl or C
2
-C
6
-alkinyl, or represents in each case 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
-alkyl-carbonylamino, 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 in each case optionally methyl- and/or ethyl-substituted aziridino, pyrrolidino, piperidino or morpholino, or represents in each case optionally fluoro-, chloro-, bromo-, cyano-

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